Compound and organic electroluminescent device

Abstract

The present invention belongs to the technical field of organic electroluminescence. Disclosed are a compound and an organic electroluminescent device. The general structural formula of the compound is shown in formula (1): formula (1), where: X is selected from NRa, CRbRc, O, S or Se; ET represents an electron-withdrawing group; L is selected from a single bond, a substituted or unsubstituted C6-C60 arylidene group or a substituted or unsubstituted C3-C60 heteroarylene group; ring A is selected from the structure shown in formula (2) or formula (3); formula (2), formula (3); X1-X12 are independently selected from CR0 or N; and there are two adjacent sites in X1-X4, X5-X6, X7-X8 and X9-X12 that are fused with a 5-membered ring containing X in formula (1). The described compound has the advantages of high optical and electrical stability, low sublimation temperature, low driving voltage, high luminous efficiency, long device life, etc., and can be used as a red light host material in OLED light-emitting devices.

Description

Compound and organic electroluminescent device Technical Field

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

[0002] Organic light-emitting diodes (OLEDs), a next-generation display technology, are gaining increasing attention in both display and lighting applications, boasting a broad range of applications. However, compared to market requirements, OLED device performance, including luminous efficiency, driving voltage, and lifespan, still requires further improvement.

[0003] Generally speaking, the basic structure of an OLED device consists of thin films of various organic functional materials sandwiched between metal electrodes, creating a sandwich-like structure. Driven by an electric current, holes and electrons are injected from the cathode and anode, respectively. After traveling a certain distance, the holes and electrons recombine in the light-emitting layer and release the energy as light or heat, thus generating the OLED's luminescence. However, the properties of phosphorescent OLEDs are not solely determined by the triplet emitter used. Other materials, such as the host material, are also crucial. The host material plays a significant role in reducing the device's driving voltage, improving its luminous efficiency, and extending its lifespan. Therefore, it is necessary to continue researching and developing new host materials to further enhance the performance of organic electroluminescent devices.

[0004] To enhance the luminous efficiency, driving voltage, and lifespan of OLED devices, various host materials have been proposed for use in organic electroluminescent devices. However, these materials have not been satisfactory in practical applications, with most exhibiting technical issues such as high driving voltages and high sublimation temperatures, which affect luminous efficiency and device lifespan. Consequently, there is a continuing need to develop host materials for improving OLED performance. Summary of the Invention

[0005] The present invention aims to solve at least one of the technical problems existing in the above-mentioned prior art. To this end, the present invention provides a compound and an organic electroluminescent device.

[0006] In order to solve the above technical problems, the first aspect of the present invention provides a compound, the general structural formula of which is shown in formula (1):

[0007] Where: X is selected from NR a , CR b R c , O, S or Se;

[0008] R a 、R b 、Rc Each is independently selected from C1-C30 alkyl, C1-C30 heteroalkyl, C3-C30 cycloalkyl, C3-C30 heterocycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C3-C30 alkylsilyl, and C6-C30 arylsilyl;

[0009] ET represents an electron-withdrawing group;

[0010] L is selected from a single bond, a substituted or unsubstituted C6-C60 arylene group, or a substituted or unsubstituted C3-C60 heteroarylene group;

[0011] Ring A is selected from the structure represented by formula (2) or formula (3);

[0012] X1-X 12 are independently selected from CR0 or N; and X1-X4, X5-X6, X7-X8, X9-X 12 There are two adjacent sites fused to the 5-membered ring containing X in formula (1);

[0013] R0 is selected from hydrogen, deuterium, halogen, cyano, nitro, C1-C40 alkyl, C1-C40 heteroalkyl, C2-C40 alkenyl, C2-C40 alkynyl, C3-C40 cycloalkyl, C3-C40 heterocycloalkyl, C6-C60 aryl, C3-C60 heteroaryl, C1-C40 alkoxy, C6-C60 aryloxy, C3-C40 alkylsilyl, C6-C60 arylsilyl, C1-C40 alkylboryl, C6-C60 arylboryl, C6-C60 arylphosphino, C6-C60 monoarylphosphino, C6-C60 diarylphosphino or C6-C60 arylamine; and two adjacent R0 may be connected to form a ring;

[0014] The substitution is substituted by at least one of deuterium, halogen, cyano, isocyano, phosphino, C1-C6 alkyl, C3-C16 cycloalkyl, C1-C6 alkyl-substituted amine, C1-C6 hydrocarbon-substituted or unsubstituted C6-C30 aryl, C1-C6 hydrocarbon-substituted or unsubstituted C3-C30 heteroaryl, wherein the number of substitutions ranges from single substitution to the maximum number of substitutions.

[0015] In some embodiments, the R a 、R b 、R c They are independently selected from C1-C20 alkyl, C1-C20 heteroalkyl, C3-C20 cycloalkyl, C3-C20 heterocycloalkyl, C6-C20 aryl, C3-C20 heteroaryl, C3-C20 alkylsilyl and C6-C20 arylsilyl.

[0016] In some embodiments, the R a 、R b 、R c They are independently selected from C1-C10 alkyl, C1-C10 heteroalkyl, C3-C10 cycloalkyl, C3-C10 heterocycloalkyl, C6-C10 aryl, and C3-C10 heteroaryl.

[0017] In some embodiments, R0 is selected from hydrogen, deuterium, halogen, cyano, nitro, C1-C30 alkyl, C1-C30 heteroalkyl, C2-C30 alkenyl, C2-C30 alkynyl, C3-C30 cycloalkyl, C3-C30 heterocycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C1-C30 alkoxy, C6-C30 aryloxy, C3-C30 alkylsilyl, C6-C30 arylsilyl, C1-C30 alkylboryl, C6-C30 arylboryl, C6-C30 arylphosphino, C6-C30 monoarylphosphino, C6-C30 diarylphosphino or C6-C30 arylamine; and two adjacent R0 can be connected to form a ring.

[0018] In some embodiments, R0 is selected from hydrogen, deuterium, halogen, cyano, nitro, C1-C20 alkyl, C1-C20 heteroalkyl, C2-C20 alkenyl, C2-C20 alkynyl, C3-C20 cycloalkyl, C3-C20 heterocycloalkyl, C6-C20 aryl, C3-C20 heteroaryl, C1-C20 alkoxy, C6-C20 aryloxy, C3-C20 alkylsilyl, C6-C20 arylsilyl, C1-C20 alkylboryl, C6-C20 arylboryl, C6-C20 arylphosphino, C6-C20 monoarylphosphino, C6-C20 diarylphosphino or C6-C20 arylamine; and two adjacent R0 can be connected to form a ring.

[0019] In some embodiments, the R0 is selected from hydrogen, deuterium, halogen, cyano, nitro, C1-C10 alkyl, C1-C10 heteroalkyl, C2-C10 alkenyl, C2-C10 alkynyl, C3-C10 cycloalkyl, C3-C10 heterocycloalkyl, C6-C12 aryl, C3-C12 heteroaryl; and two adjacent R0 can be connected to form a ring.

[0020] In some embodiments, adjacent R0 refers to R0 located on adjacent carbon atoms.

[0021] In some embodiments, the substitution is by at least one of deuterium, halogen, cyano, isocyano, phosphino, C1-C6 alkyl, C3-C12 cycloalkyl, C1-C6 alkyl-substituted amine, C6-C18 aryl, or C3-C18 heteroaryl, wherein the number of substitutions ranges from a single substitution to a maximum number of substitutions.

[0022] In some embodiments, the substitution is by at least one of deuterium, halogen, cyano, isocyano, phosphino, C1-C6 alkyl, C3-C10 cycloalkyl, C1-C6 alkyl-substituted amine, C6-C12 aryl, or C3-C12 heteroaryl, wherein the number of substitutions ranges from a single substitution to a maximum number of substitutions.

[0023] In some embodiments, the heteroatoms in the heteroaryl, heteroalkyl and heterocycloalkyl groups are independently selected from at least one of O, S, N, Se, Si and Ge.

[0024] In some embodiments, the structure represented by formula (2) or formula (3) is selected from the structures represented by formula (A-1) to (A-8):

[0025] Wherein: * represents the site of fusion with the 5-membered ring containing X in formula (1);

[0026] m is an integer of 0-10; if m is an integer not less than 2, each R0 may be the same or different, and two adjacent R0 may be connected to form a ring.

[0027] In some embodiments, the structure represented by formula (2) or formula (3) is selected from the structures represented by formula (A-9) to (A-16):

[0028] Wherein, * represents the site fused to the 5-membered ring containing X in formula (1);

[0029] t is an integer from 0 to 6; if t is an integer not less than 2, each R0 may be the same or different, and two adjacent R0s may be connected to form a ring. In some embodiments, the electron-withdrawing group is selected from the structures shown in formulas (B-1) to (B-10):

[0030] Wherein: * represents the site of connection with L in formula (1);

[0031] Z is selected from N or CR d , and at least one Z is N, and two adjacent Zs in formula (B-10) are not N at the same time;

[0032] W is selected from NR e 、O、S、SO、SO2、CR f R g or SiRh R j ;

[0033] Y is selected from NR a , CR b R c , O, S or Se, and Ra, R b 、R c R of X in claim 1 a 、R b 、R c consistent definitions;

[0034] R1, Rd-Rh, Rj are independently selected from hydrogen, deuterium, halogen, cyano, nitro, C1-C40 alkyl, C1-C40 heteroalkyl, C2-C40 alkenyl, C2-C40 alkynyl, C3-C40 cycloalkyl, C3-C40 heterocycloalkyl, C3-C40 alkylsilyl, C6-C60 arylsilyl, C1-C40 alkylboryl, C1-C40 alkoxy substituted or an unsubstituted C6-C60 aryl group, a substituted or unsubstituted C3-C60 heteroaryl group, a substituted or unsubstituted C6-C60 aryloxy group, a substituted or unsubstituted C6-C60 arylboronyl group, a substituted or unsubstituted C6-C60 arylphosphino group, a substituted or unsubstituted C6-C60 monoarylphosphino group, a substituted or unsubstituted C6-C60 diarylphosphino group, or a substituted or unsubstituted C6-C60 arylamine group;

[0035] The substitution is substituted by at least one of deuterium, halogen, cyano, isocyano, phosphino, C1-C6 alkyl, C3-C16 cycloalkyl, C1-C6 alkyl-substituted amine, C1-C6 alkyl-substituted or unsubstituted C6-C30 aryl, C1-C6 alkyl-substituted or unsubstituted C3-C30 heteroaryl, wherein the number of substitutions ranges from single substitution to the maximum number of substitutions;

[0036] n is an integer of 0-10; if n is an integer not less than 2, each R1 may be the same or different, and two adjacent R1s may be connected to form a ring.

[0037] In some embodiments, adjacent R1 refers to R1 located on adjacent carbon atoms.

[0038] In some embodiments, the Rd-Rh, Rj are independently selected from hydrogen, deuterium, halogen, cyano, nitro, C1-C30 alkyl, C1-C30 heteroalkyl, C2-C30 alkenyl, C2-C30 alkynyl, C3-C30 cycloalkyl, C3-C30 heterocycloalkyl, C3-C30 alkylsilyl, C6-C30 arylsilyl, C1-C30 alkylboryl, C1-C30 alkane an oxy-substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C3-C30 heteroaryl group, a substituted or unsubstituted C6-C30 aryloxy group, a substituted or unsubstituted C6-C30 arylboronyl group, a substituted or unsubstituted C6-C30 arylphosphino group, a substituted or unsubstituted C6-C30 monoarylphosphino group, a substituted or unsubstituted C6-C30 diarylphosphino group, or a substituted or unsubstituted C6-C30 arylamine group.

[0039] In some embodiments, the Rd-Rh, Rj are independently selected from hydrogen, deuterium, halogen, cyano, nitro, C1-C20 alkyl, C1-C20 heteroalkyl, C2-C20 alkenyl, C2-C20 alkynyl, C3-C20 cycloalkyl, C3-C20 heterocycloalkyl, C3-C20 alkylsilyl, C6-C20 arylsilyl, C1-C20 alkylboryl, C1-C20 alkane an oxy-substituted or unsubstituted C6-C20 aryl group, a substituted or unsubstituted C3-C20 heteroaryl group, a substituted or unsubstituted C6-C20 aryloxy group, a substituted or unsubstituted C6-C20 arylboronyl group, a substituted or unsubstituted C6-C20 arylphosphino group, a substituted or unsubstituted C6-C20 monoarylphosphino group, a substituted or unsubstituted C6-C20 diarylphosphino group, or a substituted or unsubstituted C6-C20 arylamine group.

[0040] In some embodiments, the Rd-Rh, Rj are independently selected from hydrogen, deuterium, halogen, cyano, nitro, C1-C10 alkyl, C1-C10 heteroalkyl, C2-C10 alkenyl, C2-C10 alkynyl, C3-C10 cycloalkyl, C3-C10 heterocycloalkyl, C3-C10 alkylsilyl, C6-C10 arylsilyl, C1-C10 alkylboryl, C1-C10 alkane an oxy-substituted or unsubstituted C6-C10 aryl group, a substituted or unsubstituted C3-C10 heteroaryl group, a substituted or unsubstituted C6-C10 aryloxy group, a substituted or unsubstituted C6-C10 arylboronyl group, a substituted or unsubstituted C6-C10 arylphosphinyl group, a substituted or unsubstituted C6-C10 monoarylphosphinyl group, a substituted or unsubstituted C6-C10 diarylphosphinyl group, or a substituted or unsubstituted C6-C10 arylamine group.

[0041] In some embodiments, Rd-Rh, and Rj are independently selected from hydrogen, deuterium, halogen, cyano, nitro, C1-C10 alkyl, C1-C10 heteroalkyl, C2-C10 alkenyl, C2-C10 alkynyl, C3-C10 cycloalkyl, C3-C10 heterocycloalkyl, C6-C10 aryl, C3-C10 heteroaryl, C6-C10 aryloxy, C6-C10 arylboronyl, C6-C10 arylphosphino, C6-C10 monoarylphosphino, C6-C10 diarylphosphino, or C6-C10 arylamine.

[0042] In some embodiments, the electron-withdrawing group is selected from the structures shown in formulas (B-11) to (B-36):

[0043] Wherein: R1 and R2 are independently selected from hydrogen, deuterium, halogen, cyano, nitro, C1-C40 alkyl, C1-C40 heteroalkyl, C2-C40 alkenyl, C2-C40 alkynyl, C3-C40 cycloalkyl, C3-C40 heterocycloalkyl, C3-C40 alkylsilyl, C6-C60 arylsilyl, C1-C40 alkylboryl, C1-C40 alkoxy substituted or unsubstituted a substituted C6-C60 aryl group, a substituted or unsubstituted C3-C60 heteroaryl group, a substituted or unsubstituted C6-C60 aryloxy group, a substituted or unsubstituted C6-C60 arylboronyl group, a substituted or unsubstituted C6-C60 arylphosphino group, a substituted or unsubstituted C6-C60 monoarylphosphino group, a substituted or unsubstituted C6-C60 diarylphosphino group, or a substituted or unsubstituted C6-C60 arylamine group.

[0044] In some embodiments, R1 and R2 are independently selected from hydrogen, deuterium, halogen, cyano, nitro, C1-C30 alkyl, C1-C30 heteroalkyl, C2-C30 alkenyl, C2-C30 alkynyl, C3-C30 cycloalkyl, C3-C30 heterocycloalkyl, C3-C30 alkylsilyl, C6-C30 arylsilyl, C1-C30 alkylboryl, C1-C30 alkoxy a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C3-C30 heteroaryl group, a substituted or unsubstituted C6-C30 aryloxy group, a substituted or unsubstituted C6-C30 arylboronyl group, a substituted or unsubstituted C6-C30 arylphosphino group, a substituted or unsubstituted C6-C30 monoarylphosphino group, a substituted or unsubstituted C6-C30 diarylphosphino group, or a substituted or unsubstituted C6-C30 arylamine group.

[0045] In some embodiments, R1 and R2 are independently selected from hydrogen, deuterium, halogen, cyano, nitro, C1-C20 alkyl, C1-C20 heteroalkyl, C2-C20 alkenyl, C2-C20 alkynyl, C3-C20 cycloalkyl, C3-C20 heterocycloalkyl, C3-C20 alkylsilyl, C6-C20 arylsilyl, C1-C20 alkylboryl, C1-C20 alkoxy a substituted or unsubstituted C6-C20 aryl group, a substituted or unsubstituted C3-C20 heteroaryl group, a substituted or unsubstituted C6-C20 aryloxy group, a substituted or unsubstituted C6-C20 arylboronyl group, a substituted or unsubstituted C6-C20 arylphosphino group, a substituted or unsubstituted C6-C20 monoarylphosphino group, a substituted or unsubstituted C6-C20 diarylphosphino group, or a substituted or unsubstituted C6-C20 arylamine group.

[0046] In some embodiments, R1 and R2 are independently selected from hydrogen, deuterium, halogen, cyano, nitro, C1-C10 alkyl, C1-C10 heteroalkyl, C2-C10 alkenyl, C2-C10 alkynyl, C3-C10 cycloalkyl, C3-C10 heterocycloalkyl, C3-C10 alkylsilyl, C6-C10 arylsilyl, C1-C10 alkylboryl, C1-C10 alkoxy a substituted or unsubstituted C6-C10 aryl group, a substituted or unsubstituted C3-C10 heteroaryl group, a substituted or unsubstituted C6-C10 aryloxy group, a substituted or unsubstituted C6-C10 arylboronyl group, a substituted or unsubstituted C6-C10 arylphosphino group, a substituted or unsubstituted C6-C10 monoarylphosphino group, a substituted or unsubstituted C6-C10 diarylphosphino group, or a substituted or unsubstituted C6-C10 arylamine group.

[0047] In some embodiments, R1 and R2 are independently selected from hydrogen, deuterium, halogen, substituted or unsubstituted C6-C20 arylene or substituted or unsubstituted C3-C20 heteroarylene; and each R1 may be the same or different, and two adjacent R1s may be connected to form a ring.

[0048] In some embodiments, R1 and R2 are independently selected from hydrogen, deuterium, halogen, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted substituted or unsubstituted carbazolyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted fluoranthene, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted benzotriazolyl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted naphthoxazolyl, substituted or unsubstituted phenanthroxazolyl, substituted or unsubstituted quinolyl, substituted or unsubstituted benzocycloalkyl, substituted or unsubstituted benzocarbazolyl, substituted or unsubstituted naphthobenzofuranyl, substituted or unsubstituted azaphenanthrenyl, or a combination of at least two of the foregoing.

[0049] In some embodiments, X is selected from CR b R c , O or S; and R in X b 、R c They are each independently selected from C1-C10 alkyl, C1-C10 heteroalkyl, C3-C10 cycloalkyl, C3-C10 heterocycloalkyl, C6-C10 aryl or C3-C10 heteroaryl.

[0050] In some embodiments, L is selected from a single bond, a substituted or unsubstituted C6-C20 arylene group, or a substituted or unsubstituted C3-C20 heteroarylene group.

[0051] In some embodiments, the L is selected from a single bond or structures represented by formula (L-1) to formula (L-14):

[0052] wherein: R is a substituent, each R being independently selected from hydrogen, deuterium, halogen, cyano, nitro, C1-C20 alkyl, C1-C20 heteroalkyl, C2-C20 alkenyl, C2-C20 alkynyl, C3-C20 cycloalkyl, C3-C20 heterocycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C1-C20 alkoxy, C6-C30 aryloxy, C3-C20 alkylsilyl, C6-C30 arylsilyl, C1-C20 alkylboryl, C6-C30 arylboryl, C6-C30 arylphosphino, C6-C30 monoarylphosphino, C6-C30 diarylphosphino, or C6-C30 arylamine; wherein the number of substitutions is from monosubstitution to the maximum number of substitutions.

[0053] In some embodiments, R is a substituent, each R being independently selected from hydrogen, deuterium, halogen, cyano, nitro, C1-C10 alkyl, C1-C10 heteroalkyl, C2-C10 alkenyl, C2-C10 alkynyl, C3-C10 cycloalkyl, C3-C10 heterocycloalkyl, C6-C20 aryl, C3-C20 heteroaryl, C1-C10 alkoxy, C6-C20 aryloxy, C3-C10 alkylsilyl, C6-C20 arylsilyl, C1-C10 alkylboryl, C6-C20 arylboryl, C6-C20 arylphosphino, C6-C20 monoarylphosphino, C6-C20 diarylphosphino, or C6-C20 arylamine; wherein the number of substitutions is from monosubstitution to the maximum number of substitutions.

[0054] In some embodiments, the compound has a structural formula of one of the structural formulas shown in Formulas CPD1 to CPD645, or a structure in which hydrogen in Formulas CPD1 to CPD645 is partially or completely replaced by deuterium, or a structure in which hydrogen in Formulas CPD1 to CPD645 is partially or completely replaced by fluorine:

[0055] A second aspect of the present invention provides an organic electroluminescent device comprising a light-emitting layer, wherein the light-emitting layer comprises the above compound.

[0056] In some embodiments, the organic electroluminescent device includes a cathode, an anode, and a light-emitting layer, wherein the cathode and anode are disposed opposite each other, and the light-emitting layer is disposed between the cathode and the anode. The light-emitting layer includes the above-described organic electroluminescent compound. The organic electroluminescent compound of the present invention can be used alone or after doping to prepare the light-emitting layer.

[0057] In some embodiments, the light-emitting layer is a red light-emitting layer, which includes a red light-emitting material and at least one of the above-mentioned organic electroluminescent compounds. The organic electroluminescent compound of the present invention serves as a host material of the red light-emitting layer.

[0058] Compared with the prior art, the above technical solution of the present invention has at least the following technical effects or advantages:

[0059] The compound synthesized in this invention exhibits advantages such as high optical and electrical stability, low sublimation temperature, low driving voltage, high luminous efficiency, and long device life. It can be used as a red light host material in OLED light-emitting devices. Furthermore, the compound synthesized in this invention has a low melting point, which improves the stability of material evaporation as a molten material. Therefore, its use as a host material has potential applications in the active-matrix organic light-emitting diode (AMOLED) industry. BRIEF DESCRIPTION OF THE DRAWINGS

[0060] FIG1 is a diagram of the compound CPD59 of the present invention. 1 H NMR spectrum;

[0061] FIG2 is a schematic structural diagram of an organic electroluminescent device according to an embodiment of the present invention. DETAILED DESCRIPTION

[0062] The present invention is described in detail below with reference to the examples to facilitate understanding of the present invention by those skilled in the art. It is necessary to point out that the examples are only used to further illustrate the present invention and are not to be construed as limiting the scope of protection of the present invention. Non-essential improvements and adjustments made to the present invention by those skilled in the art based on the above-mentioned invention should still fall within the scope of protection of the present invention. At the same time, the raw materials mentioned below that are not described in detail are all commercially available products; the process steps or preparation methods that are not mentioned in detail are all process steps or preparation methods known to those skilled in the art.

[0063] A compound, the general structural formula of which is shown in formula (1):

[0064] Where: X is selected from NR a , CR b R c , O, S or Se;

[0065] R a 、R b 、R c Each is independently selected from C1-C30 alkyl, C1-C30 heteroalkyl, C3-C30 cycloalkyl, C3-C30 heterocycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C3-C30 alkylsilyl, and C6-C30 arylsilyl;

[0066] ET represents an electron-withdrawing group;

[0067] L is selected from a single bond, a substituted or unsubstituted C6-C60 arylene group, or a substituted or unsubstituted C3-C60 heteroarylene group;

[0068] Ring A is selected from the structure represented by formula (2) or formula (3);

[0069] X1-X 12 are independently selected from CR0 or N; and X1-X4, X5-X6, X7-X8, X9-X 12 There are two adjacent sites fused to the 5-membered ring containing X in formula (1);

[0070] R0 is selected from hydrogen, deuterium, halogen, cyano, nitro, C1-C40 alkyl, C1-C40 heteroalkyl, C2-C40 alkenyl, C2-C40 alkynyl, C3-C40 cycloalkyl, C3-C40 heterocycloalkyl, C6-C60 aryl, C3-C60 heteroaryl, C1-C40 alkoxy, C6-C60 aryloxy, C3-C40 alkylsilyl, C6-C60 arylsilyl, C1-C40 alkylboryl, C6-C60 arylboryl, C6-C60 arylphosphino, C6-C60 monoarylphosphino, C6-C60 diarylphosphino or C6-C60 arylamine; and two adjacent R0 may be connected to form a ring;

[0071] The substitution is substituted by at least one of deuterium, halogen, cyano, isocyano, phosphino, C1-C6 alkyl, C3-C16 cycloalkyl, C1-C6 alkyl-substituted amine, C1-C6 hydrocarbon-substituted or unsubstituted C6-C30 aryl, C1-C6 hydrocarbon-substituted or unsubstituted C3-C30 heteroaryl, wherein the number of substitutions ranges from single substitution to the maximum number of substitutions.

[0072] Hereinafter, each group of the compound represented by formula (1), (2), and (3) will be described.

[0073] In the present invention, the "carbon number ab" in the expression "substituted or unsubstituted X group having ab carbon atoms" refers to the carbon number of the unsubstituted X group and does not include the carbon number of the substituent when the X group is substituted.

[0074] Specific examples of C1-C10 alkyl groups include linear or branched alkyl groups such as methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl and its isomers, n-hexyl and its isomers, n-heptyl and its isomers, n-octyl and its isomers, n-nonyl and its isomers, n-decyl and its isomers, etc.; preferably, they are methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, and tert-butyl; more preferably, they are propyl, isopropyl, isobutyl, sec-butyl, and tert-butyl.

[0075] Specific examples of the C3-C20 cycloalkyl group include propyl, cyclobutyl, cyclopentyl, cyclohexyl, 1-adamantyl, 2-adamantyl, 1-norbornyl, and 2-norbornyl groups, with cyclopentyl and cyclohexyl groups being preferred.

[0076] Specific examples of the C2-C10 alkenyl group include vinyl, propenyl, allyl, 1-butadienyl, 2-butadienyl, 1-hexatrienyl, 2-hexatrienyl, and 3-hexatrienyl, with propenyl and allyl being preferred.

[0077] Specific examples of C1-C10 heteroalkyl groups include linear or branched alkyl groups and cycloalkyl groups containing atoms other than carbon and hydrogen, such as mercaptomethylmethane, methoxymethane, ethoxymethane, tert-butoxymethane, N,N-dimethylmethane, butylene oxide, cyclopentyl, and hexyl oxide; preferably, methoxymethane and cyclopentyl oxide.

[0078] Specific examples of the aryl group include phenyl, naphthyl, anthracenyl, phenanthrenyl, naphthacene, pyrene, chrysene, benzo[c]phenanthrenyl, benzo[g]chrysene, fluorenyl, benzofluorenyl, dibenzofluorenyl, biphenyl, terphenyl, quaterphenyl, and fluoranthenyl, preferably phenyl or naphthyl.

[0079] Specific examples of heteroaryl groups include pyrrolyl, pyrazinyl, pyridyl, pyrimidinyl, triazinyl, indolyl, isoindolyl, imidazolyl, furyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, azadibenzofuranyl, azadibenzothiophenyl, diazadibenzofuranyl, diazadibenzothiophenyl, quinolyl, isoquinolyl, quinoxalinyl, carbazolyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, phenothiazinyl, phenoxazinyl, ... The following examples are only for the purpose of facilitating the understanding of the technical invention and should not be regarded as specific limitations of the present invention.

[0080] The raw materials and solvents involved in the synthesis of the compounds of the present invention were purchased from suppliers well known to those skilled in the art, such as Alfa and Acros.

[0081] Synthesis of compound CPD29

[0082] The synthetic route is:

[0083] Synthesis of compound CPD29-3

[0084] CPD29-1 (30.00 g, 106.56 mmol), CPD29-2 (32.47 g, 127.87 mmol), 1,1-bis(diphenylphosphino)diphenylferric palladium dichloride (1.56 g, 2.13 mmol), potassium acetate (15.69 g, 159.84 mmol), and 1,4-dioxane (450 ml) were added to a 1000 ml three-necked round-bottom flask. The vacuum atmosphere was replaced with nitrogen three times, and the system was heated to 100 ° C. for 2 hours. The reaction was monitored by TLC (ethyl acetate: n-hexane = 1:10 as the developing solvent). The raw material CPD29-1 was completely consumed.

[0085] The temperature was lowered to 60°C, and the solvent was removed by concentration under reduced pressure. Ethyl acetate (700 ml) was added, and the product was washed three times with deionized water (300 ml*3). The product was separated, mixed with silica gel, and dry-loaded onto a column. Purification was performed by silica gel column chromatography (200-300 mesh silica gel, ethyl acetate:n-hexane = 1:15 as eluent). After elution, the product was concentrated under reduced pressure at 70°C for 1 hour to obtain a white solid CPD29-3 (27.62 g, purity: 98.05%, yield: 77.07%), mass spectrum: 329.12 (M+H).

[0086] Synthesis of compound CPD29-5

[0087] CPD29-3 (25.00 g, 76.08 mmol), CPD29-4 (17.89 g, 76.08 mmol), tetrakis(triphenylphosphine)palladium (1.75 g, 1.52 mmol), potassium carbonate (15.77 g, 114.12 mmol), tetrahydrofuran (375 ml), and deionized water (125 ml) were added to a 1000 ml three-necked round-bottom flask. The vacuum atmosphere was replaced with nitrogen three times, and the system was heated to 75 ° C for 3 hours. The reaction was monitored by TLC (ethyl acetate: n-hexane = 1:10 as the developing solvent). The raw material CPD29-3 was completely consumed.

[0088] The temperature was lowered to 60°C, and the solvent was removed by concentration under reduced pressure. Ethyl acetate (700 ml) was added, and the product was washed three times with deionized water (300 ml*3). The product was separated, mixed with silica gel, and dry-loaded onto a column. Purification was performed by silica gel column chromatography (200-300 mesh silica gel, ethyl acetate:n-hexane = 1:20 as eluent). After elution, the product was concentrated under reduced pressure at 70°C for 2 hours to obtain a white solid CPD29-5 (20.45 g, purity: 99.23%, yield: 74.33%), mass spectrum: 357.22 (M+H).

[0089] Synthesis of compound CPD29-7

[0090] CPD29-5 (18.00 g, 50.45 mmol), CPD29-6 (25.94 g, 75.67 mmol), and tetrahydrofuran (270 ml) were added to a 1000 ml three-necked round-bottom flask, and the vacuum nitrogen atmosphere was replaced three times. Then, the system was cooled to 5 ° C, and sodium methoxide (5.45 g, 100.90 mmol) was added in one portion. The reaction was maintained at 5 ° C for 1 hour. The reaction was monitored by TLC (ethyl acetate: n-hexane = 1:10 as the developing solvent). The raw material CPD29-5 was completely consumed.

[0091] Deionized water (500 ml) was added, and the solvent was removed by concentration under reduced pressure. Ethyl acetate (700 ml) was added for extraction. The layers were separated and concentrated under reduced pressure at 70°C for 1 hour to afford CPD29-7 (18.44 g, 95.00% yield) as a white solid. Mass spectrum: 385.04 (M+H). The obtained compound was used directly in the next step without purification.

[0092] Synthesis of compound CPD29-8

[0093] CPD29-7 (17.00 g, 44.17 mmol) and toluene (170 ml) were added to a 500 ml three-necked round-bottom flask, and the vacuum was replaced with nitrogen three times. Then, the system was cooled to 5°C and methanesulfonic acid (8.49 g, 88.34 mmol) was slowly added dropwise over 3 minutes. The reaction was maintained at 5°C for 1 hour. The reaction was monitored by TLC (ethyl acetate:n-hexane = 1:15 as the developing solvent). The raw material CPD29-7 was completely consumed.

[0094] Methanol (200 ml) was added thereto to precipitate a large amount of white solid, which was filtered to obtain 17 g of solid. The solid was crystallized once with toluene (204 ml) and methanol (170 ml), filtered, and the filter cake was dried in vacuo at 80°C for 1 hour to obtain a white solid CPD29-8 (11.63 g, purity: 99.83%, yield: 74.62%), mass spectrum: 353.06 (M+H).

[0095] Synthesis of compound CPD29-9

[0096] Referring to the synthesis and purification method of compound CPD29-3, it is only necessary to change the corresponding raw materials to obtain the white solid target compound CPD29-9 (14.22 g, purity: 99.02%, yield: 77.63%), mass spectrum: 445.20 (M+H).

[0097] Synthesis of compound CPD29

[0098] Referring to the synthesis and purification methods for compound CPD29-5, only the corresponding starting materials were changed to obtain the target compound CPD29 (12.02 g, purity: 99.96%, yield: 75.33%) as a yellow solid. 12.02 g of crude CPD29 was purified by sublimation to obtain pure CPD29 (9.23 g, purity: 99.95%, yield: 78.78%), with a mass spectrum of 665.25 (M+H).

[0099] 1 H NMR (400MHz, CDCl3) δ8.25(d,J=2.5Hz,1H),8.19-8.14(m,2H),8.07-8.02(m,1H),8.00(d,J=8.6Hz,1H),7.98-7.94(m ,2H),7.94-7.88(m,5H),7.87-7.82(m,4H),7.55-7.43(m,8H),7.38-7.35(m,1H),7.32(d,J=7.3Hz,1H),1.74(s,6H).

[0100] Synthesis of compound CPD59

[0101] The synthetic route is:

[0102] Compound CPD25-9 (20.00 g, 45.01 mmol), CPD59-1 (16.10 g, 45.01 mmol), tetrakis(triphenylphosphine)palladium (1.04 g, 0.90 mmol), sodium hydroxide (3.6 g, 90.02 mmol), tetrahydrofuran (300 ml), and deionized water (100 ml) were added to a 1000 ml three-necked round-bottom flask. The atmosphere was replaced with nitrogen three times under vacuum, and the temperature was raised to 75°C for 6 hours. Consumption of the starting material CPD25-9 was monitored by TLC (ethyl acetate:n-hexane = 1:10 as the developing solvent).

[0103] After cooling to room temperature, methanol (200 ml) was added and stirred at room temperature for 30 minutes. Filtering with suction afforded a yellow solid. Xylene (600 ml) was added and the mixture was heated to 120°C to dissolve the product. The mixture was cooled to room temperature and filtered once through a column chromatography silica gel (50 g, 200-300 mesh). The filter cake was rinsed with 300 ml of toluene until no product remained. The combined organic phases were concentrated under reduced pressure at 70°C to afford a yellow solid. This solid was crystallized twice from xylene and methanol and dried under vacuum at 100°C for 8 hours to afford compound CPD59 (21.69 g, purity: 99.97%, yield: 75.33%). 21.69 g of crude CPD59 was purified by sublimation to afford sublimation-purified CPD59 (15.93 g, purity: 99.97%, yield: 73.44). Mass spectrum: 640.12 (M+H).

[0104] 1 H NMR (400MHz, CDCl3) δ8.26(d,J=2.5Hz,1H),8.17(d,J=9.1Hz,1H),8.11-8.00(m,4H),7.94(dd,J=8.6,2.0Hz,2H),7.91-7.82(m,5 H),7.65-7.60(m,1H),7.60-7.53(m,2H),7.53-7.47(m,5H),7.47-7.39(m,2H),7.32(d,J=7.3Hz,1H),7.26(dd,J=9.3,6.8Hz,1H).

[0105] Synthesis of compound CPD63

[0106] The synthetic route is:

[0107] Synthesis of compound CPD63-2

[0108] Referring to the synthesis and purification method of compound CPD25-3, it is only necessary to change the corresponding raw materials to obtain the white solid target compound CPD63-2 (28.79 g, purity: 99.02%, yield: 76.82%), mass spectrum: 329.12 (M+H).

[0109] Synthesis of compound CPD63-3

[0110] Referring to the synthesis and purification method of compound CPD25-5, it is only necessary to change the corresponding raw materials to obtain the white solid target compound CPD63-3 (25.03 g, purity: 99.43%, yield: 73.96%), mass spectrum: 357.22 (M+H).

[0111] Synthesis of compound CPD63-4

[0112] By referring to the synthesis and purification methods of compound CPD25-7, only the corresponding starting materials need to be changed to obtain the target compound CPD63-4 (23.02 g, yield: 95.98%) as a white solid with a mass spectrum of 385.04 (M+H). The obtained compound was used directly in the next step without purification.

[0113] Synthesis of compound CPD63-5

[0114] Referring to the synthesis and purification method of compound CPD25-8, it is only necessary to change the corresponding raw materials to obtain the white solid target compound CPD63-5 (16.66 g, purity: 99.85%, yield: 74.63%), mass spectrum: 353.06 (M+H).

[0115] Synthesis of compound CPD63-6

[0116] Referring to the synthesis and purification method of compound CPD25-9, only the corresponding raw materials need to be changed to obtain the white solid target compound CPD63-6 (15.00 g, purity: 99.03%, yield: 75.05%), mass spectrum: 445.12 (M+H).

[0117] Synthesis of compound CPD63

[0118] Referring to the synthesis and purification methods for compound CPD59, only the corresponding starting materials were changed to obtain the target compound CPD63 (15.63 g, purity: 99.97%, yield: 74.65%) as a yellow solid. 15.63 g of crude CPD63 was purified by sublimation to obtain pure CPD63 (13.00 g, purity: 99.96%, yield: 83.17%), with a mass spectrum of 626.22 (M+H).

[0119] 1 H NMR (400MHz, CDCl3) δ8.21(d,J=9.7Hz,1H),8.17(d,J=9.1Hz,1H),8.13-8.00(m,3H),7.98-7.91(m,5H),7.91- 7.83(m,3H),7.73-7.66(m,3H),7.64-7.54(m,2H),7.54-7.47(m,5H),7.47-7.38(m,3H),7.32(d,J=7.3Hz,1H).

[0120] Synthesis of compound CPD77

[0121] The synthetic route is:

[0122] Synthesis of compound CPD77-3

[0123] Compound CPD77-1 (20.00 g, 88.47 mmol), CPD77-2 (28.42 g, 88.47 mmol), tetrakis(triphenylphosphine)palladium (1.07 g, 0.88 mmol), potassium carbonate (24.45 g, 176.94 mmol), tetrahydrofuran (400 ml), and deionized water (120 ml) were added to a 1000 ml three-necked round-bottom flask. The atmosphere was replaced with nitrogen three times under vacuum, and the temperature was raised to 50°C for 8 hours. Consumption of the starting material CPD77-1 was monitored by TLC (ethyl acetate:n-hexane = 1:20 as the developing solvent).

[0124] After the reaction mixture cooled to room temperature, deionized water (700 ml) was added and stirred at room temperature for 30 minutes. The mixture was then filtered and the filter cake was rinsed with deionized water (200 ml). The filter cake was dissolved in tetrahydrofuran (2000 ml) heated to 80°C with stirring. The mixture was filtered once through a chromatography column with silica gel (20 g, 200-300 mesh) and rinsed with THF (200 ml). The filtrate was concentrated at 65°C for 2 hours to obtain a light yellow solid. The solid was crystallized once from tetrahydrofuran and methanol and dried under vacuum at 80°C for 10 hours to obtain CPD77-3 (25.57 g, purity: 99.62%, yield: 75.11%) as a light yellow solid. Mass spectrum: 385.02 (M+H).

[0125] Synthesis of compound CPD77

[0126] Referring to the synthesis and purification methods for compound CPD59, only the corresponding starting materials were modified to obtain the target compound CPD77 (18.09 g, purity: 99.95%, yield: 75.74%) as a yellow solid. 18.09 g of crude CPD77 was purified by sublimation to obtain pure CPD77 (14.85 g, purity: 99.95%, yield: 82.09%), with a mass spectrum of 667.32 (M+H).

[0127] 1 H NMR (400MHz, CDCl3) δ8.21(d,J=9.7Hz,1H),8.17(d,J=9.1Hz,1H),8.12-8.05(m,2H),8.05-8.01(m,1H),7.99-7. 87(m,8H),7.87-7.82(m,3H),7.69(d,J=2.2Hz,1H),7.55-7.47(m,6H),7.47-7.39(m,2H),7.32(d,J=7.3Hz,1H).

[0128] Synthesis of compound CPD119

[0129] The synthetic route is:

[0130] Synthesis of compound CPD119-2

[0131] Referring to the synthesis and purification method of compound CPD25-5, it is only necessary to change the corresponding raw materials to obtain the white solid target compound CPD119-2 (24.25 g, purity: 99.68%, yield: 78.08%), mass spectrum: 519.11 (M+H).

[0132] Synthesis of compound CPD119

[0133] CPD119-2 (20.00 g, 38.54 mmol), CPD77-2 (12.38 g, 38.54 mmol), bis(4-dimethylaminophenyldi-tert-butylphosphine)palladium dichloride (0.23 g, 0.38 mmol), potassium carbonate (10.65 g, 77.08 mmol), toluene (300 ml), ethanol (100 ml), and deionized water (100 ml) were added to a 1000 ml three-necked round-bottom flask. The vacuum was replaced with nitrogen three times, and the system was heated to 65 ° C for 2 hours. The reaction was monitored by TLC (ethyl acetate: n-hexane = 1:10 as the developing solvent). The raw material CPD119-2 was completely consumed.

[0134] The mixture was cooled to room temperature, methanol (300 ml) was added, and stirred at room temperature for 1 hour to precipitate a large amount of solid. Toluene (450 ml) was added, and the system was heated to 100°C and dissolved by heating. The mixture was cooled to room temperature and filtered through 200-300 mesh silica gel (20 g). The filtrate was added with methanol (450 ml) at room temperature, stirred at room temperature for 1 hour, and filtered to obtain a white solid wet product. The product was dried at 100°C for 1 hour to obtain a light yellow solid. The product was crystallized twice using toluene and methanol, filtered, and the filter cake was vacuum dried at 100°C for 10 hours to obtain a yellow solid, CPD119 (18.83 g, purity: 99.98%, yield: 72.11%). 18.83 g of crude CPD119 was purified by sublimation to obtain pure CPD119 (14.88 g, purity: 99.98%, yield: 79.03%). Mass spectrum: 678.24 (M+H).

[0135] 1H NMR (400MHz, CDCl3) δ8.23 (d, J=2.4Hz, 1H), 8.17 (dd, J=8.5, 4.2Hz, 2H), 8.07-8.01 (m, 2H), 7.98-7.87 (m, 6H), 7.85 (dd, J=7.6, 3.0Hz, 2H), 7.76 (dd, J= 7.2,2.4Hz,2H),7.70(d,J=2.0Hz,1H),7.62(dd,J=7.8,2.1Hz,1H),7.60-7 .47(m,5H),7.47-7.40(m,3H),7.37(d,J=7.4Hz,1H),7.32(d,J=7.3Hz,1H).

[0136] Synthesis of compound CPD125

[0137] The synthetic route is:

[0138] Referring to the synthesis and purification methods for compound CPD119, only the corresponding starting materials were modified to obtain the target compound CPD125 (12.63 g, purity: 99.94%, yield: 73.63%) as a yellow solid. 12.63 g of crude CPD125 was purified by sublimation to obtain pure CPD125 (10.01 g, purity: 99.94%, yield: 79.25%), with a mass spectrum of 587.20 (M+H).

[0139] 1 H NMR (400MHz, CDCl3) δ8.64 (d, J = 7.2 Hz, 1H), 8.21-8.13 (m, 2H), 8.11 (d, J = 8. 3Hz,1H),8.07-8.02(m,1H),7.94(dd,J=8.6,2.0Hz,2H),7.92-7.87(m,1H),7 .85(dd,J=7.6,3.0Hz,2H),7.72-7.64(m,4H),7.62(dd,J=8.3,2.1Hz,1H),7. 54(d,J=2.2Hz,1H),7.53-7.48(m,2H),7.48-7.40(m,6H),7.37-7.29(m,2H).

[0140] Synthesis of compound CPD137

[0141] Synthesis of compound CPD137

[0142] Referring to the synthesis and purification methods for compound CPD119, only the corresponding starting materials were modified to obtain the target compound CPD137 (14.96 g, purity: 99.95%, yield: 71.09%) as a yellow solid. 14.96 g of crude CPD137 was purified by sublimation to obtain pure CPD137 (10.06 g, purity: 99.95%, yield: 67.25%), with a mass spectrum of 497.26 (M+H).

[0143] 1 H NMR (400MHz, CDCl3) δ8.93(dd,J=4.1,2.1Hz,1H),8.84(dd,J=3.9,1.7Hz,1H),8.33(dd,J=7.6,2.1Hz,1H),8.28(d,J=2 .1Hz,1H),8.18(dd,J=9.6,8.5Hz,2H),8.12-8.01(m,2H),7.97-7.82(m,5H),7.59-7.45(m,6H),7.32(d,J=7.3Hz,1H).

[0144] Synthesis of compound CPD139

[0145] The synthetic route is:

[0146] Referring to the synthesis and purification methods for compound CPD119, only the corresponding starting materials were modified to obtain the target compound CPD139 (15.00 g, purity: 99.96%, yield: 76.63%) as a yellow solid. 15.00 g of crude CPD139 was purified by sublimation to obtain pure CPD139 (12.05 g, purity: 99.96%, yield: 80.33%), with a mass spectrum of 546.18 (M+H).

[0147] 1 H NMR (400MHz, CDCl3) δ8.82(dd,J=4.1,2.1Hz,1H),8.61(dd,J=7.6,2.1Hz,1H),8.54(dd,J=5.7,3.1Hz,1H),8.28(d,J=2.3Hz,1H),8.20 -8.12(m,2H),8.07-8.01(m,3H),7.97-7.82(m,5H),7.74-7.71(m,2H),7.57-7.46(m,5H),7.43(d,J=7.2Hz,1H),7.32(d,J=7.3Hz,1H).

[0148] Synthesis of compound CPD146

[0149] The synthetic route is:

[0150] Synthesis of compound CPD146-2

[0151] Referring to the synthesis and purification method of compound CPD25-3, it is only necessary to change the corresponding raw materials to obtain the white solid target compound CPD146-2 (25.98 g, purity: 99.02%, yield: 75.63%), mass spectrum: 322.15 (M+H).

[0152] Synthesis of compound CPD146-4

[0153] Referring to the synthesis and purification method of compound CPD25-5, it is only necessary to change the corresponding raw materials to obtain the white solid target compound CPD146-4 (22.02 g, purity: 99.52%, yield: 72.63%), mass spectrum: 334.06 (M+H).

[0154] Synthesis of compound CPD146-5

[0155] Referring to the synthesis and purification methods of compound CPD25-7, only the corresponding starting materials were changed to obtain the target compound CPD146-5 (21.06 g, yield: 97.65%) as a white solid with a mass spectrum of 362.08 (M+H). The obtained compound was used directly in the next step without purification.

[0156] Synthesis of compound CPD146-6

[0157] Referring to the synthesis and purification method of compound CPD25-8, it is only necessary to change the corresponding raw materials to obtain the white solid target compound CPD146-6 (17.06 g, purity: 99.81%, yield: 72.96%), mass spectrum: 330.02 (M+H).

[0158] Synthesis of compound CPD146-7

[0159] Referring to the synthesis and purification method of compound CPD25-9, only the corresponding raw materials need to be changed to obtain the white solid target compound CPD146-7 (15.06 g, purity: 99.23%, yield: 78.03%), mass spectrum: 422.18 (M+H).

[0160] Synthesis of compound CPD146-8

[0161] Referring to the synthesis and purification method of compound CPD77-3, it is only necessary to change the corresponding raw materials to obtain the white solid target compound CPD146-8 (16.86 g, purity: 99.59%, yield: 74.96%), mass spectrum: 485.12 (M+H).

[0162] Synthesis of compound CPD146

[0163] Referring to the synthesis and purification methods for compound CPD59, only the corresponding starting materials were modified to obtain the target compound CPD146 (18.88 g, purity: 99.95%, yield: 72.63%) as a yellow solid. 18.88 g of crude CPD146 was purified by sublimation to obtain pure CPD146 (14.73 g, purity: 99.96%, yield: 78.02%), with a mass spectrum of 767.24 (M+H).

[0164] 1 H NMR (400MHz, CDCl3) δ8.28(d,J=2.2Hz,1H),8.21(d,J=9.7Hz,1H),8.17(d,J=9.1Hz,1H),8.11-8.00(m,7H),8.00-7.96(m,1H),7 .96-7.87(m,7H),7.85(dd,J=7.6,3.0Hz,2H),7.69(d,J=2.4Hz,1H),7.54-7.46(m,6H),7.46-7.40(m,2H),7.32(d,J=7.3Hz,1H).

[0165] Synthesis of compound CPD169

[0166] The synthetic route is:

[0167] Synthesis of compound CPD169-2

[0168] Referring to the synthesis and purification method of compound CPD25-3, it is only necessary to change the corresponding raw materials to obtain the white solid target compound CPD169-2 (23.33 g, purity: 99.08%, yield: 77.06%), mass spectrum: 329.10 (M+H).

[0169] Synthesis of compound CPD169-3

[0170] Referring to the synthesis and purification method of compound CPD25-5, it is only necessary to change the corresponding raw materials to obtain the white solid target compound CPD169-3 (20.66 g, purity: 99.73%, yield: 75.63%), mass spectrum: 357.22 (M+H).

[0171] Synthesis of compound CPD169-4

[0172] By referring to the synthesis and purification methods of compound CPD25-7, only the corresponding starting materials were changed to obtain the target compound CPD169-4 (19.08 g, yield: 97.05%) as a white solid with a mass spectrum of 385.04 (M+H). The obtained compound was used directly in the next step without purification.

[0173] Synthesis of compound CPD169-5

[0174] Referring to the synthesis and purification method of compound CPD25-8, it is only necessary to change the corresponding raw materials to obtain the white solid target compound CPD169-5 (16.88 g, purity: 99.85%, yield: 40.33%), mass spectrum: 353.06 (M+H).

[0175] Synthesis of compound CPD169-6

[0176] Referring to the synthesis and purification method of compound CPD25-9, it is only necessary to change the corresponding raw materials to obtain the white solid target compound CPD169-6 (14.63 g, purity: 99.12%, yield: 74.63%), mass spectrum: 445.20 (M+H).

[0177] Synthesis of compound CPD169

[0178] Referring to the synthesis and purification methods for compound CPD25, only the corresponding starting materials were modified to obtain the target compound CPD169 (12.41 g, purity: 99.94%, yield: 73.63%) as a yellow solid. 12.41 g of crude CPD169 was purified by sublimation to obtain pure CPD169 (9.35 g, purity: 99.96%, yield: 75.35%), with a mass spectrum of 573.19 (M+H).

[0179] 1 H NMR (400MHz, CDCl3) δ8.62 (s, 1H), 8.32-8.26 (m, 2H), 8.01 (d, J = 8.9Hz, 1H), 7.99-7.92 (m, 3H), 7.92-7.85 (m,5H),7.78(d,J=2.1Hz,1H),7.74-7.67(m,3H),7.62-7.55(m,2H),7.55-7.48(m,2H),7.45-7.35(m,4H).

[0180] Synthesis of compound CPD202

[0181] The synthetic route is:

[0182] Synthesis of compound CPD202-2

[0183] Referring to the synthesis and purification method of compound CPD25-3, it is only necessary to change the corresponding raw materials to obtain the white solid target compound CPD202-2 (24.22 g, purity: 99.18%, yield: 74.96%), mass spectrum: 329.10 (M+H).

[0184] Synthesis of compound CPD202-3

[0185] Referring to the synthesis and purification method of compound CPD25-5, it is only necessary to change the corresponding raw materials to obtain the white solid target compound CPD202-3 (19.85 g, purity: 99.76%, yield: 74.62%), mass spectrum: 357.22 (M+H).

[0186] Synthesis of compound CPD202-4

[0187] Referring to the synthesis and purification methods of compound CPD25-7, only the corresponding starting materials were changed to obtain the target compound CPD202-4 (17.96 g, yield: 94.56%) as a white solid with a mass spectrum of 385.04 (M+H). The obtained compound was used directly in the next step without purification.

[0188] Synthesis of compound CPD202-5

[0189] Referring to the synthesis and purification method of compound CPD25-8, it is only necessary to change the corresponding raw materials to obtain the white solid target compound CPD202-5 (15.69 g, purity: 99.87%, yield: 42.65%), mass spectrum: 353.06 (M+H).

[0190] Synthesis of compound CPD202

[0191] Referring to the synthesis and purification methods for compound CPD119, only the corresponding starting materials were modified to obtain the target compound CPD202 (14.85 g, purity: 99.96%, yield: 74.66%) as a yellow solid. 14.85 g of crude CPD202 was purified by sublimation to obtain pure CPD202 (11.52 g, purity: 99.96%, yield: 77.58%), with a mass spectrum of 512.16 (M+H).

[0192] 1H NMR (400MHz, CDCl3) δ8.59(s,1H),8.33-8.27(m,1H),8.16(d,J=7.8Hz,1H),8.01(d,J=9.0Hz,1H),7.98-7.85(m,7H),7.78(d,J= 2.1Hz,1H),7.70(d,J=2.2Hz,1H),7.62(dd,J=7.8,2.1Hz,1H),7.56(dd,J=7.9,2.2Hz,1H),7.54-7.46(m,4H),7.46-7.37(m,2H).

[0193] Synthesis of compound CPD228

[0194] The synthetic route is:

[0195] Synthesis of compound CPD228-2

[0196] Referring to the synthesis and purification method of compound CPD25-3, it is only necessary to change the corresponding raw materials to obtain the white solid target compound CPD228-2 (20.65 g, purity: 99.00%, yield: 74.98%), mass spectrum: 329.10 (M+H).

[0197] Synthesis of compound CPD228-3

[0198] Referring to the synthesis and purification method of compound CPD25-5, it is only necessary to change the corresponding raw materials to obtain the white solid target compound CPD228-3 (17.11 g, purity: 99.41%, yield: 72.11%), mass spectrum: 357.22 (M+H).

[0199] Synthesis of compound CPD228-4

[0200] Referring to the synthesis and purification methods of compound CPD25-7, only the corresponding starting materials were changed to obtain the target compound CPD228-4 (16.33 g, yield: 92.17%) as a white solid with a mass spectrum of 385.04 (M+H). The obtained compound was used directly in the next step without purification.

[0201] Synthesis of compound CPD228-5

[0202] Referring to the synthesis and purification method of compound CPD25-8, it is only necessary to change the corresponding raw materials to obtain the white solid target compound CPD228-5 (14.62 g, purity: 99.63%, yield: 40.00%), mass spectrum: 353.06 (M+H).

[0203] Synthesis of compound CPD228-6

[0204] Referring to the synthesis and purification method of compound CPD25-9, it is only necessary to change the corresponding raw materials to obtain the white solid target compound CPD228-6 (17.69 g, purity: 98.89%, yield: 72.62%), mass spectrum: 445.20 (M+H).

[0205] Synthesis of compound CPD228

[0206] Referring to the synthesis and purification methods for compound CPD59, only the corresponding starting materials were modified to obtain the target compound CPD228 (13.05 g, purity: 99.95%, yield: 72.06%) as a yellow solid. 13.05 g of crude CPD228 was purified by sublimation to obtain pure CPD228 (10.02 g, purity: 99.96%, yield: 76.82%), with a mass spectrum of 715.22 (M+H).

[0207] 1 H NMR (400MHz, CDCl3) δ8.33-8.28(m,1H),8.26-8.17(m,4H),8.14-8.04(m,5H),7.97(d,J=7.9Hz,1H),7.92(dd,J=9.7,2.2Hz,1H),7.90 -7.87(m,1H),7.85(d,J=8.0Hz,1H),7.66(d,J=2.2Hz,1H),7.57-7.46(m,8H),7.44-7.41(m,1H),7.37-7.27(m,3H),7.22-7.14(m,3H).

[0208] Synthesis of compound CPD232

[0209] The synthetic route is:

[0210] Synthesis of compound CPD232-1

[0211] Referring to the synthesis and purification method of compound CPD25-8, it is only necessary to change the corresponding raw materials to obtain the white solid target compound CPD232-1 (14.65 g, purity: 99.52%, yield: 39.77%), mass spectrum: 353.06 (M+H).

[0212] Synthesis of compound CPD232-2

[0213] Referring to the synthesis and purification method of compound CPD25-9, it is only necessary to change the corresponding raw materials to obtain the white solid target compound CPD232-2 (15.11 g, purity: 98.08%, yield: 75.96%), mass spectrum: 445.20 (M+H).

[0214] Synthesis of compound CPD232

[0215] Referring to the synthesis and purification methods for compound CPD59, only the corresponding starting materials were modified to obtain the target compound CPD232 (12.85 g, purity: 99.96%, yield: 74.33%) as a yellow solid. 12.85 g of crude CPD232 was purified by sublimation to obtain pure CPD232 (9.52 g, purity: 99.96%, yield: 74.08%), mass spectrum: 802.20 (M+H).

[0216] 1 H NMR (400MHz, CDCl3) δ8.37(d,J=8.2Hz,1H),8.33-8.28(m,1H),8.28-8.24(m,1H),8.22(d,J=2.4Hz,1H ),8.11-8.05(m,2H),7.99-7.80(m,15H),7.65-7.60(m,4H),7.57-7.47(m,9H),7.37(d,J=7.1Hz,1H).

[0217] Synthesis of compound CPD263

[0218] The synthetic route is:

[0219] Synthesis of compound CPD263-1

[0220] Referring to the synthesis and purification method of compound CPD25-8, it is only necessary to change the corresponding raw materials to obtain the white solid target compound CPD263-1 (12.41 g, purity: 99.31%, yield: 38.45%), mass spectrum: 353.06 (M+H).

[0221] Synthesis of compound CPD263-2

[0222] Referring to the synthesis and purification method of compound CPD25-9, it is only necessary to change the corresponding raw materials to obtain the white solid target compound CPD263-2 (14.12 g, purity: 99.20%, yield: 74.10%), mass spectrum: 445.20 (M+H).

[0223] Synthesis of compound CPD263

[0224] Referring to the synthesis and purification methods for compound CPD59, only the corresponding starting materials were modified to obtain the target compound CPD263 (13.03 g, purity: 99.95%, yield: 73.02%) as a yellow solid. 13.03 g of crude CPD263 was purified by sublimation to obtain pure CPD263 (9.32 g, purity: 99.96%, yield: 71.52%), with a mass spectrum of 790.28 (M+H).

[0225] 1 H NMR (400MHz, CDCl3) δ8.34(dd,J=2.0,0.7Hz,1H),8.33-8.26(m,1H),8.21-8.17(m,2H),8.15(dd,J=9.0,2.4Hz,1H),8.12-8.05(m,3H),8.05-7.98( m,3H),7.96(d,J=8.0Hz,1H),7.94-7.92(m,1H),7.92-7.90(m,1H),7.90- 7.86(m,2H),7.68(d,J=2.3Hz,1H),7.55-7.40(m,12H),7.34-7.27(m,6H).

[0226] Synthesis of compound CPD300

[0227] The synthetic route is:

[0228] Synthesis of compound CPD300-3

[0229] Referring to the synthesis and purification method of compound CPD25-5, it is only necessary to change the corresponding raw materials to obtain the white solid target compound CPD300-3 (19.99 g, purity: 99.53%, yield: 74.63%), mass spectrum: 357.22 (M+H).

[0230] Synthesis of compound CPD300-4

[0231] By referring to the synthesis and purification methods of compound CPD25-7, only the corresponding starting materials were changed to obtain the target compound CPD300-4 (20.66 g, yield: 93.06%) as a white solid with a mass spectrum of 385.04 (M+H). The obtained compound was used directly in the next step without purification.

[0232] Synthesis of compound CPD300-5

[0233] Referring to the synthesis and purification method of compound CPD25-8, only the corresponding raw materials need to be changed to obtain the white solid target compound CPD300-5 (18.52 g, purity: 99.76%, yield: 75.52%), mass spectrum: 353.06 (M+H).

[0234] Synthesis of compound CPD300

[0235] Referring to the synthesis and purification methods for compound CPD59, only the corresponding starting materials were changed to obtain the target compound CPD300 (16.66 g, purity: 99.97%, yield: 74.85%) as a yellow solid. 16.66 g of crude CPD300 was purified by sublimation to obtain pure CPD300 (12.75 g, purity: 99.97%, yield: 76.53%), with a mass spectrum of 724.23 (M+H).

[0236] 1 H NMR (400MHz, CDCl3) δ8.79(dd,J=7.5,1.4Hz,1H),8.62-8.57(m,1H),8.55(t,J=2.2Hz,1H),8.38(d,J=6.9Hz,1H),8.35-8.29(m,1H),8 .21(d,J=9.7Hz,1H),8.19-8.12(m,2H),8.12-7.99(m,5H),7.97-7.86(m,4H),7.86-7.81(m,1H),7.71-7.59(m,3H),7.58-7.44(m,8H).

[0237] Synthesis of compound CPD344

[0238] The synthetic route is:

[0239] Synthesis of compound CPD344-2

[0240] Referring to the synthesis and purification method of compound CPD25-5, it is only necessary to change the corresponding raw materials to obtain the white solid target compound CPD344-2 (18.78 g, purity: 99.49%, yield: 71.12%), mass spectrum: 357.22 (M+H).

[0241] Synthesis of compound CPD344-3

[0242] Referring to the synthesis and purification methods of compound CPD25-7, only the corresponding starting materials were changed to obtain the target compound CPD344-3 (19.89 g, yield: 94.66%) as a white solid with a mass spectrum of 385.04 (M+H). The obtained compound was used directly in the next step without purification.

[0243] Synthesis of compound CPD344-4

[0244] Referring to the synthesis and purification method of compound CPD25-8, it is only necessary to change the corresponding raw materials to obtain the white solid target compound CPD344-4 (17.01 g, purity: 99.88%, yield: 76.11%), mass spectrum: 353.06 (M+H).

[0245] Synthesis of compound CPD344-5

[0246] Referring to the synthesis and purification method of compound CPD25-9, it is only necessary to change the corresponding raw materials to obtain the white solid target compound CPD344-5 (15.06 g, purity: 99.00%, yield: 77.33%), mass spectrum: 445.06 (M+H).

[0247] Synthesis of compound CPD344

[0248] Referring to the synthesis and purification methods for compound CPD25, only the corresponding starting materials were modified to obtain the target compound CPD344 (14.66 g, purity: 99.98%, yield: 75.63%) as a yellow solid. 14.66 g of crude CPD344 was purified by sublimation to obtain pure CPD344 (11.56 g, purity: 99.98%, yield: 78.85%), with a mass spectrum of 523.17 (M+H).

[0249] 1 H NMR(400MHz, CDCl3)δ8.86(s,1H),8.61(dd,J=8.5,3.7Hz,2H),8.46-8.39(m,1H),8.35-8.27(m,1H),8.16(d,J=9.8Hz,1H) ,8.03-7.92(m,3H),7.90-7.88(m,3H),7.67(d,J=2.3Hz,1H),7.59-7.47(m,4H),7.46-7.38(m,4H),7.32(d,J=7.3Hz,1H).

[0250] Synthesis of compound CPD364

[0251] The synthetic route is:

[0252] Referring to the synthesis and purification methods for compound CPD59, only the corresponding starting materials were modified to obtain the target compound CPD364 (17.56 g, purity: 99.95%, yield: 74.12%) as a yellow solid. 17.56 g of crude CPD364 was purified by sublimation to obtain pure CPD364 (13.08 g, purity: 99.98%, yield: 74.48%), with a mass spectrum of 640.19 (M+H).

[0253] 1 H NMR (400MHz, CDCl3) δ8.61 (dd, J=8.5, 3.7Hz, 2H), 8.49-8.38 (m, 1H), 8.35 -8.27(m,1H),8.21(d,J=9.7Hz,1H),8.13-8.00(m,3H),7.99-7.91(m,2H), 7.91-7.83(m,3H),7.69(d,J=2.3Hz,1H),7.67-7.59(m,1H),7.59-7.47(m, 6H),7.47-7.37(m,2H),7.32(d,J=7.2Hz,1H),7.26(dd,J=9.3,6.8Hz,1H).

[0254] Synthesis of compound CPD395

[0255] The synthetic route is:

[0256] Referring to the synthesis and purification methods for compound CPD59, only the corresponding starting materials were modified to obtain the target compound CPD395 (12.11 g, purity: 99.95%, yield: 75.69%) as a yellow solid. 12.11 g of crude CPD395 was purified by sublimation to obtain pure CPD395 (9.88 g, purity: 99.98%, yield: 81.58%), with a mass spectrum of 656.33 (M+H).

[0257] 1 H NMR(400MHz, CDCl3)δ8.61(dd,J=8.5,3.7Hz,2H),8.46-8.38(m,1H),8.34-8.27(m,1H),8.21(d,J=9.7Hz, 1H),7.97-7.91(m,2H),7.91-7.86(m,2H),7.69(d,J=2.2Hz,1H),7.57-7.46(m,2H),7.32(d,J=7.3Hz,1H).

[0258] Synthesis of compound CPD410

[0259] The synthetic route is:

[0260] Synthesis of compound CPD410-2

[0261] Referring to the synthesis and purification method of compound CPD25-5, it is only necessary to change the corresponding raw materials to obtain the white solid target compound CPD410-2 (17.89 g, purity: 99.63%, yield: 74.63%), mass spectrum: 413.12 (M+H).

[0262] Synthesis of compound CPD410-3

[0263] By referring to the synthesis and purification methods of compound CPD25-7, only the corresponding starting materials were changed to obtain the target compound CPD410-3 (16.56 g, yield: 95.55%) as a white solid with a mass spectrum of 441.15 (M+H). The obtained compound was used directly in the next step without purification.

[0264] Synthesis of compound CPD410-4

[0265] Referring to the synthesis and purification method of compound CPD25-8, it is only necessary to change the corresponding raw materials to obtain the white solid target compound CPD410-4 (18.33 g, purity: 99.57%, yield: 74.75%), mass spectrum: 409.13 (M+H).

[0266] Synthesis of compound CPD410-5

[0267] Referring to the synthesis and purification method of compound CPD25-9, only the corresponding raw materials need to be changed to obtain the white solid target compound CPD410-5 (16.79 g, purity: 99.21%, yield: 76.00%), mass spectrum: 501.02 (M+H).

[0268] Synthesis of compound CPD410

[0269] Referring to the synthesis and purification methods of compound CPD59, only the corresponding starting materials were changed to obtain the target compound CPD410 (12.00 g, purity: 99.95%, yield: 72.63%) as a yellow solid. 12.00 g of crude CPD410 was purified by sublimation to obtain pure CPD410 (9.00 g, purity: 99.95%, yield: 75.00%), with a mass spectrum of 710.26 (M+H).

[0270] 1H NMR (400MHz, CDCl3) δ8.60(d,J=9.3Hz,1H),8.53(d,J=8.2Hz,1H),8.33-8.28(m,1H),8.21(d,J=9.8Hz,1H),8.15-8.08(m,2H),8.08-8.00(m,1H),7 .96-7.82(m,5H),7.73-7.67(m,2H),7.66-7.59(m,1H),7.55(dd,J=6.8,1 .1Hz,1H),7.47-7.37(m,3H),7.35-7.23(m,4H),2.36(s,3H),1.34(s,9H).

[0271] Synthesis of compound CPD423

[0272] The synthetic route is:

[0273] Synthesis of compound CPD423

[0274] Referring to the synthesis and purification methods for compound CPD119, only the corresponding starting materials were modified to obtain the target compound CPD423 (13.56 g, purity: 99.96%, yield: 74.85%) as a yellow solid. 13.56 g of crude CPD423 was purified by sublimation to obtain pure CPD423 (10.11 g, purity: 99.95%, yield: 74.55%), with a mass spectrum of 587.20 (M+H).

[0275] 1 H NMR(400MHz, CDCl3)δ8.61(dd,J=8.5,3.7Hz,2H),8.47-8.39(m,1H),8.33-8.28(m,1H),8.14-8.09(m,1H),8.01-7.94(m, 3H),7.94-7.85(m,3H),7.82-7.74(m,1H),7.67-7.59(m,3H),7.59-7.46(m,8H),7.46-7.40(m,2H),7.32(d,J=7.3Hz,1H).

[0276] Synthesis of compound CPD434

[0277] The synthetic route is:

[0278] Synthesis of compound CPD434

[0279] Referring to the synthesis and purification methods for compound CPD119, only the corresponding starting materials were modified to obtain the target compound CPD434 (10.52 g, purity: 99.93%, yield: 75.00%) as a yellow solid. 10.52 g of crude CPD434 was purified by sublimation to obtain pure CPD434 (8.00 g, purity: 99.93%, yield: 76.04%), with a mass spectrum of 655.18 (M+H).

[0280] 1 H NMR (400MHz, CDCl3) δ8.61(dd,J=8.5,3.7Hz,2H),8.47-8.39(m,1H),8.33-8.28(m,1H),8.23(dd,J=7.3,1. 2Hz,1H),8.18(d,J=8.8Hz,1H),7.97-7.85(m,6H),7.72-7.64(m,3H),7.60-7.47(m,6H),7.44-7.30(m,5H).

[0281] Synthesis of compound CPD475

[0282] Synthesis of compound CPD475-1

[0283] Referring to the synthesis and purification method of compound CPD29-5, only the corresponding raw materials need to be changed to obtain the white solid target compound CPD475-1 (17.07 g, purity: 99.53%, yield: 74.33%), mass spectrum: 357.22 (M+H).

[0284] Synthesis of compound CPD475-2

[0285] Referring to the synthesis and purification methods of compound CPD29-7, only the corresponding starting materials were changed to obtain the target compound CPD475-2 (16.56 g, yield: 95.96%) as a white solid with a mass spectrum of 385.04 (M+H). The obtained compound was used directly in the next step without purification.

[0286] Synthesis of compound CPD475-3

[0287] Referring to the synthesis and purification method of compound CPD29-8, only the corresponding raw materials need to be changed to obtain the white solid target compound CPD475-3 (17.01 g, purity: 99.50%, yield: 40.33%), mass spectrum: 353.06 (M+H).

[0288] Synthesis of compound CPD475-4

[0289] Referring to the synthesis and purification method of compound CPD29-9, only the corresponding raw materials need to be changed to obtain the white solid target compound CPD475-4 (16.85 g, purity: 99.24%, yield: 75.74%), mass spectrum: 445.06 (M+H).

[0290] Synthesis of compound CPD475

[0291] Referring to the synthesis and purification methods for compound CPD59, only the corresponding starting materials were modified to obtain the target compound CPD475 (11.01 g, purity: 99.93%, yield: 74.12%) as a yellow solid. 11.01 g of crude CPD475 was purified by sublimation to obtain pure CPD475 (7.56 g, purity: 99.94%, yield: 68.66%), with a mass spectrum of 674.22 (M+H).

[0292] 1 H NMR (400MHz, CDCl3) δ8.64(d,J=9.3Hz,1H),8.46-8.41(m,1H),8.41-8.35(m,2H),8.19(dd,J=9.8,8.5Hz,2H),8.17-8.12(m,2H) ,8.11-8.02(m,6H),7.96(d,J=9.3Hz,1H),7.92(dd,J=9.7,2.2Hz,1H),7.91-7.86(m,1H),7.69-7.60(m,3H),7.55-7.46(m,7H).

[0293] Synthesis of compound CPD523

[0294] The synthetic route is:

[0295] Synthesis of compound CPD523-1

[0296] Referring to the synthesis and purification method of compound CPD25-8, it is only necessary to change the corresponding raw materials to obtain the white solid target compound CPD523-1 (14.11 g, purity: 99.31%, yield: 38.02%), mass spectrum: 353.06 (M+H).

[0297] Synthesis of compound CPD523-2

[0298] Referring to the synthesis and purification method of compound CPD25-9, only the corresponding raw materials need to be changed to obtain the white solid target compound CPD523-2 (13.85 g, purity: 99.01%, yield: 76.05%), mass spectrum: 445.06 (M+H).

[0299] Synthesis of compound CPD523-4

[0300] Referring to the synthesis and purification method of compound CPD59, only the corresponding raw materials need to be changed to obtain the white solid target compound CPD523-4 (13.85 g, purity: 99.60%, yield: 70.00%), mass spectrum: 502.10 (M+H).

[0301] Synthesis of compound CPD523

[0302] Referring to the synthesis and purification methods for compound CPD59, only the corresponding starting materials were modified to obtain the target compound CPD523 (14.62 g, purity: 99.953%, yield: 75.06%) as a yellow solid. 14.62 g of crude CPD523 was purified by sublimation to obtain pure CPD523 (11.85 g, purity: 99.94%, yield: 81.05%), with a mass spectrum of 784.23 (M+H).

[0303] 1 H NMR(400MHz, CDCl3)δ8.61(dd,J=9.0,2.2Hz,2H),8.51-8.42(m,1H),8.21-8.15(m,2H),8.09(d,J=2.5Hz,1H),8. 00-7.87(m,11H),7.84(d,J=9.5Hz,2H),7.78(s,1H),7.68(d,J=2.3Hz,1H),7.58-7.46(m,4H),7.46-7.35(m,4H).

[0304] Synthesis of compound CPD558

[0305] The synthetic route is:

[0306] Synthesis of compound CPD558-2

[0307] Referring to the synthesis and purification method of compound CPD25-5, it is only necessary to change the corresponding raw materials to obtain the white solid target compound CPD558-2 (19.02 g, purity: 99.63%, yield: 75.00%), mass spectrum: 357.22 (M+H).

[0308] Synthesis of compound CPD558-3

[0309] By referring to the synthesis and purification methods of compound CPD25-7, only the corresponding starting materials were changed to obtain the target compound CPD558-3 (18.06 g, yield: 94.33%) as a white solid with a mass spectrum of 385.04 (M+H). The obtained compound was used directly in the next step without purification.

[0310] Synthesis of compound CPD558-4

[0311] Referring to the synthesis and purification method of compound CPD25-8, it is only necessary to change the corresponding raw materials to obtain the white solid target compound CPD558-4 (18.96 g, purity: 99.63%, yield: 75.96%), mass spectrum: 353.08 (M+H).

[0312] Synthesis of compound CPD558-5

[0313] Referring to the synthesis and purification method of compound CPD25-9, it is only necessary to change the corresponding raw materials to obtain the white solid target compound CPD558-5 (20.63 g, purity: 99.01%, yield: 74.12%), mass spectrum: 445.21 (M+H).

[0314] Synthesis of compound CPD558-7

[0315] Referring to the synthesis and purification method of compound CPD25-3, it is only necessary to change the corresponding raw materials to obtain the white solid target compound CPD558-7 (22.53 g, purity: 99.32%, yield: 76.12%), mass spectrum: 420.21 (M+H).

[0316] Synthesis of compound CPD558-8

[0317] Referring to the synthesis and purification method of compound CPD77-3, it is only necessary to change the corresponding raw materials to obtain the white solid target compound CPD558-8 (18.88 g, purity: 99.68%, yield: 72.85%), mass spectrum: 420.21 (M+H).

[0318] Synthesis of compound CPD558

[0319] Referring to the synthesis and purification methods for compound CPD59, only the corresponding starting materials were changed to obtain the target compound CPD558 (15.96 g, purity: 99.95%, yield: 72.96%) as a yellow solid. 15.96 g of crude CPD558 was purified by sublimation to obtain pure CPD558 (12.01 g, purity: 99.94%, yield: 75.25%), with a mass spectrum of 765.26 (M+H).

[0320] 1 H NMR (400MHz, CDCl3) δ8.60 (dd, J=8.4, 3.3Hz, 2H), 8.49-8.38 (m, 2H), 8.28 (d d,J=7.5,1.3Hz,1H),8.18-8.11(m,3H),8.10-8.03(m,2H),8.01-7.82(m,6H ),7.73(d,J=7.7Hz,1H),7.66(d,J=2.0Hz,1H),7.58(td,J=7.7,1.3Hz,1H), 7.56-7.46(m,7H),7.42-7.38(m,1H),7.34-7.27(m,2H),7.24-7.11(m,3H).

[0321] Synthesis of compound CPD584

[0322] The synthetic route is:

[0323] Synthesis of compound CPD584-2

[0324] Referring to the synthesis and purification method of compound CPD25-3, only the corresponding raw materials need to be changed to obtain the white solid target compound CPD584-2 (25.26 g, purity: 99.02%, yield: 74.63%), mass spectrum: 345.08 (M+H).

[0325] Synthesis of compound CPD584-3

[0326] Referring to the synthesis and purification method of compound CPD25-5, it is only necessary to change the corresponding raw materials to obtain the white solid target compound CPD584-3 (22.11 g, purity: 99.52%, yield: 72.00%), mass spectrum: 373.04 (M+H).

[0327] Synthesis of compound CPD584-4

[0328] Referring to the synthesis and purification methods of compound CPD25-7, only the corresponding raw materials were changed to obtain the target compound CPD584-4 (20.63 g, yield: 94.00%) as a white solid with a mass spectrum of 401.06 (M+H). The obtained compound was used directly in the next step without purification.

[0329] Synthesis of compound CPD584-5

[0330] Referring to the synthesis and purification method of compound CPD25-8, it is only necessary to change the corresponding raw materials to obtain the white solid target compound CPD584-5 (19.89 g, purity: 99.72%, yield: 74.63%), mass spectrum: 369.04 (M+H).

[0331] Synthesis of compound CPD584-6

[0332] Referring to the synthesis and purification method of compound CPD25-9, only the corresponding raw materials need to be changed to obtain the white solid target compound CPD584-6 (18.08 g, purity: 99.33%, yield: 74.01%), mass spectrum: 461.17 (M+H).

[0333] Synthesis of compound CPD584

[0334] Referring to the synthesis and purification methods for compound CPD59, only the corresponding starting materials were modified to obtain the target compound CPD584 (17.52 g, purity: 99.95%, yield: 72.11%) as a yellow solid. 17.52 g of crude CPD584 was purified by sublimation to obtain pure CPD584 (14.01 g, purity: 99.95%, yield: 79.96%), with a mass spectrum of 783.21 (M+H).

[0335] 1 H NMR (400MHz, CDCl3) δ8.62(d,J=2.2Hz,1H),8.28(d,J=2.2Hz,1H),8.22(d,J=7.0Hz,1H),8. 11-8.01(m,9H),8.00-7.95(m,3H),7.95-7.82(m,7H),7.54-7.46(m,6H),7.46-7.36(m,2H).

[0336] Synthesis of compound CPD609

[0337] The synthetic route is:

[0338] Synthesis of compound CPD609-2

[0339] Referring to the synthesis and purification method of compound CPD25-3, it is only necessary to change the corresponding raw materials to obtain the white solid target compound CPD609-2 (20.33 g, purity: 99.08%, yield: 72.74%), mass spectrum: 477.17 (M+H).

[0340] Synthesis of compound CPD609-3

[0341] Referring to the synthesis and purification method of compound CPD25-5, it is only necessary to change the corresponding raw materials to obtain the white solid target compound CPD609-3 (19.87 g, purity: 99.63%, yield: 74.85%), mass spectrum: 505.13 (M+H).

[0342] Synthesis of compound CPD609-4

[0343] By referring to the synthesis and purification methods of compound CPD25-7, only the corresponding starting materials were changed to obtain the target compound CPD609-4 (18.96 g, yield: 96.66%) as a white solid with a mass spectrum of 533.16 (M+H). The obtained compound was used directly in the next step without further purification.

[0344] Synthesis of compound CPD609-5

[0345] Referring to the synthesis and purification method of compound CPD25-8, it is only necessary to change the corresponding raw materials to obtain the white solid target compound CPD609-5 (19.45 g, purity: 99.52%, yield: 75.05%), mass spectrum: 501.13 (M+H).

[0346] Synthesis of compound CPD609-6

[0347] Referring to the synthesis and purification method of compound CPD25-9, it is only necessary to change the corresponding raw materials to obtain the white solid target compound CPD609-6 (19.86 g, purity: 99.00%, yield: 76.52%), mass spectrum: 593.26 (M+H).

[0348] Synthesis of compound CPD609

[0349] Referring to the synthesis and purification methods for compound CPD59, only the corresponding starting materials were modified to obtain the target compound CPD609 (18.77 g, purity: 99.94%, yield: 74.87%) as a yellow solid. 18.77 g of crude CPD609 was purified by sublimation to obtain pure CPD609 (14.98 g, purity: 99.94%, yield: 79.80%), with a mass spectrum of 788.26 (M+H).

[0350] 1H NMR(400MHz, CDCl3) δ8.62(d,J=9.1Hz,1H),8.50(d,J=8.0Hz,1H),8.48-8.4 1(m,1H),8.39(d,J=2.3Hz,1H),8.25(d,J=8.9Hz,1H),8.16(d,J=7.5Hz,1H) ,8.14-7.97(m,8H),7.94(d,J=8.1Hz,1H),7.91-7.82(m,3H),7.73(d,J=9.5 Hz,1H),7.67-7.59(m,1H),7.59-7.38(m,12H),7.26(dd,J=9.3,6.8Hz,1H).

[0351] Synthesis of compound CPD617

[0352] The synthetic route is:

[0353] Synthesis of compound CPD617-2

[0354] Referring to the synthesis and purification method of compound CPD25-3, it is only necessary to change the corresponding raw materials to obtain the white solid target compound CPD617-2 (23.53 g, purity: 99.05%, yield: 74.63%), mass spectrum: 480.18 (M+H).

[0355] Synthesis of compound CPD617-3

[0356] Referring to the synthesis and purification method of compound CPD25-5, it is only necessary to change the corresponding raw materials to obtain the white solid target compound CPD617-3 (21.85 g, purity: 99.67%, yield: 75.86%), mass spectrum: 508.14 (M+H).

[0357] Synthesis of compound CPD617-4

[0358] Referring to the synthesis and purification methods of compound CPD25-7, only the corresponding starting materials were changed to obtain the target compound CPD627-4 (20.00 g, yield: 97.06%) as a white solid with a mass spectrum of 536.05 (M+H). The obtained compound was used directly in the next step without purification.

[0359] Synthesis of compound CPD617-5

[0360] Referring to the synthesis and purification method of compound CPD25-8, it is only necessary to change the corresponding raw materials to obtain the white solid target compound CPD617-5 (19.45 g, purity: 99.52%, yield: 75.05%), mass spectrum: 504.14 (M+H).

[0361] Synthesis of compound CPD617-6

[0362] Referring to the synthesis and purification method of compound CPD25-9, it is only necessary to change the corresponding raw materials to obtain the white solid target compound CPD617-6 (18.41 g, purity: 99.16%, yield: 74.51%), mass spectrum: 596.27 (M+H).

[0363] Synthesis of compound CPD617

[0364] Referring to the synthesis and purification methods for compound CPD59, only the corresponding starting materials were changed to obtain the target compound CPD617 (14.96 g, purity: 99.95%, yield: 72.96%) as a yellow solid. 14.96 g of crude CPD617 was purified by sublimation to obtain pure CPD617 (11.76 g, purity: 99.95%, yield: 78.60%), with a mass spectrum of 777.29 (M+H).

[0365] 1 H NMR (400MHz, CDCl3) δ8.48(d,J=9.4Hz,1H),8.26-8.19(m,2H),8.14(d,J=9.3Hz,1H),8.12-8.01(m,4H),7.99(d,J=6.8Hz,1H),7.97-7.87(m,5H), 7.85(d,J=8.0Hz,1H),7.73-7.66(m,2H),7.62(dd,J=6.9,1.2Hz,1H),7. 61-7.54(m,3H),7.54-7.46(m,7H),7.45-7.37(m,7H),7.25-7.22(m,1H).

[0366] Synthesis of compound CPD632

[0367] The synthetic route is:

[0368] Referring to the synthesis and purification methods for compound CPD119, only the corresponding starting materials were modified to obtain the target compound CPD632 (10.02 g, purity: 99.94%, yield: 76.87%) as a yellow solid. 10.02 g of crude CPD632 was purified by sublimation to obtain pure CPD632 (7.88 g, purity: 99.94%, yield: 78.64%), with a mass spectrum of 572.19 (M+H).

[0369] 1 H NMR (400MHz, CDCl3) δ9.26 (d, J=1.3Hz, 1H), 8.71 (dd, J=4.6, 1.3Hz, 1H), 8.61 (dd,J=8.5,3.7Hz,2H),8.50-8.37(m,1H),8.36-8.24(m,1H),8.11(d,J=7.8Hz ,1H),8.07-7.97(m,2H),7.94(d,J=8.2Hz,1H),7.91-7.83(m,2H),7.61-7.46 (m,7H),7.46-7.36(m,4H),7.32(d,J=7.3Hz,1H),7.16(dd,J=8.0,2.1Hz,1H).

[0370] Synthesis of compound CPD643

[0371] The synthetic route is:

[0372] Referring to the synthesis and purification methods for compound CPD119, only the corresponding starting materials were modified to obtain the target compound CPD643 (11.84 g, purity: 99.95%, yield: 72.02%) as a yellow solid. 11.84 g of crude CPD643 was purified by sublimation to obtain pure CPD643 (8.09 g, purity: 99.95%, yield: 68.32%), with a mass spectrum of 512.17 (M+H).

[0373] 1H NMR (400MHz, CDCl3) δ8.37(d,J=2.2Hz,1H),8.17(d,J=9.1Hz,1H),8.12(d,J=8.0Hz,1H),8.08-8.03(m,1H),7.99(d,J=8.0Hz,1H),7.96-7.9 1(m,5H),7.91-7.86(m,1H),7.85(dd,J=7.6,3.0Hz,2H),7.68-7.56(m,4H),7.55-7.48(m,2H),7.45(t,J=7.1Hz,1H),7.32(d,J=7.2Hz,1H).

[0374] Application example: Preparation of organic electroluminescent devices

[0375] Figure 2 is a schematic structural diagram of the organic electroluminescent device of the present invention, which includes, from bottom to top, a stacked glass substrate 1, an anode 2 (indium tin oxide), a hole injection layer 3, a first hole transport layer (HTL1) 4, a second hole transport layer (HTL2) 5, a light-emitting layer 6, an electron transport layer (ETL) 7, an electron injection layer 8 (EIL) and a cathode 9.

[0376] A 50 mm×50 mm×1.0 mm glass substrate with an ITO (indium tin oxide, 100 nm) transparent electrode was ultrasonically cleaned in ethanol for 10 minutes, dried at 150° C., and then treated with N 2 plasma for 30 minutes. The washed glass substrate is mounted on a substrate holder of a vacuum evaporation device, and compound NDP-9 and compound HTM1 are evaporated in a weight ratio of 97:3 to form a hole injection layer with a thickness of 10 nm, followed by evaporation of a layer of HTM1 to form a thin film with a thickness of 60 nm as HTL1 (hole transport layer 1), and then a layer of HTM2 is evaporated on the HTM1 thin film to form a thin film with a thickness of 10 nm as HTL2 (hole transport layer 2), and then, a light-emitting layer with a thickness of 40 nm is co-evaporated on the HTM2 film layer in the form of a single host or a double host (host material: red light doping material = 97%:3%, mass fraction), wherein the host materials of the single host or the double host are the organic electroluminescent compound synthesized by the present invention, RH-P and comparative compound 1-4, respectively. On the light-emitting layer, ETL (electron transport layer) material and LiQ were co-evaporated (35nm) in a weight ratio of 50:50 as an electron transport material, and then LiQ (1nm) was evaporated on the electron transport material layer as an electron injection material. Then, Mg / Ag (100nm, mass ratio of 1:9) was evaporated as the cathode material using a co-evaporation mode to produce an organic electroluminescent device.

[0377] The structural formulas of NDP-9, HTM1, HTM2, red light doping material, ETL material, LiQ, RH-P, and comparative compounds 1-4 are as follows:

[0378] Performance Testing

[0379] The performance of the organic electroluminescent device was tested. The organic electroluminescent compound synthesized by the present invention and the comparative compounds 1-4 were used as the main materials for comparison. A constant current power supply (Keithley 2400) was used to flow a fixed current density through the light-emitting element. The luminescence spectrum was measured using a spectroradiometer (CS2000). At the same time, the luminescence spectrum was measured at 10 mA / cm 2 The IVL (current-voltage-luminance) performance of the device was measured at 50 mA / cm 2 The LT95 device lifespan was tested under the following conditions. The results are shown in Tables 1 and 2.

[0380] Table 1 shows the performance test results of devices in which the organic electroluminescent compounds synthesized in the present invention and comparative compounds 1-3 are respectively used as single host materials and co-evaporated with red light doping materials to form a light-emitting layer (the examples in Table 1 use the organic electroluminescent compounds of the present invention, and the comparative examples use the above-mentioned comparative compounds).

[0381] Table 1:

[0382] The performance test results of devices using the organic electroluminescent compounds synthesized in the present invention and comparative compounds 1-4 mixed with RH-P material in a ratio of 5:5 and co-evaporated with red light doping materials to form a light-emitting layer are shown in Table 2 (the examples in Table 2 use the organic electroluminescent compounds of the present invention, and the comparative examples use the above-mentioned comparative compounds).

[0383] Table 2:

[0384] As shown in Tables 1-2, light-emitting devices fabricated using the organic electroluminescent compounds synthesized in the present invention as single-host red light-emitting materials exhibit lower driving voltages, higher luminous efficiency, and longer device lifetimes compared to devices fabricated using Comparative Compounds 1-3, at the same emission wavelength. Furthermore, when the organic electroluminescent compounds synthesized in the present invention are combined with p-type materials as dual-host materials, the luminous efficiency and lifetime are significantly improved compared to single-host red light-emitting materials due to the balanced hole and electron transport rates and the expanded exciton recombination zone in the light-emitting layer. These improvements are far superior to those achieved by devices fabricated using Comparative Compounds 1-4.

[0385] The sublimation temperatures of the organic electroluminescent compounds synthesized in the present invention and comparative compounds 1-3 were tested, and the results are shown in Table 3. Wherein: the sublimation temperature is defined as: -7 The vacuum degree of Torr and the temperature corresponding to the sublimation rate of 1 angstrom per second.

[0386] Table 3:

[0387] As can be seen from Table 3, the compounds synthesized in the present invention have lower sublimation temperatures than comparative compounds 1-3, and are more conducive to industrial application.

[0388] Therefore, the compound synthesized in the present invention has the advantages of high optical and electrical stability, low sublimation temperature, low driving voltage, high luminous efficiency, and long device life, and can be used as a red light host material in OLED light-emitting devices; at the same time, it has a low melting point, and as a molten material, it is beneficial to the stability of material evaporation. As a host material, it has the potential to be applied in the AMOLED industry.

[0389] In addition, since it is impossible to enumerate all the organic electroluminescent compounds synthesized by the present invention, the above Tables 1-3 only list the properties of some of the compounds or devices of the present invention. However, within the scope of protection claimed in the present invention, especially the compounds with specific structural formulas given in the present invention, all have advantages similar to those of the compounds used in Tables 1-3, such as high optical and electrical stability, low sublimation temperature, low driving voltage, high luminous efficiency, and long device life.

Claims

1. A compound, characterized in that Its general structural formula is shown in formula (1): Where: X is selected from NR a , CR b R c , O, S or Se; R a 、R b 、R c Each is independently selected from C1-C30 alkyl, C1-C30 heteroalkyl, C3-C30 cycloalkyl, C3-C30 heterocycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C3-C30 alkylsilyl, and C6-C30 arylsilyl; ET represents an electron-withdrawing group; L is selected from a single bond, a substituted or unsubstituted C6-C60 arylene group, or a substituted or unsubstituted C3-C60 heteroarylene group; Ring A is selected from the structure represented by formula (2) or formula (3); X1-X 12 are independently selected from CR0 or N; and X1-X4, X5-X6, X7-X8, X9-X 12 There are two adjacent sites fused to the 5-membered ring containing X in formula (1); R0 is selected from hydrogen, deuterium, halogen, cyano, nitro, C1-C40 alkyl, C1-C40 heteroalkyl, C2-C40 alkenyl, C2-C40 alkynyl, C3-C40 cycloalkyl, C3-C40 heterocycloalkyl, C6-C60 aryl, C3-C60 heteroaryl, C1-C40 alkoxy, C6-C60 aryloxy, C3-C40 alkylsilyl, C6-C60 arylsilyl, C1-C40 alkylboryl, C6-C60 arylboryl, C6-C60 arylphosphino, C6-C60 monoarylphosphino, C6-C60 diarylphosphino or C6-C60 arylamine; and two adjacent R0 may be connected to form a ring; The substitution is substituted by at least one of deuterium, halogen, cyano, isocyano, phosphino, C1-C6 alkyl, C3-C16 cycloalkyl, C1-C6 alkyl-substituted amine, C1-C6 hydrocarbon-substituted or unsubstituted C6-C30 aryl, C1-C6 hydrocarbon-substituted or unsubstituted C3-C30 heteroaryl, wherein the number of substitutions ranges from single substitution to the maximum number of substitutions.

2. The compound according to claim 1, characterized in that The R0 is selected from hydrogen, deuterium, halogen, cyano, nitro, C1-C30 alkyl, C1-C30 heteroalkyl, C2-C30 alkenyl, C2-C30 alkynyl, C3-C30 cycloalkyl, C3-C30 heterocycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C1-C30 alkoxy, C6-C30 aryloxy, C3-C30 alkylsilyl, C6-C30 arylsilyl, C1-C30 alkylboryl, C6-C30 arylboryl, C6-C30 arylphosphino, C6-C30 monoarylphosphino, C6-C30 diarylphosphino or C6-C30 arylamine; and two adjacent R0 may be connected to form a ring; and / or The substitution is substituted by at least one of deuterium, halogen, cyano, isocyano, phosphino, C1-C6 alkyl, C3-C12 cycloalkyl, C1-C6 alkyl-substituted amino, C6-C18 aryl or C3-C18 heteroaryl, wherein the number of substitutions ranges from single substitution to the maximum number of substitutions.

3. The compound according to claim 1, characterized in that The heteroatoms in the heteroaryl, heteroalkyl and heterocycloalkyl groups are independently selected from at least one of O, S, N, Se, Si and Ge; and / or, the R a 、R b 、R c They are independently selected from C1-C20 alkyl, C1-C20 heteroalkyl, C3-C20 cycloalkyl, C3-C20 heterocycloalkyl, C6-C20 aryl, C3-C20 heteroaryl, C3-C20 alkylsilyl and C6-C20 arylsilyl.

4. The compound according to claim 3, characterized in that The R a 、R b 、R c They are independently selected from C1-C10 alkyl, C1-C10 heteroalkyl, C3-C10 cycloalkyl, C3-C10 heterocycloalkyl, C6-C10 aryl, and C3-C10 heteroaryl.

5. The compound according to claim 1, characterized in that The structure represented by formula (2) or formula (3) is selected from the structures represented by formula (A-1) to (A-8): Wherein: * represents the site of fusion with the 5-membered ring containing X in formula (1); m is an integer of 0-10; if m is an integer not less than 2, each R0 may be the same or different, and two adjacent R0 may be connected to form a ring.

6. The compound according to any one of claims 1 to 5, characterized in that The structure represented by formula (2) or formula (3) is selected from the structures represented by formulas (A-9) to (A-16): Wherein, * represents the site fused to the 5-membered ring containing X in formula (1); t is an integer of 0-6; if t is an integer not less than 2, each R0 may be the same or different, and two adjacent R0 may be connected to form a ring.

7. The compound according to any one of claims 1 to 5, characterized in that The electron-withdrawing group is selected from the structures shown in formulas (B-1) to (B-10): Wherein: * represents the site of connection with L in formula (1); Z is selected from N or CR d , and at least one Z is N, and two adjacent Zs in formula (B-10) are not N at the same time; W is selected from NR e 、O、S、SO、SO2、CR f R g or SiR h R j ; Y is selected from NR a , CR b R c , O, S or Se, and Ra, R b 、R c Compared with Ra and R of X in claim 1 b 、R c consistent definitions; R1, Rd-Rh, Rj are independently selected from hydrogen, deuterium, halogen, cyano, nitro, C1-C40 alkyl, C1-C40 heteroalkyl, C2-C40 alkenyl, C2-C40 alkynyl, C3-C40 cycloalkyl, C3-C40 heterocycloalkyl, C3-C40 alkylsilyl, C6-C60 arylsilyl, C1-C40 alkylboryl, C1-C40 alkoxy substituted or an unsubstituted C6-C60 aryl group, a substituted or unsubstituted C3-C60 heteroaryl group, a substituted or unsubstituted C6-C60 aryloxy group, a substituted or unsubstituted C6-C60 arylboronyl group, a substituted or unsubstituted C6-C60 arylphosphino group, a substituted or unsubstituted C6-C60 monoarylphosphino group, a substituted or unsubstituted C6-C60 diarylphosphino group, or a substituted or unsubstituted C6-C60 arylamine group; The substitution is substituted by at least one of deuterium, halogen, cyano, isocyano, phosphino, C1-C6 alkyl, C3-C16 cycloalkyl, C1-C6 alkyl-substituted amine, C1-C6 alkyl-substituted or unsubstituted C6-C30 aryl, C1-C6 alkyl-substituted or unsubstituted C3-C30 heteroaryl, wherein the number of substitutions ranges from single substitution to the maximum number of substitutions; n is an integer of 0-10; if n is an integer not less than 2, each R1 may be the same or different, and two adjacent R1s may be connected to form a ring.

8. The compound according to claim 7, characterized in that The Rd-Rh and Rj are independently selected from hydrogen, deuterium, halogen, cyano, nitro, C1-C30 alkyl, C1-C30 heteroalkyl, C2-C30 alkenyl, C2-C30 alkynyl, C3-C30 cycloalkyl, C3-C30 heterocycloalkyl, C3-C30 alkylsilyl, C6-C30 arylsilyl, C1-C30 alkylboryl, C1-C30 alkoxy substituted or an unsubstituted C6-C30 aryl group, a substituted or unsubstituted C3-C30 heteroaryl group, a substituted or unsubstituted C6-C30 aryloxy group, a substituted or unsubstituted C6-C30 arylboronyl group, a substituted or unsubstituted C6-C30 arylphosphino group, a substituted or unsubstituted C6-C30 monoarylphosphino group, a substituted or unsubstituted C6-C30 diarylphosphino group, or a substituted or unsubstituted C6-C30 arylamine group.

9. The compound according to claim 8, characterized in that Said Rd-Rh, Rj are independently selected from hydrogen, deuterium, halogen, cyano, nitro, C1-C20 alkyl, C1-C20 heteroalkyl, C2-C20 alkenyl, C2-C20 alkynyl, C3-C20 cycloalkyl, C3-C20 heterocycloalkyl, C3-C20 alkylsilyl, C6-C20 arylsilyl, C1-C20 alkylboryl, C1-C20 alkoxy substituted or an unsubstituted C6-C20 aryl group, a substituted or unsubstituted C3-C20 heteroaryl group, a substituted or unsubstituted C6-C20 aryloxy group, a substituted or unsubstituted C6-C20 arylboronyl group, a substituted or unsubstituted C6-C20 arylphosphino group, a substituted or unsubstituted C6-C20 monoarylphosphino group, a substituted or unsubstituted C6-C20 diarylphosphino group, or a substituted or unsubstituted C6-C20 arylamine group.

10. The compound according to claim 7, characterized in that The electron-withdrawing group is selected from the structures shown in formulas (B-11) to (B-36): Wherein: R1 and R2 are independently selected from hydrogen, deuterium, halogen, cyano, nitro, C1-C40 alkyl, C1-C40 heteroalkyl, C2-C40 alkenyl, C2-C40 alkynyl, C3-C40 cycloalkyl, C3-C40 heterocycloalkyl, C3-C40 alkylsilyl, C6-C60 arylsilyl, C1-C40 alkylboryl, C1-C40 alkoxy substituted or unsubstituted a substituted C6-C60 aryl group, a substituted or unsubstituted C3-C60 heteroaryl group, a substituted or unsubstituted C6-C60 aryloxy group, a substituted or unsubstituted C6-C60 arylboronyl group, a substituted or unsubstituted C6-C60 arylphosphino group, a substituted or unsubstituted C6-C60 monoarylphosphino group, a substituted or unsubstituted C6-C60 diarylphosphino group, or a substituted or unsubstituted C6-C60 arylamine group; and / or, X is selected from CR b R c , O or S, and R in X b 、R c They are each independently selected from C1-C10 alkyl, C1-C10 heteroalkyl, C3-C10 cycloalkyl, C3-C10 heterocycloalkyl, C6-C10 aryl or C3-C10 heteroaryl.

11. The compound according to claim 10, characterized in that R1 and R2 are independently selected from hydrogen, deuterium, halogen, cyano, nitro, C1-C30 alkyl, C1-C30 heteroalkyl, C2-C30 alkenyl, C2-C30 alkynyl, C3-C30 cycloalkyl, C3-C30 heterocycloalkyl, C3-C30 alkylsilyl, C6-C30 arylsilyl, C1-C30 alkylboryl, C1-C30 alkoxy substituted or unsubstituted a substituted C6-C30 aryl group, a substituted or unsubstituted C3-C30 heteroaryl group, a substituted or unsubstituted C6-C30 aryloxy group, a substituted or unsubstituted C6-C30 arylboronyl group, a substituted or unsubstituted C6-C30 arylphosphino group, a substituted or unsubstituted C6-C30 monoarylphosphino group, a substituted or unsubstituted C6-C30 diarylphosphino group, or a substituted or unsubstituted C6-C30 arylamine group.

12. The compound according to claim 11, characterized in that R1 and R2 are independently selected from hydrogen, deuterium, halogen, cyano, nitro, C1-C20 alkyl, C1-C20 heteroalkyl, C2-C20 alkenyl, C2-C20 alkynyl, C3-C20 cycloalkyl, C3-C20 heterocycloalkyl, C3-C20 alkylsilyl, C6-C20 arylsilyl, C1-C20 alkylboryl, C1-C20 alkoxy substituted or unsubstituted a substituted C6-C20 aryl group, a substituted or unsubstituted C3-C20 heteroaryl group, a substituted or unsubstituted C6-C20 aryloxy group, a substituted or unsubstituted C6-C20 arylboronyl group, a substituted or unsubstituted C6-C20 arylphosphino group, a substituted or unsubstituted C6-C20 monoarylphosphino group, a substituted or unsubstituted C6-C20 diarylphosphino group, or a substituted or unsubstituted C6-C20 arylamine group.

13. The compound according to claim 10, characterized in that The R1 and R2 are independently selected from hydrogen, deuterium, halogen, substituted or unsubstituted C6-C20 arylene or substituted or unsubstituted C3-C20 heteroarylene; and each R1 may be the same or different, and two adjacent R1s may be connected to form a ring.

14. The compound according to any one of claims 1 to 5, characterized in that The L is selected from a single bond, a substituted or unsubstituted C6-C20 arylene group, or a substituted or unsubstituted C3-C20 heteroarylene group.

15. The compound according to any one of claims 1 to 5, characterized in that The L is selected from a single bond or a structure represented by formula (L-1) to formula (L-14): Wherein: R is a substituent, each R is independently selected from hydrogen, deuterium, halogen, cyano, nitro, C1-C20 alkyl, C1-C20 heteroalkyl, C2-C20 alkenyl, C2-C20 alkynyl, C3-C20 cycloalkyl, C3-C20 heterocycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C1-C20 alkoxy, C6-C30 aryloxy, C3-C20 alkylsilyl, C6-C30 arylsilyl, C1-C20 alkylboryl, C6-C30 arylboryl, C6-C30 arylphosphino, C6-C30 monoarylphosphino, C6-C30 diarylphosphino or C6-C30 arylamine, wherein the number of substitutions is from monosubstitution to the maximum number of substitutions.

16. The compound according to claim 1 or 2, characterized in that The structural formula of the compound is one of the structural formulas shown in Formulas CPD1 to CPD645, or a structure in which hydrogen in Formulas CPD1 to CPD645 is partially or completely replaced by deuterium, or a structure in which hydrogen in Formulas CPD1 to CPD645 is partially or completely replaced by fluorine:

17. An organic electroluminescent device, characterized in that: The invention comprises a light-emitting layer, wherein the light-emitting layer comprises the compound according to any one of claims 1 to 16.

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