Host material composition and organic electroluminescent device

Abstract

Disclosed are a host material composition and an organic electroluminescent device. The host material composition comprises at least one first host compound and at least one second host compound, the first host compound having a structure as shown in formula (1), and the second host compound being represented by the following formula (2), Z1, Z2 and Z3 each independently being selected from N or CRd; at least one of Ar3 to Ar5 is selected from the following formula (3); Y is selected from NRe, CRfRg or a chalcogen element. The host material composition has the advantages of low driving voltage, high luminous efficiency, and long device service life.

Description

A host material composition and an organic electroluminescent device Technical Field

[0001] This application belongs to the field of luminescent materials technology, and specifically relates to a host material composition and an organic electroluminescent device. Background Technology

[0002] Currently, organic light-emitting diodes (OLEDs), as a next-generation display technology, are receiving increasing attention in both display and lighting technologies. However, compared to market application requirements, the luminous efficiency, driving voltage, and lifespan of OLED devices still need further improvement.

[0003] Generally, the basic structure of an OLED device consists of thin films of various organic functional materials sandwiched between metal electrodes, resembling a sandwich structure. Driven by an electric current, electrons and holes are injected from the anode and cathode, respectively. After traveling a certain distance, the electrons and holes recombine in the emissive layer and are released as light or heat, thus achieving the luminescence effect. However, the properties of phosphorescent OLEDs are not only determined by the triplet emitter used, but also by other types of materials, such as the host material, which is also quite important. The host material plays a significant role in reducing the device's driving voltage, improving its luminous efficiency, and extending its lifespan. However, existing host materials require further improvement in reducing driving voltage, improving luminous efficiency, and extending lifespan.

[0004] Therefore, it is necessary to continue to develop new host materials and their compositions to further improve the performance of organic electroluminescent devices and to solve the aforementioned problems existing in organic electroluminescent devices. Summary of the Invention

[0005] This application aims to at least solve one of the technical problems existing in the prior art. To this end, this application proposes a host material composition and an organic electroluminescent device.

[0006] The first aspect of this application provides a body material composition.

[0007] In some embodiments, a host material composition comprises at least one first host compound and at least one second host compound; the structure of the first host compound is shown in formula (1):

[0008] Among them, ring A is selected from the following formula (1-2) or formula (1-3);

[0009] Among them, X1-X 12 Each is independently selected as CR0 or N; and X1-X4, X5- X6, X7-X8, X9-X 12 Two adjacent sites are fused with the 5-membered ring containing X in equation (1);

[0010] Ring B is selected from substituted or unsubstituted benzene rings, naphthalene rings, or phenanthrene rings;

[0011] In equation (1), X is selected from NR. a CR b R c Or oxygen group elements;

[0012] R a R b R c Each is independently selected from at least one of the following: substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C1-C30 heteroalkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C3-C30 alkylsilyl, and substituted or unsubstituted C6-C30 arylsilyl.

[0013] L is selected from single bond, substituted or unsubstituted C6-C60 arylene or substituted or unsubstituted C3-C60 heteroarylene;

[0014] Ar1 and Ar2 are independently selected from substituted or unsubstituted C6-C60 aryl and substituted or unsubstituted C3-C60 heteroaryl, respectively;

[0015] The structure of the second host compound is shown in formula (2):

[0016] Among them, Z1, Z2, and Z3 are each independently selected from N or CR. d ;

[0017] Ar3 to Ar5 each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C60 alkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, substituted or unsubstituted C3-C60 cycloalkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted tri(C1-C30)alkylsilyl, substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, -N-(R')(R”); or Ar3 to Ar5 each independently form a ring with a substituent on a carbon atom or heteroatom adjacent to the substituted position;

[0018] Among them, at least one of Ar3 to Ar5 is selected from the following formula (3):

[0019] Where Y is selected from NR e CR f R g Or oxygen group elements;

[0020] R e R f R g Each and every one is independently selected from at least one of substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C1-C30 heteroalkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C3-C30 alkylsilyl or C6-C30 arylsilyl; or R f and R g Connect them into a ring;

[0021] in, Indicates the connection sites with L1, L2, and L3 in equation (2);

[0022] Wherein, ring C is selected from substituted or unsubstituted benzene rings, naphthalene rings, and phenanthrene rings;

[0023] R0, R1, R d Each and every one is independently selected from hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted C1-C40 alkyl, substituted or unsubstituted C1-C40 heteroalkyl, substituted or unsubstituted C2-C40 alkenyl, substituted or unsubstituted C2-C40 alkynyl, substituted or unsubstituted C3-C40 cycloalkyl, substituted or unsubstituted C3-C40 heterocycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, substituted or unsubstituted The substituted C1-C40 alkoxy group, substituted or unsubstituted C6-C60 aryloxy group, substituted or unsubstituted C3-C40 alkylsilyl group, substituted or unsubstituted C6-C60 arylsilyl group, substituted or unsubstituted C1-C40 alkylboryl group, substituted or unsubstituted C6-C60 arylboryl group, substituted or unsubstituted C6-C60 arylphosphinyl group, or substituted or unsubstituted C6-C60 arylamino group; or, two adjacent R0 groups may be linked to form a fused ring;

[0024] Wherein, R' and R” each independently represent a substituted or unsubstituted C1-C30 alkyl, a substituted or unsubstituted C2-C30 alkenyl, a substituted or unsubstituted C6-C30 aryl, or a substituted or unsubstituted C3-C30 heteroaryl.

[0025] Where p is an integer from 0 to 10; if p is from 2 to 10, then each R1 can be the same or different, and adjacent R1s can be connected to form a parallel ring;

[0026] L1, L2, and L3 are selected from single bonds, substituted or unsubstituted C6-C60 arylene groups, substituted or unsubstituted C3-C60 heteroarylene groups, or substituted or unsubstituted C3-C30 cycloalkyl groups.

[0027] The R0, R1, R a ~R g In the series L, L1-L3, Ar1-Ar5, R', R", the substitution is at least one of deuterium, halogen, cyano, isocyano, phosphin, C1-C6 alkyl, C3-C16 cycloalkyl, C1-C6 alkyl-substituted amino, 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 monosubstituted to the maximum number of substitutions;

[0028] The heteroatom in the heteroaryl, heteroaryl, heteroalkyl, heterocycloalkyl, or heteroatom is independently selected from at least one of O, S, N, Se, Si, and Ge.

[0029] Compared to existing technologies, the beneficial effects of this application are as follows:

[0030] The various host materials described in this application exhibit advantages such as low driving voltage, high luminous efficiency, and long device lifespan, and even a low sublimation temperature, making them suitable as host materials for OLED light-emitting devices. They also possess a low melting point, which is beneficial for material deposition stability as molten materials. This combination of host materials, as a red light host material, has the potential for application in the AMOLED industry. Attached Figure Description

[0031] Figure 1 shows compound A226 of this application. 1 H NMR spectrum;

[0032] Figure 2 shows compound B35 of this application. 1 H NMR spectrum;

[0033] Figure 3 is a schematic diagram of the structure of an organic electroluminescent device according to an embodiment of this application. Detailed Implementation

[0034] To enable those skilled in the art to more clearly understand the technical solutions described in this application, the following embodiments are provided for illustration. It should be noted that the following embodiments do not constitute a limitation on the scope of protection claimed in this application.

[0035] Unless otherwise specified, the raw materials, reagents or devices used in the following examples are available from conventional commercial sources or can be obtained by existing known methods.

[0036] In some embodiments, a host material composition comprises at least one first host compound and at least one second host compound; the structure of the first host compound is shown in formula (1):

[0037] Among them, ring A is selected from the following formula (1-2) or formula (1-3);

[0038] Among them, X1-X 12 Each is independently selected as CR0 or N; and X1-X4, X 5- X6, X7-X8, X9-X 12 Two adjacent sites are fused with the 5-membered ring containing X in equation (1);

[0039] Ring B is selected from substituted or unsubstituted benzene rings, naphthalene rings, or phenanthrene rings;

[0040] In equation (1), X is selected from NR. a CR b R c Or oxygen group elements;

[0041] R a R b R c Each is independently selected from at least one of the following: substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C1-C30 heteroalkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C3-C30 alkylsilyl, and substituted or unsubstituted C6-C30 arylsilyl.

[0042] L is selected from single bond, substituted or unsubstituted C6-C60 arylene or substituted or unsubstituted C3-C60 heteroarylene;

[0043] Ar1 and Ar2 are independently selected from substituted or unsubstituted C6-C60 aryl and substituted or unsubstituted C3-C60 heteroaryl, respectively;

[0044] The structure of the second host compound is shown in formula (2):

[0045] Among them, Z1, Z2, and Z3 are each independently selected from N or CR. d ;

[0046] Ar3 to Ar5 each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C60 alkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, substituted or unsubstituted C3-C60 cycloalkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted tri(C1-C30)alkylsilyl, substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, -N-(R')(R”); or Ar3 to Ar5 each independently form a ring with a substituent on a carbon atom or heteroatom adjacent to the substituted position;

[0047] Among them, at least one of Ar3 to Ar5 is selected from the following formula (3):

[0048] Where Y is selected from NR e CR f R g Or oxygen group elements;

[0049] R e R f R g Each and every one is independently selected from at least one of substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C1-C30 heteroalkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C3-C30 alkylsilyl or C6-C30 arylsilyl; or R f and R g Connect them into a ring;

[0050] in, Indicates the connection sites with L1, L2, and L3 in equation (2);

[0051] Wherein, ring C is selected from substituted or unsubstituted benzene rings, naphthalene rings, and phenanthrene rings;

[0052] R0, R1, R dEach and every one is independently selected from hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted C1-C40 alkyl, substituted or unsubstituted C1-C40 heteroalkyl, substituted or unsubstituted C2-C40 alkenyl, substituted or unsubstituted C2-C40 alkynyl, substituted or unsubstituted C3-C40 cycloalkyl, substituted or unsubstituted C3-C40 heterocycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, substituted or unsubstituted The substituted C1-C40 alkoxy group, substituted or unsubstituted C6-C60 aryloxy group, substituted or unsubstituted C3-C40 alkylsilyl group, substituted or unsubstituted C6-C60 arylsilyl group, substituted or unsubstituted C1-C40 alkylboryl group, substituted or unsubstituted C6-C60 arylboryl group, substituted or unsubstituted C6-C60 arylphosphinyl group, or substituted or unsubstituted C6-C60 arylamino group; or, two adjacent R0 groups may be linked to form a fused ring;

[0053] Wherein, R' and R” each independently represent a substituted or unsubstituted C1-C30 alkyl, a substituted or unsubstituted C2-C30 alkenyl, a substituted or unsubstituted C6-C30 aryl, or a substituted or unsubstituted C3-C30 heteroaryl.

[0054] Where p is an integer from 0 to 10; if p is from 2 to 10, then each R1 can be the same or different, and adjacent R1s can be connected to form a parallel ring;

[0055] L1, L2, and L3 are selected from single-bonded, substituted or unsubstituted C6-C60 arylene or substituted or unsubstituted C3-C60 heteroarylene, or substituted or unsubstituted C3-C30 cycloalkylene.

[0056] The R0, R1, R a ~R g In the series L, L1-L3, Ar1-Ar5, R', R", the substitution is at least one of deuterium, halogen, cyano, isocyano, phosphin, C1-C6 alkyl, C3-C16 cycloalkyl, C1-C6 alkyl-substituted amino, 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 monosubstituted to the maximum number of substitutions;

[0057] The heteroatom in the heteroaryl, heteroaryl, heteroalkyl, heterocycloalkyl, or heteroatom is independently selected from at least one of O, S, N, Se, Si, and Ge.

[0058] Ar3 to Ar5 are each independently linked to substituents on the carbon atoms or heteroatoms adjacent to their substitution sites to form a ring. This means that the substituents on the substitution sites of Ar3 to Ar5 can be linked to the substituents on the carbon atoms or heteroatoms of L1 to L3 to form a ring, or when L1 to L3 are single bonds, they are linked to Z1 to Z3 to form a ring. For example, L1 and Ar3, L2 and Ar4, and L3 and Ar5 can optionally be linked to each other to form substituted or unsubstituted rings of the following: naphthalene, fluorenyl, quinoline, dibenzothiophene, dibenzofuran, carbazole, benzofuran-pyridine, benzothiophene-pyridine, indoxpyridine, benzofuran-quinoline, benzothiophene-quinoline, or indoxquinoline ring.

[0059] In some embodiments, the C6-C60 arylphosphine group includes a C6-C60 monoarylphosphine group or a C6-C60 diarylphosphine group.

[0060] In some implementations, R0, R1, R d Each and every one is independently selected from hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C1-C30 heteroalkyl, substituted or unsubstituted C2-C30 alkenyl, substituted or unsubstituted C2-C30 alkynyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, substituted or unsubstituted C6-C40 aryl, substituted or unsubstituted C3-C40 heterocycloalkyl, etc. Aryl, substituted or unsubstituted C1-C40 alkoxy, substituted or unsubstituted C6-C40 aryloxy, substituted or unsubstituted C3-C30 alkylsilyl, substituted or unsubstituted C6-C40 arylsilyl, substituted or unsubstituted C1-C30 alkylboryl, substituted or unsubstituted C6-C40 arylboryl, substituted or unsubstituted C6-C40 arylphosphinyl, or substituted or unsubstituted C6-C40 arylamine.

[0061] In some implementations, R0, R1, R dEach and every one is independently selected from hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 heteroalkyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C2-C20 alkynyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C3-C20 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heterocycloalkyl, etc. Aryl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C3-C20 alkylsilyl, substituted or unsubstituted C6-C30 arylsilyl, substituted or unsubstituted C1-C20 alkylboryl, substituted or unsubstituted C6-C30 arylboryl, substituted or unsubstituted C6-C30 arylphosphinyl, or substituted or unsubstituted C6-C30 arylamino.

[0062] In some implementations, R a R b R c Each of the following is independently selected from substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 heteroalkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C3-C20 heterocycloalkyl, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C3-C20 heteroaryl, substituted or unsubstituted C3-C20 alkylsilyl, substituted or unsubstituted C6-C20 arylsilyl, or R b and R c Linkage to form fluorene groups (e.g.) ).

[0063] In some implementations, R a R b R c Each of the following is independently selected from substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C1-C15 heteroalkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C3-C15 heterocycloalkyl, substituted or unsubstituted C6-C18 aryl, substituted or unsubstituted C3-C18 heteroaryl, substituted or unsubstituted C3-C18 alkylsilyl, and substituted or unsubstituted C6-C18 arylsilyl.

[0064] In some embodiments, Ar1 and Ar2 are independently selected from substituted or unsubstituted C6-C40 aryl groups and substituted or unsubstituted C3-C40 heteroaryl groups, respectively.

[0065] In some embodiments, Ar1 and Ar2 are independently selected from substituted or unsubstituted C6-C30 aryl groups and substituted or unsubstituted C3-C30 heteroaryl groups, respectively.

[0066] In some embodiments, Ar3 to Ar5 each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C40 alkyl, substituted or unsubstituted C6-C40 aryl, substituted or unsubstituted C3-C40 heteroaryl, substituted or unsubstituted C3-C40 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted tri(C1-C20)alkylsilyl, substituted or unsubstituted di(C1-C20)alkyl(C6-C20)arylsilyl, substituted or unsubstituted (C1-C20)alkyldi(C6-C20)arylsilyl, substituted or unsubstituted tri(C6-C20)arylsilyl, -N-(R')(R”); or Ar3 to Ar5 each independently form a ring with a substituent on a carbon atom or heteroatom adjacent to the substituted position thereto.

[0067] In some embodiments, Ar3 to Ar5 each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C1-C15 alkoxy, substituted or unsubstituted tri(C1-C15)alkylsilyl, substituted or unsubstituted di(C1-C15)alkyl(C6-C15)arylsilyl, substituted or unsubstituted (C1-C15)alkyldi(C6-C15)arylsilyl, substituted or unsubstituted tri(C6-C15)arylsilyl, -N-(R')(R”); or Ar3 to Ar5 each independently form a ring with a substituent on a carbon atom or heteroatom adjacent to the substituted position thereto.

[0068] In some embodiments, R' and R” each independently represent a substituted or unsubstituted C1-C20 alkyl, a substituted or unsubstituted C2-C20 alkenyl, a substituted or unsubstituted C6-C20 aryl, or a substituted or unsubstituted C3-C20 heteroaryl.

[0069] In some implementations, p is an integer between 0 and 4.

[0070] In some embodiments, L, L1, L2, and L3 are independently selected from single bonds, substituted or unsubstituted C6-C40 aryl groups, or substituted or unsubstituted C3-C40 heteroaryl groups.

[0071] In some embodiments, L, L1, L2, and L3 are independently selected from single bonds, substituted or unsubstituted C6-C30 aryl groups, or substituted or unsubstituted C3-C30 heteroaryl groups.

[0072] In some embodiments, L, L1, L2, and L3 are independently selected from single bonds or one of the structures shown in equations (3-1) to (3-17):

[0073] In this context, "*" represents the bond connection sites of L, L1, L2, and L3.

[0074] In some embodiments, the substitution is at least one of deuterium, halogen, cyano, isocyano, phosphin, C1-C6 alkyl, C3-C12 cycloalkyl, C1-C6 alkyl-substituted amino, C6-C20 aryl, C1-C6 alkyl-substituted or unsubstituted heteroaryl, wherein the number of substitutions ranges from monosubstituted to the maximum number of substitutions.

[0075] In some embodiments, the ring A in formula (1) is selected from one of the structures shown in formulas (1-4) to (1-11):

[0076] Where * represents the site that fused with the 5-membered ring containing X in equation (1);

[0077] Where a is an integer from 0 to 10; if a ≥ 2 or a larger integer, then each R0 can be the same or different, and adjacent R0s can be connected to form a parallel ring.

[0078] In some embodiments, the ring A in formula (1) is selected from one of the structures shown in formulas (1-12) to (1-19):

[0079] Where * represents the site that fused with the 5-membered ring containing X in equation (1);

[0080] Where a is an integer from 0 to 6; if a is an integer from 2 to 6, then each R0 can be the same or different, and adjacent R0s can be connected to form a parallel ring.

[0081] In some embodiments, ring B of formula (1) or ring C of formula (3) is independently selected from one of the structures shown in formulas (1-20) to (1-26):

[0082] Wherein, * represents the confluence site with the ring C containing the X quinary ring in formula (1) or the Y quinary ring in formula (3);

[0083] R2 is selected from hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted C1-C40 alkyl, substituted or unsubstituted C1-C40 heteroalkyl, substituted or unsubstituted C2-C40 alkenyl, substituted or unsubstituted C2-C40 alkynyl, substituted or unsubstituted C3-C40 cycloalkyl, substituted or unsubstituted C3-C40 heterocycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, substituted... Or at least one of the following: unsubstituted C1-C40 alkoxy, substituted or unsubstituted C6-C60 aryloxy, substituted or unsubstituted C3-C40 alkylsilyl, substituted or unsubstituted C6-C60 arylsilyl, substituted or unsubstituted C1-C40 alkylboron, substituted or unsubstituted C6-C60 arylboron, substituted or unsubstituted C6-C60 arylphosphine, or substituted or unsubstituted C6-C60 arylamine;

[0084] The substitution described in R2 is substituted by at least one of deuterium, halogen, cyano, isocyano, phosphin, C1-C6 alkyl, C3-C16 cycloalkyl, C1-C6 alkyl-substituted amino, C6-C30 aryl substituted or unsubstituted C1-C6 alkyl, or C3-C30 heteroaryl substituted or unsubstituted C1-C6 alkyl, wherein the number of substitutions is from monosubstituted to the maximum number of substitutions;

[0085] Where q is an integer from 0 to 10; if q is an integer from 2 to 10, then each R2 can be the same or different, and adjacent R2s can be connected to form a parallel ring.

[0086] In some embodiments, L, L1, L2, and L3 are each independently selected from arylene groups that are single bonds or substituted or unsubstituted C6-C30 heteroarylene groups.

[0087] In some implementations, X is CR b R c 、O or S.

[0088] In some implementations, the R b R c Each is independently selected from C1-C10 alkyl, C1-C10 heteroalkyl, C3-C10 cycloalkyl, C3-C10 heterocycloalkyl, C6-C10 aryl, C5-C10 heteroaryl, or R b and R c They connect to form fluorene groups.

[0089] In some implementations, X1-X 12 It contains at least one N.

[0090] In some implementations, at least two of Z1, Z2, and Z3 are N.

[0091] In some implementations, X is CR b R c 、O or S.

[0092] In some embodiments, X in the first host compound formula (1) is selected from O, and Z1, Z2 and Z3 in the second host compound formula (2) are all N.

[0093] In some embodiments, the structure of formula (3) in formula (2) of the second host compound is selected from one of the structures shown in formulas (2-1) to (2-13):

[0094] Where R1, R2, R e R f R g p and q are the same as above. In equation (2-12), R is connected to N. e .

[0095] In some embodiments, Ar1 to Ar5 are each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthraquinyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiopheneyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted 9,9-spirodifluorenyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted pyrene, substituted or unsubstituted... The group consisting of at least one of the following: substituted or unsubstituted carbazolyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted fluoranyl, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted benzotriazolyl, substituted or unsubstituted benzophenanthryl, substituted or unsubstituted naphthoxazolyl, substituted or unsubstituted benzocycloalkyl, substituted or unsubstituted phenanthoxazolyl, oxaspironyl, and substituted or unsubstituted benzocarbazolyl.

[0096] In some embodiments, the substitution is made by at least one of deuterium, halogen, cyano, isocyano, phosphin, 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 monosubstituted to the maximum number of substitutions.

[0097] In some embodiments, the substitution is made by at least one of deuterium, halogen, cyano, isocyano, phosphin, C1-C6 alkyl, C3-C10 cycloalkyl, C1-C6 alkyl-substituted amino, C6-C12 aryl, or C3-C12 heteroaryl, wherein the number of substitutions ranges from monosubstituted to the maximum number of substitutions.

[0098] In some embodiments, the aryl group is selected from phenyl, naphthyl, anthraceneyl, phenanthrene, tetraphenyl, pyrene, dinaphthyl-2, and phenyl-2-(2-) ... Acenamethanil, benzo[c]pyrene, benzo[g]phenanthryl, benzo[g]triyl, fluorenyl, spirodifluorenyl, benzo[f]fluorenyl, dibenzo[f]fluorenyl, biphenyl, triphenyl, tetraphenyl or fluoranyl.

[0099] In some embodiments, the heteroaryl group is selected from pyrrolithyl, pyrrolopyrrolithyl, furanopyrrolithyl, thienopyrrolithyl, pyridyl, pyrazolyl, pyrimidinyl, pyrazinyl, triazinyl, pyridazinyl, phenazinyl, phenothiazinyl, phenoxazinyl, indolyl, isoindolyl, imidazolyl, benzimidazolyl, triazolyl, tetrazolyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, furanofuranyl, azadibenzofuranyl, thienopyranyl, diazadibenzofuranyl, benzo[B]naphtho[1, [2-D] Furanyl, Quinolinyl, Isoquinolinyl, Quinoxolinyl, Quinazolinyl, Quinazolinoneyl, Carbazoyl, Azacarbazoyl, Diazacarbazoyl, Phenyridinyl, Prisidinyl, Acridineyl, Dihydroacridinyl, Phenyrrolinyl, Oxazolinyl, Oxazolyl, Oxadiazolyl, Benzoisoxazolyl, Thiazolyl, Benzothiazoyl, Benzoisothiazoyl, Pyrroloimidazoyl, Furazanyl, Thienyl, Benzothiaphenyl, Dibenzothiaphenyl, Azadibenzothiaphenyl, Diazadibenzothiaphenyl, Thienophenyl or o-diazanaphthyl.

[0100] In some embodiments, the compound represented by formula (1) is selected from one of the following structural formulas, or is one of the following structural formulas in which hydrogen is partially or completely substituted by deuterium or fluorine:

[0101] In some embodiments, the compound represented by formula (2) is selected from one of the following structural formulas, or is one of the following structural formulas in which hydrogen is partially or completely substituted by deuterium or fluorine:

[0102] In some embodiments, the host material composition comprises a first host compound and a second host compound, wherein the weight ratio of the first host compound to the second host compound may be from 1:99 to 99:1, preferably from 10:90 to 90:10, more preferably from 20:80 to 80:20, 30:70 to 70:30 or 40:60 to 60:40, and even more preferably from 50:50.

[0103] In some embodiments, the host material composition further comprises at least one third host compound, which is represented by formula (1) or formula (2), but is different from the first host compound or the second host compound.

[0104] In some embodiments, the first host compound is represented by formula (1), and the second and third host compounds are both represented by formula (2). The second host compound is selected from one of the structures shown in B1-B265, and the third host compound is selected from one of the structures shown in C1-C10.

[0105] In some embodiments, the host material composition comprises a first host compound, a second host compound, and a third host compound, wherein the third host compound differs from the first and second host compounds. The weight percentage of the first host compound in the host material composition is 5 wt% to 90 wt%, preferably selected from 10 wt% to 90 wt%, 10 wt% to 80 wt%, 20 wt% to 80 wt%, 15 wt% to 70 wt%, 30 wt% to 70 wt%, 20 wt% to 60 wt%, or 30 wt% to 60 wt%; the weight percentage of the second host compound is approximately 5 wt% to 90 wt%, preferably selected from 10 wt% to 90 wt%, 10 wt% to 80 wt%, etc. The first main compound may comprise 10wt% to 40wt%, 15wt% to 70wt%, 30wt% to 70wt%, 20wt% to 60wt%, or 30wt% to 60wt% by weight; the third main compound may comprise about 5wt% to 90wt%, preferably selected from 10wt% to 90wt%, 10wt% to 80wt%, 10wt% to 40wt%, 15wt% to 70wt%, 30wt% to 70wt%, 20wt% to 60wt%, or 30wt% to 60wt%. For example, the main material composition may comprise a first main compound at a weight ratio of 5wt% to 70wt%, a second main compound at a weight ratio of 5wt% to 70wt%, and a third main compound at a weight ratio of 10wt% to 90wt%. The main material composition may also comprise a first main compound at a weight ratio of 20wt% to 80wt%, a second main compound at a weight ratio of 10wt% to 40wt%, and a third main compound at a weight ratio of 10wt% to 40wt%.

[0106] A second aspect of this application provides an organic electroluminescent device.

[0107] Specifically, an organic electroluminescent device includes the aforementioned host materials.

[0108] In some embodiments, an organic electroluminescent device includes: an anode, a cathode, and at least one light-emitting layer between the anode and the cathode, wherein the light-emitting layer comprises the aforementioned combination of multiple host materials.

[0109] In some embodiments, the light-emitting layer is a red light-emitting layer, comprising a red light-emitting material and a combination of the aforementioned multiple host materials.

[0110] In some embodiments of this application, the various host material compositions described herein serve as the host material for the red luminescent layer.

[0111] A third aspect of this application provides the application of the above-mentioned compounds in the semiconductor field.

[0112] Specifically, the application of the above-mentioned multiple host material compositions in the fabrication of semiconductor devices.

[0113] In some embodiments, the semiconductor device includes an optoelectronic device.

[0114] definition

[0115] Unless otherwise stated, the scientific and technical terms used herein have the meanings commonly understood by those skilled in the art. However, for a better understanding of this invention, definitions of some terms are provided below. When the definitions of terms provided in this invention differ from the meanings commonly understood by those skilled in the art, the definitions and interpretations provided in this invention shall prevail.

[0116] The term "alkyl" refers to a straight-chain or branched saturated hydrocarbon group. Specifically, the number of carbon atoms can be 1 to 60, 1 to 40, 1 to 30, 1 to 20, 1 to 12, 1 to 6, or 1 to 3. Non-limiting examples of alkyl groups include methyl, ethyl, propyl, butyl, heptyl, decyl, etc. Each group includes various isomers; for example, butyl includes isomers such as n-butyl, isobutyl, sec-butyl, tert-butyl, etc.

[0117] The term "heteroalkyl" refers to an alkyl group in which at least one carbon atom is replaced by a non-carbon atom or a group containing a non-carbon atom. The non-carbon atom can be selected from at least one of O, S, N, P, B, Si, Ge, or Se, but does not include cases where the carbon atom in the alkyl group attached to the main structure is replaced by a non-carbon atom (e.g., alkoxy, alkylsilyl, alkylboryl). Non-limiting examples of heteroalkyl groups include mercaptomethylalkyl, methoxymethylalkyl, ethoxymethylalkyl, tert-butoxymethylalkyl, and N,N-dimethylmethylalkyl.

[0118] The term "alkoxy" refers to a group having an -O-alkyl group, i.e., an alkyl group as defined above connected to a given group or given structural formula via an oxygen atom. Non-limiting examples of alkoxy groups include methoxy, ethoxy, and tert-butoxy.

[0119] The term "alkenyl" refers to a hydrocarbon group containing at least one double bond. The number of carbon atoms in an alkenyl group can be 2 to 40, 2 to 30, 2 to 20, 2 to 12, 2 to 10, or 2 to 6. Non-limiting examples of alkenyl groups include: vinyl, propenyl, allyl, isopropenyl, 1-butadienyl, 2-butadienyl, 1-hextrienyl, 2-hextrienyl, and 3-hextrienyl.

[0120] The term "alkynyl" refers to a hydrocarbon group containing at least one triple bond. The number of carbon atoms in an alkenyl group can be 2 to 40, 2 to 30, 2 to 20, 2 to 12, 2 to 10, 2 to 6, or 2 to 4. Non-limiting examples of alkynyl groups include ethynyl and propynyl.

[0121] The term "cycloalkyl" refers to a non-aromatic carbonyl ring consisting of at least two carbon atoms, which may include monocyclic, polycyclic, and spiroalkyl groups. The number of carbon atoms in the alkenyl group may be 3 to 60, 3 to 40, 3 to 30, 3 to 20, 3 to 12, 3 to 10, or 3 to 6. Non-limiting examples of cycloalkyl groups include: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, bicyclo[3.1.1]heptyl, spiro[4.5]decyl, spiro[5.5]undecyl, adamantyl, and norbornel.

[0122] The term "heterocyclic alkyl" refers to a cycloalkyl group in which at least one carbon atom is replaced by a non-carbon atom, which may be selected from at least one of O, S, N, P, B, Si, Ge, or Se. The number of carbon atoms in a heterocyclic alkyl group may be 3 to 60, 3 to 40, 3 to 30, 3 to 20, 3 to 12, 3 to 10, or 3 to 6. Non-limiting examples of heterocyclic alkyl groups include epoxide butyl, epoxide pentyl, and epoxide hexyl.

[0123] The term "aryl" refers to an aromatic hydrocarbon group derived from an aromatic ring compound by removing one hydrogen atom, and can be monocyclic or polycyclic. At least one ring in a polycyclic aryl compound is an aromatic ring system. Multiple rings in a polycyclic aryl compound can be linked together by single bonds or can be fused together. The number of carbon atoms in the aryl group can be 6 to 60, 6 to 40, 6 to 30, 6 to 20, 6 to 12, or 6 to 10. For example, when a polycyclic aryl compound contains a fused ring structure, it can be formed by the fusion of a C3-C30 aliphatic ring (a saturated or unsaturated aliphatic ring containing 3 to 30 carbon atoms in the ring skeleton) and a C3-C30 aromatic ring (an aromatic ring containing 3 to 30 carbon atoms in the ring skeleton), more specifically, by the fusion of a C3-C20 aliphatic ring and a C6-C30 aromatic ring. Understandably, the term "arylene" refers to an aromatic hydrocarbon group derived from an aromatic ring compound by removing two hydrogen atoms.

[0124] The term "heteroaryl" refers to an aryl group in which at least one carbon atom is replaced by a non-carbon atom, wherein the non-carbon atom can be a monovalent group selected from heterocyclic aromatic systems of O, S, N, P, B, Se, Si, or Ge, but does not include cases where the aryl group is attached to the host structure via a non-carbon atom group (e.g., aryloxy, arylsilyl, arylboryl, arylphosphinyl, arylamine). Understandably, the term "hybrid aryl" refers to a divalent group having the same structure as a heteroaryl group.

[0125] "Ar3 to Ar5 are each independently linked to substituents on the carbon atoms adjacent to their substitution sites to form a ring" means that the substituents on the substitution sites of Ar3 to Ar5 can link to the substituents on the carbon atoms of L1 to L3 to form a ring, or when L1 to L3 are single bonds, the substituents on the substitution sites of Ar3 to Ar5 can link to Z1 to Z3 to form a ring. For example, L1 and Ar3, L2 and Ar4, and L3 and Ar5 can optionally link to each other to form substituted or unsubstituted rings of the following: naphthalene, fluorenyl, quinoline, dibenzothiophene, dibenzofuran, carbazole, benzofuran-pyridine, benzothiophene-pyridine, indoxpyridine, benzofuran-quinoline, benzothiophene-quinoline, or indoxquinoline ring.

[0126] The term "adjacent" refers to a direct bond between two groups or atoms, or two groups or atoms that are directly adjacent substituents (i.e., the two substituent sites are directly connected, rather than indirectly connected through other atoms or groups).

[0127] The "carbon number ab" in the statement "X group with substituted or unsubstituted carbon number ab" refers to the carbon number of the X group when it is unsubstituted, excluding the carbon number of the substituent when the X group is substituted.

[0128] "Substituted" in "substituted or unsubstituted" means that one or more hydrogen atoms are replaced by other atoms or functional groups (i.e., substituents), and unless otherwise defined, also includes one or more hydrogen atoms being replaced by groups formed by the linkage of two or more of the substituents described above.

[0129] The following embodiments are merely for the purpose of understanding the technical application and should not be regarded as specific limitations of this application.

[0130] The raw materials and solvents used in the synthesis of the compounds in this application were all purchased from suppliers well-known to those skilled in the art, such as Alfa and Acros.

[0131] Synthesis of compound A1:

[0132] Synthesis of compound A1-3:

[0133] Add A1-1 (30.00 g, 106.56 mmol), A1-2 (32.47 g, 127.87 mmol), 1,1-bis(diphenylphosphine)dipyridylferric palladium dichloride (1.56 g, 2.13 mmol), potassium acetate (15.69 g, 159.84 mmol), and 1,4-dioxane (450 mL) to a 1000 mL three-necked round-bottom flask. Purge the flask three times with nitrogen. Then heat the system to 100 °C and react for 2 hours. Monitor the reaction by TLC (ethyl acetate:n-hexane volume ratio = 1:10 as the developing solvent). Once A1-1 is completely consumed.

[0134] The sample was cooled to 60℃, concentrated under reduced pressure to remove the solvent, and ethyl acetate (700 mL) was added. The sample was washed three times with deionized water (300 mL * 3), separated, and loaded onto a silica gel column using a dry method. The sample was purified by silica gel column chromatography (200-300 mesh silica gel, ethyl acetate:n-hexane volume ratio = 1:15 as eluent). After elution, the sample was concentrated under reduced pressure at 70℃ for 1 hour to obtain a white solid, A1-3 (27.62 g, purity: 98.01%, yield: 78.88%). The mass spectrometry result was 329.12 (M+H).

[0135] Synthesis of compound A1-5:

[0136] Add A1-3 (25.00 g, 76.08 mmol), A1-4 (17.89 g, 76.08 mmol), tetra(triphenylphosphine)palladium (1.75 g, 1.52 mmol), potassium carbonate (15.77 g, 114.12 mmol), tetrahydrofuran (THF, 375 mL), and deionized water (125 mL) to a 1000 mL three-necked round-bottom flask. Purge the flask three times with nitrogen. Then heat the system to 75 °C and react for 3 hours. Monitor the reaction by TLC (ethyl acetate:n-hexane volume ratio = 1:10 as the developing solvent). Once A1-3 is completely consumed.

[0137] The solution was cooled to 60℃, concentrated under reduced pressure to remove the solvent, and ethyl acetate (700 mL) was added. The solution was washed three times with deionized water (300 mL * 3), separated, and loaded onto a silica gel column using a dry method. The solution was purified by silica gel column chromatography (200-300 mesh silica gel, ethyl acetate:n-hexane volume ratio = 1:20 as eluent). After elution, the solution was concentrated under reduced pressure at 70℃ for 2 hours to obtain a white solid, A1-5 (20.45 g, purity: 99.21%, yield: 75.32%). The mass spectrometry result was 357.22 (M+H).

[0138] Synthesis of compound A1-7

[0139] Add A1-5 (18.00 g, 50.45 mmol), A1-6 (25.94 g, 75.67 mmol), and tetrahydrofuran (270 mL) to a 1000 mL three-necked round-bottom flask, purge with nitrogen three times, then cool the system to 5 °C, add sodium methoxide (5.45 g, 100.90 mmol) all at once, maintain the reaction at 5 °C for 1 hour, monitor the reaction by TLC (ethyl acetate: n-hexane volume ratio = 1:10 as the developing solvent), and the starting material A1-5 is completely consumed;

[0140] Deionized water (500 mL) was added, and the solvent was removed by concentration under reduced pressure. Ethyl acetate (700 mL) was added for extraction, and the mixture was separated and concentrated under reduced pressure at 70 °C for 1 hour to obtain a white solid, A1-7 (18.44 g, yield: 95.00%), with a mass spectrometry result of 385.04 (M+H). The obtained compound was used directly in the next step without purification.

[0141] Synthesis of compound A1-8:

[0142] Add A1-7 (17.00 g, 44.17 mmol) and toluene (170 mL) to a 500 mL three-necked round-bottom flask, purge with nitrogen three times, then cool the system to 5 °C, and slowly add methanesulfonic acid (MsOH, 8.49 g, 88.34 mmol) dropwise over 3 minutes. Maintain the reaction at 5 °C for 1 hour, and monitor the reaction by TLC (using ethyl acetate:n-hexane volume ratio = 1:15 as the developing solvent). Once the starting material A1-7 is completely consumed,

[0143] Methanol (200 mL) was added to the mixture, and a large amount of white solid precipitated. After filtration, 17 g of solid was obtained. The solid was crystallized once with toluene (204 mL) and methanol (170 mL), filtered, and the filter cake was dried under vacuum at 80 °C for 1 hour to obtain a white solid, A1-8 (11.63 g, purity: 99.83%, yield: 74.62%). The mass spectrometry result was 353.06 (M+H).

[0144] Synthesis of compound A1

[0145] Add A1-8 (10.00 g, 28.34 mmol), A1-9 (7.30 g, 29.76 mmol), tris(dibenzylacetone)palladium (Pd2(dba)3, 0.52 g, 0.57 mmol), 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl (X-Phos, 0.54 g, 1.14 mmol), sodium tert-butoxide (NaOtBu, 4.09 g, 42.51 mmol), and toluene (150 mL) to a 500 mL three-necked round-bottom flask, purge with nitrogen three times, and then heat the system to 105 °C and react for 2 hours. Monitor the reaction by TLC (ethyl acetate:n-hexane volume ratio = 1:15 as the developing solvent). The starting material A1-8 was completely consumed.

[0146] The solution was cooled to 60°C, and methanol (150 mL) was added. The mixture was allowed to cool naturally to room temperature and stirred for 30 minutes to precipitate a large amount of solid. This solid was filtered to obtain 20 g of solid. Toluene (300 mL) was added, and the system was then heated to 100°C to dissolve and clarify. The solid was then filtered through a 30 g (300-400 mesh) silica gel filter. The silica gel surface was rinsed with toluene (50 mL), and the filtrates were combined and concentrated to obtain 18 g of solid. The solid was crystallized twice with toluene (180 mL) and methanol (90 mL), filtered, and the filter cake was dried under vacuum at 90°C for 3 hours to obtain a light yellow solid, compound A1 (14.07 g, purity: 99.94%, yield: 88.41%). The crude compound A1 was purified by sublimation to obtain sublimed pure compound A1 (11.26 g, purity: 99.95%, yield: 80.02%), with a mass spectrometry result of 562.22 (M+H).

[0147] The NMR characterization results of compound A1 are as follows: 1 ¹H NMR (400MHz, CDCl₃) δ 8.17 (d, J = 9.1Hz, 1H), 8.07–8.00 (m, 1H), 7.97–7.87 (m, 4H), 7.85 (dd, J = 7.5, 3.0Hz, 2H), 7.60–7.55 (m, 2H), 7.55–7.48 (m, 4H), 7.42–7.39 (m, 3H), 7.32 (d, J = 7.3Hz, 1H), 7.31–7.24 (m, 2H), 7.16–7.07 (m, 5H), 7.02–6.97 (m, 2H). Synthesis of compound A54:

[0148] Synthesis of compound A54-2:

[0149] Following the synthesis and purification method of compound A1-3, only the corresponding raw materials need to be changed to obtain the white solid as the target compound A54-2 (28.02 g, purity: 98.52%, yield: 77.65%), with a mass spectrometry result of 329.12 (M+H).

[0150] Synthesis of compound A54-3:

[0151] Following the synthesis and purification method of compound A1-5, only the corresponding raw materials need to be changed to obtain the white solid as the target compound A54-3 (26.33 g, purity: 99.45%, yield: 75.09%), with a mass spectrometry result of 357.22 (M+H).

[0152] Synthesis of compound A54-4:

[0153] Following the synthesis and purification method of compound A1-7, only the corresponding raw materials need to be changed to obtain the white solid as the target compound A54-4 (24.44 g, yield: 97.89%), with a mass spectrometry result of 385.04 (M+H).

[0154] Synthesis of compound A54-5:

[0155] Following the synthesis and purification method of compound A1-8, only the corresponding raw materials need to be changed to obtain the white solid as the target compound A54-5 (16.85g, purity: 99.79%, yield: 76.85%), with a mass spectrometry result of 353.06 (M+H).

[0156] Synthesis of compound A54:

[0157] Following the synthesis and purification method of compound A1, only the corresponding raw materials needed to be changed to obtain the target compound A54 (16.74 g, purity: 99.95%, yield: 78.65%), a light yellow solid. After sublimation purification of 16.74 g of crude A54, sublimed pure compound A54 (13.10 g, purity: 99.95%, yield: 78.26%) was obtained, with a mass spectrometry result of 612.22 (M+H).

[0158] The NMR characterization results of compound A54 are as follows: 1H NMR(400MHz, CDCl3)δ8.64(s,1H),8.33–8.26(m,1H),8.01(d,J=8.9Hz,1H),7.96(d,J=8.0Hz,1H),7.93–7.75(m,8H),7.61–7.53(m, 3H),7.53–7.47(m,5H),7.44–7.37(m,3H),7.22(t,J=2.2Hz,1H),7.09–7.01(m,2H),7.01–6.97(m,2H),6.86(dd,J=7.6,2.2Hz,1H).

[0159] Synthesis of compound A73:

[0160] Synthesis of compound A73-2:

[0161] Following the synthesis and purification method of compound A1-3, only the corresponding raw materials need to be changed to obtain the white solid as the target compound A73-2 (30.54 g, purity: 98.44%, yield: 77.12%), with a mass spectrometry result of 329.12 (M+H).

[0162] Synthesis of compound A73-3:

[0163] Following the synthesis and purification method of compound A1-5, only the corresponding raw materials need to be changed to obtain the white solid as the target compound A73-3 (27.09 g, purity: 99.66%, yield: 76.36%), with a mass spectrometry result of 357.22 (M+H).

[0164] Synthesis of compound A73-4:

[0165] Following the synthesis and purification method of compound A1-7, only the corresponding raw materials needed to be changed to obtain the target compound A73-4 (23.12 g, yield: 93.93%) as a white solid, with a mass spectrometry result of 385.04 (M+H). The obtained compound was used directly in the next step without purification.

[0166] Synthesis of compound A73-5:

[0167] Following the synthesis and purification method of compound A1-8, only the corresponding raw materials need to be changed to obtain the white solid as the target compound A73-5 (18.08 g, purity: 99.65%, yield: 40.20%), with a mass spectrometry result of 353.06 (M+H).

[0168] Synthesis of compound A73-8:

[0169] Following the synthesis and purification method of compound A1, only the corresponding raw materials need to be changed to obtain the white solid as the target compound A73-8 (23.11 g, purity: 99.60%, yield: 76.44%), with a mass spectrometry result of 337.13 (M+H).

[0170] Synthesis of compound A73

[0171] Following the synthesis and purification method of compound A1, only the corresponding raw materials needed to be changed to obtain the target compound A73 (16.76 g, purity: 99.92%, yield: 76.22%), which was a light yellow solid. After sublimation purification of 16.76 g of crude A73, sublimed pure A73 (14.21 g, purity: 99.92%, yield: 84.78%) was obtained, with a mass spectrometry result of 653.21 (M+H).

[0172] The NMR characterization results of compound A73 are as follows: 1 H NMR(400MHz, CDCl3)δ8.33-8.26(m,1H),8.21(dd,J=17.5,8.8Hz,2H),8.13-8.03(m,2H),8.02-7.79(m ,10H),7.55-7.46(m,3H),7.46-7.39(m,3H),7.34-7.24(m,3H),7.15-7.06(m,3H),6.98-6.96(m,1H).

[0173] Synthesis of compound A89:

[0174] Synthesis of compound A89-3:

[0175] Following the synthesis and purification method of compound A1-5, only the corresponding raw materials need to be changed to obtain the white solid as the target compound A89-3 (19.88 g, purity: 99.57%, yield: 78.08%), with a mass spectrometry result of 357.04 (M+H).

[0176] Synthesis of compound A89-4:

[0177] Following the synthesis and purification method of compound A1-7, only the corresponding raw materials needed to be changed to obtain the target compound A89-4 (25.58 g, yield: 94.35%) as a white solid, with a mass spectrometry result of 385.04 (M+H). The obtained compound was used directly in the next step without purification.

[0178] Synthesis of compound A89-5:

[0179] Following the synthesis and purification method of compound A1-8, only the corresponding raw materials need to be changed to obtain the white solid as the target compound A89-5 (20.01 g, purity: 99.74%, yield: 78.63%), with a mass spectrometry result of 353.06 (M+H).

[0180] Synthesis of compound A89:

[0181] Following the synthesis and purification method of compound A1, only the corresponding raw materials needed to be changed to obtain the target compound A89 (17.77 g, purity: 99.94%, yield: 71.06%) as a yellow solid. After sublimation purification of 17.77 g of crude A89, sublimed pure A89 (15.02 g, purity: 99.94%, yield: 84.52%) was obtained, with a mass spectrometry result of 678.22 (M+H).

[0182] The NMR characterization results of compound A89 are as follows: 1 H NMR(400MHz, CDCl3)δ8.47(dd,J=7.6,1.4Hz,1H),8.16-8.10(m,1H),8.10-8.02(m,4H),7.93-7.86(m,3H),7.82(d ,J=7.1Hz,1H),7.61-7.34(m,15H),7.32-7.30(m,1H),7.17(dd,J=7.2,2.1Hz,1H),7.03-6.97(m,2H),1.74(s,6H).

[0183] Synthesis of compound A97:

[0184] Synthesis of compound A97-2:

[0185] Following the synthesis and purification method of compound A1-3, only the corresponding raw materials need to be changed to obtain the white solid as the target compound A97-2 (32.65g, purity: 98.78%, yield: 79.05%), with a mass spectrometry result of 345.02 (M+H).

[0186] Synthesis of compound A97-3:

[0187] Following the synthesis and purification method of compound A1-5, only the corresponding raw materials need to be changed to obtain the white solid as the target compound A97-3 (29.63 g, purity: 99.75%, yield: 76.03%), with a mass spectrometry result of 373.04 (M+H).

[0188] Synthesis of compound A97-4:

[0189] Following the synthesis and purification method of compound A1-7, only the corresponding raw materials needed to be changed to obtain the target compound A97-4 (25.63 g, yield: 95.39%) as a white solid, with a mass spectrometry result of 401.14 (M+H). The obtained compound was used directly in the next step without purification.

[0190] Synthesis of compound A97-5:

[0191] Following the synthesis and purification method of compound A1-8, only the corresponding raw materials need to be changed to obtain the white solid as the target compound A97-5 (20.00 g, purity: 99.76%, yield: 78.80%), with a mass spectrometry result of 369.02 (M+H).

[0192] Synthesis of compound A97:

[0193] Following the synthesis and purification method of compound A1, only the corresponding raw materials needed to be changed to obtain the light yellow solid, which was the target compound A97 (14.33 g, purity: 99.95%, yield: 74.63%). After sublimation purification of 14.33 g of crude A97, sublimed pure A97 (12.01 g, purity: 99.95%, yield: 83.81%) was obtained, with a mass spectrometry result of 731.93 (M+H).

[0194] The NMR characterization results of compound A97 are as follows: 1 H NMR (400MHz, CDCl3) δ8.21(d,J=7.1Hz,1H),8.11–8.02(m,2H),8.02–7.97(m,1H),7.96–7.87(m,4H),7.85(d,J=8.1Hz,1H),7.75–7.6 8(m,2H),7.61–7.54(m,4H),7.54–7.47(m,8H),7.42–7.39(m,6H),7.16(dd,J=7.0,2.2Hz,1H),7.04–6.97(m,2H),6.97–6.87(m,2H).

[0195] Synthesis of compound A118:

[0196] Synthesis of compound A118-1:

[0197] Following the synthesis and purification method of compound A1, only the corresponding raw materials need to be changed to obtain the light yellow solid as the target compound A118-1 (12.11 g, purity: 99.95%, yield: 76.87%), with a mass spectrometry result of 562.32 (M+H).

[0198] The NMR characterization results of compound A118-1 are as follows: 1 H NMR(400MHz, CDCl3)δ8.33–8.26(m,1H),8.21(dd,J=17.5,8.8Hz,2H),8.13–8.08(m,1H),8.06(d,J=9.5Hz,1H),8.00–7.94 (m,2H),7.93–7.82(m,2H),7.61–7.47(m,6H),7.46–7.37(m,4H),7.34–7.25(m,3H),7.17–7.06(m,3H),7.03–6.97(m,2H).

[0199] Synthesis of compound A118:

[0200] Add A118-1 (30.00 g, 54.31 mmol), deuterated benzene-D6 (114.44 g, 1.36 mol), and trifluoroacetic acid (6.19 g, 54.31 mmol) to a 500 mL single-necked round-bottom flask, purge with nitrogen three times, and then heat the system to 50 °C and stir for 24 hours.

[0201] The system was cooled to room temperature, and the reaction was quenched dropwise with heavy water (40 mL). The mixture was stirred at room temperature for 0.5 hours, followed by washing three times with ethyl acetate (300 mL) and deionized water (200 mL). The mixture was then stirred at room temperature for 30 minutes, filtered to obtain 35 g of solid, and dried under vacuum at 90 °C for 1 hour to obtain 29 g of light yellow solid. This solid was crystallized twice with toluene (290 mL) and methanol (120 mL), filtered, and the filter cake was dried under vacuum at 90 °C for 3 hours to obtain a light yellow solid, A118 (25.20 g, purity: 99.94%, yield: 80.12%). The 25.20 g crude A118 was purified by sublimation to obtain sublimed pure A118 (21.53 g, purity: 99.95%, deuteration rate of 27 D atoms: 95.33%, yield: 85.46%), mass spectrometry result: 589.22 (M+H).

[0202] Synthesis of compound A136:

[0203] Synthesis of compound A136-2:

[0204] Following the synthesis and purification method of compound A1-5, only the corresponding raw materials need to be changed to obtain the white solid as the target compound A136-2 (22.65 g, purity: 99.52%, yield: 75.98%), with a mass spectrometry result of 382.12 (M+H).

[0205] Synthesis of compound A136-3:

[0206] Following the synthesis and purification method of compound A1-7, only the corresponding raw materials need to be changed to obtain the target compound A136-3 (20.00 g, yield: 96.08%) as a white solid, with a mass spectrometry result of 410.10 (M+H). The obtained compound was used directly in the next step without purification.

[0207] Synthesis of compound A136-4:

[0208] Following the synthesis and purification method of compound A1-8, only the corresponding raw materials need to be changed to obtain the white solid as the target compound A136-4 (16.78 g, purity: 99.78%, yield: 42.56%), with a mass spectrometry result of 378.26 (M+H).

[0209] Synthesis of compound A136:

[0210] Following the synthesis and purification method of compound A1, only the corresponding raw materials needed to be changed to obtain the light yellow solid, which was the target compound A136 (15.33 g, purity: 99.92%, yield: 77.52%). After sublimation purification of 15.33 g of crude A136, sublimed pure A136 (12.01 g, purity: 99.93%, yield: 78.35%) was obtained, with a mass spectrometry result of 601.18 (M+H).

[0211] The NMR characterization results of compound A136 are as follows: 1 H NMR(400MHz, CDCl3)δ8.44(d,J=2.0Hz,1H),8.37(d,J=8.1Hz,1H),8.28–8.22(m,1H) ,8.13(d,J=7.5Hz,1H),8.10–8.05(m,1H),8.04–7.92(m,3H),7.90(d,J=7.5Hz,1H), 7.82(d,J=7.2Hz,1H),7.70–7.59(m,2H),7.47–7.34(m,3H),7.32–7.24(m,2H),7.17 (dd,J=7.3,2.0Hz,1H),7.15–7.08(m,4H),7.07(d,J=2.1Hz,1H),7.04–7.02(m,1H).

[0212] Synthesis of compound A145:

[0213] Synthesis of compound A145-1:

[0214] Following the synthesis and purification method of compound A1-8, only the corresponding raw materials need to be changed to obtain the white solid as the target compound A145-1 (20.52 g, purity: 99.63%, yield: 75.82%), with a mass spectrometry result of 353.06 (M+H).

[0215] Synthesis of compound A145-3:

[0216] Following the synthesis and purification method of compound A1, only the corresponding raw materials need to be changed to obtain the white solid as the target compound A145-3 (25.63 g, purity: 99.87%, yield: 74.25%), with a mass spectrometry result of 320.12 (M+H).

[0217] Synthesis of compound A145:

[0218] Following the synthesis and purification method of compound A1, only the corresponding raw materials needed to be changed to obtain the target compound A145 (17.63 g, purity: 99.94%, yield: 77.06%) as a yellow solid. After sublimation purification of 17.63 g of crude A145, sublimed pure A145 (14.76 g, purity: 99.94%, yield: 83.72%) was obtained, with a mass spectrometry result of 636.22 (M+H).

[0219] The NMR characterization results of compound A145 are as follows: 1 H NMR(400MHz, CDCl3)δ8.62(d,J=9.2Hz,1H),8.57(d,J=9.3Hz,1H),8.50-8.43(m,1H) ,8.37(d,J=8.3Hz,1H),8.33-8.27(m,1H),8.25(d,J=8.1Hz,1H),8.01-7.95(m,3H),7 .92-7.87(m,5H),7.82(d,J=7.2Hz,1H),7.73(d,J=2.0Hz,1H),7.56-7.47(m,4H),7.3 7(d,J=7.1Hz,1H),7.32-7.24(m,2H),7.17-7.06(m,5H),6.89(dd,J=7.5,2.2Hz,1H).

[0220] Synthesis of compound A167:

[0221] Synthesis of compound A167-1:

[0222] Following the synthesis and purification method of compound A1-8, only the corresponding raw materials need to be changed to obtain the white solid as the target compound A167-1 (15.63 g, purity: 99.71%, yield: 42.52%), with a mass spectrometry result of 353.06 (M+H).

[0223] Synthesis of compound A167-4:

[0224] Following the synthesis and purification method of compound A1, only the corresponding raw materials need to be changed to obtain the white solid as the target compound A167 (20.62 g, purity: 99.75%, yield: 78.43%), with a mass spectrometry result of 410.20 (M+H).

[0225] Synthesis of compound A167:

[0226] Following the synthesis and purification method of compound A1, only the corresponding raw materials needed to be changed to obtain the light yellow solid, which was the target compound A167 (14.52 g, purity: 99.93%, yield: 74.62%). After sublimation purification of 14.52 g of crude A167, sublimed pure A167 (11.11 g, purity: 99.93%, yield: 76.52%) was obtained, with a mass spectrometry result of 726.28 (M+H).

[0227] The NMR characterization results of compound A167 are as follows: 1 H NMR (400MHz, CDCl3) δ8.33–8.27(m,1H),8.25–8.18(m,2H),8.15(dd,J=8.9,2.4Hz,1 H),8.02(s,1H),8.00(d,J=2.2Hz,1H),7.98–7.86(m,6H),7.85(d,J=2.0Hz,1H),7.5 5–7.48(m,5H),7.42(d,J=7.6Hz,1H),7.31(dd,J=7.5,2.2Hz,1H),7.07–7.01(m,2H) ,6.89–6.84(m,2H),2.16–2.09(m,3H),1.96(d,J=4.9Hz,6H),1.79(t,J=5.5Hz,6H).

[0228] Synthesis of compound A183:

[0229] Synthesis of compound A183-2:

[0230] Following the synthesis and purification method of compound A1-3, only the corresponding raw materials need to be changed to obtain the white solid as the target compound A183-2 (28.74 g, purity: 99.21%, yield: 74.56%), with a mass spectrometry result of 329.12 (M+H).

[0231] Synthesis of compound A183-3:

[0232] Following the synthesis and purification method of compound A1-5, only the corresponding raw materials need to be changed to obtain the white solid as the target compound A183-3 (26.32 g, purity: 99.66%, yield: 76.36%), with a mass spectrometry result of 357.22 (M+H).

[0233] Synthesis of compound A183-4:

[0234] Following the synthesis and purification method of compound A1-7, only the corresponding raw materials needed to be changed to obtain the target compound A183-4 (21.65 g, yield: 92.84%) as a white solid, with a mass spectrometry result of 385.04 (M+H). The obtained compound was used directly in the next step without purification.

[0235] Synthesis of compound A183-5:

[0236] Following the synthesis and purification method of compound A1-8, only the corresponding raw materials need to be changed to obtain the white solid as the target compound A183-5 (18.65 g, purity: 99.73%, yield: 76.85%), with a mass spectrometry result of 353.06 (M+H).

[0237] Synthesis of compound A183-7

[0238] Following the synthesis and purification method of compound A1, only the corresponding raw materials need to be changed to obtain the white solid as the target compound A183-7 (19.99g, purity: 99.87%, yield: 78.63%), with a mass spectrometry result of 310.22 (M+H).

[0239] Synthesis of compound A183:

[0240] Following the synthesis and purification method of compound A1, only the corresponding raw materials needed to be changed to obtain the target compound A183 (14.65 g, purity: 99.96%, yield: 77.14%), which was a light yellow solid. After sublimation purification of 14.65 g of crude A183, sublimed pure A183 (11.24 g, purity: 99.96%, yield: 76.73%) was obtained, with a mass spectrometry result of 626.24 (M+H).

[0241] The NMR characterization results of compound A183 are as follows: 1 H NMR (400MHz, CDCl3) δ8.36–8.28(m,2H),8.05–7.98(m,3H),7.97–7.87(m,5H),7.85(d,J=8.0Hz,1 H),7.74–7.68(m,1H),7.57–7.47(m,5H),7.42–7.41(m,1H),7.37–7.23(m,5H),7.20–7.06(m,4H).

[0242] Synthesis of compound A207:

[0243] Synthesis of compound A207-2:

[0244] Following the synthesis and purification method of compound A1-5, only the corresponding raw materials need to be changed to obtain the white solid as the target compound A207-2 (28.78 g, purity: 99.74%, yield: 76.11%), mass spectrometry: 357.24 (M+H).

[0245] Synthesis of compound A207-3:

[0246] Following the synthesis and purification method of compound A1-7, only the corresponding raw materials needed to be changed to obtain the target compound A207-3 (22.65 g, yield: 95.63%) as a white solid, with a mass spectrometry result of 385.04 (M+H). The obtained compound was used directly in the next step without purification.

[0247] Synthesis of compound A207-4:

[0248] Following the synthesis and purification method of compound A1-8, only the corresponding raw materials need to be changed to obtain the white solid as the target compound A207-4 (18.08 g, purity: 99.65%, yield: 41.20%), with a mass spectrometry result of 353.06 (M+H).

[0249] Synthesis of compound A207-5:

[0250] Following the synthesis and purification method of compound A1-3, only the corresponding raw materials need to be changed to obtain the white solid as the target compound A207-5 (20.63 g, purity: 99.00%, yield: 75.41%), with a mass spectrometry result of 445.20 (M+H).

[0251] Synthesis of compound A207:

[0252] Following the synthesis and purification method of compound A1-5, only the corresponding raw materials need to be changed to obtain the light yellow solid, which is the target compound A207 (15.12 g, purity: 99.94%, yield: 75.85%). After sublimation purification of 15.12 g of crude A207, sublimed pure A207 (12.02 g, purity: 99.94%, yield: 79.50%) was obtained, with a mass spectrometry result of 638.24 (M+H).

[0253] The NMR characterization results of compound A207 are as follows: 1 H NMR (400MHz, CDCl3) δ8.64(d,J=9.3Hz,1H),8.46–8.40(m,1H),8.38(d,J=9.6Hz,1 H),8.21(d,J=1.1Hz,2H),8.04(d,J=9.5Hz,1H),8.01–7.93(m,2H),7.92–7.86(m,1 Synthesis of compound A219: 7.78 (dd, J = 7.1, 2.4 Hz, 1H), 7.63–7.55 (m, 2H), 7.55–7.47 (m, 5H), 7.44–7.38 (m, 4H), 7.36–7.31 (m, 2H), 7.31–7.22 (m, 2H), 7.17–7.07 (m, 4H), 7.03–6.96 (m, 2H).

[0254] Synthesis of compound A219-2:

[0255] Following the synthesis and purification method of compound A1-3, only the corresponding raw materials need to be changed to obtain the white solid as the target compound A219-2 (22.54 g, purity: 98.98%, yield: 78.15%), with a mass spectrometry result of 329.12 (M+H).

[0256] Synthesis of compound A219-3:

[0257] Following the synthesis and purification method of compound A1-5, only the corresponding raw materials need to be changed to obtain the white solid as the target compound A219-3 (22.62 g, purity: 99.81%, yield: 77.63%), with a mass spectrometry result of 357.22 (M+H).

[0258] Synthesis of compound A219-4:

[0259] Following the synthesis and purification method of compound A1-7, only the corresponding raw materials needed to be changed to obtain the target compound A219-4 (19.02 g, yield: 92.06%) as a white solid, with a mass spectrometry result of 385.04 (M+H). The obtained compound was used directly in the next step without purification.

[0260] Synthesis of compound A219-5:

[0261] Following the synthesis and purification method of compound A1-8, only the corresponding raw materials need to be changed to obtain the white solid as the target compound A219-5 (187.85g, purity: 99.23%, yield: 43.05%), with a mass spectrometry result of 353.06 (M+H).

[0262] Synthesis of compound A219-7:

[0263] Following the synthesis and purification method of compound A1, only the corresponding raw materials need to be changed to obtain the white solid as the target compound A219-7 (18.63g, purity: 99.55%, yield: 78.06%), with a mass spectrometry result of 520.20 (M+H).

[0264] Synthesis of compound A219:

[0265] Following the synthesis and purification method of compound A1, only the corresponding raw materials needed to be changed to obtain the light yellow solid, which was the target compound A219 (17.96 g, purity: 99.93%, yield: 77.61%). After sublimation purification of 17.96 g of crude A219, sublimed pure A219 (15.00 g, purity: 99.93%, yield: 83.51%) was obtained, with a mass spectrometry result of 836.28 (M+H).

[0266] The NMR characterization results of compound A219 are as follows: 1 H NMR (400MHz, CDCl3) δ8.65–8.58(m,3H),8.50–8.44(m,1H),8.33(d,J=2.2Hz,2H),8.26( d,J=7.8Hz,2H),8.10(d,J=2.1Hz,1H),8.07–8.02(m,1H),8.02–7.94(m,5H),7.94–7.87( m,2H),7.58–7.45(m,4H),7.42(d,J=7.6Hz,1H),7.34(dd,J=7.7,2.2Hz,2H),7.32–7.25 (m,3H),7.17(dd,J=7.2,2.1Hz,1H),7.16–7.12(m,2H),7.11–7.08(m,1H),1.33(s,18H).

[0267] Synthesis of compound A226:

[0268] Synthesis of compound A226-2:

[0269] Following the synthesis and purification method of compound A1-3, only the corresponding raw materials need to be changed to obtain the white solid as the target compound A226-2 (35.23 g, purity: 99.21%, yield: 79.08%), with a mass spectrometry result of 329.12 (M+H).

[0270] Synthesis of compound A226-3:

[0271] Following the synthesis and purification method of compound A1-5, only the corresponding raw materials need to be changed to obtain the white solid as the target compound A226-3 (30.68 g, purity: 99.78%, yield: 74.62%), with a mass spectrometry result of 357.24 (M+H).

[0272] Synthesis of compound A226-4:

[0273] Following the synthesis and purification method of compound A1-7, only the corresponding raw materials needed to be changed to obtain the target compound A226-4 (24.55 g, yield: 96.33%) as a white solid, with a mass spectrometry result of 385.04 (M+H). The obtained compound was used directly in the next step without purification.

[0274] Synthesis of compound A226-5:

[0275] Following the synthesis and purification method of compound A1-8, only the corresponding raw materials need to be changed to obtain the white solid as the target compound A226-5 (17.99 g, purity: 99.86%, yield: 78.63%), with a mass spectrometry result of 353.06 (M+H).

[0276] Synthesis of compound A226:

[0277] Following the synthesis and purification method of compound A1, only the corresponding raw materials needed to be changed to obtain the light yellow solid, which was the target compound A226 (17.11 g, purity: 99.95%, yield: 78.74%). After sublimation purification of 17.11 g of crude A226, sublimed pure A226 (13.75 g, purity: 99.95%, yield: 80.37%) was obtained, with a mass spectrometry result of 562.24 (M+H).

[0278] Figure 1 shows compound A226 of this application. 1 1H NMR spectrum, f1 (ppm) represents chemical shift.

[0279] The NMR characterization results of compound A226 are as follows: 1 H NMR (400MHz, CDCl3) δ8.75-8.71(m,2H),8.66(d,J=8.9Hz,1H),8.42(d,J=2.2Hz,1H),8.03(dd,J=18.4,8.8Hz,2H),7. 87(d,J=8.7Hz,1H),7.75-7.52(m,8H),7.47(t,J=7.7Hz,2H),7.43-7.30(m,5H),7.26-7.19(m,4H),7.12-7.11(m,1H).

[0280] Synthesis of compound A252:

[0281] Synthesis of compound A252-2:

[0282] Following the synthesis and purification method of compound A1-5, only the corresponding raw materials need to be changed to obtain the white solid as the target compound A252-2 (18.42 g, purity: 99.52%, yield: 74.62%), with a mass spectrometry result of 433.20 (M+H).

[0283] Synthesis of compound A252-3:

[0284] Following the synthesis and purification method of compound A1-7, only the corresponding raw materials needed to be changed to obtain the target compound A252-3 (20.06 g, yield: 94.26%) as a white solid, with a mass spectrometry result of 461.12 (M+H). The obtained compound was used directly in the next step without purification.

[0285] Synthesis of compound A252-4:

[0286] Following the synthesis and purification method of compound A1-8, only the corresponding raw materials need to be changed to obtain the white solid as the target compound A252-4 (16.75 g, purity: 99.71%, yield: 74.29%), with a mass spectrometry result of 429.12 (M+H).

[0287] Synthesis of compound A252:

[0288] Following the synthesis and purification method of compound A1, only the corresponding raw materials needed to be changed to obtain the target compound A252 (14.02 g, purity: 99.93%, yield: 74.00%), a light yellow solid. After sublimation purification of 14.02 g of crude A252, sublimed pure A252 (10.58 g, purity: 99.93%, yield: 75.47%) was obtained, with a mass spectrometry result of 638.22 (M+H).

[0289] The NMR characterization results of compound A252 are as follows: 1 H NMR (400MHz, CDCl3) δ8.63–8.60(m,2H),8.26(d,J=9.0Hz,1H),8.00–7.95(m,3H),7.93–7.89(m,2H),7.80(dd,J=8.1,2.4Hz ,1H),7.61–7.49(m,6H),7.43–7.39(m,6H),7.32(d,J=7.2Hz,1H),7.31–7.24(m,2H),7.17–7.07(m,5H),7.02–6.96(m,2H).

[0290] Synthesis of compound A265:

[0291] Following the synthesis and purification method of compound A1, only the corresponding raw materials needed to be changed to obtain the light yellow solid, which was the target compound A265 (10.33 g, purity: 99.94%, yield: 78.63%). After sublimation purification of 10.33 g of crude A265, sublimed pure A265 (8.13 g, purity: 99.94%, yield: 78.71%) was obtained, with a mass spectrometry result of 668.34 (M+H).

[0292] The NMR characterization results of compound A265 are as follows: 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),8.06(d,J=2.2Hz ,1H),7.96-7.90(m,2H),7.89-7.86(m,1H),7.56-7.47(m,2H),7.42(d,J=7.5Hz,1H),7.33-7.31(m,2H).

[0293] Synthesis of compound A280:

[0294] Synthesis of compound A280-2:

[0295] Following the synthesis and purification method of compound A1-3, only the corresponding raw materials need to be changed to obtain the white solid as the target compound A280-2 (33.59 g, purity: 99.41%, yield: 74.02%), with a mass spectrometry result of 329.12 (M+H).

[0296] Synthesis of compound A280-3:

[0297] Following the synthesis and purification method of compound A1-5, only the corresponding raw materials need to be changed to obtain the white solid as the target compound A280-3 (32.63 g, purity: 99.69%, yield: 74.69%), with a mass spectrometry result of 357.24 (M+H).

[0298] Synthesis of compound A280-4:

[0299] Following the synthesis and purification method of compound A1-7, only the corresponding raw materials needed to be changed to obtain the target compound A280-4 (27.96 g, yield: 94.12%) as a white solid, with a mass spectrometry result of 385.04 (M+H). The obtained compound was used directly in the next step without purification.

[0300] Synthesis of compound A280-5:

[0301] Following the synthesis and purification method of compound A1-8, only the corresponding raw materials need to be changed to obtain the white solid as the target compound A280-5 (21.21 g, purity: 99.59%, yield: 74.63%), with a mass spectrometry result of 353.06 (M+H).

[0302] Synthesis of compound A280:

[0303] Following the synthesis and purification method of compound A1, only the corresponding raw materials needed to be changed to obtain the target compound A280 (16.06 g, purity: 99.95%, yield: 74.44%), which was a light yellow solid. After sublimation purification of 16.06 g of crude A280, sublimed pure A280 (12.90 g, purity: 99.95%, yield: 80.33%) was obtained, with a mass spectrometry result of 712.22 (M+H).

[0304] The NMR characterization results of compound A280 are as follows: 1H NMR(400MHz, CDCl3)8.64(d,J=8.9Hz,1H),8.47-8.39(m,1H),8.34-8.24(m, 2H),8.19-8.15(m,3H),8.08(dd,J=17.6,7.8Hz,2H),8.01-7.96(m,3H),7.94 (d,J=2.0Hz,1H),7.92-7.85(m,1H),7.66(d,J=8.0Hz,1H),7.61-7.57(m,1H) ,7.57-7.47(m,9H),7.46-7.37(m,4H),7.32-7.26(m,2H),7.03-6.97(m,2H).

[0305] Synthesis of compound A289:

[0306] Synthesis of compound A289-3:

[0307] Following the synthesis and purification method of compound A1, only the corresponding raw materials need to be changed to obtain the white solid as the target compound A289-3 (20.06 g, purity: 99.87%, yield: 74.63%), with a mass spectrometry result of 356.23 (M+H).

[0308] Synthesis of compound A289-4:

[0309] Following the synthesis and purification method of compound A1-8, only the corresponding raw materials need to be changed to obtain the white solid as the target compound A289-4 (10.05, purity: 99.43%, yield: 39.85%), with a mass spectrometry result of 353.06 (M+H).

[0310] Synthesis of compound A289:

[0311] Following the synthesis and purification method of compound A1, only the corresponding raw materials needed to be changed to obtain the target compound A289 (10.96 g, purity: 99.93%, yield: 78.65%), which was a light yellow solid. After sublimation purification of 10.96 g of crude A289, sublimed pure A289 (8.88 g, purity: 99.93%, yield: 81.03%) was obtained, with a mass spectrometry result of 672.32 (M+H).

[0312] The NMR characterization results of compound A289 are as follows: 1H NMR(400MHz, CDCl3)δ8.61(dd,J=9.1,2.3Hz,2H),8.48-8.44(m,1H),8.21(d,J=2.3Hz,1H ),8.17(dd,J=9.0,2.3Hz,1H),8.00(d,J=2.2Hz,1H),7.96(d,J=9.3Hz,1H),7.91-7.87(m ,1H),7.78(s,1H),7.58-7.56(m,2H),7.55-7.48(m,4H),7.44-7.38(m,4H),7.31(dd,J=7 .5,2.2Hz,1H),7.13(d,J=6.6Hz,1H),7.05-6.96(m,4H),2.13-1.90(m,4H),1.33(s,12H).

[0313] Synthesis of compound A305:

[0314] Synthesis of compound A305-3:

[0315] Following the synthesis and purification method of compound A1, only the corresponding raw materials need to be changed to obtain the white solid as the target compound A305-3 (29.45 g, purity: 99.85%, yield: 75.44%), with a mass spectrometry result of 500.20 (M+H).

[0316] Synthesis of compound A305-4:

[0317] Following the synthesis and purification method of compound A1-8, only the corresponding raw materials need to be changed to obtain the white solid as the target compound A305-4 (22.44 g, purity: 99.53%, yield: 38.43%), with a mass spectrometry result of 353.06 (M+H).

[0318] Synthesis of compound A305:

[0319] Following the synthesis and purification method of compound A1, only the corresponding raw materials needed to be changed to obtain the light yellow solid, which was the target compound A305 (17.89 g, purity: 99.94%, yield: 74.85%). After sublimation purification of 17.89 g of crude A305, sublimed pure A305 (14.88 g, purity: 99.94%, yield: 83.18%) was obtained, with a mass spectrometry result of 816.28 (M+H).

[0320] The NMR characterization results of compound A305 are as follows: 1H NMR(400MHz, CDCl3) δ8.69(d,J=8.2Hz,1H),8.62(d,J=9.3Hz,1H),8.50-8. 43(m,1H),8.24(d,J=2.1Hz,1H),8.11-8.03(m,3H),7.99-7.92(m,2H),7.92 -7.85(m,1H),7.76(d,J=7.1Hz,1H),7.70-7.63(m,3H),7.60(dd,J=8.0,1.3 Hz, 1H), 7.56-7.22 (m, 19H), 7.14-7.06 (m, 2H), 7.03 (dd, J = 7.0, 1.4Hz, 1H).

[0321] Synthesis of compound A340:

[0322] Synthesis of compound A340-2:

[0323] Following the synthesis and purification method of compound A1-5, only the corresponding raw materials need to be changed to obtain the white solid as the target compound A340-2 (20.20 g, purity: 99.52%, yield: 77.74%), with a mass spectrometry result of 357.22 (M+H).

[0324] Synthesis of compound A340-3:

[0325] Following the synthesis and purification method of compound A1-7, only the corresponding raw materials needed to be changed to obtain the target compound A340-3 (15.86 g, yield: 94.63%) as a white solid, with a mass spectrometry result of 385.04 (M+H). The obtained compound was used directly in the next step without purification.

[0326] Synthesis of compound A340-4:

[0327] Following the synthesis and purification method of compound A1-8, only the corresponding raw materials need to be changed to obtain the white solid as the target compound A340-4 (14.36 g, purity: 99.76%, yield: 76.33%), with a mass spectrometry result of 353.06 (M+H).

[0328] Synthesis of compound A340-5:

[0329] Following the synthesis and purification method of compound A1-3, only the corresponding raw materials need to be changed to obtain the white solid as the target compound A340-4 (12.37 g, purity: 98.08%, yield: 75.55%), with a mass spectrometry result of 445.20 (M+H).

[0330] Synthesis of compound A340-7:

[0331] Following the synthesis and purification method of compound A1-5, only the corresponding raw materials need to be changed to obtain the white solid as the target compound A340-7 (10.23 g, purity: 98.88%, yield: 78.96%), with a mass spectrometry result of 523.04 (M+H).

[0332] Synthesis of compound A340:

[0333] Following the synthesis and purification method of compound A1, only the corresponding raw materials needed to be changed to obtain the target compound A340 (10.28 g, purity: 99.95%, yield: 78.26%), a light yellow solid. After sublimation purification of 10.28 g of crude A340, sublimed pure A340 (8.02 g, purity: 99.95%, yield: 78.02%) was obtained, with a mass spectrometry result of 764.22 (M+H).

[0334] The NMR characterization results of compound A340 are as follows: 1 H NMR (400MHz, CDCl3) δ8.61-8.59(m,2H),8.29-8.27(m,1H),8.16-8.14(m,1H),8.06-8.01(m,2H),7.96-7.86(m,3H),7.80(d ,J=7.7Hz,1H),7.69(dd,J=7.2,2.5Hz,1H),7.64-7.45(m,14H),7.45-7.36(m,7H),7.32(d,J=7.6Hz,1H),6.96-6.91(m,4H).

[0335] Synthesis of compound A424:

[0336] Synthesis of compound A424-1:

[0337] Following the synthesis and purification method of compound A1-5, only the corresponding raw materials need to be changed to obtain the white solid as the target compound A424-1 (26.52 g, purity: 99.46%, yield: 74.52%), with a mass spectrometry result of 357.24 (M+H).

[0338] Synthesis of compound A424-2:

[0339] Following the synthesis and purification method of compound A1-7, only the corresponding raw materials need to be changed to obtain the target compound A424-2 (18.06 g, yield: 93.06%) as a white solid, with a mass spectrometry result of 385.04 (M+H). The obtained compound was used directly in the next step without purification.

[0340] Synthesis of compound A424-3:

[0341] Following the synthesis and purification method of compound A1-8, only the corresponding raw materials need to be changed to obtain the white solid as the target compound A424-3 (18.85g, purity: 99.23%, yield: 40.05%), with a mass spectrometry result of 353.06 (M+H).

[0342] Synthesis of compound A424-5:

[0343] Following the synthesis and purification method of compound A1, only the corresponding raw materials need to be changed to obtain the white solid as the target compound A424-5 (15.96 g, purity: 99.77%, yield: 79.06%), with a mass spectrometry result of 385.16 (M+H).

[0344] Synthesis of compound A424:

[0345] Following the synthesis and purification method of compound A1, only the corresponding raw materials needed to be changed to obtain the light yellow solid, which was the target compound A424 (13.06 g, purity: 99.94%, yield: 78.61%). After sublimation purification of 13.06 g of crude A424, sublimed pure A424 (10.00 g, purity: 99.94%, yield: 76.57%) was obtained, with a mass spectrometry result of 701.25 (M+H).

[0346] The NMR characterization results of compound A424 are as follows: 1 H NMR(400MHz, CDCl3)δ8.62(s,1H),8.48–8.41(m,1H),8.35–8.25(m,1H),8.16 (d,J=2.2Hz,1H),8.04–7.98(m,2H),7.96(dd,J=7.4,2.7Hz,2H),7.93–7.84(m ,6H),7.78(d,J=2.1Hz,1H),7.55–7.46(m,4H),7.42(d,J=7.6Hz,1H),7.38(d d,J=7.2,2.1Hz,1H),7.35–7.25(m,5H),7.25–7.16(m,3H),7.16–7.05(m,3H).

[0347] Synthesis of compound A481:

[0348] Synthesis of compound A481-2:

[0349] Following the synthesis and purification method of compound A1-3, only the corresponding raw materials need to be changed to obtain the white solid as the target compound A481-2 (25.77 g, purity: 98.88%, yield: 74.12%), with a mass spectrometry result of 355.12 (M+H).

[0350] Synthesis of compound A481-4:

[0351] Following the synthesis and purification method of compound A1-5, only the corresponding raw materials need to be changed to obtain the white solid as the target compound A481-4 (20.11 g, purity: 99.54%, yield: 71.52%), with a mass spectrometry result of 439.18 (M+H).

[0352] Synthesis of compound A481-5:

[0353] Following the synthesis and purification method of compound A1-7, only the corresponding raw materials need to be changed to obtain the target compound A481-5 (22.53 g, yield: 95.86%) as a white solid, with a mass spectrometry result of 467.22 (M+H). The obtained compound was used directly in the next step without purification.

[0354] Synthesis of compound A481-6:

[0355] Following the synthesis and purification method of compound A1-8, only the corresponding raw materials need to be changed to obtain the white solid as the target compound A481-6 (18.88 g, purity: 99.75%, yield: 75.62%), with a mass spectrometry result of 435.16 (M+H).

[0356] Synthesis of compound A481

[0357] Following the synthesis and purification method of compound A1, only the corresponding raw materials needed to be changed to obtain the light yellow solid, which was the target compound A481 (15.55 g, purity: 99.94%, yield: 76.22%). After sublimation purification of 15.55 g of crude A481, sublimed pure A481 (11.85 g, purity: 99.94%, yield: 76.21%) was obtained, with a mass spectrometry result of 658.30 (M+H).

[0358] The NMR characterization results of compound A481 are as follows: 1H NMR(400MHz, CDCl3)δ8.63–8.57(m,1H),8.50(d,J=8.1Hz,1H),8.28–8.22(m,1H),8.16–8.07(m,2H), 8.06(d,J=2.2Hz,1H),7.99–7.92(m,3H),7.89–7.84(m,1H),7.77(d,J=7.1Hz,1H),7.67–7.60(m,1H) ,7.56(d,J=7.9Hz,1H),7.47–7.43(m,1H),7.43–7.35(m,2H),7.31–7.24(m,2H),7.19(dd,J=7.2,2.1 Hz,1H),7.17–7.12(m,2H),7.12–7.05(m,2H),7.03(dd,J=7.3,2.2Hz,1H),1.80(s,6H),1.34(s,9H).

[0359] Synthesis of compound A488:

[0360] Synthesis of compound A488-2:

[0361] Following the synthesis and purification method of compound A1-3, only the corresponding raw materials need to be changed to obtain the white solid as the target compound A488-2 (28.77 g, purity: 99.02%, yield: 76.74%), with a mass spectrometry result of 404.14 (M+H).

[0362] Synthesis of compound A488-3:

[0363] Following the synthesis and purification method of compound A1-5, only the corresponding raw materials need to be changed to obtain the white solid as the target compound A488-3 (24.85 g, purity: 99.67%, yield: 73.62%), with a mass spectrometry result of 432.21 (M+H).

[0364] Synthesis of compound A488-4:

[0365] Following the synthesis and purification method of compound A1-7, only the corresponding raw materials needed to be changed to obtain the target compound A488-4 (23.41 g, yield: 96.66%) as a white solid, with a mass spectrometry result of 460.04 (M+H). The obtained compound was used directly in the next step without purification.

[0366] Synthesis of compound A488-5:

[0367] Following the synthesis and purification method of compound A1-8, only the corresponding raw materials need to be changed to obtain the white solid as the target compound A488-5 (20.00 g, purity: 99.87%, yield: 77.01%), with a mass spectrometry result of 428.02 (M+H).

[0368] Synthesis of compound A488:

[0369] Following the synthesis and purification method of compound A1, only the corresponding raw materials needed to be changed to obtain the target compound A488 (18.11 g, purity: 99.92%, yield: 75.98%), a light yellow solid. After sublimation purification of 18.11 g of crude A488, sublimed pure A488 (15.00 g, purity: 99.93%, yield: 82.83%) was obtained, with a mass spectrometry result of 713.24 (M+H).

[0370] The NMR characterization results of compound A488 are as follows: 1 H NMR(400MHz, CDCl3)δ8.60(d,J=9.0Hz,1H),8.52(d,J=8.0Hz,1H),8.47-8 .41(m,1H),8.27-8.22(m,1H),8.14-8.07(m,2H),8.06-8.04(m,1H),7.94( d,J=8.1Hz,1H),7.92-7.87(m,2H),7.63-7.55(m,4H),7.55-7.48(m,6H),7 .44-7.35(m,7H),7.34-7.27(m,2H),7.23-7.13(m,3H),7.04-6.97(m,4H).

[0371] Synthesis of compound A496:

[0372] Synthesis of compound A496-2:

[0373] Following the synthesis and purification method of compound A1-5, only the corresponding raw materials need to be changed to obtain the white solid as the target compound A496-2 (18.81 g, purity: 99.72%, yield: 73.62%), with a mass spectrometry result of 429.10 (M+H).

[0374] Synthesis of compound A496-3:

[0375] Following the synthesis and purification method of compound A1-7, only the corresponding raw materials needed to be changed to obtain the target compound A496-3 (18.77 g, yield: 92.626%) as a white solid, with a mass spectrometry result of 457.13 (M+H). The obtained compound was used directly in the next step without purification.

[0376] Synthesis of compound A496-4:

[0377] Following the synthesis and purification method of compound A1-8, only the corresponding raw materials need to be changed to obtain the white solid, which is the target compound A496-4 (16.85 g, purity: 99.45%, yield: 75.11%), with a mass spectrometry result of 425.24 (M+H).

[0378] Synthesis of compound A496-5:

[0379] Following the synthesis and purification method of compound A1-5, only the corresponding raw materials need to be changed to obtain the white solid as the target compound A496-5 (19.78 g, purity: 99.62%, yield: 74.44%), with a mass spectrometry result of 591.15 (M+H).

[0380] Synthesis of compound A496:

[0381] Following the synthesis and purification method of compound A1, only the corresponding raw materials needed to be changed to obtain the light yellow solid, which was the target compound A496 (12.71 g, purity: 99.95%, yield: 62.71%). After sublimation purification of 12.71 g of crude A496, sublimed pure A496 (9.84 g, purity: 99.97%, yield: 11.41%) was obtained, mass spectrometry: 800.07 (M+H).

[0382] The NMR characterization results of compound A496 are as follows: 1 H NMR (400MHz, CDCl3) δ8.62 (dd, J=13.1, 8.5Hz, 2H), 8.30 (dd, J=9.0, 0.7Hz, 1H), 8. 16(d,J=7.9Hz,1H),8.06–7.98(m,3H),7.89(dt,J=7.0,0.7Hz,1H),7.83(d,J=2.2 Hz,1H),7.79–7.70(m,2H),7.67(dd,J=9.2,2.1Hz,1H),7.61–7.50(m,6H),7.46–7 .37(m,5H),7.35–7.24(m,4H),7.17–7.06(m,3H),7.03–6.97(m,2H),0.39(s,9H).

[0383] Synthesis of compound A515:

[0384] Synthesis of compound A515-2:

[0385] Following the synthesis and purification method of compound A1-3, only the corresponding raw materials need to be changed to obtain the white solid as the target compound A515-2 (25.33 g, purity: 99.23%, yield: 78.46%), with a mass spectrometry result of 379.12 (M+H).

[0386] Synthesis of compound A515-3:

[0387] Following the synthesis and purification method of compound A1-5, only the corresponding raw materials need to be changed to obtain the white solid as the target compound A515-3 (22.11 g, purity: 99.43%, yield: 75.12%), with a mass spectrometry result of 407.06 (M+H).

[0388] Synthesis of compound A515-4:

[0389] Following the synthesis and purification method of compound A1-7, only the corresponding raw materials needed to be changed to obtain the target compound A515-4 (20.63 g, yield: 95.12%) as a white solid, with a mass spectrometry result of 435.12 (M+H). The obtained compound was used directly in the next step without purification.

[0390] Synthesis of compound A515-5:

[0391] Following the synthesis and purification method of compound A1-8, only the corresponding raw materials need to be changed to obtain the white solid as the target compound A515-5 (18.96 g, purity: 99.90%, yield: 79.63%), with a mass spectrometry result of 403.08 (M+H).

[0392] Synthesis of compound A515:

[0393] Following the synthesis and purification method of compound A1, only the corresponding raw materials needed to be changed to obtain the light yellow solid, which was the target compound A515 (16.96 g, purity: 99.93%, yield: 76.68%). After sublimation purification of 16.96 g of crude A515, sublimed pure A515 (14.33 g, purity: 99.93%, yield: 84.49%) was obtained, with a mass spectrometry result of 612.75 (M+H).

[0394] The NMR characterization results of compound A515 are as follows: 1H NMR (400MHz, CDCl3) δ8.61 (dd, J=8.5, 3.7Hz, 2H), 8.47–8.39 (m, 1H), 8.33–8 .26(m,2H),8.02(d,J=2.0Hz,1H),7.94(d,J=8.2Hz,1H),7.91–7.85(m,2H), 7.83(dd,J=7.4,2.1Hz,1H),7.61–7.49(m,6H),7.45–7.37(m,4H),7.35–7.2 4(m,3H),7.17–7.07(m,3H),7.03–6.97(m,2H),6.88(dd,J=7.6,2.3Hz,1H).

[0395] Synthesis of compound A527:

[0396] Synthesis of compound A527-2:

[0397] Following the synthesis and purification method of compound A1-3, only the corresponding raw materials need to be changed to obtain the white solid as the target compound A527-2 (22.10 g, purity: 99.10%, yield: 70.01%), with a mass spectrometry result of 405.14 (M+H).

[0398] Synthesis of compound A527-3:

[0399] Following the synthesis and purification method of compound A1-5, only the corresponding raw materials need to be changed to obtain the white solid as the target compound A527-3 (20.06 g, purity: 99.21%, yield: 72.32%), with a mass spectrometry result of 433.08 (M+H).

[0400] Synthesis of compound A527-4:

[0401] Following the synthesis and purification method of compound A1-7, only the corresponding raw materials needed to be changed to obtain the target compound A527-4 (18.06 g, yield: 94.33%) as a white solid, with a mass spectrometry result of 461.22 (M+H). The obtained compound was used directly in the next step without purification.

[0402] Synthesis of compound A527-5:

[0403] Following the synthesis and purification method of compound A1-8, only the corresponding raw materials need to be changed to obtain the white solid as the target compound A527-5 (17.63g, purity: 99.88%, yield: 42.03%), with a mass spectrometry result of 429.12 (M+H).

[0404] Synthesis of compound A527:

[0405] Following the synthesis and purification method of compound A1, only the corresponding raw materials needed to be changed to obtain the light yellow solid, which was the target compound A527 (14.63 g, purity: 99.93%, yield: 74.95%). After sublimation purification of 14.63 g of crude A527, sublimed pure A527 (12.00 g, purity: 99.93%, yield: 82.02%) was obtained, with a mass spectrometry result of 668.20 (M+H).

[0406] The NMR characterization results of compound A527 are as follows: 1 H NMR(400MHz, CDCl3)δ8.44(s,1H),8.33–8.26(m,1H),8.23–8.16(m,1H),8.01(d,J=9.0Hz,1H),7.98–7.8 3(m,7H),7.78–7.75(m,2H),7.55–7.47(m,7H),7.44–7.38(m,3H),7.32–7.24(m,2H),7.17–7.06(m,4H).

[0407] Synthesis of compound A539:

[0408] Synthesis of compound A539-2:

[0409] Following the synthesis and purification method of compound A1-3, only the corresponding raw materials need to be changed to obtain the white solid as the target compound A539-2 (18.63g, purity: 99.22%, yield: 76.52%), with a mass spectrometry result of 504.16 (M+H).

[0410] Synthesis of compound A539-3:

[0411] Following the synthesis and purification method of compound A1-5, only the corresponding raw materials need to be changed to obtain the white solid as the target compound A539-3 (17.26 g, purity: 99.12%, yield: 75.63%), with a mass spectrometry result of 532.14 (M+H).

[0412] Synthesis of compound A539-4:

[0413] Following the synthesis and purification method of compound A1-7, only the corresponding raw materials need to be changed to obtain the target compound A539-4 (15.12 g, yield: 96.33%) as a white solid, with a mass spectrometry result of 560.12 (M+H). The obtained compound was used directly in the next step without purification.

[0414] Synthesis of compound A539-5:

[0415] Following the synthesis and purification method of compound A1-8, only the corresponding raw materials need to be changed to obtain the white solid as the target compound A539-5 (14.00 g, purity: 99.87%, yield: 41.26%), with a mass spectrometry result of 528.24 (M+H).

[0416] Synthesis of compound A539:

[0417] Following the synthesis and purification method of compound A1, only the corresponding raw materials needed to be changed to obtain the light yellow solid, which was the target compound A539 (14.00 g, purity: 99.92%, yield: 76.78%). After sublimation purification of 14.00 g of crude A539, ​​sublimed pure A539 (11.52 g, purity: 99.92%, yield: 82.28%) was obtained, with a mass spectrometry result of 813.32 (M+H).

[0418] The NMR characterization results of compound A539 are as follows: 1 H NMR (400MHz, CDCl3) δ8.87(s,1H),8.51–8.49(m,1H),8.33–8.26(m,2H),8.21–8.19(m,1H),8.12(d,J=2.2Hz,1H),8.04–7.99(m,2H),7. 96(d,J=8.0Hz,1H),7.92–7.83(m,3H),7.63–7.48(m,11H),7.48–7.37(m,8H),7.34–7.26(m,2H),7.20–7.10(m,3H),7.03–6.97(m,4H).

[0419] Synthesis of compound B2:

[0420] Synthesis of compound B2:

[0421] Compounds B2-1 (12.33 g, 44.98 mmol), B2-2 (16.05 g, 44.98 mmol), tetrakis(triphenylphosphine)palladium (Pd(PPh3)4, 1.04 g, 0.90 mmol), sodium hydroxide (3.6 g, 90.02 mmol), tetrahydrofuran (200 mL), and deionized water (70 mL) were added to a 500 mL three-necked round-bottom flask. The mixture was purged three times with nitrogen under vacuum, and the temperature was raised to 75 °C for 6 hours. The consumption of compound B2-1 was monitored by TLC (ethyl acetate:n-hexane volume ratio = 1:10 as the developing solvent).

[0422] After cooling to room temperature, methanol (300 mL) was added and stirred at room temperature for 10 minutes. The mixture was then filtered to obtain a yellow solid. Xylene (500 mL) was added, and the mixture was heated to 120 °C to dissolve the material. The mixture was then cooled to room temperature and filtered once through a column chromatography line using silica gel (60 g, 200-300 mesh). The filter cake was washed with 100 mL of toluene until no product residue remained. The combined organic phases were concentrated under reduced pressure at 70 °C to obtain a yellow solid. The solid was crystallized twice using xylene and methanol and dried under vacuum at 100 °C for 8 hours to obtain a white solid, compound B2 (20.68 g, purity: 99.93%, yield: 83.49%). 20.68 g of crude compound B2 was sublimated to obtain sublimed pure compound B2 (17.67 g, purity: 99.93%, yield: 85.44%). The mass spectrometry result was 551.20 (M+H).

[0423] The NMR characterization results of compound B2 are as follows: 1 H NMR(400MHz, CDCl3)δ8.08–8.00(m,1H),7.91(dd,J=9.3,1.2Hz,1H),7.87(s,1H),7.87–7.82(m,2H),7 .82–7.74(m,2H),7.69–7.60(m,7H),7.60–7.51(m,3H),7.49–7.36(m,8H),7.27(dd,J=9.3,6.8Hz,1H).

[0424] Synthesis of compound B35:

[0425] Synthesis of compound B35-3:

[0426] Compound B35-1 (28.17 g, 75.39 mmol), compound B35-3 (22.97 g, 90.47 mmol), 1,1-bis(diphenylphosphine)diferro-palladium dichloride (0.55 g, 0.75 mmol), potassium acetate (11.10 g, 113.08 mol), and 1,4-dioxane (420 mL) were added to a 1000 mL three-necked round-bottom flask. The flask was purged with nitrogen three times, and then the system was heated to 100 °C and reacted for 2 hours. The reaction was monitored by TLC (ethyl acetate:n-hexane volume ratio = 1:15 as the developing solvent). Compound B35-1 was completely consumed.

[0427] The solution was cooled to 60℃, concentrated under reduced pressure to remove the solvent, and ethyl acetate (700 mL) was added. The solution was washed three times with deionized water (300 mL x 3), separated, and loaded onto a silica gel column using a dry chromatography method. Purification was performed by silica gel column chromatography (200-300 mesh silica gel, ethyl acetate:n-hexane volume ratio = 1:15 as eluent). After elution, the solution was concentrated under reduced pressure at 70℃ for 1 hour to obtain a white solid, compound B35-3 (24.53 g, purity: 99.42%, yield: 77.41%). Mass spectrometry result: 421.19 (M+H). Synthesis of compound B35:

[0428] Following the synthesis and purification method of compound B2, only the corresponding raw materials needed to be changed to obtain the target compound B35 (12.11 g, purity: 99.95%, yield: 79.06%) as a white solid. After sublimation purification of 12.11 g of crude compound B35, sublimed pure compound B35 (9.99 g, purity: 99.95%, yield: 82.50%) was obtained, with a mass spectrometry result of 576.24 (M+H).

[0429] Figure 2 shows compound B35 of this application. 1 H NMR spectrum.

[0430] The NMR characterization results of compound B35 are as follows: 1 H NMR (400MHz, CDCl3) δ9.41(s,1H),9.35(d,J=8.7Hz,1H),8.91–8.88(m,3H),8.73(d,J=7.3Hz,1H),8.14(d,J=7.5Hz,1H),8.08(d,J= 8.7Hz,1H),7.97(d,J=7.6Hz,1H),7.82–7.57(m,10H),7.44–7.34(m,3H),7.26(s,1H),6.96(t,J=7.5Hz,1H),6.79(d,J=7.9Hz,1H).

[0431] Synthesis of compound B51:

[0432] Synthesis of compound B51-3:

[0433] Compound B51-1 (20.00 g, 112.35 mmol), compound B51-2 (24.66 g, 112.35 mmol), tetra(triphenylphosphine)palladium (1.29 g, 1.12 mmol), potassium carbonate (23.29 g, 168.52 mmol), tetrahydrofuran (300 mL), and deionized water (100 mL) were added to a 1000 mL three-necked round-bottom flask. The mixture was purged with nitrogen three times, and then the system was heated to 75 °C and reacted for 3 hours. The reaction was monitored by TLC (ethyl acetate:n-hexane volume ratio = 1:10 as the developing solvent). Compound B51-1 was completely consumed.

[0434] The solution was cooled to 60℃, concentrated under reduced pressure to remove the solvent, and ethyl acetate (600 mL) was added. The solution was washed three times with deionized water (200 mL * 3). The solution was separated, and the mixture was loaded onto a silica gel column using a dry chromatography method. The solution was purified by silica gel column chromatography (200–300 mesh silica gel, ethyl acetate:n-hexane volume ratio = 1:20 as eluent). After elution, the solution was concentrated under reduced pressure at 70℃ for 2 hours to obtain a white solid, which was compound B51-3 (23.08 g, purity: 99.45%, yield: 75.32%). The mass spectrometry result was 273.01 (M+H).

[0435] Synthesis of compound B51-5:

[0436] Compound B51-3 (13.74 g, 50.45 mmol), compound B51-3 (25.94 g, 75.67 mmol), and tetrahydrofuran (200 mL) were added to a 500 mL three-necked round-bottom flask. The flask was purged with nitrogen three times. The system was then cooled to 5 °C, and sodium methoxide (5.45 g, 100.90 mmol) was added in one go. The reaction was maintained at 5 °C for 1 hour. The reaction was monitored by TLC (ethyl acetate: n-hexane volume ratio = 1:10 as the developing solvent). Compound B51-3 was completely consumed.

[0437] Add 500 mL of deionized water, concentrate under reduced pressure to remove the solvent, extract with 500 mL of ethyl acetate, separate the layers, and concentrate under reduced pressure at 70 °C for 1 hour to obtain a white solid, compound B51-3 (14.42 g, yield: 95.00%), with a mass spectrometry result of 301.04 (M+H). The obtained compound was used directly in the next step without purification.

[0438] Synthesis of compound B51-6:

[0439] Compound B51-5 (12.47 g, 44.17 mmol) and toluene (180 mL) were added to a 500 mL three-necked round-bottom flask. The flask was purged with nitrogen three times. The system was then 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 volume ratio = 1:15 as the developing solvent). Compound B51-5 was completely consumed.

[0440] Methanol (200 mL) was added to the mixture, and a large amount of white solid precipitated. After filtration, 13 g of solid was obtained. The solid was crystallized once with toluene (130 mL) and methanol (50 mL), filtered, and the filter cake was dried under vacuum at 80 °C for 1 hour to obtain a white solid, which was compound B51-6 (8.86 g, purity: 99.90%, yield: 74.62%). The mass spectrometry result was 269.06 (M+H).

[0441] Synthesis of compound B51-7:

[0442] Following the synthesis and purification method of compound B35-3, only the corresponding raw materials need to be changed to obtain the white solid as the target compound B51-7 (12.26 g, purity: 99.33%, yield: 76.74%), with a mass spectrometry result of 361.14 (M+H).

[0443] Synthesis of compound B51:

[0444] Following the synthesis and purification method of compound B2, only the corresponding raw materials needed to be changed to obtain the target compound B51 (15.30 g, purity: 99.94%, yield: 75.69%) as a white solid. After sublimation purification of 15.30 g of crude compound B51, sublimed pure compound B51 (12.52 g, purity: 99.94%, yield: 81.83%) was obtained, with a mass spectrometry result of 542.16 (M+H).

[0445] The NMR characterization results of compound B51 are as follows: 1 H NMR (400MHz, CDCl3) δ8.33(d,J=7.3Hz,1H),8.25–8.18(m,1H),8.15(d,J=9.5Hz,1H),8.13–8.05(m,3H),7.98( d,J=7.8Hz,1H),7.96–7.86(m,3H),7.72–7.66(m,2H),7.59–7.53(m,2H),7.53–7.47(m,5H),7.45–7.36(m,4H).

[0446] Synthesis of compound B100:

[0447] Synthesis of compound B100-3:

[0448] Following the synthesis and purification method of compound B51-3, only the corresponding raw materials need to be changed to obtain the white solid as the target compound B100-3 (23.12 g, purity: 99.21%, yield: 74.96%), with a mass spectrometry result of 257.03 (M+H).

[0449] Synthesis of compound B100-4:

[0450] Following the synthesis and purification method of compound B51-5, only the corresponding raw materials needed to be changed to obtain the target compound B100-4 (17.88 g, yield: 94.20%) as a white solid, with a mass spectrometry result of 285.06 (M+H). The obtained compound was used directly in the next step without purification.

[0451] Synthesis of compound B100-5:

[0452] Following the synthesis and purification method of compound B51-6, only the corresponding raw materials need to be changed to obtain the white solid as the target compound B100-5 (18.77 g, purity: 99.88%, yield: 78.06%), with a mass spectrometry result of 253.03 (M+H).

[0453] Synthesis of compound B100-6:

[0454] Following the synthesis and purification method of compound B35-3, only the corresponding raw materials need to be changed to obtain the white solid, which is the target compound B100-6 (15.12 g, purity: 99.43%, yield: 77.17%), with a mass spectrometry result of 345.16 (M+H).

[0455] Synthesis of compound B100:

[0456] Following the synthesis and purification method of compound B2, only the corresponding raw materials needed to be changed to obtain the white solid, which was the target compound B100 (16.26 g, purity: 99.93%, yield: 76.08%). After sublimation purification of 16.26 g of crude compound B100, sublimed pure compound B100 (14.00 g, purity: 99.93%, yield: 86.10%) was obtained, with a mass spectrometry result of 540.13 (M+H).

[0457] The NMR characterization results of compound B100 are as follows: 1H NMR (400MHz, CDCl3) δ8.27(d,J=2.3Hz,1H),8.12–8.00(m,6H),7.96(d,J=7.2Hz,1H),7.87(dd,J=9.3,1.3 Hz,1H),7.67–7.59(m,2H),7.58–7.47(m,4H),7.45–7.38(m,4H),7.31(d,J=7.2Hz,1H),7.26–7.24(m,1H).

[0458] Synthesis of compound B109:

[0459] Synthesis of compound B109-2:

[0460] Following the synthesis and purification method of compound B51-3, only the corresponding raw materials need to be changed to obtain the white solid as the target compound B109-2 (20.00 g, purity: 99.1%, yield: 75.63%), with a mass spectrometry result of 257.03 (M+H).

[0461] Synthesis of compound B109-3:

[0462] Following the synthesis and purification method of compound B51-5, only the corresponding raw materials needed to be changed to obtain the target compound B109-3 (16.78 g, yield: 96.06%) as a white solid, with a mass spectrometry result of 285.06 (M+H). The obtained compound was used directly in the next step without purification.

[0463] Synthesis of compound B109-4:

[0464] Following the synthesis and purification method of compound B51-6, only the corresponding raw materials need to be changed to obtain the white solid as the target compound B109-4 (15.63 g, purity: 99.78%, yield: 75.12%), with a mass spectrometry result of 253.03 (M+H).

[0465] Synthesis of compound B109-5:

[0466] Following the synthesis and purification method of compound B35-3, only the corresponding raw materials need to be changed to obtain the white solid, which is the target compound B109-5 (15.12 g, purity: 99.43%, yield: 76.51%), with a mass spectrometry result of 345.16 (M+H).

[0467] Synthesis of compound B109-7:

[0468] Compound B109-5 (20.00 g, 58.10 mmol), compound B109-6 (19.35 g, 58.10 mmol), tetra(triphenylphosphine)palladium (0.67 g, 0.58 mmol), potassium carbonate (12.04 g, 87.15 mmol), tetrahydrofuran (300 mL), and deionized water (100 mL) were added to a 1000 mL three-necked round-bottom flask. The flask was purged with nitrogen three times, and then the system was heated to 65 °C and reacted for 6 hours. The reaction was monitored by TLC (ethyl acetate:n-hexane volume ratio = 1:15 as the developing solvent). Compound B109-5 was completely consumed.

[0469] The solvent was removed by concentration under reduced pressure at 60℃. Ethyl acetate (700 mL) was added, and the sample was washed three times with deionized water (300 mL x 3). The mixture was separated, and the sample was loaded onto a silica gel column using a dry chromatography method. Purification was performed by silica gel column chromatography (200-300 mesh silica gel, ethyl acetate:n-hexane volume ratio = 1:20 as eluent). After elution, the sample was concentrated under reduced pressure at 70℃ for 2 hours to obtain a white solid, compound B109-7 (18.53 g, purity: 99.21%, yield: 75.32%), with a mass spectrometry result of 423.22 (M+H). Synthesis of compound B109-8:

[0470] Following the synthesis and purification method of compound B35-3, only the corresponding raw materials need to be changed to obtain the white solid, which is the target compound B109-8 (12.12 g, purity: 99.03%, yield: 78.06%), with a mass spectrometry result of 471.22 (M+H).

[0471] Synthesis of compound B109:

[0472] Following the synthesis and purification method of compound B2, only the corresponding raw materials needed to be changed to obtain the target compound B109 (15.12 g, purity: 99.94%, yield: 77.63%), which was a light yellow solid. After sublimation purification of 15.12 g of crude compound B109, sublimed pure compound B109 (12.57 g, purity: 99.94%, yield: 83.14%) was obtained, with a mass spectrometry result of 576.20 (M+H).

[0473] The NMR characterization results of compound B109 are as follows: 1H NMR (400MHz, CDCl3) δ8.41(t,J=2.2Hz,1H),8.24(t,J=2.2Hz,1H),8.18(d,J=8.3Hz,1H),8.11–8.06(m,5H),8.06–7.99(m, 3H),7.96–7.94(m,1H),7.79–7.77(m,1H),7.71–7.69(m,1H),7.67–7.57(m,2H),7.55–7.38(m,8H),7.32(d,J=7.3Hz,1H).

[0474] Synthesis of compound B170:

[0475] Synthesis of compound B170-2:

[0476] Following the synthesis and purification method of compound B35-3, only the corresponding raw materials need to be changed to obtain the white solid as the target compound B170-2 (125.23g, purity: 99.52%, yield: 74.63%), with a mass spectrometry result of 395.17 (M+H).

[0477] Synthesis of compound B170:

[0478] Following the synthesis and purification method of compound B2, only the corresponding raw materials needed to be changed to obtain the target compound B170 (13.56 g, purity: 99.93%, yield: 76.58%), a light yellow solid. After sublimation purification of 13.56 g of crude compound B170, sublimed pure compound B170 (11.00 g, purity: 99.93%, yield: 81.12%) was obtained, with a mass spectrometry result of 549.20 (M+H).

[0479] The NMR characterization results of compound B170 are as follows: 1 H NMR (400MHz, CDCl3) δ8.72–7.58(m,2H),8.20(t,J=2.1Hz,1H),8.14(dd,J=9.5,0.7Hz,1H),8.11–8.03(m, 1H),7.97(d,J=9.0Hz,1H),7.93–7.77(m,7H),7.64–7.57(m,1H),7.57–7.38(m,9H),7.29(t,J=9.2Hz,1H).

[0480] Synthesis of compound B186:

[0481] Synthesis of compound B186-2:

[0482] Following the synthesis and purification method of compound B51-3, only the corresponding raw materials need to be changed to obtain the white solid as the target compound B186-2 (20.63 g, purity: 99.45%, yield: 75.69%), with a mass spectrometry result of 307.04 (M+H).

[0483] Synthesis of compound B186-3:

[0484] Following the synthesis and purification method of compound B51-5, only the corresponding raw materials needed to be changed to obtain the target compound B186-3 (18.70 g, yield: 94.20%) as a white solid, with a mass spectrometry result of 335.80 (M+H). The obtained compound was used directly in the next step without purification.

[0485] Synthesis of compound B186-4:

[0486] Following the synthesis and purification method of compound B51-6, only the corresponding raw materials need to be changed to obtain the white solid as the target compound B186-4 (19.75 g, purity: 99.78%, yield: 76.52%), with a mass spectrometry result of 303.06 (M+H).

[0487] Synthesis of compound B186-5:

[0488] Following the synthesis and purification method of compound B35-3, only the corresponding raw materials need to be changed to obtain the white solid, which is the target compound B186-5 (15.62 g, purity: 99.16%, yield: 75.63%), with a mass spectrometry result of 395.17 (M+H).

[0489] Synthesis of compound B186:

[0490] The NMR characterization results of compound B186 were as follows: Following the synthesis and purification method of compound B2, only the corresponding raw materials needed to be changed, yielding a white solid as the target compound B186 (14.20 g, purity: 99.93%, yield: 75.06%). After sublimation purification of 14.20 g of crude compound B186, sublimed pure compound B186 (11.62 g, purity: 99.93%, yield: 81.83%) was obtained, with a mass spectrometry result of 576.20 (M+H).

[0491] The NMR characterization results of compound B186 are as follows: 1H NMR(400MHz, CDCl3)δ8.46(d,J=2.3Hz,1H),8.13–8.06(m,4H),8.06–7.98(m,3H),7.97–7.92(m,2H),7.90(d,J=7.1Hz,1 H),7.73–7.66(m,2H),7.66–7.61(m,1H),7.60–7.54(m,2H),7.54–7.45(m,3H),7.45–7.37(m,5H),7.32(d,J=7.1Hz,1H).

[0492] Synthesis of compound B251:

[0493] Synthesis of compound B251-2:

[0494] Following the synthesis and purification method of compound B51-3, only the corresponding raw materials need to be changed to obtain the white solid as the target compound B251-2 (22.06 g, purity: 99.54%, yield: 76.15%), with a mass spectrometry result of 307.04 (M+H).

[0495] Synthesis of compound B251-3:

[0496] Following the synthesis and purification method of compound B51-5, only the corresponding raw materials needed to be changed to obtain the target compound B251-3 (17.02 g, yield: 96.52%) as a white solid, with a mass spectrometry result of 335.80 (M+H). The obtained compound was used directly in the next step without purification.

[0497] Synthesis of compound B251-4:

[0498] Following the synthesis and purification method of compound B51-6, only the corresponding raw materials need to be changed to obtain the white solid as the target compound B251-4 (18.06 g, purity: 99.52%, yield: 75.44%), with a mass spectrometry result of 303.06 (M+H).

[0499] Synthesis of compound B251-5:

[0500] Following the synthesis and purification method of compound B35-3, only the corresponding raw materials need to be changed to obtain the white solid, which is the target compound B251-5 (16.00 g, purity: 99.23%, yield: 76.06%), with a mass spectrometry result of 395.17 (M+H).

[0501] Synthesis of compound B251:

[0502] Following the synthesis and purification method of compound B2, only the corresponding raw materials needed to be changed to obtain the target compound B251 (13.08 g, purity: 99.94%, yield: 77.63%) as a white solid. After sublimation purification of 13.08 g of crude compound B251, sublimed pure compound B251 (10.41 g, purity: 99.93%, yield: 79.58%) was obtained, with a mass spectrometry result of 590.18 (M+H).

[0503] The NMR characterization results of compound B251 are as follows: 1 H NMR(400MHz, CDCl3)δ8.57(s,1H),8.17(d,J=8.0Hz,1H),8.13–8.00(m,5H),8.00–7.93(m,1H), 7.92–7.81(m,3H),7.68–7.59(m,3H),7.58–7.45(m,4H),7.45–7.38(m,4H),7.28–7.24(m,1H).

[0504] Synthesis of compound C1:

[0505] Following the synthesis and purification method of compound A1, only the corresponding raw materials need to be changed to obtain the light yellow solid, which is the target compound C1 (12.13 g, purity: 99.96%, yield: 83.52%). After sublimation purification of 12.13 g of crude C1, sublimed pure C1 (9.4 g, purity: 99.97%, yield: 77.49%) was obtained, with a mass spectrometry result of 511.62 (M+H).

[0506] The NMR characterization results of compound C1 are as follows: 1 H NMR(400MHz, CDCl3)δ8.68(s,2H),8.24–8.00(m,8H),7.90(s,5H),7.75(s,4H),7.68(s,1H),7.63(s,2H),7.57–7.22(m, 22H),7.46–7.22(m,12H),7.43–7.22(m,11H),7.26(d,J=20.0Hz,6H),7.26(d,J=20.0Hz,5H),7.08(s,4H),7.00(s,2H).

[0507] Application example: Fabrication of organic electroluminescent devices

[0508] In one embodiment, as shown in FIG3, FIG3 is a schematic diagram of the structure of an organic electroluminescent device. The organic electroluminescent device includes a 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 stacked together.

[0509] A 50mm*50mm*1.0mm glass substrate with an ITO (anode 2, indium tin oxide, 100nm) transparent electrode was ultrasonically cleaned in ethanol for 10 minutes, dried at 150°C, and then treated with N2 Plasma for 30 minutes. The glass substrate was then mounted on the substrate support of a vacuum evaporation apparatus. Compound NDP-9 and compound HTM 1 were deposited at a weight ratio of 97:3 to form a hole injection layer with a thickness of 10nm. Immediately afterwards, a layer of HTM1 was deposited to form a thin film with a thickness of 60nm as HTL1 (hole transport layer 1). Then, a layer of HTM2 was deposited on the HTM1 film to form a thin film with a thickness of 10nm as HTL2 (hole transport layer 2). Then, a light-emitting layer with a thickness of 40nm (main material: red light doping material = 97%: 3%, mass fraction) was co-deposited on the HTM2 film in the form of a single host or multiple hosts. The host materials of the single host or multiple hosts are the compounds of this application and comparative compounds 1-4, respectively. An ETL (electron transport layer) material and LiQ are co-deposited in a 50:50 weight ratio (35 nm) on the light-emitting layer as an electron transport material. Then, LiQ (1 nm) is deposited on the electron transport material layer as an electron injection material to form an electron injection layer. Finally, Mg / Ag (100 nm, mass ratio 1:9) is deposited as a cathode material using a co-deposition method to obtain an organic electroluminescent device.

[0510] The structural formulas of NDP-9, HTM1, HTM2, ETL materials, red light-doped materials, LiQ, and comparative compounds 1-4 are as follows:

[0511] Effect evaluation:

[0512] The above-mentioned organic electroluminescent devices were subjected to device performance testing. The compounds prepared in this application and comparative compounds 1-4 were used as host materials for comparison. A constant current power supply (Keithley 2400) was used, and a fixed current density was applied to the light-emitting element. The emission spectrum was measured using a spectroradiometer (CS2000). Simultaneously, at 10 mA / cm²... 2 The IVL (current-voltage-luminance) performance of the device was measured at 50 mA / cm². 2 The lifetime of the LT95 device was tested. The results are shown in Tables 1 and 2 below.

[0513] The device performance data of the light-emitting layer co-deposited with red light-doping materials using the compound of this application as a dual host and comparative compounds 1-4 as a single host or dual host are shown in Table 1 (the examples in Table 1 use the compound of this application, and the comparative examples use the comparative compounds).

[0514] Table 1

[0515] In Table 1, "-" indicates no. In Example 29, the mass ratio of the first subject to the second subject is 8:2; in Example 30, the mass ratio of the first subject to the second subject is 2:8; and in other examples, as well as Comparative Examples 2 and 4-5, the mass ratio of the first subject to the second subject is 1:1.

[0516] In this embodiment, the first host compound, the second host compound, and the third host compound were vapor-deposited and mixed in a weight ratio of 2:1:1 (first host: second host: third host), and the device data of the co-deposited light-emitting layer with the red light doping material are shown in Table 2.

[0517] Table 2

[0518] As can be seen from Tables 1-2, the device lifetime of the device prepared by the compound of this application is significantly better than that of the device prepared by comparative compounds 1-5.

[0519] Sublimation temperature comparison: The definition of sublimation temperature is: at 10 -7 The vacuum level of Torr and the temperature corresponding to a sublimation rate of 1 angstrom per second are shown in Table 3.

[0520] Table 3

[0521] As can be seen from Table 3, the compounds of this application have a lower sublimation temperature compared to comparative compounds 1-4, which is beneficial for industrial application.

[0522] The compound of this application, as a dual-host red light material, has a lower voltage, higher current efficiency, and longer lifetime than the comparative compound. Due to the balance between hole and electron transport rates, it broadens the exciton recombination region in the light-emitting layer, which greatly improves the efficiency and lifetime of the device compared with comparative examples 1-5. At the same time, when the compound of this application is used as a three-host material, it greatly improves the efficiency and lifetime of the device compared with comparative example 6.

[0523] Therefore, the compound material of this application has advantages such as low sublimation temperature, low driving voltage, high luminous efficiency, and long device lifetime, and can be used as a host material in OLED light-emitting devices. It also has a low melting point, which is beneficial for the stability of material evaporation as a molten material. The compound of this application, as a host material, has the potential for application in the AMOLED industry.

[0524] Furthermore, since it is impossible to exhaustively list all the compounds in this application, Tables 1-3 above only list some of the properties of the compounds or devices in this application. However, within the scope of protection claimed in this application, especially the compounds with the specific structural formulas given in this application, all have advantages similar to Al, such as high optical and electrical stability, low sublimation temperature, low driving voltage, high luminous efficiency, and long device life.

Claims

1. A main material composition, characterized in that, The host material composition comprises at least one first host compound and at least one second host compound, wherein the structure of the first host compound is shown in formula (1): Among them, ring A is selected from the following formula (1-2) or formula (1-3); Among them, X1-X 12 Each is independently selected as CR0 or N; and X1-X4, X 5- X6, X7-X8, X9-X 12 Two adjacent sites are fused with the 5-membered ring containing X in equation (1); Ring B is selected from substituted or unsubstituted benzene rings, naphthalene rings, or phenanthrene rings; In equation (1), X is selected from NR. a CR b R c Or oxygen group elements; R a R b R c Each and every one is independently selected from at least one of substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C1-C30 heteroalkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C3-C30 alkylsilyl or C6-C30 arylsilyl; or R b and R c Connect them into a ring; L is selected from single bond, substituted or unsubstituted C6-C60 arylene or substituted or unsubstituted C3-C60 heteroarylene; Ar1 and Ar2 are independently selected from substituted or unsubstituted C6-C60 aryl and substituted or unsubstituted C3-C60 heteroaryl, respectively; The second host compound is represented by the following formula (2): Z1, Z2, and Z3 are each independently selected from N or CR. d ; Ar3 to Ar5 each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C60 alkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, substituted or unsubstituted C3-C60 cycloalkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted tri(C1-C30)alkylsilyl, substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, or -N-(R')(R”); or Ar3 to Ar5 each independently form a ring with a substituent on a carbon atom or heteroatom adjacent to the substituted position; Among them, at least one of Ar3 to Ar5 is selected from the following formula (3): Where Y is selected from NR e CR f R g Or oxygen group elements; R e R f R g Each and every one is independently selected from at least one of substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C1-C30 heteroalkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C3-C30 alkylsilyl or C6-C30 arylsilyl; or R f and R g Connect them into a ring; in, Indicates the connection sites with L1, L2, and L3 in equation (2); Wherein, ring C is selected from substituted or unsubstituted benzene rings, naphthalene rings or phenanthrene rings; R0, R1, R d Each and every one is independently selected from hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted C1-C40 alkyl, substituted or unsubstituted C1-C40 heteroalkyl, substituted or unsubstituted C2-C40 alkenyl, substituted or unsubstituted C2-C40 alkynyl, substituted or unsubstituted C3-C40 cycloalkyl, substituted or unsubstituted C3-C40 heterocycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, substituted or unsubstituted C1 At least one of the following: -C40 alkoxy, substituted or unsubstituted C6-C60 aryloxy, substituted or unsubstituted C3-C40 alkylsilyl, substituted or unsubstituted C6-C60 arylsilyl, substituted or unsubstituted C1-C40 alkylboryl, substituted or unsubstituted C6-C60 arylboryl, substituted or unsubstituted C6-C60 arylphosphine, or substituted or unsubstituted C6-C60 arylamino; or, two adjacent R0s may be linked to form a fused ring; Wherein, R' and R” each independently represent a substituted or unsubstituted C1-C30 alkyl, a substituted or unsubstituted C2-C30 alkenyl, a substituted or unsubstituted C6-C30 aryl, or a substituted or unsubstituted C3-C30 heteroaryl. Where p is an integer from 0 to 10; if p is an integer from 2 to 10, then each R1 can be the same or different, and adjacent R1s can be connected to form a parallel ring; L1, L2, and L3 are selected from single bonds, substituted or unsubstituted C6-C60 arylene groups, substituted or unsubstituted C3-C60 heteroarylene groups, or substituted or unsubstituted C3-C30 cycloalkyl groups. The R0, R1, R a ~R g In the series L, L1-L3, Ar1-Ar5, R', R", the substitution is at least one of deuterium, halogen, cyano, isocyano, phosphin, C1-C6 alkyl, C3-C16 cycloalkyl, C1-C6 alkyl-substituted amino, 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 monosubstituted to the maximum number of substitutions; The heteroatom in the heteroaryl, heteroaryl, heteroalkyl, heterocycloalkyl, or heteroatom is independently selected from at least one of O, S, N, Se, Si, and Ge.

2. The main material composition according to claim 1, characterized in that, The ring A in formula (1) is selected from one of the structures shown in formulas (1-4) to (1-11): Where * represents the site that fused with the 5-membered ring containing X in equation (1); Where a is an integer from 0 to 10; if a ≥ 2 or a larger integer, then each R0 can be the same or different, and adjacent R0s can be connected to form a parallel ring; The definition of R0 is consistent with that of claim 1.

3. The main material composition according to claim 1, characterized in that, The ring A in formula (1) is selected from one of the structures shown in formulas (1-12) to (1-19): Where * represents the site that fused with the 5-membered ring containing X in equation (1); Where a is an integer from 0 to 6; if a is an integer from 2 to 6, then each R0 can be the same or different, and adjacent R0s can be connected to form a parallel ring; The definition of R0 is consistent with that of claim 1.

4. The main material composition according to claim 1, characterized in that, The ring B of formula (1) or the ring C of formula (3) is independently selected from one of the structures shown in formulas (1-20) to (1-26): Wherein, * represents the confluence site with the ring C containing the X quinary ring in formula (1) or the Y quinary ring in formula (3); R2 is selected from hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted C1-C40 alkyl, substituted or unsubstituted C1-C40 heteroalkyl, substituted or unsubstituted C2-C40 alkenyl, substituted or unsubstituted C2-C40 alkynyl, substituted or unsubstituted C3-C40 cycloalkyl, substituted or unsubstituted C3-C40 heterocycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, substituted... Or at least one of the following: unsubstituted C1-C40 alkoxy, substituted or unsubstituted C6-C60 aryloxy, substituted or unsubstituted C3-C40 alkylsilyl, substituted or unsubstituted C6-C60 arylsilyl, substituted or unsubstituted C1-C40 alkylboron, substituted or unsubstituted C6-C60 arylboron, substituted or unsubstituted C6-C60 arylphosphine, or substituted or unsubstituted C6-C60 arylamine; The substitution described in R2 is substituted by at least one of deuterium, halogen, cyano, isocyano, phosphin, C1-C6 alkyl, C3-C16 cycloalkyl, C1-C6 alkyl-substituted amino, C6-C30 aryl substituted or unsubstituted C1-C6 alkyl, or C3-C30 heteroaryl substituted or unsubstituted C1-C6 alkyl, wherein the number of substitutions is from monosubstituted to the maximum number of substitutions; Where q is an integer from 0 to 10; if q is an integer from 2 to 10, then each R2 can be the same or different, and adjacent R2s can be connected to form a parallel ring.

5. The main material composition according to any one of claims 1-4, characterized in that, L, L1, L2, and L3 are each independently selected from single-bonded, substituted or unsubstituted C6-C30 arylene or substituted or unsubstituted C3-C30 heteroarylene. And / or, the X is CR b R c , O or S; And / or, the R b R c Each is independently selected from C1-C10 alkyl, C1-C10 heteroalkyl, C3-C10 cycloalkyl, C3-C10 heterocycloalkyl, C6-C10 aryl, C5-C10 heteroaryl, or R b and R c The linkage forms a fluorene group; And / or, X1-X 12 It contains at least one N; And / or, in equation (2), at least two of Z1, Z2, and Z3 are N; And / or, in the host material composition, the mass ratio of the first host compound to the second host compound is 1:99 to 99:

1.

6. The main material composition according to any one of claims 1-4, characterized in that, In equation (1), X is selected from O, and in equation (2), Z1, Z2, and Z3 are all N.

7. The main material composition according to any one of claims 1-4, characterized in that, The structure of formula (3) is selected from one of the structures shown in formulas (2-1) to (2-13): Where R1, R2, R e R f R g The definitions of , p, and q are consistent with those in claim 4.

8. The main material composition according to any one of claims 1-4, characterized in that, Ar1 to Ar5 are each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthraxyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiopheneyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted 9,9-spirodifluorenyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted pyrene, substituted or unsubstituted... The group consisting of at least one of the following: substituted or unsubstituted carbazolyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted fluoranyl, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted benzotriazole, substituted or unsubstituted benzophenanthryl, substituted or unsubstituted naphthoxazolyl, substituted or unsubstituted benzocycloalkyl, substituted or unsubstituted phenanthoxazolyl, oxaspironyl, or substituted or unsubstituted benzocarbazolyl.

9. The main material composition according to claim 1, characterized in that, R0, R1, R d Each of the following is independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 heteroalkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C3-C20 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl.

10. The main material composition according to claim 1, characterized in that, R a R b R c Each is independently selected from substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C1-C15 heteroalkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C3-C15 heterocycloalkyl, substituted or unsubstituted C6-C18 aryl, substituted or unsubstituted C3-C18 heteroaryl.

11. The main material composition according to claim 1, characterized in that, Ar1 and Ar2 are independently selected from substituted or unsubstituted C6-C30 aryl groups and substituted or unsubstituted C3-C30 heteroaryl groups, respectively; Ar3 to Ar5 each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C3-C30 cycloalkyl; or Ar3 to Ar5 each independently form a ring with a substituent on a carbon atom or heteroatom adjacent to the substituted position.

12. The main material composition according to claim 1, characterized in that, The compound represented by formula (1) is selected from one of the following structural formulas, or is one of the following structural formulas in which hydrogen is partially or completely substituted by deuterium or fluorine:

13. The main material composition according to claim 1, characterized in that, The compound represented by formula (2) is selected from one of the following structural formulas, or is one of the following structural formulas in which hydrogen is partially or completely substituted by deuterium or fluorine:

14. The main material composition according to claim 1, characterized in that, The host material composition further comprises at least one third host compound, which is represented by formula (1) or formula (2), but is different from the first host compound or the second host compound.

15. An organic electroluminescent device, characterized in that, Includes the main material composition according to any one of claims 1-14.

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