A host material and an organic electroluminescent device

Abstract

The present invention belongs to the technical field of organic electroluminescence, and discloses a host material and an organic electroluminescent device. The host material comprises at least one first host compound represented by formula (1) and at least one second host compound represented by formula (2): #imgabs0# formula (1), #imgabs1# formula (2); wherein ring A is selected from the following formula (1-2) or formula (1-3): #imgabs2# formula (1-2), #imgabs3# formula (1-3), X1-X 12 are independently selected from CR0 or N, and X is selected from NR a , CR b R c Or oxygen group elements. The main material has the advantages of low sublimation temperature, low driving voltage, high luminous efficiency, long device life, etc., and can be applied to organic electroluminescent devices.

Description

Technical Field

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

[0002] At present, organic electroluminescent devices (OLEDs), as a new generation of display technology, have received more and more attention in both display and lighting technology, and have a wide range of application prospects. However, compared with market application requirements, the performance of OLED devices such as luminous efficiency, driving voltage, and service life still needs to be further improved.

[0003] Generally speaking, the basic structure of an OLED device is a thin film of organic functional materials with various functions sandwiched between metal electrodes, like a sandwich structure. Driven by electric current, electrons and holes are injected from the positive and negative poles respectively. After moving a certain distance, the holes and electrons are recombined in the light-emitting layer and released in the form of light or heat, thereby achieving a luminous effect. However, the properties of phosphorescent OLEDs are not only determined by the triplet light-emitting body used. Other types of materials, such as host materials, are also very important. The host material plays a significant role in reducing the driving voltage of the device, improving the luminous efficiency of the device, and increasing the service life of the device. However, the existing host materials have limited performance improvements on OLED devices.

[0004] Therefore, it is necessary to continue to develop new host materials and compositions thereof to further improve the performance of organic electroluminescent devices and to solve the above-mentioned problems existing in organic electroluminescent devices. Summary of the invention

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

[0006] Specifically, the first embodiment of the present invention relates to a host material, wherein the host material comprises at least one first host compound and at least one second host compound, wherein the first host compound has a structure shown in formula (1): Formula (1),

[0007] Wherein, ring A is selected from the following formula (1-2) or formula (1-3);

[0008] Formula (1-2), Formula (1-3),

[0009] Among them, X1-X 12 are independently selected from CR0 or N; and X1-X4, X 5- X6, X7-X8, X9-X12 There are two adjacent sites in which the 5-membered ring containing X in formula (1) is fused;

[0010] R0 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 substituted or unsubstituted C1-C40 alkoxy, substituted or unsubstituted C6-C60 aryloxy, substituted or unsubstituted C1-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 arylphosphino, or substituted or unsubstituted C6-C60 arylamine; or, two adjacent R0s are connected to form a ring;

[0011] wherein ring B is selected from a substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthalene ring, or a substituted or unsubstituted phenanthrene ring;

[0012] Wherein, X in formula (1) is selected from NR a , CR b R c or oxygen group elements;

[0013] R a , R b , R c are independently selected from 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 C1-C30 alkylsilyl, or substituted or unsubstituted C6-C30 arylsilyl; or, R b and R c Connect into a ring;

[0014] L is selected from a single bond, a substituted or unsubstituted C6-C60 arylene group, or a substituted or unsubstituted C3-C60 heteroarylene group;

[0015] Ar1 and Ar2 are independently selected from substituted or unsubstituted C6-C60 aryl, or substituted or unsubstituted C3-C60 heteroaryl;

[0016] Wherein, the second main compound has a structure shown in formula (2):

[0017] Formula (2),

[0018] Wherein, Z1, Z2, and Z3 are each independently selected from N or CR d ;

[0019] 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 link to a substituent on a carbon atom or heteroatom adjacent to the substitution position thereof to form a ring;

[0020] Among them, at least one of Ar3 to Ar5 is selected from the following formula (2-1), formula (2-2) or formula (2-3):

[0021] ,

[0022] in, represents the connection site with L1, L2, and L3 in formula (2);

[0023] R d , R1 are each 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-C6 0 heteroaryl, substituted or unsubstituted C1-C40 alkoxy, substituted or unsubstituted C6-C60 aryloxy, substituted or unsubstituted C1-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 arylphosphino, or substituted or unsubstituted C6-C60 arylamine;

[0024] wherein R' and R" each independently represent a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C2-C30 alkenyl group, a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C3-C30 heteroaryl group;

[0025] q is an integer of 0-10, wherein when q is an integer of 2-10, each R1 may be the same or different, and adjacent R1 may be connected to form a ring;

[0026] L1, L2, and L3 are independently selected from a single bond, a substituted or unsubstituted C6-C60 arylene group, a substituted or unsubstituted C3-C60 heteroarylene group, or a substituted or unsubstituted C3-C30 cycloalkylene group;

[0027] R0, R1, R a ~R d , L, L1~L3, Ar1~Ar5, R', R", the substitution is substituted by at least one of deuterium, halogen, cyano, isocyano, phosphino, C1-C6 alkyl, C3-C16 cycloalkyl, C1-C6 alkyl substituted amine, C1-C6 hydrocarbon substituted or unsubstituted C6-C30 aryl, or C1-C6 hydrocarbon substituted or unsubstituted C3-C30 heteroaryl, wherein the number of substitutions ranges from a single substitution to a maximum number of substitutions;

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

[0029] The beneficial effects of the present invention are as follows:

[0030] The main material of the present invention has the advantages of low sublimation temperature, low driving voltage, high luminous efficiency, long device life, etc., and can be used as a main material in OLED light-emitting devices. At the same time, it has a low melting point, and as a molten material, it is beneficial to the stability of material evaporation. As a red light main material, the main material has the possibility of being applied to the AMOLED (active matrix organic light-emitting diode) industry. BRIEF DESCRIPTION OF THE DRAWINGS

[0031] Figure 1 is the compound A226 of the present invention 1 H NMR spectrum;

[0032] Figure 2 FIG. 1 is a schematic structural diagram of an organic electroluminescent device according to an embodiment of the present invention. DETAILED DESCRIPTION

[0033] In order to make the technical scheme of the present invention more clearly understood by those skilled in the art, the following embodiments are listed for illustration. It should be pointed out that the following embodiments do not limit the protection scope of the present invention.

[0034] Specifically, the first embodiment of the present invention relates to a host material, which comprises at least one first host compound and at least one second host compound, wherein the first host compound has a structure shown in formula (1):

[0035] Formula (1),

[0036] Wherein, ring A is selected from the following formula (1-2) or formula (1-3);

[0037] Formula (1-2), Formula (1-3),

[0038] Among them, X1-X 12 are independently selected from CR0 or N; and X1-X4, X 5- X6, X7-X8, X9-X 12 There are two adjacent sites in which the 5-membered ring containing X in formula (1) is fused;

[0039] R0 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 substituted or unsubstituted C1-C40 alkoxy, substituted or unsubstituted C6-C60 aryloxy, substituted or unsubstituted C1-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 arylphosphino, or substituted or unsubstituted C6-C60 arylamine; or, two adjacent R0s are connected to form a ring;

[0040] wherein ring B is selected from a substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthalene ring, or a substituted or unsubstituted phenanthrene ring;

[0041] Wherein, X in formula (1) is selected from NR a , CR b R c or oxygen group elements;

[0042] R a , R b , R care independently selected from 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 C1-C30 alkylsilyl, or substituted or unsubstituted C6-C30 arylsilyl; or, R b and R c Connect into a ring;

[0043] L is selected from a single bond, a substituted or unsubstituted C6-C60 arylene group, or a substituted or unsubstituted C3-C60 heteroarylene group;

[0044] Ar1 and Ar2 are independently selected from substituted or unsubstituted C6-C60 aryl, or substituted or unsubstituted C3-C60 heteroaryl;

[0045] Wherein, the second main compound has a structure shown in formula (2):

[0046] Formula (2),

[0047] Wherein, Z1, Z2, and Z3 are each independently selected from N or CR d ;

[0048] 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 link to a substituent on a carbon atom or heteroatom adjacent to the substitution position thereof to form a ring;

[0049] Among them, at least one of Ar3 to Ar5 is selected from the following formula (2-1), formula (2-2) or formula (2-3):

[0050] ,

[0051] in, represents the connection site with L1, L2, and L3 in formula (2);

[0052] R d, R1 are each 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-C6 0 heteroaryl, substituted or unsubstituted C1-C40 alkoxy, substituted or unsubstituted C6-C60 aryloxy, substituted or unsubstituted C1-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 arylphosphino, or substituted or unsubstituted C6-C60 arylamine;

[0053] wherein R' and R" each independently represent a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C2-C30 alkenyl group, a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C3-C30 heteroaryl group;

[0054] q is an integer of 0-10, wherein when q is an integer of 2-10, each R1 may be the same or different, and adjacent R1 may be connected to form a ring;

[0055] L1, L2, and L3 are independently selected from a single bond, a substituted or unsubstituted C6-C60 arylene group, a substituted or unsubstituted C3-C60 heteroarylene group, or a substituted or unsubstituted C3-C30 cycloalkylene group;

[0056] R0, R1, R a ~R d , L, L1~L3, Ar1~Ar5, R', R", are each independently substituted by at least one of deuterium, halogen, cyano, isocyano, phosphino, C1-C6 alkyl, C3-C16 cycloalkyl, C1-C6 alkyl substituted amine, C1-C6 hydrocarbon substituted or unsubstituted C6-C30 aryl, or C1-C6 hydrocarbon substituted or unsubstituted C3-C30 heteroaryl, wherein the number of substitutions ranges from a single substitution to a maximum number of substitutions;

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

[0058] In some embodiments, ring A is selected from one of the structures represented by the following formula (1-4) to formula (1-11):

[0059] ,

[0060] ,

[0061] in, represents the site of fusion with the 5-membered ring containing X in formula (1);

[0062] Wherein a is an integer of 0-10; when a is an integer of 2-10, each R0 may be the same or different, and adjacent R0 may be connected to form a ring.

[0063] In some embodiments, ring A is selected from one of the structures represented by the following formula (1-12) to formula (1-19):

[0064] ,

[0065] ,

[0066] in, represents the site of fusion with the 5-membered ring containing X in formula (1);

[0067] Wherein a is an integer of 0-6; when a is an integer of 2-6, each R0 may be the same or different, and adjacent R0 may be connected to form a ring.

[0068] In some embodiments, R0 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-C20 aryl, substituted or unsubstituted C3-C20 -C20 heteroaryl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C20 aryloxy, substituted or unsubstituted C1-C20 alkylsilyl, substituted or unsubstituted C6-C20 arylsilyl, substituted or unsubstituted C1-C20 alkylboryl, substituted or unsubstituted C6-C20 arylboryl, substituted or unsubstituted C6-C20 arylphosphino, or substituted or unsubstituted C6-C20 arylamine.

[0069] In some embodiments, R0 is independently selected from hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C1-C10 heteroalkyl, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C2-C10 alkynyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C3-C10 heterocycloalkyl, substituted or unsubstituted C6-C12 aryl, or substituted or unsubstituted C3-C12 heteroaryl.

[0070] In some embodiments, adjacent R0 refers to R0 located on adjacent carbon atoms.

[0071] In some embodiments, Ring B of Formula (1) is selected from one of the structures shown in the following Formulas (1-20) to (1-26):

[0072] ,

[0073] ,

[0074] in, represents the fusion site with the five-membered ring containing X in formula (1);

[0075] R g 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 a substituted or unsubstituted C1-C40 alkoxy group, a substituted or unsubstituted C6-C60 aryloxy group, a substituted or unsubstituted C1-C40 alkylsilyl group, a substituted or unsubstituted C6-C60 arylsilyl group, a substituted or unsubstituted C1-C40 alkylboryl group, a substituted or unsubstituted C6-C60 arylboryl group, a substituted or unsubstituted C6-C60 arylphosphino group, or a substituted or unsubstituted C6-C60 arylamine group;

[0076] R g The substitution is substituted by at least one of deuterium, halogen, cyano, isocyano, phosphino, C1-C6 alkyl, C3-C16 cycloalkyl, C1-C6 alkyl substituted amine, C1-C6 hydrocarbon substituted or unsubstituted C6-C30 aryl, or C1-C6 hydrocarbon substituted or unsubstituted C3-C30 heteroaryl, wherein the number of substitutions ranges from a single substitution to a maximum number of substitutions;

[0077] Where w is an integer from 0 to 10; when w is an integer from 2 to 10, each R g Can be the same or different, and adjacent R g Can be connected to form a ring.

[0078] In some embodiments, R gindependently 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-C20 aryl, substituted or unsubstituted C3-C20 heteroaryl The present invention may comprise a substituted or unsubstituted C1-C20 alkyloxy group, a substituted or unsubstituted C1-C20 alkoxy group, a substituted or unsubstituted C6-C20 aryloxy group, a substituted or unsubstituted C1-C20 alkylsilyl group, a substituted or unsubstituted C6-C20 arylsilyl group, a substituted or unsubstituted C1-C20 alkylboryl group, a substituted or unsubstituted C6-C20 arylboryl group, a substituted or unsubstituted C6-C20 arylphosphino group, or a substituted or unsubstituted C6-C20 arylamine group.

[0079] In some embodiments, R g independently selected from hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C1-C10 heteroalkyl, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C2-C10 alkynyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C3-C10 heterocycloalkyl, substituted or unsubstituted C6-C12 aryl, or substituted or unsubstituted C3-C12 heteroaryl.

[0080] In some embodiments, R g Independently selected from hydrogen, deuterium, methyl, deuterated methyl, halogen, phenyl, tert-butyl, naphthyl, cyano or cyclohexyl. Wherein, in the deuterated methyl, the deuteration can be monodeuterated, dideuterated or trideuterated.

[0081] In some embodiments, L, L1, L2, and L3 are independently selected from a single bond, a substituted or unsubstituted C6-C40 arylene group, or a substituted or unsubstituted C3-C40 heteroarylene group.

[0082] In some embodiments, L, L1, L2, and L3 are independently selected from a single bond, a substituted or unsubstituted C6-C30 arylene group, or a substituted or unsubstituted C3-C30 heteroarylene group.

[0083] In some embodiments, L, L1, L2, and L3 are independently selected from a single bond or one of the structures represented by the following formulas (3-1) to (3-17):

[0084] , ,

[0085] in, Indicates the bonding sites of L, L1, L2, and L3.

[0086] In some embodiments, X is selected from NR a , CR b R c , O, S or Se.

[0087] In some embodiments, R a , R b , R c are independently selected from substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C1-C10 heteroalkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C3-C10 heterocycloalkyl, substituted or unsubstituted C6-C10 aryl, or substituted or unsubstituted C5-C10 heteroaryl; or, R b and R c Linked to form fluorene groups (e.g. ).

[0088] In some embodiments, X1-X 12 Contains at least one N.

[0089] In some embodiments, Z1, Z2, and Z3 are each independently selected from N or CR d , R d Z1, Z2, and Z3 are independently selected from hydrogen, deuterium, halogen, cyano, nitro, or C1-C10 alkyl, and at least one of Z1, Z2, and Z3 is N.

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

[0091] In some embodiments, in formula (1), X is selected from O or S.

[0092] In some embodiments, in formula (1), X is selected from O or S; in formula (2), Z1, Z2, and Z3 are all selected from N.

[0093] In some embodiments, in formula (1), X is selected from O; in formula (2), Z1, Z2, and Z3 are all selected from N.

[0094] In some embodiments, Ar3 to Ar5 are each independently selected from 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-C20 alkoxy, substituted or unsubstituted tri(C1-C20)alkylsilyl, substituted or unsubstituted di(C1-C20)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C20)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl.

[0095] In some embodiments, in formula (2), Ar3 to Ar5 are independently selected from the structures shown in the following formula (2-4), formula (2-5) or formula (2-6):

[0096] ,

[0097] in, represents the bonding site from Ar3 to Ar5.

[0098] In some embodiments, R d R1 is each 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-C20 aryl, substituted or unsubstituted C3-C2 The present invention may be selected from the group consisting of a substituted or unsubstituted C1-C20 heteroaryl group, a substituted or unsubstituted C1-C20 alkoxy group, a substituted or unsubstituted C6-C20 aryloxy group, a substituted or unsubstituted C1-C20 alkylsilyl group, a substituted or unsubstituted C6-C20 arylsilyl group, a substituted or unsubstituted C1-C20 alkylboryl group, a substituted or unsubstituted C6-C20 arylboryl group, a substituted or unsubstituted C6-C20 arylphosphino group, or a substituted or unsubstituted C6-C20 arylamine group.

[0099] In some embodiments, R d , R1 are each independently selected from hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C1-C10 heteroalkyl, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C2-C10 alkynyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C3-C10 heterocycloalkyl, substituted or unsubstituted C6-C12 aryl, or substituted or unsubstituted C3-C12 heteroaryl.

[0100] In some embodiments, Rd , R1 are each independently selected from hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C1-C10 heteroalkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C3-C10 heterocycloalkyl, substituted or unsubstituted C6-C12 aryl, or substituted or unsubstituted C3-C12 heteroaryl.

[0101] In some embodiments, R d , R1 are each independently selected from hydrogen, deuterium, halogen, cyano, nitro or C1-C10 alkyl.

[0102] 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 anthracenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted 9,9-spirobifluorenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted pyrenyl, At least one of substituted chrysene, substituted or unsubstituted carbazolyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidyl, substituted or unsubstituted fluoranthene, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted benzotriazolyl, substituted or unsubstituted triphenylene, substituted or unsubstituted naphthoxazolyl, substituted or unsubstituted benzocycloalkyl, substituted or unsubstituted phenanthroxazolyl, oxaspirofluorene, or substituted or unsubstituted benzocarbazolyl. It is understood that at least one of Ar3 to Ar5 is selected from substituted or unsubstituted phenanthrenyl, substituted or unsubstituted triphenylene, and satisfies the structures shown in formula (2-1) to (2-3), and more specifically, satisfies the structures shown in formula (2-4) to (2-6).

[0103] In some embodiments, the substitutions are each independently substituted by at least one of deuterium, halogen, cyano, isocyano, phosphino, C1-C6 alkyl, C3-C12 cycloalkyl, C1-C6 alkyl substituted amine, C6-C18 aryl or C3-C18 heteroaryl, wherein the number of substitutions is from a single substitution to the maximum number of substitutions.

[0104] In some embodiments, the substitutions are each independently substituted by at least one of deuterium, halogen, cyano, isocyano, phosphino, C1-C6 alkyl, C3-C10 cycloalkyl, C1-C6 alkyl substituted amine, C6-C12 aryl or C3-C12 heteroaryl, wherein the number of substitutions is from a single substitution to the maximum number of substitutions.

[0105] In some embodiments, the aryl group is selected from phenyl, naphthyl, anthracenyl, phenanthrenyl, tetraphenyl, pyrenyl, perylene, chrysene, acenaphthenyl, benzopyrenyl, benzo[c]phenanthrenyl, benzo[g]chrysene, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, biphenyl, terphenyl, quaterphenyl, or fluoranthenyl.

[0106] In some embodiments, the heteroaryl group is selected from pyrrolyl, pyrrolopyrrolyl, furopyrrolyl, thienopyrrolyl, pyridinyl, pyrazolyl, pyrimidinyl, pyrazinyl, triazinyl, pyridazinyl, phenazinyl, phenothiazinyl, phenoxazinyl, indolyl, isoindolyl, imidazolyl, benzimidazolyl, triazolyl, tetrazolyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, furofuranyl, azadibenzofuranyl, thienofuranyl, diazadibenzofuranyl, benzo[B]naphtho[1, 2-D] furanyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, quinazolinonyl, carbazolyl, azacarbazolyl, diazacarbazolyl, phenanthridinyl, primary pyridinyl, acridinyl, dihydroacridinyl, phenanthrolinyl, oxazolinyl, oxazolyl, oxadiazolyl, benzisoxazolyl, thiazolyl, benzothiazolyl, benzisothiazolyl, pyrroloimidazolyl, furazanyl, thienyl, benzothienyl, dibenzothienyl, azadibenzothienyl, diazadibenzothienyl, thienothiphenyl or o-naphthyridinyl.

[0107] In some embodiments, the arylphosphino group is selected from a monoarylphosphino group or a diarylphosphino group.

[0108] 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 replaced by deuterium or fluorine:

[0109]

[0110]

[0111]

[0112]

[0113]

[0114]

[0115] In some embodiments, the compound represented by formula (2) is selected from one of the following structural formulas, or one of the following structural formulas in which hydrogen is partially or completely replaced by deuterium or fluorine:

[0116]

[0117] ,

[0118]

[0119]

[0120] In some embodiments, the host material comprises a first host compound and a second host compound, and the weight ratio of the first host compound to the second host compound can be 1:99 to 99:1, preferably 10:90 to 90:10, more preferably selected from 20:80 to 80:20, 30:70 to 70:30 or 40:60 to 60:40, and even more preferably 50:50.

[0121] In some embodiments, the host material further comprises at least one third host compound, wherein the third host compound is represented by formula (1) or formula (2) but is different from the first host compound or the second host compound.

[0122] In some embodiments, in the host material, the first host compound is represented by formula (1), the second host compound and the third host compound are both represented by formula (2), the second host compound is selected from one of the structures shown in B1-B210, and the third host compound is selected from one of the structures shown in C1-C20.

[0123] In some embodiments, the host material comprises a first host compound, a second host compound and a third host compound, and the third host compound is different from the first host compound and the second host compound. The weight ratio of the first host compound in the host material is 5wt% to 90wt%, preferably selected from 10wt% to 90wt%, 10wt% to 80wt%, 20wt% to 80wt%, 15wt% to 70wt%, 30wt% to 70wt%, 20wt% to 60wt%, or 30wt% to 60wt%; the weight ratio of the second host compound is about 5wt% to 90wt%, preferably selected from 10wt% to 90wt%, 10wt% to 80wt%, 15wt% to 70wt%, 30wt% to 70wt%, 20wt% to 60wt%, or 30wt% to 60wt%; the weight ratio of the second host compound is about 5wt% to 90wt%, preferably selected from 10wt% to 90wt%, 10wt% to 80wt%, 15wt% to 70wt%, 30wt% to 70wt%, 20wt% to 60wt%, or 30wt% to 60wt%. 0wt%~40wt%, 15wt%~70wt%, 30wt%~70wt%, 20wt%~60wt%, or 30wt%~60wt%; the weight ratio of the third host compound is about 5wt%~90wt%, preferably selected from 10wt%~90wt%, 10wt%~80wt%, 10wt%~40wt%, 15wt%~70wt%, 30wt%~70wt%, 20wt%~60wt%, or 30wt%~60wt%. For example, the host material can include a first host compound weight ratio of 5wt%~70wt%, a second host compound weight ratio of 5wt%~70wt%, and a third host compound weight ratio of 10wt%~90wt%. The host material can also include a first host compound weight ratio of 20wt%~80wt%, a second host compound weight ratio of 10wt%~40wt%, and a third host compound weight ratio of 10wt%~40wt%.

[0124] A second aspect of the present invention provides an organic electroluminescent device.

[0125] Specifically, an organic electroluminescent device includes the above-mentioned host material.

[0126] In some embodiments, an organic electroluminescent device includes an anode and a cathode, wherein a light-emitting layer is disposed between the anode and the cathode, and the light-emitting layer includes the above-mentioned host material.

[0127] In one embodiment, the light-emitting layer is a red light-emitting layer, including a red light-emitting material and the above-mentioned host material. In this embodiment, the host material is used as the host material of the red light-emitting layer.

[0128] The third aspect of the present invention provides the application of the above compound in the semiconductor field.

[0129] Specifically, the above main material is used in the preparation of semiconductor devices.

[0130] In some embodiments, the semiconductor device includes an optoelectronic device.

[0131] The main material of this embodiment has the advantages of low sublimation temperature, low driving voltage, high luminous efficiency, and long device life, and can be used as a main material in OLED light-emitting devices. At the same time, it has a low melting point, which is beneficial to the stability of material evaporation as a molten material. As a red light main material, this main material has the possibility of being applied to the AMOLED (active matrix organic light-emitting diode) industry.

[0132] definition

[0133] Unless otherwise specified, the scientific and technical terms used herein have the meanings commonly understood by those skilled in the art, but for a better understanding of the present invention, the definitions of some terms are provided below. When the definitions of terms provided by the present invention are inconsistent with the meanings commonly understood by those skilled in the art, the definitions and interpretations of the terms provided by the present invention shall prevail.

[0134] The term "alkyl" refers to a straight 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 include methyl, ethyl, propyl, butyl, heptyl, decyl, etc. Each group includes various isomers, such as butyl includes isomers such as n-butyl, isobutyl, sec-butyl, tert-butyl, etc.

[0135] The term "heteroalkyl" means that at least one carbon atom on the basis of an alkyl group is replaced by a non-carbon atom or a group containing a non-carbon atom, and 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 the case where the carbon atom connected to the main structure in the alkyl group is replaced by a non-carbon atom (such as alkoxy, alkylsilyl, alkylboryl). Non-limiting examples of heteroalkyl groups include mercaptomethyl, methoxymethyl, ethoxymethyl, tert-butoxymethyl, and N,N-dimethylmethyl.

[0136] The term "alkoxy" refers to a group having an -O-alkyl group, ie, an alkyl group as defined above attached to a given group or given formula via an oxygen atom. Non-limiting examples of alkoxy groups include: methoxy, ethoxy, and tert-butoxy.

[0137] The term "alkenyl" refers to a hydrocarbon group containing at least one double bond. The number of carbon atoms of the 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-hexatrienyl, 2-hexatrienyl, 3-hexatrienyl.

[0138] The term "alkynyl" refers to a hydrocarbon group containing at least one triple bond. The number of carbon atoms in the 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 include: ethynyl and propargyl.

[0139] The term "cycloalkyl" refers to a non-aromatic carbocyclic ring consisting of at least 3 carbon atoms, which may include monocyclic, polycyclic and spiroalkyl. The carbon number of 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 include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, bicyclo [3.1.1] heptyl, spiro [4.5] decyl, spiro [5.5] undecyl, adamantyl, norbornyl.

[0140] The term "heterocycloalkyl" refers to a cycloalkyl group in which at least one carbon atom is replaced by a non-carbon atom, and the non-carbon atom can be selected from at least one of O, S, N, P, B, Si, Ge or Se. The number of carbon atoms in the heterocycloalkyl group can 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 heterocycloalkyl groups include: butylene oxide, pentylene oxide and hexylene oxide.

[0141] The term "aryl" refers to an aromatic hydrocarbon group derived from an aromatic ring compound by removing a hydrogen atom, which can be a monocyclic aromatic group or a polycyclic aromatic group. At least one ring in the polycyclic aromatic group is an aromatic ring system. In the polycyclic aromatic group, multiple rings can be connected to each other via a single bond or can be fused to each other. The number of carbon atoms of 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 the polycyclic aromatic group contains a fused ring structure, it can be specifically formed by condensing a C3-C30 aliphatic ring (a saturated or unsaturated aliphatic ring containing 3 to 30 ring skeleton carbon atoms) and a C3-C30 aromatic ring (an aromatic ring containing 3 to 30 ring skeleton carbon atoms), more specifically, by condensing a C3-C20 aliphatic ring and a C6-C30 aromatic ring. It can be understood that the term "arylene" refers to an aromatic hydrocarbon group derived from an aromatic ring compound by removing two hydrogen atoms.

[0142] The term "heteroaryl" refers to a monovalent group in which at least one carbon atom is replaced by a non-carbon atom based on an aryl group, wherein the non-carbon atom can be selected from a heterocyclic aromatic system of O, S, N, P, B, Se, Si or Ge, but does not include the case where the aryl group is connected to the main structure through a non-carbon atom group (e.g., aryloxy, arylsilyl, arylboryl, arylphosphino, arylamine). It is understood that the term "heteroarylene" refers to a divalent group having the same structure as a heteroaryl group.

[0143] "Ar3 to Ar5 are each independently connected to a substituent on a carbon atom adjacent to the substitution position thereof to form a ring" means that the substituent on the substitution position of Ar3 to Ar5 and the substituent on the carbon atom of L1 to L3 can be connected to form a ring, or when L1 to L3 are single bonds, the substituent on the substitution position of Ar3 to Ar5 and Z1 to Z3 can be connected to form a ring. For example, L1 and Ar3, L2 and Ar4, L3 and Ar5 can be optionally connected to each other to form a substituted or unsubstituted following ring: naphthalene, fluorenyl, quinoline, dibenzothiophene, dibenzofuran, carbazole, benzofuranopyridine, benzothienopyridine, indenopyridine, benzofuranoquinoline, benzothienoquinoline, or indenoquinoline ring.

[0144] The term "adjacent" refers to two groups or atoms that are directly bonded to each other, or two groups or atoms that are directly adjacent substituents to each other (ie, the two substituents are directly connected, rather than indirectly connected through other atoms or groups).

[0145] The "carbon number ab" in the expression "a substituted or unsubstituted X group having ab carbon numbers" means the carbon number when the X group is unsubstituted, and does not include the carbon number of a substituent when the X group is substituted.

[0146] The "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 limited by the definition, it also includes that one or more hydrogen atoms are replaced by a group formed by connecting two or more of the above-mentioned substituents.

[0147] The following embodiments are only for facilitating the understanding of the technical invention and should not be regarded as specific limitations of the present invention.

[0148] The raw materials and solvents involved in the synthesis of the compounds of the present invention were purchased from suppliers familiar to those skilled in the art such as Alfa and Acros. The raw materials, reagents or devices used, unless otherwise specified, can be obtained from conventional commercial channels or can be obtained by existing known methods.

[0149] Synthesis of Compound A1

[0150] .

[0151] Synthesis of Compound A1-3

[0152] A1-1 (30.00 g, 106.56 mmol), A1-2 (32.47 g, 127.87 mmol), 1,1-bis(diphenylphosphine)dichloropalladium iron (Pd(dppf)Cl2, 1.56 g, 2.13 mmol), potassium acetate (KOAc, 15.69 g, 159.84 mmol), 1,4-dioxane (1,4-Dioxane, 450 mL) were added to a 1000 ml three-necked round-bottom flask, and the vacuum was replaced with nitrogen three times. Then, the system was heated to 100 ° C for 2 hours. The reaction was monitored by TLC (ethyl acetate: n-hexane = 1:10 as the developing solvent). A1-1 was completely consumed.

[0153] The temperature was lowered to 60°C, and the solvent was removed by concentrating under reduced pressure. Ethyl acetate (700 ml) was added, and the mixture was washed three times with deionized water (300 mL × 3). The mixture was separated, and the sample was mixed with silica gel and dry-loaded onto a column. Purification was performed by silica gel column chromatography (200-300 mesh silica gel, ethyl acetate:n-hexane = 1:15 as eluent). After elution, the mixture was concentrated under reduced pressure at 70°C for 1 hour to obtain a white solid A1-3 (27.62 g, purity: 98.01%, yield: 78.88%), with a mass spectrum of 329.12 (M+H).

[0154] Synthesis of Compound A1-5

[0155] A1-3 (25.00 g, 76.08 mmol), A1-4 (17.89 g, 76.08 mmol), tetrakis(triphenylphosphine)palladium (Pd(PPh3)4, 1.75 g, 1.52 mmol), potassium carbonate (K2CO3, 15.77 g, 114.12 mmol), tetrahydrofuran (THF, 375 mL), and deionized water (125 mL) were added to a 1000 mL three-necked round-bottom flask, and the vacuum nitrogen was replaced three times. Then, the system was heated to 75 ° C for 3 hours. The reaction was monitored by TLC (ethyl acetate: n-hexane = 1:10 as the developing solvent). A1-3 was completely consumed.

[0156] The temperature was lowered to 60°C, and the solvent was removed by concentration under reduced pressure. Ethyl acetate (700 mL) was added, and the mixture was washed three times with deionized water (300 mL × 3). The mixture was separated, and the sample was mixed with silica gel and dry-loaded onto a column. Purification was performed by silica gel column chromatography (200-300 mesh silica gel, ethyl acetate:n-hexane = 1:20 as eluent). After elution, the mixture was concentrated under reduced pressure at 70°C for 2 hours to obtain a white solid A1-5 (20.45 g, purity: 99.21%, yield: 75.32%), with a mass spectrum of 357.22 (M+H).

[0157] Synthesis of Compound A1-7

[0158] A1-5 (18.00 g, 50.45 mmol), A1-6 (25.94 g, 75.67 mmol), and tetrahydrofuran (THF, 270 ml) were added to a 1000 mL three-necked round-bottom flask, and the vacuum nitrogen was replaced three times. Then the system was cooled to 5°C, and sodium methoxide (NaOMe, 5.45 g, 100.90 mmol) was added at once. The reaction was maintained at 5°C for 1 hour. The reaction was monitored by TLC (ethyl acetate: n-hexane = 1:10 as the developing solvent). The raw material A1-5 was completely consumed.

[0159] Deionized water (500 mL) was added, the solvent was removed by concentration under reduced pressure, ethyl acetate (700 mL) was added for extraction, the liquids were separated, and the mixture was concentrated under reduced pressure at 70°C for 1 hour to obtain a white solid A1-7 (18.44 g, yield: 95.00%), mass spectrum: 385.04 (M+H). The obtained compound was used directly in the next step without purification.

[0160] Synthesis of Compound A1-8

[0161] A1-7 (17.00 g, 44.17 mmol) and toluene (170 ml) were added to a 500 mL three-necked round-bottom flask, and the vacuum was replaced with nitrogen three times. Then the system was cooled to 5°C, and methanesulfonic acid (MsOH, 8.49 g, 88.34 mmol) was slowly added dropwise. The addition was completed within 3 minutes, and the reaction was maintained at 5°C for 1 hour. The reaction was monitored by TLC (ethyl acetate: n-hexane = 1:15 as the developing solvent). The raw material A1-7 was completely consumed.

[0162] Methanol (200 mL) was added thereto to precipitate a large amount of white solid, which was filtered to obtain 17 g of solid. Toluene (204 mL) and methanol (170 mL) were used for crystallization once, and the filter cake was filtered off under vacuum at 80 ° C for 1 hour to obtain a white solid A1-8 (11.63 g, purity: 99.83%, yield: 74.62%), mass spectrum: 353.06 (M+H).

[0163] Synthesis of Compound A1

[0164] A1-8 (10.00 g, 28.34 mmol), A1-9 (7.30 g, 29.76 mmol), tris(dibenzylideneacetone)dipalladium (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) were added to a 500 mL three-necked round-bottom flask, and the vacuum nitrogen was replaced three times. Then, the system was heated to 105 ° C for 2 hours. The reaction was monitored by TLC (ethyl acetate: n-hexane = 1:15 as the developing solvent). The raw material A1-8 was consumed.

[0165] The temperature was lowered to 60°C, methanol (150 mL) was added, and the mixture was naturally cooled to room temperature and stirred for 30 minutes to precipitate a large amount of solids. The mixture was filtered to obtain 20 g of solids. Toluene (300 mL) was added, and the system was then heated to 100°C to dissolve and clarify. 30 g of silica gel (300-400 mesh) was spread and filtered. The surface of the silica gel was rinsed with toluene (50 mL). The filtrate was combined and concentrated to obtain 18 g. Toluene (180 mL) and methanol (90 mL) were used for crystallization twice, and the mixture was filtered and dried under vacuum at 90°C for 3 hours to obtain a light yellow solid A1 (14.07 g, purity: 99.94%, yield: 88.41%). 14.07 g of crude A1 was purified by sublimation to obtain sublimation pure A1 (11.26 g, purity: 99.95%, yield: 80.02%), with a mass spectrum of 562.22 (M+H).

[0166] 1H NMR (400 MHz, CDCl3) δ 8.17 (d, J = 9.1 Hz, 1H), 8.07 - 8.00 (m,1H), 7.97 - 7.87 (m, 4H), 7.85 (dd, J = 7.5, 3.0 Hz, 2H), 7.60 - 7.55 (m,2H), 7.55 - 7.48 (m, 4H), 7.42 - 7.39 (m, 3H), 7.32 (d, J = 7.3 Hz, 1H), 7.31- 7.24 (m, 2H), 7.16 - 7.07 (m, 5H), 7.02 - 6.97 (m, 2H).

[0167] Synthesis of Compound A54

[0168] .

[0169] Synthesis of Compound A54-2

[0170] Referring to the synthesis and purification method of compound A1-3, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound A54-2 (28.02 g, purity: 98.52%, yield: 77.65%), mass spectrum: 329.12 (M+H).

[0171] Synthesis of Compound A54-3

[0172] Referring to the synthesis and purification method of compound A1-5, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound A54-3 (26.33 g, purity: 99.45%, yield: 75.09%), mass spectrum: 357.22 (M+H).

[0173] Synthesis of Compound A54-4

[0174] Referring to the synthesis and purification method of compound A1-7, only the corresponding raw materials need to be changed to obtain the target compound A54-4 (24.44 g, yield: 97.89%) as a white solid, with a mass spectrum of 385.04 (M+H). The obtained compound was used directly in the next step without purification.

[0175] Synthesis of Compound A54-5

[0176] Referring to the synthesis and purification method of compound A1-8, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound A54-5 (16.85 g, purity: 99.79%, yield: 76.85%), mass spectrum: 353.06 (M+H).

[0177] Synthesis of compound A54

[0178] Referring to the synthesis and purification method of compound A1, only the corresponding raw materials need to be changed to obtain the target compound A54 (16.74 g, purity: 99.95%, yield: 78.65%) as a light yellow solid. 16.74 g of crude A54 was purified by sublimation to obtain sublimation pure A54 (13.10 g, purity: 99.95%, yield: 78.26%), mass spectrum: 612.22 (M+H).

[0179] 1 H NMR (400 MHz, CDCl3) δ 8.64 (s, 1H), 8.33 – 8.26 (m, 1H), 8.01 (d,J = 8.9 Hz, 1H), 7.96 (d, J = 8.0 Hz, 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 = 2.2 Hz, 1H), 7.09 – 7.01 (m, 2H), 7.01 – 6.97 (m, 2H), 6.86 (dd, J = 7.6, 2.2 Hz, 1H).

[0180] Synthesis of compound A73

[0181] .

[0182] Synthesis of Compound A73-2

[0183] Referring to the synthesis and purification method of compound A1-3, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound A73-2 (30.54 g, purity: 98.44%, yield: 77.12%), mass spectrum: 329.12 (M+H).

[0184] Synthesis of Compound A73-3

[0185] Referring to the synthesis and purification method of compound A1-5, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound A73-3 (27.09 g, purity: 99.66%, yield: 76.36%), mass spectrum: 357.22 (M+H).

[0186] Synthesis of Compound A73-4

[0187] Referring to the synthesis and purification method of compound A1-7, only the corresponding raw materials need to be changed to obtain the target compound A73-4 (23.12 g, yield: 93.93%) as a white solid, with a mass spectrum of 385.04 (M+H). The obtained compound was used directly in the next step without purification.

[0188] Synthesis of Compound A73-5

[0189] Referring to the synthesis and purification method of compound A1-8, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound A73-5 (18.08 g, purity: 99.65%, yield: 40.20%), mass spectrum: 353.06 (M+H).

[0190] Synthesis of Compound A73-8

[0191] Referring to the synthesis and purification method of compound A1, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound A73-8 (23.11 g, purity: 99.60%, yield: 76.44%), mass spectrum: 337.13 (M+H).

[0192] Synthesis of compound A73

[0193] Referring to the synthesis and purification method of compound A1, only the corresponding raw materials need to be changed to obtain the target compound A73 (16.76 g, purity: 99.92%, yield: 76.22%) as a light yellow solid. 16.76 g of crude A73 was purified by sublimation to obtain sublimation pure A73 (14.21 g, purity: 99.92%, yield: 84.78%), mass spectrum: 653.21 (M+H).

[0194] 1 H NMR (400 MHz, CDCl3) δ 8.33 - 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).

[0195] Synthesis of Compound A89

[0196] .

[0197] Synthesis of Compound A89-3

[0198] Referring to the synthesis and purification method of compound A1-5, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound A89-3 (19.88 g, purity: 99.57%, yield: 78.08%), mass spectrum: 357.04 (M+H).

[0199] Synthesis of Compound A89-4

[0200] Referring to the synthesis and purification method of compound A1-7, only the corresponding raw materials need to be changed to obtain the target compound A89-4 (25.58 g, yield: 94.35%) as a white solid, with a mass spectrum of 385.04 (M+H). The obtained compound was used directly in the next step without purification.

[0201] Synthesis of Compound A89-5

[0202] Referring to the synthesis and purification method of compound A1-8, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound A89-5 (20.01 g, purity: 99.74%, yield: 78.63%), mass spectrum: 353.06 (M+H).

[0203] Synthesis of Compound A89

[0204] Referring to the synthesis and purification method of compound A1, only the corresponding raw materials need to be changed to obtain the yellow solid as the target compound A89 (17.77 g, purity: 99.94%, yield: 71.06%). 17.77 g of crude A89 was purified by sublimation to obtain sublimation pure A89 (15.02 g, purity: 99.94%, yield: 84.52%), mass spectrum: 678.22 (M+H).

[0205] 1 H NMR (400 MHz, CDCl3) δ 8.47 (dd, J = 7.6, 1.4 Hz, 1H), 8.16 - 8.10(m, 1H), 8.10 - 8.02 (m, 4H), 7.93 - 7.86 (m, 3H), 7.82 (d, J = 7.1 Hz, 1H), 7.61 - 7.34 (m, 15H), 7.32 - 7.30 (m, 1H), 7.17 (dd, J = 7.2, 2.1 Hz, 1H), 7.03 - 6.97 (m, 2H), 1.74 (s, 6H).

[0206] Synthesis of Compound A97

[0207] .

[0208] Synthesis of Compound A97-2

[0209] Referring to the synthesis and purification method of compound A1-3, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound A97-2 (32.65 g, purity: 98.78%, yield: 79.05%), mass spectrum: 345.02 (M+H).

[0210] Synthesis of Compound A97-3

[0211] Referring to the synthesis and purification method of compound A1-5, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound A97-3 (29.63 g, purity: 99.75%, yield: 76.03%), mass spectrum: 373.04 (M+H).

[0212] Synthesis of Compound A97-4

[0213] Referring to the synthesis and purification method of compound A1-7, only the corresponding raw materials need to be changed to obtain the target compound A97-4 (25.63 g, yield: 95.39%) as a white solid, with a mass spectrum of 401.14 (M+H). The obtained compound was used directly in the next step without purification.

[0214] Synthesis of Compound A97-5

[0215] Referring to the synthesis and purification method of compound A1-8, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound A97-5 (20.00 g, purity: 99.76%, yield: 78.80%), mass spectrum: 369.02 (M+H).

[0216] Synthesis of Compound A97

[0217] Referring to the synthesis and purification method of compound A1, only the corresponding raw materials need to be changed to obtain the target compound A97 (14.33 g, purity: 99.95%, yield: 74.63%) as a light yellow solid. 14.33 g of crude A97 was purified by sublimation to obtain sublimation pure A97 (12.01 g, purity: 99.95%, yield: 83.81), mass spectrum: 731.93 (M+H).

[0218] 1H NMR (400 MHz, CDCl3) δ 8.21 (d, J = 7.1 Hz, 1H), 8.11 – 8.02 (m,2H), 8.02 – 7.97 (m, 1H), 7.96 – 7.87 (m, 4H), 7.85 (d, J = 8.1 Hz, 1H), 7.75– 7.68 (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, 2.2 Hz, 1H), 7.04 – 6.97 (m, 2H), 6.97 – 6.87 (m,2H).

[0219] Synthesis of Compound A118

[0220] .

[0221] Synthesis of Compound A118-1

[0222] Referring to the synthesis and purification method of compound A1, it is only necessary to change the corresponding raw materials to obtain a light yellow solid as the target compound A118-1 (12.11 g, purity: 99.95%, yield: 76.87%), mass spectrum: 562.32 (M+H).

[0223] 1 H NMR (400 MHz, CDCl3) δ 8.33 – 8.26 (m, 1H), 8.21 (dd, J = 17.5, 8.8Hz, 2H), 8.13 – 8.08 (m, 1H), 8.06 (d, J = 9.5 Hz, 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).

[0224] Synthesis of Compound A118

[0225] 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) were added to a 500 ml single-necked round-bottom flask, and the vacuum was replaced with nitrogen three times. The system was then heated to 50°C and stirred for 24 hours.

[0226] The system was cooled to room temperature, and heavy water (40 ml) was added to quench the reaction. The mixture was stirred at room temperature for 0.5 hours, and then ethyl acetate (300 ml) and deionized water (200 ml) were added to wash three times. The mixture was slurried at room temperature for 30 minutes, and 35 g of solid was obtained by suction filtration. The mixture was vacuum dried at 90°C for 1 hour to obtain 29 g of light yellow solid. The mixture was crystallized twice with toluene (290 ml) and methanol (120 ml), and suction filtration was performed. The filter cake was vacuum dried at 90°C for 3 hours to obtain a light yellow solid A118 (25.20 g, purity: 99.94%, yield: 80.12%). 25.20 g of crude A118 was purified by sublimation to obtain sublimation pure A118 (21.53 g, purity: 99.95%, deuteration rate of 27 Ds was 95.33%, yield: 85.46%), with a mass spectrum of 589.22 (M+H).

[0227] Synthesis of Compound A136

[0228] .

[0229] Synthesis of Compound A136-2

[0230] Referring to the synthesis and purification method of compound A1-5, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound A136-2 (22.65 g, purity: 99.52%, yield: 75.98%), mass spectrum: 382.12 (M+H).

[0231] Synthesis of Compound A136-3

[0232] Referring to 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 spectrum of 410.10 (M+H). The obtained compound was used directly in the next step without purification.

[0233] Synthesis of Compound A136-4

[0234] Referring to the synthesis and purification method of compound A1-8, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound A136-4 (16.78 g, purity: 99.78%, yield: 42.56%), mass spectrum: 378.26 (M+H).

[0235] Synthesis of Compound A136

[0236] Referring to the synthesis and purification method of compound A1, only the corresponding raw materials need to be changed to obtain the target compound A136 (15.33 g, purity: 99.92%, yield: 77.52%) as a light yellow solid. 15.33 g of crude A136 was purified by sublimation to obtain sublimation pure A136 (12.01 g, purity: 99.93%, yield: 78.35%), mass spectrum: 601.18 (M+H).

[0237] 1 H NMR (400 MHz, CDCl3) δ 8.44 (d, J = 2.0 Hz, 1H), 8.37 (d, J = 8.1Hz, 1H), 8.28 – 8.22 (m, 1H), 8.13 (d, J = 7.5 Hz, 1H), 8.10 – 8.05 (m, 1H),8.04 – 7.92 (m, 3H), 7.90 (d, J = 7.5 Hz, 1H), 7.82 (d, J = 7.2 Hz, 1H), 7.70– 7.59 (m, 2H), 7.47 – 7.34 (m, 3H), 7.32 – 7.24 (m, 2H), 7.17 (dd, J = 7.3,2.0 Hz, 1H), 7.15 – 7.08 (m, 4H), 7.07 (d, J = 2.1 Hz, 1H), 7.04 – 7.02 (m,1H).

[0238] Synthesis of Compound A145

[0239] .

[0240] Synthesis of Compound A145-1

[0241] Referring to the synthesis and purification method of compound A1-8, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound A145-1 (20.52 g, purity: 99.63%, yield: 75.82%), mass spectrum: 353.06 (M+H).

[0242] Synthesis of Compound A145-3

[0243] Referring to the synthesis and purification method of compound A1, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound A145-3 (25.63 g, purity: 99.87%, yield: 74.25%), mass spectrum: 320.12 (M+H).

[0244] Synthesis of compound A145

[0245] Referring to the synthesis and purification method of compound A1, only the corresponding raw materials need to be changed to obtain the yellow solid as the target compound A145 (17.63 g, purity: 99.94%, yield: 77.06%). 17.63 g of crude A145 was purified by sublimation to obtain sublimation pure A145 (14.76 g, purity: 99.94%, yield: 83.72%), mass spectrum: 636.22 (M+H).

[0246] 1 H NMR (400 MHz, CDCl3) δ 8.62 (d, J = 9.2 Hz, 1H), 8.57 (d, J = 9.3Hz, 1H), 8.50 - 8.43 (m, 1H), 8.37 (d, J = 8.3 Hz, 1H), 8.33 - 8.27 (m, 1H),8.25 (d, J = 8.1 Hz, 1H), 8.01 - 7.95 (m, 3H), 7.92 - 7.87 (m, 5H), 7.82 (d,J = 7.2 Hz, 1H), 7.73 (d, J = 2.0 Hz, 1H), 7.56 - 7.47 (m, 4H), 7.37 (d, J =7.1 Hz, 1H), 7.32 - 7.24 (m, 2H), 7.17 - 7.06 (m, 5H), 6.89 (dd, J = 7.5, 2.2Hz, 1H).

[0247] Synthesis of Compound A167

[0248] .

[0249] Synthesis of Compound A167-1

[0250] Referring to the synthesis and purification method of compound A1-8, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound A167-1 (15.63 g, purity: 99.71%, yield: 42.52%), mass spectrum: 353.06 (M+H).

[0251] Synthesis of Compound A167-4

[0252] Referring to the synthesis and purification method of compound A1, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound A167 (20.62 g, purity: 99.75%, yield: 78.43%), mass spectrum: 410.20 (M+H).

[0253] Synthesis of Compound A167

[0254] Referring to the synthesis and purification method of compound A1, only the corresponding raw materials need to be changed to obtain the target compound A167 (14.52 g, purity: 99.93%, yield: 74.62%) as a light yellow solid. 14.52 g of crude A167 was purified by sublimation to obtain sublimation pure A167 (11.11 g, purity: 99.93%, yield: 76.52%), mass spectrum: 726.28 (M+H).

[0255] 1 H NMR (400 MHz, CDCl3) δ 8.33 – 8.27 (m, 1H), 8.25 – 8.18 (m, 2H), 8.15 (dd, J = 8.9, 2.4 Hz, 1H), 8.02 (s, 1H), 8.00 (d, J = 2.2 Hz, 1H), 7.98– 7.86 (m, 6H), 7.85 (d, J = 2.0 Hz, 1H), 7.55 – 7.48 (m, 5H), 7.42 (d, J =7.6 Hz, 1H), 7.31 (dd, J = 7.5, 2.2 Hz, 1H), 7.07 – 7.01 (m, 2H), 6.89 – 6.84(m, 2H), 2.16 – 2.09 (m, 3H), 1.96 (d, J = 4.9 Hz, 6H), 1.79 (t, J = 5.5 Hz, 6H).

[0256] Synthesis of Compound A183

[0257] .

[0258] Synthesis of Compound A183-2

[0259] Referring to the synthesis and purification method of compound A1-3, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound A183-2 (28.74 g, purity: 99.21%, yield: 74.56%), mass spectrum: 329.12 (M+H).

[0260] Synthesis of Compound A183-3

[0261] Referring to the synthesis and purification method of compound A1-5, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound A183-3 (26.32 g, purity: 99.66%, yield: 76.36%), mass spectrum: 357.22 (M+H).

[0262] Synthesis of Compound A183-4

[0263] Referring to the synthesis and purification method of compound A1-7, only the corresponding raw materials need to be changed to obtain the target compound A183-4 (21.65 g, yield: 92.84%) as a white solid, with a mass spectrum of 385.04 (M+H). The obtained compound was used directly in the next step without purification.

[0264] Synthesis of Compound A183-5

[0265] Referring to the synthesis and purification method of compound A1-8, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound A183-5 (18.65 g, purity: 99.73%, yield: 76.85%), mass spectrum: 353.06 (M+H).

[0266] Synthesis of Compound A183-7

[0267] Referring to the synthesis and purification method of compound A1, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound A183-7 (19.99 g, purity: 99.87%, yield: 78.63%), mass spectrum: 310.22 (M+H).

[0268] Synthesis of Compound A183

[0269] Referring to the synthesis and purification method of compound A1, only the corresponding raw materials need to be changed to obtain the target compound A183 (14.65 g, purity: 99.96%, yield: 77.14%) as a light yellow solid. 14.65 g of crude A183 was purified by sublimation to obtain sublimation pure A183 (11.24 g, purity: 99.96%, yield: 76.73%), mass spectrum: 626.24 (M+H).

[0270] 1H NMR (400 MHz, CDCl3) δ 8.36 – 8.28 (m, 2H), 8.05 – 7.98 (m, 3H), 7.97 – 7.87 (m, 5H), 7.85 (d, J = 8.0 Hz, 1H), 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).

[0271] Synthesis of Compound A207

[0272] .

[0273] Synthesis of Compound A207-2

[0274] Referring to the synthesis and purification method of compound A1-5, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound A207-2 (28.78 g, purity: 99.74%, yield: 76.11%), mass spectrum: 357.24 (M+H).

[0275] Synthesis of Compound A207-3

[0276] Referring to the synthesis and purification method of compound A1-7, only the corresponding raw materials need to be changed to obtain the target compound A207-3 (22.65 g, yield: 95.63%) as a white solid, with a mass spectrum of 385.04 (M+H). The obtained compound was used directly in the next step without purification.

[0277] Synthesis of Compound A207-4

[0278] Referring to the synthesis and purification method of compound A1-8, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound A207-4 (18.08 g, purity: 99.65%, yield: 41.20%), mass spectrum: 353.06 (M+H).

[0279] Synthesis of Compound A207-5

[0280] Referring to the synthesis and purification method of compound A1-3, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound A207-5 (20.63 g, purity: 99.00%, yield: 75.41%), mass spectrum: 445.20 (M+H).

[0281] Synthesis of Compound A207

[0282] Referring to the synthesis and purification method of compound A1-5, only the corresponding raw materials need to be changed to obtain the target compound A207 (15.12 g, purity: 99.94%, yield: 75.85%) as a light yellow solid. 15.12 g of crude A207 was purified by sublimation to obtain sublimation pure A207 (12.02 g, purity: 99.94%, yield: 79.50%), mass spectrum: 638.24 (M+H).

[0283] 1 H NMR (400 MHz, CDCl3) δ 8.64 (d, J = 9.3 Hz, 1H), 8.46 – 8.40 (m,1H), 8.38 (d, J = 9.6 Hz, 1H), 8.21 (d, J = 1.1 Hz, 2H), 8.04 (d, J = 9.5 Hz,1H), 8.01 – 7.93 (m, 2H), 7.92 – 7.86 (m, 1H), 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).

[0284] Synthesis of compound A219

[0285] .

[0286] Synthesis of Compound A219-2

[0287] Referring to the synthesis and purification method of compound A1-3, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound A219-2 (22.54 g, purity: 98.98%, yield: 78.15%), mass spectrum: 329.12 (M+H).

[0288] Synthesis of Compound A219-3

[0289] Referring to the synthesis and purification method of compound A1-5, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound A219-3 (22.62 g, purity: 99.81%, yield: 77.63%), mass spectrum: 357.22 (M+H).

[0290] Synthesis of Compound A219-4

[0291] Referring to the synthesis and purification method of compound A1-7, only the corresponding raw materials need to be changed to obtain the target compound A219-4 (19.02 g, yield: 92.06%) as a white solid, with a mass spectrum of 385.04 (M+H). The obtained compound was used directly in the next step without purification.

[0292] Synthesis of Compound A219-5

[0293] Referring to the synthesis and purification method of compound A1-8, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound A219-5 (187.85 g, purity: 99.23%, yield: 43.05%), mass spectrum: 353.06 (M+H).

[0294] Synthesis of Compound A219-7

[0295] Referring to the synthesis and purification method of compound A1, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound A219-7 (18.63 g, purity: 99.55%, yield: 78.06%), mass spectrum: 520.20 (M+H).

[0296] Synthesis of compound A219

[0297] Referring to the synthesis and purification method of compound A1, only the corresponding raw materials need to be changed to obtain the target compound A219 (17.96 g, purity: 99.93%, yield: 77.61%) as a light yellow solid. 17.96 g of crude A219 was purified by sublimation to obtain sublimation pure A219 (15.00 g, purity: 99.93%, yield: 83.51%), mass spectrum: 836.28 (M+H).

[0298] 1H NMR (400 MHz, CDCl3) δ 8.65 – 8.58 (m, 3H), 8.50 – 8.44 (m, 1H), 8.33 (d, J = 2.2 Hz, 2H), 8.26 (d, J = 7.8 Hz, 2H), 8.10 (d, J = 2.1 Hz, 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 = 7.6 Hz, 1H), 7.34 (dd, J = 7.7, 2.2 Hz, 2H), 7.32 –7.25 (m, 3H), 7.17 (dd, J = 7.2, 2.1 Hz, 1H), 7.16 – 7.12 (m, 2H), 7.11 –7.08 (m, 1H), 1.33 (s, 18H).

[0299] Synthesis of Compound A226

[0300] .

[0301] Synthesis of Compound A226-2

[0302] Referring to the synthesis and purification method of compound A1-3, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound A226-2 (35.23 g, purity: 99.21%, yield: 79.08%), mass spectrum: 329.12 (M+H).

[0303] Synthesis of Compound A226-3

[0304] Referring to the synthesis and purification method of compound A1-5, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound A226-3 (30.68 g, purity: 99.78%, yield: 74.62%), mass spectrum: 357.24 (M+H).

[0305] Synthesis of Compound A226-4

[0306] Referring to the synthesis and purification method of compound A1-7, only the corresponding raw materials need to be changed to obtain the target compound A226-4 (24.55 g, yield: 96.33%) as a white solid, with a mass spectrum of 385.04 (M+H). The obtained compound was used directly in the next step without purification.

[0307] Synthesis of Compound A226-5

[0308] Referring to the synthesis and purification method of compound A1-8, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound A226-5 (17.99 g, purity: 99.86%, yield: 78.63%), mass spectrum: 353.06 (M+H).

[0309] Synthesis of Compound A226

[0310] Referring to the synthesis and purification method of compound A1, only the corresponding raw materials need to be changed to obtain the target compound A226 (17.11 g, purity: 99.95%, yield: 78.74%) as a light yellow solid. 17.11 g of crude A226 was purified by sublimation to obtain sublimation pure A226 (13.75 g, purity: 99.95%, yield: 80.37%), mass spectrum: 562.24 (M+H).

[0311] 1 H NMR (400 MHz, CDCl3) δ 8.75 - 8.71 (m, 2H), 8.66 (d, J = 8.9 Hz,1H), 8.42 (d, J = 2.2 Hz, 1H), 8.03 (dd, J = 18.4, 8.8 Hz, 2H), 7.87 (d, J =8.7 Hz, 1H), 7.75 - 7.52 (m, 8H), 7.47 (t, J = 7.7 Hz, 2H), 7.43 - 7.30 (m,5H), 7.26 - 7.19 (m, 4H), 7.12 - 7.11 (m, 1H).

[0312] Synthesis of compound A252

[0313] .

[0314] Synthesis of Compound A252-2

[0315] Referring to the synthesis and purification method of compound A1-5, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound A252-2 (18.42 g, purity: 99.52%, yield: 74.62%), mass spectrum: 433.20 (M+H).

[0316] Synthesis of compound A252-3

[0317] Referring to the synthesis and purification method of compound A1-7, only the corresponding raw materials need to be changed to obtain the target compound A252-3 (20.06 g, yield: 94.26%) as a white solid, with a mass spectrum of 461.12 (M+H). The obtained compound was used directly in the next step without purification.

[0318] Synthesis of Compound A252-4

[0319] Referring to the synthesis and purification method of compound A1-8, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound A252-4 (16.75 g, purity: 99.71%, yield: 74.29%), mass spectrum: 429.12 (M+H).

[0320] Synthesis of Compound A252

[0321] Referring to the synthesis and purification method of compound A1, only the corresponding raw materials need to be changed to obtain the target compound A252 (14.02 g, purity: 99.93%, yield: 74.00%) as a light yellow solid. 14.02 g of crude A252 was purified by sublimation to obtain sublimation pure A252 (10.58 g, purity: 99.93%, yield: 75.47%), mass spectrum: 638.22 (M+H).

[0322] 1 H NMR (400 MHz, CDCl3) δ 8.63 – 8.60 (m, 2H), 8.26 (d, J = 9.0 Hz,1H), 8.00 – 7.95 (m, 3H), 7.93 – 7.89 (m, 2H), 7.80 (dd, J = 8.1, 2.4 Hz,1H), 7.61 – 7.49 (m, 6H), 7.43 – 7.39 (m, 6H), 7.32 (d, J = 7.2 Hz, 1H), 7.31– 7.24 (m, 2H), 7.17 – 7.07 (m, 5H), 7.02 – 6.96 (m, 2H).

[0323] Synthesis of compound A265

[0324] .

[0325] Synthesis of compound A265

[0326] Referring to the synthesis and purification method of compound A1, only the corresponding raw materials need to be changed to obtain the target compound A265 (10.33 g, purity: 99.94%, yield: 78.63%) as a light yellow solid. 10.33 g of crude A265 was purified by sublimation to obtain sublimation pure A265 (8.13 g, purity: 99.94%, yield: 78.71%), mass spectrum: 668.34 (M+H).

[0327] 1 H NMR (400 MHz, CDCl3) δ 8.61 (dd, J = 8.5, 3.7 Hz, 2H), 8.47 - 8.39(m, 1H), 8.33 - 8.28 (m, 1H), 8.06 (d, J = 2.2 Hz, 1H), 7.96 - 7.90 (m, 2H),7.89 - 7.86 (m, 1H), 7.56 - 7.47 (m, 2H), 7.42 (d, J = 7.5 Hz, 1H), 7.33 -7.31 (m, 2H).

[0328] Synthesis of compound A280

[0329] .

[0330] Synthesis of Compound A280-2

[0331] Referring to the synthesis and purification method of compound A1-3, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound A280-2 (33.59 g, purity: 99.41%, yield: 74.02%), mass spectrum: 329.12 (M+H).

[0332] Synthesis of Compound A280-3

[0333] Referring to the synthesis and purification method of compound A1-5, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound A280-3 (32.63 g, purity: 99.69%, yield: 74.69%), mass spectrum: 357.24 (M+H).

[0334] Synthesis of Compound A280-4

[0335] Referring to the synthesis and purification method of compound A1-7, only the corresponding raw materials need to be changed to obtain the target compound A280-4 (27.96 g, yield: 94.12%) as a white solid, with a mass spectrum of 385.04 (M+H). The obtained compound was used directly in the next step without purification.

[0336] Synthesis of Compound A280-5

[0337] Referring to the synthesis and purification method of compound A1-8, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound A280-5 (21.21 g, purity: 99.59%, yield: 74.63%), mass spectrum: 353.06 (M+H).

[0338] Synthesis of compound A280

[0339] Referring to the synthesis and purification method of compound A1, only the corresponding raw materials need to be changed to obtain the target compound A280 (16.06 g, purity: 99.95%, yield: 74.44%) as a light yellow solid. 16.06 g of crude A280 was purified by sublimation to obtain sublimation pure A280 (12.90 g, purity: 99.95%, yield: 80.33%), mass spectrum: 712.22 (M+H).

[0340] 1 H NMR (400 MHz, CDCl3) 8.64 (d, J = 8.9 Hz, 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, 7.8 Hz, 2H),8.01 - 7.96 (m, 3H), 7.94 (d, J = 2.0 Hz, 1H), 7.92 - 7.85 (m, 1H), 7.66 (d,J = 8.0 Hz, 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).

[0341] Synthesis of compound A289

[0342] .

[0343] Synthesis of Compound A289-3

[0344] Referring to the synthesis and purification method of compound A1, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound A289-3 (20.06 g, purity: 99.87%, yield: 74.63%), mass spectrum: 356.23 (M+H).

[0345] Synthesis of Compound A289-4

[0346] Referring to the synthesis and purification method of compound A1-8, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound A289-4 (10.05, purity: 99.43%, yield: 39.85%), mass spectrum: 353.06 (M+H).

[0347] Synthesis of compound A289

[0348] Referring to the synthesis and purification method of compound A1, only the corresponding raw materials need to be changed to obtain the target compound A289 (10.96 g, purity: 99.93%, yield: 78.65%) as a light yellow solid. 10.96 g of crude A289 was purified by sublimation to obtain sublimation pure A289 (8.88 g, purity: 99.93%, yield: 81.03%), mass spectrum: 672.32 (M+H).

[0349] 1 H NMR (400 MHz, CDCl3)δ 8.61 (dd, J = 9.1, 2.3 Hz, 2H), 8.48 - 8.44(m, 1H), 8.21 (d, J = 2.3 Hz, 1H), 8.17 (dd, J = 9.0, 2.3 Hz, 1H), 8.00 (d, J = 2.2 Hz, 1H), 7.96 (d, J = 9.3 Hz, 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, 2.2 Hz, 1H), 7.13 (d, J = 6.6 Hz, 1H), 7.05 - 6.96 (m, 4H), 2.13 - 1.90 (m, 4H), 1.33 (s, 12H).

[0350] Synthesis of compound A305

[0351] .

[0352] Synthesis of compound A305-3

[0353] Referring to the synthesis and purification method of compound A1, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound A305-3 (29.45 g, purity: 99.85%, yield: 75.44%), mass spectrum: 500.20 (M+H).

[0354] Synthesis of Compound A305-4

[0355] Referring to the synthesis and purification method of compound A1-8, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound A305-4 (22.44 g, purity: 99.53%, yield: 38.43%), mass spectrum: 353.06 (M+H).

[0356] Synthesis of compound A305

[0357] Referring to the synthesis and purification method of compound A1, only the corresponding raw materials need to be changed to obtain the target compound A305 (17.89 g, purity: 99.94%, yield: 74.85%) as a light yellow solid. 17.89 g of crude A305 was purified by sublimation to obtain sublimation pure A305 (14.88 g, purity: 99.94%, yield: 83.18%), mass spectrum: 816.28 (M+H).

[0358] 1 H NMR (400 MHz, CDCl3) δ 8.69 (d, J = 8.2 Hz, 1H), 8.62 (d, J = 9.3Hz, 1H), 8.50 - 8.43 (m, 1H), 8.24 (d, J = 2.1 Hz, 1H), 8.11 - 8.03 (m, 3H),7.99 - 7.92 (m, 2H), 7.92 - 7.85 (m, 1H), 7.76 (d, J = 7.1 Hz, 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, 1.4 Hz, 1H).

[0359] Synthesis of compound A340

[0360] .

[0361] Synthesis of Compound A340-2

[0362] Referring to the synthesis and purification method of compound A1-5, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound A340-2 (20.20 g, purity: 99.52%, yield: 77.74%), mass spectrum: 357.22 (M+H).

[0363] Synthesis of Compound A340-3

[0364] Referring to the synthesis and purification method of compound A1-7, only the corresponding raw materials need to be changed to obtain the target compound A340-3 (15.86 g, yield: 94.63%) as a white solid, with a mass spectrum of 385.04 (M+H). The obtained compound was used directly in the next step without purification.

[0365] Synthesis of Compound A340-4

[0366] Referring to the synthesis and purification method of compound A1-8, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound A340-4 (14.36 g, purity: 99.76%, yield: 76.33%), mass spectrum: 353.06 (M+H).

[0367] Synthesis of Compound A340-5

[0368] Referring to the synthesis and purification method of compound A1-3, it is only necessary to change the corresponding raw materials to obtain the white solid as the target compound A340-4 (12.37 g, purity: 98.08%, yield: 75.55%), mass spectrum: 445.20 (M+H).

[0369] Synthesis of Compound A340-7

[0370] Referring to the synthesis and purification method of compound A1-5, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound A340-7 (10.23 g, purity: 98.88%, yield: 78.96%), mass spectrum: 523.04 (M+H).

[0371] Synthesis of compound A340

[0372] Referring to the synthesis and purification method of compound A1, only the corresponding raw materials need to be changed to obtain the target compound A340 (10.28 g, purity: 99.95%, yield: 78.26%) as a light yellow solid. 10.28 g of crude A340 was purified by sublimation to obtain sublimation pure A340 (8.02 g, purity: 99.95%, yield: 78.02%), mass spectrum: 764.22 (M+H).

[0373] 1H NMR (400 MHz, CDCl3) δ 8.61- 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 =7.7 Hz, 1H), 7.69 (dd, J = 7.2, 2.5 Hz, 1H), 7.64 - 7.45 (m, 14H), 7.45 -7.36 (m, 7H), 7.32 (d, J = 7.6 Hz, 1H), 6.96 - 6.91 (m, 4H).

[0374] Synthesis of Compound A424

[0375] .

[0376] Synthesis of Compound A424-1

[0377] Referring to the synthesis and purification method of compound A1-5, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound A424-1 (26.52 g, purity: 99.46%, yield: 74.52%), mass spectrum: 357.24 (M+H).

[0378] Synthesis of Compound A424-2

[0379] Referring to 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 spectrum of 385.04 (M+H). The obtained compound was used directly in the next step without purification.

[0380] Synthesis of Compound A424-3

[0381] Referring to the synthesis and purification method of compound A1-8, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound A424-3 (18.85 g, purity: 99.23%, yield: 40.05%), mass spectrum: 353.06 (M+H).

[0382] Synthesis of Compound A424-5

[0383] Referring to the synthesis and purification method of compound A1, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound A424-5 (15.96 g, purity: 99.77%, yield: 79.06%), mass spectrum: 385.16 (M+H).

[0384] Synthesis of Compound A424

[0385] Referring to the synthesis and purification method of compound A1, only the corresponding raw materials need to be changed to obtain the target compound A424 (13.06 g, purity: 99.94%, yield: 78.61%) as a light yellow solid. 13.06 g of crude A424 was purified by sublimation to obtain sublimation pure A424 (10.00 g, purity: 99.94%, yield: 76.57%), mass spectrum: 701.25 (M+H).

[0386] 1 H NMR (400 MHz, CDCl3) δ 8.62 (s, 1H), 8.48 – 8.41 (m, 1H), 8.35 –8.25 (m, 1H), 8.16 (d, J = 2.2 Hz, 1H), 8.04 – 7.98 (m, 2H), 7.96 (dd, J =7.4, 2.7 Hz, 2H), 7.93 – 7.84 (m, 6H), 7.78 (d, J = 2.1 Hz, 1H), 7.55 – 7.46(m, 4H), 7.42 (d, J = 7.6 Hz, 1H), 7.38 (dd, J = 7.2, 2.1 Hz, 1H), 7.35 –7.25 (m, 5H), 7.25 – 7.16 (m, 3H), 7.16 – 7.05 (m, 3H).

[0387] Synthesis of Compound A481

[0388] .

[0389] Synthesis of Compound A481-2

[0390] Referring to the synthesis and purification method of compound A1-3, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound A481-2 (25.77 g, purity: 98.88%, yield: 74.12%), mass spectrum: 355.12 (M+H).

[0391] Synthesis of Compound A481-4

[0392] Referring to the synthesis and purification method of compound A1-5, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound A481-4 (20.11 g, purity: 99.54%, yield: 71.52%), mass spectrum: 439.18 (M+H).

[0393] Synthesis of Compound A481-5

[0394] Referring to 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 spectrum of 467.22 (M+H). The obtained compound was used directly in the next step without purification.

[0395] Synthesis of Compound A481-6

[0396] Referring to the synthesis and purification method of compound A1-8, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound A481-6 (18.88 g, purity: 99.75%, yield: 75.62%), mass spectrum: 435.16 (M+H).

[0397] Synthesis of Compound A481

[0398] Referring to the synthesis and purification method of compound A1, only the corresponding raw materials need to be changed to obtain the target compound A481 (15.55 g, purity: 99.94%, yield: 76.22%) as a light yellow solid. 15.55 g of crude A481 was purified by sublimation to obtain sublimation pure A481 (11.85 g, purity: 99.94%, yield: 76.21%), mass spectrum: 658.30 (M+H).

[0399] 1H NMR (400 MHz, CDCl3) δ 8.63 – 8.57 (m, 1H), 8.50 (d, J = 8.1 Hz, 1H), 8.28 – 8.22 (m, 1H), 8.16 – 8.07 (m, 2H), 8.06 (d, J = 2.2 Hz, 1H), 7.99– 7.92 (m, 3H), 7.89 – 7.84 (m, 1H), 7.77 (d, J = 7.1 Hz, 1H), 7.67 – 7.60(m, 1H), 7.56 (d, J = 7.9 Hz, 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, 2.2 Hz, 1H), 1.80 (s, 6H), 1.34 (s, 9H).

[0400] Synthesis of Compound A488

[0401] ,

[0402] .

[0403] Synthesis of Compound A488-2

[0404] Referring to the synthesis and purification method of compound A1-3, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound A488-2 (28.77 g, purity: 99.02%, yield: 76.74%), mass spectrum: 404.14 (M+H).

[0405] Synthesis of Compound A488-3

[0406] Referring to the synthesis and purification method of compound A1-5, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound A488-3 (24.85 g, purity: 99.67%, yield: 73.62%), mass spectrum: 432.21 (M+H).

[0407] Synthesis of Compound A488-4

[0408] Referring to the synthesis and purification method of compound A1-7, only the corresponding raw materials need to be changed to obtain the target compound A488-4 (23.41 g, yield: 96.66%) as a white solid, with a mass spectrum of 460.04 (M+H). The obtained compound was used directly in the next step without purification.

[0409] Synthesis of Compound A488-5

[0410] Referring to the synthesis and purification method of compound A1-8, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound A488-5 (20.00 g, purity: 99.87%, yield: 77.01%), mass spectrum: 428.02 (M+H).

[0411] Synthesis of Compound A488

[0412] Referring to the synthesis and purification method of compound A1, only the corresponding raw materials need to be changed to obtain the target compound A488 (18.11 g, purity: 99.92%, yield: 75.98%) as a light yellow solid. 18.11 g of crude A488 was purified by sublimation to obtain sublimation pure A488 (15.00 g, purity: 99.93%, yield: 82.83%), mass spectrum: 713.24 (M+H).

[0413] 1 H NMR (400 MHz, CDCl3) δ 8.60 (d, J = 9.0 Hz, 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 = 8.1 Hz, 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).

[0414] Synthesis of Compound A496

[0415] .

[0416] Synthesis of Compound A496-2

[0417] Referring to the synthesis and purification method of compound A1-5, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound A496-2 (18.81 g, purity: 99.72%, yield: 73.62%), mass spectrum: 429.10 (M+H).

[0418] Synthesis of Compound A496-3

[0419] Referring to the synthesis and purification method of compound A1-7, only the corresponding raw materials need to be changed to obtain the target compound A496-3 (18.77 g, yield: 92.626%) as a white solid, with a mass spectrum of 457.13 (M+H). The obtained compound was used directly in the next step without purification.

[0420] Synthesis of Compound A496-4

[0421] Referring to the synthesis and purification method of compound A1-8, only the corresponding raw materials need to be changed to obtain the target compound A496-4 (16.85 g, purity: 99.45%, yield: 75.11%) as a white solid, mass spectrum: 425.24 (M+H)

[0422] Synthesis of Compound A496-5

[0423] Referring to the synthesis and purification method of compound A1-5, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound A496-5 (19.78 g, purity: 99.62%, yield: 74.44%), mass spectrum: 591.15 (M+H).

[0424] Synthesis of Compound A496

[0425] Referring to the synthesis and purification method of compound A1, only the corresponding raw materials need to be changed to obtain the target compound A496 (12.71, purity: 99.95%, yield: 62.71%) as a light yellow solid. 12.71 grams of crude A496 was purified by sublimation to obtain sublimation pure A496 (9.84 g, purity: 99.97%, yield: 11.41%), mass spectrum: 800.07 (M+H).

[0426] 1H NMR (400 MHz, CDCl3)δ 8.62 (dd, J = 13.1, 8.5 Hz, 2H), 8.30 (dd, J= 9.0, 0.7 Hz, 1H), 8.16 (d, J = 7.9 Hz, 1H), 8.06 – 7.98 (m, 3H), 7.89 (dt,J = 7.0, 0.7 Hz, 1H), 7.83 (d, J = 2.2 Hz, 1H), 7.79 – 7.70 (m, 2H), 7.67(dd, J = 9.2, 2.1 Hz, 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).

[0427] Synthesis of Compound A515

[0428] .

[0429] Synthesis of Compound A515-2

[0430] Referring to the synthesis and purification method of compound A1-3, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound A515-2 (25.33 g, purity: 99.23%, yield: 78.46%), mass spectrum: 379.12 (M+H).

[0431] Synthesis of Compound A515-3

[0432] Referring to the synthesis and purification method of compound A1-5, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound A515-3 (22.11 g, purity: 99.43%, yield: 75.12%), mass spectrum: 407.06 (M+H).

[0433] Synthesis of Compound A515-4

[0434] Referring to the synthesis and purification method of compound A1-7, only the corresponding raw materials need to be changed to obtain the target compound A515-4 (20.63 g, yield: 95.12%) as a white solid, with a mass spectrum of 435.12 (M+H). The obtained compound was used directly in the next step without purification.

[0435] Synthesis of Compound A515-5

[0436] Referring to the synthesis and purification method of compound A1-8, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound A515-5 (18.96 g, purity: 99.90%, yield: 79.63%), mass spectrum: 403.08 (M+H).

[0437] Synthesis of compound A515

[0438] Referring to the synthesis and purification method of compound A1, only the corresponding raw materials need to be changed to obtain the target compound A515 (16.96 g, purity: 99.93%, yield: 76.68%) as a light yellow solid. 16.96 g of crude A515 was purified by sublimation to obtain sublimation pure A515 (14.33 g, purity: 99.93%, yield: 84.49%), mass spectrum: 612.75 (M+H).

[0439] 1 H NMR (400 MHz, CDCl3) δ 8.61 (dd, J = 8.5, 3.7 Hz, 2H), 8.47 – 8.39(m, 1H), 8.33 – 8.26 (m, 2H), 8.02 (d, J = 2.0 Hz, 1H), 7.94 (d, J = 8.2 Hz,1H), 7.91 – 7.85 (m, 2H), 7.83 (dd, J = 7.4, 2.1 Hz, 1H), 7.61 – 7.49 (m,6H), 7.45 – 7.37 (m, 4H), 7.35 – 7.24 (m, 3H), 7.17 – 7.07 (m, 3H), 7.03 –6.97 (m, 2H), 6.88 (dd, J = 7.6, 2.3 Hz, 1H).

[0440] Synthesis of Compound A527

[0441] .

[0442] Synthesis of Compound A527-2

[0443] Referring to the synthesis and purification method of compound A1-3, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound A527-2 (22.10 g, purity: 99.10%, yield: 70.01%), mass spectrum: 405.14 (M+H).

[0444] Synthesis of Compound A527-3

[0445] Referring to the synthesis and purification method of compound A1-5, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound A527-3 (20.06 g, purity: 99.21%, yield: 72.32%), mass spectrum: 433.08 (M+H).

[0446] Synthesis of Compound A527-4

[0447] Referring to the synthesis and purification method of compound A1-7, only the corresponding raw materials need to be changed to obtain the target compound A527-4 (18.06 g, yield: 94.33%) as a white solid, with a mass spectrum of 461.22 (M+H). The obtained compound was used directly in the next step without purification.

[0448] Synthesis of Compound A527-5

[0449] Referring to the synthesis and purification method of compound A1-8, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound A527-5 (17.63 g, purity: 99.88%, yield: 42.03%), mass spectrum: 429.12 (M+H).

[0450] Synthesis of Compound A527

[0451] Referring to the synthesis and purification method of compound A1, only the corresponding raw materials need to be changed to obtain the target compound A527 (14.63 g, purity: 99.93%, yield: 74.95%) as a light yellow solid. 14.63 g of crude A527 was purified by sublimation to obtain sublimation pure A527 (12.00 g, purity: 99.93%, yield: 82.02%), mass spectrum: 668.20 (M+H).

[0452] 1 H NMR (400 MHz, CDCl3) δ 8.44 (s, 1H), 8.33 – 8.26 (m, 1H), 8.23 ​​–8.16 (m, 1H), 8.01 (d, J = 9.0 Hz, 1H), 7.98 – 7.83 (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).

[0453] Synthesis of Compound A539

[0454] .

[0455] Synthesis of Compound A539-2

[0456] Referring to the synthesis and purification method of compound A1-3, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound A539-2 (18.63 g, purity: 99.22%, yield: 76.52%), mass spectrum: 504.16 (M+H).

[0457] Synthesis of Compound A539-3

[0458] Referring to the synthesis and purification method of compound A1-5, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound A539-3 (17.26 g, purity: 99.12%, yield: 75.63%), mass spectrum: 532.14 (M+H).

[0459] Synthesis of Compound A539-4

[0460] Referring to 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 spectrum of 560.12 (M+H). The obtained compound was used directly in the next step without purification.

[0461] Synthesis of Compound A539-5

[0462] Referring to the synthesis and purification method of compound A1-8, it is only necessary to change the corresponding raw materials to obtain a white solid as the target compound A539-5 (14.00 g, purity: 99.87%, yield: 41.26%), mass spectrum: 528.24 (M+H).

[0463] Synthesis of Compound A539

[0464] Referring to the synthesis and purification method of compound A1, only the corresponding raw materials need to be changed to obtain the target compound A539 (14.00 g, purity: 99.92%, yield: 76.78%) as a light yellow solid. 14.00 g of crude A539 was purified by sublimation to obtain sublimation pure A539 (11.52 g, purity: 99.92%, yield: 82.28%), mass spectrum: 813.32 (M+H).

[0465] 1H NMR (400 MHz, CDCl3) δ 8.87 (s, 1H), 8.51 – 8.49 (m, 1H), 8.33 –8.26 (m, 2H), 8.21 – 8.19 (m, 1H), 8.12 (d, J = 2.2 Hz, 1H), 8.04 – 7.99 (m,2H), 7.96 (d, J = 8.0 Hz, 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) .

[0466] Synthesis of compound B3

[0467] .

[0468] Synthesis of compound B3

[0469] Compound B3-1 (13.69 g, 45.00 mmol), B3-2 (16.10 g, 45.00 mmol), tetrakis(triphenylphosphine)palladium (Pd(PPh3)4, 1.04 g, 0.90 mmol), sodium hydroxide (NaOH, 3.6 g, 90.02 mmol), tetrahydrofuran (THF, 300 mL), and deionized water (100 mL) were added to a 1000 mL three-necked round-bottom flask, and the atmosphere was replaced with vacuum nitrogen three times. The temperature was raised to 75°C and the reaction was continued for 6 hours. The consumption of compound B3-1 was monitored by TLC (ethyl acetate: n-hexane = 1:10 as the developing solvent).

[0470] After cooling to room temperature, methanol (300 mL) was added and stirred at room temperature for 30 minutes, and a yellow solid was obtained by suction filtration. Xylene (600 mL) was added, and the mixture was heated to 120°C to dissolve the material, and the mixture was cooled to room temperature and filtered once with column chromatography silica gel (60 g, 200-300 mesh). The filter cake was rinsed with 300 mL of toluene until no product remained. The organic phases were combined and concentrated under reduced pressure at 70°C to obtain a yellow solid, which was crystallized twice with xylene and methanol, and dried under vacuum at 100°C for 8 hours to obtain a light yellow solid, which was compound B3 (19.72 g, purity: 99.95%, yield: 87.70%). 19.72 g of crude compound B3 was purified by sublimation to obtain sublimation-purified compound B3 (16.68 g, purity: 99.95%, yield: 84.59%), with a mass spectrum of 500.16 (M+H).

[0471] 1H NMR (400 MHz, CDCl3) δ 8.59 – 8.57(m, 1H), 8.36 – 8.27 (m, 2H), 8.13 – 7.96 (m, 5H), 7.92 – 7.82 (m, 3H), 7.66 – 7.59 (m, 1H), 7.58 – 7.48(m, 6H), 7.45 – 7.38 (m, 2H), 7.28 – 7.24 (m, 1H).

[0472] Synthesis of compound B32

[0473] .

[0474] Synthesis of compound B32

[0475] Referring to the synthesis and purification method of compound B3, only the corresponding raw materials need to be changed to obtain the target compound B32 (12.15 g, purity: 99.92%, yield: 77.65%) as a light yellow solid. 12.15 g of crude compound B32 was purified by sublimation to obtain sublimation pure compound B32 (10.00 g, purity: 99.92%, yield: 82.31%), mass spectrum: 591.20 (M+H).

[0476] 1 H NMR (400 MHz, CDCl3) δ 8.46 – 8.35 (m, 3H), 8.30 – 8.25 (m, 1H), 8.21 – 8.13 (m, 1H), 8.11 (dd, J = 9.0, 1.1 Hz, 1H), 8.04 (s, 1H), 8.02 –7.95 (m, 1H), 7.94 – 7.86 (m, 3H), 7.73 – 7.70 (mz, 1H), 7.60 – 7.44 (m,11H), 7.42 – 7.39 (m, 3H).

[0477] Synthesis of compound B105

[0478] .

[0479] Synthesis of compound B105-2

[0480] Compound B32-1 (20.00 g, 65.75 mmol), compound B105-1 (21.89 g, 65.75 mmol), tetrakis(triphenylphosphine)palladium (Pd(PPh3)4, 0.76 g, 0.66 mmol), potassium carbonate (K2CO3, 13.635 g, 98.62 mmol), tetrahydrofuran (300 mL), and deionized water (60 mL) were added to a 1000 mL three-necked round-bottom flask, and the vacuum nitrogen was replaced three times. Then, the system was heated to 65 ° C for 6 hours. The reaction was monitored by TLC (ethyl acetate: n-hexane = 1:15 as the developing solvent). The compound B3-1 was completely consumed.

[0481] The temperature was lowered to 60°C and the solvent was removed by concentrating under reduced pressure. Ethyl acetate (700 ml) was added and the mixture was washed three times with deionized water (300 ml × 3). The mixture was separated and the sample was mixed with silica gel and dry-loaded onto a column. Purification was performed by silica gel column chromatography (200-300 mesh silica gel, ethyl acetate:n-hexane = 1:20 as the eluent). After elution, the mixture was concentrated under reduced pressure at 70°C for 2 hours to obtain a white solid, which was compound B105-2 (18.53 g, purity: 99.56%, yield: 73.52%), with a mass spectrum of 383.04 (M+H).

[0482] Synthesis of compound B105-4

[0483] Compound B105-2 (18.00 g, 46.96 mmol), compound B105-3 (14.31 g, 56.35 mmol), 1,1-bis(diphenylphosphine)dichloropalladium iron (Pd(dppf)Cl2, 0.34 g, 0.47 mmol), potassium acetate (KOAc, 26.91 g, 70.44 mol), 1,4-dioxane (1,4-Dioxane, 270 ml) were added to a 500 ml three-necked round-bottom flask, and the vacuum nitrogen was replaced three times. Then, the system was heated to 100 ° C for 2 hours. The reaction was monitored by TLC (ethyl acetate: n-hexane = 1:15 as the developing solvent). Compound B105-2 was completely consumed.

[0484] The temperature was lowered to 60°C, and the solvent was removed by concentration under reduced pressure. Ethyl acetate (700 ml) was added, and the mixture was washed three times with deionized water (300 ml × 3). The mixture was separated, and the sample was mixed with silica gel and dry-loaded onto a column. Purification was performed by silica gel column chromatography (200-300 mesh silica gel, ethyl acetate: n-hexane = 1:15 as eluent). After elution, the mixture was concentrated under reduced pressure at 70°C for 1 hour to obtain a white solid as compound B105-4 (17.71 g, purity: 98.78%, yield: 87.65%), with a mass spectrum of 431.22 (M+H).

[0485] Synthesis of compound B105

[0486] Referring to the synthesis and purification method of compound B3, only the corresponding raw materials need to be changed to obtain the target compound B105 (16.52, purity: 99.93%, yield: 74.62%) as a light yellow solid. 16.52 grams of crude compound B105 was purified by sublimation to obtain sublimation pure compound B105 (13.54 g, purity: 99.93%, yield: 81.97%), mass spectrum: 586.24 (M+H).

[0487] 1 H NMR (400 MHz, CDCl3) δ 8.55 (s, 1H), 8.48 – 8.40 (m, 3H), 8.13 – 8.04 (m, 6H), 8.04 – 7.93 (m, 4H), 7.93 – 7.81 (m, 3H), 7.62 – 7.58 (m, 1H),7.56 – 7.44 (m, 9H).

[0488] Synthesis of compound B162

[0489] .

[0490] Synthesis of compound B162-2

[0491] Referring to the synthesis and purification method of compound B105-4, it is only necessary to change the corresponding raw materials to obtain a light yellow solid as the target compound B162-2 (17.63, purity: 99.02%, yield: 77.96%), mass spectrum: 381.19 (M+H).

[0492] Synthesis of compound B162

[0493] Referring to the synthesis and purification method of compound B3, only the corresponding raw materials need to be changed to obtain the target compound B162 (14.44 g, purity: 99.96%, yield: 76.74%) as a light yellow solid. 14.44 g of crude compound B162 was purified by sublimation to obtain sublimation pure compound B162 (11.76 g, purity: 99.96%, yield: 81.44%), mass spectrum: 576.22 (M+H).

[0494] 1H NMR (400 MHz, CDCl3) δ 8.45 – 8.41 (m, 2H), 8.35 (d, J = 2.5 Hz,1H), 8.26 (d, J = 8.0 Hz, 1H), 8.13 – 8.06 (m, 2H), 8.06 – 8.01 (m, 1H), 8.01– 7.94 (m, 1H), 7.87 (dd, J = 9.3, 1.3 Hz, 1H), 7.68 – 7.60 (m, 2H), 7.60 –7.54 (m, 3H), 7.54 – 7.46 (m, 5H), 7.46 – 7.34 (m, 5H), 7.28 – 7.24 (m, 1H).

[0495] Synthesis of compound B177

[0496] .

[0497] Synthesis of compound B177

[0498] Referring to the synthesis and purification method of compound B3, it is only necessary to change the corresponding raw materials to obtain a light yellow solid as the target compound B177 (21.69 g, purity: 99.93%, yield: 87.70%). 21.69 grams of the crude compound B177 was sublimated and purified to obtain the sublimation pure compound B177 (17.85 g, purity: 99.93%, yield: 82.29%), mass spectrum: 550.20 (M+H).

[0499] 1 H NMR (400 MHz, CDCl3) δ 10.33 (s, 1H), 9.04 (d, J = 8.5 Hz, 1H), 8.92 – 8.76 (m, 4H), 8.51 (d, J = 7.6 Hz, 1H), 8.19 (d, J = 8.2 Hz, 1H), 8.11(d, J = 9.3 Hz, 1H), 8.09 – 7.98 (m, 2H), 7.87 (d, J = 7.8 Hz, 1H), 7.75 –7.65 (m, 5H), 7.60 – 7.50 (m, 3H), 7.26 – 7.21 (m, 3H).

[0500] Synthesis of compound B179

[0501] .

[0502] Synthesis of compound B179

[0503] Compound B177 (15.00 g, 27.29 mmol), deuterated benzene-D6 (4.52 g, 54.58 mol), and trifluoroacetic acid (3.11 g, 27.29 mmol) were added to a 250 mL single-necked round-bottom flask, and the vacuum was replaced with nitrogen three times. The system was then heated to 50 °C and stirred for 24 hours.

[0504] The system was cooled to room temperature, and heavy water (30 mL) was added to quench the reaction. The mixture was stirred at room temperature for 0.5 hours, and then ethyl acetate (200 mL) and deionized water (100 mL) were added to wash three times. The mixture was slurried at room temperature for 30 minutes, and 17 g of solid was obtained by suction filtration. The mixture was vacuum dried at 90 ° C for 1 hour to obtain 16 g of light yellow solid. Toluene (160 mL) and methanol (80 mL) were used for crystallization twice, and the filter cake was vacuum dried at 90 ° C for 3 hours to obtain a light yellow solid compound B179 (12.52 g, purity: 99.94%, yield: 80.12%). 12.52 g of crude compound B179 was sublimated and purified to obtain sublimation pure compound B179 (9.99 g, purity: 99.95%, deuteration rate of 23 Ds was 95.02%, yield: 79.80%), mass spectrum: 573.33 (M+H).

[0505] Synthesis of compound B182

[0506] .

[0507] Synthesis of compound B182

[0508] Referring to the synthesis and purification method of compound B3, it is only necessary to change the corresponding raw materials to obtain a light yellow solid as the target compound B182 (17.06 g, purity: 99.96%, yield: 67.86%). 17.06 grams of the crude compound B182 was sublimated and purified to obtain the sublimation pure compound B182 (14.02 g, purity: 99.96%, yield: 82.18%), mass spectrum: 509.19 (M+H).

[0509] 1H NMR (400 MHz, CDCl3) δ 8.62 (d, J = 8.9 Hz, 1H), 8.57 (d, J = 9.1Hz, 1H), 8.50 – 8.43 (m, 2H), 8.33 (d, J = 9.8 Hz, 1H), 8.21 – 8.19 (m, 1H),8.14 (dd, J = 9.0, 2.2 Hz, 1H), 8.08 – 8.06 (m, 1H), 7.98 – 7.95 (m, 2H),7.92 – 7.82 (m, 6H), 7.80 – 7.88 (m, 1H), 7.56 – 7.47 (m, 4H), 7.46 – 7.37(m, 3H).

[0510] Synthesis of compound B188

[0511] .

[0512] Synthesis of compound B188

[0513] Referring to the synthesis and purification method of compound B3, only the corresponding raw materials need to be changed to obtain a light yellow solid as the target compound B188 (13.33 g, purity: 99.92%, yield: 75.63%). 13.33 grams of crude compound B188 was sublimated and purified to obtain sublimation pure compound B188 (10.02 g, purity: 99.92%, yield: 76.52%), mass spectrum: 550.20 (M+H).

[0514] 1 H NMR (400 MHz, CDCl3) δ 8.62 (d, J = 9.3 Hz, 1H), 8.50 – 8.43 (m,2H), 8.35 (d, J = 7.5 Hz, 1H), 8.15 (d, J = 9.5 Hz, 1H), 8.13 – 8.00 (m, 4H), 7.96 (d, J = 9.3 Hz, 1H), 7.92 – 7.84 (m, 2H), 7.66 – 7.59 (m, 1H), 7.58 –7.38 (m, 9H), 7.28 – 7.24 (m, 1H).

[0515] Synthesis of compound B201

[0516] .

[0517] Synthesis of compound B201

[0518] Referring to the synthesis and purification method of compound B3, only the corresponding raw materials need to be changed to obtain the target compound B201 (12.15 g, purity: 99.93%, yield: 77.86%) as a light yellow solid. 12.15 g of crude compound B201 was purified by sublimation to obtain sublimation pure compound B201 (9.52 g, purity: 99.93%, yield: 78.36%), mass spectrum: 550.20 (M+H).

[0519] 1 H NMR (400 MHz, CDCl3) δ 8.57 – 8.55 (m, 1H), 8.33 – 8.26 (m, 1H), 8.19 (d, J = 9.9 Hz, 1H), 8.10 – 8.00 (m, 5H), 7.96 (d, J = 8.0 Hz, 1H), 7.93– 7.84 (m, 4H), 7.66 – 7.59 (m, 1H), 7.55 – 7.45 (m, 6H), 7.45 – 7.38 (m,2H), 7.26 – 7.24 (m, 1H).

[0520] Synthesis of compound C16

[0521] .

[0522] Synthesis of compound C16

[0523] Compound C16-1 (9.00 g, 34.25 mmol), compound C16-2 (11.49 g, 34.25 mmol), tris(dibenzylideneacetone)dipalladium (Pd2(dba)3, 0.31 g, 0.34 mmol), 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl (X-Phos, 0.32 g, 0.68 mmol), sodium tert-butoxide (NaOtBu, 4.94 g, 51.37 mmol), and toluene (135 mL) were added to a 500 mL three-necked round-bottom flask, and the vacuum was replaced with nitrogen three times. The system was then heated to 105 °C for 2 hours. The reaction was monitored by TLC (ethyl acetate: n-hexane = 1:15 as the developing solvent). The consumption of compound C16-1 was complete.

[0524] The temperature was lowered to 60°C, methanol (150 mL) was added, and the mixture was naturally cooled to room temperature and stirred for 30 minutes to precipitate a large amount of solids. The mixture was filtered to obtain 20 g of solids. Toluene (300 mL) was added, and the system was then heated to 100°C to dissolve and clarify. 30 g of silica gel (300-400 mesh) was spread and filtered. The surface of the silica gel was rinsed with toluene (50 mL), and the filtrate was combined and concentrated to obtain 17 g. Toluene (170 mL) and methanol (80 mL) were used for crystallization twice, and the mixture was filtered and the filter cake was vacuum dried at 90°C for 3 hours to obtain a light yellow solid as the target compound C16 (15.05 g, purity: 99.96%, yield: 78.20%). 15.05 g of crude compound C16 was sublimated and purified to obtain sublimation-purified compound C16 (12.61 g, purity: 99.96%, yield: 83.79%), with a mass spectrum of 562.24 (M+H).

[0525] 1 H NMR (400 MHz, CDCl3) δ 8.63 – 8.56 (m, 2H), 8.50 – 8.43 (m, 1H), 8.03 – 7.93 (m, 3H), 7.93 – 7.85 (m, 2H), 7.83 (d, J = 2.1 Hz, 1H), 7.73 (d,J = 2.0 Hz, 1H), 7.67 – 7.59 (m, 1H), 7.59 – 7.56 (m, 2H), 7.56 – 7.47 (m,4H), 7.47 – 7.37 (m, 6H), 7.32 – 7.30 (m, 1H), 7.03 – 6.97 (m, 2H), 6.90 –6.88 (m, 1H).

[0526] Application example: Fabrication of organic electroluminescent devices

[0527] In one embodiment, if Figure 2 As shown, Figure 2 Schematic diagram of the structure of an organic electroluminescent device, which includes a stacked glass substrate 1, an anode 2 (indium tin oxide), a hole injection layer 3, a first hole transport layer (HTL1) 4, a second hole transport layer (HTL2) 5, a light-emitting layer 6, an electron transport layer (ETL) 7, an electron injection layer 8 (EIL) and a cathode 9.

[0528] A 50 mm×50 mm×1.0 mm glass substrate with an ITO (anode 2, indium tin oxide, 100 nm) transparent electrode was ultrasonically cleaned in ethanol for 10 minutes, dried at 150° C., and then treated with N 2 Plasma (plasma gas) for 30 minutes. The washed glass substrate is mounted on a substrate holder of a vacuum evaporation device, and compound NDP-9 and compound HTM 1 are evaporated at a weight ratio of 97:3 to form a hole injection layer with a thickness of 10 nm, followed by evaporation of a layer of HTM 1 to form a thin film with a thickness of 60 nm as HTL1 (hole transport layer 1), and then a layer of HTM 2 is evaporated on the HTM 1 thin film to form a thin film with a thickness of 10 nm as HTL2 (hole transport layer 2), and then, a light-emitting layer with a thickness of 40 nm is co-evaporated on the HTM 2 film layer in the form of a single host or multiple hosts (host material: red light doping material = 97%: 3%, mass fraction), wherein the host material of the single host or multiple hosts is selected from the compounds of the present invention and comparative compounds 1-4. On the light-emitting layer, ETL (electron transport layer) material and LiQ are co-evaporated (35nm) in a weight ratio of 50:50 as an electron transport material, and then LiQ (1nm) is evaporated on the electron transport material layer as an electron injection material to form an electron injection layer. Then, Mg / Ag (100nm, mass ratio of 1:9) is evaporated as a cathode material using a co-evaporation mode to produce an organic electroluminescent device.

[0529] The structural formulas of NDP-9, HTM1, HTM2, ETL materials, red light doping materials, LiQ, and comparative compounds 1-4 are as follows:

[0530]

[0531] evaluate:

[0532] The above organic electroluminescent device was tested for device performance, and the compound prepared by the present invention and the comparative compounds 1-4 were used as the main materials for comparison. A constant current power supply (Keithley 2400) was used to flow a fixed current density through the light-emitting element, and the luminescence spectrum was tested using a spectroscopic radiation system (CS 2000). At the same time, the luminescence spectrum was measured at 10 mA / cm 2 The IVL (current-voltage-luminance) performance of the device was measured at 50 mA / cm 2 The life of LT95 devices was tested. The results are shown in Tables 1-1, 1-2 and 2 below.

[0533] The device performance data using the compound of the present invention as a dual host and containing comparative compounds 1-4 as a single host or a dual host, which are co-evaporated with red light doping materials to form a light-emitting layer, are shown in Table 1-1 and Table 1-2 (the examples in the table use the compounds of the present invention, and the comparative examples use at least one comparative compound).

[0534] Table 1-1

[0535]

[0536] Table 1-2

[0537]

[0538] In Table 1-1 and Table 1-2, in Example 29, the weight ratio of A54:B3 is 8:2, and in Example 30, the weight ratio of A54:B3 is 2:8. In addition, in the dual-main materials of other embodiments and comparative examples, the weight ratio of the two main materials is 1:1.

[0539] In this embodiment, the first host compound, the second host compound and the third host compound are mixed by vapor deposition in a weight ratio of 2:1:1 (first host: second host: third host), and the device data of the light-emitting layer are co-evaporated with the red light doping material as shown in Table 2.

[0540] Table 2

[0541]

[0542] It can be seen from the above table that the device life corresponding to the device prepared by the compound of the present invention is significantly better than the efficiency and life of the device prepared by using the comparative compounds 1-4.

[0543] Sublimation temperature comparison: Sublimation temperature is defined as: at 10 -7 The vacuum degree is 10000 Torr, and the temperature corresponding to the sublimation rate is 1 angstrom per second. The test results are shown in Table 3.

[0544] Table 3

[0545]

[0546] It can be seen from Table 3 that the compounds of the present invention have lower sublimation temperatures than the comparative compounds 1-4, which is conducive to industrial application.

[0547] The compound of the present invention, as a dual-host red light material, has lower voltage, higher current efficiency and longer life than the comparative compound. Since the hole and electron transfer rates are balanced and the exciton recombination area in the light-emitting layer is broadened, the efficiency and life of the device are greatly improved compared with comparative examples 1-5. At the same time, when the compound of the present invention is used as a triple-host material, the efficiency and life of the device are greatly improved compared with comparative example 6.

[0548] Therefore, the compound material of the present invention has the advantages of high optical and electrical stability, low sublimation temperature, low driving voltage, high luminous efficiency, long device life, etc., and can be used as a main material in OLED light-emitting devices. At the same time, it has a low melting point, which is beneficial to the stability of material evaporation as a molten material. The compound of the present invention, as a main material, has the possibility of being applied to the AMOLED industry.

[0549] In addition, since it is impossible to enumerate all the compounds of the present invention, the above Tables 1-1, 1-2, 2 and 3 only list some of the compounds or device properties of the present invention. However, within the scope of protection requested by the present invention, especially the compounds with specific structural formulas given in the present invention, all have the advantages similar to A1, 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, characterized in that: The host material comprises at least one first host compound and at least one second host compound, wherein the first host compound has a structure shown in formula (1): Formula (1), Wherein, ring A is selected from the following formula (1-2) or formula (1-3); Formula (1-2), Formula (1-3), Among them, X1-X 12 are independently selected from CR0 or N; and X1-X 12 Contains at least one N, X1-X4, X 5- X6, X7-X8, X9-X 12 There are two adjacent sites in the formula (1) that are fused to the 5-membered ring containing X; Alternatively, ring A is selected from one of the structures represented by the following formula (1-4) to formula (1-11): ， ， in, represents the site of fusion with the 5-membered ring containing X in formula (1); a is an integer of 0-10; when a is an integer of 2-10, each R0 may be the same or different; R0 is independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C3-C20 heteroaryl, substituted or unsubstituted C1-C20 alkylsilyl, substituted or unsubstituted C6-C20 arylsilyl; Wherein, ring B is selected from one of the structures represented by the following formula (1-20) to formula (1-26): ， in, represents the fusion site with the five-membered ring containing X in formula (1); R g independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C6-C12 aryl, or substituted or unsubstituted C3-C12 heteroaryl; w is an integer of 0-10; when w is an integer of 2-10, each R g Can be the same or different; Wherein, X in formula (1) is selected from NR a , CR b R c , O or S; R a , R b , R c are independently selected from substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C6-C10 aryl, or substituted or unsubstituted C5-C10 heteroaryl; Ar1 and Ar2 are independently selected from substituted or unsubstituted C6-C60 aryl, or substituted or unsubstituted C3-C60 heteroaryl; Wherein, the second main compound has a structure shown in formula (2): Formula (2), Wherein, Z1, Z2, and Z3 are each independently selected from N or CR d , and at least two of Z1, Z2, and Z3 are N; Ar3 to Ar5 each independently represent a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C3-C30 heteroaryl group; Among them, at least one of Ar3 to Ar5 is selected from the following formula (2-1), formula (2-2) or formula (2-3): ， in, represents the connection site with L1, L2, and L3 in formula (2); R d is selected from hydrogen, deuterium, halogen or cyano; R1 is independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C6-C12 aryl, or substituted or unsubstituted C3-C12 heteroaryl; q is an integer from 0 to 10, wherein when q is an integer from 2 to 10, each R1 may be the same or different; The L, L1, L2, and L3 are independently selected from a single bond, a substituted or unsubstituted C6-C30 arylene group, or a substituted or unsubstituted C3-C30 heteroarylene group; R0, R1, R a ~R c , R g , L, L1~L3, Ar1~Ar5, the substitution is substituted by at least one of deuterium, halogen, cyano, C1-C6 alkyl, C3-C16 cycloalkyl, C1-C6 alkyl substituted or unsubstituted C6-C30 aryl, or C1-C6 alkyl substituted or unsubstituted C3-C30 heteroaryl, wherein the number of substitutions ranges from a single substitution to a maximum number of substitutions; The heteroatoms in the heteroarylene or heteroaryl are independently selected from at least one of O, S, N, Se, Si or Ge; The aryl group, arylene group, heteroaryl group and heteroarylene group are each independently selected from a monocyclic or polycyclic structure, wherein a plurality of rings in the polycyclic structure are connected to each other via a single bond or fused to each other.

2. The main body material according to claim 1, characterized in that In formula (1), ring A is selected from one of the structures represented by the following formulas (1-12) to (1-19): ， ， in, represents the site of fusion with the 5-membered ring containing X in formula (1); wherein a is an integer of 0-6; when a is an integer of 2-6, each R0 may be the same or different.

3. The main body material according to any one of claims 1 to 2, characterized in that: In formula (2), at least one of Ar3 to Ar5 is selected from the structure represented by the following formula (2-4), formula (2-5) or formula (2-6): ， in, represents the bonding site from Ar3 to Ar5.

4. The main body material according to claim 3, characterized in that The X is selected from O, and the Z1, Z2, and Z3 are all N; and / or, L, L1, L2, and L3 are independently selected from a single bond or one of the structures represented by the following formula (3-1) to formula (3-17): ， ， in, Indicates the bonding sites of L, L1, L2, and L3.

5. The main body material according to any one of claims 1 to 2, characterized in that: The Ar1 to Ar5 are each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted 9,9-spirobifluorenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted chrysene, The invention may be selected from the group consisting of at least one of a substituted or unsubstituted carbazolyl, a substituted or unsubstituted pyridyl, a substituted or unsubstituted pyrimidinyl, a substituted or unsubstituted fluoranthene, a substituted or unsubstituted benzoxazolyl, a substituted or unsubstituted benzimidazolyl, a substituted or unsubstituted benzotriazolyl, a substituted or unsubstituted benzophenanthryl, a substituted or unsubstituted naphthoxazolyl, a substituted or unsubstituted benzocycloalkyl, a substituted or unsubstituted phenanthroxazolyl, an oxaspirofluorenyl, and a substituted or unsubstituted benzocarbazolyl.

6. The main body material 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 replaced by deuterium or fluorine: ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ； And / or, 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 replaced by deuterium or fluorine: ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， 。 7. The main body material according to claim 1, characterized in that The host material further comprises at least one third host compound, wherein the first host compound is represented by formula (1), the second host compound is selected from one of the structures shown in B1-B210, B1-B210 is as defined in claim 6; the third host compound is selected from one of the following structural formulas, or one of the following structural formulas in which hydrogen is partially or completely replaced by deuterium or fluorine: ， 。 8. An organic electroluminescent device, characterized in that: Comprising the main material as described in any one of claims 1-7.

9. The organic electroluminescent device according to claim 8, characterized in that: It comprises a light-emitting layer, wherein the light-emitting layer comprises the host material.

10. A semiconductor device, characterized in that: The semiconductor device comprises the host material according to any one of claims 1-7.

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