Host material and organic electroluminescent device

Abstract

Disclosed are 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), wherein ring A is selected from formula (1-2) or formula (1-3), X1-X12 are each independently selected from CR0 or N, and X is selected from NRa, CRbRc or an oxygen family element. The host material has the advantages of low sublimation temperature, low driving voltage, high light emitting efficiency, long device service life and the like, and can be applied to an organic electroluminescent device.

Description

A host material and an organic electroluminescent device TECHNICAL FIELD

[0001] The present application belongs to the technical field of organic electroluminescence, and particularly relates to a host material and an organic electroluminescent device. BACKGROUND

[0002] At present, the organic electroluminescent device (OLED) as a new generation of display technology has obtained more and more attention in display and lighting technology, and has a very wide application prospect. However, compared with the market application requirements, the performance of the OLED device such as the luminous efficiency, the driving voltage and the service life still needs to be improved.

[0003] Generally, the basic structure of the OLED device is a sandwich structure in which various different functional organic functional material thin films are sandwiched between metal electrodes. Under the driving of the current, electrons and holes are injected from the cathode and anode respectively, the holes and the electrons are combined in the light-emitting layer after moving a distance, and are released in the form of light or heat, so as to achieve the light-emitting effect. However, the properties of the phosphorescent OLED are not only determined by the used triplet light emitter. Other types of materials, such as the host material, are also quite important. The host material has a significant effect on reducing the driving voltage of the device, improving the luminous efficiency of the device and improving the service life of the device. However, the existing host material has a limited performance improvement range for the OLED device.

[0004] Therefore, it is necessary to continue to develop new host materials and their compositions to further improve the performance of the organic electroluminescent device, so as to solve the above problems existing in the organic electroluminescent device. SUMMARY

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

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

[0007] wherein ring A is selected from formula (1-2) or formula (1-3);

[0008] wherein X1-X 12 are independently selected from CR0 or N; and X1-X4, X 5- X6, X7-X8, X9-X 12two adjacent positions are fused to the 5-membered ring containing X in Formula (1);

[0009] wherein ring B is selected from a substituted or unsubstituted phenyl ring, a substituted or unsubstituted naphthyl ring, or a substituted or unsubstituted phenanthrene ring;

[0010] wherein X in Formula (1) is selected from NR a , CR b R c , or an oxygen group;

[0011] R a , R b , R c are each independently selected from a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C1-C30 heteroalkyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C3-C30 heterocycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C3-C30 heteroaryl group, a substituted or unsubstituted C1-C30 alkylsilyl group, or a substituted or unsubstituted C6-C30 arylsilyl group; or, R b and R c are linked to form a ring;

[0012] L is selected from a single bond, a substituted or unsubstituted C6-C60 arylene group, or a substituted or unsubstituted C3-C60 heteroarylene group;

[0013] Ar1and Ar2are each independently selected from a substituted or unsubstituted C6-C60 aryl group, or a substituted or unsubstituted C3-C60 heteroaryl group;

[0014] wherein the second host compound has a structure represented by Formula (2):

[0015] wherein Z1, Z2, Z3are each independently selected from N or CR d ;

[0016] Ar3to Ar5each independently represent hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C3-C60 heteroaryl group, a substituted or unsubstituted C3-C60 cycloalkyl group, a substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted tri(C1-C30)alkylsilyl group, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl group, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl group, a substituted or unsubstituted tri(C6-C30)arylsilyl group, or -N-(R’)(R”), or Ar3to Ar5are each independently linked to form a ring with the substituents on the carbon atom or heteroatom adjacent to the substitution site thereof;

[0017] wherein at least one of Ar3to Ar5is selected from the following formula (2-1), formula (2-2), or formula (2-3):

[0018] wherein “*” represents the connection site with L1, L2, L3in formula (2);

[0019] R d , R0, R1are each independently selected from hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted C1-C40alkyl, substituted or unsubstituted C1-C40heteroalkyl, substituted or unsubstituted C2-C40alkenyl, substituted or unsubstituted C2-C40alkynyl, substituted or unsubstituted C3-C40cycloalkyl, substituted or unsubstituted C3-C40heterocycloalkyl, substituted or unsubstituted C6-C60aryl, substituted or unsubstituted C3-C60heteroaryl, substituted or unsubstituted C1-C40alkoxy, substituted or unsubstituted C6-C60aryloxy, substituted or unsubstituted C1-C40alkylsilyl, substituted or unsubstituted C6-C60arylsilyl, substituted or unsubstituted C1-C40alkylboronyl, substituted or unsubstituted C6-C60arylboryl, substituted or unsubstituted C6-C60arylphosphino, or substituted or unsubstituted C6-C60arylamino; or, two adjacent R0are connected to form a fused ring;

[0020] wherein R’ and R” each independently represent substituted or unsubstituted C1-C30alkyl, substituted or unsubstituted C2-C30alkenyl, substituted or unsubstituted C6-C30aryl, or substituted or unsubstituted C3-C30heteroaryl;

[0021] q is an integer from 0 to 10, wherein when q is an integer from 2 to 10, then each R1may be the same or different, and adjacent R1may be connected to form a fused ring;

[0022] L1, L2, L3are independently selected from a single bond, substituted or unsubstituted C6-C60arylene, or substituted or unsubstituted C3-C60heteroarylene, or substituted or unsubstituted C3-C30cycloalkylene;

[0023] the R0, R1, R a , R d , L, L1-L3, Ar1-Ar5, R’, R” are substituted with at least one of deuterium, halogen, cyano, isocyano, phosphino, C1-C6alkyl, C3-C16cycloalkyl, C1-C6alkyl substituted or unsubstituted amine, C1-C6hydrocarbyl substituted or unsubstituted C6-C30aryl, or C1-C6hydrocarbyl substituted or unsubstituted C3-C30heteroaryl, wherein the number of substitutions is from monosubstitution to the maximum number of substitutions;

[0024] The heteroatom in the heteroarylene, heteroaryl, heteroalkyl, heterocycloalkyl or heteroatom is independently selected from at least one of O, S, N, Se, Si or Ge.

[0025] The beneficial effects of the present application are as follows:

[0026] The host material has the advantages of low sublimation temperature, low driving voltage, high luminous efficiency, long device life, etc., and can be used as a host material in an OLED light-emitting device. At the same time, it has a relatively low melting point, which is beneficial to the stability of material evaporation as a melt type material. As a red light host material, it has the possibility of application in the AMOLED (active matrix organic light-emitting diode) industry. BRIEF DESCRIPTION OF DRAWINGS

[0027] Figure 1 is a structure of compound A226 according to the present application. 1 H NMR spectrum;

[0028] Figure 2 is a structure diagram of an organic electroluminescent device according to an embodiment of the present application. DETAILED DESCRIPTION

[0029] In order to make those skilled in the art more clearly understand the technical solutions of the present application, the following examples are given for illustration. It should be pointed out that the following examples do not constitute a limitation on the scope of protection required by the present application.

[0030] Specifically, the first aspect of the present application relates to a host material comprising at least one first host compound and at least one second host compound, wherein the first host compound has a structure represented by formula (1):

[0031] wherein ring A is selected from the following formula (1-2) or formula (1-3);

[0032] wherein X1-X 12 are independently selected from CR0 or N; and X1-X4, X 5- X6, X7-X8, X9-X 12 two adjacent sites are fused to the 5-membered ring containing X in formula (1);

[0033] 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;

[0034] wherein X in formula (1) is selected from NR a , CR b R c or an oxygen element;

[0035] R a , Rb , R c are each 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 are linked to form a ring;

[0036] L is selected from a single bond, substituted or unsubstituted C6-C60 arylene, or substituted or unsubstituted C3-C60 heteroarylene;

[0037] Ar1and Ar2are each independently selected from substituted or unsubstituted C6-C60 aryl, or substituted or unsubstituted C3-C60 heteroaryl;

[0038] wherein the second host compound has a structure represented by Formula (2):

[0039] wherein Z1, Z2, Z3are each independently selected from N or CR d ;

[0040] Ar3to Ar5each 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 Ar3to Ar5are each independently linked to a substituent on a carbon atom or a heteroatom adjacent to the substitution site thereof to form a ring;

[0041] wherein at least one of Ar3to Ar5is selected from the following Formula (2-1), Formula (2-2), or Formula (2-3):

[0042] wherein “*” represents a connection site to L1, L2, L3in Formula (2);

[0043] R d, R0, R1are each independently selected from hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted C1-C40alkyl, substituted or unsubstituted C1-C40heteroalkyl, substituted or unsubstituted C2-C40alkenyl, substituted or unsubstituted C2-C40alkynyl, substituted or unsubstituted C3-C40cycloalkyl, substituted or unsubstituted C3-C40heterocycloalkyl, substituted or unsubstituted C6-C60aryl, substituted or unsubstituted C3-C60heteroaryl, substituted or unsubstituted C1-C40alkoxy, substituted or unsubstituted C6-C60aryloxy, substituted or unsubstituted C1-C40alkylsilyl, substituted or unsubstituted C6-C60arylsilyl, substituted or unsubstituted C1-C40alkylboron, substituted or unsubstituted C6-C60arylboron, substituted or unsubstituted C6-C60arylphosphine, or substituted or unsubstituted C6-C60arylamines; or, two adjacent R0are linked to form a fused ring;

[0044] wherein R’ and R” are each independently represent substituted or unsubstituted C1-C30alkyl, substituted or unsubstituted C2-C30alkenyl, substituted or unsubstituted C6-C30aryl, or substituted or unsubstituted C3-C30heteroaryl;

[0045] q is an integer from 0 to 10, wherein when q is an integer from 2 to 10, then each R1may be the same or different, and adjacent R1may be linked to form a fused ring;

[0046] L1, L2, L3are independently selected from a single bond, substituted or unsubstituted C6-C60arylene, or substituted or unsubstituted C3-C60heteroarylene, or substituted or unsubstituted C3-C30cycloalkylene;

[0047] the R0, R1, R a ~R d , L, L1~L3, Ar1~Ar5, R’, R” are each independently substituted with at least one of deuterium, halogen, cyano, isocyano, phosphino, C1-C6alkyl, C3-C16cycloalkyl, C1-C6alkyl substituted or unsubstituted amine, C1-C6hydrocarbyl substituted or unsubstituted C6-C30aryl, or C1-C6hydrocarbyl substituted or unsubstituted C3-C30heteroaryl, wherein the number of substitutions is mono-substitution to the maximum number of substitutions;

[0048] wherein the heteroatom in heteroarylene, heteroaryl, heteroalkyl, heterocycloalkyl, or heteroatom is independently selected from at least one of O, S, N, Se, Si, or Ge.

[0049] In some embodiments, ring A is selected from one of the following structures shown in formula (1-4) to formula (1-11):

[0050] wherein "*" indicates the site of fusion to the X-containing 5-membered ring in Formula (1);

[0051] wherein a is an integer from 0 to 10; when a is an integer from 2 to 10, then each R0may be the same or different, and adjacent R0may be connected to form a fused ring.

[0052] In some embodiments, ring A is selected from one of the structures depicted in the following Formula (1-12) to Formula (1-19):

[0053] wherein "*" indicates the site of fusion to the X-containing 5-membered ring in Formula (1);

[0054] wherein a is an integer from 0 to 6; when a is an integer from 2 to 6, then each R0may be the same or different, and adjacent R0may be connected to form a fused ring.

[0055] In some embodiments, adjacent R0refers to R0on adjacent carbon atoms.

[0056] In some embodiments, ring B in Formula (1) is selected from one of the structures depicted in the following Formula (1-20) to Formula (1-26):

[0057] wherein "*" indicates the site of fusion to the X-containing 5-membered ring in Formula (1);

[0058] R g is independently selected from hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted C1-C40alkyl, substituted or unsubstituted C1-C40heteroalkyl, substituted or unsubstituted C2-C40alkenyl, substituted or unsubstituted C2-C40alkynyl, substituted or unsubstituted C3-C40cycloalkyl, substituted or unsubstituted C3-C40heterocycloalkyl, substituted or unsubstituted C6-C60aryl, substituted or unsubstituted C3-C60heteroaryl, substituted or unsubstituted C1-C40alkoxy, substituted or unsubstituted C6-C60aryloxy, substituted or unsubstituted C1-C40alkylsilyl, substituted or unsubstituted C6-C60arylsilyl, substituted or unsubstituted C1-C40alkylboronyl, substituted or unsubstituted C6-C60arylboryl, substituted or unsubstituted C6-C60arylphosphino, or substituted or unsubstituted C6-C60arylamino;

[0059] R gsubstituted with at least one of deuterium, halogen, cyano, isocyano, phosphino, C1-C6alkyl, C3-C16cycloalkyl, C1-C6alkyl-substituted or unsubstituted amine, C1-C6hydrocarbyl-substituted or unsubstituted C6-C30aryl, or C1-C6hydrocarbyl-substituted or unsubstituted C3-C30heteroaryl, wherein the number of substitutions ranges from mono-substitution to the maximum number of substitutions;

[0060] wherein w is an integer from 0 to 10; when w is an integer from 2 to 10, then each R g may be the same or different, and adjacent R g may be connected to form a fused ring.

[0061] In some embodiments, L, L1, L2, L3are independently selected from a single bond, substituted or unsubstituted C6-C40arylene, or substituted or unsubstituted C3-C40heteroarylene.

[0062] In some embodiments, L, L1, L2, L3are independently selected from a single bond, substituted or unsubstituted C6-C30arylene, or substituted or unsubstituted C3-C30heteroarylene.

[0063] In some embodiments, L, L1, L2, L3are independently selected from a single bond or one of the structures shown in Formula (3-1) to Formula (3-17):

[0064] wherein “*” indicates the bond connection site of L, L1, L2, L3.

[0065] In some embodiments, X is selected from NR a , CR b R c , O, S, or Se.

[0066] In some embodiments, R a , R b , R c are each independently selected from substituted or unsubstituted C1-C10alkyl, substituted or unsubstituted C1-C10heteroalkyl, substituted or unsubstituted C3-C10cycloalkyl, substituted or unsubstituted C3-C10heterocycloalkyl, substituted or unsubstituted C6-C10aryl, or substituted or unsubstituted C5-C10heteroaryl; or, R b and R c are connected to form a fluorene group (e.g. ).

[0067] In some embodiments, X1-X 12 contains at least one N.

[0068] In some embodiments, Z1, Z2, Z3are each independently selected from N or CRd , R d is independently selected from hydrogen, deuterium, halogen, cyano, nitro, or C1-C10 alkyl, and at least one of Z1, Z2, Z3 is N.

[0069] In some embodiments, at least two of Z1, Z2, Z3 are N.

[0070] In some embodiments, in formula (1), X is selected from O or S.

[0071] In some embodiments, in formula (1), X is selected from O or S; in formula (2), Z1, Z2, Z3 are all selected from N.

[0072] In some embodiments, in formula (1), X is selected from O; in formula (2), Z1, Z2, Z3 are all selected from N.

[0073] 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.

[0074] In some embodiments, in formula (2), Ar3 to Ar5 are independently selected from the structure represented by formula (2-4), formula (2-5), or formula (2-6):

[0075] wherein “*” represents the bonding site of Ar3 to Ar5.

[0076] In some embodiments, R d , R0, R1, R geach 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 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 alkylboron, substituted or unsubstituted C6-C20 arylboron, substituted or unsubstituted C6-C20 arylphosphine, or substituted or unsubstituted C6-C20 arylamine.

[0077] In some embodiments, R d , R0, R1, R g 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.

[0078] In some embodiments, R d , R0, R1, R g 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.

[0079] In some embodiments, R d , R0, R1each independently selected from hydrogen, deuterium, halogen, cyano, nitro, or C1-C10 alkyl.

[0080] In some embodiments, R g is independently selected from hydrogen, deuterium, methyl, deuterated methyl, halogen, phenyl, t-butyl, naphthyl, cyano, or cyclohexyl. Wherein the deuterated methyl is mono-deuterated, di-deuterated, or tri-deuterated.

[0081] In some embodiments, Ar1to Ar5are each independently selected from at least one of 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 In some embodiments, Ar1to Ar5are each independently selected from at least one of 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

[0082] In some embodiments, wherein the substituents are each independently at least one of deuterium, halogen, cyano, isocyano, phosphino, C1-C6alkyl, C3-C12cycloalkyl, C1-C6alkyl-substituted amine, C6-C18aryl, or C3-C18heteroaryl, wherein the number of substituents ranges from monosubstitution to the maximum number of substitution.

[0083] In some embodiments, wherein the substituents are each independently at least one of deuterium, halogen, cyano, isocyano, phosphino, C1-C6alkyl, C3-C10cycloalkyl, C1-C6alkyl-substituted amine, C6-C12aryl, or C3-C12heteroaryl, wherein the number of substituents ranges from monosubstitution to the maximum number of substitution.

[0084] In some embodiments, the aryl group is selected from phenyl, naphthyl, anthracenyl, phenanthrenyl, naphthacenyl, pyrenyl, In some embodiments, the aryl group is selected from phenyl, naphthyl, anthracenyl, phenanthrenyl, naphthacenyl, pyrenyl,

[0085] In some embodiments, the heteroaryl group is selected from pyrrolyl, pyrrolopyrrolyl, furopyrrolyl, thienopyrrolyl, pyridyl, pyrazolyl, pyrimidinyl, pyrazinyl, pyridazinyl, phenoxazinyl, phenothiazinyl, phenoxazinyl, indolyl, isoindolyl, imidazolyl, benzimidazolyl, triazolyl, tetrazolyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, furopyrrolofuranyl, azadibenzofuranyl, thienofuranyl, diazadibenzofuranyl, benzo[B]naphtho[1,2-D]furanyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, quinazolinonyl, carbazolyl, azacarbazolyl, diazacarbazolyl, phenanthridinyl, perimidinyl, acridinyl, dihydroacridinyl, phenanthrolinyl, oxazolinyl, oxazolyl, oxadiazolyl, benzisoxazolyl, thiazolyl, benzothiazolyl, benzisothiazolyl, pyrroloimidazolyl, furazanyl, thienyl, benzothienyl, dibenzothienyl, azadibenzothienyl, diazadibenzothienyl, thienothienyl, or phthalazinyl.

[0086] In some embodiments, the aryl phosphine group is selected from monoaryl phosphine or diaryl phosphine.

[0087] In some embodiments, the compound of Formula (1) is selected from one of the following structural formulae, or one of the following structural formulae in which the hydrogens are partially or completely replaced by deuterium or fluorine:

[0088] In some embodiments, the compound of Formula (2) is selected from one of the following structural formulae, or one of the following structural formulae in which the hydrogens are partially or completely replaced by deuterium or fluorine:

[0089] 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 in the range of 1 :99 to 99: 1, preferably in the range of 10:90 to 90: 10, more preferably selected from the range of 20:80 to 80:20, 30:70 to 70:30, or 40:60 to 60:40, even more preferably 50:50.

[0090] In some embodiments, the host material further comprises at least one third host compound, which is represented by the formula (1) or formula (2), but is different from the first host compound or the second host compound.

[0091] In some embodiments, 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 represented by B1-B210, and the third host compound is selected from one of the structures represented by C1-C20.

[0092] In some embodiments, the host material composition comprises a first host compound, a second host compound, and a third host compound, which is different from the first host compound and the second host compound. The weight ratio of the first host compound in the host material composition is in the range of 5wt% to 90wt%, preferably selected from the range of 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 in the range of about 5wt% to 90wt%, preferably selected from the range of 10wt% to 90wt%, 10wt% to 80wt%, 10wt% to 40wt%, 15wt% to 70wt%, 30wt% to 70wt%, 20wt% to 60wt%, or 30wt% to 60wt%; and the weight ratio of the third host compound is in the range of about 5wt% to 90wt%, preferably selected from the range of 10wt% to 90wt%, 10wt% to 80wt%, 10wt% to 40wt%, 15wt% to 70wt%, 30wt% to 70wt%, 20wt% to 60wt%, or 30wt% to 60wt%. For example, the host material composition can comprise a first host compound in the weight ratio of 5wt% to 70wt%, a second host compound in the weight ratio of 5wt% to 70wt%, and a third host compound in the weight ratio of 10wt% to 90wt%. The host material composition can also comprise a first host compound in the weight ratio of 20wt% to 80wt%, a second host compound in the weight ratio of 10wt% to 40wt%, and a third host compound in the weight ratio of 10wt% to 40wt%.

[0093] The second aspect of the present application provides an organic electroluminescent device.

[0094] Specifically, the organic electroluminescent device comprises the host material.

[0095] In some embodiments, the organic electroluminescent device comprises an anode and a cathode, and a light-emitting layer is contained between the anode and the cathode, wherein the light-emitting layer comprises the host material.

[0096] In one embodiment, the light-emitting layer is a red light-emitting layer, and comprises a red light-emitting material and the host material. In this embodiment, the host material serves as a host material of the red light-emitting layer.

[0097] The third aspect of the present application provides an application of the compound in the field of semiconductors.

[0098] Specifically, the application of the host material in the preparation of a semiconductor device.

[0099] In some embodiments, the semiconductor device is a photoelectric device.

[0100] The host material of the present application has the advantages of low sublimation temperature, low driving voltage, high luminous efficiency, long device lifetime, and the like, and can be used as a host material in OLED light-emitting devices. At the same time, the host material has a relatively low melting point, and is advantageous as a melt-type material in terms of material evaporation stability. The host material, as a red light-emitting host material, has the potential to be applied in the AMOLED (active matrix organic light-emitting diode) industry.

[0101] Definitions

[0102] Unless otherwise defined, scientific and technical terms used in this text have meanings commonly understood by those skilled in the art, however, in order to better understand the present application, the definitions of some terms are provided below. When the definitions of the terms provided in the present application are inconsistent with the meanings commonly understood by those skilled in the art, the definitions and explanations of the terms provided in the present application shall prevail.

[0103] The term "alkyl" refers to straight-chain or branched-chain saturated hydrocarbon groups. Specifically, the number of carbon atoms can be 1 to 60, 1 to 40, 1 to 30, 1 to 20, 1 to 12, 1 to 6, or 1 to 3. Non-limiting examples of alkyl groups include methyl, ethyl, propyl, butyl, heptyl, decyl, and the like. Each group includes various isomers, such as butyl which includes n-butyl, isobutyl, sec-butyl, t-butyl, and the like.

[0104] The term "heteroalkyl" refers to at least one carbon atom replaced by a non-carbon atom or a group containing a non-carbon atom on the basis of an alkyl group, which non-carbon atom can be selected from at least one of O, S, N, P, B, Si, Ge, or Se, but excluding the case where the carbon atom attached to the main structure is replaced by a non-carbon atom (e.g., alkoxy, alkylsilyl, alkylboron). Non-limiting examples of heteroalkyl groups include mercaptomethanyl, methoxymethanyl, ethoxymethanyl, t-butoxymethanyl, N,N-dimethylmethanyl.

[0105] The term "alkoxy" refers to a group having -O-alkyl, i.e., 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 t-butoxy.

[0106] The term "alkenyl" refers to a hydrocarbon group containing at least one double bond. The number of carbon atoms in an alkenyl group can be 2 to 40, 2 to 30, 2 to 20, 2 to 12, 2 to 10, or 2 to 6. Non-limiting examples of alkenyl groups include: ethenyl, propenyl, allyl, isopropenyl, 1-butyldienyl, 2-butyldienyl, 1-hexatrienyl, 2-hexatrienyl, 3-hexatrienyl.

[0107] The term "alkynyl" refers to a hydrocarbon group containing at least one triple bond. The number of carbon atoms in an alkenyl group can be 2 to 40, 2 to 30, 2 to 20, 2 to 12, 2 to 10, 2 to 6, or 2 to 4. Non-limiting examples of alkynyl groups include: ethynyl and propargyl.

[0108] The term "cycloalkyl" refers to a non-aromatic carbon-based ring consisting of at least 3 carbon atoms, which can include single-, multiple-, and spirocyclic alkyl groups. The number of carbon atoms in a cycloalkyl 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 cycloalkyl groups include: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, bicyclo[3.1.1]heptyl, spiro[4.5]decyl, spiro[5.5]undecyl, adamantyl, norbornyl.

[0109] The term "heterocycloalkyl" refers to at least one carbon atom replaced by a non-carbon atom on the basis of a cycloalkyl group, which 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 a 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: cyclobutanonyl, cyclopentanonyl, and cyclohexanonyl.

[0110] The term "aryl" refers to an aromatic hydrocarbon group derived from a parent aromatic ring compound by removal of one hydrogen atom, and can be a monocyclic aryl group or a polycyclic aryl group. At least one ring in a polycyclic aryl group is an aromatic ring system. Multiple rings in a polycyclic aryl group can be connected to each other via single bonds or can be fused to each other. The number of carbon atoms in an aryl group can be 6 to 60, 6 to 40, 6 to 30, 6 to 20, 6 to 12, or 6 to 10. For example, when a polycyclic aryl group contains a fused ring structure, it can be specifically formed by the fusion of 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 the fusion of a C3-C20 aliphatic ring and a C6-C30 aromatic ring. Understandably, the term "arylene" refers to a divalent group derived from an aromatic ring compound by removal of two hydrogen atoms.

[0111] The term "heteroaryl" refers to a monovalent group of a heterocyclic aromatic system in which at least one carbon atom is replaced by a non-carbon atom selected from O, S, N, P, B, Se, Si, or Ge, on the basis of an aryl group, but excluding the case where an aryl group is connected to the main structure through a non-carbon atom group (for example, aryloxy, arylsilyl, arylboron, arylphosphine, arylamine). Understandably, the term "heteroarylene" refers to a divalent group having the same structure as a heteroaryl group.

[0112] "Ar3 to Ar5 are each independently and the substituents on the carbon atoms adjacent to the substitution sites thereof are cyclized", means that the substituents on the substitution sites of Ar3 to Ar5 and the substituents on the carbon atoms of L1 to L3 can be cyclized, or when L1 to L3 are single bonds, the substituents on the substitution sites of Ar3 to Ar5 and Z1 to Z3 are cyclized. For example, L1 and Ar3, L2 and Ar4, L3 and Ar5, can be optionally connected to each other to form a substituted or unsubstituted naphthalene, fluorenyl, quinoline, dibenzothiophene, dibenzofuran, carbazole, benzofuro[3,2-g]pyridine, benzothieno[3,2-g]pyridine, indeno[1,2-g]pyridine, benzofuro[3,2-g]quinoline, benzothieno[3,2-g]quinoline, or indeno[1,2-g]quinoline ring.

[0113] The term "adjacent" means that two groups or atoms are directly bonded, or two groups or atoms are directly adjacent substituents to each other (i.e., two substitution sites are directly connected, not indirectly connected through other atoms or groups).

[0114] "Substituted or unsubstituted X group having a-b carbon number" in this expression means the carbon number of the X group when it is unsubstituted, excluding the carbon number of the substituents when the X group is substituted.

[0115] "Substituted" in "substituted or unsubstituted" means that one or more hydrogen atoms are replaced by other atoms or functional groups (i.e., substituents), and also includes replacement of one or more hydrogen atoms by a group formed by linking two or more of the above substituents, unless otherwise limited by definition.

[0116] The following examples are merely intended to facilitate the understanding of the technical invention, and should not be regarded as specific limitations of the present invention.

[0117] The raw materials and solvents involved in the synthesis of the compounds in the present application are purchased from suppliers well known to those skilled in the art such as Alfa, Acros, etc. 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.

[0118] Synthesis of compound A1

[0119] Synthesis of compound A1-3

[0120] A1-1 (30.00 g, 106.56 mmol), A1-2 (32.47 g, 127.87 mmol), 1,1-bis(diphenylphosphino)ferrocene palladium dichloride (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 into a 1000 ml three-necked round-bottom flask, replaced with vacuum nitrogen three times, then the system was heated to 100°C for 2 hours, and the reaction was monitored by TLC (ethyl acetate: n-hexane = 1:10 as developing agent), and A1-1 was consumed.

[0121] The temperature was lowered to 60°C, and the solvent was removed by concentration under reduced pressure, ethyl acetate (700 ml) was added, washed with deionized water three times (300 mL x 3), separated, and the silica gel sample was mixed and dried, and column chromatography was performed (200-300 mesh silica gel, ethyl acetate: n-hexane = 1:15 as eluent), and after elution, 70°C under reduced pressure for 1 hour to obtain white solid A1-3 (27.62 g, purity: 98.01%, yield: 78.88%), mass spectrum: 329.12 (M+H).

[0122] Synthesis of compound A1-5

[0123] A1-3 (25.00 g, 76.08 mmol), A1-4 (17.89 g, 76.08 mmol), Pd(PPh3)4 (1.75 g, 1.52 mmol), K2CO3 (15.77 g, 114.12 mmol), THF (375 mL), DI water (125 mL) were added into a 1000 mL three-necked round-bottom flask, replaced with nitrogen for three times, then the system was heated to 75 °C for 3 hours, TLC (ethyl acetate: n-hexane = 1:10 as developing agent) was used to monitor the reaction, and A1-3 was consumed completely.

[0124] The system was cooled to 60 °C, and the solvent was removed by concentration under reduced pressure. Ethyl acetate (700 mL) was added, and the mixture was washed with DI water three times (300 mL x 3). The mixture was separated, and the silica gel was used to dry the sample. The sample was purified by silica gel column chromatography (200-300 mesh silica gel, ethyl acetate: n-hexane = 1:20 as eluent). After elution, the white solid was obtained by concentration under reduced pressure at 70 °C for 2 hours. The white solid was A1-5 (20.45 g, purity: 99.21%, yield: 75.32%), and the mass was 357.22 (M+H).

[0125] Synthesis of compound A1-7

[0126] A1-5 (18.00 g, 50.45 mmol), A1-6 (25.94 g, 75.67 mmol), THF (270 mL) were added into a 1000 mL three-necked round-bottom flask, replaced with nitrogen for three times, then the system was cooled to 5 °C, and NaOMe (5.45 g, 100.90 mmol) was added at one time. The reaction was maintained at 5 °C for 1 hour, and TLC (ethyl acetate: n-hexane = 1:10 as developing agent) was used to monitor the reaction. The starting material A1-5 was consumed completely.

[0127] DI water (500 mL) was added, and the solvent was removed by concentration under reduced pressure. Ethyl acetate (700 mL) was added to extract the mixture, and the mixture was separated. The white solid was obtained by concentration under reduced pressure at 70 °C for 1 hour. The white solid was A1-7 (18.44 g, yield: 95.00%), and the mass was 385.04 (M+H). The obtained compound was used directly in the next step without purification.

[0128] Synthesis of compound A1-8

[0129] A1-7 (17.00 g, 44.17 mmol), Toluene (170 ml) were added into a 500 ml three-necked round-bottom flask, replaced with vacuum nitrogen for three times, then the system was cooled to 5 °C, methylsulfonic acid (MsOH, 8.49 g, 88.34 mmol) was added slowly dropwise, 3 minutes dropwise was completed, maintained 5 °C for 1 hour, TLC (ethyl acetate: n-hexane = 1:15 as developing agent) was used to monitor the reaction, the raw material A1-7 was consumed completely.

[0130] Methanol (200 ml) was added, a large amount of white solid was precipitated, 17 g solid was obtained by suction filtration, crystallized once with Toluene (204 ml) and methanol (170 ml), suction filtration, the filter cake was dried at 80 °C for 1 hour to obtain white solid A1-8 (11.63 g, purity: 99.83%, yield: 74.62%), mass spectrum: 353.06 (M+H).

[0131] Synthesis of compound A1

[0132] 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-dicyclohexylphosphino-2',4',6'-triisopropyl biphenyl (X-Phos, 0.54 g, 1.14 mmol), sodium tert-butoxide (NaOtBu, 4.09 g, 42.51 mmol), Toluene (150 ml) were added into a 500 ml three-necked round-bottom flask, replaced with vacuum nitrogen for three times, then the system was heated to 105 °C for 2 hours, TLC (ethyl acetate: n-hexane = 1:15 as developing agent) was used to monitor the reaction, the raw material A1-8 was consumed completely.

[0133] cooled to 60 °C, methanol (150 ml) was added, and the system was naturally cooled to room temperature and stirred for 30 minutes to precipitate a large amount of solid, suction filtration was performed to obtain 20 g of solid, Toluene (300 ml) was added, then the system was heated to 100 °C to dissolve and clarify, 30 g (300-400 mesh) of silica gel was laid on the filter to filter, Toluene (50 ml) was used to rinse the surface of the silica gel, and the combined filtrate was concentrated to obtain 18 g. Crystallization was performed twice with Toluene (180 ml) and methanol (90 ml), suction filtration was performed, and the filter cake was dried at 90 °C for 3 hours to obtain light yellow solid A1 (14.07 g, purity: 99.94%, yield: 88.41%). The 14.07 g of crude A1 was purified by sublimation to obtain sublimed A1 (11.26 g, purity: 99.95%, yield: 80.02%), mass spectrum: 562.22 (M+H).

[0134] 1H NMR (400 MHz, CDC13) 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).

[0135] Synthesis of compound A54

[0136] Synthesis of compound A54-2

[0137] Referring to the synthesis and purification method of compound A1-3, only the corresponding starting materials need to be changed to obtain the target compound A54-2 (28.02 g, purity: 98.52%, yield: 77.65%) as a white solid, mass spectrum: 329.12 (M+H).

[0138] Synthesis of compound A54-3

[0139] Referring to the synthesis and purification method of compound A1-5, only the corresponding starting materials need to be changed to obtain the target compound A54-3 (26.33 g, purity: 99.45%, yield: 75.09%) as a white solid, mass spectrum: 357.22 (M+H).

[0140] Synthesis of compound A54-4

[0141] Referring to the synthesis and purification method of compound A1-7, only the corresponding starting materials need to be changed to obtain the target compound A54-4 (24.44 g, yield: 97.89%) as a white solid, mass spectrum: 385.04 (M+H). The obtained compound is directly used in the next step without purification.

[0142] Synthesis of compound A54-5

[0143] Referring to the synthesis and purification method of compound A1-8, only the corresponding starting materials need to be changed to obtain the target compound A54-5 (16.85 g, purity: 99.79%, yield: 76.85%) as a white solid, mass spectrum: 353.06 (M+H).

[0144] Synthesis of compound A54

[0145] The synthesis and purification process of compound A1-3 were referred to, and only the corresponding raw materials were changed to obtain the target compound A73-2 (30.54 g, purity: 98.44%, yield: 77.12%) in the form of a white solid, mass spectrum: 329.12 (M+H).

[0146] 1 H NMR (400 MHz, CDC13) 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).

[0147] Synthesis of compound A73

[0148] Synthesis of compound A73-2

[0149] The synthesis and purification process of compound A1-3 were referred to, and only the corresponding raw materials were changed to obtain the target compound A73-2 (30.54 g, purity: 98.44%, yield: 77.12%) in the form of a white solid, mass spectrum: 329.12 (M+H).

[0150] Synthesis of compound A73-3

[0151] The synthesis and purification process of compound A1-5 were referred to, and only the corresponding raw materials were changed to obtain the target compound A73-3 (27.09 g, purity: 99.66%, yield: 76.36%) in the form of a white solid, mass spectrum: 357.22 (M+H).

[0152] Synthesis of compound A73-4

[0153] The synthesis and purification process of compound A1-7 were referred to, and only the corresponding raw materials were changed to obtain the target compound A73-4 (23.12 g, yield: 93.93%) in the form of a white solid, mass spectrum: 385.04 (M+H). The obtained compound was directly used in the next step without purification.

[0154] Synthesis of compound A73-5

[0155] The synthesis and purification process of compound A1-8 were referred to, only the corresponding raw materials were changed, and the target compound A73-5 was obtained as a white solid (18.08 g, purity: 99.65%, yield: 40.20%). Mass spectrum: 353.06 (M+H).

[0156] Synthesis of compound A73-8

[0157] The synthesis and purification process of compound A1 were referred to, only the corresponding raw materials were changed, and the target compound A73-8 was obtained as a white solid (23.11 g, purity: 99.60%, yield: 76.44%). Mass spectrum: 337.13 (M+H).

[0158] Synthesis of compound A73

[0159] The synthesis and purification process of compound A1 were referred to, only the corresponding raw materials were changed, and the target compound A73 was obtained as a light yellow solid (16.76 g, purity: 99.92%, yield: 76.22%). After sublimation purification of 16.76 g of A73 crude product, sublimed A73 was obtained (14.21 g, purity: 99.92%, yield: 84.78%). Mass spectrum: 653.21 (M+H).

[0160] 1 H NMR (400 MHz, CDCl3) δ 8.33-8.26 (m, 1H), 8.21 (dd, J = 17.5, 8.8 Hz, 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).

[0161] Synthesis of compound A89

[0162] Synthesis of compound A89-3

[0163] The synthesis and purification process of compound A1-5 were referred to, only the corresponding raw materials were changed, and the target compound A89-3 was obtained as a white solid (19.88 g, purity: 99.57%, yield: 78.08%). Mass spectrum: 357.04 (M+H).

[0164] Synthesis of compound A89-4

[0165] The synthesis and purification method of compound A1-7 were referred to, only the corresponding raw materials were changed, and the target compound A89-4 was obtained as a white solid (25.58 g, yield: 94.35%), mass spectrum: 385.04 (M+H). The obtained compound was directly used in the next step without purification.

[0166] Synthesis of compound A89-5

[0167] The synthesis and purification method of compound A1-8 were referred to, only the corresponding raw materials were changed, and the target compound A89-5 was obtained as a white solid (20.01 g, purity: 99.74%, yield: 78.63%), mass spectrum: 353.06 (M+H).

[0168] Synthesis of compound A89

[0169] The synthesis and purification method of compound A1 were referred to, only the corresponding raw materials were changed, and the target compound A89 was obtained as a yellow solid (17.77 g, purity: 99.94%, yield: 71.06%). After sublimation purification of 17.77 g of A89 crude product, sublimation pure A89 was obtained (15.02 g, purity: 99.94%, yield: 84.52%), mass spectrum: 678.22 (M+H).

[0170] 1 H NMR (400 MHz, CDC13) 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).

[0171] Synthesis of compound A97

[0172] Synthesis of compound A97-2

[0173] The synthesis and purification method of compound A1-3 were referred to, only the corresponding raw materials were changed, and the target compound A97-2 was obtained as a white solid (32.65 g, purity: 98.78%, yield: 79.05%), mass spectrum: 345.02 (M+H).

[0174] Synthesis of compound A97-3

[0175] The synthesis and purification method of compound A1-5 were referred to, only the corresponding raw materials were changed, to obtain the target compound A97-3 (29.63 g, purity: 99.75%, yield: 76.03%) as a white solid, mass spectrum: 373.04 (M+H).

[0176] Synthesis of compound A97-4

[0177] The synthesis and purification method of compound A1-7 were referred to, only the corresponding raw materials were changed, to obtain the target compound A97-4 (25.63 g, yield: 95.39%) as a white solid, mass spectrum: 401.14 (M+H). The obtained compound was directly used in the next step without purification.

[0178] Synthesis of compound A97-5

[0179] The synthesis and purification method of compound A1-8 were referred to, only the corresponding raw materials were changed, to obtain the target compound A97-5 (20.00 g, purity: 99.76%, yield: 78.80%) as a white solid, mass spectrum: 369.02 (M+H).

[0180] Synthesis of compound A97

[0181] The synthesis and purification method of compound A1 were referred to, only the corresponding raw materials were changed, to obtain the target compound A97 (14.33 g, purity: 99.95%, yield: 74.63%) as a light yellow solid. After sublimation purification of 14.33 g of A97 crude product, sublimation pure A97 (12.01 g, purity: 99.95%, yield: 83.81) was obtained, mass spectrum: 731.93 (M+H).

[0182] 1 H 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).

[0183] Synthesis of compound A118

[0184] Synthesis of compound A118-1

[0185] Referring to the synthesis and purification method of compound A1, only the corresponding starting material needs to be changed to obtain the target compound A118-1 (12.11 g, purity: 99.95%, yield: 76.87%) as a light yellow solid, mass spectrum: 562.32 (M+H).

[0186] 1 H NMR (400 MHz, CDC13) δ 8.33 - 8.26 (m, 1H), 8.21 (dd, J = 17.5, 8.8 Hz, 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).

[0187] Synthesis of compound A118

[0188] A118-1 (30.00 g, 54.31 mmol), deuterated benzene-D6 (114.44 g, 1.36 mol), trifluoroacetic acid (6.19 g, 54.31 mmol) were added into a 500 ml single-necked round-bottom flask, replaced with vacuum nitrogen three times, and then the system was heated to 50°C and stirred for 24 hours.

[0189] The system was cooled to room temperature, heavy water was added dropwise to quench the reaction (40 ml), stirred at room temperature for 0.5 hours, then ethyl acetate (300 ml) and deionized water were added and washed three times (200 ml) to form a slurry at room temperature for 30 minutes, and then filtered to obtain 35 g of solid, which was dried at 90°C under vacuum for 1 hour to obtain 29 g of light yellow solid. The light yellow solid was crystallized twice with toluene (290 ml) and methanol (120 ml), filtered, and the filter cake was dried at 90°C under vacuum for 3 hours to obtain A118 (25.20 g, purity: 99.94%, yield: 80.12%) as a light yellow solid. After sublimation purification of 25.20 g of crude A118, sublimed A118 (21.53 g, purity: 99.95%, deuterium substitution rate of 27 D: 95.33%, yield: 85.46%) was obtained, mass spectrum: 589.22 (M+H).

[0190] Synthesis of compound A136

[0191] Synthesis of compound A136-2

[0192] The synthesis and purification method of Compound A1-5 were referred to, only the corresponding raw materials were changed, to obtain the target compound A136-2 (22.65 g, purity: 99.52%, yield: 75.98%) as a white solid, mass spectrum: 382.12 (M+H).

[0193] Synthesis of compound A136-3

[0194] The synthesis and purification method of Compound A1-7 were referred to, only the corresponding raw materials were changed, to obtain the target compound A136-3 (20.00 g, yield: 96.08%) as a white solid, mass spectrum: 410.10 (M+H). The obtained compound was directly used in the next step without purification.

[0195] Synthesis of compound A136-4

[0196] The synthesis and purification method of Compound A1-8 were referred to, only the corresponding raw materials were changed, to obtain the target compound A136-4 (16.78 g, purity: 99.78%, yield: 42.56%) as a white solid, mass spectrum: 378.26 (M+H).

[0197] Synthesis of compound A136

[0198] The synthesis and purification method of Compound A1 were referred to, only the corresponding raw materials were changed, to obtain the target compound A136 (15.33 g, purity: 99.92%, yield: 77.52%) as a light yellow solid. After sublimation purification of 15.33 g of A136 crude product, sublimed A136 (12.01 g, purity: 99.93%, yield: 78.35%) was obtained, mass spectrum: 601.18 (M+H).

[0199] 1 H NMR (400 MHz, CDCl3) δ 8.44 (d, J = 2.0 Hz, 1H), 8.37 (d, J = 8.1 Hz, 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).

[0200] Synthesis of compound A145

[0201] Synthesis of compound A145-1

[0202] The synthesis and purification of reference compound A1-8 were repeated by changing the corresponding starting materials to obtain the target compound A145-1 (20.52 g, purity: 99.63%, yield: 75.82%) as a white solid, mass: 353.06 (M+H).

[0203] Synthesis of compound A145-3

[0204] The synthesis and purification of reference compound A1 were repeated by changing the corresponding starting materials to obtain the target compound A145-3 (25.63 g, purity: 99.87%, yield: 74.25%) as a white solid, mass: 320.12 (M+H).

[0205] Synthesis of compound A145

[0206] The synthesis and purification of reference compound A1 were repeated by changing the corresponding starting materials to obtain the target compound A145 (17.63 g, purity: 99.94%, yield: 77.06%) as a yellow solid. After sublimation purification of 17.63 g of the crude A145, sublimed A145 (14.76 g, purity: 99.94%, yield: 83.72%) was obtained, mass: 636.22 (M+H).

[0207] 1 H NMR (400 MHz, CDCl3) δ 8.62 (d, J = 9.2 Hz, 1H), 8.57 (d, J = 9.3 Hz, 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, 2.2 Hz, 1H).

[0208] Synthesis of compound A167

[0209] Synthesis of compound A167-1

[0210] The synthesis and purification process of reference compound A1-8 was referred to, only the corresponding raw materials were changed, to obtain the target compound A167-1 (15.63 g, purity: 99.71%, yield: 42.52%) as a white solid, mass spectrum: 353.06 (M+H).

[0211] Synthesis of compound A167-4

[0212] The synthesis and purification process of reference compound A1 was referred to, only the corresponding raw materials were changed, to obtain the target compound A167 (20.62 g, purity: 99.75%, yield: 78.43%) as a white solid, mass spectrum: 410.20 (M+H).

[0213] Synthesis of compound A167

[0214] The synthesis and purification process of reference compound A1 was referred to, only the corresponding raw materials were changed, to obtain the target compound A167 (20.62 g, purity: 99.75%, yield: 78.43%) as a white solid, mass spectrum: 410.20 (M+H).

[0215] 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).

[0216] Synthesis of compound A183

[0217] Synthesis of compound A183-2

[0218] The synthesis and purification process of reference compound A1-3 was referred to, only the corresponding raw materials were changed, to obtain the target compound A183-2 (28.74 g, purity: 99.21%, yield: 74.56%) as a white solid, mass spectrum: 329.12 (M+H).

[0219] Synthesis of compound A183-3

[0220] The synthesis and purification of reference compound A1-5 were repeated by changing the corresponding starting materials to obtain the target compound A183-3 (26.32 g, purity: 99.66%, yield: 76.36%) as a white solid. Mass: 357.22 (M+H).

[0221] Synthesis of compound A183-4

[0222] The synthesis and purification of reference compound A1-7 were repeated by changing the corresponding starting materials to obtain the target compound A183-4 (21.65 g, yield: 92.84%) as a white solid. Mass: 385.04 (M+H). The obtained compound was used in the next step without purification.

[0223] Synthesis of compound A183-5

[0224] The synthesis and purification of reference compound A1-8 were repeated by changing the corresponding starting materials to obtain the target compound A183-5 (18.65 g, purity: 99.73%, yield: 76.85%) as a white solid. Mass: 353.06 (M+H).

[0225] Synthesis of compound A183-7

[0226] The synthesis and purification of reference compound A1 were repeated by changing the corresponding starting materials to obtain the target compound A183-7 (19.99 g, purity: 99.87%, yield: 78.63%) as a white solid. Mass: 310.22 (M+H).

[0227] Synthesis of compound A183

[0228] The synthesis and purification of reference compound A1 were repeated by changing the corresponding starting materials to obtain the target compound A183 (14.65 g, purity: 99.96%, yield: 77.14%) as a light yellow solid. After sublimation purification of 14.65 g of crude A183, sublimed A183 (11.24 g, purity: 99.96%, yield: 76.73%) was obtained. Mass: 626.24 (M+H).

[0229] 1H NMR (400 MHz, CDC13) 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).

[0230] Synthesis of compound A207

[0231] Synthesis of compound A207-2

[0232] Referring to the synthesis and purification method of compound A1-5, only the corresponding starting material needs to be changed to obtain the target compound A207-2 (28.78 g, purity: 99.74%, yield: 76.11%) as a white solid, mass spectrum: 357.24 (M+H).

[0233] Synthesis of compound A207-3

[0234] Referring to the synthesis and purification method of compound A1-7, only the corresponding starting material needs to be changed to obtain the target compound A207-3 (22.65 g, yield: 95.63%) as a white solid, mass spectrum: 385.04 (M+H). The obtained compound is directly used in the next step without purification.

[0235] Synthesis of compound A207-4

[0236] Referring to the synthesis and purification method of compound A1-8, only the corresponding starting material needs to be changed to obtain the target compound A207-4 (18.08 g, purity: 99.65%, yield: 41.20%) as a white solid, mass spectrum: 353.06 (M+H).

[0237] Synthesis of compound A207-5

[0238] Referring to the synthesis and purification method of compound A1-3, only the corresponding starting material needs to be changed to obtain the target compound A207-5 (20.63 g, purity: 99.00%, yield: 75.41%) as a white solid, mass spectrum: 445.20 (M+H).

[0239] Synthesis of compound A207

[0240] The synthesis and purification method of compound A1-5 were referred to, only the corresponding raw materials were changed, and the target compound A207 was obtained as a light yellow solid (15.12 g, purity: 99.94%, yield: 75.85%). After sublimation purification of 15.12 g of A207 crude product, sublimed A207 (12.02 g, purity: 99.94%, yield: 79.50%) was obtained, mass spectrum: 638.24 (M+H).

[0241] 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).

[0242] Synthesis of compound A219

[0243] Synthesis of compound A219-2

[0244] The synthesis and purification method of compound A1-3 were referred to, only the corresponding raw materials were changed, and the target compound A219-2 was obtained as a white solid (22.54 g, purity: 98.98%, yield: 78.15%), mass spectrum: 329.12 (M+H).

[0245] Synthesis of compound A219-3

[0246] The synthesis and purification method of compound A1-5 were referred to, only the corresponding raw materials were changed, and the target compound A219-3 was obtained as a white solid (22.62 g, purity: 99.81%, yield: 77.63%), mass spectrum: 357.22 (M+H).

[0247] Synthesis of compound A219-4

[0248] The synthesis and purification method of compound A1-7 were referred to, only the corresponding raw materials were changed, to obtain the target compound A219-4 (19.02 g, yield: 92.06%) as a white solid, mass spectrum: 385.04 (M+H). The obtained compound was directly used in the next step without purification.

[0249] Synthesis of compound A219-5

[0250] The synthesis and purification method of compound A1-8 were referred to, only the corresponding raw materials were changed, to obtain the target compound A219-5 (187.85 g, purity: 99.23%, yield: 43.05%) as a white solid, mass spectrum: 353.06 (M+H).

[0251] Synthesis of compound A219-7

[0252] The synthesis and purification method of compound A1 were referred to, only the corresponding raw materials were changed, to obtain the target compound A219-7 (18.63 g, purity: 99.55%, yield: 78.06%) as a white solid, mass spectrum: 520.20 (M+H).

[0253] Synthesis of compound A219

[0254] The synthesis and purification method of compound A1 were referred to, only the corresponding raw materials were changed, to obtain the target compound A219 (17.96 g, purity: 99.93%, yield: 77.61%) as a light yellow solid. After sublimation purification of 17.96 g of A219 crude product, sublimation pure A219 (15.00 g, purity: 99.93%, yield: 83.51%) was obtained, mass spectrum: 836.28 (M+H).

[0255] 1 H 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).

[0256] Synthesis of compound A226

[0257] Synthesis of compound A226-2

[0258] The synthesis and purification of reference compound A1-3 were repeated with the corresponding starting materials changed to give the target compound A226-2 as a white solid (35.23 g, purity: 99.21%, yield: 79.08%), mass: 329.12 (M+H).

[0259] Synthesis of compound A226-3

[0260] The synthesis and purification of reference compound A1-5 were repeated with the corresponding starting materials changed to give the target compound A226-3 as a white solid (30.68 g, purity: 99.78%, yield: 74.62%), mass: 357.24 (M+H).

[0261] Synthesis of compound A226-4

[0262] The synthesis and purification of reference compound A1-7 were repeated with the corresponding starting materials changed to give the target compound A226-4 as a white solid (24.55 g, yield: 96.33%), mass: 385.04 (M+H). The obtained compound was used directly in the next step without purification.

[0263] Synthesis of compound A226-5

[0264] The synthesis and purification of reference compound A1-8 were repeated with the corresponding starting materials changed to give the target compound A226-5 as a white solid (17.99 g, purity: 99.86%, yield: 78.63%), mass: 353.06 (M+H).

[0265] Synthesis of compound A226

[0266] The synthesis and purification of reference compound A1 were repeated with the corresponding starting materials changed to give the target compound A226 as a light yellow solid (17.11 g, purity: 99.95%, yield: 78.74%). After sublimation purification of 17.11 g of crude A226, sublimed A226 was obtained (13.75 g, purity: 99.95%, yield: 80.37%), mass: 562.24 (M+H).

[0267] 1H NMR (400 MHz, CDC13) 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).

[0268] Synthesis of compound A252

[0269] Synthesis of compound A252-2

[0270] Referring to the synthesis and purification method of compound A1-5, only the corresponding starting materials need to be changed to obtain the target compound A252-2 (18.42 g, purity: 99.52%, yield: 74.62%) as a white solid, mass spectrum: 433.20 (M+H).

[0271] Synthesis of compound A252-3

[0272] Referring to the synthesis and purification method of compound A1-7, only the corresponding starting materials need to be changed to obtain the target compound A252-3 (20.06 g, yield: 94.26%) as a white solid, mass spectrum: 461.12 (M+H). The obtained compound was directly used in the next step without purification.

[0273] Synthesis of compound A252-4

[0274] Referring to the synthesis and purification method of compound A1-8, only the corresponding starting materials need to be changed to obtain the target compound A252-4 (16.75 g, purity: 99.71%, yield: 74.29%) as a white solid, mass spectrum: 429.12 (M+H).

[0275] Synthesis of compound A252

[0276] Referring to the synthesis and purification method of compound A1, only the corresponding starting 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. After sublimation purification of 14.02 g of crude A252, sublimed A252 (10.58 g, purity: 99.93%, yield: 75.47%) was obtained, mass spectrum: 638.22 (M+H).

[0277] 1H NMR (400 MHz, CDC13) 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).

[0278] Synthesis of compound A265

[0279] Synthesis of compound A265

[0280] Referring to the synthesis and purification method of compound A1, only the corresponding raw materials need to be changed, and the target compound A265 (10.33 g, purity: 99.94%, yield: 78.63%) is obtained as a light yellow solid. After sublimation purification of 10.33 g of A265 crude product, sublimed A265 (8.13 g, purity: 99.94%, yield: 78.71%) is obtained, mass spectrum: 668.34 (M+H).

[0281] 1 H NMR (400 MHz, CDC13) 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).

[0282] Synthesis of compound A280

[0283] Synthesis of compound A280-2

[0284] Referring to the synthesis and purification method of compound A1-3, only the corresponding raw materials need to be changed, and the target compound A280-2 (33.59 g, purity: 99.41%, yield: 74.02%) is obtained as a white solid, mass spectrum: 329.12 (M+H).

[0285] Synthesis of compound A280-3

[0286] The synthesis and purification method of Compound A1-5 were referred to, only the corresponding raw materials were changed, to obtain the target compound A280-3 (32.63 g, purity: 99.69%, yield: 74.69%) as a white solid, mass spectrum: 357.24 (M+H).

[0287] Synthesis of compound A280-4

[0288] The synthesis and purification method of Compound A1-7 were referred to, only the corresponding raw materials were changed, to obtain the target compound A280-4 (27.96 g, yield: 94.12%) as a white solid, mass spectrum: 385.04 (M+H). The obtained compound was directly used in the next step without purification.

[0289] Synthesis of compound A280-5

[0290] The synthesis and purification method of Compound A1-8 were referred to, only the corresponding raw materials were changed, to obtain the target compound A280-5 (21.21 g, purity: 99.59%, yield: 74.63%) as a white solid, mass spectrum: 353.06 (M+H).

[0291] Synthesis of compound A280

[0292] The synthesis and purification method of Compound A1 were referred to, only the corresponding raw materials were changed, to obtain the target compound A280 (16.06 g, purity: 99.95%, yield: 74.44%) as a light yellow solid. After sublimation purification of 16.06 g of A280 crude product, sublimation pure A280 (12.90 g, purity: 99.95%, yield: 80.33%) was obtained, mass spectrum: 712.22 (M+H).

[0293] 1 H NMR (400 MHz, CDC13) 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).

[0294] Synthesis of compound A289

[0295] Synthesis of compound A289-3

[0296] The synthesis and purification process of reference compound A1 was referred to, only the corresponding raw materials were changed, to obtain the target compound A289-3 (20.06 g, purity: 99.87%, yield: 74.63%) as a white solid, mass spectrum: 356.23 (M+H).

[0297] Synthesis of compound A289-4

[0298] The synthesis and purification process of reference compound A1-8 was referred to, only the corresponding raw materials were changed, to obtain the target compound A289-4 (10.05, purity: 99.43%, yield: 39.85%) as a white solid, mass spectrum: 353.06 (M+H).

[0299] Synthesis of compound A289

[0300] The synthesis and purification process of reference compound A1 was referred to, only the corresponding raw materials were changed, to obtain the target compound A289 (10.96 g, purity: 99.93%, yield: 78.65%) as a light yellow solid. After sublimation purification of 10.96 g of A289 crude product, sublimation pure A289 (8.88 g, purity: 99.93%, yield: 81.03%) was obtained, mass spectrum: 672.32 (M+H).

[0301] 1 H NMR (400 MHz, CDC13) 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).

[0302] Synthesis of compound A305

[0303] Synthesis of compound A305-3

[0304] The synthesis and purification method of Compound A1-8 were referred to, and only the corresponding raw materials were changed to obtain the target compound A305-4 (22.44 g, purity: 99.53%, yield: 38.43%) in white solid. Mass spectrum: 353.06 (M+H).

[0305] Synthesis of compound A305-4

[0306] The synthesis and purification method of Compound A1-8 were referred to, and only the corresponding raw materials were changed to obtain the target compound A305-4 (22.44 g, purity: 99.53%, yield: 38.43%) in white solid. Mass spectrum: 353.06 (M+H).

[0307] Synthesis of compound A305

[0308] The synthesis and purification method of Compound A1-8 were referred to, and only the corresponding raw materials were changed to obtain the target compound A305-4 (22.44 g, purity: 99.53%, yield: 38.43%) in white solid. Mass spectrum: 353.06 (M+H).

[0309] 1 H NMR (400 MHz, CDCl3) δ 8.69 (d, J = 8.2 Hz, 1H), 8.62 (d, J = 9.3 Hz, 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).

[0310] Synthesis of compound A340

[0311] Synthesis of compound A340-2

[0312] The synthesis and purification method of Compound A1-8 were referred to, and only the corresponding raw materials were changed to obtain the target compound A305-4 (22.44 g, purity: 99.53%, yield: 38.43%) in white solid. Mass spectrum: 353.06 (M+H).

[0313] Synthesis of compound A340-3

[0314] The synthesis and purification of reference compound A1-7 were followed, except that the corresponding starting materials were changed, to give the target compound A340-3 (15.86 g, yield: 94.63%) as a white solid. Mass: 385.04 (M+H). The obtained compound was used directly in the next step without purification.

[0315] Synthesis of compound A340-4

[0316] The synthesis and purification of reference compound A1-8 were followed, except that the corresponding starting materials were changed, to give the target compound A340-4 (14.36 g, purity: 99.76%, yield: 76.33%) as a white solid. Mass: 353.06 (M+H).

[0317] Synthesis of compound A340-5

[0318] The synthesis and purification of reference compound A1-3 were followed, except that the corresponding starting materials were changed, to give the target compound A340-4 (12.37 g, purity: 98.08%, yield: 75.55%) as a white solid. Mass: 445.20 (M+H).

[0319] Synthesis of compound A340-7

[0320] The synthesis and purification of reference compound A1-5 were followed, except that the corresponding starting materials were changed, to give the target compound A340-7 (10.23 g, purity: 98.88%, yield: 78.96%) as a white solid. Mass: 523.04 (M+H).

[0321] Synthesis of compound A340

[0322] The synthesis and purification of reference compound A1 were followed, except that the corresponding starting materials were changed, to give the target compound A340 (10.28 g, purity: 99.95%, yield: 78.26%) as a light yellow solid. After sublimation purification of 10.28 g of crude A340, sublimed A340 (8.02 g, purity: 99.95%, yield: 78.02%) was obtained. Mass: 764.22 (M+H).

[0323] 1H NMR (400 MHz, CDC13) 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).

[0324] Synthesis of compound A424

[0325] Synthesis of compound A424-1

[0326] Referring to the synthesis and purification method of compound A1-5, only the corresponding starting materials need to be changed to obtain the target compound A424-1 (26.52 g, purity: 99.46%, yield: 74.52%) as a white solid, mass spectrum: 357.24 (M+H).

[0327] Synthesis of compound A424-2

[0328] Referring to the synthesis and purification method of compound A1-7, only the corresponding starting materials need to be changed to obtain the target compound A424-2 (18.06 g, yield: 93.06%) as a white solid, mass spectrum: 385.04 (M+H). The obtained compound is directly used in the next step without purification.

[0329] Synthesis of compound A424-3

[0330] Referring to the synthesis and purification method of compound A1-8, only the corresponding starting materials need to be changed to obtain the target compound A424-3 (18.85 g, purity: 99.23%, yield: 40.05%) as a white solid, mass spectrum: 353.06 (M+H).

[0331] Synthesis of compound A424-5

[0332] Referring to the synthesis and purification method of compound A1, only the corresponding starting materials need to be changed to obtain the target compound A424-5 (15.96 g, purity: 99.77%, yield: 79.06%) as a white solid, mass spectrum: 385.16 (M+H).

[0333] Synthesis of compound A424

[0334] The synthesis and purification method of compound A1-3 were referred to, only the corresponding raw materials were changed, the target compound A481-2 was obtained as a white solid (25.77 g, purity: 98.88%, yield: 74.12%), mass spectrum: 355.12 (M+H).

[0335] 1 H NMR (400 MHz, CDC13) 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).

[0336] Synthesis of compound A481

[0337] Synthesis of compound A481-2

[0338] The synthesis and purification method of compound A1-3 were referred to, only the corresponding raw materials were changed, the target compound A481-2 was obtained as a white solid (25.77 g, purity: 98.88%, yield: 74.12%), mass spectrum: 355.12 (M+H).

[0339] Synthesis of compound A481-4

[0340] The synthesis and purification method of compound A1-3 were referred to, only the corresponding raw materials were changed, the target compound A481-2 was obtained as a white solid (25.77 g, purity: 98.88%, yield: 74.12%), mass spectrum: 355.12 (M+H).

[0341] Synthesis of compound A481-5

[0342] The synthesis and purification method of compound A1-3 were referred to, only the corresponding raw materials were changed, the target compound A481-2 was obtained as a white solid (25.77 g, purity: 98.88%, yield: 74.12%), mass spectrum: 355.12 (M+H).

[0343] Synthesis of compound A481-6

[0344] 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 A481-6 (18.88 g, purity: 99.75%, yield: 75.62%) as a white solid, mass spectrum: 435.16 (M+H).

[0345] Synthesis of compound A481

[0346] 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. After sublimation purification of 15.55 grams of A481 crude product, sublimed A481 (11.85 g, purity: 99.94%, yield: 76.21%) was obtained, mass spectrum: 658.30 (M+H).

[0347] 1 H 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).

[0348] Synthesis of compound A488

[0349] Synthesis of compound A488-2

[0350] Referring to the synthesis and purification method of compound A1-3, only the corresponding raw materials need to be changed to obtain the target compound A488-2 (28.77 g, purity: 99.02%, yield: 76.74%) as a white solid, mass spectrum: 404.14 (M+H).

[0351] Synthesis of compound A488-3

[0352] The synthesis and purification method of compound A1-5 was referred to, only the corresponding raw materials were changed, to obtain the target compound A488-3 (24.85 g, purity: 99.67%, yield: 73.62%) as a white solid, mass spectrum: 432.21 (M+H).

[0353] Synthesis of compound A488-4

[0354] The synthesis and purification method of compound A1-7 was referred to, only the corresponding raw materials were changed, to obtain the target compound A488-4 (23.41 g, yield: 96.66%) as a white solid, mass spectrum: 460.04 (M+H). The obtained compound was directly used in the next step without purification.

[0355] Synthesis of compound A488-5

[0356] The synthesis and purification method of compound A1-8 was referred to, only the corresponding raw materials were changed, to obtain the target compound A488-5 (20.00 g, purity: 99.87%, yield: 77.01%) as a white solid, mass spectrum: 428.02 (M+H).

[0357] Synthesis of compound A488

[0358] The synthesis and purification method of compound A1 was referred to, only the corresponding raw materials were changed, to obtain the target compound A488 (18.11 g, purity: 99.92%, yield: 75.98%) as a light yellow solid. After sublimation purification of 18.11 g of A488 crude product, sublimation pure A488 (15.00 g, purity: 99.93%, yield: 82.83%) was obtained, mass spectrum: 713.24 (M+H).

[0359] 1 H NMR (400 MHz, CDC13) δ 8.60 (d, J = 9.0 Hz, 1H), 8.52 (d, J = 8.0 Hz, 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).

[0360] Synthesis of compound A496

[0361] Synthesis of compound A496-2

[0362] The synthesis and purification method of reference compound A1-5 was referred to, only the corresponding raw materials were changed, and the target compound A496-2 was obtained as a white solid (18.81 g, purity: 99.72%, yield: 73.62%). Mass spectrum: 429.10 (M+H).

[0363] Synthesis of compound A496-3

[0364] The synthesis and purification method of reference compound A1-7 was referred to, only the corresponding raw materials were changed, and the target compound A496-3 was obtained as a white solid (18.77 g, yield: 92.626%). Mass spectrum: 457.13 (M+H). The obtained compound was directly used in the next step without purification.

[0365] Synthesis of compound A496-4

[0366] The synthesis and purification method of reference compound A1-8 was referred to, only the corresponding raw materials were changed, and the target compound A496-4 was obtained as a white solid (16.85 g, purity: 99.45%, yield: 75.11%). Mass spectrum: 425.24 (M+H)

[0367] Synthesis of compound A496-5

[0368] The synthesis and purification method of reference compound A1-5 was referred to, only the corresponding raw materials were changed, and the target compound A496-5 was obtained as a white solid (19.78 g, purity: 99.62%, yield: 74.44%). Mass spectrum: 591.15 (M+H).

[0369] Synthesis of compound A496

[0370] The synthesis and purification method of reference compound A1 was referred to, only the corresponding raw materials were changed, and the target compound A496 was obtained as a light yellow solid (12.71, purity: 99.95%, yield: 62.71%). After sublimation purification of 12.71 g of A496 crude, sublimed A496 was obtained (9.84 g, purity: 99.97%, yield: 11.41%). Mass spectrum: 800.07 (M+H).

[0371] 1H NMR (400 MHz, CDC13) 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).

[0372] Synthesis of compound A515

[0373] Synthesis of compound A515-2

[0374] Referring to the synthesis and purification method of compound A1-3, only the corresponding starting materials need to be changed to obtain the target compound A515-2 (25.33 g, purity: 99.23%, yield: 78.46%) as a white solid, mass spectrum: 379.12 (M+H).

[0375] Synthesis of compound A515-3

[0376] Referring to the synthesis and purification method of compound A1-5, only the corresponding starting materials need to be changed to obtain the target compound A515-3 (22.11 g, purity: 99.43%, yield: 75.12%) as a white solid, mass spectrum: 407.06 (M+H).

[0377] Synthesis of compound A515-4

[0378] Referring to the synthesis and purification method of compound A1-7, only the corresponding starting materials need to be changed to obtain the target compound A515-4 (20.63 g, yield: 95.12%) as a white solid, mass spectrum: 435.12 (M+H). The obtained compound is directly used in the next step without purification.

[0379] Synthesis of compound A515-5

[0380] Referring to the synthesis and purification method of compound A1-8, only the corresponding starting materials need to be changed to obtain the target compound A515-5 (18.96 g, purity: 99.90%, yield: 79.63%) as a white solid, mass spectrum: 403.08 (M+H).

[0381] Synthesis of compound A515

[0382] Referring to the synthesis and purification method of compound A1, only the corresponding starting 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. After sublimation purification of 16.96 g of A515 crude product, sublimed A515 (14.33 g, purity: 99.93%, yield: 84.49%) was obtained, mass spectrum: 612.75 (M+H).

[0383] 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).

[0384] Synthesis of compound A527

[0385] Synthesis of compound A527-2

[0386] Referring to the synthesis and purification method of compound A1-3, only the corresponding starting materials need to be changed to obtain the target compound A527-2 (22.10 g, purity: 99.10%, yield: 70.01%) as a white solid, mass spectrum: 405.14 (M+H).

[0387] Synthesis of compound A527-3

[0388] Referring to the synthesis and purification method of compound A1-5, only the corresponding starting materials need to be changed to obtain the target compound A527-3 (20.06 g, purity: 99.21%, yield: 72.32%) as a white solid, mass spectrum: 433.08 (M+H).

[0389] Synthesis of compound A527-4

[0390] The synthesis and purification method of compound A1-7 were referred to, only the corresponding raw materials were changed, and the target compound A527-4 was obtained as a white solid (18.06 g, yield: 94.33%), mass spectrum: 461.22 (M+H). The obtained compound was directly used in the next step without purification.

[0391] Synthesis of compound A527-5

[0392] The synthesis and purification method of compound A1-8 were referred to, only the corresponding raw materials were changed, and the target compound A527-5 was obtained as a white solid (17.63 g, purity: 99.88%, yield: 42.03%), mass spectrum: 429.12 (M+H).

[0393] Synthesis of compound A527

[0394] The synthesis and purification method of compound A1 were referred to, only the corresponding raw materials were changed, and the target compound A527 was obtained as a light yellow solid (14.63 g, purity: 99.93%, yield: 74.95%). After sublimation purification of 14.63 g of A527 crude product, sublimed A527 was obtained (12.00 g, purity: 99.93%, yield: 82.02%), mass spectrum: 668.20 (M+H).

[0395] 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).

[0396] Synthesis of compound A539

[0397] Synthesis of compound A539-2

[0398] The synthesis and purification method of compound A1-3 were referred to, only the corresponding raw materials were changed, and the target compound A539-2 was obtained as a white solid (18.63 g, purity: 99.22%, yield: 76.52%), mass spectrum: 504.16 (M+H).

[0399] Synthesis of compound A539-3

[0400] The synthesis and purification method of compound A1-5 was referred to, only the corresponding raw material was changed, to obtain the target compound A539-3 (17.26 g, purity: 99.12%, yield: 75.63%) as a white solid, mass spectrum: 532.14 (M+H).

[0401] Synthesis of compound A539-4

[0402] The synthesis and purification method of compound A1-7 was referred to, only the corresponding raw material was changed, to obtain the target compound A539-4 (15.12 g, yield: 96.33%) as a white solid, mass spectrum: 560.12 (M+H). The obtained compound was directly used in the next step without purification.

[0403] Synthesis of compound A539-5

[0404] The synthesis and purification method of compound A1-8 was referred to, only the corresponding raw material was changed, to obtain the target compound A539-5 (14.00 g, purity: 99.87%, yield: 41.26%) as a white solid, mass spectrum: 528.24 (M+H).

[0405] Synthesis of compound A539

[0406] The synthesis and purification method of compound A1 was referred to, only the corresponding raw material was changed, to obtain the target compound A539 (14.00 g, purity: 99.92%, yield: 76.78%) as a light yellow solid. After sublimation purification of 14.00 grams of A539 crude product, sublimation pure A539 (11.52 g, purity: 99.92%, yield: 82.28%) was obtained, mass spectrum: 813.32 (M+H).

[0407] 1 H 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).

[0408] Synthesis of compound B3

[0409] Synthesis of compound B3

[0410] 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), deionized water (100 mL) were added into a 1000 mL three-necked round-bottom flask, vacuum nitrogen replacement for three times, and the temperature was raised to 75 °C for 6 hours. TLC (ethyl acetate: n-hexane = 1:10 as developing agent) was used to monitor the consumption of compound B3-1.

[0411] After cooling to room temperature, methanol (300 mL) was added and stirred at room temperature for 30 minutes. Filtration was performed to obtain a yellow solid. Xylene (600 mL) was added, and the material was dissolved by heating to 120 °C. After cooling to room temperature, column chromatography on silica gel (60 g, 200-300 mesh) was performed once. The filter cake was washed with 300 mL of xylene until no product residue was observed. The organic phases were combined and concentrated under reduced pressure at 70 °C to obtain a yellow solid. The yellow solid was crystallized twice with xylene and methanol. After vacuum drying at 100 °C for 8 hours, a light yellow solid was obtained as compound B3 (19.72 g, purity: 99.95%, yield: 87.70%). After sublimation purification of 19.72 g of crude compound B3, sublimation purified compound B3 (16.68 g, purity: 99.95%, yield: 84.59%) was obtained. Mass spectrum: 500.16 (M+H).

[0412] 1 H 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).

[0413] Synthesis of compound B32

[0414] Synthesis of compound B32

[0415] Referring to the synthesis and purification method of compound B3, only the corresponding starting materials need to be changed. A light yellow solid was obtained as target compound B32 (12.15 g, purity: 99.92%, yield: 77.65%). After sublimation purification of 12.15 g of crude compound B32, sublimation purified compound B32 (10.00 g, purity: 99.92%, yield: 82.31%) was obtained. Mass spectrum: 591.20 (M+H).

[0416] 1H NMR (400 MHz, CDC13) 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).

[0417] Synthesis of compound B105

[0418] Synthesis of compound B105-2

[0419] 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), deionized water (60 mL) were added into a 1000 mL three-necked round-bottom flask, replaced with vacuum nitrogen three times, then the system was heated to 65 °C for 6 hours, TLC (ethyl acetate: n-hexane = 1:15 as developing agent) was used to monitor the reaction, and compound B3-1 was consumed completely.

[0420] The temperature was decreased to 60 °C, and the solvent was removed by concentration under reduced pressure. Ethyl acetate (700 ml) was added, and deionized water was washed three times (300 ml x 3), and the mixture was separated. The silica gel was mixed and dried, and column chromatography was performed (200-300 mesh silica gel, ethyl acetate: n-hexane = 1:20 as eluent). After elution, the white solid was obtained by concentration under reduced pressure at 70 °C for 2 hours, and the compound B105-2 (18.53 g, purity: 99.56%, yield: 73.52%) was obtained. Mass: 383.04 (M+H).

[0421] Synthesis of compound B105-4

[0422] Compound B105-2 (18.00 g, 46.96 mmol), compound B105-3 (14.31 g, 56.35 mmol), 1,1-bis(diphenylphosphino)ferrocene palladium dichloride (Pd(dppf)Cl2, 0.34 g, 0.47 mmol), potassium acetate (KOAc, 26.91 g, 70.44 mol), 1,4-dioxane (270 ml) were added into a 500 ml three-necked round-bottom flask, replaced with vacuum nitrogen three times, then the system was heated to 100°C for 2 hours, TLC (ethyl acetate: n-hexane = 1:15 as developing agent) was used to monitor the reaction, and compound B105-2 was consumed completely.

[0423] The temperature was lowered to 60°C, and the solvent was removed by concentration under reduced pressure. Ethyl acetate (700 ml) was added, and deionized water was washed three times (300 ml x 3), and the liquid was separated. The silica gel was mixed and dried, and column chromatography was performed (200-300 mesh silica gel, ethyl acetate: n-hexane = 1:15 as eluent). After elution, 70°C was reduced pressure concentration for 1 hour to obtain white solid compound B105-4 (17.71 g, purity: 98.78%, yield: 87.65%).

[0424] Synthesis of compound B105

[0425] 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. After sublimation purification of 16.52 g of compound B105 crude product, sublimation compound B105 (13.54 g, purity: 99.93%, yield: 81.97%) was obtained, mass spectrum: 586.24 (M+H).

[0426] 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).

[0427] Synthesis of compound B162

[0428] Synthesis of compound B162-2

[0429] The synthesis and purification method of compound B105-4 were referred to, only the corresponding raw materials were changed, and the target compound B162-2 was obtained as a light yellow solid (17.63, purity: 99.02%, yield: 77.96%). Mass spectrum: 381.19 (M+H).

[0430] Synthesis of compound B162

[0431] The synthesis and purification method of compound B3 were referred to, only the corresponding raw materials were changed, and the target compound B162 was obtained as a light yellow solid (14.44 g, purity: 99.96%, yield: 76.74%). After sublimation purification of 14.44 g of compound B162 crude product, sublimation purified compound B162 was obtained (11.76 g, purity: 99.96%, yield: 81.44%). Mass spectrum: 576.22 (M+H).

[0432] 1 H 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).

[0433] Synthesis of compound B177

[0434] Synthesis of compound B177

[0435] The synthesis and purification method of compound B3 were referred to, only the corresponding raw materials were changed, and the target compound B177 was obtained as a light yellow solid (21.69 g, purity: 99.93%, yield: 87.70%). After sublimation purification of 21.69 g of compound B177 crude product, sublimation purified compound B177 was obtained (17.85 g, purity: 99.93%, yield: 82.29%). Mass spectrum: 550.20 (M+H).

[0436] 1H NMR (400 MHz, CDC13) 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).

[0437] Synthesis of compound B179

[0438] Synthesis of compound B179

[0439] Compound B177 (15.00 g, 27.29 mmol), deuterated benzene-D6 (4.52 g, 54.58 mol), trifluoroacetic acid (3.11 g, 27.29 mmol) were added into a 250 mL single necked round bottom flask, purged with vacuum nitrogen three times, then the system was heated to 50 °C and stirred for 24 hours.

[0440] The system was cooled to room temperature, and heavy water was added dropwise to quench the reaction (30 mL), stirred at room temperature for 0.5 hours, then ethyl acetate (200 mL) and deionized water were added and washed three times (100 mL) at room temperature for 30 minutes, and then filtered under vacuum to obtain 17 g of solid, which was dried at 90 °C for 1 hour to obtain 16 g of light yellow solid. The light yellow solid was crystallized twice with toluene (160 mL) and methanol (80 mL), filtered under vacuum, and the filter cake was dried at 90 °C for 3 hours to obtain light yellow solid as compound B179 (12.52 g, purity: 99.94%, yield: 80.12%). The 12.52 g of crude compound B179 was sublimed and purified to obtain sublimed and purified compound B179 (9.99 g, purity: 99.95%, deuterium substitution rate of 23 D: 95.02%, yield: 79.80%), mass spectrum: 573.33 (M+H).

[0441] Synthesis of compound B182

[0442] Synthesis of compound B182

[0443] The synthesis and purification method of compound B3 were referred to, only the corresponding raw materials were changed, to obtain the target compound B182 (17.06 g, purity: 99.96%, yield: 67.86%) as a light yellow solid. After sublimation purification of 17.06 g of compound B182 crude product, sublimation compound B182 (14.02 g, purity: 99.96%, yield: 82.18%) was obtained, mass spectrum: 509.19 (M+H).

[0444] 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).

[0445] Synthesis of compound B188

[0446] Synthesis of compound B188

[0447] The synthesis and purification method of compound B3 were referred to, only the corresponding raw materials were changed, to obtain the target compound B188 (13.33 g, purity: 99.92%, yield: 75.63%) as a light yellow solid. After sublimation purification of 13.33 g of compound B188 crude product, sublimation compound B188 (10.02 g, purity: 99.92%, yield: 76.52%) was obtained, mass spectrum: 550.20 (M+H).

[0448] 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).

[0449] Synthesis of compound B201

[0450] Synthesis of compound B201

[0451] The synthesis and purification of reference compound B3 were followed, except that the corresponding starting materials were changed, to give the target compound B201 as a light yellow solid (12.15 g, purity: 99.93%, yield: 77.86%). After sublimation purification of 12.15 g of the crude compound B201, sublimation-purified compound B201 (9.52 g, purity: 99.93%, yield: 78.36%) was obtained, mass: 550.20 (M+H).

[0452] 1 H NMR (400 MHz, CDC13) 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).

[0453] Synthesis of compound C16

[0454] Synthesis of compound C16

[0455] 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-dicyclohexylphosphino-2',4',6'-triisopropyl biphenyl (X-Phos, 0.32 g, 0.68 mmol), sodium tert-butoxide (NaOtBu, 4.94 g, 51.37 mmol), toluene (135 mL) were added to a 500 mL three-necked round-bottom flask, and the system was replaced with nitrogen three times, followed by heating to 105°C for 2 hours. The reaction was monitored by TLC (ethyl acetate:n-hexane = 1:15 as the developing agent), and compound C16-1 was consumed.

[0456] The temperature was decreased to 60°C, and methanol (150 mL) was added. The temperature was decreased to room temperature, and the mixture was stirred for 30 minutes to precipitate a large amount of solid. The solid was filtered, and 30 g (300-400 mesh) of silica gel was added to the filtrate. The mixture was heated to 100°C to dissolve the solid, and then the mixture was filtered through the silica gel. The surface of the silica gel was washed with toluene (50 mL), and the filtrate was concentrated to obtain 17 g of a solid. The solid was crystallized twice from toluene (170 mL) and methanol (80 mL). The solid was filtered, and the filter cake was dried at 90°C under vacuum for 3 hours to obtain 15.05 g of a light yellow solid as the target compound C16 (purity: 99.96%, yield: 78.20%). The 15.05 g of the crude compound C16 was purified by sublimation to obtain 12.61 g of the sublimation-purified compound C16 (purity: 99.96%, yield: 83.79%). Mass: 562.24 (M+H).

[0457] 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).

[0458] Application Example: Fabrication of an Organic Electroluminescent Device

[0459] In one embodiment, as shown in FIG. 2, the organic electroluminescent device includes a glass substrate 1, an anode 2 (indium tin oxide), a hole injection layer 3, a first hole transport layer (HTL1) 4, a second hole transport layer (HTL2) 5, a light-emitting layer 6, an electron transport layer (ETL) 7, an electron injection layer 8 (EIL), and a cathode 9, which are stacked.

[0460] A 50 mm x 50 mm x 1.0 mm glass substrate with ITO (anode 2, indium tin oxide, 100 nm) transparent electrode was cleaned ultrasonically in ethanol for 10 minutes, dried at 150°C and then treated with N2 Plasma for 30 minutes. The cleaned glass substrate was mounted on a substrate holder in a vacuum deposition apparatus and compound NDP-9 and compound HTM 1 were co-deposited to form a 10 nm thick hole injection layer in a weight ratio of 97:3, followed by deposition of a 60 nm thick film of HTM 1 as HTL1 (hole transport layer 1), followed by deposition of a 10 nm thick film of HTM 2 as HTL2 (hole transport layer 2) on the HTM 1 film, followed by co-deposition of a 40 nm thick emissive layer (host material: red dopant = 97:3, mass fraction) on the HTM 2 film, in which the host material is selected from the compound of the application, comparative compounds 1-4, either as a single host or as a plurality of hosts. An ETL (electron transport layer) material and LiQ were co-deposited (35 nm) as an electron transport material in a weight ratio of 50:50 on the emissive layer, followed by deposition of LiQ (1 nm) as an electron injection layer on the electron transport material, followed by deposition of Mg / Ag (100 nm, mass ratio 1:9) as a cathode material, to produce an organic electroluminescent device.

[0461] The structural formulae of NDP-9, HTM1, HTM2, ETL material, red dopant, LiQ, comparative compounds 1-4 are as follows:

[0462] Evaluation:

[0463] The organic electroluminescent device was tested for device performance, and the compound of the application and comparative compounds 1-4 were used as host materials for comparison. A constant current power supply (Keithley 2400) was used to flow a fixed current density through the light-emitting element, and a spectroradiometer (CS2000) was used to test the luminescence spectrum. The IVL (current-voltage-luminance) performance of the device was also determined at 10 mA / cm 2 and the LT95 device lifetime was tested at 50 mA / cm 2 The results are shown in Tables 1 and 2.

[0464] The device performance data for devices in which the compound of the application was used as a dual host, and comparative compounds 1-4 were used as a single host or dual host, and co-deposited with a red dopant to form an emissive layer, are shown in Tables 1-1 and 1-2 (in the tables, examples are devices in which the compound of the application was used, and comparative examples are devices in which at least one comparative compound was used).

[0465] Table 1-1

[0466] Table 1-2

[0467] In Table 1-1, Table 1-2, Example 29, the weight ratio of A54:B3 is 8:2, and in Example 30, the weight ratio of A54:B3 is 2:8, and in the dual-host material of other examples and comparative examples, the weight ratio of the two host materials is 1:1.

[0468] In this embodiment, the first host compound, the second host compound and the third host compound are mixed by evaporation at a weight ratio of 2:1:1 (first host: second host: third host), and the device data of the light-emitting layer co-evaporated with the red light-doped material are shown in Table 2.

[0469] Table 2

[0470] As can be seen from the above table, the device prepared by the compound of the present application has significantly better efficiency and longer service life than the device prepared by using comparative compounds 1-4.

[0471] Sublimation temperature comparison: the definition of sublimation temperature is: at a vacuum degree of 10 -7 Torr, the temperature corresponding to a sublimation rate of 1 angstrom per second. The test results are shown in Table 3.

[0472] Table 3

[0473] As can be seen from Table 3, the compound of the present application has a lower sublimation temperature than comparative compounds 1-4, which is beneficial to industrial application.

[0474] The compound of the present application as a dual-host red light material has lower voltage, higher current efficiency and longer service life than comparative compounds, because the hole and electron transport rates are balanced, the exciton recombination region in the light-emitting layer is widened, and the efficiency and service life of the device are greatly improved compared with comparative examples 1-5; at the same time, when the compound of the present application is used as a triple-host material, the efficiency and service life of the device are greatly improved compared with comparative example 6.

[0475] Therefore, the compound material of the present application has the advantages of high optical and electrical stability, low sublimation temperature, low driving voltage, high luminous efficiency, long device service life, etc., and can be used as a host material in an OLED light-emitting device. At the same time, it has a low melting point, which is beneficial to the stability of material evaporation as a melting type material. The compound of the present application as a host material has the possibility of being applied to the AMOLED industry.

[0476] In addition, since the compounds of the present application cannot be exhausted one by one, the above Tables 1-3 only list the properties of some of the compounds or devices of the present application, but within the scope of the present application, especially the compounds of the present application specifically given in the structural formula, all have the advantages of high optical and electrical stability, low sublimation temperature, low driving voltage, high luminous efficiency, long device life, etc. similar to Al.

Claims

1. A host 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 represented by formula (1): wherein ring A is selected from the following formula (1-2) or formula (1-3); Among them, X1-X 12 Each is independently selected as CR0 or N; and X1-X4, X 5- X6, X7-X8, X9-X 12 Two adjacent sites in the middle are fused with the 5-membered ring containing X in equation (1); wherein ring B is selected from a substituted or unsubstituted phenyl ring, a substituted or unsubstituted naphthalene ring, or a substituted or unsubstituted phenanthrene ring; wherein X in formula (1) is selected from NR a , CR b R c or an oxygen group element; R a , R b , R c are each independently selected from substituted or unsubstituted C1-C30alkyl, substituted or unsubstituted C1-C30heteroalkyl, substituted or unsubstituted C3-C30cycloalkyl, substituted or unsubstituted C3-C30heterocycloalkyl, substituted or unsubstituted C6-C30aryl, substituted or unsubstituted C3-C30heteroaryl, substituted or unsubstituted C1-C30alkylsilyl, or substituted or unsubstituted C6-C30arylsilyl; or, R b and R c are linked into a ring; L is selected from a single bond, a substituted or unsubstituted C6-C60 arylene group, or a substituted or unsubstituted C3-C60 heteroarylene group; Ar1and Ar2are each independently selected from a substituted or unsubstituted C6-C60 aryl group, or a substituted or unsubstituted C3-C60 heteroaryl group; wherein the second host compound has a structure represented by formula (2): wherein Z1, Z2, Z3are each independently selected from N or CR d ; Ar3to Ar5each independently represent hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C3-C60 heteroaryl group, a substituted or unsubstituted C3-C60 cycloalkyl group, a substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted tri(C1-C30)alkylsilyl group, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl group, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl group, a substituted or unsubstituted tri(C6-C30)arylsilyl group, or -N-(R’)(R”), or Ar3to Ar5are each independently and with the substituents on the carbon atoms or heteroatoms adjacent thereto, linked to form a ring; wherein at least one of Ar3to Ar5is selected from the following formula (2-1), formula (2-2), or formula (2-3): wherein “*” represents the site of attachment to L1, L2, L3in formula (2); R d each R0, R1is independently selected from hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted C1-C40alkyl, substituted or unsubstituted C1-C40heteroalkyl, substituted or unsubstituted C2-C40alkenyl, substituted or unsubstituted C2-C40alkynyl, substituted or unsubstituted C3-C40cycloalkyl, substituted or unsubstituted C3-C40heterocycloalkyl, substituted or unsubstituted C6-C60aryl, substituted or unsubstituted C3-C60heteroaryl, substituted or unsubstituted C1-C40alkoxy, substituted or unsubstituted C6-C60aryloxy, substituted or unsubstituted C1-C40alkylsilyl, substituted or unsubstituted C6-C60arylsilyl, substituted or unsubstituted C1-C40alkylboronyl, substituted or unsubstituted C6-C60arylboronyl, substituted or unsubstituted C6-C60arylophosphino, or substituted or unsubstituted C6-C60arylamino; or, two adjacent R0may be joined into a fused ring; 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; q is an integer from 0 to 10, wherein when q is an integer from 2 to 10, then each R1may be the same or different, and adjacent R1may be linked to form a fused ring; L1, L2, L3are 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; R0, R1, R a R d , L, L1~L3, Ar1~Ar5, R', R" are substituted with at least one of deuterium, halogen, cyano, isocyano, phosphino, C1-C6alkyl, C3-C16cycloalkyl, C1-C6alkyl substituted amine, C1-C6hydrocarbon substituted or unsubstituted C6-C30aryl, or C1-C6hydrocarbon substituted or unsubstituted C3-C30heteroaryl, wherein the number of substitutions is mono-substitution to the maximum number of substitutions; the heteroatoms in the heteroaryl group, heteroalkyl group, heterocycloalkyl group, or heteroatom are independently selected from at least one of O, S, N, Se, Si, or Ge.

2. The host material of claim 1, wherein, In formula (1), X1-X 12 contains at least one N; Alternatively, ring A is selected from one of the structures shown in formula (1-4) to formula (1-11): wherein “*” represents the site of attachment to the 5-membered ring containing X in formula (1); wherein a is an integer from 0 to 10; when a is an integer from 2 to 10, then each R0may be the same or different, and adjacent R0may be linked to form a fused ring.

3. The host material of claim 1, wherein, In formula (1), ring A is selected from one of the structures shown in formulae (1-12) to (1-19): wherein “*” represents the site of attachment to the 5-membered ring containing X in formula (1); wherein a is an integer from 0 to 6; when a is an integer from 2 to 6, then each R0may be the same or different, and adjacent R0may be linked to form a fused ring.

4. The host material of claim 1, wherein, In formula (1), ring B is selected from one of the structures shown in formulae (1-20) to (1-26): wherein “*” represents the site of attachment to the 5-membered ring containing X in formula (1); R g independently selected from hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted C1-C40alkyl, substituted or unsubstituted C1-C40heteroalkyl, substituted or unsubstituted C2-C40alkenyl, substituted or unsubstituted C2-C40alkynyl, substituted or unsubstituted C3-C40cycloalkyl, substituted or unsubstituted C3-C40heterocycloalkyl, substituted or unsubstituted C6-C60aryl, substituted or unsubstituted C3-C60heteroaryl, substituted or unsubstituted C1-C40alkoxy, substituted or unsubstituted C6-C60aryloxy, substituted or unsubstituted C1-C40alkylsilyl, substituted or unsubstituted C6-C60arylsilyl, substituted or unsubstituted C1-C40alkylboronyl, substituted or unsubstituted C6-C60arylboryl, substituted or unsubstituted C6-C60arylphosphino, or substituted or unsubstituted C6-C60arylamino; R g substituted with at least one of deuterium, halogen, cyano, isocyano, phosphino, C1-C6alkyl, C3-C16cycloalkyl, C1-C6alkyl substituted amine, C1-C6hydrocarbyl substituted or unsubstituted C6-C30aryl, or C1-C6hydrocarbyl substituted or unsubstituted C3-C30heteroaryl, wherein the number of substitutions ranges from mono-substitution to the maximum number of substitutions; wherein w is an integer from 0 to 10; when w is an integer from 2 to 10, then each R g may be the same or different, and adjacent R g may be connected to form a fused ring.

5. The host material according to any one of claims 1 to 4, characterized in that the L, L1, L2, L3are independently selected from a single bond, a substituted or unsubstituted C6-C30 arylene group, or a substituted or unsubstituted C3-C30 heteroarylene group; and / or, said X is selected from NR a , CR b R c , O, S or Se; and / or, R a , R b , R c are each independently selected from C1-C10 alkyl, C1-C10 heteroalkyl, C3-C10 cycloalkyl, C3-C10 heterocycloalkyl, or C6-C10 aryl or C5-C10 heteroaryl; or, R b and R c are joined to form a fluorene group; and / or, at least two of Z1, Z2, Z3are N; and / or, In formula (2), at least one of Ar3to Ar5is selected from the structures represented by formula (2-4), formula (2-5), or formula (2-6): wherein “*” represents the site of attachment of Ar3to Ar5.

6. The host material of claim 5, wherein, the X is selected from O, and Z1, Z2, Z3are all N.

7. The host material of claim 5, wherein, L, L1, L2, L3are independently selected from a single bond or one of the structures shown in formula (3-1) to formula (3-17): wherein "*" indicates a bonding site of L, L1, L2, L3.

8. The host material according to any one of claims 1 to 4, characterized in that Ar1to Ar5are each independently selected from at least one of 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 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 9. The host material of claim 1, wherein, R d each R0, R1is independently selected from hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted C1-C10alkyl, substituted or unsubstituted C1-C10heteroalkyl, substituted or unsubstituted C3-C10cycloalkyl, substituted or unsubstituted C3-C10heterocycloalkyl, substituted or unsubstituted C6-C12aryl, or substituted or unsubstituted C3-C12heteroaryl.

10. The host material of claim 1, wherein, R g independently selected from hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted C1-C10alkyl, substituted or unsubstituted C1-C10heteroalkyl, substituted or unsubstituted C2-C10alkenyl, substituted or unsubstituted C2-C10alkynyl, substituted or unsubstituted C3-C10cycloalkyl, substituted or unsubstituted C3-C10heterocycloalkyl, substituted or unsubstituted C6-C12aryl, or substituted or unsubstituted C3-C12heteroaryl.

11. The host material of claim 1, wherein, Ar3to Ar5are each independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted C1-C30alkyl group, a substituted or unsubstituted C6-C30aryl group, a substituted or unsubstituted C3-C30heteroaryl group, a substituted or unsubstituted C3-C30cycloalkyl group, a substituted or unsubstituted C1-C20alkoxy group, a substituted or unsubstituted tri(C1-C20)alkylsilyl group, a substituted or unsubstituted di(C1-C20)alkyl(C6-C30)arylsilyl group, a substituted or unsubstituted (C1-C20)alkyl-di(C6-C30)arylsilyl group, a substituted or unsubstituted tri(C6-C30)arylsilyl group.

12. The host material of claim 1, wherein, The compound of formula (1) is selected from one of the following structural formulae, or one of the following structural formulae in which the hydrogen has been partially or completely replaced by deuterium or fluorine:

13. The host material of claim 1, wherein, The compound of formula (2) is selected from one of the following structural formulae, or one of the following structural formulae in which the hydrogen is partially or completely replaced by deuterium or fluorine:

14. The host material of claim 1, wherein, The host material composition further comprises at least one third host compound represented by the formula (1) or formula (2), but different from the first host compound or the second host compound.

15. An organic electroluminescent device, characterized by A host material as claimed in any one of claims 1 to 14.

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