Compound and organic electroluminescent device

Abstract

The present invention relates to the technical field of organic electroluminescence, and provides a compound and an organic electroluminescent device. The compound has a general structural formula as represented by formula (1). Formula (1), wherein ring A is selected from formulas (2)-(5) below, and * represents a site fused to a 5-membered ring comprising X; in one of formulas (2)-(5), hydrogen on the four benzene rings of benzophenanthrene can be substituted with deuterium or fluorine; in formula (1), X is selected from NRa1, CRbRc, or a chalcogen. The compound has the advantages of low driving voltage, high luminous efficiency, and long device service life, and can be used as a host material in OLED light-emitting devices.

Description

A compound and an organic electroluminescence device TECHNICAL FIELD

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

[0002] Organic electroluminescence devices (OLED) are widely used in display and lighting technology. However, compared with market application requirements, the performance of OLED devices such as luminous efficiency, driving voltage, service life, etc. still needs to be improved.

[0003] The performance of organic functional materials has an important influence on the OLED light-emitting performance, because the basic structure of the OLED device is a sandwich structure of various different functional organic functional material films in the middle of the metal electrode, under the driving of the current, holes and electrons are injected from the cathode and anode respectively, and after moving a distance, the holes and electrons are recombined in the light-emitting layer and released in the form of light or heat, thereby achieving the light-emitting effect. The performance of the organic functional material affects the movement of the holes and electrons, and further affects the OLED light-emitting performance.

[0004] However, the properties of phosphorescent OLEDs are not only determined by the triplet light-emitting body used. Other types of materials, such as host materials, are also 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. In addition, the existing types of organic functional materials with good performance are few, which makes the market supply insufficient.

[0005] Therefore, it is necessary to continue to develop new types of organic functional materials. SUMMARY

[0006] 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 compound and an organic electroluminescence device.

[0007] The first aspect of the present application provides a compound.

[0008] In some embodiments, a compound has a general structure as shown in formula (1):

[0009] In formula (1), X is selected from NR

[0010] In formula (2)-formula (5), the hydrogens on the four benzophenone rings can be replaced by deuterium or fluorine;

[0011] In formula (1), X is selected from NRa1 , CR b R c or a chalcogen element;

[0012] wherein a represents an integer from 1 to 4, b represents an integer from 1 to 10, wherein when a > 2, the two adjacent R0may be connected to form a fused ring;

[0013] R0is selected from hydrogen, deuterium, halogen, cyano, nitro, C1-C40alkyl, C1-C40heteroalkyl, C2-C40alkenyl, C2-C40alkynyl, C3-C40cycloalkyl, C3-C40heterocycloalkyl, substituted or unsubstituted C6-C60aryl, substituted or unsubstituted C3-C60heteroaryl, C1-C40alkoxy, C6-C60aryloxy, C3-C40alkylsilyl, C6-C60arylsilyl, C1-C40alkylboronyl, C6-C60arylboronyl, C6-C60arylphosphino, or C6-C60arylamino;

[0014] R1represents -L-ETor -L-NAr1Ar2;

[0015] L is selected from a single bond, substituted or unsubstituted C6-C60arylene, or substituted or unsubstituted C3-C60heteroarylene;

[0016] ETrepresents an electron withdrawing group;

[0017] Ar1and Ar2are each independently selected from substituted or unsubstituted C6-C36aryl, substituted or unsubstituted C2-C36heteroaryl;

[0018] R a1 , R b , R c are each independently selected from C1-C30alkyl, C1-C30heteroalkyl, C3-C30cycloalkyl, C3-C30heterocycloalkyl, C6-C30aryl, C3-C30heteroaryl, C3-C30alkylsilyl, C6-C30arylsilyl, or substituted or unsubstituted amino, when X is CR b R c , R b , R c may be connected to each other to form a ring;

[0019] the substitution is at least one of deuterium, halogen, cyano, isocyano, phosphino, C1-C6alkyl, C3-C16cycloalkyl, or C1-C6alkyl substituted amine, C1-C6hydrocarbyl substituted or unsubstituted C6-C30aryl, C1-C6hydrocarbyl substituted or unsubstituted C3-C30heteroaryl, wherein the number of substitutions is from monosubstitution to the maximum number of substitutions.

[0020] In the above formulae (2) to (5), the hydrogen on the four benzene rings of the triphenylene group can be replaced by deuterium or fluorine, meaning that the hydrogen on the four benzene rings of the triphenylene group can be partially or completely replaced by deuterium or fluorine.

[0021] In some embodiments, R0is selected from hydrogen, deuterium, halogen, cyano, nitro, C1-C30alkyl, C1-C30heteroalkyl, C2-C30alkenyl, C2-C30alkynyl, C3-C30cycloalkyl, C3-C30heterocycloalkyl, C6-C30aryl, C3-C30heteroaryl, C1-C30alkoxy, C6-C30aryloxy, C3-C30alkylsilyl, C6-C30arylsilyl, C1-C30alkylboronyl, C6-C30arylboronyl, C6-C30arylphosphino, or C6-C30arylamino.

[0022] In some embodiments, R0is selected from hydrogen, deuterium, halogen, cyano, nitro, C1-C20alkyl, C1-C20heteroalkyl, C2-C20alkenyl, C2-C20alkynyl, C3-C20cycloalkyl, C3-C20heterocycloalkyl, C6-C20aryl, C3-C20heteroaryl, C1-C20alkoxy, C6-C20aryloxy, C3-C20alkylsilyl, C6-C20arylsilyl, C1-C20alkylboronyl, C6-C20arylboronyl, C6-C20arylphosphino, or C6-C20arylamino.

[0023] In some embodiments, the R0is selected from hydrogen, deuterium, halogen, cyano, nitro, C1-C10alkyl, C1-C10heteroalkyl, C2-C10alkenyl, C2-C10alkynyl, C3-C10cycloalkyl, C3-C10heterocycloalkyl, C6-C12aryl, C3-C12heteroaryl.

[0024] In some embodiments of the present application, adjacent R0refers to R0on adjacent carbon atoms.

[0025] In some embodiments of the present application, the substitution is by 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 substitutions is from mono-substitution to the maximum number of substitutions.

[0026] In some embodiments of the application, the substitution is by 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 substitutions ranges from mono-substitution to the maximum number of substitutions.

[0027] In some embodiments, the chalcogen element is selected from O, S, or Se.

[0028] In some embodiments, the R a1 , R b , R c are each independently selected from C1-C20alkyl, C1-C20heteroalkyl, C3-C20cycloalkyl, C3-C20heterocycloalkyl, C6-C20aryl, C5-C20heteroaryl, C3-C20alkylsilyl, C6-C20arylsilyl.

[0029] In some embodiments, the R a1 , R b , R c are each independently selected from C1-C15alkyl, C1-C15heteroalkyl, C3-C15cycloalkyl, C3-C15heterocycloalkyl, C6-C18aryl, C5-C18heteroaryl, C3-C15alkylsilyl, C6-C18arylsilyl.

[0030] In some embodiments, the Ar1and Ar2are each independently selected from substituted or unsubstituted C6-C30aryl, substituted or unsubstituted C2-C30heteroaryl.

[0031] In some embodiments, the Ar1and Ar2are each independently selected from substituted or unsubstituted C6-C18aryl, substituted or unsubstituted C2-C18heteroaryl.

[0032] In some embodiments, the Ar1and Ar2are each independently selected from substituted or unsubstituted C6-C12aryl, substituted or unsubstituted C2-C12heteroaryl.

[0033] In some embodiments, the heteroatom in the heteroaryl, heteroalkyl, or heterocycloalkyl is independently selected from at least one of O, S, N, Se, Si, Ge.

[0034] In some embodiments, the structure represented by Formula (2) to Formula (5) is selected from the structures represented by Formula (6) to Formula (9):

[0035] wherein * indicates the site of fusion to the 5-membered ring containing X in Formula (1).

[0036] In some embodiments, the ET representing electron withdrawing group is selected from the structures shown in the following Formulas B-1 to B-10:

[0037] wherein each Z is independently N or CR d , and at least one Z in Formulas (B-1) to (B-3) and (B-6) to (B-10) is N, and the two adjacent Zs in (B-10) are not both N;

[0038] each W is independently NR e , O, S, SO, SO2, CR f R g , or SiR h R j ;

[0039] each Y is independently NR a1 , CR b R c , O, S, or Se; R a1 , R b , R c are as defined above;

[0040] R2, R d - R h , R j are independently selected from hydrogen, deuterium, halogen, cyano, nitro, C1-C40 alkyl, C1-C40 heteroalkyl, C2-C40 alkenyl, C2-C40 alkynyl, C3-C40 cycloalkyl, C3-C40 heterocycloalkyl, C3-C40 alkylsilyl, C6-C60 arylsilyl, C1-C40 alkylboron, C1-C40 alkoxy, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, substituted or unsubstituted C6-C60 aryloxy, substituted or unsubstituted C6-C60 arylboron, substituted or unsubstituted C6-C60 arylphosphine, or substituted or unsubstituted C6-C60 arylamine;

[0041] wherein n is an integer from 0 to 10; if n is an integer of 2 or more, each R2may be the same or different, and adjacent R2may be connected to form a ring.

[0042] In some embodiments, adjacent R2refers to R2on adjacent carbon atoms.

[0043] In some embodiments, the ET representing electron withdrawing group is selected from the structures shown in the following Formulas (B-11) to (B-36):

[0044] wherein each R2is independently selected from hydrogen, deuterium, halogen, cyano, nitro, C1-C40 alkyl, C1-C40 heteroalkyl, C2-C40 alkenyl, C2-C40 alkynyl, C3-C40 cycloalkyl, C3-C40 heterocycloalkyl, substituted or unsubstituted C6-C60 aryl, C5-C60 heteroaryl, C1-C40 alkoxy, C6-C60 aryloxy, C3-C40 alkylsilyl, C6-C60 arylsilyl, C1-C40 alkylboronyl, C6-C60 arylboronyl, C6-C60 arylphosphino, or C6-C60 arylamino;

[0045] n is an integer from 0 to 6, and if n > 2, each R2may be the same or different, and adjacent R2may be joined to form a ring.

[0046] In some embodiments, R2is selected from hydrogen, deuterium, halogen, cyano, nitro, C1-C30 alkyl, C1-C30 heteroalkyl, C2-C30 alkenyl, C2-C30 alkynyl, C3-C30 cycloalkyl, C3-C30 heterocycloalkyl, substituted or unsubstituted C6-C40 aryl, C5-C40 heteroaryl, C1-C30 alkoxy, C6-C40 aryloxy, C3-C30 alkylsilyl, C6-C40 arylsilyl, C1-C30 alkylboronyl, C6-C40 arylboronyl, C6-C30 arylphosphino, or C6-C30 arylamino.

[0047] In some embodiments, R2is selected from hydrogen, deuterium, halogen, cyano, nitro, C1-C20 alkyl, C1-C20 heteroalkyl, C2-C20 alkenyl, C2-C20 alkynyl, C3-C20 cycloalkyl, C3-C20 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, C5-C30 heteroaryl, C1-C20 alkoxy, C6-C30 aryloxy, C3-C20 alkylsilyl, C6-C30 arylsilyl, C1-C20 alkylboronyl, C6-C30 arylboronyl, C6-C20 arylphosphino, or C6-C20 arylamino.

[0048] In some embodiments, the L is a substituted or unsubstituted C6-C20 arylene or heteroarylene.

[0049] In some embodiments, the L is selected from a single bond and the structures represented by Formula L-1 to Formula L-14:

[0050] wherein R4is a substituent, each R4is independently selected from hydrogen, deuterium, halogen, cyano, nitro, C1-C20alkyl, C1-C20heteroalkyl, C2-C20alkenyl, C2-C20alkynyl, C3-C20cycloalkyl, C3-C20heterocycloalkyl, C6-C30aryl, C5-C30heteroaryl, C1-C20alkoxy, C6-C30aryloxy, C3-C20alkylsilyl, C6-C30arylsilyl, C1-C20alkylboron, C6-C30arylboron, C6-C30arylphosphine, or C6-C30arylamines, and m is a single substitution to a maximum number of substitutions.

[0051] In some embodiments, m has a value of 1-16, and m can have a value of 1-14, 1-12, 1-10, or 2-8, in particular.

[0052] In some embodiments, X is CR b R c , O, or S.

[0053] In some embodiments, R b , R c are each independently selected from C1-C10alkyl, C1-C10heteroalkyl, C3-C10cycloalkyl, C3-C10heterocycloalkyl, C6-C10aryl, or C5-C10heteroaryl.

[0054] In some embodiments, Ar1and Ar2are each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted 9,9-spirobifluorenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted pyrenyl, substituted or unsubstituted In some embodiments, Ar1and Ar2are each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted 9,9-spirobifluorenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted pyrenyl, substituted or unsubstituted

[0055] In some embodiments of the application, the substituents are at least one of deuterium, halogen, cyano, isocyano, phosphino, C1-C6 alkyl, C3-C12 cycloalkyl, C1-C6 alkyl substituted amine, C6-C18 aryl, or C3-C18 heteroaryl, wherein the number of substitutions is from mono-substitution to the maximum number of substitutions.

[0056] In some embodiments of the application, the substituents are at least one of deuterium, halogen, cyano, isocyano, phosphino, C1-C6 alkyl, C3-C10 cycloalkyl, C1-C6 alkyl substituted amine, C6-C12 aryl, or C3-C12 heteroaryl, wherein the number of substitutions is from mono-substitution to the maximum number of substitutions.

[0057] In some embodiments of the application, aryl is selected from phenyl, naphthyl, anthryl, phenanthryl, naphthacene, pyrenyl, In some embodiments of the application, aryl is selected from phenyl, naphthyl, anthryl, phenanthryl, naphthacene, pyrenyl,

[0058] In some embodiments of the application, heteroaryl is selected from pyrrolyl, pyrazinyl, pyridyl, pyrimidinyl, triazinyl, indolyl, isoindolyl, imidazolyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, azadibenzofuranyl, azadibenzothiophenyl, diazadibenzofuranyl, diazadibenzothiophenyl, quinolyl, isoquinolyl, quinoxalyl, carbazolyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, phenothiazinyl, phenoxazinyl, oxazolinyl, oxadiazolyl, furazanyl, thiophenyl, benzothiophenyl, dihydroacridinyl, azacarbazolyl, diazacarbazolyl, or quinazolinyl.

[0059] In some embodiments, the compound is one of the following structural formulae, or a structure in which hydrogen is partially or completely replaced by deuterium, fluorine:

[0060] A second aspect of the present application provides an organic electroluminescent device.

[0061] An organic electroluminescent device comprising the above compound.

[0062] In some embodiments, an organic electroluminescent device includes: a cathode and an anode, the cathode and the anode being disposed opposite to each other, and a light-emitting layer being disposed between the cathode and the anode, the light-emitting layer comprising the aforementioned compound.

[0063] The compounds described in this invention can be used alone or after doping to prepare luminescent layers.

[0064] In one embodiment, the light-emitting layer is a red light-emitting layer, comprising a red light-emitting material and at least one of the above-described compounds. In one embodiment, the compound of the present invention serves as the host material of the red light-emitting layer.

[0065] Compared with the prior art, the beneficial effects of the present invention are as follows:

[0066] The compound described in this invention possesses advantages such as low driving voltage, high luminous efficiency, and long device lifetime, making it suitable as a host material in OLED light-emitting devices. It also exhibits a low melting point and low sublimation temperature, which is beneficial for material deposition stability as a molten material. As a host material for red light, the compound described in this invention has the potential for application in the AMOLED industry. Attached Figure Description

[0067] Figure 1 shows the compound CPD346 of this invention. 1 H NMR spectrum;

[0068] Figure 2 is a schematic diagram of the structure of an organic electroluminescent device according to an embodiment of the present invention. Detailed Implementation

[0069] To enable those skilled in the art to more clearly understand the technical solutions described in this invention, the following embodiments are provided for illustration. It should be noted that the following embodiments do not constitute a limitation on the scope of protection claimed by this invention.

[0070] Unless otherwise specified, the raw materials, reagents or devices used in the following examples are available from conventional commercial sources or can be obtained by existing known methods.

[0071] A compound with the general structural formula shown in formula (1):

[0072] Wherein, ring A is selected from the following formulas (2)-(5), and * indicates the site that is fused with the 5-membered ring containing X;

[0073] In one of formulas (2) to (5), the hydrogen atoms on the four benzene rings of benzo[a]phenanthrene can be replaced by deuterium or fluorine;

[0074] In equation (1), X is selected from NR. a1 CR b Rc Or oxygen group elements;

[0075] Where a represents an integer from 1 to 4, b represents an integer from 1 to 10, and when a or b ≥ 2, multiple R0s can be the same or different, multiple R1s can be the same or different, and two adjacent R0s can be connected to form a parallel ring;

[0076] R0 is selected from hydrogen, deuterium, halogen, cyano, nitro, C1-C40 alkyl, C1-C40 heteroalkyl, C2-C40 alkenyl, C2-C40 alkynyl, C3-C40 cycloalkyl, C3-C40 heterocycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, C1-C40 alkoxy, C6-C60 aryloxy, C3-C40 alkylsilyl, C6-C60 arylsilyl, C1-C40 alkylboryl, C6-C60 arylboryl, C6-C60 arylphosphinyl, or C6-C60 arylamine.

[0077] R1 represents -L-ET or -L-NAr1Ar2;

[0078] L is selected from single bond, substituted or unsubstituted C6-C60 aryl group or substituted or unsubstituted C3-C60 heteroaryl group;

[0079] ET indicates an electron-withdrawing group;

[0080] Ar1 and Ar2 are independently selected from substituted or unsubstituted C6-C36 aryl or substituted or unsubstituted C2-C36 heteroaryl, respectively;

[0081] R a1 R b R c Each amino group is independently selected from C1-C30 alkyl, C1-C30 heteroalkyl, C3-C30 cycloalkyl, C3-C30 heterocycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C3-C30 alkylsilyl, C6-C30 arylsilyl, or substituted or unsubstituted amino groups, when X is CR b R c At that time, R b R c They can be connected to form a ring;

[0082] The substitution is at least one of the following: a amine group substituted with deuterium, halogen, cyano, isocyano, phosphin, C1-C6 alkyl, C3-C16 cycloalkyl or C1-C6 alkyl, an amino group substituted with C1-C6 hydrocarbon or an unsubstituted C6-C30 aryl or a C1-C6 hydrocarbon or an unsubstituted C3-C30 heteroaryl, wherein the number of substitutions is from monosubstituted to the maximum number of substitutions.

[0083] the heteroatoms in the heteroaryl, heteroalkyl or heterocycloalkyl group are independently selected from at least one of O, S, N, Se, Si, Ge;

[0084] Hereinafter, examples of each group of the compounds represented by formulae (1) to (5) are described.

[0085] Note that, in the present specification, "carbon number a ~ b" in the expression "substituted or unsubstituted X group having carbon number a ~ b" means the carbon number of the X group in the case where the X group is not substituted, and does not include the carbon number of the substituent when the X group is substituted.

[0086] The "plurality" of the present application means a number of 2 or more, for example, 2, 3, 6, 8, etc.

[0087] As a specific example of the alkyl group, there are straight-chain or branched-chain alkyl groups, specifically, for example, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, t-butyl, n-pentyl and its isomers, n-hexyl and its isomers, n-heptyl and its isomers, n-octyl and its isomers, n-nonyl and its isomers, or n-decyl and its isomers, etc., and preferably methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, t-butyl, and more preferably propyl, isopropyl, isobutyl, sec-butyl, or t-butyl.

[0088] As a specific example of the cycloalkyl group, there are, for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 1-adamantyl, 2-adamantyl, 1-norbornyl, 2-norbornyl, etc., and preferably cyclopentyl or cyclohexyl.

[0089] As a specific example of the alkenyl group, there are, for example, ethenyl, propenyl, allyl, 1-butyldienyl, 2-butyldienyl, 1-hexatrienyl, 2-hexatrienyl, 3-hexatrienyl, etc., and preferably propenyl or allyl.

[0090] As a specific example of the heteroalkyl group, there are straight-chain or branched-chain alkyl groups, cycloalkyl groups, etc. composed of atoms other than carbon and hydrogen, for example, mercaptomethylmethane group, methoxymethylmethane group, ethoxymethylmethane group, t-butoxymethylmethane group, N,N-dimethylmethane group, epoxybutane group, epoxy pentane group, or epoxyhexane group, etc., and preferably methoxymethylmethane group, epoxy pentane group.

[0091] As a specific example of the aryl group, there are, for example, phenyl, naphthyl, anthryl, phenanthryl, tetracenyl, pyrenyl,

[0092] ​As specific examples of the heteroaryl group, for example, pyrrolyl, pyrazinyl, pyridyl, pyrimidinyl, triazinyl, indolyl, isoindolyl, imidazolyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, azadibenzofuranyl, azadibenzothiophenyl, diazadibenzofuranyl, diazadibenzothiophenyl, quinolyl, isoquinolyl, quinoxalyl, carbazolyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, phenothiazinyl, phenoxazinyl, oxazolinyl, oxadiazolyl, furazanyl, thiophenyl, benzothiophenyl, dihydroacridinyl, azacarbazolyl, diazacarbazolyl, quinazolinyl, and the like, preferably pyridyl, pyrimidinyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, azadibenzofuranyl, azadibenzothiophenyl, diazadibenzofuranyl, diazadibenzothiophenyl, carbazolyl, azacarbazolyl, or diazacarbazolyl.

[0093] The following examples are merely for the purpose of facilitating the understanding of the technical invention and should not be regarded as specific limitations of the present invention.

[0094] 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.

[0095] Synthesis of compound CPD10

[0096] The synthetic route is as follows:

[0097] Synthesis of compound CPD10-3

[0098] CPD10-1 (25.00 g, 117.92 mmol), CPD10-2 (31.78 g, 117.92 mmol), tetrakis(triphenylphosphine)palladium (Pd(PPh3)4, 1.36 g, 1.18 mmol), potassium carbonate (24.45 g, 176.88 mmol), tetrahydrofuran (THF, 480 mL), deionized water (160 mL) were added into a 1000 mL three-necked round-bottom flask, replaced with vacuum nitrogen three times, then the system was heated to 75°C for 3 hours, and the reaction was monitored by TLC (ethyl acetate: n-hexane = 1:10 as developing agent), and the raw material CPD10-2 was consumed completely;

[0099] The temperature was lowered to 60°C, and the solvent was removed by concentration under reduced pressure. Ethyl acetate (700 mL) was added, and the mixture was washed with deionized water three times (300 mL*3). The mixture was separated, and the silica gel was dried and columned. The mixture was purified by silica gel column chromatography (200-300 mesh silica gel, ethyl acetate:n-hexane = 1:20 as eluent). After elution, the mixture was concentrated under reduced pressure at 70°C for 2 hours to obtain white solid CPD10-3 (31.27 g, mass fraction purity: 99.23%, yield: 74.33%).

[0100] Synthesis of compound CPD10-5

[0101] CPD10-3 (28.00 g, 78.47 mmol), CPD10-4 (40.35 g, 117.71 mmol), and tetrahydrofuran (450 mL) were added to a 1000 mL three-necked round-bottom flask, and the system was replaced with nitrogen three times. Then the temperature was lowered to 5°C, and sodium methoxide (8.48 g, 156.95 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. When the raw material CPD10-3 was consumed completely,

[0102] Deionized 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 mixture was concentrated under reduced pressure at 70°C for 1 hour to obtain white solid CPD10-5 (28.69 g, yield: 95.00%). The mass spectrometry characterization result was 385.09 (M+H). The obtained compound was directly used in the next step without purification.

[0103] Synthesis of compound CPD10-6

[0104] CPD10-5 (26.00 g, 67.56 mmol) and toluene (260 mL) were added to a 1000 mL three-necked round-bottom flask, and the system was replaced with nitrogen three times. Then the temperature was lowered to 5°C, and methyl sulfonic acid (MsOH, 12.98 g, 135.11 mmol) was slowly added dropwise. The dropwise addition was completed in 3 minutes, and the reaction was maintained at 5°C for 1 hour. TLC (ethyl acetate:n-hexane = 1:15 as developing agent) was used to monitor the reaction. When the raw material CPD10-5 was consumed completely,

[0105] Methanol (260 mL) was added to the mixture, and a large amount of white solid was precipitated. Filtration under suction gave 23 g of solid. The solid was crystallized once with toluene (230 mL) and methanol (230 mL), and then the mixture was filtered under suction. The filter cake was dried under vacuum at 80°C for 1 hour to obtain white solid CPD10-6 (17.79 g, mass fraction purity: 99.83%, yield: 60.00%). The mass spectrometry characterization result was 353.06 (M+H).

[0106] Synthesis of compound CPD10-8

[0107] CPD10-6 (25.00 g, 70.86 mmol), CPD10-7 (21.59 g, 85.03 mmol), tris(dibenzylideneacetone)dipalladium (Pd2(dba)3, 1.30 g, 1.42 mmol), 2-dicyclohexylphosphino-2',4',6'-triisopropyl biphenyl (X-Phos, 1.35 g, 2.84 mmol), potassium acetate (13.91 g, 141.72 mmol), 1,4-dioxane (375 ml) were added into a 1000 mL three-necked round-bottom flask, which was replaced with nitrogen for three times, then the system was heated to 100 °C for 2 hours, TLC (ethyl acetate: n-hexane = 1:10 as developing agent) was used to monitor the reaction, and the raw material CPD10-6 was consumed completely.

[0108] 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 deionized water three times (300 ml*3). The mixture was separated, and the silica gel was mixed and dried. The sample was column-purified by silica gel column chromatography (200-300 mesh silica gel, ethyl acetate: n-hexane = 1:15 as eluent). After elution, the white solid was obtained by concentration under reduced pressure at 70 °C for 1 hour. The mass fraction purity of CPD10-8 was 98.05%, and the yield was 77.07%. The mass spectrometry characterization result was 445.12 (M+H).

[0109] Synthesis of compound CPD10

[0110] CPD10-8 (24.00 g, 54.01 mmol), CPD10-9 (22.63 g, 54.01 mmol), tetrakis(triphenylphosphine)palladium (1.25 g, 1.08 mmol), potassium carbonate (11.20 g, 81.02 mmol), tetrahydrofuran (360 mL), deionized water (120 mL) were added into a 1000 mL three-necked round-bottom flask, which was 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 the raw material CPD10-9 was consumed completely.

[0111] The temperature was decreased to 60 °C, and the solvent was removed by concentration under reduced pressure. The yellow solid was obtained by filtration. Xylene (760 mL) was added, and the material was dissolved by heating to 120 °C. The temperature was decreased to room temperature, and the material was filtered once through a column chromatography on silica gel (50 g, 200-300 mesh). The filter cake was washed with 300 mL of xylene until no product residue was present. The organic phases were combined and concentrated under reduced pressure at 70 °C for 2 hours to obtain a yellow solid. The yellow solid was crystallized twice with xylene and methanol. The yellow solid was dried under vacuum at 100 °C for 8 hours to obtain compound CPD10 (28.52 g, mass fraction purity: 99.97%, yield: 75.33%). The 28.52 g of crude CPD10 was purified by sublimation to obtain sublimed CPD10 (20.94 g, mass fraction purity: 99.97%, yield: 73.43%). Mass spectrometry characterization result: 701.25 (M+H). Nuclear magnetic resonance characterization result: 1 H NMR (400 MHz, CDC13) δ 8.64 (d, J = 9.5 Hz, 1H), 8.50 (d, J = 2.4 Hz, 1H), 8.36 (d, J = 9.5 Hz, 1H), 8.20 (d, J = 9.7 Hz, 1H), 8.14 - 8.07 (m, 2H), 8.04 (d, J = 9.7 Hz, 1H), 8.02 - 7.95 (m, 2H), 7.95 - 7.91 (m, 1H), 7.87 (s, 1H), 7.83 - 7.78 (m, 4H), 7.67 - 7.61 (m, 5H), 7.58 - 7.55 (m, 4H), 7.45 - 7.37 (m, 8H).

[0112] Synthesis of compound CPD16

[0113] The synthesis route is as follows:

[0114] Synthesis of compound CPD16

[0115] Referring to the synthesis and purification method of compound CPD10, only the corresponding starting materials need to be changed. The yellow solid obtained is the target compound CPD16 (20.52 g, mass fraction purity: 99.96%, yield: 75.06%). The 20.52 g of crude CPD16 was purified by sublimation to obtain sublimed CPD16 (17.06 g, mass fraction purity: 99.96%, yield: 83.14%). Mass spectrometry characterization result: 523.17 (M+H). Nuclear magnetic resonance characterization result: 1H NMR (400 MHz, CDC13) δ 8.88 (s, 1H), 8.64 (d, J = 9.3 Hz, 1H), 8.47 (d, J = 2.4 Hz, 1H), 8.36 (d, J = 9.6 Hz, 1H), 8.20 (d, J = 9.7 Hz, 1H), 8.09 (d, J = 9.5 Hz, 1H), 8.08 - 8.02 (m, 2H), 8.02 - 7.95 (m, 3H), 7.93 (d, J = 9.4 Hz, 1H), 7.89 (dd, J = 7.3, 1.2 Hz, 1H), 7.67 - 7.60 (m, 1H), 7.58 - 7.50 (m, 2H), 7.47 - 7.36 (m, 6H).

[0116] Synthesis of compound CPD29

[0117] The synthesis route is as follows:

[0118] Synthesis of compound CPD29

[0119] Compound CPD10-8 (20.00 g, 45.01 mmol), CPD29-1 (16.10 g, 45.01 mmol), tetrakis(triphenylphosphine)palladium (1.04 g, 0.90 mmol), sodium hydroxide (3.6 g, 90.02 mmol), tetrahydrofuran (300 ml), deionized water (100 ml) were added into a 1000 ml three-necked round-bottom flask, vacuum nitrogen replacement three times, and the temperature was raised to 75 °C for 3 hours. TLC (ethyl acetate: n-hexane = 1:10 as developing agent) was used to monitor the consumption of raw material CPD29-1.

[0120] After cooling to room temperature, methanol (200 ml) was added and stirred at room temperature for 30 minutes. Filtration was performed to obtain a yellow solid. Xylene (500 ml) was added, and the material was dissolved by heating to 120 °C. After cooling to room temperature, column chromatography on silica gel (50 g, 200-300 mesh) was performed once. The filter cake was washed with 200 ml of xylene until no product residue was left. The organic phase was 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 yellow solid was obtained as compound CPD29 (21.69 g, mass fraction purity: 99.97%, yield: 75.33%). After sublimation purification of 21.69 g of CPD29 crude product, sublimation pure CPD29 (16.01 g, mass fraction purity: 99.97%, yield: 73.84) was obtained. Mass spectrometry characterization results: 640.12 (M+H). NMR characterization results: 1H NMR (400 MHz, CDC13) δ 8.64 (d, J = 9.3 Hz, 1H), 8.47 (d, J = 2.6 Hz, 1H), 8.36 (d, J = 9.6 Hz, 1H), 8.20 (d, J = 9.7 Hz, 1H), 8.14 - 8.06 (m, 4H), 8.06 - 8.00 (m, 3H), 7.99 - 7.95 (m, 1H), 7.93 (d, J = 9.2 Hz, 1H), 7.87 (dd, J = 9.3, 1.3 Hz, 1H), 7.67 - 7.59 (m, 2H), 7.55 (dd, J = 6.8, 1.1 Hz, 1H), 7.53 - 7.47 (m, 3H), 7.46 - 7.36 (m, 4H), 7.26 (dd, J = 9.3, 6.8 Hz, 1H).

[0121] Synthesis of compound CPD41

[0122] The synthesis route is as follows:

[0123] Synthesis of compound CPD41-2

[0124] Referring to the synthesis and purification method of compound CPD10-3, only the corresponding raw materials need to be changed, and the target compound CPD41-2 (28.79 g, mass fraction purity: 99.02%, yield: 76.82%) is obtained as a white solid, and the mass spectrometry characterization result is: 357.06 (M+H).

[0125] Synthesis of compound CPD41-3

[0126] Referring to the synthesis and purification method of compound CPD10-5, only the corresponding raw materials need to be changed, and the target compound CPD41-3 (23.02 g, yield: 95.98%) is obtained as a white solid, and the mass spectrometry characterization result is: 385.09 (M+H). The obtained compound is directly used in the next step without purification.

[0127] Synthesis of compound CPD41-4

[0128] Referring to the synthesis and purification method of compound CPD10-6, only the corresponding raw materials need to be changed, and the target compound CPD41-4 (18.08 g, mass fraction purity: 99.85%, yield: 60.63%) is obtained as a white solid, and the mass spectrometry characterization result is: 353.06 (M+H).

[0129] Synthesis of compound CPD41-5

[0130] The synthesis and purification method of reference compound CPD10-8 was referred to, only the corresponding raw materials were changed, and a white solid, target compound CPD41-5 was obtained (17.89 g, mass fraction purity: 99.03%, yield: 75.05%). The mass spectrometry characterization result was: 445.12 (M+H).

[0131] Synthesis of compound CPD41

[0132] The synthesis and purification method of reference compound CPD29 was referred to, only the corresponding raw materials were changed, and a yellow solid, target compound CPD41 was obtained (18.88 g, mass fraction purity: 99.96%, yield: 74.65%). After sublimation purification of 18.88 g of the crude CPD41, sublimation pure CPD41 was obtained (15.70 g, mass fraction purity: 99.96%, yield: 83.16%). The mass spectrometry characterization result was: 667.21 (M+H). The nuclear magnetic resonance characterization result was: 1 H NMR (400 MHz, CDCl3) δ 8.62 (d, J = 3.2 Hz, 1H), 8.61 (d, J = 2.1 Hz, 1H), 8.47 (d, J = 2.4 Hz, 1H), 8.13-7.99 (m, 6H), 7.99-7.88 (m, 5H), 7.74 (dd, J = 8.9, 1.2 Hz, 1H), 7.67-7.59 (m, 1H), 7.55-7.46 (m, 4H), 7.46-7.39 (m, 4H), 7.37-7.29 (m, 2H).

[0133] Synthesis of compound CPD59:

[0134] The synthesis route was:

[0135] The synthesis and purification method of reference compound CPD29 was referred to, only the corresponding raw materials were changed, and a yellow solid, target compound CPD59 was obtained (10.52 g, mass fraction purity: 99.93%, yield: 71.32%). After sublimation purification of 10.52 g of the crude CPD59, sublimation pure CPD59 was obtained (7.44 g, mass fraction purity: 99.96%, yield: 70.72%). The mass spectrometry characterization result was: 643.72 (M+H). The nuclear magnetic resonance characterization result was: 1H NMR (400 MHz, CDC13) δ 8.67 (d, J = 20.0 Hz, 24H), 8.36 (s, 13H), 8.17 (d, J = 17.2 Hz, 14H), 7.97 (d, J = 10.0 Hz, 22H), 7.87 (s, 2H), 7.87 - 7.50 (m, 58H), 7.54 (s, 22H), 7.44 (dt, J = 50.0, 30.0 Hz, 79H), 7.39 (s, 7H), 7.35 (d, J = 40.0 Hz, 24H), 7.31 (s, 4H), 7.25 (s, 17H).

[0136] Synthesis of compound CPD61

[0137] The synthesis route is as follows:

[0138] Synthesis of compound CPD61-1

[0139] Referring to the synthesis and purification method of compound CPD10-6, only the corresponding raw materials need to be changed, and the target compound CPD61-1 (12.65 g, mass fraction purity: 99.73%, yield: 40.06%) is obtained as a white solid. Mass spectrometry characterization result: 353.06 (M+H).

[0140] Synthesis of compound CPD61-2

[0141] Referring to the synthesis and purification method of compound CPD10-8, only the corresponding raw materials need to be changed, and the target compound CPD61-2 (14.87 g, mass fraction purity: 99.05%, yield: 77.96%) is obtained as a white solid. Mass spectrometry characterization result: 445.12 (M+H).

[0142] Synthesis of compound CPD61

[0143] Referring to the synthesis and purification method of compound CPD10, only the corresponding raw materials need to be changed, and the target compound CPD61 (14.63 g, mass fraction purity: 99.95%, yield: 75.06%) is obtained as a yellow solid. After sublimation purification of 14.63 g of crude CPD61, sublimed CPD61 (12.10 g, mass fraction purity: 99.95%, yield: 82.71%) is obtained. Mass spectrometry characterization result: 598.22 (M+H). Nuclear magnetic resonance characterization result: 1H NMR (400 MHz, CDC13) δ 8.64 - 8.58 (m, 3H), 8.36 (d, J = 2.4 Hz, 1H), 8.13 (t, J = 2.2 Hz, 1H), 8.03 - 7.92 (m, 8H), 7.92 - 7.76 (m, 4H), 7.67 - 7.62 (m, 1H), 7.62 - 7.47 (m, 4H), 7.47 - 7.37 (m, 5H).

[0144] Synthesis of compound CPD64

[0145] The synthetic route is as follows:

[0146] Referring to the synthesis and purification method of compound CPD29, only the corresponding raw materials need to be changed to obtain the target compound CPD64 (11.37 g, mass fraction purity: 99.94%, yield: 77.25%) as a yellow solid. After sublimation purification of 11.37 g of CPD64 crude product, sublimation pure CPD64 (7.81 g, mass fraction purity: 99.96%, yield: 68.68%) was obtained. Mass spectrometry characterization result: 763.81 (M+H). Nuclear magnetic resonance characterization results: 1 H NMR (400 MHz, CDC13) δ 8.64 - 8.58 (m, 3H), 8.36 (d, J = 2.4 Hz, 1H), 8.13 (t, J = 2.2 Hz, 1H), 8.03 - 7.92 (m, 8H), 7.92 - 7.76 (m, 4H), 7.67 - 7.62 (m, 1H), 7.62 - 7.47 (m, 4H), 7.47 - 7.37 (m, 5H).

[0147] Synthesis of compound CPD73

[0148] The synthetic route is as follows:

[0149] Synthesis of compound CPD73-2

[0150] Referring to the synthesis and purification method of compound CPD10, only the corresponding raw materials need to be changed to obtain the target compound CPD73-2 (24.25 g, mass fraction purity: 99.68%, yield: 78.08%) as a white solid. Mass spectrometry characterization result: 519.11 (M+H).

[0151] Synthesis of compound CPD73

[0152] CPD73-2 (20.00 g, 38.54 mmol), CPD73-3 (12.38 g, 38.54 mmol), bis(4- dimethylaminophenyl di-tert-butylphosphine) palladium dichloride (0.23 g, 0.38 mmol), potassium carbonate (10.65 g, 77.08 mmol), toluene (300 mL), ethanol (100 mL), deionized water (100 mL) were added into a 1000 mL three-necked round-bottom flask, which was purged with nitrogen for three times, then the system was heated to 65 °C for 2 hours, TLC (ethyl acetate: n-hexane = 1:10 as developing agent) was used to monitor the reaction, the raw material CPD73-2 was consumed completely;

[0153] The system was cooled to room temperature, methanol (300 mL) was added, stirred at room temperature for 1 hour, a large amount of solid was precipitated. Toluene (450 mL) was added, the system was heated to 100 °C to dissolve, then cooled to room temperature, filtered once with 200-300 mesh silica gel (20 g), the filtrate was added with methanol (450 mL) at room temperature, stirred at room temperature for 1 hour, suction filtered to obtain white solid wet product, which was dried at 100 °C for 1 hour to obtain light yellow solid; the light yellow solid was crystallized twice with toluene and methanol, suction filtered, and the filter cake was dried at 100 °C under vacuum for 10 hours to obtain yellow solid as CPD73 (15.62 g, mass fraction purity: 99.97%, yield: 68.88%). The 15.62 g of crude CPD73 was purified by sublimation to obtain sublimed pure CPD73 (12.88 g, mass fraction purity: 99.97%, yield: 82.45%), mass spectrometry characterization result: 678.24 (M+H). Nuclear magnetic resonance characterization result: 1 H NMR (400 MHz, CDCl3) δ 8.64-8.58 (m, 3H), 8.39 (d, J = 2.4 Hz, 1H), 8.23 (d, J = 2.4 Hz, 1H), 8.16 (d, J = 8.0 Hz, 1H), 8.01-7.86 (m, 8H), 7.80-7.75 (m, 2H), 7.70 (d, J = 2.0 Hz, 1H), 7.66-7.59 (m, 2H), 7.59-7.39 (m, 7H), 7.37 (d, J = 7.4 Hz, 1H).

[0154] Synthesis of compound CPD75

[0155] The synthesis route is as follows:

[0156] Synthesis of compound CPD75-3

[0157] The synthesis and purification method of reference compound CPD10-3 were referred to, only the corresponding raw materials were changed, and the target compound CPD75-3 was obtained as a white solid (28.63 g, mass fraction purity: 99.79%, yield: 76.84%). The mass spectrometry characterization result was: 291.02 (M+H).

[0158] Synthesis of compound CPD75

[0159] The synthesis and purification method of reference compound CPD73 were referred to, only the corresponding raw materials were changed, and the target compound CPD75 was obtained as a yellow solid (17.00 g, mass fraction purity: 99.95%, yield: 77.11%). After sublimation purification of 17.00 grams of the crude CPD75, sublimation pure CPD75 was obtained (13.45 g, mass fraction purity: 99.97%, yield: 79.12%). The mass spectrometry characterization result was: 573.20 (M+H). The nuclear magnetic resonance characterization result was: 1 H NMR (400 MHz, CDCl3) δ 8.93 (dd, J = 4.1, 2.1 Hz, 1H), 8.84 (dd, J = 3.9, 1.7 Hz, 1H), 8.64-8.58 (m, 3H), 8.39 (d, J = 2.3 Hz, 1H), 8.33 (dd, J = 7.6, 2.1 Hz, 1H), 8.27 (d, J = 2.3 Hz, 1H), 8.10-8.08 (m, 1H), 8.01-7.93 (m, 4H), 7.89 (d, J = 9.2 Hz, 1H), 7.82-7.74 (m, 2H), 7.67-7.59 (m, 1H), 7.59-7.49 (m, 5H), 7.47-7.38 (m, 2H).

[0160] Synthesis of compound CPD76

[0161] The synthesis route was:

[0162] Synthesis of compound CPD76

[0163] The synthesis and purification method of reference compound CPD10 were referred to, only the corresponding raw materials were changed, and the target compound CPD76 was obtained as a yellow solid (15.00 g, mass fraction purity: 99.96%, yield: 75.77%). After sublimation purification of 15.00 grams of the crude CPD76, sublimation pure CPD76 was obtained (12.11 g, mass fraction purity: 99.96%, yield: 80.73%). The mass spectrometry characterization result was: 546.12 (M+H). The nuclear magnetic resonance characterization result was: 1H NMR (400 MHz, CDC13) δ 8.82 (dd, J = 4.1, 2.1 Hz, 1H), 8.64 - 8.58 (m, 4H), 8.54 (dd, J = 5.7, 3.1 Hz, 1H), 8.39 (d, J = 2.5 Hz, 1H), 8.28 (d, J = 2.3 Hz, 1H), 8.19 - 8.12 (m, 1H), 8.04 (d, J = 8.3 Hz, 1H), 8.01 - 7.93 (m, 4H), 7.89 (d, J = 9.4 Hz, 1H), 7.80 - 7.77 (m, 2H), 7.67 - 7.60 (m, 1H), 7.57 - 7.38 (m, 5H).

[0164] Synthesis of compound CPD78

[0165] The synthetic route is:

[0166] Synthesis of compound CPD78

[0167] Referring to the synthesis and purification method of compound CPD10, only the corresponding raw materials need to be changed, and the target compound CPD78 is obtained as a yellow solid (16.33 g, mass fraction purity: 99.97%, yield: 76.52%). After sublimation purification of 16.33 g of CPD78 crude product, sublimation pure CPD78 (13.15 g, mass fraction purity: 99.97%, yield: 80.52%) was obtained. Mass spectrometry characterization results: 655.16 (M+H). Nuclear magnetic resonance characterization results: 1 H NMR (400 MHz, CDC13) δ 8.82 (dd, J = 4.1, 2.1 Hz, 1H), 8.64 - 8.58 (m, 4H), 8.54 (dd, J = 5.7, 3.1 Hz, 1H), 8.39 (d, J = 2.5 Hz, 1H), 8.28 (d, J = 2.3 Hz, 1H), 8.19 - 8.12 (m, 1H), 8.04 (d, J = 8.3 Hz, 1H), 8.01 - 7.93 (m, 4H), 7.89 (d, J = 9.4 Hz, 1H), 7.80 - 7.77 (m, 2H), 7.67 - 7.60 (m, 1H), 7.57 - 7.38 (m, 5H).

[0168] Synthesis of compound CPD92

[0169] The synthetic route is:

[0170] Synthesis of compound CPD92-1

[0171] The synthesis and purification method of reference compound CPD10-6 were referred to, only the corresponding raw materials were changed, and the target compound CPD92-1 was obtained as a white solid (16.77 g, mass fraction purity: 99.81%, yield: 40.00%). Mass spectrometry characterization result: 353.06 (M+H).

[0172] Synthesis of compound CPD92-2

[0173] The synthesis and purification method of reference compound CPD10-8 were referred to, only the corresponding raw materials were changed, and the target compound CPD92-2 was obtained as a white solid (14.00 g, mass fraction purity: 99.02%, yield: 78.06%). Mass spectrometry characterization result: 445.12 (M+H).

[0174] Synthesis of compound CPD92

[0175] The synthesis and purification method of reference compound CPD29 were referred to, only the corresponding raw materials were changed, and the target compound CPD92 was obtained as a yellow solid (16.55 g, mass fraction purity: 99.95%, yield: 78.65%). After sublimation purification of 16.55 g of the crude CPD92, sublimed CPD92 was obtained (13.24 g, mass fraction purity: 99.95%, yield: 80.00%). Mass spectrometry characterization result: 702.24 (M+H). Nuclear magnetic resonance characterization result: 1 H NMR (400 MHz, CDCl3) δ 8.61 (dd, J = 10.6, 9.1 Hz, 2H), 8.47 (d, J = 2.5 Hz, 1H), 8.17 (dd, J = 9.1, 2.5 Hz, 1H), 8.12-8.05 (m, 4H), 8.05-7.98 (m, 1H), 7.98-7.90 (m, 3H), 7.87 (d, J = 9.0 Hz, 1H), 7.78 (s, 1H), 7.67-7.60 (m, 2H), 7.58-7.56 (m, 4H), 7.55-7.45 (m, 3H), 7.43-7.39 (m, 8H).

[0176] Synthesis of compound CPD103

[0177] The synthesis route is:

[0178] Synthesis of compound CPD103

[0179] The synthesis and purification method of reference compound CPD29 was referred to, only the corresponding raw materials were changed, and yellow solid target compound CPD103 (15.33 g, mass fraction purity: 99.96%, yield: 78.33%) was obtained. After sublimation purification of 15.33 g of the crude CPD103, sublimed CPD103 (12.84 g, mass fraction purity: 99.96%, yield: 83.76%) was obtained, and the mass spectrometry characterization result was: 690.22 (M+H). The nuclear magnetic resonance characterization result was: 1 H NMR (400 MHz, CDC13) δ 8.64 - 8.54 (m, 3H), 8.47 (d, J = 2.4 Hz, 1H), 8.17 (dd, J = 9.1, 2.4 Hz, 1H), 8.12 - 8.08 (m, 3H), 8.08 - 8.06 (m, 2H), 8.06 - 7.95 (m, 4H), 7.93 (d, J = 9.2 Hz, 1H), 7.84 (d, J = 9.9 Hz, 1H), 7.78 (s, 1H), 7.67 - 7.59 (m, 2H), 7.55 - 7.45 (m, 3H), 7.45 - 7.38 (m, 4H), 7.32 (d, J = 7.3 Hz, 1H).

[0180] Synthesis of compound CPD125

[0181] The synthesis route is:

[0182] Synthesis of compound CPD125-2

[0183] The synthesis and purification method of reference compound CPD10-3 was referred to, only the corresponding raw materials were changed, and white solid target compound CPD125-2 (25.63 g, mass fraction purity: 99.52%, yield: 77.62%) was obtained, and the mass spectrometry characterization result was: 357.06 (M+H).

[0184] Synthesis of compound CPD125-3

[0185] The synthesis and purification method of reference compound CPD10-5 was referred to, only the corresponding raw materials were changed, and white solid target compound CPD125-3 (22.11 g, yield: 96.33%, mass spectrum: 385.09 (M+H)) was obtained. The obtained compound was directly used in the next step without purification.

[0186] Synthesis of compound CPD125-4

[0187] The synthesis and purification method of reference compound CPD10-6 were referred to, only the corresponding raw materials were changed, and the target compound CPD125-4 was obtained as a white solid (16.85 g, mass fraction purity: 99.82%, yield: 75.62%).

[0188] Synthesis of compound CPD125-5

[0189] The synthesis and purification method of reference compound CPD10-8 were referred to, only the corresponding raw materials were changed, and the target compound CPD125-5 was obtained as a white solid (16.74 g, mass fraction purity: 99.25%, yield: 76.76%).

[0190] Synthesis of compound CPD125

[0191] The synthesis and purification method of reference compound CPD10 were referred to, only the corresponding raw materials were changed, and the target compound CPD125 was obtained as a yellow solid (15.25 g, mass fraction purity: 99.95%, yield: 75.80%). After sublimation purification of 15.25 g of the crude CPD125, sublimed CPD125 (12.20 g, mass fraction purity: 99.95%, yield: 80.00%) was obtained. Mass spectrometry characterization result: 587.24 (M+H). Nuclear magnetic resonance characterization result: 1 H NMR (400 MHz, CDCl3) δ 8.61 (dd, J = 8.5, 5.7 Hz, 2H), 8.26 (d, J = 9.0 Hz, 1H), 8.12-8.03 (m, 2H), 8.01-7.93 (m, 4H), 7.90 (d, J = 7.1 Hz, 1H), 7.83-7.76 (m, 2H), 7.66-7.57 (m, 4H), 7.57-7.46 (m, 5H), 7.46-7.39 (m, 4H), 7.32 (d, J = 7.3 Hz, 1H).

[0192] Synthesis of compound CPD128

[0193] The synthesis route is:

[0194] Synthesis of compound CPD128-2

[0195] The synthesis and purification method of reference compound CPD10-3 were referred to, only the corresponding raw materials were changed, and the target compound CPD128-2 was obtained as a white solid (20.58 g, mass fraction purity: 99.83%, yield: 74.62%). Mass spectrometry characterization result: 306.27 (M+H).

[0196] Synthesis of compound CPD128

[0197] The synthesis and purification process of reference compound CPD73 was referred to, only the corresponding raw materials were changed, and yellow solid target compound CPD128 (16.45 g, mass fraction purity: 99.96%, yield: 76.52%) was obtained. After sublimation purification of 16.45 g of CPD128 crude product, sublimation pure CPD128 (13.01 g, mass fraction purity: 99.96%, yield: 79.09%) was obtained, and the mass spectrometry characterization result was: 588.42 (M+H). The nuclear magnetic characterization result was: 1 H NMR (400 MHz, CDCl3) δ 8.61 (dd, J = 8.5, 5.7 Hz, 2H), 8.38 (dd, J = 9.8, 2.2 Hz, 2H), 8.26 (d, J = 9.0 Hz, 1H), 8.12-8.04 (m, 1H), 8.02-7.96 (m, 3H), 7.95-7.93 (m, 3H), 7.90 (d, J = 7.1 Hz, 1H), 7.82-7.76 (m, 2H), 7.63 (dd, J = 3.8, 2.4 Hz, 1H), 7.62-7.54 (m, 4H), 7.52-7.38 (m, 4H), 7.32 (d, J = 7.3 Hz, 1H).

[0198] Synthesis of compound CPD159

[0199] The synthesis route is:

[0200] Synthesis of compound CPD159

[0201] The synthesis and purification process of reference compound CPD29 was referred to, only the corresponding raw materials were changed, and yellow solid target compound CPD159 (17.62 g, mass fraction purity: 99.96%, yield: 77.77%) was obtained. After sublimation purification of 17.62 g of CPD159 crude product, sublimation pure CPD159 (14.43 g, mass fraction purity: 99.96%, yield: 81.90%) was obtained, and the mass spectrometry characterization result was: 640.19 (M+H). The nuclear magnetic characterization result was: 1H NMR (400 MHz, CDC13) δ 8.61 (dd, J = 8.5, 2.1 Hz, 2H), 8.47 (d, J = 2.4 Hz, 1H), 8.26 (d, J = 9.0 Hz, 1H), 8.12 - 8.06 (m, 4H), 8.06 - 7.94 (m, 3H), 7.92 - 7.84 (m, 2H), 7.67 - 7.59 (m, 2H), 7.58 - 7.45 (m, 4H), 7.45 - 7.38 (m, 4H), 7.32 (d, J = 7.3 Hz, 1H), 7.26 (dd, J = 9.3, 6.8 Hz, 1H).

[0202] Synthesis of compound CPD186

[0203] The synthesis route is as follows:

[0204] Synthesis of compound CPD186-2

[0205] Referring to the synthesis and purification method of compound CPD10-3, only the corresponding raw materials need to be changed, and the target compound CPD186-2 (25.33 g, mass fraction purity: 99.32%, yield: 77.85%) is obtained as a white solid. The mass spectrometry characterization result is: 357.06 (M+H).

[0206] Synthesis of compound CPD186-3

[0207] Referring to the synthesis and purification method of compound CPD10-5, only the corresponding raw materials need to be changed, and the target compound CPD186-3 (22.44 g, yield: 96.69%) is obtained as a white solid. The mass spectrometry characterization result is: 385.09 (M+H). The obtained compound is directly used in the next step without purification.

[0208] Synthesis of compound CPD186-4

[0209] Referring to the synthesis and purification method of compound CPD10-6, only the corresponding raw materials need to be changed, and the target compound CPD186-4 (19.87 g, mass fraction purity: 99.89%, yield: 80.06%) is obtained as a white solid. The mass spectrometry characterization result is: 353.06 (M+H).

[0210] Synthesis of compound CPD186-5

[0211] The synthesis and purification method of reference compound CPD10-8 was referred to, only the corresponding raw materials were changed, and the target compound CPD186-5 was obtained as a white solid (18.09 g, mass fraction purity: 99.24%, yield: 75.67%). The mass spectrometry characterization result was: 445.12 (M+H).

[0212] Synthesis of compound CPD186

[0213] The synthesis and purification method of reference compound CPD29 was referred to, only the corresponding raw materials were changed, and the target compound CPD186 was obtained as a yellow solid (15.96 g, mass fraction purity: 99.95%, yield: 75.90%). After sublimation purification of 15.96 g of the crude CPD186, sublimation pure CPD186 was obtained (12.11 g, mass fraction purity: 99.95%, yield: 75.87%). The mass spectrometry characterization result was: 802.21 (M+H). The nuclear magnetic resonance characterization result was: 1 H NMR (400 MHz, CDCl3) δ 8.66 (d, J = 9.1 Hz, 1H), 8.47 (d, J = 2.4 Hz, 1H), 8.32 (d, J = 8.1 Hz, 1H), 8.17 (d, J = 8.1 Hz, 1H), 8.14-8.05 (m, 4H), 8.05-7.94 (m, 3H), 7.94-7.90 (m, 4H), 7.90-7.79 (m, 6H), 7.69-7.59 (m, 6H), 7.58-7.48 (m, 6H), 7.48-7.38 (m, 2H).

[0214] Synthesis of compound CPD201

[0215] The synthesis route was:

[0216] Synthesis of compound CPD201-2

[0217] The synthesis and purification method of reference compound CPD10 was referred to, only the corresponding raw materials were changed, and the target compound CPD201-2 was obtained as a white solid (22.65 g, mass fraction purity: 99.69%, yield: 79.08%). The mass spectrometry characterization result was: 479.12 (M+H).

[0218] Synthesis of compound CPD201-3

[0219] The synthesis and purification method of reference compound CPD10-8 was referred to, only the corresponding raw materials were changed, and the target compound CPD201-3 was obtained as a white solid (20.01 g, mass fraction purity: 99.03%, yield: 76.65%). The mass spectrometry characterization result was: 571.24 (M+H).

[0220] Synthesis of compound CPD201

[0221] The synthesis and purification method of reference compound CPD29 was referred to, only the corresponding raw materials were changed, and yellow solid target compound CPD201 (17.76 g, mass fraction purity: 99.96%, yield: 76.63%) was obtained. After sublimation purification of 17.76 g of CPD201 crude product, sublimation pure CPD201 (14.62 g, mass fraction purity: 99.96%, yield: 82.31%) was obtained. Mass spectrometry characterization result: 676.23 (M+H). Nuclear magnetic resonance characterization result: 1 H NMR (400 MHz, CDC13) δ 8.65 (d, J = 9.0 Hz, 1H), 8.39 (d, J = 2.4 Hz, 1H), 8.32 (d, J = 8.0 Hz, 1H), 8.24 (t, J = 2.2 Hz, 1H), 8.17 (d, J = 8.0 Hz, 1H), 8.14 - 8.01 (m, 7H), 8.01 - 7.92 (m, 4H), 7.79 (dd, J = 8.1, 2.4 Hz, 1H), 7.70 (dd, J = 9.3, 2.1 Hz, 1H), 7.68 - 7.57 (m, 3H), 7.54 - 7.46 (m, 6H), 7.46 - 7.38 (m, 2H).

[0222] Synthesis of compound CPD214

[0223] The synthesis route is:

[0224] Synthesis of compound CPD214-2

[0225] The synthesis and purification method of reference compound CPD10-3 was referred to, only the corresponding raw materials were changed, and white solid target compound CPD214-2 (25.06 g, mass fraction purity: 99.32%, yield: 72.53%) was obtained. Mass spectrometry characterization result: 505.12 (M+H).

[0226] Synthesis of compound CPD214-3

[0227] The synthesis and purification method of reference compound CPD10-5 was referred to, only the corresponding raw materials were changed, and white solid target compound CPD214-3 (22.55 g, yield: 94.96%) was obtained. Mass spectrometry characterization result: 533.14 (M+H). The obtained compound was directly used in the next step without purification.

[0228] Synthesis of compound CPD214-4

[0229] The synthesis and purification method of reference compound CPD10-6 were referred to, only the corresponding raw materials were changed, and the target compound CPD214-4 was obtained as a white solid (19.88 g, mass fraction purity: 99.87%, yield: 78.69%).

[0230] Synthesis of compound CPD214-5

[0231] The synthesis and purification method of reference compound CPD10-8 were referred to, only the corresponding raw materials were changed, and the target compound CPD214-5 was obtained as a white solid (18.06 g, mass fraction purity: 99.33%, yield: 77.62%).

[0232] Synthesis of compound CPD214

[0233] The synthesis and purification method of reference compound CPD29 were referred to, only the corresponding raw materials were changed, and the target compound CPD214 was obtained as a yellow solid (17.66 g, mass fraction purity: 99.96%, yield: 76.52%). After sublimation purification of 17.66 g of the crude CPD214, sublimed CPD214 (14.98 g, mass fraction purity: 99.96%, yield: 84.83%) was obtained. Mass spectrometry characterization result: 698.26 (M+H). Nuclear magnetic resonance characterization result: 1 H NMR (400 MHz, CDCl3) δ 8.60 (d, J = 8.9 Hz, 1H), 8.50 (d, J = 8.1 Hz, 1H), 8.47 (d, J = 2.4 Hz, 1H), 8.34 (dd, J = 6.9, 1.3 Hz, 1H), 8.25 (d, J = 8.9 Hz, 1H), 8.16 (d, J = 7.5 Hz, 1H), 8.13-8.05 (m, 5H), 8.05-7.94 (m, 7H), 7.88 (d, J = 7.6 Hz, 1H), 7.58-7.42 (m, 12H).

[0234] Synthesis of compound CPD215

[0235] The synthesis route is as follows:

[0236] Synthesis of compound CPD215-2

[0237] The synthesis and purification method of reference compound CPD10-3 were referred to, only the corresponding raw materials were changed, and the target compound CPD215-2 was obtained as a white solid (24.22 g, mass fraction purity: 99.06%, yield: 73.09%). Mass spectrometry characterization result: 432.11 (M+H).

[0238] Synthesis of compound CPD215-3

[0239] Refer to the synthesis and purification method of compound CPD10-5, only need to change the corresponding raw material, the target compound CPD215-3 (23.66g, yield: 96.06%) was obtained as a white solid, mass spectrometry characterization results: 460.12 (M+H). The obtained compound was directly used in the next step without purification.

[0240] Synthesis of compound CPD215-4

[0241] Refer to the synthesis and purification method of compound CPD10-6, only need to change the corresponding raw material, the target compound CPD215-4 (21.63g, mass fraction purity: 99.75%, yield: 77.01%) was obtained as a white solid, mass spectrometry characterization results: 428.11 (M+H).

[0242] Synthesis of compound CPD215-5

[0243] Refer to the synthesis and purification method of compound CPD10-8, only need to change the corresponding raw material, the target compound CPD215-5 (19.88g, mass fraction purity: 99.21%, yield: 78.74%) was obtained as a white solid, mass spectrometry characterization results: 520.24 (M+H).

[0244] Synthesis of compound CPD215

[0245] Refer to the synthesis and purification method of compound CPD29, only need to change the corresponding raw material, the target compound CPD215 (18.06g, mass fraction purity: 99.97%, yield: 77.08%) was obtained as a yellow solid. After sublimation purification of 18.06 grams of CPD215 crude product, sublimation pure CPD215 (15.09g, mass fraction purity: 99.97%, yield: 83.56%) was obtained, mass spectrometry characterization results: 653.26 (M+H). Nuclear magnetic resonance characterization results: 1H NMR (400 MHz, CDC13) δ 8.60 (d, J = 9.0 Hz, 1H), 8.52 (d, J = 8.1 Hz, 1H), 8.47 (d, J = 2.5 Hz, 1H), 8.36 (dd, J = 7.0, 1.4 Hz, 1H), 8.28 - 8.22 (m, 1H), 8.10 (d, J = 2.4 Hz, 1H), 8.10 - 7.94 (m, 4H), 7.88 - 7.82 (m, 4H), 7.54 (dd, J = 6.3, 1.6 Hz, 1H), 7.44 - 7.41 (m, 1H), 7.34 - 7.25 (m, 7H), 7.22 - 7.13 (m, 3H), 2.36 (s, 6H).

[0246] Synthesis of compound CPD222

[0247] The synthesis route is as follows:

[0248] Synthesis of compound CPD222-3

[0249] Referring to the synthesis and purification method of compound CPD10-3, only the corresponding raw materials need to be changed, and the target compound CPD222-3 (21.11 g, mass fraction purity: 99.09%, yield: 75.96%) is obtained as a white solid. Mass spectrometry characterization result: 357.06 (M+H).

[0250] Synthesis of compound CPD222-4

[0251] Referring to the synthesis and purification method of compound CPD10-5, only the corresponding raw materials need to be changed, and the target compound CPD222-4 (20.00 g, yield: 94.52%) is obtained as a white solid. Mass spectrometry characterization result: 385.09 (M+H). The obtained compound is directly used in the next step without purification.

[0252] Synthesis of compound CPD224-5

[0253] Referring to the synthesis and purification method of compound CPD10-6, only the corresponding raw materials need to be changed, and the target compound CPD224-5 (18.06 g, mass fraction purity: 99.70%, yield: 74.65%) is obtained as a white solid. Mass spectrometry characterization result: 353.07 (M+H).

[0254] Synthesis of compound CPD222-6

[0255] The synthesis and purification method of reference compound CPD10-8 was referred to, only the corresponding raw materials were changed, and the target compound CPD222-6 was obtained in the form of a white solid (17.68 g, mass fraction purity: 99.42%, yield: 76.78%). Mass spectrometry characterization result: 445.20 (M+H).

[0256] Synthesis of compound CPD222

[0257] The synthesis and purification method of reference compound CPD29 was referred to, only the corresponding raw materials were changed, and the target compound CPD222 was obtained in the form of a yellow solid (17.11 g, mass fraction purity: 99.95%, yield: 71.56%). After sublimation purification of 17.11 g of the crude CPD222, sublimed CPD222 (14.33 g, mass fraction purity: 99.95%, yield: 83.76%) was obtained. Mass spectrometry characterization result: 900.40 (M+H). Nuclear magnetic resonance characterization result: 1 H NMR (400 MHz, CDCl3) δ 8.60 (d, J = 8.1 Hz, 1H), 8.40-8.36 (m, 1H), 8.35 (d, J = 2.1 Hz, 1H), 8.33 (d, J = 2.2 Hz, 2H), 8.31-8.23 (m, 4H), 8.15 (dd, J = 9.2, 1.5 Hz, 1H), 8.13-8.06 (m, 3H), 8.06-8.02 (m, 3H), 8.02-7.97 (m, 3H), 7.63-7.55 (m, 2H), 7.54-7.46 (m, 5H), 7.46-7.37 (m, 3H), 7.34 (dd, J = 7.7, 2.2 Hz, 2H), 1.33 (s, 18H).

[0258] Synthesis of compound CPD264

[0259] The synthesis route is as follows:

[0260] Synthesis of compound CPD264-3

[0261] CPD264-1 (20.00 g, 80.94 mmol), CPD264-2 (20.85 g, 84.99 mmol), tris(dibenzylideneacetone)dipalladium (1.48 g, 1.62 mmol), 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (1.55 g, 3.24 mmol), sodium tert-butoxide (11.66 g, 121.41 mmol), toluene (300 ml) were charged into a 1000 ml three-necked round-bottom flask, and the system was replaced with nitrogen three times, then the system was heated to 90°C for 6 hours, and the reaction was monitored by TLC (ethyl acetate: n-hexane = 1:15 as developing agent). The raw material CPD264-1 was consumed.

[0262] The temperature was lowered to 60°C, methanol (300 ml) was added, and the system was stirred at room temperature for 30 minutes to precipitate a large amount of solid. Filtration was performed to obtain 35 g of solid. Toluene (700 ml) was added, and then the system was heated to 100°C to dissolve and clarify. 50 g (300-400 mesh) of silica gel was laid on the surface of the silica gel, and the system was filtered. Toluene (100 ml) was used to rinse the surface of the silica gel, and the filtrate was concentrated to obtain 33 g. Crystallization was performed twice using toluene (330 ml) and methanol (150 ml). Filtration was performed, and the filter cake was dried at 90°C under vacuum for 3 hours to obtain CPD264-3 (29.45 g, mass fraction purity: 99.94%, yield: 88.42%) as a light yellow solid. Mass spectrometry characterization result: 412.16 (M+H).

[0263] Synthesis of compound CPD264

[0264] Referring to the synthesis and purification method of compound CPD264-3, only the corresponding raw material needs to be changed to obtain the target compound CPD264 (19.87 g, mass fraction purity: 99.96%, yield: 78.74%) as a yellow solid. After sublimation purification of 19.87 g of CPD264 crude product, sublimation pure CPD264 (16.00 g, mass fraction purity: 99.96%, yield: 80.53%) was obtained. Mass spectrometry characterization result: 728.25 (M+H). Nuclear magnetic resonance characterization result: 1H NMR (400 MHz, CDC13) δ 8.62 (d, J = 9.3 Hz, 1H), 8.34 (d, J = 9.7 Hz, 1H), 8.20 (d, J = 9.7 Hz, 1H), 8.12 - 7.97 (m, 5H), 7.91 (d, J = 7.6 Hz, 1H), 7.83 (d, J = 2.2 Hz, 1H), 7.75 - 7.68 (m, 3H), 7.67 - 7.59 (m, 2H), 7.59 - 7.55 (m, 2H), 7.55 - 7.42 (m, 7H), 7.45 - 7.391 (m, 5H), 7.31 (dd, J = 7.6, 2.1 Hz, 1H), 6.97 - 6.86 (m, 3H).

[0265] Synthesis of compound CPD287

[0266] The synthetic route is as follows:

[0267] Synthesis of compound CPD287-1

[0268] Referring to the synthesis and purification method of compound CPD10, only the corresponding raw materials need to be changed, and the target compound CPD287-1 (23.65 g, mass fraction purity: 99.82%, yield: 76.75%) is obtained as a white solid. Mass spectrometry characterization result: 479.12 (M+H).

[0269] Synthesis of compound CPD287

[0270] Referring to the synthesis and purification method of compound CPD264, only the corresponding raw materials need to be changed, and the target compound CPD287 (17.77 g, mass fraction purity: 99.96%, yield: 75.96%) is obtained as a yellow solid. After sublimation purification of 17.77 grams of CPD287 crude product, sublimation pure CPD287 (14.52 g, mass fraction purity: 99.96%, yield: 81.71%) is obtained. Mass spectrometry characterization result: 736.26 (M+H). Nuclear magnetic resonance characterization result: 1 H NMR (400 MHz, CDC13) δ 8.62 (d, J = 9.3 Hz, 1H), 8.34 (d, J = 9.7 Hz, 1H), 8.20 (d, J = 9.7 Hz, 1H), 8.12 - 7.97 (m, 5H), 7.91 (d, J = 7.6 Hz, 1H), 7.83 (d, J = 2.2 Hz, 1H), 7.75 - 7.68 (m, 3H), 7.67 - 7.59 (m, 2H), 7.59 - 7.55 (m, 2H), 7.55 - 7.42 (m, 7H), 7.45 - 7.391 (m, 5H), 7.31 (dd, J = 7.6, 2.1 Hz, 1H), 6.97 - 6.86 (m, 3H).

[0271] Synthesis of compound CPD296

[0272] The synthetic route is as follows:

[0273] Synthesis of compound CPD296

[0274] Referring to the synthesis and purification method of compound CPD264, only the corresponding raw materials need to be changed, and the target compound CPD296 is obtained as a yellow solid (22.63 g, mass fraction purity: 99.97%, yield: 76.96%). After sublimation purification of 22.63 grams of CPD296 crude product, sublimation pure CPD296 (19.74 g, mass fraction purity: 99.96%, yield: 87.23%) is obtained. Mass spectrometry characterization result: 562.22 (M+H). Nuclear magnetic resonance characterization result: 1 H NMR (400 MHz, CDCI3) δ 8.64-8.58 (m, 3H), 8.01-7.95 (m, 4H), 7.95-7.88 (m, 1H), 7.73 (d, J = 2.0 Hz, 1H), 7.67-7.59 (m, 1H), 7.59-7.50 (m, 4H), 7.47-7.37 (m, 5H), 7.32-7.24 (m, 2H), 7.17-7.11 (m, 2H), 7.11-7.06 (m, 1H), 7.03-6.97 (m, 2H), 6.90-6.88 (m, 1H).

[0275] Synthesis of compound CPD308

[0276] The synthetic route is as follows:

[0277] Synthesis of compound CPD308-2

[0278] Referring to the synthesis and purification method of compound CPD10-8, only the corresponding raw materials need to be changed, and the target compound CPD308-2 is obtained as a white solid (25.66 g, mass fraction purity: 99.06%, yield: 78.06%). Mass spectrometry characterization result: 371.11 (M+H).

[0279] Synthesis of compound CPD308-3

[0280] Referring to the synthesis and purification method of compound CPD10-3, only the corresponding raw materials need to be changed, and the target compound CPD308-3 is obtained as a white solid (22.62 g, mass fraction purity: 99.34%, yield: 75.00%). Mass spectrometry characterization result: 433.08 (M+H).

[0281] Synthesis of compound CPD308-4

[0282] The synthesis and purification process of reference compound CPD10-5 was referred to, only the corresponding raw materials were changed, and the target compound CPD308-4 was obtained as a white solid (20.00 g, yield: 96.06%), mass spectrometry characterization result: 461.12 (M+H). The obtained compound was directly used in the next step without purification.

[0283] Synthesis of compound CPD308-5

[0284] The synthesis and purification process of reference compound CPD10-6 was referred to, only the corresponding raw materials were changed, and the target compound CPD308-5 was obtained as a white solid (16.77 g, mass fraction purity: 99.77%, yield: 60.03%), mass spectrometry characterization result: 429.11 (M+H).

[0285] Synthesis of compound CPD308

[0286] The synthesis and purification process of reference compound CPD264 was referred to, only the corresponding raw materials were changed, and the target compound CPD308 was obtained as a yellow solid (15.68 g, mass fraction purity: 99.96%, yield: 75.84%). After sublimation purification of 15.68 g of the crude CPD308, sublimed CPD308 was obtained (12.86 g, mass fraction purity: 99.96%, yield: 82.02%), mass spectrometry characterization result: 638.24 (M+H). Nuclear magnetic resonance characterization result: 1 H NMR (400 MHz, CDCl3) δ 8.67-8.59 (m, 3H), 8.01-7.94 (m, 2H), 7.91 (d, J = 7.7 Hz, 1H), 7.78 (d, J = 2.1 Hz, 1H), 7.73 (d, J = 2.0 Hz, 1H), 7.65 (dd, J = 7.5, 1.1 Hz, 1H), 7.61-7.49 (m, 7H), 7.42-7.39 (m, 6H), 7.35-7.23 (m, 3H), 7.17-7.06 (m, 3H), 7.03-6.97 (m, 2H), 6.90-6.88 (m, 1H).

[0287] Synthesis of compound CPD341

[0288] The synthesis route is:

[0289] Synthesis of compound CPD341-2

[0290] The synthesis and purification method of reference compound CPD10-3 were referred to, only the corresponding raw materials were changed, and the target compound CPD341-2 was obtained in the form of white solid (24.44 g, mass fraction purity: 99.62%, yield: 77.96%).

[0291] Synthesis of compound CPD341-3

[0292] The synthesis and purification method of reference compound CPD10-5 were referred to, only the corresponding raw materials were changed, and the target compound CPD341-3 was obtained in the form of white solid (23.82 g, yield: 95.55%), and the mass spectrometry characterization result was 411.14 (M+H). The obtained compound was directly used in the next step without purification.

[0293] Synthesis of compound CPD341-4

[0294] The synthesis and purification method of reference compound CPD10-6 were referred to, only the corresponding raw materials were changed, and the target compound CPD341-4 was obtained in the form of white solid (21.21 g, mass fraction purity: 99.75%, yield: 60.15%), and the mass spectrometry characterization result was 379.12 (M+H).

[0295] Synthesis of compound CPD341

[0296] The synthesis and purification method of reference compound CPD264 were referred to, only the corresponding raw materials were changed, and the target compound CPD341 was obtained in the form of yellow solid (17.67 g, mass fraction purity: 99.96%, yield: 76.15%). After sublimation purification of 17.67 g of the crude CPD341, sublimation pure CPD341 was obtained in the form of white solid (15.00 g, mass fraction purity: 99.96%, yield: 84.89%), and the mass spectrometry characterization result was 588.26 (M+H). The nuclear magnetic resonance characterization result was: 1 H NMR (400 MHz, CDCl3) δ 8.83 (s, 1H), 8.64-8.57 (m, 2H), 8.53 (d, J = 2.4 Hz, 1H), 8.17 (dd, J = 8.9, 2.3 Hz, 1H), 8.01-7.96 (m, 1H), 7.92-7.90 (m, 2H), 7.73 (d, J = 2.0 Hz, 1H), 7.61-7.44 (m, 6H), 7.42-7.37 (m, 3H), 7.37-7.33 (m, 1H), 7.32-7.24 (m, 2H), 7.17-7.11 (m, 2H), 7.11-7.06 (m, 1H), 7.03-6.97 (m, 2H), 6.89 (dd, J = 7.4, 2.1 Hz, 1H), 1.74 (s, 6H).

[0297] Synthesis of compound CPD346

[0298] The synthetic route is as follows:

[0299] Synthesis of compound CPD346

[0300] The synthesis and purification method of reference compound CPD264 is used, and only the corresponding raw materials are changed to obtain the target compound CPD346 (18.26 g, mass fraction purity: 99.98%, yield: 77.86%) in the form of a yellow solid. After sublimation purification of 18.26 g of the crude CPD346, sublimation pure CPD346 (15.25 g, mass fraction purity: 99.96%, yield: 83.52%) is obtained, and the mass spectrometry characterization result is: 562.22 (M+H). The nuclear magnetic resonance characterization result is: 1 H NMR (400 MHz, CDCl3) δ 9.07 (d, J = 9.0 Hz, 1H), 8.70 (d, J = 8.0 Hz, 1H), 8.54 (s, 1H), 8.40 (d, J = 8.9 Hz, 1H), 8.02-7.94 (m, 4H), 7.89 (d, J = 8.7 Hz, 1H), 7.74 (d, J = 8.2 Hz, 1H), 7.63 (d, J = 8.1 Hz, 2H), 7.58-7.40 (m, 7H), 7.37-7.26 (m, 7H), 7.12 (t, J = 7.2 Hz, 1H).

[0301] Figure 1 is a1H NMR spectrum of the compound CPD346 of the present application. 1 The "f1" in Figure 1 represents the chemical shift.

[0302] Synthesis of compound CPD353

[0303] The synthetic route is as follows:

[0304] Synthesis of compound CPD353

[0305] The synthesis and purification method of reference compound CPD264 is used, and only the corresponding raw materials are changed to obtain the target compound CPD353 (19.87 g, mass fraction purity: 99.97%, yield: 76.67%) in the form of a yellow solid. After sublimation purification of 19.87 g of the crude CPD353, sublimation pure CPD353 (16.01 g, mass fraction purity: 99.96%, yield: 80.58%) is obtained, and the mass spectrometry characterization result is: 652.24 (M+H). The nuclear magnetic resonance characterization result is: 1H NMR (400 MHz, CDC13) δ 8.61 (dd, J = 8.5, 2.1 Hz, 2H), 8.26 (d, J = 9.0 Hz, 1H), 8.16 - 8.10 (m, 2H), 8.10 - 8.05 (m, 1H), 8.00 - 7.96 (m, 1H), 7.96 - 7.87 (m, 2H), 7.73 (d, J = 2.0 Hz, 1H), 7.67 - 7.60 (m, 2H), 7.60 - 7.52 (m, 2H), 7.49 - 7.47 (m, 1H), 7.45 - 7.37 (m, 7H), 7.37 - 7.30 (m, 2H), 7.14 - 7.05 (m, 2H), 7.05 - 6.99 (m, 2H), 6.89 (dd, J = 7.5, 2.2 Hz, 1H).

[0306] Synthesis of compound CPD377

[0307] The synthesis route is as follows:

[0308] Synthesis of compound CPD377-2

[0309] Referring to the synthesis and purification method of compound CPD10-3, only the corresponding raw materials need to be changed, and the target compound CPD377-2 (24.52 g, mass fraction purity: 99.02%, yield: 77.62%) is obtained as a white solid, and the mass spectrometry characterization result is: 373.04 (M+H).

[0310] Synthesis of compound CPD377-3

[0311] Referring to the synthesis and purification method of compound CPD10-5, only the corresponding raw materials need to be changed, and the target compound CPD377-3 (23.23 g, yield: 95.45%, mass spectrum: 401.06 (M+H)) is obtained as a white solid. The obtained compound is directly used in the next step without purification.

[0312] Synthesis of compound CPD377-4

[0313] Referring to the synthesis and purification method of compound CPD10-6, only the corresponding raw materials need to be changed, and the target compound CPD377-4 (20.05 g, mass fraction purity: 99.83%, yield: 76.59%) is obtained as a white solid, and the mass spectrometry characterization result is: 369.04 (M+H).

[0314] Synthesis of compound CPD377-5

[0315] The synthesis and purification method of reference compound CPD10-8 were referred to, only the corresponding raw materials were changed, and the target compound CPD377-5 was obtained in the form of a white solid (18.88 g, mass fraction purity: 99.00%, yield: 75.00%).

[0316] Synthesis of compound CPD377-6

[0317] The synthesis and purification method of reference compound CPD10 were referred to, only the corresponding raw materials were changed, and the target compound CPD377-6 was obtained in the form of a white solid (17.07 g, mass fraction purity: 99.63%, yield: 78.05%).

[0318] Synthesis of compound CPD377

[0319] The synthesis and purification method of reference compound CPD264 were referred to, only the corresponding raw materials were changed, and the target compound CPD377 was obtained in the form of a yellow solid (14.55 g, mass fraction purity: 99.96%, yield: 72.85%). After sublimation purification of 14.55 g of the crude CPD377, sublimed CPD377 was obtained in the form of a white solid (12.21 g, mass fraction purity: 99.96%, yield: 83.92%). Mass spectrometry characterization result: 744.24 (M+H). Nuclear magnetic resonance characterization result: 1 H NMR (400 MHz, CDCl3) δ 8.60 (d, J = 9.0 Hz, 1H), 8.47 (d, J = 8.1 Hz, 1H), 8.39 (d, J = 2.4 Hz, 1H), 8.33-8.28 (m, 1H), 8.28-8.19 (m, 3H), 8.16 (d, J = 7.8 Hz, 1H), 8.01-7.89 (m, 3H), 7.83 (d, J = 2.2 Hz, 1H), 7.79 (dd, J = 8.0, 2.4 Hz, 1H), 7.61-7.47 (m, 8H), 7.44-7.37 (m, 4H), 7.34-7.24 (m, 3H), 7.17-7.07 (m, 3H), 7.03-6.97 (m, 2H).

[0320] Synthesis of compound CPD404

[0321] The synthesis route is:

[0322] Synthesis of compound CPD404-3

[0323] The synthesis and purification method of reference compound CPD264-3 were referred to, only the corresponding raw materials were changed, and the target compound CPD404-3 was obtained as a white solid (19.89 g, mass fraction purity: 99.92%, yield: 79.58%). Mass spectrometry characterization result: 387.14 (M+H).

[0324] Synthesis of compound CPD404

[0325] The synthesis and purification method of reference compound CPD264 were referred to, only the corresponding raw materials were changed, and the target compound CPD404 was obtained as a yellow solid (16.78 g, mass fraction purity: 99.95%, yield: 73.06%). After sublimation purification of 16.78 g of the crude CPD404, sublimed CPD404 (13.54 g, mass fraction purity: 99.96%, yield: 80.78%) was obtained. Mass spectrometry characterization result: 703.22 (M+H). Nuclear magnetic resonance characterization result: 1 H NMR (400 MHz, CDCl3) δ 8.66 (d, J = 9.0 Hz, 1H), 8.32 (d, J = 8.0 Hz, 1H), 8.17 (dd, J = 5.1, 2.9 Hz, 2H), 8.11 (dd, J = 8.1, 1.9 Hz, 2H), 8.06-7.95 (m, 5H), 7.95-7.86 (m, 4H), 7.73 (d, J = 2.0 Hz, 1H), 7.70-7.60 (m, 2H), 7.56-7.46 (m, 1H), 7.46-7.36 (m, 4H), 7.33-7.22 (m, 2H), 7.19-7.04 (m, 3H), 6.89 (dd, J = 7.5, 2.2 Hz, 2H).

[0326] Synthesis of compound CPD422

[0327] The synthesis route is:

[0328] Synthesis of compound CPD422-2

[0329] The synthesis and purification method of reference compound CPD10-3 were referred to, only the corresponding raw materials were changed, and the target compound CPD422-2 was obtained as a white solid (20.02 g, mass fraction purity: 99.52%, yield: 75.63%). Mass spectrometry characterization result: 432.11 (M+H).

[0330] Synthesis of compound CPD422-3

[0331] The synthesis and purification method of compound CPD10-5 were referred to, only the corresponding raw materials were changed, and a white solid of target compound CPD422-3 was obtained (18.82 g, yield: 95.96%), and the mass spectrometry characterization result was 460.12 (M+H). The obtained compound was directly used in the next step without purification.

[0332] Synthesis of compound CPD422-4

[0333] The synthesis and purification method of compound CPD10-6 were referred to, only the corresponding raw materials were changed, and a white solid of target compound CPD422-4 was obtained (17.42 g, mass fraction purity: 99.63%, yield: 76.52%), and the mass spectrometry characterization result was 428.11 (M+H).

[0334] Synthesis of compound CPD422

[0335] The synthesis and purification method of compound CPD264 were referred to, only the corresponding raw materials were changed, and a yellow solid of target compound CPD422 was obtained (15.00 g, mass fraction purity: 99.95%, yield: 74.69%). After sublimation purification of 15.00 g of the crude CPD422, 12.00 g of sublimation pure CPD422 (mass fraction purity: 99.95%, yield: 80.00%) was obtained, and the mass spectrometry characterization result was 637.20 (M+H). The nuclear magnetic resonance characterization result was: 1 H NMR (400 MHz, CDCl3) δ 8.65 (d, J = 8.9 Hz, 1H), 8.37 (d, J = 8.0 Hz, 1H), 8.22-8.09 (m, 5H), 7.91 (d, J = 7.8 Hz, 1H), 7.73 (d, J = 2.0 Hz, 1H), 7.61-7.50 (m, 5H), 7.46-7.37 (m, 4H), 7.34-7.24 (m, 5H), 7.20-7.13 (m, 5H), 7.12-7.08 (m, 1H), 7.03-6.97 (m, 2H), 6.90-6.88 (m, 1H).

[0336] Synthesis of compound CPD451

[0337] The synthesis route is

[0338] Synthesis of compound CPD451-3

[0339] The synthesis and purification method of reference compound CPD10-3 was referred to, only the corresponding raw material was changed, to obtain the target compound CPD451-3 (19.58 g, mass fraction purity: 99.63%, yield: 76.09%) in white solid. The mass spectrometry characterization result was 357.06 (M+H).

[0340] Synthesis of compound CPD451-4

[0341] The synthesis and purification method of reference compound CPD10-5 was referred to, only the corresponding raw material was changed, to obtain the target compound CPD451-4 (18.56 g, yield: 95.55%) in white solid. The mass spectrometry characterization result was 385.09 (M+H). The obtained compound was directly used in the next step without purification.

[0342] Synthesis of compound CPD451-5

[0343] The synthesis and purification method of reference compound CPD10-6 was referred to, only the corresponding raw material was changed, to obtain the target compound CPD451-5 (17.52 g, mass fraction purity: 99.82%, yield: 76.15%) in white solid. The mass spectrometry characterization result was 353.07 (M+H).

[0344] Synthesis of compound CPD451-7

[0345] The synthesis and purification method of reference compound CPD264 was referred to, only the corresponding raw material was changed, to obtain the target compound CPD451-7 (14.52 g, mass fraction purity: 99.96%, yield: 75.26%) in yellow solid. The mass spectrometry characterization result was 576.12 (M+H).

[0346] NMR characterization result of compound CPD451-7: 1 H NMR (400 MHz, CDCl3) δ 8.53-8.43 (m, 2H), 8.34 (d, J = 8.2 Hz, 1H), 8.13 (d, J = 7.5 Hz, 1H), 8.10-8.01 (m, 2H), 8.01-7.91 (m, 2H), 7.67-7.57 (m, 2H), 7.57-7.48 (m, 2H), 7.48-7.37 (m, 5H), 7.31-7.24 (m, 3H), 7.18-7.05 (m, 4H), 7.03 (dd, J = 7.3, 2.2 Hz, 1H).

[0347]

[0348] Synthesis of compound CPD451

[0349] ​Compound CPD451-7 (15.00 g, 26.06 mmol), deuterated benzene-D6 (54.82 g, 651.50 mmol), trifluoroacetic acid (5.94 g, 52.12 mmol) were added into a 250 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.

[0350] The system was cooled to room temperature, and heavy water (50 ml) was added dropwise to quench the reaction, stirred at room temperature for 0.5 hours, then ethyl acetate (300 ml) was added, and the system was slurried with deionized water at room temperature for 1 hour, filtered, the filter cake was washed with deionized water three times (200 ml*3), and the filter cake was dried at 100°C under vacuum for 12 hours to obtain white solid CPD451 (14.42 g, mass fraction purity: 99.96%, HR-MS deuterium substitution calculation method see patent

CN115266981B

[0351] Application Example: Fabrication of an Organic Electroluminescent Device

[0352] In an embodiment, as shown in FIG. 2, which is a schematic diagram of an organic electroluminescent device structure, the organic electroluminescent device comprises 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.

[0353] A glass substrate with ITO (anode 2, indium tin oxide, 100 nm) transparent electrode of 50 mm*50 mm*1.0 mm was cleaned by ultrasonic washing in ethanol for 10 minutes, and then dried at 150°C and treated by N2 Plasma for 30 minutes. The washed glass substrate was installed on the substrate holder of a vacuum evaporation device, and compound NDP-9 and compound HTM 1 were evaporated to form a hole injection layer with a film thickness of 10 nm in a weight ratio of 97:3, followed by evaporation of a layer of HTM1 to form a film with a film thickness of 60 nm as HTL1 (hole transport layer 1), and then a layer of HTM2 was evaporated on the HTM1 film to form a film with a film thickness of 10 nm as HTL2 (hole transport layer 2), and then a light-emitting layer (host material: red light dopant = 97%:3%, mass fraction) with a film thickness of 40 nm was co-evaporated on the HTM2 film layer in the form of a single host or a double host, wherein the host material of the single host or the double host was the compound of the application, RH-P, RH-N, and comparative compounds 1-5, respectively. On the light-emitting layer, an ETL (electron transport layer) material and LiQ were co-evaporated (35 nm) in a weight ratio of 50:50 as an electron transport material, followed by evaporation of LiQ (1 nm) on the electron transport material layer as an electron injection material to form an electron injection layer, followed by co-evaporation of Mg / Ag (100 nm, mass ratio 1:9) as a cathode material, to obtain an organic electroluminescent device.

[0354] The structural formulas of NDP-9, HTM1, HTM2, ETL material, red light dopant, LiQ, RH-P, RH-N, and comparative compounds 1-6 are as follows:

[0355] Evaluation:

[0356] The above organic electroluminescent device was tested for device performance, and the compounds prepared by the application and comparative compounds 1-6 were used as host materials for comparison. A constant current power supply (Keithley 2400) was used, a fixed current density was used to flow through the light-emitting element, and a spectroradiometer (CS2000) was used to test the luminescence spectrum. At the same time, the IVL (current-voltage-luminance) performance of the device was 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.

[0357] The device performance data of the light-emitting layer co-evaporated with the compound of the application and comparative compounds 1-6 as a single host and a red light dopant are shown in Table 1 (the examples in Table 1 use the compound of the application, and the comparative examples use the comparative compounds).

[0358] Table 1

[0359] The device data of the devices in which the compound of the present application, the comparative compound and RH-P, RH-N material are mixed at a ratio of 5:5 and co-evaporated with a red light doping material to form a light-emitting layer are shown in Table 2.

[0360] Table 2

[0361] As can be seen from Tables 1-2, the device prepared by using the compound of the present application has a significantly longer service life than the devices prepared by using the comparative compounds 1-6, and also has better device performance compared with RH-P and RH-N. In particular, the compound of the present application used in combination with RH-P as a double host material also has better device performance.

[0362] Compared with the relatively twisted structure of the comparative compound 3, the benzophenanthrene four-ring of the compound of the present application has a linear and relatively planar structure, which makes the intermolecular π-π stacking more compact and the hole or electron transport faster. Such a compound has a faster mobility, which is conducive to reducing the voltage and improving the efficiency and service life.

[0363] The compound of the present application and the comparative compound are subjected to a heat-resistant experiment in a sealed tube to verify the stability of the compound after long-time heating. The sample is vacuum-sealed in an ampoule and placed in a heat stability tester, heated to 280℃ at a vacuum degree of 10 -7 Torr, for 300h, and then taken out for testing the purity and device performance:

[0364] Table 3: Comparison of purity before and after heat resistance

[0365] Table 4: Performance of the device prepared by using the compound after heat resistance (the device is prepared according to the conditions in Table 2)

[0366] As can be seen from Tables 3-4, the purity of the compound of the present application does not decrease significantly after long-time heating, and can be greater than 99.9% (mass fraction), and the performance of the device prepared by using the compound after long-time heating is basically the same as that before heat resistance. However, the purity of the comparative compound 1 and the comparative compound 6 decreases significantly after long-time heating, and the service life of the device prepared by using the compound after heat resistance decreases significantly, which indicates that the comparative compound has poor stability.

[0367] Therefore, the compound of the present application has high thermal stability, and can maintain stable product structure after long-time heating and evaporation, and has good mass production property.

[0368] Sublimation temperature comparison: the definition of sublimation temperature is that the sample is heated to 280℃ at a vacuum degree of 10 -7Torr, the sublimation rate of 1 angstrom per second corresponds to the temperature. The test results are shown in Table 5.

[0369] Table 5

[0370] As can be seen from Table 5, the compound of the present application has a lower sublimation temperature than comparative compounds 1-4, which is beneficial to industrial application.

[0371] As a single host red material, the compound of the present application has a lower voltage, higher current efficiency and longer life than the comparative compounds; at the same time, when the N-type compound of the present application is matched with the P-type material or the P-type compound of the present application is matched with the N-type material as a double host material, the hole and electron transport rates are balanced, the exciton recombination region in the light-emitting layer is widened, the exciton density is reduced, and the exciton annihilation is reduced, compared with the comparative compounds 1-6, the efficiency and life of the device are greatly improved.

[0372] Therefore, the compound material of the present application has the advantages of high optical, electrical and thermal stability, low sublimation temperature, low driving voltage, high luminous efficiency, long device life and the like, 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 the 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.

[0373] In addition, since it is impossible to enumerate all the compounds of the present application, the above Tables 1-5 only list the performance of some compounds or devices of the present application, but within the scope of the present application, especially the compounds specifically given in the structural formula of the present application all have the advantages of high optical, electrical and thermal stability, low sublimation temperature, low driving voltage, high luminous efficiency, long device life and the like similar to CPD346.

Claims

1. A compound, characterized in that, Its general structural formula is shown in equation (1): Wherein, ring A is selected from one of the following formulas (2)-(5), and * indicates the site that is fused with the 5-membered ring containing X; In equations (2)-(5), the hydrogen atoms on the four benzene rings of benzo[4]phenanthrene can be replaced by deuterium or fluorine; In equation (1), X is selected from NR. a1 CR b R c Or oxalic elements; Where a represents an integer from 1 to 4, and b represents an integer from 1 to 10, and when a≥2, two adjacent R0s can be connected to form a parallel ring; R0 is selected from hydrogen, deuterium, halogen, cyano, nitro, C1-C40 alkyl, C1-C40 heteroalkyl, C2-C40 alkenyl, C2-C40 alkynyl, C3-C40 cycloalkyl, C3-C40 heterocycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, C1-C40 alkoxy, C6-C60 aryloxy, C3-C40 alkylsilyl, C6-C60 arylsilyl, C1-C40 alkylboryl, C6-C60 arylboryl, C6-C60 arylphosphinyl, or C6-C60 arylamine. R1 represents -L-ET or -L-NAr1Ar2; L is selected from single bond, substituted or unsubstituted C6-C60 aryl group or substituted or unsubstituted C3-C60 heteroaryl group; ET indicates an electron-withdrawing group; Ar1 and Ar2 are independently selected from substituted or unsubstituted C6-C36 aryl and substituted or unsubstituted C2-C36 heteroaryl, respectively; R a1 R b R c Each amino group is independently selected from C1-C30 alkyl, C1-C30 heteroalkyl, C3-C30 cycloalkyl, C3-C30 heterocycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C3-C30 alkylsilyl, C6-C30 arylsilyl, or substituted or unsubstituted amino groups, when X is CR b R c At that time, R b R c They can be connected to form a ring; The substitution is at least one of the following: a amine group substituted with deuterium, halogen, cyano, isocyano, phosphin, C1-C6 alkyl, C3-C16 cycloalkyl or C1-C6 alkyl, an aryl group substituted with or unsubstituted with C6-C30 alkyl, or a heteroaryl group substituted with or unsubstituted with C1-C6 alkyl, wherein the number of substitutions ranges from monosubstituted to the maximum number of substitutions.

2. The compound according to claim 1, characterized in that, The R0 is selected from hydrogen, deuterium, halogen, cyano, nitro, C1-C20 alkyl, C1-C20 heteroalkyl, C2-C20 alkenyl, C2-C20 alkynyl, C3-C20 cycloalkyl, C3-C20 heterocycloalkyl, C6-C20 aryl, C3-C20 heteroaryl, C1-C20 alkoxy, C6-C20 aryloxy, C3-C20 alkylsilyl, C6-C20 arylsilyl, C1-C20 alkylboryl, C6-C20 arylboryl, C6-C20 arylphosphinyl, or C6-C20 arylamino; and / or The R a1 R b R c Each of the following is independently selected from C1-C20 alkyl, C1-C20 heteroalkyl, C3-C20 cycloalkyl, C3-C20 heterocycloalkyl, C6-C20 aryl, C5-C20 heteroaryl, C3-C20 alkylsilyl, and C6-C20 arylsilyl; and / or Ar1 and Ar2 are independently selected from substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C2-C30 heteroaryl groups, and / or The substitution is performed by at least one of deuterium, halogen, cyano, isocyano, phosphinyl, C1-C6 alkyl, C3-C12 cycloalkyl, C1-C6 alkyl-substituted amino, C6-C18 aryl, or C3-C18 heteroaryl, wherein the number of substitutions ranges from monosubstituted to the maximum number of substitutions; and / or The L is a substituted or unsubstituted C6-C20 arylene or heteroarylene.

3. The compound according to claim 1, characterized in that, The R0 is selected from hydrogen, deuterium, halogen, cyano, nitro, C1-C30 alkyl, C1-C30 heteroalkyl, C2-C30 alkenyl, C2-C30 alkynyl, C3-C30 heterocycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C1-C30 alkoxy, C6-C30 aryloxy, C3-C30 alkylsilyl, C6-C30 arylsilyl, C1-C30 alkylboronyl, C6-C30 arylboronyl, C6-C30 arylphosphinyl, or C6-C30 arylamino; and / or, the R a1 R b R c Each of the following is independently selected from C1-C15 alkyl, C1-C15 heteroalkyl, C3-C15 cycloalkyl, C3-C15 heterocycloalkyl, C6-C18 aryl, C5-C18 heteroaryl, C3-C15 alkylsilyl, and C6-C18 arylsilyl.

4. The compound according to claim 1, characterized in that, The R0 is selected from hydrogen, deuterium, halogen, cyano, nitro, C1-C10 alkyl, C1-C10 heteroalkyl, C2-C10 alkenyl, C2-C10 alkynyl, C3-C10 cycloalkyl, C3-C10 heterocycloalkyl, C6-C12 aryl, C3-C12 heteroaryl; and / or The substitution is made by at least one of deuterium, halogen, cyano, isocyano, phosphin, C1-C6 alkyl, C3-C10 cycloalkyl, C1-C6 alkyl-substituted amino, C6-C12 aryl, or C3-C12 heteroaryl, wherein the number of substitutions ranges from monosubstituted to the maximum number of substitutions.

5. The compound according to claim 1, characterized in that, The oxalic elements are selected from O, S, or Se.

6. The compound according to claim 1, characterized in that, X is CR b R c , O or S; The R b R c Each of the following is independently selected from C1-C10 alkyl, C1-C10 heteroalkyl, C3-C10 cycloalkyl, C3-C10 heterocycloalkyl, C6-C10 aryl or C5-C10 heteroaryl.

7. The compound according to claim 1, characterized in that, The heteroatom in the heteroaryl, heteroalkyl, or heterocycloalkyl group is independently selected from at least one of O, S, N, Se, Si, and Ge.

8. The compound according to claim 1, characterized in that, The structures shown in equations (2) to (5) are selected from the structures shown in equations (6) to (9): Where * represents the site that fused with the 5-membered ring containing X in equation (1).

9. The compound according to claim 1, characterized in that, The electron-withdrawing group represented by ET is selected from the structures shown in Formulas B-1 to B-10: Where Z is independently either N or CR. d And at least one Z in equations (B-1) to (B-3) and equations (B-6) to (B-10) is N, and no two adjacent Z in (B-10) are N at the same time; W is independently NR e O, S, SO, SO2, CR f R g or SiR h R j ; Y is independently NR a1 CR b R c , O, S or Se; R a1 R b R c Consistent with the aforementioned definition; R2, R d -R h R j Independently selected from hydrogen, deuterium, halogen, cyano, nitro, C1-C40 alkyl, C1-C40 heteroalkyl, C2-C40 alkenyl, C2-C40 alkynyl, C3-C40 cycloalkyl, C3-C40 heterocycloalkyl, C3-C40 alkylsilyl, C6-C60 arylsilyl, C1-C40 alkylboronyl, C1-C40 alkoxy-substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, substituted or unsubstituted C6-C60 aryloxy, substituted or unsubstituted C6-C60 arylboronyl, substituted or unsubstituted C6-C60 arylphosphinyl or substituted or unsubstituted C6-C60 arylamine; Where n is an integer from 0 to 10; if n is an integer of 2 or greater, each R2 can be the same or different, and adjacent R2s can be connected to form a parallel ring.

10. The compound according to claim 9, characterized in that, The R2 is selected from hydrogen, deuterium, halogen, cyano, nitro, C1-C30 alkyl, C1-C30 heteroalkyl, C2-C30 alkenyl, C2-C30 alkynyl, C3-C30 cycloalkyl, C3-C30 heterocycloalkyl, substituted or unsubstituted C6-C40 aryl, C5-C40 heteroaryl, C1-C30 alkoxy, C6-C40 aryloxy, C3-C30 alkylsilyl, C6-C40 arylsilyl, C1-C30 alkylboryl, C6-C40 arylboryl, C6-C30 arylphosphinyl, or C6-C30 arylamine.

11. The compound according to claim 10, characterized in that, The R2 is selected from hydrogen, deuterium, halogen, cyano, nitro, C1-C20 alkyl, C1-C20 heteroalkyl, C2-C20 alkenyl, C2-C20 alkynyl, C3-C20 cycloalkyl, C3-C20 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, C5-C30 heteroaryl, C1-C20 alkoxy, C6-C30 aryloxy, C3-C20 alkylsilyl, C6-C30 arylsilyl, C1-C20 alkylboryl, C6-C30 arylboryl, C6-C20 arylphosphinyl, or C6-C20 arylamine.

12. The compound according to claim 1, characterized in that, The electron-withdrawing group represented by ET is selected from the structures shown in formulas (B-11) to (B-36): Each R2 is independently selected from hydrogen, deuterium, halogen, cyano, nitro, C1-C40 alkyl, C1-C40 heteroalkyl, C2-C40 alkenyl, C2-C40 alkynyl, C3-C40 cycloalkyl, C3-C40 heterocycloalkyl, substituted or unsubstituted C6-C60 aryl, C5-C60 heteroaryl, C1-C40 alkoxy, C6-C60 aryloxy, C3-C40 alkylsilyl, C6-C60 arylsilyl, C1-C40 alkylboryl, C6-C60 arylboryl, C6-C60 arylphosphinyl or C6-C60 arylamine; n is an integer from 0 to 6. If n≥2, then each R2 can be the same or different, and adjacent R2 can be connected to form a parallel ring.

13. The compound according to claim 1, characterized in that, The L is selected from single bonds and the structures shown in formulas L-1 to L-14 below: Wherein R4 is a substituent, each R4 is independently selected from hydrogen, deuterium, halogen, cyano, nitro, C1-C20 alkyl, C1-C20 heteroalkyl, C2-C20 alkenyl, C2-C20 alkynyl, C3-C20 cycloalkyl, C3-C20 heterocycloalkyl, C6-C30 aryl, C5-C30 heteroaryl, C1-C20 alkoxy, C6-C30 aryloxy, C3-C20 alkylsilyl, C6-C30 arylsilyl, C1-C20 alkylboryl, C6-C30 arylboryl, C6-C30 arylphosphinyl or C6-C30 arylamino, and m is from monosubstituted to the maximum number of substituted groups.

14. The compound according to any one of claims 1-13, characterized in that, The compound is one of the following structural formulas, or a structure in which hydrogen is partially or completely substituted by deuterium or fluorine:

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

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