An organic electroluminescence element and an electronic device including the same

Abstract

The present application provides a kind of high-performance organic electroluminescent element, including anode, cathode, including emitting layer between anode and cathode Organic functional layer, the anode and emitting layer between include hole transport region, it is characterized in that, the hole transport region includes the compound shown in formula (2), formula (2) the organic electroluminescent element of application in the present application can realize the effect of further promoting the driving voltage reduction, efficiency and life of element after using formula (2) compound.

Description

Technical Field

[0001] This invention relates to the field of organic electroluminescence technology, and more specifically, to an organic electroluminescent element and an electronic device. Background Technology

[0002] Organic light-emitting diodes (OLEDs) are self-emissive display devices based on organic electroluminescent materials. Unlike existing liquid crystal displays (LCDs), they do not require a backlight and are thin, making them suitable for flexible devices (flexible light-emitting display devices). OLED technology can be used to manufacture new display products as well as new lighting products, and it is expected to replace existing liquid crystal displays and fluorescent lighting, with a very wide range of applications.

[0003] Organic light-emitting diodes (OLEDs) consist of an anode, a cathode, and an organic functional layer located between the anode and cathode. When a voltage is applied between the two electrodes, electrons are injected into the light-emitting region from the cathode side, and holes are injected into the light-emitting region from the anode side. The injected electrons and holes recombine in the light-emitting region to generate an excited state, which emits light when it returns to the ground state. Therefore, developing high-performance organic light-emitting diodes is important.

[0004] Current research on improving the performance of organic electroluminescent devices includes reducing the driving voltage, increasing the luminous efficiency, and extending the device's lifespan. The characteristics of the organic compounds contained in each layer have a significant impact on the device's driving voltage, luminous efficiency, and lifespan. Therefore, continuous research and innovation in organic electroluminescent functional materials to manufacture higher-performance organic electroluminescent functional materials, thereby producing high-performance organic electroluminescent devices, is an inevitable trend. Summary of the Invention

[0005] The purpose of this invention is to provide a high-performance organic electroluminescent element and an electronic device comprising the organic electroluminescent element.

[0006] The technical solution of the present invention is as follows:

[0007] In a first aspect, an organic electroluminescent element includes an anode, a cathode, and an organic functional layer including a light-emitting layer located between the anode and the cathode, wherein a hole transport region is included between the anode and the light-emitting layer, and the hole transport region includes a compound represented by formula (2).

[0008]

[0009] Equation (2)

[0010] Ar1 is selected from substituted or unsubstituted naphthyl groups.

[0011] Ar2 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted dibenzofuranyl, preferably from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted fluorenyl, more preferably from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, and most preferably from substituted or unsubstituted naphthyl; the fluorenyl is preferably selected from C1-C1. 10 The alkyl-substituted fluorene is more preferably selected from methyl-substituted fluorene, and more preferably from 9,9'-dimethylfluorene;

[0012] Ar3 is selected from substituted or unsubstituted helical fluorene groups.

[0013] L1 and L2 are each independently selected from substituted or unsubstituted phenyl groups, or substituted or unsubstituted naphthyl groups.

[0014] L3 and L4 are each independently selected from single-bonded, substituted, or unsubstituted C6-C30 phenylene groups. L3 and L4 cannot both be single bonds.

[0015] R1 and R2 are each independently selected from hydrogen, substituted or unsubstituted C1-C10 alkyl groups, substituted or unsubstituted phenyl groups, and R1 and R2 are connected to each other to form a ring structure or are not connected to each other.

[0016] The substituents in the "substituted or unsubstituted" designation are each independently selected from one or a combination of deuterium, halogen, cyano, C1-C10 alkyl, C1-C10 alkoxy, amino, C3-C10 cycloalkyl, C3-C10 cycloalkoxy, C6-C30 aryl, C3-C30 heteroaryl, C1-C10 alkenyl, and C1-C10 alkynyl, preferably selected from deuterium, halogen, cyano, and C1-C10 alkyl, halogen, cyano, and alkyl, halogen, cyano ... The alkyl group, C1-C10 alkoxy group, amino group, C3-C10 cycloalkoxy group, C6-C30 aryl group, C3-C30 heteroaryl group, C1-C10 alkenyl group, and C1-C10 alkynyl group are selected from one or a combination thereof, more preferably from one or a combination thereof, from deuterium, halogen, cyano group, C1-C10 alkyl group, C6-C30 aryl group, and C3-C30 heteroaryl group, more preferably from deuterium and halogen, and most preferably from deuterium.

[0017] The heteroatom of the heteroaryl group is selected from one or more of N, O, S, Si, P, and B, preferably from one or more of N, O, S, Si, and P, more preferably from one or more of N, O, S, and P, more preferably from one or more of N, O, and S, particularly preferably from one or more of N and O, and most preferably from one or more of N.

[0018] Preferably, the above-mentioned compound may not contain or may contain at least one deuterium.

[0019] Preferably, the compound represented by formula (2) is not...

[0020] .

[0021] Preferably, the Ar1 is selected from , More preferably, the Ar1 is selected from... Preferably, the above-mentioned groups are unsubstituted or substituted with one or more substituents selected from deuterium, fluorine, and cyano; more preferably, the above-mentioned groups are unsubstituted or substituted with one or more substituents selected from deuterium and fluorine; more preferably, the above-mentioned groups are unsubstituted or substituted with one or more deuterium groups; most preferably, the above-mentioned groups are unsubstituted. "Indicates the connection position.

[0022] Preferably, the Ar3 is selected from substituted or unsubstituted spirobifluorenyl groups, and preferably, the substituent in "substituted or unsubstituted" is defined as above; more preferably, the Ar3 is selected from... , , , Preferably, the above-mentioned groups are unsubstituted or substituted with one or more substituents selected from deuterium, fluorine, and cyano; more preferably, the above-mentioned groups are unsubstituted or substituted with one or more substituents selected from deuterium and fluorine; more preferably, the above-mentioned groups are unsubstituted or substituted with one or more deuterium groups; most preferably, the above-mentioned groups are unsubstituted. "Indicates the connection position.

[0023] Preferably, L1 and L2 are each independently selected from substituted or unsubstituted phenylene groups, and preferably, the substituents in "substituted or unsubstituted" are defined as above; more preferably, L1 and L2 are each independently selected from... , Preferably, the above-mentioned groups are unsubstituted or substituted with one or more substituents selected from deuterium, fluorine, and cyano; more preferably, the above-mentioned groups are unsubstituted or substituted with one or more substituents selected from deuterium and fluorine; more preferably, the above-mentioned groups are unsubstituted or substituted with one or more deuterium groups; most preferably, the above-mentioned groups are unsubstituted. "Indicates the connection position.

[0024] Preferably, L3 and L4 are each independently selected from single bonds and phenylene, and L3 and L4 cannot be single bonds simultaneously; more preferably, L3 is selected from single bonds and L4 is selected from phenylene, or L4 is selected from single bonds and L3 is selected from phenylene, or both L3 and L4 are selected from phenylene; preferably, the above groups are unsubstituted or substituted by one or more substituents selected from deuterium, fluorine, and cyano; more preferably, the above groups are unsubstituted or substituted by one or more substituents selected from deuterium and fluorine; more preferably, the above groups are unsubstituted or substituted by one or more deuterium; most preferably, the above groups are unsubstituted.

[0025] Preferably, R1 and R2 are each independently selected from hydrogen, methyl, ethyl, tert-butyl, or R1 and R2 are connected to each other to form a ring structure, wherein the ring structure is preferably selected from C1-C8 alkyl-substituted fluorenyl groups; more preferably, R1 and R2 are each independently selected from hydrogen, and R1 and R2 are connected to each other to form a ring structure, wherein the ring structure is preferably selected from 9,9-dimethylfluorenyl; preferably, the above groups are unsubstituted or substituted by one or more substituents selected from deuterium, fluorine, or cyano; more preferably, the above groups are unsubstituted or substituted by one or more substituents selected from deuterium or fluorine; more preferably, the above groups are unsubstituted or substituted by one or more deuterium groups; most preferably, the above groups are unsubstituted.

[0026] Preferably, the substituents in the "substituted or unsubstituted" configuration are each independently selected from one or more combinations of deuterium, fluoro, cyano, methyl, ethyl, tert-butyl, cyclohexyl, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, pyrene, fluoranyl, triphenylene, phenylene, dibenzofuranyl, and dibenzothiophene. More preferably, the substituents in the "substituted or unsubstituted" configuration are each independently selected from one or more combinations of deuterium, fluoro, tert-butyl, phenyl, biphenyl, dibenzofuranyl, and dibenzothiophene.

[0027] Preferably, the compound represented by formula (2) has the structure shown in formula 2-1A.

[0028]

[0029] Formula 2-1A

[0030] The definitions of Ar1, Ar2, L1-L4, R1, and R2 are the same as above;

[0031] The definition of substituents in the phrase "substituted or unsubstituted" is the same as above;

[0032] Preferably, the above-mentioned compound may not contain or may contain at least one deuterium.

[0033] Preferably, the compound represented by formula (2) has the structure shown in formulas 2-1B to 2-1E.

[0034] ,

[0035] The definitions of Ar1, Ar2, L1-L4, R1, and R2 are the same as above;

[0036] The definition of substituents in the phrase "substituted or unsubstituted" is the same as above;

[0037] Preferably, the above-mentioned compound may not contain or may contain at least one deuterium.

[0038] Preferably, in equation (2), the preferred embodiment is... Selected from the following groups, whether substituted or unsubstituted: , Preferably, the definition of the substituent in "substituted or unsubstituted" is the same as above; more preferably, the... Selected from the following groups: , , or the aforementioned Selected from the following groups: , ;

[0039] “ " indicates the connection position with N;

[0040] Preferably, the above-mentioned groups are unsubstituted or substituted with one or more substituents selected from deuterium, fluorine, and cyano; more preferably, the above-mentioned groups are unsubstituted or substituted with one or more substituents selected from deuterium and fluorine; more preferably, the above-mentioned groups are unsubstituted or substituted with one or more deuterium groups; most preferably, the above-mentioned groups are unsubstituted.

[0041] Preferably, the compound represented by formula (2) has the structure shown in formulas 2-1 to 2-8.

[0042]

[0043]

[0044] ,

[0045] The definitions of Ar1, Ar2, L1-L4, R1, and R2 are the same as above;

[0046] The definition of substituents in the phrase "substituted or unsubstituted" is the same as above;

[0047] Preferably, the above-mentioned compound may not contain or may contain at least one deuterium.

[0048] Preferably, in equation (2), the preferred embodiment is... Selected from the following groups, whether substituted or unsubstituted:

[0049]

[0050]

[0051] More preferably, the Selected from the following groups, whether substituted or unsubstituted:

[0052]

[0053] The most preferred option is the one described above. Selected from the following groups, whether substituted or unsubstituted:

[0054] ;

[0055] “ " indicates the connection position with N;

[0056] Preferably, the definition of the substituent in "substituted or unsubstituted" is the same as above;

[0057] Preferably, the above-mentioned groups are unsubstituted or substituted with one or more substituents selected from deuterium, fluorine, and cyano; more preferably, the above-mentioned groups are unsubstituted or substituted with one or more substituents selected from deuterium and fluorine; more preferably, the above-mentioned groups are unsubstituted or substituted with one or more deuterium groups; most preferably, the above-mentioned groups are unsubstituted.

[0058] Preferably, the compound represented by formula (2) is as follows:

[0059]

[0060]

[0061]

[0062]

[0063]

[0064]

[0065]

[0066]

[0067]

[0068]

[0069]

[0070]

[0071]

[0072]

[0073]

[0074]

[0075]

[0076]

[0077]

[0078]

[0079]

[0080]

[0081]

[0082]

[0083]

[0085]

[0086]

[0087]

[0088]

[0089]

[0090]

[0091]

[0092]

[0093]

[0094]

[0095]

[0096]

[0097]

[0098]

[0099] .

[0100] Preferably, the organic electroluminescent element can be a single-layer device or a multilayer device.

[0101] Preferably, in the organic electroluminescent element, the hole transport region includes one or more of a hole injection layer, a hole transport layer, and a light-emitting auxiliary layer, wherein the hole injection layer is close to the anode, the hole transport layer is located between the hole injection layer and the light-emitting auxiliary layer, the light-emitting auxiliary layer is located between the hole transport layer and the light-emitting layer, and at least one layer in the hole transport region includes the compound shown in formula (2).

[0102] Preferably, the light-emitting auxiliary layer comprises the compound shown in formula (2).

[0103] More preferably, in the single-layer device, the light-emitting auxiliary layer comprises the compound shown in formula (2).

[0104] More preferably, in the stacked device, the at least one light-emitting auxiliary layer comprises the compound shown in formula (2).

[0105] Preferably, in the organic electroluminescent element described in the first aspect above, the light-emitting layer further includes a compound comprising a boron-nitrogen structure, wherein the boron-nitrogen structure is preferably [missing information]. .

[0106] Preferably, in the organic electroluminescent element described in the first aspect above, the light-emitting layer further comprises a compound represented by formula (1).

[0107]

[0108] Equation (1)

[0109] in,

[0110] A, Ar4-Ar7 are each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, alkyl-substituted silane with C1-C10 carbon atoms, and aryl-substituted silane with 6-30 carbon atoms.

[0111] Alternatively, A and Ar4 may link together to form substituted or unsubstituted carbazole groups.

[0112] L5 is selected from single-bonded, substituted, or unsubstituted C6-C30 aryl groups.

[0113] R5-R8 are each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C10 alkyl, alkyl-substituted silane with C1-C10 atoms, and aryl-substituted silane with 6-30 carbon atoms.

[0114] The structure of formula (1) is unsubstituted or substituted with one or more of the following substituents: deuterium, halogen, cyano, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C1-C10 alkoxy, substituted or unsubstituted amino, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C3-C10 cycloalkoxy, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C1-C10 alkenyl, substituted or unsubstituted C1-C10 alkynyl, substituted or unsubstituted silyl.

[0115] The substituents in the "substituted or unsubstituted" designation are each independently selected from one or a combination of deuterium, halogen, cyano, C1-C10 alkyl, C1-C10 alkoxy, amino, C3-C10 cycloalkyl, C3-C10 cycloalkoxy, C6-C30 aryl, C3-C30 heteroaryl, C1-C10 alkenyl, C1-C10 alkynyl, silyl having a C1-C10 alkyl substituted group, and silyl having an aryl substituted group with 6-30 carbon atoms.

[0116] The heteroatom of the heteroaryl group is selected from one or more of N, O, S, Si, P, and B, preferably from one or more of N, O, S, Si, and B, more preferably from one or more of N, O, S, and Si, more preferably from one or more of N, O, and S, particularly preferably from one or more of O and S, and most preferably from O.

[0117] Preferably, the above-mentioned compound may not contain or may contain at least one deuterium.

[0118] Preferably, in the organic electroluminescent element described in the first aspect above, the light-emitting layer further comprises a compound represented by formula (1).

[0119]

[0120] Equation (1)

[0121] in,

[0122] A is “ " indicates the connection position with N, where n is an integer between 0 and 1.

[0123] Ar4-Ar7 are each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, alkyl-substituted silane with C1-C10 carbon atoms, and aryl-substituted silane with 6-30 carbon atoms.

[0124] Alternatively, A and Ar4 may link together to form substituted or unsubstituted carbazole groups.

[0125] L5 is selected from single-bonded, substituted, or unsubstituted C6-C30 aryl groups.

[0126] R3-R8 are each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C10 alkyl, alkyl-substituted silane with C1-C10 atoms, and aryl-substituted silane with 6-30 carbon atoms.

[0127] The substituents in the "substituted or unsubstituted" designation are each independently selected from one or a combination of deuterium, halogen, cyano, C1-C10 alkyl, C1-C10 alkoxy, amino, C3-C10 cycloalkyl, C3-C10 cycloalkoxy, C6-C30 aryl, C3-C30 heteroaryl, C1-C10 alkenyl, C1-C10 alkynyl, silyl having a C1-C10 alkyl substituted group, and silyl having an aryl substituted group with 6-30 carbon atoms.

[0128] The heteroatom of the heteroaryl group is selected from one or more of N, O, S, Si, P, and B, preferably from one or more of N, O, S, Si, and B, more preferably from one or more of N, O, S, and Si, more preferably from one or more of N, O, and S, particularly preferably from one or more of O and S, and most preferably from O.

[0129] Preferably, the above-mentioned compound may not contain or may contain at least one deuterium.

[0130] Preferably, in the organic electroluminescent element described in the first aspect above, the light-emitting layer further comprises a compound represented by formula (1).

[0131]

[0132] Equation (1)

[0133] The definitions of A, Ar4-Ar8, L5, and R5-R8 are the same as above;

[0134] The definition of the substituent in the phrase "substituted or unsubstituted" is the same as above.

[0135] Preferably, the above-mentioned compound may not contain or may contain at least one deuterium.

[0136] Preferably, the compound represented by formula (1) contains at least one deuterium or halogen; more preferably, when n is 1, the compound represented by formula (1) contains at least one deuterium or halogen, and when n is 0, the compound represented by formula (1) contains at least one halogen.

[0137] Preferably, in formula (1), L5 is selected from single-bonded, substituted or unsubstituted phenylene, and preferably the substituent in "substituted or unsubstituted" is defined as above; more preferably, L5 is selected from single-bonded or phenylene; most preferably, L5 is selected from single-bonded.

[0138] Preferably, in formula (1), each of Ar4-Ar7 is independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C6-C30 aryl, or substituted or unsubstituted C3-C30 heteroaryl; more preferably, each of Ar4-Ar7 is independently selected from substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C6-C30 aryl, or substituted or unsubstituted C3-C30 heteroaryl; and most preferably, each of Ar4-Ar7 is... Ar4-Ar7 are each independently selected from substituted or unsubstituted C6-C30 aryl groups and substituted or unsubstituted C3-C30 heteroaryl groups; more preferably, each of Ar4-Ar7 is independently selected from substituted or unsubstituted phenyl groups, substituted or unsubstituted biphenyl groups, and substituted or unsubstituted dibenzothiophene groups; particularly preferably, each of Ar4-Ar7 is independently selected from substituted or unsubstituted phenyl groups; especially preferably, each of Ar4-Ar7 is independently selected from phenyl-substituted phenyl groups, tert-butyl-substituted phenyl groups, deuterium-substituted phenyl groups, and fluorine-substituted phenyl groups.

[0139] Preferably, the definition of the substituent in "substituted or unsubstituted" is the same as above;

[0140] The heteroatom of the heteroaryl group is preferably selected from one or more of N, O, S, Si, P, and B, more preferably selected from one or more of N, O, S, Si, and B, more preferably selected from one or more of N, O, S, and Si, more preferably selected from one or more of N, O, and S, particularly preferably selected from one or more of O and S, and most preferably selected from O.

[0141] Preferably, in formula (1), each of R3-R8 is independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C10 alkyl groups, and preferably the substituents in "substituted or unsubstituted" are defined as above; more preferably, each of R3-R8 is independently selected from hydrogen, deuterium, fluorine, or C1-C10 alkyl groups; most preferably, each of R3-R8 is independently selected from hydrogen, deuterium, or tert-butyl.

[0142] Preferably, in formula (1), the substituents in the "substituted or unsubstituted" group are each independently selected from one or more combinations of deuterium, fluoro, cyano, methyl, ethyl, tert-butyl, cyclohexyl, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, pyrene, fluoranyl, triphenylene, phenylene, dibenzofuranyl, and dibenzothiophene; more preferably, the substituents in the "substituted or unsubstituted" group are each independently selected from one or more combinations of deuterium, fluoro, tert-butyl, phenyl, biphenyl, dibenzofuranyl, and dibenzothiophene; most preferably, the substituents in the "substituted or unsubstituted" group are each independently selected from one or more combinations of deuterium, fluoro, and phenyl.

[0143] In a second aspect, the present invention provides an organic electroluminescent element, comprising an anode, a cathode, and an organic functional layer including a light-emitting layer located between the anode and the cathode, wherein the light-emitting layer comprises a compound represented by formula (1).

[0144]

[0145] Equation (1)

[0146] in,

[0147] A is “ " indicates the connection position with N, where n is an integer between 0 and 1.

[0148] Ar4-Ar7 are each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl.

[0149] Alternatively, A and Ar4 may link together to form substituted or unsubstituted carbazole groups.

[0150] L5 is selected from single-bonded, substituted, or unsubstituted C6-C30 aryl groups.

[0151] R3-R8 are each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C10 alkyl groups.

[0152] When n is 1, the compound represented by formula (1) contains at least one deuterium or halogen.

[0153] When n is 0, the compound shown in formula (1) contains at least one halogen.

[0154] The substituents in the "substituted or unsubstituted" designation are each independently selected from one or a combination of deuterium, halogen, cyano, C1-C10 alkyl, C1-C10 alkoxy, amino, C3-C10 cycloalkyl, C3-C10 cycloalkoxy, C6-C30 aryl, C3-C30 heteroaryl, C1-C10 alkenyl, C1-C10 alkynyl, silyl having a C1-C10 alkyl substituted group, and silyl having an aryl substituted group with 6-30 carbon atoms.

[0155] The heteroatom of the heteroaryl group is selected from one or more of N, O, S, Si, P, and B, preferably from one or more of N, O, S, Si, and B, more preferably from one or more of N, O, S, and Si, more preferably from one or more of N, O, and S, particularly preferably from one or more of O and S, and most preferably from O.

[0156] Preferably, the above-mentioned compound may not contain or may contain at least one deuterium.

[0157] Preferably, the light-emitting layer of the organic electroluminescent element comprises a compound of formula (1).

[0158]

[0159] Equation (1)

[0160] The definitions of A, Ar4-Ar8, L5, and R5-R8 are the same as above;

[0161] The definition of substituents in the phrase "substituted or unsubstituted" is the same as above;

[0162] Preferably, the above-mentioned compound may not contain or may contain at least one deuterium.

[0163] Preferably, the light-emitting layer of the organic electroluminescent element comprises a compound of formula (1).

[0164]

[0165] Equation (1)

[0166] in,

[0167] A is “ " indicates the connection position with N, where n is an integer between 0 and 1;

[0168] Ar4-Ar7 are each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl.

[0169] L5 is selected from single-bonded, substituted or unsubstituted C6-C30 aryl groups;

[0170] The definitions of R3-R8 are the same as above;

[0171] The definition of n is the same as above;

[0172] The definition of substituents in the phrase "substituted or unsubstituted" is the same as above;

[0173] The heteroatom of the heteroaryl group is preferably selected from one or more of N, O, S, Si, P, and B, more preferably selected from one or more of N, O, S, Si, and B, more preferably selected from one or more of N, O, S, and Si, more preferably selected from one or more of N, O, and S, particularly preferably selected from one or more of O and S, and most preferably selected from O.

[0174] Preferably, the above-mentioned compound may not contain or may contain at least one deuterium.

[0175] Preferably, the compound represented by formula (1) is represented by formula (1-1A) or formula (1-2A):

[0176]

[0177] The L5 is preferably selected from single-bonded, substituted or unsubstituted phenylene oxides;

[0178] The definitions of Ar4-Ar7 and R3-R8 are the same as above;

[0179] The definition of substituents in the phrase "substituted or unsubstituted" is the same as above;

[0180] Preferably, the above-mentioned compound may not contain or may contain at least one deuterium.

[0181] Preferably, in equation (1),

[0182] Preferably, L5 is selected from single-bonded, substituted or unsubstituted phenylene; more preferably, L5 is selected from single-bonded or phenylene; most preferably, L5 is selected from single-bonded.

[0183] Preferably, each of Ar4-Ar7 is independently selected from substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C6-C30 aryl, or substituted or unsubstituted C3-C30 heteroaryl; more preferably, each of Ar4-Ar7 is independently selected from substituted or unsubstituted C6-C30 aryl or substituted or unsubstituted C3-C30 heteroaryl; more preferably, each of Ar4-Ar7 is independently selected from substituted or unsubstituted C6-C30 aryl; the heteroatom of the heteroaryl group is preferably selected from one or more of N, O, S, Si, P, and B, more preferably from one or more of N, O, S, Si, and B, more preferably from one or more of N, O, S, and Si, more preferably from one or more of N, O, and S, particularly preferably from one or more of O and S, and most preferably from O;

[0184] Preferably, each of R3-R8 is independently selected from hydrogen, deuterium, fluorine, and C1-C10 alkyl groups; more preferably, each of R3-R8 is independently selected from hydrogen, deuterium, fluorine, methyl, ethyl, and tert-butyl; more preferably, each of R3-R8 is independently selected from hydrogen, deuterium, fluorine, and tert-butyl; even more preferably, each of R3-R8 is independently selected from hydrogen, deuterium, and tert-butyl.

[0185] Preferably, the definition of the substituent in "substituted or unsubstituted" is the same as above;

[0186] Preferably, the above-mentioned groups are unsubstituted or substituted with one or more substituents selected from deuterium, fluorine, and cyano; more preferably, the above-mentioned groups are unsubstituted or substituted with one or more substituents selected from deuterium and fluorine; more preferably, the above-mentioned groups are unsubstituted or substituted with one or more deuterium groups; most preferably, the above-mentioned groups are unsubstituted.

[0187] Preferably, the substituents in the "substituted or unsubstituted" configuration are each independently selected from one or more combinations of deuterium, fluoro, cyano, methyl, ethyl, tert-butyl, cyclohexyl, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, pyrene, fluoranyl, triphenylene, phenylene, dibenzofuranyl, and dibenzothiophene. More preferably, the substituents in the "substituted or unsubstituted" configuration are each independently selected from one or more combinations of deuterium, fluoro, tert-butyl, phenyl, biphenyl, dibenzofuranyl, and dibenzothiophene.

[0188] Preferably, in formula (1), L5 is selected from single bonds.

[0189] Preferably, in formula (1), Ar4 is preferably selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted dibenzothiophene, more preferably selected from substituted or unsubstituted phenyl, more preferably selected from unsubstituted phenyl, deuterated phenyl, fluorinated phenyl, tert-butyl substituted phenyl, and even more preferably selected from tert-butyl substituted phenyl; preferably, the substituent in "substituted or unsubstituted" is defined as above.

[0190] Preferably, in formula (1), Ar5 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted dibenzofuranyl, more preferably from substituted or unsubstituted phenyl, more preferably from unsubstituted phenyl, deuterated phenyl, fluorinated phenyl, tert-butyl substituted phenyl, and even more preferably from tert-butyl substituted phenyl; preferably, the substituent in "substituted or unsubstituted" is defined as above.

[0191] Preferably, in formula (1), Ar6 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted carbazolyl, more preferably from substituted or unsubstituted phenyl, more preferably from unsubstituted phenyl, deuterated phenyl, fluorinated phenyl, tert-butyl substituted phenyl, more preferably from deuterated phenyl, fluorinated phenyl, and even more preferably from deuterated phenyl; preferably, the substituent in "substituted or unsubstituted" is defined as above.

[0192] Preferably, in formula (1), Ar7 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted dibenzofuranyl, more preferably from substituted or unsubstituted phenyl, more preferably from unsubstituted phenyl, deuterated phenyl, fluorinated phenyl, tert-butyl substituted phenyl, and even more preferably from tert-butyl substituted phenyl; preferably, the substituent in "substituted or unsubstituted" is defined as above.

[0193] Preferably, in formula (1), the substituents in the "substituted or unsubstituted" are each independently selected from one or more combinations of deuterium, fluoro, tert-butyl, and phenyl.

[0194] Preferably, in formula (1), R3 is selected from hydrogen; R4 is selected from hydrogen; R5 is selected from hydrogen or deuterium; R6 is selected from hydrogen or deuterium; R7 is selected from hydrogen or deuterium; and R8 is selected from tert-butyl.

[0195] Preferably, in formula (1), R3 is selected from hydrogen; R4 is selected from hydrogen; R5 is selected from hydrogen; R6 is selected from hydrogen; R7 is selected from hydrogen; and R8 is selected from tert-butyl.

[0196] Preferably, the compound represented by formula (1) is as shown in 1-1 to 1-36 below:

[0197]

[0198]

[0199]

[0200]

[0201]

[0202]

[0203]

[0204]

[0205]

[0206]

[0207]

[0208] .

[0209] Preferably, the organic electroluminescent element can be a single-layer device or a multilayer device;

[0210] Preferably, in the single-layer device, the light-emitting layer comprises a compound represented by formula (1);

[0211] Preferably, in the stacked device, the at least one light-emitting layer comprises a compound represented by formula (1).

[0212] Preferably, in the organic electroluminescent element described in the second aspect above, a hole transport region is further included between the anode and the light-emitting layer, and the hole transport region includes a helical fluorene compound.

[0213] Preferably, in the organic electroluminescent element described in the second aspect above, a hole transport region is further included between the anode and the light-emitting layer, the hole transport region comprising the compound shown in formula (2).

[0214]

[0215] Equation (2)

[0216] in,

[0217] Ar1 and Ar2 are each independently selected from substituted or unsubstituted C6-C30 aryl groups and substituted or unsubstituted C3-C30 heteroaryl groups.

[0218] Ar3 is selected from substituted or unsubstituted helical fluorene groups.

[0219] L1 and L2 are each independently selected from single-bonded, substituted, or unsubstituted C6-C30 aryl groups.

[0220] L3 and L4 are each independently selected from single-bonded, substituted, or unsubstituted C6-C30 aryl groups.

[0221] Rx is selected from hydrogen, deuterium, halogen, cyano, and phenyl.

[0222] R1 and R2 are each independently selected from hydrogen, substituted or unsubstituted C1-C10 alkyl groups, substituted or unsubstituted phenyl groups, and R1 and R2 are connected to each other to form a ring structure or are not connected to each other.

[0223] p is an integer from 0 to 4. When p is 2 or greater, multiple Rx values ​​may be the same or different from each other.

[0224] The structure of formula (2) is unsubstituted or substituted with one or more substituents selected from the following: deuterium, halogen, cyano, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C1-C10 alkoxy, substituted or unsubstituted amino, substituted or unsubstituted C3-C10 cycloalkoxy, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C1-C10 alkenyl, substituted or unsubstituted C1-C10 alkynyl.

[0225] The substituents in the "substituted or unsubstituted" designation are each independently selected from one or a combination of deuterium, halogen, cyano, C1-C10 alkyl, C1-C10 alkoxy, amino, C3-C10 cycloalkoxy, C6-C30 aryl, C3-C30 heteroaryl, C1-C10 alkenyl, and C1-C10 alkynyl.

[0226] The heteroatom of the heteroaryl group is selected from one or more of N, O, S, Si, P, and B, preferably from one or more of N, O, S, Si, and P, more preferably from one or more of N, O, S, and P, more preferably from one or more of N, O, and S, particularly preferably from one or more of N and O, and most preferably from N.

[0227] Preferably, the above-mentioned compound may not contain or may contain at least one deuterium;

[0228] Preferably, the compound represented by formula (2) is not...

[0229] .

[0230] As a preferred embodiment, the structural formula of equation (2) is as follows:

[0231]

[0232] Equation (2)

[0233] in,

[0234] Ar1 is preferably selected from substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C3-C30 heteroaryl groups, more preferably selected from substituted or unsubstituted aryl groups, more preferably selected from substituted or unsubstituted phenyl groups, substituted or unsubstituted naphthyl groups, especially preferably selected from substituted or unsubstituted naphthyl groups, and most preferably selected from unsubstituted naphthyl groups.

[0235] Ar2 is preferably selected from substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C3-C30 heteroaryl groups, more preferably selected from substituted or unsubstituted phenyl groups, substituted or unsubstituted naphthyl groups, substituted or unsubstituted fluorenyl groups, substituted or unsubstituted dibenzofuranyl groups, more preferably selected from substituted or unsubstituted phenyl groups, substituted or unsubstituted naphthyl groups, and especially preferably selected from unsubstituted phenyl groups and unsubstituted naphthyl groups.

[0236] Ar3 is preferably selected from substituted or unsubstituted spirofluorenyl groups, more preferably from substituted or unsubstituted spirodifluorenyl groups, and most preferably from unsubstituted spirodifluorenyl groups;

[0237] L1 and L2 are each independently selected from single-bonded, substituted or unsubstituted C6-C30 arylene groups, and L1 and L2 cannot be single-bonded simultaneously; more preferably selected from substituted or unsubstituted C6-C30 arylene groups; more preferably selected from substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted terphenylene, substituted or unsubstituted naphthylene; particularly preferably selected from substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene; most preferably selected from unsubstituted phenylene, unsubstituted naphthylene.

[0238] L3 and L4 are each independently selected from single-bonded, substituted, or unsubstituted C6-C30 arylene groups, and L3 and L4 cannot be single-bonded simultaneously; more preferably selected from single-bonded, substituted, or unsubstituted phenylene, substituted, or unsubstituted biphenylene, substituted, or unsubstituted terphenylene, substituted, or unsubstituted naphthylene, and L3 and L4 cannot be single-bonded simultaneously; particularly preferably selected from single-bonded, substituted, or unsubstituted phenylene, substituted, or unsubstituted biphenylene, substituted, or unsubstituted naphthylene, and L3 and L4 cannot be single-bonded simultaneously; even more preferably selected from single-bonded, substituted, or unsubstituted phenylene, substituted, or unsubstituted biphenylene, and L3 and L4 cannot be single-bonded simultaneously; especially preferably selected from single-bonded, substituted, or unsubstituted phenylene, and L3 and L4 cannot be single-bonded simultaneously; most preferably selected from single-bonded, unsubstituted phenylene, and L3 and L4 cannot be single-bonded simultaneously.

[0239] R1 and R2 are each independently selected from hydrogen, substituted or unsubstituted C1-C10 alkyl groups, substituted or unsubstituted phenyl groups, or R1 and R2 are interconnected to form a ring structure or are not interconnected; more preferably, R1 and R2 are each independently selected from hydrogen, methyl, ethyl, tert-butyl, or R1 and R2 are interconnected to form a ring structure, wherein the ring structure is preferably selected from C1-C8 alkyl-substituted fluorene groups; more preferably, R1 and R2 are each independently selected from hydrogen, methyl, tert-butyl, or R1 and R2 are interconnected to form a ring structure, wherein the ring structure is preferably selected from C1-C8 alkyl-substituted fluorene groups; The elements are connected to form a ring structure, preferably selected from 9,9-dimethylfluorenyl; particularly preferably, R1 and R2 are each independently selected from hydrogen and methyl, or R1 and R2 are connected to each other to form a ring structure, preferably selected from 9,9-dimethylfluorenyl; most preferably, R1 and R2 are each independently selected from hydrogen;

[0240] The structure of formula (2) is unsubstituted or substituted with one or more substituents selected from the following: deuterium, halogen, cyano, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C1-C10 alkoxy, substituted or unsubstituted amino, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C3-C10 cycloalkoxy, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C1-C10 The alkenyl, substituted or unsubstituted C1-C10 alkynyl group; more preferably, the structure of formula (2) is unsubstituted or substituted with one or more substituents selected from the following: deuterium, fluoro, tert-butyl, phenyl; more preferably, the structure of formula (2) is unsubstituted or substituted with one or more substituents selected from the following: deuterium, fluoro, phenyl; particularly preferably, the structure of formula (2) is unsubstituted or substituted with one or more substituents selected from the following: phenyl; most preferably, the structure of formula (2) is unsubstituted;

[0241] The substituents in the "substituted or unsubstituted" group are each independently selected from one or a combination of deuterium, halogen, cyano, C1-C10 alkyl, C1-C10 alkoxy, amino, C3-C10 cycloalkyl, C3-C10 cycloalkoxy, C6-C30 aryl, C3-C30 heteroaryl, C1-C10 alkenyl, and C1-C10 alkynyl; more preferably, the substituents in the "substituted or unsubstituted" group are each independently selected from deuterium, fluoro, cyano, methyl, ethyl, tert-butyl, and cyclohexyl. The substituents are selected from one or more combinations of deuterium, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, pyrene, fluoranyl, triphenylene, phenylene, dibenzofuranyl, and dibenzothiophene; more preferably, the substituents in the "substituted or unsubstituted" category are each independently selected from one or more combinations of deuterium, fluoro, tert-butyl, phenyl, biphenyl, dibenzofuranyl, and dibenzothiophene; most preferably, the substituents in the "substituted or unsubstituted" category are each independently selected from one or more combinations of deuterium, fluoro, and phenyl.

[0242] The heteroatom of the heteroaryl group is selected from one or more of N, O, S, Si, P, and B, preferably from one or more of N, O, S, Si, and P, more preferably from one or more of N, O, S, and P, more preferably from one or more of N, O, and S, particularly preferably from one or more of N and O, and most preferably from N.

[0243] Preferably, the above-mentioned compound may not contain or may contain at least one deuterium.

[0244] Preferably, the Ar1 is selected from... , The best choice is selected from .

[0245] Preferably, the Ar3 is selected from... , , , .

[0246] Preferably, L1 is selected from... , The best choice is selected from .

[0247] Preferably, L2 is selected from... , The best choice is selected from .

[0248] Preferably, L3 is selected from... , The best choice is selected from .

[0249] Preferably, the L4 is selected from... , The best choice is selected from Preferably, the organic electroluminescent element can be a single-layer device or a multilayer device;

[0250] Preferably, in the organic electroluminescent element, the hole transport region includes one or more of a hole injection layer, a hole transport layer, and a light-emitting auxiliary layer, wherein the hole injection layer is close to the anode, the hole transport layer is located between the hole injection layer and the light-emitting auxiliary layer, the light-emitting auxiliary layer is located between the hole transport layer and the light-emitting layer, and the light-emitting auxiliary layer includes the compound shown in formula (2).

[0251] Preferably, in the organic electroluminescent element described in the first or second aspect above, the light-emitting layer further comprises a compound represented by formula (3).

[0252]

[0253] Equation (3)

[0254] R 32 R 33 R 36 R 37 Each is independently selected from hydrogen, deuterium, substituted or unsubstituted C6-C30 aryl groups, R 31 R 34 R 35 R 38 Each is independently selected from hydrogen or deuterium.

[0255] Ar 31 Ar 32 Each is independently selected from substituted or unsubstituted C6-C30 aryl groups and substituted or unsubstituted C3-C30 heteroaryl groups.

[0256] The structure of formula (3) is unsubstituted or substituted with one or more of the following substituents: deuterium, halogen, cyano, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C1-C10 alkoxy, substituted or unsubstituted amino, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C3-C10 cycloalkoxy, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C1-C10 alkenyl, substituted or unsubstituted C1-C10 alkynyl, substituted or unsubstituted silyl.

[0257] The substituents in the "substituted or unsubstituted" designation are each independently selected from one or a combination of deuterium, halogen, cyano, C1-C10 alkyl, C1-C10 alkoxy, amino, C3-C10 cycloalkyl, C3-C10 cycloalkoxy, C6-C30 aryl, C3-C30 heteroaryl, C1-C10 alkenyl, and C1-C10 alkynyl.

[0258] The heteroatom of the heteroaryl group is selected from one or more of N, O, S, Si, P, and B, preferably from one or more of N, O, S, Si, and P, more preferably from one or more of N, O, S, and P, more preferably from one or more of N, O, and S, particularly preferably from one or more of O and S, and most preferably from O.

[0259] Preferably, the above-mentioned compound may not contain or may contain at least one deuterium.

[0260] Preferably, in the compound represented by formula (3),

[0261] Preferred, R 32 R 33 R 36 R 37 Each is independently selected from hydrogen, deuterium, substituted or unsubstituted phenyl groups, R 31 R 34 R 35 R 38 Each is independently selected from either hydrogen or deuterium;

[0262] Preferably, the Ar 31 Ar 32 At least one aryl group selected from substituted or unsubstituted C6-C30;

[0263] Preferably, the substituents in the "substituted or unsubstituted" configuration are each independently selected from one or more combinations of deuterium, fluoro, cyano, methyl, ethyl, tert-butyl, cyclohexyl, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, pyrene, fluoranyl, triphenylene, phenylene, dibenzofuranyl, and dibenzothiophene; more preferably, the substituents in the "substituted or unsubstituted" configuration are each independently selected from one or more combinations of deuterium, fluoro, tert-butyl, phenyl, biphenyl, dibenzofuranyl, dibenzothiophene, and carbazole.

[0264] Preferably, in the compound represented by formula (3), R is preferred. 31 -R 38 All are selected from hydrogen or deuterium, or the R 32 R 33 R 36 R 37At least one of the compounds is selected from substituted or unsubstituted phenyl groups, and the remainder is selected from hydrogen or deuterium; more preferably, the R... 31 -R 38 All are selected from hydrogen or deuterium, or the R 32 R 33 R 36 R 37 One of the constituents is selected from a substituted or unsubstituted phenyl group, and the remainder is selected from hydrogen or deuterium; most preferably, the R group... 31 -R 38 All are selected from hydrogen or deuterium, or the R 32 R 33 R 36 R 37 One of them is selected from unsubstituted phenyl, and the rest are selected from hydrogen or deuterium; preferably, the substituents in the "substituted or unsubstituted" are defined as above.

[0265] In a preferred embodiment, in the compound represented by formula (3), R 31 -R 38 All are selected from hydrogen, or the R 31 -R 38 All are selected from hydrogen or deuterium, or the R 32 Selected from unsubstituted phenyl groups, said R 31 R 33 -R 38 All are selected from hydrogen, or the R 32 Selected from unsubstituted phenyl groups, said R 31 R 33 -R 38 All are selected from deuterium, or the R mentioned above. 32 Selected from unsubstituted phenyl groups, said R 31 R 33 R 34 All are selected from hydrogen, and the R 35 -R 38 All are selected from deuterium; preferably, the definition of substituents in the "substituted or unsubstituted" is the same as above.

[0266] Preferably, in the compound represented by formula (3), R is preferred. 31 -R 38 All are selected from hydrogen or deuterium.

[0267] Preferably, in the compound represented by formula (3), R is preferred. 31 -R 38 All are selected from hydrogen.

[0268] Preferably, in the compound represented by formula (3), R is preferred. 31 -R 38 All were selected from deuterium.

[0269] Preferably, in the compound represented by formula (3), R is preferred. 31 -R 38 All are selected from hydrogen or deuterium; preferably, the R 31 -R 38 At least one of them is selected from deuterium, and the remainder is hydrogen; more preferably, the R 31 -R 38 At least two of the R atoms are selected from deuterium, and the remainder are hydrogen; more preferably, the R atoms are selected from deuterium. 31 -R 38 At least three of the elements are selected from deuterium, and the remainder is hydrogen; more preferably, the R... 31 -R 38 At least four of the elements are selected from deuterium, and the remainder are hydrogen; more preferably, the R... 31 -R 38 At least five of them are selected from deuterium, and the remainder are hydrogen; more preferably, the R 31 -R 38 At least six of them are selected from deuterium, and the remainder are hydrogen; more preferably, the R 31 -R 38 At least seven of the elements are selected from deuterium, and the remainder are hydrogen; most preferably, the R... 31 -R 38 Selected from deuterium.

[0270] Preferably, in the compound represented by formula (3), the Ar 31 Ar is selected from substituted or unsubstituted C6-C30 aryl groups. 32 Selected from substituted or unsubstituted C3-C30 heteroaryl groups, or the Ar 31 Ar 32 All are selected from substituted or unsubstituted C6-C30 aryl groups; preferably, in the compound represented by formula (3), the Ar 31 Ar is selected from substituted or unsubstituted C6-C30 aryl groups. 32 The heteroaryl group is selected from substituted or unsubstituted C3-C30 heteroaryls; preferably, the heteroatom of the heteroaryl group is selected from one or more of N, O, S, Si, P, and B, more preferably from one or more of N, O, S, Si, and P, more preferably from one or more of N, O, S, and P, particularly preferably from one or more of O and S, and most preferably from O.

[0271] Preferably, in the compound represented by formula (3), the Ar 31Selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted biphenyl, substituted or unsubstituted phenylnaphthyl, or selected from substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzonaphthiofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazoleyl; the Ar 32 The group is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted biphenyl, substituted or unsubstituted phenylnaphthyl, or selected from substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzonaphthiofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazoleyl; preferably, the definition of the substituent when substituted is used in the phrase “substituted or unsubstituted” is the same as above.

[0272] Preferably, in the compound represented by formula (3), the Ar 31 The component is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted biphenyl, substituted or unsubstituted phenylnaphthyl, preferably selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted biphenyl, more preferably selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, more preferably selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, and most preferably selected from substituted or unsubstituted phenyl; the Ar 32 The group is selected from substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzonaphthiofuranyl, substituted or unsubstituted dibenzothiophenyl, and substituted or unsubstituted carbazoleyl, preferably from substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzonaphthiofuranyl, more preferably from substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzonaphthiofuranyl, and most preferably from substituted or unsubstituted benzonaphthiofuranyl; the definition of substituents in "substituted or unsubstituted" is the same as above.

[0273] Preferably, the benzonaphthofuranyl group is... The preferred option is The most preferred option is ; "Indicates the connection position.

[0274] Preferably, in the compound represented by formula (3), the Ar 31 Ar 32 Each of the following groups, whether substituted or unsubstituted, is independently selected:

[0275]

[0276]

[0277] ,

[0278] “ "Indicates the connection position;

[0279] Preferably, the definition of the substituent in the "substituted or unsubstituted" is the same as above.

[0280] Preferably, in the compound represented by formula (3), the Ar 31 Ar 32 Each of the following groups is independently selected from unsubstituted, partially deuterated, or fully deuterated groups:

[0281]

[0282]

[0283] ,

[0284] “ "Indicates the connection position.

[0285] Preferably, in the compound represented by formula (3), the Ar 31 Ar 32 Each of the following groups is independently selected from unsubstituted, partially deuterated, or fully deuterated groups:

[0286]

[0287]

[0288] ,

[0289] “ " indicates the connection position. Preferably, in the compound represented by formula (3), the Ar 31 Ar 32 Each of the following groups is independently selected from unsubstituted, partially deuterated, or fully deuterated groups:

[0290]

[0291]

[0292] ,

[0293] “ "Indicates the connection position.

[0294] Preferably, in the compound represented by formula (3), the Ar 31 Ar 32 Each of the following groups is independently selected from unsubstituted, partially deuterated, or fully deuterated groups:

[0295]

[0296] ;

[0297] The Ar 31 Ar 32 Each group is preferably selected independently from the following unsubstituted, partially deuterated, or fully deuterated groups:

[0298]

[0299] ;

[0300] The Ar 31 Ar 32 Each of the following groups, individually and preferably selected, is unsubstituted, partially deuterated, or fully deuterated:

[0301] ;

[0302] The Ar 31 Ar 32 Each of the following groups, individually and preferably selected, is unsubstituted, partially deuterated, or fully deuterated:

[0303] ;

[0304] The Ar 31 Ar 32 More preferably, each of the following groups is independently selected from unsubstituted, partially deuterated, or fully deuterated groups:

[0305] ;

[0306] “ "Indicates the connection position.

[0307] Preferably, in the compound represented by formula (3), the Ar 31 Ar 32 Each of the following groups is independently selected from unsubstituted, partially deuterated, or fully deuterated groups:

[0308]

[0309] ;

[0310] The Ar 31 Ar 32 Each group is preferably selected independently from the following unsubstituted, partially deuterated, or fully deuterated groups:

[0311] ;

[0312] The Ar 31 Ar 32 Each of the following groups, individually and preferably selected, is unsubstituted, partially deuterated, or fully deuterated:

[0313] ;

[0314] The Ar 31 Ar 32 More preferably, each of the following groups is independently selected from unsubstituted, partially deuterated, or fully deuterated groups:

[0315] ;

[0316] The Ar 31 Ar 32 Each group, independently and particularly preferably selected from unsubstituted, partially deuterated, or fully deuterated groups, includes the following:

[0317] ;

[0318] The Ar 31 Ar 32 Each of the following groups, independently and most preferably selected, is unsubstituted, partially deuterated, or fully deuterated:

[0319] ;

[0320] “ "Indicates the connection position.

[0321] Preferably, in the compound represented by formula (3), the Ar 31 Ar 32 Each of the following groups is independently selected from unsubstituted, partially deuterated, or fully deuterated groups:

[0322] ;

[0323] The Ar 31 Ar 32Each group is preferably selected independently from the following unsubstituted, partially deuterated, or fully deuterated groups:

[0324] ;

[0325] The Ar 31 Ar 32 Each of the following groups, individually and preferably selected, is unsubstituted, partially deuterated, or fully deuterated:

[0326] ;

[0327] The Ar 31 Ar 32 More preferably, each of the following groups is independently selected from unsubstituted, partially deuterated, or fully deuterated groups:

[0328] ;

[0329] The Ar 31 Ar 32 Each group, independently and particularly preferably selected from unsubstituted, partially deuterated, or fully deuterated groups, includes the following:

[0330] ;

[0331] “ "Indicates the connection position.

[0332] Preferably, in the compound represented by formula (3), the Ar 31 Ar 32 Each of the following groups is independently selected from unsubstituted, partially deuterated, or fully deuterated groups:

[0333] ;

[0334] “ "Indicates the connection position.

[0335] Preferably, in the compound represented by formula (3), the Ar 31 Ar 32 Each of the following groups is independently selected from unsubstituted, partially deuterated, or fully deuterated groups:

[0336] ;

[0337] “ "Indicates the connection position.

[0338] Preferably, in the compound represented by formula (3), the Ar 31 Selected from the following groups that are unsubstituted, partially deuterated, or fully deuterated:

[0339]

[0340]

[0341] ;

[0342] The Ar 31 Preferably, the following groups are selected from unsubstituted, partially deuterated, or fully deuterated groups:

[0343]

[0344]

[0345] ;

[0346] The Ar 31 Preferably, the following groups are selected from unsubstituted, partially deuterated, or fully deuterated groups:

[0347] ,

[0348] The Ar 31 Preferably, the following groups are selected from unsubstituted, partially deuterated, or fully deuterated groups:

[0349] ,

[0350] The Ar 31 More preferably, the following groups are selected from unsubstituted, partially deuterated, or fully deuterated groups:

[0351] ,

[0352] The Ar 31 Particularly preferred are the following groups selected from unsubstituted, partially deuterated, or fully deuterated groups:

[0353] ,

[0354] The Ar 31 Particularly preferred are the following groups selected from unsubstituted, partially deuterated, or fully deuterated groups:

[0355] ,

[0356] The Ar 31 Particularly preferred are the following groups selected from unsubstituted, partially deuterated, or fully deuterated groups:

[0357] ,

[0358] “ "Indicates the connection position.

[0359] Preferably, in the compound represented by formula (3), the Ar 32 Selected from the following groups that are unsubstituted, partially deuterated, or fully deuterated:

[0360]

[0361]

[0362] ;

[0363] The Ar 32 Preferably, the following groups are selected from unsubstituted, partially deuterated, or fully deuterated groups:

[0364]

[0365]

[0366] ;

[0367] The Ar 32 Preferably, the following groups are selected from unsubstituted, partially deuterated, or fully deuterated groups:

[0368]

[0369] ;

[0370] The Ar 32 Preferably, the following groups are selected from unsubstituted, partially deuterated, or fully deuterated groups:

[0371] ;

[0372] The Ar 32 More preferably, the following groups are selected from unsubstituted, partially deuterated, or fully deuterated groups:

[0373] ;

[0374] The Ar 32 Particularly preferred are the following groups selected from unsubstituted, partially deuterated, or fully deuterated groups:

[0375] ;

[0376] The Ar 32 The most preferred group is selected from the following groups that are unsubstituted, partially deuterated, or fully deuterated:

[0377] ;

[0378] “ "Indicates the connection position.

[0379] Preferably, the compound represented by formula (3) is as follows:

[0380]

[0381]

[0382]

[0383]

[0384]

[0385]

[0386]

[0387]

[0388]

[0389]

[0390]

[0391]

[0392]

[0393]

[0394]

[0395]

[0396]

[0397] .

[0398] Preferably, the organic electroluminescent element can be a single-layer device or a multilayer device.

[0399] Preferably, in the single-layer device, the light-emitting layer includes the compound shown in formula (1) and the compound shown in formula (3), or in the single-layer device, the light-emitting layer includes the compound shown in formula (3) and the hole transport region includes the compound shown in formula (2), or in the single-layer device, the light-emitting layer includes the compound shown in formula (1) and the compound shown in formula (3) and the hole transport region includes the compound shown in formula (2).

[0400] Preferably, in the stacked device, the at least one light-emitting layer comprises the compound shown in formula (1) and the compound shown in formula (3), or in the stacked device, at least one light-emitting layer comprises the compound shown in formula (1), and at least one light-emitting layer other than the light-emitting layer comprising the compound shown in formula (2) comprises the compound shown in formula (3), and in the stacked device, the at least one hole transport region comprises the compound shown in formula (2), or in the stacked device, the at least one light-emitting layer comprises the compound shown in formula (1) and the compound shown in formula (3), and at least one hole transport region comprises the compound shown in formula (2), or in the stacked device, at least one light-emitting layer comprises the compound shown in formula (1), and at least one light-emitting layer other than the light-emitting layer comprising the compound shown in formula (2) comprises the compound shown in formula (3), and at least one hole transport region comprises the compound shown in formula (2).

[0401] Thirdly, preferably, an organic electroluminescent element includes an anode, a cathode, and an organic functional layer including a light-emitting layer located between the anode and the cathode, wherein a hole transport region is included between the anode and the light-emitting layer, the light-emitting layer includes a compound represented by formula (1), and the hole transport region includes a compound represented by formula (2).

[0402]

[0403] Equation (1)

[0404] A is “ " indicates the connection position with N, where n is an integer between 0 and 1.

[0405] Ar4-Ar7 are each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl.

[0406] Alternatively, A and Ar4 may link together to form substituted or unsubstituted carbazole groups.

[0407] L5 is selected from single-bonded, substituted, or unsubstituted C6-C30 aryl groups.

[0408] R3-R8 are each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C10 alkyl groups.

[0409] When n is 1, the compound represented by formula (1) contains at least one deuterium or halogen.

[0410] When n is 0, the compound shown in formula (1) contains at least one halogen.

[0411] The substituents in the "substituted or unsubstituted" designation are each independently selected from one or a combination of deuterium, halogen, cyano, C1-C10 alkyl, C1-C10 alkoxy, amino, C3-C10 cycloalkyl, C3-C10 cycloalkoxy, C6-C30 aryl, C3-C30 heteroaryl, C1-C10 alkenyl, C1-C10 alkynyl, silyl having a C1-C10 alkyl substituted group, and silyl having an aryl substituted group with 6-30 carbon atoms.

[0412] The heteroatom of the heteroaryl group is selected from one or more of N, O, S, Si, P, and B, preferably from one or more of N, O, S, Si, and B, more preferably from one or more of N, O, S, and Si, more preferably from one or more of N, O, and S, particularly preferably from one or more of O and S, and most preferably from O.

[0413]

[0414] Equation (2)

[0415] Ar1 is selected from substituted or unsubstituted naphthyl groups.

[0416] Ar2 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted dibenzofuranyl.

[0417] Ar3 is selected from substituted or unsubstituted helical fluorene groups.

[0418] L1 and L2 are each independently selected from substituted or unsubstituted phenyl or substituted or unsubstituted naphthyl groups.

[0419] L3 and L4 are each independently selected from single-bonded, substituted, or unsubstituted phenylene compounds. L3 and L4 cannot both be single bonds.

[0420] R1 and R2 are each independently selected from hydrogen, substituted or unsubstituted C1-C10 alkyl groups, substituted or unsubstituted phenyl groups, and R1 and R2 are connected to each other to form a ring structure or are not connected to each other.

[0421] The substituents in the "substituted or unsubstituted" designation are each independently selected from one or a combination of deuterium, halogen, cyano, C1-C10 alkyl, C1-C10 alkoxy, amino, C3-C10 cycloalkyl, C3-C10 cycloalkoxy, C6-C30 aryl, C3-C30 heteroaryl, C1-C10 alkenyl, and C1-C10 alkynyl.

[0422] The heteroatom of the heteroaryl group is selected from one or more of N, O, S, Si, P, and B, preferably from one or more of N, O, S, Si, and P, more preferably from one or more of N, O, S, and P, more preferably from one or more of N, O, and S, particularly preferably from one or more of N and O, and most preferably from one or more of N.

[0423] Preferably, the above-mentioned compound may not contain or may contain at least one deuterium.

[0424] Preferably, the definition of formula (1) can be the same as that defined in the first aspect of the present invention.

[0425] Preferably, the definition of formula (2) can be the same as that defined in the second aspect of the present invention described above.

[0426] Preferably, the organic electroluminescent element can be a single-layer device or a multilayer device.

[0427] Preferably, in the organic electroluminescent element, the hole transport region includes one or more of a hole injection layer, a hole transport layer, and a light-emitting auxiliary layer. The hole injection layer is close to the anode, the hole transport layer is located between the hole injection layer and the light-emitting auxiliary layer, the light-emitting auxiliary layer is located between the hole transport layer and the light-emitting layer, the light-emitting layer includes the compound shown in formula (1), and the light-emitting auxiliary layer includes the compound shown in formula (2).

[0428] Preferably, in the single-layer device, the light-emitting layer comprises the compound shown in formula (1), and the light-emitting auxiliary layer comprises the compound shown in formula (2).

[0429] Preferably, in the stacked device, the at least one light-emitting layer comprises the compound shown in formula (1), and the at least one light-emitting auxiliary layer comprises the compound shown in formula (2).

[0430] Fourthly, an electronic device, including a display or lighting device, comprising any of the organic electroluminescent elements described in this invention.

[0431] Of all the compounds involved in the first to fourth aspects mentioned above, the halogen is preferably F, Br, Cl, or I;

[0432] And / or, the C1-C10 alkyl group is preferably methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, sec-butyl, n-pentyl, neopentyl, isopentyl, n-hexyl, n-heptyl, n-octyl, n-decyl, isooctyl, nonyl, 2-ethylhexyl;

[0433] And / or, the aryl group of the C6-C30 is preferably phenyl, biphenyl, terphenyl, naphthyl, anthracene, tetraphenyl, phenanthryl, fluorenyl, indene, pyrene, perylene, fluoranyl, benzophenanthryl, triphenylene, phenylene, spirofluorenyl, benzopyrene, or benzo[a] ...

[0434] And / or, the arylene group of the C6-C30 is preferably phenylene, biphenylene, terphenylene, naphthylene, anthracene, tetraphenylene, phenanthrene, fluorene, indene, pyrene, perylene, fluoranthylene, benzophenanthrene, trimethyleneene, cyclophenylene, spirofluorene, benzopyrene, benzo[a]cyclo ...

[0435] And / or, the heteroaryl group of the C3-C30 is preferably thienyl, furanyl, pyrroleyl, thiazolyl, oxazolyl, imidazolyl, pyrazolyl, triazolyl, benzothienyl, benzofuranyl, indolyl, isoindolyl, benzothiazolyl, benzooxazolyl, benzoimidazolyl, benzotriazolyl, purinyl, carbazoleyl, dibenzothienyl, dibenzofuranyl, pyridyl, pyrimidinyl, triazinyl, phenazinyl, quinolinyl, isoquinolinyl, naphridinyl, acridineyl, phenanthrolinel, carbolinyl, bipyridinyl, terpyridinyl;

[0436] And / or, the alkoxy groups of the C1-C10 are preferably methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentoxy, neopentoxy, isopentoxy, n-hexyloxy, n-octoxy, isooctoxy, n-decoxy, n-nonoxy, n-heptoxy;

[0437] And / or, the C3-C10 cycloalkyl group is preferably cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclooctyl, cyclononyl, cyclodecyl, norbornyl, or adamantane;

[0438] And / or, the cycloalkoxy group of the C3-C10 is preferably cyclopropoxy, cyclobutoxy, cyclopentoxy, cyclohexyloxy, cycloheptoxy, cyclooctoxy, cyclononoxy, or cyclodecoxy;

[0439] And / or, the aryloxy group of the C6-C30 is preferably phenoxy, toluoxy, biphenyloxy, naphthoxy, anthraceneoxy, phenanthroxy, or benzyloxy.

[0440] According to the above-mentioned compounds containing polycyclic aryl structures, the halogen is preferably F, Br, Cl, or I, more preferably F, Br, or Cl, more preferably F or Cl, and most preferably F.

[0441] According to the above-mentioned compounds containing polycyclic aryl structures, the C1-C10 alkyl group is preferably methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, sec-butyl, n-pentyl, neopentyl, isopentyl, n-hexyl, n-heptyl, n-octyl, n-decyl, isooctyl, nonyl, 2-ethylhexyl, more preferably methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, sec-butyl, n-pentyl, neopentyl, isopentyl, n-hexyl, n-octyl, n-heptane, and more preferably methyl Ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, sec-butyl, n-pentyl, neopentyl, isopentyl, n-hexyl, more preferably methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, sec-butyl, n-pentyl, particularly preferably methyl, ethyl, n-propyl, isopropyl, tert-butyl, n-pentyl, especially preferably methyl, ethyl, n-propyl, isopropyl, tert-butyl, particularly preferably methyl, ethyl, tert-butyl, particularly preferably methyl, ethyl, most preferably methyl.

[0442] According to the above-mentioned compounds containing polycyclic aryl structures, the C6-C30 aryl group is preferably phenyl, biphenyl, terphenyl, naphthyl, anthracene, tetraphenyl, phenanthryl, fluorenyl, indene, pyrene, perylene, fluoranthyl, benzo[a]phenanthryl, triphenylene, phenylene, spirofluorenyl, benzo[a]pyrene, benzo[a]phenylene, more preferably phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthryl, fluoranthyl, triphenylene, perylene, pyrene, benzo[a]pyrene, phenylene, benzo[a]phenylene, more preferably phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthryl, more preferably phenyl, biphenyl, naphthyl, anthracene, phenanthryl, more preferably phenyl, biphenyl, naphthyl, phenanthryl, particularly preferably biphenyl, phenyl, naphthyl, especially preferably phenyl, naphthyl, and most preferably phenyl.

[0443] According to the above-mentioned compounds containing polycyclic aryl structures, the C6-C30 arylene group is preferably phenylene, biphenylene, terphenylene, naphthylene, anthracene, tetraphenylene, phenanthrene, fluorene, indene, pyrene, perylene, fluorene-anthryl, benzo[a]phenanthryl, triphenylene, spirofluorene, benzo[a]pyrene, benzo[a]phenanthryl, and more preferably phenylene, biphenylene, terphenylene, naphthylene, anthracene, phenanthrene, and fluorene-anthryl. Anthrayl, triphenylene, perylene, pyrene, benzo[a]pyrene, benzo[a]benzo[a]benzo[a]phenylene, more preferably phenylene, biphenylene, terphenylene, naphthylene, anthraylene, phenanthrene, more preferably phenylene, biphenylene, naphthylene, anthraylene, phenanthrene, more preferably phenylene, biphenylene, naphthylene, phenanthrene, particularly preferably biphenylene, phenylene, naphthylene, especially preferably phenylene, naphthylene, most preferably phenylene.

[0444] According to the above-mentioned compounds containing polycyclic aryl structures, the C3-C30 heteroaryl group is preferably thienyl, furanyl, pyrroleyl, thiazolyl, oxazolyl, imidazolyl, pyrazolyl, triazolyl, benzothienyl, bipyridyl, terpyridyl, benzofuranyl, indolyl, isoyindolyl, benzothiazolyl, benzooxazolyl, benzimidazolyl, benzotriazolyl, purinyl, carbazoleyl, dibenzothienyl, dibenzofuranyl, pyridyl, pyrimidinyl, triazinyl, phenazinyl, quinolinyl, isoquinolinyl, naphridyl, acridineyl, phenanthrolinel, carbolinyl, and more preferably thienyl, furanyl, bipyridyl, terpyridyl, pyridyl, etc. The compounds are pyrrolyl, imidazolyl, pyrazolyl, benzothiophene, benzofuranyl, benzoimidazolyl, carbazole, dibenzothiophene, dibenzofuranyl, pyridyl, pyrimidinyl, triazine, phenazine, quinolinyl, isoquinolinyl, phenanthroline, more preferably pyrrolyl, imidazolyl, carbazole, dibenzothiophene, bipyridyl, terpyridyl, dibenzofuranyl, pyridyl, pyrimidinyl, triazine, particularly preferably dibenzothiophene, dibenzofuranyl, pyridyl, triazine, pyrimidinyl, especially preferably dibenzothiophene, dibenzofuranyl, pyridyl, pyrimidinyl, particularly preferably pyridyl, pyrimidinyl, most preferably pyridyl.

[0445] According to the above-mentioned compounds containing polycyclic aryl structures, the C1-C10 alkoxy group is preferably methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentoxy, neopentoxy, isopentoxy, n-hexyloxy, n-octoxy, isooctoxy, n-decoxy, n-nonoxy, n-heptoxy, more preferably methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentoxy, neopentoxy, isopentoxy, n-hexyloxy, n-octyloxy, n-heptoxy, and more preferably methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentoxy, neopentoxy, isopentoxy, n-hexyloxy, more preferably methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentoxy, particularly preferably methoxy, ethoxy, n-propoxy, isopropoxy, tert-butoxy, n-pentoxy, especially preferably methoxy, ethoxy, n-propoxy, isopropoxy, tert-butoxy, particularly preferably methoxy, ethoxy, tert-butoxy, particularly preferably methoxy, ethoxy, tert-butoxy, most preferably methoxy.

[0446] According to the above-mentioned compounds containing polycyclic aryl structures, the C3-C10 cycloalkyl group is preferably cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclooctyl, cyclononyl, cyclodecyl, norbornyl, or adamantane; more preferably cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, or adamantane; more preferably cyclopropyl, cyclopentyl, cyclohexyl, or adamantane; particularly preferably cyclopropyl, cyclopentyl, or cyclohexyl; especially preferably cyclohexyl or cyclopropyl; and most preferably cyclohexyl.

[0447] According to the above-mentioned compounds containing polycyclic aryl structures, the C3-C10 cycloalkoxy group is preferably cyclopropoxy, cyclobutoxy, cyclopentoxy, cyclohexyloxy, cycloheptoxy, cyclooctoxy, cyclononoxy, or cyclodecoxy, more preferably cyclopropoxy, cyclobutoxy, cyclopentoxy, cyclohexyloxy, or cycloheptoxy, more preferably cyclopropoxy, cyclobutoxy, cyclopentoxy, or cyclohexyloxy, particularly preferably cyclopropoxy, cyclobutoxy, or cyclopentoxy, especially preferably cyclopropoxy or cyclopentoxy, and most preferably cyclopropoxy.

[0448] According to the above-mentioned compounds containing polycyclic aryl structures, the aryloxy group of C6-C30 is preferably phenoxy, toluoxy, biphenyloxy, naphthoxy, anthraceneoxy, phenanthroxy, or benzyloxy, more preferably phenoxy, toluoxy, or benzyloxy, more preferably phenoxy or toluoxy, and most preferably phenoxy.

[0449] According to the above-mentioned compounds containing polycyclic aryl structures, the substituents in the phrase "substituted or unsubstituted" are preferably each independently selected from deuterium, fluorinyl, cyano, methyl, ethyl, propyl, n-butyl, tert-butyl, cyclopentyl, cyclohexyl, adamantyl, fluorenyl, spirofluorenyl, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthryl, pyrene, fluoranyl, triphenylene, phenylene, dibenzofuranyl, carbazoyl, phenantholinyl, dibenzothiophene, pyrroleyl, furanyl, triazinyl, pyrazinyl, pyridazinyl, oxazolyl, thiophene, benzothiophene, benzofuranyl, benzooxazolyl, imidazoyl, quinazolinyl, methoxy, ethoxy, propoxy, n-butoxy, tert-butoxy, indoleyl, indazole, thiophene, pyridine The compounds are selected from one or more combinations of deuterium, fluorine, cyano, methyl, ethyl, propyl, tert-butyl, cyclopentyl, cyclohexyl, adamantyl, fluorenyl, phenyl, biphenyl, naphthyl, anthracene, dibenzofuranyl, carbazole, phenantholinyl, dibenzothiophene, pyrroleyl, furanyl, triazinyl, oxazolyl, thiophene, benzothiophene, benzofuranyl, benzooxazolyl, imidazolyl, thiophene, pyridyl, pyrimidinyl, quinoline, isoquinoline, and pyridyl; more preferably, they are selected from one or more combinations of deuterium, fluorine, cyano, methyl, tert-butyl, cyclopentyl, cyclohexyl, adamantyl, phenyl, biphenyl, naphthyl, anthracene, dibenzofuranyl, dibenzothiophene, and pyridyl. The compound is selected from one or more combinations of pyrolyl, furanyl, thiophenel, benzothiophenel, benzofuranyl, pyridyl, pyrimidinyl, quinolinyl, and isoquinolinyl; particularly preferably selected from one or more combinations of deuterium, fluorine, cyano, methyl, cyclopentyl, cyclohexyl, phenyl, biphenyl, naphthyl, anthracenel, dibenzofuranyl, dibenzothiophenel, pyridyl, pyrimidinyl, quinolinyl, and isoquinolinyl; particularly preferably selected from one or more combinations of deuterium, fluorine, cyano, methyl, phenyl, biphenyl, naphthyl, anthracenel, dibenzofuranyl, dibenzothiophenel, pyridyl, pyrimidinyl, quinolinyl, and isoquinolinyl, especially preferably selected from deuterium, fluorine, cyano, methyl, phenyl, dibenzofuranyl, pyridyl, pyrimidinyl, quinolinyl, and isoquinolinyl. One or more combinations thereof; particularly preferably selected from one or more combinations of deuterium, fluorine, cyano, methyl, phenyl, dibenzofuranyl, pyridyl, pyrimidinyl, quinolinyl, and isoquinolinyl; particularly preferably selected from one or more combinations of deuterium, fluorine, cyano, methyl, phenyl, dibenzofuranyl, pyridyl, and pyrimidinyl; particularly preferably selected from one or more combinations of deuterium, fluorine, cyano, methyl, phenyl, dibenzofuranyl, and pyridyl; particularly preferably selected from one or more combinations of deuterium, fluorine, cyano, methyl, phenyl, and pyridyl; particularly preferably selected from one or more combinations of deuterium, fluorine, methyl, and phenyl; particularly preferably selected from one or more combinations of deuterium, fluorine, methyl, and phenyl.Particularly preferred are those selected from one or more combinations of deuterium, fluorine, and phenyl; particularly preferred are those selected from one or more combinations of deuterium and phenyl; most preferred are deuterium.

[0450] The beneficial effects of this invention are:

[0451] 1. When the organic electroluminescent element of the present invention contains the compound of formula (2), the increased length of the aromatic group in its structure improves the stability of the molecule, thereby enhancing the device performance. In particular, the performance improvement is more obvious when the compound of formula (1) is applied to blue fluorescent devices.

[0452] 2. The light-emitting layer of the organic electroluminescent element of the present invention comprises a compound of formula (1). The method of introducing deuterated or fluorinated biphenyl or dibenzofuran into the compound can improve thermal stability and exhibit better carrier transport capability. In addition, the compound of formula (1) can also effectively improve the energy transfer performance and exciton utilization efficiency between it and the host. The nitrogen-containing steric hindrance group can effectively reduce the interaction force between light-emitting molecules, thereby achieving the effects of low driving voltage, high current efficiency and long service life.

[0453] 3. The light-emitting layer of the organic electroluminescent element of the present invention comprises a compound of formula (1). Since the compound contains fluorine-substituted groups, especially fluorine-substituted phenyl groups, trifluoromethyl-substituted phenyl groups, etc., in some specific structures, it can stably emit purer blue light, and at the same time improve the stability and heat resistance of the device to avoid the decomposition of the compound during evaporation and use.

[0454] 4. When the organic electroluminescent element of the present invention comprises a blue fluorescent host compound of formula (3), it contains an anthracene structure that plays a core role, especially when one side of the anthracene is an aryl group and the other side is a dibenzofuran or its derivative structure (particularly ), which draws out coupling energy, and when used together with the compound of formula (1) and / or the compound of formula (2) in the same organic electroluminescent element, it can reduce the driving voltage of the organic light-emitting device and improve the lifetime characteristics. In particular, when the organic electroluminescent element of the present invention includes the blue fluorescent host compound of formula (3), the compound of formula (1) and the compound of formula (2), it can significantly reduce the driving voltage of the organic light-emitting device, improve efficiency and improve lifetime.

[0455] 5. The organic electroluminescent element of the present invention, containing a compound of formula (2), exhibits excellent performance when using a compound with a specific core structure as the light-emitting auxiliary layer material—it can better confine charge carriers within the light-emitting layer, thereby reducing the efficiency decrease caused by charge carrier overflow. It is suitable for preparing high-performance organic electroluminescent elements, especially when using… or When using compounds with specific parent nucleus structures, the organic electroluminescent elements prepared exhibit significantly superior performance;

[0456] 6. The organic electroluminescent element of the present invention contains a compound of formula (2), particularly when using... Organic electroluminescent devices made from compounds with specific core structures exhibit lower driving voltages, wherein the compounds of the present invention use compounds without... The side chains exhibit higher current efficiency and lifetime; furthermore, when the specific side chains of the compounds of the present invention are... for or At that time, relative to a specific sidechain for or At that time, it has a significant lifespan advantage. Attached Figure Description

[0457] Figure 1 This is a schematic diagram of the structure of the organic electroluminescent element described in Example 1; wherein: Figure 1 The markings in the diagram represent: 1. Anode, 2. Hole injection layer, 3. Hole transport layer, 4. Luminescent auxiliary layer, 5. Luminescent layer, 6. Electron transport layer, 7. Electron injection layer, and 8. Cathode. Markers 2, 3, and 4 are in the hole transport region, and marks 6 and 7 are in the electron transport region.

[0458] Figure 2 This is the mass spectrum (LC-MS) of compound 1-1 prepared in Synthesis Example 1 of the compound preparation examples.

[0459] Figure 3 The NMR (nuclear magnetic resonance) of compound 1-1 prepared in Synthesis Example 1 of the compound preparation examples is shown. 1 1H NMR spectrum.

[0460] Figure 4 This is the mass spectrum (LC-MS) of compounds 1-2 prepared in Synthesis Example 2 of the compound preparation examples.

[0461] Figure 5 The NMR spectra of compounds 1-2 prepared in Synthesis Example 2 of the compound preparation examples are shown. 1 1H NMR spectrum.

[0462] Figure 6 This is the mass spectrum (LC-MS) of compounds 1-34 prepared in Synthesis Example 3 of the compound preparation examples.

[0463] Figure 7 The NMR spectra of compounds 1-34 prepared in Synthesis Example 3 of the compound preparation examples are shown. 11H NMR spectrum.

[0464] Figure 8 This is the mass spectrum (LC-MS) of compounds 1-35 prepared in Synthesis Example 4 of the compound preparation examples.

[0465] Figure 9 The NMR spectra of compounds 1-35 prepared in Synthesis Example 4 of the compound preparation examples are shown. 1 1H NMR spectrum.

[0466] Figure 10 This is the mass spectrum (LC-MS) of compounds 1-28 prepared in Synthesis Example 5 of the compound preparation examples.

[0467] Figure 11 The NMR spectra of compounds 1-28 prepared in Synthesis Example 5 of the compound preparation examples are shown. 1 1H NMR spectrum.

[0468] Figure 12 This is the mass spectrum (LC-MS) of compounds 1-36 prepared in Synthesis Example 6 of the compound preparation examples.

[0469] Figure 13 The NMR spectra of compounds 1-36 prepared in Synthesis Example 6 of the compound preparation examples are shown. 1 1H NMR spectrum.

[0470] Figure 14 This is the mass spectrum (LC-MS) of compound 2-1 prepared in synthesis example 7 of the compound preparation examples.

[0471] Figure 15 The NMR (nuclear magnetic resonance) of compound 2-1 prepared in Synthesis Example 7 of the compound preparation examples is shown. 1 1H NMR spectrum.

[0472] Figure 16 The NMR spectra of compounds 2-19 prepared in Synthesis Example 8 of the compound preparation examples are shown. 1 1H NMR spectrum.

[0473] Figure 17 This is the mass spectrum (LC-MS) of compounds 2-20 prepared in Synthesis Example 9 of the compound preparation examples.

[0474] Figure 18 The NMR spectra of compounds 2-20 prepared in Synthesis Example 9 of the compound preparation examples are shown. 1 1H NMR spectrum.

[0475] Figure 19The NMR spectra of compounds 2-23 prepared in Synthesis Example 10 of the compound preparation examples are shown. 1 ¹H NMR spectrum.

[0476] Figure 20 This is the mass spectrum (LC-MS) of compounds 2-25 prepared in Synthesis Example 11 of the compound preparation examples.

[0477] Figure 21 The NMR spectra of compounds 2-25 prepared in Synthesis Example 11 of the compound preparation examples are shown. 1 ¹H NMR spectrum.

[0478] Figure 22 This is the mass spectrum (LC-MS) of compounds 1-91 prepared in Synthesis Example 12 of the compound preparation examples.

[0479] Figure 23 The NMR spectra of compounds 1-91 prepared in Synthesis Example 12 of the compound preparation examples are shown. 1 ¹H NMR spectrum.

[0480] Figure 24 This is the mass spectrum (LC-MS) of compounds 2-3 prepared in Synthesis Example 13 of the compound preparation examples.

[0481] Figure 25 The NMR spectra of compounds 2-3 prepared in Synthesis Example 13 of the compound preparation examples are shown. 1 1H NMR spectrum.

[0482] Figure 26 This is the mass spectrum (LC-MS) of compounds 1-94 prepared in Synthesis Example 14 of the compound preparation examples.

[0483] Figure 27 The NMR spectra of compounds 1-94 prepared in Synthesis Example 14 of the compound preparation examples are shown. 1 ¹H NMR spectrum.

[0484] Figure 28 This is the mass spectrum (LC-MS) of compound 1-112 prepared in synthesis example 15 of the compound preparation examples.

[0485] Figure 29 The NMR spectra of compounds 1-112 prepared in Synthesis Example 15 of the compound preparation examples are shown. 1 ¹H NMR spectrum.

[0486] Figure 30 This is the mass spectrum (LC-MS) of compound 1-118 prepared in synthesis example 16 of the compound preparation examples.

[0487] Figure 31 The NMR spectra of compounds 1-118 prepared in Synthesis Example 16 of the compound preparation examples are shown. 1 ¹H NMR spectrum.

[0488] Figure 32 This is the mass spectrum (LC-MS) of compounds 1-44 prepared in Synthesis Example 17 of the compound preparation examples.

[0489] Figure 33 The NMR spectra of compounds 1-44 prepared in Synthesis Example 17 of the compound preparation examples are shown. 1 ¹H NMR spectrum. Detailed Implementation

[0490] Exemplary embodiments will now be described in detail, examples of which are illustrated in the accompanying drawings, wherein the same reference numerals always refer to the same elements. In this respect, these exemplary embodiments may take different forms and should not be construed as limited to the description set forth herein. Therefore, the exemplary embodiments are described below only by reference to the accompanying drawings to illustrate aspects. As used herein, the term “and / or” includes any and all combinations of one or more of the associated enumerated items. Expressions such as “at least one” modify the entire list of elements when preceding or following the list of elements, but do not modify individual elements of the list.

[0491] It will be further understood that the terms “comprising” or “including” as used in this specification indicate the presence of the stated features, regions, integrals, steps, operations, elements, and / or components, but do not preclude the presence or addition of one or more additional features, regions, integrals, steps, operations, elements, components, and / or sets thereof.

[0492] Unless otherwise defined, all terms used herein (including technical and scientific terms) have the same meaning as commonly understood by one of ordinary skill in the art to which this general inventive concept pertains. It will be further understood that terms, such as those defined in commonly used dictionaries, should be interpreted as having meanings consistent with their meanings in the relevant field and in the context of this disclosure, and will not be interpreted in an idealized or overly formal sense unless clearly defined herein.

[0493] The present invention will be further illustrated below with reference to specific embodiments. It should be understood that these embodiments are for illustrative purposes only and are not intended to limit the scope of protection of the present invention. Furthermore, it should be understood that after reading the disclosure of this invention, those skilled in the art can make various modifications or alterations to the present invention, and these equivalent forms also fall within the scope of protection defined by this invention.

[0494] In this invention, unless otherwise specified, all parts and percentages are by weight, and the equipment and raw materials used are commercially available or commonly used in the art. Unless otherwise specified, the methods in the following embodiments are conventional methods in the art.

[0495] Unless otherwise specified, the experimental methods used in the following examples are conventional methods; the starting materials, reaction materials, intermediates, reagents, and materials used in the following examples are all commercially available unless otherwise specified.

[0496] Terminology Explanation

[0497] As used in this invention, the term "halogen" may include fluorine, chlorine, bromine, or iodine.

[0498] As used in this invention, the term "C1-C10 alkyl" refers to a monovalent substituent derived from a straight-chain or branched saturated hydrocarbon having 1 to 10 carbon atoms, examples of which include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, and hexyl.

[0499] In this invention, the term "C1-C10 alkoxy" refers to a monovalent substituent having 1 to 10 carbon atoms, represented by RO-, where R refers to an alkyl group having 1 to 10 carbon atoms. Specific examples include, but are not limited to, methoxy, ethoxy, n-propoxy, isopropoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentoxy, neopentoxy, isopentoxy, n-hexyloxy, etc.

[0500] As in this invention, the term "C3-C" 10 "Cycloalkyl" refers to a monovalent substituent derived from a monocyclic or polycyclic nonaromatic hydrocarbon having 3 to 10 carbon atoms. Examples of such cycloalkyl groups include, but are not limited to, cyclopropane, cyclobutane, cyclopentane, cyclohexane, norbornyl, and adamantane.

[0501] In this invention, the term "C3-C10 cycloalkoxy" refers to a monovalent substituent having 3 to 10 carbon atoms, represented by RO-, where R refers to a cycloalkyl group having 3 to 10 carbon atoms. Specific examples include, but are not limited to, cyclopropoxy, cyclobutoxy, cyclopentoxy, and cyclohexoxy.

[0502] As used herein, the term "C6-C30 aryl" refers to a monovalent substituent derived from an aromatic hydrocarbon having a single ring or a combination of two or more rings and having 6 to 30 carbon atoms. Further, such an aryl group may have two or more rings simply side-attached to or fused together with each other. Examples of such aryl groups include, but are not limited to, phenyl, biphenyl, naphthyl, phenanthryl, anthracene, pyrene, triphenylene, fluoranthyl, dimethyl-9,9-dimethylfluorene, 9,9-diphenylfluorene, spirodifluorene, etc.

[0503] As used in this invention, the term "arylene" refers to a divalent aryl group derived by removing one hydrogen atom from an "aryl" group, for example, a phenyl group by removing one hydrogen atom to form a phenylene group, and a naphthyl group by removing one hydrogen atom to form a naphthylene group.

[0504] As used in this invention, the term "C3-C30 heteroaryl" refers to a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 3 to 30 carbon atoms. In this connection, at least one carbon in the ring, preferably 1 to 3 carbons, is substituted with a heteroatom, such as N, O, S, P, B, or Si. Furthermore, such a heteroaryl can have a form in which two or more rings are simply side-attached to each other, fused together, or fused with an aryl group. Examples of such heteroaryl groups include pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, indoleazinyl, indoleyl, indolepyridinyl, purineyl, phenanthrolinel, quinolinyl, isoquinolinyl, quinazolinyl, quinoxolinyl, thiazolyl, imidazolyl, oxazolyl, furanyl, thiophene, benzofuranyl, benzothiophene, benzothiazolyl, benzoimidazolyl, benzooxazolyl, carbazole, dibenzofuranyl, dibenzothiophene, etc., but the present invention is not limited thereto.

[0505] As in this invention, the term "C1-C" 10 "Alkenyl" refers to a monovalent substituent formed by removing one hydrogen atom from an olefin molecule having 1 to 10 carbon atoms. Examples include, but are not limited to, vinyl and 1-propenyl groups.

[0506] As in this invention, the term "C1-C" 10 "Alynyl" refers to a monovalent substituent formed by removing one hydrogen atom from an alkyne molecule having 1 to 10 carbon atoms. Examples include, but are not limited to, ethynyl and propynyl.

[0507] In this invention, the term "amine" refers to a functional group composed of nitrogen and hydrogen, which differs from an amino group in that it can be attached to an organic group (such as methyl, ethyl, etc.), and is usually represented by R-NH2. R represents an organic group, examples of which include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, phenyl, naphthyl, acetyl, etc.

[0508] In this invention, the term "silyl group having C1-C10 alkyl substitution" refers to a monovalent substituent formed by replacing a silyl group with an alkyl group having 1 to 10 carbon atoms, examples of which include, but are not limited to, trimethylsilyl (-(CH3)3Si).

[0509] In this invention, the term "aryl-substituted silane having 6 to 30 carbon atoms" refers to a monovalent substituent formed by replacing a silane with an aryl group having 6 to 30 carbon atoms, examples of which include, but are not limited to, triphenylsilane (-(Ph)3Si).

[0510] As used in this invention, the expression "AA-BB number of carbon atoms" or "C(AA-BB) Z group" means the number of carbon atoms in the Z group when it is unsubstituted, excluding the number of carbon atoms in the substituents when substituted. For example, an aryl group with C6-C30 means that when it is unsubstituted, the number of carbon atoms in the aryl group is any integer from 6 to 30. That is, when it is unsubstituted, the number of carbon atoms can be 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20...30.

[0511] As used in this invention, the term "single bond" refers to groups directly connected, such as in formula (2). L3 in the middle is selected from a single bond, which means .

[0512] As used in this invention, group A" When n is 0, group A is " When n is 1, group A is " ".

[0513] In this invention, the term "substituted or unsubstituted" means that the hydrogen atoms in a compound are substituted by non-hydrogen groups or are not substituted by non-hydrogen groups. The number of substituents is not limited, as long as it can be obtained through a chemical reaction. It is not limited to a specific position, as long as the hydrogen at that position can be substituted by a substituent. For example, a carbazolyl group, unless otherwise specified in this specification, includes any of the following groups, but is not limited thereto.

[0514] “ "" indicates the substitution position. "Unsubstituted" means that the hydrogen atom is retained.

[0515] When two or more substituents are present, the two or more substituents may be the same or different. In this invention, the term "benzonaphthofuranyl" refers to a monovalent substituent formed by fused a benzene ring onto a dibenzofuranyl group, examples of which include, but are not limited to, those formed by fusion of a benzene ring onto a dibenzofuranyl group. wait.

[0516] In this invention, the term "phenylnaphthyl" refers to a phenyl-substituted naphthyl or a naphthyl-substituted phenyl, examples of which include, but are not limited to, those substituted with, a phenyl group. wait.

[0517] In this invention, unless otherwise specified, "Indicates the connection position.

[0518] As used in this invention, terms such as 1, 2, A, B, etc. are used. These terms are only used to distinguish constituent elements and do not limit the nature or order of the constituent elements corresponding to the terms.

[0519] Compound preparation examples

[0520] LC-MS Brand: Waters, Model: SQ Detector 2

[0521] MRI brand: Bruker, model: AVANCE NEO 400

[0522] Those skilled in the art can synthesize the compounds of the present invention by referring to the following compounds and known synthetic methods.

[0523] Synthesis Example 1: Preparation of Compound 1-1

[0524]

[0525]

[0526] Step 1: Add 1-1-1 (7.62 g, 25 mmol) and sodium tert-butoxide (7.21 g, 75 mmol) to a three-necked flask, add toluene (150 mL), purge twice with nitrogen, then add 1-1-2 (13.47 g, 25 mmol) and catalyst Pd. 2( The reaction mixture was 0.87 g (0.95 mmol) of dba3, purged three times with nitrogen, and then injected with tri-tert-butylphosphine (1.2 mL, 5 mmol). The mixture was heated to 70 °C and reacted for 1 h. After cooling, the mixture was washed with water, passed through diatomaceous earth to remove the palladium catalyst, evaporated to dryness, and recrystallized with dichloromethane / petroleum ether to obtain a solid. The solid was then washed with a toluene / ethyl acetate mixture at 45 °C for 2 h and filtered to obtain intermediate 1-1-3 (15.63 g, yield 82%).

[0527] LC-MS (APCI): 763.13 (M+H) + .

[0528] Step 2: Add 1-1-3 (19.07 g, 25 mmol) and sodium tert-butoxide (7.21 g, 75 mmol) to a three-necked flask, add toluene (150 mL) and purge twice with nitrogen, then add 1-1-4 (8.44 g, 25 mmol) and catalyst Pd2(dba)3 (0.87 g, 0.95 mmol), purge three times with nitrogen, then inject tri-tert-butylphosphine (1.2 mL, 5 mmol), heat to 90 °C, react for 1 h, cool, wash with water, remove palladium catalyst with diatomaceous earth, evaporate to dryness, recrystallize with dichloromethane / petroleum ether to obtain a solid, wash with a toluene / ethyl acetate mixed solvent at 45 °C for 2 h, filter to obtain intermediate 1-1-5 (19.11 g, yield 75%).

[0529] LC-MS (APCI): 1019.95 (M+H) + .

[0530] Step 3: Dissolve 1-1-5 (15.29 g, 15 mmol) in 1,4-dioxane (130 mL), and add an aqueous solution containing 1-1-6 (19.04 g, 15 mmol), Pd(PPh3)4 (0.18 g, 0.15 mmol), and K2CO3 (12.8 g, 93 mmol). Stir at 100 °C for 6 hours, cool the result to room temperature, and extract with distilled water and ethyl acetate. Dry the organic layer with MgSO4, then filter and concentrate. Purify using column chromatography with ethyl acetate and hexane as the developing solvent to obtain intermediate 1-1-7 (10.87 g, 68% yield).

[0531] LC-MS (APCI): 1066.54 (M+H) + .

[0532] Step 4: Under nitrogen atmosphere, 1-1-7 (19.08 g, 17.9 mmol) was dissolved in tert-butylbenzene (180 mL), and tert-butyllithium (1.3 mol / L, 15.2 mL) was slowly added dropwise at -40 °C. After the addition was complete, the temperature was raised to 70 °C and stirred for 0.5 h. Then, the components with boiling points lower than tert-butylbenzene were distilled off under reduced pressure. The mixture was cooled to -30 °C and BBr3 (5.4 g, 21.5 mmol) was added, and the mixture was stirred at 180 °C for 10 h. The reaction solution was chilled, and N,N-diisopropylethylamine (20.0 g) was added. The mixture was concentrated by diatomaceous earth filtration, extracted with ethyl acetate, and the organic layer was concentrated and separated by column chromatography to obtain 1-1 (4.84 g, yield 26%).

[0533] LC-MS (APCI): 1040.82 (M+H) + The corresponding mass spectrum can be found in the instruction manual appendix. Figure 2 .

[0534] 1 H NMR (400 MHz, Methylene Chloride-d2) δ 8.52 (d, 1H), 7.80 (d, 1H),7.73 – 7.66 (m, 2H), 7.52 (d, 1H), 7.44 – 7.24 (m, 6H), 7.24 – 7.16 (m, 2H),7.16 – 7.10 (m, 2H), 7.06 (d, 2H), 7.02 – 6.85 (m, 3H), 6.81 – 6.69 (m, 1H),6.50 (d, 3H), 6.34 (d, 1H), 6.06 (d, 1H), 5.66 (d, 1H), 1.39 (s, 9H), 1.25(d, 18H), 1.03 (s, 10H), 1.01 (s, 9H); see the corresponding NMR spectra in the appendix of the instruction manual. Figure 3 .

[0535] Synthesis Example 2: Preparation of Compounds 1-2

[0536]

[0537] Compound 1-2 was synthesized by referring to the synthesis steps and reaction conditions of compound 1-1 in Example 1. Compound 1-1-2 was replaced with compound 1-2-2, and the above-described synthesis route was followed to synthesize compound 1-2.

[0538] The final step of the synthesis of 1-2-7 reacting with BBr3 is as follows: Under nitrogen atmosphere, 1-2-7 (45 g, 42.22 mmol) and 450 mL of tert-butylbenzene were added sequentially to a four-necked flask. The reaction temperature was lowered to -40 °C, and tert-butyllithium (48.8 mL, 78.12 mmol, 1.6 mol / L) was added. The mixture was stirred for 0.5 h, and BBr3 (20 g, 80 mmol) was added. The mixture was slowly heated to room temperature, and diisopropylethylamine (10.3 g, 80 mmol) was added. The mixture was heated to reflux for 3 h, cooled to room temperature, and quenched with 100 mL of water. The mixture was washed with water until neutral, the aqueous phase was discarded, and the organic phase was passed through a silica gel funnel. The organic phase was evaporated to dryness and slurried with n-hexane to obtain 1-2 solid (5 g, yield 11%).

[0539] LC-MS (APCI): 1041.96 (M+H) + The corresponding mass spectrum can be found in the instruction manual appendix. Figure 4 .

[0540] 1H NMR (400 MHz, Methylene Chloride-d2) δ 7.92 (dd, 1H), 7.85 – 7.77(m, 2H), 7.64 (dt, 1H), 7.57 – 7.49 (m, 2H), 7.46 (dd, 1H), 7.42 (d, 1H),7.40 (d, 1H), 7.36 – 7.30 (m, 2H), 7.34 – 7.22 (m, 2H), 7.19 (d, 2H), 7.14 –6.99 (m, 3H), 6.88 (dd, 1H), 6.62 (dd, 1H), 6.46 (d, 1H), 6.44 (s, 2H), 6.19 (d, 1H), 5.79 (d, 1H), 1.51 (s, 9H), 1.37 (d, 18H), 1.13 (s, 9H); see the corresponding NMR spectra in the appendix of the instruction manual. Figure 5 .

[0541] Synthetic Example 3: Preparation of Compounds 1-34

[0542]

[0543] Compound 1-34 was synthesized following the synthetic steps and reaction conditions of compound 1-1 in Example 1. Compound 1-1-2 was replaced with compound 1-34-2, and compound 1-1-6 was replaced with compound 1-34-6. Following the above synthetic route, 4.04 g of compound 1-34 was synthesized, with a yield of 20% (the yield of the reaction of 1-34-7 with BBr3).

[0544] LC-MS (APCI): 1131.60 (M+H) + The corresponding mass spectrum can be found in the instruction manual appendix. Figure 6 .

[0545] 1H NMR (400 MHz, Chloroform-d) δ 7.89 (d, J = 8.5 Hz, 1H), 7.83 (d, J= 7.7 Hz, 1H), 7.69 (dd, J = 8.5, 2.1 Hz, 3H), 7.51 (dd, J = 8.3, 4.1 Hz, 3H), 7.42 (dd, J = 8.6, 1.7 Hz, 1H), 7.34 – 7.27 (m, 7H), 7.25 (s, 1H), 7.20 –7.10 (m, 4H), 7.07 (dd, J = 8.4, 1.9 Hz, 1H), 7.02 (d, J = 2.1 Hz, 1H), 6.63(d, J = 1.8 Hz, 1H), 6.49 (s, 1H), 6.37 (d, J = 1.6 Hz, 1H), 6.32 (d, J = 2.1Hz, 1H), 1.37 (s, 9H), 1.34 (s, 9H), 1.08 (s, 9H), 0.91 (s, 9H); the corresponding NMR spectra are attached to the instruction manual. Figure 7 .

[0546] Synthetic Example 4: Preparation of Compounds 1-35

[0547]

[0548] Step 1: Under nitrogen atmosphere, add the following to a four-necked flask sequentially: 1-35-2 (25 g, 46.06 mmol), 1-35-1 (27.89 g, 48.36 mmol), tris(dibenzylacetone)palladium (1.6 g, 1.8 mmol), 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl (3.4 g, 7.2 mmol), sodium tert-butoxide (9 g, 95 mmol), and 250 mL of toluene. Heat to reflux for 3 h, cool to room temperature, pass through a silica gel funnel, evaporate the organic phase to dryness, and slurry with methanol to obtain 1-35-3 solid (43 g, 87% yield).

[0549] LC-MS (APCI): 1070.37 (M+H) + .

[0550] Step 2: Under nitrogen atmosphere, 1-35-3 (43 g, 40.19 mmol) and 430 mL of tert-butylbenzene were added sequentially to a four-necked flask. The reaction temperature was lowered to -40 °C, and tert-butyllithium (46.45 mL, 74.36 mmol, 1.6 mol / L) was added. The mixture was stirred for 0.5 h, and boron tribromide (19 g, 76.15 mmol) was added. The mixture was slowly heated to room temperature, and diisopropylethylamine (9.8 g, 76.15 mmol) was added. The mixture was heated to reflux for 3 h, cooled to room temperature, and quenched with 100 mL of water. The mixture was washed with water until neutral, the aqueous phase was discarded, and the organic phase was passed through a silica gel funnel. The organic phase was evaporated to dryness and slurried with n-hexane to obtain 1-35 solid (4.8 g, yield 11%).

[0551] LC-MS (APCI): 1053.91 (M+H) + The corresponding mass spectrum can be found in the instruction manual appendix. Figure 8 .

[0552] 1 H NMR (400 MHz, Methylene Chloride-d2) δ 8.05 – 7.98 (m, 1H), 7.87(d, J = 8.5 Hz, 1H), 7.82 – 7.74 (m, 2H), 7.67 (dd, J = 7.7, 1.1 Hz, 1H),7.54 – 7.34 (m, 8H), 7.25 – 7.08 (m, 5H), 7.01 (dd, J = 7.9, 1.1 Hz, 1H), 6.91 (ddd, J = 8.8, 5.4, 3.1 Hz, 5H), 6.86 – 6.78 (m, 2H), 6.59 (d, J = 1.7Hz, 1H), 6.38 (d, J = 1.3 Hz, 1H), 6.15 (d, J = 1.3 Hz, 1H), 5.87 (d, J = 2.2 Hz, 1H), 1.48 (s, 9H), 1.35 (s, 9H), 1.19 (s, 9H), 1.09 (s, 9H); the corresponding NMR spectra are attached to the instruction manual. Figure 9 .

[0553] Synthetic Example 5: Preparation of Compounds 1-28

[0554]

[0555] Step 1: Under nitrogen atmosphere, add the following to a four-necked flask sequentially: 1-28-2 (25 g, 47.64 mmol), 1-35-1 (28.84 g, 50.02 mmol), tris(dibenzylacetone)palladium (1.9 g, 2.1 mmol), 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl (3.4 g, 7.2 mmol), sodium tert-butoxide (6.86 g, 71.46 mmol), and 250 mL of toluene. Heat to reflux for 3 h, cool to room temperature, pass through a silica gel funnel, evaporate the organic phase to dryness, and slurry with methanol to obtain 1-28-3 solid (40 g, 79% yield).

[0556] LC-MS (APCI): 1065.73 (M+H) + .

[0557] Step 2: Under nitrogen atmosphere, 1-28-3 (40 g, 37.56 mmol) and 400 mL of tert-butylbenzene were added sequentially to a four-necked flask. The reaction temperature was lowered to -40 °C, and tert-butyllithium (43.4 mL, 69.49 mmol, 1.6 mol / L) was added. The mixture was stirred for 0.5 h, and boron tribromide (17.79 g, 71.17 mmol) was added. The mixture was slowly heated to room temperature, and diisopropylethylamine (9.16 g, 71.17 mmol) was added. The mixture was heated to reflux for 3 h, cooled to room temperature, and quenched with 100 mL of water. The mixture was washed with water until neutral, the aqueous phase was discarded, and the organic phase was passed through a silica gel funnel. The organic phase was evaporated to dryness and slurried with n-hexane to obtain 1-28 solid (3.8 g, yield 10%).

[0558] LC-MS (APCI): 1038.82 (M+H) + The corresponding mass spectrum can be found in the instruction manual appendix. Figure 10 .

[0559] 1H NMR (400 MHz, Methylene Chloride-d2) δ 7.85 (dd, J = 8.4, 0.6 Hz,1H), 7.82 – 7.76 (m, 2H), 7.54 – 7.46 (m, 4H), 7.41 (dd, J = 8.5, 1.8 Hz,1H), 7.32 – 7.12 (m, 6H), 7.15 – 7.05 (m, 6H), 7.09 – 6.97 (m, 3H), 6.92 (dddd, J = 8.8, 6.5, 2.4, 1.2 Hz, 2H), 6.83 – 6.75 (m, 3H), 6.58 (dd, J =1.9, 0.6 Hz, 1H), 6.42 (d, J = 1.2 Hz, 1H), 6.29 (d, J = 1.3 Hz, 1H), 5.92 (d, J = 2.1 Hz, 1H), 1.48 (s, 9H), 1.33 (s, 9H), 1.26 (s, 9H), 1.09 (s, 9H); See the attached instruction manual for the corresponding NMR spectra. Figure 11 .

[0560] Synthetic Example 6: Preparation of Compounds 1-36

[0561]

[0562] Step 1: Under nitrogen atmosphere, add the following to a four-necked flask sequentially: 1-36-2 (25 g, 47.28 mmol), 1-36-1 (28.62 g, 49.64 mmol), tris(dibenzylacetone)palladium (1.74 g, 1.9 mmol), 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl (3.57 g, 7.6 mmol), sodium tert-butoxide (6.8 g, 70.92 mmol), and 250 mL of toluene. Heat to reflux for 3 h, cool to room temperature, pass through a silica gel funnel, evaporate the organic phase to dryness, and slurry with methanol to obtain 1-36-3 solid (46 g, 91% yield).

[0563] LC-MS (APCI): 1069.76 (M+H) + .

[0564] Step 2: Under nitrogen atmosphere, add 1-36-3 (46 g, 43.03 mmol) and 460 mL of tert-butylbenzene sequentially to a four-necked flask. Cool the reaction to -40 °C, add tert-butyllithium (49.7 mL, 79.61 mmol, 1.6 mol / L), stir for 0.5 h, add boron tribromide (20.38 g, 81.5 mmol), slowly raise the temperature to room temperature, add diisopropylethylamine (10.5 g, 81.5 mmol), heat to reflux for 3 h, cool to room temperature, quench with 100 mL of water, wash with water until neutral, discard the aqueous phase, pass the organic phase through a silica gel funnel, evaporate the organic phase to dryness, and slurry with n-hexane to obtain 1-36 solid (5.6 g, yield 13%).

[0565] LC-MS (APCI): 1039.94 (M+H) + The corresponding mass spectrum can be found in the instruction manual appendix. Figure 12 .

[0566] 1 H NMR (400 MHz, Methylene Chloride-d2) δ 7.85 (dd, J = 8.4, 0.6 Hz,1H), 7.82 – 7.76 (m, 2H), 7.54 – 7.46 (m, 4H), 7.41 (dd, J = 8.5, 1.8 Hz,1H), 7.32 – 7.12 (m, 6H), 7.15 – 7.05 (m, 6H), 7.09 – 6.97 (m, 3H), 6.92 (dddd, J = 8.8, 6.5, 2.4, 1.2 Hz, 2H), 6.83 – 6.75 (m, 3H), 6.58 (dd, J =1.9, 0.6 Hz, 1H), 6.42 (d, J = 1.2 Hz, 1H), 6.29 (d, J = 1.3 Hz, 1H), 5.92 (d, J = 2.1 Hz, 1H), 1.48 (s, 9H), 1.33 (s, 9H), 1.26 (s, 9H), 1.09 (s, 9H); the corresponding mass spectra are attached to the instruction manual. Figure 13 .

[0567] Synthesis Example 7: Preparation of Compound 2-1

[0568] Step 1: Synthesis of intermediate 2-1-1:

[0569]

[0570] Compound A, Compound B, Intermediate 2-1-1

[0571] Under a nitrogen atmosphere, compound A (10 g, 35 mmol), compound B (5.8 g, 37 mmol), K2CO3 (7.32 g, 53 mmol), and Pd(pph3)2Cl2 (0.49 g, 0.7 mmol) were added to a four-necked reaction flask. 40 mL of toluene, 20 mL of THF, and 20 mL of H2O were added, and the mixture was heated to reflux for 3 h. After cooling, 100 mL of H2O was added, and the mixture was filtered. The solid was dissolved in 300 mL of toluene, passed through a silica gel funnel, and washed with toluene. The filtrate was evaporated under reduced pressure, and 100 mL of toluene was added to slurry to obtain intermediate 2-1-1 (8.8 g, 80% yield).

[0572] Step 2: Synthesis of Compound 2-1

[0573]

[0574] Intermediate 2-1-1 Compound C Compound 2-1

[0575] Under a nitrogen atmosphere, intermediate 2-1-1 (9 g, 16 mmol), compound C (5.32 g, 16.9 mmol), and 100 mL of toluene were added to a four-necked reaction flask. The mixture was heated to separate the water, and after distilling off 20 mL, the temperature was lowered to 40 °C. Then, t-BuONa (2.32 g, 24 mmol), Pd2(DBA)3 (0.29 g, 0.3 mmol), and S-PHOS (0.53 g, 1.3 mmol) were added. The mixture was heated to reflux for 2 h, then cooled. The reaction solution was washed with water, passed through a silica gel funnel, evaporated to dryness, and then passed through a column (hexane:dichloromethane volume ratio = 10:1). The solution was evaporated to dryness under reduced pressure to obtain compound 2-1 (10 g, yield 74%).

[0576] LC-MS (APCI): 839.70 [M+H] + The corresponding mass spectrum can be found in the instruction manual appendix. Figure 14 .

[0577] 1H NMR (400 MHz, Methylene Chloride-d2) δ 8.10 (t, 1H), 7.96 – 7.86 (m, 3H), 7.83 – 7.74 (m, 4H), 7.69 (ddt, 2H), 7.61 – 7.57 (m, 2H), 7.56 –7.48 (m, 4H), 7.48 – 7.42 (m, 1H), 7.42 – 7.24 (m, 11H), 7.18 – 7.01 (m, 9H), 6.97 (t, 1H), 6.70 (dt, 1H), 6.50 (dt, 1H), 6.40 (dd, 1H), 6.18 (td, 1H),5.99 (dt, 1H); the corresponding NMR spectrum is shown in the appendix of the instruction manual. Figure 15 .

[0578] Synthetic Example 8: Preparation of Compounds 2-19

[0579] Step 1: Synthesis of intermediate 2-19-1:

[0580]

[0581] Under a nitrogen atmosphere, compound D (4.3 g, 19.641 mmol), compound A (5.4 g, 19.069 mmol), Pd-132 (270 mg, 0.381 mmol), and potassium carbonate (5.3 g, 38.139 mmol) were added to a 250 mL four-necked flask, along with 90 mL of tetrahydrofuran and 30 mL of deionized water. The mixture was heated to 70 °C and refluxed, then stirred for 8 h. Samples were spotted onto a plate and sent for testing. Once the test results were confirmed (compound A < 2%), the reaction was considered complete, heating was stopped, and the reaction solution was allowed to cool naturally to room temperature (25 °C). The product precipitated and was directly filtered. The filter cake was dissolved in 150 mL of toluene by heating (110 °C), then concentrated at atmospheric pressure (170 °C) to approximately 40 mL of solvent remaining. The mixture was allowed to cool naturally to room temperature (25 °C) to induce crystallization. After reaching the set temperature, stirring was continued at room temperature (25 °C) for 2 h, followed by filtration. The product was dissolved in 200 mL of dichloromethane and 40 mL of ethyl acetate at 70 °C. Approximately 160 mL of solvent was then distilled off at atmospheric pressure (80 °C). The mixture was allowed to cool naturally to room temperature (25 °C) to crystallize. After reaching the desired temperature, the mixture was stirred at room temperature (25 °C) for 2 h, and then filtered. The filter cake was rotary dried at 80 °C for 1 h to obtain 5.7 g of intermediate 2-19-1, which was set aside for later use. The HPLC purity was 99.4%, and the molar yield was 96.4%.

[0582] Step 2: Synthesis of intermediate 2-19-2

[0583]

[0584] Under a nitrogen atmosphere, intermediate 2-19-1 (5.7 g, 19.296 mmol), compound E (8.2 g, 19.296 mmol), Pd2(dba)3 (530 mg, 0.578 mmol), Sphos (792 mg, 1.926 mmol), and sodium tert-butoxide (3.7 g, 38.593 mmol) were added to a 250 mL four-necked flask, along with 100 mL of xylene. The mixture was heated to 140 °C and refluxed, then stirred for 4 h. Samples were spotted onto a TLC plate and sent for analysis. Once the results were confirmed (starting compound E < 2%), the reaction was considered complete, heating was stopped, and the reaction solution was allowed to cool naturally to room temperature (25 °C). The sample was passed through a 100-200 mesh silica gel column (5 cm high, 4 cm diameter), eluted with 1500 mL of toluene, and concentrated at atmospheric pressure (170 °C) to crystallize down to 50 mL of toluene. The mixture was allowed to cool naturally to room temperature (25 °C) to precipitate a solid. Stirring was continued at room temperature (25 °C) for 0.5 h, and the product was filtered. 150 mL of ethyl acetate was added to the product, and the mixture was stirred and refluxed at 80 °C for 1 h. The mixture was then concentrated at atmospheric pressure (80 °C) to 50 mL of solvent. After cooling naturally to room temperature (25 °C), stirring was continued at room temperature (25 °C) for 0.5 h, and the mixture was filtered. The filter cake was dried by rotary evaporation (80 °C) for 1 h to obtain 5.9 g of intermediate 2-19-2, which was set aside for later use. The HPLC purity was 99.4%, and the molar yield was 44.7%.

[0585] Step 3: Synthesis of compound 2-19

[0586]

[0587] Under a nitrogen atmosphere, intermediate 2-19-2 (5.9 g, 8.602 mmol), compound F (2.6 g, 8.602 mmol), Pd2(dba)3 (236 mg, 0.258 mmol), Sphos (353 mg, 0.860 mmol), and sodium tert-butoxide (1.6 g, 17.204 mmol) were added to a 250 mL four-necked flask, along with 100 mL of xylene. The mixture was heated to 140 °C and refluxed, then stirred for 4 h. Samples were spotted onto a TLC plate and sent for analysis. Once the results were confirmed (compound F < 2%), the reaction was considered complete, heating was stopped, and the reaction solution was allowed to cool naturally to room temperature (25 °C). The sample was passed through a 100-200 mesh silica gel column (5 cm high, 4 cm diameter), washed with 1800 mL of toluene, and concentrated at atmospheric pressure (170 °C) to crystallize down to 50 mL of toluene. The sample was then allowed to cool naturally to room temperature (25 °C) to precipitate a solid. After stirring at room temperature (25 °C) for 2 h, the sample was filtered to obtain the crude product. The purified product was a yellowish-white color and dried under vacuum at 130 °C for 6 h to obtain 2.5 g of compound 2-19 with a purity of 99.2% and a yield of 32%.

[0588] LC-MS (APCI): 914.75 (M+H + ).Calculated for: C 71 H 47 N.

[0589] 1 H NMR (400 MHz, Methylene Chloride-d2) δ 8.10 (d, J = 1.9 Hz, 1H), 7.97 – 7.85 (m, 3H), 7.84 – 7.74 (m, 4H), 7.70 (ddd, J = 8.3, 2.1, 1.2 Hz, 2H), 7.66 – 7.57 (m, 6H), 7.57 – 7.40 (m, 9H), 7.40 – 7.22 (m, 7H), 7.18 –7.02 (m, 9H), 6.98 (t, J = 7.6 Hz, 1H), 6.71 (dt, J = 7.6, 0.9 Hz, 1H), 6.50(dt, J = 7.6, 1.0 Hz, 1H), 6.41 (dd, J = 7.5, 1.1 Hz, 1H), 6.23 (td, J = 7.5, 1.1 Hz, 1H), 6.01 (dt, J = 7.6, 1.0 Hz, 1H). See the attached instruction manual for the corresponding NMR spectra. Figure 16 .

[0590] Synthesis Example 9: Preparation of Compounds 2-20

[0591]

[0592] Under nitrogen protection, intermediate 2-19-2 (4.5 g, 6.6 mmol), compound G (2.0 g, 6.5 mmol), sodium tert-butoxide (1.26 g, 13.1 mmol), S-Phos (0.27 g, 0.66 mmol), and Pd2(dba)3 (0.12 g, 0.13 mmol) were placed in a four-necked reaction flask, followed by the addition of 100 mL of toluene. The mixture was heated to reflux (110 °C) and then stirred at this temperature for 3 h. Samples were spotted onto a plate and sent for testing. After confirmation of the test results (intermediate 2-19-2 < 2%), the reaction was stopped, heating was turned off, and the mixture was allowed to cool naturally to room temperature (25℃). 100 mL of water and 50 mL of ethyl acetate were added, and the mixture was extracted and separated. The organic phase was mixed and passed through a column (10 g of 200-300 mesh silica gel, column diameter 5 cm, column height 15 cm; eluent: n-hexane: dichloromethane = 10:1, 8:1, 5:1, 4:1). The column solutions were combined and concentrated under reduced pressure by rotary evaporation to about 100 mL of solvent remaining. The mixture was allowed to cool naturally to room temperature (25℃), and a solid precipitated. The solid was filtered to obtain compound 2-20 as a crude white solid. The purified compound was dried (120℃, 6 h) to obtain 2.5 g of compound 2-20 with a purity of 99.96% and a yield of 42%.

[0593] LC-MS (APCI): 914.75 (M+H) + ).Calculated for: C 71 H 47 N 913.37, the corresponding mass spectrum can be found in the instruction manual. Figure 17 .

[0594] 1H NMR (400 MHz, Methylene Chloride-d2) δ 8.10 (d, J = 1.8 Hz, 1H), 7.97 – 7.84 (m,3H), 7.84 – 7.74 (m, 4H), 7.69 (dt, J = 7.4, 1.1 Hz, 2H), 7.64– 7.27 (m, 22H), 7.20 – 6.93 (m,10H), 6.71 (dt, J = 7.7, 0.9 Hz, 1H), 6.50 (dt, J = 7.6, 1.0 Hz,1H), 6.42 (dd, J = 7.5, 1.1 Hz,1H), 6.15 (td, J = 7.5,1.1 Hz, 1H), 6.02 (dt, J = 7.5, 1.0 Hz, 1H). See the attached instruction manual for the corresponding NMR spectrum. Figure 18 .

[0595] Synthetic Example 10: Preparation of Compounds 2-23

[0596]

[0597] Under nitrogen protection, compound 2-16-2 (10.0 g, 14.6 mmol) and compound I (3.8 g, 15.9 mmol) were placed in a four-necked reaction flask, followed by the addition of 120 mL of toluene. The mixture was heated to an external temperature of 130 °C, and 10 mL of toluene was distilled off. The mixture was then cooled to 30 °C, and sodium tert-butoxide (2.1 g, 21.9 mmol), Pd2(dba)3 (200 mg, 0.22 mmol), and X-Phos (280 mg, 0.59 mmol) were added. The mixture was purged with nitrogen three times and then heated to an external temperature of 70 °C to react. After the reaction was complete (approximately 3 hours), the reaction solution was cooled to room temperature, washed three times with 50 mL of water, the aqueous phase was discarded, and the organic phase was passed through a silica gel fast column. The solution was eluted with 100 mL of toluene, dried by rotary evaporation, and 100 mL of ethyl acetate was added. The mixture was heated to 80 °C and stirred for 1 hour. The mixture was then cooled to room temperature and filtered to obtain the crude product. After purification, 2.5 g of compound 2-23 was obtained, with a yield of 19.3%.

[0598] LC-MS (APCI): 888.72 (M+H + Molecular formula: C 69 H 45 N.

[0599] 1H NMR (400 MHz, Methylene Chloride-d2) δ 7.93 (ddd, J = 7.8, 2.9,1.3 Hz, 2H), 7.89 – 7.81 (m, 5H), 7.78 (dt, J = 7.6, 0.9 Hz, 1H), 7.73 – 7.67(m, 2H), 7.61 (dd, J = 6.4, 1.6 Hz, 2H), 7.53 – 7.42 (m, 13H), 7.39 – 7.28(m, 4H), 7.19 – 7.04 (m, 10H), 6.99 (t, J = 7.6 Hz, 1H), 6.71 (dt, J = 7.7,0.9 Hz, 1H), 6.50 (dt, J = 7.5, 1.0 Hz, 1H), 6.42 (dd, J = 7.5, 1.1 Hz, 1H), 6.14 (t, J = 7.4 Hz, 1H), 6.03 (dt, J = 7.6, 1.0 Hz, 1H). See the attached instruction manual for the corresponding NMR spectra. Figure 19 .

[0600] Synthetic Example 11: Preparation of Compounds 2-25

[0601]

[0602] Under a nitrogen atmosphere, intermediate 2-19-2 (50.0 g, 72.99 mmol), compound A (24.8 g, 87.6 mmol), t-BuONa (14.0 g, 145.6 mmol), and Pd132 (1.6 g, 2.3 mmol) were placed in a four-necked reaction flask, and 500 mL of xylene was added. The mixture was heated to 140 °C and reacted for 12 h. LC-MS results showed that 20% of intermediate 2-19-2 remained. Compound A was added in a 0.2-fold volume, and the reaction continued for another 4 h. LC-MS after this time showed that intermediate 2-19-2 had completely reacted. The reaction solution was allowed to cool naturally to 50 °C and then passed through a rapid column chromatography system. The solution was washed with 1000 mL of toluene using a 100-200 mesh silica gel column (20 cm high, 16 cm diameter). The organic phase was evaporated to dryness to obtain the crude product, which was purified to give 34 g of compound 2-25, yield: 52%.

[0603] LC-MS (APCI): 888.75 (M+H) + ).Calculated for: C 69 H 45 For N, please refer to the attached instruction manual for the corresponding mass spectrum. Figure 20 .

[0604] 1 ¹H NMR (400 MHz, Methylene Chloride-d²) δ 8.10 (d, J = 1.9 Hz, 1H), 7.96 – 7.75 (m, 11H), 7.72 – 7.65 (m, 2H), 7.63 – 7.41 (m, 12H), 7.39 – 7.28 (m, 4H), 7.20 – 6.96 (m, 10H), 6.70 (dt, J = 7.7, 1.0 Hz, 1H), 6.50 (dt, J = 7.6, 1.0 Hz, 1H), 6.41 (dd, J = 7.5, 1.1 Hz, 1H), 6.13 – 5.98 (m, 2H). See the attached datasheet for the corresponding NMR spectra. Figure 21 .

[0605] Synthetic Example 12: Preparation of Compounds 1-91

[0606]

[0607] Under a nitrogen atmosphere, intermediate 2-19-2 (12.70 g, 18.52 mmol), compound J (5.50 g, 19.44 mmol), Pd2(dba)3 (0.51 g, 0.55 mmol), S-Phos (0.76 g, 1.85 mmol), and sodium tert-butoxide (3.50 g, 37.03 mmol) were added to a 250 mL four-necked flask, along with 200 mL of xylene. The mixture was heated to 140 °C and refluxed, then stirred for 4 h. Samples were spotted onto a TLC plate and sent for analysis. Once the results were confirmed (intermediate 2-19-2 < 2%), the reaction was considered complete, heating was stopped, and the reaction solution was allowed to cool naturally to room temperature (25 °C). The sample was passed through a 100-200 mesh silica gel column (5 cm high, 4 cm diameter), washed with 1500 mL of toluene, and evaporated to dryness by rotary evaporation (80°C). 100 mL of toluene and 20 mL of ethyl acetate were added, and the mixture was heated to 100°C and refluxed. After stirring for 1 h, the mixture was allowed to cool naturally to room temperature (25°C) to precipitate a solid. The mixture was stirred at room temperature (25°C) for another 2 h, filtered to obtain the crude product, purified to obtain a white product, and dried under vacuum at 140°C for 6 h to obtain 12.20 g of compound 1-91 with a purity of 99.74% and a yield of 74.19%.

[0608] LC-MS (APCI): 888.44 [M+H] + .Calcd for:C 69 H 45The mass spectrum corresponding to N, 887.35 can be found in the instruction manual. Figure 22 ;

[0609] 1 H NMR (400 MHz, Methylene Chloride-d2) δ 8.14 (d, J = 1.9 Hz, 1H), 7.97 (t, J = 7.5 Hz, 2H), 7.94 – 7.90 (m, 2H), 7.87 – 7.81 (m, 4H), 7.80 –7.71 (m, 5H), 7.67 (td, J = 7.7, 1.6 Hz, 1H), 7.59 – 7.49 (m, 6H), 7.47 (dd,J = 8.5, 1.5 Hz, 1H), 7.42 – 7.34 (m, 5H), 7.30 (dt, J = 7.4, 2.3 Hz, 3H),7.23 – 7.09 (m, 9H), 7.06 (t, J = 7.6 Hz, 1H), 6.77 (dt, J = 7.6, 1.0 Hz, 1H), 6.58 (dt, J = 7.5, 1.1 Hz, 1H), 6.49 (dd, J = 7.5, 1.1 Hz, 1H), 6.18 –6.10 (m, 2H). See section 23 of the instruction manual for the corresponding NMR spectra.

[0610] Synthesis Example 13: Preparation of Compounds 2-3

[0611] Step 1: Synthesis of intermediate 2-3-1

[0612]

[0613] Under nitrogen protection, compound K (60.00 g, 166.6 mmol), compound L (33.48 g, 174.9 mmol), Pd(PPh3)2Cl2 (1.17 g, 1.67 mmol), and potassium carbonate (34.52 g, 249.8 mmol) were placed in a 1 L four-necked reaction flask, followed by the addition of 300 mL tetrahydrofuran and 100 mL water. The mixture was purged with nitrogen three times and heated to 80 °C for reaction. After the reaction was complete (approximately 5 hours), the reaction solution was cooled to room temperature (25 °C), 100 mL of water was added for washing, the layers were separated, the aqueous phase was discarded, and the organic phase was passed through a silica gel rapid column (300-400 mesh silica gel, column height 2 cm, column diameter 8 cm). The solution was washed with 500 mL of dichloromethane, and the filtrate was concentrated under reduced pressure to obtain crude intermediate 2-3-1. After purification, 39.0 g of white solid intermediate 2-3-1 was obtained with a purity of 99.75% and a yield of 54.84%.

[0614] Step 2: Synthesis of compounds 2-3

[0615]

[0616] Under a nitrogen atmosphere, compound AE (4.19 g, 9.36 mmol), intermediate 2-3-1 (4.00 g, 9.37 mmol), sodium tert-butoxide (1.80 g, 18.73 mmol), Pd2(dba)3 (0.25 g, 0.27 mmol), and Sphos (0.23 g, 0.56 mmol) were placed in a four-necked reaction flask, and 150 mL of toluene was added. The reaction was carried out at 105 °C for 3 h. After the reaction was completed, the mixture was cooled to room temperature (approximately 16 °C), extracted with dichloromethane, and the extract was evaporated to dryness. The extract was dissolved in dichloromethane and passed through a silica gel column (100-200 mesh silica gel, 8 cm diameter, 8 cm height). The column was washed with dichloromethane, and the column extract was evaporated to dryness to obtain a crude product. After purification, the crude product was dried at 140 °C to obtain 5 g of compound 2-3 with a purity of 99.97% and a yield of 64%.

[0617] LC-MS (APCI): 838.52 (M+H) + ).Calculated for: C 65 H 43 For N, please refer to the attached instruction manual for the corresponding mass spectrum. Figure 24 .

[0618] 1 ¹H NMR (400 MHz, Methylene Chloride-d²) δ 8.01 – 7.85 (m, 7H), 7.76 – 7.64 (m, 3H), 7.62 – 7.43 (m, 10H), 7.43 – 7.27 (m, 11H), 7.22 – 7.05 (m, 8H), 6.93 (d, J = 1.6 Hz, 1H), 6.72 (ddt, J = 23.8, 7.7, 0.9 Hz, 3H). See the attached datasheet for the corresponding NMR spectra. Figure 25 .

[0619] Synthetic Example 14: Preparation of Compounds 1-94

[0620]

[0621] Under a nitrogen atmosphere, intermediate 2-3-1 (5.49 g, 12.88 mmol), compound AN (5.24 g, 11.72 mmol), t-BuONa (2.25 g, 23.41 mmol), Pd2(dba)3 (0.32 g, 0.35 mmol), and SPhos (0.29 g, 0.71 mmol) were added to a 250 mL four-necked flask, along with 60 mL of toluene. The mixture was heated to 110 °C and stirred for 4 h. Samples were taken for testing. Once the test results were confirmed (compound AN <2%), the reaction was considered complete, heating was stopped, and the reaction solution was allowed to cool naturally to room temperature (25 °C). The reaction solution was directly passed through a fast column (200-300 mesh), eluted with toluene (3 L) on the column, and the liquid was concentrated to obtain a crude yellow oily product. After purification, a pale yellow solid was obtained and dried under vacuum at 130 °C for 8 h to give 6.90 g of a pale yellow solid compound 1-94 with a purity of 99.93%. The yield was 70.34%.

[0622] LC-MS (APCI): 838.45 [M+H] + Calculated for: C 65 H 43 N 837. 34, the corresponding mass spectrum can be found in the instruction manual appendix. Figure 26 .

[0623] 1 ¹H NMR (400 MHz, Methylene Chloride-d²) δ 8.16 (d, J = 1.8 Hz, 1H), 7.96 (ddd, J = 19.1, 8.0, 3.8 Hz, 7H), 7.85 (dd, J = 8.5, 2.1 Hz, 3H), 7.77 – 7.67 (m, 3H), 7.63 – 7.50 (m, 6H), 7.47 – 7.26 (m, 11H), 7.24 – 7.05 (m, 8H), 6.97 (d, J = 1.7 Hz, 1H), 6.76 (dd, J = 23.2, 7.6 Hz, 3H). See the attached datasheet for the corresponding NMR spectra. Figure 27 .

[0624] Synthetic Example 15: Preparation of Compounds 1-112

[0625] Step 1: Synthesis of intermediate 1-112-1

[0626]

[0627] Under nitrogen protection, compound E (12.00 g, 28.1 mmol) and compound V (6.16 g, 28.1 mmol) were added to a 500 mL four-necked reaction flask, followed by 200 mL of toluene. The mixture was heated to 150 °C and evaporated under normal pressure until 150 mL of solvent remained. The mixture was then cooled to room temperature (25 °C), and sodium tert-butoxide (5.40 g, 56.2 mmol), Pd2(dba)3 (0.51 g, 0.56 mmol), and S-phos (0.92 g, 2.24 mmol) were added. The mixture was purged with nitrogen three times and then heated to 110 °C. After the reaction was complete (approximately 2 h), the reaction solution was cooled to room temperature (25 °C), washed with 200 mL of water, and separated into layers. The aqueous phase was discarded, and the organic phase was passed through a silica gel fast column (300-400 mesh silica gel, column height 5 cm, column diameter 8 cm). The solution was eluted with 100 mL of toluene, and the column buffer was evaporated to dryness. The crude product was dissolved in 50 mL of dichloromethane and 200 mL of n-hexane at 60 °C while being evaporated at atmospheric pressure until 200 mL of solvent remained. The mixture was then cooled to room temperature (25 °C) and stirred for 3 h, followed by filtration. The crude product was then added to 100 mL of ethyl acetate and stirred at 80 °C for 1 h. The mixture was then cooled to room temperature (25 °C) and filtered to obtain 14.0 g of intermediate 1-112-1 with a purity of 98.48% and a yield of 81.87%.

[0628] Step 1: Synthesis of Compound 1-112

[0629]

[0630] Under a nitrogen atmosphere, intermediate 1-112-1 (7.77 g, 12.7 mmol), compound U (4.97 g, 14.00 mmol), and 100 mL of toluene were added to a 250 mL four-necked reaction flask. The mixture was heated to 150 °C to remove 20 mL of toluene. Under nitrogen protection, the mixture was cooled to 25 °C, and then Pd2(dba)3 (0.23 g, 0.25 mmol), X-phos (0.49 g, 1.03 mmol), and sodium tert-butoxide (2.45 g, 25.5 mmol) were added. The mixture was heated to 80 °C and reacted. After the reaction was complete (approximately 15 h), the mixture was stirred and cooled to 25 °C. The mixture was then passed through a 50 g 200-300 mesh 150 mL silica gel funnel, washed with 100 mL of DCM, and the organic phase was evaporated to dryness. 30 mL of DCM was then added. EA was heated to 80℃ to dissolve, and then cooled to 25℃ with natural stirring for 15 hours to crystallize. After filtration, crude product was obtained. After purification, the product was dried under vacuum at 120℃ to obtain 2.9g of compound 1-112 with a purity of 99.89% and a yield of 24.52%.

[0631] LC-MS (APCI): (M+H) + 928.58.Calcd for: C 72 H 49The mass spectrum corresponding to N can be found in the instruction manual. Figure 28 .

[0632] 1 H NMR (400 MHz, Methylene Chloride-d2) δ 8.16 (d, J = 1.8 Hz, 1H), 8.02 – 7.91 (m, 5H), 7.91 – 7.85 (m, 2H), 7.81 (d, J = 7.6 Hz, 1H), 7.77 –7.62 (m, 7H), 7.61 – 7.48 (m, 5H), 7.48 – 7.39 (m, 3H), 7.39 – 7.33 (m, 3H), 7.30 (d, J = 8.2 Hz, 1H), 7.25 – 7.01 (m, 9H), 6.97 (dd, J = 8.2, 2.1 Hz,1H), 6.75 (d, J = 7.6 6.51 (d, J = 7.6 Hz, 1H), 6.44 (dd, J = 7.5, 1.1 Hz, 1H), 6.03 (td, J = 7.5, 1.1 Hz, 1H), 5.92 (d, J = 7.6 Hz, 1H), 1.26 (d, J = 24.7 Hz, 6H). See the attached instruction manual for the corresponding NMR spectra. Figure 29 .

[0633] Synthetic Example 16: Preparation of Compounds 1-118

[0634] Step 1: Synthesis of intermediate 1-118-1

[0635]

[0636] Under a nitrogen atmosphere, compound AB (20.13 g, 102.98 mmol), compound Z (20.37 g, 118.4 mmol), potassium carbonate (28.47 g, 205.9 mmol), and Pd-132 (2.18 g, 3.07 mmol) were placed in a 1 L four-necked reaction flask, along with 250 mL of tetrahydrofuran and 75 mL of water. The mixture was heated to 65 °C for reaction. After the reaction was complete (approximately 1 h), the reaction solution was cooled to 25 °C, the aqueous phase was separated, and the organic phase was evaporated to dryness. The product was dissolved in dichloromethane, stirred, and filtered through a 13 cm column (8 cm diameter, packed with 100-200 mesh silica gel). The developing solvent was dichloromethane:n-hexane = 1:50. The product was collected and evaporated to dryness, yielding 24.5 g of intermediate 1-118-1, a white solid. The HPLC yield was 93.62%, with a recovery rate of 91.75%.

[0637] Step 2: Synthesis of intermediate 1-118-2

[0638]

[0639] Under a nitrogen atmosphere, intermediate 1-118-1 (10.89 g, 44.9 mmol), compound AC (15.95 g, 62.8 mmol), potassium acetate (8.81 g, 89.8 mmol), Pd(OAc)2 (0.30 g, 1.34 mmol), and X-Phos (1.28 g, 2.68 mmol) were placed in a 1 L four-necked reaction flask, followed by the addition of 190 mL of 1,4-dioxane. The mixture was then heated to 99 °C to allow the reaction to proceed. After the reaction was complete (approximately 1 hour), the reaction solution was cooled to 25°C. The reaction solution was then passed through a diatomaceous earth mat, and the black filtrate was collected and evaporated to dryness. The filtrate was dissolved in dichloromethane, mixed, and then passed through a column with an 8 cm diameter, packed with 100-200 mesh silica gel, and a column height of 12 cm. The developing solvent was ethyl acetate:n-hexane = 1:50. The product was collected to obtain 11.67 g of intermediate 1-118-2, with an HPLC yield of 99.94% and a recovery rate of 77.8%.

[0640] Step 3: Synthesis of intermediate 1-118-3

[0641]

[0642] Under a nitrogen atmosphere, intermediate 1-118-2 (11.4 g, 34.1 mmol), compound AD (5.22 g, 29.65 mmol), potassium carbonate (8.2 g, 59.33 mmol), and Pd-132 (0.63 g, 0.89 mmol) were added to a 500 mL four-necked reaction flask, along with 90 mL of tetrahydrofuran and 27 mL of water. The mixture was heated to 65 °C. After the reaction was complete (approximately 2 hours), the reaction solution was cooled to 25 °C, and 40 mL of water was added. The mixture was filtered to obtain a grayish-black solid. The product was dissolved in dichloromethane and then passed through a rapid column (4 cm diameter, packed with 100-200 mesh silica gel, 5 cm high). The column was washed with dichloromethane, collected, and evaporated to dryness. Then, the mixture was stirred overnight in a mixed solvent of 80 mL ethyl acetate, 30 mL dichloromethane, and 30 mL tetrahydrofuran. The mixture was then filtered to obtain 6.4 g of light brown powder intermediate 1-118-3, with a yield of 71.1%.

[0643] LC-MS (APCI): 304.28 (M+H + ).Calcd for C 22 H9D8N.

[0644] Step 4: Synthesis of intermediate 1-118-4

[0645]

[0646] Under a nitrogen atmosphere, intermediate 1-118-3 (4.59 g, 15.1 mmol), compound E (6.15 g, 14.4 mmol), sodium tert-butoxide (2.77 g, 28.8 mmol), Pd2(dba)3 (0.26 g, 0.28 mmol), and S-Phos (0.24 g, 0.58 mmol) were added to a 500 mL four-necked reaction flask, followed by 100 mL of toluene. The mixture was heated to 105 °C. After the reaction was complete (approximately 1 h), the reaction solution was cooled to 25 °C, and 40 mL of water was added to quench the reaction. The product was filtered to obtain a gray solid. The product was dissolved in dichloromethane and then passed through a rapid column (4 cm diameter, packed with 100-200 mesh silica gel, 5 cm high). The column was washed with dichloromethane, collected, and evaporated to dryness. The product was then dissolved under reflux with 30 mL of dichloromethane, 20 mL of ethanol was added, and 25 mL of dichloromethane was removed under normal pressure. After cooling to 25 °C, the product was filtered to obtain the final product. The product was then dissolved under reflux with 12 mL of toluene, and 6 mL of toluene was removed under normal pressure. After cooling to 80 °C, 6 mL of ethyl acetate was added, and the mixture was cooled to crystallize. After filtration at 25 °C, 8.1 g of solid intermediate 1-118-4 was obtained, with an HPLC yield of 99.65% and a yield of 81%.

[0647] LC-MS (APCI): 694.52 (M+H + ).Calcd for C 53 H 27 D8N.

[0648] Step 5: Synthesis of Compound 1-118

[0649]

[0650] Under a nitrogen atmosphere, intermediates 1-118-4 (7.71 g, 11.1 mmol), 1-118-1 (3.05 g, 12.6 mmol), sodium tert-butoxide (2.14 g, 22.3 mmol), Pd2(dba)3 (0.31 g, 0.34 mmol), and X-Phos (0.32 g, 0.67 mmol) were placed in a 500 mL four-necked flask, and 100 mL of toluene was added. The mixture was heated to 80 °C and reacted. After the reaction was complete (approximately 6 h), the reaction solution was cooled to 25 °C, and 40 mL of water was added. The aqueous phase was separated, and the organic phase was evaporated to dryness to obtain a crude product. After purification, the crude product was dried in a vacuum oven at 120 °C to obtain 6.1 g of compound 1-118 as a white solid with a purity of 99.96% and a yield of 61%.

[0651] LC-MS (APCI): 900.60 (M+H) +).Calcd for:C 69 H 33 D 12 For N, please refer to the attached instruction manual for the corresponding mass spectrum. Figure 30 .

[0652] 1 H NMR (400 MHz, Methylene Chloride-d2) δ 8.11 (d, J = 1.9 Hz, 1H),7.96 – 7.91 (m, 2H), 7.90 – 7.79 (m, 6H), 7.76 (dt, J = 7.6, 1.0 Hz, 1H),7.69 (ddt, J = 13.5, 7.7, 1.0 Hz, 2H), 7.63 – 7.43 (m, 8H), 7.35 – 7.28 (m,2H), 7.17 (ddd, J = 8.1, 7.1, 1.2 Hz, 1H), 7.11 – 6.96 (m, 5H), 6.71 (dt, J =7.7, 1.0 Hz, 1H), 6.50 (dt, J = 7.6, 1.0 Hz, 1H), 6.41 (dd, J = 7.5, 1.1 Hz, 1H), 6.13 – 6.06 (m, 1H), 6.01 (dt, J = 7.5, 1.0 Hz, 1H). See the attached instruction manual for the corresponding NMR spectra. Figure 31 .

[0653] Synthetic Example 17: Preparation of Compounds 2-44

[0654] Step 1: Synthesis of intermediate 2-44-1

[0655]

[0656] Under a nitrogen atmosphere, compound BC (15.00 g, 35.1 mmol), intermediate 2-19-1 (10.90 g, 36.9 mmol), and 150 mL of toluene were added to a four-necked reaction flask. The mixture was heated to 150 °C to remove 20 mL of toluene. Under nitrogen protection, the mixture was cooled to 25 °C, and then Pd2(dba)3 (0.64 g, 0.699 mmol), S-phos (1.15 g, 2.8 mmol), and sodium tert-butoxide (6.75 g, 70.24 mmol) were added. The mixture was heated to 80 °C and reacted. After the reaction was complete (approximately 2 hours), the mixture was stirred naturally and cooled to 25 °C. 50 mL of water was added to quench the reaction, and the mixture was separated. The organic phase was passed through a 20 g 200-300 mesh 150 mL silica gel funnel and washed with 100 mL of DCM. The organic phase was evaporated to dryness, and 100 mL of DCM was added to the solution. Ethanol was stirred at 80℃ for 2 hours, cooled to 25℃ and filtered to obtain 18.00 g of intermediate 2-44-1, with a yield of 74.69%.

[0657] LC-MS(APCI): (M+H+) 686.60.

[0658] Step 2: Synthesis of Compounds 2-44

[0659]

[0660] Under a nitrogen atmosphere, intermediate 2-44-1 (10.00 g, 14.6 mmol), compound BD (3.74 g, 16.04 mmol), and 150 mL of toluene were added to a four-necked reaction flask. The mixture was heated to 150 °C to remove 20 mL of toluene. Under nitrogen protection, the mixture was cooled to 25 °C, and then Pd2(dba)3 (0.27 g, 0.295 mmol), X-phos (0.56 g, 1.17 mmol), and sodium tert-butoxide (2.8 g, 29.1 mmol) were added. The mixture was heated to 80 °C and reacted. After the reaction was complete (approximately 3 hours), the mixture was stirred naturally and cooled to 25 °C. 50 mL of water was added to quench the reaction, and the mixture was separated. The organic phase was passed through a 20 g 200-300 mesh 150 mL silica gel funnel, washed with 100 mL of toluene, and the organic phase was evaporated to dryness before adding 100 mL of EA. Dissolved at 80℃, naturally cooled to 25℃ for recrystallization, filtered to obtain crude product, purified and dried under vacuum at 120℃ for 8 hours to obtain 3.0 g of compound 2-44 with a purity of 99.92% and a yield of 24.55%.

[0661] LC-MS (APCI): (M+H) + 838.63.Calcd for: C 59 H 43 For N, please refer to the attached instruction manual for the corresponding mass spectrum. Figure 32 .

[0662] 1H NMR (400 MHz, Methylene Chloride-d2) δ 8.18 (d, J = 1.8 Hz, 1H),8.04 – 7.96 (m, 2H), 7.95 – 7.82 (m, 5H), 7.78 – 7.67 (m, 5H), 7.64 – 7.51(m, 4H), 7.47 (dd, J = 8.4, 7.0 Hz, 2H), 7.42 – 7.21 (m, 13H), 7.12 (td, J =7.5, 1.1 Hz, 1H), 6.92 (td, J = 7.5, 1.1 Hz, 2H), 6.84 – 6.74 (m, 4H), 6.72 –6.65 (m, 2H), 6.57 (dt, J = 7.6, 0.9 Hz, 2H). See the attached instruction manual for the corresponding NMR spectrum. Figure 33 .

[0663] Synthetic Example 18: Preparation of Compounds 1-97

[0664] Step 1: Preparation of intermediate 1-97-1

[0665]

[0666] Under a nitrogen atmosphere, compound I (9.81 g, 41.1 mmol) and intermediate 2-19-1 (12.14 g, 41.1 mmol) were added to a 500 mL four-necked reaction flask. 250 mL of toluene was added as solvent and the mixture was stirred. The mixture was heated to 160 °C to remove 10.0 mL of solvent. The mixture was then cooled to 25 °C in a water bath. Pd₂(dba)₃ (0.37 g, 0.4 mmol), S-phos (0.67 g, 1.63 mmol), and sodium tert-butoxide (5.92 g, 61.6 mmol) were added. The mixture was purged with nitrogen three times and then heated to 70 °C. After the reaction was complete (approximately 8 hours), the reaction solution was allowed to cool naturally to 25 °C. 50.0 mL of water was added, and a solid precipitated. The solid was filtered directly (using a 150 mL funnel), and the filter cake was washed with 200 mL of ethanol to obtain the solid. The solid was dissolved in 500 mL of toluene and heated to 120 °C. The solution was passed through a silica gel funnel (150 mL funnel, 100-200 mesh silica gel, column height 5 cm). The filter cake was washed with 300 mL of toluene and collected and evaporated to dryness to obtain 8.00 g of intermediate 1-97-1 with a purity of 99.0%.

[0667] LC-MS (APCI): 498.41 (M+H) + ).

[0668] Step 2: Synthesis of compounds 1-97

[0669]

[0670] Under a nitrogen atmosphere, intermediates 1-97-1 (7.75 g, 15.6 mmol) and 2-3-1 (6.98 g, 16.3 mmol) were added to a 500 mL four-necked reaction flask. 200 mL of toluene was added as solvent and the mixture was stirred. The mixture was heated to 160 °C, and 10.0 mL of solvent was distilled off. The mixture was then cooled to 25 °C in a water bath. Pd2(dba)3 (0.14 g, 0.15 mmol), X-phos (0.29 g, 0.61 mmol), and sodium tert-butoxide (2.24 g, 23.3 mmol) were added. The mixture was purged with nitrogen three times and then heated to 60 °C. After the reaction was complete (approximately 8 h), the reaction solution was allowed to cool naturally to 25 °C. 50.0 mL of water was added, and the aqueous phase was separated. The organic phase was directly passed through a silica gel funnel (150 mL funnel, 200-300 mesh silica gel, 5 cm column height). The filtrate was collected and evaporated under reduced pressure to obtain the crude product. After purification, the compound was dried under vacuum at 120°C for 8 hours to obtain 2.50 g of compound 1-97 with a purity of 99.90% and an overall yield of 25.4%.

[0671] LC-MS (APCI): 888.57 (M+H) + ).Calculated for: C 69 H 45 N.

[0672] 1 H NMR (400 MHz, Methylene Chloride-d2) δ 8.08 (d, J = 1.9 Hz, 1H),8.04 – 7.88 (m, 10H), 7.83 – 7.74 (m, 3H), 7.73 – 7.49 (m, 13H), 7.47 – 7.40(m, 5H), 7.30 – 7.22 (m, 4H), 7.22 – 7.14 (m, 5H), 6.98 (d, J = 1.6 Hz, 1H), 6.83 – 6.70 (m, 3H).

[0673] Synthetic Example 19: Preparation of Compounds 2-15

[0674]

[0675] Under a nitrogen atmosphere, compound H (7.54 g, 11.00 mmol), compound F (3.39 g, 11.00 mmol), t-BuONa (2.11 g, 22.00 mmol), Pd2(dba)3 (0.20 g, 0.22 mmol), and S-phos (0.23 g, 0.55 mmol) were placed in a four-necked flask, and 70 mL of toluene was added. The mixture was heated to 100 °C and reacted for 2 h. LC-MS results showed that the reaction was complete, and the reaction was stopped. The reaction solution was allowed to cool naturally to 30 °C, and 70 mL of water was added. The mixture was extracted and separated, and the organic phase was evaporated to dryness. The crude product was an oily substance. After purification, the product was dried under vacuum at 140 °C for 6 h to obtain 2.70 g of compound 2-15 with a purity of 99.98% and an overall yield of 26.87%.

[0676] LC-MS (APCI): 914.57 [M+H]+ . Calcd for: C 71 H 47 N, 913.37.

[0677] 1H NMR (400 MHz, Methylene Chloride-d2) δ 7.96 – 7.85 (m, 3H), 7.79(dt, J = 7.6, 0.9 Hz, 1H), 7.71 (ddt, J = 9.8, 7.7, 1.2 Hz, 2H), 7.67 – 7.58(m, 6H), 7.56 – 7.42 (m, 13H), 7.41 – 7.27 (m, 7H), 7.18 – 7.02 (m, 9H), 6.99(t, J = 7.6 Hz, 1H), 6.71 (dt, J = 7.6, 0.9 Hz, 1H), 6.51 (dt, J = 7.6, 1.0Hz, 1H), 6.43 (dd, J = 7.5, 1.1 Hz, 1H), 6.26 (td, J = 7.5, 1.1 Hz, 1H), 6.03 (dt, J = 7.5, 0.9 Hz, 1H).

[0678] Synthetic Example 20: Preparation of Compounds 2-16

[0679] Step 1: Preparation of intermediate 2-16-1

[0680]

[0681] Under nitrogen protection, compound J (40.00 g, 141.3 mmol), compound D (32.50 g, 148.3 mmol), potassium carbonate (39.06 g, 282.6 mmol), and Pd(PPh3)2Cl2 (1.97 g, 2.8 mmol) were placed in a 1 L four-necked reaction flask. 450 mL of tetrahydrofuran and 150 mL of water were added, the mixture was purged with nitrogen three times, and the mixture was heated to 80 °C to react. After the reaction was complete (approximately 8 hours), the reaction solution was cooled to room temperature (25 °C), separated into layers, the aqueous phase was discarded, the organic phase was evaporated to dryness, dissolved in 500 mL of dichloromethane, and passed through a silica gel rapid column (200-300 mesh silica gel, column height 5 cm, column diameter 8 cm). The solution was washed with 100 mL of dichloromethane, evaporated to dryness, and 500 mL of ethanol was added. The mixture was stirred overnight (12 hours) at room temperature (25 °C), and then filtered to obtain 33.15 g of intermediate 2-16-1 with a purity of 99.00% and a yield of 79.45%.

[0682] Step 2: Preparation of intermediate 2-16-2

[0683]

[0684] Under nitrogen protection, intermediate 2-16-1 (22.20 g, 75.2 mmol) and compound E (30.49 g, 71.4 mmol) were placed in a 1 L four-necked reaction flask, followed by 600 mL of toluene. The mixture was heated to 120 °C, and 100 mL of solvent was distilled off under normal pressure. The mixture was then cooled to room temperature (25 °C), and sodium tert-butoxide (14.45 g, 150.4 mmol), Pd2(dba)3 (1.38 g, 1.5 mmol), and S-phos (2.47 g, 6.02 mmol) were added. The mixture was purged with nitrogen three times, and then heated to 80 °C. After the reaction was complete (approximately 4 h), the reaction solution was cooled to room temperature (25 °C), washed once with 200 mL of water, and the layers were separated. The aqueous phase was discarded, and the organic phase was passed through a silica gel fast column (200-300 mesh silica gel, column height 5 cm, column diameter 8 cm). The solution was eluted with 100 mL of toluene, and the column buffer was evaporated to dryness. The crude product was added to 30 mL of dichloromethane and 500 mL of ethanol, heated to 80 °C and stirred for 1 h, then cooled to room temperature (25 °C) and filtered to obtain the crude product. The crude product from the previous step was then added to 20 mL of toluene, 200 mL of ethanol, and 500 mL of ethyl acetate, heated to 80 °C and stirred for 1 h, then cooled to room temperature (25 °C) and filtered to obtain the crude product. The crude product from the previous step was then added to 500 mL of ethyl acetate, stirred overnight (12 h) at room temperature (25 °C), and filtered to obtain 33.0 g of intermediate 2-16-2, with a purity of 99.00% and a yield of 67.57%.

[0685] Step 3: Preparation of compound 2-16

[0686]

[0687] Under a nitrogen atmosphere, intermediate 2-16-2 (65.40 g, 95.4 mmol) and compound G (29.48 g, 95.4 mmol) were placed in a 2 L four-necked reaction flask. 1000 mL of toluene was added, the temperature was raised to 120 °C, 200 mL of solvent was evaporated under normal pressure, and the temperature was lowered to room temperature (25 °C). Sodium tert-butoxide (18.27 g, 190.1 mmol) and Pd2(dba)3 (1.35 g, 1.9 mmol) were then added to the 2 L four-necked reaction flask. The mixture was purged with nitrogen three times and then heated to 105 °C to react. After the reaction was completed overnight (approximately 16 h), the reaction solution was cooled to room temperature (25 °C), 300 mL of water was added, and the layers were separated. The organic phase was passed through a silica gel fast column (200-300 mesh silica gel, column height 5 cm, column diameter 8 cm). The organic phase was eluted with 200 mL of toluene, and the column eluent was evaporated to dryness. 100 mL of dichloromethane and 500 mL of ethyl acetate were added to dissolve the eluent. The mixture was then subjected to reduced pressure at room temperature (25 °C) to a final volume of 400 mL. The mixture was stirred overnight at room temperature (25 °C) (16 h) to precipitate crystals. The crystals were filtered to obtain the crude product. After purification, the product was dried under vacuum at 120 °C for 8 hours to obtain 65.0 g of compound 2-16 with a purity of 99.75% and an overall yield of 76.42%.

[0688] LC-MS (APCI): 914.75 (M+H + ).Calculated for: C 71 H 47 N.

[0689] 1H NMR (400 MHz, Methylene Chloride-d2) δ 7.96 – 7.90 (m, 2H), 7.87(dt, J = 8.2, 1.1 Hz, 1H), 7.78 (dt, J = 7.6, 1.0 Hz, 1H), 7.70 (td, J = 7.7,7.2, 1.2 Hz, 2H), 7.64 – 7.59 (m, 2H), 7.59 – 7.28 (m, 22H), 7.18 – 7.06 (m,10H), 7.06 – 6.97 (m, 2H), 6.71 (dt, J = 7.6, 0.9 Hz, 1H), 6.51 (dt, J = 7.6,1.0 Hz, 1H), 6.43 (dd, J = 7.5, 1.1 Hz, 1H), 6.19 (td, J = 7.5, 1.1 Hz, 1H), 6.03 (dt, J = 7.6, 1.0 Hz, 1H).

[0690] Synthetic Example 21: Preparation of Compounds 1-95

[0691] Step 1: Preparation of intermediate 1-95-1

[0692]

[0693] Under a nitrogen atmosphere, compound BE (10.00 g, 27.8 mmol), compound BF (7.17 g, 29.2 mmol), and 200 mL of toluene were added to a four-necked reaction flask. The mixture was heated to 150 °C to remove 20 mL of toluene. Under nitrogen protection, the mixture was cooled to 25 °C, and then Pd2(dba)3 (0.51 g, 0.56 mmol), S-phos (0.91 g, 2.2 mmol), and sodium tert-butoxide (4.01 g, 41.7 mmol) were added. The mixture was heated to 75 °C and reacted. After the reaction was completed (approximately 3 hours), the mixture was stirred and cooled to 25 °C. A large amount of solid precipitated out. 200 mL of water was added, and the mixture was filtered directly. The solid was dried under vacuum, washed with 50 mL of EtOH, and then washed with 50 mL of ToL to obtain a wet product of 16.00 g. The product was dried under vacuum at 80 °C to obtain 14 g of intermediate 1-95-1 with a purity of 99.75%.

[0694] LC-MS (APCI): (M+H) + 524.42.

[0695] Step 2: Preparation of Compounds 1-95

[0696]

[0697] Under a nitrogen atmosphere, intermediates 1-95-1 (14.00 g, 26.7 mmol), 2-3-1 (11.98 g, 28.1 mmol), and 200 mL of toluene were added to a four-necked reaction flask. The mixture was heated to 150 °C to remove 20 mL of toluene. Under nitrogen protection, the mixture was cooled to 25 °C, and then Pd2(dba)3 (0.49 g, 0.54 mmol), X-phos (1.02 g, 2.14 mmol), and sodium tert-butoxide (3.85 g, 40.1 mmol) were added. The mixture was heated to 70 °C and reacted. After the reaction was completed (approximately 3 hours), the mixture was naturally stirred and cooled to 25 °C. 50 mL of water was added to quench the reaction, and the mixture was separated. The organic phase was passed through a 20 g 200-300 mesh 150 mL silica gel funnel and washed with 100 mL of DCM. The organic phase was then evaporated to dryness to obtain the crude product. After purification, the product was dried under vacuum at 120°C for 8 hours to obtain 7.0 g of compound 1-95 with a purity of 99.86% and an overall yield of 28.66%.

[0698] LC-MS (APCI): (M+H) + 914.61 .Calcd for: C 71 H 47 N,

[0699] 1H NMR (400 MHz, Methylene Chloride-d2) δ 7.89 – 7.77 (m, 7H), 7.63 –7.54 (m, 9H), 7.50 – 7.41 (m, 7H), 7.38 – 7.33 (m, 4H), 7.32 – 7.24 (m, 6H), 7.12 – 6.98 (m, 10H), 6.84 (d, J = 1.6 Hz, 1H), 6.65 (dd, J = 7.6, 0.9 Hz, 2H), 6.62 – 6.56 (m, 1H).

[0700] Synthetic Example 22: Preparation of Compounds 1-126

[0701]

[0702] The synthesis method of compound 1-126 is the same as that of compound 2-44, except that compound BI is used instead of intermediate 2-19-1.

[0703] LC-MS (APCI): (M+H) + 838.63.

[0704] Synthesis Example 23: Preparation of Compound 2-12

[0705]

[0706] The synthesis method of compound 2-12 is the same as that of compound 2-1, except that compound BG is used instead of intermediate 2-1-1.

[0707] LC-MS (APCI): (M+H) + 839.75.

[0708] 1 H NMR (400 MHz, Methylene Chloride-d2) δ 7.91 – 7.84 (m, 2H), 7.78(dt, J = 7.7, 1.0 Hz, 2H), 7.72 (dt, J = 7.7, 1.0 Hz, 1H), 7.67 – 7.64 (m,1H), 7.59 – 7.54 (m, 2H), 7.51 – 7.25 (m, 20H), 7.13 – 6.94 (m, 9H), 6.77 (t,J = 7.2 Hz, 1H), 6.68 (dt, J = 7.6, 0.9 Hz, 1H), 6.40 (dd, J = 7.5, 1.1 Hz,1H), 6.34 (d, J = 7.6 Hz, 1H), 6.20 (td, J = 7.5, 1.2 Hz, 1H), 6.00 (dt, J =7.6, 1.0 Hz, 1H).

[0709] Synthetic Example 24: Preparation of Compounds 1-96

[0710]

[0711] The synthesis method of compounds 1-96 is the same as that of compounds 1-95, except that intermediate 1-109-1 is used instead of compound BF.

[0712] LC-MS (APCI): (M+H) + 914.61. Calculated for: C 71 H 47 N.

[0713] 1H NMR (400 MHz, Methylene Chloride-d2) δ 7.93 – 7.76 (m, 7H), 7.72(t, J = 1.8 Hz, 1H), 7.67 – 7.60 (m, 2H), 7.60 – 7.55 (m, 3H), 7.54 – 7.44(m, 9H), 7.44 – 7.34 (m, 6H), 7.34 – 7.25 (m, 6H), 7.16 – 7.08 (m, 4H), 7.07– 7.00 (m, 5H), 6.87 – 6.80 (m, 1H), 6.66 (dt, J = 7.6, 0.9 Hz, 2H), 6.60(dt, J = 7.6, 1.0 Hz, 1H).

[0714] Device fabrication examples

[0715] Device Comparison Example 1

[0716] This embodiment provides an organic electroluminescent element, such as... Figure 1 As shown, it includes, from bottom to top, 1. an anode, 2. a hole injection layer, 3. a hole transport layer, 4. a light-emitting auxiliary layer, 5. a light-emitting layer, 6. an electron transport layer, 7. an electron injection layer, and 8. a cathode.

[0717] The specific device structure is as follows:

[0718] ITO / HT:PD(10nm,98:2) / HT(130nm) / BP-1(15nm) / BH-1:BD-1 (97:3v / v%)(30nm) / ET:Liq(35nm,1:1) / Yb(1nm) / Mg:Ag (130nm,1:9).

[0719] Device fabrication process:

[0720] A hole injection layer (HIL) with a thickness of 10 nm was formed by evaporating HT:PD (98:2) on an ITO substrate. A hole transport layer (HTL) with a thickness of 130 nm was then formed by evaporating HT on the hole injection layer. A light-emitting auxiliary layer (EBL) with a thickness of 5 nm was formed by evaporating BP-1 on the hole transport layer. A light-emitting layer (EML) with a thickness of 30 nm was formed by evaporating BH-1:BD-1 (97:3v / v%) on the light-emitting auxiliary layer. An electron transport layer (ETL) with a thickness of 35 nm was then formed by evaporating ET:Liq (1:1). After the electron injection layer (Yb, 1 nm) was sequentially deposited, Mg and Ag (weight ratio 1:9, 130 nm) were co-evaporated to form a semi-transparent cathode, thereby fabricating an organic electroluminescent element 1. This is referred to as Comparative Example 1.

[0721] The abbreviated compounds mentioned above are specifically:

[0722]

[0723]

[0724]

[0725] Device Examples 2-14

[0726] The light-emitting layer was prepared by replacing BD-1 with compound BD-2, and an organic electroluminescent element 134 was fabricated using the same method as in Comparative Example 1. This is referred to as Comparative Example 2.

[0727] The light-emitting layer was prepared by replacing BD-1 with compound BD-3, and an organic electroluminescent element 135 was fabricated using the same method as in Comparative Example 1. This is referred to as Comparative Example 3.

[0728] The light-emitting layer was prepared by replacing BD-1 with compound BD-4, and an organic electroluminescent element 136 was fabricated using the same method as in Comparative Example 1. This is referred to as Comparative Example 4.

[0729] The light-emitting layer was prepared by replacing BD-1 with compound BD-5, and an organic electroluminescent element 137 was fabricated using the same method as in Comparative Example 1. This is referred to as Comparative Example 5.

[0730] The light-emitting layer was prepared by replacing BD-1 with compound BD-6, and an organic electroluminescent element 138 was fabricated using the same method as in Comparative Example 1. This is referred to as Comparative Example 6.

[0731] The light-emitting layer was prepared by replacing BD-1 with compound BD-7, and an organic electroluminescent element 139 was fabricated using the same method as in Comparative Example 1. This is referred to as Comparative Example 7.

[0732] An organic electroluminescent element 140 was fabricated using compound BD-8 instead of BD-1 to prepare the light-emitting layer, and the same method as in Comparative Example 1 was used to fabricate the device. This is referred to as Comparative Example 8.

[0733] The light-emitting layer was prepared by replacing BP-1 with compound BP-2, and an organic electroluminescent element 141 was fabricated using the same method as in Comparative Example 1. This is referred to as Comparative Example 9.

[0734] The light-emitting layer was prepared by replacing BP-1 with compound BP-3, and an organic electroluminescent element 142 was fabricated using the same method as in Comparative Example 1. This is referred to as Comparative Example 10.

[0735] The light-emitting layer was prepared by replacing BP-1 with compound BP-4, and an organic electroluminescent element 143 was fabricated using the same method as in Comparative Example 1. This is referred to as Comparative Example 11.

[0736] The light-emitting layer was prepared by replacing BP-1 with compound BP-5, and an organic electroluminescent element 144 was fabricated using the same method as in Comparative Example 1. This is referred to as Comparative Example 12.

[0737] The light-emitting layer was prepared by replacing BP-1 with compound BP-6, and an organic electroluminescent element 145 was fabricated using the same method as in Comparative Example 1. This is referred to as Comparative Example 13.

[0738] An organic electroluminescent element 146 was fabricated using the same method as Comparative Example 14, with the luminescent layer prepared by replacing BP-1 with compound BP-7.

[0739] Device Examples 1-12

[0740] The light-emitting layer was prepared by replacing BD-1 with the synthetic compound 1-1 of the present invention, and the organic electroluminescent element 2 was fabricated using the same method as in Device Comparative Example 1. This is referred to as Example 1.

[0741] The light-emitting layer was prepared by replacing BD-1 with the synthetic compound 1-2 of the present invention, and the organic electroluminescent element 3 was fabricated using the same method as in Device Comparative Example 1. This is referred to as Example 2.

[0742] The light-emitting layer was prepared by replacing BD-1 with compound 1-34 synthesized in this invention, and the organic electroluminescent element 4 was fabricated using the same method as in Device Comparative Example 1. This is referred to as Example 3.

[0743] The light-emitting layer was prepared by replacing BD-1 with compound 1-35 synthesized in this invention, and an organic electroluminescent element 5 was fabricated using the same method as in Device Comparative Example 1. This is referred to as Example 4.

[0744] The light-emitting layer was prepared by replacing BD-1 with compound 1-28 synthesized in this invention, and an organic electroluminescent element 6 was fabricated using the same method as in Device Comparative Example 1. This is referred to as Example 5.

[0745] The light-emitting layer was prepared by replacing BD-1 with compound 1-36 synthesized in this invention, and an organic electroluminescent element 7 was fabricated using the same method as in Device Comparative Example 1, which is referred to as Example 6.

[0746] An organic electroluminescent element 8 was prepared by replacing BP-1 with compound 2-1 synthesized in this invention, and preparing an organic electroluminescent element 8 by replacing BD-1 with compound 1-1 synthesized in this invention. This was recorded as Example 7.

[0747] The light-emitting auxiliary layer was prepared by replacing BP-1 with compound 2-1 synthesized in this invention, and an organic electroluminescent element 9 was fabricated using the same method as in Device Comparative Example 1. This is referred to as Example 8.

[0748] The light-emitting auxiliary layer was prepared by replacing BP-1 with compound 2-19 synthesized in this invention, and an organic electroluminescent element 10 was fabricated using the same method as in Device Comparative Example 1. This is referred to as Example 9.

[0749] The light-emitting auxiliary layer was prepared by replacing BP-1 with compound 2-20 synthesized in this invention, and an organic electroluminescent element 11 was fabricated using the same method as in Device Comparative Example 1. This is referred to as Example 10.

[0750] The light-emitting auxiliary layer was prepared by replacing BP-1 with compound 2-23 synthesized in this invention, and an organic electroluminescent element 12 was fabricated using the same method as in Device Comparative Example 1. This is referred to as Example 11.

[0751] The light-emitting auxiliary layer was prepared by replacing BP-1 with compound 2-25 synthesized in this invention, and an organic electroluminescent element 13 was fabricated using the same method as in Device Comparative Example 1, which is referred to as Example 12.

[0752] The light-emitting auxiliary layer was prepared by replacing BP-1 with the synthetic compound 1-91 of the present invention, and the organic electroluminescent element 14 was fabricated using the same method as in Device Comparative Example 1, which is recorded as Example 13.

[0753] The light-emitting auxiliary layer was prepared by replacing BP-1 with compound 2-3 synthesized in this invention, and an organic electroluminescent element 15 was fabricated using the same method as in Device Comparative Example 1, which is referred to as Example 14.

[0754] The light-emitting auxiliary layer was prepared by replacing BP-1 with compound 1-94 synthesized in this invention, and an organic electroluminescent element 16 was fabricated using the same method as in Device Comparative Example 1, which is referred to as Example 15.

[0755] The light-emitting auxiliary layer was prepared by replacing BP-1 with the synthetic compound 1-112 of the present invention, and the organic electroluminescent element 17 was fabricated using the same method as in Device Comparative Example 1, which is referred to as Example 16.

[0756] The light-emitting auxiliary layer was prepared by replacing BP-1 with compound 1-118 synthesized in this invention, and an organic electroluminescent element 18 was fabricated using the same method as in Device Comparative Example 1, which is referred to as Example 17.

[0757] The light-emitting auxiliary layer was prepared by replacing BP-1 with compound 2-44 synthesized in this invention, and an organic electroluminescent element 19 was fabricated using the same method as in Device Comparative Example 1, which is referred to as Example 18.

[0758] The light-emitting auxiliary layer was prepared by replacing BP-1 with compound 1-97 synthesized in this invention, and an organic electroluminescent element 20 was fabricated using the same method as in Device Comparative Example 1. This is referred to as Example 19.

[0759] The light-emitting auxiliary layer was prepared by replacing BP-1 with compound 2-15 synthesized in this invention, and an organic electroluminescent element 21 was fabricated using the same method as in Device Comparative Example 1. This is referred to as Example 20.

[0760] The light-emitting auxiliary layer was prepared by replacing BP-1 with compound 2-16 synthesized in this invention, and an organic electroluminescent element 22 was fabricated using the same method as in Device Comparative Example 1. This is referred to as Example 21.

[0761] The light-emitting auxiliary layer was prepared by replacing BP-1 with compound 1-95 synthesized in this invention, and an organic electroluminescent element 23 was fabricated using the same method as in Device Comparative Example 1. This is referred to as Example 22.

[0762] The light-emitting auxiliary layer was prepared by replacing BP-1 with compound 1-126 synthesized in this invention, and an organic electroluminescent element 24 was fabricated using the same method as in Device Comparative Example 1. This is referred to as Example 23.

[0763] The light-emitting auxiliary layer was prepared by replacing BP-1 with compound 2-12 synthesized in this invention, and an organic electroluminescent element 25 was fabricated using the same method as in Device Comparative Example 1. This is referred to as Example 24.

[0764] The light-emitting auxiliary layer was prepared by replacing BP-1 with compound 1-96 synthesized in this invention, and an organic electroluminescent element 26 was fabricated using the same method as in Device Comparative Example 1. This is referred to as Example 25.

[0765] An organic electroluminescent element 27 was prepared by replacing BP-1 with compound 2-1 synthesized in this invention, and by replacing BD-1 with compound 1-2 synthesized in this invention. This was recorded as Example 26.

[0766] An organic electroluminescent element 28 was prepared by replacing BP-1 with compound 2-1 synthesized in this invention, and an organic electroluminescent element 28 was prepared by replacing BD-1 with compound 1-28 synthesized in this invention. This was recorded as Example 27.

[0767] An organic electroluminescent element 29 was prepared by replacing BP-1 with compound 2-19 synthesized in this invention, and by replacing BD-1 with compound 1-1 synthesized in this invention. This was recorded as Example 28.

[0768] An organic electroluminescent element 30 was prepared by replacing BP-1 with compound 2-19 synthesized in this invention, and replacing BD-1 with compound 1-2 synthesized in this invention. This was recorded as Example 29.

[0769] An organic electroluminescent element 31 was prepared by replacing BP-1 with compound 2-19 synthesized in this invention, and replacing BD-1 with compound 1-28 synthesized in this invention. This was recorded as Example 30.

[0770] The light-emitting auxiliary layer was prepared by replacing BP-1 with the synthetic compound 2-25 of the present invention, and the light-emitting layer was prepared by replacing BD-1 with the synthetic compound 1-1 of the present invention. The organic electroluminescent element 32 was fabricated using the same method as in Device Comparative Example 1, and this is referred to as Example 31.

[0771] The light-emitting auxiliary layer was prepared by replacing BP-1 with the synthetic compound 2-25 of the present invention, and the light-emitting layer was prepared by replacing BD-1 with the synthetic compound 1-2 of the present invention. The organic electroluminescent element 33 was fabricated using the same method as in Device Comparative Example 1, and this is referred to as Example 32.

[0772] The light-emitting auxiliary layer was prepared by replacing BP-1 with the synthetic compound 2-25 of the present invention, and the light-emitting layer was prepared by replacing BD-1 with the synthetic compound 1-28 of the present invention. The organic electroluminescent element 34 was fabricated using the same method as in Device Comparative Example 1, and this is referred to as Example 33.

[0773] An organic electroluminescent element 35 was prepared by replacing BP-1 with compound 1-94 synthesized in this invention, and by replacing BD-1 with compound 1-1 synthesized in this invention. This was recorded as Example 34.

[0774] An organic electroluminescent element 36 was prepared by replacing BP-1 with compound 1-94 synthesized in this invention, and by replacing BD-1 with compound 1-2 synthesized in this invention. This was recorded as Example 35.

[0775] An organic electroluminescent element 37 was prepared by replacing BP-1 with compound 1-94 synthesized in this invention, and by replacing BD-1 with compound 1-28 synthesized in this invention. This was recorded as Example 36.

[0776] An organic electroluminescent element 38 was prepared by replacing BP-1 with compound 2-44 synthesized in this invention, and BD-1 with compound 1-1 synthesized in this invention, and an organic electroluminescent element 38 was prepared using the same method as in Comparative Example 1. This is referred to as Example 37.

[0777] An organic electroluminescent element 39 was prepared by replacing BP-1 with compound 2-44 synthesized in this invention, and by replacing BD-1 with compound 1-2 synthesized in this invention. This was recorded as Example 38.

[0778] An organic electroluminescent element 40 was prepared by replacing BP-1 with compound 2-44 synthesized in this invention, and replacing BD-1 with compound 1-28 synthesized in this invention. This was recorded as Example 39.

[0779] An organic electroluminescent element 41 was prepared by replacing BP-1 with compound 1-97 synthesized in this invention, and by replacing BD-1 with compound 1-1 synthesized in this invention. This was recorded as Example 40.

[0780] An organic electroluminescent element 42 was prepared by replacing BP-1 with compound 1-97 synthesized in this invention, and BD-1 with compound 1-2 synthesized in this invention. This was recorded as Example 41.

[0781] An organic electroluminescent element 43 was prepared by replacing BP-1 with compound 1-97 synthesized in this invention and replacing BD-1 with compound 1-28 synthesized in this invention. This was recorded as Example 42.

[0782] An organic electroluminescent element 44 was prepared by replacing BP-1 with compound 1-95 synthesized in this invention, and BD-1 with compound 1-1 synthesized in this invention, and the same method as in Device Comparative Example 1 was used to prepare the light-emitting auxiliary layer. This was recorded as Example 43.

[0783] An organic electroluminescent element 45 was prepared by replacing BP-1 with compound 1-95 synthesized in this invention, and an organic electroluminescent element 45 was prepared by replacing BD-1 with compound 1-2 synthesized in this invention. This was recorded as Example 44.

[0784] An organic electroluminescent element 46 was prepared by replacing BP-1 with compound 1-95 synthesized in this invention, and by replacing BD-1 with compound 1-28 synthesized in this invention. This was recorded as Example 45.

[0785] The light-emitting auxiliary layer was prepared by replacing BP-1 with compound 2-1 synthesized in this invention, and the light-emitting layer was prepared by replacing BH-1 with compound 3-10. The organic electroluminescent element 47 was fabricated using the same method as in Device Comparative Example 1, and is referred to as Example 46.

[0786] The light-emitting auxiliary layer was prepared by replacing BP-1 with compound 2-1 synthesized in this invention, and the light-emitting layer was prepared by replacing BH-1 with compound 3-26. The organic electroluminescent element 48 was fabricated using the same method as in Device Comparative Example 1, and this is referred to as Example 47.

[0787] The light-emitting auxiliary layer was prepared by replacing BP-1 with compound 2-1 synthesized in this invention, and the light-emitting layer was prepared by replacing BH-1 with compound 3-35. The organic electroluminescent element 49 was fabricated using the same method as in Device Comparative Example 1, and this is recorded as Example 48.

[0788] The light-emitting auxiliary layer was prepared by replacing BP-1 with compound 2-1 synthesized in this invention, and the light-emitting layer was prepared by replacing BH-1 with compound 3-36. The organic electroluminescent element 50 was fabricated using the same method as in Device Comparative Example 1, and this is recorded as Example 49.

[0789] The light-emitting auxiliary layer was prepared by replacing BP-1 with compound 2-1 synthesized in this invention, and the light-emitting layer was prepared by replacing BH-1 with compound 3-65. The organic electroluminescent element 51 was fabricated using the same method as in Device Comparative Example 1, and this is recorded as Example 50.

[0790] The light-emitting auxiliary layer was prepared by replacing BP-1 with compound 2-1 synthesized in this invention, and the light-emitting layer was prepared by replacing BH-1 with compound 3-74. The organic electroluminescent element 52 was fabricated using the same method as in Device Comparative Example 1, and this is referred to as Example 51.

[0791] The light-emitting auxiliary layer was prepared by replacing BP-1 with compound 2-19 synthesized in this invention, and the light-emitting layer was prepared by replacing BH-1 with compound 3-10. The organic electroluminescent element 53 was fabricated using the same method as in Device Comparative Example 1, and this is recorded as Example 52.

[0792] The light-emitting auxiliary layer was prepared by replacing BP-1 with compound 2-19 synthesized in this invention, and the light-emitting layer was prepared by replacing BH-1 with compound 3-26. The organic electroluminescent element 54 was fabricated using the same method as in Device Comparative Example 1, and this is recorded as Example 53.

[0793] The light-emitting auxiliary layer was prepared by replacing BP-1 with compound 2-19 synthesized in this invention, and the light-emitting layer was prepared by replacing BH-1 with compound 3-35. The organic electroluminescent element 55 was fabricated using the same method as in Device Comparative Example 1, and this is recorded as Example 54.

[0794] The light-emitting auxiliary layer was prepared by replacing BP-1 with compound 2-19 synthesized in this invention, and the light-emitting layer was prepared by replacing BH-1 with compound 3-36. The organic electroluminescent element 56 was fabricated using the same method as in Device Comparative Example 1, and this is referred to as Example 55.

[0795] The light-emitting auxiliary layer was prepared by replacing BP-1 with compound 2-19 synthesized in this invention, and the light-emitting layer was prepared by replacing BH-1 with compound 3-65. The organic electroluminescent element 57 was fabricated using the same method as in Device Comparative Example 1, and this is recorded as Example 56.

[0796] The light-emitting auxiliary layer was prepared by replacing BP-1 with compound 2-19 synthesized in this invention, and the light-emitting layer was prepared by replacing BH-1 with compound 3-74. The organic electroluminescent element 58 was fabricated using the same method as in Device Comparative Example 1, and this is recorded as Example 57.

[0797] The light-emitting auxiliary layer was prepared by replacing BP-1 with compound 2-25 synthesized in this invention, and the light-emitting layer was prepared by replacing BH-1 with compound 3-10. The organic electroluminescent element 59 was fabricated using the same method as in Device Comparative Example 1, and this is recorded as Example 58.

[0798] The light-emitting auxiliary layer was prepared by replacing BP-1 with compound 2-25 synthesized in this invention, and the light-emitting layer was prepared by replacing BH-1 with compound 3-26. The organic electroluminescent element 60 was fabricated using the same method as in Device Comparative Example 1, and this is recorded as Example 59.

[0799] The light-emitting auxiliary layer was prepared by replacing BP-1 with compound 2-25 synthesized in this invention, and the light-emitting layer was prepared by replacing BH-1 with compound 3-35. The organic electroluminescent element 61 was fabricated using the same method as in Device Comparative Example 1, and this is recorded as Example 60.

[0800] The light-emitting auxiliary layer was prepared by replacing BP-1 with compound 2-25 synthesized in this invention, and the light-emitting layer was prepared by replacing BH-1 with compound 3-36. The organic electroluminescent element 62 was fabricated using the same method as in Device Comparative Example 1, and this is referred to as Example 61.

[0801] The light-emitting auxiliary layer was prepared by replacing BP-1 with compound 2-25 synthesized in this invention, and the light-emitting layer was prepared by replacing BH-1 with compound 3-65. The organic electroluminescent element 63 was fabricated using the same method as in Device Comparative Example 1, and this is referred to as Example 62.

[0802] The light-emitting auxiliary layer was prepared by replacing BP-1 with compound 2-25 synthesized in this invention, and the light-emitting layer was prepared by replacing BH-1 with compound 3-74. The organic electroluminescent element 64 was fabricated using the same method as in Device Comparative Example 1, and this is referred to as Example 63.

[0803] The light-emitting auxiliary layer was prepared by replacing BP-1 with compound 1-94 synthesized in this invention, and the light-emitting layer was prepared by replacing BH-1 with compound 3-35. The organic electroluminescent element 65 was fabricated using the same method as in Device Comparative Example 1, and this is recorded as Example 64.

[0804] The light-emitting auxiliary layer was prepared by replacing BP-1 with compound 1-94 synthesized in this invention, and the light-emitting layer was prepared by replacing BH-1 with compound 3-65. The organic electroluminescent element 66 was fabricated using the same method as in Device Comparative Example 1, and is referred to as Example 65.

[0805] The light-emitting auxiliary layer was prepared by replacing BP-1 with compound 1-94 synthesized in this invention, and the light-emitting layer was prepared by replacing BH-1 with compound 3-74. The organic electroluminescent element 67 was fabricated using the same method as in Device Comparative Example 1, and this is referred to as Example 66.

[0806] The light-emitting auxiliary layer was prepared by replacing BP-1 with compound 2-44 synthesized in this invention, and the light-emitting layer was prepared by replacing BH-1 with compound 3-10. The organic electroluminescent element 68 was fabricated using the same method as in Device Comparative Example 1, and this is recorded as Example 67.

[0807] The light-emitting auxiliary layer was prepared by replacing BP-1 with compound 2-44 synthesized in this invention, and the light-emitting layer was prepared by replacing BH-1 with compound 3-26. The organic electroluminescent element 69 was fabricated using the same method as in Device Comparative Example 1, and this is referred to as Example 68.

[0808] The light-emitting auxiliary layer was prepared by replacing BP-1 with compound 2-44 synthesized in this invention, and the light-emitting layer was prepared by replacing BH-1 with compound 3-35. The organic electroluminescent element 70 was fabricated using the same method as in Device Comparative Example 1, and this is recorded as Example 69.

[0809] The light-emitting auxiliary layer was prepared by replacing BP-1 with compound 2-44 synthesized in this invention, and the light-emitting layer was prepared by replacing BH-1 with compound 3-36. The organic electroluminescent element 71 was fabricated using the same method as in Device Comparative Example 1, and this is referred to as Example 70.

[0810] The light-emitting auxiliary layer was prepared by replacing BP-1 with compound 2-44 synthesized in this invention, and the light-emitting layer was prepared by replacing BH-1 with compound 3-65. The organic electroluminescent element 72 was fabricated using the same method as in Device Comparative Example 1, and this is referred to as Example 71.

[0811] The light-emitting auxiliary layer was prepared by replacing BP-1 with compound 2-44 synthesized in this invention, and the light-emitting layer was prepared by replacing BH-1 with compound 3-74. The organic electroluminescent element 73 was fabricated using the same method as in Device Comparative Example 1, and this is referred to as Example 72.

[0812] The light-emitting auxiliary layer was prepared by replacing BP-1 with compound 1-97 synthesized in this invention, and the light-emitting layer was prepared by replacing BH-1 with compound 3-35. The organic electroluminescent element 74 was fabricated using the same method as in Device Comparative Example 1, and this is referred to as Example 73.

[0813] The light-emitting auxiliary layer was prepared by replacing BP-1 with compound 1-97 synthesized in this invention, and the light-emitting layer was prepared by replacing BH-1 with compound 3-65. The organic electroluminescent element 75 was fabricated using the same method as in Device Comparative Example 1, and this is recorded as Example 74.

[0814] The light-emitting auxiliary layer was prepared by replacing BP-1 with compound 1-97 synthesized in this invention, and the light-emitting layer was prepared by replacing BH-1 with compound 3-74. The organic electroluminescent element 76 was fabricated using the same method as in Device Comparative Example 1, and this is referred to as Example 75.

[0815] The light-emitting auxiliary layer was prepared by replacing BP-1 with compound 1-95 synthesized in this invention, and the light-emitting layer was prepared by replacing BH-1 with compound 3-35. The organic electroluminescent element 77 was fabricated using the same method as in Device Comparative Example 1, and this is referred to as Example 76.

[0816] The light-emitting auxiliary layer was prepared by replacing BP-1 with compound 1-95 synthesized in this invention, and the light-emitting layer was prepared by replacing BH-1 with compound 3-65. The organic electroluminescent element 78 was fabricated using the same method as in Device Comparative Example 1, and this is referred to as Example 77.

[0817] The light-emitting auxiliary layer was prepared by replacing BP-1 with compound 1-95 synthesized in this invention, and the light-emitting layer was prepared by replacing BH-1 with compound 3-74. The organic electroluminescent element 79 was fabricated using the same method as in Device Comparative Example 1, and this is referred to as Example 78.

[0818] The light-emitting layer was prepared by replacing BD-1 with compound 1-1 synthesized in this invention, and the light-emitting layer was prepared by replacing BH-1 with compound 3-10. The organic electroluminescent element 80 was fabricated using the same method as in Device Comparative Example 1, and is referred to as Example 79.

[0819] The light-emitting layer was prepared by replacing BD-1 with compound 1-1 synthesized in this invention, and the light-emitting layer was prepared by replacing BH-1 with compound 3-26. The organic electroluminescent element 81 was fabricated using the same method as in Device Comparative Example 1, and this is referred to as Example 80.

[0820] The light-emitting layer was prepared by replacing BD-1 with compound 1-1 synthesized in this invention, and the light-emitting layer was prepared by replacing BH-1 with compound 3-35. The organic electroluminescent element 82 was fabricated using the same method as in Device Comparative Example 1, and is referred to as Example 81.

[0821] The light-emitting layer was prepared by replacing BD-1 with compound 1-1 synthesized in this invention, and the light-emitting layer was prepared by replacing BH-1 with compound 3-36. The organic electroluminescent element 83 was fabricated using the same method as in Device Comparative Example 1, and is referred to as Example 82.

[0822] The light-emitting layer was prepared by replacing BD-1 with compound 1-1 synthesized in this invention, and the light-emitting layer was prepared by replacing BH-1 with compound 3-65. The organic electroluminescent element 84 was fabricated using the same method as in Device Comparative Example 1, and is referred to as Example 83.

[0823] The light-emitting layer was prepared by replacing BD-1 with compound 1-1 synthesized in this invention, and the light-emitting layer was prepared by replacing BH-1 with compound 3-74. The organic electroluminescent element 85 was fabricated using the same method as in Device Comparative Example 1, and this is referred to as Example 84.

[0824] The light-emitting layer was prepared by replacing BD-1 with compound 1-2 synthesized in this invention, and the light-emitting layer was prepared by replacing BH-1 with compound 3-10. The organic electroluminescent element 86 was prepared using the same method as in Device Comparative Example 1, and is referred to as Example 85.

[0825] The light-emitting layer was prepared by replacing BD-1 with compound 1-2 synthesized in this invention, and the light-emitting layer was prepared by replacing BH-1 with compound 3-26. The organic electroluminescent element 87 was fabricated using the same method as in Device Comparative Example 1, and is referred to as Example 86.

[0826] The light-emitting layer was prepared by replacing BD-1 with compound 1-2 synthesized in this invention, and the light-emitting layer was prepared by replacing BH-1 with compound 3-35. The organic electroluminescent element 88 was prepared using the same method as in Device Comparative Example 1, and this is recorded as Example 87.

[0827] The light-emitting layer was prepared by replacing BD-1 with compound 1-2 synthesized in this invention, and the light-emitting layer was prepared by replacing BH-1 with compound 3-36. The organic electroluminescent element 89 was fabricated using the same method as in Device Comparative Example 1, and is referred to as Example 88.

[0828] The light-emitting layer was prepared by replacing BD-1 with compound 1-2 synthesized in this invention, and the light-emitting layer was prepared by replacing BH-1 with compound 3-65. The organic electroluminescent element 90 was fabricated using the same method as in Device Comparative Example 1, and this is recorded as Example 89.

[0829] The light-emitting layer was prepared by replacing BD-1 with compound 1-2 synthesized in this invention, and the light-emitting layer was prepared by replacing BH-1 with compound 3-74. The organic electroluminescent element 91 was fabricated using the same method as in Device Comparative Example 1, and this is recorded as Example 90.

[0830] The light-emitting layer was prepared by replacing BD-1 with compound 1-28 synthesized in this invention, and the light-emitting layer was prepared by replacing BH-1 with compound 3-10. The organic electroluminescent element 92 was fabricated using the same method as in Device Comparative Example 1, and is referred to as Example 91.

[0831] The light-emitting layer was prepared by replacing BD-1 with compound 1-28 synthesized in this invention, and the light-emitting layer was prepared by replacing BH-1 with compound 3-26. The organic electroluminescent element 93 was fabricated using the same method as in Device Comparative Example 1, and is referred to as Example 92.

[0832] The light-emitting layer was prepared by replacing BD-1 with compound 1-28 synthesized in this invention, and the light-emitting layer was prepared by replacing BH-1 with compound 3-35. The organic electroluminescent element 94 was fabricated using the same method as in Device Comparative Example 1, and is referred to as Example 93.

[0833] The light-emitting layer was prepared by replacing BD-1 with compound 1-28 synthesized in this invention, and the light-emitting layer was prepared by replacing BH-1 with compound 3-36. The organic electroluminescent element 95 was fabricated using the same method as in Device Comparative Example 1, and is referred to as Example 94.

[0834] The light-emitting layer was prepared by replacing BD-1 with compound 1-28 synthesized in this invention, and the light-emitting layer was prepared by replacing BH-1 with compound 3-65. The organic electroluminescent element 96 was fabricated using the same method as in Device Comparative Example 1, and is referred to as Example 95.

[0835] The light-emitting layer was prepared by replacing BD-1 with compound 1-28 synthesized in this invention, and the light-emitting layer was prepared by replacing BH-1 with compound 3-74. The organic electroluminescent element 97 was fabricated using the same method as in Device Comparative Example 1, and is referred to as Example 96.

[0836] An organic electroluminescent element 98 was prepared by replacing BP-1 with compound 2-1 synthesized in this invention, replacing BD-1 with compound 1-1 synthesized in this invention, and replacing BH-1 with compound 3-35. This was recorded as Example 97.

[0837] An organic electroluminescent element 99 was prepared by replacing BP-1 with compound 2-1 synthesized in this invention, replacing BD-1 with compound 1-1 synthesized in this invention, and replacing BH-1 with compound 3-65. This was recorded as Example 98.

[0838] An organic electroluminescent element 100 was prepared by replacing BP-1 with compound 2-1 synthesized in this invention, replacing BD-1 with compound 1-1 synthesized in this invention, and replacing BH-1 with compound 3-74 with compound 3-74. This was recorded as Example 99.

[0839] The light-emitting auxiliary layer was prepared by replacing BP-1 with compound 2-1 synthesized in this invention, the light-emitting layer was prepared by replacing BD-1 with compound 1-2 synthesized in this invention, and the light-emitting layer was prepared by replacing BH-1 with compound 3-35. The organic electroluminescent element 101 was fabricated using the same method as in Device Comparative Example 1, and this is referred to as Example 100.

[0840] The light-emitting auxiliary layer was prepared by replacing BP-1 with compound 2-1 synthesized in this invention, the light-emitting layer was prepared by replacing BD-1 with compound 1-2 synthesized in this invention, and the light-emitting layer was prepared by replacing BH-1 with compound 3-65. The organic electroluminescent element 102 was fabricated using the same method as in Device Comparative Example 1, and this is referred to as Example 101.

[0841] The light-emitting auxiliary layer was prepared by replacing BP-1 with compound 2-1 synthesized in this invention, the light-emitting layer was prepared by replacing BD-1 with compound 1-2 synthesized in this invention, and the light-emitting layer was prepared by replacing BH-1 with compound 3-74. The organic electroluminescent element 103 was fabricated using the same method as in Device Comparative Example 1, and this is referred to as Example 102.

[0842] The light-emitting auxiliary layer was prepared by replacing BP-1 with compound 2-1 synthesized in this invention, the light-emitting layer was prepared by replacing BD-1 with compound 1-28 synthesized in this invention, and the light-emitting layer was prepared by replacing BH-1 with compound 3-35. The organic electroluminescent element 104 was fabricated using the same method as in Device Comparative Example 1, and this is referred to as Example 103.

[0843] The light-emitting auxiliary layer was prepared by replacing BP-1 with compound 2-1 synthesized in this invention, the light-emitting layer was prepared by replacing BD-1 with compound 1-28 synthesized in this invention, and the light-emitting layer was prepared by replacing BH-1 with compound 3-65. The organic electroluminescent element 105 was fabricated using the same method as in Device Comparative Example 1, and this is recorded as Example 104.

[0844] The light-emitting auxiliary layer was prepared by replacing BP-1 with compound 2-1 synthesized in this invention, the light-emitting layer was prepared by replacing BD-1 with compound 1-28 synthesized in this invention, and the light-emitting layer was prepared by replacing BH-1 with compound 3-74. The organic electroluminescent element 106 was fabricated using the same method as in Device Comparative Example 1, and this is referred to as Example 105.

[0845] The light-emitting auxiliary layer was prepared by replacing BP-1 with compound 2-19 synthesized in this invention, the light-emitting layer was prepared by replacing BD-1 with compound 1-1 synthesized in this invention, and the light-emitting layer was prepared by replacing BH-1 with compound 3-35. The organic electroluminescent element 107 was fabricated using the same method as in Device Comparative Example 1, and this is referred to as Example 106.

[0846] The light-emitting auxiliary layer was prepared by replacing BP-1 with compound 2-19 synthesized in this invention, the light-emitting layer was prepared by replacing BD-1 with compound 1-1 synthesized in this invention, and the light-emitting layer was prepared by replacing BH-1 with compound 3-65. The organic electroluminescent element 108 was fabricated using the same method as in Device Comparative Example 1, and this is recorded as Example 107.

[0847] The light-emitting auxiliary layer was prepared by replacing BP-1 with compound 2-19 synthesized in this invention, the light-emitting layer was prepared by replacing BD-1 with compound 1-1 synthesized in this invention, and the light-emitting layer was prepared by replacing BH-1 with compound 3-74. The organic electroluminescent element 109 was fabricated using the same method as in Device Comparative Example 1, and this is recorded as Example 108.

[0848] An organic electroluminescent element 110 was prepared by replacing BP-1 with compound 2-19 synthesized in this invention, replacing BD-1 with compound 1-2 synthesized in this invention, and replacing BH-1 with compound 3-35. This was recorded as Example 109.

[0849] The light-emitting auxiliary layer was prepared by replacing BP-1 with compound 2-19 synthesized in this invention, the light-emitting layer was prepared by replacing BD-1 with compound 1-2 synthesized in this invention, and the light-emitting layer was prepared by replacing BH-1 with compound 3-65. The organic electroluminescent element 111 was fabricated using the same method as in Device Comparative Example 1, and this is referred to as Example 110.

[0850] The light-emitting auxiliary layer was prepared by replacing BP-1 with compound 2-19 synthesized in this invention, the light-emitting layer was prepared by replacing BD-1 with compound 1-2 synthesized in this invention, and the light-emitting layer was prepared by replacing BH-1 with compound 3-74. The organic electroluminescent element 112 was fabricated using the same method as in Device Comparative Example 1, and this is referred to as Example 111.

[0851] The light-emitting auxiliary layer was prepared by replacing BP-1 with compound 2-19 synthesized in this invention, the light-emitting layer was prepared by replacing BD-1 with compound 1-28 synthesized in this invention, and the light-emitting layer was prepared by replacing BH-1 with compound 3-35. The organic electroluminescent element 113 was fabricated using the same method as in Device Comparative Example 1, and this is referred to as Example 112.

[0852] The light-emitting auxiliary layer was prepared by replacing BP-1 with compound 2-19 synthesized in this invention, the light-emitting layer was prepared by replacing BD-1 with compound 1-28 synthesized in this invention, and the light-emitting layer was prepared by replacing BH-1 with compound 3-65. The organic electroluminescent element 114 was fabricated using the same method as in Device Comparative Example 1, and this is referred to as Example 113.

[0853] The light-emitting auxiliary layer was prepared by replacing BP-1 with compound 2-19 synthesized in this invention, the light-emitting layer was prepared by replacing BD-1 with compound 1-28 synthesized in this invention, and the light-emitting layer was prepared by replacing BH-1 with compound 3-74. The organic electroluminescent element 115 was fabricated using the same method as in Device Comparative Example 1, and this is referred to as Example 114.

[0854] The light-emitting auxiliary layer was prepared by replacing BP-1 with compound 2-25 synthesized in this invention, the light-emitting layer was prepared by replacing BD-1 with compound 1-1 synthesized in this invention, and the light-emitting layer was prepared by replacing BH-1 with compound 3-35. The organic electroluminescent element 116 was fabricated using the same method as in Device Comparative Example 1, and this is referred to as Example 115.

[0855] The light-emitting auxiliary layer was prepared by replacing BP-1 with compound 2-25 synthesized in this invention, the light-emitting layer was prepared by replacing BD-1 with compound 1-1 synthesized in this invention, and the light-emitting layer was prepared by replacing BH-1 with compound 3-65. The organic electroluminescent element 117 was fabricated using the same method as in Device Comparative Example 1, and this is referred to as Example 116.

[0856] The light-emitting auxiliary layer was prepared by replacing BP-1 with compound 2-25 synthesized in this invention, the light-emitting layer was prepared by replacing BD-1 with compound 1-1 synthesized in this invention, and the light-emitting layer was prepared by replacing BH-1 with compound 3-74. The organic electroluminescent element 118 was fabricated using the same method as in Device Comparative Example 1, and this is referred to as Example 117.

[0857] The light-emitting auxiliary layer was prepared by replacing BP-1 with compound 2-25 synthesized in this invention, the light-emitting layer was prepared by replacing BD-1 with compound 1-2 synthesized in this invention, and the light-emitting layer was prepared by replacing BH-1 with compound 3-35. The organic electroluminescent element 119 was fabricated using the same method as in Device Comparative Example 1, and this is referred to as Example 118.

[0858] The light-emitting auxiliary layer was prepared by replacing BP-1 with compound 2-25 synthesized in this invention, the light-emitting layer was prepared by replacing BD-1 with compound 1-2 synthesized in this invention, and the light-emitting layer was prepared by replacing BH-1 with compound 3-65. The organic electroluminescent element 120 was fabricated using the same method as in Device Comparative Example 1, and this is referred to as Example 119.

[0859] The light-emitting auxiliary layer was prepared by replacing BP-1 with compound 2-25 synthesized in this invention, the light-emitting layer was prepared by replacing BD-1 with compound 1-2 synthesized in this invention, and the light-emitting layer was prepared by replacing BH-1 with compound 3-74. The organic electroluminescent element 121 was fabricated using the same method as in Device Comparative Example 1, and this is referred to as Example 120.

[0860] The light-emitting auxiliary layer was prepared by replacing BP-1 with compound 2-25 synthesized in this invention, the light-emitting layer was prepared by replacing BD-1 with compound 1-28 synthesized in this invention, and the light-emitting layer was prepared by replacing BH-1 with compound 3-35. The organic electroluminescent element 122 was fabricated using the same method as in Device Comparative Example 1, and this is referred to as Example 121.

[0861] The light-emitting auxiliary layer was prepared by replacing BP-1 with compound 2-25 synthesized in this invention, the light-emitting layer was prepared by replacing BD-1 with compound 1-28 synthesized in this invention, and the light-emitting layer was prepared by replacing BH-1 with compound 3-65. The organic electroluminescent element 123 was fabricated using the same method as in Device Comparative Example 1, and this is referred to as Example 122.

[0862] The light-emitting auxiliary layer was prepared by replacing BP-1 with compound 2-25 synthesized in this invention, the light-emitting layer was prepared by replacing BD-1 with compound 1-28 synthesized in this invention, and the light-emitting layer was prepared by replacing BH-1 with compound 3-74. The organic electroluminescent element 124 was fabricated using the same method as in Device Comparative Example 1, and this is referred to as Example 123.

[0863] The light-emitting auxiliary layer was prepared by replacing BP-1 with compound 2-44 synthesized in this invention, the light-emitting layer was prepared by replacing BD-1 with compound 1-1 synthesized in this invention, and the light-emitting layer was prepared by replacing BH-1 with compound 3-35. The organic electroluminescent element 125 was fabricated using the same method as in Comparative Example 1, and this is referred to as Example 124.

[0864] The light-emitting auxiliary layer was prepared by replacing BP-1 with compound 2-44 synthesized in this invention, the light-emitting layer was prepared by replacing BD-1 with compound 1-1 synthesized in this invention, and the light-emitting layer was prepared by replacing BH-1 with compound 3-65. The organic electroluminescent element 126 was fabricated using the same method as in Device Comparative Example 1, and this is referred to as Example 125.

[0865] The light-emitting auxiliary layer was prepared by replacing BP-1 with compound 2-44 synthesized in this invention, the light-emitting layer was prepared by replacing BD-1 with compound 1-1 synthesized in this invention, and the light-emitting layer was prepared by replacing BH-1 with compound 3-74. The organic electroluminescent element 127 was fabricated using the same method as in Device Comparative Example 1, and this is referred to as Example 126.

[0866] The light-emitting auxiliary layer was prepared by replacing BP-1 with compound 2-44 synthesized in this invention, the light-emitting layer was prepared by replacing BD-1 with compound 1-2 synthesized in this invention, and the light-emitting layer was prepared by replacing BH-1 with compound 3-35. The organic electroluminescent element 128 was fabricated using the same method as in Device Comparative Example 1, and this is referred to as Example 127.

[0867] The light-emitting auxiliary layer was prepared by replacing BP-1 with compound 2-44 synthesized in this invention, the light-emitting layer was prepared by replacing BD-1 with compound 1-2 synthesized in this invention, and the light-emitting layer was prepared by replacing BH-1 with compound 3-65. The organic electroluminescent element 129 was fabricated using the same method as in Device Comparative Example 1, and this is referred to as Example 128.

[0868] The light-emitting auxiliary layer was prepared by replacing BP-1 with compound 2-44 synthesized in this invention, the light-emitting layer was prepared by replacing BD-1 with compound 1-2 synthesized in this invention, and the light-emitting layer was prepared by replacing BH-1 with compound 3-74. The organic electroluminescent element 130 was fabricated using the same method as in Device Comparative Example 1, and is referred to as Example 129.

[0869] The light-emitting auxiliary layer was prepared by replacing BP-1 with compound 2-44 synthesized in this invention, the light-emitting layer was prepared by replacing BD-1 with compound 1-28 synthesized in this invention, and the light-emitting layer was prepared by replacing BH-1 with compound 3-35. The organic electroluminescent element 131 was fabricated using the same method as in Device Comparative Example 1, and this is referred to as Example 130.

[0870] The light-emitting auxiliary layer was prepared by replacing BP-1 with compound 2-44 synthesized in this invention, the light-emitting layer was prepared by replacing BD-1 with compound 1-28 synthesized in this invention, and the light-emitting layer was prepared by replacing BH-1 with compound 3-65. The organic electroluminescent element 132 was fabricated using the same method as in Device Comparative Example 1, and this is referred to as Example 131.

[0871] The light-emitting auxiliary layer was prepared by replacing BP-1 with compound 2-44 synthesized in this invention, the light-emitting layer was prepared by replacing BD-1 with compound 1-28 synthesized in this invention, and the light-emitting layer was prepared by replacing BH-1 with compound 3-74. The organic electroluminescent element 133 was fabricated using the same method as in Device Comparative Example 1, and this is referred to as Example 132.

[0872] Test Results

[0873] The method for testing luminescence properties is as follows:

[0874] At a current density of 15 mA / cm 2 The driving voltage (unit: V) was tested, with the driving voltage of Comparative Example 1 as 100%.

[0875] The driving voltage of other device embodiments relative to Comparative Example 1 was obtained as follows: Driving voltage (in %) = (Measured driving voltage data of each embodiment and comparative example / Measured driving voltage data of Comparative Example 1) × 100%.

[0876] At a current density of 15 mA / cm 2 The device efficiency (unit: cd / A) was tested. With the efficiency of Comparative Example 1 as 100%, the efficiency of other device embodiments relative to Comparative Example 1 was obtained: Efficiency (unit %) = (Measured current efficiency data of each embodiment and comparative example / Measured current efficiency data of Comparative Example 1) × 100%.

[0877] A voltage was applied to the obtained organic electroluminescent element to achieve a current density of 30 mA / cm². 2 The time (LT95, in hours) from when the brightness becomes 95% of the initial brightness was measured was taken as 100% of the time from when the initial brightness of Comparative Example 1 becomes 95%. The lifetime of other device embodiments relative to Comparative Example 1 was obtained: lifetime (LT95, in %) = (measured lifetime data of each embodiment and comparative example / measured lifetime data of Comparative Example 1) × 100%.

[0878] IVL testing instrument: F STAR Optical Measurement Systems, model: FS-2000GA4; atmospheric environment, room temperature.

[0879] The test results are shown in Tables 1-6.

[0880] Table 1

[0881]

[0882] As can be seen from Table 1, when the light-emitting layer BD-1 is replaced with the compound of formula (1) of this invention, the driving voltage of the organic electroluminescent element is reduced and the efficiency and lifetime are further improved.

[0883] Table 2

[0884]

[0885] As can be seen from Table 2, when the light-emitting auxiliary layer BP-1 is replaced with the compound of formula (2) of this invention, the driving voltage of the organic electroluminescent element is reduced and the efficiency or lifetime is further improved.

[0886] Table 3

[0887]

[0888] As can be seen from Table 3, when the light-emitting layer BD-1 is replaced with the compound of formula (1) of the present invention and the light-emitting auxiliary layer BP-1 is replaced with the compound of formula (2) of the present invention, the driving voltage of the organic electroluminescent element is reduced compared with Comparative Example 1 and the combinations in Tables 1-2, and the efficiency or lifetime is further improved.

[0889] Table 4

[0890]

[0891]

[0892] As can be seen from Table 4, when the light-emitting layer BH-1 is replaced with the compound of formula (3) of the present invention and the light-emitting auxiliary layer BP-1 is replaced with the compound of formula (2) of the present invention, the driving voltage of the organic electroluminescent element is significantly reduced compared with Comparative Example 1 and the combinations in Tables 1-2, and the efficiency or lifetime is further improved.

[0893] Table 5

[0894]

[0895] As can be seen from Table 5, when the light-emitting layer BH-1 is replaced with the compound of formula (3) of the present invention and the light-emitting layer BD-1 is replaced with the compound of formula (1) of the present invention, the driving voltage of the organic electroluminescent element is significantly reduced compared with Comparative Example 1 and the combinations in Tables 1-2, and the efficiency or lifetime is further improved.

[0896] Table 6

[0897]

[0898]

[0899] As can be seen from Table 6, when the light-emitting layer BH-1 is replaced with the compound of formula (3) of the present invention, the light-emitting layer BD-1 is replaced with the compound of formula (1) of the present invention, and the light-emitting auxiliary layer BP-1 is replaced with the compound of formula (2) of the present invention, the driving voltage of the organic electroluminescent element is significantly reduced compared with Comparative Example 1 and the combinations in Tables 1-5, and the efficiency or lifetime is further improved.

[0900] The foregoing has shown and described the basic principles, main features, and advantages of the present invention. Those skilled in the art should understand that the present invention is not limited to the above embodiments. The embodiments and descriptions in the specification are merely illustrative of the principles of the invention. Various changes and modifications can be made to the invention without departing from its spirit and scope, and all such changes and modifications fall within the scope of the present invention as claimed. The scope of protection of this invention is defined by the appended claims and their equivalents.

Claims

1. An organic electroluminescent element, comprising an anode, a cathode, and an organic functional layer including a light-emitting layer located between the anode and the cathode, wherein a hole transport region is included between the anode and the light-emitting layer, characterized in that, The hole transport region contains the compound shown in formula (2). Equation (2) Ar1 is selected from substituted or unsubstituted naphthyl groups. Ar2 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted fluorenyl. Ar3 is selected from substituted or unsubstituted helical fluorene groups. L1 and L2 are each independently selected from substituted or unsubstituted phenylene or substituted or unsubstituted naphthylene, wherein L2 is selected from... , L3 and L4 are each independently selected from single-bonded, substituted, or unsubstituted phenylene compounds. L3 and L4 cannot both be single bonds. R1 and R2 are each independently selected from hydrogen, substituted or unsubstituted C1-C10 alkyl groups, substituted or unsubstituted phenyl groups, and R1 and R2 are connected to each other to form a ring structure or are not connected to each other. The substituents in "substituted or unsubstituted" are each independently selected from one or a combination of deuterium, halogen, cyano, C1-C10 alkyl, C6-C30 aryl, and C3-C30 heteroaryl. The heteroatom of the heteroaryl group is selected from one or more of N, O, S, Si, P, and B. The above compounds may or may not contain at least one deuterium; The light-emitting layer of the organic electroluminescent element further comprises the compound shown in formula (3). Equation (3) R 32 R 33 R 36 -R 37 Each is independently selected from hydrogen, deuterium, substituted or unsubstituted C6-C30 aryl groups, R 31 R 34 R 35 R 38 Each is independently selected from hydrogen or deuterium. Ar 31 Ar 32 Each is independently selected from substituted or unsubstituted C6-C30 aryl groups and substituted or unsubstituted C3-C30 heteroaryl groups. The structure of formula (3) is unsubstituted or substituted with one or more of the following substituents: deuterium, halogen, cyano, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C1-C10 alkoxy, substituted or unsubstituted amino, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C3-C10 cycloalkoxy, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C1-C10 alkenyl, substituted or unsubstituted C1-C10 alkynyl, substituted or unsubstituted silyl. The substituents in "substituted or unsubstituted" are each independently selected from one or a combination of deuterium, halogen, cyano, C1-C10 alkyl, C1-C10 alkoxy, amino, C3-C10 cycloalkyl, C3-C10 cycloalkoxy, C6-C30 aryl, C3-C30 heteroaryl, C1-C10 alkenyl, and C1-C10 alkynyl. The heteroatom of the heteroaryl group is selected from one or more of N, O, S, Si, P, and B.

2. The organic electroluminescent element according to claim 1, characterized in that, The compound represented by formula (2) has the structures shown in formulas 2-1 to 2-8. ， The definitions of Ar1, Ar2, L1-L4, R1, and R2 are the same as above; The definition of substituents in "substituted or unsubstituted" is the same as above; The above compounds may or may not contain at least one deuterium.

3. The organic electroluminescent element according to claim 1, characterized in that, In the compound represented by formula (2) Selected from the following groups, whether substituted or unsubstituted: ； " "Indicates the connection position with N; The definition of substituents in "substituted or unsubstituted" is the same as above.

4. The organic electroluminescent element according to claim 1, characterized in that, The compound represented by formula (2) is shown below: 。 5. The organic electroluminescent element according to any one of claims 1-4, characterized in that, In the compound represented by formula (3), the Ar 31 Selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted biphenyl, substituted or unsubstituted phenylnaphthyl, or selected from substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzonaphthiofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazoleyl; the Ar 32 It is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted biphenyl, substituted or unsubstituted phenylnaphthyl, or selected from substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzonaphthuryl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazoyl.

6. The organic electroluminescent element according to any one of claims 1-5, characterized in that, In the compound represented by formula (3), the Ar 31 Selected from the following groups that are unsubstituted, partially deuterated, or fully deuterated: ， The Ar 32 Selected from the following groups that are unsubstituted, partially deuterated, or fully deuterated: 。 7. The organic electroluminescent element according to any one of claims 1-6, characterized in that, The compound represented by formula (3) is shown in the following 3-1 to 3-76: 。 8. An organic electroluminescent element, comprising an anode, a cathode, and an organic functional layer including a light-emitting layer located between the anode and the cathode, characterized in that, The luminescent layer comprises the compound of formula (1), as shown in 1-1 to 1-36 below: 。 9. The organic electroluminescent element according to claim 8, characterized in that, The light-emitting layer of the organic electroluminescent element further comprises a compound represented by formula (3), which is shown in 3-1 to 3-76 below: 。 10. An electronic device, comprising a display or lighting device, characterized in that, The electronic device comprises the organic electroluminescent element according to any one of claims 1-9.

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