Organic compound, light-emitting element, and display panel

Abstract

The application discloses an organic compound, a light-emitting element and a display panel. The organic compound has a structure shown in formula (1). The organic compound provided by the application has a heterocycle and an amine group at the same time, and the heterocycle and the amine group can be connected to the same benzene ring, so that the conjugation effect and resonance effect of the organic compound are enhanced, the performance of the organic compound is improved, and when the organic compound is used in the light-emitting element, the light-emitting efficiency of the light-emitting element can be improved, and the service life of the light-emitting element can be prolonged.

Description

TECHNICAL FIELD

[0001] The present application relates to the technical field of display, in particular to an organic compound, a light-emitting element and a display panel. BACKGROUND

[0002] At present, an organic electroluminescent element generally has a positive electrode, a negative electrode and an organic layer between the two, and the organic matter of the organic layer is used to convert electrical energy into light energy, so as to realize organic electroluminescence. In order to improve the luminous efficiency and service life of the organic electroluminescent element, the organic layer is often multi-layered, and the organic matter of each layer is different. Specifically, the organic layer mainly includes a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer and the like. A voltage is applied between the positive electrode and the negative electrode of the organic electroluminescent element, the positive electrode injects holes into the organic layer, and the negative electrode injects electrons into the organic layer. The injected holes and electrons meet to form excitons, and the excitons emit light when they transition back to the ground state, thereby realizing the light emission of the organic electroluminescent element. The organic electroluminescent device has the characteristics of self-luminous, high brightness, high efficiency, low voltage driving, wide viewing angle, high contrast and high response, etc. Therefore, the organic electroluminescent device has a wide application prospect.

[0003] Correspondingly, the material development of the organic light emitting diode (OLED) has also been widely concerned due to a series of advantages such as diversity in synthesis, simple composition and process. At the same time, in order to improve the luminous efficiency of the organic electroluminescent element, people have tried various energy transfer and conversion mechanism material systems, but the luminous efficiency, stability and life performance of the light-emitting material applied to the OLED element (especially the light-emitting material of the blue light-emitting OLED element) are still low, which limits the performance improvement of the OLED element.

[0004] Therefore, there is an urgent need for an organic compound, a light-emitting element and a display panel to solve the above technical problems. SUMMARY

[0005] The present application provides an organic compound, a light-emitting element and a display panel, which can improve the luminous efficiency and service life of the light-emitting element.

[0006] The present application provides an organic compound, which has a structure as shown in formula (1):

[0007] (1);

[0008] wherein Z is selected from CR1R2, NR3, O or S;

[0009] X and Y are independently selected from O or NR4;

[0010] R1to R4are independently selected from at least one of a substituted or unsubstituted alkyl group having 1-20 carbon atoms, a substituted or unsubstituted aromatic group having 6-30 carbon atoms, a substituted or unsubstituted heteroaromatic group having 5-30 carbon atoms;

[0011] R1, R2are linked to form a ring or are independent of each other;

[0012] R is selected from at least one of H, D, a substituted or unsubstituted alkyl group having 1-20 carbon atoms, a substituted or unsubstituted aromatic group having 6-30 carbon atoms, a substituted or unsubstituted heteroaromatic group having 5-30 carbon atoms;

[0013] Ar1to Ar3are selected from at least one of D, a substituted or unsubstituted alkyl group having 1-20 carbon atoms, a substituted or unsubstituted aromatic group having 6-30 carbon atoms, a substituted or unsubstituted heteroaromatic group having 5-30 carbon atoms;

[0014] Ar4and Ar5are independently selected from at least one of a substituted or unsubstituted aromatic group having 6-30 carbon atoms, a substituted or unsubstituted heteroaromatic group having 5-30 carbon atoms;

[0015] Ar6and Ar7are independently selected from at least one of a substituted or unsubstituted alkyl group having 1-20 carbon atoms, a substituted or unsubstituted aromatic group having 6-30 carbon atoms, a substituted or unsubstituted heteroaromatic group having 5-30 carbon atoms, Ar6and Ar7are linked to form a ring or are independent of each other;

[0016] a, b and c are independently selected from any one of an integer from 0 to 5.

[0017] According to the above purposes of the present application, the embodiments of the present application further provide a light-emitting element, which comprises:

[0018] a first electrode;

[0019] a second electrode located on one side of the first electrode;

[0020] an organic functional layer located between the first electrode and the second electrode;

[0021] wherein the material of the organic functional layer comprises at least one organic compound as described above.

[0022] According to the above purposes of the present application, the embodiments of the present application further provide a display panel, which comprises the light-emitting element as described above.

[0023] The application provides an organic compound, a light-emitting element and a display panel, the organic compound simultaneously has a heterocycle and an amine group, the heterocycle and the amine group can be connected to the same benzene ring, the conjugation effect and the resonance effect of the organic compound are enhanced, the performance of the organic compound is improved, when the organic compound is used in the light-emitting element, the light-emitting efficiency of the light-emitting element can be improved, meanwhile, the service life of the light-emitting element can be prolonged. BRIEF DESCRIPTION OF DRAWINGS

[0024] In order to more clearly illustrate the technical solutions in the embodiments of the application, the following will briefly introduce the drawings needed to be used in the embodiments description. Obviously, the drawings in the following description only constitute some of the embodiments of the application, and for those skilled in the art, other drawings can also be obtained from these drawings without creative labor.

[0025] Figure 1 A structural schematic diagram of the light-emitting element provided by the embodiments of the application. DETAILED DESCRIPTION

[0026] The technical solutions in the embodiments of the application will be described clearly and completely in the following with reference to the drawings in the embodiments of the application. Obviously, the described embodiments only constitute some of the embodiments of the application, rather than all the embodiments. Based on the embodiments in the application, all other embodiments obtained by those skilled in the art without creative labor fall within the protection scope of the application. In addition, it should be understood that the specific embodiments described herein are only used to illustrate and explain the application, and are not used to limit the application. In the application, the orientation words such as "upper" and "lower" generally refer to the upper and lower in the actual use or working state of the device, and specifically refer to the direction of the drawing in the drawings. And "inner" and "outer" refer to the outline of the device. In the application, "optionally", "optional" and "optionally" mean optional, that is, selected from two parallel schemes of "yes" or "no". If there are multiple "optionally" in a technical solution, if there is no special description, and there is no contradictory relationship or mutual restriction, each "optionally" is independent. In the application, the technical features described in an open manner include the closed technical solution composed of the listed features, and also includes the open technical solution containing the listed features.

[0027] In the present application, the terms "aromatic group", "aromatic", "aromatic ring system" have the same meaning and are interchangeable. "Aryl or aromatic group or aromatic ring system" means an aromatic hydrocarbon group derived by removal of a hydrogen atom from a aromatic ring compound, which can be a monocyclic aryl group, or a fused ring aryl group, or a polycyclic aryl group, and for polycyclic ring systems, at least one is an aromatic ring system. For example, "substituted or unsubstituted aryl group having 6 to 40 ring atoms" means an aryl group having 6 to 40 ring atoms, preferably a substituted or unsubstituted aryl group having 6 to 30 ring atoms, more preferably a substituted or unsubstituted aryl group having 6 to 18 ring atoms, particularly preferably a substituted or unsubstituted aryl group having 6 to 14 ring atoms, and the aryl group is optionally further substituted; suitable examples include, but are not limited to: phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, fluoranthenyl, fluorantenyl, pyrenyl, perylenyl, naphthacene, fluorenyl, rylenyl, and derivatives thereof. Understandably, multiple aryl groups can also be interrupted by short non-aromatic units (e.g. <10% non-H atoms such as C, N or O atoms), in particular as in acenaphthene, fluorene, or 9,9-dialkylfluorene, triarylamine, diaryl ether systems should also be included in the definition of aryl.

[0028] In the present application, the terms "heteroaromatic group", "heteroaromatic", "heteroaromatic ring system" have the same meaning and are interchangeable. "Heteroaryl or heteroaromatic group or heteroaromatic ring system" means an aromatic hydrocarbon group derived by removal of a hydrogen atom from an aryl group, in which at least one carbon atom is replaced by a non-carbon atom, which can be an N atom, an O atom, an S atom, etc. For example, "substituted or unsubstituted heteroaryl group having 5 to 40 ring atoms" means a heteroaryl group having 5 to 40 ring atoms, preferably a substituted or unsubstituted heteroaryl group having 6 to 30 ring atoms, more preferably a substituted or unsubstituted heteroaryl group having 6 to 18 ring atoms, particularly preferably a substituted or unsubstituted heteroaryl group having 6 to 14 ring atoms, and the heteroaryl group is optionally further substituted; suitable examples include, but are not limited to: thienyl, furanyl, pyrrolyl, dioxazolyl, triazolyl, imidazolyl, pyridyl, bipyridyl, pyrimidyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, benzothienyl, benzofuranyl, indolyl, pyrroloimidazolyl, pyrrolopyrrolyl, thienopyrrolyl, thienothienyl, furanopyrrolyl, furanofuranyl, thienofuranyl, benzisoxazolyl, benzisothiazolyl, benzimidazolyl, perylenyl, phenanthridinyl, perimidinyl, quinazolinonyl, dibenzothienyl, dibenzofuranyl, carbazolyl, and derivatives thereof.

[0029] In the present application, "substituted" means that one or more hydrogen atoms in a substituent is replaced by a substituent, and when the same substituent appears multiple times, it can be independently selected from different groups, such as when a general formula contains multiple R, R can be independently selected from different groups. In the embodiments of the present application, "substituted or unsubstituted" means that the defined group can be substituted or unsubstituted; when the defined group is substituted, it is understood that the defined group can be substituted with one or more substituents R selected from, but not limited to, a deuterium atom, a cyano group, an isocyano group, a nitro group, or a halogen, an alkyl group containing 1-20 C atoms, a heterocyclic group containing 3-20 ring atoms, an aromatic group containing 6-20 ring atoms, a heteroaromatic group containing 5-20 ring atoms, -NR'R", a silyl group, a carbonyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, a carbamoyl group, a halogen carboxyl group, a formyl group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a trifluoromethyl group, and the above-mentioned groups can be further substituted with an acceptable substituent in the art; wherein R' and R" in -NR'R" are each independently selected from, but not limited to, H, a deuterium atom, a cyano group, an isocyano group, a nitro group, or a halogen, an alkyl group containing 1-10 C atoms, a heterocyclic group containing 3-20 ring atoms, an aromatic group containing 6-20 ring atoms, a heteroaromatic group containing 5-20 ring atoms. Preferably, R is selected from, but not limited to, a deuterium atom, a cyano group, an isocyano group, a nitro group, or a halogen, an alkyl group containing 1-10 C atoms, a heterocyclic group containing 3-10 ring atoms, an aromatic group containing 6-20 ring atoms, a heteroaromatic group containing 5-20 ring atoms, a silyl group, a carbonyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, a carbamoyl group, a halogen carboxyl group, a formyl group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a trifluoromethyl group, and the above-mentioned groups can be further substituted with an acceptable substituent in the art.

[0030] In the present application, "amine group" refers to a derivative of amine, having the structural feature of formula -NR'R", and R' and R" have the same meaning as described above.

[0031] In the present application, "ring atom number" refers to the number of atoms in a structural compound (for example, monocyclic compound, fused ring compound, cross-linked compound, carbocyclic compound, heterocyclic compound) that is obtained by bonding atoms into a ring; when the ring is substituted with a substituent, the atoms contained in the substituent are not included in the ring-forming atoms, and the same applies to the "ring atom number" described below without special conditions, for example, the ring atom number of a benzene ring is 6, the ring atom number of a naphthalene ring is 10, and the ring atom number of a thiophene group is 5.

[0032] In the present application, "*" connected with a single bond represents a connection or a fused site; when the connection site of a group is not specified, it means that an optional connection site in the group is taken as the connection site; when a plurality of substituents with the same symbol are contained on the same group, each substituent can be the same as or different from each other, for example , the 6 R on the benzene ring can be the same as or different from each other; the single bond to which the substituent is connected runs through the corresponding ring, indicating that the substituent can be connected to an optional position of the ring, for example , R is connected to any substitutable position of the benzene ring.

[0033] At present, due to the low performance of the light-emitting material applied to the OLED element, such as the light-emitting efficiency, stability and service life, there is a problem that the performance of the OLED element is difficult to improve. The present application provides an organic compound which can be used as a light-emitting material of an OLED element to improve the performance of the OLED element.

[0034] The present application provides an organic compound, characterized in that the organic compound has a structure as shown in formula (1):

[0035] (1);

[0036] wherein Z is selected from CR1R2, NR3, O or S;

[0037] X and Y are independently selected from O or NR4;

[0038] R1 to R4 are independently selected from at least one of a substituted or unsubstituted alkyl group having 1-20 carbon atoms, a substituted or unsubstituted aromatic group having 6-30 carbon atoms, and a substituted or unsubstituted heteroaromatic group having 5-30 carbon atoms;

[0039] R1 and R2 are connected to form a ring or are independent of each other;

[0040] R is selected from at least one of H, D, a substituted or unsubstituted alkyl group having 1-20 carbon atoms, a substituted or unsubstituted aromatic group having 6-30 carbon atoms, and a substituted or unsubstituted heteroaromatic group having 5-30 carbon atoms;

[0041] Ar1 to Ar3 are independently selected from at least one of D, a substituted or unsubstituted alkyl group having 1-20 carbon atoms, a substituted or unsubstituted aromatic group having 6-30 carbon atoms, and a substituted or unsubstituted heteroaromatic group having 5-30 carbon atoms;

[0042] Ar4 and Ar5 are independently selected from at least one of a substituted or unsubstituted aromatic group having 6-30 carbon atoms and a substituted or unsubstituted heteroaromatic group having 5-30 carbon atoms;

[0043] Ar6and Ar7are independently selected from at least one of a substituted or unsubstituted alkyl group having 1-20 carbon atoms, a substituted or unsubstituted aromatic group having 6-30 carbon atoms, a substituted or unsubstituted heteroaromatic group having 5-30 carbon atoms, and Ar6and Ar7are connected into a ring or are independent of each other;

[0044] a, b and c are independently selected from any one of an integer from 0 to 5.

[0045] In the implementation process, the organic compound provided by the embodiment of the present application has a heterocyclic ring and an amine group at the same time, wherein the heterocyclic ring and the amine group can be connected to the same benzene ring, thereby enhancing the conjugation effect and resonance effect of the organic compound, improving the performance of the organic compound, and when the organic compound provided by the present application is used in a light-emitting element, the light-emitting efficiency of the light-emitting element can be improved, and the service life of the light-emitting element can also be prolonged.

[0046] Specifically, the present application provides an organic compound, characterized in that the organic compound has a structure as shown in formula (1):

[0047] (1);

[0048] wherein Z in formula (1) is selected from CR1R2, NR3, O or S.

[0049] X and Y in formula (1) are independently selected from O or NR4.

[0050] In some embodiments, X and Y can be simultaneously selected from O.

[0051] R1to R4are independently selected from at least one of a substituted or unsubstituted alkyl group having 1-20 carbon atoms, a substituted or unsubstituted aromatic group having 6-30 carbon atoms, a substituted or unsubstituted heteroaromatic group having 5-30 carbon atoms.

[0052] In some embodiments, R1to R4are independently selected from at least one of a substituted or unsubstituted alkyl group having 1-12 carbon atoms, a substituted or unsubstituted aromatic group having 6-20 carbon atoms, a substituted or unsubstituted heteroaromatic group having 5-20 carbon atoms.

[0053] In some embodiments, R1to R4are independently selected from at least one of a substituted or unsubstituted alkyl group having 1-8 carbon atoms, a substituted or unsubstituted aromatic group having 6-15 carbon atoms, a substituted or unsubstituted heteroaromatic group having 5-15 carbon atoms.

[0054] In some embodiments, R1to R3are independently selected from one of an alkyl group having a number of carbon atoms from 1 to 5, a substituted or unsubstituted phenyl group; R4is selected from a methyl group, a substituted or unsubstituted phenyl group, a naphthyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a fluorenyl group, or a carbazolyl group.

[0055] In some embodiments, R1to R3are selected from a methyl group.

[0056] In some embodiments, R4is selected from a phenyl group or a phenyl group substituted with an alkyl group having a number of carbon atoms from 1 to 5; R4is selected from a phenyl group substituted with at least one methyl group or a tert-butylphenyl group.

[0057] In some embodiments, R1, R2are linked into a ring or are independent from each other.

[0058] Further, R in formula (1) is selected from at least one of H, D, a substituted or unsubstituted alkyl group having a number of carbon atoms from 1 to 20, a substituted or unsubstituted aromatic group having a number of carbon atoms from 6 to 30, a substituted or unsubstituted heteroaromatic group having a number of carbon atoms from 5 to 30.

[0059] In some embodiments, R is selected from H or D.

[0060] Ar1to Ar3in formula (1) are independently selected from at least one of D, a substituted or unsubstituted alkyl group having a number of carbon atoms from 1 to 20, a substituted or unsubstituted aromatic group having a number of carbon atoms from 6 to 30, a substituted or unsubstituted heteroaromatic group having a number of carbon atoms from 5 to 30.

[0061] In some embodiments, Ar1to Ar3are independently selected from H, D, a substituted or unsubstituted alkyl group having a number of carbon atoms from 1 to 12, a substituted or unsubstituted aromatic group having a number of carbon atoms from 6 to 20, a substituted or unsubstituted heteroaromatic group having a number of carbon atoms from 5 to 20. Preferably, Ar1to Ar3are selected from at least one of H, D, a substituted or unsubstituted alkyl group having a number of carbon atoms from 1 to 8, a substituted or unsubstituted aromatic group having a number of carbon atoms from 6 to 15, a substituted or unsubstituted heteroaromatic group having a number of carbon atoms from 5 to 15.

[0062] In some embodiments, Ar1to Ar3are independently selected from H, D, a methyl group, an isopropyl group, a tert-butyl group, a tert-pentyl group, a substituted or unsubstituted phenyl group, a naphthyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a fluorenyl group, a carbazolyl group, or an amine group.

[0063] In some embodiments, Ar1to Ar3are independently selected from H, D, or an alkyl group having a number of carbon atoms from 1 to 5; further, Ar1to Ar3are independently selected from H, D, or a methyl group.

[0064] Ar4and Ar5in formula (1) are independently selected from at least one of a substituted or unsubstituted aromatic group of 6 to 30 carbon atoms, a substituted or unsubstituted heteroaromatic group of 5 to 30 carbon atoms.

[0065] In some embodiments, Ar4and Ar5are independently selected from a substituted or unsubstituted aromatic group of 6 to 20 carbon atoms, a substituted or unsubstituted heteroaromatic group of 5 to 20 carbon atoms. Preferably, Ar4and Ar5are independently selected from a substituted or unsubstituted aromatic group of 6 to 15 carbon atoms, a substituted or unsubstituted heteroaromatic group of 5 to 15 carbon atoms.

[0066] In some embodiments, Ar4and Ar5are independently selected from a substituted or unsubstituted phenyl group, a substituted or unsubstituted benzothiophene group, a naphthyl group, a triphenylene group, a dibenzofurane group, a dibenzothiophene group, a fluorene group, a carbazole group, or a substituted or unsubstituted diphenylamine group.

[0067] In some embodiments, Ar4is a phenyl group or a deuterated phenyl group.

[0068] In some embodiments, Ar5contains a phenyl group, a phenyl group substituted with an alkyl group having 1 to 5 carbon atoms, a benzothiophene group substituted with an alkyl group having 1 to 5 carbon atoms, or a diphenylamine group substituted with an alkyl group having 1 to 5 carbon atoms; that is, Ar5may be selected from a phenyl group, a phenyl group substituted with an alkyl group having 1 to 5 carbon atoms, a benzothiophene group substituted with an alkyl group having 1 to 5 carbon atoms, or a diphenylamine group substituted with an alkyl group having 1 to 5 carbon atoms, or Ar5may be a group containing a phenyl group, a phenyl group substituted with an alkyl group having 1 to 5 carbon atoms, a benzothiophene group substituted with an alkyl group having 1 to 5 carbon atoms, or a diphenylamine group substituted with an alkyl group having 1 to 5 carbon atoms.

[0069] Further, in some embodiments, Ar5contains a phenyl group, a methylphenyl group, a tert-butylphenyl group, a tert-butylbenzothiophene group, or a diphenylamine group substituted with at least one methyl group; that is, Ar5may be selected from a phenyl group, a methylphenyl group, a tert-butylphenyl group, a tert-butylbenzothiophene group, or a diphenylamine group substituted with at least one methyl group, or Ar5may be a group containing a phenyl group, a methylphenyl group, a tert-butylphenyl group, a tert-butylbenzothiophene group, or a diphenylamine group substituted with at least one methyl group.

[0070] Ar6and Ar7in formula (1) are independently selected from at least one of a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aromatic group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaromatic group having 5 to 30 carbon atoms.

[0071] It is to be noted that Ar6and Ar7are linked to form a ring or are independent of each other.

[0072] In some embodiments, Ar6and Ar7are independently selected from substituted or unsubstituted alkyl having 1-12 carbon atoms, substituted or unsubstituted aromatic group having 6-20 carbon atoms, substituted or unsubstituted heteroaromatic group having 5-20 carbon atoms. Preferably, Ar6-Ar9are independently selected from substituted or unsubstituted alkyl having 1-8 carbon atoms, substituted or unsubstituted aromatic group having 6-15 carbon atoms, substituted or unsubstituted heteroaromatic group having 5-15 carbon atoms.

[0073] In some embodiments, Ar6and Ar7are independently selected from substituted or unsubstituted phenyl, naphthyl, triphenylene, dibenzofuranyl, dibenzothiophenyl, fluorenyl, carbazolyl, or methyl.

[0074] In some embodiments, Ar6and Ar7are independently selected from phenyl or phenyl substituted with alkyl having 1 to 5 carbon atoms; further, Ar6and Ar7are independently selected from phenyl, phenyl substituted with at least one methyl group, or t-butylphenyl.

[0075] a, b, and c in formula (1) are independently selected from any integer from 0 to 5, for example, a, b, and c are independently selected from 0, 1, 2, 3, 4, or 5.

[0076] In some embodiments, the organic compound has a structure as shown in any one of formula (2) to formula (7):

[0077] (2) (3);

[0078] (4) (5);

[0079] (6) (7).

[0080] In some embodiments, Ar1, Ar2, Ar3, Ar4, Ar5, Ar6, Ar7, R, R1, R2, R3, R4, X, Y, Z, a, b, and c in formula (2) to formula (7) are defined the same as described in the above embodiments, or the same as defined in formula (1).

[0081] In some embodiments, the organic compound has a structure as shown in any one of formula (8) to formula (13):

[0082] (8) (9);

[0083] (10) (11);

[0084] (12) (13).

[0085] In some embodiments, the definitions of Ar1, Ar2, Ar3, Ar4, Ar5, Ar6, Ar7, R, R1, R2, R3, R4, X, Y, Z, a, b, and c in equations (8) to (13) are the same as those described in the above embodiments, or the same as those defined in equation (1).

[0086] In some embodiments, the organic compound has a structure as shown in formula (14):

[0087] (14);

[0088] Ar8 and Ar9 are independently selected from at least one of substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted aromatic groups having 6-30 carbon atoms, and substituted or unsubstituted heteroaromatic groups having 5-30 carbon atoms.

[0089] Ar 10 It is selected from at least one of a substituted or unsubstituted aromatic group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 30 carbon atoms.

[0090] In some embodiments, Ar8 and Ar9 are independently selected from substituted or unsubstituted alkyl groups having 1-12 carbon atoms, substituted or unsubstituted aromatic groups having 6-20 carbon atoms, and substituted or unsubstituted heteroaromatic groups having 5-20 carbon atoms. Preferably, Ar6-Ar9 are each independently selected from substituted or unsubstituted alkyl groups having 1-8 carbon atoms, substituted or unsubstituted aromatic groups having 6-15 carbon atoms, and substituted or unsubstituted heteroaromatic groups having 5-15 carbon atoms.

[0091] In some embodiments, Ar8 and Ar9 are independently selected from phenyl, phenyl substituted with alkyl groups having 1 to 5 carbon atoms, biphenyl, naphthyl, triphenylene, dibenzofuranyl, dibenzothiophene, fluorenyl, carbazoleyl, or methyl.

[0092] In some embodiments, Ar8 and Ar9 are independently selected from phenyl, biphenyl, or phenyl substituted with an alkyl group having 1 to 5 carbon atoms; further, Ar8 and Ar9 are independently selected from phenyl, biphenyl, methylphenyl, or tert-butylphenyl.

[0093] In some embodiments, Ar 10selected from the group consisting of phenyl.

[0094] In some embodiments, the organic compound is selected from any one of the following compounds:

[0095]

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[0255] In the above, the organic compound provided by the embodiments of the present application has a larger conjugated system and a larger rigid plane formed by connecting the aromatic ring and the heteroaromatic ring through the heterocycle, which effectively suppresses the vibration relaxation caused by the vibration and rotation of the organic compound molecule, improves the light-emitting efficiency and thermal stability of the organic compound, and further enhances the conjugation and resonance effect of the organic compound by introducing the amine group, thereby improving the performance of the organic compound, improving the light-emitting efficiency of the light-emitting element using the organic compound, and prolonging the light-emitting life of the light-emitting element.

[0256] Further, referring to Figure 1 The embodiments of the present application also provide a light-emitting element, which comprises a first electrode 101, a second electrode 102, and an organic functional layer 103; the second electrode 102 is located on one side of the first electrode 101; and the organic functional layer 103 is located between the first electrode 101 and the second electrode 102.

[0257] In the above, the material of the organic functional layer 103 comprises at least one organic compound as described in the above embodiments.

[0258] In some embodiments, the first electrode 101 can be selected from one of an anode and a cathode, and the second electrode 102 can be selected from the other of the anode and the cathode; for example, the first electrode 101 can be an anode, and the second electrode 102 can be a cathode.

[0259] In some embodiments, the light-emitting element can be used in an organic light-emitting diode, an organic photovoltaic cell, an organic light-emitting cell, an organic field effect transistor, an organic light-emitting field effect transistor, an organic laser, an organic spintronic device, an organic sensor, and an organic plasmonic emission diode, preferably an organic light-emitting diode, an organic light-emitting cell, and an organic light-emitting field effect transistor.

[0260] In some embodiments, the light emitting element can be applied to various electronic devices, such as display panels, lighting devices, light sources, etc.

[0261] In some embodiments, the organic functional layer 103 can be a single layer, in which case the organic functional layer 103 is a mixture layer including a first compound selected from one or more of the organic compounds described above and a second compound selected from one or more of a hole injection material, a hole transport material, an electron transport material, a hole blocking material, a light emitting guest material, a light emitting host material, and an organic dye.

[0262] When the second compound is selected from one or more of a hole injection material, a hole transport material, an electron transport material, a hole blocking material, a light emitting host material, and an organic dye, the mass ratio of the first compound to the second compound is 1:99 to 30:70, preferably 1:99 to 10:90.

[0263] When the second compound is a light emitting guest material, the mass ratio of the first compound to the second compound is 70:30 to 99:1, preferably 90:10 to 99:1.

[0264] In some embodiments, the organic functional layer 103 can include multiple layers. When the organic functional layer 103 is a multiple layer, the organic functional layer 103 includes at least a light emitting layer 107; preferably, the organic functional layer 103 includes a hole injection layer 104, a hole transport layer 105, a light emitting layer 107, an electron blocking layer 106, an electron transport layer 108, an electron injection layer 109, or a hole blocking layer.

[0265] In some embodiments, the first electrode 101 (anode) is a hole-injecting electrode, and the first electrode 101 can inject holes into the organic functional layer 103, such as the anode injecting holes into the hole-injecting layer 104, the hole-transporting layer 105, or the light-emitting layer 107. The first electrode 101 can include at least one of a conductive metal, a conductive metal oxide, or a conductive polymer. Preferably, the absolute value of the difference between the work function of the first electrode 101 and the HOMO (Highest Occupied Molecular Orbital) level or valence band level of the light-emitting material in the light-emitting layer is less than 0.5 eV; or, the absolute value of the difference between the work function of the first electrode 101 and the HOMO (Highest Occupied Molecular Orbital) level or valence band level of the p-type semiconductor material as the hole-injecting layer 104 or the hole-transporting layer 105 or the electron-blocking layer 106 is less than 0.5 eV, preferably less than 0.3 eV, and more preferably less than 0.2 eV. The material of the first electrode 101 includes, but is not limited to, at least one of Al, Cu, Au, Ag, Mg, Fe, Co, Ni, Mn, Pd, Pt, ITO (Indium Tin Oxide), aluminum-doped zinc oxide (AZO), and the like, or other suitable and known anode materials, which can be readily selected by one of ordinary skill in the art. The material of the first electrode 101 can be deposited using any suitable technique, such as suitable physical vapor deposition methods, including radio frequency magnetron sputtering, vacuum thermal evaporation, e-beam, and the like. In some embodiments, the first electrode 101 is patternable, such as a patterned ITO conductive substrate, which is commercially available and can be used to fabricate the light-emitting element according to the present application.

[0266] In some embodiments, the second electrode 102 is an electron-injecting electrode, and the second electrode 102 can inject electrons into the organic functional layer 103, such as the electron-injecting layer 109, the electron-transporting layer 108, or the light-emitting layer 107. The second electrode 102 can include at least one of a conductive metal or a conductive metal oxide. Preferably, the absolute value of the difference between the work function of the second electrode 102 and the LUMO (Lowest Unoccupied Molecular Orbital) level or the conduction band level of the light-emitting material in the light-emitting layer is less than 0.5 eV; or the absolute value of the difference between the work function of the second electrode 102 and the LUMO (Lowest Unoccupied Molecular Orbital) level or the conduction band level of the n-type semiconductor material as the electron-injecting layer 109 or the electron-transporting layer 108 or the hole-blocking layer is less than 0.5 eV, preferably less than 0.3 eV, and more preferably less than 0.2 eV. All materials that can be used as the cathode of the light-emitting element can be used as the material of the second electrode 102 of the light-emitting element described in the present application, including but not limited to at least one of Al, Au, Ag, Ca, Ba, Mg, LiF / Al, MgAg alloy, BaF2 / Al, Cu, Fe, Co, Ni, Mn, Pd, Pt, ITO, etc. The material of the second electrode 102 can be deposited using any suitable technique, such as a suitable physical vapor deposition method, including radio frequency magnetron sputtering, vacuum thermal evaporation, e-beam, etc.

[0267] In some embodiments, the hole-injecting layer 104 is used to facilitate the injection of holes from the first electrode 101 to the light-emitting layer 107, and the hole-injecting layer 104 includes a hole-injecting material, which is a material that can receive holes injected from the positive electrode at a low voltage, and preferably, the HOMO (Highest Occupied Molecular Orbital) of the hole-injecting material is between the work function of the material of the anode and the HOMO of the functional material of the film layer on the side of the hole-injecting layer 104 away from the first electrode 101, such as the hole-transporting material of the hole-transporting layer. The hole-injecting material includes but is not limited to at least one of a metal porphyrin, an oligothiophene, an arylamine-based organic material, a hexacarbonitrile hexaazatriphenylene-based organic material, a quinacridone-based organic material, a perylene-based organic material, an anthraquinone, a polyaniline-based and a polythiophene-based conductive polymer, etc.

[0268] In some embodiments, the hole transport layer 105 can be used to transport holes to the light emitting layer 107, and the hole transport layer 105 includes a hole transport material that receives holes transported from the anode or the hole injection layer 104 and transfers holes to the light emitting layer 107. The hole transport material is a material known in the art to have a high hole mobility, and the hole transport material can include, but is not limited to, at least one of an arylamine-based organic material, a conductive polymer, a block copolymer having both a conjugated portion and a non-conjugated portion, and the like.

[0269] In some embodiments, the electron transport layer 108 is used to transport electrons, and the electron transport layer 108 includes an electron transport material that receives electrons injected from the negative electrode and transfers electrons to the light emitting layer 107. The electron transport material is a material known in the art to have a high electron mobility, and the electron transport material can include, but is not limited to, at least one of an Al complex of 8-hydroxyquinoline, a complex including Alq3, an organic radical compound, a hydroxyflavone-metal complex, lithium 8-hydroxyquinoline (LiQ), and a benzimidazole-based compound.

[0270] In some embodiments, the electron injection layer 109 is used to inject electrons, and the electron injection layer 109 includes an electron injection material that is preferably a material having a capability of transporting electrons, having an effect of injecting electrons from the second electrode 102, having an excellent effect of injecting electrons into the light emitting layer 107 or a light emitting material, and having an effect of preventing excitons generated by the light emitting layer 107 from moving to the hole injection layer 104, and further having an excellent capability of forming a thin film. The electron injection material includes, but is not limited to, at least one of lithium 8-hydroxyquinoline (LiQ), fluorenone, anthraquinone dimethane, diphenylquinone, thiopyran dioxide, oxazole, diazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenylidene methane, anthrone, and the like, derivatives thereof, a metal complex compound, a nitrogen-containing 5-membered ring derivative, and the like.

[0271] In some embodiments, the hole blocking layer is used to block holes from reaching the second electrode 102, and can generally be formed under the same conditions as the hole injection layer 104. The hole blocking layer includes a hole blocking material that includes, but is not limited to, at least one of a diazole derivative or a triazole derivative, a phenanthroline derivative, BCP, an aluminum complex, and the like.

[0272] Preferably, the light emitting layer 107 includes a host material and a guest material, and the guest material includes one or more of the organic compounds described above.

[0273] Preferably, the mass ratio of the host material to the guest material is 70:30 to 99:1, such as 90:10, 85:15, 80:20, 75:25, and the like. The guest material is dispersed in the host material, and the mass ratio of the host material to the guest material is 70:30 to 99:1, which is advantageous to inhibit crystallization of the light-emitting layer 107 and inhibit concentration quenching of the guest material due to high concentration, thereby improving the light-emitting efficiency of the light-emitting element.

[0274] Preferably, the host material can be anthracene, boroxine, or exciplex host material.

[0275] The light-emitting wavelength of the light-emitting element can be between 300 nm and 1000 nm, preferably between 350 nm and 900 nm, and more preferably between 400 and 800 nm. The light emitted by the light-emitting element can be red, green, or blue light, preferably blue light.

[0276] In some embodiments, the light-emitting element further includes a substrate, and the first electrode 101, the hole injection layer 104, the hole transport layer 105, the electron blocking layer 106, the light-emitting layer 107, the electron transport layer 108, the electron injection layer 109, and the second electrode 102 can be sequentially stacked on the substrate. The substrate can be a transparent substrate or an opaque substrate, and when the substrate is a transparent substrate, a transparent light-emitting element can be made. The substrate can be a rigid substrate or a flexible substrate with elasticity, and the material of the substrate can include but is not limited to plastic, polymer, metal, semiconductor wafer, or glass, etc. Preferably, the substrate includes at least one smooth surface for forming the anode on the surface. More preferably, the surface is free of surface defects. Preferably, the material of the substrate is a polymer film or plastic, including but not limited to polyethylene terephthalate (PET material) and polyethylene glycol (2,6-naphthalene) (PEN material), and the glass transition temperature of the substrate is greater than or equal to 150°C, preferably greater than or equal to 200°C, more preferably greater than or equal to 250°C, and most preferably greater than or equal to 300°C.

[0277] In some embodiments, the mixture layer or the light-emitting layer 107 can be formed by a printing or coating process of the composition. The printing or coating process includes inkjet printing, nozzle printing, letterpress printing, screen printing, dip coating, spin coating, blade coating, roller printing, twist roll printing, offset printing, flexographic printing, rotary printing, spray coating, brush coating, pad printing, slit extrusion coating, and the like. Preferably, it is gravure printing, nozzle printing, and inkjet printing.

[0278] The composition can be a solution or a suspension, and can include a dispersant and a dispersoid. The dispersoid is one or more of the organic compounds as described above, and the dispersant is used to disperse the dispersoid.

[0279] The mass fraction of the organic compound as described above in the composition can range from 0.01% to 10%, preferably from 0.1% to 15%, more preferably from 0.2% to 5%, and most preferably from 0.25% to 3%.

[0280] Preferably, the Hansen solubility parameter of the dispersant is in the following ranges: the dispersant's δd (dispersion force) is in the range of 17.0 to 23.2 MPa 1 / 2 , preferably in the range of 18.5 to 21.0 MPa 1 / 2 ; the dispersant's δp (polar force) is in the range of 0.2 to 12.5 MPa 1 / 2 , preferably in the range of 2.0 to 6.0 MPa 1 / 2 ; the dispersant's δh (hydrogen bonding force) is in the range of 0.9 to 14.2 MPa 1 / 2 , preferably in the range of 2.0 to 6.0 MPa 1 / 2 .

[0281] Preferably, the boiling point of the dispersant is greater than or equal to 150°C; preferably greater than or equal to 180°C; more preferably greater than or equal to 200°C; even more preferably greater than or equal to 250°C; further preferably greater than or equal to 275°C, and most preferably greater than or equal to 300°C. The boiling point of the dispersant is at least greater than or equal to 150°C is advantageous in preventing clogging of the nozzles of the inkjet print head during inkjet printing, and the higher the boiling point is the more advantageous it is in preventing clogging.

[0282] The dispersant can include at least one organic solvent that can evaporate from the solvent system to form a thin film of the functional material. The organic solvent can include at least one first organic solvent that can be selected from aromatic or heteroaromatic. In particular, the first organic solvent can be selected from p-diisopropylbenzene, amylbenzene, tetralin, cyclohexylbenzene, chloronaphthalene, 1,4-dimethylnaphthalene, 3-isopropylbiphenyl, p-cymene, diamylbenzene, triamylbenzene, pentyltoluene, o-diethylbenzene, m-diethylbenzene, p-diethylbenzene, 1,2,3,4-tetramethylbenzene, 1,2,3,5-tetramethylbenzene, 1,2,4,5-tetramethylbenzene, butylbenzene, dodecylbenzene, dihexylbenzene, dibutylbenzene, p-diisopropylbenzene, cyclohexylbenzene, benzylbutylbenzene, dimethylnaphthalene, 3-isopropylbiphenyl, p-cymene, 1-methylnaphthalene, 1,2,4-trichlorobenzene, 4,4-difluorobenzyl, 1,2-dimethoxy-4-(1-propenyl)benzene, diphenylmethane, 2-phenylpyridine, 3-phenylpyridine, N-methylaniline, 4-isopropylbiphenyl, α,α-dichlorodiphenylmethane, 4-(3-phenylpropyl)pyridine, benzyl benzoate, 1,1-bis(3,4-dimethylphenyl)ethane, 2-isopropyl naphthalene, quinoline, isoquinoline, methyl 2-furoate, ethyl 2-furoate, and the like.

[0283] The first organic solvent can be selected from aromatic ketone solvents. In particular, the first organic solvent can be selected from 1-tetralone, 2-tetralone, 2-(phenyloxy)tetralone, 6-(methyloxy)tetralone, acetophenone, propiophenone, benzophenone, and derivatives thereof, such as 4-methylacetophenone, 3-methylacetophenone, 2-methylacetophenone, 4-methylpropiophenone, 3-methylpropiophenone, 2-methylpropiophenone, and the like.

[0284] The first organic solvent can be selected from aromatic ether solvents. In particular, the first organic solvent can be selected from 3-phenoxytoluene, butoxybenzene, p-anisaldehyde dimethyl acetal, tetrahydro-2-phenoxy-2H-pyran, 1,2-dimethoxy-4-(1-propenyl)benzene, 1,4-benzodioxane, 1,3-dipropylbenzene, 2,5-dimethoxytoluene, 4-ethylbenzyl ethyl ether, 1,3-dipropoxybenzene, 1,2,4-trimethoxybenzene, 4-(1-propenyl)-1,2-dimethoxybenzene, 1,3-dimethoxybenzene, glycidyl phenyl ether, dibenzyl ether, 4-tert-butyl anisole, trans-p-allylanisole, 1,2-dimethoxybenzene, 1-methoxynaphthalene, diphenyl ether, 2-phenoxy methyl ether, 2-phenoxytetrahydrofuran, ethyl-2-naphthyl ether, and the like.

[0285] The first organic solvent can be selected from aliphatic ketones. Specifically, the first organic solvent can be selected from aliphatic ketones such as 2-nonanone, 3-nonanone, 5-nonanone, 2-decanone, 2,5-hexanedione, 2,6,8-trimethyl-4-nonanone, fenchone, p-methylacetophenone, isophorone, di-n-pentyl ketone, and the like; or aliphatic ethers such as pentyl ether, hexyl ether, dioctyl ether, ethylene glycol dibutyl ether, diethylene glycol diethyl ether, diethylene glycol butyl methyl ether, diethylene glycol dibutyl ether, triethylene glycol dimethyl ether, triethylene glycol ethyl methyl ether, triethylene glycol butyl methyl ether, tripropylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, and the like.

[0286] The first organic solvent can be selected from organic ester solvents. Specifically, the first solvent can be selected from octanoic acid alkyl esters, sebacic acid alkyl esters, stearic acid alkyl esters, benzoic acid alkyl esters, phenylacetic acid alkyl esters, cinnamic acid alkyl esters, oxalic acid alkyl esters, maleic acid alkyl esters, alkyl lactones, oleic acid alkyl esters, and the like. Particularly preferred are octanoic acid octyl ester, diethyl sebacate, diallyl phthalate, isononyl isononanoate, and the like.

[0287] The organic solvent can further include a second organic solvent, which can be selected from one or more of methanol, ethanol, 2-methoxyethanol, dichloromethane, trichloromethane, chlorobenzene, o-dichlorobenzene, tetrahydrofuran, anisole, morpholine, toluene, o-xylene, m-xylene, p-xylene, 1,4-dioxane, acetone, methyl ethyl ketone, 1,2-dichloroethane, 3-phenoxytoluene, 1,1,1-trichloroethane, 1,1,2,2-tetrachloroethane, ethyl acetate, butyl acetate, dimethylformamide, dimethylacetamide, dimethyl sulfoxide, tetralin, decalin, indene, and the like.

[0288] The composition can further include one or more components such as a surface active compound, a lubricant, a wetting agent, a dispersant, a hydrophobic agent, a binder, and the like, in addition to the dispersoid and the dispersant, for adjusting viscosity, film formation properties, improving adhesion, and the like.

[0289] The preparation scheme of the organic compound provided by the embodiments of the present application will be described in detail below in connection with specific examples, as shown in the following exemplary Examples 1 to 17.

[0290] Example 1

[0291] Synthesis of the organic compound M1

[0292] Synthetic route of the organic compound M1

[0293]

[0294] Specific synthetic steps of the organic compound M1 are as follows:​

[0295] Synthesis of intermediate M1-3: Compound M1-1 (28.2 g, 100 mmol), compound M1-2 (28.1 g, 100 mmol), compound Pd2(dba)3 (2.76 g, 3 mmol), compound tri-tert-butylphosphine (1.2 g, 6 mmol), compound sodium tert-butoxide (18.2 g, 200 mmol) and 250 mL anhydrous toluene were mixed under nitrogen environment, heated to 60 °C, stirred for 6 hours, cooled to room temperature, quenched with water, most of the solvent was removed by rotary evaporation, dissolved in dichloromethane and washed with water for 3 times, collected the organic liquid, mixed with silica gel and purified by column chromatography, the yield was 75%. The atmospheric pressure solid analysis probe mass spectrometry (ASAP-MS) result of intermediate M1-3: mass-to-charge ratio was 482 [M + ].

[0296] Synthesis of intermediate M1-6: Compound M1-4 (19.7 g, 100 mmol), compound M1-5 (48.4 g, 100 mmol), compound Pd2(dba)3 (2.76 g, 3 mmol), compound tri-tert-butylphosphine (1.2 g, 6 mmol), compound sodium tert-butoxide (18.2 g, 200 mmol) and 250 mL anhydrous toluene were mixed under nitrogen environment, heated to 110 °C, stirred for 6 hours, cooled to room temperature, quenched with water, most of the solvent was removed by rotary evaporation, dissolved in dichloromethane and washed with water for 3 times, collected the organic liquid, mixed with silica gel and purified by column chromatography, the yield was 38%. The atmospheric pressure solid analysis probe mass spectrometry (ASAP-MS) result of intermediate M1-6: mass-to-charge ratio was 601 [M + ].

[0297] Synthesis of intermediate M1-8: Compound M1-6 (30.0 g, 50 mmol), compound M1-7 (7.5 g, 50 mmol), compound Pd2(dba)3 (1.38 g, 1.5 mmol), compound X-Phos (1.4 g, 3 mmol), compound sodium tert-butoxide (9.6 g, 100 mmol) and 250 mL anhydrous toluene were mixed under nitrogen environment, heated to 60 °C, stirred for 6 hours, cooled to room temperature, quenched with water, most of the solvent was removed by rotary evaporation, dissolved in dichloromethane and washed with water for 3 times, collected the organic liquid, mixed with silica gel and purified by column chromatography, the yield was 88%. The atmospheric pressure solid analysis probe mass spectrometry (ASAP-MS) result of intermediate M1-8: mass-to-charge ratio was 714 [M + ].

[0298] Synthesis of intermediate M1-9: (28.5 g, 40 mmol) of compound M1-8, (19.3 g, 40 mmol) of compound M1-3, (1.10 g, 1.2 mmol) of compound Pd2(dba)3, (1.1 g, 2.4 mmol) of compound X-Phos, (7.7 g, 80 mmol) of compound sodium tert-butoxide and 250 mL of anhydrous toluene were mixed under nitrogen atmosphere, heated to 110 °C, stirred for 6 hours, cooled to room temperature, quenched with water, the reaction solution was evaporated to remove most of the solvent, dissolved with dichloromethane and washed with water for 3 times, the organic solution was collected and purified by column chromatography on silica gel, the yield was 78%. The atmospheric pressure solid analysis probe mass spectrometry (ASAP-MS) result of intermediate M1-9: mass-to-charge ratio was 1159 [M + ].

[0299] Synthesis of organic compound M1: (34.8 g, 30 mmol) of compound M1-9 and 300 mL of toluene were mixed under nitrogen atmosphere, 120 mmol of tert-butyllithium solution was slowly added dropwise at room temperature, after the dropwise addition was completed, the reaction was allowed to rise to 60 °C and stirred for 2 hours, then the reaction was allowed to cool to -30 °C, 180 mmol of boron tribromide was added at one time, the reaction was allowed to naturally rise to room temperature and reacted for 1 hour, then 240 mmol of N,N-diisopropylethylamine was added, and the reaction was slowly warmed to room temperature for 1 hour, the reaction was ended, cooled to room temperature, and quenched with the addition of an aqueous sodium acetate solution, most of the solvent was evaporated by rotary evaporation, dissolved with dichloromethane and washed with water for 3 times, the organic solution was collected and evaporated by rotary evaporation, then purified by column chromatography, the yield was 17%. The atmospheric pressure solid analysis probe mass spectrometry (ASAP-MS) result of organic compound M1: mass-to-charge ratio was 1132 [M + ].

[0300] Example 2

[0301] Synthesis of organic compound M2( )

[0302] The synthesis route of organic compound M2 is as follows:

[0303]

[0304] The specific synthesis steps of organic compound M2 are as follows:

[0305] Synthesis of intermediate M2-1 : Compound M1-1 (28.2 g, 100 mmol), compound Pd(OAc)2 (0.45 g, 2 mmol), compound S-Phos (1.9 g, 4 mmol), LDA (2.0 M in THF) (60 mL, 120 mmol) and 200 mL anhydrous toluene were mixed under nitrogen atmosphere and heated to 110 °C with stirring for 12 h, cooled to room temperature, quenched with water, the reaction was evaporated to dryness, dissolved in dichloromethane and washed with water for 3 times, the organic layer was collected and purified by column chromatography on silica gel, yield 48%. Atmospheric solids analysis probe mass spectrometry (ASAP-MS) result of intermediate M2-1 : mass-to-charge ratio of 398 [M + ].

[0306] Synthesis of intermediate M2-3: Following the synthesis procedure of intermediate M2-1, intermediate M2-2 was used to replace intermediate M1-1, yield 49%. Atmospheric solids analysis probe mass spectrometry (ASAP-MS) result of intermediate M2-3: mass-to-charge ratio of 308 [M + ].

[0307] Synthesis of intermediate M2-4: Following the synthesis procedure of intermediate M1-8, intermediate M2-3 was used to replace intermediate M1-6, yield 79%. Atmospheric solids analysis probe mass spectrometry (ASAP-MS) result of intermediate M2-4: mass-to-charge ratio of 421 [M + ].

[0308] Synthesis of intermediate M2-5: Following the synthesis procedure of intermediate M1-6, intermediate M2-4 was used to replace intermediate M1-4, yield 69%. Atmospheric solids analysis probe mass spectrometry (ASAP-MS) result of intermediate M2-5: mass-to-charge ratio of 824 [M + ].

[0309] Synthesis of intermediate M2-6: Following the synthesis procedure of intermediate M1-8, intermediate M2-5 was used to replace intermediate M1-6, yield 78%. Atmospheric solids analysis probe mass spectrometry (ASAP-MS) result of intermediate M2-6: mass-to-charge ratio of 937 [M + ].

[0310] Synthesis of intermediate M2-7: Following the synthesis procedure of intermediate M1-9, intermediate M2-6 and intermediate M2-1 were used to replace intermediate M1-8 and compound M1-3, respectively, yield 74%. Atmospheric solids analysis probe mass spectrometry (ASAP-MS) result of intermediate M2-7: mass-to-charge ratio of 1298 [M + ].

[0311] Synthesis of organic compound M2: according to the synthesis method of organic compound M1, intermediate M2-7 is used to replace intermediate M1-9, and the yield is 15%. The atmospheric pressure solid-phase analysis probe mass spectrum (ASAP-MS) result of organic compound M2 is: the mass-to-charge ratio is 1272 [M + ].

[0312] It should be noted that in the synthesis process of some organic compounds in the embodiments of the present application, the synthesis method of other organic compounds or intermediates is referred to, which means that the corresponding reactants are replaced, and the molar amount of the reactants and other conditions are the same.

[0313] Example 3

[0314] Synthesis of organic compound M3 ).

[0315] The synthesis route of organic compound M3 is as follows:

[0316]

[0317] The specific synthesis steps of organic compound M3 are as follows:

[0318] Synthesis of intermediate M3-2: according to the synthesis method of intermediate M2-1, intermediate M3-1 is used to replace intermediate M1-1, and the yield is 45%. The atmospheric pressure solid-phase analysis probe mass spectrum (ASAP-MS) result of intermediate M3-2 is: the mass-to-charge ratio is 398 [M + ].

[0319] Synthesis of intermediate M3-4: according to the synthesis method of intermediate M2-4, intermediate M3-3 is used to replace intermediate M1-7, and the yield is 78%. The atmospheric pressure solid-phase analysis probe mass spectrum (ASAP-MS) result of intermediate M3-4 is: the mass-to-charge ratio is 393 [M + ].

[0320] Synthesis of intermediate M3-7: under nitrogen environment, compound M3-5 (54.1 g, 200 mmol) and 200 mL of anhydrous tetrahydrofuran solvent are mixed, cooled to-78℃, and 220 mmol of n-butyllithium solution is slowly added and stirred for 1 h; again, compound M3-6 (54.9 g, 200 mmol) is added at one time, and the reaction is allowed to recover to room temperature for 1 h; quenched with water, the reaction liquid is rotary evaporated to remove most of the solvent, dissolved with dichloromethane and washed with water for 3 times, the organic liquid is collected and mixed with silica gel for column chromatography purification, and the yield is 51%. The atmospheric pressure solid-phase analysis probe mass spectrum (ASAP-MS) result of intermediate M3-7 is: the mass-to-charge ratio is 464 [M + ].

[0321] Synthesis of intermediate M3-8: Compound M3-7 (46.4 g, 100 mmol) was dissolved in 200 mL of anhydrous tetrahydrofuran under nitrogen, and the solution was cooled to -78 °C. Then 120 mmol of LDA solution was added dropwise, and the reaction was stirred for 1 h. Then 120 mmol of hexachloroethane was added at once, and the reaction was allowed to recover to room temperature for 1 h. The reaction was quenched with water, and most of the solvent was removed by rotary evaporation. The residue was dissolved in dichloromethane and washed with water for 3 times. The organic phase was collected and purified by column chromatography on silica gel. The yield was 65%. The atmospheric pressure solid analysis probe mass spectrometry (ASAP-MS) result of intermediate M3-8: mass-to-charge ratio was 498 [M + ].

[0322] Synthesis of intermediate M3-9: According to the synthesis method of intermediate M2-5, intermediate M3-8 and M3-4 were used to replace intermediate M1-5 and M2-4, respectively. The yield was 74%. The atmospheric pressure solid analysis probe mass spectrometry (ASAP-MS) result of intermediate M3-9: mass-to-charge ratio was 810 [M + ].

[0323] Synthesis of intermediate M3-10: According to the synthesis method of intermediate M2-6, intermediate M3-9 was used to replace intermediate M2-5. The yield was 79%. The atmospheric pressure solid analysis probe mass spectrometry (ASAP-MS) result of intermediate M3-10: mass-to-charge ratio was 923 [M + ].

[0324] Synthesis of intermediate M3-11: According to the synthesis method of intermediate M2-7, intermediate M3-9 and M3-2 were used to replace intermediate M2-6 and M2-1, respectively. The yield was 75%. The atmospheric pressure solid analysis probe mass spectrometry (ASAP-MS) result of intermediate M3-11: mass-to-charge ratio was 1284 [M + ].

[0325] Synthesis of organic compound M3: According to the synthesis method of organic compound M1, intermediate M3-11 was used to replace intermediate M1-9. The yield was 18%. The atmospheric pressure solid analysis probe mass spectrometry (ASAP-MS) result of organic compound M3: mass-to-charge ratio was: 1258 [M + ].

[0326] Example 4

[0327] Synthesis of organic compound M4( ).

[0328] The synthesis route of organic compound M4 is as follows:

[0329]

[0330] The specific synthesis steps of the organic compound M4 are as follows:

[0331] Synthesis of intermediate M4-2: according to the synthesis method of intermediate M2-1, intermediate M4-1 was replaced by intermediate M1-1, with a yield of 47%. The atmospheric pressure solid analysis probe mass spectrometry (ASAP-MS) result of intermediate M4-2: mass-to-charge ratio was 424 [M + ].

[0332] Synthesis of intermediate M4-3: according to the synthesis method of intermediate M1-6, intermediate M3-8 and M2-4 were replaced by intermediate M1-5 and 1-4, respectively, with a yield of 73%. The atmospheric pressure solid analysis probe mass spectrometry (ASAP-MS) result of intermediate M4-3: mass-to-charge ratio was 838 [M + ].

[0333] Synthesis of intermediate M4-4: according to the synthesis method of intermediate M1-8, intermediate M4-3 was replaced by intermediate M1-6, with a yield of 79%. The atmospheric pressure solid analysis probe mass spectrometry (ASAP-MS) result of intermediate M4-4: mass-to-charge ratio was 951 [M + ].

[0334] Synthesis of intermediate M4-5: according to the synthesis method of intermediate M1-9, intermediate M4-4 and M4-2 were replaced by intermediate M1-8 and 1-3, respectively, with a yield of 71%. The atmospheric pressure solid analysis probe mass spectrometry (ASAP-MS) result of intermediate M4-5: mass-to-charge ratio was 1338 [M + ].

[0335] Synthesis of organic compound M4: according to the synthesis method of organic compound M1, intermediate M4-5 was replaced by intermediate M1-9, with a yield of 17%. The atmospheric pressure solid analysis probe mass spectrometry (ASAP-MS) result of organic compound M4: mass-to-charge ratio was: 1312 [M + ].

[0336] Example 5

[0337] Synthesis of organic compound M5 ) of Example 5

[0338] The synthesis route of organic compound M5 is as follows:

[0339]

[0340] The specific synthesis steps of the organic compound M5 are as follows:

[0341] Synthesis of intermediate M5-3: Compound M5-1 (28 g, 100 mmol), NaOH (6 g, 150 mmol) and 100 mL dimethylformamide were added into a 250 mL flask under nitrogen atmosphere, stirred for 1 hour, then compound M5-2 (14.2 g, 100 mmol) was added at once, stirred for 4 hours, after the reaction was completed, the reaction solution was poured into 400 mL pure water, stirred and then filtered to obtain a solid, which was purified by recrystallization with a mixed solution of ethanol and dichloromethane, with a yield of 84%. The atmospheric pressure solid analysis probe mass spectrometry (ASAP-MS) result of intermediate M5-3: mass-to-charge ratio was 295 [M + ].

[0342] Synthesis of intermediate M5-4: According to the synthesis method of intermediate M2-1, intermediate M5-3 was replaced by intermediate M1-1, with a yield of 50%. The atmospheric pressure solid analysis probe mass spectrometry (ASAP-MS) result of intermediate M5-4: mass-to-charge ratio was 411 [M + ].

[0343] Synthesis of intermediate M5-6: According to the synthesis method of intermediate M3-7, intermediate M5-5 was replaced by intermediate M3-6, with a yield of 56%. The atmospheric pressure solid analysis probe mass spectrometry (ASAP-MS) result of intermediate M5-6: mass-to-charge ratio was 465 [M + ].

[0344] Synthesis of intermediate M5-7: According to the synthesis method of intermediate M3-8, intermediate M5-6 was replaced by intermediate M3-7, with a yield of 64%. The atmospheric pressure solid analysis probe mass spectrometry (ASAP-MS) result of intermediate M5-7: mass-to-charge ratio was 499 [M + ].

[0345] Synthesis of intermediate M5-8: According to the synthesis method of intermediate M3-9, intermediate M5-7 and M2-4 were respectively replaced by intermediate M3-8 and M3-4, with a yield of 83%. The atmospheric pressure solid analysis probe mass spectrometry (ASAP-MS) result of intermediate M5-8: mass-to-charge ratio was 839 [M + ].

[0346] Synthesis of intermediate M5-9: According to the synthesis method of intermediate M3-10, intermediate M5-8 was replaced by intermediate M3-9, with a yield of 80%. The atmospheric pressure solid analysis probe mass spectrometry (ASAP-MS) result of intermediate M5-9: mass-to-charge ratio was 952 [M + ].

[0347] Synthesis of intermediate M5-10: Following the procedure for the synthesis of intermediate M3-11, intermediate M5-9 and M5-4 were used to replace intermediate M3-10 and M3-2, respectively, in 79% yield. Atmospheric solids analysis probe mass spectrometry (ASAP-MS) result for intermediate M5-10: mass-to-charge ratio of 1326 [M + ].

[0348] Synthesis of organic compound M5: Following the procedure for the synthesis of organic compound M1, intermediate M5-10 was used to replace intermediate M1-9 in 16% yield. Atmospheric solids analysis probe mass spectrometry (ASAP-MS) result for organic compound M5: mass-to-charge ratio of 1300 [M + ].

[0349] Example 6

[0350] Synthesis of organic compound M6 ).

[0351] The synthetic route of organic compound M6 is as follows:

[0352]

[0353] The specific synthesis steps of organic compound M6 are as follows:

[0354] Synthesis of intermediate M6-2: Following the procedure for the synthesis of intermediate M2-1, intermediate M6-1 was used to replace intermediate M1-1 in 46% yield. Atmospheric solids analysis probe mass spectrometry (ASAP-MS) result for intermediate M6-2: mass-to-charge ratio of 414 [M + ].

[0355] Synthesis of intermediate M6-3: Following the procedure for the synthesis of intermediate M5-10, intermediate M6-2 was used to replace intermediate M5-4 in 72% yield. Atmospheric solids analysis probe mass spectrometry (ASAP-MS) result for intermediate M6-3: mass-to-charge ratio of 1329 [M + ].

[0356] Synthesis of organic compound M6: Following the procedure for the synthesis of organic compound M1, intermediate M6-3 was used to replace intermediate M1-9 in 18% yield. Atmospheric solids analysis probe mass spectrometry (ASAP-MS) result for organic compound M6: mass-to-charge ratio of 1303 [M + ].

[0357] Example 7

[0358] Synthesis of organic compound M7 ).

[0359] The synthetic route of organic compound M7 is as follows:

[0360]

[0361] The specific synthesis steps of the organic compound M7 are as follows:

[0362] Synthesis of intermediate M7-2: according to the synthesis method of intermediate M2-1, intermediate M7-1 is replaced by intermediate M1-1, with a yield of 46%. The atmospheric pressure solid analysis probe mass spectrometry (ASAP-MS) result of intermediate M7-2 is: mass-to-charge ratio is 398 [M + ].

[0363] Synthesis of intermediate M7-3: according to the synthesis method of intermediate M5-10, intermediate M7-2 is replaced by intermediate M5-4, with a yield of 72%. The atmospheric pressure solid analysis probe mass spectrometry (ASAP-MS) result of intermediate M7-3 is: mass-to-charge ratio is 1313 [M + ].

[0364] Synthesis of organic compound M7: according to the synthesis method of organic compound M1, compound M7-3 is replaced by compound M1-9, with a yield of 19%. The atmospheric pressure solid analysis probe mass spectrometry (ASAP-MS) result of organic compound M7 is: mass-to-charge ratio is: 1287 [M + ].

[0365] Example 8

[0366] Synthesis of organic compound M8( )

[0367] The synthesis route of organic compound M8 is as follows:

[0368]

[0369] The specific synthesis steps of the organic compound M8 are as follows:

[0370] Synthesis of intermediate M8-2: under nitrogen environment, compound M1-5 (48.4 g, 100 mmol), compound M8-1 (15 g, 100 mmol), CuI (0.57 g, 3 mmol), potassium carbonate (13.8 g, 100 mmol) and 150 mL dimethylformamide are mixed, heated to 110°C, stirred for 12 hours, cooled to room temperature, the reaction solution is rotary evaporated to remove most of the solvent, dissolved with dichloromethane and washed with water for 3 times, the organic liquid is collected and mixed with silica gel for column chromatography purification, with a yield of 61%. The atmospheric pressure solid analysis probe mass spectrometry (ASAP-MS) result of intermediate M8-2 is: mass-to-charge ratio is 554 [M + ].

[0371] Synthesis of intermediate M8-3: according to the synthetic method of intermediate M1-8, intermediate M8-2 was replaced by intermediate M1-6, with a yield of 79%. The atmospheric solid analysis probe mass spectrometry (ASAP-MS) result of intermediate M8-3: mass-to-charge ratio was 666 [M + ].

[0372] Synthesis of intermediate M8-4: according to the synthetic method of intermediate M1-9, intermediate M8-3 was replaced by intermediate M1-8, with a yield of 75%. The atmospheric solid analysis probe mass spectrometry (ASAP-MS) result of intermediate M8-4: mass-to-charge ratio was 1112 [M + ].

[0373] Synthesis of organic compound M8: according to the synthetic method of organic compound M1, compound M1-9 was replaced by compound M8-4, with a yield of 23%. The atmospheric solid analysis probe mass spectrometry (ASAP-MS) result of organic compound M8: mass-to-charge ratio was: 1085 [M + ].

[0374] Example 9

[0375] Synthesis of organic compound M9( ).

[0376] The synthetic route of organic compound M9 is as follows:

[0377]

[0378] The specific synthesis steps of organic compound M9 are as follows:

[0379] Synthesis of intermediate M9-3: under nitrogen environment, compound M9-1 (42.3 g, 100 mmol), compound M9-2 (17.3 g, 100 mmol), cesium carbonate (65.2 g, 200 mmol) and 200 mL of dimethylformamide were mixed, heated to reflux for 12 hours, after the reaction was completed, the reaction liquid was allowed to drop to room temperature, most of the solvent was rotary evaporated, extracted with dichloromethane, washed with water for three times, the organic liquid was collected and mixed with silica gel for column chromatography purification, with a yield of 62%. The atmospheric solid analysis probe mass spectrometry (ASAP-MS) result of intermediate M9-3: mass-to-charge ratio was 576 [M + ].

[0380] Synthesis of intermediate M9-4: according to the synthetic method of intermediate M2-1, intermediate M1-1 was replaced by intermediate M9-3, with a yield of 45%. The atmospheric solid analysis probe mass spectrometry (ASAP-MS) result of intermediate M9-4: mass-to-charge ratio was 693 [M +].

[0381] Synthesis of intermediate M9-5: according to the synthetic method of intermediate M2-6, intermediate M9-4 was replaced by intermediate M2-5 with a yield of 75%. The atmospheric solids analysis probe mass spectrometry (ASAP-MS) result of intermediate M9-5: mass to charge ratio was 806 [M + ]。

[0382] Synthesis of intermediate M9-6: according to the synthetic method of intermediate M2-7, intermediate M9-5 was replaced by intermediate M2-6 with a yield of 66%. The atmospheric solids analysis probe mass spectrometry (ASAP-MS) result of intermediate M9-6: mass to charge ratio was 1167 [M + ]。

[0383] Synthesis of compound M9: according to the synthetic method of organic compound M1, intermediate M9-6 was replaced by intermediate M1-9 with a yield of 24%. The atmospheric solids analysis probe mass spectrometry (ASAP-MS) result of organic compound M9: mass to charge ratio was: 1140 [M + ]。

[0384] Example 10

[0385] Synthesis of organic compound M10 ) according to the synthetic method of organic compound M1, intermediate M10-4 was replaced by intermediate M1-9 with a yield of 24%. The atmospheric solids analysis probe mass spectrometry (ASAP-MS) result of organic compound M10: mass to charge ratio was: 1140 [M

[0386] The synthetic route of organic compound M10 is as follows:

[0387]

[0388] The specific synthetic steps of organic compound M10 are as follows:

[0389] Synthesis of intermediate M10-3: according to the synthetic method of intermediate M3-7, intermediates M10-1 and M10-2 were replaced by intermediates M3-5 and M3-6, respectively, with a yield of 54%. The atmospheric solids analysis probe mass spectrometry (ASAP-MS) result of intermediate M10-3: mass to charge ratio was 407 [M + ]。

[0390] Synthesis of intermediate M10-4: according to the synthetic method of intermediate M9-3, intermediate M10-3 was replaced by intermediate M9-1 with a yield of 62%. The atmospheric solids analysis probe mass spectrometry (ASAP-MS) result of intermediate M10-4: mass to charge ratio was 560 [M + ]。

[0391] Synthesis of intermediate M10-6: following the procedure for the synthesis of intermediate M9-3, intermediate M10-4 and M10-5 were used to replace intermediate M9-1 and M9-2, respectively, in a yield of 55%. The atmospheric solids analysis probe mass spectrometry (ASAP-MS) result of intermediate M10-6: mass-to-charge ratio of 803 [M + ].

[0392] Synthesis of intermediate M10-7: following the procedure for the synthesis of intermediate M2-1, intermediate M10-6 was used to replace intermediate M1-1 and 2-fold molar equivalent of intermediate M1-4, in a yield of 55%. The atmospheric solids analysis probe mass spectrometry (ASAP-MS) result of intermediate M10-7: mass-to-charge ratio of 1036 [M + ].

[0393] Synthesis of organic compound M10: following the procedure for the synthesis of organic compound M1, intermediate M10-7 was used to replace intermediate M1-9, in a yield of 26%. The atmospheric solids analysis probe mass spectrometry (ASAP-MS) result of organic compound M10: mass-to-charge ratio of: 1009 [M + ].

[0394] Example 11

[0395] Synthesis of organic compound M11 ) following the procedure for the synthesis of organic compound M1.

[0396] The synthetic route of organic compound M11 is as follows:

[0397]

[0398] The specific synthesis steps of organic compound M11 are as follows:

[0399] Synthesis of intermediate M11-1: following the procedure for the synthesis of intermediate M3-7, intermediate M10-1 and M5-5 were used to replace intermediate M3-5 and M3-6, respectively, in a yield of 54%. The atmospheric solids analysis probe mass spectrometry (ASAP-MS) result of intermediate M11-1: mass-to-charge ratio of 422 [M + ].

[0400] Synthesis of intermediate M11-2: following the procedure for the synthesis of intermediate M9-3, intermediate M11-1 was used to replace intermediate M9-1, in a yield of 62%. The atmospheric solids analysis probe mass spectrometry (ASAP-MS) result of intermediate M11-2: mass-to-charge ratio of 575 [M + ].

[0401] Synthesis of intermediate M11-4: according to the synthetic method of intermediate M9-3, intermediate M11-2 and M11-3 replaced intermediate M9-1 and M9-2 respectively, yield 55%. Atmospheric pressure solid analysis probe mass spectrometry (ASAP-MS) result of intermediate M11-4: mass-to-charge ratio was 844 [M + ].

[0402] Synthesis of intermediate M11-5: according to the synthetic method of intermediate M10-7, intermediate M11-4 replaced intermediate M10-6, yield 45%. Atmospheric pressure solid analysis probe mass spectrometry (ASAP-MS) result of intermediate M11-5: mass-to-charge ratio was 1077 [M + ].

[0403] Synthesis of organic compound M11: according to the synthetic method of organic compound M1, intermediate M11-5 replaced intermediate M1-9, yield 25%. Atmospheric pressure solid analysis probe mass spectrometry (ASAP-MS) result of organic compound M11: mass-to-charge ratio was: 1050 [M + ].

[0404] Example 12

[0405] Synthesis of organic compound M12 ).

[0406] The synthetic route of organic compound M12 is as follows:

[0407]

[0408] The specific synthesis steps of organic compound M12 are as follows:

[0409] Synthesis of intermediate M12-2: according to the synthetic method of intermediate M1-3, intermediate M12-1 replaced intermediate M1-1, yield 78%. Atmospheric pressure solid analysis probe mass spectrometry (ASAP-MS) result of intermediate M12-2: mass-to-charge ratio was 498 [M + ].

[0410] Synthesis of intermediate M12-3: according to the synthetic method of intermediate M2-5, intermediate M1-7 and M1-5 replaced intermediate M2-4 and M1-5 respectively, the reaction temperature was adjusted to 80°C, yield 76%. Atmospheric pressure solid analysis probe mass spectrometry (ASAP-MS) result of intermediate M12-3: mass-to-charge ratio was 553 [M + ].

[0411] Synthesis of intermediate M12-5: following the procedure for the synthesis of intermediate M2-5, intermediate M12-3 and M12-4 were used to replace intermediate M2-4 and M1-5, respectively, in 78% yield. Atmospheric solids analysis probe mass spectrometry (ASAP-MS) result for intermediate M12-5: mass-to-charge ratio of 741 [M + ].

[0412] Synthesis of intermediate M12-6: following the procedure for the synthesis of intermediate M1-8, intermediate M12-5 was used to replace intermediate M1-6 in 79% yield. Atmospheric solids analysis probe mass spectrometry (ASAP-MS) result for intermediate M12-6: mass-to-charge ratio of 854 [M + ].

[0413] Synthesis of intermediate M12-7: following the procedure for the synthesis of intermediate M1-9, intermediate M12-6 and M12-2 were used to replace intermediate M1-8 and M1-3, respectively, in 83% yield. Atmospheric solids analysis probe mass spectrometry (ASAP-MS) result for intermediate M12-7: mass-to-charge ratio of 1315 [M + ].

[0414] Synthesis of organic compound M12: following the procedure for the synthesis of organic compound M1, intermediate M12-7 was used to replace intermediate M1-9 in 14% yield. Atmospheric solids analysis probe mass spectrometry (ASAP-MS) result for organic compound M12: mass-to-charge ratio of: 1289 [M + ].

[0415] Example 13

[0416] Synthesis of organic compound M13 ) following the procedure for the synthesis of organic compound M1.

[0417] The synthetic route of organic compound M13 is as follows:

[0418]

[0419] The specific synthesis steps of organic compound M13 are as follows:

[0420] Synthesis of intermediate M13-1: following the procedure for the synthesis of intermediate M8-2, intermediate M5-7 and M10-5 were used to replace intermediate M1-5 and M8-1, respectively, in 55% yield. Atmospheric solids analysis probe mass spectrometry (ASAP-MS) result for intermediate M13-1: mass-to-charge ratio of 682 [M + ].

[0421] Synthesis of intermediate M13-2: Following the procedure for the synthesis of intermediate M2-1, intermediate M13-1 was used to replace intermediate M1-1, in a yield of 49%. The atmospheric solids analysis probe mass spectrometry (ASAP-MS) result of intermediate M13-2: mass-to-charge ratio of 798 [M + ].

[0422] Synthesis of intermediate M13-3: Following the procedure for the synthesis of intermediate M1-9, intermediate M13-2 and M2-4 were used to replace intermediate M1-3 and M1-8, respectively, in a yield of 82%. The atmospheric solids analysis probe mass spectrometry (ASAP-MS) result of intermediate M13-3: mass-to-charge ratio of 1182 [M + ].

[0423] Synthesis of organic compound M13: Following the procedure for the synthesis of organic compound M1, intermediate M13-3 was used to replace intermediate M1-9, in a yield of 23%. The atmospheric solids analysis probe mass spectrometry (ASAP-MS) result of organic compound M13: mass-to-charge ratio of: 1155 [M + ].

[0424] Example 14

[0425] Synthesis of organic compound M14 ) following the procedure for the synthesis of organic compound M1.

[0426] The synthetic route of organic compound M14 is as follows:

[0427]

[0428] The specific synthesis steps of organic compound M14 are as follows:

[0429] Synthesis of intermediate M14-3: Compound M14-1 (46.6 g, 200 mmol), compound M14-2 (29.8 g, 200 mmol), Pd2(dba)3 (1.83 g, 2 mmol), TTBP (10% in TOL) (8.1 mL, 4 mmol), sodium tert-butoxide (38.4 g, 400 mmol) and 400 mL of toluene were mixed under nitrogen atmosphere, and the mixture was reacted at 70 °C for 4 hours. After the reaction was completed, the reaction solution was allowed to cool to room temperature, most of the solvent was removed by rotary evaporation, extraction was performed with dichloromethane, water washing was performed three times, the organic liquid was collected and silica gel was added for column chromatography purification, in a yield of 82%. The atmospheric solids analysis probe mass spectrometry (ASAP-MS) result of intermediate M14-3: mass-to-charge ratio of 301 [M + ].

[0430] Synthesis of intermediate M14-4: following the procedure for the synthesis of intermediate M2-3, intermediate M14-3 was replaced by intermediate M1-4 in a yield of 52%. Atmospheric solids analysis probe mass spectrometry (ASAP-MS) results for intermediate M14-4: mass to charge ratio of 412 [M + ].

[0431] Synthesis of intermediate M14-5: following the procedure for the synthesis of intermediate M2-4, intermediate M14-4 was replaced by intermediate M2-3 in a yield of 85%. Atmospheric solids analysis probe mass spectrometry (ASAP-MS) results for intermediate M14-5: mass to charge ratio of 525 [M + ].

[0432] Synthesis of intermediate M14-6: following the procedure for the synthesis of intermediate M2-5, intermediate M14-5 was replaced by intermediate M2-4 in a yield of 80%. Atmospheric solids analysis probe mass spectrometry (ASAP-MS) results for intermediate M14-6: mass to charge ratio of 928 [M + ].

[0433] Synthesis of intermediate M14-7: following the procedure for the synthesis of intermediate M2-6, intermediate M14-6 was replaced by intermediate M2-5 in a yield of 75%. Atmospheric solids analysis probe mass spectrometry (ASAP-MS) results for intermediate M14-7: mass to charge ratio of 1041 [M + ].

[0434] Synthesis of intermediate M14-8: following the procedure for the synthesis of intermediate M2-7, intermediate M14-7 was replaced by intermediate M2-6 in a yield of 79%. Atmospheric solids analysis probe mass spectrometry (ASAP-MS) results for intermediate M14-8: mass to charge ratio of 1487 [M + ].

[0435] Synthesis of organic compound M14: following the procedure for the synthesis of organic compound M1, intermediate M14-8 was replaced by intermediate M1-9 in a yield of 20%. Atmospheric solids analysis probe mass spectrometry (ASAP-MS) results for organic compound M14: mass to charge ratio of: 1460 [M + ].

[0436] Example 15

[0437] Synthesis of organic compound M15( ).

[0438] The synthesis route of organic compound M15 is as follows:

[0439]

[0440] The specific synthesis steps of the organic compound M15 are as follows:

[0441] Synthesis of intermediate M15-2: according to the synthetic method of intermediate M2-1, intermediate M15-1 was replaced by intermediate M1-4, with a yield of 47%. The atmospheric pressure solid analysis probe mass spectrometry (ASAP-MS) result of intermediate M15-2: mass-to-charge ratio was 424 [M + ].

[0442] Synthesis of intermediate M15-3: according to the synthetic method of intermediate M2-7, intermediate M15-2 and M14-7 were replaced by intermediate M2-1 and M2-6, respectively, with a yield of 79%. The atmospheric pressure solid analysis probe mass spectrometry (ASAP-MS) result of intermediate M15-3: mass-to-charge ratio was 1428 [M + ].

[0443] Synthesis of the organic compound M15: according to the synthetic method of organic compound M1, intermediate M15-3 was replaced by intermediate M1-9, with a yield of 19%. The atmospheric pressure solid analysis probe mass spectrometry (ASAP-MS) result of organic compound M15: mass-to-charge ratio was: 1402 [M + ].

[0444] Example 16

[0445] Synthesis of the organic compound M16 ).

[0446] The synthetic route of the organic compound M16 is as follows:

[0447]

[0448] The specific synthesis steps of the organic compound M16 are as follows:

[0449] Synthesis of intermediate M16-2: according to the synthetic method of intermediate M2-1, intermediate M16-1 was replaced by intermediate M1-1, with a yield of 52%. The atmospheric pressure solid analysis probe mass spectrometry (ASAP-MS) result of intermediate M16-2: mass-to-charge ratio was 404 [M + ].

[0450] Synthesis of intermediate M16-3: according to the synthetic method of intermediate M1-9, intermediate M16-2 and intermediate M2-6 were replaced by intermediate M1-3 and intermediate M1-6, respectively, with a yield of 74%. The atmospheric pressure solid analysis probe mass spectrometry (ASAP-MS) result of intermediate M16-3: mass-to-charge ratio was 1303 [M + ].

[0451] Synthesis of organic compound M16: according to the synthetic method of organic compound Ml, intermediate M16-3 was used to replace intermediate Ml-9, with a yield of 17%. The atmospheric solids analysis probe mass spectrometry (ASAP-MS) result of organic compound M16: mass-to-charge ratio was 1277 [M + ].

[0452] Example 17

[0453] Synthesis of organic compound M17 ).

[0454] The synthetic route of organic compound M17 is as follows:

[0455]

[0456] The specific synthesis steps of organic compound M17 are as follows:

[0457] Synthesis of intermediate M17-1: according to the synthetic method of intermediate M2-1, intermediate M15-1 and M16-1 were used to replace intermediate Ml-4 and Ml-1 respectively, with a yield of 45%. The atmospheric solids analysis probe mass spectrometry (ASAP-MS) result of intermediate M17-1: mass-to-charge ratio was 430 [M + ].

[0458] Synthesis of intermediate M17-2: according to the synthetic method of intermediate M14-3, intermediate Ml-7 was used to replace intermediate M14-2, with a yield of 89%. The atmospheric solids analysis probe mass spectrometry (ASAP-MS) result of intermediate M17-2: mass-to-charge ratio was 301 [M + ].

[0459] Synthesis of intermediate M17-3: according to the synthetic method of intermediate M2-3, intermediate M17-2 was used to replace intermediate Ml-4, with a yield of 55%. The atmospheric solids analysis probe mass spectrometry (ASAP-MS) result of intermediate M17-3: mass-to-charge ratio was 412 [M + ].

[0460] Synthesis of intermediate M17-4: according to the synthetic method of intermediate M2-4, intermediate M17-3 was used to replace intermediate M2-3, with a yield of 86%. The atmospheric solids analysis probe mass spectrometry (ASAP-MS) result of intermediate M17-4: mass-to-charge ratio was 525 [M + ].

[0461] Synthesis of intermediate M17-5: according to the synthetic method of intermediate M2-5, intermediate M17-4 was replaced by intermediate M2-4, with a yield of 80%. The atmospheric pressure solid analysis probe mass spectrometry (ASAP-MS) result of intermediate M17-5: mass-to-charge ratio was 928 [M + ].

[0462] Synthesis of intermediate M17-6: according to the synthetic method of intermediate M2-6, intermediate M17-5 was replaced by intermediate M2-5, with a yield of 77%. The atmospheric pressure solid analysis probe mass spectrometry (ASAP-MS) result of intermediate M17-6: mass-to-charge ratio was 1041 [M + ].

[0463] Synthesis of intermediate M17-7: according to the synthetic method of intermediate M2-7, intermediate M17-6 was replaced by intermediate M2-6, with a yield of 81%. The atmospheric pressure solid analysis probe mass spectrometry (ASAP-MS) result of intermediate M17-7: mass-to-charge ratio was 1433 [M + ].

[0464] Synthesis of organic compound M17: according to the synthetic method of organic compound M1, intermediate M17-7 was replaced by intermediate M1-9, with a yield of 15%. The atmospheric pressure solid analysis probe mass spectrometry (ASAP-MS) result of organic compound M17: mass-to-charge ratio was: 1407 [M + ].

[0465] The example manufacturing steps of the light-emitting element provided in the embodiments of the present application are shown in the following example device embodiment 1.

[0466] Device embodiment 1

[0467] In this embodiment, the manufacturing steps of the light-emitting element with a first electrode (anode) (ITO) / hole injection layer (40 nm) / hole transport layer (100 nm) / light-emitting layer (host material: 3% (mass ratio) guest material) (50 nm) / electron transport layer (25 nm) / second electrode (cathode) (LiQ (1 nm) / Al (150 nm) are as follows:

[0468] a. Cleaning of the substrate containing the first electrode (i.e. conductive glass substrate): when used for the first time, it can be cleaned with various solvents, such as chloroform, ketone, isopropanol, and then subjected to ultraviolet ozone plasma treatment;

[0469] b. Sequentially depositing films in the order of hole injection layer (40 nm), hole transport layer (100 nm), light-emitting layer (50 nm), and electron transport layer (25 nm) by thermal evaporation in high vacuum (1 x 10 -6 mbar);

[0470] c、Second electrode: LiQ (1 nm) / Al (150 nm) was prepared by thermal evaporation in high vacuum (1 x 10 -6 mbar) ;

[0471] d、Packaging: The device was packaged with ultraviolet curing resin in a nitrogen glove box.

[0472] In this embodiment, the guest materials in the light-emitting layer are organic compounds M1-M17, respectively, to form light-emitting elements 1-17, and the guest material Ref-1 is used to form comparative element 1.

[0473] The structural formula of Ref-1 is: .

[0474] In the light-emitting elements 1-17 and comparative element 1,

[0475] The structural formula of the material of the hole injection layer is: .

[0476] The structural formula of the material of the hole transport layer is: .

[0477] The structural formula of the host material in the light-emitting layer is: .

[0478] The structural formula of the material of the electron transport layer is: .

[0479] The structural formula of LiQ is: .

[0480] In this embodiment, the external quantum efficiency (EQE) and light-emitting lifetime (T90@1000nits, referring to the time for the device under test to decay from 1000 nit to 900 nit) of light-emitting elements 1-17 and comparative element 1 were tested, and the results are shown in Table 1.

[0481] Table 1 Performance data of light-emitting elements 1-17 and comparative element 1

[0482]

[0483] As can be seen from the data in Table 1, when the external quantum efficiency and light-emitting lifetime of comparative element 1 are taken as the reference value 1, the external quantum efficiency of light-emitting elements 1-17 is significantly improved, and the light-emitting lifetime is also effectively prolonged. It shows that the introduction of amine substituents can simultaneously connect the benzene ring to the heterocyclic structure and the amine group, enhance the resonance effect and steric effect of the organic compound, improve the performance of the guest material, and effectively improve the light-emitting efficiency and light-emitting lifetime of the light-emitting element.

[0484] The light-emitting element disclosed in the embodiments of the present application uses an organic compound containing an amine group, which has a large steric hindering group, a heterocycle and an amine group at the same time, thereby enhancing the conjugation effect and resonance effect of the material used in the light-emitting element, further narrowing the light-emitting spectrum, improving the material performance, increasing the light-emitting efficiency of the light-emitting element and prolonging the light-emitting life of the light-emitting element.

[0485] In addition, the embodiments of the present application also provide a display panel, which comprises the light-emitting element as described in the above embodiments.

[0486] In some embodiments, the display panel further comprises an array substrate located on one side of the light-emitting element, and an encapsulation layer located on a side of the light-emitting element away from the array substrate and covering the light-emitting element.

[0487] In some embodiments, the display panel further comprises a polarizer located on a side of the encapsulation layer away from the light-emitting element, and a cover plate located on a side of the polarizer away from the light-emitting element.

[0488] The polarizer can be replaced by a color filter layer, which can comprise a plurality of color resist and a black matrix located between adjacent color resist.

[0489] In addition, the embodiments of the present application also provide a display device, which comprises the display panel as described in the above embodiments.

[0490] In some embodiments, the display device can comprise a mobile phone, a computer, a tablet, a television, a watch, a virtual reality device, etc.

[0491] The display panel and the display device provided by the embodiments of the present application use the light-emitting element of the organic compound containing the amine group, which has the heterocycle and the amine group at the same time, thereby enhancing the conjugation effect and resonance effect of the material used in the light-emitting element, improving the material performance, increasing the light-emitting efficiency of the light-emitting element and prolonging the light-emitting life of the light-emitting element, thereby improving the light-emitting efficiency of the display panel and prolonging the service life of the display panel.

[0492] The above describes the organic compound, the light-emitting element and the display panel provided by the embodiments of the present application in detail, and the specific examples are applied to describe the principles and implementation modes of the present application; the above embodiments are only used to help understand the method and the core idea of the present application; meanwhile, for those skilled in the art, according to the idea of the present application, the specific implementation mode and the application range can be changed; in conclusion, the content of the present application should not be understood as the limitation of the present application.

Claims

1. An organic compound, characterized by, The organic compound has a structure as shown in formula (14): (14)； Z is selected from CR1R2, NR3, O or S; X and Y are independently selected from O or NR4; R1 to R3 are independently selected from an alkyl group having 1 to 5 carbon atoms; R4 is selected from a methyl group, a phenyl group or a phenyl group substituted with an alkyl group having 1 to 5 carbon atoms; R is selected from H or D; Ar1 to Ar3 are selected from H, D, a methyl group, an isopropyl group, a tert-butyl group or a tert-pentyl group; Ar4 is selected from a phenyl group or a deuterated phenyl group; Ar6 and Ar7 are independently selected from a phenyl group or a phenyl group substituted with an alkyl group having 1 to 5 carbon atoms, and Ar6 and Ar7 are connected into a ring or are independent of each other; Ar8 and Ar9 are independently selected from a phenyl group, a phenyl group substituted with an alkyl group having 1 to 5 carbon atoms or a biphenyl group; Ar 10 selected from phenyl; a, b and c are independently selected from any integer from 0 to 5.

2. The organic compound according to claim 1, characterized by X and Y are independently selected from O or NR4, or X and Y are selected from O.

3. The organic compound according to claim 1, characterized by The organic compound is selected from any one of the following compounds: 。 4. A light emitting element characterized by comprising: a first electrode; a second electrode located on one side of the first electrode; an organic functional layer located between the first electrode and the second electrode; wherein the material of the organic functional layer comprises at least one organic compound as claimed in any one of claims 1 to 3.

5. The light-emitting element according to claim 4, wherein The organic functional layer comprises a light-emitting layer, and the light-emitting layer comprises a host material and a guest material, and the guest material comprises at least one organic compound.

6. The light-emitting element according to claim 5, wherein In the light-emitting layer, the mass ratio of the host material to the guest material is 70:30 to 99:

1.

7. A display panel, characterized by, The display panel comprises the light-emitting element as claimed in any one of claims 4 to 6.

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