A heterocyclic compound containing a dibenzocarbazole structure and use thereof

Abstract

The application provides a heterocyclic compound containing a dibenzocarbazole structure, which has the structure shown in the following formula (1): The heterocyclic compound containing the dibenzocarbazole structure has better film forming property and thermal stability, and is beneficial to prolong the service life of an organic electroluminescent device.

Description

Technical Field

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

[0002] Organic light-emitting diodes (OLEDs) are self-emissive display elements based on organic electroluminescent materials. Unlike existing liquid crystal display elements, they do not require a backlight and are thin, making them a suitable technology for flexible element devices (flexible light-emitting display devices).

[0003] Organic electroluminescent devices have an anode and a cathode, and an organic material layer between the two electrodes. They can be simple elements with a single light-emitting unit or series-connected elements with multiple light-emitting units. The organic material layer is typically composed of a multilayer structure made of various materials, such as a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer. This allows charge carriers of holes and electrons to recombine in the light-emitting layer, generating excitons. These excitons then transition from the excited state to the ground state to produce light.

[0004] Current research on improving the performance of organic electroluminescent devices includes reducing the driving voltage, increasing the luminous efficiency, and extending the device's lifespan. The characteristics of the organic compounds contained in each layer have a significant impact on the device's driving voltage, luminous efficiency, and lifespan. Therefore, the use of specific organic materials with excellent performance is considered important in organic electroluminescent devices.

[0005] Therefore, continuous research and innovation are needed to develop organic electroluminescent functional materials, produce higher-performance organic electroluminescent functional materials, and then manufacture organic electroluminescent devices with excellent performance. Summary of the Invention

[0006] The purpose of this invention is to develop a heterocyclic compound containing a dibenzocarbazole structure that can be used as an organic electroluminescent material, thereby improving the performance of organic electroluminescent elements.

[0007] The technical solution of the present invention is as follows:

[0008] In a first aspect, the present invention provides a heterocyclic compound containing a dibenzocarbazole structure, said heterocyclic compound having the structure shown in formula (1).

[0009]

[0010] in, for , , , Preferably , , The most preferred option is ; “ "Indicates the connection position;

[0011] L 1 L 2 Each is independently selected from straight, substituted, or unsubstituted C6-C bonds. 30 aryl, substituted or unsubstituted C3-C 30 heteroaryl;

[0012] L 3 It is selected from substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted naphthyl, substituted or unsubstituted dibenzothiophenyl, preferably selected from substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted naphthyl, and most preferably selected from substituted or unsubstituted dibenzofuranyl;

[0013] Ar 1 Ar 2 Each is independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C. 20 Alkyl groups, substituted or unsubstituted C3-C 20 cycloalkyl, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C3-C 30 The heteroaryl group is preferably selected from hydrogen, deuterium, fluorine, cyano, substituted or unsubstituted C1-C. 20 Alkyl groups, substituted or unsubstituted C3-C 20 cycloalkyl, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C3-C 30 The heteroaryl group is preferably selected from hydrogen, deuterium, fluorine, cyano, substituted or unsubstituted C3-C. 20 cycloalkyl, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C3-C 30 The heteroaryl group is more preferably selected from hydrogen, deuterium, fluorine, cyano, substituted or unsubstituted C6-C. 30 aryl, substituted or unsubstituted C3-C 30 The heteroaryl group is particularly preferably selected from hydrogen, deuterium, fluorine, substituted or unsubstituted C6-C groups. 30 aryl, substituted or unsubstituted C3-C 30The heteroaryl group is most preferably selected from hydrogen, deuterium, substituted or unsubstituted C6-C. 30 aryl, substituted or unsubstituted C3-C 30 heteroaryl groups;

[0014] R 1 R 2 Each is independently selected from hydrogen, substituted or unsubstituted C6-C. 30 The aryl group or deuterium is preferably selected from hydrogen, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, or deuterium, more preferably selected from hydrogen, deuterated or unsubstituted phenyl, deuterated or unsubstituted naphthyl, or deuterium, more preferably selected from hydrogen, deuterated or unsubstituted phenyl, or deuterium, even more preferably selected from hydrogen, unsubstituted phenyl, or deuterium, and most preferably selected from hydrogen or deuterium.

[0015] a is an integer selected from 0 to 6, more preferably an integer from 0 to 5, more preferably an integer from 0 to 4, more preferably 0, 1, 2, 3, particularly preferably 0, 1, 2, especially preferably 0, 1, and most preferably 0; when a is 2 or greater, multiple R 1 They are the same or different from each other;

[0016] b is selected from an integer from 0 to 6, more preferably an integer from 0 to 5, more preferably an integer from 0 to 4, more preferably 0, 1, 2, 3, particularly preferably 0, 1, 2, especially preferably 0, 1, and most preferably 0; when b is 2 or greater, multiple R 2 They are the same or different from each other;

[0017] R 3 Selected from hydrogen, deuterium, substituted or unsubstituted C1-C 20 Alkyl, substituted or unsubstituted C6-C 30 The aryl group or halogen is preferably selected from hydrogen, deuterium, or substituted or unsubstituted C1-C atoms. 20 Alkyl, substituted or unsubstituted C6-C 30 The aryl or fluorine group is more preferably selected from hydrogen, deuterium, substituted or unsubstituted C1-C. 20 Alkyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, fluoro, more preferably selected from hydrogen, deuterium, substituted or unsubstituted C1-C 20 Alkyl groups, deuterated or unsubstituted phenyl groups, deuterated or unsubstituted naphthyl groups, fluoro groups, particularly preferably selected from hydrogen, deuterium, deuterated or unsubstituted phenyl groups, deuterated or unsubstituted naphthyl groups, fluoro groups, particularly preferably selected from hydrogen, deuterium, unsubstituted phenyl groups, unsubstituted naphthyl groups, fluoro groups, particularly preferably selected from hydrogen, deuterium, unsubstituted phenyl groups, fluoro groups, especially preferably selected from hydrogen, deuterium, unsubstituted phenyl groups, and most preferably selected from hydrogen or deuterium;

[0018] c is selected from an integer between 0 and 4, preferably an integer between 0 and 3, more preferably 0, 1, or 2, more preferably 0 or 1, and most preferably 0; when c is 2 or greater, multiple R 3 Whether they are the same or different, R 3 The two Rs do not bond to each other or at least two Rs 3 They are interconnected to form a ring structure; the ring structure is preferably an aromatic ring or a heteroaromatic ring structure, more preferably an aromatic ring structure, and most preferably a benzene ring structure;

[0019] In the phrase "substituted or unsubstituted," the substituents for substitution are independently selected from deuterium, halogen, cyano, C1-C. 20 Alkyl, C1-C 20 alkoxy groups, C3-C 20 cycloalkyl, C3-C 10 Cycloalkoxy, C6-C 30 aryl, C6-C 30 aryloxy groups, C3-C 30 One or a combination of heteroaryl groups; preferably selected from deuterium, halogen, cyano, C1-C 10 Alkyl, C1-C 10 alkoxy groups, C3-C 10 cycloalkyl, C3-C 10 Cycloalkoxy, C6-C 60 aryl, C2-C 60 One or a combination of heteroaryl groups; more preferably selected from deuterium, halogen, cyano, C1-C 10 Alkyl, C1-C 10 alkoxy groups, C3-C 10 cycloalkyl, C6-C 60 aryl, C2-C 60 One or a combination of heteroaryl groups; more preferably selected from deuterium, halogen, cyano, C1-C 10 Alkyl, C3-C 10 cycloalkyl, C6-C 60 aryl, C2-C 60 One or a combination of heteroaryl groups; more preferably selected from deuterium, fluoro, cyano, C1-C 10 Alkyl, C3-C 10 cycloalkyl, C6-C 60 aryl, C2-C 60 One or a combination of heteroaryl groups; more preferably selected from deuterium, fluoro, cyano, C1-C 10 Alkyl, C6-C 60 aryl, C2-C 60One or a combination of heteroaryl groups; more preferably selected from deuterium, fluoro, cyano, C1-C 10 Alkyl, C6-C 60 One or a combination of aryl groups; particularly preferably selected from deuterium, fluorine, cyano, C6-C 60 One or a combination of aryl groups; particularly preferably selected from one or a combination of deuterium, fluoro group, and cyano group; particularly preferably selected from one or a combination of deuterium and fluoro group; most preferably selected from one or a combination of deuterium.

[0020] The heteroatom in the heteroaryl group is selected from one or more of N, O, S, Si, P, and B;

[0021] When Ar 1 When L is hydrogen, deuterium, halogen, or cyano, 1 Not a straight key;

[0022] When Ar 2 When L is hydrogen, deuterium, halogen, or cyano, 2 Not a straight key;

[0023] Preferably, the heterocyclic compound may not contain or may contain at least one substituent selected from deuterium, fluorine, or cyano; more preferably, the heterocyclic compound may not contain or may contain at least one substituent selected from deuterium or fluorine; more preferably, the heterocyclic compound may not contain or may contain at least one deuterium.

[0024] According to the above heterocyclic compound, the structure of the heterocyclic compound is preferably shown in Formula 1-1:

[0025]

[0026] Equation 1-1

[0027] Among them, L 1 , L 2 , L 3 Ar 1 Ar 2 , R 1 , R 2 , R 3 The definitions of a, b, and c are the same as above;

[0028] Preferably, the heterocyclic compound may not contain or may contain at least one substituent selected from deuterium, fluorine, or cyano; more preferably, the heterocyclic compound may not contain or may contain at least one substituent selected from deuterium or fluorine; more preferably, the heterocyclic compound may not contain or may contain at least one deuterium.

[0029] According to the above-mentioned heterocyclic compounds, the heterocyclic compounds are preferably selected from the following structures:

[0030] , ,

[0031] Among them, L 1 , L 2 , L 3 Ar 1 Ar 2 , R 1 , R 2 , R 3 The definitions of a, b, and c are the same as above;

[0032] Preferably, the heterocyclic compound may not contain or may contain at least one substituent selected from deuterium, fluorine, or cyano; more preferably, the heterocyclic compound may not contain or may contain at least one substituent selected from deuterium or fluorine; more preferably, the heterocyclic compound may not contain or may contain at least one deuterium.

[0033] According to the above-mentioned heterocyclic compounds, the heterocyclic compounds are preferably selected from the following structures:

[0034] , , ,

[0035] , ,

[0036] Among them, L 1 , L 2 Ar 1 Ar 2 , R 1 , R 2 , R 3 The definitions of a, b, and c are the same as above;

[0037] Preferably, the heterocyclic compound may not contain or may contain at least one substituent selected from deuterium, fluorine, or cyano; more preferably, the heterocyclic compound may not contain or may contain at least one substituent selected from deuterium or fluorine; more preferably, the heterocyclic compound may not contain or may contain at least one deuterium.

[0038] According to the above-mentioned heterocyclic compounds, the heterocyclic compounds are preferably selected from the following structures:

[0039] Among them, L 1 , L 2 Ar 1 Ar 2 , R 1 , R 2, R 3 The definitions of a, b, and c are the same as above;

[0040] Preferably, the heterocyclic compound may not contain or may contain at least one substituent selected from deuterium, fluorine, or cyano; more preferably, the heterocyclic compound may not contain or may contain at least one substituent selected from deuterium or fluorine; more preferably, the heterocyclic compound may not contain or may contain at least one deuterium.

[0041] According to the above-mentioned heterocyclic compounds, the heterocyclic compounds are preferably selected from the following structures:

[0042]

[0043] Among them, L 1 , L 2 Ar 1 Ar 2 , R 1 , R 2 , R 3 The definitions of a, b, and c are the same as above;

[0044] Preferably, the heterocyclic compound may not contain or may contain at least one substituent selected from deuterium, fluorine, or cyano; more preferably, the heterocyclic compound may not contain or may contain at least one substituent selected from deuterium or fluorine; more preferably, the heterocyclic compound may not contain or may contain at least one deuterium.

[0045] According to the above-mentioned heterocyclic compounds, the heterocyclic compounds are preferably selected from the following structures:

[0046]

[0047] Among them, L 1 , L 2 Ar 1 Ar 2 , R 1 , R 2 , R 3 The definitions of a, b, and c are the same as above;

[0048] Preferably, the heterocyclic compound may not contain or may contain at least one substituent selected from deuterium, fluorine, or cyano; more preferably, the heterocyclic compound may not contain or may contain at least one substituent selected from deuterium or fluorine; more preferably, the heterocyclic compound may not contain or may contain at least one deuterium.

[0049] According to the above-mentioned heterocyclic compounds, the heterocyclic compounds are preferably selected from the following structures:

[0050]

[0051] Among them, L 1 , L 2 Ar 1 Ar 2 , R 1 , R 2 , R 3 The definitions of a, b, and c are the same as above;

[0052] Preferably, the heterocyclic compound may not contain or may contain at least one substituent selected from deuterium, fluorine, or cyano; more preferably, the heterocyclic compound may not contain or may contain at least one substituent selected from deuterium or fluorine; more preferably, the heterocyclic compound may not contain or may contain at least one deuterium.

[0053] According to the above-mentioned heterocyclic compounds, the heterocyclic compounds are preferably selected from the following structures:

[0054]

[0055] Among them, L 1 , L 2 Ar 1 Ar 2 , R 1 , R 2 , R 3 The definitions of a, b, and c are the same as above;

[0056] Preferably, the heterocyclic compound may not contain or may contain at least one substituent selected from deuterium, fluorine, or cyano; more preferably, the heterocyclic compound may not contain or may contain at least one substituent selected from deuterium or fluorine; more preferably, the heterocyclic compound may not contain or may contain at least one deuterium.

[0057] According to the above heterocyclic compound, the Preferably , , , , , , , The preferred option is , , , More preferably , , Especially preferred is , The most preferred option is ;

[0058] in," "Indicates the connection position;

[0059] The definitions of a and b are the same as above;

[0060] Preferably, the above-mentioned group is unsubstituted or substituted with one or more substituents selected from deuterium, fluorine, and cyano; more preferably, the above-mentioned group is unsubstituted or substituted with one or more substituents selected from deuterium and fluorine; more preferably, the above-mentioned group is unsubstituted or substituted with one or more deuterium groups; even more preferably, the above-mentioned group is unsubstituted or substituted with one or more deuterium groups; most preferably, the above-mentioned group is unsubstituted.

[0061] According to the above heterocyclic compound, the Preferably , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , The preferred option is , , , , , , , , , , , , , , , , , , , , , , , , , More preferably, , , , , , , , , , , , , , , , , , , Especially preferred is , , , , , , , , , , , Especially preferred is , , , , , , , Especially preferred is , , , , Especially preferred is , The most preferred option is ;

[0062] The Preferably , , , , , , , , , , , , , , , , , , , , , , , , The preferred option is , , , , , , , , , , , , , , , , , , , , More preferably , , , , , , , , , , , , , More preferably , , , , , , , , Especially preferred is , , , , Especially preferred is , , Especially preferred is , The most preferred option is ;

[0063] in," "Indicates the connection position;

[0064] Preferably, the above-mentioned group is unsubstituted or substituted with one or more substituents selected from deuterium, fluorine, and cyano; more preferably, the above-mentioned group is unsubstituted or substituted with one or more substituents selected from deuterium and fluorine; more preferably, the above-mentioned group is unsubstituted or substituted with one or more deuterium groups; even more preferably, the above-mentioned group is unsubstituted or substituted with one or more deuterium groups; most preferably, the above-mentioned group is unsubstituted.

[0065] According to the above heterocyclic compound, the R 1 R 2 R 3 Each is independently selected from hydrogen or deuterium, and / or, the L 1 L 2 Each is independently selected from straight, substituted, or unsubstituted C6-C bonds. 30 aryl, substituted or unsubstituted C3-C 30 The heteroaryl group, and / or the Ar 1 Ar 2 Each is independently selected from hydrogen, deuterium, substituted or unsubstituted C6-C. 30 aryl, substituted or unsubstituted C3-C 30 The heteroaryl group; preferably, the R 1 R 2 R 3 Each is independently selected from hydrogen, and / or, the L 1 L 2 Each is independently selected from straight, substituted, or unsubstituted C6-C bonds. 30 aryl, substituted or unsubstituted C3-C 30 The heteroaryl group, and / or the Ar 1 Ar 2 Each is independently selected from hydrogen, deuterium, substituted or unsubstituted C6-C. 30 aryl, substituted or unsubstituted C3-C 30 heteroaryl; when Ar 1 When it is hydrogen or deuterium, L 1 Not a straight key; when Ar 2 When it is hydrogen or deuterium, L 2 Not a straight bond; the definitions of a, b, and c are the same as above, and the definitions of substituents in "substituted or unsubstituted" are the same as above.

[0066] According to the above heterocyclic compound, the L 1L 2 Each group is independently selected from linear, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, substituted or unsubstituted dibenzofuranyl; preferably selected from linear, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, more preferably selected from linear, substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, more preferably selected from linear, substituted or unsubstituted groups of the following: , , , , , , , , , , , , , , , , Particularly preferred are groups selected from straight bonds, substituted or unsubstituted groups, including: , , , , Most preferably, the groups are selected from the following groups, which are straight, substituted, or unsubstituted: , , , ;in," "" indicates the connection position; preferably, the definition of the substituent when "substituted or unsubstituted" is the same as above; more preferably, the above group is unsubstituted or substituted by one or more substituents selected from deuterium, fluorine, and cyano; more preferably, the above group is unsubstituted or substituted by one or more substituents selected from deuterium and fluorine; more preferably, the above group is unsubstituted or substituted by one or more deuterium; most preferably, the above group is unsubstituted or substituted by one or more deuterium.

[0067] According to the above heterocyclic compound, the Ar 1 Ar 2 Each group is independently selected from hydrogen, deuterium, or substituted or unsubstituted groups, including:

[0068] ,

[0069] in," "Indicates the connection position;

[0070] Preferably, the substituent in "substituted or unsubstituted" is defined as above; more preferably, the group is unsubstituted or substituted with one or more substituents selected from deuterium, fluorine, and cyano; more preferably, the group is unsubstituted or substituted with one or more substituents selected from deuterium and fluorine; more preferably, the group is unsubstituted or substituted with one or more deuterium; most preferably, the group is unsubstituted or substituted with one or more deuterium.

[0071] According to the above heterocyclic compound, the -L 1 -Ar 1 -L 2 -Ar 2 Each of the following groups, whether substituted or unsubstituted, is independently selected:

[0072] , , , ,

[0073] , , , ,

[0074] , , , , , , , , ,

[0075] , , , , ,

[0076] , , , , , , ,

[0077] , , , , , , , , ,

[0078] Preferably selected from , , , , , , , , , , , , , , , , , , Preferred selections are from , , , , , , , , , More preferably selected from , , , , , , , Especially preferred are those selected from , , , , , , Especially preferred are those selected from , , , , , Especially preferred are those selected from , , , , The best option is selected from , , , ;

[0079] in," "Indicates the connection position;

[0080] Preferably, the substituent in "substituted or unsubstituted" is defined as above; more preferably, the group is unsubstituted or substituted with one or more substituents selected from deuterium, fluorine, and cyano; more preferably, the group is unsubstituted or substituted with one or more substituents selected from deuterium and fluorine; more preferably, the group is unsubstituted or substituted with one or more deuterium; most preferably, the group is unsubstituted or substituted with one or more deuterium.

[0081] According to the above heterocyclic compounds, the halogen is preferably F, Br, Cl, or I;

[0082] And / or, the C1-C 20 The alkyl group is preferably methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, sec-butyl, n-pentyl, neopentyl, isopentyl, n-hexyl, n-heptyl, n-octyl, n-decyl, isooctyl, nonyl, 2-ethylhexyl;

[0083] And / or, the C1-C 20 The preferred alkoxy groups are methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentoxy, neopentoxy, isopentoxy, n-hexyloxy, n-octoxy, isooctoxy, n-decoxy, n-nonoxy, and n-heptoxy.

[0084] And / or, the C3-C 20 The cycloalkyl group is preferably cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclooctyl, cyclononyl, cyclodecyl, norbornyl, or adamantyl.

[0085] And / or, the C3-C 10 The cycloalkoxy group is preferably cyclopropoxy, cyclobutoxy, cyclopentoxy, cyclohexoxy, cycloheptoxy, cyclooctoxy, cyclononoxy, or cyclodecoxy.

[0086] And / or, the C6-C 30 The aryl group is preferably phenyl, biphenyl, terphenyl, naphthyl, anthracene, tetraphenyl, phenanthrene, fluorenyl, indene, pyrene, perylene, fluoranyl, benzophenanthrene, triphenylene, or phenylene;

[0087] And / or, the C6-C 30 The preferred arylene groups are phenylene, biphenylene, terphenylene, naphthylene, anthracene, tetraphenylene, phenanthrene, fluorene, indene, pyrene, perylene, fluorene-anthrene, benzophenone, triphenylene, and phenylene;

[0088] And / or, the C6-C 30The aryloxy group is preferably phenoxy, toluoxy, biphenyloxy, naphthoxy, anthraceneoxy, phenanthroxy, or benzyloxy;

[0089] And / or, the C3-C 30 The heteroaryl groups are preferably thienyl, furanyl, pyrroleyl, thiazolyl, oxazolyl, imidazolyl, pyrazolyl, triazolyl, benzothienyl, benzofuranyl, indolyl, isoindolyl, benzothiazolyl, benzooxazolyl, benzoimidazolyl, benzotriazolyl, purinyl, carbazoleyl, dibenzothienyl, dibenzofuranyl, pyridyl, pyrimidinyl, triazinyl, phenazinyl, quinolinyl, isoquinolinyl, naphridinyl, acridineyl, phenanthrolinel, and carbolinyl.

[0090] And / or, the C3-C 30 The preferred heteroaryl groups are thienyl, furanyl, pyrrolyl, thiazolyl, oxazolyl, imidazolyl, pyrazolyl, triazolyl, benzothienyl, benzofuranyl, indoleyl, isoindoleyl, benzothiazolyl, benzoxazolyl, benzoimidazolyl, benzotriazolyl, purineyl, carbazolyl, dibenzothienyl, dibenzofuranyl, pyridinyl, pyrimidinyl, triazinyl, phenazinyl, quinolinyl, isoquinolinyl, naphridinyl, acridineyl, phenanthrolineyl, and carbazolyl.

[0091] According to the above heterocyclic compound, the halogen is preferably F, Br, Cl, or I, more preferably F, Br, or Cl, more preferably F or Cl, and most preferably F.

[0092] According to the above heterocyclic compounds, the C1-C 20 The alkyl group is preferably methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, sec-butyl, n-pentyl, neopentyl, isopentyl, n-hexyl, n-heptyl, n-octyl, n-decyl, isooctyl, nonyl, 2-ethylhexyl, more preferably methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, sec-butyl, n-pentyl, neopentyl, isopentyl, n-hexyl, n-octyl, n-heptane, and even more preferably methyl, ethyl, n-propyl, isopropyl, n-... Butyl, isobutyl, tert-butyl, sec-butyl, n-pentyl, neopentyl, isopentyl, n-hexyl, more preferably methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, sec-butyl, n-pentyl, particularly preferably methyl, ethyl, n-propyl, isopropyl, tert-butyl, n-pentyl, especially preferably methyl, ethyl, n-propyl, isopropyl, tert-butyl, particularly preferably methyl, ethyl, tert-butyl, particularly preferably methyl, ethyl, most preferably methyl.

[0093] According to the above heterocyclic compounds, the C1-C 20The alkoxy group is preferably methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentoxy, neopentoxy, isopentoxy, n-hexyloxy, n-octoxy, isooctoxy, n-decoxy, n-nonoxy, n-heptoxy, more preferably methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentoxy, neopentoxy, isopentoxy, n-hexyloxy, n-octyloxy, n-heptoxy, and even more preferably methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, n-butoxy Oxygen, isobutoxy, tert-butoxy, sec-butoxy, n-pentoxy, neopentoxy, isopentoxy, n-hexyloxy, more preferably methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentoxy, particularly preferably methoxy, ethoxy, n-propoxy, isopropoxy, tert-butoxy, n-pentoxy, especially preferably methoxy, ethoxy, n-propoxy, isopropoxy, tert-butoxy, particularly preferably methoxy, ethoxy, tert-butoxy, particularly preferably methoxy, ethoxy, most preferably methoxy.

[0094] According to the above heterocyclic compound, the C3-C 20 The cycloalkyl group is preferably cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclooctyl, cyclononyl, cyclodecyl, norbornyl, or adamantyl; more preferably cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, or adamantyl; more preferably cyclopropyl, cyclopentyl, cyclohexyl, or adamantyl; particularly preferably cyclopentyl, cyclohexyl, or adamantyl; especially preferably cyclohexyl or cyclopentyl; and most preferably cyclohexyl.

[0095] According to the above heterocyclic compound, the C3-C 10 The cycloalkoxy group is preferably cyclopropoxy, cyclobutoxy, cyclopentoxy, cyclohexyloxy, cycloheptoxy, cyclooctoxy, cyclononoxy, or cyclodecoxy, more preferably cyclopropoxy, cyclobutoxy, cyclopentoxy, cyclohexyloxy, or cycloheptoxy, more preferably cyclopropoxy, cyclobutoxy, cyclopentoxy, or cyclohexyloxy, particularly preferably cyclopropoxy, cyclobutoxy, or cyclopentoxy, especially preferably cyclopropoxy or cyclopentoxy, and most preferably cyclopropoxy.

[0096] According to the above heterocyclic compound, the C6-C 30The aryl group is preferably phenyl, biphenyl, terphenyl, naphthyl, anthracene, tetraphenyl, phenanthryl, fluorenyl, indene, pyrene, perylene, fluoranthyl, benzo[a]phenanthryl, triphenylene, or benzo[a] ... More preferably, it is phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthryl, fluoranthyl, triphenylene, perylene, pyrene, benzo[a]pyrene, hydroxyl, benzo[a]hydroxyl; particularly preferably, it is phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthryl, pyrene, fluoranthyl, triphenylene, hydroxyl; especially preferably, it is phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthryl; even more preferably, it is phenyl, biphenyl, terphenyl, naphthyl, phenanthryl; even more preferably, it is phenyl, naphthyl, biphenyl; even more preferably, it is phenyl, biphenyl; most preferably, it is phenyl.

[0097] According to the above heterocyclic compound, the C6-C 30 The arylene group is preferably phenylene, biphenylene, terphenylene, naphthylene, anthracene, tetraphenylene, phenanthrene, fluorene, indene, pyrene, perylene, fluoranthylene, benzo[a]phenanthrene, triphenylene, or benzo[a]phenanthrene, and more preferably phenylene, biphenylene, terphenylene, naphthylene, anthracene, tetraphenylene, phenanthrene, fluorene, indenepyrene, perylene, fluoranthylene, benzo[a]phenanthrene, triphenylene, or benzo[a]phenanthrene, benzo[a]phenanthrene, benzo[a]phenanthrene, benzo[a]phenanthrene, benzo[a]phenanthrene, benzo[a]phenanthrene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, spirodifluorene, phenylnaphthylene, naphthylnaphthylene, phenylphenanthrene, naphthylphenanthrene, phenylanthracene, naphthylanthracene, benzo[a]pyrene, or benzo[a] ... More preferably, it is phenylene, biphenylene, terphenylene, naphthylene, anthraquinone, phenanthrene, fluoranthylene, triphenylene, perylene, pyrene, benzo[a]pyrene, phenylene, benzo[a]phenylene; particularly preferably, it is phenylene, biphenylene, terphenylene, naphthylene, anthraquinone, phenanthrene, pyrene, fluoranthylene, triphenylene, phenylene; especially preferably, it is phenylene, biphenylene, terphenylene, naphthylene, anthraquinone, phenanthrene; even more preferably, it is phenylene, biphenylene, terphenylene, naphthylene, phenanthrene; even more preferably, it is phenylene, naphthylene, biphenylene; even more preferably, it is phenylene, biphenylene; most preferably, it is phenylene.

[0098] According to the above heterocyclic compound, the C6-C 30The aryloxy group is preferably phenoxy, toluoxy, biphenyloxy, naphthoxy, anthraquinoneoxy, phenanthreneoxy, or benzyloxy, more preferably phenoxy, toluoxy, or benzyloxy, more preferably phenoxy or toluoxy, and most preferably phenoxy.

[0099] According to the above heterocyclic compound, the C3-C 30 The heteroaryl group is preferably thienyl, furanyl, pyrroleyl, thiazolyl, oxazolyl, imidazolyl, pyrazolyl, triazolyl, benzothienyl, benzofuranyl, indolyl, isoindolyl, benzothiazolyl, benzooxazolyl, benzoimidazolyl, benzotriazolyl, purinyl, carbazoleyl, dibenzothienyl, dibenzofuranyl, pyridyl, pyrimidinyl, triazinyl, phenazinyl, quinolinyl, isoquinolinyl, naphridyl, acridineyl, phenanthrolinel, carbolinyl, and more preferably thienyl, furanyl, pyrroleyl, thiazolyl, oxazolyl, imidazolyl, pyrazolyl The following are listed: benzothiophene, benzofuran, indole, isoindole, benzothiazolyl, benzooxazolyl, benzimidazolyl, benzotriazolyl, carbazole, dibenzothiaphene, dibenzofuran, pyridyl, pyrimidinyl, triazinyl, phenazinyl, quinolinyl, isoquinolinyl, phenanthrolinel, more preferably thiaphene, furanyl, pyrroloyl, pyrazolyl, benzothiaphene, benzofuran, indole, isoindole, benzothiazolyl, benzooxazolyl, benzimidazolyl, benzotriazolyl, carbazole, dibenzothiaphene, dibenzofuran The compounds are pyridyl, pyrimidinyl, triazine, phenazine, quinolinyl, isoquinolinyl, and phenanthroline, particularly preferably thienyl, furanyl, benzothienyl, benzofuranyl, dibenzothienyl, dibenzofuranyl, pyridyl, pyrimidinyl, triazine, phenazine, quinolinyl, isoquinolinyl, and phenanthroline, particularly preferably benzothienyl, benzofuranyl, dibenzothienyl, dibenzofuranyl, pyridyl, thienyl, furanyl, pyrimidinyl, triazine, quinolinyl, isoquinolinyl, and phenanthroline, particularly preferably benzothienyl, benzofuranyl, dibenzothienyl, dibenzofuranyl, pyridyl, thienyl, furanyl, pyrimidinyl, triazine, quinolinyl, isoquinolinyl, and phenanthroline, particularly preferably benzothienyl, benzo... The compounds are benzo[a]furanyl, dibenzothiopheneyl, dibenzofuranyl, pyridyl, thiopheneyl, furanyl, pyrimidinyl, quinolinyl, and isoquinolinyl, particularly preferably benzo[a]furanyl, dibenzothiopheneyl, dibenzofuranyl, pyridyl, pyrimidinyl, quinolinyl, and isoquinolinyl, particularly preferably dibenzothiopheneyl, dibenzofuranyl, pyridyl, pyrimidinyl, quinolinyl, and isoquinolinyl, particularly preferably dibenzothiopheneyl, dibenzofuranyl, and pyridyl, particularly preferably dibenzofuranyl and pyridyl, and most preferably dibenzofuranyl.

[0100] According to the above heterocyclic compound, the C3-C 30The heteroaryl group is preferably thienyl, furanyl, pyrrolyl, thiazolyl, oxazolyl, imidazolyl, pyrazoleyl, triazolyl, benzothienyl, benzofuranyl, indoleyl, isoyindoleyl, benzothiazolyl, benzoxazolyl, benzoimidazolyl, benzotriazolyl, purineyl, carbazolyl, dibenzothienyl, dibenzofuranyl, pyridinyl, pyrimidinyl, triazinyl, phenazinyl, quinolinyl, isoquinolinyl, naphthinyl, acridineyl, phenanthrolineyl, carbazolyl, and more preferably thienyl, furanyl, pyrrolyl, thiazolyl, oxazolyl, or imidazolyl. The following groups are listed: pyrazolyl, triazolyl, benzothiophene, benzofuranyl, indoleyl, isoindoleyl, benzothiazolyl, benzoxazolyl, benzimidazolyl, benzotriazolyl, carbazolyl, dibenzothiaphene, dibenzofuranyl, pyridinyl, pyrimidinyl, triazinyl, phenazinyl, quinolinyl, isoquinolinyl, phenanthrolineyl, more preferably thiaphene, furanyl, pyrrolyl, pyrazolyl, benzothiaphene, benzofuranyl, indoleyl, isoindoleyl, benzothiazolyl, benzoxazolyl, benzimidazolyl, benzotriazolyl, carbazolyl, dibenzothiaphene, and more preferably pyridyl ... Dibenzofuranyl, pyridinyl, pyrimidinyl, triazineyl, phenazineyl, quinolinyl, isoquinolinyl, phenanthrolineyl, particularly preferably thiopheneyl, furanyl, benzothiopheneyl, benzofuranyl, dibenzothiopheneyl, dibenzofuranyl, pyridinyl, pyrimidinyl, triazineyl, phenazineyl, quinolinyl, isoquinolinyl, phenanthrolineyl, particularly preferably benzothiopheneyl, benzofuranyl, dibenzothiopheneyl, dibenzofuranyl, pyridinyl, thiopheneyl, furanyl, pyrimidinyl, triazineyl, quinolinyl, isoquinolinyl, phenanthrolineyl, particularly preferably benzothiopheneyl, benzofuranyl, dibenzothiopheneyl, dibenzofuranyl, pyridinyl, thiopheneyl, furanyl, pyrimidinyl, triazineyl, quinolinyl, isoquinolinyl, phenanthrolineyl, particularly preferably benzothiopheneyl Thiophene, benzofuranyl, dibenzothiophene, dibenzofuranyl, pyridinyl, thiophene, benzofuranyl, pyrimidinyl, quinolinyl, isoquinolinyl, particularly preferably benzothiophene, benzofuranyl, dibenzothiophene, dibenzofuranyl, pyridinyl, pyrimidinyl, quinolinyl, isoquinolinyl, particularly preferably dibenzothiophene, dibenzofuranyl, pyridinyl, pyrimidinyl, quinolinyl, isoquinolinyl, particularly preferably dibenzothiophene, dibenzofuranyl, pyridinyl, particularly preferably dibenzofuranyl, pyridinyl, most preferably dibenzofuranyl.

[0101] According to the above heterocyclic compounds, the substituents in the "substituted or unsubstituted" category are preferably each independently selected from deuterium, fluorinyl, cyano, methyl, ethyl, propyl, n-butyl, tert-butyl, cyclopentyl, cyclohexyl, adamantyl, fluorenyl, spirofluorenyl, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthryl, pyrene, fluoranyl, triphenylene, phenylene, dibenzofuranyl, carbazoyl, phenantholinyl, dibenzothiophene, pyrroleyl, furanyl, triazinyl, pyrazinyl, pyridazinyl, oxazolyl, thiophene, benzothiophene, benzofuranyl, benzooxazolyl, imidazoyl, quinazolinyl, methoxy, ethoxy, propoxy, n-butoxy, tert-butoxy, indoleyl, indazole, pyrimidinyl, quinolinyl, isoquinoline. A combination of one or more of linyl and pyridyl groups; more preferably selected from one or more of deuterium, fluorinyl, cyano, methyl, ethyl, tert-butyl, cyclopentyl, cyclohexyl, adamantyl, fluorenyl, spirofluorenyl, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthryl, dibenzofuranyl, carbazoleyl, dibenzothiopheneyl, pyrroleyl, furanyl, pyrazinyl, pyridazinyl, oxazolyl, benzothiopheneyl, benzofuranyl, benzooxazolyl, imidazolyl, quinazolinyl, methoxy, tert-butoxy, thiopheneyl, pyridyl, pyrimidinyl, quinolinyl, and isoquinolinyl groups; more preferably selected from one or more of deuterium, fluorinyl, cyano, methyl, tert-butyl, cyclopentyl, adamantyl, fluorenyl, spirofluorenyl, phenyl, biphenyl, terphenyl, naphthyl, and anthracene. phenanthryl, dibenzofuranyl, carbazole, dibenzothiophenyl, benzothiophenyl, benzofuranyl, methoxy, quinolinyl, isoquinolinyl, pyridyl; particularly preferably selected from one or more combinations of deuterium, fluoryl, cyano, methyl, tert-butyl, cyclopentyl, adamantyl, fluorenyl, spirofluorenyl, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthryl, dibenzofuranyl, carbazole, dibenzothiophenyl, benzothiophenyl, benzofuranyl, methoxy; particularly preferably selected from one or more combinations of deuterium, fluoryl, cyano, methyl, tert-butyl, fluorenyl, spirofluorenyl, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthryl, dibenzofuranyl, dibenzothiophenyl; especially preferred The material is selected from one or more combinations of deuterium, fluoro, cyano, phenyl, dibenzofuranyl, naphthyl, biphenyl, and dibenzothiophene; particularly preferably selected from one or more combinations of deuterium, fluoro, cyano, phenyl, dibenzofuranyl, naphthyl, and biphenyl; particularly preferably selected from one or more combinations of deuterium, fluoro, phenyl, dibenzofuranyl, naphthyl, and biphenyl; particularly preferably selected from one or more combinations of deuterium, fluoro, phenyl, naphthyl, and biphenyl; particularly preferably selected from one or more combinations of deuterium, phenyl, and biphenyl; particularly preferably selected from one or more combinations of deuterium and phenyl; most preferably deuterium.

[0102] According to the above-mentioned heterocyclic compounds, the heterocyclic compounds are preferably selected from the following structures:

[0103]

[0104]

[0105]

[0106]

[0107]

[0108]

[0109]

[0110]

[0111]

[0112]

[0113]

[0114]

[0115]

[0116]

[0117]

[0118]

[0119]

[0120]

[0121]

[0122]

[0123]

[0124]

[0125]

[0126]

[0127]

[0128]

[0129]

[0130]

[0131]

[0132]

[0133]

[0134]

[0135]

[0136]

[0137]

[0138]

[0139]

[0140]

[0141]

[0142]

[0143]

[0144]

[0145]

[0146]

[0147]

[0148] .

[0149] Secondly, a material for an organic element comprising the aforementioned heterocyclic compound.

[0150] Preferably, the material is a material for a light-emitting auxiliary layer, an electron blocking layer, a hole transport layer, or a hole injection layer; more preferably, the material is a material for a light-emitting auxiliary layer, an electron blocking layer, or a hole transport layer; more preferably, the material is a material for a light-emitting auxiliary layer, an electron blocking layer, or a second hole transport layer; even more preferably, the material is a material for a light-emitting auxiliary layer or a second hole transport layer; most preferably, the material is a material for a second hole transport layer.

[0151] Thirdly, an organic electroluminescent element, characterized in that the organic electroluminescent element comprises: a cathode, an anode, and one or more organic material layers disposed between the cathode and the anode and including a light-emitting layer, wherein one or more layers of the organic material layer contain the aforementioned heterocyclic compound, and when two or more layers contain the aforementioned heterocyclic compound, the contained heterocyclic compounds may be the same or different.

[0152] Preferably, the organic electroluminescent element can be a single-layer device or a multilayer device.

[0153] Preferably, the organic electroluminescent element comprises a substrate, an anode, a hole transport region, an emissive layer, an electron transport region, and a cathode. The emissive layer is located between the anode and the cathode, the hole transport region is located between the anode and the emissive layer, and the electron transport region is located between the emissive layer and the cathode. The hole transport region comprises the aforementioned heterocyclic compound.

[0154] Preferably, in the organic electroluminescent element, the hole transport region includes one or more of a hole injection layer, a first hole transport layer, and a second hole transport layer. The hole injection layer is close to the anode, the first hole transport layer is located between the hole injection layer and the second hole transport layer, and the second hole transport layer is located between the first hole transport layer and the light-emitting layer. The second hole transport layer contains the aforementioned heterocyclic compound.

[0155] More preferably, in the single-layer device, the second hole transport layer comprises the aforementioned heterocyclic compound.

[0156] More preferably, in the stacked device, the at least one second hole transport layer comprises the aforementioned heterocyclic compound.

[0157] Fourthly, an electronic device includes one or more of a display, a monitor, and a lighting device, wherein the device comprises the aforementioned heterocyclic compound, the aforementioned organic element material, or the aforementioned organic electroluminescent element.

[0158] In summary, compared with the prior art, the above-described technical solutions conceived by this invention can achieve the following beneficial effects:

[0159] Compared with the prior art, this invention can effectively regulate molecular stacking by introducing a dibenzocarbazole group with a rigid planar structure, avoiding excessive disordered arrangement, and giving the material better film-forming properties and thermal stability, which is beneficial to improving the service life of organic electroluminescent devices. Attached Figure Description

[0160] Figure 1 This is a schematic diagram of the structure of the organic electroluminescent element described in Example 1; wherein: Figure 1 The markings in the diagram represent: 1. First electrode layer, 2. Hole injection layer, 3. Hole transport layer, 4. Second hole transport layer, 5. Light emission layer, 6. Hole blocking layer, 7. Electron transport layer, 8. Electron injection layer, 9. Second electrode layer.

[0161] Figure 2 This is the mass spectrum (LC-MS) of compound 2 prepared in synthesis example 1 in the compound preparation examples.

[0162] Figure 3 The NMR (nuclear magnetic resonance) of compound 2, prepared in synthesis example 1, is shown in the compound preparation examples. 1 ¹H NMR spectrum.

[0163] Figure 4 This is the mass spectrum (LC-MS) of compound 3 prepared in synthesis example 2 of the compound preparation examples.

[0164] Figure 5 The NMR (nuclear magnetic resonance) of compound 3, prepared in synthesis example 2, is shown in the compound preparation examples. 1 ¹H NMR spectrum.

[0165] Figure 6 This is the mass spectrum (LC-MS) of compound 4 prepared in synthesis example 3 in the compound preparation examples.

[0166] Figure 7 The NMR (nuclear magnetic resonance) of compound 4, prepared in synthesis example 3, is shown in the compound preparation examples. 1 ¹H NMR spectrum.

[0167] Figure 8 This is the mass spectrum (LC-MS) of compound 5 obtained from synthesis example 4 in the compound preparation examples.

[0168] Figure 9 The NMR (nuclear magnetic resonance) of compound 5, prepared in synthesis example 4, is shown in the compound preparation examples. 1 ¹H NMR spectrum.

[0169] Figure 10This is the mass spectrum (LC-MS) of compound 7 prepared in synthesis example 5 of the compound preparation examples.

[0170] Figure 11 The NMR (nuclear magnetic resonance) of compound 7, prepared in synthesis example 5, is shown in the compound preparation examples. 1 ¹H NMR spectrum.

[0171] Figure 12 This is the mass spectrum (LC-MS) of compound 11 prepared in synthesis example 6 of the compound preparation examples.

[0172] Figure 13 The NMR of compound 11 prepared in synthesis example 6 of the compound preparation examples is shown in the figure. 1 ¹H NMR spectrum.

[0173] Figure 14 This is the mass spectrum (LC-MS) of compound 153 prepared in synthesis example 7 of the compound preparation examples.

[0174] Figure 15 The NMR of compound 153 prepared in Synthesis Example 7 of the compound preparation examples is shown in the figure. 1 ¹H NMR spectrum. Detailed Implementation

[0175] Exemplary embodiments will now be described in detail, examples of which are illustrated in the accompanying drawings, wherein the same reference numerals always refer to the same elements. In this respect, these exemplary embodiments may take different forms and should not be construed as limited to the description set forth herein. Therefore, the exemplary embodiments are described below only by reference to the accompanying drawings to illustrate aspects. As used herein, the term “and / or” includes any and all combinations of one or more of the associated enumerated items. Expressions such as “at least one” modify the entire list of elements when preceding or following the list of elements, but do not modify individual elements of the list.

[0176] It will be further understood that the terms “comprising” or “including” as used in this specification indicate the presence of the stated features, areas, integrals, steps, operations, elements, and / or components, but do not preclude the presence or addition of one or more additional features, areas, integrals, steps, operations, elements, components, and / or sets thereof.

[0177] Unless otherwise defined, all terms used herein (including technical and scientific terms) have the same meaning as commonly understood by one of ordinary skill in the art to which this general inventive concept pertains. It will be further understood that terms, such as those defined in commonly used dictionaries, should be interpreted as having meanings consistent with their meanings in the relevant field and in the context of this disclosure, and will not be interpreted in an idealized or overly formal sense unless clearly defined herein.

[0178] The present invention will be further illustrated below with reference to specific embodiments. It should be understood that these embodiments are for illustrative purposes only and are not intended to limit the scope of protection of the present invention. Furthermore, it should be understood that after reading the disclosure of this invention, those skilled in the art can make various modifications or alterations to the invention, and these equivalent forms also fall within the scope of protection defined by this invention.

[0179] In this invention, unless otherwise specified, all parts and percentages are by weight, and the equipment and raw materials used are commercially available or commonly used in the art. Unless otherwise specified, the methods in the following embodiments are conventional methods in the art.

[0180] Unless otherwise specified, the experimental methods used in the following examples are conventional methods; the starting materials, reaction materials, intermediates, reagents, and materials used in the following examples are all commercially available unless otherwise specified.

[0181] Terminology Explanation

[0182] In this invention, the term "halogen" may include fluorine, chlorine, bromine or iodine.

[0183] In this invention, the term "C1-C" 20 "Alkyl" refers to a monovalent substituent derived from a straight-chain or branched saturated hydrocarbon having 1 to 20 carbon atoms, including but not limited to methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, and hexyl.

[0184] In this invention, the term "C1-C" 20 "Alkoxy" refers to a monovalent substituent represented by RO- having 1 to 20 carbon atoms, where R refers to an alkyl group having 1 to 20 carbon atoms. Specific examples include, but are not limited to, methoxy, ethoxy, n-propoxy, isopropoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentoxy, neopentoxy, isopentoxy, n-hexyloxy, etc.

[0185] In this invention, the term "C3-C" 20"Cycloalkyl" refers to a monovalent substituent derived from a monocyclic or polycyclic nonaromatic hydrocarbon having 3 to 20 carbon atoms. Examples of such cycloalkyl groups include, but are not limited to, cyclopropane, cyclobutane, cyclopentane, cyclohexane, norbornyl, and adamantane.

[0186] In this invention, the term "torr" is a unit of pressure, with the unit symbol torr. 1 torr = 1.33322 * 10 2 Pa. By convention, 1 Torr = 1 mmHg.

[0187] In this invention, the term "C3-C" 10 "Cycloalkoxy" refers to a monovalent substituent represented by RO-, having 3 to 10 carbon atoms, where R refers to a cycloalkyl group with 3 to 10 carbon atoms. Specific examples include, but are not limited to, cyclopropoxy, cyclobutoxy, cyclopentoxy, and cyclohexoxy.

[0188] In this invention, the term "C6-C" 30 "Aryl" refers to a monovalent substituent derived from an aromatic hydrocarbon having a single ring or a combination of two or more rings and having 6 to 30 carbon atoms. Further, such an aryl group can have two or more rings simply side-attached to or fused together with each other. Examples of such aryl groups include, but are not limited to, phenyl, biphenyl, naphthyl, phenanthryl, anthracene, pyrene, triphenylene, fluoranthyl, 9,9-dimethylfluorene, 9,9-diphenylfluorene, spirodifluorene, etc.

[0189] In this invention, the term "aryl" refers to a divalent aryl group derived by removing one hydrogen atom from an "aryl" group, such as a phenyl group by removing one hydrogen atom to form a phenylene group, or a naphthyl group by removing one hydrogen atom to form a naphthylene group.

[0190] In this invention, the term "C3-C" 30 "Heteroaryl" refers to a monovalent substituent derived from a mono- or poly-heterocyclic aromatic hydrocarbon having 3 to 30 carbon atoms. In this connection, at least one carbon atom, preferably 1 to 3 carbons, in the ring is substituted by a heteroatom, such as N, O, S, P, B, or Si. Furthermore, such heteroaryl can have two or more rings simply side-attached to each other, fused together, or fused with an aryl group. Examples of such heteroaryl include pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, indoleazinyl, indoleyl, indole-pyridinyl, purinyl, phenanthrolinel, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, thiazolyl, imidazolyl, oxazolyl, furanyl, thiopheneyl, benzofuranyl, benzothiopheneyl, benzothiazolyl, benzoimidazolyl, benzooxazolyl, carbazoleyl, dibenzofuranyl, dibenzothiopheneyl, etc., but the invention is not limited thereto.

[0191] In this invention, the term "hybrid aryl" refers to a divalent heteroaryl group derived by removing a hydrogen atom from an "aryl" group. For example, pyridyl group is formed by removing a hydrogen atom to form pyridylene group, and pyrazinyl group is formed by removing a hydrogen atom to form pyrazinylene group.

[0192] In this invention, the expression "AA-BB number of carbon atoms" or "C(AA-BB) Z group" means that the Z group has no carbon atoms when it is unsubstituted, excluding the number of carbon atoms of the substituents when substituted. For example, an aryl group with C6-C30 means that when it is unsubstituted, the number of carbon atoms in the aryl group is any integer from 6 to 30. That is, when it is unsubstituted, the number of carbon atoms can be 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20...30.

[0193] In this invention, the term "substituted or unsubstituted" means that the hydrogen atoms in a compound are substituted by non-hydrogen groups or are not substituted by non-hydrogen groups. The number of substituents is not limited, as long as it can be obtained through a chemical reaction. It is not limited to a specific position, as long as the hydrogen at that position can be substituted by a substituent. For example, a carbazolyl group, unless otherwise specified in this specification, includes any of the following groups, but is not limited thereto.

[0194] “ "" indicates the connection position, and "unreplaced" means that the hydrogen atom is retained.

[0195] In this invention, " "Indicates the connection position.

[0196] When two or more substituents are present, the two or more substituents can be the same or different.

[0197] As used in this invention, terms such as 1, 2, A, B, etc. are used. These terms are only used to distinguish constituent elements and do not limit the nature or order of the constituent elements corresponding to the terms.

[0198] Compound preparation examples

[0199] LC-MS Brand: Waters, Model: SQ Detector 2

[0200] MRI brand: Bruker, model: AVANCE NEO 400

[0201] Those skilled in the art can synthesize the compounds of the present invention by referring to the following compounds and known synthetic methods.

[0202] 1. Synthesis Example 1: Synthesis of Compound 2

[0203] (1) Synthesis of intermediate 1

[0204]

[0205] Under nitrogen protection, 7H-dibenzocarbazole (20.00 g, 74.81 mmol), o-bromofluorobenzene (39.28 g, 224.46 mmol), and cesium carbonate (48.75 g, 149.62 mmol) were added to a 500 mL four-necked reaction flask, followed by 200 mL of N,N-dimethylformamide. The mixture was heated to 155 °C and reacted for 24 h. After the reaction was complete, the temperature of the reaction solution was lowered to 25 °C, and 200 mL of water was added. The reaction solution was extracted with ethyl acetate and separated. The organic phase was dried over anhydrous sodium sulfate. The organic phase was evaporated to dryness, and the crude product was purified by silica gel chromatography (developing solvent: hexane:dichloromethane = 4:1) to obtain intermediate 1 (26.43 g, yield 83.7%) as a white solid.

[0206] (2) Synthesis of intermediate 2

[0207]

[0208] Under nitrogen protection, intermediate 1 (26.43 g, 62.58 mmol), pinacol diborate (19.07 g, 75.10 mmol), dichloro[1,1'-bis(diphenylphosphine)ferrocene]palladium (2.87 g, 3.13 mmol), 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl (1.28 g, 3.12 mmol), and potassium acetate (12.28 g, 125.13 mmol) were added to a 500 mL four-necked reaction flask, followed by 300 mL of dioxane. The mixture was heated to 100 °C and reacted for 8 h. After the reaction was complete, the temperature of the reaction solution was lowered to 25 °C. 100 mL of water was added to the reaction solution, and the mixture was extracted with ethyl acetate and separated. The organic phase was dried over anhydrous sodium sulfate and then evaporated to dryness. The crude product was purified by silica gel chromatography (developing solvent: hexane: dichloromethane = 3:1) to obtain intermediate 2 as a white solid (19.8 g, yield 67.4%).

[0209] (3) Synthesis of intermediate 3

[0210]

[0211] Under nitrogen protection, intermediate 2 (19.80 g, 42.18 mmol), 4-bromo-1-chlorodibenzofuran (11.86 g, 43.14 mmol), tetrakis(triphenylphosphine)palladium (0.97 g, 0.84 mmol), and potassium carbonate (11.66 g, 84.36 mmol) were added to a 500 mL four-necked reaction flask, followed by 200 mL of toluene, 80 mL of ethanol, and 50 mL of water. The mixture was heated to 80 °C and reacted for 3 h. After the reaction was complete, the temperature of the reaction solution was lowered to 25 °C, and the reaction solution was extracted with ethyl acetate and separated. The organic phase was dried over anhydrous sodium sulfate and then evaporated to dryness. The crude product was purified by silica gel chromatography (developing solvent: hexane:dichloromethane = 10:1) to obtain intermediate 3 (16.98 g, yield 74%) as a pale yellow solid.

[0212] (4) Synthesis of compound 2

[0213]

[0214] Under nitrogen protection, intermediate 3 (6.80 g, 12.50 mmol), di([1,1'-diphenyl]-4-yl)amine (4.02 g, 12.51 mmol), tris(dibenzylacetone)dipalladium (0.23 g, 0.25 mmol), 2-dicyclohexylphosphine-2′,6′-dimethoxy-biphenyl (0.26 g, 0.63 mmol), and sodium tert-butoxide (2.40 g, 24.97 mmol) were added to a 250 mL four-necked reaction flask, followed by 100 mL of toluene. The mixture was heated to 110 °C and reacted for 2 h. After the reaction was complete, the temperature of the reaction solution was lowered to 25 °C. The reaction solution was extracted with ethyl acetate and separated. The organic phase was dried over anhydrous sodium sulfate and then evaporated to dryness. The crude product was purified by silica gel chromatography (developing solvent: hexane: dichloromethane = 1:1) to give compound 2 as a white solid (5.80 g, yield 56.0%).

[0215] LC-MS (APCI): 829.56 [M+H] + Calculated for: C 62 H 40 N2O 828.31. See the attached instruction manual for the corresponding mass spectrum. Figure 2 .

[0216] 1H NMR (400 MHz, Methylene Chloride-d2) δ 9.05-8.98 (d, J = 33 Hz,2H), 8.08-8.04 (d, J=16Hz,1H), 8.00-7.94 (d, J = 33 Hz, 2H), 7.89-7.79 (m,3H), 7.69-7.65 (d, J = 33 Hz, 2H), 7.61-7.56 (d, J = 34 Hz, 2H), 7.51-7.45(m, 8H), 7.44-7.38 (d, J =66 Hz, 4H), 7.33-7.25 (d, J = 34 Hz, 2H), 7.14-7.09(d, J = 66 Hz, 4H), 7.08-7.02 (d, J = 33 Hz, 2H), 6.93-6.87 (d, J = 34 Hz, 2H), 6.87-6.79 (d, J = 18 Hz, 1H), 6.65-6.57 (d, J = 66 Hz, 4H), 6.54-6.49(d, J = 16 Hz, 1H).

[0217] The corresponding NMR spectrum can be found in the instruction manual appendix. Figure 3 .

[0218] 2. Synthesis Example 2: Synthesis of Compound 3

[0219]

[0220] Under nitrogen protection, intermediate 3 (6.80 g, 12.50 mmol), 4-(2-naphthyl)-N-phenylamino (3.70 g, 12.51 mmol), tris(dibenzylideneacetone)palladium (0.23 g, 0.25 mmol), 2-dicyclohexylphosphine-2′,6′-dimethoxy-biphenyl (0.26 g, 0.63 mmol), and sodium tert-butoxide (2.40 g, 24.97 mmol) were added to a 250 mL four-necked reaction flask, followed by 100 mL of toluene. The mixture was heated to 110 °C and reacted for 2.5 h. After the reaction was complete, the reaction temperature was lowered to 25 °C, and the reaction solution was extracted with ethyl acetate and separated. The organic phase was dried over anhydrous sodium sulfate and then evaporated to dryness. The crude product was purified by silica gel chromatography (developing solvent: hexane: dichloromethane = 1:1) to give compound 3 as a white solid (6.12 g, yield 61.1%).

[0221] LC-MS (APCI): 803.45 [M+H]+ .Calcd for: C 60 H 38 N2O 802.30. See the attached instruction manual for the corresponding mass spectrum. Figure 4 .

[0222] 1 ¹H NMR (400 MHz, Methylene Chloride-d²) δ 9.06 (d, J = 8.4 Hz, 2H), 8.10 – 8.05 (m, 1H), 8.03 – 7.82 (m, 9H), 7.76 – 7.61 (m, 5H), 7.61 – 7.46 (m, 6H), 7.19 (d, J = 8.7 Hz, 2H), 7.13 – 6.82 (m, 8H), 6.79 – 6.67 (m, 2H), 6.54 (dd, J = 8.5, 2.2 Hz, 3H). See the attached manual for the corresponding NMR spectra. Figure 5 .

[0223] 3. Synthesis Example 3: Synthesis of Compound 4

[0224]

[0225] Under nitrogen protection, intermediate 3 (6.80 g, 12.50 mmol), N-phenyl-[1,1':4',1''-terphenyl]-4-amine (4.02 g, 12.51 mmol), tris(dibenzylacetone)palladium (0.23 g, 0.25 mmol), 2-dicyclohexylphosphine-2′,6′-dimethoxy-biphenyl (0.26 g, 0.63 mmol), and sodium tert-butoxide (2.40 g, 24.97 mmol) were added to a 250 mL four-necked reaction flask, followed by 100 mL of toluene. The mixture was heated to 110 °C and reacted for 3 h. After the reaction was complete, the reaction temperature was lowered to 25 °C, and the reaction solution was extracted with ethyl acetate and separated. The organic phase was dried over anhydrous sodium sulfate and then evaporated to dryness. The crude product was purified by silica gel chromatography (developing solvent: hexane: dichloromethane = 1:1) to give compound 4 as a white solid (6.15 g, yield 59.3%).

[0226] LC-MS (APCI): 829.52 [M+H] + .Calcd for: C 62 H 40 N2O 828.31. See the attached instruction manual for the corresponding mass spectrum. Figure 6 .

[0227] 1 ¹H NMR (400 MHz, Methylene Chloride-d²) δ 9.06 (d, J = 8.4 Hz, 2H), 8.12 – 8.07 (m, 1H), 8.01 (dd, J = 8.1, 1.4 Hz, 2H), 7.92 – 7.83 (m, 3H), 7.71 (dd, J = 8.3, 1.4 Hz, 6H), 7.68 – 7.47 (m, 10H), 7.44 – 7.35 (m, 1H), 7.17 – 6.97 (m, 6H), 6.97 – 6.81 (m, 4H), 6.76 – 6.67 (m, 2H), 6.59 – 6.48 (m, 3H). See the attached datasheet for the corresponding NMR spectra. Figure 7 .

[0228] 4. Synthesis Example 4: Synthesis of Compound 5

[0229]

[0230] The synthesis of compound 5 was performed using the same method as that of compound 2, except that intermediate 4 was used instead of di([1,1'-diphenyl]-4-yl)amine.

[0231] LC-MS (APCI): 829.70 [M+H] + .Calcd for: C 62 H 40 For the corresponding mass spectrum of N2O, please refer to the instruction manual. Figure 8 .

[0232] 1 ¹H NMR (400 MHz, Methylene Chloride-d²) δ 9.00 (d, J = 8.5 Hz, 2H), 8.07 – 8.02 (m, 1H), 7.96 (dd, J = 8.1, 1.5 Hz, 2H), 7.87 – 7.79 (m, 3H), 7.71 – 7.63 (m, 5H), 7.58 – 7.36 (m, 12H), 7.09 – 6.93 (m, 6H), 6.91 – 6.79 (m, 4H), 6.72 – 6.65 (m, 2H), 6.48 (dd, J = 8.3, 1.2 Hz, 3H). See the attached datasheet for the corresponding NMR spectra. Figure 9 .

[0233] 5. Synthesis Example 5: Synthesis of Compound 7

[0234]

[0235] The synthesis of compound 7 follows the same method as that of compound 2, except that intermediate 5 is used instead of di([1,1'-diphenyl]-4-yl)amine.

[0236] LC-MS (APCI): 753.47 [M+H] + .Calcd for: C 56 H 36 For the corresponding mass spectrum of N2O, please refer to the instruction manual. Figure 10 .

[0237] 1 H NMR (400 MHz, Methylene Chloride-d2) δ 9.01 (d, J = 8.5 Hz, 2H),8.08 – 8.01 (m, 1H), 7.96 (dd, J = 8.1, 1.4 Hz, 2H), 7.87 – 7.76 (m, 3H),7.66 (d, J = 8.8 Hz, 2H), 7.59 (ddd, J = 8.4, 6.8, 1.5 Hz, 2H), 7.53 – 7.44(m, 6H), 7.43 – 7.36 (m, 2H), 7.33 – 7.25 (m, 1H), 7.07 – 6.78 (m, 10H), 6.70– 6.61 (m, 2H), 6.53 – 6.43 (m, 3H). See the attached instruction manual for the corresponding NMR spectrum. Figure 11 .

[0238] 6. Synthesis Example 6: Synthesis of Compound 11

[0239]

[0240] The synthesis of compound 11 was performed using the same method as that of compound 2, except that intermediate 6 was used instead of di([1,1'-diphenyl]-4-yl)amine.

[0241] LC-MS (APCI): 803.56 [M+H] + .Calcd for: C 60 H 38 For the corresponding mass spectrum of N2O, please refer to the instruction manual. Figure 12 .

[0242] 1 ¹H NMR (400 MHz, Methylene Chloride-d²) δ 8.98 (d, J = 8.4 Hz, 2H), 8.10 – 8.01 (m, 1H), 7.99 – 7.76 (m, 8H), 7.66 (d, J = 8.8 Hz, 2H), 7.57 – 7.36 (m, 9H), 7.31 (dd, J = 7.1, 1.3 Hz, 1H), 7.16 – 6.81 (m, 10H), 6.72 – 6.45 (m, 5H). See the attached datasheet for the corresponding NMR spectra. Figure 13 .

[0243] 7. Synthesis Example 7: Synthesis of Compound 153

[0244]

[0245] The synthesis of intermediate 8 follows the same method as intermediate 3, except that intermediate 7 is used instead of 4-bromo-1-chlorodibenzofuran.

[0246] The synthesis of compound 153 was carried out by the same method as that of compound 2, except that intermediate 3 was replaced by intermediate 8 and di([1,1'-diphenyl]-4-yl)amine was replaced by intermediate 5.

[0247] LC-MS (APCI): 713.53 [M+H] + .Calcd for: C 54 H 36 The mass spectrum for N2O can be found in the instruction manual. Figure 14 .

[0248] 1 ¹H NMR (400 MHz, Methylene Chloride-d²) δ 9.12 (dd, J = 8.5, 4.4 Hz, 2H), 8.05 (d, J = 8.0 Hz, 1H), 8.00 – 7.82 (m, 7H), 7.71 – 7.63 (m, 3H), 7.59– 7.39 (m, 8H), 7.37 – 7.23 (m, 3H), 7.17 (ddd, J = 8.3, 6.8, 1.3 Hz, 1H), 7.04 – 6.78 (m, 6H), 6.73 – 6.54 (m, 3H), 6.36 (s, 2H). See the attached datasheet for the corresponding NMR spectra. Figure 15 .

[0249] Device fabrication examples

[0250] Device Comparison Example 1

[0251] This embodiment provides an organic electroluminescent element, such as... Figure 1 As shown, it includes a first electrode layer 1, a hole injection layer 2, a hole transport layer 3, a second hole transport layer 4, a light-emitting layer 5, a hole blocking layer 6, an electron transport layer 7, an electron injection layer 8, and a second electrode layer 9, which are stacked in sequence.

[0252] The specific device structure is as follows:

[0253] ITO / HT1-PD3%(10nm) / HT1(60nm) / EB-1(5nm) / BH-BD3%(20nm) / HB(5nm) / ET-LiQ50%(30nm) / Yb(1.5nm) / Mg:Ag 1:9(100nm).

[0254] Device fabrication process:

[0255] The bottom-emitting glass substrate 1 used in this embodiment was purchased from Guangdong Xinli Display Technology Co., Ltd., and ITO was used as the anode 2. First, the bottom-emitting glass substrate was cleaned sequentially with ITO cleaning agent, deionized water, and isopropanol. Then, the bottom-emitting glass substrate was baked at 180 degrees Celsius for 30 minutes to dry it.

[0256] Then, the bottom-emitting glass substrate is placed in the evaporation chamber, under a vacuum of approximately 10... -8 Under the condition of Turbo, organic layers were sequentially deposited on the ITO anode by thermal vacuum evaporation at a rate of 0.2-2 Å / s. Specifically, 3% PD was doped onto HT1 to form a 10 nm thick hole injection layer 2; HT1 was formed to a 60 nm thick first hole transport layer 3; EB-1 was deposited on HT1 to a thickness of 5 nm to form a second hole transport layer 4; 3% BD was doped onto the anthracene substrate BH to form a 20 nm thick blue emitting layer 5; HB was formed to a 5 nm thick hole blocking layer 6; ET was doped with 50% Liq to form a 30 nm thick electron transport layer 7; 1.5 nm Yb was deposited on the electron transport layer as an electron injection layer 8; and Mg:Ag (1:9) was formed to a thickness of 100 nm as a cathode 9. Finally, the device was transferred back to a glove box and sealed with a glass cover and desiccant to complete the device, designated as Organic Electronic Component 1, as Comparative Example 1.

[0257] The specific structures of the compounds involved are as follows:

[0258]

[0259]

[0260]

[0261]

[0262] Device Comparison Example 2

[0263] The second hole transport layer was prepared by replacing EB-1 with compound EB-2, and the organic electronic component 2 was fabricated using the same method as Comparative Example 1. This is referred to as Comparative Example 2.

[0264] Device Comparison Example 3

[0265] The second hole transport layer was prepared by replacing EB-1 with compound EB-3, and the organic electronic component 10 was fabricated using the same method as in Comparative Example 1. This is referred to as Comparative Example 3.

[0266] Device Example 1

[0267] The second hole transport layer was prepared by replacing EB-1 with compound 2 from the synthesis example 1 of the present invention, and the organic electronic component 3 was fabricated using the same method as in device comparison example 1. This is referred to as Example 1.

[0268] Device Example 2

[0269] The second hole transport layer was prepared by replacing EB-1 with compound 3 from the synthesis example 2 of the present invention, and the organic electronic component 4 was fabricated using the same method as in device comparison example 1. This is referred to as Example 2.

[0270] Device Example 3

[0271] The second hole transport layer was prepared by replacing EB-1 with compound 4 from the synthesis example 3 of the present invention, and the organic electronic component 5 was fabricated using the same method as in device comparison example 1. This is referred to as Example 3.

[0272] Device Example 4

[0273] The second hole transport layer was prepared by replacing EB-1 with compound 5 from the synthesis example 4 of the present invention, and the organic electronic component 6 was fabricated using the same method as in device comparison example 1. This is referred to as Example 4.

[0274] Device Example 5

[0275] The second hole transport layer was prepared by replacing EB-1 with compound 7 from the synthesis example 5 of the present invention, and the organic electronic component 7 was fabricated using the same method as in device comparison example 1. This is referred to as Example 5.

[0276] Device Example 6

[0277] The second hole transport layer was prepared by replacing EB-1 with compound 11 from the synthesis example 6 of the present invention, and the organic electronic component 8 was fabricated using the same method as in device comparison example 1. This is referred to as Example 6.

[0278] Device Example 7

[0279] The second hole transport layer was prepared by replacing EB-1 with compound 153 from the synthesis example 7 of the present invention, and the organic electronic component 9 was fabricated using the same method as in device comparative example 1. This is referred to as Example 7.

[0280] Test Results

[0281] Lifetime testing method: A voltage is applied to the obtained organic electroluminescent element to achieve a current density of 60 mA / cm². 2 The time it takes for the brightness to become 95% of the initial brightness is measured (LT95 (unit: hour)).

[0282] The test results are shown in Table 1.

[0283] Table 1

[0284] Organic electronic component 1 (Comparative Example 1) EB-1 41 Organic electronic component 2 (Comparative Example 2) EB-2 38 Organic electronic component 10 (Comparative Example 3) EB-3 54 Organic electronic component 3 (Example 1) Compound 2 78 Organic electronic component 4 (Example 2) Compound 3 81 Organic electronic component 5 (Example 3) Compound 4 85 Organic electronic component 6 (Example 4) Compound 5 82 Organic electronic component 7 (Example 5) Compound 7 89 Organic electronic component 8 (Example 6) Compound 11 73 Organic electronic component 9 (Example 7) Compound 153 94

[0285] As can be seen from Table 1, the organic electronic components 3-9 prepared by the compounds of this application have a longer service life compared with organic electronic components 1, 2, and 10. Therefore, the compounds of this invention are suitable for preparing high-performance organic electroluminescent components.

[0286] Those skilled in the art will readily understand that the above description is merely a preferred embodiment of the present invention and is not intended to limit the present invention. Any modifications, equivalent substitutions, and improvements made within the spirit and principles of the present invention should be included within the scope of protection of the present invention.

Claims

1. A heterocyclic compound containing a dibenzocarbazole structure, characterized in that, The heterocyclic compound has the structure shown in formula (1): in, for , , , ; " "Indicates the connection position; L 1 L 2 Each is independently selected from straight, substituted, or unsubstituted C6-C bonds. 30 aryl, substituted or unsubstituted C3-C 30 heteroaryl groups; L 3 Selected from substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted naphthyl, substituted or unsubstituted dibenzothiopheneyl; Ar 1 Ar 2 Each is independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C. 20 Alkyl groups, substituted or unsubstituted C3-C 20 cycloalkyl, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C3-C 30 heteroaryl groups; R 1 R 2 Each is independently selected from hydrogen, substituted or unsubstituted C6-C. 30 Aryl or deuterium; a is an integer selected from 0 to 6; when a is 2 or greater, multiple R... 1 They are the same or different from each other; b is selected from integers between 0 and 6; when b is 2 or greater, multiple R... 2 They are the same or different from each other; R 3 Selected from hydrogen, deuterium, substituted or unsubstituted C1-C 20 Alkyl groups, substituted or unsubstituted C6-C 30 Aryl and halogenated compounds; c is selected from integers between 0 and 4; when c is 2 or greater, multiple R... 3 Whether they are the same or different, R 3 The two Rs do not bond to each other or at least two Rs 3 They are interconnected to form a ring structure; In the phrase "substituted or unsubstituted", the substituents in the substituted state are each independently selected from deuterium, halogen, cyano, C1-C. 20 Alkyl, C1-C 20 alkoxy groups, C3-C 20 cycloalkyl, C3-C 10 Cycloalkoxy, C6-C 30 aryl, C6-C 30 aryloxy groups, C3-C 30 One or a combination of heteroaryl groups; The heteroatom in the heteroaryl group is selected from one or more of N, O, S, Si, P, and B; When Ar 1 When L is hydrogen, deuterium, halogen, or cyano, 1 Not a straight key; When Ar 2 When L is hydrogen, deuterium, halogen, or cyano, 2 Not a straight key; The heterocyclic compound may contain no substituent or contain at least one substituent selected from deuterium, fluorine, or cyano.

2. The heterocyclic compound according to claim 1, characterized in that... The structure of the heterocyclic compound is shown in Formula 1-1 below: Equation 1-1 Among them, L 1 , L 2 , L 3 Ar 1 Ar 2 , R 1 , R 2 , R 3 The definitions of a, b, and c are the same as above; The heterocyclic compound may contain no substituent or contain at least one substituent selected from deuterium, fluorine, or cyano.

3. The heterocyclic compound according to claim 1, characterized in that, The heterocyclic compound is selected from the following structures: Among them, L 1 , L 2 Ar 1 Ar 2 , R 1 , R 2 , R 3 The definitions of a, b, and c are the same as above; The heterocyclic compound may contain no substituent or contain at least one substituent selected from deuterium, fluorine, or cyano.

4. The heterocyclic compound according to claim 1, characterized in that, The heterocyclic compound is selected from the following structures: Among them, L 1 , L 2 Ar 1 Ar 2 , R 1 , R 2 , R 3 The definitions of a, b, and c are the same as above; The heterocyclic compound may contain no substituent or contain at least one substituent selected from deuterium, fluorine, or cyano.

5. The heterocyclic compound according to any one of claims 1-4, characterized in that, Among them, L 1 , L 2 Ar 1 Ar 2 , R 1 , R 2 , R 3 The definitions of a, b, and c are the same as above; The heterocyclic compound may contain no substituent or contain at least one substituent selected from deuterium, fluorine, or cyano; The Preferably , , , , , , , The definitions of a and b are the same as above. The Preferably , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , ; The Preferably , , , , , , , , , , , , , , , , , , , , , , , , ; in," "Indicates the connection position; The above groups are either unsubstituted or substituted by one or more substituents selected from deuterium, fluorine, or cyano.

6. The heterocyclic compound according to any one of claims 1-5, characterized in that, The R 1 R 2 R 3 Each is independently selected from hydrogen or deuterium, and / or, the L 1 L 2 Each is independently selected from straight, substituted, or unsubstituted C6-C bonds. 30 aryl, substituted or unsubstituted C3-C 30 The heteroaryl group, and / or the Ar 1 Ar 2 Each is independently selected from hydrogen, deuterium, substituted or unsubstituted C6-C. 30 aryl, substituted or unsubstituted C3-C 30 heteroaryl; when Ar 1 When it is hydrogen or deuterium, L 1 Not a straight key; when Ar 2 When it is hydrogen or deuterium, L 2 Not a straight bond; the definitions of a, b, and c are the same as above, and the definitions of substituents in "substituted or unsubstituted" are the same as above; Preferably, the L 1 L 2 Each is independently selected from straight-linked, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, substituted or unsubstituted dibenzofuranyl.

7. The heterocyclic compound according to any one of claims 1-5, characterized in that, The Ar 1 Ar 2 Each group is independently selected from hydrogen, deuterium, or the following substituted or unsubstituted groups: ， in," "Indicates the connection position; The definition of substituents in "substituted or unsubstituted" is the same as above.

8. The heterocyclic compound according to any one of claims 1-5, characterized in that, The -L 1 -Ar 1 -L 2 -Ar 2 Each of the following groups, whether substituted or unsubstituted, is independently selected: 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 ； in," "Indicates the connection position; The definition of substituents in "substituted or unsubstituted" is the same as above.

9. The heterocyclic compound according to any one of claims 1-6, characterized in that, The halogens are F, Br, Cl, and I; And / or, the C1-C 20 The alkyl groups are methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, sec-butyl, n-pentyl, neopentyl, isopentyl, n-hexyl, n-heptyl, n-octyl, n-decyl, isooctyl, nonyl, and 2-ethylhexyl. And / or, the C1-C 20 The alkoxy groups are methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentoxy, neopentoxy, isopentoxy, n-hexyloxy, n-octoxy, isooctoxy, n-decoxy, n-nonoxy, and n-heptoxy. And / or, the C3-C 20 The cycloalkyl groups are cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclooctyl, cyclononyl, cyclodecyl, norbornyl, and adamantyl. And / or, the C3-C 10 The cycloalkoxy groups are cyclopropoxy, cyclobutoxy, cyclopentoxy, cyclohexoxy, cycloheptoxy, cyclooctoxy, cyclononoxy, and cyclodecoxy. And / or, the C6-C 30 The aryl groups are phenyl, biphenyl, terphenyl, naphthyl, anthracene, tetraphenyl, phenanthryl, fluorenyl, indene, pyrene, perylene, fluoranyl, benzophenanthryl, triphenylene, and phenylene; And / or, the C6-C 30 The arylene groups are phenylene, biphenylene, terphenylene, naphthylene, anthracene, tetraphenylene, phenanthrene, fluorene, indene, pyrene, perylene, fluorene-anthrene, benzophenanthrene, triphenylene, and phenylene; And / or, the C6-C 30 The aryl groups are phenoxy, tolyloxy, biphenyloxy, naphthoxy, anthraceneoxy, phenanthroxy, and benzyloxy; And / or, the C3-C 30 The heteroaryl groups are thienyl, furanyl, pyrroleyl, thiazolyl, oxazolyl, imidazolyl, pyrazolyl, triazolyl, benzothienyl, benzofuranyl, indolyl, isoindolyl, benzothiazolyl, benzooxazolyl, benzoimidazolyl, benzotriazolyl, purinyl, carbazoleyl, dibenzothienyl, dibenzofuranyl, pyridyl, pyrimidinyl, triazinyl, phenazinyl, quinolinyl, isoquinolinyl, naphridinyl, acridineyl, phenanthrolinel, and carbolinyl. And / or, the C3-C 30 The heteroaryl groups are thienyl, furanyl, pyrrolyl, thiazolyl, oxazolyl, imidazolyl, pyrazolyl, triazolyl, benzothienyl, benzofuranyl, indoleyl, isoindoleyl, benzothiazolyl, benzoxazolyl, benzoimidazolyl, benzotriazolyl, purineyl, carbazolyl, dibenzothienyl, dibenzofuranyl, pyridinyl, pyrimidinyl, triazinyl, phenazinyl, quinolinyl, isoquinolinyl, naphridinyl, acridineyl, phenanthrolineyl, and carbazolyl.

10. The heterocyclic compound according to claim 1, characterized in that, The heterocyclic compound is preferably selected from the following structures: 。 11. A material for organic components, characterized in that, The material comprises a heterocyclic compound as described in any one of claims 1-10; preferably, the material is a material for a light-emitting auxiliary layer, an electron blocking layer, a hole transport layer, or a hole injection layer.

12. An organic electroluminescent element, characterized in that, The organic electroluminescent element includes: a cathode, an anode, and one or more organic material layers disposed between the cathode and the anode and including a light-emitting layer, wherein one or more layers of the organic material layer comprise a heterocyclic compound as described in any one of claims 1-10; Preferably, the organic electroluminescent element includes a substrate, an anode, a hole transport region, a light-emitting layer, an electron transport region, and a cathode. The light-emitting layer is located between the anode and the cathode, the hole transport region is located between the anode and the light-emitting layer, the electron transport region is located between the light-emitting layer and the cathode, and the hole transport region comprises the heterocyclic compound according to any one of claims 1-10.

13. An electronic device, comprising: One or more of the following: displays, monitors, and lighting devices, comprising the heterocyclic compound described in any one of claims 1-10, the material for organic elements as described in claim 11, or the organic electroluminescent element as described in any one of claims 12.

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