Heterocyclic compound and organic electroluminescent element comprising same

Abstract

Provided are a heterocyclic compound, and an organic electroluminescent element comprising same. The heterocyclic compound has a structure as shown in formula (1), X1 being selected from O or S, L1-L8 each being independently selected from a linking bond, a substituted or unsubstituted C6-C30 arylene group, or a substituted or unsubstituted C3-C30 heteroarylene group. The organic electroluminescent element prepared using said heterocyclic compound can achieve a reduced driving voltage and a long-lasting service life.

Description

A heterocyclic compound and an organic electroluminescent element containing the same

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS

[0002] This application claims priority to and the benefit of the following Chinese patent applications filed with the State Intellectual Property Office of China, the entire contents of which are incorporated herein by reference:

[0003] Chinese patent application number CN202310783446.5, filed on June 29, 2023, entitled “A heterocyclic compound and an organic electroluminescent element containing the same”; and

[0004] A Chinese patent application with application number CN202311157915.9 and application name “A heterocyclic compound and an organic electroluminescent element containing the same” submitted on September 8, 2023. Technical Field

[0005] The present invention belongs to the technical field of photoelectric materials, and in particular relates to a heterocyclic compound and an organic electroluminescent element containing the same. Background Art

[0006] An organic light emitting diode (OLED) is a self-luminous display element based on organic electroluminescent materials. Unlike existing liquid crystal display elements, it does not require a backlight and is thin, making it a technology suitable for flexible element devices (flexible light emitting display devices).

[0007] An organic light-emitting device has an anode and a cathode, and an organic thin film disposed between the two electrodes. It can be a simple device comprising a single light-emitting unit or a tandem-type device comprising multiple light-emitting units.

[0008] Simple components typically consist of a hole transport layer, a light-emitting layer, and an electron transport layer. Because the electron mobility of the electron transport layer material is much lower than the hole mobility of the hole transport layer material, an imbalance between holes and electrons entering the light-emitting layer results, affecting the component's luminous efficiency and lifespan.

[0009] Tandem devices typically incorporate a charge generation layer between the light-emitting units to ensure efficient charge distribution across the stacked layers while also improving current efficiency within each individual light-emitting layer. Typically, the charge generation layer has a PN junction, with an N-type charge generation layer and a P-type charge generation layer stacked in sequence.

[0010] The injection barrier of electrons from the charge generation layer to the adjacent electron transport layer is relatively large. Therefore, electrons accumulate at the interface between the N-type charge generation layer and the adjacent electron transport layer, which easily causes degradation of the interface and shortens the life of the component.

[0011] Therefore, there is an urgent need to develop new materials to increase the life of components.

[0012] Summary of the Invention

[0013] The object of the present invention is to provide a heterocyclic compound, wherein an organic electroluminescent element prepared using the compound can achieve a reduced driving voltage and a long service life.

[0014] The technical solution adopted by the present invention to solve its technical problem is:

[0015] A heterocyclic compound having the structure shown in formula (1)

[0016] in

[0017] X 1 Selected from O or S,

[0018] L 1 -L 8 are each independently selected from a linking bond, a substituted or unsubstituted C6-C30 arylene group, and a substituted or unsubstituted C3-C30 heteroarylene group,

[0019] n1 is selected from 0, 1, 2, 3, n2 is selected from 0, 1, 2, 3, n3 is selected from 0, 1, 2, 3, n4 is selected from 0, 1, 2, 3, n5 is selected from 0, 1, 2, 3, n6 is selected from 0, 1, 2, 3, n7 is selected from 0, 1, 2, 3, n8 is selected from 0, 1, 2, 3,

[0020] R 1 -R 8 At least one of them is selected from substituted or unsubstituted heteroaryl groups having 2 or more N atoms,

[0021] R 1 -R 8 The remaining groups are each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl,

[0022] The substitution in the substituted C6-C30 arylene group, substituted C3-C30 heteroarylene group, substituted C6-C30 aryl group, substituted C3-C30 heteroaryl group, and substituted heteroaryl group having 2 or more N atoms means that one or more hydrogen atoms therein are independently replaced by one or more of deuterium, halogen, cyano, C1-C10 alkyl group, C3-C10 cycloalkyl group, C6-C30 aryl group, and C3-C30 heteroaryl group.

[0023] The substitution in the substituted C1-C10 alkyl group and the substituted C3-C10 cycloalkyl group means that one or more hydrogen atoms are replaced by deuterium.

[0024] The invention provides an application of the heterocyclic compound as an organic electroluminescent element material.

[0025] An organic electroluminescent element comprises an anode, a cathode, and an organic layer located between the anode and the cathode, wherein the organic layer comprises the heterocyclic compound of the present invention.

[0026] Preferably, the organic layer comprises an electron transport layer and a light emitting layer, and the electron transport layer comprises the heterocyclic compound according to any one of claims 1 to 6.

[0027] Preferably, the organic layer comprises two or more light-emitting units, a charge generation layer is contained between the light-emitting units, the light-emitting units comprise an electron transport layer, and at least one of the charge generation layer and the electron transport layer comprises the heterocyclic compound described in the present invention.

[0028] Preferably, the organic layer comprises two or more light-emitting units, a charge generation layer is included between the light-emitting units, the light-emitting units include an electron transport layer, the charge generation layer includes an N-type charge generation layer and a P-type charge generation layer, and at least one of the N-type charge generation layer and the electron transport layer includes the heterocyclic compound described in the present invention.

[0029] The electron transport layer comprises the electron transport layer of each light-emitting unit, and at least one of the N-type charge generation layer and the electron transport layer comprises the heterocyclic compound of the present invention, which means that one N-type charge generation layer comprises the heterocyclic compound of the present invention; or multiple N-type charge generation layers comprise the heterocyclic compound of the present invention; or one electron transport layer in a light-emitting unit comprises the heterocyclic compound of the present invention; or one N-type charge generation layer and one electron transport layer in a light-emitting unit comprise the heterocyclic compound of the present invention; or one N-type charge generation layer and each electron transport layer in multiple light-emitting units comprise the heterocyclic compound of the present invention; or multiple N-type charge generation layers and each electron transport layer in multiple light-emitting units comprise the heterocyclic compound of the present invention, etc. When two or more layers comprise the heterocyclic compound of the present invention, the heterocyclic compounds may be the same or different.

[0030] The stacked structure of the present invention refers to n light-emitting units, where n is greater than or equal to 2, and the number of N-type charge generation layers is n-1.

[0031] Compared with the prior art, the present invention has the following beneficial effects:

[0032] 1. The organic electroluminescent compound of the present invention has a phenanthrofuran / thiophene structure, which improves the electron injection and transmission capabilities;

[0033] An organic electroluminescent element prepared using the compound can achieve a reduced driving voltage and a durable service life.

[0034] 2. Organic electroluminescent elements have a better lifespan. BRIEF DESCRIPTION OF THE DRAWINGS

[0035] Figure 1 is a schematic structural diagram of the organic electroluminescent element described in Application Example 1, wherein the first electrode layer 1, the hole injection layer 2, the hole transport layer 3, the light-emitting layer 4, the electron transport layer 5, the N-type charge generation layer 6, the P-type charge generation layer 7, the hole transport layer 8, the light-emitting layer 9, the electron transport layer 10, the electron injection layer 11 and the second electrode layer 12, wherein 100 is the first light-emitting unit and 200 is the second light-emitting unit. DETAILED DESCRIPTION

[0036] It should be noted that the following detailed descriptions are illustrative and intended to provide further explanation of the present application. Unless otherwise specified, all technical and scientific terms used herein have the same meaning as commonly understood by those skilled in the art to which the present application belongs.

[0037] It should be noted that the terms used herein are only for describing specific embodiments and are not intended to limit the exemplary embodiments according to the present application. As used herein, unless the context clearly indicates otherwise, the singular form is intended to include the plural form. In addition, it should be understood that when the terms "include" and / or "including" are used in this specification, they indicate that they are not limited to the contents disclosed in this specification.

[0038] The present invention will now be further described in conjunction with specific examples. The following examples are only intended to explain the present invention but do not limit the present invention. The test samples and test procedures used in the following examples include the following (if the specific experimental conditions are not specified in the examples, they are usually based on conventional conditions or the conditions recommended by the reagent company; the reagents, consumables, etc. used in the following examples, unless otherwise specified, can be obtained from commercial sources).

[0039] In order to more fully describe the present invention to those skilled in the art, embodiments of the present invention are provided. The scope of the present invention is not limited to the following embodiments. These embodiments can make the present invention more thorough and complete, and fully convey the concept of the present invention to those skilled in the art.

[0040] As used herein, the term "halogen" may include fluorine, chlorine, bromine or iodine.

[0041] As used herein, the term "C1-C10 alkyl" refers to a monovalent substituent derived from a straight or branched chain saturated hydrocarbon having 1 to 10 carbon atoms, examples of which include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, and hexyl.

[0042] As used herein, the term "C3-C10 cycloalkyl" refers to a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 10 carbon atoms. Examples of such cycloalkyl groups include, but are not limited to, cyclopropane, cyclobutane, cyclopentane, cyclohexane, norbornyl, adamantane, and the like.

[0043] As used in the present invention, the term "C6-C30 aryl" refers to a monovalent substituent derived from an aromatic hydrocarbon having a monocyclic or a combination of two or more rings and having 6 to 30 carbon atoms. Further, this aryl can have a form in which two or more rings are simply lateral or fused to each other. Examples of such aryl groups include, but are not limited to, phenyl, biphenyl, terphenyl, phenyl-substituted naphthyl, naphthyl-substituted phenyl, naphthyl, phenanthrenyl, anthracenyl, pyrenyl, triphenylene, fluoranthenyl, dimethyl 9,9-dimethylfluorene, 9,9-diphenylfluorene, spirobifluorenyl, etc.

[0044] As used herein, the term "arylene" refers to a divalent aromatic group derived from an "aryl" group by removing a hydrogen atom. For example, a phenyl group can be converted to a phenylene group by removing a hydrogen atom, and a naphthyl group can be converted to a naphthylene group by removing a hydrogen atom.

[0045] As used herein, the term "C3-C30 heteroaryl" refers to a monovalent substituent derived from a monocyclic or polycyclic heterocyclic aromatic hydrocarbon having 3 to 30 carbon atoms. In this connection, at least one carbon, preferably 1 to 3 carbon atoms, in the ring is substituted with a heteroatom such as N, O, S, P, B, or Si. In addition, such a heteroaryl group may have a form in which two or more rings are simply attached to each other or fused to each other or to an aromatic group. Examples of such heteroaryl groups include pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, indolizinyl, indolyl, indolopyridinyl, purinyl, phenanthroline, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, thiazolyl, imidazolyl, oxazolyl, furanyl, thienyl, benzofuranyl, benzothienyl, benzothiazolyl, benzimidazolyl, benzoxazolyl, carbazolyl, dibenzofuranyl, dibenzothienyl, and the like, but the present invention is not limited thereto.

[0046] As used herein, the term "heteroarylene" refers to a divalent heteroaryl group derived from a "heteroaryl" by removing a hydrogen atom. For example, a pyridyl group can be converted into a pyridylene group by removing a hydrogen atom from a pyridyl group.

[0047] As used in the present invention, the "carbon number of AA-BB" in the expression "Z group having AA-BB carbon atoms" or "Z group having C(AA-BB)" means the carbon number of AA-BB carbon atoms in the Z group when it is unsubstituted, and does not include the carbon number of the substituent when it is substituted. For example, a C6-C30 aryl group means that when it is unsubstituted, the number of carbon atoms in the aryl group is any integer between 6 and 30, that is, the number of carbon atoms when it is unsubstituted can be 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20...30.

[0048] As used in the present invention, the term "substituted" means that a hydrogen atom in a compound is replaced by another substituent. The position where the substitution occurs can be the position where the hydrogen atom is replaced, that is, the position is not limited to a specific position, as long as the hydrogen at the position can be replaced by a substituent. The number of substitutions, if not explicitly defined, includes all possible substitutions. For example, carbazolyl includes any of the following groups, but is not limited thereto, unless otherwise specified in this specification: "Unsubstituted" means that hydrogen atoms remain, and in this case, hydrogen atoms include protium, deuterium, and tritium.

[0049] When two or more substituents are present, the two or more substituents may be the same or different.

[0050] As used in the present invention, hydrogen atoms include protium, deuterium, and tritium. The compounds of the present invention may contain deuterium atoms from natural sources, or deuterium atoms may be introduced by deuterating a portion or all of the raw material compounds. If deuterium atoms are introduced from the raw materials, the deuteration rate may be 100%, or less than 100%, or less than 95%, or less than 90%, or less than 80%. The deuteration rate may also be greater than 1%, or greater than 5%, or greater than 10%. If the deuteration rate is not 100%, it represents a mixture of deuterated and undeuterated compounds, or a mixture of a fully deuterated and incompletely deuterated compound, or a mixture of a fully deuterated and undeuterated compound and an incompletely deuterated compound.

[0051] As used in the present invention, terms such as first, second, A, and B are used. The above terms are only used to distinguish components and do not limit the nature or order of the components to which the terms correspond.

[0052] The core of the present invention is a heterocyclic compound having the structure shown in formula (1)

[0053] X 1 Selected from O or S,

[0054] L 1 -L 8are each independently selected from a linking bond, a substituted or unsubstituted C6-C30 arylene group, and a substituted or unsubstituted C3-C30 heteroarylene group,

[0055] n1 is selected from 0, 1, 2, 3, n2 is selected from 0, 1, 2, 3, n3 is selected from 0, 1, 2, 3, n4 is selected from 0, 1, 2, 3, n5 is selected from 0, 1, 2, 3, n6 is selected from 0, 1, 2, 3, n7 is selected from 0, 1, 2, 3, n8 is selected from 0, 1, 2, 3,

[0056] R 1 -R 8 At least one of them is selected from substituted or unsubstituted heteroaryl groups having 2 or more N atoms,

[0057] R 1 -R 8 The remaining groups are each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl,

[0058] The substitution in the substituted C6-C30 arylene group, substituted C3-C30 heteroarylene group, substituted C6-C30 aryl group, substituted C3-C30 heteroaryl group, and substituted heteroaryl group having 2 or more N atoms means that one or more hydrogen atoms therein are independently replaced by one or more of deuterium, halogen, cyano, C1-C10 alkyl group, C3-C10 cycloalkyl group, C6-C30 aryl group, and C3-C30 heteroaryl group.

[0059] The substitution in the substituted C1-C10 alkyl group and the substituted C3-C10 cycloalkyl group means that one or more hydrogen atoms are replaced by deuterium.

[0060] Preferably, R 1 -R 8 One or both of them are selected from substituted or unsubstituted heteroaryl groups having 2 or more N atoms. More preferably, R 1 -R 8 The remaining groups are independently selected from hydrogen, deuterium, halogen, phenyl, and deuterated phenyl.

[0061] Preferably, R 1 -R 8 One or both of them are selected from substituted or unsubstituted heteroaryl groups having 2 or more N atoms. More preferably, R 1 -R 8 The remaining groups are independently selected from hydrogen and deuterium.

[0062] Preferably, R 1 -R 8One of them is selected from substituted or unsubstituted heteroaryl groups having 2 or more N atoms. More preferably, R 1 -R 8 The remaining groups are independently selected from hydrogen, deuterium, halogen, phenyl, and deuterated phenyl.

[0063] Preferably, R 1 -R 8 One of them is selected from substituted or unsubstituted heteroaryl groups having 2 or more N atoms. More preferably, R 1 -R 8 The remaining groups are independently selected from hydrogen and deuterium.

[0064] Preferably, the C1-C10 alkyl group is selected from methyl, ethyl, and tert-butyl.

[0065] Preferably, the C3-C10 cycloalkyl group is selected from cyclopropyl and cyclohexyl groups.

[0066] Preferably, the C6-C30 aryl group is selected from phenyl, naphthyl, anthracenyl, phenanthrenyl, fluoranthenyl, pyrene, triphenylene, biphenyl, terphenyl, phenyl-substituted naphthyl, naphthyl-substituted phenyl, and phenyl-substituted anthracenyl.

[0067] Preferably, the C3-C30 heteroaryl group is selected from pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, benzoquinolyl, benzoisoquinolyl, quinazolinyl, quinoxalinyl, naphthyridinyl, phenanthroline, benzimidazolyl, bipyridyl, terpyridyl, phenyl-substituted pyridyl, pyridyl-substituted phenyl, dibenzofuranyl, dibenzothiophenyl, benzonaphthofuranyl, and benzonaphthothiophenyl.

[0068] Preferably, the heteroaryl group having 2 or more N atoms is selected from a heteroaryl group having 2 N atoms.

[0069] Preferably, the heteroaryl group having 2 or more N atoms is selected from pyrimidinyl, pyrazinyl, pyridazinyl, quinazolinyl, quinoxalinyl, naphthyridinyl, phenanthroline, benzimidazolyl, and bipyridyl.

[0070] Preferably, the heteroaryl group having 2 or more N atoms is selected from phenanthroline.

[0071] Preferably, n1+n2+n3+n4+n5+n6+n7+n8=0.

[0072] Preferably, n1+n2+n3+n4+n5+n6+n7+n8=1.

[0073] Preferably, n1+n2+n3+n4+n5+n6+n7+n8=2.

[0074] Preferably, n1+n2+n3+n4+n5+n6+n7+n8=3.

[0075] Preferably, n1+n2+n3+n4+n5+n6+n7+n8=4.

[0076] In one embodiment, R 1 -R 8 One of them is selected from a substituted or unsubstituted heteroaryl group having 2 or more N atoms, wherein the heteroaryl group having 2 or more N atoms is selected from the following groups: pyrimidinyl, pyrazinyl, pyridazinyl, quinazolinyl, quinoxalinyl, naphthyridinyl, phenanthrolinyl, benzimidazolyl, bipyridyl, and the substituent of the substituted heteroaryl group having 2 or more N atoms refers to a combination in which one or more hydrogen atoms are independently selected from deuterium, halogen, cyano, phenyl, biphenyl, naphthyl, pyridinyl, phenyl-substituted naphthyl, naphthyl-substituted phenyl, and methyl;

[0077] n1+n2+n3+n4+n5+n6+n7+n8=an integer from 0 to 4, specifically 0, 1, 2, 3, 4;

[0078] L 1 -L 8 are each independently selected from a linking bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted anthrylene group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenylyl group, and a substituted or unsubstituted biphenyl group,

[0079] The substitution in the substituted phenylene, substituted naphthylene, substituted anthrylene, substituted phenanthrenyl, substituted pyrenylene, substituted dibenzofuranylene, substituted dibenzothiophenylene and substituted biphenylyl means that one or more hydrogen atoms therein are independently replaced by one or a combination of deuterium, halogen, cyano, phenyl, biphenylyl, naphthyl, anthryl and phenanthrenyl.

[0080] In one embodiment, R 1 -R 8 wherein two of them are selected from substituted or unsubstituted heteroaryl groups having 2 or more N atoms, wherein the heteroaryl groups having 2 or more N atoms are selected from the following groups: pyrimidinyl, pyrazinyl, pyridazinyl, quinazolinyl, quinoxalinyl, naphthyridinyl, phenanthrolinyl, benzimidazolyl, bipyridyl, and the substituent of the substituted heteroaryl groups having 2 or more N atoms refers to a combination in which one or more hydrogen atoms are independently selected from deuterium, halogen, cyano, phenyl, biphenyl, naphthyl, pyridinyl, phenyl-substituted naphthyl, naphthyl-substituted phenyl, and methyl;

[0081] n1+n2+n3+n4+n5+n6+n7+n8=an integer from 0 to 4, specifically 0, 1, 2, 3, 4;

[0082] L 1 -L 8 are each independently selected from a linking bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted anthrylene group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenylene group, and a substituted or unsubstituted biphenylene group,

[0083] The substitution in the substituted phenylene, substituted naphthylene, substituted anthrylene, substituted phenanthrenyl, substituted pyrenyl, substituted dibenzofuranyl, substituted dibenzothiophenylene, and substituted biphenylene means that one or more hydrogen atoms therein are independently replaced by one or a combination of deuterium, halogen, cyano, phenyl, biphenyl, naphthyl, anthryl, and phenanthrenyl.

[0084] In one embodiment, R 1 substituted or unsubstituted heteroaryl groups having 2 or more N atoms, wherein the heteroaryl groups having 2 or more N atoms are selected from the following groups: pyrimidinyl, pyrazinyl, pyridazinyl, quinazolinyl, quinoxalinyl, naphthyridinyl, phenanthrolinyl, benzimidazolyl, bipyridyl, and the substituent of the substituted heteroaryl groups having 2 or more N atoms refers to a combination in which one or more hydrogen atoms are independently selected from deuterium, halogen, cyano, phenyl, biphenyl, naphthyl, pyridinyl, phenyl-substituted naphthyl, naphthyl-substituted phenyl, and methyl;

[0085] n1 is selected from 0, 1 or 2;

[0086] n2+n3+n4+n5+n6+n7+n8=an integer from 0 to 2, specifically 0, 1, 2;

[0087] L 1 -L 8 are each independently selected from a linking bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted anthrylene group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenylyl group, and a substituted or unsubstituted biphenyl group,

[0088] The substitution in the substituted phenylene, substituted naphthylene, substituted anthrylene, substituted phenanthrenyl, substituted pyrenylene, substituted dibenzofuranylene, substituted dibenzothiophenylene and substituted biphenylyl means that one or more hydrogen atoms therein are independently replaced by one or a combination of deuterium, halogen, cyano, phenyl, biphenylyl, naphthyl, anthryl and phenanthrenyl.

[0089] Preferably, n2 is selected from 0, n3 is selected from 0, n4 is selected from 0, n5 is selected from 0, n6 is selected from 0, n7 is selected from 0, and n8 is selected from 0, 1 or 2.

[0090] Preferably, R 1 is selected from substituted or unsubstituted phenanthroline groups, wherein the substituents are selected from one or more combinations of deuterium, halogen, cyano, phenyl, biphenyl, naphthyl, pyridyl, phenyl-substituted naphthyl, naphthyl-substituted phenyl, and methyl. Preferably, R 2 -R 8 are each independently selected from hydrogen or deuterium.

[0091] In one embodiment, R 2 substituted or unsubstituted heteroaryl groups having 2 or more N atoms, wherein the heteroaryl groups having 2 or more N atoms are selected from the following groups: pyrimidinyl, pyrazinyl, pyridazinyl, quinazolinyl, quinoxalinyl, naphthyridinyl, phenanthrolinyl, benzimidazolyl, bipyridyl, and the substituent of the substituted heteroaryl groups having 2 or more N atoms refers to a combination in which one or more hydrogen atoms are independently selected from deuterium, halogen, cyano, phenyl, biphenyl, naphthyl, pyridinyl, phenyl-substituted naphthyl, naphthyl-substituted phenyl, and methyl;

[0092] n2 is selected from 0, 1 or 2, n1+n3+n4+n5+n6+n7+n8=an integer from 0 to 2,

[0093] L 1 -L 8 are each independently selected from a linking bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted anthrylene group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenylyl group, and a substituted or unsubstituted biphenyl group,

[0094] The substitution in the substituted phenylene, substituted naphthylene, substituted anthrylene, substituted phenanthrenyl, substituted pyrenylene, substituted dibenzofuranylene, substituted dibenzothiophenylene and substituted biphenylyl means that one or more hydrogen atoms therein are independently replaced by one or a combination of deuterium, halogen, cyano, phenyl, biphenylyl, naphthyl, anthryl and phenanthrenyl.

[0095] Preferably, n1 is selected from 0, n3 is selected from 0, n4 is selected from 0, n5 is selected from 0, n6 is selected from 0, n7 is selected from 0, and n8 is selected from 0.

[0096] Preferably, R 2is selected from substituted or unsubstituted phenanthroline groups, wherein the substituents are selected from one or more combinations of deuterium, halogen, cyano, phenyl, biphenyl, naphthyl, pyridyl, phenyl-substituted naphthyl, naphthyl-substituted phenyl, and methyl. Preferably, R 1 、R 3 -R 8 are each independently selected from hydrogen or deuterium.

[0097] In one embodiment, R 3 substituted or unsubstituted heteroaryl groups having 2 or more N atoms, wherein the heteroaryl groups having 2 or more N atoms are selected from the following groups: pyrimidinyl, pyrazinyl, pyridazinyl, quinazolinyl, quinoxalinyl, naphthyridinyl, phenanthrolinyl, benzimidazolyl, bipyridyl, and the substituent of the substituted heteroaryl groups having 2 or more N atoms refers to a combination in which one or more hydrogen atoms are independently selected from deuterium, halogen, cyano, phenyl, biphenyl, naphthyl, pyridinyl, phenyl-substituted naphthyl, naphthyl-substituted phenyl, and methyl;

[0098] n3 is selected from 0, 1 or 2, n2+n1+n4+n5+n6+n7+n8=an integer from 0 to 2,

[0099] L 1 -L 8 are each independently selected from a linking bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted anthrylene group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenylyl group, and a substituted or unsubstituted biphenyl group,

[0100] The substitution in the substituted phenylene, substituted naphthylene, substituted anthrylene, substituted phenanthrenyl, substituted pyrenylene, substituted dibenzofuranylene, substituted dibenzothiophenylene and substituted biphenylyl means that one or more hydrogen atoms therein are independently replaced by one or a combination of deuterium, halogen, cyano, phenyl, biphenylyl, naphthyl, anthryl and phenanthrenyl.

[0101] Preferably, n1 is selected from 0, n2 is selected from 0, n4 is selected from 0, n5 is selected from 0, n6 is selected from 0, n7 is selected from 0, and n8 is selected from 0.

[0102] Preferably, R 3 is selected from substituted or unsubstituted phenanthroline groups, wherein the substituents are selected from one or more combinations of deuterium, halogen, cyano, phenyl, biphenyl, naphthyl, pyridyl, phenyl-substituted naphthyl, naphthyl-substituted phenyl, and methyl. Preferably, R 1 -R 2 、R 4 -R 8 are each independently selected from hydrogen or deuterium.

[0103] In one embodiment, R 4 substituted or unsubstituted heteroaryl groups having 2 or more N atoms, wherein the heteroaryl groups having 2 or more N atoms are selected from the following groups: pyrimidinyl, pyrazinyl, pyridazinyl, quinazolinyl, quinoxalinyl, naphthyridinyl, phenanthrolinyl, benzimidazolyl, bipyridyl, and the substituent of the substituted heteroaryl groups having 2 or more N atoms refers to a combination in which one or more hydrogen atoms are independently selected from deuterium, halogen, cyano, phenyl, biphenyl, naphthyl, pyridinyl, phenyl-substituted naphthyl, naphthyl-substituted phenyl, and methyl;

[0104] n4 is selected from 0, 1 or 2, n2+n3+n1+n5+n6+n7+n8=an integer from 0 to 2,

[0105] L 1 -L 8 are each independently selected from a linking bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted anthrylene group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenylyl group, and a substituted or unsubstituted biphenyl group,

[0106] The substitution in the substituted phenylene, substituted naphthylene, substituted anthrylene, substituted phenanthrenyl, substituted pyrenylene, substituted dibenzofuranylene, substituted dibenzothiophenylene and substituted biphenylyl means that one or more hydrogen atoms therein are independently replaced by one or a combination of deuterium, halogen, cyano, phenyl, biphenylyl, naphthyl, anthryl and phenanthrenyl.

[0107] Preferably, n1 is selected from 0, n2 is selected from 0, n3 is selected from 0, n5 is selected from 0, n6 is selected from 0, n7 is selected from 0, and n8 is selected from 0.

[0108] Preferably, R 4 is selected from substituted or unsubstituted phenanthroline groups, wherein the substituents are selected from one or more combinations of deuterium, halogen, cyano, phenyl, biphenyl, naphthyl, pyridyl, phenyl-substituted naphthyl, naphthyl-substituted phenyl, and methyl. Preferably, R 1 -R 3 、R 5 -R 8 are each independently selected from hydrogen or deuterium.

[0109] In this application, multiple L 1 Same or different; multiple L 2 Same or different; multiple L 3 Same or different; multiple L 4 Same or different; multiple L 5 Same or different; multiple L 6 Same or different; multiple L7 Same or different; multiple L 8 The same or different. Multiple means greater than or equal to two.

[0110] The heterocyclic compound of the present invention, i.e. the compound of formula (1), is selected from any of the following compounds

[0111] Organic electroluminescent elements

[0112] The structure of the organic electroluminescent element of the present invention is a disclosed structure, comprising an anode, a cathode and an organic layer located between the anode and the cathode. The organic layer comprises a light-emitting layer, and at least one layer of the organic layer comprises the compound of the present invention.

[0113] The organic layer further includes one or more of a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer, and an electron injection layer, but is not limited thereto.

[0114] The light-emitting element of the present invention may emit fluorescence, phosphorescence, or a combination thereof. The light-emitting element may emit light alone or in the form of a series connection of multiple light-emitting units.

[0115] As simple light emitting elements, the following may be mentioned, but are not limited to these:

[0116] (1) hole transport layer / fluorescent light emitting layer / electron transport layer;

[0117] (2) hole transport layer / phosphorescent light emitting layer / electron transport layer;

[0118] (3) hole transport layer / first fluorescent light-emitting layer / second fluorescent light-emitting layer / electron transport layer;

[0119] (4) hole transport layer / first phosphorescent light-emitting layer / second phosphorescent light-emitting layer / electron transport layer;

[0120] (5) hole transport layer / fluorescent emitting layer / spacer layer / phosphorescent emitting layer / electron transport layer;

[0121] (6) hole transport layer / electron blocking layer / fluorescent light emitting layer / electron transport layer;

[0122] (7) hole transport layer / electron blocking layer / fluorescent light emitting layer / hole blocking layer / electron transport layer;

[0123] (8) hole transport layer / electron blocking layer / phosphorescent light emitting layer / electron transport layer;

[0124] (9) hole transport layer / electron blocking layer / phosphorescent light emitting layer / hole blocking layer / electron transport layer;

[0125] (10) hole injection layer / hole transport layer / phosphorescent light emitting layer / electron transport layer / electron injection layer;

[0126] (11) hole injection layer / hole transport layer / fluorescent light emitting layer / electron transport layer / electron injection layer;

[0127] (12) hole injection layer / hole transport layer / electron blocking layer / phosphorescent light emitting layer / electron transport layer / electron injection layer;

[0128] (13) hole injection layer / hole transport layer / electron blocking layer / fluorescent light emitting layer / electron transport layer / electron injection layer;

[0129] The phosphorescent / fluorescent light-emitting layers may each emit light of a different color.

[0130] As a tandem organic electroluminescent element, it can be an anode / first light-emitting unit / intermediate layer / second light-emitting unit / cathode. The intermediate layer can also generally be called a charge generation layer, an electron extraction layer, a connecting layer, etc. For example, when stacking a fluorescent light-emitting layer and a phosphorescent light-emitting layer, an intermediate layer is placed between the fluorescent light-emitting layer and the phosphorescent light-emitting layer in order to prevent the excitons generated by the phosphorescent light-emitting layer from diffusing to the fluorescent light-emitting layer or to adjust the balance of carriers.

[0131] When the organic light emitting element includes a plurality of organic material layers, the organic material layers may be formed of the same material or different materials.

[0132] The organic electroluminescent element of the present specification can be manufactured by using materials and methods known in the art, except that one or more of the organic material layers is prepared by using a compound comprising Formula I.

[0133] Anode materials may include materials with relatively large work functions, such as transparent conductive oxides, metals, and conductive polymers. Specific examples of anode materials include, but are not limited to, metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; and conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline.

[0134] Cathode materials typically use materials with a low work function to facilitate electron injection into the organic material layer. Examples of cathode materials include metals, metal oxides, and conductive polymers. Specific examples of cathode materials include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; and multilayered structures such as LiF / Al or LiO2 / Al.

[0135] The hole injection layer (HIL) injects holes from the electrodes and has the ability to transport them. To reduce the energy level difference between the electrodes, the HIL is primarily based on aromatic amine compounds. Other materials include copper phthalocyanine for metal complexes and HATCN (2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene) with a phenylene structure for the lowest unoccupied molecular orbital (LUMO) energy level. When used as a luminescent host and dopant, F4-TCNQ (2,2,3,5,6-tetrafluoro-7,7',8,8'-tetracyanodimethyl-p-benzoquinone) derivatives with the lowest unoccupied molecular orbital (LUMO) energy level can be doped into aromatic amine compounds.

[0136] The hole transport material is a layer that receives holes from the hole injection layer and transports the holes to the light-emitting layer. The hole transport material can appropriately receive holes from the anode or the hole injection layer and transfer the holes to the light-emitting layer. Aromatic amine derivatives, triphenyldiamine derivatives, etc. can be used, and low molecular weight or high molecular weight materials can also be used.

[0137] A luminescent material is a material that receives holes and electrons from the hole transport layer and electron transport layer, respectively, and combines the holes and electrons to emit light in the visible light region. The luminescent layer material includes a host material and a dopant material. Red, green, or blue luminescent materials can be used, and two or more luminescent materials can be mixed as needed. Both fluorescent and phosphorescent materials can be used as luminescent materials. The luminescent material can be a single-component material or a multi-component material.

[0138] The electron transport material is a layer that receives electrons from the electron injection layer and transports the electrons to the light-emitting layer, and the electron transport material can receive electrons from the cathode and transfer the electrons to the light-emitting layer. It is a material with high electron mobility. Triazine derivatives, oxadiazole derivatives, benzoquinone and its derivatives, naphthoquinone and its derivatives, anthraquinone and its derivatives, fluorenone derivatives, diphenyl dicyanoethylene and its derivatives, 8-hydroxyquinoline and its derivatives, etc. can be used. Metal complexes, and polymer materials and small molecule materials can also be used.

[0139] The electron injection layer is a layer that injects electrons from the electrode. This application uses LiF, however, this application is not limited thereto.

[0140] The hole blocking layer is a layer that blocks holes from reaching the cathode.

[0141] The electron blocking layer is a layer that blocks electrons from reaching the anode.

[0142] The organic light-emitting element of the present specification may be a top-emitting element, a bottom-emitting element, or a dual-emission element depending on the materials used.

[0143] The charge generation layer (CGL) is the intermediate layer between the anode and cathode in a tandem-structured device. It generates holes and electrons through charge separation. The CGL typically consists of a P-type layer on the cathode side and an N-type layer on the anode side, enabling efficient charge separation and carrier transport.

[0144] Those skilled in the art can refer to the synthesis of the following compounds and known synthesis methods to synthesize the compounds of the present invention. The compounds of the present invention can be prepared by coupling reactions. The following general formula is only one of the synthesis methods.

[0145] The following are specific examples of the synthesis of the compounds of the present invention, but are not limited to the compounds exemplified below. Synthesis Example 1: Synthesis of Compound 109

[0146] Under a nitrogen atmosphere, raw material 1 (7 g, 25.8 mmol), raw material 2 (10.8 g, 28.4 mmol), tetrakis(triphenylphosphine)palladium (Pd(PPh3)4, 0.59 g, 0.52 mmol), and potassium carbonate (7.1 g, 51.6 mmol) were added to 90 ml of tetrahydrofuran and 30 ml of water, and the temperature was raised to reflux for 6 hours. After completion of the reaction, the reaction solution was cooled to room temperature, extracted with dichloromethane, and dried over anhydrous sodium sulfate, and the solvent was removed. Compound 109 was purified by silica gel chromatography (developing solvent: dichloromethane) to obtain 9 g of compound 109, with a yield of 88%.

[0147] LC-MS (APCI): 447.37 (M+H + ).

[0148] 1 H NMR(400MHz,CD2Cl2)δ9.22(dd,1H),8.59–8.53(m,2H),8.42(d,1H),8.35–8.25(m,3H ),8.10(d,1H),8.01–7.95(m,3H),7.93–7.83(m,4H),7.79(d,1H),7.74–7.67(m,2H).

[0149] Synthesis Example 2: Synthesis of Compound 1

[0150] (1) Synthesis of intermediate 1-1

[0151] Under a nitrogen atmosphere, raw material 3 (50 g, 247.5 mmol), raw material 4 (55 g, 297 mmol), K2CO3 (68 g, 495 mmol), and Pd(PPh3)4 (5.7 g, 4.95 mmol) were placed in a four-necked reaction flask. 500 mL of toluene:ethanol:water (7:3:3 by volume) was added and heated to reflux. The reaction was complete after 3 h. After completion of the reaction, the product was extracted with ethyl acetate and purified by column chromatography (n-hexane:ethyl acetate, 20:1 by volume) to obtain 38 g of intermediate 1-1, with a yield of 58%.

[0152] LC-MS (APCI): 265.07 (M+H + ).

[0153] (2) Synthesis of Intermediate 2

[0154] Under a nitrogen atmosphere, intermediate 1-1 (38 g, 144 mmol), potassium carbonate (40 g, 288 mmol), and dimethyl (1-diazo-2-oxopropyl)phosphonate (41 g, 216 mmol) were placed in a three-necked flask. 1 L of anhydrous methanol was added and the reaction was allowed to react at room temperature. The reaction was monitored by TLC until the starting material was completely consumed (approximately 3 h). After the reaction was completed, water was added to quench the reaction, and the product was extracted three times with ethyl acetate. The organic phase was concentrated to dryness to obtain 35 g of intermediate 1-2 (oil), which was directly carried to the next step without further purification.

[0155] LC-MS (APCI): 261.12 (M+H + ).

[0156] (3) Synthesis of Intermediates 1-3

[0157] Under a nitrogen atmosphere, intermediate 1-2 (35 g, 134 mmol) and platinum dichloride (4.5 g, 13.4 mmol) were placed in a three-necked flask. 1 L of anhydrous toluene was added and the mixture was heated to reflux. The reaction was monitored by TLC until the starting material was completely consumed (approximately 13 h). After completion of the reaction, water was added to quench the reaction, and the product was extracted twice with ethyl acetate. Purification by column chromatography (n-hexane:ethyl acetate, volume ratio 50:1) afforded 10 g of intermediate 1-3, a 29% yield.

[0158] LC-MS (APCI): 261.15 (M+H + ).

[0159] (4) Synthesis of Intermediates 1-4

[0160] Under a nitrogen atmosphere, intermediate 1-3 (10 g, 38.3 mmol) was placed in a three-necked flask and added with 200 mL of anhydrous dichloromethane. The temperature was then cooled to -40°C, followed by the dropwise addition of boron tribromide (14 g, 57 mmol). After the addition was complete, the temperature was slowly raised to room temperature. The reaction was monitored by TLC until the starting material was completely consumed (approximately 4 h). After completion of the reaction, ice water was added to quench the reaction, and the product was extracted twice with ethyl acetate. Purification by column chromatography (n-hexane:ethyl acetate, volume ratio 20:1) afforded 8 g of intermediate 1-4, with a yield of 85%.

[0161] LC-MS (APCI): 247.11 (M+H + ).

[0162] (5) Synthesis of Intermediate 1-5

[0163] Under a nitrogen atmosphere, intermediate 1-4 (8 g, 32 mmol) and potassium carbonate (8.9 g, 65 mmol) were placed in a three-necked flask. 100 mL of N-methylpyrrolidone was added and the mixture was heated to 120°C. The reaction was monitored by TLC until the starting material was completely consumed (approximately 15 h). After completion of the reaction, water was added to quench the reaction, and the product was extracted three times with ethyl acetate. The product was then purified by column chromatography (pure hexane) to afford 6.5 g of intermediate 1-5, a 75% yield.

[0164] LC-MS (APCI): 227.25 (M+H + ).

[0165] (6) Synthesis of Compound 1

[0166] Under a nitrogen atmosphere, intermediate 1-5 (6.5 g, 26.4 mmol), raw material 2 (12 g, 31 mmol), K2CO3 (7.3 g, 52.8 mmol), Pd132 (dichlorodi-tert-butyl-(4-dimethylaminophenyl)phosphine palladium (II), 0.6 g, 0.79 mmol) were placed in a four-necked reaction flask, and 80 mL of toluene: ethanol: water (volume ratio 7:3:3) was added. The mixture was heated to reflux for reaction. The reaction was complete after 5 h. After the reaction, a large amount of solid was precipitated, which was then directly filtered to obtain 9.6 g of crude product. The product was then refluxed with ethyl acetate to obtain 8.3 g of compound 1, with a yield of 70%.

[0167] LC-MS (APCI): 447.27 (M+H + ).

[0168] 1 HNMR(400MHz,DMSO-d6)δ9.22(dd,1H),8.73(d,2H),8.66(d,1H),8.52(m,5H),8.42(d,2H),8.13(d,1H),8.03(m,3H),7.97(m,2H),7.83(dd,1H).

[0169] Synthesis Example 3: Synthesis of Compound 110

[0170] (1) Synthesis of Intermediate 110-1

[0171] Under nitrogen atmosphere, 6.77g of raw material 1, 7.61g of pinacol borate, 4.89g of potassium acetate, and 0.35g of bistriphenylphosphine palladium dichloride were added to a four-necked reaction flask, and 140ml of 1,4-dioxane was added and heated to 90°C. After 2 hours of reaction, TLC detection showed that the raw material reaction was complete. Water was added to quench the reaction, and dichloromethane was added to extract the reaction. The product was separated and purified by chromatography using an eluent of ethyl acetate: n-hexane in a volume ratio of 1:1. 6.94g of the product was obtained with a yield of 87.4%.

[0172] LC-MS (APCI): 319.18 (M+H + ).Calcd for C 20 H 19 Bo3

[0173] (2) Synthesis of Compound 110

[0174] Under nitrogen atmosphere, 6.65g of intermediate 110-1, 8.04g of 2-(4-bromo-1-naphthyl)-1,10-phenanthroline, 1.76g of potassium carbonate, and 0.93g of bistriphenylphosphine palladium dichloride were added to a four-necked reaction flask. 170ml of tetrahydrofuran and 55ml of water were then added. The temperature was raised to 75°C for reaction. After the reaction, 7.89g of the product was obtained by direct filtration, with a yield of 76.1%.

[0175] LC-MS (APCI): 497.42 (M+H + ).Calcd for C 36 H 20 N2O

[0176] 1 H NMR(400MHz,CD2Cl2)δ9.09–9.08(d,1H),8.39–8.37(d,1H),8.26–8.18(d,2H),8.08(s,1H),7.99–7.9 7(d,1H),7.88–7.80(m,5H),7.75–7.70(m,2H),7.68–7.57(m,4H),7.43–7.37(m,2H),7.30–7.26(m,1H)

[0177] Synthesis Example 4: Synthesis of Compound 112

[0178] Under a nitrogen atmosphere, raw material 1 (13.5 g, 0.0498 mol), raw material 6 (23.97 g, 0.0523 mol), tetrakis(triphenylphosphine)palladium (0.58 g, 0.5 mmol) and potassium carbonate (13.74 g, 0.0996 mol) were added to 360 ml of tetrahydrofuran and 120 ml of water and refluxed for 3 hours. The reaction solution was cooled to room temperature and filtered to obtain a crude solid. The solid was slurried with tetrahydrofuran. 22.1 g of white solid compound 112 was obtained with a yield of 83%.

[0179] MS (APCI): 523.40 (M+H + ).Calcd for C 38 H 22 N2O.

[0180] 1 H NMR(400MHz,CD2Cl2)δ8.71–8.65(m,2H),8.50–8.45(m,2H),8.40(dd,2H),8.31(d,1H),8.22–8.1 5(m,2H),8.06(dd,3H),7.94(d,1H),7.91–7.85(m,3H),7.72(dd,2H),7.62(dd,2H),7.51(t,2H).

[0181] Synthesis Example 5 Synthesis of Compound 115

[0182] (1) Synthesis of Intermediate 115-1

[0183] Under a nitrogen atmosphere, 1,6-dibromopyrene (57.6 g, 160.0 mmol), pinacol diboron (101.2 g, 400.0 mmol), 1,1'-bis(diphenylphosphinoferrocenepalladium) dichloride (3.51 g, 4.8 mmol), and potassium acetate (78.4 g, 800.0 mmol) were added to 750 ml of 1,4-dioxane and heated to reflux for 4 hours. After completion of the reaction, the reaction solution was cooled to room temperature, extracted with dichloromethane, dried over anhydrous sodium sulfate, and the solvent was removed. Purification by silica gel chromatography (developing solvent: n-hexane:ethyl acetate = 9:1 by volume) afforded Intermediate 115-1 (57.0 g, 78.5% yield).

[0184] LC-MS (APCI): 455.53 (M+H + ).Calcd for C 28 H 32 B2O4

[0185] (2) Synthesis of Intermediate 115-2

[0186] Under a nitrogen atmosphere, Intermediate 115-1 (30.0 g, 66.0 mmol), 2-bromo-1,10-phenanthroline (17.0 g, 66.0 mmol), tetrakistriphenylphosphine palladium (1.14 g, 0.99 mmol), and potassium carbonate (18.2 g, 132.0 mmol) were added to 350 ml of toluene, 150 ml of ethanol, and 150 ml of water. The mixture was heated to reflux and reacted for 4 hours. After completion of the reaction, the reaction solution was cooled to room temperature, extracted with dichloromethane, dried over anhydrous sodium sulfate, and the solvent was removed. Purification by silica gel chromatography (developing solvent: n-hexane:ethyl acetate = 1:1) afforded Intermediate 115-2 (16.0 g, 48.0% yield).

[0187] LC-MS (APCI): 507.47 (M+H + ).Calcd for C 34 H 27 BN2O2

[0188] (3) Synthesis of Compound 115

[0189] Under a nitrogen atmosphere, intermediate 115-2 (10.7 g, 21.1 mmol), starting material 1 (6.0 g, 22.2 mmol), tetrakis(triphenylphosphine)palladium (1.2 g, 1.0 mmol), and potassium carbonate (5.8 g, 42.2 mmol) were added to 210 ml of tetrahydrofuran and 70 ml of water, and the mixture was heated to reflux for 3 hours. After completion of the reaction, the reaction solution was cooled to room temperature, extracted with dichloromethane, dried over anhydrous sodium sulfate, and the solvent was removed. Purification by silica gel chromatography (developing solvent: tetrahydrofuran:dichloromethane = volume ratio 1:10) gave compound 115 (7.0 g, yield 58.3%).

[0190] LC-MS (APCI): 571.48 (M+H + ).Calcd for C 42 H 22 N2O

[0191] 1 H NMR(400MHz,Methylene Chloride-d2)δ9.18(dd,1H),8.60(d,1H),8.52(d,1H),8.46–8.31(m,4H),8.30–8 .20(m,3H),8.15(d,1H),8.10–7.88(m,6H),7.82–7.64(m,4H),7.48–7.39(m,1H).

[0192] The following application examples further illustrate the application of the heterocyclic compound of the present invention and the organic electroluminescent device containing the heterocyclic compound.

[0193] Application Example 1

[0194] This embodiment provides an organic electroluminescent element, as shown in Figure 1, including a stacked first electrode layer 1, a hole injection layer 2, a hole transport layer 3, a light-emitting layer 4, an electron transport layer 5, an N-type charge generation layer 6, a P-type charge generation layer 7, a hole transport layer 8, a light-emitting layer 9, an electron transport layer 10, an electron injection layer 11 and a second electrode layer 12, wherein 100 is a first light-emitting unit and 200 is a second light-emitting unit.

[0195] The specific component structure is:

[0196] ITO(100nm) / NPD:F4-TCNQ(10%)(10nm) / NPD(120nm) / BH:BD(3%)(20nm) / TmPyPB(10nm) / Bphen:Li(2%)( 10nm) / NPD:F4-TCNQ(10%)(20nm) / NPD(20nm) / BH:BD(3%)(20nm) / Alq3(10nm) / LiF(0.5nm) / Al(200nm).

[0197] Component preparation process:

[0198] The bottom-emitting glass substrate used in this example was purchased from Guangdong Truly Display Technology Co., Ltd., and 100 nm ITO was used as the first electrode layer 1. First, the bottom-emitting glass substrate was cleaned using an ITO cleaner, deionized water, and isopropyl alcohol, in that order. The bottom-emitting glass substrate was then baked at 180 degrees Celsius for 30 minutes to dry it.

[0199] Then put the bottom luminescent glass substrate into the evaporation chamber and -8Each organic layer is deposited on the ITO anode in sequence by thermal vacuum evaporation at a rate of 0.2-2 angstroms / second under the condition of torr. Among them, F4-TCNQ (mass content 10%) is doped into NPD to form a thickness of 10nm as a hole injection layer. NPD is formed to a thickness of 120nm as a hole transport layer, and a pyrene dopant 1,6-bis(diphenylamino)pyrene with a mass content of 3% is doped on the anthracene host ADN (9,10-di(naphtha-2-yl-)anthracene) to form a blue light-emitting layer with a thickness of 20nm. TmPyPB is formed to a thickness of 10nm as the first electron transport layer, and BPhen (4,7-Diphenyl-1,10-phenanthroline) is doped with 2% Li by mass to form an N-type charge generation layer 6 with a thickness of 10nm. F4-TCNQ with a mass content of 10% is doped on NPD. A P-type charge generation layer with a thickness of 20 nm is formed, NPD is formed with a thickness of 20 nm as a hole transport layer, the anthracene main body ADN (9,10-di(naphtha-2-yl-)anthracene) is doped with a pyrene dopant 1,6-bis(diphenylamino)pyrene with a mass content of 3% to form a blue light-emitting layer with a thickness of 20 nm, Alq3 (Tris-(8-hydroxyquinolinato)aluminum) is formed with a thickness of 10 nm as a second electron transport layer, LiF is formed with a thickness of 0.5 nm as an electron injection layer, and Al is formed with a thickness of 200 nm as a cathode.

[0200] Finally, the component was transferred back to the glove box and encapsulated with a glass cover and a moisture absorbent to complete the component, which was recorded as organic electronic component 1.

[0201] Contrast structure

[0202] Bphen(4,7-Diphenyl-1,10-phenanthroline)

[0203] Examples and Comparative Examples

[0204] The charge generation layer 6 is prepared by using the compound prepared in Example 1 of the present invention instead of the Bphen material. The organic electronic element 2 is prepared using the same method.

[0205] The charge generation layer 6 is prepared by using the compound prepared in Example 2 of the present invention instead of the Bphen material, and the organic electronic element 3 is prepared using the same method.

[0206] The charge generation layer 6 is prepared by using the compound prepared in Example 3 of the present invention instead of the Bphen material, and the organic electronic element 4 is prepared using the same method.

[0207] The charge generation layer 6 is prepared by using the compound prepared in Example 4 of the present invention instead of the Bphen material, and the organic electronic element 5 is prepared by the same method.

[0208] The charge generation layer 6 is prepared by using the compound prepared in Example 5 of the present invention instead of the Bphen material, and the organic electronic element 6 is prepared by the same method.

[0209] Life test method: Apply voltage to the obtained organic electroluminescent element so that the current density reaches 30mA / cm 2 The time until the brightness reaches 95% of the initial brightness (LT95 (unit: hour)) was measured.

[0210] The driving voltage is at a current density of 15 mA / cm 2 The following test results are shown in Table 1.

[0211] Table 1

[0212] The organic electroluminescent element prepared from the compound of the present invention has a lower driving voltage and a longer service life than the organic electroluminescent element prepared from BPHEN, and therefore is suitable as a material for an organic electroluminescent element.

[0213] The various embodiments in this specification are described in a progressive manner, with each embodiment focusing on its differences from the other embodiments. Reference can be made to the descriptions of the identical or similar parts between the various embodiments. For the devices disclosed in the embodiments, since they correspond to the methods disclosed in the embodiments, the descriptions are relatively simple, and the relevant parts can be referred to the descriptions of the methods.

[0214] The above is a detailed introduction to a heterocyclic compound provided by the present invention and an organic electroluminescent element containing the same. Specific examples are used herein to illustrate the principles and implementation methods of the present invention. The description of the above embodiments is only used to help understand the method of the present invention and its core idea. It should be pointed out that for ordinary technicians in this technical field, without departing from the principles of the present invention, the present invention can also be improved and modified in several ways, and these improvements and modifications also fall within the scope of protection of the claims of the present invention.

Claims

1. A heterocyclic compound, characterized in that The compound has the structure shown in formula (1): in X 1 Selected from O or S, L 1 -L 8 are each independently selected from a linking bond, a substituted or unsubstituted C6-C30 arylene group, and a substituted or unsubstituted C3-C30 heteroarylene group, n1 is selected from 0, 1, 2, 3, n2 is selected from 0, 1, 2, 3, n3 is selected from 0, 1, 2, 3, n4 is selected from 0, 1, 2, 3, n5 is selected from 0, 1, 2, 3, n6 is selected from 0, 1, 2, 3, n7 is selected from 0, 1, 2, 3, n8 is selected from 0, 1, 2, 3, R 1 -R 8 At least one of them is selected from substituted or unsubstituted heteroaryl groups having 2 or more N atoms, R 1 -R 8 The remaining groups are each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, The substitution in the substituted C6-C30 arylene group, substituted C3-C30 heteroarylene group, substituted C6-C30 aryl group, substituted C3-C30 heteroaryl group, and substituted heteroaryl group having 2 or more N atoms means that one or more hydrogen atoms therein are independently replaced by a combination of one or more of deuterium, halogen, cyano, C1-C10 alkyl group, C3-C10 cycloalkyl group, C6-C30 aryl group, and C3-C30 heteroaryl group, The substitution in the substituted C1-C10 alkyl and substituted C3-C10 cycloalkyl means that one or more hydrogen atoms are replaced by deuterium.

2. The heterocyclic compound according to claim 1, characterized in that R 1 -R 8 One or both are selected from substituted or unsubstituted heteroaryl groups having 2 or more N atoms.

3. The heterocyclic compound according to claim 1, characterized in that The heteroaryl group having 2 or more N atoms is selected from pyrimidinyl, pyrazinyl, pyridazinyl, quinazolinyl, quinoxalinyl, naphthyridinyl, phenanthroline, benzimidazolyl, and bipyridine.

4. The heterocyclic compound according to claim 1, wherein L 1 -L 8 Each independently selected from a linking bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted anthrylene group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, and a substituted or unsubstituted biphenyl group, The substitution in the substituted phenylene, substituted naphthylene, substituted anthrylene, substituted phenanthrylene, substituted pyrene, substituted dibenzofuranylene, substituted dibenzothiophenylene and substituted biphenylyl means that one or more hydrogen therein is independently replaced by one or a combination of deuterium, halogen, cyano, phenyl, biphenylyl, naphthyl, anthracenyl and phenanthryl.

5. The heterocyclic compound according to claim 1, characterized in that The C1-C10 alkyl group is selected from methyl, ethyl, and tert-butyl; The C3-C10 cycloalkyl group is selected from cyclopropane and cyclohexane; The C6-C30 aryl group is selected from phenyl, naphthyl, anthracenyl, phenanthrenyl, fluoranthenyl, pyrene, triphenylene, biphenyl, terphenyl, phenyl-substituted naphthyl, naphthyl-substituted phenyl, phenyl-substituted anthracenyl; The C3-C30 heteroaryl group is selected from pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, benzoquinolyl, benzoisoquinolyl, quinazolinyl, quinoxalinyl, naphthyridinyl, phenanthrolinyl, benzimidazolyl, bipyridyl, terpyridyl, phenyl-substituted pyridyl, pyridyl-substituted phenyl, dibenzofuranyl, dibenzothiophenyl, benzonaphthofuranyl, and benzonaphthothiophenyl.

6. The heterocyclic compound according to claim 1, characterized in that Formula (1) is selected from any of the following compounds 7. Use of the heterocyclic compound according to any one of claims 1 to 6 as an organic electroluminescent element material. 8 . An organic electroluminescent element comprising an anode, a cathode, and an organic layer located between the anode and the cathode, wherein the organic layer comprises the heterocyclic compound according to claim 1 . 9 . The organic electroluminescent element according to claim 8 , wherein the organic layer comprises an electron transport layer and a light emitting layer, and the electron transport layer comprises the heterocyclic compound according to claim 1 .

10. The organic electroluminescent element according to claim 8, wherein the organic layer comprises two or more light-emitting units, a charge generation layer is included between the light-emitting units, and the light-emitting units comprise an electron transport layer, characterized in that At least one of the charge generation layer and the electron transport layer comprises the heterocyclic compound according to any one of claims 1 to 6.

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