Heterocyclic compound and organic electroluminescent element comprising same

Abstract

The invention belongs to the technical field of photoelectric materials, and provides a heterocyclic compound and an organic electroluminescent element comprising the same. A heterocyclic compound having a structure # imgabs0 # represented by formula (1) wherein X1 is selected from O or S, and L1-L8 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. The organic electroluminescent element prepared by using the compound can realize reduced driving voltage and durable service life. The organic electroluminescent element has better performance.

Description

Technical Field

[0001] The invention belongs to the technical field of optoelectronic materials, and particularly relates to a heterocyclic compound and an organic electroluminescent element containing the heterocyclic compound. Background Art

[0002] 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 source and is thin, making it a technology suitable for flexible element devices (flexible light-emitting display devices).

[0003] The organic light-emitting device has an anode and a cathode, and a structure in which an organic thin film is placed between the two electrodes. It can be a simple element including a single light-emitting unit or a tandem element including multiple light-emitting units.

[0004] Simple components usually include a hole transport layer, a light-emitting layer, and an electron transport layer. Since the electron mobility of the electron transport layer material is much lower than the hole mobility of the hole transport layer material, the holes and electrons entering the light-emitting layer are unbalanced, affecting the light-emitting efficiency and life of the component.

[0005] A series element usually has a charge generation layer between the light-emitting units to ensure that the charge is effectively distributed to the light-emitting stack while improving the current efficiency in each light-emitting layer. Usually, the charge generation layer has a PN junction in which an N-type charge generation layer and a P-type charge generation layer are stacked in sequence.

[0006] 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 can easily cause degradation of the interface and shorten the life of the component.

[0007] Therefore, there is an urgent need to develop new materials to increase the life of components. Summary of the invention

[0008] The object of the present invention is to provide a heterocyclic compound, the organic electroluminescent element prepared by using the compound can achieve a reduced driving voltage and a durable service life.

[0009] The technical solution adopted by the present invention to solve its technical problem is:

[0010] A heterocyclic compound having a structure shown in formula (1)

[0011] in

[0012] X 1 Selected from O or S,

[0013] 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,

[0014] 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,

[0015] R 1 -R 8 At least one of them is selected from substituted or unsubstituted heteroaryl groups having 2 or more N atoms,

[0016] 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,

[0017] 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,

[0018] The substitution in the substituted C1-C10 alkyl and substituted C3-C10 cycloalkyl means that one or more hydrogen atoms are replaced by deuterium.

[0019] A use of the heterocyclic compound of the present invention as an organic electroluminescent element material.

[0020] 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.

[0021] 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.

[0022] Preferably, the organic layer comprises more than or equal to two light-emitting units, a charge generation layer is comprised 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.

[0023] Preferably, the organic layer comprises more than or equal to two light-emitting units, a charge generation layer is comprised between the light-emitting units, the light-emitting units comprise an electron transport layer, the charge generation layer comprises 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 comprises the heterocyclic compound described in the present invention.

[0024] 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 described in the present invention, which means that one N-type charge generation layer comprises the heterocyclic compound described in the present invention; or multiple N-type charge generation layers comprise the heterocyclic compound described in the present invention; or one electron transport layer in one light-emitting unit comprises the heterocyclic compound described in the present invention; or one N-type charge generation layer and one electron transport layer in one light-emitting unit comprise the heterocyclic compound described in the present invention; or one N-type charge generation layer and each electron transport layer in multiple light-emitting units comprise the heterocyclic compound described in the present invention; or multiple N-type charge generation layers and each electron transport layer in multiple light-emitting units comprise the heterocyclic compound described in the present invention, etc. When two or more layers comprise the heterocyclic compound described in the present invention, the heterocyclic compounds are the same or different.

[0025] 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.

[0026] Compared with the prior art, the present invention has the following beneficial effects:

[0027] 1. The organic electroluminescent compound of the present invention has a phenanthrofuran / thiophene structure, which improves the electron injection and transmission capabilities;

[0028] The organic electroluminescent element prepared using the compound can achieve reduced driving voltage and durable service life.

[0029] 2. Organic electroluminescent elements have a better lifespan. BRIEF DESCRIPTION OF THE DRAWINGS

[0030] Figure 1It is a schematic diagram of the structure 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

[0031] It should be noted that the following detailed descriptions are illustrative and are intended to provide further explanation of the present application. Unless otherwise specified, all technical and scientific terms used herein have the same meanings as those commonly understood by those skilled in the art to which the present application belongs.

[0032] 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 also intended to include the plural form. In addition, it should be understood that when the terms "include" and / or "include" are used in this specification, they indicate that they are not limited to the contents disclosed in this specification.

[0033] The present invention is now further described in conjunction with specific examples. The following examples are only for explaining the present invention, but do not constitute a limitation of the present invention. The test samples and test processes used in the following examples include the following (if the specific experimental conditions are not indicated in the examples, they are usually in accordance with conventional conditions or the conditions recommended by the reagent company; the reagents, consumables, etc. used in the following examples, if not otherwise specified, can all be obtained from commercial channels).

[0034] 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 viewpoints of the present invention to those skilled in the art.

[0035] As used herein, the term "halogen" may include fluorine, chlorine, bromine or iodine.

[0036] As used in the present invention, 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.

[0037] As used in the present invention, 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 include, but are not limited to, cyclopropane, cyclobutane, cyclopentane, cyclohexane, norbornyl, adamantane, and the like.

[0038] As used in the present invention, the term "C6-C30 aryl" refers to a monovalent substituent derived from an aromatic hydrocarbon having a monocyclic ring 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 this aryl 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.

[0039] As used herein, the term "arylene group" refers to a divalent aromatic group derived from an "aryl group" by removing a hydrogen atom. For example, a phenyl group is substituted by removing a hydrogen atom to form a phenylene group, and a naphthyl group is substituted by removing a hydrogen atom to form a naphthylene group.

[0040] As used in the present invention, the term "C3-C30 heteroaryl group" refers to a monovalent substituent derived from a monocyclic heterocyclic or polycyclic aromatic hydrocarbon having 3 to 30 carbon atoms. In this connection, at least one carbon, preferably 1 to 3 carbons in the ring are substituted with a heteroatom such as N, O, S, P, B or Si. In addition, this heteroaryl group may have a form in which two or more rings are simply lateral to each other or fused to each other or fused 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.

[0041] As used in the present invention, the term "heteroarylene" refers to a divalent heteroaryl group derived from a "heteroaryl" by removing a hydrogen atom. For example, a pyridyl group is derived from a pyridylene group by removing a hydrogen atom.

[0042] As used in the present invention, the "carbon number is AA-BB" in the expression "Z group having carbon atoms AA-BB" or "Z group having C(AA-BB)" means the carbon number of 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.

[0043] 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 the possible substitutions. For example, carbazolyl includes any of the following groups, but is not limited thereto, unless otherwise specified in this specification,

[0044]

[0045] Indicates the position of substitution. "Unsubstituted" means that hydrogen atoms remain, in this case, hydrogen atoms include protium, deuterium, tritium.

[0046] When two or more substituents are present, the two or more substituents may be the same or different.

[0047] As used in the present invention, hydrogen atoms include protium, deuterium and tritium. The compounds of the present invention may contain deuterium atoms of natural origin, or may introduce deuterium atoms 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 may be less than 100%, or less than 95%, or less than 90%, or less than 80%, and the deuteration rate may also be more than 1%, or more than 5%, or more than 10%. If the deuteration rate is not 100%, it means a mixture of deuterated compounds and undeuterated compounds, or a mixture of completely deuterated compounds and incompletely deuterated compounds, or a mixture of completely deuterated compounds and undeuterated compounds and incompletely deuterated compounds.

[0048] As used in the present invention, terms such as first, second, A, B, etc. 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.

[0049] The core of the present invention is a heterocyclic compound having the structure shown in formula (1):

[0050]

[0051] X 1 Selected from O or S,

[0052] 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,

[0053] 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,

[0054] R 1 -R 8 At least one of them is selected from substituted or unsubstituted heteroaryl groups having 2 or more N atoms,

[0055] 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,

[0056] 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,

[0057] The substitution in the substituted C1-C10 alkyl and substituted C3-C10 cycloalkyl means that one or more hydrogen atoms are replaced by deuterium.

[0058] 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 in are each independently selected from hydrogen, deuterium, halogen, phenyl, and deuterated phenyl.

[0059] 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 -R8 The remaining groups are independently selected from hydrogen and deuterium.

[0060] Preferably, R 1 -R 8 One of them is selected from a substituted or unsubstituted heteroaryl group having a nitrogen atom number greater than or equal to 2. More preferably, R 1 -R 8 The remaining groups in are each independently selected from hydrogen, deuterium, halogen, phenyl, and deuterated phenyl.

[0061] Preferably, R 1 -R 8 One of them is selected from a substituted or unsubstituted heteroaryl group having a nitrogen atom number greater than or equal to 2. More preferably, R 1 -R 8 The remaining groups are independently selected from hydrogen and deuterium.

[0062] Preferably, the C1-C10 alkyl group is selected from methyl, ethyl and tert-butyl.

[0063] Preferably, the C3-C10 cycloalkyl group is selected from cyclopropane and cyclohexane.

[0064] Preferably, the C6-C30 aryl group is selected from phenyl, naphthyl, anthracenyl, phenanthryl, fluoranthenyl, pyrene, triphenylene, biphenyl, terphenyl, phenyl-substituted naphthyl, naphthyl-substituted phenyl, and phenyl-substituted anthracenyl.

[0065] 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.

[0066] Preferably, the heteroaryl group having 2 or more N atoms is selected from the heteroaryl group having 2 N atoms.

[0067] Preferably, the heteroaryl group having 2 or more N atoms is selected from pyrimidinyl, pyrazinyl, pyridazinyl, quinazolinyl, quinoxalinyl, naphthyridinyl, phenanthroline, benzimidazolyl, and bipyridyl.

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

[0069] Preferably, n1+n2+n3+n4+n5+n6+n7+n8=0.

[0070] Preferably, n1+n2+n3+n4+n5+n6+n7+n8=1.

[0071] Preferably, n1+n2+n3+n4+n5+n6+n7+n8=2.

[0072] Preferably, n1+n2+n3+n4+n5+n6+n7+n8=3.

[0073] Preferably, n1+n2+n3+n4+n5+n6+n7+n8=4.

[0074] 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, phenanthroline, 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;

[0075] n1+n2+n3+n4+n5+n6+n7+n8=an integer from 0 to 4, specifically 0, 1, 2, 3, 4;

[0076] 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,

[0077] 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.

[0078] In one embodiment, R 1 -R 8 wherein two of them are selected from substituted or unsubstituted heteroaryl groups with N atoms greater than or equal to 2, wherein the heteroaryl groups with N atoms greater than or equal to 2 are selected from the following groups: pyrimidinyl, pyrazinyl, pyridazinyl, quinazolinyl, quinoxalinyl, naphthyridinyl, phenanthroline, benzimidazolyl, bipyridyl, and the substituent of the substituted heteroaryl groups with N atoms greater than or equal to 2 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;

[0079] n1+n2+n3+n4+n5+n6+n7+n8=an integer from 0 to 4, specifically 0, 1, 2, 3, 4;

[0080] 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, a substituted or unsubstituted biphenylene group,

[0081] The substitution in the substituted phenylene, substituted naphthylene, substituted anthrylene, substituted phenanthrenyl, substituted pyrenyl, substituted dibenzofuranyl, substituted dibenzothienyl, and substituted biphenylene means that one or more hydrogen therein is independently replaced by one or a combination of deuterium, halogen, cyano, phenyl, biphenyl, naphthyl, anthracenyl, and phenanthryl.

[0082] In one embodiment, R 1 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, phenanthroline, 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;

[0083] n1 is selected from 0, 1 or 2;

[0084] n2+n3+n4+n5+n6+n7+n8=an integer from 0 to 2, specifically 0, 1, 2;

[0085] 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,

[0086] 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.

[0087] 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.

[0088] Preferably, R 1 is selected from substituted or unsubstituted phenanthroline, wherein the substituent is 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.

[0089] In one embodiment, R 2 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, phenanthroline, 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;

[0090] n2 is selected from 0, 1 or 2, n1+n3+n4+n5+n6+n7+n8=an integer from 0 to 2,

[0091] 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,

[0092] 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.

[0093] 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.

[0094] Preferably, R 2 is selected from substituted or unsubstituted phenanthroline, wherein the substituent is 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.

[0095] In one embodiment, R 3 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, phenanthroline, 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;

[0096] n3 is selected from 0, 1 or 2, n2+n1+n4+n5+n6+n7+n8=an integer from 0 to 2,

[0097] 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,

[0098] 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.

[0099] 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.

[0100] Preferably, R 3 is selected from substituted or unsubstituted phenanthroline, wherein the substituent is selected from one or more combinations of deuterium, halogen, cyano, phenyl, biphenyl, naphthyl, pyridyl, phenyl substituted naphthyl, naphthyl substituted phenyl, and methyl. Preferably, R1 -R 2 , R 4 -R 8 are each independently selected from hydrogen or deuterium.

[0101] In one embodiment, R 4 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, phenanthroline, 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;

[0102] n4 is selected from 0, 1 or 2, n2+n3+n1+n5+n6+n7+n8=an integer from 0 to 2,

[0103] 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,

[0104] 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.

[0105] 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.

[0106] Preferably, R 4 is selected from substituted or unsubstituted phenanthroline, wherein the substituent is 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.

[0107] In this application, multiple L 1 Same or different; multiple L 2 Same or different; multiple L3 Same or different; multiple L 4 Same or different; multiple L 5 Same or different; multiple L 6 Same or different; multiple L 7 Same or different; multiple L 8 The same or different. Multiple means greater than or equal to two.

[0108] The heterocyclic compound of the present invention, i.e. the compound of formula (1), is selected from any of the following compounds

[0109]

[0110]

[0111]

[0112]

[0113]

[0114]

[0115]

[0116]

[0117]

[0118]

[0119] Organic electroluminescent element

[0120] 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, wherein the organic layer comprises a light-emitting layer, and at least one layer of the organic layer comprises the compound of the present invention.

[0121] The organic layer may further include 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.

[0122] The light-emitting element of the present invention may emit fluorescence or phosphorescence or a combination thereof. The light-emitting element may emit light alone or in series with multiple light-emitting units.

[0123] As simple light emitting elements, the following may be cited, but are not limited thereto:

[0124] (1) hole transport layer / fluorescent light emitting layer / electron transport layer;

[0125] (2) hole transport layer / phosphorescent light emitting layer / electron transport layer;

[0126] (3) hole transport layer / first fluorescent light-emitting layer / second fluorescent light-emitting layer / electron transport layer;

[0127] (4) hole transport layer / first phosphorescent light-emitting layer / second phosphorescent light-emitting layer / electron transport layer;

[0128] (5) hole transport layer / fluorescent emitting layer / spacer layer / phosphorescent emitting layer / electron transport layer;

[0129] (6) hole transport layer / electron blocking layer / fluorescent light emitting layer / electron transport layer;

[0130] (7) hole transport layer / electron blocking layer / fluorescent light emitting layer / hole blocking layer / electron transport layer;

[0131] (8) hole transport layer / electron blocking layer / phosphorescent light emitting layer / electron transport layer;

[0132] (9) hole transport layer / electron blocking layer / phosphorescent emitting layer / hole blocking layer / electron transport layer;

[0133] (10) hole injection layer / hole transport layer / phosphorescent light emitting layer / electron transport layer / electron injection layer;

[0134] (11) hole injection layer / hole transport layer / fluorescent light emitting layer / electron transport layer / electron injection layer;

[0135] (12) hole injection layer / hole transport layer / electron blocking layer / phosphorescent light emitting layer / electron transport layer / electron injection layer;

[0136] (13) hole injection layer / hole transport layer / electron blocking layer / fluorescent light emitting layer / electron transport layer / electron injection layer;

[0137] The phosphorescent / fluorescent light-emitting layers mentioned above can each emit light of a different color.

[0138] As a tandem type organic electroluminescent element, it can be an anode / first light-emitting unit / intermediate layer / second light-emitting unit / cathode. The intermediate layer can also be generally 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.

[0139] 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.

[0140] 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.

[0141] As the anode material, a material having a relatively large work function may be used, and a transparent conductive oxide, a metal, a conductive polymer, etc. may be used. Specific examples of the anode material include: 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; conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline, etc., but are not limited thereto.

[0142] As the cathode material, a material with a low work function is generally used to facilitate electron injection into the organic material layer, and metals, metal oxides, conductive polymers, etc. can be used. Specific examples of cathode materials include: metals, such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof; multilayer structure materials, such as LiF / Al or LiO2 / Al, etc., but are not limited thereto.

[0143] The hole injection layer is a layer that injects holes from the electrode and has the ability to transport holes. In order to reduce the energy level difference between the electrodes, the hole injection layer is mainly prepared based on aromatic amine compounds, and can also be prepared using the following materials, such as copper phthalocyanine in the metal complex, and HATCN (2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene) with a phenylene structure in the material with the lowest unoccupied molecular orbital energy level. When used as a light-emitting host and dopant, F4-TCNQ (2 2,3,5,6-tetrafluoro-7,7',8,8'-tetracyanodimethyl-p-benzoquinone) inducer with the lowest unoccupied molecular orbital energy level can be doped in the aromatic amine compound.

[0144] The hole transport material is a layer that receives holes from the hole injection layer and transports the holes to the light-emitting layer, and 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 or high molecular materials can also be used.

[0145] The luminescent material is a material that receives holes and electrons from the hole transport layer and the 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 doping material. Red, green or blue luminescent materials can be used, and two or more luminescent materials can be mixed as needed. As the luminescent material, a fluorescent material can be used, and a phosphorescent material can also be used. As the luminescent material, a single component material can be used, and a multi-component material can also be used.

[0146] 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. The metal complexes of 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, and polymer materials and small molecule materials can also be used.

[0147] The electron injection layer is a layer that injects electrons from the electrode. The present application uses LiF, however, the present application is not limited thereto.

[0148] The hole blocking layer is a layer that blocks holes from reaching the cathode.

[0149] The electron blocking layer is a layer that blocks electrons from reaching the anode.

[0150] 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.

[0151] The charge generation layer is an intermediate layer between the anode and cathode in a tandem structure element, and is a layer that generates holes and electrons by charge separation. The charge generation layer is usually formed by a P-type layer on the cathode side and an N-type layer on the anode side, and can effectively separate charges and effectively transport carriers.

[0152] 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 reaction. The following general formula is only one of the synthesis methods.

[0153]

[0154]

[0155] 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

[0156]

[0157] Under 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 the reaction was completed, the reaction solution was cooled to room temperature, extracted with dichloromethane, and dried over anhydrous sodium sulfate to remove the solvent. Compound 109 was purified by silica gel chromatography (developing solvent: dichloromethane) to obtain 9 g of compound 109 with a yield of 88%.

[0158] LC-MS (APCI): 447.37 (M+H + ).

[0159] 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).

[0160] Synthesis Example 2: Synthesis of Compound 1

[0161] (1) Synthesis of intermediate 1-1

[0162]

[0163] Under nitrogen atmosphere, raw material 3 (50 g, 247.5 mmol), raw material 4 (55 g, 297 mmol), K2CO3 (68 g, 495 mmol), Pd(PPh3)4 (5.7 g, 4.95 mmol) were placed in a four-necked reaction bottle, and then 500 mL of toluene: ethanol: water (volume ratio 7:3:3) was added, and the mixture was heated to reflux for reaction. The reaction was completed after 3 h. After the reaction was completed, the mixture was extracted with ethyl acetate and then purified by column chromatography (volume ratio of n-hexane: ethyl acetate 20:1) to obtain 38 g of intermediate 1-1 with a yield of 58%.

[0164] LC-MS (APCI): 265.07 (M+H + ).

[0165] (2) Synthesis of Intermediate 2

[0166]

[0167] Under nitrogen atmosphere, intermediate 1-1 (38 g, 144 mmol), potassium carbonate (40 g, 288 mmol), (1-diazo-2-oxopropyl) phosphonic acid dimethyl ester (41 g, 216 mmol) were placed in a three-necked flask, and 1 L of anhydrous methanol was added to react at room temperature. The reaction was monitored by TLC until the raw materials were completely consumed (about 3 h). After the reaction was completed, water was added to quench the reaction, and the mixture 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 out to the next step without further purification.

[0168] LC-MS (APCI): 261.12 (M+H + ).

[0169] (3) Synthesis of intermediate 1-3

[0170]

[0171] Under 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, and 1 L of anhydrous toluene was added. The reaction was heated under reflux and monitored by TLC until the raw materials were completely consumed (about 13 h). After the reaction was completed, water was added to quench the reaction, and the mixture was extracted twice with ethyl acetate, and then purified by column chromatography (n-hexane: ethyl acetate volume ratio 50:1) to obtain 10 g of intermediate 1-3 with a yield of 29%.

[0172] LC-MS (APCI): 261.15 (M+H + ).

[0173] (4) Synthesis of Intermediates 1-4

[0174]

[0175] Under nitrogen atmosphere, take intermediate 1-3 (10 g, 38.3 mmol) in a three-necked flask, add 200 mL of anhydrous dichloromethane, then cool to -40 ° C, then add boron tribromide (14 g, 57 mmol) dropwise at this temperature, slowly warm to room temperature after the addition is complete, monitor the reaction by TLC until the raw material is completely consumed (about 4 h). After the reaction is completed, add ice water to quench the reaction, extract twice with ethyl acetate, and then purify by column chromatography (n-hexane: ethyl acetate volume ratio 20: 1) to obtain 8 g of intermediate 1-4, with a yield of 85%.

[0176] LC-MS (APCI): 247.11 (M+H + ).

[0177] (5) Synthesis of Intermediate 1-5

[0178]

[0179] Under nitrogen atmosphere, intermediate 1-4 (8 g, 32 mmol) and potassium carbonate (8.9 g, 65 mmol) were placed in a three-necked flask, and 100 mL of N-methylpyrrolidone was added, and the mixture was heated to 120°C for reaction. The reaction was monitored by TLC until the raw material was completely consumed (about 15 h). After the reaction was completed, water was added to quench the reaction, and the mixture was extracted three times with ethyl acetate, and then purified by column chromatography (pure hexane) to obtain 6.5 g of intermediate 1-5 with a yield of 75%.

[0180] LC-MS (APCI): 227.25 (M+H + ).

[0181] (6) Synthesis of Compound 1

[0182]

[0183] Under 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 bottle, and toluene: ethanol: water (volume ratio 7:3:3) was added in total of 80 mL, and the temperature was raised to reflux reaction. After 5 h, the reaction was complete. After the reaction was completed, a large amount of solid was precipitated, and then directly filtered to obtain 9.6 g of crude product, and then refluxed with ethyl acetate to obtain 8.3 g of compound 1, with a yield of 70%.

[0184] LC-MS (APCI): 447.27 (M+H + ).

[0185] 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).

[0186] Synthesis Example 3: Synthesis of Compound 110

[0187] (1) Synthesis of Intermediate 110-1

[0188]

[0189] 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 bottle, and then 140ml of 1,4-dioxane was added and heated to 90°C. After 2h of reaction, TLC detected that the raw material had reacted. Water was added to quench, and dichloromethane was added to extract the reaction. Separate and purify by chromatography column, and the eluent was ethyl acetate: n-hexane in a volume ratio of 1:1. 6.94g of product was obtained, with a yield of 87.4%

[0190] LC-MS (APCI): 319.18 (M+H + ).Calcd for C 20 H 19 BO3

[0191] (2) Synthesis of Compound 110

[0192]

[0193] 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 bottle, and then 170ml of tetrahydrofuran and 55ml of water were added; the temperature was raised to 75°C for reaction. After the reaction was completed, the product was directly filtered to obtain 7.89g, with a yield of 76.1%.

[0194] LC-MS (APCI): 497.42 (M+H + ).Calcd for C 36 H 20 N2O

[0195] 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)

[0196] Synthesis Example 4: Synthesis of Compound 112

[0197]

[0198]

[0199] Under 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 with 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. Thus, 22.1 g of white solid compound 112 was obtained with a yield of 83%.

[0200] MS (APCI): 523.40 (M+H + ).Calcd for C 38 H 22 N2O.

[0201] 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).

[0202] Synthesis Example 5 Synthesis of Compound 115

[0203] (1) Synthesis of Intermediate 115-1

[0204]

[0205] Under nitrogen atmosphere, 1,6-dibromopyrene (57.6 g, 160.0 mmol), biboronic acid pinacol ester (101.2 g, 400.0 mmol), 1,1'-bis(diphenylphosphino)ferrocene palladium 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 the reaction was completed, the reaction solution was cooled to room temperature, extracted with dichloromethane, and dried over anhydrous sodium sulfate to remove the solvent. Purification by silica gel chromatography (developing solvent: n-hexane: ethyl acetate = volume ratio 9:1) gave intermediate 115-1 (57.0 g, yield 78.5%).

[0206] LC-MS (APCI): 455.53 (M+H + ).Calcd for C 28 H 32 B2O4

[0207] (2) Synthesis of Intermediate 115-2

[0208]

[0209] Under nitrogen atmosphere, add 350 ml toluene, 150 ml ethanol, 150 ml water to intermediate 115-1 (30.0 g, 66.0 mmol), 2-bromo-1,10-phenanthroline (17.0 g, 66.0 mmol), tetrakis(triphenylphosphine)palladium (1.14 g, 0.99 mmol) and potassium carbonate (18.2 g, 132.0 mmol), and heat to reflux for 4 hours. After the reaction is completed, the reaction solution is cooled to room temperature, extracted with dichloromethane, and dried with anhydrous sodium sulfate to remove the solvent. Purification by silica gel chromatography (developing solvent: n-hexane: ethyl acetate = 1:1) gives intermediate 115-2 (16.0 g, yield 48.0%).

[0210] LC-MS (APCI): 507.47 (M+H + ).Calcd for C 34 H 27 BN2O2

[0211] (3) Synthesis of Compound 115

[0212]

[0213] Under nitrogen atmosphere, intermediate 115-2 (10.7 g, 21.1 mmol), raw 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 temperature was raised to reflux for 3 hours. After the reaction was completed, the reaction solution was cooled to room temperature, extracted with dichloromethane, and dried over anhydrous sodium sulfate to remove the solvent. Compound 115 (7.0 g, yield 58.3%) was obtained by purification by silica gel chromatography (developing solvent: tetrahydrofuran: dichloromethane = volume ratio 1:10).

[0214] LC-MS (APCI): 571.48 (M+H + ).Calcd for C 42 H 22 N2O

[0215] 1H 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).

[0216] The following application examples further illustrate the application of the heterocyclic compound of the present invention and the organic electroluminescent element containing the heterocyclic compound.

[0217] Application Example 1

[0218] This embodiment provides an organic electroluminescent element, such as Figure 1 As shown, it includes 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.

[0219] The specific component structure is:

[0220] 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).

[0221] Component preparation process:

[0222] The bottom-emitting glass substrate used in this embodiment was purchased from Guangdong Xinli Display Technology Co., Ltd., and 100 nm ITO was used as the first electrode layer 1. First, the bottom-emitting glass substrate was cleaned with ITO cleaning agent, deionized water, and isopropyl alcohol in sequence, and then the bottom-emitting glass substrate was baked at 180 degrees Celsius for 30 minutes to dry it.

[0223] Then put the bottom luminescent glass substrate into the evaporation chamber and place it in a vacuum chamber of about 10 -8In the case of torr, each organic layer is deposited on the ITO anode in sequence by thermal vacuum evaporation at a rate of 0.2-2 angstroms / second. 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 the anthracene main body ADN (9,10-di(naphtha-2-yl-)anthracene) is doped with a 3% mass content of pyrene dopant 1,6-bis(diphenylamino)pyrene 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% mass content of Li 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 with a thickness of 20 nm is formed as a hole transport layer, an 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.

[0224] 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.

[0225]

[0226] Contrast structure

[0227] Bphen(4,7-Diphenyl-1,10-phenanthroline)

[0228]

[0229] Examples and Comparative Examples

[0230] Charge Generation Layer The N-type charge generation layer 6 is prepared by using the compound prepared in Example 1 of the present invention instead of the Bphen material, and the organic electronic element 2 is prepared by the same method.

[0231] The charge generation layer uses the compound prepared in Example 2 of the present invention instead of the Bphen material to prepare the N-type charge generation layer 6, and the organic electronic element 3 is manufactured by the same method.

[0232] Charge Generation Layer The N-type 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 by the same method.

[0233] The charge generation layer uses the compound prepared in Example 4 of the present invention instead of Bphen material to prepare an N-type charge generation layer 6, and the organic electronic element 5 is manufactured using the same method.

[0234] Charge Generation Layer The N-type 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.

[0235] 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: hours)) was measured. The driving voltage was set at a current density of 15 mA / cm 2 The following test results are shown in Table 1.

[0236] Table 1

[0237] Driving voltage, v Life LT95, hours Organic electronic components1 7.07 58 Organic Electronic Components2 6.90 94 Organic Electronic Components3 6.90 98 Organic Electronic Components4 6.90 94 Organic electronic components5 6.89 92 Organic electronic components6 6.89 93

[0238] The organic electroluminescent element prepared by the compound of the present invention has a lower driving voltage and a longer service life than the organic electroluminescent element prepared by BPHEN, and therefore, is suitable as a material for an organic electroluminescent element.

[0239] In this specification, each embodiment is described in a progressive manner, and each embodiment focuses on the differences from other embodiments. The same or similar parts between the embodiments can be referred to each other. For the device disclosed in the embodiment, since it corresponds to the method disclosed in the embodiment, the description is relatively simple, and the relevant parts can be referred to the method part.

[0240] The above is a detailed introduction to a heterocyclic compound provided by the present invention and an organic electroluminescent element containing the heterocyclic compound. 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 principle of the present invention, the present invention can also be improved and modified in a number of 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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