Heterocyclic compound and organic electroluminescent device

Abstract

The invention belongs to the technical field of luminescent materials, and particularly discloses a heterocyclic compound and an organic electroluminescent device. The structural general formula of the heterocyclic compound is shown as a formula (1) or a formula (2). The heterocyclic compound disclosed by the invention has the advantages of low driving voltage, high luminous efficiency, long device service life and the like, and can be used as an electron transport material, a hole blocking layer material and an N-type charge generation layer material in OLED (Organic Light Emitting Diode) luminescent devices.

Description

Technical Field

[0001] This invention belongs to the field of organic electroluminescence technology, and specifically relates to a heterocyclic compound and an organic electroluminescence device. Background Technology

[0002] Currently, organic light-emitting diodes (OLEDs), as a next-generation display technology, have received widespread attention in the display and lighting fields, demonstrating broad application prospects. With the continuous development of OLED technology in display and lighting, higher demands are being placed on the performance of OLED devices, especially in terms of low power consumption, high efficiency, and long lifespan. Therefore, developing higher-performance functional materials and optimizing device structures have become current research hotspots.

[0003] In the most common OLED device structures, the following functional materials are typically included: hole injection materials, hole transport materials, electron transport materials, and luminescent materials (including host and guest materials). Electron transport materials, as a crucial functional material, directly influence electron mobility, ultimately affecting the OLED's luminous efficiency. Therefore, improving the mobility of electron transport materials and reducing device power consumption have become important directions for improving OLED device performance. By forming a tandem OLED structure, stacking multiple luminescent layers and sandwiching charge generation layers between them, mobility can be further improved. Charge generation layers typically include N-type and P-type charge generation layers, with the N-type charge generation layer playing a vital role as an electron transport material in improving mobility and reducing power consumption. However, performance improvements in these materials remain limited, and device efficiency and lifetime still require further improvement.

[0004] Therefore, it is necessary to develop charge generation layer materials with higher mobility. Summary of the Invention

[0005] The present invention aims to at least solve one of the technical problems existing in the prior art. To this end, the present invention provides a heterocyclic compound that can be used to prepare the N-type charge generation layer of OLEDs, exhibiting high electron mobility, effectively reducing device power consumption, improving luminous efficiency, and extending device lifespan.

[0006] To achieve the above objectives, the present invention adopts the following technical solution:

[0007] In one aspect, the present invention provides a heterocyclic compound having the structure shown in formula (1) or formula (2):

[0008]

[0009] Where A is selected from one of the structures shown in Equations (3) to (8), and * indicates the connection site with Equations (1) and (2);

[0010]

[0011] Ar1 is selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C60 heteroaryl, or substituted or unsubstituted C8-C30 benzocycloalkyl, and Ar1 must meet the following conditions:

[0012] I and Ar1 do not contain substituted or unsubstituted six-membered nitrogen heteroaromatic rings;

[0013] II. When A is selected from formula (6), Ar1 does not contain substituted or unsubstituted pyrene or substituted or unsubstituted dibenzofuran.

[0014] Ⅲ. When A is selected from formula (7) or (8), Ar1 does not contain substituted or unsubstituted oxazolyl, substituted or unsubstituted aryl-oxazolyl or substituted or unsubstituted carbazoyl.

[0015] Ar2-Ar9 are each independently selected from substituted or unsubstituted C6-C30 aryl groups or substituted or unsubstituted C3-C60 heteroaryl groups.

[0016] Each time R1 to R7 appears, they are independently selected from hydrogen, deuterium, halogen, cyano, nitro, C1-C40 alkyl, C1-C40 heteroalkyl, C2-C40 alkenyl, C2-C40 alkynyl, C3-C40 cycloalkyl, C3-C40 heterocycloalkyl, C6-C60 aryl, C5-C60 heteroaryl, C1-C40 alkoxy, C6-C60 aryloxy, C3-C40 alkylsilyl, C6-C60 arylsilyl, C1-C40 alkylboryl, C6-C60 arylboryl, C6-C60 arylphosphinyl, or C6-C60 arylamine.

[0017] L1 and L2 are independently selected from single-bonded, substituted or unsubstituted C6-C30 arylene or substituted or unsubstituted C2-C30 heteroarylene, respectively;

[0018] The substitutions described in Ar1, Ar2-Ar9, L1, and L2 are substituted by at least one selected from deuterium, halogen, cyano, C1-C40 alkyl, C6-C60 aryl, or C3-C60 heteroaryl, wherein the number of substitutions ranges from monosubstituted to the maximum number of substitutions.

[0019] The heteroatom in the heteroaryl, heteroaryl, heteroalkyl, or heterocycloalkyl group is independently selected from at least one of O, S, N, Se, Si, or Ge.

[0020] The beneficial effects of this invention are as follows:

[0021] The heterocyclic compound of this invention has a terpyridine structure, multiple coordination sites, and high mobility, making it suitable as a charge generation layer material for OLEDs. Specifically, the multiple coordination sites of this compound allow for better coordination with dopants (such as alkali metals, alkaline earth metals, and lanthanides) and metal ions, reducing material degradation caused by metal ion migration in the device. The heterocyclic compound of this invention can reduce the energy level difference between the N-type and P-type charge generation layers, thereby promoting electron injection into the N-type charge generation layer and maximizing electron transfer from the N-type charge generation layer to the adjacent electron transport layer, further improving device performance.

[0022] When applied to OLED devices, this compound can effectively reduce driving voltage, improve luminous efficiency, and extend device lifespan, showing potential for application in the AMOLED industry. Attached Figure Description

[0023] Figure 1 This is a schematic diagram of the structure of an organic electroluminescent device according to an embodiment of the present invention. Detailed Implementation

[0024] To enable those skilled in the art to more clearly understand the technical solutions described in this invention, the following embodiments are provided for illustration. It should be noted that the following embodiments do not constitute a limitation on the scope of protection claimed by this invention.

[0025] Unless otherwise specified, the raw materials, reagents or devices used in the following examples are available from conventional commercial sources or can be obtained by existing known methods.

[0026] A first aspect of the present invention provides a heterocyclic compound having a structure represented by formula (1) or formula (2):

[0027]

[0028] Where A is selected from one of the structures shown in Equations (3) to (8), and * indicates the connection site with Equations (1) and (2);

[0029]

[0030] Ar1 is selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C60 heteroaryl, or substituted or unsubstituted C8-C30 benzocycloalkyl, and Ar1 must meet the following conditions:

[0031] I and Ar1 do not contain substituted or unsubstituted six-membered nitrogen heteroaromatic rings;

[0032] II. When A is selected from formula (6), Ar1 does not contain substituted or unsubstituted pyrene or substituted or unsubstituted dibenzofuran.

[0033] Ⅲ. When A is selected from formula (7) or (8), Ar1 does not contain substituted or unsubstituted oxazolyl, substituted or unsubstituted aryl-oxazolyl or substituted or unsubstituted carbazoyl.

[0034] Ar2-Ar9 are each independently selected from substituted or unsubstituted C6-C30 aryl groups or substituted or unsubstituted C3-C60 heteroaryl groups.

[0035] Each time R1 to R7 appears, they are independently selected from hydrogen, deuterium, halogen, cyano, nitro, C1-C40 alkyl, C1-C40 heteroalkyl, C2-C40 alkenyl, C2-C40 alkynyl, C3-C40 cycloalkyl, C3-C40 heterocycloalkyl, C6-C60 aryl, C5-C60 heteroaryl, C1-C40 alkoxy, C6-C60 aryloxy, C3-C40 alkylsilyl, C6-C60 arylsilyl, C1-C40 alkylboryl, C6-C60 arylboryl, C6-C60 arylphosphinyl, or C6-C60 arylamine.

[0036] L1 and L2 are independently selected from single-bonded, substituted or unsubstituted C6-C30 arylene or substituted or unsubstituted C2-C30 heteroarylene, respectively;

[0037] The substitutions described in Ar1, Ar2-Ar9, L1, and L2 are substituted by at least one selected from deuterium, halogen, cyano, C1-C40 alkyl, C6-C60 aryl, or C3-C60 heteroaryl, wherein the number of substitutions ranges from monosubstituted to the maximum number of substitutions.

[0038] The heteroatom in the heteroaryl, heteroaryl, heteroalkyl, or heterocycloalkyl group is independently selected from at least one of O, S, N, Se, Si, or Ge.

[0039] In some embodiments, Ar1 is selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 heteroaryl, or substituted or unsubstituted C8-C30 benzocycloalkyl, wherein the substitution is by being substituted by at least one selected from deuterium, halogen, cyano, C1-C20 alkyl, C6-C30 aryl, or C3-C30 heteroaryl;

[0040] The condition is that I and Ar1 do not contain substituted or unsubstituted six-membered nitrogen heteroaromatic rings;

[0041] II. When A is selected from formula (6), Ar1 does not contain substituted or unsubstituted pyrene or substituted or unsubstituted dibenzofuran.

[0042] When A is selected from formulas (7) and (8), Ar1 does not contain substituted or unsubstituted oxazolyl, substituted or unsubstituted aryl-oxazolyl, or substituted or unsubstituted carbazoyl.

[0043] Preferably, Ar1 is selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C8-C30 benzocycloalkyl, substituted or unsubstituted Replaced or not replaced Wherein, X is selected from O, S or Se, ring B and ring C are each independently absent, benzene ring or naphthalene ring, and at least one of ring B and ring C is present; the substitution is substituted by at least one selected from deuterium, halogen, cyano, C1-C12 alkyl, C6-C20 aryl or C3-C20 heteroaryl;

[0044] The condition is that I and Ar1 do not contain substituted or unsubstituted six-membered nitrogen heteroaromatic rings;

[0045] II. When A is selected from formula (6), Ar1 does not contain substituted or unsubstituted pyrene or substituted or unsubstituted dibenzofuran.

[0046] When A is selected from formulas (7) and (8), Ar1 does not contain substituted or unsubstituted oxazolyl, substituted or unsubstituted aryl-oxazolyl, or substituted or unsubstituted carbazoyl.

[0047] More preferably, Ar1 is selected from one of the following structures:

[0048]

[0049] Each R8 is independently selected from deuterium, halogen, cyano, C1-C12 alkyl or C6-C20 aryl;

[0050] a represents an integer from 0 to 4. When a takes the value of an integer from 2 to 4, each R8 is either the same or different; the condition is that when A is selected from equation (6), Ar1 is not equal to 0. Furthermore, R8 is not a pyrene group.

[0051] More preferably, Ar1 is selected from one of the following structures:

[0052]

[0053] The condition is:

[0054] When A is selected from equation (6), Ar1 is not...

[0055] In some embodiments, each of the R1 to R7 is independently selected from hydrogen, deuterium, halogen, cyano, nitro, C1-C20 alkyl, C1-C20 heteroalkyl, C2-C20 alkenyl, C2-C20 alkynyl, C3-C20 cycloalkyl, C3-C20 heterocycloalkyl, C6-C20 aryl, or C5-C20 heteroaryl.

[0056] In some embodiments, Ar2-Ar9 are each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted diphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthraceneyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiopheneyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirodifluorenyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted pyreneyl, substituted or unsubstituted carbazoleyl, etc. The substitution is a combination of one or more of the following: substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted fluoranyl, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted benzotriazolyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted benzophenanthryl, and substituted or unsubstituted benzocycloalkyl; wherein the substitution is by at least one selected from deuterium, halogen, cyano, C1-C12 alkyl, C6-C20 aryl, or C3-C20 heteroaryl.

[0057] Preferably, R1 and R2 are hydrogen.

[0058] More preferably, the heterocyclic compound is selected from one of the structures shown in formulas (A-1) to (A-4):

[0059]

[0060] In the formula, A, Ar1, Ar2, L1, and L2 have the definitions described above.

[0061] Preferably, A is selected from one of the following structures:

[0062]

[0063] In some embodiments, L1 and L2 are each independently selected from single-bonded, substituted or unsubstituted C6-C12 arylene or substituted or unsubstituted C2-C12 heteroarylene, wherein the substitution is by being substituted by at least one selected from deuterium, halogen, cyano, C1-C12 alkyl, C6-C20 aryl or C3-C20 heteroaryl, wherein the number of substitutions is from monosubstituted to the maximum number of substitutions.

[0064] Preferably, L1 and L2 are independently selected from single bonds, phenylene, biphenylene, naphthylene, and phenanthrene, respectively.

[0065] In some embodiments, the heterocyclic compound is one of the following structural formulas, or one of the following structural formulas in which hydrogen is partially or completely substituted by deuterium or fluorine:

[0066]

[0067]

[0068]

[0069]

[0070]

[0071]

[0072]

[0073]

[0074]

[0075]

[0076]

[0077] A second aspect of the present invention provides an organic electroluminescent device comprising the heterocyclic compound described above.

[0078] In some embodiments, the organic electroluminescent device includes an anode and a cathode, with a functional layer between the anode and the cathode, the functional layer containing the aforementioned heterocyclic compound.

[0079] In some embodiments, a first light-emitting unit, a charge-generating layer, and a second light-emitting unit are sequentially stacked from the anode side to the cathode side in the functional layer, wherein the charge-generating layer contains the aforementioned heterocyclic compound.

[0080] In some embodiments, an N-type charge generation layer and a P-type charge generation layer are sequentially stacked from the first light-emitting unit side to the second light-emitting unit side, wherein the N-type charge generation layer contains the aforementioned heterocyclic compound.

[0081] In some implementations, the N-type charge generation layer also contains doped material.

[0082] In some embodiments, the dopant material is selected from at least one of alkali metals (e.g., Li, Na, K), alkaline earth metals (e.g., Ca, Mg) or lanthanides (e.g., La, Yb, Ce).

[0083] In some embodiments, the mass percentage of the doped material in the N-type charge generation layer can be 0.1%-20%, or 1%-10%, or 1%-5%; the mass percentage of the heterocyclic compound can be 80%-99.9%, or 90%-99%, or 95%-99%.

[0084] In some embodiments, a first hole functional layer, a first light-emitting layer, and a first electron functional layer are sequentially stacked from the anode side to the charge generation layer side in the first light-emitting unit. As an example, a hole injection layer, a first hole transport layer, and a first electron blocking layer are sequentially stacked from the anode side to the first light-emitting layer side in the first hole functional layer; the first electron functional layer includes a first electron transport layer.

[0085] In some embodiments, the second light-emitting unit is provided with a second hole functional layer, a second light-emitting layer, and a second electron functional layer stacked sequentially from the charge generation layer towards the cathode side. As an example, the second hole functional layer is provided with a second hole transport layer and a second electron blocking layer stacked sequentially from the charge generation layer side towards the second light-emitting layer side; the second electron functional layer is provided with a second electron transport layer and an electron injection layer stacked sequentially from the second light-emitting layer side towards the cathode side.

[0086] In some embodiments, the functional layers are stacked sequentially from the anode side to the cathode side, including a hole injection layer, a first hole transport layer, a first electron blocking layer, a first light-emitting layer, a first electron transport layer, an N-type charge generation layer, a P-type charge generation layer, a second hole transport layer, a second electron blocking layer, a second light-emitting layer, a second electron transport layer, and an electron injection layer; wherein the N-type charge generation layer contains the aforementioned heterocyclic compound.

[0087] It should be noted that the present invention does not limit the stacked structure of the light-emitting unit, and those skilled in the art can use any stacked structure known in the prior art.

[0088] A third aspect of the present invention provides an optoelectronic element comprising the heterocyclic compound described above or the organic electroluminescent device described above.

[0089] Non-limiting examples of optoelectronic components include: lighting fixtures (such as lamps), displays (such as automotive displays, computer displays, or television displays, where the display type may be an AMOLED display), or sensors, etc.

[0090] Based on the role of this heterocyclic compound in improving electron mobility, it can be used as a charge generation layer material in OLED devices. This can effectively reduce driving voltage, improve luminous efficiency, and extend device lifetime, showing potential for application in the AMOLED industry. Specifically, the compound's multiple coordination sites allow for better coordination with dopants (such as alkali metals, alkaline earth metals, and lanthanides) and metal ions, reducing material degradation caused by metal ion migration within the device. This heterocyclic compound can reduce the energy level difference between the N-type and P-type charge generation layers, thereby promoting electron injection into the N-type charge generation layer and maximizing electron transfer from the N-type charge generation layer to the adjacent electron transport layer, further improving device performance.

[0091] definition

[0092] Unless otherwise specified, all general formulas and their subordinate general formulas (e.g., group designation Ar1, etc.) involved in this invention have the same scope of interpretation in all embodiments of this invention. The definitions of different symbols can be freely combined, and all such combinations fall within the protection scope of this invention.

[0093] Unless otherwise stated, the scientific and technical terms used herein have the meanings commonly understood by those skilled in the art. However, for a better understanding of this invention, definitions of some terms are provided below. When the definitions of terms provided in this invention differ from the meanings commonly understood by those skilled in the art, the definitions and interpretations provided in this invention shall prevail.

[0094] The term "halogen" refers to one or more of fluorine, chlorine, bromine, or iodine, typically including fluorine, chlorine, or bromine.

[0095] The term "alkyl" refers to a straight-chain or branched saturated hydrocarbon group. In some embodiments, the alkyl group can be a C1-C40 (e.g., C1-C30, C1-C20, C1-C12, C1-C10, C1-C6, C1-C4) alkyl group. Non-limiting examples of alkyl groups include methyl, ethyl, propyl, butyl, heptyl, decyl, etc. Each group includes various isomers; for example, butyl includes isomers such as n-butyl, isobutyl, sec-butyl, tert-butyl, etc.

[0096] The term "heteroalkyl" refers to an alkyl group in which at least one carbon atom is replaced by a non-carbon atom or a group containing a non-carbon atom. The non-carbon atom can be selected from at least one of O, S, N, Si, Ge, or Se, but excludes cases where the carbon atom serving as a linking site is replaced by a non-carbon atom (e.g., alkoxy, alkylsilyl, alkylboryl). In some embodiments, the heteroalkyl group can be a C1-C40 (e.g., C1-C30, C1-C20, C1-C12, C1-C10, C1-C6, C1-C4) heteroalkyl group. Non-limiting examples of heteroalkyl groups include mercaptomethylmethane, methoxymethane, ethoxymethane, tert-butoxymethane, N,N-dimethylmethane, etc.

[0097] The term "alkoxy" refers to a group having an -O-alkyl group, i.e., an alkyl group as defined above connected to a given group or given structural formula via an oxygen atom. Non-limiting examples of alkoxy groups include methoxy, ethoxy, and tert-butoxy.

[0098] The term "alkenyl" refers to a hydrocarbon group containing at least one double bond. In some embodiments, the alkenyl group can be a C2-C40 (e.g., C2-C20, C2-C12, C2-C10, C2-C6, C2-C4) alkenyl group. Non-limiting examples of alkenyl groups include: vinyl, propenyl, allyl, isopropenyl, 1-butadienyl, 2-butadienyl, 1-hextrienyl, 2-hextrienyl, and 3-hextrienyl.

[0099] The term "alkynyl" refers to a hydrocarbon group containing at least one triple bond. In some embodiments, the alkynyl group can be a C2-C40 (e.g., C2-C20, C2-C12, C2-C10, C2-C6, C2-C4) alkynyl group. Non-limiting examples of alkynyl groups include ethynyl and propynyl.

[0100] The term "cycloalkyl" refers to a non-aromatic carbonyl ring consisting of at least three carbon atoms, which may include monocyclic, polycyclic, and spiroalkyl rings. In some embodiments, the cycloalkyl ring may be, for example, a C3-C40 (e.g., C3-C30, C3-C20, C3-C12, C3-C8, C3-C6, C4-C6) cycloalkyl ring. Non-limiting examples of cycloalkyl rings include: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, bicyclo[3.1.1]heptyl, spiro[4.5]decyl, spiro[5.5]undecyl, adamantyl (including 1-adamantyl, 2-adamantyl), 1-norbornyl, or 2-norbornyl, etc.

[0101] The term "heterocyclic alkyl" refers to a cycloalkyl group in which at least one carbon atom is replaced by a non-carbon atom, which may be selected from at least one of O, S, N, Si, Ge, or Se. In some embodiments, the heterocyclic alkyl group may be, for example, a C3-C40 (e.g., C3-C30, C3-C20, C3-C12, C3-C8, C3-C6, C4-C6) heterocyclic alkyl group. Non-limiting examples of heterocyclic alkyl groups include epoxide butyl, epoxide pentyl, and epoxide hexyl.

[0102] The term "aryl" refers to an aromatic hydrocarbon group derived from an aromatic ring compound by removing one hydrogen atom, and can be monocyclic or polycyclic. At least one ring in a polycyclic aryl compound is an aromatic ring system. Multiple rings in a polycyclic aryl compound can be linked together by single bonds or can be fused together. When a polycyclic aryl compound contains a fused ring structure, it can be formed by the fusion of an aliphatic ring (saturated or unsaturated aliphatic ring) and an aromatic ring. In some embodiments, the aryl group can be, for example, C6–C60 aryl, C6–C50 aryl, C6–C40 aryl, C6–C30 aryl, C6–C20 aryl, C6–C12 aryl, or C6–C10 aryl. Specific examples of aryl groups include phenyl, naphthyl, anthraceneyl, phenanthryl, tetraphenyl, pyrene, dinaphthylphenyl, acenaphthyl, benzo[g]pyrene, benzo[g]phenanthryl, benzo[g]triylyl, fluorenyl, spirodifluorenyl, benzo[g]fluorenyl, dibenzo[g]fluorenyl, diphenyl, triphenyl, tetraphenyl, and fluoranthyl, etc. Benzo[g]phenanthryl includes 1,2-benzo[g]phenanthryl. 3,4-benzophenanthryl, 9,10-benzophenanthryl, etc.

[0103] The term "aryloxy group" refers to a group having an -O-aryl group, i.e., an aryl group as defined above connected to a given group or given structural formula via an oxygen atom. Non-limiting examples of aryloxy groups include phenoxy groups, naphthoxy groups, etc.

[0104] The term "heteroaryl" refers to an aryl group in which at least one carbon atom is replaced by a non-carbon atom, wherein the non-carbon atom can be a monovalent group selected from a heterocyclic aromatic system of O, S, N, Se, Si, or Ge, but does not include cases where the aryl group is attached to the host structure via a non-carbon atom group (e.g., aryloxy, arylsilyl, arylboryl, arylphosphinyl, arylamine). In some embodiments, the heteroaryl group may be a C3–C60 (e.g., C5–C60, C3–C50, C3–C40, C3–C30, C3–C20, C3–C12, C3–C10) heteroaryl group containing one or more (e.g., two or three) heteroatoms independently selected from O, S, N, Se, or Si. Specific examples of heteroaryl groups include pyrrole, pyrrolopyrrole, furanopyrrole, thienopyrrole, pyridyl, pyrazolyl, pyrimidinyl, pyrazinyl, triazinyl, pyridazinyl, phenazinyl, phenothiazinyl, phenoxazinyl, indole, isoindole, imidazolyl, benzimidazolyl, triazolyl, tetrazolyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, furanofuranyl, azadibenzofuranyl, thienofuranyl, diazadibenzofuranyl, benzo[B]naphtho[1,2- [D] furanyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, quinazolinoneyl, carbazoyl, azacarbazoyl, diazacarbazoyl, phenanthrynyl, primidyl, acridineyl, dihydroacridyl, phenanthrynyl, oxazolinyl, oxazolyl, oxadiazolyl, benzoisooxazolyl, thiazoyl, benzothiazoyl, benzoisothiazoyl, pyrroloimidazoyl, furazolyl, thienyl, benzothiaphenyl, dibenzothiaphenyl, azadibenzothiaphenyl, diazadibenzothiaphenyl, thienobenzothiaphenyl, and o-diazanaphthyl, etc.

[0105] The term "six-membered nitrogen heteroaromatic ring" refers to a six-membered heteroaromatic ring containing one, two, or three nitrogen atoms. It is generally assumed that a six-membered nitrogen heteroaromatic ring does not contain any heteroatoms other than the nitrogen atom. Specific examples of six-membered nitrogen heteroaromatic rings include pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, and triazinyl.

[0106] The terms "arylene" and "heteroarylene" correspond to divalent groups with the same structure as aryl and heteroaryl groups, respectively. In some embodiments, the arylene can be, for example, a C6-C60 (e.g., C6-C30, C6-C20, C6-C12, C6-C10) arylene; the heteroarylene can be, for example, a C2-C60 (e.g., C2-C40, C2-C30, C2-C20, C2-C12, C2-C10, C2-C6, C3-C12, C3-C6) heteroarylene.

[0107] The term "hydrocarbon group" refers to a group consisting only of carbon and hydrogen atoms, including saturated hydrocarbon groups (e.g., alkyl, cycloalkyl), unsaturated non-aromatic hydrocarbon groups (e.g., alkenyl, ynyl), and aromatic hydrocarbon groups (e.g., phenyl).

[0108] In the terms "alkylsilyl" or "arylsilyl," the number of alkyl or aryl groups can be one to three. "alkylboryl" includes monoalkylboryl and dialkylboryl, "arylboryl" includes monoarylboryl and diarylboryl, "arylphosphine" includes monoarylphosphine and diarylphosphine, and "arylamine" includes monoarylamine and diarylamine. In alkylsilyl, arylsilyl, alkylboryl, arylboryl, arylphosphine, and arylamine, the defined carbon number refers to the total number of carbons in the corresponding group.

[0109] It should be noted that Y does not contain one or more substituted or unsubstituted groups Z, meaning that neither the main structure of Y nor its substituents contain Z, nor does it contain Z substituted by substituents.

[0110] "At least two combinations" means that at least two defined groups are linked by a single bond or fused together, for example, phenyl groups fused together to form a naphthyl group, or phenyl groups linked by a single bond to form a phenyl-substituted naphthyl group. It should be understood that the combination of groups is contingent upon satisfying the defined carbon number range.

[0111] In the statement “R group of Ca-Cb with or without substitution”, “Ca-Cb” refers to the number of carbons a to b when the R group is unsubstituted, excluding the number of carbons of the substituent when the R group is substituted.

[0112] In the phrase “substituted or unsubstituted,” “substituted” means that one or more hydrogen atoms are replaced by other atoms or functional groups (i.e., substituents), and unless otherwise defined, also includes the replacement of one or more hydrogen atoms by groups formed by the linkage of two or more of the aforementioned substituents. The number of substitutions ranges from monosubstituted to the maximum number of substitutions.

[0113] "Maximum number of substitutions" refers to the maximum number of hydrogen atoms contained in the group when there are no substituents other than hydrogen.

[0114] The following embodiments are merely for the purpose of understanding the technical invention and should not be regarded as specific limitations of the present invention.

[0115] The raw materials and solvents involved in the synthesis of the compounds in this invention are all purchased from suppliers well known to those skilled in the art, such as Alfa and Acros.

[0116] The synthetic route for compound A3 is as follows:

[0117]

[0118] Synthesis of compound A3-3

[0119] Compound A3-1 (15.00 g, 75.75 mmol), compound A3-2 (17.11 g, 75.75 mmol), tetra(triphenylphosphine)palladium (0.87 g, 0.76 mmol), potassium carbonate (26.17 g, 189.37 mmol), tetrahydrofuran (500 ml), and deionized water (100 ml) were added to a 1000 ml three-necked round-bottom flask. The mixture was purged with nitrogen three times, and then the system was heated to 75 °C and reacted for 3 hours. The reaction was monitored by TLC (ethyl acetate: n-hexane = 1:15 as the developing solvent). Compound A3-1 was completely consumed.

[0120] Cool to room temperature, concentrate under reduced pressure to remove some of the solvent, add ethyl acetate (500 ml), wash three times with deionized water (90 ml * 3), separate the contents, dry-pick up the sample onto a silica gel column, and perform silica gel column chromatography purification (200-300 mesh silica gel, ethyl acetate: n-hexane = 1:20 as eluent). After elution, concentrate under reduced pressure at 60 °C for 1 hour to obtain a white solid, compound A3-3 (16.42 g, purity: 99.49%, yield: 72.45%), mass spectrometry: 299.03 (M+H).

[0121] Synthesis of compound A3-5

[0122] Compound A3-3 (16.00 g, 53.48 mmol), compound A3-4 (28.52 g, 112.30 mmol), tris(dibenzylacetone)palladium (0.49 g, 0.53 mmol), 2-dicyclohexylphosphine-2′,4′,6′-triisopropylbiphenyl (0.51 g, 1.07 mmol), potassium acetate (13.12 g, 133.69 mmol), and 1,4-dioxane (500 ml) were added to a 1000 ml three-necked round-bottom flask. The flask was purged with nitrogen three times, and then the system was heated to 100 °C and reacted for 2 hours. The reaction was monitored by TLC (using n-hexane:ethyl acetate = 10:1 as the developing solvent). Compound A3-3 was completely consumed.

[0123] The solution was cooled to 60℃, concentrated under reduced pressure to remove the solvent, and ethyl acetate (500 ml) was added. The solution was washed three times with deionized water (100 ml * 3), separated, mixed with silica gel, and dry-mounted onto a column for silica gel column chromatography purification (200-300 mesh silica gel, n-hexane:ethyl acetate = 10:1 as eluent). After elution, the solution was concentrated under reduced pressure at 60℃ for 1 hour to obtain the target compound A3-5 (18.41 g, purity: 99.25%, yield: 71.39%), mass spectrometry: 483.28 (M+H).

[0124] Synthesis of compound A3

[0125] Following the synthesis and purification method of compound A3-3, only the corresponding raw materials need to be changed to obtain the target compound A3 (14.93 g, purity: 99.92%, yield: 69.28%). After sublimation purification of 14.93 g of crude compound A3, sublimed pure compound A3 (11.38 g, purity: 99.98%, yield: 76.22%) was obtained, with a mass spectrometry reading of 693.27 (M+H). The CAS number for A3-6 is 149817-62-9.

[0126] 1 H NMR (400MHz, CDCl3) δ8.73(s,4H),8.70(dd,J=4.0,1.7Hz,4H),8.62(dd,J=8.3,1.4Hz,4H),8.26(t,J=2.2Hz,1H),8.0 3(d,J=2.2Hz,2H),7.78(dd,J=8.5,7.1Hz,4H),7.60–7.44(m,8H),7.39(d,J=7.2Hz,1H),7.22(dd,J=7.2,4.1Hz,4H).

[0127] Synthesis of intermediate A95-4

[0128]

[0129] Synthesis of compound A95-3

[0130] Following the synthetic and purification method for obtaining compound A3-3 from compound A3-1, only the corresponding raw materials need to be changed (as given in the synthetic route) to obtain the target compound A95-3 (19.56 g, purity: 99.37%, yield: 70.80%) from compound A95-1. The CAS number for A95-1 is 1219080-58-6.

[0131] Synthesis of intermediate A95-4

[0132] Referring to the synthesis and purification method for obtaining compound A3-5 from compound A3-3, only the corresponding raw materials need to be changed (as given in the synthesis route) to obtain the target compound A95-4 (15.72g, purity: 99.24%, yield: 76.09%) from compound A95-3.

[0133] Synthesis of intermediate A161-3

[0134]

[0135] Synthesis of compound A161-2

[0136] Following the synthetic and purification method for obtaining compound A3-3 from compound A3-1, only the corresponding raw materials need to be changed (as given in the synthetic route) to obtain the target compound A161-2 (18.21 g, purity: 99.42%, yield: 71.97%) from compound A161-1. The CAS number for A161-1 is 162607-19-4.

[0137] Synthesis of intermediate A161-3

[0138] Referring to the synthesis and purification method for obtaining compound A3-5 from compound A3-3, only the corresponding raw materials need to be changed (as given in the synthesis route) to obtain the target compound A161-3 (14.50g, purity: 99.19%, yield: 75.37%) from compound A161-2.

[0139] Intermediate A188-3

[0140]

[0141] Synthesis of compound A188-2

[0142] Following the synthetic and purification method for obtaining compound A3-3 from compound A3-1, only the corresponding raw materials need to be changed (as given in the synthetic route) to obtain the target compound A188-2 (14.92 g, purity: 99.42%, yield: 73.11%) from compound A188-1. The CAS number for A188-1 is 768-35-4.

[0143] Synthesis of intermediate A188-3

[0144] Referring to the synthesis and purification method for obtaining compound A3-5 from compound A3-3, only the corresponding raw materials need to be changed (as given in the synthesis route) to obtain the target compound A188-3 (12.08g, purity: 99.35%, yield: 74.08%) from compound A188-2.

[0145] Intermediate A285-3

[0146]

[0147] Synthesis of compound A285-2

[0148] Following the synthetic and purification method for obtaining compound A3-3 from compound A3-1, only the corresponding raw materials need to be changed (as given in the synthetic route) to obtain the target compound A285-2 (19.27 g, purity: 99.33%, yield: 69.75%) from compound A285-1. The CAS number for A285-1 is 745784-12-7.

[0149] Synthesis of intermediate A285-3

[0150] Referring to the synthesis and purification method for obtaining compound A3-5 from compound A3-3, only the corresponding raw materials need to be changed (as given in the synthesis route) to obtain the target compound A285-3 (15.30g, purity: 99.42%, yield: 74.06%) from compound A285-2.

[0151] Intermediate A306-2

[0152]

[0153] Synthesis of intermediate A306-2

[0154] Following the synthetic and purification method for obtaining compound A3-5 from compound A3-3, only the corresponding raw materials need to be changed (as given in the synthetic route) to obtain the target compound A306-2 (12.35 g, purity: 99.25%, yield: 70.21%) from compound A306-1. The CAS number for A306-2 is 2695499-74-0.

[0155] Based on the above intermediates, compounds A23, A48, A66, A76, A92, A95, A106, A161, A188, A205, A285, and A306 were prepared using the same synthetic method as compound A3, except that the raw materials used were different, as shown below.

[0156]

[0157]

[0158]

[0159] Synthesis of compound A42

[0160]

[0161] Synthesis of compound A42-3

[0162] Compound A42-1 (15.00 g, 51.27 mmol, CAS: 1445904-43-7) and dry tetrahydrofuran (300 ml) were added to a 500 ml three-necked round-bottom flask. The flask was purged with nitrogen three times. The system was then cooled to -78 °C. A solution of n-butyllithium in n-hexane (24.61 ml, 61.53 mmol, concentration 2.5 mol / L) was then added dropwise, keeping the internal temperature below -70 °C. The addition was completed over 5 minutes, and the system was stirred at -78 °C for 1 hour. Finally, compound A42-2 (13.57 g, 61.53 mmol, CAS: 1079-66-9) was added dropwise over 10 minutes. After the system was allowed to cool to room temperature, TLC was performed (using dichloromethane:methanol = 10:1 as the developing solvent). Compound A42-1 was completely consumed.

[0163] The reaction was quenched dropwise with deionized water (100 ml), and the mixture was directly separated. The aqueous phase was extracted twice with dichloromethane (200 ml * 2). The organic phases were combined and concentrated under reduced pressure at 65 °C for 1 hour to obtain a pale yellow oily substance, which was compound A42-3 (16.74 g, yield: 82.07%). The obtained compound was used directly in the next step without purification. Mass spectrometry: 398.08 (M + H).

[0164] Synthesis of compound A42-4

[0165] Compound A42-3 (16.00 g, 40.22 mmol) was added to a 500 mL single-necked reaction flask and dichloromethane (300 mL) was added. The mixture was stirred at room temperature, and hydrogen peroxide (30%, 2.05 g, 60.33 mmol) was slowly added dropwise. After reacting for 1 h, the reaction was monitored by TLC (dichloromethane:ethyl acetate = 10:1 as the developing solvent). Compound A42-3 was completely consumed.

[0166] After the reaction was complete, the liquid was separated directly, and the organic phase was then evaporated to dryness (60℃). 100g of silica gel (200-300 mesh) was added for column chromatography to separate the product (eluent: dichloromethane: ethyl acetate = 7:1). After elution, the product was concentrated under reduced pressure at 60℃ for 1 hour to obtain a yellow oily crude product. The yellow oily crude product was placed in a 500ml flask and 200ml of n-hexane was added. The mixture was stirred at room temperature for 2 hours, and then filtered to obtain a white solid, compound A42-4 (10.92g, purity: 99.17%, yield: 65.61%), mass spectrometry: 414.07 (M+H).

[0167] Synthesis of compound A42-5

[0168] Referring to the synthesis and purification method for obtaining compound A3-5 from compound A3-3, only the corresponding raw materials need to be changed (as given in the synthesis route) to obtain the target compound A42-5 (9.22g, purity: 99.51%, yield: 75.50%) from compound A42-4.

[0169] Synthesis of compound A42

[0170] Following the synthetic and purification method for compound A3 obtained from compound A3-5, only the corresponding raw materials need to be changed (as given in the synthetic route) to obtain the target compound A42 (7.79 g, purity: 99.90%, yield: 71.63%) from compound A42-5. After sublimation purification of 7.79 g of crude compound A42, sublimed pure compound A42 (5.97 g, purity: 99.95%, yield: 76.63%) was obtained, mass spectrometry: 611.19 (M+H).

[0171] 1 H NMR (400MHz, CDCl3) δ8.70(dd,J=4.0,1.8Hz,2H),8.62(dd,J=8.3,1.4Hz,2H),8.56(s,2H),8.08(t,J=2.1Hz,1H),8.02(t,J=2.2H z,1H),7.86–7.83(m,3H),7.81–7.74(m,4H),7.70–7.65(m,4H),7.58–7.53(m,2H),7.50–7.45(m,4H),7.22(dd,J=7.1,4.1Hz,2H).

[0172] Compound A255 was prepared by the same synthetic method as compound A42, except that the raw materials used were different, as shown below.

[0173]

[0174] Synthesis of compound A325

[0175]

[0176] Synthesis of compound A325

[0177] Compound A205 (15.00 g, 23.45 mmol), platinum dioxide (0.64 g, 2.81 mmol), and heavy water (300 ml) were added to a 500 ml pressure-resistant reactor, purged three times with argon gas, heated to 250 °C, and reacted for 20 hours.

[0178] Cool to room temperature, add dichloromethane (300 ml), wash three times with deionized water (100 ml * 3), separate the contents, mix with silica gel, and dry-pile onto a column for silica gel column chromatography purification (200-300 mesh silica gel, dichloromethane: n-hexane = 1:5 as eluent). After elution, concentrate under reduced pressure at 60 °C for 1 hour to obtain the target compound A325 (8.06 g, purity: 99.90%, yield: 51.39%). Sublimation purification of the 8.06 g crude compound A325 yielded sublimed pure compound A325 (5.49 g, purity: 99.94%, yield: 68.12%), mass spectrometry: 669.42 (M+H).

[0179] Application example: Fabrication of organic electroluminescent devices

[0180] like Figure 1 The diagram shows a schematic of an organic electroluminescent device, comprising a glass substrate 01, an anode 02, a hole injection layer 03, a first hole transport layer 04, a first electron blocking layer 05, a first light-emitting layer 06, a first electron transport layer 07, an N-type charge generation layer 08, a P-type charge generation layer 09, a second hole transport layer 10, a second electron blocking layer 11, a second light-emitting layer 12, a second electron transport layer 13, an electron injection layer 14, and a cathode 15, stacked sequentially.

[0181] Component fabrication method:

[0182] A glass substrate 01 with an ITO transparent electrode (anode) on its surface is provided, wherein the thickness of the anode is 1000 nm;

[0183] The glass substrate 01 was washed sequentially with deionized water, ethanol, acetone and deionized water, then dried at 80°C and then treated with oxygen plasma for 30 minutes.

[0184] The compound HATCN was vapor-deposited on the surface of the anode 02 to form a hole injection layer 03 with a thickness of 20 nm.

[0185] HTL is deposited on one side of the hole injection layer 03 to form the first hole transport layer 04 with a thickness of 10 nm.

[0186] An EBL is deposited on one side of the first hole transport layer 04 to form a first electron blocking layer 05 with a thickness of 5 nm.

[0187] A host material (BH) and a guest material (BD) are co-deposited on one side of the first electron blocking layer 05 to form a first light-emitting layer 06, wherein the weight ratio of BH to BD is 97:3 and the thickness of the first light-emitting layer 06 is 20nm.

[0188] ET and LiQ are co-deposited on one side of the first light-emitting layer to form a first electron transport layer 07, wherein the weight ratio of ET to LiQ is 1:1 and the thickness of the first electron transport layer 07 is 35nm.

[0189] A heterocyclic compound and a doped material (metal Yb) are co-deposited on one side of the first electron transport layer 07 to form an N-type charge generation layer 08 (N-CGL). The types of heterocyclic compounds in the N-CGL layers of each embodiment and comparative example are shown in Table 1. The weight ratio of the heterocyclic compound to Yb is 95:5, and the thickness of the N-type charge generation layer is 100 nm.

[0190] HATCN was deposited on one side of the N-type charge generation layer 08 to form a P-type charge generation layer 09 with a thickness of 10 nm.

[0191] HTL is deposited on one side of the P-type charge generation layer 09 to form a second hole transport layer 10 with a thickness of 10 nm.

[0192] An EBL is deposited on one side of the second hole transport layer 10 to form a second electron blocking layer 11 with a thickness of 5 nm.

[0193] A host material (BH) and a guest material (BD) are co-deposited on one side surface of the second electron blocking layer 11 to form a second light-emitting layer 12, wherein the weight ratio of BH to BD is 97:3 and the thickness of the second light-emitting layer 12 is 20 nm.

[0194] ET and LiQ are co-deposited on one side of the second light-emitting layer 12 to form a second electron transport layer 13, wherein the weight ratio of ET to LiQ is 1:1 and the thickness of the second electron transport layer 13 is 35nm.

[0195] Yb is vapor-deposited on one side of the second electron transport layer 13 to form an electron injection layer 14 with a thickness of 1 nm;

[0196] Ag is vapor-deposited on one side of the electron injection layer 14 to form a cathode 15 with a thickness of 1000 nm, thus obtaining an organic electroluminescent device.

[0197] The structural formulas of HAT-CN, HTL, EBL, BH, BD, ET, LiQ, and comparative compounds 1-4 are as follows:

[0198] Comparative compounds

[0199]

[0200] evaluate:

[0201] The fabricated organic electroluminescent device was subjected to device performance testing. A constant current power supply (Keithley 2400) was used to flow a fixed current density through the light-emitting element, and the emission spectrum was measured using a spectroradiometer (CS2000). Simultaneously, at 10 mA / cm²... 2 The IVL (current-voltage-luminance) performance of the device was measured at 50 mA / cm². 2 The lifetime of the LT95 device was tested, and the drift voltage of the device (the difference between the voltage at which the lifetime decays to LT95 and the initial voltage) was also tested.

[0202] The test results are shown in Table 1:

[0203] Table 1

[0204]

[0205]

[0206] As shown in Table 1, the N-CGL layer prepared using the heterocyclic compound of the present invention, when used in a series organic light-emitting device, exhibits a significantly lower operating voltage compared to comparative compounds 1-4, effectively reducing device power consumption. Simultaneously, current efficiency and device lifetime are significantly improved, and the voltage drift value is also lower, indicating high long-term stability of the device. This heterocyclic compound, as an N-type charge-generating layer material, is suitable for OLED light-emitting devices and has potential application in the AMOLED industry.

Claims

1. A heterocyclic compound, characterized in that, The heterocyclic compound has the structure shown in formula (1) or formula (2): Where A is selected from one of the structures shown in Equations (3) to (8), and * indicates the connection site with Equations (1) and (2); Ar1 is selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C60 heteroaryl, or substituted or unsubstituted C8-C30 benzocycloalkyl, and Ar1 must meet the following conditions: I and Ar1 do not contain substituted or unsubstituted six-membered nitrogen heteroaromatic rings; II. When A is selected from formula (6), Ar1 does not contain substituted or unsubstituted pyrene or substituted or unsubstituted dibenzofuran. Ⅲ. When A is selected from formula (7) or (8), Ar1 does not contain substituted or unsubstituted oxazolyl, substituted or unsubstituted aryl-oxazolyl or substituted or unsubstituted carbazoyl. Ar2-Ar9 are each independently selected from substituted or unsubstituted C6-C30 aryl or substituted or unsubstituted C3-C60 heteroaryl; Each time R1 to R7 appears, they are independently selected from hydrogen, deuterium, halogen, cyano, nitro, C1-C40 alkyl, C1-C40 heteroalkyl, C2-C40 alkenyl, C2-C40 alkynyl, C3-C40 cycloalkyl, C3-C40 heterocycloalkyl, C6-C60 aryl, C5-C60 heteroaryl, C1-C40 alkoxy, C6-C60 aryloxy, C3-C40 alkylsilyl, C6-C60 arylsilyl, C1-C40 alkylboryl, C6-C60 arylboryl, C6-C60 arylphosphinyl, or C6-C60 arylamine. L1 and L2 are independently selected from single-bonded, substituted or unsubstituted C6-C30 arylene or substituted or unsubstituted C2-C30 heteroarylene, respectively; The substitutions described in Ar1, Ar2-Ar9, L1, and L2 are substituted by at least one selected from deuterium, halogen, cyano, C1-C40 alkyl, C6-C60 aryl, or C3-C60 heteroaryl, wherein the number of substitutions ranges from monosubstituted to the maximum number of substitutions. The heteroatom in the heteroaryl, heteroaryl, heteroalkyl, or heterocycloalkyl group is independently selected from at least one of O, S, N, Se, Si, or Ge.

2. The heterocyclic compound according to claim 1, characterized in that, Ar1 is selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 heteroaryl, or substituted or unsubstituted C8-C30 benzocycloalkyl, wherein the substitution is by at least one selected from deuterium, halogen, cyano, C1-C20 alkyl, C6-C30 aryl, or C3-C30 heteroaryl; provided that: I and Ar1 do not contain substituted or unsubstituted six-membered nitrogen heteroaromatic rings; II. When A is selected from formula (6), Ar1 does not contain substituted or unsubstituted pyrene or substituted or unsubstituted dibenzofuran. When A is selected from formulas (7) and (8), Ar1 does not contain substituted or unsubstituted oxazolyl, substituted or unsubstituted aryl-oxazolyl, or substituted or unsubstituted carbazoyl.

3. The heterocyclic compound according to claim 2, characterized in that, Ar1 is selected from one of the following structures: Each R8 is independently selected from deuterium, halogen, cyano, C1-C12 alkyl or C6-C20 aryl; 'a' represents an integer from 0 to 4. When 'a' is an integer from 2 to 4, all R8 values ​​are either the same or different; the condition is: When A is selected from equation (6), Ar1 is not... Furthermore, R8 is not a pyrene group.

4. The heterocyclic compound according to claim 1, characterized in that, Each time R1 to R7 appears, it is independently selected from hydrogen, deuterium, halogen, cyano, nitro, C1-C20 alkyl, C1-C20 heteroalkyl, C2-C20 alkenyl, C2-C20 alkynyl, C3-C20 cycloalkyl, C3-C20 heterocycloalkyl, C6-C20 aryl, or C5-C20 heteroaryl.

5. The heterocyclic compound according to claim 1, characterized in that, The heterocyclic compound is selected from one of the structures shown in formulas (A-1) to (A-4): In the formula, A, Ar1, Ar2, L1 and L2 have the definitions as described in claim 1.

6. The heterocyclic compound according to claim 1, characterized in that, The Ar2-Ar9 groups are each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted diphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthraceneyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiopheneyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirodifluorenyl, substituted or unsubstituted phenanthreneyl, etc. The combination of one or more of the following: substituted or unsubstituted pyrene, substituted or unsubstituted carbazolyl, substituted or unsubstituted pyridinyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted fluoranthyl, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted benzotriazolyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted benzophenanthryl, and substituted or unsubstituted benzocycloalkyl.

7. The heterocyclic compound according to claim 1, characterized in that, L1 and L2 are independently selected from single-bonded, substituted or unsubstituted C6-C12 arylene or substituted or unsubstituted C2-C12 heteroarylene, respectively; and / or, A is selected from one of the following structures:

8. The heterocyclic compound according to claim 1, characterized in that, The heterocyclic compound is selected from one of the following structures:

9. An organic electroluminescent device, characterized in that, It includes an anode and a cathode, with a functional layer between the cathode and the anode, the functional layer comprising a heterocyclic compound as described in any one of claims 1-8.

10. The organic electroluminescent device according to claim 9, characterized in that, The functional layer is provided with a first light-emitting unit, a charge-generating layer and a second light-emitting unit stacked sequentially from the anode side to the cathode side, and the charge-generating layer contains the heterocyclic compound; Optionally, the charge generation layer is provided with an N-type charge generation layer and a P-type charge generation layer stacked sequentially from the first light-emitting unit side to the second light-emitting unit side, wherein the N-type charge generation layer contains the heterocyclic compound; Optionally, the N-type charge generation layer further comprises a doping material selected from at least one of alkali metals, alkaline earth metals, or lanthanides. Optionally, the N-type charge generation layer contains 0.1% to 20% by mass of doped material.

11. A photoelectric element, characterized in that, It includes the heterocyclic compound as described in any one of claims 1-8 or the organic electroluminescent device as described in any one of claims 9-10.

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