Heterocyclic compound and organic electroluminescent device

Abstract

The invention belongs to the technical field of organic electroluminescence, and discloses a compound and an organic electroluminescence device. The structural general formula of the compound is as shown in formula (1), in the formula (1), A is selected from a substituted or unsubstituted anthracene ring, a substituted or unsubstituted pyrene ring or a substituted or unsubstituted ring; b is selected from a formula (B-1) or a formula (B-2) and represents a connection site with L2 in the formula (1); the compound can effectively reduce the driving voltage, improve the luminous efficiency and prolong the service life of a device, and can be used as a charge generation layer material to be applied to an OLED (Organic Light Emitting Diode) device.

Description

TECHNICAL FIELD

[0001] The present application belongs to the technical field of organic electroluminescence, and particularly relates to a heterocyclic compound and an organic electroluminescent device. BACKGROUND

[0002] At present, as a new generation of display technology, the organic electroluminescent device (OLED) has been widely concerned in the fields of display and lighting, and has shown a broad application prospect. With the continuous development of OLED technology in the fields of display and lighting, people have put forward higher requirements for the performance of OLED devices, especially in the aspects of low power consumption, high efficiency and long service life. Therefore, developing higher performance functional materials and optimizing the device structure have become the current research focus.

[0003] In the most common OLED device structure, the following functional materials are usually included: hole injection material, hole transport material, electron transport material, and light emitting material (including host material and guest material) and the like. As an important functional material, the electron transport material has a direct influence on the electron mobility, and ultimately affects the light emitting efficiency of the OLED. Therefore, improving the mobility of the electron transport material and reducing the power consumption of the device have become an important direction to improve the performance of the OLED device. By forming a series OLED structure, multiple light emitting layers are stacked and a charge generation layer is sandwiched therebetween, which can further improve the mobility. The charge generation layer usually includes an N-type charge generation layer and a P-type charge generation layer, wherein the N-type charge generation layer as an electron transport material plays an important role in improving the mobility and reducing the power consumption. However, the performance of the related material is still limited, and the device efficiency or service life still needs to be further improved.

[0004] Therefore, it is necessary to develop a charge generation layer material with higher mobility. SUMMARY

[0005] The present application aims to at least solve one of the technical problems existing in the prior art. To this end, the present application provides a heterocyclic compound, which can be used to prepare an N-type charge generation layer of an OLED, has a higher electron mobility, can effectively reduce the power consumption of the device, improve the light emitting efficiency, and prolong the service life of the device.

[0006] The first aspect of the present application provides a heterocyclic compound, which has a structure shown in formula (1): Formula (1) Wherein, A is selected from a substituted or unsubstituted anthracene ring, a substituted or unsubstituted pyrene ring, or a substituted or unsubstituted chrysene ring; B is selected from one of the following formula (B-1) or formula (B-2), Indicates the connection site with L2 in formula (1);

[0007] R a ~R b are each 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, C3-C60 heteroaryl, C1-C40 alkoxy, C6-C60 aryloxy, C3-C40 alkylsilyl, C6-C60 arylsilyl, C1-C40 alkylboronyl, C6-C60 arylboronyl, C6-C60 arylphosphino, or C6-C60 arylamino, or two adjacent R a or R b may be linked to form a ring; R c is selected from hydrogen, deuterium, cyano, halogen, C1-C18 alkyl, or C3-C30 cycloalkyl; m, n are each independently selected from an integer from 0 to 4, p is selected from an integer from 0 to 3, and x is selected from an integer from 0 to 2; L1, L2 are each independently selected from a single bond, substituted or unsubstituted C6-C60 arylene, or substituted or unsubstituted C3-C60 heteroarylene; Ar1 is selected from substituted or unsubstituted C6-C60 aryl, or substituted or unsubstituted C3-C60 heteroaryl; the heteroatoms in the heteroaryl, heteroarylene, heteroalkyl, or heterocycloalkyl are independently selected from at least one of O, S, N, Se, Si, or Ge; the substitutions in A are each independently selected from at least one of 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, C3-C60 heteroaryl, C1-C40 alkoxy, C6-C60 aryloxy, C3-C40 alkylsilyl, C6-C60 arylsilyl, C1-C40 alkylboronyl, C6-C60 arylboronyl, C6-C60 arylphosphino, or C6-C60 arylamino, wherein the number of substitutions is from mono-substitution to the maximum number of substitutions; the substitutions in L1, L2, and Ar1 are each independently selected from at least one of deuterium, halogen, cyano, isocyano, nitro, C1-C6 alkyl, C3-C16 cycloalkyl, C1-C6 alkyl-substituted amine, C1-C6 hydrocarbyl-substituted or unsubstituted C6-C30 aryl, or C1-C6 hydrocarbyl-substituted or unsubstituted C3-C30 heteroaryl, wherein the number of substitutions is from mono-substitution to the maximum number of substitutions.

[0008] The second aspect of the present application provides an organic electroluminescent device, comprising an anode and a cathode, and a functional layer between the cathode and the anode, wherein the functional layer comprises the heterocyclic compound according to the first aspect of the present application.

[0009] The third aspect of the present application provides a photoelectric element, comprising the heterocyclic compound according to the first aspect of the present application or the organic electroluminescent device according to the second aspect of the present application.

[0010] Advantages of the present application: Based on the role of the heterocyclic compound in improving electron mobility, it can be applied as a charge generation layer material in OLED devices, which can effectively reduce the driving voltage, improve the luminous efficiency, and prolong the device life, and has the potential to be applied in the AMOLED industry. Specifically, the multiple coordination sites of the compound can better coordinate with metal ions with dopants (such as alkali metals, alkaline earth metals, lanthanide metals), reducing the material cracking caused by the migration of metal ions in the device. The heterocyclic compound can reduce the energy level difference between the N-type charge generation layer and the P-type charge generation layer, thereby promoting the injection of electrons into the N-type charge generation layer, while maximizing the transfer of electrons from the N-type charge generation layer to the adjacent electron transport layer, further improving the performance of the device. BRIEF DESCRIPTION OF DRAWINGS

[0011] Figure 1 The structure of an organic electroluminescent device according to an embodiment of the present application. DETAILED DESCRIPTION

[0012] In order to make those skilled in the art more clearly understand the technical solutions of the present application, the following examples are given for illustration. It should be pointed out that the following examples do not constitute a limitation on the scope of protection required by the present application.

[0013] The first aspect of the present application provides a heterocyclic compound, which has the structure shown in formula (1): Formula (1) Wherein, A is selected from substituted or unsubstituted anthracene ring, substituted or unsubstituted pyrene ring or substituted or unsubstituted chrysene ring; B is selected from one of the following formula (B-1) or formula (B-2), Indicates the connection site with L2 in formula (1);

[0014] R a ~R beach 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, C3-C60 heteroaryl, C1-C40 alkoxy, C6-C60 aryloxy, C3-C40 alkylsilyl, C6-C60 arylsilyl, C1-C40 alkylboronyl, C6-C60 arylboronyl, C6-C60 arylphosphino, or C6-C60 arylamino, or two R a or R b may be linked to form a ring; R c selected from hydrogen, deuterium, cyano, halogen, C1-C18 alkyl, or C3-C30 cycloalkyl; m, n are each independently selected from 0, 1, 2, 3, or 4, and p is selected from 0, 1, 2, or 3; x is selected from 0, 1, or 2; L1, L2 are each independently selected from a single bond, substituted or unsubstituted C6-C60 arylene, or substituted or unsubstituted C3-C60 heteroarylene; Ar1 is selected from substituted or unsubstituted C6-C60 aryl, or substituted or unsubstituted C3-C60 heteroaryl; the heteroatoms in the heteroaryl, heteroarylene, heteroalkyl, or heterocycloalkyl are independently selected from at least one of O, S, N, Se, Si, or Ge; the substitutions in A are each independently selected from substitution by at least one of 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, C3-C60 heteroaryl, C1-C40 alkoxy, C6-C60 aryloxy, C3-C40 alkylsilyl, C6-C60 arylsilyl, C1-C40 alkylboronyl, C6-C60 arylboronyl, C6-C60 arylphosphino, or C6-C60 arylamino, wherein the number of substitutions is from mono-substitution to the maximum number of substitutions; the substitutions in L1, L2, and Ar1 are each independently selected from substitution by at least one of deuterium, halogen, cyano, isocyano, nitro, C1-C6 alkyl, C3-C16 cycloalkyl, C1-C6 alkyl-substituted amine, C1-C6 hydrocarbyl-substituted or unsubstituted C6-C30 aryl, or C1-C6 hydrocarbyl-substituted or unsubstituted C3-C30 heteroaryl, wherein the number of substitutions is from mono-substitution to the maximum number of substitutions.

[0015] In some embodiments, A is selected from one of the following structures shown in Formula (A-1) to Formula (A-5):

[0016] represents a connection site to L1, L2; wherein R1~R5are each independently selected from hydrogen, deuterium, halogen, cyano, nitro, C1-C20alkyl, C1-C20heteroalkyl, C2-C20alkenyl, C2-C20alkynyl, C3-C20cycloalkyl, C3-C20heterocycloalkyl, C6-C30aryl, C3-C30heteroaryl, C1-C20alkoxy, C6-C30aryloxy, C3-C20alkylsilyl, C6-C30arylsilyl, C1-C20alkylboron, C6-C30arylboron, C6-C30arylphosphine, or C6-C30arylamine; a, b, c, or d are each independently selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; e is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10.

[0017] In some embodiments, R1~R5are each independently selected from hydrogen, deuterium, halogen, cyano, nitro, C1-C10alkyl, C1-C10heteroalkyl, C2-C10alkenyl, C2-C10alkynyl, C3-C10cycloalkyl, C3-C10heterocycloalkyl, C6-C12aryl, or C3-C12heteroaryl.

[0018] In some embodiments, R1~R5are each independently selected from hydrogen, deuterium, cyano, or halogen.

[0019] In some embodiments, R1~R5are each independently selected from hydrogen or deuterium.

[0020] In some embodiments, the R a ~R b are each independently selected from hydrogen, deuterium, halogen, cyano, nitro, C1-C20alkyl, C1-C20heteroalkyl, C2-C20alkenyl, C2-C20alkynyl, C3-C20cycloalkyl, C3-C20heterocycloalkyl, C6-C30aryl, or C3-C30heteroaryl, or two adjacent R a or R b may be joined to form a C6-C20aryl.

[0021] In some embodiments, the R a ~R beach independently selected from hydrogen, deuterium, halogen, cyano, nitro, C1-C10 alkyl, C1-C10 heteroalkyl, C2-C10 alkenyl, C2-C10 alkynyl, C3-C10 cycloalkyl, C3-C10 heterocycloalkyl, C6-C12 aryl, C5-C12 heteroaryl, or two R a or R b may be linked to form a C6-C12 aryl.

[0022] In some embodiments, the R a or R b are each independently selected from hydrogen, deuterium, cyano, or halogen; or two R a or R b form a C6-C12 aryl.

[0023] In some embodiments, the R a or R b are each independently selected from hydrogen or deuterium; or two R a or R b form a phenyl.

[0024] In some embodiments, L1, L2in the heterocyclic compound are each independently selected from a single bond, substituted or unsubstituted C6-C40 arylene, or substituted or unsubstituted C3-C40 heteroarylene.

[0025] In some embodiments, L1, L2in the heterocyclic compound are each independently selected from a single bond, substituted or unsubstituted C6-C25 arylene, or substituted or unsubstituted C3-C20 heteroarylene.

[0026] In some embodiments, L1, L2are each independently selected from a single bond, deuterated or non-deuterated one of the structures represented by Formula (C-1) to Formula (C-13):

[0027] represents the site of attachment to A, B, or -CN.

[0028] In some embodiments, Ar1is selected from substituted or unsubstituted C6-C30 aryl or substituted or unsubstituted C3-C30 heteroaryl.

[0029] In some embodiments, Ar1is selected from substituted or unsubstituted C6-C25 aryl or substituted or unsubstituted C3-C20 heteroaryl.

[0030] In some embodiments, said Ar1is selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted pyrenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted pyridinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted fluoranthenyl, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted benzotriazolyl, substituted or unsubstituted phenanthrolinyl, or a combination of at least two of the foregoing.

[0031] In some embodiments, said Ar1is selected from substituted or unsubstituted phenyl, substituted or unsubstituted pyridinyl, substituted or unsubstituted naphthyl, substituted or unsubstituted bi-phenyl, or substituted or unsubstituted tri-phenyl, wherein said phenyl, pyridinyl, naphthyl, bi-phenyl, or tri-phenyl can be optionally substituted with one or more hydrogen, deuterium, phenyl, pyridinyl, or naphthyl.

[0032] In some embodiments, said Ar1is selected from substituted or unsubstituted phenyl, substituted or unsubstituted pyridinyl, substituted or unsubstituted naphthyl, or substituted or unsubstituted bi-phenyl, said substitution being substitution with deuterium.

[0033] In some embodiments, said substitution in L1, L2, and Ar1is at least one substitution with deuterium, halogen, cyano, isocyano, phosphino, C1-C6alkyl, C3-C12cycloalkyl, or C1-C6alkyl substituted amine, wherein the number of substitutions is from mono-substitution to the maximum number of substitutions.

[0034] In some embodiments, said substitution in L1, L2, and Ar1is at least one substitution with deuterium, halogen, cyano, isocyano, phosphino, C1-C6alkyl, C3-C10cycloalkyl, wherein the number of substitutions is from mono-substitution to the maximum number of substitutions.

[0035] In some embodiments, said heterocyclic compound satisfies at least one of the following: (1) A is selected from one of the structures represented by formula (A-6) to formula (A-10) with or without deuterium:

[0036] wherein represents the site of attachment to L1or L2; (2) B is selected from one of the structures represented by formula (B-3) to formula (B-5) with or without deuterium:

[0037] wherein represents the site of attachment to L2in Formula (1); (3) L1or L2are each independently selected from one of the structures depicted in Formula (C-14) through Formula (C-19):

[0038] wherein represents the site of attachment to A, B, or -CN.

[0039] In some embodiments, the heterocyclic compound is one of the following structural formulae, or one of the following structural formulae in which the hydrogens are partially or fully replaced by deuterium, fluorine:

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[0128] The second aspect embodiment of the present application provides an organic electroluminescent device comprising the above-mentioned heterocyclic compound.

[0129] In some embodiments, the organic electroluminescent device includes an anode and a cathode, and a functional layer provided between the anode and the cathode, the functional layer comprising the above-mentioned heterocyclic compound.

[0130] In some embodiments, the functional layers are stacked in order from the anode side to the cathode side as the first light-emitting unit, the charge generation layer, and the second light-emitting unit, wherein the charge generation layer contains the heterocyclic compound described above.

[0131] In some embodiments, the functional layers are stacked in order from the first light-emitting unit side to the second light-emitting unit side as the N-type charge generation layer and the P-type charge generation layer, wherein the N-type charge generation layer contains the heterocyclic compound described above.

[0132] In some embodiments, the N-type charge generation layer further contains a doping material.

[0133] In some embodiments, the doping material is selected from at least one of alkali metals (e.g., Li, Na, K), alkaline earth metals (e.g., Ca, Mg), or lanthanide metals (e.g., La, Yb, Ce).

[0134] In some embodiments, in the N-type charge generation layer, the mass percentage of the doping material can be 0.1%-20%, or 1%-10%, or 1%-5%; and the mass percentage of the heterocyclic compound described above can be 80%-99.9%, or 90%-99%, or 95%-99%.

[0135] In some embodiments, the first light-emitting unit is stacked in order from the anode side to the charge generation layer side as the first hole functional layer, the first light-emitting layer, and the first electron functional layer. As an example, the first hole functional layer is stacked in order from the anode side to the first light-emitting layer side as a hole injection layer, a first hole transport layer, and a first electron blocking layer; and the first electron functional layer includes a first electron transport layer.

[0136] In some embodiments, the second light-emitting unit is stacked in order from the charge generation layer to the cathode side as the second hole functional layer, the second light-emitting layer, and the second electron functional layer. As an example, the second hole functional layer is stacked in order from the charge generation layer side to the second light-emitting layer side as a second hole transport layer and a second electron blocking layer; and the second electron functional layer is stacked in order from the second light-emitting layer side to the cathode side as a second electron transport layer and an electron injection layer.

[0137] In some embodiments, the functional layers are stacked in order from the anode side to the cathode side as 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 heterocyclic compound described above.

[0138] It should be noted that the present application does not limit the stacking structure of the light-emitting unit, and any stacking structure known in the prior art can be used by those skilled in the art.

[0139] A third aspect embodiment of the present application provides an optoelectronic element comprising the organic electroluminescent device described above.

[0140] Non-limiting examples of the optoelectronic element include: a lighting appliance (such as a lamp), a display (such as a vehicle display, a computer display, or a television display, wherein the display type can be an AMOLED display), or a sensor, etc.

[0141] Definitions Unless otherwise defined, scientific and technical terms used in this document shall have the meanings commonly understood by one of ordinary skill in the art, although it is intended that the definitions provided herein be applicable to the meanings of the terms as they are used throughout this application. Whereas the definitions provided herein are intended to apply to the terms as they are used in the context of this application, the definitions provided herein are not intended to apply to the terms as they are used in any context other than as provided herein.

[0142] In this specification, denotes a point of attachment to other groups.

[0143] As used herein, the term “and / or” means that the listed items are individually present or combined. In fact, the term means that “at least one” or “one or more” of the listed items is used or present.

[0144] The term “plurality” means a number greater than or equal to 2, such as 2, 3, 4, 5, 6, 7, 8, 9, 10, etc.

[0145] “0-10 integer” can be any one of 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10 or a range formed by any two of them. “0-2 integer”, “0-3 integer”, “0-4 integer”, or “0-8 integer” are similar.

[0146] “Halogen” means fluorine, chlorine, bromine, or iodine.

[0147] “Alkyl” means a straight-chain or branched-chain saturated hydrocarbon group. The number of carbon atoms can be C1-C60, C1-C40, C1-C30, C1-C20, C1-C12, C1-C10, C1-C6, or C1-C4. Non-limiting examples include methyl, ethyl, propyl, butyl, heptyl, and decyl, etc. Each group includes various isomers, such as butyl includes n-butyl, isobutyl, sec-butyl, t-butyl, and the like.

[0148] "Cycloalkyl" refers to an alkyl group with a cyclic structure, which can include monocyclic, polycyclic, and spiroalkyl groups. The number of carbon atoms can be C3-C60, C3-C40, C3-C30, C3-C20, C3-C12, C3-C10, or C3-C6. Non-limiting examples include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 1-adamantyl, 2-adamantyl, 1-norbornyl, and 2-norbornyl, among others.

[0149] "Alkenyl" refers to a hydrocarbon comprising at least one unsaturated carbon-carbon double bond. The number of carbon atoms can be C2-C40, C2-C30, C2-C20, C2-C12, C2-C10, C2-C6, or C2-C4. Non-limiting examples include ethenyl, propenyl, allyl, butadienyl, hexatrienyl, and the like.

[0150] "Alkynyl" refers to a hydrocarbon comprising at least one unsaturated carbon-carbon triple bond. The number of carbon atoms can be C2-C40, C2-C30, C2-C20, C2-C12, C2-C10, C2-C6, or C2-C4. Non-limiting examples include ethynyl and propynyl, among others.

[0151] "Heteroalkyl" refers to an alkyl group in which at least one carbon atom is replaced by a non-carbon atom, excluding cases where the carbon atom that is the point of attachment is replaced by a non-carbon atom (e.g., alkoxy, alkylsilyl groups). The number of carbon atoms can be C1-C40, C1-C30, C1-C20, C1-C12, C1-C10, C1-C6, or C1-C4. For example, mercaptomethylmethane, methoxymethylmethane, ethoxymethylmethane, t-butoxymethylmethane, N,N-dimethylmethylmethane.

[0152] "Heterocycloalkyl" refers to a cycloalkyl group in which at least one ring carbon atom is replaced by a non-carbon atom, which can be selected from at least one of O, S, N, P, B, Si, Ge, or Se. The number of ring carbon atoms can be C3-C40, C3-C30, C3-C20, C3-C12, C3-C10, or C3-C6. Non-limiting examples include cyclobutanoxyl, cyclopentanoxyl, and cyclohexanoxyl.

[0153] "Aryl" means an aromatic hydrocarbon group derived by removing a hydrogen atom from a aromatic ring compound, which can be a monocyclic aryl group or a polycyclic aryl group. At least one ring in the polycyclic aryl group is an aromatic ring system. Multiple rings in the polycyclic aryl group can be connected to each other via a single bond or can be fused to each other, for example, a phenyl group and a phenyl group are fused to form a naphthyl group, or a phenyl group and a phenyl group are connected by a single bond to form a biphenyl group. The number of carbon atoms can be C6-C60, C6-C30, C6-C20, C6-C12, or C6-C10. Non-limiting examples include phenyl, naphthyl, anthryl, phenanthryl, tetracenyl, pyrenyl, perylenyl, acenaphthyl, benzopyrenyl, benzophenanthryl, benzo[g]chrysenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, biphenyl, terphenyl, quaterphenyl, and fluoranthenyl, and the like. Benzophenanthryl includes 1,2 benzophenanthrene, 3,4-benzophenanthrene, 9,10-benzophenanthrene, and the like.

[0154] "Heteroaryl" means an aromatic group in which at least one carbon atom is replaced by a non-carbon atom, which can be a monocyclic heteroaryl group or a polycyclic heteroaryl group. Multiple rings in the polycyclic heteroaryl group can be connected to each other via a single bond or can be fused to each other, wherein at least one ring has at least one carbon atom replaced by a non-carbon atom, for example, a phenyl group and a carbazolyl group are fused to form a benzocarbazolyl group, or a phenyl group and a carbazolyl group are connected by a single bond to form a phenyl-substituted carbazolyl group or a carbazolyl-substituted phenyl group. The non-carbon atom can be selected from a monovalent group of a heterocyclic aromatic system of O, S, N, Se, Si, or Ge, but does not include the case where aryl is connected to a non-carbon atom as a connecting site (for example, aryloxy, arylsilyl, arylamine). The number of carbon atoms can be C3-C30, C3-C20, C3-C12, C3-C10, or C3-C6. Non-limiting examples include pyrrolyl, pyrrolopyrrolyl, furopyrrolyl, thienopyrrolyl, pyridyl, pyrazolyl, pyrimidinyl, pyrazinyl, pyridazinyl, phenoxazinyl, phenothiazinyl, phenoxazinyl, indolyl, isoindolyl, indolazolyl, imidazolyl, benzimidazolyl, triazolyl, tetrazolyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, furopyranyl, azadibenzofuranyl, thienofuranyl, diazadibenzofuranyl, benzo[B]naphtho[1,2-D]furanyl, quinolyl, isoquinolyl, quinoxalyl, quinazolinyl, quinazolinonyl, carbazolyl, azacarbazolyl, diazacarbazolyl, phenanthridinyl, perimidinyl, acridinyl, dihydroacridinyl, phenanthrolinyl, oxazolinyl, oxazolyl, oxadiazolyl, benzisoxazolyl, thiazolyl, benzothiazolyl, benzisothiazolyl, pyrroloimidazolyl, furazanyl, thienyl, benzothienyl, dibenzothienyl, azadibenzothienyl, diazadibenzothienyl, thienothienyl, and phthalazinyl, and the like.

[0155] "Alkoxy" refers to a group having an "O-alkyl" structure, meaning that the alkyl group as defined above is connected to the parent nucleus via an oxygen atom. Non-limiting examples include: methoxy, ethoxy, and tert-butoxy (-OC(CH3)3 or... OtBu), etc.

[0156] "Aryloxy group" refers to a group having an "O-aryl" structure, that is, an aryl group as defined above is attached to the parent nucleus via an oxygen atom. Non-limiting examples of aryloxy groups include phenoxy, naphthoxy, or biphenyloxy groups.

[0157] "Aryl group" refers to an alkyl group substituted with an aryl group, wherein the definitions of "aryl" and "alkyl" are as described above. The number of carbon atoms in an aryl group can be C7-C30, C7-20, C7-12, or C7-10. Non-limiting examples include benzyl, phenethyl, phenylpropyl, tolylmethyl, and p-tolylmethyl, etc.

[0158] "Alkylamine" refers to an amino group substituted with an alkyl group, where "alkyl" is defined as previously stated. The number of carbon atoms in an alkylamine group can be C0-C20, C0-C12, C0-C10, C0-C6, or C0-C4. When the alkylamine group is C0, i.e., has 0 carbon atoms, it represents a -NH2 group. Other non-limiting examples of alkylamine groups include: methylamino, ethylamino, dimethylaminotriethylammonium diisopropylamino, and trimethylammonium.

[0159] arylene and heteroarylene correspond to divalent groups in aryl and heteroaryl structures, respectively.

[0160] In expressions such as "the R group of substituted or unsubstituted Ca-Cb", "Ca-Cb" refers to the number of carbon atoms a to b when the R group is unsubstituted, excluding the number of carbon atoms in the substituents when the R group is substituted.

[0161] "Substitution" in "substituted or unsubstituted" means that one or more hydrogen atoms are replaced by other atoms or groups, and unless otherwise defined, it also includes the replacement of one or more hydrogen atoms by groups formed by the connection of two or more of the substituents described above.

[0162] "Maximum number of substitutions" refers to the maximum number of hydrogen atoms contained in the group when there are no substituents other than hydrogen.

[0163] When any group is referred to as “optionally substituted,” unless specifically defined, it means that the group is substituted or not substituted, provided that such substitution does not violate conventional bonding principles known to those skilled in the art.

[0164] "combination of at least two" means that at least two defined groups are connected by a single bond or fused. For example, phenyl and phenyl are fused to form naphthyl, or phenyl and phenyl are connected by a single bond to form biphenyl. It should be understood that the combination of groups is subject to the range of carbon numbers defined.

[0165] "two R a or R b "may be connected to form a fused ring" means that two R a "may be connected to form a fused ring" or two R b "may be connected to form a fused ring".

[0166] "Biphenyl" refers to a general term for aromatic groups formed by two or more benzene rings directly connected by a single bond, including but not limited to biphenyl, terphenyl, quaterphenyl, etc. "Biphenylene" refers to a general term for divalent aromatic groups formed by two or more benzene rings directly connected by a single bond (without heteroatoms or bridges intervening), including but not limited to biphenylene, terphenylene, quaterphenylene, etc.

[0167] The following examples are only for the convenience of understanding the technical invention, and should not be regarded as specific limitations of the invention.

[0168] The raw materials and solvents involved in the synthesis of the compounds in the present application are purchased from Alfa, Acros, and other suppliers well known to those skilled in the art.

[0169] Synthesis of compound A1

[0170] Synthesis of compound A1-3 Compound A1-1 (15.00 g, 2102.08 mmol, CAS: 126747-14-6), compound A1-2 (41.16 g, 122.20 mmol, CAS: 523-27-3), [1,1'-bis(diphenylphosphino)ferrocene] dichloropalladium (0.75 g, 1.02 mmol), potassium carbonate (29.63 g, 214.37 mmol), 1,4-dioxane (250 ml), deionized water (50 ml) were added to a 500 ml three-necked round-bottom flask, replaced with vacuum nitrogen three times, then the system was heated to 75°C for 6 hours, TLC (ethyl acetate: n-hexane = 1:10 as developing agent) was used to monitor the reaction, and compound A1-1 was consumed.

[0171] Cool to 60°C, concentrate under reduced pressure to remove the solvent, add dichloromethane (150 ml), wash with deionized water three times (50 ml 3), liquid-liquid extraction, silica gel mixing, dry column, silica gel column chromatography purification (200-300 mesh silica gel, ethyl acetate: n-hexane = 1:15 as eluent), after elution, 60°C reduced pressure concentration 1 hour to obtain solid compound A1-3 (17.43g, purity: 99.33%, yield: 47.66%), mass spectrum: 358.02 (M+H).

[0172] Synthesis of compound A1 Compound A1-3 (15.00g, 41.87mmol), compound A1-4 (15.04g, 41.87mmol, CAS: 1176879-36-9), tetrakis(triphenylphosphine)palladium (0.18g, 0.42mmol), potassium carbonate (14.47g, 104.68mmol), 1,4-dioxane (250ml), deionized water (50ml) were added into a 500ml three-necked round-bottom flask, replaced with vacuum nitrogen three times, then the system was heated to 75°C for 6 hours, TLC (dichloromethane:methanol = 10:1 as developing agent) was used to monitor the reaction, and compound A1-4 was consumed.

[0173] After the reaction was completed, it was cooled to room temperature, dichloromethane (90ml 3) and deionized water (50ml) were used for extraction, and the organic phase was dried (60°C) to obtain a light yellow solid. Silica gel mixing, dry column, silica gel column chromatography purification (200-300 mesh silica gel, dichloromethane as eluent), after elution, 60°C reduced pressure concentration 1 hour to obtain white solid compound A1 (14.43g, purity: 99.95%, yield: 67.49%). 14.43g of crude compound A1 was purified by sublimation to obtain sublimation purified compound A1 (12.14, purity: 99.95%, yield: 864.13%), mass spectrum: 511.18 (M+H).

[0174] 1 H NMR (400 MHz, CDCl3) δ 8.74 (s, 2H), 8.70 (dd, J = 4.0, 1.7 Hz,2H), 8.62 (dd, J = 8.3, 1.4 Hz, 2H), 8.23 – 8.18 (m, 4H), 7.81 – 7.73 (m,4H), 7.64 – 7.61 (m, 2H), 7.51 – 7.48 (m, 4H), 7.24-7.20 (m, 2H). Synthesis of intermediate A214-4

[0175] Synthesis of compound A214-2 Referring to the synthesis and purification method of compound A1, only the corresponding starting material needs to be changed to obtain target compound A214-2 (12.64 g, purity: 99.35%, yield: 72.09%), mass spectrum: 420.12 (M+H). Among them, A214-1 CAS: 126866-33-9.

[0176] Synthesis of intermediate A214-4 Compound A214-2 (12.50 g, 29.77 mmol), compound A214-3 (7.56 g, 29.77 mmol), tris(dibenzylideneacetone)dipalladium (0.27 g, 0.30 mmol), 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (0.28 g, 0.60 mmol), potassium acetate (6.43 g, 65.49 mmol), 1,4-dioxane (200 ml) were added to a 500 ml single-necked round-bottomed flask, replaced with vacuum nitrogen three times, then the system was heated to 100°C for 2 hours, TLC (dichloromethane:methanol=10:1 as developing agent) was used to monitor the reaction, and compound A214-2 was consumed.

[0177] Cool to 60°C, concentrate under reduced pressure to remove the solvent, add dichloromethane (200 ml), wash with deionized water three times (50 ml 3), extract and separate, mix with silica gel, dry column, and perform silica gel column chromatography purification (200-300 mesh silica gel, dichloromethane:methanol=20:1 as eluent), after elution, concentrate under reduced pressure at 60°C for 1 hour to obtain white solid compound A214-4 (11.23 g, purity: 99.03%, yield: 73.76%), mass spectrum: 512.24 (M+H).

[0178] Synthesis of intermediate A266-2

[0179] Synthesis of intermediate A266-2 Referring to the synthesis and purification method of compound A214-4, only the corresponding starting material needs to be changed to obtain target compound A266-2 (11.57 g, purity: 99.20%, yield: 74.28%), mass spectrum: 436.21 (M+H). Among them, A266-1 CAS: 2620442-38-6.

[0180] Synthesis of intermediate A299-4

[0181] Synthesis of compound A299-3 Reference to the synthesis and purification method of compound A1, only need to change the corresponding raw material can be obtained target compound A299-3 (13.48g, purity: 99.27%, yield: 69.41%), mass spectrum: 471.13 (M+H). Wherein A299-1 CAS:925890-48-8.

[0182] Synthesis of intermediate A299-4 Reference to the synthesis and purification method of compound A214-4, only need to change the corresponding raw material can be obtained target compound A299-4 (11.18g, purity: 99.16%, yield: 72.01%), mass spectrum: 563.25 (M+H).

[0183] Synthesis of intermediate A444-4

[0184] Synthesis of compound A444-3 Compound A444-1 (16.43g, 94.98mmol, CAS:1219080-58-6), compound A444-2 (15.00g, 43.17mmol, CAS:2533347-68-9), tris (dibenzylideneacetone) dipalladium (0.40g, 0.43mmol), 2-dicyclohexylphosphino-2',4',6'-triisopropyl biphenyl (0.41g, 0.86mmol), potassium carbonate (13.13g, 94.98mmol), 1,4-dioxane (250ml), deionized water (50ml) were added into a 500ml single necked round bottom flask, replaced with vacuum nitrogen three times, then the system was heated to 75°C for 6 hours, TLC (dichloromethane:methanol=10:1 as developing agent) monitoring reaction, compound A444-2 was consumed.

[0185] Cool to 60°C, concentrated under reduced pressure to remove the solvent, dichloromethane (200ml) was added, washed with deionized water three times (50ml 3), extraction and separation, silica gel sample mixing, dry column, silica gel column chromatography purification (200-300 mesh silica gel, dichloromethane:methanol=10:1 as eluent), after elution, 60°C under reduced pressure for 1 hour to get white solid as compound A444-3 (11.75g, purity: 99.10%, yield: 61.31%), mass spectrum: 444.12 (M+H).

[0186] Synthesis of intermediate A444-4 Following the synthesis and purification method of compound A214-4, only the corresponding raw materials need to be changed to obtain the target compound A444-4 (10.31 g, purity: 99.31%, yield: 74.33%), mass spectrometry: 536.25 (M+H).

[0187] Combining the above intermediates, compounds A27, A37, A64, A81, A102, A130, A171, A214, A243, A266, A299, A401, A442, and A444 were prepared using a similar synthetic method to compound A1-3, the difference being the different raw materials used, as shown in the table below.

[0188]

[0189] Application example: Fabrication of organic electroluminescent devices 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.

[0190] Component fabrication method: A glass substrate 01 with an ITO transparent electrode (anode) on its surface is provided, wherein the thickness of the anode is 1000 nm; 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. 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. 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. 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. 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. 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. 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. 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. 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. 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. A host material (BH) and a guest material (BD) are co-deposited on one side 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. 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. Yb is deposited on one side of the second electron transport layer 13 to form an electron injection layer 14 with a thickness of 1 nm. 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.

[0191] The structural formulas of HAT-CN, HTL, EBL, BH, BD, ET, LiQ, and comparative compounds 1-4 are as follows:

[0192] Comparative compounds

[0193] evaluate: The prepared organic electroluminescent device is subjected to device performance test. A constant current power supply (Keithley 2400) is used to flow through the light-emitting element with a fixed current density, and a spectroradiometric luminance meter (CS 2000) is used to test the light-emitting spectrum. Meanwhile, the IVL (current-voltage-luminance) performance of the device is determined at 10 mA / cm 2 and the LT95 device lifetime is tested, and the drift voltage of the device (the difference between the voltage at the time of LT95 and the initial voltage) is tested. 2

[0194] The test results are shown in Table 1: Table 1

[0195] As can be seen from Table 1, the anthracene-containing heterocyclic compound of the embodiment of the present application is beneficial to the stability of metal coordination by specific connection of the cyano substituent group. At the same time, the energy level can be fine-tuned, and the electron injection energy barrier is low. The N-CGL layer prepared by the heterocyclic compound of the embodiment of the present application has a significantly reduced device operating voltage when used in a tandem organic electroluminescent device, effectively reducing the power consumption of the device. At the same time, the current efficiency and the device lifetime are significantly improved, and the device has a lower voltage and a drift voltage, indicating that the long-time working stability of the device is also relatively high. The heterocyclic compound as an N-type charge generation layer material is suitable for OLED light-emitting devices and has potential applications in the AMOLED industry.​

Claims

1. A heterocyclic compound, characterized in that, It has the structure shown in equation (1): in, A is selected from substituted or unsubstituted anthracene rings, substituted or unsubstituted pyrene rings, or substituted or unsubstituted β rings; B is selected from one of the structures shown in formula (B-1) or formula (B-2). This indicates the connection point with L2 in equation (1). R a ~R b Each of the following groups is independently selected from hydrogen, deuterium, halogen, cyano, nitro, C1-C40 alkyl, C1-C40 heteroalkyl, C2-C40 alkenyl, C2-C40 alkynyl, C3-C40 heterocycloalkyl, C6-C60 aryl, C3-C60 heteroaryl, C1-C40 alkoxy, C6-C60 aryloxy, C3-C40 alkylsilyl, C6-C60 arylsilyl, C1-C40 alkylboron, C6-C60 arylboron, C6-C60 arylphosphine, or C6-C60 arylamine, or two adjacent R groups. a or R b They can be connected to form a ring; R c Selected from hydrogen, deuterium, cyano, halogen, C1-C18 alkyl or C3-C30 cycloalkyl; m and n are independently selected from integers from 0 to 4, p is selected from integers from 0 to 3, and x is selected from integers from 0 to 2; L1 and L2 are independently selected from single-bonded, substituted or unsubstituted C6-C60 arylene or substituted or unsubstituted C3-C60 heteroarylene, respectively; Ar1 is selected from substituted or unsubstituted C6-C60 aryl or substituted or unsubstituted C3-C60 heteroaryl; 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; The substitutions described in A are each independently selected from at least one of hydrogen, deuterium, halogen, cyano, nitro, C1-C40 alkyl, C1-C40 heteroalkyl, C2-C40 alkenyl, C2-C40 alkynyl, C3-C40 heterocycloalkyl, C6-C60 aryl, C3-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 arylamino, wherein the number of substitutions ranges from monosubstituted to the maximum number of substitutions; The substitutions described in L1, L2 and Ar1 are each independently selected from at least one of deuterium, halogen, cyano, isocyano, nitro, C1-C6 alkyl, C3-C16 cycloalkyl, C1-C6 alkyl-substituted amino, C6-C30 aryl substituted or unsubstituted C1-C6 alkyl, or C3-C30 heteroaryl substituted or unsubstituted C1-C6 alkyl, wherein the number of substitutions ranges from monosubstituted to the maximum number of substitutions.

2. The heterocyclic compound according to claim 1, characterized in that, A is selected from one of the structures shown in equations (A-1) to (A-5): Indicates the connection site with L1 or L2; In the formula, R1 to R5 are 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-C30 aryl, C3-C30 heteroaryl, C1-C20 alkoxy, C6-C30 aryloxy, C3-C20 alkylsilyl, C6-C30 arylsilyl, C1-C20 alkylboryl, C6-C30 arylboryl, C6-C30 arylphosphinyl or C6-C30 arylamino. a, b, c, or d are each independently selected from integers from 0 to 8; e is selected from integers from 0 to 10.

3. The heterocyclic compound according to claim 1 or 2, characterized in that, The R a ~R b Each of the following 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-C30 aryl or C3-C30 heteroaryl, or two adjacent Rs. a or R b They can be linked to form C6-C20 aryl groups; Or, R c Selected from hydrogen, deuterium, cyano, halogen, C1-C6 alkyl or C3-C12 cycloalkyl; Alternatively, L1 and L2 are independently selected from single-bonded, substituted or unsubstituted C6-C40 arylene or substituted or unsubstituted C3-C40 heteroarylene, respectively; Alternatively, the Ar1 is selected from substituted or unsubstituted C6-C30 aryl or substituted or unsubstituted C3-C30 heteroaryl; Alternatively, R1 to R5 are each independently selected from hydrogen, deuterium, halogen, cyano, nitro, C1-C10 alkyl, C1-C10 heteroalkyl, C2-C10 alkenyl, C2-C10 alkynyl, C3-C10 cycloalkyl, C3-C10 heterocycloalkyl, C6-C12 aryl or C3-C12 heteroaryl; Wherein, the substitution in L1, L2 and Ar1 is at least one substituted amino group substituted by deuterium, halogen, cyano, isocyano, phosphin, C1-C6 alkyl, C3-C12 cycloalkyl or C1-C6 alkyl, wherein the number of substitutions is from monosubstituted to the maximum number of substitutions.

4. The heterocyclic compound according to claim 1 or 2, characterized in that, The R a or R b Each R group is independently selected from hydrogen, deuterium, cyano, or halogen; or two adjacent R groups. a or R b Formation of C6-C12 aryl groups; Or, the R c Selected from hydrogen or deuterium; Alternatively, R1 to R5 may be independently selected from hydrogen, deuterium, cyano, or halogen; Alternatively, L1 and L2 are independently selected from single-bonded, substituted or unsubstituted C6-C25 arylene or substituted or unsubstituted C3-C20 heteroarylene, respectively; Alternatively, Ar1 may be selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthraquinyl, 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, substituted or unsubstituted pyridyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted pyrimidinyl, etc. The Ar1 is selected from substituted or unsubstituted fluoranthracene, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted benzotriazolyl, substituted or unsubstituted benzophenanthryl, or a combination of at least two of the above; optionally, the Ar1 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthrayl, substituted or unsubstituted diphenyl, or substituted or unsubstituted terphenyl, wherein the phenyl, pyridyl, naphthyl, anthrayl, diphenyl, or terphenyl may optionally be substituted by one or more hydrogen, deuterium, phenyl, pyridyl, or naphthyl; The substitutions in L1, L2 and Ar1 are made by at least one of deuterium, halogen, cyano, isocyano, C1-C6 alkyl or C3-C10 cycloalkyl, wherein the number of substitutions ranges from monosubstituted to the maximum number of substitutions.

5. The heterocyclic compound according to claim 1, characterized in that, L1 and L2 are each independently selected from one of the structures shown in formulas (C-1) to (C-13) that are single-bonded, deuterated, or undeuterated: Indicates the connection site with A, -CN, or B.

6. The heterocyclic compound according to claim 1, characterized in that, The heterocyclic compound satisfies at least one of the following: (1) A is selected from one of the structures shown in formulas (A-6) to (A-10) that are deuterated or undeuterated: in Indicates the connection site with L1 or L2; (2) B is selected from one of the structures shown in formulas (B-3) to (B-5) that are deuterated or undeuterated: in Indicates the connection point with L2 in equation (1); (3) L1 or L2 is independently selected from one of the structures shown in formulas (C-14) to (C-19) that are single-bonded, deuterated, or undeuterated: in Indicates the connection site with A, B, or -CN.

7. The heterocyclic compound according to claim 1, characterized in that, The heterocyclic compound has one of the following structural formulas, or in the following structural formulas, at least one hydrogen atom is substituted with deuterium. 。 8. An organic electroluminescent device, characterized in that, It includes an anode and a cathode, with a functional layer provided between the anode and the cathode, the functional layer comprising a heterocyclic compound as described in any one of claims 1-7.

9. The organic electroluminescent device according to claim 8, characterized in that, The functional layer comprises a first light-emitting unit, an N-type charge-generating layer, a P-type charge-generating layer, and a second light-emitting unit, which are sequentially stacked from the anode side to the cathode side. The N-type charge-generating layer comprises a heterocyclic compound as described in any one of claims 1-7.

10. A photoelectric element, characterized in that, Includes heterocyclic compounds as described in any one of claims 1-7 or organic electroluminescent devices as described in any one of claims 8-9.

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