Heterocyclic compounds and organic electroluminescent devices and electronic devices

Abstract

This application relates to the technical field of organic electroluminescent materials and provides a heterocyclic compound, an organic electroluminescent device, and an electronic device containing the same. The heterocyclic compound of the present application comprises a parent core structure of naphthofuroxazole / thiazole and a triarylamine. When used as a host material or hole-adjusting layer in an organic electroluminescent device, the compound can significantly improve the device's luminous efficiency and lifetime.

Description

Technical Field

[0001] The present application relates to the technical field of organic electroluminescent materials, and in particular to heterocyclic compounds and organic electroluminescent devices and electronic devices containing the same. Background Art

[0002] With the development of electronic technology and the progress of materials science, the application scope of electronic components for realizing electroluminescence or photoelectric conversion is becoming more and more extensive. Organic electroluminescent devices (OLEDs) generally include: a cathode and an anode arranged opposite to each other, and a functional layer arranged between the cathode and the anode. The functional layer is composed of multiple organic or inorganic film layers, and generally includes an organic light-emitting layer, a hole transport layer, an electron transport layer, etc. When voltage is applied to the anode and cathode, the two electrodes generate an electric field. Under the action of the electric field, the electrons on the cathode side move toward the electroluminescent layer, and the holes on the anode side also move toward the light-emitting layer. The electrons and holes combine in the electroluminescent layer to form excitons. The excitons are in an excited state and release energy outward, thereby causing the electroluminescent layer to emit light outward.

[0003] The main problems with existing organic electroluminescent devices are lifespan and efficiency. As displays become larger, the driving voltage also increases, and the luminous efficiency and current efficiency also need to be improved. Therefore, it is necessary to continue to develop new materials to further improve the performance of organic electroluminescent devices. Summary of the Invention

[0004] In view of the above problems existing in the prior art, the purpose of the present application is to provide a heterocyclic compound and an organic electroluminescent device and an electronic device containing the same. The heterocyclic compound is used in the organic electroluminescent device to improve the performance of the device.

[0005] According to a first aspect of the present application, a heterocyclic compound is provided, wherein the heterocyclic compound has a structure represented by Formula 1:

[0006]

[0007] wherein Y is selected from S or O;

[0008] One of X and Z is —N=, and the other is O or S;

[0009] Ring A is selected from a naphthalene ring or a phenanthrene ring;

[0010] L, L1 and L2 are the same or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;

[0011] Ar1, Ar2 and Ar3 are the same or different and are each independently selected from a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 40 carbon atoms, an alkyl group having 1 to 10 carbon atoms or a cycloalkyl group having 3 to 10 carbon atoms;

[0012] The substituents in L, L1, L2, Ar1, Ar2 and Ar3 are the same or different and are independently selected from deuterium, cyano, halogen, alkyl having 1 to 10 carbon atoms, haloalkyl having 1 to 10 carbon atoms, deuterated alkyl having 1 to 10 carbon atoms, trialkylsilyl having 3 to 12 carbon atoms, triphenylsilyl, aryl having 6 to 20 carbon atoms, deuterated aryl having 6 to 20 carbon atoms, heteroaryl having 3 to 20 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, alkoxy having 1 to 10 carbon atoms, alkylthio having 1 to 10 carbon atoms, aryloxy having 6 to 20 carbon atoms or arylthio having 6 to 20 carbon atoms; optionally, any two adjacent substituents form a saturated or unsaturated 3 to 15-membered ring;

[0013] Each R is the same or different and is independently selected from hydrogen, deuterium, cyano, a halogen group, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, a triphenylsilyl group, an aryl group having 6 to 20 carbon atoms, a heteroaryl group having 3 to 20 carbon atoms, or a cycloalkyl group having 3 to 10 carbon atoms; optionally, any two adjacent R groups form a ring; and n is selected from 1, 2, 3, 4, 5, 6, 7, 8 or 9.

[0014] According to a second aspect of the present application, an organic electroluminescent device is provided, comprising an anode and a cathode disposed opposite to each other, and a functional layer disposed between the anode and the cathode; the functional layer comprises the above-mentioned heterocyclic compound.

[0015] According to a third aspect of the present application, an electronic device is provided, comprising the organic electroluminescent device according to the second aspect.

[0016] The present application's compound structure includes the structure of naphthalene (phenanthrene) furan and oxazole / thiazole and triarylamine, wherein arylamine is connected to the naphthalene ring of naphthalene (phenanthrene) furan group. After naphthalene (phenanthrene) furan is fused with oxazole / thiazole, the conjugated system of the compound is increased, which helps to pile up between molecules, thereby significantly enhancing the hole transport ability of the present application's compound. The present application's compound and electron transport material are mixed to form a hybrid host material, which can improve carrier balance in the luminescent layer, widen the carrier recombination region, improve exciton generation and utilization efficiency, and improve device luminous efficiency and lifespan. BRIEF DESCRIPTION OF THE DRAWINGS

[0017] The accompanying drawings are used to provide further understanding of the present application and constitute a part of the specification. Together with the following specific embodiments, they are used to explain the present application, but do not constitute a limitation to the present application.

[0018] Figure 1 It is a schematic structural diagram of an organic electroluminescent device according to one embodiment of the present application.

[0019] Figure 2 It is a schematic structural diagram of an electronic device according to one embodiment of the present application.

[0020] Reference numerals

[0021] 100, anode 200, cathode 300, functional layer 310, hole injection layer

[0022] 321, hole transport layer 322, hole adjustment layer 330, organic light emitting layer 340, electron transport layer

[0023] 350, electron injection layer 400, electronic device DETAILED DESCRIPTION

[0024] The exemplary embodiments will now be described more fully with reference to the accompanying drawings. However, the exemplary embodiments can be implemented in a variety of forms and should not be construed as limited to the examples set forth herein; rather, these embodiments are provided so that this application will be more comprehensive and complete and will fully convey the concepts of the exemplary embodiments to those skilled in the art. The described features, structures, or characteristics may be combined in any suitable manner in one or more embodiments. In the following description, numerous specific details are provided to provide a full understanding of the embodiments of the present application.

[0025] In a first aspect, the present application provides a heterocyclic compound having a structure shown in Formula 1:

[0026]

[0027] wherein Y is selected from S or O;

[0028] One of X and Z is —N=, and the other is O or S;

[0029] Ring A is selected from a naphthalene ring or a phenanthrene ring;

[0030] L, L1 and L2 are the same or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;

[0031] Ar1, Ar2 and Ar3 are the same or different and are each independently selected from a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 40 carbon atoms, an alkyl group having 1 to 10 carbon atoms or a cycloalkyl group having 3 to 10 carbon atoms;

[0032] The substituents in L, L1, L2, Ar1, Ar2 and Ar3 are the same or different and are independently selected from deuterium, cyano, halogen, alkyl having 1 to 10 carbon atoms, haloalkyl having 1 to 10 carbon atoms, deuterated alkyl having 1 to 10 carbon atoms, trialkylsilyl having 3 to 12 carbon atoms, triphenylsilyl, aryl having 6 to 20 carbon atoms, deuterated aryl having 6 to 20 carbon atoms, heteroaryl having 3 to 20 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, alkoxy having 1 to 10 carbon atoms, alkylthio having 1 to 10 carbon atoms, aryloxy having 6 to 20 carbon atoms or arylthio having 6 to 20 carbon atoms; optionally, any two adjacent substituents form a saturated or unsaturated 3 to 15-membered ring;

[0033] Each R is the same or different and is independently selected from hydrogen, deuterium, cyano, a halogen group, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, a triphenylsilyl group, an aryl group having 6 to 20 carbon atoms, a heteroaryl group having 3 to 20 carbon atoms, or a cycloalkyl group having 3 to 10 carbon atoms; optionally, any two adjacent R groups form a ring; and n is selected from 1, 2, 3, 4, 5, 6, 7, 8, or 9.

[0034] In this application, the terms "optionally" and "optionally" mean that the event or environment described subsequently may or may not occur. For example, "optionally, among Ar1, Ar2 and Ar, any two adjacent substituents form a saturated or unsaturated 3-15 membered ring" includes: the scenario where any two adjacent substituents form a ring, and the scenario where any two adjacent substituents exist independently and do not form a ring. "Any two adjacent" can include two substituents on the same atom, and can also include one substituent on each of two adjacent atoms; wherein, when there are two substituents on the same atom, the two substituents can form a saturated or unsaturated spiro ring with the atom to which they are connected; when there is one substituent on each of two adjacent atoms, the two substituents can be fused into a ring.

[0035] In this application, the descriptions “each independently is”, “each independently is” and “each independently is” are interchangeable and should be understood in a broad sense. They can mean that in different groups, the specific options expressed by the same symbols do not affect each other, or in the same group, the specific options expressed by the same symbols do not affect each other. For example, Wherein, each q is independently 0, 1, 2 or 3, and each R" is independently selected from hydrogen, deuterium, fluorine, and chlorine. The meaning is: Formula Q-1 represents that there are q substituents R" on the benzene ring, and each R" can be the same or different, and the options of each R" do not affect each other; Formula Q-2 represents that there are q substituents R" on each benzene ring of biphenyl, and the number q of R" substituents on the two benzene rings can be the same or different, and each R" can be the same or different, and the options of each R" do not affect each other.

[0036] In this application, the term "substituted or unsubstituted" means that the functional group described after the term may or may not have a substituent (hereinafter, for ease of description, the substituents are collectively referred to as Rc). For example, "substituted or unsubstituted aryl" refers to an aryl group having a substituent Rc or an unsubstituted aryl group. The substituent Rc can be, for example, deuterium, a halogen group, a cyano group, a heteroaryl group, an aryl group, a trialkylsilyl group, an alkyl group, a haloalkyl group, a cycloalkyl group, a deuterated phenyl group, etc. The number of substitutions can be one or more.

[0037] In this application, "plurality" refers to two or more, for example, 2, 3, 4, 5, 6, etc.

[0038] In the present application, the number of carbon atoms in a substituted or unsubstituted functional group refers to the number of all carbon atoms.

[0039] The hydrogen atoms in the structures of the compounds of the present application include various isotope atoms of the hydrogen element, such as hydrogen (H), deuterium (D) or tritium (T).

[0040] In the present application, aryl refers to an optional functional group or substituent derived from an aromatic carbocyclic ring. Aryl can be a monocyclic aryl (such as phenyl) or a polycyclic aryl. In other words, aryl can be a monocyclic aryl, a condensed ring aryl, two or more monocyclic aryl groups connected by carbon-carbon bond conjugation, a monocyclic aryl and a condensed ring aryl connected by carbon-carbon bond conjugation, two or more condensed ring aryl groups connected by carbon-carbon bond conjugation. That is, unless otherwise indicated, two or more aromatic groups connected by carbon-carbon bond conjugation can also be considered as aryl of the present application. Wherein, condensed ring aryl, for example, can include bicyclic condensed aryl (such as naphthyl), tricyclic condensed aryl (such as phenanthrenyl, fluorenyl, anthracenyl) etc. Aryl does not contain heteroatoms such as B, N, O, S, P, Se and Si. Examples of aryl groups include, but are not limited to, phenyl, naphthyl, fluorenyl, spirobifluorenyl, anthracenyl, phenanthrenyl, biphenyl, terphenyl, triphenylene, peryl, benzo[9,10]phenanthrenyl, pyrenyl, benzofluoranthenyl, Ji et al.

[0041] In the present application, the arylene group refers to a divalent group formed by further losing one or more hydrogen atoms from an aryl group.

[0042] In this application, terphenyl includes

[0043] In the present application, the number of carbon atoms in the substituted or unsubstituted aryl (arylene) group may be 6, 8, 10, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, or 40. In some embodiments, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, in other embodiments, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, in other embodiments, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, and in other embodiments, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group having 6 to 15 carbon atoms.

[0044] In the present application, the fluorenyl group may be substituted by one or more substituents. In the case where the fluorenyl group is substituted, the substituted fluorenyl group may be: etc., but not limited thereto.

[0045] In the present application, examples of aryl groups as substituents for L, L1, L2, Ar3, Ar1, and Ar2 include, but are not limited to, phenyl, naphthyl, phenanthrenyl, biphenyl, fluorenyl, dimethylfluorenyl, and the like.

[0046] In the present application, a heteroaryl group refers to a monovalent aromatic ring or a derivative thereof containing 1, 2, 3, 4, 5 or 6 heteroatoms in the ring, wherein the heteroatoms may be one or more of B, O, N, P, Si, Se and S. A heteroaryl group may be a monocyclic heteroaryl group or a polycyclic heteroaryl group. In other words, a heteroaryl group may be a single aromatic ring system or a plurality of aromatic ring systems connected by conjugated carbon-carbon bonds, and any aromatic ring system may be an aromatic monocyclic ring or an aromatic condensed ring. For example, the heteroaryl group may include a thienyl group, a furyl group, a pyrrolyl group, an imidazolyl group, a thiazolyl group, an oxazolyl group, an oxadiazolyl group, a triazolyl group, a pyridyl group, a bipyridyl group, a pyrimidyl group, a triazinyl group, an acridinyl group, a pyridazinyl group, a pyrazinyl group, a quinolyl group, a quinazolinyl group, a quinoxalinyl group, a phenoxazinyl group, a phthalazinyl group, a pyridopyrimidinyl group, a pyridopyrazinyl group, a pyrazinopyrazinyl group, an isoquinolyl group, an indolyl group, a carbazolyl group, a benzoxazolyl group, a benzimidazolyl group, a benzothiazolyl group, a benzocarbazolyl group, a benzothienyl group, a dibenzothienyl group, a thienothiphenyl group, a benzofuranyl group, a phenanthrolinyl group, an isoxazolyl group, a thiadiazolyl group, a phenothiazinyl group, a silafluorenyl group, a dibenzofuranyl group, and an N-phenylcarbazolyl group, an N-pyridylcarbazolyl group, an N-methylcarbazolyl group, and the like, without being limited thereto.

[0047] In the present application, the heteroarylene group refers to a divalent or multivalent group formed by further losing one or more hydrogen atoms from a heteroaryl group.

[0048] In the present application, the number of carbon atoms in the substituted or unsubstituted heteroaryl (heteroarylene) can be selected from 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40. In some embodiments, the substituted or unsubstituted heteroaryl is a substituted or unsubstituted heteroaryl having a total carbon number of 3 to 30, in other embodiments, the substituted or unsubstituted heteroaryl is a substituted or unsubstituted heteroaryl having a total carbon number of 12 to 18, and in other embodiments, the substituted or unsubstituted heteroaryl is a substituted or unsubstituted heteroaryl having a total carbon number of 5 to 12.

[0049] In the present application, examples of heteroaryl groups as substituents for L, L1, L2, Ar3, Ar1, and Ar2 include, but are not limited to, pyridyl, carbazolyl, dibenzothiophenyl, dibenzofuranyl, benzoxazolyl, benzothiazolyl, and benzimidazolyl.

[0050] In the present application, the substituted heteroaryl group may be a heteroaryl group in which one or more hydrogen atoms are replaced by groups such as a deuterium atom, a halogen group, -CN, an aryl group, a heteroaryl group, a trialkylsilyl group, an alkyl group, a cycloalkyl group, a haloalkyl group, or the like.

[0051] In the present application, the alkyl group having 1 to 10 carbon atoms may include a straight-chain alkyl group having 1 to 10 carbon atoms and a branched-chain alkyl group having 3 to 10 carbon atoms. The number of carbon atoms in the alkyl group may be, for example, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10. Specific examples of the alkyl group include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, and n-hexyl.

[0052] In the present application, the halogen group may be, for example, fluorine, chlorine, bromine, or iodine.

[0053] In the present application, specific examples of trialkylsilyl include, but are not limited to, trimethylsilyl, triethylsilyl, and the like.

[0054] In the present application, specific examples of haloalkyl include, but are not limited to, trifluoromethyl.

[0055] In the present application, the number of carbon atoms in the cycloalkyl group having 3 to 10 carbon atoms may be, for example, 3, 4, 5, 6, 7, 8 or 10. Specific examples of the cycloalkyl group include, but are not limited to, cyclopentyl, cyclohexyl, and adamantyl.

[0056] In the present application, the number of carbon atoms in a deuterated alkyl group having 1 to 10 carbon atoms is, for example, 1, 2, 3, 4, 5, 6, 7, 8 or 10. Specific examples of the deuterated alkyl group include, but are not limited to, trideuterated methyl.

[0057] In the present application, the carbon number of the haloalkyl group having 1 to 10 is, for example, 1, 2, 3, 4, 5, 6, 7, 8 or 10. Specific examples of the haloalkyl group include, but are not limited to, trifluoromethyl.

[0058] In this application, a ring system formed by n atoms is referred to as an n-membered ring. For example, phenyl is a 6-membered ring. A 3- to 15-membered ring refers to a cyclic group with 3 to 15 ring atoms. Examples of 3- to 15-membered rings include cyclopentane, cyclohexane, fluorene, and benzene rings.

[0059] In this application, Refers to the chemical bonds that connect to other groups.

[0060] In this application, no single bond extending from the ring system is involved in the positioning of the connecting bond. This means that one end of the link can be connected to any position in the ring system that the link passes through, and the other end is connected to the rest of the compound molecule. For example, as shown in the following formula (f), the naphthyl represented by formula (f) is connected to other positions of the molecule via two non-positional linkers that pass through the bicyclic ring. The meaning of this includes any possible connection method shown in formulas (f-1) to (f-10):

[0061]

[0062] For example, as shown in the following formula (X'), the dibenzofuranyl group represented by formula (X') is connected to other positions of the molecule through a non-positional connecting bond extending from the middle of one benzene ring. The meaning represented by it includes any possible connection method shown in formulas (X'-1) to (X'-4):

[0063]

[0064] A non-positional substituent herein refers to a substituent connected via a single bond extending from the center of the ring system, indicating that the substituent can be attached at any possible position within the ring system. For example, as shown in the following formula (Y), the substituent R' represented by formula (Y) is connected to the quinoline ring via a non-positional bond, and its meaning includes any possible connection method shown in formulas (Y-1) to (Y-7):

[0065]

[0066] In some embodiments, the compound represented by Formula 1 has the structure represented by Formulas 1-1 to 1-16:

[0067]

[0068]

[0069] In some embodiments, the compound represented by Formula 1 has the structure represented by the following formulas (2-1) to (2-15):

[0070]

[0071] In some embodiments, Ar1, Ar2, and Ar3 are the same or different and are each independently selected from a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 24 carbon atoms.

[0072] In some embodiments, Ar1, Ar2 and Ar3 are each independently selected from substituted or unsubstituted aryl groups having 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24 or 25 carbon atoms, and substituted or unsubstituted heteroaryl groups having 5, 6, 7, 8, 9, 10, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23 or 24 carbon atoms.

[0073] In some embodiments, the substituents in Ar1, Ar2 and Ar3 are each independently selected from deuterium, a halogen group, a cyano group, a haloalkyl group having 1 to 4 carbon atoms, a deuterated alkyl group having 1 to 4 carbon atoms, an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, an aryl group having 6 to 15 carbon atoms, a heteroaryl group having 5 to 12 carbon atoms, a trialkylsilyl group having 3 to 8 carbon atoms or a deuterated aryl group having 6 to 15 carbon atoms, and optionally, any two adjacent substituents form a benzene ring or a fluorene ring.

[0074] In some embodiments, Ar1, Ar2 and Ar3 are each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted pyrenyl, substituted or unsubstituted peryl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted benzothiazolyl, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted benzimidazolyl.

[0075] Optionally, the substituents in Ar1, Ar2 and Ar3 are each independently selected from deuterium, fluorine, cyano, trideuteromethyl, trimethylsilyl, trifluoromethyl, cyclopentyl, cyclohexyl, adamantyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, pyridyl, dibenzofuranyl, dibenzothiophenyl or carbazolyl, and optionally, in Ar1 and Ar2, any two adjacent substituents form a benzene ring.

[0076] In some embodiments, Ar1, Ar2 and Ar3 are each independently selected from a substituted or unsubstituted group W; wherein the unsubstituted group W is selected from the group consisting of:

[0077]

[0078] The substituted group W has one or more substituents, and the substituents of the substituted group W are each independently selected from deuterium, fluorine, cyano, trideuteromethyl, trimethylsilyl, trifluoromethyl, cyclopentyl, cyclohexyl, adamantyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, dibenzofuranyl, dibenzothiophenyl or carbazolyl, and when the number of substituents on the group W is greater than 1, the substituents are the same or different.

[0079] In some embodiments, Ar1 and Ar2 are independently selected from the group consisting of:

[0080]

[0081]

[0082] In some embodiments, Ar3 is selected from a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, or a substituted or unsubstituted heteroaryl group having 12 to 18 carbon atoms; the substituents in Ar3 are each independently selected from deuterium, fluorine, cyano, trideuteromethyl, trimethylsilyl, trifluoromethyl, cyclopentyl, cyclohexyl, adamantyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, pyridyl or deuterated phenyl.

[0083] In some embodiments, Ar3 is selected from the group consisting of:

[0084]

[0085]

[0086] In some embodiments, L, L1, and L2 are the same or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 18 carbon atoms, or a substituted or unsubstituted heteroarylene group having 5 to 18 carbon atoms.

[0087] In some embodiments, L, L1 and L2 are the same or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6, 7, 8, 9, 10, 11, 12, 13, 14 or 15 carbon atoms, or a substituted or unsubstituted heteroarylene group having 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17 or 18 carbon atoms.

[0088] Optionally, the substituents in L, L1 and L2 are each independently selected from deuterium, fluorine, cyano, an alkyl group having 1 to 5 carbon atoms, a trialkylsilyl group having 3 to 8 carbon atoms, a fluoroalkyl group having 1 to 4 carbon atoms, a deuterated alkyl group having 1 to 4 carbon atoms, a phenyl group or a naphthyl group.

[0089] In some embodiments, L, L1 and L2 are each independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted phenanthrenylene group, a substituted or unsubstituted dibenzothienylene group, a substituted or unsubstituted dibenzofuranylene group, or a substituted or unsubstituted carbazolylene group.

[0090] Optionally, the substituents in L, L1 and L2 are the same or different and are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuterated methyl, trimethylsilyl or phenyl.

[0091] In some embodiments, L, L1 and L2 are each independently selected from a single bond, a substituted or unsubstituted group Q, and the unsubstituted group Q is selected from the following groups:

[0092]

[0093] The substituted group Q has one or more substituents, and the substituents of the substituted group Q are each independently selected from deuterium, fluorine, cyano, trideuteromethyl, trimethylsilyl, trifluoromethyl, cyclopentyl, cyclohexyl, adamantyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, dibenzofuranyl, dibenzothienyl or carbazolyl, and when the number of substituents on the group Q is greater than 1, the substituents are the same or different.

[0094] In some embodiments, L is selected from the group consisting of a single bond or the following groups:

[0095]

[0096] In some embodiments, L1 and L2 are each independently selected from the group consisting of a single bond or the following groups:

[0097]

[0098] In some embodiments, each R is the same or different and is independently selected from deuterium, cyano, fluorine, trideuteromethyl, trimethylsilyl, trifluoromethyl, cyclopentyl, cyclohexyl, adamantyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, dibenzofuranyl, dibenzothienyl or carbazolyl; optionally, any two adjacent substituents form a benzene ring.

[0099] In some embodiments, the heterocyclic compound is selected from the group consisting of:

[0100]

[0101]

[0102]

[0103]

[0104]

[0105]

[0106]

[0107]

[0108]

[0109]

[0110]

[0111]

[0112]

[0113]

[0114]

[0115] In a second aspect, the present application provides an organic electroluminescent device comprising an anode, a cathode, and a functional layer disposed between the anode and the cathode; wherein the functional layer comprises the heterocyclic compound described in the first aspect of the present application.

[0116] The heterocyclic compound provided in the present application can be used to form at least one organic film layer in the functional layer to improve the luminous efficiency, lifespan and other characteristics of the organic electroluminescent device.

[0117] Optionally, the functional layer includes an organic light-emitting layer, and the organic light-emitting layer includes the heterocyclic compound. The organic light-emitting layer can be composed of the heterocyclic compound provided in this application, or can be composed of the heterocyclic compound provided in this application and other materials.

[0118] Optionally, the functional layer further comprises a hole transport layer and a hole adjustment layer, wherein the hole transport layer is located between the anode and the organic light-emitting layer, and the hole adjustment layer is located between the hole transport layer and the organic light-emitting layer. In some embodiments, the hole adjustment layer is composed of the heterocyclic compound provided in this application, or is composed of the heterocyclic compound provided in this application and other materials.

[0119] According to a specific embodiment, the organic electroluminescent device is as follows Figure 1 As shown, it includes an anode 100, a hole injection layer 310, a hole transport layer 321, a hole adjustment layer (also called a hole auxiliary layer) 322, an organic light-emitting layer 330, an electron transport layer 340, an electron injection layer 350 and a cathode 200 stacked in sequence.

[0120] In the present application, the anode 100 includes an anode material, which is preferably a material with a large work function that facilitates hole injection into the functional layer. Specific examples of anode materials include: metals such as nickel, platinum, vanadium, chromium, copper, zinc, and gold or their alloys; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combined metals and oxides such as ZnO:Al or SnO2:Sb; or conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole, and polyaniline, but are not limited thereto. Preferably, a transparent electrode comprising indium tin oxide (ITO) as an anode is included.

[0121] In the present application, the hole transport layer or the hole adjustment layer may include one or more hole transport materials, respectively. The hole transport layer material may be selected from carbazole polymers, carbazole-linked triarylamine compounds, or other types of compounds, and may specifically be selected from the following compounds or any combination thereof:

[0122]

[0123] In one embodiment, the hole transport layer 321 may be composed of α-NPD.

[0124] In one embodiment, the hole-regulating layer 322 is composed of HT-1.

[0125] In one embodiment of the present application, the hole adjustment layer 322 is composed of the heterocyclic compound of the present application.

[0126] Optionally, a hole injection layer 310 is provided between the anode 100 and the hole transport layer 321 to enhance the ability to inject holes into the hole transport layer 321. The hole injection layer 310 may be made of a benzidine derivative, a starburst arylamine compound, a phthalocyanine derivative, or other materials, and this application does not impose any particular limitation thereto. The material of the hole injection layer 310 may be selected from the following compounds or any combination thereof, for example:

[0127]

[0128]

[0129] In one embodiment of the present application, the hole injection layer 310 is composed of PD.

[0130] Alternatively, the organic light-emitting layer 330 may be composed of a single light-emitting material, or may include a host material and a guest material. Alternatively, the organic light-emitting layer 330 may be composed of a host material and a guest material. Holes and electrons injected into the organic light-emitting layer 330 may recombine in the organic light-emitting layer 330 to form excitons. The excitons transfer energy to the host material, and the host material transfers energy to the guest material, thereby enabling the guest material to emit light.

[0131] The host material of the organic light-emitting layer 330 may include a metal chelate compound, a bisphenylethylene derivative, an aromatic amine derivative, a dibenzofuran derivative, or other types of materials. The host material of the organic light-emitting layer 330 may be a single compound or a combination of two or more compounds. Optionally, the host material includes the heterocyclic compound of the present application.

[0132] The guest material of the organic light-emitting layer 330 can be a compound having a condensed aromatic ring or a derivative thereof, a compound having a heteroaromatic ring or a derivative thereof, an aromatic amine derivative or other materials, and this application does not impose any special restrictions on this. The guest material is also called a doping material or a dopant. According to the type of luminescence, it can be divided into fluorescent dopants and phosphorescent dopants. For example, specific examples of the phosphorescent dopant include, but are not limited to,

[0133] In one embodiment of the present application, the organic electroluminescent device is a red organic electroluminescent device. In a more specific embodiment, the host material of the organic light-emitting layer 330 comprises the heterocyclic compound of the present application. The guest material may be, for example, RD-1.

[0134] In another embodiment, the organic electroluminescent device is a green organic electroluminescent device. In a more specific embodiment, the host material of the organic light-emitting layer 330 comprises the heterocyclic compound of the present application. The guest material may be, for example, fac-Ir(ppy)3.

[0135] The electron transport layer 340 may be a single-layer structure or a multi-layer structure, and may include one or more electron transport materials. The electron transport material may be selected from, but not limited to, ET-1, BmPyPhB, LiQ, benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives, or other electron transport materials, and this application does not impose any particular restrictions on this. The materials of the electron transport layer 340 include, but are not limited to, the following compounds:

[0136]

[0137] In one embodiment of the present application, the electron transport layer 340 is composed of ET-1 and LiQ.

[0138] In the present application, cathode 200 includes a cathode material having a small work function that facilitates electron injection into the functional layer. Specific examples of cathode materials include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; or multilayer materials such as LiF / Al, Liq / Al, LiO2 / Al, LiF / Ca, LiF / Al, and BaF2 / Ca. Alternatively, a metal electrode containing magnesium and silver may be used as the cathode.

[0139] Optionally, an electron injection layer 350 is further provided between the cathode 200 and the electron transport layer 340 to enhance the ability to inject electrons into the electron transport layer 340. The electron injection layer 350 may include an inorganic material such as an alkali metal sulfide or an alkali metal halide, or may include a complex of an alkali metal and an organic matter. In one embodiment of the present application, the electron injection layer 350 includes ytterbium (Yb).

[0140] A third aspect of the present application provides an electronic device comprising the organic electroluminescent device described in the second aspect of the present application.

[0141] According to one embodiment, Figure 2 As shown, the provided electronic device is electronic device 400, which includes the above-mentioned organic electroluminescent device. Electronic device 400 can be, for example, a display device, a lighting device, an optical communication device, or other types of electronic devices, including but not limited to computer screens, mobile phone screens, televisions, electronic paper, emergency lighting, optical modules, etc.

[0142] The synthesis method of the heterocyclic compound of the present application is specifically described below in conjunction with synthesis examples, but the present disclosure is not limited thereto.

[0143] Synthesis Example

[0144] Those skilled in the art will recognize that the chemical reactions described herein can be used to appropriately prepare many of the heterocyclic compounds described herein, and that other methods for preparing the compounds described herein are considered within the scope of this application. For example, the synthesis of compounds not exemplified herein can be successfully accomplished by one skilled in the art through modifications such as appropriate protection of interfering groups, the use of known reagents other than those described herein, or conventional modifications of reaction conditions. Compounds for which no synthetic method is described herein are commercially available raw materials.

[0145] Synthesis of 7-bromo-1-iodo-2-naphthol:

[0146]

[0147] Under nitrogen, 7-bromo-1-iodo-2-naphthylamine (CAS: 2411719-24-7, 17.40 g, 50 mmol), concentrated hydrochloric acid (25 mL), and deionized water (25 mL) were added sequentially to a 1000 mL three-necked flask. The mixture was cooled to 0°C in an ice-water bath. A solution of sodium nitrite (3.45 g, 50 mmol) in water (25 mL) was added dropwise. Following the addition, a solution of potassium thiocyanate (9.72 g, 100 mmol) and ferric chloride (4.1 g, 25 mmol) in water (25 mL) were added dropwise. After the addition was complete, the mixture was slowly warmed to room temperature and stirred overnight. The reaction mixture was poured into deionized water (200 mL) and extracted with dichloromethane (3 times with 100 mL). The organic phases were combined, dried over anhydrous sodium sulfate, filtered, and the solvent removed by vacuum distillation to obtain the crude product, which was used directly in the next step without purification.

[0148] Under a nitrogen atmosphere, the crude product, sodium sulfide nonahydrate (9.61 g, 100 mmol), ethanol (180 mL), and deionized water (360 mL) were added to a 1000 mL three-necked flask in one portion. The mixture was heated to reflux and stirred for 16 h. After the reaction system cooled to room temperature, it was filtered, and the filtrate was acidified to pH 2 with 1 M hydrochloric acid. The mixture was then extracted with dichloromethane (100 mL x 3). The organic phases were combined, dried over anhydrous sodium sulfate, filtered, and the solvent was removed by distillation under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography using n-heptane as the mobile phase to obtain 7-bromo-1-iodo-2-naphthol (8.03 g, 44% yield) as a white solid.

[0149] Synthesis of Sub-a1:

[0150]

[0151] Under nitrogen atmosphere, 7-bromo-2-phenylbenzoxazole (CAS: 1268137-13-8, 12.06 g, 44 mmol), diboronic acid pinacol ester (12.28 g, 48.4 mmol), potassium acetate (9.50 g, 96.8 mmol) and 1,4-dioxane (120 mL) were added to a 500 mL three-necked flask in sequence. Stirring and heating were started. When the system was heated to 40 ° C, tris(dibenzylideneacetone)dipalladium (Pd2(dba)3, 0.40 g, 0.44 mmol) and 2-dicyclohexylphosphine-2',4',6'triisopropylbiphenyl (XPhos, 0.42 g, 0.88 mmol) were quickly added. The temperature was continued to rise to reflux and the reaction was stirred overnight. After the system was cooled to room temperature, 200 mL of water was added to the system, and the mixture was stirred thoroughly for 30 min. The mixture was filtered under reduced pressure, and the filter cake was washed with deionized water until neutral, then rinsed with 100 mL of anhydrous ethanol. The filter cake was collected to obtain a gray solid. The crude product was slurried once with n-heptane, dissolved in 200 mL of toluene, and passed through a silica gel column to remove the catalyst. After concentration, a white solid Sub-a1 (10.17 g, 72% yield) was obtained.

[0152] Referring to the synthesis of Sub-a1, Sub-a2 to Sub-a4 were synthesized by using reactant A shown in Table 1 instead of 7-bromo-2-phenylbenzoxazole.

[0153] Table 1: Synthesis of Sub-a2 and Sub-a4

[0154]

[0155]

[0156] Synthesis of Sub-b1:

[0157]

[0158] Under nitrogen, a 500 mL three-necked flask was charged with Sub-a1 (17.66 g, 55 mmol), 7-bromo-1-iodo-2-hydroxynaphthalene (17.45 g, 50 mmol), tetrakistriphenylphosphine palladium (Pd(PPh3)4, 0.58 g, 0.5 mmol), anhydrous sodium carbonate (10.60 g, 100 mmol), toluene (180 mL), anhydrous ethanol (45 mL), and deionized water (45 mL). Stirring and heating were initiated, and the temperature was raised to reflux for 16 h. After cooling to room temperature, the system was extracted with dichloromethane (150 mL x 3). The organic phases were combined, dried over anhydrous magnesium sulfate, filtered, and the filtrate was evaporated under reduced pressure to remove the solvent to obtain a crude product. Purification by silica gel column chromatography using n-heptane as the mobile phase afforded Sub-b1 (11.03 g, 53% yield) as a white solid.

[0159] Referring to the synthesis of Sub-b1, Sub-b2 to Sub-b11 were synthesized by using reactant B shown in Table 2 instead of Sub-a1 and reactant C instead of 7-bromo-1-iodo-2-hydroxynaphthalene.

[0160] Table 2: Synthesis of Sub-b2 to Sub-b11

[0161]

[0162]

[0163] Synthesis of Sub-c1:

[0164]

[0165] Under a nitrogen atmosphere, Sub-b1 (20.81 g, 50 mmol), tert-butyl peroxybenzoate (BzOOt-Bu, 19.42 g, 100 mmol), palladium acetate (1.12 g, 5 mmol), 3-nitropyridine (0.62 g, 5 mmol), hexafluorobenzene (C6F6, 210 mL), and N,N'-dimethylimidazolidinone (DMI, 140 mL) were added sequentially to a 500 mL three-necked flask. Stirring and heating were initiated, and the temperature was raised to 90°C for 4 h. After cooling to room temperature, the mixture was extracted with ethyl acetate (100 mL x 3). The organic phase was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed from the filtrate under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography using n-heptane / dichloromethane as the mobile phase to obtain Sub-c1 (10.77 g, 52% yield) as a white solid.

[0166] Sub-c2 to Sub-c11 were synthesized by referring to Sub-c1 and using reactant D shown in Table 3 instead of Sub-b1.

[0167] Table 3: Synthesis of Sub-c2 to Sub-c11

[0168]

[0169]

[0170] Synthesis of Sub-c11:

[0171]

[0172] Under a nitrogen atmosphere, Sub-c1 (10.36 g, 25 mmol) and 200 mL of deuterated benzene-D6 were added to a 100 mL three-necked flask. The temperature was raised to 60°C, and trifluoromethanesulfonic acid (22.51 g, 150 mmol) was added. The temperature was continued to rise to boiling and stirred for 24 hours. After the reaction system cooled to room temperature, 50 mL of heavy water was added, stirred for 10 minutes, and then saturated aqueous K3PO4 was added to neutralize the reaction solution. The organic layer was extracted with dichloromethane (50 mL × 3 times), the organic phases were combined, dried over anhydrous sodium sulfate, filtered, and the filtrate was distilled off under reduced pressure to remove the solvent to obtain the crude product. The crude product was purified by silica gel column chromatography using n-heptane / dichloromethane as the mobile phase to obtain Sub-c11 (6.82 g, 64% yield) as a white solid.

[0173] Synthesis of Sub-c12:

[0174]

[0175] Under a nitrogen atmosphere, Sub-b12 (10.80 g, 25 mmol), palladium dichloride (0.22 g, 1.25 mmol), and DMSO (120 mL) were added to a 250 mL three-necked flask, heated to 140°C, and stirred for 12 hours. After the reaction system cooled to room temperature, the organic layer was extracted with dichloromethane (50 mL × 3 times). The organic phases were combined and dried over anhydrous sodium sulfate, filtered, and the filtrate was distilled off under reduced pressure to remove the solvent to obtain a crude product. The crude product was purified by silica gel column chromatography using n-heptane / dichloromethane as the mobile phase to obtain Sub-c12 (7.85 g, 73% yield) as a white solid.

[0176] Synthesis of Sub-d1:

[0177]

[0178] Under a nitrogen atmosphere, Sub-c1 (13.36 g, 50 mmol), 4-chlorophenylboronic acid (8.60 g, 55 mmol), tetrakis(triphenylphosphine)palladium (Pd(PPh3)4, 0.58 g, 0.5 mmol), anhydrous sodium carbonate (10.60 g, 100 mmol), toluene (140 mL), anhydrous ethanol (35 mL), and deionized water (35 mL) were added sequentially to a 500 mL three-necked flask. Stirring and heating were initiated, and the temperature was raised to reflux for 16 h. After the system cooled to room temperature, it was extracted with dichloromethane (100 mL × 3 times). The organic phases were combined, dried over anhydrous magnesium sulfate, filtered, and the filtrate was evaporated under reduced pressure to remove the solvent to obtain a crude product. The crude product was purified by silica gel column chromatography using n-heptane as the mobile phase to obtain Sub-d1 (13.82 g, 62% yield) as a white solid.

[0179] Referring to the synthesis of Sub-d1, reactant E shown in Table 4 was used instead of Sub-c1, and reactant F was used instead of 4-chlorophenylboronic acid to synthesize Sub-d2 to Sub-d8.

[0180] Table 4: Synthesis of Sub-d2 to Sub-d8

[0181]

[0182]

[0183] Synthesis of compound 3:

[0184]

[0185] Under a nitrogen atmosphere, Sub-c1 (10.35 g, 25 mmol), SM-1 (CAS: 1322090-81-2, 6.88 g, 27.5 mmol), tris(dibenzylideneacetone)dipalladium (0.46 g, 0.5 mmol), 2-dicyclohexylphosphine-2',4',6'triisopropylbiphenyl (0.48 g, 1 mmol), sodium tert-butoxide (4.80 g, 50 mmol) and xylene (xylene, 100 mL) were added sequentially to a 250 mL three-necked flask, the temperature was raised to reflux, and the reaction was stirred overnight; after the system was cooled to room temperature, it was extracted with dichloromethane (100 mL × 3 times), the organic phases were combined and dried over anhydrous magnesium sulfate, filtered, and the solvent was distilled off under reduced pressure to obtain a crude product. The crude product was purified by silica gel column chromatography using n-heptane as the mobile phase to obtain white solid compound 3 (7.73 g, yield 53%, m / z = 584.2 [M+H] + ).

[0186] Referring to the synthesis of compound 3, the compounds in Table 5 were synthesized by using reactant H shown in Table 5 instead of Sub-c1 and reactant H instead of SM-1.

[0187] Table 5: Synthesis of compounds

[0188]

[0189]

[0190]

[0191]

[0192]

[0193]

[0194] Compound 130 NMR:1 H-NMR(400MHz,CD2Cl2)δppm:8.35(d,2H),8.06(d,1H),7.99(d,1H),7.89(d,1H),7.86-7.72(m,7H),7.65(d ,1H),7.60-7.44(m,7H),7.42-7.34(m,5H),7.26(d,1H),7.05(s,1H),6.85(d,1H),6.73(d,1H),6.42(d,1H);

[0195] Compound 348 NMR: 1 H-NMR (400MHz, CD2Cl2) δppm: (8.38-8.26(m,5H),8.06(d,1H),7.97(d,1H),7.85-7.81(m,2H),7.78-7.70(m ,3H),7.63-7.46(m,5H),7.43-7.35(m,2H),7.26(t,2H),6.87(s,1H),6.67(d,1H),6.62(t,1H),6.36(d,2H).

[0196] Preparation and evaluation of organic electroluminescent devices:

[0197] Example 1: Preparation of red organic electroluminescent device

[0198] First, the anode pretreatment is carried out through the following process: On the ITO / Ag / ITO substrate, the surface treatment was performed using ultraviolet ozone and O2:N2 plasma to increase the work function of the anode, and the surface of the ITO substrate was cleaned with an organic solvent to remove impurities and oil stains on the surface of the ITO substrate.

[0199] PD was vacuum-deposited on the experimental substrate (anode) to form a Then, α-NPD was vacuum-deposited on the hole injection layer to form a hole injection layer with a thickness of hole transport layer.

[0200] Compound HT-1 is vacuum-deposited on the hole transport layer to form a layer with a thickness of Hole Adjustment Layer.

[0201] Next, compound 3:RH-N:RD-1 was co-deposited on the hole adjustment layer at a deposition rate ratio of 49%:49%:2% to form a layer with a thickness of Red light emitting layer (EML)

[0202] On the light-emitting layer, compound ET-1 and LiQ were mixed in a weight ratio of 1:1 and evaporated to form Yb is evaporated on the electron transport layer to form a layer with a thickness of Then, magnesium (Mg) and silver (Ag) were mixed at a 1:9 evaporation rate and vacuum evaporated on the electron injection layer to form a layer with a thickness of cathode.

[0203] In addition, the thickness of the vacuum evaporation layer on the cathode is CP, thereby completing the manufacture of red organic electroluminescent devices.

[0204] Examples 2 to 40

[0205] An organic electroluminescent device was prepared by the same method as in Example 1, except that Compound X in Table 6 below was used instead of Compound 3 in Example 1 when preparing the light-emitting layer.

[0206] Comparative Examples 1 to 3

[0207] An organic electroluminescent device was prepared using the same method as in Example 1, except that Compound A, Compound B, and Compound C were used to replace Compound 3 in Example 1 when preparing the light-emitting layer.

[0208] Among them, when preparing each embodiment and comparative example, the compound structure used is as follows:

[0209]

[0210]

[0211] The performance of the red organic electroluminescent devices prepared in Examples 1 to 40 and Comparative Examples 1 to 3 was tested. Specifically, at 10 mA / cm 2 The IVL performance of the device was tested under the conditions of T95 device life at 20mA / cm 2 The test was carried out under the conditions of , and the test results are shown in Table 6.

[0212] Table 6

[0213]

[0214]

[0215] As can be seen from Table 6 above, when the compound of the present invention is used as the host material of a red organic electroluminescent device, the efficiency is increased by at least 10.6% and the lifespan is increased by at least 11.3%.

[0216] The reason is that the structure of the compound of the present application includes a naphthalene (phenanthrene) furan and oxazole / thiazole - triarylamine structure, wherein the arylamine is connected to the naphthalene ring (phenanthrene ring) of the naphthalene (phenanthrene) furan group. (Phenanthrene) naphthofuran is fused with oxazole / thiazole to increase the conjugated system of the compound, which helps to pile up between molecules, thereby significantly enhancing the hole transport ability of the compound of the present application. The compound of the present application and the electron transport material are mixed to form a hybrid host material, which can improve the carrier balance in the light-emitting layer, widen the carrier recombination region, improve exciton generation and utilization efficiency, and improve device luminous efficiency and life.

[0217] The preferred embodiments of the present invention are described in detail above in conjunction with the accompanying drawings. However, the present invention is not limited to the specific details in the above embodiments. Within the technical concept of the present invention, various simple modifications can be made to the technical solution of the present invention, and these simple modifications all fall within the scope of protection of the present invention.

Claims

1. A heterocyclic compound, characterized in that The heterocyclic compound has a structure shown in Formula 1: wherein Y is selected from S or O; One of X and Z is —N=, and the other is O or S; Ring A is selected from a naphthalene ring; L is selected from a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted naphthylene group, and the substituents in L are the same or different and are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuteromethyl, trimethylsilyl, or phenyl; L1 and L2 are the same or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms; Ar1 and Ar2 are the same or different and are each independently selected from a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 40 carbon atoms; The substituents in Ar1 and Ar2 are each independently selected from deuterium, a halogen group, a cyano group, a haloalkyl group having 1 to 4 carbon atoms, a deuterated alkyl group having 1 to 4 carbon atoms, an alkyl group having 1 to 4 carbon atoms, an aryl group having 6 to 15 carbon atoms, a heteroaryl group having 5 to 12 carbon atoms, a trialkylsilyl group having 3 to 8 carbon atoms, or a deuterated aryl group having 6 to 15 carbon atoms, and optionally, any two adjacent substituents form a benzene ring or a fluorene ring; The substituents in L1 and L2 are each independently selected from deuterium, fluorine, cyano, an alkyl group having 1 to 5 carbon atoms, a fluoroalkyl group having 1 to 4 carbon atoms, a deuterated alkyl group having 1 to 4 carbon atoms, a phenyl group or a naphthyl group; Ar3 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl or substituted or unsubstituted phenanthrenyl; The substituents in Ar3 are each independently selected from deuterium, fluorine, cyano, trideuteromethyl, trimethylsilyl, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl, phenyl or naphthyl; Each R is the same or different and is independently selected from hydrogen, deuterium, cyano, a halogen group, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, or a phenyl group; n is selected from 1, 2, 3, 4, 5, 6 or 7.

2. The heterocyclic compound according to claim 1, wherein The compound represented by Formula 1 has the structures represented by Formulas 1-1 to 1-12:

3. The heterocyclic compound according to claim 1, wherein Ar1 and Ar2 are the same or different and are each independently selected from a substituted or unsubstituted aryl group having 6 to 25 carbon atoms and a substituted or unsubstituted heteroaryl group having 5 to 24 carbon atoms.

4. The heterocyclic compound according to claim 1, wherein Ar1 and Ar2 are each independently selected from a substituted or unsubstituted group W; the unsubstituted group W is selected from the group consisting of: The substituted group W has one or more substituents, and the substituents of the substituted group W are each independently selected from deuterium, fluorine, cyano, trideuteromethyl, trimethylsilyl, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, dibenzofuranyl, dibenzothiophenyl or carbazolyl, and when the number of substituents on the group W is greater than 1, each substituent is the same or different.

5. The heterocyclic compound according to claim 1, wherein L1 and L2 are the same or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 18 carbon atoms, or a substituted or unsubstituted heteroarylene group having 5 to 18 carbon atoms; The substituents in L1 and L2 are each independently selected from deuterium, fluorine, cyano, an alkyl group having 1 to 5 carbon atoms, a fluoroalkyl group having 1 to 4 carbon atoms, a deuterated alkyl group having 1 to 4 carbon atoms, a phenyl group, or a naphthyl group. The heterocyclic compound according to claim 1, wherein L1 and L2 are each independently selected from a single bond, a substituted or unsubstituted group Q, and the unsubstituted group Q is selected from the following groups: The substituted group Q has one or more substituents, and the substituents of the substituted group Q are each independently selected from deuterium, fluorine, cyano, trideuteromethyl, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, and naphthyl, and when the number of substituents on the group Q is greater than 1, the substituents are the same or different.

7. The heterocyclic compound according to claim 1, wherein L is selected from the group consisting of a single bond or the following groups:

8. The heterocyclic compound according to claim 7, wherein L1 and L2 are each independently selected from the group consisting of a single bond or the following groups:

9. The heterocyclic compound according to claim 1, wherein Ar1 and Ar2 are independently selected from the group consisting of: Ar3 is selected from the group consisting of:

10. The heterocyclic compound according to claim 1, wherein Each R is the same or different and is independently selected from deuterium, cyano, fluorine, trideuterated methyl, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl or phenyl.

11. The heterocyclic compound according to claim 1, wherein The heterocyclic compound is selected from the group consisting of the following compounds:

12. An organic electroluminescent device comprising an anode and a cathode disposed opposite to each other, and a functional layer disposed between the anode and the cathode; characterized in that: The functional layer comprises the heterocyclic compound according to any one of claims 1 to 11.

13. The organic electroluminescent device according to claim 12, wherein: The functional layer includes an organic light-emitting layer, and the organic light-emitting layer contains the heterocyclic compound; and / or The functional layer further includes a hole adjustment layer, and the hole adjustment layer includes the heterocyclic compound.

14. An electronic device, characterized in that The organic electroluminescent device according to claim 12 or 13.

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