Heterocyclic compound and organic electroluminescent device thereof

Abstract

The invention provides a heterocyclic compound and an organic electroluminescent device thereof, and particularly relates to the technical field of organic photoelectric materials. When the compound is used as a light-emitting layer main body material in the organic light-emitting device, the mobility of electrons and holes can be improved, the recombination efficiency of the electrons and the holes can be improved, and meanwhile, the energy loss can be limited, so that the photoelectric property of the organic light-emitting device is improved. The compound provided by the invention has good thermal stability and refractive index when being used as a covering layer material, can reduce the loss of light reflected by a nearby electrode during luminescence, effectively improves the stability of a film layer, and improves the performance of a device. The preparation method of the compound is simple, raw materials are easy to obtain, and the compound can be widely applied to the fields of organic thin film transistors, panel display and the like and has good application effects and industrialization prospects.

Description

Technical Field

[0001] This invention relates to the field of organic optoelectronic materials technology, specifically to a heterocyclic compound and its organic electroluminescent device. Background Technology

[0002] Organic light-emitting diodes (OLEDs) are light-emitting devices that directly convert electrical energy into light energy based on organic optoelectronic materials. Compared with traditional LEDs, they can emit light directly using organic materials, resulting in higher luminous efficiency, faster response speed, greater flexibility, and simpler fabrication processes. They are expected to replace traditional liquid crystal displays and fluorescent lighting, and are fully utilized in the field of electronic displays and lighting products, with a wider range of application and development prospects.

[0003] Organic light-emitting diodes (OLEDs) mainly consist of three parts: anode and cathode electrode material films and functional layers of different organic materials. Their light-emitting principle involves applying a voltage to the electrodes, injecting electrons and holes from the cathode and anode into the light-emitting layer, respectively. The recombination of electrons and holes generates excitons, which then undergo radiative transitions to achieve light emission. The electrode material films and functional layers of OLEDs are composed of various organic semiconductor materials.

[0004] Superior organic light-emitting devices (OLEDs) require functional materials with characteristics such as low driving voltage, high luminous efficiency, and long lifespan. Specifically, the main material of the emitting layer in OLED devices needs to possess good bipolarity and appropriate HOMO / LUMO energy levels, while the capping layer material needs to have suitable refractive index and thickness. However, due to the influence of the physicochemical properties of organic semiconductor materials, OLED devices suffer from problems such as low luminous efficiency, decreased resolution, and increased driving voltage, hindering the optimization and development of organic light-emitting devices.

[0005] Therefore, in response to the problems encountered in the main material and capping material of the light-emitting layer in current organic light-emitting devices, there is an urgent need to design and develop high-performance organic functional materials to break through the constraints, improve the photoelectric properties such as luminous efficiency and resolution frequency of the devices, and promote the deeper application and development of OLED devices. Summary of the Invention

[0006] To address the aforementioned problems, the present invention aims to provide a heterocyclic compound and its organic electroluminescent device, which can improve the luminous efficiency of the organic electroluminescent device and extend its service life.

[0007] This invention provides a heterocyclic compound having a structure represented by Formula I:

[0008] Wherein, Ar1, Ar2, and Ar3 are independently selected from any one of formula a, formula b, hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C1-C25 heterocyclic alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C1-C25 heterocyclic alkane and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl; at least one of Ar1, Ar2, and Ar3 is selected from formula a, and at least one is selected from formula a or formula b; The i is independently selected from CH and N, and when i is bonded to other groups, the i is selected from C atoms; The v is independently selected from any one of CH and N, and when v is bonded to other groups, the v is selected from C atoms; X is selected from O, S, C(R) p R q ), N(R s Any one of the following; The Y is selected from either O or S; E is selected from O, S, N(R) v Any one of the following; Group 1:

[0009] Ring A and ring B are independently selected from any one of the substituted or unsubstituted structures in group 1; and at least one of ring A and ring B is not selected from ; The z is selected from C(R) t Any one of N; The R a R b R p R q R tIt is independently selected from any one of hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C1-C25 heterocyclic alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C1-C25 heterocyclic alkane and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl; The R s R v It is independently selected from any one of hydrogen, deuterium, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C1-C25 heterocyclic alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C1-C25 heterocyclic alkane and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl; a1 is selected from 0, 1, 2, 3 or 4; when there are two or more R a At that time, two or more R a The same or different between each other, or two adjacent R a They connect with each other to form substituted or unsubstituted rings; b1 is selected from 0, 1, 2, 3, 4, or 5; when there are two or more R b At that time, two or more R b The same or different between each other, or two adjacent R b They connect with each other to form substituted or unsubstituted rings; L1, L2, L3, L4, and L5 are independently selected from any one of the following: single bond, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C6-C30 heteroarylene, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic rings, and substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic rings.

[0010] The present invention also provides an organic electroluminescent device, comprising an anode, a cathode, and an organic layer located between the anode and the cathode or on the side of the cathode opposite to the anode, the organic layer comprising at least one of the heterocyclic compounds described in the present invention.

[0011] Beneficial effects

[0012] This invention provides a heterocyclic compound that, when used as the host material for the light-emitting layer in organic light-emitting devices (OLEDs), improves the mobility and recombination efficiency of electrons and holes while limiting energy loss, thereby enhancing the photoelectric performance of OLEDs. When used as a capping layer material, the compound exhibits excellent thermal stability and refractive index, reducing light loss due to reflection from nearby electrodes during emission, effectively improving film stability and device performance. The compound provided by this invention has a stable structure, a simple preparation process, and is suitable for mass production, demonstrating promising application and industrialization prospects. Detailed Implementation

[0013] The technical solutions of the embodiments of the present invention will be clearly and completely described below. Obviously, the described embodiments are only some embodiments of the present invention, and not all embodiments. After reading the present invention, any modifications of the present invention in various equivalent forms by those skilled in the art fall within the scope defined by the present invention.

[0014] Examples of halogen atoms described in this invention may include fluorine, chlorine, bromine, and iodine.

[0015] The alkyl group described in this invention refers to a monovalent group formed by removing one hydrogen atom from an alkane molecule. It can include straight-chain alkyl groups or branched alkyl groups, preferably having 1 to 25 carbon atoms, more preferably having 1 to 12 carbon atoms, more preferably 1 to 8 carbon atoms, and particularly preferably 1 to 6 carbon atoms. The straight-chain alkyl group includes, but is not limited to, methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, undecyl, and dodecyl groups; the branched alkyl group includes, but is not limited to, isomers of isopropyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, and n-decyl groups.

[0016] The cycloalkyl group described in this invention refers to a monovalent group formed by removing one hydrogen atom from a cyclic alkane molecule, preferably having 3 to 25 carbon atoms, more preferably 3 to 12 carbon atoms, particularly preferably 5 to 10 carbon atoms, and most preferably 5 to 7 carbon atoms. Examples include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornel, camphenyl, etc., but are not limited thereto.

[0017] The heterocyclic alkyl group described in this invention refers to a group formed by removing one hydrogen atom from a heterocyclic molecule in which the atoms constituting the ring contain at least one heteroatom in addition to carbon atoms. The heteroatom includes, but is not limited to, oxygen, sulfur, nitrogen, or phosphorus, and preferably has 1 to 25 carbon atoms, more preferably 1 to 15 carbon atoms, more preferably 2 to 12 carbon atoms, and particularly preferably 2 to 6 carbon atoms. Examples include piperidinyl, piperazine, tetrahydropyrrolyl, morpholinyl, thiomorpholinyl, ethylene oxide, cyclothioethanediyl, etc., but are not limited thereto.

[0018] The aryl group described in this invention refers to a group formed by removing a hydrogen atom from one of the aromatic carbon atoms of an aromatic hydrocarbon molecule. It can be a monocyclic aryl, polycyclic aryl, or fused-ring aryl, preferably having 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 15 carbon atoms, and most preferably 6 to 12 carbon atoms. The monocyclic aryl refers to an aryl group with only one aromatic ring in the molecule, such as phenyl, but not limited thereto. The polycyclic aryl refers to an aryl group containing two or more independent aromatic rings in the molecule, such as biphenyl, terphenyl, tetraphenyl, pentaphenyl, etc., but not limited thereto. The fused-ring aryl refers to an aryl group containing two or more aromatic rings fused together by sharing two adjacent carbon atoms, such as naphthyl, anthracene, phenanthryl, pyrene, peryl, thionyl, fluorene, benzo[a]fluorene, triphenylene, fluoranyl, spirodifluorene, etc., but not limited thereto.

[0019] The heteroaryl group described in this invention refers to a group formed by replacing one or more aromatic carbon atoms in an aryl group with heteroatoms. The heteroatoms include, but are not limited to, oxygen, sulfur, nitrogen, or phosphorus. The heteroaryl group can be a monocyclic heteroaryl, a polycyclic heteroaryl, or a fused-ring heteroaryl, preferably having 2 to 30 carbon atoms, more preferably 2 to 18 carbon atoms, particularly preferably 2 to 15 carbon atoms, and most preferably 2 to 12 carbon atoms. The monocyclic heteroaryl groups include, but are not limited to, pyridinyl, pyrimidinyl, triazinyl, furanyl, thiopheneyl, pyrroloyl, oxazolyl, thiazolyl, imidazoleyl, etc.; the polycyclic heteroaryl groups include, but are not limited to, bipyridinyl, bipyrimidinyl, phenylpyridinyl, etc.; the fused-ring heteroaryl groups include, but are not limited to, quinolinyl, isoquinolinyl, benzofuranyl, benzothiopheneyl, indolyl, benzoxazolyl, benzothiazolyl, benzoimidazolyl, dibenzofuranyl, benzodibenzofuranyl, dibenzothiapheneyl, benzodibenzothiapheneyl, carbazolyl, benzocarbazolyl, acridineyl, 9,10-dihydroacridinyl, phenoxazinyl, phenthiazinyl, phenoxthiazyl, etc., but are not limited to.

[0020] The arylene group described in this invention refers to a divalent group formed by removing one hydrogen atom from each of the two aromatic carbon atoms of an aromatic hydrocarbon molecule. It can be a divalent monocyclic aryl group or a divalent fused-ring aryl group, preferably having 6 to 30 carbon atoms, more preferably 6 to 25 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 18 carbon atoms, and most preferably 6 to 12 carbon atoms. Examples of arylene groups include phenylene, biphenylene, terphenylene, naphthylene, anthracene, phenanthrene, trimethyleneene, fluorene, pyrene, perylene, etc., but are not limited thereto.

[0021] The heteroaryl group described in this invention refers to a group formed by replacing one or more aromatic carbon atoms in an aryl group with heteroatoms. The heteroatoms include, but are not limited to, oxygen, sulfur, nitrogen, or phosphorus. The divalent heteroaryl group can be a divalent monocyclic heteroaryl or a divalent fused-ring heteroaryl, preferably having 2 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, and particularly preferably 6 to 15 carbon atoms. For example, it can be selected from pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, bipyridinyl, bipyrimidinyl, phenylpyridinyl, phenylpyrimidinyl, quinolineyl, isoquinolineyl, furanyl, thiopheneyl, carbazolyl, benzofuranyl, benzothiopheneyl, benzocarbazolyl, dibenzofuranyl, dibenzothiopheneyl, dibenzocarbazolyl, benzodibenzofuranyl, benzodibenzothiopheneyl, etc., but is not limited thereto.

[0022] The fused alicyclic and aromatic ring groups described in this invention refer to the collective term for the monovalent groups obtained after removing one hydrogen atom from the fused alicyclic and aromatic rings. Preferably, they have 7 to 30 carbon atoms, more preferably 7 to 18 carbon atoms, and most preferably 7 to 13 carbon atoms. The fused alicyclic and aromatic ring groups may include, but are not limited to, benzocyclopropane, benzocyclobutane, dihydroindenyl, indenyl, tetrahydronaphthyl, dihydronaphthyl, benzocycloheptane, benzocycloheptenyl, etc.

[0023] The fused cyclic group of heterocyclic alkanes and aromatic rings described in this invention refers to the collective term for the monovalent group obtained after removing one hydrogen atom from the fused heterocyclic alkanes and aromatic rings. Preferably, it has 6 to 30 carbon atoms, more preferably 7 to 18 carbon atoms, and most preferably 7 to 13 carbon atoms. The fused cyclic group of heterocyclic alkanes and aromatic rings may include, but is not limited to, benzo[a]tetrahydropyrrole, naph[a]tetrahydropyrrole, phenanthrene[a]tetrahydropyrrole, benzo[a]hexacyclic butyl, benzo[a]hexacyclic heptyl, benzo[a]piperidinyl, naph[a]piperidinyl, phenanthrene[a]piperidinyl, etc.

[0024] The fused cyclic group of alicyclic and heteroaromatic rings in this invention refers to the general term for the monovalent group obtained after removing one hydrogen atom from the fused alicyclic and heteroaromatic rings. Preferably, it has 5 to 30 carbon atoms, more preferably 5 to 18 carbon atoms, and most preferably 5 to 12 carbon atoms. The fused cyclic group of alicyclic and heteroaromatic rings may include pyridocyclopropyl, pyridocyclobutyl, pyridocyclopentyl, pyridocyclohexyl, pyridocycloheptyl, pyridocyclopentenyl, pyrimidinylcyclopropyl, pyrimidinylcyclobutyl, pyrimidinylcyclopentyl, pyrimidinylcyclohexyl, pyrimidinylcycloheptyl, pyrimidinylcyclopentenyl, and dibenzofuran. Cyclopropyl, dibenzofuranocyclobutyl, dibenzofuranocyclopentyl, dibenzofuranocyclohexyl, dibenzofuranocycloheptyl, dibenzothiophenecyclopropyl, dibenzothiophenecyclobutyl, dibenzothiophenecyclopentyl, dibenzothiophenecyclohexyl, dibenzothiophenecycloheptyl, carbazocyclopropyl, carbazocyclobutyl, carbazocyclopentyl, carbazocyclohexyl, carbazocycloheptyl, carbazocyclopentenyl, etc., but not limited to these.

[0025] The alicyclic and aromatic ring fused cyclic groups described in this invention refer to the divalent groups formed by removing two hydrogen atoms after the alicyclic and aromatic rings are fused together. Preferably, they have 7 to 30 carbon atoms, more preferably 7 to 18 carbon atoms, and most preferably 7 to 13 carbon atoms. Examples include, but are not limited to, benzo[a]cyclopropyl, benzo[a]cyclobutyl, benzo[a]cyclopentyl, benzo[a]cyclohexyl, benzo[a]cycloheptyl, naphtho[a]cyclopropyl, naphtho[a]cyclobutyl, naphtho[a]cyclopentyl, and naphtho[a]cyclohexyl.

[0026] The fused alicyclic and heteroaromatic ring cyclic groups described in this invention refer to the divalent groups formed by removing two hydrogen atoms after the alicyclic and heteroaromatic rings are fused together. Preferably, they have 5 to 30 carbon atoms, more preferably 5 to 18 carbon atoms, and most preferably 5 to 12 carbon atoms. Examples include dibenzofuranocyclopropyl, dibenzofuranocyclobutyl, dibenzofuranocyclopentyl, dibenzofuranocyclohexyl, dibenzofuranocycloheptyl, dibenzothiophenocyclopropyl, dibenzothiophenocyclobutyl, dibenzothiophenocyclopentyl, and dibenzothiophenocyclohexyl. Dibenzothiophene-cycloheptyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, pyridinyl-cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, benzophenyl-cycloheptyl, pyrimidinyl-cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, benzophenyl-cycloheptyl, pyrimidinyl-cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, benzophenyl-cycloheptyl, etc., but not limited to these.

[0027] The substituents described in the "substituted or unsubstituted" of this invention may be independently selected from deuterium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcohols of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic rings, substituted or unsubstituted C1-C12 alkoxy, substituted or unsubstituted C1-C6 alkylthio, substituted or unsubstituted C1-C12 alkylamino, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C6-C30 arylamino, etc., but are not limited thereto, or adjacent substituents may be linked to form a ring. Preferred compounds include deuterium, halogen, cyano, nitro, substituted or unsubstituted silyl groups, C1-C25 alkyl groups, C3-C25 cycloalkyl groups, C6-C30 aryl groups, C2-C30 heteroaryl groups, C3-C30 alicyclic and C6-C30 fused cycloyl groups, and C1-C12 alkoxy groups. Specific examples may include deuterium, fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, ethyl, propyl, butyl, cyclopropyl, cyclohexyl, adamantyl, norbornel, phenyl, tolyl, mesitylene, pentadeuterated phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenylene, perylene, pyrene, fluoranyl, indene, dihydroindene, dihydronaphthyl, tetrahydronaphthyl, and 9,9 -Dimethylfluorenyl, 9,9-diphenylfluorenyl, 9-methyl-9-phenylfluorenyl, spirodifluorenyl, carbazolyl, 9-phenylcarbazolyl, carbazo-indoleyl, pyrrololyl, furanyl, thiophene, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, pyridyl, pyrimidinyl, pyrazinyl, pyrazinyl, triazinyl, oxazolyl, thiazolyl, imidazolyl, benzooxazolyl, benzothiazolyl, benzotriazolyl, benzoimidazolyl, quinolinyl, isoquinolinyl, quinoxolinyl, quinazolinyl, phenothiazinyl, phenothiazinyl, acridineyl, benzocyclobutyl, benzocyclobutenyl, benzocyclopentyl, benzocyclopentenyl, benzocyclohexyl, benzocyclohexenyl, etc., but not limited to these. Or, when there are multiple substituents, the multiple substituents may be the same or different from each other; or adjacent substituents may be connected to form a ring.

[0028] The "substituted or unsubstituted silyl group" mentioned in this invention refers to -Si(R n )3 groups, wherein each R nThe same or different from any one selected from hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C1-C25 heterocyclic alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C1-C25 heterocyclic alkane and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl. The substituted or unsubstituted silyl group may include, but is not limited to, trimethylsilyl, triethylsilyl, ethyl dimethylsilyl, triisopropylsilyl, propyl dimethylsilyl, tri-tert-butylsilyl, tert-butyl dimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, vinyl dimethylsilyl, etc.

[0029] In this specification, " "This refers to the portion that is connected to another substituent." "It can be attached to any optional position of the attached group / fragment."

[0030] In this specification, when a substituent or linking site lies within a bond that extends through two or more rings, it indicates that the substituent or linking site can be linked to any one of the two or more rings, specifically to any one of the corresponding optional sites within the ring. For example, Can represent or ; Can represent , , And so on.

[0031] In this specification, when the position of a substituent or linking site on the ring is not fixed, it means that it can be linked to any of the optional sites on the ring.

[0032] For example, Can represent , , ; Can represent , , ; Can represent , , , , , , , , , .

[0033] And so on.

[0034] The "linked ring formation" described in this invention refers to two groups being linked together by chemical bonds and optionally undergoing aromatization. Examples are shown below:

[0035] In this invention, the ring formed by the connection can be an aromatic ring system, an aliphatic ring system, or a ring system formed by the fusion of the two. The ring formed by the connection can be a three-membered ring, a four-membered ring, a five-membered ring, a six-membered ring, or a fused ring, such as benzene, naphthalene, indene, cyclopentene, cyclopentane, cyclopentanophenene, cyclohexene, cyclohexane, cyclohexanophenene, quinoline, isoquinoline, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, phenanthrene, or pyrene, but is not limited thereto.

[0036] In this invention, "at least one" includes one, two, three, or more. "Two or more" may include two, three, four, or more, where permissible.

[0037] This invention provides a heterocyclic compound having a structure represented by Formula I:

[0038] Wherein, Ar1, Ar2, and Ar3 are independently selected from any one of formula a, formula b, hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C1-C25 heterocyclic alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C1-C25 heterocyclic alkane and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl; at least one of Ar1, Ar2, and Ar3 is selected from formula a, and at least one is selected from formula a or formula b; The i is independently selected from CH and N, and when i is bonded to other groups, the i is selected from C atoms; The v is independently selected from any one of CH and N, and when v is bonded to other groups, the v is selected from C atoms; X is selected from O, S, C(R) p R q ), N(R s Any one of the following; The Y is selected from either O or S; E is selected from O, S, N(R) v Any one of the following; Group 1:

[0039] Ring A and ring B are independently selected from any one of the substituted or unsubstituted structures in group 1; and at least one of ring A and ring B is not selected from ; The z is selected from C(R) t Any one of N; The R a R b R p R q R t It is independently selected from any one of hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C1-C25 heterocyclic alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C1-C25 heterocyclic alkane and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl; The R s R v It is independently selected from any one of hydrogen, deuterium, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C1-C25 heterocyclic alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C1-C25 heterocyclic alkane and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl; a1 is selected from 0, 1, 2, 3 or 4; when there are two or more R a At that time, two or more R a The same or different between each other, or two adjacent R a They connect with each other to form substituted or unsubstituted rings; b1 is selected from 0, 1, 2, 3, 4, or 5; when there are two or more R b At that time, two or more R bThe same or different between each other, or two adjacent R b They connect with each other to form substituted or unsubstituted rings; L1, L2, L3, L4, and L5 are independently selected from any one of the following: single bond, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C6-C30 heteroarylene, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic rings, and substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic rings.

[0040] Preferably, the heterocyclic compound is selected from any one of the following structures:

[0041] Ar3, ring A, ring B, Y, L1, L2, L3, L4, L5, X, i, R a R b The definitions of a1, b1, and E are the same as those in Equation I.

[0042] Preferably, the Selected from any one of the following groups:

[0043] Y1 is selected from O, S, C(R) x R y ), N(R z Any one of the following; The R a R x Ry Independently selected from any one of hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C1-C25 heterocyclic alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C1-C25 heterocyclic alkane and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl, or R x R y The links between them form substituted or unsubstituted rings; The R z It is independently selected from any one of hydrogen, deuterium, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C1-C25 heterocyclic alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C1-C25 heterocyclic alkane and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl; a1 is selected from 0, 1, 2, 3, or 4; a2 is selected from 0, 1, 2, or 3; a3 is selected from 0, 1, or 2; a4 is selected from 0, 1, 2, 3, 4, 5, or 6; a5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; when there are two or more R... a At that time, two or more R a They may be the same as or different from each other.

[0044] More preferably, the Selected from any one of the following groups:

[0045] The R a R x R y The group independently selected from hydrogen, deuterium, halogen, cyano, nitro, or substituted or unsubstituted groups, including: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, vinyldimethylsilyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropane, naphthocyclopropane, benzocyclobutane, naphthocyclobutane, benzocyclopentane, naphthocyclopentane, benzocyclohexane, naphthocyclohexane, benzocycloheptane, benzocyclobutenyl, benzene Benzylcyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthraceneyl, phenanthrene, pyrene, perylene, fluoranthyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, benzofuranyl, dibenzofuranyl, benzodibenzofuranyl, thiopheneyl, benzothiopheneyl, dibenzothiopheneyl, benzodibenzothiopheneyl, indoleyl, carbazoleyl, Pyrrole, oxazolyl, benzoxazolyl, dibenzoxazolyl, thiazolyl, benzothiazolyl, dibenzothiazolyl, imidazolyl, benzoimidazolyl, dibenzoimidazolyl, quinolinyl, benzoquinolinyl, isoquinolinyl, benzoisoquinolinyl, quinazolinyl, benzoquinazolinyl, quinoxalinyl, benzoquinoxalinyl, phenantholinyl, naphridinyl, indoleyl, acridineyl, phenoxazinyl, phenothiazinyl, any one of these, or R x R y The links between them form substituted or unsubstituted rings; The R zThe following groups are independently selected from hydrogen, deuterium, substituted or unsubstituted groups: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, ethylene. The following are all of the following: dimethylsilyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropane, naphthocyclopropane, benzocyclobutane, naphthocyclobutane, benzocyclopentane, naphthocyclopentane, benzocyclohexane, naphthocyclohexane, benzocycloheptane, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthraceneyl, phenanthrene, triphenylene, pyrene, perylene, fluoranyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, and triazinyl; a1 is selected from 0, 1, 2, 3, or 4; a2 is selected from 0, 1, 2, or 3; a3 is selected from 0, 1, or 2; a4 is selected from 0, 1, 2, 3, 4, 5, or 6; a5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; when there are two or more R... a At that time, two or more R a They may be the same as or different from each other.

[0046] Preferably, formula a is selected from any one of the following groups:

[0047] The x is independently selected from either CH or N; The Y is independently selected from either O or S; The R dThe group is independently selected from hydrogen, deuterium, halogen, cyano, nitro, and substituted or unsubstituted groups of the following: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornel, trimethylsilyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, vinyldimethylsilyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropane, naphthocyclopropane, benzocyclobutane, naphthocyclobutane, benzocyclopentane, naphthocyclopentane, benzocyclohexane, naphthocyclohexane, benzocycloheptane, benzocyclobutenyl. Benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenylene, pyrene, perylene, fluoranthyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, benzofuranyl, dibenzofuranyl, benzodibenzofuranyl, thiophene, benzothiophene, dibenzothiophene, benzodibenzothiophene, indole, carbazole The following are all of the following: yl, pyrrole, oxazolyl, benzoxazolyl, dibenzoxazolyl, thiazolyl, benzothiazolyl, dibenzothiazolyl, imidazolyl, benzoimidazolyl, dibenzoimidazolyl, quinolinyl, benzoquinolinyl, isoquinolinyl, benzoisoquinolinyl, quinazolinyl, benzoquinazolinyl, quinoxalinyl, benzoquinoxalinyl, phenantholinyl, naphridinyl, indolyl, acridinel, phenoxazinyl, phenothiazinyl; The d1 is selected from 0, 1, 2, 3, 4, 5, or 6; the d2 is selected from 0, 1, 2, or 3; the d3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; the d4 is selected from 0, 1, 2, 3, or 4; the d5 is selected from 0, 1, 2, 3, 4, or 5; the d6 is selected from 0, 1, 2, 3, 4, 5, 6, or 7; when there are two or more R... d At that time, two or more R d They may be the same as or different from each other.

[0048] Preferably, at most three, two, or one x in each group are selected from N.

[0049] Preferably, in each six-membered ring containing x, at most two or at most one x are selected from N.

[0050] More preferably, formula a is selected from any one of the following groups: .

[0051] Preferably, formula b is selected from any one of the following groups:

[0052]

[0053] The R bThe group is independently selected from hydrogen, deuterium, halogen, cyano, nitro, and substituted or unsubstituted groups of the following: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornel, trimethylsilyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, vinyldimethylsilyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropane, naphthocyclopropane, benzocyclobutane, naphthocyclobutane, benzocyclopentane, naphthocyclopentane, benzocyclohexane, naphthocyclohexane, benzocycloheptane, benzocyclobutenyl. Benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenylene, pyrene, perylene, fluoranthyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, benzofuranyl, dibenzofuranyl, benzodibenzofuranyl, thiophene, benzothiophene, dibenzothiophene, benzodibenzothiophene, indole, carbazole The following are all of the following: yl, pyrrole, oxazolyl, benzoxazolyl, dibenzoxazolyl, thiazolyl, benzothiazolyl, dibenzothiazolyl, imidazolyl, benzoimidazolyl, dibenzoimidazolyl, quinolinyl, benzoquinolinyl, isoquinolinyl, benzoisoquinolinyl, quinazolinyl, benzoquinazolinyl, quinoxalinyl, benzoquinoxalinyl, phenantholinyl, naphridinyl, indolyl, acridinel, phenoxazinyl, phenothiazinyl; The R v The group independently selected from hydrogen, deuterium, halogen, cyano, nitro, or substituted or unsubstituted groups, including: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl Alkyl, vinyldimethylsilyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropane, naphthocyclopropane, benzocyclobutane, naphthocyclobutane, benzocyclopentane, naphthocyclopentane, benzocyclohexane, naphthocyclohexane, benzocycloheptane, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthraceneyl, phenanthrene, triphenylene, pyrene, perylene, fluoranyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl; b1 is selected from 0, 1, 2, 3, 4, or 5; b2 is selected from 0, 1, 2, 3, 4, 5, 6, or 7; b3 is selected from 0, 1, or 2; b4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; b5 is selected from 0 or 1; b6 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9; when there are two or more R... b At that time, two or more R b They may be the same as or different from each other.

[0054] Preferably, at most three, two, or one v in each group are selected from N.

[0055] Preferably, in each six-membered ring containing v, at most two or at most one v is selected from N.

[0056] More preferably, formula b is selected from any one of the following groups: .

[0057] Preferably, when Ar1, Ar2, and Ar3 are not selected from formulas a and b, Ar1, Ar2, and Ar3 are independently selected from hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted silyl group, substituted or unsubstituted C1-C25 alkyl group, substituted or unsubstituted C3-C25 cycloalkyl group, substituted or unsubstituted C1-C25 heterocycloalkyl group, or any one of the following groups:

[0058] The u is independently selected from any one of CH and N atoms; when u is bonded to other groups, the u is selected from C atoms. The ring D is selected from substituted or unsubstituted C3~C10 alicyclic rings; X4 is selected from O, S, N(R) w Any one of the following; The X5 is selected from C(R)u R r ), N(R w Any one of the following; X6 and X7 are independently selected from O, S, and C(R). u R r ), N(R w Any one of the following; The R e R e 'Independently selected from any one of hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C1-C25 heterocyclic alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C1-C25 heterocyclic alkane and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl; The R u R r Independently selected from any one of hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, or R u R r The links between them form substituted or unsubstituted rings; The R w It is independently selected from any one of hydrogen, deuterium, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl; The value of e1 is selected from 0, 1, 2, 3, 4, or 5; the value of e2 is selected from 0, 1, 2, 3, or 4; the value of e3 is selected from 0, 1, 2, 3, 4, 5, 6, or 7; the value of e4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9; the value of e5 is selected from 0, 1, or 2; the value of e6 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11; the value of e7 is selected from 0, 1, 2, or 3; the value of e8 is selected from 0, 1, 2, 3, 4, 5, or 6; when there are two or more R... e At that time, two or more R eThe same or different between each other, or two adjacent R e They connect with each other to form substituted or unsubstituted rings; The term e'1 is selected from 0, 1, or 2; when there are two or more R... e At that time, two or more R e 'They are the same as or different from each other.'

[0059] More preferably, when Ar1, Ar2, and Ar3 are not selected from formulas a and b, Ar1, Ar2, and Ar3 are independently selected from hydrogen, deuterium, halogen, cyano, nitro, and substituted or unsubstituted groups such as: methyl, ethyl, propyl, butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, vinyldimethylsilyl, tetrahydropyrrolyl, piperidinyl, and any one of the following groups:

[0060] The R e R e '、R u R rThe group is independently selected from hydrogen, deuterium, fluorine, trifluoromethyl, nitro, and substituted or unsubstituted groups of the following: methyl, ethyl, propyl, butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, vinyldimethylsilyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropane, naphthocyclopropane, benzocyclobutane, naphthocyclobutane, benzocyclopentane, naphthocyclopentane, benzocyclohexane, naphthocyclohexane, benzocycloheptane, benzocyclobutenyl, benzocyclopentenyl. Benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthraceneyl, phenanthrene, pyrene, perylene, phenylene, acenaphthene, fluoranyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, benzofuranyl, dibenzofuranyl, benzodibenzofuranyl, thiopheneyl, benzothiopheneyl, dibenzothiopheneyl, benzodibenzothiopheneyl, pyrroleyl, indole Any one of the following: doloyl, carbazolyl, oxazolyl, benzoxazolyl, dibenzoxazolyl, thiazolyl, benzothiazolyl, dibenzothiazolyl, imidazolyl, benzoimidazolyl, dibenzoimidazolyl, quinolinyl, benzoquinolinyl, isoquinolinyl, benzoisoquinolinyl, quinazolinyl, benzoquinazolinyl, quinoxalinyl, benzoquinoxalinyl, phenantholinyl, naphridyl, acridineyl, phenoxazinyl, phenothiazinyl; The R w The following groups are independently selected from hydrogen, deuterium, substituted or unsubstituted groups: methyl, ethyl, propyl, butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenyl Any one of the following: silyl, vinyldimethylsilyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropane, naphthocyclopropane, benzocyclobutane, naphthocyclobutane, benzocyclopentane, naphthocyclopentane, benzocyclohexane, naphthocyclohexane, benzocycloheptane, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, naphthyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl; The value of e1 is selected from 0, 1, 2, 3, 4, or 5; the value of e2 is selected from 0, 1, 2, 3, or 4; the value of e3 is selected from 0, 1, 2, 3, 4, 5, 6, or 7; the value of e4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9; the value of e5 is selected from 0, 1, or 2; the value of e6 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11; the value of e7 is selected from 0, 1, 2, or 3; the value of e8 is selected from 0, 1, 2, 3, 4, 5, or 6; the value of e9 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; when there are two or more R... e At that time, two or more R e The same or different between each other, or two adjacent R e They connect with each other to form substituted or unsubstituted rings; The term e'1 is selected from 0, 1, or 2; the term e'2 is selected from 0, 1, 2, 3, or 4; the term e'3 is selected from 0, 1, 2, 3, 4, 5, or 6; the term e'4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; the term e'5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; when there are two or more R... e At that time, two or more R e 'They are the same as or different from each other.'

[0061] More preferably, when Ar1, Ar2, and Ar3 are not selected from formulas a and b, Ar1, Ar2, and Ar3 are independently selected from hydrogen, deuterium, halogen, cyano, nitro, methyl, ethyl, propyl, butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornel, trimethylsilyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, vinyldimethylsilyl, tetrahydropyrrolyl, piperidinyl, and any one of the following groups:

[0062]

[0063]

[0064]

[0065]

[0066]

[0067]

[0068]

[0069]

[0070]

[0071]

[0072]

[0073]

[0074] .

[0075] Preferably, L1, L2, L3, L4, and L5 are independently selected from single bonds or any one of the following groups, or a combination of two or more of the following groups:

[0076]

[0077] X1 and X2 are independently selected from O, S, and N(R). k Any one of the following; X3 is selected from O, S, C(R) i R j ), N(R k Any one of the following; The term 'e' is independently selected from either CH or N; The ring C is selected from substituted or unsubstituted C3~C10 alicyclic rings; The R c R c '、R i R j Independently selected from any one of hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C25 heterocyclic alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C1-C25 heterocyclic alkane and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl, or R i R j The links between them form substituted or unsubstituted rings; The R kIndependently selected from any one of hydrogen, deuterium, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C25 heterocyclic alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C1-C25 heterocyclic alkane and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl; p is selected from 1, 2, 3, or 4; c1 is selected from 0, 1, 2, 3, or 4; c2 is selected from 0, 1, 2, 3, 4, 5, or 6; c3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; c4 is selected from 0, 1, or 2; when there are two or more R... c At that time, two or more R c The same or different between each other, or two adjacent R c They connect with each other to form substituted or unsubstituted rings; The c'1 is selected from 0, 1, or 2; when there are two or more R... c At that time, two or more R c 'They are the same as or different from each other.'

[0078] More preferably, L1, L2, L3, L4, and L5 are independently selected from single bonds or any one of the following groups, or a combination of two or more of the following groups:

[0079] The R c R cThe group is independently selected from hydrogen, deuterium, fluorine, cyano, nitro, and the following groups, whether substituted or unsubstituted: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornel, trimethylsilyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, vinyldimethylsilyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropane, naphthocyclopropane, benzocyclobutane, naphthocyclobutane, benzocyclopentane, naphthocyclopentane, benzocyclohexane, naphthocyclohexane, benzocycloheptane, benzocyclobutenyl. Benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenylene, pyrene, perylene, fluoranthyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, benzofuranyl, dibenzofuranyl, benzodibenzofuranyl, thiophene, benzothiophene, dibenzothiophene, benzodibenzothiophene, indole, carbazole The following are all of the following: yl, pyrrole, oxazolyl, benzoxazolyl, dibenzoxazolyl, thiazolyl, benzothiazolyl, dibenzothiazolyl, imidazolyl, benzoimidazolyl, dibenzoimidazolyl, quinolinyl, benzoquinolinyl, isoquinolinyl, benzoisoquinolinyl, quinazolinyl, benzoquinazolinyl, quinoxalinyl, benzoquinoxalinyl, phenantholinyl, naphridinyl, indolyl, acridinel, phenoxazinyl, phenothiazinyl; The R i R j The group independently selected from hydrogen, deuterium, fluorine, cyano, nitro, or substituted or unsubstituted groups, including: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl Alkyl, vinyldimethylsilyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropane, naphthocyclopropane, benzocyclobutane, naphthocyclobutane, benzocyclopentane, naphthocyclopentane, benzocyclohexane, naphthocyclohexane, benzocycloheptane, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthraceneyl, phenanthrene, triphenylene, pyrene, perylene, fluoranyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl; The R kThe following groups are independently selected from hydrogen, deuterium, substituted or unsubstituted groups: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, ethylene. The following are all of the following: dimethylsilyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropane, naphthocyclopropane, benzocyclobutane, naphthocyclobutane, benzocyclopentane, naphthocyclopentane, benzocyclohexane, naphthocyclohexane, benzocycloheptane, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthraceneyl, phenanthrene, triphenylene, pyrene, perylene, fluoranyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, and triazinyl; c1 is selected from 0, 1, 2, 3, or 4; c2 is selected from 0, 1, 2, 3, 4, 5, or 6; c3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; c4 is selected from 0, 1, or 2; c5 is selected from 0, 1, 2, or 3; c6 is selected from 0, 1, 2, 3, 4, or 5; c7 is selected from 0, 1, 2, 3, 4, 5, 6, or 7; when there are two or more R... c At that time, two or more R c The same or different between each other, or two adjacent R c They connect with each other to form substituted or unsubstituted rings; c'1 is selected from 0, 1, or 2; c'2 is selected from 0, 1, 2, 3, or 4; c'3 is selected from 0, 1, 2, 3, 4, 5, or 6; c'4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; c'5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; c'6 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, or 14; when there are two or more R... c At that time, two or more R c 'They are the same as or different from each other.'

[0080] More preferably, L1, L2, L3, L4, and L5 are independently selected from single bonds or any one of the following groups, or a combination of two or more of the following groups: .

[0081] Most preferably, formula I is selected from any of the following structures: 。

[0082] The above lists some specific structural forms of heterocyclic compounds represented by chemical formula I according to the present invention. However, the present invention is not limited to these listed chemical structures. Any structure based on the structure shown in chemical formula I, with substituents as defined above, should be included.

[0083] The present invention provides an organic electroluminescent device, comprising an anode, a cathode, and an organic layer located between the anode and the cathode or on the side of the cathode opposite to the anode, wherein the organic layer comprises at least one of the heterocyclic compounds described in the present invention.

[0084] Preferably, the organic layer is located between the anode and the cathode, and the organic layer includes at least one of a hole transport region, a light-emitting layer, and an electron transport layer.

[0085] Preferably, the hole transport region includes at least one of a hole injection layer, a hole transport layer, and an electron blocking layer.

[0086] Preferably, the hole transport layer includes a first hole transport layer and a second hole transport layer, wherein the first hole transport layer is located between the anode and the light-emitting layer, and the second hole transport layer is located between the first hole transport layer and the light-emitting layer.

[0087] Preferably, the hole transport layer includes a first hole transport layer, a second hole transport layer, and a third hole transport layer, wherein the first hole transport layer is located between the anode and the light-emitting layer, the second hole transport layer is located between the first hole transport layer and the light-emitting layer, and the third hole transport layer is located between the second hole transport layer and the light-emitting layer.

[0088] Preferably, the organic layer is located between the anode and the cathode, and the organic layer comprises at least one of the light-emitting layers, wherein the at least one of the light-emitting layers comprises at least one of the heterocyclic compounds described in this invention.

[0089] Preferably, the light-emitting layer comprises a host material and a dopant material.

[0090] More preferably, the light-emitting layer comprises a host material, which comprises at least one of the heterocyclic compounds described in this invention.

[0091] Preferably, the electron transport region comprises at least one of an electron injection layer, an electron transport layer, and a hole blocking layer.

[0092] Preferably, the organic layer is located on the side of the cathode opposite to the anode, and the organic layer includes a capping layer containing at least one of the heterocyclic compounds described in this invention.

[0093] The anode material described in this invention is preferably a high work function material, including metals, alloys, conductive compounds, and mixtures thereof. Specific examples include, but are not limited to, metals such as platinum (Pt), chromium (Cr), copper (Cu), zinc (Zn), palladium (Pd), titanium (Ti), and gold (Au), or alloys thereof; metal oxides such as zinc oxide (ZnO), indium oxide (InO), tin oxide (SnO2), indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as zinc oxide / aluminum (ZnO / Al), silver / indium tin oxide (Ag / ITO), and indium tin oxide / silver / indium tin oxide (ITO / Ag / ITO); conductive polymers such as poly[3,4-(ethylene-1,2-dioxothiophene)] (PEDOT), polypyrrole (PPY), and polyaniline (PANI), but are not limited thereto.

[0094] The hole injection layer of this invention is preferably made of a material with high hole injectability. The hole injection layer material may include metal compounds, quinone derivatives, aromatic amine derivatives, polycyano conjugated organic compounds, polymers, etc. Specific examples include, but are not limited to, tetracyanoquinone dimethyl ether (TCNQ), 2,3,5,6-tetrafluoro-7,7',8,8'-tetracyanoquinone-dimethyl ether (F4-TCNQ), 4,4',4''-tris(N,N-diphenylamino)triphenylamine (TDATA), 4,4',4''-tris(N-3-methylphenyl-N-phenylamino)triphenylamine (m-MTDATA), 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (DPAB), 4,4'-bis(N-{4-[N'-(3-methylphenyl)-N' [-phenylamino]phenyl}-N-phenylamino)biphenyl (DNTPD), molybdenum trioxide (MoO3), vanadium pentoxide (V2O5), tungsten trioxide (WO3), nickel oxide (NiO), titanium dioxide (TiO2), copper phthalocyanine (CuPc), titanium phthalocyanine (TiOPC), 4,4',4”-tris[2-naphthylphenylamino]triphenylamine (2T-NATA), 1,4,5,8,9,11-hexaazabenzonitrile (HAT-CN), poly(3,4-ethylenedioxythiophene) / poly(styrenesulfonic acid) (PEDOT / PSS), etc.

[0095] The hole transport layer described in this invention is preferably made of a material with high hole transport properties. Hole transport layer materials may include aromatic amine derivatives, biphenyl diamine derivatives, carbazole derivatives, fluorene derivatives, stilbene derivatives, phthalocyanine compounds, anthraquinone compounds, quinacridone compounds, hexanitrile hexaazabenzophenanthrene compounds, etc. Specific examples of hole transport materials include, but are not limited to, N,N'-diphenyl-N,N'-(1-naphthyl)-1,1'-biphenyl-4,4'-diamine (NPB), N4,N4,N4',N4'-tetra([1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4,4'-diamine, 4,4'-cyclohexylbis[N,N-di(4-methylphenyl)aniline] (TAPC), N,N'-diphenyl-N,N'-di(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine (TPD), 2,2,7,7-tetra(diphenylamino)-9,9-spirodifluorene (Spiro-TAD), and 4,4',4”-tris(carbazole-9-yl)triphenylamine (TCTA), etc.

[0096] The electron blocking layer described in this invention is preferably made of a material with good hole transport capability and electron blocking capability. Electron blocking layer materials may include aromatic amine derivatives, carbazole derivatives, etc. Specific examples of the electron blocking layer include, but are not limited to, N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (TPD), 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB), etc., but are not limited thereto.

[0097] The luminescent layer of this invention may include a single material, a host material (also called a matrix material), and a dopant material (also called a guest material). The luminescent layer material may include multiple host materials and multiple dopant materials. The type of dopant material can be fluorescent, phosphorescent, or TADF. Fluorescent dopant materials may include: fused polycyclic aromatic derivatives, styrene-based amine derivatives, fused-ring amine derivatives, boron-containing compounds, pyrrole derivatives, indole derivatives, carbazole derivatives, etc., such as C545T, BCzVBi, DPAVBi, etc. Phosphorescent dopant materials may include: heavy metal complexes, phosphorescent rare-earth metal complexes, etc., such as FIrpic, Ir(ppy)3, Ir(ppy)2(acac), etc. In addition to the heterocyclic compounds provided in this invention, the host material of the luminescent layer may also include fused aromatic ring derivatives, heterocyclic compounds, etc. Fused aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentane derivatives, phenanthrene derivatives, fluoranthene derivatives, etc., and heterocyclic compounds include carbazole derivatives, dibenzofuran derivatives, dibenzothiophene derivatives, pyrimidine derivatives, etc., such as Alq3, BAlq, TPBi, TPD, CBP, TCTA, ADN, etc., but are not limited thereto. Heterocyclic compounds of the present invention are preferred.

[0098] The hole-blocking layer described in this invention can typically be formed under the same conditions as the hole injection layer. It may include aluminum complexes, lithium complexes, beryllium complexes, oxazole derivatives, benzoxazole derivatives, thiazole derivatives, benzothiazole derivatives, imidazole derivatives, benzimidazole derivatives, phenanthrene derivatives, polymers, rare earth derivatives, triazine derivatives, quinoline derivatives, diazanphenanthrene derivatives, azirbenzene derivatives, anthrone derivatives, etc. Specific examples of the hole-blocking layer material include, but are not limited to, BCP, BAlq, TPBi, etc.

[0099] The electron transport layer described in this invention is preferably made of a material with high electron transport properties. Electron transport layer materials may include metal complexes, pyridine derivatives, imidazole derivatives, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, etc. The electron transport materials include, but are not limited to, tris(8-hydroxyquinoline)aluminum(III) (Alq3), 3,3'-[5'-[3-(3-pyridyl)phenyl](TmPyPB), 1,3,5-tris(N-phenyl-2-benzimidazole)benzene (TPBi), 2-(4-biphenyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (PBD), 3-(biphenyl-4-yl)-4-phenyl-5-(4-tert-butylphenyl)-1,2,4-triazole (TAZ), 4,7-diphenyl-1,10-phenanthroline (Bphen), bis(10-hydroxybenzo[h]quinoline)beryllium (BeBq2), and bis(2-methyl-8-hydroxyquinoline)(4-phenylphenol)aluminum(III) (BAlq), etc.

[0100] The electron injection layer described in this invention is preferably made of a material with high electron injection properties, including metals, metal salts, and metal oxides. The electron injection materials include, but are not limited to, lithium (Li), cesium (Cs), lithium fluoride (LiF), lithium oxide (Li₂O), cesium fluoride (CsF), magnesium phosphide (MgP), cesium carbonate (Cs₂CO₃), lithium oxide (Li₂O), lithium boron oxide (LiBO₂), aluminum oxide (Al₂O₃), and vanadium oxide (V₂O₅).

[0101] The cathode of this invention is preferably made of a material with a low work function. The cathode materials of this invention include, but are not limited to, metals, metal alloys, conductive compounds, and mixtures thereof. Specific examples of the cathode materials include, but are not limited to, aluminum (Al), silver (Ag), gold (Au), lead (Pb), lithium (Li), magnesium (Mg), ytterbium (Yb), calcium (Ca), magnesium-silver alloy (Mg:Al), lithium-aluminum alloy (Li:Al), and calcium / silver (Ca / Ag).

[0102] The capping material described in this invention is preferably a material with photocoupling properties. In addition to the heterocyclic compounds provided in this invention, the capping material also includes imidazole derivatives, oxazole derivatives, thiazole derivatives, aromatic amine derivatives, etc. Specific examples of the capping material include, but are not limited to, tris(8-hydroxyquinoline)aluminum(III) (Alq3), N,N'-di(naphthyl-1-yl)-N,N'-di(phenyl)-2,2'-dimethylbenzidine (NPD), 4,4'-di(9-carbazole)biphenyl (CBP), N4,N4,N4',N4'-tetra(4-methoxyphenyl)-[1,1'-biphenyl]-4,4'-diamine (MeO-TPD), lithium fluoride, magnesium fluoride, etc. The heterocyclic compounds of this invention are preferred.

[0103] The following is one method for preparing the compound represented by chemical formula I of this invention, but the preparation method of this invention is not limited thereto. The core structure of the compound of chemical formula I can be prepared by the reaction route shown below. Substituents can be bonded by methods known in the art, and the type and position or number of substituents can be changed according to techniques known in the art.

[0104] [Synthesis Route]

[0105] when , Similarly, the compound of formula I is prepared via the following route:

[0106] When Ar3 and L3 are single bonds, the compound of formula I is prepared via the following route:

[0107] Xa, Xb, Xc, Xd, Xe, Xf, Xg, and Xh are each independently selected from any one of Cl, Br, and I; Ar1, Ar2, Ar3, L1, L2, L3, and R... a The restrictions on a1 and i are the same as those mentioned above.

[0108] Description of raw materials, reagents, and characterization equipment: The present invention does not impose any particular restrictions on the source of raw materials and reagents used in the following embodiments, which can be commercially available products or prepared using preparation methods well known to those skilled in the art.

[0109] Mass spectrometry was performed using a Waters G2-Si quadrupole tandem time-of-flight high-resolution mass spectrometer, with chloroform as the solvent. Elemental analysis was performed using a VarioELcube organic elemental analyzer from Elementar GmbH, Germany, with sample masses ranging from 5 to 10 mg.

[0110] Synthesis Example 1: Preparation of Compound 3

[0111] Preparation of intermediate A-3

[0112] Under nitrogen protection, a-3 (24.10 g, 70 mmol), b-3 (18.35 g, 70 mmol), and K2CO3 (19.35 g, 140.00 mmol) were dissolved in 350 mL of toluene / ethanol / water (2:1:1). Pd(dppf)Cl2 (1.02 g, 1.40 mmol) was added with stirring, and the mixture was heated under reflux for 5.5 h. After the reaction was complete, the reaction mixture was cooled to room temperature, filtered, washed with distilled water, and then recrystallized from the solid using toluene / ethanol in an 8:1 ratio to give intermediate A-3 (22.37 g, 80% yield); HPLC purity ≥ 99.87%. Mass spectrometry m / z: 399.1274 (theoretical value: 399.1259).

[0113] Preparation of compound 3

[0114] Under nitrogen protection, A-3 (19.97 g, 50.00 mmol), c-3 (14.86 g, 50.00 mmol), and sodium tert-butoxide (7.21 g, 75.00 mmol) dissolved in 225 mL of toluene were added to a reaction flask. Pd₂(dba)₃ (0.46 g, 0.50 mmol) and X-Phos (0.48 g, 1.00 mmol) were added with stirring. The mixture of the above reactants was heated under reflux for 7.5 h. After the reaction was complete, the mixture was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure. Recrystallization from toluene gave compound 3 (22.16 g, 72% yield). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 615.1842 (theoretical value: 615.1834). Theoretical elemental content C 44 H 25 NO3, C, 85.84; H, 4.09; N, 2.28; (%) Measured element content (%): C, 85.86; H, 4.15; N, 2.23.

[0115] Synthesis Example 2: Preparation of Compound 63

[0116] According to the preparation method in Example 1, a-3 was replaced with an equimolar amount of a-63, and c-3 was replaced with an equimolar amount of c-63, yielding compound 63 (19.33 g). HPLC analysis showed a solid purity ≥ 99.99%. Mass spectrometry m / z: 515.1531 (theoretical value: 515.1521). Theoretical elemental content (%) C 36 H 21 NO3: C, 83.87; H, 4.11; N, 2.72. Measured elemental content (%): C, 83.93; H, 4.16; N, 2.67.

[0117] Synthesis Example 3: Preparation of Compound 68

[0118] According to the preparation method in Example 1, a-3 was replaced with an equimolar amount of a-63, b-3 with an equimolar amount of b-68, and c-3 with an equimolar amount of c-68, yielding compound 68 (21.60 g). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 591.1846 (theoretical value: 591.1834). Theoretical elemental content (%) C 42 H 25 NO3: C, 85.26; H, 4.26; N, 2.37. Measured elemental content (%): C, 85.29; H, 4.24; N, 2.40.

[0119] Synthesis Example 4: Preparation of Compound 133

[0120] According to the preparation method in Synthesis Example 1, a-3 was replaced with an equimolar amount of a-63, b-3 with an equimolar amount of b-133, and c-3 with an equimolar amount of c-133, yielding compound 133 (20.93 g). HPLC analysis showed a solid purity ≥ 99.98%. Mass spectrometry m / z: 565.1689 (theoretical value: 565.1678). Theoretical elemental content (%) C 40 H 23 NO3: C, 84.94; H, 4.10; N, 2.48. Measured elemental content (%): C, 84.89; H, 4.16; N, 2.43.

[0121] Synthesis Example 5: Preparation of Compound 147

[0122] Preparation of intermediate A-147

[0123] Under nitrogen protection, a-63 (34.17 g, 140 mmol), b-147 (23.87 g, 70 mmol), and K₂CO₃ (29.02 g, 210.00 mmol) were dissolved in 525 mL of toluene / ethanol / water (2:1:1). Pd(dppf)Cl₂ (1.54 g, 2.10 mmol) was added with stirring, and the mixture was heated under reflux for 6.5 h. After the reaction was complete, the reaction mixture was cooled to room temperature, filtered, washed with distilled water, and then recrystallized from the solid using toluene / ethanol in an 8:1 ratio to give intermediate A-147 (23.56 g, 81% yield); HPLC purity ≥ 99.87%. Mass spectrometry m / z: 415.1217 (theoretical value: 415.1208).

[0124] Preparation of compound 147

[0125] Under nitrogen protection, A-147 (20.77 g, 50.00 mmol), c-3 (14.86 g, 50.00 mmol), and sodium tert-butoxide (7.21 g, 75.00 mmol) dissolved in 225 mL of toluene were added to a reaction flask with stirring. Pd₂(dba)₃ (0.46 g, 0.50 mmol) and X-Phos (0.48 g, 1.00 mmol) were then added. The mixture of the above reactants was heated under reflux for 7 h. After the reaction was complete, the mixture was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure. Recrystallization from toluene yielded compound 147 (22.74 g, 72% yield). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 631.1796 (theoretical value: 631.1784). Theoretical elemental content C 44 H 25 NO4, C, 83.66; H, 3.99; N, 2.22; (%) Measured element content (%): C, 83.71; H, 3.97; N, 2.28.

[0126] Synthesis Example 6: Preparation of Compound 164

[0127] According to the preparation method in Synthesis Example 5, b-147 was replaced with an equimolar amount of b-164, and c-3 was replaced with an equimolar amount of c-164 to obtain compound 164 (24.42 g). HPLC analysis showed that the solid purity was ≥99.93%. Mass spectrometry m / z: 707.2084 (theoretical value: 707.2097). Theoretical elemental content (%) C 50 H 29NO4: C, 84.85; H, 4.13; N, 1.98. Measured elemental content (%): C, 84.91; H, 4.17; N, 1.94.

[0128] Synthesis Example 7: Preparation of Compound 251

[0129] According to the preparation method in Example 1, c-3 was replaced with an equimolar amount of c-251 to obtain compound 251 (21.63 g). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 592.1795 (theoretical value: 592.1787). Theoretical elemental content (%) C 41 H 24 N2O3: C, 83.09; H, 4.08; N, 4.73. Measured elemental content (%): C, 83.14; H, 4.01; N, 4.76.

[0130] Synthesis Example 8: Preparation of Compound 374

[0131] According to the preparation method in Synthesis Example 5, a-63 was replaced with an equimolar amount of a-374, and b-147 was replaced with an equimolar amount of b-164, yielding compound 374 (23.57 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 663.1339 (theoretical value: 663.1327). Theoretical elemental content (%) C 44 H 25 NO2S2: C, 79.61; H, 3.80; N, 2.11. Measured elemental content (%): C, 79.68; H, 3.75; N, 2.16.

[0132] Synthesis Example 9: Preparation of Compound 423

[0133] According to the preparation method in Example 1, c-3 was replaced with an equimolar amount of c-423 to obtain compound 423 (21.88 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 607.1619 (theoretical value: 607.1606). Theoretical elemental content (%) C 42 H 25 NO2S: C, 83.01; H, 4.15; N, 2.30. Measured elemental content (%): C, 83.05; H, 4.21; N, 2.25.

[0134] Synthesis Example 10: Preparation of Compound 490

[0135] According to the preparation method in Synthesis Example 1, a-3 was replaced with an equimolar amount of a-490, b-3 with an equimolar amount of b-490, and c-3 with an equimolar amount of c-490, yielding compound 490 (25.26 g). HPLC analysis showed a solid purity ≥ 99.93%. Mass spectrometry m / z: 742.2635 (theoretical value: 742.2620). Theoretical elemental content (%) C 54 H 34 N2O2: C, 87.31; H, 4.61; N, 3.77. Measured elemental content (%): C, 87.33; H, 4.62; N, 3.79.

[0136] Synthetic Example 11: Preparation of Compound 514

[0137] According to the preparation method in Synthesis Example 5, a-63 was replaced with an equimolar amount of a-514, b-147 was replaced with an equimolar amount of b-164, and c-3 was replaced with an equimolar amount of c-514, yielding compound 514 (27.63 g). HPLC analysis showed a solid purity ≥ 99.91%. Mass spectrometry m / z: 849.2177 (theoretical value: 849.2160). Theoretical elemental content (%) C 60 H 35 NOS2: C, 84.78; H, 4.15; N, 1.65. Measured elemental content (%): C, 84.72; H, 4.19; N, 1.61.

[0138] Synthesis Example 12: Preparation of Compound 554

[0139] According to the preparation method in Synthesis Example 5, a-63 was replaced with an equimolar amount of a-554, b-147 was replaced with an equimolar amount of b-164, and c-3 was replaced with an equimolar amount of c-554, yielding compound 554 (26.80 g). HPLC analysis showed a solid purity ≥ 99.92%. Mass spectrometry m / z: 799.2173 (theoretical value: 799.2181). Theoretical elemental content (%) C 56 H 33 NO3S: C, 84.08; H, 4.16; N, 1.75. Measured elemental content (%): C, 84.11; H, 4.13; N, 1.82.

[0140] Synthesis Example 13: Preparation of Compound 618

[0141] According to the preparation method in Example 1, a-3 was replaced with an equimolar amount of a-618, and c-3 was replaced with an equimolar amount of c-554 to obtain compound 618 (24.50 g). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 699.1678 (theoretical value: 699.1691). Theoretical elemental content (%) C 48 H 29 NOS2: C, 82.37; H, 4.18; N, 2.00. Measured elemental content (%): C, 82.33; H, 4.14; N, 2.06.

[0142] Synthetic Example 14: Preparation of Compound 756

[0143] Preparation of intermediate A-756

[0144] Under nitrogen protection, a-63 (24.41 g, 100 mmol), b-756 (31.26 g, 100 mmol), and K₂CO₃ (27.64 g, 200.00 mmol) were dissolved in 500 mL of toluene / ethanol / water (2:1:1). Pd(dppf)Cl₂ (1.46 g, 2.00 mmol) was added with stirring, and the mixture was heated under reflux for 5.5 h. After the reaction was complete, the reaction mixture was cooled to room temperature, filtered, washed with distilled water, and then recrystallized from the solid using toluene / ethanol in an 8:1 ratio to give intermediate A-756 (29.04 g, 83% yield); HPLC purity ≥ 99.78%. Mass spectrometry m / z: 349.0345 (theoretical value: 349.0328).

[0145] Preparation of intermediate B-756

[0146] Under argon protection, A-756 (26.24 g, 75.00 mmol), a-374 (19.51 g, 75.00 mmol), K2CO3 (15.55 g, 112.50 mmol), and 625 mL of toluene / ethanol / water (2:1:1) mixed solvent were added to the reaction flask. After purging the air three times with argon, Pd(PPh3)4 (0.87 g, 0.75 mmol) was added. The mixture was stirred and heated under reflux for 6 hours. After the reaction was completed, the mixture was cooled to room temperature, distilled water was added, and the toluene layer was separated and dried with anhydrous magnesium sulfate. The solvent was concentrated by rotary evaporation after filtration, and crystals were precipitated by cooling and filtration. The crystals were then recrystallized from toluene / methanol at a ratio of 10:1 to obtain intermediate B-756 (25.18 g, yield 75%) with an HPLC purity ≥99.86%. Mass spectrometry m / z: 447.0766 (theoretical value: 447.0752).

[0147] Preparation of compound 756

[0148] Under nitrogen protection, B-756 (22.38 g, 50.00 mmol), c-756 (14.86 g, 50.00 mmol), and sodium tert-butoxide (7.21 g, 75.00 mmol) dissolved in 225 mL of toluene were added to a reaction flask with stirring. Pd₂(dba)₃ (0.46 g, 0.50 mmol) and X-Phos (0.48 g, 1.00 mmol) were then added. The mixture of the above reactants was heated under reflux for 7.5 h. After the reaction was complete, the mixture was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure. Recrystallization from toluene yielded compound 756 (23.57 g, 71% yield). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 663.1320 (theoretical value: 663.1327). Theoretical elemental content (%) C 44 H 25 NO2S2: C, 79.61; H, 3.80; N, 2.11. Measured elemental content (%): C, 79.67; H, 3.81; N, 2.15.

[0149] Synthesis Example 15: Preparation of Compound 779

[0150] According to the preparation method in Synthesis Example 5, a-63 was replaced with an equimolar amount of a-3, b-147 was replaced with an equimolar amount of b-779, and c-3 was replaced with an equimolar amount of c-779, yielding compound 779 (27.19 g). HPLC analysis showed a solid purity ≥ 99.91%. Mass spectrometry m / z: 823.2193 (theoretical value: 823.2181). Theoretical elemental content (%) C 58 H 33 NO3S: C, 84.55; H, 4.04; N, 1.70. Measured elemental content (%): C, 84.57; H, 4.09; N, 1.65.

[0151] Synthesis Example 16: Preparation of Compound 801

[0152] According to the preparation method in Example 1, a-3 was replaced with an equimolar amount of a-374, b-3 with an equimolar amount of b-801, and c-3 with an equimolar amount of c-801, yielding compound 801 (22.46 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 623.1389 (theoretical value: 623.1378). Theoretical elemental content (%) C 42 H25 NOS2: C, 80.87; H, 4.04; N, 2.25. Measured elemental content (%): C, 80.89; H, 4.09; N, 2.18.

[0153] Synthesis Example 17: Preparation of Compound 826

[0154] According to the preparation method in Synthesis Example 14, a-63 was replaced with an equimolar amount of a-514, and c-756 was replaced with an equimolar amount of c-3, yielding compound 826 (26.52 g). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 779.1423 (theoretical value: 779.1411). Theoretical elemental content (%) C 52 H 29 NOS3: C, 80.07; H, 3.75; N, 1.80. Measured elemental content (%): C, 80.02; H, 3.81; N, 1.85.

[0155] Synthesis Example 18: Preparation of Compound 849

[0156] According to the preparation method in Synthesis Example 5, a-63 was replaced with an equimolar amount of a-849, b-147 was replaced with an equimolar amount of b-779, and c-3 was replaced with an equimolar amount of c-849, yielding compound 849 (28.93 g). HPLC analysis showed a solid purity ≥ 99.92%. Mass spectrometry m / z: 889.2118 (theoretical value: 889.2109). Theoretical elemental content (%) C 62 H 35 NO2S2: C, 83.66; H, 3.96; N, 1.57. Measured elemental content (%): C, 83.62; H, 3.99; N, 1.54.

[0157] Synthesis Example 19: Preparation of Compound 858

[0158] According to the preparation method in Synthesis Example 5, a-63 was replaced with an equimolar amount of a-858, b-147 was replaced with an equimolar amount of b-779, and c-3 was replaced with an equimolar amount of c-858, yielding compound 858 (26.73 g). HPLC analysis showed a solid purity ≥ 99.93%. Mass spectrometry m / z: 797.2514 (theoretical value: 797.2501). Theoretical elemental content (%) C 56 H 35N3OS: C, 84.29; H, 4.42; N, 5.27. Measured elemental content (%): C, 84.34; H, 4.41; N, 5.23.

[0159] Synthesis Example 20: Preparation of Compound 887

[0160] According to the preparation method in Synthesis Example 5, a-63 was replaced with an equimolar amount of a-514, b-147 with an equimolar amount of b-779, and c-3 with an equimolar amount of c-554, yielding compound 887 (29.13 g). HPLC analysis showed a solid purity ≥ 99.91%. Mass spectrometry m / z: 895.1482 (theoretical value: 895.1496). Theoretical elemental content (%) C 60 H 33 NS4: C, 80.42; H, 3.71; N, 1.56. Measured elemental content (%): C, 80.47; H, 3.68; N, 1.52.

[0161] Synthesis Example 21: Preparation of Compound 934

[0162] Following the preparation method of Synthesis Example 14, a-374 was replaced with an equimolar amount of d-934, and c-756 was replaced with an equimolar amount of c-554, yielding compound 934 (26.83 g). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 788.1968 (theoretical value: 788.1956). Theoretical elemental content (%) C 54 H 32 N₂OS₂: C, 82.21; H, 4.09; N, 3.55. Measured elemental content (%): C, 82.25; H, 4.05; N, 3.51.

[0163] Synthesis Example 22: Preparation of Compound 1020

[0164] According to the preparation method in Synthesis Example 14, a-63 was replaced with an equimolar amount of a-1020, a-374 was replaced with an equimolar amount of d-1020, and c-756 was replaced with an equimolar amount of c-1020, yielding compound 1020 (27.16 g). HPLC analysis showed a solid purity ≥ 99.92%. Mass spectrometry m / z: 822.1281 (theoretical value: 822.1292). Theoretical elemental content (%) C 53 H 30N2S4: C, 77.34; H, 3.67; N, 3.40. Measured elemental content (%): C, 77.30; H, 3.61; N, 3.42.

[0165] Synthesis Example 23: Preparation of Compound 1048

[0166] According to the preparation method in Synthesis Example 14, a-63 was replaced with an equimolar amount of a-1048, a-374 was replaced with an equimolar amount of d-1048, and c-756 was replaced with an equimolar amount of c-1048, yielding compound 1048 (24.73 g). HPLC analysis showed a solid purity ≥ 99.93%. Mass spectrometry m / z: 716.1427 (theoretical value: 716.1415). Theoretical elemental content (%) C 47 H 28 N2S3: C, 78.74; H, 3.94; N, 3.91. Measured elemental content (%): C, 78.77; H, 3.95; N, 3.94.

[0167] Synthesis Example 24: Preparation of Compound 1098

[0168] According to the preparation method in Synthesis Example 14, b-756 was replaced with an equimolar amount of b-1098, a-374 was replaced with an equimolar amount of d-1098, and c-756 was replaced with an equimolar amount of c-3, yielding compound 1098 (23.71 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 667.2522 (theoretical value: 667.2511). Theoretical elemental content (%) C 49 H 33 NO2: C, 88.13; H, 4.98; N, 2.10. Measured elemental content (%): C, 88.08; H, 4.92; N, 2.12.

[0169] Synthesis Example 25: Preparation of Compound 1251

[0170] According to the preparation method in Example 1, a-3 was replaced with an equimolar amount of a-374, b-3 with an equimolar amount of b-1251, and c-3 with an equimolar amount of c-1251, yielding compound 1251 (22.15 g). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 606.1746 (theoretical value: 606.1766). Theoretical elemental content (%) C 42 H 26N₂OS: C, 83.14; H, 4.32; N, 4.62. Measured elemental content (%): C, 83.12; H, 4.35; N, 4.66.

[0171] Synthesis Example 26: Preparation of Compound 1329

[0172] According to the preparation method in Example 1, c-3 was replaced with an equimolar amount of c-1329 to obtain compound 1329 (22.20 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 616.1798 (theoretical value: 616.1787). Theoretical elemental content (%) C 43 H 24 N2O3: C, 83.75; H, 3.92; N, 4.54. Measured elemental content (%): C, 83.72; H, 3.94; N, 4.58.

[0173] Synthesis Example 27: Preparation of Compound 1345

[0174] According to the preparation method in Example 1, a-3 was replaced with an equimolar amount of a-1345 to obtain compound 1345 (23.23 g). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 663.2221 (theoretical value: 663.2230). Theoretical elemental content (%) C 45 H 33 NO3Si: C, 81.42; H, 5.01; N, 2.11. Measured elemental content (%): C, 81.40; H, 5.04; N, 2.17.

[0175] Synthesis Example 28: Preparation of Compound 1354

[0176] According to the preparation method in Example 1, a-3 was replaced with an equimolar amount of a-374, and c-3 was replaced with an equimolar amount of c-1354, yielding compound 1354 (19.97 g). HPLC analysis showed a solid purity ≥ 99.98%. Mass spectrometry m / z: 539.1784 (theoretical value: 539.1795). Theoretical elemental content (%) C 36 H 13 D8NO2S: C, 80.12; H, 5.41; N, 2.60. Measured elemental content (%): C, 80.16; H, 5.37; N, 2.62.

[0177] Synthesis Example 29: Preparation of Compound 1371

[0178] According to the preparation method in Synthesis Example 14, a-374 was replaced with an equimolar amount of d-1371, and c-756 was replaced with an equimolar amount of c-1251, yielding compound 1371 (26.13 g). HPLC analysis showed a solid purity ≥ 99.92%. Mass spectrometry m / z: 779.2872 (theoretical value: 779.2858). Theoretical elemental content (%) C 55 H 41 NO2S: C, 84.69; H, 5.30; N, 1.80. Measured elemental content (%): C, 84.73; H, 5.36; N, 1.75.

[0179] Synthesis Example 30: Preparation of Compound 1373

[0180] Following the preparation method of Synthesis Example 14, a-63 was replaced with an equimolar amount of a-1373, and c-756 was replaced with an equimolar amount of c-3, yielding compound 1373 (25.77 g). HPLC analysis showed a solid purity ≥ 99.93%. Mass spectrometry m / z: 757.2482 (theoretical value: 757.2473). Theoretical elemental content (%) C 52 H 39 NOS2: C, 82.40; H, 5.19; N, 1.85. Measured elemental content (%): C, 82.41; H, 5.16; N, 1.89.

[0181] Synthesis Example 31: Preparation of Compound 1378

[0182] Following the preparation method of Synthesis Example 14, a-63 was replaced with an equimolar amount of a-1378, and c-756 was replaced with an equimolar amount of c-63, yielding compound 1378 (24.21 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 691.1266 (theoretical value: 691.1251). Theoretical elemental content (%) C 43 H 24 F3NOS2: C, 74.66; H, 3.50; N, 2.02. Measured elemental content (%): C, 74.62; H, 3.54; N, 2.00.

[0183] Synthesis Example 32: Preparation of Compound 1385

[0184] According to the preparation method in Synthesis Example 1, a-3 was replaced with an equimolar amount of a-1385, b-3 with an equimolar amount of b-801, and c-3 with an equimolar amount of c-554, yielding compound 1385 (22.60 g). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 627.1641 (theoretical value: 627.1629). Theoretical elemental content (%) C 42 H 21 D4NOS2: C, 80.35; H, 4.65; N, 2.23. Measured elemental content (%): C, 80.37; H, 4.64; N, 2.28.

[0185] Synthesis Example 33: Preparation of Compound 1417

[0186] According to the preparation method in Synthesis Example 5, a-63 was replaced with an equimolar amount of a-1417, b-147 was replaced with an equimolar amount of b-164, and c-3 was replaced with an equimolar amount of c-1417, yielding compound 1417 (26.66 g). HPLC analysis showed a solid purity ≥ 99.92%. Mass spectrometry m / z: 807.2421 (theoretical value: 807.2410). Theoretical elemental content (%) C 58 H 33 NO4: C, 86.23; H, 4.12; N, 1.73. Measured elemental content (%): C, 86.21; H, 4.15; N, 1.77.

[0187] Synthetic Example 34: Preparation of Compound 1419

[0188] According to the preparation method in Synthesis Example 5, a-63 was replaced with an equimolar amount of a-1419, and b-147 was replaced with an equimolar amount of b-164, yielding compound 1419 (23.57 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 663.1317 (theoretical value: 663.1327). Theoretical elemental content (%) C 44 H 25 NO2S2: C, 79.61; H, 3.80; N, 2.11. Measured elemental content (%): C, 79.58; H, 3.84; N, 2.05.

[0189] Synthesis Example 35: Preparation of Compound 1448

[0190] According to the preparation method in Synthesis Example 14, a-63 was replaced with an equimolar amount of a-1448, a-374 was replaced with an equimolar amount of d-1448, and c-756 was replaced with an equimolar amount of c-1448, yielding compound 1448 (25.53 g). HPLC analysis showed a solid purity ≥ 99.93%. Mass spectrometry m / z: 739.1448 (theoretical value: 739.1462). Theoretical elemental content (%) C 50 H 29 NS3: C, 81.16; H, 3.95; N, 1.89. Measured elemental content (%): C, 81.19; H, 3.89; N, 1.91.

[0191] [Device Examples]

[0192] A combined IVL testing system was used to test the luminous efficiency of organic electroluminescent devices (OLEDs), comprising testing software, a computer, a Keithley K2400 digital source meter, and a PhotoResearch PR788 spectral scanning luminance meter. Lifetime testing was performed using the McScience M6000 OLED lifetime testing system.

[0193] [Example 1]

[0194] The glass substrate was cleaned using distilled water and ultrasonic cleaning. After distilled water washing, ultrasonic cleaning was performed using solvents such as isopropanol, acetone, and methanol, followed by drying. After drying, the substrate was transferred to a plasma cleaner, and then transferred to an evaporation deposition machine. ITO / Ag / ITO was coated onto the glass substrate to form an anode. HI-1:HT-1 (mass ratio 3:97) was deposited on the anode to form a hole injection layer with a thickness of 150 Å. HT-1 was deposited on the hole injection layer to form a hole transport layer with a thickness of 1200 Å. A light-emitting layer was deposited on the hole transport layer, using H-1 as the host material and doped with 3 wt% D-1 to form a light-emitting layer with a thickness of 350 Å. ET-1:LiQ (mass ratio 1:1) was deposited on the light-emitting layer to form an electron transport layer with a thickness of 350 Å. LiF was deposited on the electron transport layer to form an electron injection layer with a thickness of 10 Å. A Mg:Ag mixture (mass ratio 1:9) is deposited on the electron injection layer to form a cathode with a thickness of 150 Å. Compound 3 of the present invention is then deposited on the cathode layer to form a capping layer with a thickness of 650 Å. This forms an organic light-emitting device.

[0195]

[0196]

[0197] [Examples 1-35]

[0198] Compounds 63, 68, 133, 147, 164, 251, 374, 423, 490, 514, 554, 618, 756, 779, 801, 826, 849, 858, 887, 934, 1020, 1048, 1098, 1251, 1329, 1345, 1354, 1371, 1373, 1378, 1385, 1417, 1419, and 1448 of the present invention were used to replace compound 3 in Example 1 as the capping layer material. Otherwise, an organic electroluminescent device was prepared using the same preparation method as in Example 1.

[0199] [Comparative Examples 1-2]

[0200] Compounds P-1 and P-2 were used to replace compound 3 in device example 1 as the capping material. Otherwise, an organic electroluminescent device was prepared using the same preparation method as device example 1.

[0201] The test environment was atmospheric, and the temperature was room temperature. The luminescence characteristics test results of the organic electroluminescent devices obtained by devices 1-35 and comparative examples 1-2 in the embodiments of the present invention are shown in Table 1 below.

[0202] Table 1:

[0203]

[0204] As shown in Table 1, when the heterocyclic compounds of the present invention are applied to the capping layer of organic electroluminescent devices, the devices exhibit higher luminous efficiency and longer lifespan compared to comparative compounds P-1 to P-2. The compounds of the present invention are high-performance capping layer materials.

[0205] [Example 36]

[0206] The glass substrate was cleaned using distilled water and ultrasonic cleaning. After distilled water washing, ultrasonic cleaning was performed using solvents such as isopropanol, acetone, and methanol, followed by drying. After drying, the substrate was transferred to a plasma cleaner, and then transferred to an evaporation deposition machine. Indium tin oxide (ITO) was coated onto the glass substrate to form an anode. HI-1:HT-2 (mass ratio 3:97) was deposited on the anode to form a hole injection layer with a thickness of 100 Å. HT-2 was deposited on the hole injection layer to form a hole transport layer with a thickness of 1300 Å. A light-emitting layer was deposited on the hole transport layer, using H-2:compound 3 of this invention (mass ratio 1:1) as the host material and doped with 7 wt% D-2 to form a light-emitting layer with a thickness of 400 Å. ET-2:LiQ (mass ratio 1:1) was deposited on the light-emitting layer to form an electron transport layer with a thickness of 300 Å. LiF was deposited on the electron transport layer to form an electron injection layer with a thickness of 10 Å. Al is deposited on the electron injection layer to form a cathode with a thickness of 1200 Å, thus forming an organic light-emitting device.

[0207]

[0208] [Examples 37-70]

[0209] Compounds 63, 68, 133, 147, 164, 251, 374, 423, 490, 514, 554, 618, 756, 779, 801, 826, 849, 858, 887, 934, 1020, 1048, 1098, 1251, 1329, 1345, 1354, 1371, 1373, 1378, 1385, 1417, 1419, and 1448 of the present invention were used to replace compound 3 in Example 36 as the light-emitting layer material. Otherwise, an organic electroluminescent device was prepared using the same preparation method as in Example 36.

[0210] [Comparative Examples 3-5]

[0211] Compounds P-3, P-4, and P-5 were used to replace compound 3 in Example 36 as the light-emitting layer material, and organic electroluminescent devices were prepared using the same preparation method as in Example 36.

[0212] The test environment was atmospheric, and the temperature was room temperature. The luminescence characteristics test results of the organic electroluminescent devices obtained by devices 36-70 and comparative examples 3-5 in the embodiments of the present invention are shown in Table 2 below.

[0213] Table 2:

[0214]

[0215] As shown in Table 2, when the heterocyclic compounds of the present invention are applied to the light-emitting layer of organic electroluminescent devices, the devices exhibit higher luminous efficiency and longer lifespan compared to comparative compounds P-3 to P-5. The compounds of the present invention are high-performance light-emitting layer materials.

[0216] It should be noted that the present invention has been specifically described with reference to individual embodiments, but those skilled in the art can make various forms or details of improvements to the present invention without departing from the principles of the present invention, and these improvements also fall within the protection scope of the present invention.

Claims

1. A heterocyclic compound, characterized in that, The heterocyclic compound has the structure represented by Formula I: Wherein, Ar1, Ar2, and Ar3 are independently selected from any one of formula a, formula b, hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C1-C25 heterocyclic alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C1-C25 heterocyclic alkane and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl; at least one of Ar1, Ar2, and Ar3 is selected from formula a, and at least one is selected from formula a or formula b; The i is independently selected from CH and N, and when i is bonded to other groups, the i is selected from C atoms; The v is independently selected from any one of CH and N, and when v is bonded to other groups, the v is selected from C atoms; X is selected from O, S, C(R) p R q ), N(R s Any one of the following; The Y is selected from either O or S; E is selected from O, S, N(R) v Any one of the following; Group 1: Ring A and ring B are independently selected from any one of the substituted or unsubstituted structures in group 1; and at least one of ring A and ring B is not selected from ; The z is selected from C(R) t Any one of N; The R a R b R p R q R t It is independently selected from any one of hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C1-C25 heterocyclic alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C1-C25 heterocyclic alkane and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl; The R s R v It is independently selected from any one of hydrogen, deuterium, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C1-C25 heterocyclic alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C1-C25 heterocyclic alkane and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl; a1 is selected from 0, 1, 2, 3, or 4; when there are two or more R a At that time, two or more R a The same or different between each other, or two adjacent R a They connect with each other to form substituted or unsubstituted rings; b1 is selected from 0, 1, 2, 3, 4, or 5; when there are two or more R b At that time, two or more R b The same or different between each other, or two adjacent R b They connect with each other to form substituted or unsubstituted rings; L1, L2, L3, L4, and L5 are independently selected from any one of the following: single bond, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C6-C30 heteroarylene, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic rings, and substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic rings.

2. The heterocyclic compound according to claim 1, characterized in that, The heterocyclic compound is selected from any one of the following structures: Ar3, ring A, ring B, Y, L1, L2, L3, L4, L5, X, i, R a R b The definitions of a1, b1, and E are the same as those in Equation I.

3. A heterocyclic compound according to claim 1, characterized in that, The Selected from any one of the following groups: Y1 is selected from O, S, C(R) x R y ), N(R z Any one of the following; The R a R x R y Independently selected from any one of hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C1-C25 heterocyclic alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C1-C25 heterocyclic alkane and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl, or R x R y The links between them form substituted or unsubstituted rings; The R z It is independently selected from any one of hydrogen, deuterium, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C1-C25 heterocyclic alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C1-C25 heterocyclic alkane and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl; a1 is selected from 0, 1, 2, 3, or 4; a2 is selected from 0, 1, 2, or 3; a3 is selected from 0, 1, or 2; a4 is selected from 0, 1, 2, 3, 4, 5, or 6; a5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; when there are two or more R... a At that time, two or more R a They may be the same as or different from each other.

4. A heterocyclic compound according to claim 1, characterized in that, Formula a is selected from any one of the following groups: The x is independently selected from either CH or N; The Y is independently selected from either O or S; The R d The group is independently selected from hydrogen, deuterium, halogen, cyano, nitro, and substituted or unsubstituted groups of the following: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornel, trimethylsilyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, vinyldimethylsilyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropane, naphthocyclopropane, benzocyclobutane, naphthocyclobutane, benzocyclopentane, naphthocyclopentane, benzocyclohexane, naphthocyclohexane, benzocycloheptane, benzocyclobutenyl. Benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenylene, pyrene, perylene, fluoranthyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, benzofuranyl, dibenzofuranyl, benzodibenzofuranyl, thiophene, benzothiophene, dibenzothiophene, benzodibenzothiophene, indole, carbazole The following are all of the following: yl, pyrrole, oxazolyl, benzoxazolyl, dibenzoxazolyl, thiazolyl, benzothiazolyl, dibenzothiazolyl, imidazolyl, benzoimidazolyl, dibenzoimidazolyl, quinolinyl, benzoquinolinyl, isoquinolinyl, benzoisoquinolinyl, quinazolinyl, benzoquinazolinyl, quinoxalinyl, benzoquinoxalinyl, phenantholinyl, naphridinyl, indolyl, acridinel, phenoxazinyl, phenothiazinyl; The d1 is selected from 0, 1, 2, 3, 4, 5, or 6; the d2 is selected from 0, 1, 2, or 3; the d3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; the d4 is selected from 0, 1, 2, 3, or 4; the d5 is selected from 0, 1, 2, 3, 4, or 5; the d6 is selected from 0, 1, 2, 3, 4, 5, 6, or 7; when there are two or more R... d At that time, two or more R d They may be the same as or different from each other.

5. A heterocyclic compound according to claim 1, characterized in that, Formula b is selected from any one of the following groups: The R b The group is independently selected from hydrogen, deuterium, halogen, cyano, nitro, and substituted or unsubstituted groups of the following: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornel, trimethylsilyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, vinyldimethylsilyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropane, naphthocyclopropane, benzocyclobutane, naphthocyclobutane, benzocyclopentane, naphthocyclopentane, benzocyclohexane, naphthocyclohexane, benzocycloheptane, benzocyclobutenyl. Benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenylene, pyrene, perylene, fluoranthyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, benzofuranyl, dibenzofuranyl, benzodibenzofuranyl, thiophene, benzothiophene, dibenzothiophene, benzodibenzothiophene, indole, carbazole The following are all of the following: yl, pyrrole, oxazolyl, benzoxazolyl, dibenzoxazolyl, thiazolyl, benzothiazolyl, dibenzothiazolyl, imidazolyl, benzoimidazolyl, dibenzoimidazolyl, quinolinyl, benzoquinolinyl, isoquinolinyl, benzoisoquinolinyl, quinazolinyl, benzoquinazolinyl, quinoxalinyl, benzoquinoxalinyl, phenantholinyl, naphridinyl, indolyl, acridinel, phenoxazinyl, phenothiazinyl; The R v The group independently selected from hydrogen, deuterium, halogen, cyano, nitro, or substituted or unsubstituted groups, including: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, ethyldimethylsilyl, triisopropylsilyl, propyldimethylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl Alkyl, vinyldimethylsilyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropane, naphthocyclopropane, benzocyclobutane, naphthocyclobutane, benzocyclopentane, naphthocyclopentane, benzocyclohexane, naphthocyclohexane, benzocycloheptane, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthraceneyl, phenanthrene, triphenylene, pyrene, perylene, fluoranyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl; b1 is selected from 0, 1, 2, 3, 4, or 5; b2 is selected from 0, 1, 2, 3, 4, 5, 6, or 7; b3 is selected from 0, 1, or 2; b4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; b5 is selected from 0 or 1; b6 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9; when there are two or more R... b At that time, two or more R b They may be the same as or different from each other.

6. A heterocyclic compound according to claim 1, characterized in that, When Ar1, Ar2, and Ar3 are not selected from formulas a and b, Ar1, Ar2, and Ar3 are independently selected from hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted silyl group, substituted or unsubstituted C1-C25 alkyl group, substituted or unsubstituted C3-C25 cycloalkyl group, substituted or unsubstituted C1-C25 heterocycloalkyl group, and any one of the following groups: The u is independently selected from any one of CH and N atoms; when u is bonded to other groups, the u is selected from C atoms. The ring D is selected from substituted or unsubstituted C3~C10 alicyclic rings; X4 is selected from O, S, N(R) w Any one of the following; The X5 is selected from C(R) u R r ), N(R w Any one of the following; X6 and X7 are independently selected from O, S, and C(R). u R r ), N(R w Any one of the following; The R e R e 'Independently selected from any one of hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C1-C25 heterocyclic alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C1-C25 heterocyclic alkane and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl; The R u R r Independently selected from any one of hydrogen, deuterium, fluorine, trifluoromethyl, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, or R u R r The links between them form substituted or unsubstituted rings; The R w It is independently selected from any one of hydrogen, deuterium, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl; The value of e1 is selected from 0, 1, 2, 3, 4, or 5; the value of e2 is selected from 0, 1, 2, 3, or 4; the value of e3 is selected from 0, 1, 2, 3, 4, 5, 6, or 7; the value of e4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9; the value of e5 is selected from 0, 1, or 2; the value of e6 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11; the value of e7 is selected from 0, 1, 2, or 3; the value of e8 is selected from 0, 1, 2, 3, 4, 5, or 6; when there are two or more R... e At that time, two or more R e The same or different between each other, or two adjacent R e They connect with each other to form substituted or unsubstituted rings; The term e'1 is selected from 0, 1, or 2; when there are two or more R... e At that time, two or more R e 'They are the same as or different from each other.' 7. A heterocyclic compound according to claim 1, characterized in that, The compound of formula I is selected from any one of the following structures: 。 8. An organic electroluminescent device, comprising an anode, a cathode, and an organic layer located between the anode and the cathode or on the side of the cathode facing away from the anode, characterized in that, The organic layer comprises at least one of the heterocyclic compounds according to any one of claims 1 to 7.

9. An organic electroluminescent device according to claim 8, wherein the organic layer is located between the anode and the cathode, characterized in that, The organic layer includes a light-emitting layer, which contains at least one of the heterocyclic compounds according to any one of claims 1 to 7.

10. An organic electroluminescent device according to claim 8, wherein the organic layer is located on the side of the cathode opposite to the anode, characterized in that, The organic layer includes a capping layer, which contains at least one of the heterocyclic compounds according to any one of claims 1 to 7.

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