Heterocyclic compound and organic electroluminescent device thereof

Abstract

The application provides a heterocyclic compound and an organic electroluminescent device thereof, and relates to the technical field of organic electroluminescent materials.The heterocyclic compound has good stability and film-forming property, has a suitable triplet energy level when applied to an organic electroluminescent device, can effectively reduce a driving voltage, improve the luminous efficiency of the device, and prolong the service life of the device, and meanwhile, the preparation method of the compound is simple, raw materials are easy to obtain, and the compound can meet the industrialization demand, and has a good industrialization prospect in the fields of flat panel display and solid-state lighting.

Description

Technical Field

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

[0002] With the continuous upgrading of electronic devices such as mobile phones and computers in recent years, people's requirements and reliance on displays have also increased day by day. Organic optoelectronic functional materials have attracted much attention in the display field due to their excellent performance. Organic light-emitting diodes (OLEDs) have greater advantages and broader application prospects than LCDs due to their superior characteristics such as faster response speed, wider color gamut, and lower power consumption.

[0003] Organic light-emitting diodes (OLEDs) are a type of sandwich-type multilayer thin-film structure. The most typical OLED generally consists of three organic layers: a hole transport layer (HIL), an emitting layer (ELL), and an electron transport layer (ETL). To further improve the device's luminous efficiency, brightness, and other performance parameters, researchers are continuously refining the device structure by adding material layers with independent functions. This involves adding buffer layers inside the electrodes, such as electron injection layers, hole injection layers, electron blocking layers, and hole blocking layers.

[0004] Electron transport materials suffer from significantly lower electron mobility and lower hole mobility compared to hole transport materials, resulting in inefficient electron and hole transport to the emissive layer. Furthermore, energy level mismatch causes some electrons and holes to escape from the emissive layer, leading to reduced luminous efficiency and increased driving voltage in organic light-emitting devices (OLEDs). Conversely, the emissive layer itself experiences imbalanced electron and hole migration due to triplet energy level mismatch between the host and guest materials, resulting in low efficiency in exciton formation and further reducing OLED luminous efficiency.

[0005] Therefore, developing organic electron transport materials with high mobility and good stability, hole blocking materials that can effectively block hole escape, and light-emitting layer host materials that enable higher exciton utilization efficiency, thereby improving the various performance characteristics of organic electroluminescent devices, is the direction we should study. Summary of the Invention

[0006] To address the aforementioned problems, this invention provides a heterocyclic compound and its organic electroluminescent device. Applying this heterocyclic compound to an organic light-emitting device can effectively improve the device's luminous efficiency and extend its lifespan.

[0007] Specifically, the present invention provides a heterocyclic compound having a structure represented by Formula I:

[0008]

[0009] Group 1:

[0010]

[0011] Wherein, Ar1 is selected from either Formula II or Formula III;

[0012] The ring A is selected from any one of the structures in Group 1; * represents the fusion site;

[0013] The ring B is selected from any one of the aryl groups from C6 to C18;

[0014] X is selected from CH and N, and at least one of X is selected from N;

[0015] The Y is selected from O, S, N(R) d Any one of the following;

[0016] Y1 and Y2 are independently selected from O, S, and C(R). a R b ), N(R c Any one of the following;

[0017] The V is selected from either CH or N;

[0018] The Ar2 is selected from any one of the following: Formula II, Formula III, substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C2-C30 heteroaryl groups, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused ring groups, substituted or unsubstituted C1-C25 heterocyclic alkanes and C6-C30 aromatic fused ring groups, and substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic fused ring groups.

[0019] The L is selected from any one of the following: single bond, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C2-C30 heteroarylene, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic rings with fused cycloyl groups, and substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic rings with fused cycloyl groups, and at least one or more of Ar1, Ar2, L, and R2 contain deuterium;

[0020] R0, R1, R2, R3, and R4 are independently selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C1-C30 silyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C6-C20 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 alkanes and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaryl ring fused cycloyl;

[0021] The a0 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; when there are two or more R0s, the two or more R0s are the same as or different from each other;

[0022] a1 is selected from 0 or 1;

[0023] a2 is selected from 0, 1 or 2; when there are two R2s, the two R2s are the same or different from each other;

[0024] The a3 is selected from 0, 1, 2, 3 or 4; when there are two or more R3s, the two or more R3s are the same or different from each other, or two adjacent R3s are connected to each other to form a substituted or unsubstituted ring;

[0025] The a4 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 R4s, the two or more R4s are the same or different from each other, or two adjacent R4s are connected to each other to form a substituted or unsubstituted ring;

[0026] The R a R b Independently selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C1-C30 silyl, substituted or unsubstituted C3-C12 cycloalkyl, 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 groups, substituted or unsubstituted C1-C25 heterocyclic alkanes and C6-C30 aromatic ring fused cycloyl groups, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl groups, or R a R b The links between them form substituted or unsubstituted rings;

[0027] The R cIt is selected from any one of the following: substituted or unsubstituted C1-C25 alkyl groups, substituted or unsubstituted C1-C30 silyl groups, substituted or unsubstituted C3-C25 cycloalkyl groups, substituted or unsubstituted C6-C20 aryl groups, substituted or unsubstituted C2-C30 heteroaryl groups, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl groups, substituted or unsubstituted C1-C25 heterocyclic alkanes and C6-C30 aromatic ring fused cycloyl groups, and substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl groups.

[0028] 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, wherein the organic layer comprises at least one of the heterocyclic compounds described in the present invention.

[0029] Beneficial effects:

[0030] This invention provides a heterocyclic compound with high electron mobility and triplet energy levels, exhibiting good film-forming properties and thermal stability when applied to organic electroluminescent devices. When used as an electron transport material, it improves electron mobility, enabling efficient electron transport to the emissive layer; when used as a hole blocking material, it prevents holes from escaping from the emissive layer, increasing the recombination probability of excitons within the emissive layer; when used as the host material of the emissive layer, it results in a more balanced distribution of electrons and holes within the emissive layer, a wider exciton recombination region, and improved exciton utilization, ultimately enhancing the luminous efficiency and extending the device's lifespan. Furthermore, the preparation method of this compound is simple, the raw materials are readily available, it meets industrialization requirements, and it has promising prospects for industrialization. Detailed Implementation

[0031] 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.

[0032] In this specification, "-*" refers to the portion connected to another substituent. "-*" can be attached to any optional position of the group / fraction to which it is attached.

[0033] 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 rings. For example, Can represent Can represent And so on.

[0034] 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.

[0035] For example, Can represent Can represent Can represent And so on.

[0036] Examples of halogens described in this invention may include fluorine, chlorine, bromine, and iodine.

[0037] 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:

[0038]

[0039] 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.

[0040] In this invention, the term "substituted or unsubstituted" such as "substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted silyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted arylene, substituted or unsubstituted heteroaryl" indicates that at least one hydrogen atom on the group is replaced by a substituent. When multiple hydrogens are replaced by multiple substituents, the multiple substituents may be the same or different. The substituents represented by "substituted or unsubstituted" in the above-mentioned phrase can be independently selected from deuterium, tritium, cyano, nitro, amino, halogen atom, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C30 silyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, 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 to these, or adjacent substituents can be linked to form a ring. Preferred atoms include deuterium, tritium, cyano, nitro, amino, halogen atoms, C1-C12 alkyl, C3-C15 silyl, C3-C12 cycloalkyl, C6-C30 aryl, C2-C30 heteroaryl, and C1-C12 alkoxy. Specific examples may include deuterium, tritium, fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, trimethylsilyl, triethylsilyl, tritert-butylsilyl, triphenylsilyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornel, trifluoromethyl, trifluoroethyl, trideuterated methyl, methoxy, ethoxy, phenyl, tolyl, mesitylene, pentadeuterated phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, and tri- Phenylidene, Perylene, Pyrene, Fluoranthryl, Benzocyclopropane, Benzocyclobutane, Benzocyclopentane, Benzocyclohexane, Benzocycloheptane, Benzocyclobutenyl, Benzocyclopentenyl, Benzocyclohexenyl, 9,9-Dimethylfluorenyl, 9,9-Diphenylfluorenyl, 9-Methyl-9-phenylfluorenyl, Spirofluorenyl, 9-Phenycarbazolyl, 9,9'-Spirodifluorenyl, Carbazoindolyl, Pyrrole Substituents include, but are not limited to, alkyl, furanyl, thienyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, pyridyl, pyrimidinyl, pyrazinyl, triazinyl, oxazolyl, thiazolyl, imidazolyl, benzoxazolyl, benzothiazolyl, benzotriazolyl, benzoimidazolyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, phenothiazinyl, phenothiazinyl, acridineyl, etc. When there are multiple substituents, the multiple substituents may be the same or different from each other; or adjacent substituents may be linked to form a ring.

[0041] The alkyl group referred to in this invention refers to the general term for monovalent groups obtained by removing one hydrogen atom from an alkane molecule. It can be a straight-chain alkyl group or a branched-chain alkyl group, preferably having 1 to 25 carbon atoms, more preferably 1 to 12 carbon atoms, and particularly preferably 1 to 6 carbon atoms. Specific examples may include methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, undecyl, dodecyl, isopropyl, isobutyl, sec-butyl, tert-butyl, isopentyl, etc., but are not limited thereto.

[0042] The cycloalkyl group described in this invention refers to the general term for monovalent groups obtained 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. Specific examples may include adamantyl, norbornel, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, etc., but are not limited thereto.

[0043] The silane group described in this invention can be represented by the group described in —SiH3; the substituted silane group described in this invention can be represented by the group described in —Si(Rs)(Rs)(Rs), where Rs is hydrogen, deuterium, tritium, the aforementioned substituted or unsubstituted alkyl groups, substituted or unsubstituted alkoxy groups, substituted or unsubstituted cycloalkyl groups, substituted or unsubstituted aryl groups, substituted or unsubstituted heteroaryl groups, etc., but not simultaneously hydrogen, deuterium, and tritium; the multiple Rs in —Si(Rs)(Rs)(Rs) can be the same or different; preferably The sample may have 1 to 30 carbon atoms, preferably 1 to 25 carbon atoms, more preferably 3 to 22 carbon atoms, and most preferably 3 to 18 carbon atoms. Examples may include trimethylsilyl, triethylsilyl, triisopropylsilyl, tritert-butylsilyl, dimethylethylsilyl, dimethylisopropylsilyl, dimethyltert-butylsilyl, tricyclopentylsilyl, tricyclohexylsilyl, triphenylsilyl, triphenylsilyl, tripyridylsilyl, tripyridylsilyl, etc., but are not limited thereto.

[0044] The alicyclic group mentioned in this invention refers to the general term for monovalent groups obtained by removing one hydrogen atom from an alicyclic hydrocarbon molecule. It can be cycloalkyl, cycloalkenyl, etc., preferably having 3 to 25 carbon atoms, more preferably 3 to 20 carbon atoms, particularly preferably 3 to 15 carbon atoms, more preferably 5 to 10 carbon atoms, and most preferably 5 to 7 carbon atoms. Specific examples may include adamantyl, norbornel, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, etc., but are not limited thereto.

[0045] The heterocyclic alkyl group described in this invention refers to the general term for groups obtained by replacing one or more carbon atoms in a cycloalkyl group with heteroatoms. These heteroatoms include, but are not limited to, oxygen, sulfur, nitrogen, silicon, or phosphorus atoms, and preferably have 1 to 15 carbon atoms, more preferably 2 to 12 carbon atoms, and particularly preferably 2 to 6 carbon atoms. Specific examples may include tetrahydropyrrolyl, piperidinyl, etc., but are not limited thereto.

[0046] The aryl group mentioned in this invention refers to the general term for the monovalent group obtained by removing a hydrogen atom from the aromatic carbon atom of an aromatic compound 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 group refers to an aryl group with only one aromatic ring in the molecule, such as phenyl, but not limited to this; the polycyclic aryl group refers to an aryl group with two or more independent aromatic rings in the molecule, and specific examples may include biphenyl, terphenyl, tetraphenyl, 1-phenylnaphthyl, 2-phenylnaphthyl, etc., but not limited to this; the fused-ring aryl group refers to an aryl group with two or more aromatic rings in the molecule that are fused together by sharing two adjacent carbon atoms, and specific examples may include naphthyl, anthraceneyl, phenanthryl, pyrene, peryl, fluorenyl, benzo[a]fluorenyl, triphenylene, fluoranyl, spirofluorenyl, spirodifluorenyl, etc., but not limited to this.

[0047] The heteroaryl group described in this invention refers to the general term for groups obtained 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, silicon, or phosphorus atoms, and preferably have 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 linking site of the heteroaryl group can be located on a cyclic carbon atom or on a cyclic heteroatom. The heteroaryl group can be a monocyclic heteroaryl, polycyclic heteroaryl, or fused-ring heteroaryl. Specific examples of the monocyclic heteroaryl group may include pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, thiopheneyl, pyrroloyl, oxazolyl, thiazolyl, imidazolyl, etc., but are not limited thereto; specific examples of the polycyclic heteroaryl group may include bipyridyl, bipyrimidinyl, phenylpyridinyl, phenylpyrimidinyl, etc., but are not limited thereto; specific examples of the fused-ring heteroaryl group may include quinolinyl, isoquinolinyl, benzo[a]quinolinyl, benzo[a]isoquinolinyl, quinazolinyl, quinoxalinyl, benzo[a]quinazolinyl, benzo[a]quinazolinyl, benzo[a] Quinoxolinyl, o-phenantholinyl, naphridyl, indolyl, benzothiopheneyl, benzofuranyl, benzooxazolyl, benzoimidazoyl, benzothiazoyl, dibenzofuranyl, benzodibenzofuranyl, dibenzothiopheneyl, benzodibenzothiopheneyl, dibenzooxazolyl, dibenzoimidazoyl, dibenzothiazoyl, carbazoleyl, benzocarbazoleyl, acridineyl, 9,10-dihydroacridyl, phenoxazinyl, phenthiazinyl, phenoxazinyl, spirofluorenexanthraceneyl, spirofluorenethixanthraceneyl, etc., but not limited to these.

[0048] The fused alicyclic and aromatic cyclic groups described in this invention refer to the general term for monovalent groups obtained by removing one hydrogen atom 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. Specific examples may include benzocyclopropyl, benzocyclobutyl, benzocyclopentyl, benzocyclohexyl, benzocycloheptyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, naphthocyclopropyl, naphthocyclobutyl, naphthocyclopentyl, naphthocyclohexyl, etc., but are not limited thereto.

[0049] The fused cyclic group of heterocyclic alkanes and aromatic rings described in this invention refers to the general term for the monovalent group obtained by removing one hydrogen atom after a heterocyclic alkanes and aromatic rings are fused together. Preferably, it has 6 to 30 carbon atoms, more preferably 7 to 18 carbon atoms, and most preferably 7 to 13 carbon atoms. Specific examples may include benzo[a]hexacyclic butyl, benzo[tetrahydropyrrolyl], benzo[piperidinyl], benzo[a]hexacyclic heptyl, naphtho[tetrahydropyrrolyl], naphtho[piperidinyl], phenanthrene[tetrahydropyrrolyl], phenanthrene[piperidinyl], etc., but are not limited thereto.

[0050] The fused cyclic groups of alicyclic and heteroaromatic rings mentioned in this invention refer to the general term for monovalent groups obtained by removing one hydrogen atom after alicyclic and heteroaromatic rings are fused together. Preferably, it has 5 to 30 carbon atoms, more preferably 5 to 18 carbon atoms, and most preferably 5 to 12 carbon atoms. Specific examples may include pyridocyclopropyl, pyridocyclobutyl, pyridocyclopentyl, pyridocyclohexyl, pyridinium benzocycloheptyl, pyrimidinium cyclopropyl, pyrimidinium cyclobutyl, pyrimidinium cyclopentyl, pyrimidinium benzocyclohexyl, dibenzofuranocyclopropyl, dibenzofuranocyclobutyl, dibenzofuranocyclopentyl, dibenzofuranocyclohexyl, dibenzofuranocycloheptyl, dibenzothiophenecyclopropyl, dibenzothiophenecyclobutyl, dibenzothiophenecyclopentyl, dibenzothiophenecyclohexyl, dibenzothiophenecycloheptyl, carbazoleocyclopropyl, carbazoleocyclobutyl, carbazoleocyclopentyl, carbazoleocyclohexyl, carbazoleocycloheptyl, etc., but are not limited thereto.

[0051] The term "cyclohexene group" as used in this invention refers to the general term for divalent groups obtained by removing two hydrogen atoms from an alicyclic hydrocarbon molecule. These groups can be cyclohexene alkyl groups, cyclohexene alkenyl groups, etc., preferably having 3 to 25 carbon atoms, more preferably 3 to 20 carbon atoms, particularly preferably 3 to 15 carbon atoms, more preferably 5 to 10 carbon atoms, and most preferably 5 to 7 carbon atoms. Specific examples may include cyclohexene propyl, cyclohexene butyl, cyclohexene pentyl, cyclohexene heptyl, adamantyl, norbornelyl, cyclohexene propenyl, cyclohexene butylenyl, cyclohexene pentenyl, cyclohexene heptenyl, etc., but are not limited thereto.

[0052] The arylene group referred to in this invention is a general term for the divalent group obtained by removing two hydrogen atoms from the aromatic nucleus of an aromatic hydrocarbon molecule. It can be a monocyclic arylene, a polycyclic arylene, or a fused-ring arylene, 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. Specific examples may include phenylene, biphenylene, terphenylene, naphthylene, anthracene, phenanthrene, pyrene, trimethyleneene, perylene, fluorene, fluorenylene, phenylfluorene, etc., but are not limited thereto.

[0053] The heteroaryl group described in this invention refers to the general term for the group obtained by replacing one or more aromatic carbon atoms in an aryl group with heteroatoms. These heteroatoms include, but are not limited to, oxygen, sulfur, nitrogen, or phosphorus atoms. Preferably, it has 2 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, and particularly preferably 6 to 15 carbon atoms. The linking site of the heteroaryl group can be located on a cyclic carbon atom or a cyclic nitrogen atom. The heteroaryl group can be a monocyclic heteroaryl group, a polycyclic heteroaryl group, or a fused-ring heteroaryl group. Specific examples of the monocyclic and fused-ring heteroaryl groups may include, but are not limited to, pyridinyl, pyrimidinyl, triazineyl, furanyl, thiopheneyl, carbazolyl, benzofuranyl, benzothiopheneyl, benzocarbazolyl, dibenzofuranyl, dibenzothiopheneyl, and dibenzocarbazolyl; specific examples of the polycyclic heteroaryl groups may include, but are not limited to, bipyridinyl, bipyrimidinyl, and phenylpyridinyl.

[0054] The alicyclic and aromatic ring fused cyclic groups described in this invention refer to the general term for divalent groups obtained 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. Specific examples may include, but are not limited to, benzo[a]cyclopropyl, benzo[a]cyclobutyl, benzo[a]cyclopentyl, benzo[a]cyclohexyl, benzo[a]cycloheptyl, benzo[a]cyclopentenyl, benzo[a]cyclohexenyl, benzo[a]cycloheptenyl, naphtho[a]cyclopropyl, naphtho[a]cyclobutyl, naphtho[a]cyclopentyl, and naphtho[a]cyclohexyl, etc.

[0055] The fused alicyclic and heteroaromatic ring groups described in this invention refer to the general term for divalent groups obtained 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. Specific examples may include pyridinocyclopropyl, pyridinocyclobutyl, pyridinocyclopentyl, pyridinocyclohexyl, pyridinobenzocycloheptyl, pyrimidinoxocyclopropyl, pyrimidinoxocyclobutyl, pyrimidinoxocyclopentyl, pyrimidinoxocyclohexyl, pyrimidinoxobenzocycloheptyl, dibenzofuranocyclopropyl, and dibenzofuranocyclopropyl. Furanocyclobutyl, dibenzofuranocyclopentyl, dibenzofuranocyclohexyl, dibenzofuranocyclohepyl, dibenzothiophenecyclopropyl, dibenzothiophenecyclobutyl, dibenzothiophenecyclopentyl, dibenzothiophenecyclohexyl, dibenzothiophenecyclohepyl, carbazocyclopropyl, carbazocyclobutyl, carbazocyclopentyl, carbazocyclohexyl, carbazocyclohepyl, etc., but not limited to these.

[0056] The terms "at least one" and "one or more" as used in this invention include, where permitted, one, two, three, four, five, six, seven, eight, or more.

[0057] This invention provides a heterocyclic compound having a structure represented by Formula I:

[0058]

[0059] Group 1:

[0060]

[0061] Wherein, Ar1 is selected from either Formula II or Formula III;

[0062] The ring A is selected from any one of the structures in Group 1; * represents the fusion site;

[0063] The ring B is selected from any one of the aryl groups from C6 to C18;

[0064] X is selected from CH and N, and at least one of X is selected from N;

[0065] The Y is selected from O, S, N(R) d Any one of the following;

[0066] Y1 and Y2 are independently selected from O, S, and C(R). a R b ), N(R c Any one of the following;

[0067] The V is selected from either CH or N;

[0068] The Ar2 is selected from any one of the following: Formula II, Formula III, substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C2-C30 heteroaryl groups, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused ring groups, substituted or unsubstituted C1-C25 heterocyclic alkanes and C6-C30 aromatic fused ring groups, and substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic fused ring groups.

[0069] The L is selected from any one of the following: single bond, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C2-C30 heteroarylene, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic rings with fused cycloyl groups, and substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic rings with fused cycloyl groups, and at least one or more of Ar1, Ar2, L, and R2 contain deuterium;

[0070] R0, R1, R2, R3, and R4 are independently selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C1-C30 silyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C6-C20 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 alkanes and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaryl ring fused cycloyl;

[0071] The a0 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; when there are two or more R0s, the two or more R0s are the same as or different from each other;

[0072] a1 is selected from 0 or 1;

[0073] a2 is selected from 0, 1 or 2; when there are two R2s, the two R2s are the same or different from each other;

[0074] The a3 is selected from 0, 1, 2, 3 or 4; when there are two or more R3s, the two or more R3s are the same or different from each other, or two adjacent R3s are connected to each other to form a substituted or unsubstituted ring;

[0075] The a4 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 R4s, the two or more R4s are the same or different from each other, or two adjacent R4s are connected to each other to form a substituted or unsubstituted ring;

[0076] The R a R b Independently selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C1-C30 silyl, substituted or unsubstituted C3-C12 cycloalkyl, 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 groups, substituted or unsubstituted C1-C25 heterocyclic alkanes and C6-C30 aromatic ring fused cycloyl groups, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl groups, or R a R b The links between them form substituted or unsubstituted rings;

[0077] The R c It is selected from any one of the following: substituted or unsubstituted C1-C25 alkyl groups, substituted or unsubstituted C1-C30 silyl groups, substituted or unsubstituted C3-C25 cycloalkyl groups, substituted or unsubstituted C6-C20 aryl groups, substituted or unsubstituted C2-C30 heteroaryl groups, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl groups, substituted or unsubstituted C1-C25 heterocyclic alkanes and C6-C30 aromatic ring fused cycloyl groups, and substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl groups.

[0078] Preferably, R0 and R1 are independently selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted n-propyl, substituted or unsubstituted isopropyl, substituted or unsubstituted n-butyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted benzocyclopropyl, substituted or unsubstituted naphthocyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted benzocyclobutyl, substituted or unsubstituted naphthocyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted benzocyclopentyl, substituted or unsubstituted naphthocyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted benzocyclohexyl, substituted or unsubstituted naphthocyclohexyl, substituted or unsubstituted cycloheptyl Substituted or unsubstituted benzocycloheptyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornel, substituted or unsubstituted tetrahydropyrrole, substituted or unsubstituted piperidinyl, substituted or unsubstituted trimethylsilyl, substituted or unsubstituted triethylsilyl, substituted or unsubstituted triisopropylsilyl, substituted or unsubstituted tri-tert-butylsilyl, substituted or unsubstituted triphenylsilyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthraceneyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted pyrene, substituted or unsubstituted perylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted Substituted spirofluorenyl, substituted or unsubstituted fluoranyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted furanyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzodibenzofuranyl, substituted or unsubstituted thiopheneyl, substituted or unsubstituted benzothiopheneyl, substituted or unsubstituted dibenzothiopheneyl, substituted or unsubstituted carbazoyl, substituted or unsubstituted benzocarbazoyl, substituted or unsubstituted pyrroleyl, substituted or unsubstituted oxazolyl, substituted or unsubstituted benzooxazolyl, substituted or unsubstituted dibenzooxazolyl Azolium, substituted or unsubstituted thiazolyl, substituted or unsubstituted benzothiazolyl, substituted or unsubstituted dibenzothiazolyl, substituted or unsubstituted imidazolyl, substituted or unsubstituted benzimidazolium, substituted or unsubstituted dibenzoimidazolyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted benzoquinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted benzoisoquinolinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted benzoquinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted benzoquinoxalinyl, substituted or unsubstituted phenantholinyl, substituted or unsubstituted naphridyl, substituted or unsubstituted indolyl, substituted or unsubstituted acridinel, substituted or unsubstituted phenoxazinyl, substituted or unsubstituted phenothiazinyl,Any one of substituted or unsubstituted spirofluorenexanthracene or substituted or unsubstituted spirofluorenethixanthracene.

[0079] Preferably, the heterocyclic compound is selected from any one of the following structures:

[0080]

[0081]

[0082] The R p R q R r Independently selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C1-C30 silyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C6-C20 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 alkanes and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl;

[0083] The g1 is selected from 0, 1, 2, 3, 4, 5, or 6; the g2 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; the g3 is selected from 0, 1, 2, 3, 4, or 5; the g4 is selected from 0, 1, 2, 3, 4, 5, 6, or 7; when there are two or more R... q At that time, two or more R q The same or different between each other, or two adjacent R q They connect with each other to form substituted or unsubstituted rings;

[0084] h1 is selected from 0, 1, 2, 3 or 4; when there are two or more R r At that time, two or more R r The same or different between each other, or two adjacent R r They connect with each other to form substituted or unsubstituted rings.

[0085] Preferably, the R p R q R rEach is independently selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted n-propyl, substituted or unsubstituted isopropyl, substituted or unsubstituted n-butyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted benzocyclopropyl, substituted or unsubstituted naphthocyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted benzocyclobutyl, substituted or unsubstituted naphthocyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted benzocyclopentyl, substituted or unsubstituted naphthocyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted benzocyclohexyl, substituted or unsubstituted naphthocyclohexyl, substituted or unsubstituted cycloheptyl, substituted or Unsubstituted benzocycloheptanyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornel, substituted or unsubstituted tetrahydropyrrolyl, substituted or unsubstituted piperidinyl, substituted or unsubstituted trimethylsilyl, substituted or unsubstituted triethylsilyl, substituted or unsubstituted triisopropylsilyl, substituted or unsubstituted tritert-butylsilyl, substituted or unsubstituted triphenylsilyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthraceneyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted triphenylene, substituted or unsubstituted pyrene, substituted or unsubstituted perylyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spiro... Fluorenyl, substituted or unsubstituted fluoranyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted furanyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzodibenzofuranyl, substituted or unsubstituted thiopheneyl, substituted or unsubstituted benzothiopheneyl, substituted or unsubstituted dibenzothiopheneyl, substituted or unsubstituted carbazoyl, substituted or unsubstituted benzocarbazoyl, substituted or unsubstituted pyrroleyl, substituted or unsubstituted oxazolyl, substituted or unsubstituted benzooxazolyl, substituted or unsubstituted dibenzooxazolyl substituted or unsubstituted thiazolyl, substituted or unsubstituted benzothiazolyl, substituted or unsubstituted dibenzothiazolyl, substituted or unsubstituted imidazolyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted dibenzoimidazolyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted benzoquinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted benzoisoquinolinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted benzoquinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted benzoquinoxalinyl, substituted or unsubstituted phenantholinyl, substituted or unsubstituted naphridyl, substituted or unsubstituted indolyl, substituted or unsubstituted acridinel, substituted or unsubstituted phenoxazinyl, substituted or unsubstituted phenothiazinyl,Any one of substituted or unsubstituted spirofluorenexanthracene or substituted or unsubstituted spirofluorenethixanthracene.

[0086] More preferably, the heterocyclic compound is selected from any one of the following structures:

[0087]

[0088] Preferably, in Group 1 and each structure derived from Group 1, there are 0 V atoms selected from N atoms, or in Group 1 and each structure derived from Group 1, there is 1 V atom selected from N atoms, or in Group 1 and each structure derived from Group 1, there are 2 V atoms selected from N atoms.

[0089] Preferably, the Choose from any of the following structures:

[0090]

[0091]

[0092] Preferably, Formula II is selected from any one of the following structures:

[0093]

[0094]

[0095] The R9 is selected from any one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C1-C30 silyl, substituted or unsubstituted C3-C25 cycloalkyl, 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 alkanes and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl;

[0096] The f1 is selected from 1, 2, 3, 4 or 5; the f2 is selected from 1, 2, 3, 4, 5, 6 or 7; the f3 is selected from 1, 2, 3, 4, 5, 6, 7, 8 or 9; the f4 is selected from 1 or 2; the f5 is selected from 1, 2, 3, 4, 5, 6, 7 or 8; the f6 is selected from 1, 2, 3 or 4; the f7 is selected from 1, 2 or 3; when there are two or more R9s, the two or more R9s are the same or different from each other, or two adjacent R9s are connected to each other to form a substituted or unsubstituted ring.

[0097] Preferably, R9 is selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted n-propyl, substituted or unsubstituted isopropyl, substituted or unsubstituted n-butyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted benzocyclopropyl, substituted or unsubstituted naphthocyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted benzocyclobutyl, substituted or unsubstituted naphthocyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted benzocyclopentyl, substituted or unsubstituted naphthocyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted benzocyclohexyl, substituted or unsubstituted naphthocyclohexyl, substituted or unsubstituted cycloheptyl, substituted or Unsubstituted benzocycloheptanyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornel, substituted or unsubstituted tetrahydropyrrolyl, substituted or unsubstituted piperidinyl, substituted or unsubstituted trimethylsilyl, substituted or unsubstituted triethylsilyl, substituted or unsubstituted triisopropylsilyl, substituted or unsubstituted tritert-butylsilyl, substituted or unsubstituted triphenylsilyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthraceneyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted triphenylene, substituted or unsubstituted pyrene, substituted or unsubstituted perylyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spiro... Fluorenyl, substituted or unsubstituted fluoranyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted furanyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzodibenzofuranyl, substituted or unsubstituted thiopheneyl, substituted or unsubstituted benzothiopheneyl, substituted or unsubstituted dibenzothiopheneyl, substituted or unsubstituted carbazoyl, substituted or unsubstituted benzocarbazoyl, substituted or unsubstituted pyrroleyl, substituted or unsubstituted oxazolyl, substituted or unsubstituted benzooxazolyl, substituted or unsubstituted dibenzooxazolyl substituted or unsubstituted thiazolyl, substituted or unsubstituted benzothiazolyl, substituted or unsubstituted dibenzothiazolyl, substituted or unsubstituted imidazolyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted dibenzoimidazolyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted benzoquinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted benzoisoquinolinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted benzoquinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted benzoquinoxalinyl, substituted or unsubstituted phenantholinyl, substituted or unsubstituted naphridyl, substituted or unsubstituted indolyl, substituted or unsubstituted acridinel, substituted or unsubstituted phenoxazinyl, substituted or unsubstituted phenothiazinyl,Any one of substituted or unsubstituted spirofluorenexanthracene or substituted or unsubstituted spirofluorenethixanthracene.

[0098] In one implementation, one, two, or more of the R9s in each structure are selected from deuterium.

[0099] Preferably, R9 in each structure is not hydrogen.

[0100] Preferably, R9 in each structure is selected from deuterium.

[0101] Preferably, Formula III is selected from any one of the following structures:

[0102]

[0103]

[0104]

[0105] The R5 is selected from any one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C1-C30 silyl, substituted or unsubstituted C3-C25 cycloalkyl, 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 alkanes and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl;

[0106] The b1 is selected from 1, 2, 3, 4, or 5; the b2 is selected from 1, 2, 3, 4, 5, 6, or 7; the b3 is selected from 1, 2, 3, 4, 5, 6, 7, 8, or 9; the b4 is selected from 1 or 2; the b5 is selected from 1, 2, 3, 4, 5, 6, 7, or 8; the b6 is selected from 1, 2, 3, or 4; the b7 is selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11; the b8 is selected from 1, 2, 3, 4, 5, or 6; the b9 is selected from 1, 2, or 3; when there are two or more R5s, the two or more R5s are the same as or different from each other, or two adjacent R5s are connected to each other to form a substituted or unsubstituted ring.

[0107] Preferably, R5, Ra, and Rb are independently selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted n-propyl, substituted or unsubstituted isopropyl, substituted or unsubstituted n-butyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted benzocyclopropyl, substituted or unsubstituted naphthocyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted benzocyclobutyl, substituted or unsubstituted naphthocyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted benzocyclopentyl, substituted or unsubstituted naphthocyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted benzocyclohexyl, substituted or unsubstituted naphthocyclohexyl, substituted or unsubstituted Substituted cycloheptyl, substituted or unsubstituted benzocycloheptyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornel, substituted or unsubstituted tetrahydropyrrolyl, substituted or unsubstituted piperidinyl, substituted or unsubstituted trimethylsilyl, substituted or unsubstituted triethylsilyl, substituted or unsubstituted triisopropylsilyl, substituted or unsubstituted tri-tert-butylsilyl, substituted or unsubstituted triphenylsilyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthraceneyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted pyrene, substituted or unsubstituted perylene, substituted or unsubstituted Fluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted fluoranyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted furanyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzodibenzofuranyl, substituted or unsubstituted thiopheneyl, substituted or unsubstituted benzothiopheneyl, substituted or unsubstituted dibenzothiopheneyl, substituted or unsubstituted benzodibenzothiopheneyl, substituted or unsubstituted carbazoyl, substituted or unsubstituted benzocarbazoyl, substituted or unsubstituted pyrroleyl, substituted or unsubstituted oxazolyl, substituted or unsubstituted benzooxazolyl, etc. Substituted or unsubstituted dibenzoxazolyl, substituted or unsubstituted thiazolyl, substituted or unsubstituted benzothiazolyl, substituted or unsubstituted dibenzothiazolyl, substituted or unsubstituted imidazolyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted dibenzoimidazolyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted benzoquinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted benzoisoquinolinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted benzoquinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted benzoquinoxalinyl, substituted or unsubstituted phenanthrolinel, substituted or unsubstituted naphridyl, substituted or unsubstituted indolyl, substituted or unsubstituted acridinel, substituted or unsubstituted phenoxazinylAny one of the following: substituted or unsubstituted phenthiazinyl, substituted or unsubstituted spirofluorenoxanthyl, or substituted or unsubstituted spirofluorenthixanthyl.

[0108] Preferably, the R cSelected from substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted n-propyl, substituted or unsubstituted isopropyl, substituted or unsubstituted n-butyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted benzocyclopropyl, substituted or unsubstituted naphthocyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted benzocyclobutyl, substituted or unsubstituted naphthocyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted benzocyclopentyl, substituted or unsubstituted naphthocyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted benzocyclohexyl, substituted or unsubstituted cycloheptyl, substituted or unsubstituted benzocycloheptyl, substituted or unsubstituted adamantyl Alkyl, substituted or unsubstituted norbornel alkyl, substituted or unsubstituted tetrahydropyrrolyl, substituted or unsubstituted piperidinyl, substituted or unsubstituted trimethylsilyl, substituted or unsubstituted triethylsilyl, substituted or unsubstituted triisopropylsilyl, substituted or unsubstituted tritert-butylsilyl, substituted or unsubstituted triphenylsilyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthraceneyl, substituted or unsubstituted phenanthrene, substituted or unsubstituted pyrene, substituted or unsubstituted perylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted fluoranthyl, substituted or Unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted furanyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzodibenzofuranyl, substituted or unsubstituted thiopheneyl, substituted or unsubstituted benzothiopheneyl, substituted or unsubstituted dibenzothiopheneyl, substituted or unsubstituted carbazoleyl, substituted or unsubstituted benzocarbazoleyl, substituted or unsubstituted pyrroleyl, substituted or unsubstituted oxazolyl, substituted or unsubstituted benzooxazolyl, substituted or unsubstituted dibenzooxazolyl, substituted or unsubstituted thiazolyl, substituted or Unsubstituted benzothiazolyl, substituted or unsubstituted dibenzothiazolyl, substituted or unsubstituted imidazolyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted dibenzoimidazolyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted benzoquinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted benzoisoquinolinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted benzoquinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted benzoquinoxalinyl, substituted or unsubstituted phenantholinyl, substituted or unsubstituted naphridyl, substituted or unsubstituted indolyl, substituted or unsubstituted acridineyl, substituted or unsubstituted phenoxazinyl, substituted or unsubstituted phenothiazinyl, substituted or unsubstituted spirofluoroxanthyl,Any one of the substituted or unsubstituted spirofluorenethionanthyl groups.

[0109] In one implementation, one, two, or more of R5 in each structure are selected from deuterium.

[0110] Preferably, R5 in each structure is not hydrogen.

[0111] Preferably, R5 in each structure is selected from deuterium.

[0112] Preferably, when Ar2 is not of formula II or formula III, it is selected from any one of the following structures:

[0113]

[0114]

[0115] The R6 is the same or different from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C1-C30 silyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused cycloyl, substituted or unsubstituted C1-C25 heterocyclic alkanes and C6-C30 aromatic fused cycloyl, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic fused cycloyl;

[0116] The c1 is selected from 0, 1, 2, 3, 4 or 5; the c2 is selected from 0, 1, 2, 3 or 4; the c3 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; the c4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; the c5 is selected from 0, 1 or 2; the c6 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11; the c7 is selected from 0, 1, 2 or 3; when there are two or more R6, the two or more R6 are the same or different from each other, or two adjacent R6 are connected to each other to form a substituted or unsubstituted ring;

[0117] The R d The independent group is selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C1-C30 silyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl.

[0118] Z is selected from either CH or N;

[0119] Y4 and Y5 are each independently selected from O, S, and C(R).e R f ), N(R g Any one of the following;

[0120] The R e R f Independently selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C1-C30 silyl, substituted or unsubstituted C3-C12 cycloalkyl, 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 groups, substituted or unsubstituted C1-C25 heterocyclic alkanes and C6-C30 aromatic ring fused cycloyl groups, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl groups, or R e R f The links between them form substituted or unsubstituted rings;

[0121] The R g It is selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C1-C30 silyl, substituted or unsubstituted C3-C12 cycloalkyl, 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 alkanes and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaryl ring fused cycloyl.

[0122] More preferably, when Ar2 is not of formula II or formula III, it is selected from any one of the following structures:

[0123]

[0124]

[0125]

[0126] The R8 is the same as or different from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C1-C30 silyl, substituted or unsubstituted C3-C25 cycloalkyl, 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 alkanes and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaryl ring fused cycloyl;

[0127] The e1 is selected from 0, 1, 2, 3, 4, or 5; the e2 is selected from 0, 1, 2, 3, or 4; the e3 is selected from 0, 1, 2, or 3; the e4 is selected from 0, 1, or 2; the e5 is selected from 0 or 1; the e6 is selected from 0, 1, 2, 3, 4, 5, 6, or 7; the e7 is selected from 0, 1, 2, 3, 4, 5, or 6; the e8 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9; the e9 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; the e 10 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11; the e 11 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; the e 12 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, or 13; the e 13 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12; the e 14 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, or 15; the e 15 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13 or 14; when there are two or more R8s, the two or more R8s are the same or different from each other, or two adjacent R8s are connected to each other to form a substituted or unsubstituted ring;

[0128] The R m R nEach of the following is independently selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C1-C30 silyl, substituted or unsubstituted C3-C12 cycloalkyl, 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 groups, substituted or unsubstituted C1-C25 heterocyclic alkanes and C6-C30 aromatic ring fused cycloyl groups, and substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaryl ring fused cycloyl groups.

[0129] Preferably, R8 is selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted n-propyl, substituted or unsubstituted isopropyl, substituted or unsubstituted n-butyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted benzocyclopropyl, substituted or unsubstituted naphthocyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted benzocyclobutyl, substituted or unsubstituted naphthocyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted benzocyclopentyl, substituted or unsubstituted naphthocyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted benzocyclohexyl, substituted or unsubstituted naphthocyclohexyl, substituted or unsubstituted cycloheptyl, etc. Substituted or unsubstituted benzocycloheptyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornel, substituted or unsubstituted tetrahydropyrrolyl, substituted or unsubstituted piperidinyl, substituted or unsubstituted trimethylsilyl, substituted or unsubstituted triethylsilyl, substituted or unsubstituted triisopropylsilyl, substituted or unsubstituted tri-tert-butylsilyl, substituted or unsubstituted triphenylsilyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthraceneyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted triphenylene, substituted or unsubstituted pyrene, substituted or unsubstituted perylyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted Spirofluorenyl, substituted or unsubstituted fluoranyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted furanyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzodibenzofuranyl, substituted or unsubstituted thiopheneyl, substituted or unsubstituted benzothiopheneyl, substituted or unsubstituted dibenzothiopheneyl, substituted or unsubstituted carbazoyl, substituted or unsubstituted benzocarbazoyl, substituted or unsubstituted pyrroleyl, substituted or unsubstituted oxazolyl, substituted or unsubstituted benzooxazolyl, substituted or unsubstituted dibenzooxazolyl Azolium, substituted or unsubstituted thiazolyl, substituted or unsubstituted benzothiazolyl, substituted or unsubstituted dibenzothiazolyl, substituted or unsubstituted imidazolyl, substituted or unsubstituted benzimidazolium, substituted or unsubstituted dibenzoimidazolyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted benzoquinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted benzoisoquinolinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted benzoquinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted benzoquinoxalinyl, substituted or unsubstituted phenantholinyl, substituted or unsubstituted naphridyl, substituted or unsubstituted indolyl, substituted or unsubstituted acridinel, substituted or unsubstituted phenoxazinyl, substituted or unsubstituted phenothiazinyl,Any one of substituted or unsubstituted spirofluorenexanthracene or substituted or unsubstituted spirofluorenethixanthracene.

[0130] In one implementation, one, two, or more of the R8s in each structure are selected from deuterium.

[0131] Preferably, R8 in each structure is not hydrogen.

[0132] Preferably, R8 in each structure is selected from deuterium.

[0133] Preferably, L is selected from a single bond or any one of the following structures:

[0134]

[0135] The R7 is independently selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C1-C30 silyl, substituted or unsubstituted C3-C25 cycloalkyl, 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 alkanes and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaryl ring fused cycloyl;

[0136] The d1 is selected from 0, 1, 2, 3 or 4; the d2 is selected from 0, 1, 2, 3, 4, 5 or 6; the d3 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; the d4 is selected from 0, 1 or 2; the d5 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; when there are two or more R7s, the two or more R7s are the same as or different from each other, or two adjacent R7s are connected to each other to form a substituted or unsubstituted ring;

[0137] The L1 is selected from any one of the following: single bond, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C2-C30 heteroarylene, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl group, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl group;

[0138] J is selected from either CH or N;

[0139] The R hIt is selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C1-C30 silyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl;

[0140] Y6, Y7, and Y8 are independently selected from O, S, and C(R). i R j ), N(R k Any one of the following;

[0141] The R i R j Each and every one is independently selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C1-C30 silyl, substituted or unsubstituted C3-C12 cycloalkyl, 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 groups, substituted or unsubstituted C1-C25 heterocyclic alkanes and C6-C30 aromatic ring fused cycloyl groups, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl groups, or R i R j The links between them form substituted or unsubstituted rings;

[0142] The R k It is selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C1-C30 silyl, substituted or unsubstituted C3-C12 cycloalkyl, 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 alkanes and C6-C30 aromatic ring fused cycloyl, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaryl ring fused cycloyl.

[0143] More preferably, L is selected from a single bond or any one of the following structures:

[0144]

[0145]

[0146]

[0147] Preferably, at least one of Ar1, Ar2, and L is selected from those of the aforementioned groups that contain deuterium.

[0148] More preferably, Ar1 is selected from those of the aforementioned groups that contain deuterium.

[0149] More preferably, Ar2 is selected from those of the aforementioned groups that contain deuterium.

[0150] More preferably, L is selected from those of the aforementioned groups that contain deuterium.

[0151] Preferably, R2 is selected from deuterium.

[0152] Preferably, the compound of the present invention contains at least one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two, twenty-three, twenty-four, or twenty-five deuterium atoms.

[0153] Preferably, at least one of Ar1, Ar2, and L is replaced by one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two, twenty-three, twenty-four, or twenty-five deuterium atoms.

[0154] Preferably, the Ar1 is replaced by one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two, twenty-three, twenty-four, or twenty-five deuterium atoms.

[0155] Preferably, the Ar2 is replaced by one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two, twenty-three, twenty-four, or twenty-five deuterium atoms.

[0156] Preferably, the L is replaced by one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen, nineteen, twenty, twenty-one, twenty-two, twenty-three, twenty-four, or twenty-five deuterium atoms.

[0157] Most preferably, the compound of formula I is selected from any one of the following structures:

[0158]

[0159]

[0160]

[0161]

[0162]

[0163]

[0164]

[0165]

[0166]

[0167]

[0168]

[0169]

[0170]

[0171]

[0172]

[0173]

[0174]

[0175]

[0176] 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.

[0177] 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, wherein the organic layer comprises at least one of the heterocyclic compounds described in the present invention.

[0178] Preferably, the organic layer comprises at least one of an electron transport layer and a hole blocking layer, wherein the at least one of the electron transport layer and the hole blocking layer comprises at least one of the heterocyclic compounds described in this invention.

[0179] Preferably, the organic layer includes a light-emitting layer, which contains at least one of the heterocyclic compounds described in this invention.

[0180] More preferably, the organic layer includes an electron transport layer, which includes at least one of the heterocyclic compounds described in this invention.

[0181] More preferably, the organic layer includes a hole-blocking layer, which includes at least one of the heterocyclic compounds described in this invention.

[0182] This invention does not particularly limit the materials of the thin films in the organic electroluminescent device; substances known in the art can be used. The organic functional layers of the aforementioned organic electroluminescent device and the electrodes on both sides of the device are described below:

[0183] The anode material described in this invention is preferably a material with a high work function, in order to improve hole injection efficiency. The anode can be a transmitting electrode, a reflecting electrode, or a semi-transmitting electrode. When the anode is a transmitting electrode, the material used to form the anode can be selected from indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), or any combination thereof; when the anode is a semi-transmitting electrode or a reflecting electrode, the material used to form the anode can be selected from magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), or any combination thereof. The anode can have a single-layer structure or a multilayer structure including two or more layers. For example, the anode can have a single-layer structure of Al or a three-layer structure of ITO / Ag / ITO, but the structure of the anode is not limited to these.

[0184] The cathode material described in this invention is preferably a material with a low work function, in order to improve the electron injection efficiency. The cathode can be selected from Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF / Ca, LiF / Al, Mo, Ti, compounds thereof, or mixtures thereof (e.g., mixtures of Ag and Mg), but is not limited thereto.

[0185] The hole injection layer material described in this invention is preferably a material with good hole injection capability and a suitable HOMO energy level, so as to reduce the interfacial barrier between the anode and the hole transport layer and improve the hole injection capability. The hole injection layer material may include, but is not limited to, metalloporphyrins, oligothiophenes, anthraquinone compounds, arylamine derivatives, perylene derivatives, hexanitrile hexaazabenzophenanthrene compounds, quinacridone compounds, anthraquinone compounds, and conductive polymers based on polyaniline and polythiophene.

[0186] The hole transport layer material described in this invention is preferably a material with high hole mobility to facilitate hole injection. The hole transport layer material may include, but is not limited to, biphenyl diamine derivatives, triarylamine derivatives, carbazole derivatives, fluorene derivatives, stilbene derivatives, phthalocyanine compounds, anthraquinone compounds, quinacridone compounds, hexanitrile hexaazabenzophenanthrene compounds, polythiophene, polyaniline, polyvinylcarbazole, etc.

[0187] The electron blocking layer material of the present invention is preferably a material with good hole transport capability and electron blocking capability, so as to effectively transport holes and restrict electrons from escaping to the light-emitting layer interface. The electron blocking layer material can be selected from materials such as aromatic amine derivatives and carbazole derivatives. Specific examples may include N,N-bis([1,1'-biphenyl]-4-yl)-(9H-carbazole-9-yl)-[1,1'-biphenyl]-4-amine, N-(4'-(9H-carbazole-9-yl)-[1,1'-biphenyl]-4-N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-9H-fluorene-2-amine, N,N'-bis(naphthyl-1-yl)-N,N'-diphenyl-benzidine (NPD), etc., but are not limited thereto.

[0188] The luminescent layer material described in this invention can use red, green, or blue luminescent materials, and typically comprises a host material (also called a matrix material) and a dopant material (also called a guest material). The luminescent layer material can contain multiple host materials and multiple dopant materials. The guest material can be a simple fluorescent material or a phosphorescent material, or a combination of fluorescent and phosphorescent materials. The host material of the luminescent layer needs to possess bipolar charge transport properties and appropriate energy levels to effectively transfer excitation energy to the guest luminescent material. In addition to the heterocyclic compounds provided in this invention, the host material of the luminescent layer can also include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentane derivatives, phenanthrene derivatives, fluoranthene derivatives, etc., and heterocyclic compounds including carbazole derivatives, dibenzofuran derivatives, dibenzothiophene derivatives, pyrimidine derivatives, stilbeneylaryl derivatives, mestilbene derivatives, etc., but is not limited to these. The guest material may include, but is not limited to, metal complexes (such as iridium complexes, platinum complexes, osmium complexes, rhodium complexes, terbium complexes, europium complexes, etc.), anthracene derivatives, pyrene derivatives, perylene derivatives, pyrrole derivatives, indole derivatives, carbazole derivatives, etc.

[0189] The hole-blocking layer of the present invention is preferably made of a material with good electron transport capability and hole blocking capability, so as to effectively transport electrons and limit the escape of holes to the light-emitting layer interface. The hole-blocking layer material can be selected from the following materials: metal complexes, quinoline derivatives, imidazole derivatives, o-phenanthroline derivatives, triazole derivatives, azirbenzene derivatives, etc., preferably at least one of the heterocyclic compounds described in the present invention. Specific examples may include bis(2-methyl-8-hydroxyquinoline-N1,O8)-(1,1'-biphenyl-4-hydroxy)aluminum (BAlq), 1,3,5-tris(N-phenyl-2-benzimidazole)benzene (TPBi), 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 3,3'-[5'-[3-(3-pyridyl)phenyl][1,1':3',1”-terphenyl]-3,3”-diyl]dipyridine (TmPyPB), etc., but is not limited thereto.

[0190] The electron transport layer material described in this invention is preferably a material with high electron mobility to facilitate electron injection. The electron transport layer material may include the heterocyclic compound described in this invention or any one or more of the following structures: thiazole derivatives, quinoline derivatives, benzimidazole derivatives, oxazazole derivatives, azirbenzene derivatives, diazanthracene derivatives, silicon-containing heterocyclic compounds, boron-containing heterocyclic compounds, cyano compounds, phenanthroline derivatives, metal chelates, etc., but is not limited thereto.

[0191] The electron injection layer material described in this invention is preferably a material with good electron injection capability and a suitable LUMO energy level, so as to reduce the interface barrier between the cathode and the electron transport layer and improve the electron injection capability. The electron injection layer material may include metals, alkali metals, alkaline earth metals, alkali metal halides, alkaline earth metal halides, alkali metal oxides, alkaline earth metal oxides, alkali metal salts, alkaline earth metal salts, metal complexes, metal oxides, and other substances with high electron injection capability. Specific examples may include: Li, Ca, Sr, LiF, CsF, CaF2, BaO, Li2CO3, CaCO3, Li2C2O4, Cs2C2O4, CsAlF4, Al2O3, MoO3, MgF2, LiOx, Yb, Tb, cesium 8-hydroxyquinoline, tris(8-hydroxyquinoline)aluminum, etc., but are not limited to these.

[0192] The coating material described in this invention is preferably a material with a high refractive index in order to improve light extraction efficiency. The coating material may include, but is not limited to, tris(8-hydroxyquinoline)aluminum (Alq3), N,N'-di(naphthyl-1-yl)-N,N'-di(phenyl)-2,2'-dimethylbenzidine (NPD), 4,4'-di(9-carbazole)biphenyl (CBP), etc.

[0193] There are no particular limitations on the preparation method of each thin film in the organic electroluminescent device of the present invention. Vacuum evaporation, sputtering, spin coating, spraying, screen printing, laser transfer, etc. can be used, but it is not limited to these methods.

[0194] The organic electroluminescent device of this invention is mainly used in the fields of information display technology and lighting. In terms of information display, it is widely used in various information displays, such as mobile phones, tablet computers, flat-screen TVs, smartwatches, VR, in-vehicle systems, digital cameras, wearable devices, etc.

[0195] 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.

[0196] [Synthesis Route]

[0197] Preparation of compound I:

[0198]

[0199] The raw materials used in this invention are not particularly limited in their source; they can be commercially available products or prepared using methods well-known to those skilled in the art. For example, intermediate d can be prepared by the following synthetic route:

[0200] Preparation of intermediate d:

[0201]

[0202] Xa, Xb, Xc, Xd, Xe, and Xf are each independently selected from any one of Cl, Br, and I; the restrictions on rings A, Ar1, Ar2, L, X, Y, R0, R1, R2, a0, a1, and a2 are the same as those described above.

[0203] Description of raw materials, reagents, and characterization equipment:

[0204] 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 by methods known to those skilled in the art.

[0205] Mass spectrometry was performed using a Waters G2-Si quadrupole tandem time-of-flight high-resolution mass spectrometer, with chloroform as the solvent.

[0206] Elemental analysis was performed using a VarioELcube organic elemental analyzer from Elementar GmbH, Germany, with sample masses ranging from 5 to 10 mg.

[0207] Synthesis Example 1: Preparation of Compound 3

[0208]

[0209] Preparation of A-3:

[0210] Under nitrogen protection, two iodine grains were added to magnesium (4.08 g, 168 mmol), followed by 50 mL of anhydrous tetrahydrofuran solvent. Then, 100 mL of tetrahydrofuran solution of b-3 (31.52 g, 160 mmol) was slowly added dropwise to initiate the Grignard reaction. After the addition was complete, the mixture was reacted at room temperature for 7 h. After the reaction was completed, the mixture was cooled to room temperature.

[0211] Under nitrogen protection, a-3 (29.50 g, 160 mmol) was added to the reaction flask, followed by 200 mL of tetrahydrofuran solvent. The system temperature was lowered to -5 °C, and then the Grignard reagent prepared in step 1 was slowly added dropwise over 2–3 hours. After the addition was complete, the reaction was carried out at -5 °C for 6 hours. After the reaction was completed, the reaction solution was poured into 12% dilute hydrochloric acid and stirred thoroughly for 30 minutes. Then, it was extracted with dichloromethane (300 mL × 3 times) to separate the organic phase. The organic phase was dried over anhydrous magnesium sulfate, and the solvent was concentrated by vacuum distillation. After filtration, it was recrystallized from tetrahydrofuran to obtain intermediate A-3 (33.21 g, yield 78%) with an HPLC purity ≥ 99.75%. Mass spectrometry m / z: 264.9828 (theoretical value: 264.9810).

[0212] Preparation of B-3:

[0213] Under nitrogen protection, intermediates A-3 (23.42 g, 88 mmol), C-3 (10.16 g, 80 mmol), and anhydrous potassium carbonate (22.11 g, 160 mmol) were added to a reaction flask, followed by 200 mL of toluene solution. After purging the air three times with nitrogen, tetrakis(triphenylphosphine)palladium (0.92 g, 0.8 mmol) was added, and the mixture was stirred and heated for 8 hours. After the reaction was completed, the mixture was cooled to room temperature, the solvent was concentrated by vacuum distillation, filtered, and the filter cake was washed with ethanol. The resulting filter cake was recrystallized from toluene to give intermediate B-3 (18.77 g, 75% yield), with an HPLC purity ≥99.85%. Mass spectrometry m / z: 312.0839 (theoretical value: 312.0826).

[0214] Preparation of compound 3:

[0215] Under nitrogen protection, B-3 (12.51 g, 40 mmol), d-3 (13.57 g, 40 mmol), and potassium carbonate (11.06 g, 80 mmol) were added to the reaction flask. Then, 150 mL of a toluene / ethanol / water mixture (toluene:ethanol:water volume ratio = 2:1:1) was added, followed by palladium acetate (0.18 g, 0.8 mmol). After purging the air three times with nitrogen, Xphos (0.76 g, 1.6 mmol) was added. After the reaction was complete, the reactants were cooled to room temperature, distilled water was added, and the mixture was allowed to stand and separate. The separated organic phase was concentrated by vacuum distillation, filtered, and the filter cake was washed with ethanol and distilled water. The resulting filter cake was recrystallized from toluene to give compound 3 (16.46 g, 72%), with an HPLC purity ≥ 99.99% and a mass spectrometry m / z of 571.2043 (theoretical value: 571.2057). Theoretical elemental content (%) C 38 H 17 D5N4O2: C, 79.84; H, 4.76; N, 9.80. Measured elemental content (%): C, 79.87; H, 4.74; N, 9.82.

[0216] Synthesis Example 2: Preparation of Compound 4

[0217]

[0218] Following the same preparation method as compound 3 in Synthesis Example 1, d-3 was replaced with an equimolar amount of d-4, with all other steps remaining the same, to obtain compound 4 (16.69 g). HPLC analysis showed a solid purity ≥99.98%. Mass spectrometry m / z: 571.2041 (theoretical value: 571.2057). Theoretical elemental content (%) C 38 H 17 D5N4O2: C, 79.84; H, 4.76; N, 9.80. Measured elemental content (%): C, 79.85; H, 4.73; N, 9.84.

[0219] Synthesis Example 3: Preparation of Compound 10

[0220]

[0221] Following the same preparation method as compound 3 in Synthesis Example 1, c-3 was replaced with an equimolar amount of c-10, with all other steps remaining the same, to obtain compound 10 (17.99 g). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 651.2635 (theoretical value: 651.2621). Theoretical elemental content (%) C 44 H 17D9N4O2: C, 81.08; H, 5.41; N, 8.60. Measured elemental content (%): C, 81.05; H, 5.42; N, 8.63.

[0222] Synthesis Example 4: Preparation of Compound 28

[0223]

[0224] Following the same preparation method as compound 3 in Synthesis Example 1, c-3 and d-3 were replaced with equimolar amounts of c-28 and d-28, respectively, with all other steps remaining the same, to obtain compound 28 (18.41 g). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 676.2586 (theoretical value: 676.2573). Theoretical elemental content (%) C 45 H 16 D9N5O2: C, 79.86; H, 5.06; N, 10.35. Measured elemental content (%): C, 79.82; H, 5.05; N, 10.37.

[0225] Synthesis Example 5: Preparation of Compound 93

[0226]

[0227] Following the same preparation method as compound 3 in Synthesis Example 1, b-3 was replaced with an equimolar amount of b-93, with all other steps remaining the same, to obtain compound 93 (16.93 g). HPLC analysis showed a solid purity ≥99.99%. Mass spectrometry m / z: 587.1811 (theoretical value: 587.1828). Theoretical elemental content (%) C 38 H 17 D5N4OS: C, 77.66; H, 4.63; N, 9.53. Measured elemental content (%): C, 77.68; H, 4.64; N, 9.52.

[0228] Synthesis Example 6: Preparation of Compound 100

[0229]

[0230] Following the same preparation method as compound 3 in Synthesis Example 1, A-3, c-3, and d-3 were replaced with equimolar amounts of A-93, c-100, and d-4, respectively. All other steps were the same, yielding compound 100 (19.10 g). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 712.2249 (theoretical value: 712.2235). Theoretical elemental content (%) C 48 H 24D4N4OS: C, 80.87; H, 4.52; N, 7.86. Measured elemental content (%): C, 80.85; H, 4.53; N, 7.83.

[0231] Synthesis Example 7: Preparation of Compound 102

[0232]

[0233] Following the same preparation method as compound 3 in Synthesis Example 1, b-3, c-3, and d-3 were replaced with equimolar amounts of b-102, c-102, and d-4, respectively. All other steps were the same, yielding compound 102 (18.82 g). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 691.2381 (theoretical value: 691.2392). Theoretical elemental content (%) C 46 H 17 D9N4OS: C, 79.86; H, 5.10; N, 8.10. Measured elemental content (%): C, 79.85; H, 5.13; N, 8.13.

[0234] Synthesis Example 8: Preparation of Compound 138

[0235]

[0236] Following the same preparation method as compound 3 in Synthesis Example 1, b-3 was replaced with an equimolar amount of b-138, with all other steps remaining the same, to obtain compound 138 (17.66 g). HPLC analysis showed a solid purity ≥99.98%. Mass spectrometry m / z: 621.2226 (theoretical value: 621.2213). Theoretical elemental content (%) C 42 H 19 D5N4O2: C, 81.14; H, 4.70; N, 9.01. Measured elemental content (%): C, 81.11; H, 4.74; N, 9.02.

[0237] Synthesis Example 9: Preparation of Compound 144

[0238]

[0239] Following the same preparation method as compound 3 in Synthesis Example 1, b-3 and c-3 were replaced with equimolar amounts of b-144 and c-144, respectively, with all other steps remaining the same, to obtain compound 144 (17.49 g). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 633.2232 (theoretical value: 633.2244). Theoretical elemental content (%) C 43 H 23D3N4O2: C, 81.50; H, 4.61; N, 8.84. Measured elemental content (%): C, 81.53; H, 4.62; N, 8.82.

[0240] Synthesis Example 10: Preparation of Compound 147

[0241]

[0242] Following the same preparation method as compound 3 in Synthesis Example 1, b-3 was replaced with an equimolar amount of b-147, with all other steps remaining the same, to obtain compound 147 (17.41 g). HPLC analysis showed a solid purity ≥99.97%. Mass spectrometry m / z: 621.2227 (theoretical value: 621.2213). Theoretical elemental content (%) C 42 H 19 D5N4O2: C, 81.14; H, 4.70; N, 9.01. Measured elemental content (%): C, 81.16; H, 4.73; N, 9.02.

[0243] Synthetic Example 11: Preparation of Compound 151

[0244]

[0245] Following the same preparation method as compound 3 in Synthesis Example 1, b-3 was replaced with an equimolar amount of b-151, with all other steps remaining the same, to obtain compound 151 (17.66 g). HPLC analysis showed a solid purity ≥99.98%. Mass spectrometry m / z: 621.2229 (theoretical value: 621.2213). Theoretical elemental content (%) C 42 H 19 D5N4O2: C, 81.14; H, 4.70; N, 9.01. Measured elemental content (%): C, 81.16; H, 4.71; N, 9.02.

[0246] Synthesis Example 12: Preparation of Compound 155

[0247]

[0248] Following the same preparation method as compound 3 in Synthesis Example 1, A-3 and c-3 were replaced with equimolar amounts of A-151 and c-155, respectively, with all other steps remaining the same, to obtain compound 155 (18.95 g). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 696.2474 (theoretical value: 696.2463). Theoretical elemental content (%) C 48 H 24D4N4O2: C, 82.74; H, 4.63; N, 8.04. Measured elemental content (%): C, 82.75; H, 4.66; N, 8.03.

[0249] Synthesis Example 13: Preparation of Compound 159

[0250]

[0251] Following the same preparation method as compound 3 in Synthesis Example 1, b-3 and c-3 were replaced with equimolar amounts of b-159 and c-159, respectively, with all other steps remaining the same, to obtain compound 159 (17.21 g). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 623.2325 (theoretical value: 623.2339). Theoretical elemental content (%) C 42 H 17 D7N4O2: C, 80.88; H, 5.01; N, 8.98. Measured elemental content (%): C, 80.85; H, 5.03; N, 8.96.

[0252] Synthesis Example 14: Preparation of Compound 161

[0253]

[0254] Following the same preparation method as compound 3 in Synthesis Example 1, A-3 and c-3 were replaced with equimolar amounts of A-159 and c-161, respectively, with all other steps remaining the same, to obtain compound 161 (20.01 g). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 757.3448 (theoretical value: 757.3434). Theoretical elemental content (%) C 52 H 31 D7N4O2: C, 82.40; H, 5.98; N, 7.39. Measured elemental content (%): C, 82.42; H, 5.95; N, 7.38.

[0255] Synthetic Example 15: Preparation of Compound 164

[0256]

[0257] Following the same preparation method as compound 3 in Synthesis Example 1, A-3 and c-3 were replaced with equimolar amounts of A-159 and c-164, respectively, with all other steps remaining the same, to obtain compound 164 (18.49 g). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 679.2977 (theoretical value: 679.2965). Theoretical elemental content (%) C 46 H 25D7N4O2: C, 81.27; H, 5.78; N, 8.24. Measured elemental content (%): C, 81.28; H, 5.76; N, 8.28.

[0258] Synthetic Example 16: Preparation of Compound 165

[0259]

[0260] Following the same preparation method as compound 3 in Synthesis Example 1, b-3 and c-3 were replaced with equimolar amounts of b-165 and c-165, respectively, with all other steps remaining the same, to obtain compound 165 (17.91 g). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 648.2282 (theoretical value: 648.2291). Theoretical elemental content (%) C 43 H 16 D7N5O2: C, 79.61; H, 4.66; N, 10.80. Measured elemental content (%): C, 79.62; H, 4.63; N, 10.84.

[0261] Synthetic Example 17: Preparation of Compound 173

[0262]

[0263] Following the same preparation method as compound 3 in Synthesis Example 1, A-3 was replaced with an equimolar amount of A-159, with all other steps remaining the same, to obtain compound 173 (17.86 g). HPLC analysis showed a solid purity ≥99.98%. Mass spectrometry m / z: 628.2663 (theoretical value: 628.2652). Theoretical elemental content (%) C 42 H 12 D 12 N4O2: C, 80.23; H, 5.77; N, 8.91. Measured elemental content (%): C, 80.25; H, 5.75; N, 8.94.

[0264] Synthetic Example 18: Preparation of Compound 174

[0265]

[0266] Following the same preparation method as compound 3 in Synthesis Example 1, A-3 and c-3 were replaced with equimolar amounts of A-159 and c-174, respectively, with all other steps remaining the same, to obtain compound 174 (19.32 g). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 720.2871 (theoretical value: 720.2884). Theoretical elemental content (%) C 48 H 12 D 14N4O3: C, 79.98; H, 5.59; N, 7.77. Measured elemental content (%): C, 79.95; H, 5.57; N, 7.78.

[0267] Synthetic Example 19: Preparation of Compound 175

[0268]

[0269] Following the same preparation method as compound 3 in Synthesis Example 1, b-3 was replaced with an equimolar amount of b-175, with all other steps remaining the same, to obtain compound 175 (18.11 g). HPLC analysis showed a solid purity ≥99.98%. Mass spectrometry m / z: 637.1971 (theoretical value: 637.1985). Theoretical elemental content (%) C 42 H 19 D5N4OS: C, 79.10; H, 4.58; N, 8.78. Measured elemental content (%): C, 79.12; H, 4.55; N, 8.76.

[0270] Synthesis Example 20: Preparation of Compound 188

[0271]

[0272] Following the same preparation method as compound 3 in Synthesis Example 1, b-3 and c-3 were replaced with equimolar amounts of b-188 and c-188, respectively, with all other steps remaining the same, to obtain compound 188 (20.48 g). HPLC analysis showed a solid purity ≥99.91%. Mass spectrometry m / z: 799.3346 (theoretical value: 799.3359). Theoretical elemental content (%) C 57 H 33 D5N4O: C, 85.58; H, 5.42; N, 7.00. Measured elemental content (%): C, 85.56; H, 5.45; N, 7.03.

[0273] Synthesis Example 21: Preparation of Compound 199

[0274]

[0275] Preparation of d-199:

[0276] Under nitrogen protection, e-199 (29.70 g, 70 mmol), pinacol diboronate (18.66 g, 73.5 mmol), and KOAc (20.61 g, 210 mmol) were added to the reaction flask. Then, 300 mL of 1,4-dioxane was added. After purging the air with nitrogen three times, Pd(dppf)Cl2 (0.59 g, 0.8 mmol) was added. The reaction was stirred at 90 °C for 5 hours. After the reaction was completed, the reactants were cooled to room temperature, distilled water was added, and the mixture was extracted with ethyl acetate (500 mL × 3 times) to separate the organic phase. The organic phase was dried with anhydrous magnesium sulfate, and the obtained solid was purified with hexane:EA = 7:1 (v / v) to obtain d-199 (27.06 g, 82%) with HPLC purity ≥ 99.84% and mass spectrometry m / z: 471.2017 (theoretical value: 471.2006).

[0277] Following the same preparation method as compound 3 in Synthesis Example 1, b-3 and d-3 were replaced with equimolar amounts of b-199 and d-199, respectively, with all other steps remaining the same, yielding compound 199 (19.72 g). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 746.2859 (theoretical value: 746.2842). Theoretical elemental content (%) C 52 H 26 D5N5O: C, 83.62; H, 4.86; N, 9.38. Measured elemental content (%): C, 83.63; H, 4.84; N, 9.36.

[0278] Synthesis Example 22: Preparation of Compound 207

[0279]

[0280] Following the same preparation method as compound 3 in Synthesis Example 1, b-3 was replaced with an equimolar amount of b-207, with all other steps remaining the same, to obtain compound 207 (18.54 g). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 671.2385 (theoretical value: 671.2370). Theoretical elemental content (%) C 46 H 21 D5N4O2: C, 82.25; H, 4.65; N, 8.34. Measured elemental content (%): C, 82.23; H, 4.66; N, 8.32.

[0281] Synthesis Example 23: Preparation of Compound 216

[0282]

[0283] Preparation of e-216:

[0284] Under nitrogen protection, f-216 (28.69 g, 100 mmol), d-3 (33.92 g, 100 mmol), and potassium carbonate (27.64 g, 200 mmol) were added to the reaction flask, followed by 350 mL of a toluene / ethanol / water mixture (toluene:ethanol:water volume ratio = 2:1:1). Then, tetrakis(triphenylphosphine)palladium (0.12 g, 0.10 mmol) was added. The reaction was carried out under stirring and reflux for 4 h. After the reaction was completed, the reactants were cooled to room temperature, distilled water was added, and the mixture was allowed to stand and separate. The separated organic phase was concentrated by vacuum distillation, filtered, and the filter cake was washed with ethanol. The obtained filter cake was recrystallized from toluene to obtain e-216 (38.62 g, 85%) with an HPLC purity of ≥99.81% and a mass spectrometry m / z of 453.0651 (theoretical value: 453.0666).

[0285] Preparation of d-216:

[0286] Under nitrogen protection, e-216 (31.81 g, 70 mmol), pinacol diboronate (18.66 g, 73.5 mmol), and KOAc (20.61 g, 210 mmol) were added to the reaction flask, followed by 300 mL of 1,4-dioxane. After purging the air with nitrogen three times, Pd(dppf)Cl2 (0.59 g, 0.8 mmol) was added. The mixture was stirred at 90 °C for 6 hours. After the reaction was completed, the reactants were cooled to room temperature, distilled water was added, and the mixture was extracted with ethyl acetate (500 mL × 3 times) to separate the organic phase. The organic phase was dried with anhydrous magnesium sulfate, and the resulting solid was purified with hexane:EA = 7:1 (v / v) to obtain d-216 (29.13 g, 83%) with an HPLC purity of ≥99.84% and a mass spectrometry m / z of 501.2427 (theoretical value: 501.2413).

[0287] Following the same preparation method as compound 3 in Synthesis Example 1, c-3 and d-3 were replaced with equimolar amounts of c-159 and d-216, respectively, with all other steps remaining the same, to obtain compound 216 (18.37 g). HPLC analysis showed a solid purity ≥99.98%. Mass spectrometry m / z: 646.2323 (theoretical value: 646.2307). Theoretical elemental content (%) C 44 H 22 D4N4O2: C, 81.71; H, 4.67; N, 8.66. Measured elemental content (%): C, 81.74; H, 4.65; N, 8.67.

[0288] Synthesis Example 24: Preparation of Compound 229

[0289]

[0290] Following the same preparation method as compound 216 in synthesis Example 23, f-216 and d-216 were replaced with equimolar amounts of f-229 and d-229, respectively. All other steps were the same, yielding compound 229 (19.01 g). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 698.2577 (theoretical value: 698.2589). Theoretical elemental content (%) C 48 H 22 D6N4O2: C, 82.50; H, 4.90; N, 8.02. Measured elemental content (%): C, 82.52; H, 4.93; N, 8.01.

[0291] Synthesis Example 25: Preparation of Compound 237

[0292]

[0293] Following the same preparation method as compound 216 in synthesis example 23, f-216, B-216, and d-216 were replaced with equimolar amounts of f-237, B-3, and d-237, respectively. All other steps were the same, yielding compound 237 (18.25 g). HPLC analysis showed a solid purity ≥99.97%. Mass spectrometry m / z: 651.2638 (theoretical value: 651.2621). Theoretical elemental content (%) C 44 H 17 D9N4O2: C, 81.08; H, 5.41; N, 8.60. Measured elemental content (%): C, 81.06; H, 5.45; N, 8.63.

[0294] Synthesis Example 26: Preparation of Compound 290

[0295]

[0296] Following the same preparation method as compound 3 in Synthesis Example 1, A-3, c-3, and d-3 were replaced with equimolar amounts of A-151, c-290, and d-290, respectively. All other steps were the same, yielding compound 290 (19.80 g). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 749.2822 (theoretical value: 749.2808). Theoretical elemental content (%) C 52 H 23 D7N4O2: C, 83.29; H, 4.97; N, 7.47. Measured elemental content (%): C, 83.28; H, 4.95; N, 7.46.

[0297] Synthesis Example 27: Preparation of Compound 295

[0298]

[0299] Preparation of g-295:

[0300] Under nitrogen protection, h-295 (52.39 g, 140 mmol), pinacol diboronate (37.33 g, 147 mmol), and KOAc (41.22 g, 420 mmol) were added to the reaction flask. Then, 600 mL of 1,4-dioxane was added. After purging the air with nitrogen three times, Pd(dppf)Cl2 (1.17 g, 1.6 mmol) was added. The mixture was stirred at 90 °C for 6.5 hours. After the reaction was completed, the reactants were cooled to room temperature, distilled water was added, and the mixture was extracted with ethyl acetate (500 mL × 3 times) to separate the organic phase. The organic phase was dried with anhydrous magnesium sulfate. The obtained solid was purified with hexane:EA = 7:1 (v / v) to obtain g-295 (50.72 g, 86%) with an HPLC purity of ≥99.76% and a mass spectrometry m / z of 421.1836 (theoretical value: 421.1849).

[0301] Following the same preparation method as compound 216 in Synthesis Example 23, f-216, d-3, A-3, and d-216 were replaced with equimolar amounts of f-237, g-295, A-175, and d-295, respectively. All other steps were the same, yielding compound 295 (19.10 g). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 712.2247 (theoretical value: 712.2235). Theoretical elemental content (%) C 48 H 24 D4N4OS: C, 80.87; H, 4.52; N, 7.86. Measured elemental content (%): C, 80.86; H, 4.54; N, 7.88.

[0302] Synthesis Example 28: Preparation of Compound 311

[0303]

[0304] Following the same preparation method as compound 3 in Synthesis Example 1, d-3 was replaced with an equimolar amount of d-311, with all other steps remaining the same, to obtain compound 311 (16.93 g). HPLC analysis showed a solid purity ≥99.99%. Mass spectrometry m / z: 587.1815 (theoretical value: 587.1828). Theoretical elemental content (%) C 38 H 17 D5N4OS: C, 77.66; H, 4.63; N, 9.53. Measured elemental content (%): C, 77.68; H, 4.64; N, 9.55.

[0305] Synthesis Example 29: Preparation of Compound 334

[0306]

[0307] Following the same preparation method as compound 3 in Synthesis Example 1, b-3 and d-3 were replaced with equimolar amounts of b-334 and d-311, respectively, with all other steps remaining the same, to obtain compound 334 (18.11 g). HPLC analysis showed a solid purity ≥99.98%. Mass spectrometry m / z: 637.1974 (theoretical value: 637.1985). Theoretical elemental content (%) C 42 H 19 D5N4OS: C, 79.10; H, 4.58; N, 8.78. Measured elemental content (%): C, 79.12; H, 4.55; N, 8.76.

[0308] Synthesis Example 30: Preparation of Compound 394

[0309]

[0310] Following the same preparation method as compound 3 in Synthesis Example 1, A-3, c-3, and d-3 were replaced with equimolar amounts of A-147, c-394, and d-311, respectively. All other steps were the same, yielding compound 394 (19.10 g). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 712.2223 (theoretical value: 712.2235). Theoretical elemental content (%) C 48 H 24 D4N4OS: C, 80.87; H, 4.52; N, 7.86. Measured elemental content (%): C, 80.86; H, 4.54; N, 7.87.

[0311] Synthesis Example 31: Preparation of Compound 405

[0312]

[0313] Following the same preparation method as compound 3 in Synthesis Example 1, B-3 and d-3 were replaced with equimolar amounts of B-175 and d-311, respectively, with all other steps remaining the same, to obtain compound 405 (18.05 g). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 653.1742 (theoretical value: 653.1756). Theoretical elemental content (%) C 42 H 19 D5N4S2: C, 77.15; H, 4.47; N, 8.57. Measured elemental content (%): C, 77.16; H, 4.49; N, 8.55.

[0314] Synthesis Example 32: Preparation of Compound 429

[0315]

[0316] Following the same preparation method as compound 216 in Synthesis Example 23, f-216, d-3, b-3, c-159, and d-216 were replaced with equimolar amounts of f-429, d-311, b-429, c-429, and d-429, respectively. All other steps were the same, yielding compound 429 (20.36 g). HPLC analysis showed a solid purity ≥99.92%. Mass spectrometry m / z: 782.2968 (theoretical value: 782.2955). Theoretical elemental content (%) C 53 H 26 D8N4OS: C, 81.30; H, 5.41; N, 7.16. Measured elemental content (%): C, 81.33; H, 5.42; N, 7.15.

[0317] Synthesis Example 33: Preparation of Compound 454

[0318]

[0319] Following the same preparation method as compound 216 in Synthesis Example 23, f-216, d-3, B-216, and d-216 were replaced with equimolar amounts of f-237, d-311, B-295, and d-454, respectively. All other steps were the same, yielding compound 454 (19.54 g). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 728.2021 (theoretical value: 728.2006). Theoretical elemental content (%) C 48 H 24 D4N4S2: C, 79.09; H, 4.42; N, 7.69. Measured elemental content (%): C, 79.08; H, 4.45; N, 7.65.

[0320] Synthesis Example 34: Preparation of Compound 461

[0321]

[0322] Following the same preparation method as compound 216 in Synthesis Example 23, e-216, B-216, and d-216 were replaced with equimolar amounts of e-461, B-3, and d-461, respectively. All other steps were the same, yielding compound 461 (17.19 g). HPLC analysis showed a solid purity ≥99.99%. Mass spectrometry m / z: 596.2361 (theoretical value: 596.2373). Theoretical elemental content (%) C 40 H 20D5N5O: C, 80.52; H, 5.07; N, 11.74. Measured elemental content (%): C, 80.54; H, 5.04; N, 11.72.

[0323] Synthesis Example 35: Preparation of Compound 510

[0324]

[0325] Following the same preparation method as compound 216 in Synthesis Example 23, e-216, a-3, b-3, c-159, and d-216 were replaced with equimolar amounts of e-510, a-510, b-510, c-3, and d-510, respectively. All other steps were the same, yielding compound 510 (17.12 g). HPLC analysis showed a solid purity ≥99.98%. Mass spectrometry m / z: 602.1633 (theoretical value: 602.1647). Theoretical elemental content (%) C 39 H 18 D5N3S2: C, 77.71; H, 4.68; N, 6.97. Measured elemental content (%): C, 77.72; H, 4.65; N, 6.96.

[0326] Synthesis Example 36: Preparation of Compound 531

[0327]

[0328] Following the same preparation method as compound 3 in Synthesis Example 1, a-3, b-3, and d-3 were replaced with equimolar amounts of a-531, b-531, and d-311, respectively. All other steps were the same, yielding compound 531 (17.55 g). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 635.2096 (theoretical value: 635.2080). Theoretical elemental content (%) C 44 H 21 D5N2OS: C, 83.12; H, 4.91; N, 4.41. Measured elemental content (%): C, 83.15; H, 4.92; N, 4.43.

[0329] [Device Example 1]

[0330] The glass substrate was cleaned with distilled water and ultrasonically. After distilled water washing, it was ultrasonically cleaned using solvents such as isopropanol, acetone, and methanol, and then dried. An anode was formed on the substrate with the reflective layer, using indium tin oxide (ITO). Compound HI was then vacuum-deposited onto the anode to form a layer with a thickness of [thickness missing]. A hole injection layer (HIL) is formed. Compound HT is deposited on the hole injection layer to form a thickness of [missing information]. A hole transport layer. Compound EB is deposited on the hole transport layer to form a layer with a thickness of [thickness missing]. An electron blocking layer is formed. On the electron blocking layer, compound 3 and compound H-1 of the present invention are mixed in a weight ratio of 60%:40% to form a mixed matrix. The mixed matrix and dopant Ir(piq)2(acac) are then vacuum-deposited together at a deposition rate ratio of 94%:6% to form a layer with a thickness of [missing information]. The light-emitting layer (EML) is formed. Compound HB is deposited on the light-emitting layer to form a thickness of [missing information]. A hole-blocking layer was formed. Compounds ET and LiQ were mixed in a 50%:50% weight ratio and deposited by vapor deposition to form a thickness of [thickness value missing]. An electron transport layer (ETL) is formed. LiF is deposited on the electron transport layer to form a layer with a thickness of [missing information]. An electron-injected layer (EIL) is formed. Magnesium (Mg) and silver (Ag) are mixed at a 1:9 evaporation rate and vacuum-deposited to form a layer with a thickness of [missing information]. The cathode. CP is deposited on the cathode to form a thickness of... An organic coating layer (CPL) is applied, thus completing the fabrication of the organic light-emitting device.

[0331]

[0332] [Device Examples 2-36]

[0333] Compounds 4, 10, 28, 93, 100, 102, 138, 144, 147, 151, 155, 159, 161, 164, 165, 173, 174, 175, 188, 199, 207, 216, 229, 237, 290, 295, 311, 334, 394, 405, 429, 454, 461, 510, and 531 of the present invention were used to replace compound 3 in device example 1 as the main material of the light-emitting layer. Otherwise, an organic electroluminescent device was prepared using the same preparation method as device example 1.

[0334] [Comparative Device Examples 1-5]

[0335] Compounds H-2, H-3, H-4, H-5, and H-6 were used to replace compound 3 in device example 1 as the main material of the light-emitting layer. Otherwise, an organic electroluminescent device was prepared using the same preparation method as device example 1.

[0336] 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.

[0337] The test environment was atmospheric, and the temperature was room temperature. The luminescence characteristics test results of devices 1-36 in the device embodiments of the present invention, and those of comparative embodiments 1-5, are shown in Table 1 below.

[0338] Table 1:

[0339]

[0340]

[0341]

[0342] As shown in Table 1, when the heterocyclic compound described in this invention is applied to the host material of the light-emitting layer of an organic electroluminescent device, the device exhibits higher luminous efficiency and a longer lifespan. The compound described in this invention is a high-performance host material for the light-emitting layer.

[0343] [Device Example 37]

[0344] The glass substrate was cleaned with distilled water and ultrasonically. After distilled water washing, it was ultrasonically cleaned using solvents such as isopropanol, acetone, and methanol, and then dried. An anode was formed on the substrate with the reflective layer, using indium tin oxide (ITO). HI-2 was then vacuum-deposited onto the anode to form a layer with a thickness of [missing information]. A hole injection layer (HIL) is formed. Compound HT-2 is deposited on the hole injection layer to form a thickness of [missing information]. A hole transport layer. Compound EB is deposited on the hole transport layer to form a layer with a thickness of [thickness missing]. An electron blocking layer was formed. On this electron blocking layer, compound H-7 and dopant Ir(ppy)2(acac) were co-deposited in a vacuum vapor deposition ratio of 95%:5% to form a layer with a thickness of [missing information]. The light-emitting layer (EML) is formed. Compound HB-2 is deposited on the EML to form a layer with a thickness of [missing information]. A hole-blocking layer. On the hole-blocking layer, compound 3 of the present invention is vapor-deposited to form a layer with a thickness of [thickness missing]. An electron transport layer (ETL) is formed. LiF is deposited on the electron transport layer to form a layer with a thickness of [missing information]. An electron-injected layer (EIL) is formed. Magnesium (Mg) and silver (Ag) are mixed at a 1:9 evaporation rate and vacuum-deposited to form a layer with a thickness of [missing information]. The cathode is used to complete the fabrication of the organic light-emitting device.

[0345]

[0346] [Device Examples 38–72]

[0347] Compounds 4, 10, 28, 93, 100, 102, 138, 144, 147, 151, 155, 159, 161, 164, 165, 173, 174, 175, 188, 199, 207, 216, 229, 237, 290, 295, 311, 334, 394, 405, 429, 454, 461, 510, and 531 of the present invention were used to replace compound 3 in device example 37 as electron transport materials. Otherwise, an organic electroluminescent device was prepared using the same preparation method as device example 37.

[0348] [Comparative Device Examples 6-10]

[0349] Compounds H-2, H-3, H-4, H-5, and H-6 were used to replace compound 3 in device example 37 as electron transport materials. Otherwise, an organic electroluminescent device was prepared using the same preparation method as device example 37.

[0350] 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.

[0351] The test environment was atmospheric, and the temperature was room temperature. The luminescence characteristics test results of devices 37-72 in the device embodiments of this invention, and those of comparative embodiments 6-10, are shown in Table 2 below.

[0352] Table 2:

[0353]

[0354]

[0355] As shown in Table 2, when the heterocyclic compound described in this invention is applied to the electron transport layer material of organic electroluminescent devices, the device has higher luminous efficiency and longer lifespan. The compound of this invention is a high-performance electron transport layer material.

[0356] [Device Example 73]

[0357] The glass substrate was cleaned with distilled water and ultrasonically. After distilled water washing, it was ultrasonically cleaned using solvents such as isopropanol, acetone, and methanol, and then dried. An anode was formed on the substrate with the reflective layer. HI-3 was then vacuum-deposited onto the anode to form a layer with a thickness of [missing information]. A hole injection layer (HIL) is formed. Compound HT-3 is deposited on the hole injection layer to form a thickness of [missing information]. A hole transport layer. Compound EB is deposited on the hole transport layer to form a layer with a thickness of [thickness missing]. An electron blocking layer was formed. On the electron blocking layer, compound H-8 and dopant Ir(ppy)3 were co-deposited in a vacuum vapor deposition ratio of 93%:7% to form a layer with a thickness of [missing information]. The light-emitting layer (EML) is formed. Compound 3 of the present invention is deposited on the light-emitting layer to form a thickness of [thickness missing]. A hole-blocking layer was formed. Compounds ET and LiQ were mixed in a 50%:50% weight ratio and deposited by vapor deposition to form a thickness of [thickness value missing]. An electron transport layer (ETL) is formed. LiF is deposited on the electron transport layer to form a layer with a thickness of [missing information]. An electron-injected layer (EIL) is formed. Magnesium (Mg) and silver (Ag) are mixed at a 1:9 evaporation rate and vacuum-deposited to form a layer with a thickness of [missing information]. The cathode is used to complete the fabrication of the organic light-emitting device.

[0358]

[0359] [Device Examples 74-108]

[0360] Compounds 4, 10, 28, 93, 100, 102, 138, 144, 147, 151, 155, 159, 161, 164, 165, 173, 174, 175, 188, 199, 207, 216, 229, 237, 290, 295, 311, 334, 394, 405, 429, 454, 461, 510, and 531 of the present invention were used to replace compound 3 in device example 73 as hole blocking materials. Otherwise, an organic electroluminescent device was prepared using the same preparation method as device example 73.

[0361] [Comparative Device Examples 11-15]

[0362] Compounds H-2, H-3, H-4, H-5, and H-6 were used to replace compound 3 in device example 73 as hole blocking materials. Otherwise, an organic electroluminescent device was prepared using the same preparation method as device example 73.

[0363] 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.

[0364] The test environment was atmospheric, and the temperature was room temperature. The luminescence characteristics test results of devices 73-108 in the device embodiments of this invention, and those obtained in comparative embodiments 11-15, are shown in Table 3 below.

[0365] Table 3:

[0366]

[0367]

[0368]

[0369] As shown in Table 3, when the heterocyclic compound described in this invention is applied to the hole blocking layer material of organic electroluminescent devices, the device has higher luminous efficiency and longer lifespan. The compound of this invention is a hole blocking layer material with good performance.

[0370] It should be noted that the present invention has been specifically described with reference to specific embodiments. For those skilled in the art, various improvements and modifications can be made to the present invention without departing from the principle of the present invention, and these improvements and modifications also fall within the protection scope of the present invention.

Claims

1. A heterocyclic compound, characterized in that, The heterocyclic compound is selected from any one of the following structures: The V is selected from either CH or N; and each structure has 0 V atoms selected from N atoms, or 1 V atom selected from N atoms; The Y is selected from either O or S; The R p Independently selected from any one of the unsubstituted aryl groups of C6 to C12; The R q R r Independently selected from hydrogen; The g2 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; the g3 is selected from 0, 1, 2, 3, 4 or 5; the g4 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; h1 is selected from 0, 1, 2, 3 or 4; The Choose any one of the following structures: The R2 is selected from hydrogen; The a 21 Selected from 1; the a2 is selected from 2; Ar1 is selected from either Formula II or Formula III; Formula II is selected from any of the following structures: R9 is selected from hydrogen; The f1 is selected from 1, 2, 3, 4, or 5; the f2 is selected from 1, 2, 3, 4, 5, 6, or 7; the formula III is selected from any of the following structures: R5 is selected from either hydrogen or deuterium; The R a R b Independently selected from any one of unsubstituted C1-C6 alkyl groups and unsubstituted phenyl groups; The R c Selected from any one of the unsubstituted C6-C12 aryl groups; b1 is selected from 5; b2 is selected from 7; b3 is selected from 9; b6 is selected from 4; b8 is selected from 6; b9 is selected from 3; when there are two or more R5s, the two or more R5s are the same as each other; The Ar2 is selected from any one of Formula II, Formula III, or the structure shown below: The R8 is selected from either hydrogen or deuterium; The R 8a The same or different are selected from any one of hydrogen, cyano, unsubstituted C1-C6 alkyl, and unsubstituted C3-C10 cycloalkyl; The R 8b Selected from deuterium; The R 8c Selected from hydrogen; The e1 is selected from 5; the e2 is selected from 4; the e6 is selected from 7; the e8 is selected from 9; the e 10 Selected from 11; the e 12 Selected from 13; When there are two or more R8s, the two or more R8s are the same as each other; The e 1a Selected from 0, 1, 2, 3, 4, or 5; when there are two or more R values... 8a At that time, two or more R 8a They are the same as or different from each other; The L is selected from a single bond or any of the following structures: ； The condition is that at least one of Ar1, Ar2, and L is selected from those of the aforementioned groups that contain deuterium.

2. The heterocyclic compound according to claim 1, characterized in that, The heterocyclic compound is selected from any one of the following structures: V is selected from either CH or N.

3. The heterocyclic compound according to claim 1, characterized in that, Formula II is selected from any of the following structures: 。 4. The heterocyclic compound according to claim 1, characterized in that, Formula III is selected from any of the following structures: The R a R b Independently selected from any unsubstituted C1-C6 alkyl group.

5. The heterocyclic compound according to claim 1, characterized in that, The L is selected from a single bond or any of the following structures: 。 6. The heterocyclic compound according to claim 1, characterized in that, When Ar2 is not a formula II or III, it is selected from any of the following structures: The R8 is selected from either hydrogen or deuterium; The R 8a Selected from hydrogen; The R 8b Selected from deuterium.

7. A heterocyclic compound, characterized in that, The compound is selected from any 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, characterized in that, The organic layer comprises at least one of the heterocyclic compounds according to any one of claims 1 to 7.

9. The organic electroluminescent device according to claim 8, characterized in that, The organic layer comprises at least one of an electron transport layer and a hole blocking layer, wherein the at least one of the electron transport layer and the hole blocking layer comprises at least one of the heterocyclic compounds according to any one of claims 1 to 7.

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