A condensed heterocyclic compound and an organic electroluminescent device thereof

Abstract

This invention provides a fused heterocyclic compound and its organic electroluminescent device, specifically relating to the field of organic electroluminescent materials technology. The fused heterocyclic compound provided by this invention possesses excellent electron transport capabilities, suitable HOMO and LUMO energy levels, and a high triplet energy level, which can reduce the electron transport barrier and improve the balance of electron and hole transport. Simultaneously, it can effectively confine holes within the luminescent layer, increasing the probability of effective exciton recombination, thereby reducing the driving voltage, improving luminous efficiency, and extending device lifetime. Furthermore, this fused heterocyclic compound exhibits strong rigidity and a high glass transition temperature, making it less prone to crystallization and aggregation during vapor deposition, thus possessing good film-forming properties and thermal stability. This improves the stability of organic electroluminescent devices and extends the lifespan of electronic components.

Description

Technical Field

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

[0002] OLED (Organic Light Emitting Diode) is a light-emitting device that uses organic solid-state semiconductors as light-emitting materials. It has many advantages such as being all-solid-state, having high luminous efficiency, high color contrast, fast response speed, no viewing angle limitation, being ultra-thin, having low power consumption, and being easy to realize flexible displays and 3D displays. It is a new display technology with broad development prospects.

[0003] The light-emitting principle of organic light-emitting diodes (OLEDs) mainly involves holes and electrons being injected from the cathode and anode into the organic layer under the influence of an applied electric field. They then pass through the hole transport region and electron transport region respectively into the light-emitting layer. Within the light-emitting layer, holes and electrons recombine to generate excitons, which then undergo radiative decay to emit light. Currently, OLED device structures are mostly sandwich-like, consisting of a cathode, an anode, and an organic layer placed between them. The organic layer is further divided into hole transport regions, electron transport regions, and the light-emitting layer, depending on their function. The hole transport region can be further divided into a hole injection layer, a hole transport layer, and an electron blocking layer; the electron transport region can be further divided into an electron injection layer, an electron transport layer, and a hole blocking layer; the light-emitting layer often employs host-guest doping, consisting of a host material and a guest material.

[0004] With the continuous development of organic electroluminescent devices, organic electroluminescent materials have become a research hotspot in this field. Currently, there are still some problems with electron transport region materials and emissive layer materials. Electron transport region materials mainly suffer from low electron transport efficiency, an imbalance between electron and hole transport, and the inability of both to effectively transport to the emissive layer. Energy level mismatch leads to some electrons and holes escaping outside the emissive layer, all of which reduce the luminous efficiency of organic electroluminescent devices and increase the driving voltage. Within the emissive layer, there are also problems such as an imbalance in electron and hole migration and triplet energy level mismatch between host and guest materials, which also result in low efficiency of electron-hole recombination to form excitons, further affecting the luminous efficiency of organic electroluminescent devices.

[0005] Optimization and performance improvement of OLED devices can be further achieved by improving the materials of different functional layers within the device. Therefore, to address the current problems with materials in the electron transport region and the emissive layer, it is necessary to develop electron transport materials, hole blocking materials, and emissive layer substrate materials with superior performance. Summary of the Invention

[0006] To address the problems existing in the prior art, the present invention provides a fused heterocyclic compound and its organic electroluminescent device, which can solve the problems of high driving voltage, low luminous efficiency and short device life of organic electroluminescent devices in the prior art.

[0007] Specifically, the present invention provides a fused heterocyclic compound, wherein the fused heterocyclic compound is selected from the structure represented by formula I:

[0008]

[0009] In Formula I, E is selected from any one of the following groups:

[0010]

[0011] Sites marked with "*" are loop sites;

[0012] The X atom is independently selected from C(R2) or N atoms;

[0013] R0 and R2 are independently selected from any one of hydrogen, deuterium, tritium, cyano, nitro, hydroxyl, halogen atom, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C30 silyl, substituted or unsubstituted C1-C12 alkoxy, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl.

[0014] X0 is selected from O, S or N (R3);

[0015] The R3 is selected from any one of the following: substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C30 silyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl.

[0016] L0, L1, and L2 are independently selected from any one of single-bonded, substituted or unsubstituted C6-C30 arylene, or substituted or unsubstituted C2-C30 heteroarylene.

[0017] Ar1 and Ar2 are independently selected from any one of the following: substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C2-C30 heteroaryl groups, fused cycloalkanes of substituted or unsubstituted C6-C30 aromatic rings and C3-C12 alicyclic groups, and fused cycloalkanes of substituted or unsubstituted C2-C30 heteroaryl rings and C3-C12 alicyclic groups.

[0018] The R1 is independently selected from any one of hydrogen, deuterium, tritium, cyano, nitro, hydroxyl, halogen atom, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C30 silyl, substituted or unsubstituted C1-C12 alkoxy, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl; or two adjacent R1s are connected to form a substituted or unsubstituted ring;

[0019] The m is selected from 1, 2, or 3;

[0020] The condition is that the structure of Formula I contains one or more A groups;

[0021] A is represented by the group described in Formula II:

[0022] Ra, Rb, and Rc are independently selected from any one of substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C1-C12 alkoxy, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl.

[0023] The L3 is selected from any one of single-bonded, substituted or unsubstituted C6-C30 aryl groups, or substituted or unsubstituted C2-C30 heteroaryl groups.

[0024] The present invention also provides an organic electroluminescent device comprising an anode, a cathode, and an organic layer, wherein the organic layer comprises at least one of the fused heterocyclic compounds described in the present invention.

[0025] Beneficial effects:

[0026] The fused heterocyclic compound provided by this invention possesses high electron mobility, suitable HOMO and LUMO energy levels, and a high triplet energy level. On the one hand, it can reduce the electron transport barrier and improve the transport balance between electrons and holes. On the other hand, it can prevent holes from escaping to the electron transport layer side, effectively confining holes within the emissive layer and increasing the recombination probability of excitons in the emissive layer. When used as a hole transport layer or electron blocking layer, it can reduce the driving voltage of organic electroluminescent devices, improve luminous efficiency, and extend lifespan. When used as the host material of the emissive layer, it can improve electron injection and transport performance. Especially when used in combination with a hole-type host, it can balance the distribution of electrons and holes in the emissive layer, improve exciton utilization, avoid efficiency roll-off, reduce the driving voltage of organic electroluminescent devices, improve luminous efficiency, and extend lifespan.

[0027] The fused heterocyclic compound provided by this invention possesses strong rigidity and a high glass transition temperature. During vapor deposition, it is not prone to crystallization or aggregation, exhibiting excellent film-forming properties and thermal stability. In particular, the introduction of large-volume silicon-containing groups into the structure allows for greater intermolecular distance in the thin film state, reducing energy quenching, improving efficiency, and lowering the sublimation temperature. Furthermore, the introduction of silicon-containing groups provides significant steric hindrance, reducing intermolecular stacking effects in the overall molecular structure, improving the film morphology of the fused heterocyclic compound, increasing the glass transition temperature, and enhancing its physical and chemical stability. This, in turn, improves the stability of organic electroluminescent devices and extends the lifespan of electronic components. Detailed Implementation

[0028] The present invention will be further illustrated below with reference to specific embodiments. It should be understood that these embodiments are for illustrative purposes only and are not intended to limit the scope of the invention. After reading the present invention, any modifications of the present invention in various equivalent forms by those skilled in the art will fall within the scope of protection claimed in this application.

[0029] In the compounds of the present invention, any atom not specified as a particular isotope is included as any stable isotope of that atom, and includes atoms at both their natural and non-natural isotopic abundances.

[0030] The halogen atoms described in this invention include fluorine, chlorine, bromine, and iodine.

[0031] In this invention, when the position of the substituent on the ring is not fixed, it means that it can be attached to any of the corresponding optional sites on the ring.

[0032] For example, Can represent Can represent Can represent And so on.

[0033] In this invention, "forming a ring by connecting two adjacent groups" refers to the formation of a substituted or unsubstituted aromatic ring, heteroaromatic ring, aliphatic ring, or aliphatic heterocycle by combining adjacent groups with each other and optionally aromatizing them. The aliphatic ring or aliphatic heterocycle can be a saturated ring or an unsaturated ring. Specifically, the ring formed by the connection can be a three-membered ring, a four-membered ring, a five-membered ring, a six-membered ring, a seven-membered ring, a spirocyclic ring, or a fused ring. Further, the ring formed by the connection can be, for example, benzene, naphthalene, indene, cyclopentene, cyclopentane, cyclopentanophenene, cyclohexene, cyclohexane, cyclohexanophenene, pyridine, quinoline, isoquinoline, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, phenanthrene, or pyrene, but is not limited to these.

[0034]

[0035] In this invention, "substituted or unsubstituted" as used in terms 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" means 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 terms include, but are not limited to, the following groups: deuterium, tritium, cyano, nitro, hydroxyl, halogen atom, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 silyl, substituted or unsubstituted C1-C12 alkoxy, substituted or unsubstituted C1-C12 alkylthio, substituted or unsubstituted C1-C12 alkylamino, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C6-C30 arylamino, etc. The substituents are preferably the following groups: deuterium, tritium, cyano, fluorine, chlorine, bromine, iodine, nitro, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cyclobutenyl, cyclopentenyl, cyclohexenyl, cyclopentadienyl, cyclohexadienyl, adamantyl, norbornel, trifluoromethyl, trifluoroethyl, trimethylsilyl, triethylsilyl, tri-tert-butylsilyl, triphenylsilyl, trideuterated methyl, methoxy, ethoxy, phenyl, biphenyl, terphenyl, naphthyl, phenanthrene, triphenylene, anthracene, pyrene. The following are listed: benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9-methyl-9-phenylfluorenyl, 9,9'-spirodifluorenyl, diphenylamino, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxolinyl, benzoquinolinyl, benzoisoquinolinyl, phenanthrolinel, oxazolyl, benzooxazolyl, thiazolyl, benzothiazolyl, imidazolyl, benzoimidazolyl, benzofuranyl, dibenzofuranyl, benzothiophene, dibenzothiophene, indolyl, carbazoleyl, etc. Furthermore, each of the above substituents can be substituted or unsubstituted, and two adjacent substituents can be linked to form a ring.

[0036] The alkyl group described in this invention refers to a monovalent group in an alkane molecule after removing one hydrogen atom. It can be a straight-chain alkyl group or a branched-chain alkyl group, preferably having 1 to 12 carbon atoms, more preferably having 1 to 8 carbon atoms, and particularly preferably having 1 to 6 carbon atoms. Examples may include methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, isobutyl, sec-butyl, n-pentyl, isopentyl, n-hexyl, etc., but are not limited thereto.

[0037] The cycloalkyl group described in this invention refers to a monovalent group in a cyclic alkane molecule after removing one hydrogen atom, preferably having 3 to 12 carbon atoms, more preferably having 3 to 10 carbon atoms, and particularly preferably having 3 to 6 carbon atoms. Examples may include cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornene, etc., but are not limited thereto.

[0038] The alkoxy group described in this invention is represented by an -O-alkyl group. It can be a straight-chain alkoxy group or a branched-chain alkoxy group, preferably having 1 to 12 carbon atoms, more preferably 1 to 8 carbon atoms, and particularly preferably 1 to 6 carbon atoms. Examples may include methoxy, ethoxy, propoxy, butoxy, pentoxy, hexoxy, etc., but are not limited thereto.

[0039] The aryl group referred to in this invention refers to the general term for a monovalent group remaining after removing a hydrogen atom from the aromatic carbon atom of an aromatic compound molecule. The aryl group includes monocyclic aryl, polycyclic aryl, fused-ring aryl, or combinations thereof. Preferably, it has 6 to 30 carbon atoms, particularly preferably 6 to 18 carbon atoms, and most preferably 6 to 12 carbon atoms. Examples include the following groups: phenyl, biphenyl, terphenyl, tetraphenyl, naphthyl, phenanthryl, anthracene, phenylenetriene, fluorenyl, benzo[a]fluorenyl, spirodifluorenyl, benzo[a]spirodifluorenyl, pyrene, fluoranyl, etc. Basic, etc., but not limited to this.

[0040] The heteroaryl group described in this invention refers to a monovalent group obtained by replacing one or more aromatic carbon atoms in an aromatic hydrocarbon molecule with heteroatoms. The heteroatoms include, but are not limited to, oxygen, sulfur, nitrogen, silicon, or phosphorus atoms, preferably 2 to 30 carbon atoms, particularly preferably 2 to 18 carbon atoms, and most preferably 2 to 12 carbon atoms. Examples of heteroaryl groups include, but are not limited to, the following groups: oxazolyl, benzoxazolyl, naphthoxazolyl, phenanthoxazolyl, anthraquinonexazolyl, tri-benzoxazolyl, pyridinonexazolyl, thiazolyl, benzothiazolyl, naphthothiazolyl, phenanthiazolyl, anthraquinonexazolyl, tri-benzothiazolyl, pyridinonexazolyl, imidazole, benzoimidazolyl, naphthoimidazolyl, phenanthiazolyl, anthraquinonexazolyl, tri-benzoimidazolyl, pyridinonexazolyl, spirofluorenoxanthracene, spirofluorenthionthanthracene, furanyl, benzofuranyl, pyridinonexranthracene, naphthofuranyl, phenanthracene, anthraquinonexranthracene, tri-benzofuranyl, diphenyl The following are examples of compounds, but not limited to: furanyl, benzodibenzofuranyl, thiophenyl, benzothiophenyl, pyridinyl, naphthothiophenyl, phenanthreneyl, anthraquinoneyl, tri-benzothiophenyl, dibenzothiophenyl, benzodibenzothiophenyl, indoleyl, naphthoindoleyl, phenanthreneindoleyl, anthraquinoneindoleyl, tri-benzoindoleyl, carbazoyl, pyridinyl, pyrimidinyl, bipyridinyl, bipyrimidinyl, phenylpyridinyl, phenylpyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthophenonelinyl, benzoquinolinyl, benzoisoquinolinyl, benzoquinazoline, benzoquinoxaline, etc.

[0041] 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 3 to 30 carbon atoms, preferably 3 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.

[0042] The alicyclic rings described in this invention can be saturated or unsaturated rings, and may include cycloalkyl, cycloalkenyl, cycloalkyne, 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. Examples may include cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornene, cyclopropene, cyclobutene, cyclopentene, cyclohexene, cycloheptene, etc., but are not limited thereto.

[0043] The fused cyclic group of aromatic and alicyclic rings described in this invention refers to the general term for a monovalent group remaining after removing one hydrogen atom from an aromatic ring and an alicyclic ring fused together. The alicyclic ring preferably has 3 to 12 carbon atoms, more preferably 3 to 10 carbon atoms, and particularly preferably 3 to 6 carbon atoms. The aromatic ring preferably has 6 to 30 carbon atoms, more preferably 6 to 18 carbon atoms, and particularly preferably 6 to 12 carbon atoms. Examples may include groups such as benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, etc., but are not limited thereto.

[0044] The fused cyclic group of alicyclic and heteroaromatic rings described in this invention refers to the general term for a monovalent group remaining after alicyclic and heteroaromatic rings are fused together and one hydrogen atom is removed. The alicyclic ring preferably has 3 to 12 carbon atoms, more preferably 3 to 10 carbon atoms, and particularly preferably 3 to 6 carbon atoms. The heteroaromatic ring preferably has 2 to 30 carbon atoms, more preferably 2 to 18 carbon atoms, and particularly preferably 2 to 12 carbon atoms. Examples may include the following groups, but are not limited to: pyridocyclobutyl, pyridocyclopentyl, pyridocyclohexyl, pyridocycloheptyl, pyridocyclopentenyl, pyridocyclohexenyl, etc.

[0045] The arylene group described in this invention refers to an aryl group with two bonding sites, i.e., divalent groups. Apart from being divalent groups, they can be described in the same way as the aryl group described above.

[0046] The term "hybrid aryl" as used in this invention refers to a heteroaryl group having two bonding sites, i.e., divalent groups. These sites, apart from being divalent groups, are subject to the above description of heteroaryl groups.

[0047] The term "at least one" as used in this invention includes one, two, three, four, five, six, seven, eight, or more.

[0048] The term "one or more" in this invention includes one, two, three, four, five, six, seven, eight, or more.

[0049] This invention provides a fused heterocyclic compound selected from the structure represented by Formula I:

[0050]

[0051] In Formula I, E is selected from any one of the following groups:

[0052]

[0053] Sites marked with "*" are loop sites;

[0054] The X atom is independently selected from C(R2) or N atoms;

[0055] R0 and R2 are independently selected from any one of hydrogen, deuterium, tritium, cyano, nitro, hydroxyl, halogen atom, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C30 silyl, substituted or unsubstituted C1-C12 alkoxy, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl.

[0056] X0 is selected from O, S or N (R3);

[0057] The R3 is selected from any one of the following: substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C30 silyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl.

[0058] L0, L1, and L2 are independently selected from any one of single-bonded, substituted or unsubstituted C6-C30 arylene, or substituted or unsubstituted C2-C30 heteroarylene.

[0059] Ar1 and Ar2 are independently selected from any one of the following: substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C2-C30 heteroaryl groups, fused cycloalkanes of substituted or unsubstituted C6-C30 aromatic rings and C3-C12 alicyclic groups, and fused cycloalkanes of substituted or unsubstituted C2-C30 heteroaryl rings and C3-C12 alicyclic groups.

[0060] The R1 is independently selected from any one of hydrogen, deuterium, tritium, cyano, nitro, hydroxyl, halogen atom, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C30 silyl, substituted or unsubstituted C1-C12 alkoxy, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl; or two adjacent R1s are connected to form a substituted or unsubstituted ring;

[0061] The m is selected from 1, 2, or 3;

[0062] The condition is that the structure of Formula I contains one or more A groups;

[0063] A is represented by the group described in Formula II:

[0064] Ra, Rb, and Rc are independently selected from any one of substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C1-C12 alkoxy, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl.

[0065] The L3 is selected from any one of single-bonded, substituted or unsubstituted C6-C30 aryl groups, or substituted or unsubstituted C2-C30 heteroaryl groups.

[0066] Preferably, the fused heterocyclic compound is selected from any one of the following structures:

[0067]

[0068] The definitions of E, R0, X0, L0, L1, L2, Ar1, Ar2, R1, and m are the same as those in Equation I.

[0069] Preferably, at least one of E, R0, R1, R3, L0, L1, L2, Ar1, and Ar2 contains one or more A groups; more preferably, at least one of E, R0, R1, Ar1, and Ar2 contains one or more A groups; even more preferably, at least one of E, R0, Ar1, and Ar2 contains one or more A groups; more preferably, at least one of E or R0 contains one or more A groups.

[0070] The inclusion of one or more A groups in E, R0, R1, R3, L0, L1, L2, Ar1, and Ar2 means that at least one hydrogen atom in E, R0, R1, R3, L0, L1, L2, Ar1, and Ar2 is replaced by an A group. Specifically, the inclusion of one or more A groups in E means that at least one hydrogen atom in E is replaced by an A group; the inclusion of one or more A groups in R0 means that at least one hydrogen atom in R0 is replaced by an A group; the inclusion of one or more A groups in Ar1 means that at least one hydrogen atom in Ar1 is replaced by an A group; the inclusion of one or more A groups in Ar2 means that at least one hydrogen atom in Ar2 is replaced by an A group, and so on.

[0071] Preferably, at least one of E, R0, R1, R3, L0, L1, L2, Ar1, and Ar2 contains one, two, three, four, five, six, seven, eight, or more A groups.

[0072] Preferably, the structure represented by Formula I contains one, two, three, four, five, six, seven, eight or more A groups.

[0073] More preferably, the structure represented by Formula I contains one, two, three, or four A groups.

[0074] Preferably, the fused heterocyclic compound is selected from any one of the structures represented by formula III-1, III-2, III-3, III-4, III-5, or III-6:

[0075]

[0076] In formulas III-1, III-2, III-3, III-4, III-5, and III-6, E is independently selected from any one of the following groups:

[0077]

[0078] Sites marked with "*" are fused ring sites; X is independently selected from C(R2) or N atoms;

[0079] R0 and R2 are independently selected from any one of hydrogen, deuterium, tritium, cyano, nitro, hydroxyl, halogen atom, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C30 silyl, substituted or unsubstituted C1-C12 alkoxy, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl.

[0080] The X0 is independently selected from O, S, or N (R3);

[0081] The R3 is independently selected from any one of the following: substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C30 silyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl.

[0082] L0, L1, and L2 are independently selected from any one of single-bonded, substituted or unsubstituted C6-C30 arylene, or substituted or unsubstituted C2-C30 heteroarylene.

[0083] Ar1 and Ar2 are independently selected from any one of the following: substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C2-C30 heteroaryl groups, fused cycloalkanes of substituted or unsubstituted C6-C30 aromatic rings and C3-C12 alicyclic groups, and fused cycloalkanes of substituted or unsubstituted C2-C30 heteroaryl rings and C3-C12 alicyclic groups.

[0084] The R1 is independently selected from any one of hydrogen, deuterium, tritium, cyano, nitro, hydroxyl, halogen atom, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C30 silyl, substituted or unsubstituted C1-C12 alkoxy, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl; or two adjacent R1s are connected to form a substituted or unsubstituted ring;

[0085] The m is independently selected from 1, 2, or 3;

[0086] The A independent group is represented by the group described in Formula II:

[0087] Ra, Rb, and Rc are independently selected from any one of substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C1-C12 alkoxy, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl.

[0088] The L3 is selected from any one of single-bonded, substituted or unsubstituted C6-C30 aryl groups, or substituted or unsubstituted C2-C30 heteroaryl groups.

[0089] Preferably, in this invention, L0, L1, and L2 are connected in a meta position on the benzene ring; or L1 and L2 are connected in an ortho position on the benzene ring, with L0 connected to L1 or L2 in a meta position.

[0090] The "substituted" group in the above-mentioned substituted or unsubstituted group is selected from any one of deuterium, tritium, cyano, nitro, hydroxyl, halogen atom, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C30 silyl, substituted or unsubstituted C1-C12 alkoxy, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl;

[0091] The b is independently selected from 1, 2, 3, 4, or 5.

[0092] Preferably, Formula III-1 is selected from any one of the following structures:

[0093]

[0094] The definitions of E, A, X0, L0, L1, L2, Ar1, Ar2, R1, R0, m, and b are the same as those in Equation III-1;

[0095] Formula III-3 is selected from any of the following structures:

[0096]

[0097] The definitions of E, A, X0, L0, L1, L2, Ar1, Ar2, R1, R0, m, and b are the same as those in Equation III-3;

[0098] Formula III-4 is selected from any of the following structures:

[0099]

[0100] The definitions of E, A, X0, L0, L1, L2, Ar1, Ar2, R1, R0, m, and b are the same as those in Equation III-4;

[0101] Formula III-6 is selected from any of the following structures:

[0102]

[0103] The definitions of E, A, X0, L0, L1, L2, Ar1, Ar2, R1, R0, m, and b are the same as those in Equation III-4.

[0104] Preferably, R1 is independently selected from hydrogen, deuterium, cyano, nitro, fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, methoxy, ethoxy, adamantane, norbornel, phenyl, biphenyl, terphenyl, naphthyl, pyridyl, quinolinyl, isoquinolinyl, benzoxazolyl, benzothiazolyl, benzofuranyl, benzothiophene, deuterated methyl, deuterated ethyl, deuterated iso... The following groups are present: propyl, deuterated tert-butyl, deuterated phenyl, deuterated biphenyl, deuterated naphthyl, fluorinated methyl, fluorinated ethyl, fluorinated isopropyl, fluorinated tert-butyl, fluorinated phenyl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, adamantyl-substituted phenyl, cyano-substituted phenyl, cyano-substituted biphenyl, and A group; when two or more R1 groups are present, adjacent R1 groups may be linked to form a benzene ring.

[0105] Preferably, one, two, or three of R1 are independently selected from group A.

[0106] Preferably, Ra, Rb, and Rc in Formula II are independently selected from any one or more of the following groups: unsubstituted or substituted methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, adamantane, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, and pyridyl.

[0107] Preferably, L3 in Formula II is independently selected from any one of the following: single bond, substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted triphenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted pyridyl, and substituted or unsubstituted pyrimidinyl.

[0108] More preferably, the group represented by Formula II is selected from any one of the following groups:

[0109]

[0110]

[0111] Preferably, the Selected from any one of the following groups:

[0112]

[0113] The definitions of rings E, X0, and R0 are the same as those in Equation I.

[0114] Preferably, the Selected from any one of the following groups:

[0115]

[0116] The definitions of X, X0, and R0 are the same as those in Formula I; the X bonded to the L0 or A group is selected from C atoms. More preferably, the... Selected from any one of the following groups:

[0117]

[0118] More preferably, the Selected from any one of the following groups:

[0119]

[0120] Preferably, the aforementioned At most three X's are selected from N atoms, more preferably, at most two X's are selected from N atoms, and even more preferably, at most one X's are selected from N atoms.

[0121] Further preferably, the Selected from any one of the following groups:

[0122]

[0123]

[0124]

[0125] The definitions of R2 and X0 are the same as those in Equation I;

[0126] P1 is independently selected from 1, 2, 3, 4, 5 or 6; P2 is independently selected from 1, 2, 3, 4 or 5; P3 is independently selected from 1, 2, 3, 4, 5, 6, 7 or 8; P4 is independently selected from 1, 2, 3, 4, 5, 6 or 7; and P5 is independently selected from 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10.

[0127] More preferably, the Selected from any one of the following groups:

[0128]

[0129]

[0130]

[0131] The definitions of R0, R2, and X0 are the same as those in Equation I;

[0132] p1 is independently selected from 1, 2, 3, 4, 5 or 6; p2 is independently selected from 1, 2, 3, 4 or 5; p3 is independently selected from 1, 2, 3, 4, 5, 6, 7 or 8; p4 is independently selected from 1, 2, 3, 4, 5, 6 or 7; p6 is independently selected from 1, 2, 3 or 4; and p7 is independently selected from 1, 2, 3, 4, 5, 6, 7, 8 or 9.

[0133] Preferably, R2 is independently selected from hydrogen, deuterium, tritium, cyano, nitro, hydroxyl, fluorine, chlorine, bromine, iodine, 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 isobutyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted cyclopropane, substituted or unsubstituted cyclobutane, substituted or unsubstituted cyclopentane, substituted or unsubstituted cyclohexane, substituted or unsubstituted cycloheptane, substituted or unsubstituted adamantane, substituted or unsubstituted norbornene, substituted or unsubstituted benzocyclopropane, substituted or unsubstituted benzocyclobutane, substituted or unsubstituted benzocyclopentane, substituted or unsubstituted benzocyclohexane, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthalene. alkyl, substituted or unsubstituted anthraceneyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted 9,9'-spirodifluorenyl, substituted or unsubstituted furanyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzodibenzofuranyl, substituted or unsubstituted thiazolyl The following groups are included: phenyl group, substituted or unsubstituted benzothiophenyl group, substituted or unsubstituted dibenzothiophenyl group, substituted or unsubstituted benzodibenzothiophenyl group, substituted or unsubstituted pyridyl group, substituted or unsubstituted pyrazinyl group, substituted or unsubstituted pyridazinyl group, substituted or unsubstituted quinolinyl group, substituted or unsubstituted isoquinolinyl group, substituted or unsubstituted quinazolinyl group, substituted or unsubstituted quinoxalinyl group, and group A.

[0134] Preferably, one, two, or three of the R2 groups are independently selected from the A group.

[0135] Preferably, the R0 is independently selected from hydrogen, deuterium, tritium, cyano, nitro, hydroxyl, fluorine, chlorine, bromine, iodine, 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 isobutyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted cyclopropane, substituted or unsubstituted cyclobutane, substituted or unsubstituted cyclopentane, substituted or unsubstituted cyclohexyl Alkyl, substituted or unsubstituted cycloheptyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornel, substituted or unsubstituted benzocyclopropane, substituted or unsubstituted benzocyclobutane, substituted or unsubstituted benzocyclopentane, substituted or unsubstituted benzocyclohexane, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracene, substituted or unsubstituted phenanthrene 9,9-dimethylfluorenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted 9,9'-spirodifluorenyl, 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 The following groups are included: substituted or unsubstituted benzodibenzothiophene, substituted or unsubstituted pyridinyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted benzoxazoleyl, substituted or unsubstituted benzothiophene, substituted or unsubstituted benzimidazolyl, and group A.

[0136] Preferably, the R0 is independently selected from the A group.

[0137] Preferably, Ar1 and Ar2 are independently selected from any one of the following groups:

[0138]

[0139] The Z atoms independently are selected from C(R7) or N atoms; the Z atoms connected to L1 or L2 are selected from C atoms;

[0140] The M is independently selected from at least one of substituted or unsubstituted ternary aliphatic rings, quaternary aliphatic rings, pentacetic aliphatic rings, hexaphyllic aliphatic rings, and heptaphyllic aliphatic rings;

[0141] The R4 is independently selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C30 silyl, substituted or unsubstituted C1-C12 alkoxy, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl; or two adjacent R4s are connected to form a substituted or unsubstituted spirocyclic structure;

[0142] The R5 is independently selected from any one of the following: substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C30 silyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl.

[0143] The R7 is independently selected from any one of hydrogen, deuterium, tritium, cyano, nitro, hydroxyl, halogen atom, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C30 silyl, substituted or unsubstituted C1-C12 alkoxy, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl; or two adjacent R7s are connected to form a substituted or unsubstituted ring;

[0144] Y1 is selected from O or S; Y2 is selected from O, S, C(R8)2 or N(R9); Y3 is selected from C(R6) or N atoms; Y4 is selected from C(R6) or N atoms;

[0145] The R6 is independently selected from any one of hydrogen, deuterium, cyano, nitro, hydroxyl, halogen atom, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C1-C12 alkoxy, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl;

[0146] The R8 is independently selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C1-C12 alkoxy, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl.

[0147] The R9 is independently selected from any one of substituted or unsubstituted C1-C12 alkyl groups, substituted or unsubstituted C3-C12 cycloalkyl groups, substituted or unsubstituted C6-C30 aryl groups, and substituted or unsubstituted C2-C30 heteroaryl groups.

[0148] Preferably, M is independently selected from any one of the following groups:

[0149]

[0150] The R 10 Independently selected from any one of hydrogen, deuterium, tritium, cyano, nitro, hydroxyl, halogen atom, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C30 silyl, substituted or unsubstituted C1-C12 alkoxy, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl; or two adjacent Rs 10 The links between them form substituted or unsubstituted rings;

[0151] The a4 is independently selected from 1 or 2, the a2 is independently selected from 1, 2, 3 or 4, the a9 is independently selected from 1, 2, 3, 4, 5, 6, and the a 10 Independently selected from 1, 2, 3, 4, 5, 6, 7, 8, wherein a 11 The independent selection is from 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10.

[0152] More preferably, Ar1 and Ar2 are independently selected from any one of the following groups:

[0153]

[0154]

[0155]

[0156] The a1 is independently selected from 1, 2, 3, 4, or 5; the a2 is independently selected from 1, 2, 3, or 4; the a3 is independently selected from 1, 2, or 3; the a4 is independently selected from 1 or 2; the a5 is independently selected from 1, 2, 3, 4, 5, 6, or 7; the a6 is independently selected from 1, 2, 3, 4, 5, 6, 7, 8, or 9; the a7 is independently selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11; the a8 is independently selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, or 13; the a9 is independently selected from 1, 2, 3, 4, 5, or 6; the a 10 The independent selection is from 1, 2, 3, 4, 5, 6, 7, or 8.

[0157] Preferably, R7 is independently selected from hydrogen, deuterium, cyano, nitro, fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, methoxy, ethoxy, adamantane, norbornel, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, phenyl, biphenyl, terphenyl, naphthyl, pyridyl, pyrazinyl, pyridazinyl, quinolinyl, isoquinolinyl, naphthinyl, quinoxolinyl, quinazolinyl, benzoxazolyl, benzothiazolyl, benzimidazolyl, benzofuranyl, benzothiophene, deuterated The following groups are included: methyl, deuterated ethyl, deuterated isopropyl, deuterated tert-butyl, deuterated phenyl, deuterated biphenyl, deuterated naphthyl, deuterated pyridyl, fluorinated methyl, fluorinated ethyl, fluorinated isopropyl, fluorinated tert-butyl, fluorinated phenyl, fluorinated pyridyl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, adamantyl-substituted phenyl, methyl-substituted pyridyl, ethyl-substituted pyridyl, isopropyl-substituted pyridyl, tert-butyl-substituted pyridyl, cyano-substituted phenyl, cyano-substituted biphenyl, phenyl-substituted quinoxalinyl, phenyl-substituted quinazolinyl, and group A.

[0158] Preferably, one, two, or three of the R7s are independently selected from the A group.

[0159] Preferably, one, two, or three of the R7 groups in Ar1 are independently selected from A groups; one, two, or three of the R7 groups in Ar2 are independently selected from A groups; or one, two, or three of the R7 groups in Ar2 are independently selected from A groups; or one, two, or three of the R7 groups in Ar1 are independently selected from A groups.

[0160] Preferably, R4 is independently selected from any one of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopentyl, cyclohexyl, adamantyl, norbornel, phenyl, biphenyl, naphthyl, benzocyclopentyl, benzocyclohexyl, benzofuranyl, benzothiophenyl, pyridyl, pyrimidinyl, quinolinyl, isoquinolinyl, deuterated methyl, deuterated ethyl, deuterated isopropyl, deuterated tert-butyl, deuterated phenyl, deuterated biphenyl, and deuterated pyridyl; or two adjacent R4s are connected to form a spirocyclic structure as shown below:

[0161]

[0162] "*" indicates a fusion site;

[0163] The R 11The components are independently selected from any one of hydrogen, deuterium, cyano, nitro, fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopentyl, cyclohexyl, adamantyl, norbornel, phenyl, biphenyl, naphthyl, benzocyclopentyl, benzocyclohexyl, benzofuranyl, benzothiophene, pyridyl, pyrimidinyl, quinolinyl, isoquinolinyl, deuterated methyl, deuterated ethyl, deuterated isopropyl, deuterated tert-butyl, deuterated phenyl, deuterated biphenyl, deuterated pyridyl, fluorinated methyl, fluorinated ethyl, fluorinated isopropyl, and fluorinated tert-butyl;

[0164] The q1 is independently selected from 1, 2, 3, 4, 5, 6, 7 or 8, and the q2 is independently selected from 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10.

[0165] Preferably, R5 is independently selected from any one of phenyl, biphenyl, terphenyl, naphthyl, phenanthrene, benzocyclopentyl, benzocyclohexyl, benzofuranyl, benzothiophene, 9,9-dimethylfluorenyl, pyridyl, pyrimidinyl, quinolinyl, isoquinolinyl, deuterated phenyl, deuterated biphenyl, and deuterated pyridyl.

[0166] Preferably, R8 is independently selected from hydrogen, deuterium, cyano, nitro, fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornene, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, phenyl, biphenyl, terphenyl, naphthyl, pyridyl, pyrimidinyl, and pyrazine. The following are all of the following: methyl, pyridazinyl, quinolinyl, isoquinolinyl, naphthidyl, quinoxolinyl, quinazolinyl, benzoxazolyl, benzothiazolyl, benzimidazolyl, benzofuranyl, benzothiopheneyl, deuterated methyl, deuterated ethyl, deuterated isopropyl, deuterated tert-butyl, deuterated phenyl, deuterated biphenyl, deuterated naphthyl, deuterated pyridinyl, fluorinated methyl, fluorinated ethyl, fluorinated isopropyl, fluorinated tert-butyl, and fluorinated phenyl.

[0167] Preferably, R9 is independently selected from any one of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornene, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, phenyl, biphenyl, terphenyl, naphthyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolinyl, isoquinolinyl, naphthidyl, quinoxolinyl, quinazolinyl, benzoxazolyl, benzothiazolyl, benzimidazolyl, benzofuranyl, benzothiophene, deuterated methyl, deuterated ethyl, deuterated isopropyl, deuterated tert-butyl, deuterated phenyl, deuterated biphenyl, deuterated naphthyl, and deuterated pyridyl.

[0168] Preferably, the R 10 The individual compounds are selected independently from any one of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornel, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, phenyl, biphenyl, terphenyl, naphthyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolinyl, isoquinolinyl, naphthidyl, quinoxolinyl, quinazolinyl, benzoxazolyl, benzothiazolyl, benzimidazolyl, benzofuranyl, benzothiophenyl, deuterated methyl, deuterated ethyl, deuterated isopropyl, deuterated tert-butyl, deuterated phenyl, deuterated biphenyl, deuterated naphthyl, and deuterated pyridyl.

[0169] Preferably, L0, L1, and L2 are independently selected from single bonds or at least one of the following groups:

[0170]

[0171] Rx is independently selected from any one of hydrogen, deuterium, tritium, cyano, nitro, hydroxyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C30 silyl, substituted or unsubstituted C1-C12 alkoxy, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl;

[0172] The Ry is independently selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C1-C12 alkoxy, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl.

[0173] The Rz is independently selected from any one of hydrogen, deuterium, tritium, cyano, nitro, hydroxyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C30 silyl, substituted or unsubstituted C1-C12 alkoxy, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl;

[0174] The n1 is independently selected from 1, 2, 3 or 4; the n2 is independently selected from 1, 2 or 3; the n3 is independently selected from 1 or 2; the n4 is selected from 1, 2, 3, 4, 5 or 6; and the n5 is selected from 1, 2, 3, 4, 5, 6, 7 or 8.

[0175] Preferably, Rx is independently selected from hydrogen, deuterium, tritium, cyano, nitro, hydroxyl, fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, trifluoromethyl, trifluoroethyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornel, phenyl, biphenyl, terphenyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, naphthyl, anthracene, phenanthrene, phenylenetriene, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinazolinyl. The following groups are included: quinoxalinyl, naphthidyl, o-phenanthroline, deuterated methyl, deuterated ethyl, deuterated n-propyl, deuterated isopropyl, deuterated n-butyl, deuterated isobutyl, deuterated tert-butyl, deuterated adamantyl, deuterated phenyl, deuterated biphenyl, deuterated naphthyl, deuterated pyridinyl, deuterated pyrazinyl, deuterated quinoxalinyl, deuterated isoquinoxalinyl, deuterated quinoxalinyl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, adamantyl-substituted phenyl, norbornel-substituted phenyl, methyl-substituted biphenyl, ethyl-substituted biphenyl, and group A.

[0176] Preferably, one or both of the Rx groups are selected from A groups.

[0177] Preferably, one or both of the Rx groups of L0 are independently selected from A groups.

[0178] Preferably, one or both of the Rx groups in L1 are independently selected from A groups.

[0179] Preferably, one or both of the Rx groups in L2 are independently selected from A groups.

[0180] More preferably, L0 is selected from a single bond or any one of the following groups:

[0181]

[0182]

[0183] More preferably, L1 and L2 are selected from single bonds or any one of the following groups:

[0184]

[0185]

[0186] Most preferably, the fused heterocyclic compound is selected from any one of the following structures:

[0187]

[0188]

[0189]

[0190]

[0191]

[0192]

[0193]

[0194]

[0195]

[0196]

[0197]

[0198]

[0199]

[0200]

[0201]

[0202]

[0203]

[0204]

[0205]

[0206]

[0207] The above lists some specific chemical structures of fused heterocyclic compounds represented by Formula I of the present invention. However, the present invention is not limited to these listed chemical structures. Any structure based on the structure shown in Formula I with substituents as defined above should be included.

[0208] The present invention also provides an organic electroluminescent device comprising an anode, a cathode, and an organic layer, wherein the organic layer comprises at least one of the fused heterocyclic compounds described in the present invention.

[0209] Preferably, the organic layer is located between the anode and the cathode, or outside at least one of the electrodes of the anode or cathode, and the organic layer contains at least one of the fused heterocyclic compounds described in this invention.

[0210] Preferably, the organic layer includes a light-emitting layer, which includes at least one of the fused heterocyclic compounds described in this invention.

[0211] Preferably, the light-emitting layer comprises a host material, which comprises at least one of the fused heterocyclic compounds described in this invention.

[0212] Preferably, the organic layer comprises at least one of an electron transport layer or a hole blocking layer, wherein the at least one of the electron transport layer or hole blocking layer comprises at least one of the fused heterocyclic compounds described in this invention.

[0213] Preferably, the electron transport layer is located between the electron injection layer and the light-emitting layer, and the hole blocking layer is located between the electron transport layer and the light-emitting layer.

[0214] Preferably, the organic layer comprises an electron transport layer, which comprises at least one of the fused heterocyclic compounds described in this invention.

[0215] Preferably, the organic layer includes a hole-blocking layer, which includes at least one of the fused heterocyclic compounds described in this invention.

[0216] Preferably, the organic layer comprises a light extraction layer, which comprises at least one of the fused heterocyclic compounds described in this invention.

[0217] The organic electroluminescent device of the present invention comprises at least an anode, a cathode, and an organic layer. An organic electroluminescent device may include one or more organic layers, and the organic layers may be located between the anode and the cathode, or outside at least one electrode of the anode or cathode. Specifically, the organic layer located between the anode and the cathode may include one or more of the following: a hole injection layer, a hole transport layer, a light-emitting auxiliary layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer; the organic layer located outside at least one electrode of the anode or cathode includes a light extraction layer. Each of the above functional layers may be composed of a single-layer thin film or multiple thin films, and each thin film may be composed of only one material or multiple materials.

[0218] 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:

[0219] The anode of this invention needs to have a high work function in order to improve hole injection efficiency. The anode material can be selected from materials such as metal oxides, combinations of metals and oxides, metals or their alloys. Specific examples may include indium tin oxide (ITO), indium zinc oxide (IZO), aluminum (Al), titanium (Ti), gold (Au), platinum (Pt), copper (Cu), silver (Ag), indium tin oxide / silver / indium tin oxide (ITO / Ag / ITO), etc., but are not limited to these.

[0220] The cathode of this invention needs to have a low work function in order to improve electron injection efficiency. The cathode material can be selected from materials such as metals or their alloys. Specific examples may include aluminum (Al), silver (Ag), calcium (Ca), indium (In), magnesium:silver (Mg:Ag), etc., but are not limited to these.

[0221] The hole injection layer material of this invention needs to have good hole injection capability and a suitable HOMO energy level in order to reduce the interfacial barrier between the anode and the hole transport layer and improve the hole injection capability. The hole injection layer material can be selected from materials such as aromatic amine derivatives, metal oxides, phthalocyanine metal complexes, polycyano conjugated organic compounds, and polymers. Specific examples may include, but are not limited to, 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazabenzophenanthrene (HAT-CN), copper phthalocyanine (CuPC), 4,4',4”-tris(N,N-2-naphthylphenylamino)triphenylamine (2-TNATA), 4,4',4”-tris(N-3-methylphenyl-N-phenylamino)triphenylamine (m-MTDATA), 2,3,5,6-tetrafluoro-7,7',8,8'-tetracyanodimethyl-p-benzoquinone (F4-TCNQ), poly(4-vinyltriphenylamine) (PVTPA), etc.

[0222] The hole transport layer material of this invention needs to have a high hole mobility to facilitate hole injection. The hole transport layer material can be selected from materials such as aromatic amine derivatives, carbazole derivatives, fluorene derivatives, and polymers. Specific examples may include, but are not limited to, N,N'-diphenyl-N,N'-(1-naphthyl)-1,1'-biphenyl-4,4'-diamine (NPB), N,N'-diphenyl-N,N'-di(2-naphthyl)-1,1'-biphenyl-4,4'-diamine (β-NPB), N,N,N',N'-tetra-1-naphthyl[1,1'-biphenyl]-4,4'-diamine (α-TNB), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (TPD), 4,4'-cyclohexylbis[N,N-di(4-methylphenyl)aniline] (TAPC), 4,4',4”-tris(carbazole-9-yl)triphenylamine (TCTA), and polyvinylcarbazole (PVC).

[0223] The electron blocking layer material of this invention needs to have good hole transport capability and electron blocking capability in order to effectively transport holes and limit the escape of electrons 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.

[0224] As the luminescent layer material described in this invention, red, green, or blue luminescent materials can be used. These materials typically contain a guest (doped) material and a host material. The guest material can be a simple fluorescent material, phosphorescent material, or TADF material, or a combination of fluorescent and phosphorescent materials. The host material of the luminescent layer not only needs to possess bipolar charge transport properties but also requires appropriate energy levels to effectively transfer excitation energy to the guest luminescent material. Examples of such materials include stilbene aryl derivatives, stilbene derivatives, carbazole derivatives, triarylamine derivatives, anthracene derivatives, and pyrene derivatives, with at least one of the fused heterocyclic compounds described in this invention being preferred. Specific examples may include 4,4'-bis(9-carbazole)biphenyl (CBP), 4,4'-bis(9-carbazole)-2,2'-dimethylbiphenyl (CDBP), 9-(4-tert-butylphenyl)-3,6-bis(triphenylsilyl)-9H-carbazole (CZSi), 9,9'-(2,6-pyridinidyldi-3,1-phenylene)bis-9H-carbazole (26DCZPPY), and 9,9'-diphenyl-9H,9' H-3,3'-Bicarbazole (BCzPh), 9-(5-(3-(9H-carbazole-9-yl)phenyl)pyridin-3-yl)-9H-carbazole (CPPyC), 4,4'-bis(carbazole-9-yl)-2,2'-dimethylbiphenyl (CDBP), 1,3-bis(N-carbazole)phenyl (MCP), 9,9-dimethyl-N,N-diphenyl-7-(4-(1-phenyl-1Hbenzi[d]imidazole-2- 10-(4'-(diphenylamino)biphenyl-4-yl)acridin-9(10H)-one (ADBP), tris[4-(pyrene)-phenyl]amine (TPyPA), 9,10-di(2-naphthyl)anthracene (ADN), 2-tert-butyl-9,10-di(2-naphthyl)anthracene (TBADN), 1-(7-[9,9'-bianthra]-10-yl-9,9- Dioctyl-9H-fluorene-2-yl)pyrene (BAnF8Pye), 9,9,9',9'-tetra(4-methylphenyl)-2,2'-bi-9H-fluorene (BDAF), tris(6-fluoro-8-hydroxyquinoline)aluminum (6FAlq3), tris(8-hydroxyquinoline)aluminum (Alq3), bis(10-hydroxybenzo[H]quinoline)beryllium (BeBq2), bis(8-hydroxyquinoline)zinc (Znq2), etc., but not limited to these.

[0225] The guest material can be selected from any one or more of the following structures: metal complexes (e.g., iridium complexes, platinum complexes, osmium complexes, rhodium complexes, etc.), anthracene derivatives, pyrene derivatives, perylene derivatives, etc., but not limited to these. Specific examples may include bis(2-(naphth-2-yl)pyridine)(acetylacetone)iridium (Ir(npy)2acac), tris[2-phenyl-4-methylquinoline)]iridium (Ir(Mphq)3), bis(2-phenylpyridine)iridium acetylacetonate (Ir(ppy)2(acac)), tris[2-(3-methyl-2-pyridyl)phenyl]iridium (Ir(3mppy)3), bis(2-benzo[H]quinoline-C2,N')(acetylacetone)iridium (Ir(bzq)2(acac)), tris(2-(3,5-dimethylphenyl)quinoline-C2,N')iridium (Ir) (dmpq)3), bis(1-phenyl-isoquinoline)(acetylacetone)iridium (Ir(piq)2(acac)), 2,5,8,11-tetra-tert-butylperylene (TBPe), rubrene, 9-(9-phenylcarbazole-3-yl)-10-(naphth-1-yl) (PCAN), 1,4-bis(4-(9H-carbazole-9-yl)styryl)benzene (BCzSB), 1,1'-(4,4'-(4-phenyl-4H-1,2,4-triazol-3,5-diyl)bis(4,1-phenylene))bis(1H-phenoxazine) (2PXZ-TAZ), etc., but not limited to these.

[0226] The hole-blocking layer of the present invention has 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 fused 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.

[0227] The electron transport material of the present invention needs to have a high electron mobility to facilitate electron injection. The electron transport layer material can be selected from the following materials: quinoline derivatives, imidazole derivatives, o-phenanthroline derivatives, triazole derivatives, metal chelates, azirbenzene derivatives, diazanthracene derivatives, silicon-containing heterocyclic compounds, boron-containing heterocyclic compounds, etc., preferably at least one of the fused heterocyclic compounds described in the present invention. Specific examples may include, but are not limited to, 8-hydroxyquinoline aluminum (Alq3), 2,9-bis(naphthyl-2-yl)-4,7-diphenyl-1,10-phenanthroline (NBphen), 1,3,5-tris(4-pyridin-3-ylphenyl)benzene (TpPyPB), 1,3,5-tris(4-pyridylquinoline-2-yl)benzene (TPyQB), 3-(biphenyl-4-yl)-4-phenyl-5-(4-tert-butylphenyl)-1,2,4-triazole (TAZ), 1,3,5-tris(N-phenyl-2-benzimidazole)benzene (TPBi), and tris[2,4,6-trimethyl-3-(3-pyridinyl)phenyl]borane (3TPYMB).

[0228] The electron injection material of this invention needs to have good electron injection capability and a suitable LUMO energy level in order to reduce the interface barrier between the cathode and the electron transport layer and improve the electron injection capability. The electron injection layer material includes, but is not limited to, the following materials: metals, alkali metals, alkaline earth metals, metal compounds, metal oxides, metal halides, alkaline earth metal compounds, alkaline earth metal oxides, alkaline earth metal halides, alkali metal compounds, alkali metal oxides, alkali metal halides, etc. Specific examples may include lithium (Li), strontium (Sr), ytterbium (Yb), lithium fluoride (LiF), sodium fluoride (NaF), cesium fluoride (CsF), calcium fluoride (CaF2), lithium 8-hydroxyquinoline (Liq), aluminum tris(8-hydroxyquinoline) (Alq3), cesium carbonate (Cs2CO3), rubidium acetate (CH3COORb), lithium oxide (Li2O), barium oxide (BaO), etc., but is not limited to these.

[0229] The light extraction layer of this invention has the function of optical coupling to improve light extraction efficiency. The light extraction layer material may include materials such as metal compounds, triarylamine derivatives, benzidine derivatives, and carbazole derivatives, preferably at least one of the fused heterocyclic compounds described in this invention. Specific examples may include tris(8-hydroxyquinoline)aluminum (Alq3), N,N'-di(naphthyl-1-yl)-N,N'-di(phenyl)-2,2'-dimethylbenzidine (NPD), and 4,4'-di(9-carbazole)biphenyl (CBP), etc.

[0230] 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.

[0231] 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.

[0232] Synthesis Examples

[0233] Raw materials and reagents: The present invention does not impose any particular restrictions on the raw materials or reagents used in the following synthesis examples. They can be commercially available products or prepared using methods well known to those skilled in the art.

[0234] Instruments: G2-Si quadrupole tandem time-of-flight high-resolution mass spectrometer (Waters Corporation, UK); Vario ELcube organic elemental analyzer (Elementar Corporation, Germany).

[0235] The core structure of the compound of Formula I of this invention can be prepared by the reaction route shown below. The substituents can be bonded by methods known in the art, and the type, position and number of substituents can be changed according to techniques known in the art.

[0236] Synthesis route:

[0237]

[0238] The main reaction type involved in this invention is the Suzuki coupling reaction. The starting materials in the synthetic route provided by this invention can be commercially available products or prepared by methods known in the art. For example, starting material b can be prepared by the following synthetic route:

[0239]

[0240] Raw material c can be prepared via the following synthetic route:

[0241]

[0242] Raw material d can be prepared by the following synthetic route:

[0243]

[0244] Xa, Xb, Xc, Xd, and Xe are independently selected from Cl, Br, and I.

[0245] When L1-Ar1 and L2-Ar2 are the same, the above-mentioned L1-Ar1 and L2-Ar2 groups can also be introduced together in one step to obtain the present invention.

[0246] Fused heterocyclic compounds represented by Formula 1, for example:

[0247]

[0248] Alternatively, the order of the above reactions can be changed to obtain the fused heterocyclic compound represented by Formula I of the present invention.

[0249] Synthesis Example 1: Preparation of Intermediate c-1

[0250]

[0251] J-1 (34.53 g, 150.00 mmol), pinacol diboronate (41.90 g, 165.00 mmol), CH3COOK (32.39 g, 330.00 mmol), and DMF (750 mL) were added to the reaction flask. After purging the air three times with nitrogen, Pd(dppf)Cl2 (1.21 g, 1.65 mmol) was added. The mixture was heated and stirred for 8.5 hours. After the reaction was completed, the mixture was cooled to room temperature, distilled water was added, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, the solvent was concentrated by vacuum distillation, and crystals were precipitated by cooling. The crystals were filtered and recrystallized from toluene to give intermediate C-1 (35.76 g, 86%) with an HPLC purity of ≥99.82%. Mass spectrometry m / z: 277.1681 (theoretical value: 277.1669).

[0252] According to the above preparation method, the following intermediates were also synthesized in this invention:

[0253]

[0254]

[0255]

[0256] Synthesis Example 2: Preparation of Intermediate d-71

[0257]

[0258] Preparation of intermediate O-71:

[0259] Compounds m-71 (118.46 g, 630.00 mmol), n-71 (80.23 g, 756.00 mmol), NaCN (30.87 g, 630.00 mmol), and DMF (3000 mL) were added to a reaction flask, and the mixture was stirred at 100 °C for 9 hours. After the reaction was completed, the reaction solution was cooled to room temperature, distilled water was added, and the mixture was extracted with ethyl acetate. The organic layer was separated, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated by vacuum distillation. Crystallization was carried out at a lower temperature, and the resulting solid was recrystallized from toluene to give intermediate o-71 (130.70 g, yield 76%). The purity of the solid was ≥99.78% as determined by HPLC. Mass spectrometry m / z: 272.9780 (theoretical value: 272.9789).

[0260] Preparation of intermediate r-71:

[0261] O-71 (104.16 g, 380.00 mmol), P-71 (70.07 g, 380.00 mmol), Na2CO3 (60.41 g, 570.00 mmol), and 1500 mL of toluene / ethanol / water (2:1:1) mixed solvent were added to the reaction flask. After purging the air three times with nitrogen, Pd(PPh3)4 (4.39 g, 3.80 mmol) was added to the reaction flask. The mixture was stirred under nitrogen protection for 15 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, filtered, washed with distilled water, and then the obtained solid was recrystallized from toluene to give intermediate R-71 (102.73 g, yield 81%). The purity of the solid was ≥99.70% as determined by HPLC. Mass spectrometry m / z: 333.0542 (theoretical value: 333.0557).

[0262] Preparation of intermediate S-71:

[0263] R-71 (93.46 g, 280.00 mmol), (methoxymethyl)triphenylphosphine chloride (143.98 g, 420.00 mmol), and 1400 mL THF were added to a reaction flask. The mixture was stirred and then cooled to below 0 °C. Potassium tert-butoxide (1 M, in THF, 700 mL) was slowly added dropwise to the mixture. After the addition was complete, the temperature of the mixture was slowly increased, and the mixture was stirred at room temperature for 12 hours. After the reaction was completed, the mixture was cooled to room temperature, distilled water was added, and the mixture was extracted with dichloromethane. The layers were allowed to stand and separated, and the organic layer was collected, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated by vacuum distillation. The mixture was cooled to crystallize, filtered, and the resulting solid was recrystallized from toluene / methanol at an 8:1 ratio to obtain intermediate S-71 (79.02 g, 78%). The purity of the solid was ≥99.73% as determined by HPLC. Mass spectrometry m / z: 361.0852 (theoretical value: 361.0870).

[0264] Preparation of intermediate t-71:

[0265] S-71 (68.75 g, 190.00 mmol), 320 mL of Eaton reagent (7.7 wt% phosphorus pentoxide methanesulfonic acid solution), and 500 mL of chlorobenzene were added to the reaction flask. The mixture was refluxed for 12 hours. After the reaction was completed, the mixture was cooled to room temperature and then extracted with dichloromethane. The organic phase was dried over anhydrous magnesium sulfate, filtered, and the solvent was concentrated by vacuum distillation. Crystallization was carried out at a lower temperature, filtered, and then recrystallized from toluene to obtain intermediate T-71 (50.13 g, 80%). The purity of the solid was ≥99.81% as determined by HPLC. Mass spectrometry m / z: 329.0618 (theoretical value: 329.0607).

[0266] Preparation of intermediate d-71:

[0267] T-71 (46.17 g, 140.00 mmol), pinacol diboronate (39.11 g, 154.00 mmol), CH3COOK (30.23 g, 308.00 mmol), and DMF (700 mL) were added to the reaction flask. After purging the air three times with nitrogen, Pd(dppf)Cl2 (1.13 g, 1.54 mmol) was added. The mixture was heated and stirred for 8 hours. After the reaction was completed, the mixture was cooled to room temperature, distilled water was added, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, the solvent was concentrated by vacuum distillation, and crystals were precipitated by cooling. The crystals were filtered and recrystallized from toluene to obtain intermediate d-71 (48.94 g, 83%) with an HPLC purity ≥ 99.85%. Mass spectrometry m / z: 421.1830 (theoretical value: 421.1849).

[0268] According to the above preparation method, the following intermediates were also synthesized in this invention:

[0269]

[0270]

[0271]

[0272] Synthesis Example 3: Preparation of Intermediate d1-45

[0273]

[0274] Preparation of intermediate h-45:

[0275] Add d-45 (36.43 g, 100.00 mmol), g-45 (19.15 g, 100.00 mmol), Na2CO3 (15.90 g, 150.00 mmol), and 500 mL of toluene / ethanol / water (2:1:1) mixed solvent to the reaction flask. After purging the air three times with nitrogen, add Pd(PPh3)4 (1.16 g, 1.00 mmol). Stir the reaction mixture under nitrogen protection for 8 hours. After the reaction is complete, cool the reaction mixture to room temperature, filter, wash with distilled water, and then recrystallize the obtained solid from toluene to obtain intermediate h-45 (28.01 g). HPLC analysis showed that the purity of the solid was ≥99.79%. Mass spectrometry m / z: 345.0363 (theoretical value: 345.0379).

[0276] Preparation of intermediate d1-45:

[0277] h-45 (24.21 g, 70.00 mmol), pinacol diboronate (19.55 g, 77.00 mmol), CH3COOK (15.11 g, 154.00 mmol), and DMF (350 mL) were added to the reaction flask. After purging the air three times with nitrogen, Pd(dppf)Cl2 (0.56 g, 0.77 mmol) was added. The mixture was heated and stirred for 4 hours. After the reaction was completed, the mixture was cooled to room temperature, distilled water was added, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, the solvent was concentrated by vacuum distillation, and crystals were precipitated by cooling. The crystals were filtered and recrystallized from toluene to obtain intermediate d1-45 (23.88 g); HPLC purity ≥ 99.87%. Mass spectrometry m / z: 437.1629 (theoretical value: 437.1621).

[0278] According to the above preparation method, the following intermediates were also synthesized in this invention:

[0279]

[0280]

[0281] Synthesis Example 4: Preparation of Compound 1

[0282]

[0283] Preparation of intermediate A-1:

[0284] Add a-1 (22.21 g, 70.00 mmol), b-1 (12.11 g, 70.00 mmol), Na2CO3 (11.13 g, 105.00 mmol), and 350 mL of toluene / ethanol / water (2:1:1) mixed solvent to the reaction flask. After purging the air three times with nitrogen, add Pd(PPh3)4 (0.81 g, 0.70 mmol). Stir the reaction mixture under nitrogen protection for 5 hours. After the reaction is complete, cool the reaction mixture to room temperature, filter, wash with distilled water, and then recrystallize the obtained solid with toluene / methanol = 10:1 to obtain intermediate A-1 (18.96 g, yield 85%). HPLC analysis showed that the purity of the solid was ≥99.70%. Mass spectrometry m / z: 316.9620 (theoretical value: 316.9607).

[0285] Preparation of intermediate B-1:

[0286] Add A-1 (15.93 g, 50.00 mmol), c-1 (13.86 g, 50.00 mmol), K2CO3 (10.37 g, 75.00 mmol), and 250 mL of 1,4-dioxane to a reaction flask. After purging the air three times with nitrogen, add Pd(PPh3)4 (0.58 g, 0.50 mmol). Stir the reaction mixture under nitrogen protection for 4 hours. After the reaction is complete, cool the reaction mixture to room temperature, add distilled water, and extract with dichloromethane. Dry the organic layer with anhydrous MgSO4, remove the solvent under reduced pressure, and recrystallize with ethyl acetate to obtain intermediate B-1 (15.95 g, yield 82%). HPLC analysis showed that the solid purity was ≥99.73%. Mass spectrometry m / z: 388.1154 (theoretical value: 388.1163).

[0287] Preparation of compound 1:

[0288] Add B-1 (11.67 g, 30.00 mmol), d-1 (13.12 g, 30.00 mmol), K2CO3 (6.22 g, 45.00 mmol), and 150 mL of toluene / ethanol / water (2:1:1) mixed solvent to a reaction flask. After purging the air three times with nitrogen, add Pd2(dba)3 (0.27 g, 0.30 mmol) and P(t-Bu)3 (0.5 M toluene solution) (1.2 mL, 0.6 mmol). Stir the reaction under nitrogen protection for 3.5 hours. After the reaction is complete, cool the reaction mixture to room temperature, filter, wash with distilled water, and then recrystallize the obtained solid from toluene to give compound 1 (15.54 g, yield 78%). HPLC analysis showed that the purity of the solid was ≥99.91%. Mass spectrometry m / z: 663.2179 (theoretical value: 663.2164). Theoretical element content (%) C44 H 33 N3SSi: C, 79.60; H, 5.01; N, 6.33. Measured elemental content (%): C, 79.63; H, 5.05; N, 6.29.

[0289] Synthesis Example 5: Preparation of Compound 30

[0290]

[0291] Following the same preparation method as Compound 1 in Synthesis Example 4, b-1, c-1, and d-1 were replaced with equimolar amounts of b-30, c-30, and d-30, respectively, to obtain Compound 30 (18.00 g). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 821.2760 (theoretical value: 821.2750). Theoretical elemental content (%) C 59 H 39 NO2Si: C, 86.20; H, 4.78; N, 1.70. Measured elemental content (%): C, 86.17; H, 4.82; N, 1.66.

[0292] Synthesis Example 6: Preparation of Compound 45

[0293]

[0294] Following the same preparation method as Compound 1 in Synthesis Example 4, b-1, c-1, and d-1 were replaced with equimolar amounts of b-45, c-45, and d1-45, respectively, to obtain Compound 45 (18.13 g). HPLC analysis showed a solid purity ≥99.98%. Mass spectrometry m / z: 850.2852 (theoretical value: 850.2869). Theoretical elemental content (%) C 56 H 46 N2OSSi2: C, 79.02; H, 5.45; N, 3.29. Measured elemental content (%): C, 79.06; H, 5.42; N, 3.31.

[0295] Synthesis Example 7: Preparation of Compound 71

[0296]

[0297] Following the same preparation method as compound 1 in Example 4, b-1, c-1, and d-1 were replaced with equimolar amounts of b-71, c-71, and d1-71, respectively, to obtain compound 71 (18.19 g). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 841.3476 (theoretical value: 841.3488). Theoretical elemental content (%) C 59 H 47N3OSi: C, 84.15; H, 5.63; N, 4.99. Measured elemental content (%): C, 84.10; H, 5.59; N, 4.96.

[0298] Synthesis Example 8: Preparation of Compound 97

[0299]

[0300] Preparation of intermediate C-97:

[0301] Add a-97 (13.52 g, 50.00 mmol), c-1 (27.72 g, 100.00 mmol), Na2CO3 (15.90 g, 150.00 mmol), and 500 mL of toluene / ethanol / water (2:1:1) mixed solvent to a reaction flask. After purging the air three times with nitrogen, add Pd(PPh3)4 (1.16 g, 1.00 mmol). Stir the reaction mixture under nitrogen protection for 8 hours. After the reaction is complete, cool the reaction mixture to room temperature, filter, wash with distilled water, and then recrystallize the obtained solid with toluene / methanol = 8:1 to obtain intermediate C-97 (17.06 g, yield 83%). HPLC analysis showed that the purity of the solid was ≥99.83%. Mass spectrometry m / z: 410.1416 (theoretical value: 410.1401).

[0302] Preparation of compound 97:

[0303] C-97 (12.33 g, 30.00 mmol), d-97 (12.64 g, 30.00 mmol), Na2CO3 (4.77 g, 45.00 mmol), and 150 mL THF were added to a reaction flask. After purging the air three times with nitrogen, Pd2(dba)3 (0.27 g, 0.30 mmol) and P(t-Bu)3 (0.5 M toluene solution, 1.2 mL, 0.6 mmol) were added to the reaction flask. The mixture was stirred under nitrogen protection for 3 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, filtered, washed with distilled water, and then recrystallized from toluene to give compound 97 (16.08 g, yield 80%). HPLC analysis showed that the purity of the solid was ≥99.97%. Mass spectrometry m / z: 669.2643 (theoretical value: 669.2632). Theoretical elemental content (%) C 43 H 39 N3OSi2: C, 77.09; H, 5.87; N, 6.27. Measured elemental content (%): C, 77.12; H, 5.91; N, 6.22.

[0304] Synthesis Example 9: Preparation of Compound 106

[0305]

[0306] Following the same preparation method as compound 97 in Example 8, a-97, c-1, and d-97 were replaced with equimolar amounts of a-106, c-106, and d-106, respectively, to obtain compound 106 (17.74 g). HPLC analysis showed a solid purity ≥99.92%. Mass spectrometry m / z: 767.3026 (theoretical value: 767.3040). Theoretical elemental content (%) C 53 H 45 NOSi2: C, 82.88; H, 5.91; N, 1.82. Measured elemental content (%): C, 82.92; H, 5.89; N, 1.78.

[0307] Synthesis Example 10: Preparation of Compound 113

[0308]

[0309] Following the same preparation method as compound 97 in Synthesis Example 8, c-1 and d-97 were replaced with equimolar amounts of c-113 and d-113, respectively, to obtain compound 113 (18.63 g). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 838.2995 (theoretical value: 838.2982). Theoretical elemental content (%) C 54 H 46 N4SSi2: C, 77.29; H, 5.53; N, 6.68. Measured elemental content (%): C, 77.32; H, 5.49; N, 6.65.

[0310] Synthetic Example 11: Preparation of Compound 127

[0311]

[0312] Following the same preparation method as compound 97 in Synthesis Example 8, c-1 and d-97 were replaced with equimolar amounts of c-127 and d-127, respectively, to obtain compound 127 (16.22 g). HPLC analysis showed a solid purity ≥99.91%. Mass spectrometry m / z: 692.2670 (theoretical value: 692.2679). Theoretical elemental content (%) C 46 H 40 N₂OSi₂: C, 79.73; H, 5.82; N, 4.04. Measured elemental content (%): C, 79.77; H, 5.78; N, 4.07.

[0313] Synthesis Example 12: Preparation of Compound 143

[0314]

[0315] Following the same preparation method as compound 97 in Synthesis Example 8, c-1 and d-97 were replaced with equimolar amounts of c-143 and d-143, respectively, to obtain compound 143 (15.44 g). HPLC analysis showed a solid purity ≥99.98%. Mass spectrometry m / z: 685.2411 (theoretical value: 685.2403). Theoretical elemental content (%) C 43 H 39 N3SSi2: C, 75.28; H, 5.73; N, 6.13. Measured elemental content (%): C, 75.30; H, 5.76; N, 6.18.

[0316] Synthesis Example 13: Preparation of Compound 204

[0317]

[0318] Following the same preparation method as compound 97 in Synthesis Example 8, c-1 and d-97 were replaced with equimolar amounts of c-204 and d1-204, respectively, to obtain compound 204 (18.11 g). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 849.2859 (theoretical value: 849.2843). Theoretical elemental content (%) C 55 H 43 N3O3Si2: C, 77.71; H, 5.10; N, 4.94. Measured elemental content (%): C, 77.76; H, 5.06; N, 4.91.

[0319] Synthesis Example 14: Preparation of Compound 215

[0320]

[0321] Following the same preparation method as compound 97 in Synthesis Example 8, c-1 and d-97 were replaced with equimolar amounts of b-215 and d-215, respectively, to obtain compound 215 (17.65 g). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 773.2850 (theoretical value: 773.2862). Theoretical elemental content (%) C 54 H 39 N3OSi: C, 83.80; H, 5.08; N, 5.43. Measured elemental content (%): C, 83.76; H, 5.11; N, 5.45.

[0322] Synthesis Example 15: Preparation of Compound 219

[0323]

[0324] Following the same preparation method as compound 97 in Synthesis Example 8, c-1 and d-97 were replaced with equimolar amounts of b-219 and d-219, respectively, to obtain compound 219 (16.06 g). HPLC analysis showed a solid purity ≥99.92%. Mass spectrometry m / z: 677.2145 (theoretical value: 677.2135). Theoretical elemental content (%) C 44 H 31 N3O3Si: C, 77.97; H, 4.61; N, 6.20. Measured elemental content (%): C, 77.92; H, 4.58; N, 6.16.

[0325] Synthesis Example 16: Preparation of Compound 229

[0326]

[0327] Following the same preparation method as compound 1 in Example 4, b-1, c-1, and d-1 were replaced with equimolar amounts of b-229, c-229, and d-219, respectively, to obtain compound 229 (17.19 g). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 763.3038 (theoretical value: 763.3019). Theoretical elemental content (%) C 53 H 41 N3OSi: C, 83.32; H, 5.41; N, 5.50. Measured elemental content (%): C, 83.35; H, 5.37; N, 5.55.

[0328] Synthesis Example 17: Preparation of Compound 240

[0329]

[0330] Following the same preparation method as compound 97 in Example 8, c-1 and d-97 were replaced with equimolar amounts of b-240 and d-240, respectively, to obtain compound 240 (17.63 g). HPLC analysis showed a solid purity ≥99.97%. Mass spectrometry m / z: 793.3224 (theoretical value: 793.3237). Theoretical elemental content (%) C 53 H 43 N5OSi: C, 80.17; H, 5.46; N, 8.82. Measured elemental content (%): C, 80.22; H, 5.43; N, 8.79.

[0331] Synthesis Example 18: Preparation of Compound 242

[0332]

[0333] Following the same preparation method as compound 97 in Example 8, c-1 and d-97 were replaced with equimolar amounts of b-242 and d-242, respectively, to obtain compound 242 (14.53 g). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 597.2227 (theoretical value: 597.2236). Theoretical elemental content (%) C 40 H 31 N3OSi: C, 80.37; H, 5.23; N, 7.03. Measured elemental content (%): C, 80.40; H, 5.27; N, 7.05.

[0334] Synthesis Example 19: Preparation of Compound 247

[0335]

[0336] Following the same preparation method as compound 97 in Synthesis Example 8, c-1 and d-97 were replaced with equimolar amounts of b-247 and d-247, respectively, to obtain compound 247 (16.33 g). HPLC analysis showed a solid purity ≥99.91%. Mass spectrometry m / z: 697.2567 (theoretical value: 697.2549). Theoretical elemental content (%) C 48 H 35 N3OSi: C, 82.61; H, 5.06; N, 6.02. Measured elemental content (%): C, 82.59; H, 5.10; N, 6.06.

[0337] Synthesis Example 20: Preparation of Compound 251

[0338]

[0339] Following the same preparation method as compound 97 in Example 8, c-1 and d-97 were replaced with equimolar amounts of b-251 and d-242, respectively, to obtain compound 251 (16.22 g). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 675.2219 (theoretical value: 675.2230). Theoretical elemental content (%) C 46 H 33 NO3Si: C, 81.75; H, 4.92; N, 2.07. Measured elemental content (%): C, 81.71; H, 4.88; N, 2.10.

[0340] Synthesis Example 21: Preparation of Compound 264

[0341]

[0342] Following the same preparation method as compound 97 in Synthesis Example 8, c-1 and d-97 were replaced with equimolar amounts of b-264 and d-242, respectively, to obtain compound 264 (17.10 g). HPLC analysis showed a solid purity ≥99.97%. Mass spectrometry m / z: 749.2871 (theoretical value: 749.2862). Theoretical elemental content (%) C 52 H 39 N3OSi: C, 83.28; H, 5.24; N, 5.60. Measured elemental content (%): C, 83.30; H, 5.28; N, 5.57.

[0343] Synthesis Example 22: Preparation of Compound 291

[0344]

[0345] Following the same preparation method as compound 97 in Synthesis Example 8, c-1 and d-97 were replaced with equimolar amounts of b-291 and d-291, respectively, to obtain compound 291 (15.16 g). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 673.2530 (theoretical value: 673.2549). Theoretical elemental content (%) C 46 H 35 N3OSi: C, 81.99; H, 5.24; N, 6.24. Measured elemental content (%): C, 81.95; H, 5.27; N, 6.19.

[0346] Synthesis Example 23: Preparation of Compound 301

[0347]

[0348] Following the same preparation method as compound 97 in Example 8, c-1 and d-97 were replaced with equimolar amounts of b-301 and d1-301, respectively, to obtain compound 301 (17.83 g). HPLC analysis showed a solid purity ≥99.98%. Mass spectrometry m / z: 836.2110 (theoretical value: 836.2100). Theoretical elemental content (%) C 53 H 36 N4OS2Si: C, 76.05; H, 4.33; N, 6.69. Measured elemental content (%): C, 76.01; H, 4.29; N, 6.72.

[0349] Synthesis Example 24: Preparation of Compound 316

[0350]

[0351] Following the same preparation method as compound 97 in Synthesis Example 8, c-1 and d-97 were replaced with equimolar amounts of b-316 and d1-316, respectively, to obtain compound 316 (19.10 g). HPLC analysis showed a solid purity ≥99.92%. Mass spectrometry m / z: 883.2382 (theoretical value: 883.2399). Theoretical elemental content (%) C 60 H 41 NOS2Si: C, 81.50; H, 4.67; N, 1.58. Measured elemental content (%): C, 81.46; H, 4.71; N, 1.60.

[0352] Synthesis Example 25: Preparation of Compound 368

[0353]

[0354] Following the same preparation method as compound 97 in Synthesis Example 8, c-1 and d-97 were replaced with equimolar amounts of b-368 and d-368, respectively, to obtain compound 368 (16.55 g). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 787.1886 (theoretical value: 787.1896). Theoretical elemental content (%) C 48 H 33 N5OS2Si: C, 73.16; H, 4.22; N, 8.89. Measured elemental content (%): C, 73.20; H, 4.18; N, 8.92.

[0355] Synthesis Example 26: Preparation of Compound 379

[0356]

[0357] Following the same preparation method as compound 97 in Synthesis Example 8, c-1 and d-97 were replaced with equimolar amounts of b-379 and d1-379, respectively, to obtain compound 379 (18.14 g). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 888.2981 (theoretical value: 888.2994). Theoretical elemental content (%) C 63 H 44 N₂SSi: C, 85.10; H, 4.99; N, 3.15. Measured elemental content (%): C, 85.06; H, 4.96; N, 3.19.

[0358] Synthesis Example 27: Preparation of Compound 390

[0359]

[0360] Following the same preparation method as compound 97 in Synthesis Example 8, a-97, c-1, and d-97 were replaced with equimolar amounts of a-390, b-242, and d-106, respectively, to obtain compound 390 (13.99 g). HPLC analysis showed a solid purity ≥99.91%. Mass spectrometry m / z: 597.2252 (theoretical value: 597.2236). Theoretical elemental content (%) C 40 H 31 N3OSi: C, 80.37; H, 5.23; N, 7.03. Measured elemental content (%): C, 80.40; H, 5.18; N, 7.07.

[0361] Synthesis Example 28: Preparation of Compound 433

[0362]

[0363] Following the same preparation method as compound 97 in Synthesis Example 8, c-1 and d-97 were replaced with equimolar amounts of b-433 and d-433, respectively, to obtain compound 433 (18.74 g). HPLC analysis showed a solid purity ≥99.97%. Mass spectrometry m / z: 843.2863 (theoretical value: 843.2852). Theoretical elemental content (%) C 56 H 41 N5SSi: C, 79.68; H, 4.90; N, 8.30. Measured elemental content (%): C, 79.70; H, 4.86; N, 8.27.

[0364] Synthesis Example 29: Preparation of Compound 435

[0365]

[0366] Following the same preparation method as compound 97 in Synthesis Example 8, a-97, c-1, and d-97 were replaced with equimolar amounts of a-435, b-435, and d-433, respectively, to obtain compound 435 (17.85 g). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 887.3022 (theoretical value: 887.3002). Theoretical elemental content (%) C 59 H 45 N3O2SSi: C, 79.79; H, 5.11; N, 4.73. Measured elemental content (%): C, 79.82; H, 5.07; N, 4.76.

[0367] Synthesis Example 30: Preparation of Compound 436

[0368]

[0369] Following the same preparation method as compound 97 in Synthesis Example 8, c-1 and d-97 were replaced with equimolar amounts of b-436 and d-436, respectively, to obtain compound 436 (17.81 g). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 812.2665 (theoretical value: 812.2681). Theoretical elemental content (%) C 57 H 40 N₂SSi: C, 84.20; H, 4.96; N, 3.45. Measured elemental content (%): C, 84.16; H, 4.93; N, 3.48.

[0370] Synthesis Example 31: Preparation of Compound 445

[0371]

[0372] Following the same preparation method as compound 97 in Example 8, a-97, c-1, and d-97 were replaced with equimolar amounts of a-106, b-445, and d-445, respectively, to obtain compound 445 (15.57 g). HPLC analysis showed a solid purity ≥99.98%. Mass spectrometry m / z: 691.2234 (theoretical value: 691.2226). Theoretical elemental content (%) C 44 H 33 N5SSi: C, 76.38; H, 4.81; N, 10.12. Measured elemental content (%): C, 76.42; H, 4.79; N, 10.16.

[0373] Synthesis Example 32: Preparation of Compound 453

[0374]

[0375] Following the same preparation method as compound 97 in Synthesis Example 8, c-1 and d-97 were replaced with equimolar amounts of b-453 and d-453, respectively, to obtain compound 453 (19.17 g). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 899.2771 (theoretical value: 899.2790). Theoretical elemental content (%) C 63 H 41 N3SSi: C, 84.06; H, 4.59; N, 4.67. Measured elemental content (%): C, 84.10; H, 4.62; N, 4.63.

[0376] Synthesis Example 33: Preparation of Compound 467

[0377]

[0378] Following the same preparation method as compound 97 in Example 8, c-1 and d-97 were replaced with equimolar amounts of b-467 and d-467, respectively, to obtain compound 467 (18.84 g). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 909.2713 (theoretical value: 909.2701). Theoretical elemental content (%) C 58 H 47 N3S3Si: C, 76.53; H, 5.20; N, 4.62. Measured elemental content (%): C, 76.49; H, 5.23; N, 4.59.

[0379] Synthesis Example 34: Preparation of Compound 507

[0380]

[0381] Following the same preparation method as compound 97 in Synthesis Example 8, c-1 and d-97 were replaced with equimolar amounts of b-507 and d-507, respectively, to obtain compound 507 (17.14 g). HPLC analysis showed a solid purity ≥99.97%. Mass spectrometry m / z: 771.2781 (theoretical value: 771.2790). Theoretical elemental content (%) C 50 H 33 D4N5SSi: C, 77.79; H, 5.35; N, 9.07. Measured elemental content (%): C, 77.82; H, 5.30; N, 9.11.

[0382] Synthesis Example 35: Preparation of Compound 511

[0383]

[0384] Following the same preparation method as compound 97 in Synthesis Example 8, c-1 and d-97 were replaced with equimolar amounts of b-511 and d1-511, respectively, to obtain compound 511 (17.67 g). HPLC analysis showed a solid purity ≥99.92%. Mass spectrometry m / z: 817.2454 (theoretical value: 817.2471). Theoretical elemental content (%) C 56 H 39 NO2SSi: C, 82.22; H, 4.81; N, 1.71. Measured elemental content (%): C, 82.19; H, 4.77; N, 1.75.

[0385] Synthesis Example 36: Preparation of Compound 555

[0386]

[0387] Following the same preparation method as compound 97 in Synthesis Example 8, c-1 and d-97 were replaced with equimolar amounts of c-555 and d1-555, respectively, to obtain compound 555 (18.53 g). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 845.3519 (theoretical value: 845.3509). Theoretical elemental content (%) C 59 H 51 NOSi2: C, 83.74; H, 6.07; N, 1.66. Measured elemental content (%): C, 83.78; H, 6.10; N, 1.61.

[0388] Synthesis Example 37: Preparation of Compound 578

[0389]

[0390] Following the same preparation method as compound 97 in Synthesis Example 8, c-1 and d-97 were replaced with equimolar amounts of c-578 and d-578, respectively, to obtain compound 578 (16.25 g). HPLC analysis showed a solid purity ≥99.91%. Mass spectrometry m / z: 721.2679 (theoretical value: 721.2693). Theoretical elemental content (%) C 45 H 39 N5OSi2: C, 74.86; H, 5.44; N, 9.70. Measured elemental content (%): C, 74.89; H, 5.40; N, 9.66.

[0391] Synthesis Example 38: Preparation of Compound 670

[0392]

[0393] Following the same preparation method as compound 97 in Synthesis Example 8, c-1 and d-97 were replaced with equimolar amounts of c-670 and d-670, respectively, to obtain compound 670 (18.26 g). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 844.3436 (theoretical value: 844.3418). Theoretical elemental content (%) C 57 H 48 N4Si2: C, 81.00; H, 5.72; N, 6.63. Measured elemental content (%): C, 81.05; H, 5.69; N, 6.67.

[0394] Synthesis Example 39: Preparation of Compound 191

[0395]

[0396] Following the same preparation method as compound 97 in Synthesis Example 8, c-1 and d-97 were replaced with equimolar amounts of c-127 and d-191, respectively, to obtain compound 191 (15.39 g). HPLC analysis showed a solid purity ≥99.98%. Mass spectrometry m / z: 667.2745 (theoretical value: 667.2727). Theoretical elemental content (%) C 45 H 41 NOSi2: C, 80.91; H, 6.19; N, 2.10. Measured elemental content (%): C, 80.93; H, 6.15; N, 2.13.

[0397] Synthesis Example 40: Preparation of Compound 223

[0398]

[0399] Following the same preparation method as compound 97 in Synthesis Example 8, c-1 and d-97 were replaced with equimolar amounts of c-223 and d-219, respectively, to obtain compound 223 (18.63 g). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 827.3566 (theoretical value: 827.3583). Theoretical elemental content (%) C 60 H 49 NOSi: C, 87.02; H, 5.96; N, 1.69. Measured elemental content (%): C, 87.05; H, 5.93; N, 1.73.

[0400] Device Examples

[0401] The following examples, 1-106 and 1-4, detail the application effects of the OLED material synthesized in this invention in organic electroluminescent devices.

[0402] Test methods: Driving voltage and luminous efficiency were tested using a combined IVL testing system consisting of testing software, a computer, a Keithley K2400 digital source meter, and a Photo Research PR788 spectral scanning luminance meter. Lifetime was tested using a McScience M6000 OLED lifetime testing system. The test environment was atmospheric, at room temperature.

[0403] The materials used in fabricating the organic electroluminescent device and the contrast device are shown below:

[0404]

[0405]

[0406] Device Example 1: Fabrication of a Green Organic Light Emitting Device

[0407] The ITO / Ag / ITO glass substrate was ultrasonically cleaned twice with a 5% glass cleaning solution for 20 minutes each time, followed by ultrasonic cleaning twice with deionized water for 10 minutes each time. It was then ultrasonically cleaned sequentially with acetone and isoacetone for 20 minutes each time, and dried at 120°C. All organic materials were sublimated and had a purity of over 99.99%. A mixture of HI-P and HT-1 (HI-P:HT-1 mass ratio = 3:97) was vacuum-deposited on the ITO / Ag / ITO glass substrate as a hole injection layer with a thickness of 10 nm. A 120 nm thick layer of HT-1 was vacuum-deposited on the hole injection layer as a hole transport layer. A 30 nm thick layer of EB-1 was vacuum-deposited on the hole transport layer as an electron blocking layer. Finally, a mixture of compound 1, GH-1, and GD-1 (compound 1:GH-1:GD-1 mass ratio) was deposited on the electron blocking layer. =47:47:6) to form a light-emitting layer with a deposition thickness of 40nm. Then, a mixture of ET-1 and Liq (ET-1:Liq mass ratio = 1:1) is vacuum-deposited on the light-emitting layer as an electron transport layer with a deposition thickness of 30nm. Then, Yb with a deposition thickness of 1nm is deposited as an electron injection layer. On the electron injection layer, a Mg:Ag alloy (Mg:Ag mass ratio = 1:9) is vacuum-deposited as a cathode with a deposition thickness of 15nm. Then, CP-1 is vacuum-deposited on the cathode as a light extraction layer with a deposition thickness of 70nm.

[0408] Device Examples 2 to 35:

[0409] The fabrication processes of Device Embodiments 2 to 35 of the present invention are completely identical to those of Device Embodiment 1, and the same substrate material, electrode material, and other organic functional layer materials are used. The film thickness of the electrode material and other organic functional layer materials is also kept consistent. The difference is that the main material of the light-emitting layer in the device is replaced. Accordingly, Compound 1 in Device Embodiment 1 is replaced with Compound 30, Compound 45, Compound 71, Compound 97, Compound 106, Compound 113, Compound 127, Compound 143, Compound 204, Compound 215, Compound 219, Compound 229, Compound 240, Compound 242, Compound 247, Compound 251, Compound 264, Compound 291, Compound 301, Compound 316, Compound 368, Compound 379, Compound 390, Compound 433, Compound 435, Compound 436, Compound 445, Compound 453, Compound 467, Compound 507, Compound 511, Compound 555, Compound 578, and Compound 670.

[0410] Comparative device example 1:

[0411] The manufacturing process of Comparative Device Example 1 is exactly the same as that of Device Example 1, and the same substrate material, electrode material and other organic functional layer materials are used. The film thickness of the electrode material and other organic functional layer materials is also kept consistent. The difference is that the main material of the light-emitting layer in the device is replaced, and correspondingly, Comparative Compound 1 is used to replace Compound 1 in Device Example 1.

[0412] Table 1: Test data on the luminescence characteristics of organic electroluminescent devices prepared in Device Examples 1-35 and Comparative Device Example 1

[0413]

[0414]

[0415] As can be seen from the results in Table 1, compared with the comparative devices, when the compound provided by the present invention is used as the main material of the light-emitting layer, the balance of electron and hole transport can be balanced, the injection barrier of holes and electrons can be reduced, and the organic electroluminescent device can have a lower driving voltage, higher luminous efficiency and longer service life.

[0416] Device Example 36: Fabrication of a Blue Organic Light Emitting Device

[0417] The ITO glass substrate was ultrasonically cleaned twice with a 5% glass cleaning solution for 20 minutes each time, followed by ultrasonic cleaning twice with deionized water for 10 minutes each time. It was then ultrasonically cleaned sequentially with acetone and isoacetone for 20 minutes each, and dried at 120°C. All organic materials were sublimated and had a purity of over 99.99%. A 10nm thick hole injection layer of a mixture of HI-P and HT-1 (HI-P:HT-1 mass ratio = 3:97) was vacuum-deposited onto the ITO glass substrate. A 120nm thick HT-1 layer was then vacuum-deposited onto the hole injection layer as a hole transport layer. A 10nm thick EB-2 layer was then vacuum-deposited onto the hole transport layer as an electron blocking layer. Finally, a 97:3 thick mixture of BH-1 and BD-1 was deposited onto the electron blocking layer. A light-emitting layer is formed with a deposition thickness of 25 nm. Then, compound 1 of the present invention with a thickness of 10 nm is vacuum-deposited on the light-emitting layer as a hole-blocking layer. Then, a mixture of ET-1 and Liq (ET-1:Liq mass ratio = 1:1) is vacuum-deposited on the hole-blocking layer as an electron transport layer with a deposition thickness of 35 nm. LiF is vacuum-deposited on the electron transport layer as an electron injection layer with a deposition thickness of 1 nm. Al is vacuum-deposited on the electron injection layer as a cathode with a thickness of 150 nm.

[0418] Device Examples 36 to 70:

[0419] Device Examples 36 to 70 of the present invention are fabricated in the same way as Device Example 36, and use the same substrate material, electrode material, and other organic functional layer materials. The film thickness of the electrode material and other organic functional layer materials is also kept consistent. The difference is that the hole blocking layer material in the device is replaced. Accordingly, compound 1 in Device Example 36 is replaced with compound 30, compound 45, compound 71, compound 97, compound 106, compound 113, compound 127, compound 143, compound 204, compound 215, compound 219, compound 229, compound 240, compound 242, compound 247, compound 251, compound 264, compound 291, compound 301, compound 316, compound 368, compound 379, compound 390, compound 433, compound 435, compound 436, compound 445, compound 453, compound 467, compound 507, compound 511, compound 555, compound 578, and compound 670.

[0420] Comparative device example 2:

[0421] The fabrication processes of Comparative Device Example 1 and Device Example 36 are exactly the same, and the same substrate material, electrode material and other organic functional layer materials are used. The film thickness of the electrode material and other organic functional layer materials is also consistent. The difference is that the hole blocking layer material in the device is replaced, and correspondingly, Comparative Compound 1 is used to replace Compound 1 in Device Example 36.

[0422] Table 2: Test data on the luminescence characteristics of the organic electroluminescent devices prepared in Device Examples 36-70 and Comparative Device Example 2

[0423]

[0424]

[0425] As shown in Table 2, compared with the comparative devices, when the compound provided by the present invention is used as the hole blocking layer material, it can effectively block the escape to the electron transport layer side, and at the same time reduce the electron transport barrier, so that the transport of electrons and holes can be balanced, thereby enabling the organic electroluminescent device to have a lower driving voltage, higher luminous efficiency and longer service life.

[0426] Device Example 71: Fabrication of a Blue Organic Light Emitting Device

[0427] A 10 nm thick layer of a mixture of HI-P and HT-1 (HI-P:HT-1 mass ratio = 3:97) was vacuum-deposited onto a cleaned and dried ITO glass substrate. A 120 nm thick layer of HT-1 was then vacuum-deposited onto the hole injection layer as a hole transport layer. A 10 nm thick layer of EB-2 was then vacuum-deposited onto the hole transport layer as an electron blocking layer. Finally, a 97:3 thick layer of a mixture of BH-1 and BD-1 was deposited onto the electron blocking layer. A light-emitting layer is formed in this way, with a deposition thickness of 25 nm. Then, HB-1 with a thickness of 10 nm is vacuum-deposited on the light-emitting layer as a hole-blocking layer. Then, a mixture of compound 1 of the present invention and Liq (mass ratio of compound 1 to Liq of the present invention = 1:1) is vacuum-deposited on the hole-blocking layer as an electron transport layer with a deposition thickness of 35 nm. LiF is vacuum-deposited on the electron transport layer as an electron injection layer with a deposition thickness of 1 nm. Al is vacuum-deposited on the electron injection layer as a cathode with a thickness of 150 nm.

[0428] Device Examples 72 to 96:

[0429] Compound 1 in Device Example 71 was replaced with compounds 30, 71, 97, 106, 113, 127, 204, 215, 219, 223, 229, 240, 242, 251, 264, 316, 368, 390, 433, 436, 445, 453, 467, 507, and 670, and devices 72 to 96 were prepared using the exact same preparation process as Device Example 71.

[0430] Comparative device example 3:

[0431] Comparative device 3 was prepared by replacing compound 1 in device example 71 with comparative compound 1 and using the exact same process.

[0432] Table 3: Test data on the luminescence characteristics of the organic electroluminescent devices prepared in Device Examples 71-96 and Comparative Device Example 3

[0433]

[0434]

[0435] As shown in Table 3, compared with the comparative devices, the compound provided by this invention has a higher electron transport rate and a suitable HOMO energy level when used as the electron transport layer material. This reduces the electron transport barrier and balances the transport of electrons and holes, resulting in organic electroluminescent devices with lower driving voltage, higher luminous efficiency, and longer lifespan.

[0436] Device Example 97: Fabrication of a Green Organic Light Emitting Device

[0437] A 10 nm thick hole injection layer was formed by vacuum evaporating a mixture of HI-P and HT-1 (HI-P:HT-1 mass ratio = 3:97) onto a cleaned and dried ITO / Ag / ITO glass substrate. A 130 nm thick layer of HT-1 was then vacuum evaporated onto the hole injection layer as a hole transport layer. Finally, a 47:47:6 thick mixture of GH-2, GH-1, and GD-1 was deposited onto the hole transport layer to form the light-emitting layer. The evaporation thickness of the light-emitting layer is 35 nm. Then, a mixture of ET-1 and Liq (ET-1:Liq mass ratio = 1:1) is vacuum-evaporated on the light-emitting layer as an electron transport layer with a evaporation thickness of 30 nm. Then, Yb with a thickness of 1 nm is vacuum-evaporated as an electron injection layer. On the electron injection layer, a Mg:Ag alloy (Mg:Ag mass ratio = 1:9) is vacuum-evaporated as a cathode with a evaporation thickness of 15 nm. Then, compound 106 of the present invention is vacuum-evaporated on the cathode as a light extraction layer with a evaporation thickness of 70 nm.

[0438] Device Examples 98 to 106:

[0439] Replace compound 106 in device example 96 with compounds 191, 219, 242, 251, 301, 316, 435, 507, and 511, and prepare devices 97 to 105 using the same preparation process as device example 96.

[0440] Comparative device example 4:

[0441] Comparative device 4 was prepared by replacing compound 106 in device example 97 with comparative compound 2, using the same fabrication process as device example 97.

[0442] Table 4: Test data on the luminescence characteristics of the organic electroluminescent devices prepared in Device Examples 97-106 and Comparative Device Example 4

[0443]

[0444] As can be seen from the results in Table 4, compared with the comparative device 4, the fused heterocyclic compound provided by the present invention has a higher refractive index, which can couple out the light inside the organic electroluminescent device, improve the light extraction efficiency, and at the same time isolate water and oxygen, thus extending the lifespan.

[0445] It should be noted that the present invention has been specifically described with reference to individual embodiments, but those skilled in the art can make various forms or details of improvements to the present invention without departing from the principles of the present invention, and these improvements also fall within the protection scope of the present invention.

Claims

1. A fused heterocyclic compound, characterized in that, The fused heterocyclic compound is selected from the following structures: In Equation I, the " "Selected from any one of the following groups:" ； The p4 is independently selected from 1, 2, 3, 4, 5, 6, or 7; The R2 is independently selected from any one of hydrogen, deuterium, and tritium; The R0 is independently selected from any one of substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted pyridyl, and A group; the substituent represented by "substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted pyridyl" is selected from: deuterium, tritium, and cyano; X0 is selected from O, S or N (R3); The R3 is selected from any one of substituted or unsubstituted C6-C12 aryl groups; the substituent represented by "substituted or unsubstituted C6-C12 aryl groups" is selected from: deuterium and tritium; The L0 is selected from a single bond or one of the following groups: ； The L1 and L2 are independently selected from single bonds or one of the following groups: ； Rx is independently selected from any one of hydrogen, deuterium, and tritium; Rx' is independently selected from any one of hydrogen, deuterium, and tritium; The n1 is independently selected from 1, 2, 3 or 4, and the n2 is independently selected from 1, 2 or 3; The Ar1 and Ar2 are independently selected from any one of the following groups: ； The a1 is independently selected from 1, 2, 3, 4, or 5; the a2 is independently selected from 1, 2, 3, or 4; the a3 is independently selected from 1, 2, or 3; the a4 is independently selected from 1 or 2; the a5 is independently selected from 1, 2, 3, 4, 5, 6, or 7; the a9 is independently selected from 1, 2, 3, 4, 5, or 6; the a 10 The independent selection is from 1, 2, 3, 4, 5, 6, 7, or 8; The R4 is independently selected from any one of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, and tert-butyl. The R 7a Independently selected from any one of hydrogen, deuterium, or A groups; The R 7b Independently selected from any one of hydrogen, deuterium, and phenyl; The R7 is independently selected from either hydrogen or deuterium; The R 10 'Selected from any one of phenyl, biphenyl, and naphthyl;' The R 10 Independently selected from any one of hydrogen, deuterium, tritium, methyl, and deuterated methyl; R1 is independently selected from any one of hydrogen, deuterium, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, and tert-butyl; The m is selected from 1, 2, or 3; The condition is that the structure of Formula I contains one or two A groups, and R0 is selected from A groups or the R of Ar1. 7a One of the R groups selected from A group and Ar2 is said to be R. 7a One or more of the R groups are selected from A groups or Ar2. 7a One of the R groups selected from A and Ar1 7a One or more of the elements are selected from group A; A is represented by the group described in Formula II: In Formula II, Ra, Rb, and Rc are independently selected from any one of unsubstituted or deuterated methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, and phenyl. The L3 is selected from any one of a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted naphthylene, or a substituted or unsubstituted pyridylene, and the L3 in the A group of Ar1 and Ar2 is selected from a single bond; the substituent represented by "substituted or unsubstituted phenylene, a substituted or unsubstituted naphthylene, or a substituted or unsubstituted pyridylene" is selected from deuterium and tritium.

2. The fused heterocyclic compound according to claim 1, characterized in that, The group represented by Formula II is selected from any one of the following groups: 。 3. The fused heterocyclic compound according to claim 1, characterized in that, The Ar1 and Ar2 are independently selected from any one of the following groups: 。 4. The fused heterocyclic compound according to claim 1, characterized in that, The L0 is selected from a single bond or at least one of the following groups: 。 5. The fused heterocyclic compound according to claim 1, characterized in that, The fused heterocyclic compound is selected from any one of the following structures: 。 6. An organic electroluminescent device, comprising an anode, a cathode, and an organic layer, characterized in that, The organic layer comprises at least one of the fused heterocyclic compounds according to any one of claims 1 to 5.

7. An organic electroluminescent device according to claim 6, characterized in that, The organic layer includes a light-emitting layer, the light-emitting layer includes a host material, and the host material includes at least one of the fused heterocyclic compounds according to any one of claims 1 to 5.

8. An organic electroluminescent device according to claim 6, characterized in that, The organic layer comprises at least one of an electron transport layer or a hole blocking layer, wherein the at least one of the electron transport layer or hole blocking layer comprises at least one of the fused heterocyclic compounds according to any one of claims 1 to 5.

Images