A compound comprising a fused aromatic ring and an organic electroluminescent device thereof

Abstract

The application provides a compound containing a fused aromatic ring and an organic electroluminescent device thereof, and relates to the technical field of organic optoelectronic materials. In order to solve the problems of low luminous efficiency, high driving voltage, short service life and the like of an organic electroluminescent device caused by unbalanced electron and hole transport, the application provides a compound containing a fused aromatic ring. The compound has excellent electron transport property, a high triplet energy level, suitable HOMO and LUMO energy levels, is conducive to electron transport, makes the hole and electron transport balanced, can reduce the electron transport barrier, and improves the recombination probability of the electron and the hole. Meanwhile, the compound has a high refractive index, can improve the light extraction efficiency of the device, and improve the luminous efficiency of the device. Meanwhile, the compound contains a large conjugated group, the rigidity is enhanced, the glass transition temperature of the material is improved, the thermal stability is enhanced, and the compound is not easy to crystallize. When the compound is applied to an organic electroluminescent device, the service life of the device can be improved.

Description

TECHNICAL FIELD

[0001] The present application relates to the technical field of organic optoelectronic materials, in particular to a compound containing a fused aromatic ring and an organic electroluminescent device thereof. BACKGROUND

[0002] Organic Light Emitting Diode (OLED) is considered as a very potential new generation display technology due to its self-emitting, wide viewing angle, fast response speed, high definition, high brightness, good flexibility and many other advantages, and is deeply researched. The organic electroluminescent element is a self-emitting element using the following principle: under the action of an external electric field, holes generated by an anode material and electrons generated by a cathode material are transported into an organic light-emitting layer, and then recombine to form an exciton; the exciton transfers energy to an organic light-emitting molecule in the light-emitting layer, and the molecule jumps from a ground state to an excited state due to the energy; the molecule in the excited state returns to the ground state in a radiative transition manner, and energy is released in the form of light energy in the transition process, resulting in electroluminescence.

[0003] It has the following structure: an anode, a cathode and an organic material layer between the two. In order to improve the efficiency and stability of the organic electroluminescent element, the organic material layer usually includes multiple layers with different materials, such as a hole injection layer (HIL), a hole transport layer (HTL), a light-emitting layer, an electron transport layer (ETL) and an electron injection layer (EIL). The electron transport layer is a key component in the OLED structure, and the materials currently used in the electron transport layer usually contain electron-withdrawing groups such as pyridine, pyrimidine, triazine, imidazole and other nitrogen-containing heterocycles with electron transport properties, but the electron mobility of general organic materials is low, while the hole mobility is relatively high, which causes an imbalance between electrons and holes inside the light-emitting device, and holes tend to escape to the side of the electron transport layer, resulting in high driving voltage, low luminous efficiency, poor stability, short service life and other problems of the device. At the same time, the current organic electroluminescent device has low light extraction efficiency, and light is totally reflected at the interface, resulting in low luminous efficiency.

[0004] Therefore, it is a technical problem to be solved in the art that a high-mobility electron transport / hole blocking material capable of blocking holes, a high-refractive-index cover layer material capable of improving light extraction efficiency, thereby reducing the driving voltage of the organic electroluminescent device, improving the luminous efficiency and prolonging the service life are developed. SUMMARY

[0005] In order to solve the above problems, the present application provides a compound containing a fused ring and an organic electroluminescent device thereof, which can effectively improve the driving voltage, luminous efficiency and service life of the organic electroluminescent device. Specifically, the technical scheme of the present application is as follows:

[0006] The present application provides a kind of compound comprising fused aromatic ring, the compound comprising fused aromatic ring has the structure shown in formula 1:

[0007]

[0008] In formula 1, the A is selected from the group shown in formula 1-1 or formula 1-2:

[0009]

[0010] The Z is independently selected from any one of single bond, O atom, S atom, C (R2) (R3), N (R z ) ;

[0011] The R2, R3 is independently selected from any one of hydrogen, deuterium, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl; or any one of R2, R3 is directly bonded with E1; or R2, R3 can be connected to form a substituted or unsubstituted ring;

[0012] The R z is independently selected from any one of hydrogen, deuterium, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl; or adjacent two R z Between them can be connected to form a substituted or unsubstituted ring;

[0013] The R4 is independently selected from any one of hydrogen, deuterium, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl;

[0014] The n2 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; when n2 is greater than 1, two or more R4 are the same or different, or adjacent two R4 form a substituted or unsubstituted ring;

[0015] The E1, E2 is independently selected from any one of the following groups:

[0016]

[0017] R5is independently selected from any one of hydrogen, deuterium, cyano, substituted or unsubstituted C1-C12alkyl, substituted or unsubstituted C3-C12cycloalkyl, substituted or unsubstituted C6-C30aryl, substituted or unsubstituted C2-C30heteroaryl; or two adjacent R5are linked to form a substituted or unsubstituted ring;

[0018] m1is independently selected from 0, 1, 2, 3, 4, 5, 6, m2is independently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8, m3is independently selected from 0, 1, 2, 3 or 4, m4is independently selected from 0, 1 or 2, and m5is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10;

[0019] X is independently selected from a C atom or a N atom;

[0020] Y is independently selected from an O atom or an S atom;

[0021] L1and L2are independently selected from any one of a single bond, substituted or unsubstituted C6-C30arylene, substituted or unsubstituted C2-C30heteroarylene;

[0022] R1is independently selected from any one of hydrogen, deuterium, cyano, substituted or unsubstituted C1-C12alkyl, substituted or unsubstituted C3-C12cycloalkyl, substituted or unsubstituted C6-C30aryl, substituted or unsubstituted C2-C30heteroaryl;

[0023] n1is independently selected from 0, 1, 2, 3, 4 or 5.

[0024] The present application also provides an organic electroluminescent device comprising an anode, a cathode, and an organic layer between or outside at least one of the anode and the cathode, wherein the organic layer comprises any one or more of the compounds comprising a fused aromatic ring according to the present application.

[0025] Advantages

[0026] The compound containing a condensed aromatic ring according to the present invention has excellent electron transport properties, which is conducive to the transmission of electrons. The compound containing a condensed aromatic ring has a higher triplet energy level and suitable HOMO and LUMO energy levels, so that the energy levels of adjacent functional layers are more matched, electron transport is easier, and the driving voltage of the organic electroluminescent device can be effectively reduced. At the same time, holes can also be blocked in the luminescent layer, thereby increasing the recombination probability of electrons and holes, and improving the luminous efficiency of the organic electroluminescent device. The compound containing a condensed aromatic ring according to the present invention has increased conjugation, enhanced rigidity, increased glass transition temperature of the material, enhanced thermal stability, and is not easy to crystallize. When applied to an organic electroluminescent device, the life of the device can be increased. At the same time, the compound containing a condensed aromatic ring has a higher refractive index. When applied to the covering layer of an organic electroluminescent device, the light extraction efficiency of the device can be improved, and the luminous efficiency of the device can be improved. More preferably, when the condensed aromatic ring compound is used in combination with the triarylamine derivative provided by the present invention, carrier transport is balanced, excitons are effectively recombinated, a synergistic effect is achieved, and the luminous efficiency of the organic electroluminescent device is higher. DETAILED DESCRIPTION

[0027] The following will be a clear and complete description of the technical solutions of the specific embodiments of the present invention. Obviously, the embodiments described are only part of the embodiments of the present invention, not all of them. Based on the embodiments of the present invention, all other embodiments obtained by those skilled in the art without making any creative efforts shall fall within the scope of protection of the present invention.

[0028] In the compounds of the present invention, any atom not designated as a specific isotope is included as any stable isotope of that atom, and includes the atom at both its natural isotopic abundance and unnatural abundance.

[0029] In this specification, "*" means a portion connected to another substituent. "*" can be connected to any optional position of the connected group / fragment. Can be represented And so on.

[0030] Examples of the halogen atom according to the present invention may include fluorine, chlorine, bromine and iodine.

[0031] The alkyl group described in the present invention refers to a monovalent group obtained by removing a hydrogen atom from an alkane molecule. It can be a straight-chain alkyl group or a branched-chain alkyl group, preferably having 1 to 15 carbon atoms, more preferably 1 to 12 carbon atoms, and particularly preferably 1 to 6 carbon atoms. The alkyl group can be substituted or unsubstituted. Specific examples include, but are not limited to, methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, undecyl, dodecyl, isopropyl, isobutyl, sec-butyl, tert-butyl, and isopentyl.

[0032] The cycloalkyl group according to the present application refers to a monovalent group obtained by removing one hydrogen atom from a cyclic alkane molecule, preferably having 3 to 18 carbon atoms, more preferably 3 to 12 carbon atoms, and particularly preferably 3 to 6 carbon atoms. The cycloalkyl group can be substituted or unsubstituted. Specific examples can include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, and the like, but are not limited thereto.

[0033] The aryl group according to the present application refers to a monovalent group obtained by removing one hydrogen atom from an aromatic carbon of an aromatic compound molecule, which can be a monocyclic aryl group, a polycyclic aryl group, or a fused ring aryl group, preferably having 6 to 60 carbon atoms, more preferably 6 to 30 carbon atoms, particularly preferably 6 to 18 carbon atoms, and most preferably 6 to 12 carbon atoms. The aryl group includes a monocyclic aryl group, a polycyclic aryl group, or a fused ring aryl group, and the like. The aryl group can be substituted or unsubstituted. Specific examples can include phenyl, biphenyl, terphenyl, quaterphenyl, 1-phenylnaphthyl, 2-phenylnaphthyl, naphthyl, anthryl, phenanthryl, pyrenyl, perylenyl, fluorenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9-methyl-9-phenylfluorenyl, benzofluorenyl, triphenylenyl, fluoranthenyl, 9,9'-spirobifluorenyl, and the like, but are not limited thereto.

[0034] The heteroaryl group according to the present application refers to a general term for a group obtained by replacing one or more aromatic carbon atoms in an aryl group with a heteroatom, including but not limited to oxygen, sulfur, nitrogen, silicon, or phosphorus atoms, preferably having 2 to 60 carbon atoms, more preferably 2 to 30 carbon atoms, particularly preferably 2 to 18 carbon atoms, and most preferably 2 to 12 carbon atoms. The attachment site of the heteroaryl group can be on a ring-forming carbon atom or on a ring-forming heteroatom. The heteroaryl group can be a monocyclic heteroaryl group, a polycyclic heteroaryl group, or a fused ring heteroaryl group, and the like. The heteroaryl group can be substituted or unsubstituted. Specific examples can include pyridyl, pyrimidyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, thiophenyl, pyrrolyl, oxazolyl, thiazolyl, imidazolyl, bipyridyl, bipyrimidyl, phenylpyridyl, phenylpyrimidyl, quinolyl, isoquinolyl, benzoquinolyl, benzoisoquinolyl, quinazolyl, quinoxalyl, benzoquinazolyl, benzoquinoxalyl, phenanthroline, naphthylidene, indolyl, benzothiophenyl, benzofuranyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, naphthofuranyl, phenanthrofuranyl, naphthothiophenyl, phenanthrothiophenyl, naphthoxazolyl, naphthimidazolyl, naphthothiazolyl, phenanthrooxazolyl, phenanthrothiazolyl, phenanthroimidazolyl, carbazolyl, benzocarbazolyl, acridyl, 9,10-dihydroacridyl, phenoxazinyl, phenothiazinyl, phenoxathiazinyl, spirofluorenoxanthrene, spirofluorenothiophene, and the like, but are not limited thereto.

[0035] The arylene group according to the present application means a group having two bonding sites, i.e., a divalent group, on an aryl group. They can apply the above-described explanation of the aryl group except that they are divalent groups, respectively.

[0036] The heteroarylene group according to the present application means a group having two bonding sites, i.e., a divalent group, on a heteroaryl group. They can apply the above-described explanation of the heteroaryl group except that they are divalent groups, respectively.

[0037] The "substituted" according to the present application, such as "substituted alkyl, substituted cycloalkyl, substituted aryl, substituted heteroaryl, substituted arylene, substituted heteroarylene" means independently mono- or poly-substituted with deuterium, cyano, nitro, halogen atom, substituted or unsubstituted C1 to C12 alkyl, substituted or unsubstituted C2 to C12 alkenyl, substituted or unsubstituted C3 to C12 cycloalkyl, substituted or unsubstituted C2 to C12 heterocycloalkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heteroaryl, substituted or unsubstituted C1 to C12 alkoxy, substituted or unsubstituted C1 to C12 alkylthio, substituted or unsubstituted C1 to C12 alkylamino, substituted or unsubstituted C6 to C30 aryloxy, substituted or unsubstituted C6 to C30 arylamino, and the like, but not limited thereto, or adjacent two substituents can be linked to form a ring. Preferably, mono- or poly-substituted with deuterium, fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, ethyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cyclopentadienyl, cyclohexadienyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, triphenylenyl, perylenyl, pyrenyl, benzyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9-methyl-9-phenylfluorenyl, 9,9'-spirobifluorenyl, diphenylamino, pyridyl, pyrimidyl, triazinyl, carbazolyl, acridinyl, furanyl, thienyl, benzofuranyl, benzothienyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, dibenzofuranyl, dibenzothienyl, phenothiazinyl, phenoxazinyl, indolyl, and the like, but not limited thereto.

[0038] The "linked to form a ring" according to the present application means that two groups are linked to each other by a chemical bond and optionally aromatized. The following is exemplified:

[0039]

[0040] In the present application, the ring formed by the connection can be an aromatic ring system, an aliphatic ring system or a ring system formed by the fusion of both, the ring formed by the connection can be a three-membered ring, a four-membered ring, a five-membered ring, a six-membered ring or a fused ring, and specific examples of the aromatic ring system formed can include benzene, naphthalene, fluorene, pyridine, quinoline, isoquinoline, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, phenanthrene, pyrene, but are not limited thereto; specific examples of the aliphatic ring system can include cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclobutene, cyclopentene, cyclohexene, etc., but are not limited thereto; and specific examples of the ring system formed by the fusion of both can include indene, benzocyclopentane, benzocyclohexane, benzocyclohexene, benzocyclobutane, benzocyclobutene, etc., but are not limited thereto.

[0041] The present application provides a compound comprising a fused ring, the compound comprising a fused aromatic ring having a structure represented by Formula 1:

[0042]

[0043] In Formula 1, the A is selected from a group represented by Formula 1-1 or Formula 1-2:

[0044]

[0045] The Z is independently selected from any one of a single bond, an O atom, an S atom, C(R2)(R3), N(R z ) and a hydrogen atom;

[0046] The R2and R3are independently selected from any one of a hydrogen atom, a deuterium atom, a cyano group, a substituted or unsubstituted C1 to C12 alkyl group, a substituted or unsubstituted C3 to C12 cycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, and a substituted or unsubstituted C2 to C30 heteroaryl group; or any one of the R2and R3is directly bonded to the E1; or the R2and R3may be connected to form a substituted or unsubstituted ring;

[0047] The R z are independently selected from any one of a hydrogen atom, a deuterium atom, a cyano group, a substituted or unsubstituted C1 to C12 alkyl group, a substituted or unsubstituted C3 to C12 cycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, and a substituted or unsubstituted C2 to C30 heteroaryl group; or adjacent two R z may be connected to form a substituted or unsubstituted ring;

[0048] The R4is independently selected from any one of a hydrogen atom, a deuterium atom, a cyano group, a substituted or unsubstituted C1 to C12 alkyl group, a substituted or unsubstituted C3 to C12 cycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, and a substituted or unsubstituted C2 to C30 heteroaryl group;

[0049] n2 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; when n2 is greater than 1, two or more R4are the same or different from each other, or adjacent two R4form a substituted or unsubstituted ring;

[0050] E1and E2are independently selected from any one of the following groups:

[0051]

[0052] R5is independently selected from any one of hydrogen, deuterium, cyano, substituted or unsubstituted C1-C12alkyl, substituted or unsubstituted C3-C12cycloalkyl, substituted or unsubstituted C6-C30aryl, substituted or unsubstituted C2-C30heteroaryl; or adjacent two R5are connected to form a substituted or unsubstituted ring;

[0053] m1is independently selected from 0, 1, 2, 3, 4, 5, or 6, m2is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8, m3is independently selected from 0, 1, 2, 3, or 4, m4is independently selected from 0, 1, or 2, and m5is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10;

[0054] X is independently selected from a C atom or an N atom;

[0055] Y is independently selected from an O atom or an S atom;

[0056] L1and L2are independently selected from any one of a single bond, substituted or unsubstituted C6-C30arylene, substituted or unsubstituted C2-C30heteroarylene;

[0057] R1is independently selected from any one of hydrogen, deuterium, cyano, substituted or unsubstituted C1-C12alkyl, substituted or unsubstituted C3-C12cycloalkyl, substituted or unsubstituted C6-C30aryl, substituted or unsubstituted C2-C30heteroaryl;

[0058] n1is independently selected from 0, 1, 2, 3, 4, or 5.

[0059] Preferably, A is selected from any one of the following groups:

[0060]

[0061] R6and R7are independently selected from any one of hydrogen, deuterium, cyano, substituted or unsubstituted C1-C12alkyl, substituted or unsubstituted C3-C12cycloalkyl, substituted or unsubstituted C6-C18aryl, substituted or unsubstituted C2-C18heteroaryl;

[0062] R8, R9, R 10 R 11 independently selected from any one or more of hydrogen, deuterium, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl;

[0063] said "substituted" group is selected from any one or more of deuterium, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl;

[0064] said n2 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8, said n3 is independently selected from 0, 1, 2, 3, 4, 5, 6, or 7, said pi is independently selected from 0, 1, 2, 3, or 4, said p2 is independently selected from 0, 1, 2, 3, 4, 5, or 6, said p3 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8, said p4 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10, said p5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, or 14, said p6 is selected from 0, 1, or 2, and said p7 is independently selected from 0, 1, 2, 3, 4, or 5.

[0065] R6, R7 are independently selected from any one of hydrogen, deuterium, methyl, ethyl, iso-propyl, n-propyl, n-butyl, iso-butyl, t-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornane, deuterated methyl, deuterated ethyl, deuterated iso-propyl, deuterated n-propyl, deuterated t-butyl, phenyl, biphenyl, terphenyl, deuterated phenyl, deuterated biphenyl, deuterated terphenyl, naphthyl, anthryl, phenanthryl, triphenylene, deuterated naphthyl, deuterated anthryl, deuterated phenanthryl, deuterated triphenylene, phenyl-naphthyl, naphthyl-phenyl, fluorenyl, dibenzofuranyl, dibenzothiophenyl, pyridyl, pyrimidyl, quinolyl, isoquinolyl, quinazolyl, quinoxalyl, deuterated pyridyl, deuterated pyrimidyl, deuterated quinolyl, deuterated isoquinolyl.

[0066] Preferably, the R4 is independently selected from hydrogen, deuterium, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, benzocyclopropyl, benzocyclobutane, benzocyclopentyl, benzocyclohexane, naphthyl, anthracenyl, phenanthrenyl, triphenylene, 9-phenylene, 1-phenylene, 2-phenylene, 3-phenylene, 4-phenylene, 5-phenylene, 6-phenylene, 7-phenylene, 8-phenylene, 9-phenylene, 10-phenylene, 11-phenylene, 12-phenylene, 13-phenylene, 14-phenylene, 15-phenylene, 16-phenylene, 17-phenylene, 18-phenylene, 19-phenylene, 21-phenylene, 22-phenylene, 23-phenylene, 24-phenylene, 25-phenylene, 26-phenylene, 27-phenylene, 28-phenylene, 29-phenylene, 30-phenylene, 31-phenylene, 32-phenylene, 33-phenylene, 34-phenylene, 35-phenylene, 36-phenylene, 37-phenylene, 38-phenylene, 39-phenylene, 40-phenylene, 41-phenylene, 42-phenylene, 43-phenylene, 44-phenylene, 45-phenylene, 46-phenylene, 47-phenylene, 48-phenylene, 49-phenylene, 50-phenylene, 51-phenylene, 52-phenylene, 53-phenylene, 54-phenylene, 55- , 9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9,9-spirobifluorenyl, 9-methyl-9-phenylfluorenyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, deuterated methyl, deuterated ethyl, deuterated n-propyl, deuterated isopropyl, deuterated n-butyl, deuterated isobutyl, deuterated tert-butyl, deuterated cyclopropyl, deuterated cyclobutyl, deuterated cyclopentyl alkyl, deuterated cyclohexyl, deuterated adamantyl, deuterated norbornyl, deuterated phenyl, deuterated biphenyl, deuterated terphenyl, deuterated benzocyclopropane, deuterated benzocyclobutane, deuterated benzocyclopentane, deuterated benzocyclohexane, deuterated naphthyl, deuterated anthracenyl, deuterated phenanthryl, deuterated triphenylene, deuterated 9,9-dimethylfluorenyl, deuterated 9,9-diphenylfluorenyl, deuterated 9,9-spiro Any one of difluorenyl, deuterated 9-methyl-9-phenylfluorenyl, deuterated pyridinyl, deuterated pyrimidinyl, deuterated pyrazinyl, deuterated pyridazinyl, deuterated quinolyl, deuterated isoquinolyl, deuterated quinoxalinyl, deuterated quinazolinyl, pyridyl-phenyl, phenyl-pyridinyl, or any one of two adjacent R4 connected to form a substituted or unsubstituted benzene ring, a five-membered aliphatic ring, or a six-membered aliphatic ring;

[0067] More preferably, the A is independently selected from any one of the following groups:

[0068]

[0069]

[0070]

[0071]

[0072] Preferably, E1 and E2 are independently selected from any one of the following groups:

[0073]

[0074] R5 is independently selected from hydrogen, deuterium, cyano, or substituted or unsubstituted methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, benzocyclopropyl, benzocyclobutyl, benzocyclopentyl, benzocyclohexyl, benzocycloheptyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, pyridyl, pyrimidinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, benzoxazolyl, benzothiazolyl, fluorenyl, dibenzofuranyl, and dibenzothiophenyl;

[0075] The "substituted" group is selected from any one or more of deuterium, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl.

[0076] Preferably, the Any one selected from the following groups:

[0077]

[0078]

[0079] Preferably, L1 and L2 are independently selected from a single bond or any one of the following groups:

[0080]

[0081] Most preferably, the compound comprising a fused aromatic ring is selected from any one of the following structures:

[0082]

[0083]

[0084]

[0085]

[0086]

[0087]

[0088]

[0089]

[0090]

[0091]

[0092]

[0093]

[0094]

[0095] The above lists some specific structural forms of the compound of formula 1 according to the present application, but the present application is not limited to the listed chemical structures, and any structure based on the structure of formula 1 and having substituents as defined above should be included.

[0096] The present application also provides an organic electroluminescent device comprising an anode, a cathode, and an organic layer between the anode and the cathode or outside at least one of the anode and the cathode, wherein the organic layer comprises any one or more of the compounds containing a fused aromatic ring according to the present application.

[0097] Preferably, the organic electroluminescent device according to the present application can comprise one or more organic layers, which can comprise a light-emitting layer, a hole-injection layer, a hole-transport layer, an electron-transport layer, an electron-injection layer, a hole-blocking layer, an electron-blocking layer, a cover layer, and the like. Specifically, the organic layer between the anode and the cathode can comprise a light-emitting layer, a hole-injection layer, a hole-transport layer, an electron-transport layer, an electron-injection layer, a hole-blocking layer, an electron-blocking layer, and the like, and the organic layer outside at least one of the anode and the cathode can comprise a cover layer, and the like.

[0098] Preferably, the organic layer comprises at least one of a hole-blocking layer, an electron-transport layer, or a cover layer, and the at least one of a hole-blocking layer, an electron-transport layer, or a cover layer comprises any one or more of the compounds containing a fused aromatic ring according to the present application.

[0099] More preferably, the organic layer is between the anode and the cathode, and the organic layer comprises at least one of a hole-blocking layer or an electron-transport layer, and the at least one of a hole-blocking layer or an electron-transport layer comprises any one or more of the compounds containing a fused aromatic ring according to the present application.

[0100] More preferably, the organic layer comprises an electron-transport layer, and the electron-transport layer comprises any one or more of the compounds containing a fused aromatic ring according to the present application.

[0101] More preferably, the organic layer comprises a hole-blocking layer, and the hole-blocking layer comprises any one or more of the compounds containing a fused aromatic ring according to the present application.

[0102] Preferably, the organic layer is located outside of at least one of the anode and the cathode, and the organic layer comprises a capping layer, wherein the capping layer comprises any one or more of the compounds comprising fused aromatic rings according to the present application.

[0103] Preferably, the organic layer further comprises a hole transport layer, wherein the hole transport layer comprises a structure represented by Formula 2:

[0104]

[0105] The Araand the Arb are independently selected from any one of hydrogen, deuterium, a substituted or unsubstituted C1-C12 alkyl, a substituted or unsubstituted C3-C12 cycloalkyl, a substituted or unsubstituted C6-C30 aryl, and a substituted or unsubstituted C2-C30 heteroaryl;

[0106]

[0107] The Rd is independently selected from any one of hydrogen, deuterium, a substituted or unsubstituted C1-C12 alkyl, a substituted or unsubstituted C3-C12 cycloalkyl, a substituted or unsubstituted C6-C30 aryl, and a substituted or unsubstituted C2-C30 heteroaryl; or two adjacent Rd can be linked to form a substituted or unsubstituted ring;

[0108] The Re is independently selected from any one of hydrogen, deuterium, a substituted or unsubstituted C1-C12 alkyl, a substituted or unsubstituted C3-C12 cycloalkyl, a substituted or unsubstituted C6-C30 aryl, and a substituted or unsubstituted C2-C30 heteroaryl; or two Re can be linked to form a substituted or unsubstituted ring;

[0109] The d1 is independently selected from 0, 1, 2, 3, 4, or 5, the d2 is independently selected from 0, 1, 2, 3, or 4, and the d3 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8;

[0110] The Arc is selected from any one of a substituted or unsubstituted C6-C30 aryl and a substituted or unsubstituted C2-C30 heteroaryl; or the Arc is directly bonded to the Lc, and when directly bonded to the Lc, the Arc is selected from a single bond;

[0111] The Ra is independently selected from any one of hydrogen, deuterium, a substituted or unsubstituted C1-C12 alkyl, a substituted or unsubstituted C3-C12 cycloalkyl, a substituted or unsubstituted C6-C30 aryl, and a substituted or unsubstituted C2-C30 heteroaryl;

[0112] Rb is independently selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl; or adjacent two Rb can be linked to form a substituted or unsubstituted ring;

[0113] Rc is independently selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl; or adjacent two Rc can be linked to form a substituted or unsubstituted ring;

[0114] b1 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8, b2 is selected from 0, 1, 2 or 3, and b3 is selected from 0, 1, 2, 3 or 4;

[0115] La-Ld is independently selected from any one of single bond, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C2-C30 heteroarylene.

[0116] More preferably, the hole transport layer comprises at least one of a first hole transport layer or a second hole transport layer, and the at least one of the first hole transport layer or the second hole transport layer comprises the triarylamine derivative represented by Formula 2 of the present application.

[0117] More preferably, the first hole transport layer is located between the anode and the light-emitting layer, and the second hole transport layer is located between the first hole transport layer and the light-emitting layer.

[0118] Preferably, the hole transport layer comprises any one of the structures represented by Formula 2-1 to Formula 2-3:

[0119]

[0120] Rc is independently selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl; or adjacent two Rc can be linked to form a substituted or unsubstituted ring;

[0121] the "substituted" group is selected from any one or more of deuterium, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C18 aryl, substituted or unsubstituted C3-C18 cycloalkyl;

[0122] the b2 is independently selected from 0, 1, 2, or 3, the b3 is selected from 0, 1, 2, 3, or 4, and the b4 is selected from 0, 1, or 2.

[0123] Preferably, the is independently selected from any one of the following groups:

[0124]

[0125] the Re' is independently selected from any one of hydrogen, tritium, substituted or unsubstituted methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornane, phenyl, biphenyl, terphenyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, naphthyl, anthryl, phenanthryl, triphenylene, fluorenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl;

[0126] the "substituted" group is selected from any one or more of deuterium, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C18 aryl, substituted or unsubstituted C3-C18 cycloalkyl;

[0127] the Rf is independently selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl;

[0128] the d3 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8, the d4 is independently selected from 0, 1, 2, 3, 4, 5, 6, or 7, the d5 is independently selected from 0, 1, 2, 3, 4, 5, or 6, the d6 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10, and the d7 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, or 14.

[0129] Preferably, the Ara, Arb is independently selected from any one of the following groups:

[0130]

[0131]

[0132]

[0133] Preferably, said Ld is selected from any one of a single bond, phenylene, biphenylene, terphenylene, naphthylene, benzocyclopropanylene, benzocyclobutaniene, benzocyclopentaniene, benzocyclohexaniene, deutero-phenylene, deutero-biphenylene, deutero-terphenylene, deutero-naphthylene, deutero-benzocyclopropanylene, deutero-benzocyclobutaniene, deutero-benzocyclopentaniene, deutero-benzocyclohexaniene.

[0134] Preferably, said Lc is selected from any one of a single bond, substituted or unsubstituted:

[0135]

[0136] Said "substituted" group is selected from any one of deuterium, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, adamantyl, norbornyl, phenyl.

[0137] Preferably, said La, Lb are independently selected from any one of a single bond, phenylene, biphenylene, terphenylene, naphthylene, benzocyclopropanylene, benzocyclobutaniene, benzocyclopentaniene, benzocyclohexaniene, fluorenylene, phenanthrylene, phenylene-naphthylene, phenylene-benzocyclopropanylene, phenylene-benzocyclobutaniene, phenylene-benzocyclopentaniene, phenylene-benzocyclohexaniene, deutero-phenylene, deutero-biphenylene, deutero-terphenylene, deutero-naphthylene, deutero-benzocyclopropanylene, deutero-benzocyclobutaniene, deutero-benzocyclopentaniene, deutero-benzocyclohexaniene.

[0138] Said Arc is selected from any one of phenyl, biphenyl, terphenyl, naphthyl, anthryl, fluorenyl, phenanthryl, triphenylyl, benzocyclopropanyl, benzocyclobutanyl, benzocyclopentanyl, benzocyclohexanyl, dibenzofuranyl, dibenzothiophenyl, deutero-phenyl, methyl-substituted phenyl, i-propyl-substituted phenyl, t-butyl-substituted phenyl, adamantyl-substituted phenyl, norbornyl-substituted phenyl, deutero-biphenyl, methyl-substituted biphenyl, i-propyl-substituted biphenyl, t-butyl-substituted biphenyl, adamantyl-substituted biphenyl, norbornyl-substituted biphenyl, deutero-terphenyl, deutero-naphthyl, deutero-anthryl, deutero-fluorenyl, deutero-phenanthryl, deutero-triphenylyl, deutero-benzocyclopropanyl, deutero-benzocyclobutanyl, deutero-benzocyclopentanyl, deutero-benzocyclohexanyl, deutero-dibenzofuranyl, deutero-dibenzothiophenyl.

[0139] Most preferably, said triarylamine derivative of formula 2 is selected from any one of the following structures:

[0140]

[0141]

[0142]

[0143]

[0144]

[0145]

[0146]

[0147]

[0148]

[0149]

[0150]

[0151]

[0152] The above lists some specific structural forms of the compound of formula 2 according to the present application, but the present application is not limited to the listed chemical structures, and any structure based on the structure of formula 2 and having substituents as defined above should be included.

[0153] The material of each layer of thin film in the organic electroluminescent device according to the present application is not particularly limited, and any material known in the art can be used. The following describes each organic functional layer of the organic electroluminescent device mentioned above and the electrodes on both sides of the device:

[0154] As the anode material according to the present application, a material having a high work function is preferred. The material for forming the anode can be selected from indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), or any combination thereof; magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), or any combination thereof.

[0155] As the hole injection layer material according to the present application, a material having a high work function is preferred, and can be selected from any one or more of the following structures: metalloporphyrin, oligothiophene, arylamine derivative, perylene derivative, hexacyno hexaazatriphenylene compound, quinacridone compound, anthraquinone compound, and conductive polymer based on polyaniline and polysthiophene, but is not limited thereto.

[0156] As the hole transport layer material of the present application, a material having high hole mobility is preferred, and in addition to the triarylamine derivative represented by Formula 2 provided in the present application, a carbazole derivative, a triarylamine derivative, a diphenylamine derivative, a fluorene derivative, a stilbene derivative, a phthalocyanine compound, a hexacyno hexaazatriphenylene compound, a quinacridone compound, an anthraquinone compound, polyaniline, polythiophene, polyvinylcarbazole, or the like can be used, but is not limited thereto.

[0157] As the light emitting layer material of the present application, a host material can be included, and a guest (dopant) can be further optionally included, and in the case where the host and guest materials are included, the content of the host material can be in the range of 70 to 99.9 wt%, and the content of the guest material can be in the range of 0.1 to 30 wt%. As the host material, a material having a bipolar charge transport property is preferred, and at the same time, a proper energy level is required to effectively transfer excitation energy to the guest light emitting material, and specifically, an aluminum complex, a beryllium complex, an anthracene derivative, a pyrene derivative, a triphenylene derivative, a carbazole derivative, a diphenyl furan derivative, a diphenyl thiophene derivative, or a combination of one or more thereof can be used. The guest material can be selected from any one or several of the following structures: a metal complex (for example, an iridium complex, a platinum complex, an osmium complex, a rhodium complex, etc.), an anthracene derivative, a pyrene derivative, a perylene derivative, an arylamine derivative, etc., but is not limited thereto.

[0158] As the electron transport layer material of the present application, a material having high electron mobility is preferred, and in addition to the compound including a fused aromatic ring provided in the present application, a metal chelate, an oxazol derivative, a thiazol derivative, a diazol derivative, an azabenzene derivative, a diazanthracene derivative, a silicon-containing heterocyclic compound, a boron-containing heterocyclic compound, a cyano compound, a quinoline derivative, a phenanthroline derivative, a benzimidazole derivative, or the like can be used, but is not limited thereto.

[0159] As the hole blocking layer material of the present application, a material having a lower energy level, a wider band gap, and a hole blocking ability is preferred, and in addition to the compound including a fused aromatic ring provided in the present application, a phenanthroline derivative, a rare earth derivative, an oxazol derivative, a triazol derivative, a triazine derivative, or the like can be used, but is not limited thereto.

[0160] As the electron injection layer material of the present application, a material having a low work function is preferable, and specific examples can include: metals, alkali metals, alkaline earth metals, halides of alkali metals, halides of alkaline earth metals, oxides of alkali metals, oxides of alkaline earth metals, salts of alkali metals, salts of alkaline earth metals, metal complexes, other substances having high electron injection property. For example, Li, Ca, Sr, LiF, CsF, CaF2, BaO, Li2CO3, CaCO3, Li2C2O4, Cs2C2O4, CsAlF4, LiOx, Yb, Tb, cesium 8-hydroxyquinoline, tris(8-hydroxyquinoline)aluminum, etc., but not limited thereto.

[0161] As the cathode material of the present application, a material having a low work function is preferable, and the cathode can be selected from a transmissive electrode, a semi-reflective electrode, or a reflective electrode. When the cathode is a transmissive electrode, the material used to form the cathode can be selected from transparent metal oxides (e.g., ITO, IZO, etc.); when the cathode is a semi-reflective electrode or a reflective electrode, the material used to form the cathode can be selected from Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF / Ca, LiF / Al, Mo, Ti, compounds including the same, or mixtures thereof (e.g., a mixture of Ag and Mg), but not limited thereto.

[0162] As the cover layer material of the present application, any one or more of the following structures can be selected: inorganic compounds (e.g., metal oxides, metal nitrides, metal fluorides, etc.), organic compounds (arylamine derivatives, carbazole derivatives, benzimidazole derivatives, benzoxazole derivatives, benzothiazole derivatives, triazole derivatives, etc.), or mixtures of inorganic compounds and organic compounds, but not limited thereto.

[0163] The present application also provides a method for preparing a compound of Formula 1 or Formula 2, but the preparation method of the present application is not limited thereto. The core structure of the compound of Formula 1 or Formula 2 can be prepared by the following reaction scheme, the substituents can be bonded by methods known in the art, and the types and positions of the substituents or the number of the substituents can be changed according to techniques known in the art.

[0164] [Synthesis route of the compound of Formula 1]

[0165]

[0166] The above reactions involve two main reaction types: Suzuki-Miyaura reaction, Miyaura boronation reaction. Xa, Xb, Xc, Xd, Xe, Xf, Xg, Xh are independently selected from any one of I, Br, Cl.

[0167] In the above reaction, when L1is a single bond, the starting material a can be directly reacted with the starting material b to prepare the intermediate A; when L2is a single bond, the intermediate D can be directly reacted with the starting material d to prepare the compound of formula 1.

[0168] [Synthetic route of the compound of formula 2]

[0169]

[0170] The above reaction involves the main reaction type of Buchwald reaction, and Xmand Xnare independently selected from any one of I, Br and Cl.

[0171] Description of starting materials, reagents and characterization equipment:

[0172] The starting materials and reagents used in the following examples of the present application are not particularly limited and can be commercially available products or prepared by methods well known to those skilled in the art.

[0173] Mass spectrometry uses a Waters G2-Si quadrupole tandem time-of-flight high-resolution mass spectrometer in the United Kingdom, chloroform as the solvent;

[0174] Elemental analysis uses a Vario EL cube organic elemental analyzer of Elementar Company in Germany, and the sample mass is 5-10 mg.

[0175] [Synthesis Example 1] Preparation of compound 1

[0176]

[0177] Preparation of intermediate A-1:

[0178] The starting material a-1 (28.57 g, 120.00 mmol), the starting material b-1 (28.98 g, 120.00 mmol), Na2CO3 (25.44 g, 240.00 mmol), Pd(PPh3)4 (1.39 g, 1.20 mmol) and 600 mL of a mixed solvent of toluene / ethanol / water (2:1:1) were added to a reaction bottle. After nitrogen degassing for three times, the reaction was heated to reflux for 2 hours; after the reaction was completed, the reaction mixture was cooled to room temperature, and the filter cake was extracted and washed with ethanol, and finally the filter cake was recrystallized with toluene / ethanol = 20:3 to obtain the intermediate A-1 (37.05 g, yield 87%), HPLC purity ≥ 99.53%. Mass spectrometry m / z: 354.1186 (theoretical value: 354.1175).

[0179] Preparation of intermediate B-1:

[0180] Into a reaction flask was placed intermediate A-1 (33.71 g, 95.00 mmol), B2Pin2 (26.66 g, 105.00 mmol), KOAc (18.65 g, 190.00 mmol), Pd(dppf)Cl2 (0.84 g, 1.15 mmol), DMF (500 mL). After three times of nitrogen degassing, the reaction was heated for 3 hours; after the reaction was completed, the reaction mixture was allowed to cool to room temperature, distilled water was added thereto, and then extraction was performed with dichloromethane, the organic layer was dried with anhydrous magnesium sulfate, the solvent was removed by rotary evaporation, recrystallization was performed with ethyl acetate, and drying was performed to obtain intermediate B-1 (36.05 g, yield 85%), HPLC purity ≥ 99.82%. Mass spectrum m / z: 446.2430 (theoretical value: 446.2417).

[0181] Preparation of intermediate C-1

[0182] Into a reaction flask was placed intermediate B-1 (29.02 g, 65.00 mmol), raw material c-1 (18.95 g, 65.00 mmol), K2CO3 (17.97 g, 130.00 mmol), Pd(dppf)Cl2 (0.48 g, 0.65 mmol), and 350 mL of a mixed solvent of toluene / ethanol / water (2:1:1). After three times of nitrogen degassing, the reaction was heated to reflux for 3.5 hours; after the reaction was completed, the reaction mixture was allowed to cool to room temperature, filtration was performed to obtain a filter cake, the filter cake was washed with ethanol, and finally the filter cake was recrystallized with toluene / ethanol = 10:1 to obtain intermediate C-1 (27.87 g, yield 82%), HPLC purity ≥ 99.75%. Mass spectrum m / z: 530.1817 (theoretical value: 530.1801).

[0183] Preparation of intermediate D-1

[0184] Into a reaction flask was placed intermediate C-1 (23.90 g, 45.000 mmol), B2Pin2 (12.70 g, 50.00 mmol), KOAc (13.82 g, 100.00 mmol), Pd(dppf)Cl2 (0.40 g, 0.55 mmol), DMF (250 mL). After three times of nitrogen degassing, the reaction was heated for 4 hours; after the reaction was completed, the reaction mixture was allowed to cool to room temperature, distilled water was added thereto, and then extraction was performed with dichloromethane, the organic layer was dried with anhydrous magnesium sulfate, the solvent was removed by rotary evaporation, recrystallization was performed with ethyl acetate, and drying was performed to obtain intermediate D-1 (22.41 g, yield 80%), HPLC purity ≥ 99.87%. Mass spectrum m / z: 622.3055 (theoretical value: 622.3043).

[0185] Preparation of compound 1

[0186] Intermediate D-1 (13.07 g, 21.00 mmol), starting material d-1 (3.96 g, 20.00 mmol), K2CO3(5.53 g, 40.00 mmol), Pd2(dba)3(0.19 g, 0.21 mmol), P(t-Bu)3(0.14 g, 0.70 mmol) and 200 mL of toluene solvent were added into a reaction bottle, degassed with nitrogen for three times, and then heated to reflux for 5 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, and then filtered to obtain a filter cake which was washed with ethanol. Finally, the filter cake was recrystallized with toluene to obtain compound 1 (9.57 g, yield 78%). HPLC purity ≥ 99.98%. Mass spectrum m / z: 613.2421 (theoretical value: 613.2406). Theoretical elemental content (%) C 46 H 31 NO: C, 90.02; H, 5.09; N, 2.28. Measured elemental content (%): C, 89.98; H, 5.12; N, 2.31.

[0187] [Synthesis Example 2] Preparation of compound 7

[0188]

[0189] According to the method of Example 1, starting material a-1 was replaced with an equal mole of a-7, starting material b-1 was replaced with an equal mole of b-7, and starting material c-1 was replaced with an equal mole of c-7 to obtain compound 7 (9.85 g), HPLC detection solid purity ≧ 99.97%. Mass spectrum m / z: 639.2551 (theoretical value: 639.2562). Theoretical elemental content (%) C 48 H 33 NO: C, 90.02; H, 5.09; N, 2.28. Measured elemental content (%): C, 89.98; H, 5.12; N, 2.31.

[0190] [Synthesis Example 3] Preparation of compound 22

[0191]

[0192] According to the method of Example 1, starting material a-1 was replaced with an equal mole of a-22, starting material b-1 was replaced with an equal mole of b-7, and starting material c-1 was replaced with an equal mole of c-22 to obtain compound 22 (11.13 g), HPLC detection solid purity ≧ 99.94%. Mass spectrum m / z: 751.2528 (theoretical value: 751.2511). Theoretical elemental content (%) C 56 H 33NO2: C, 89.46; H, 4.42; N, 1.86. Found (%): C, 89.50; H, 4.37; N, 1.92.

[0193] [Synthesis Example 4] Preparation of Compound 30

[0194]

[0195] According to the method of Example 1, replacing raw material a-1 with equimolar a-30, raw material b-1 with equimolar b-30, compound 30 (11.47 g) was obtained with solid purity ≧ 99.93% detected by HPLC. Mass m / z: 785.2711 (theoretical value: 785.2719). Theoretical elemental content (%) C 60 H 35 NO2: C, 91.69; H, 4.49; N, 1.78. Found (%): C, 91.73; H, 4.55; N, 1.73.

[0196] [Synthesis Example 5] Preparation of Compound 51

[0197]

[0198] According to the method of Example 1, replacing raw material a-1 with equimolar a-51, raw material b-1 with equimolar b-30, raw material c-1 with equimolar c-22, raw material d-1 with equimolar d-51, compound 51 (12.27 g) was obtained with solid purity ≧ 99.80% detected by HPLC. Mass m / z: 863.3173 (theoretical value: 863.3188). Theoretical elemental content (%) C 66 H 41 NO2: C, 91.69; H, 4.49; N, 1.78. Found (%): C, 91.73; H, 4.55; N, 1.73.

[0199] [Synthesis Example 6] Preparation of Compound 56

[0200]

[0201] According to the method of Example 1, replacing raw material a-1 with equimolar a-56, raw material c-1 with equimolar c-56, compound 56 (10.56 g) was obtained with solid purity ≧ 99.95% detected by HPLC. Mass m / z: 703.2890 (theoretical value: 703.2875). Theoretical elemental content (%) C 53 H 37NO: C, 90.44; H, 5.30; N, 1.99. Found (%): C, 90.39; H, 5.27; N, 2.05.

[0202] [Synthesis Example 7] Preparation of Compound 60

[0203]

[0204] According to the method of Example 1, replacing raw material a-1 with equimolar a-60, raw material b-1 with equimolar b-60, and raw material c-1 with equimolar c-56, Compound 60 (10.22 g) was obtained with solid purity > 99.97% by HPLC. Mass m / z: 663.2576 (theoretical value: 663.2562). Theoretical elemental content (%) C 50 H 33 NO: C, 90.47; H, 5.01; N, 2.11. Found (%): C, 90.52; H, 4.97; N, 2.07.

[0205] [Synthesis Example 8] Preparation of Compound 64

[0206]

[0207] According to the method of Example 1, replacing raw material a-1 with equimolar a-64, raw material b-1 with equimolar b-7, and raw material c-1 with equimolar c-64, Compound 64 (11.18 g) was obtained with solid purity > 99.94% by HPLC. Mass m / z: 755.3204 (theoretical value: 755.3188). Theoretical elemental content (%) C 57 H 41 NO: C, 90.56; H, 5.47; N, 1.85. Found (%): C, 90.59; H, 5.52; N, 1.79.

[0208] [Synthesis Example 9] Preparation of Compound 71

[0209]

[0210] According to the method of Example 1, replacing raw material a-1 with equimolar a-71, raw material b-1 with equimolar b-71, and raw material c-1 with equimolar c-56, Compound 71 (11.92 g) was obtained with solid purity > 99.92% by HPLC. Mass m / z: 827.3176 (theoretical value: 827.3188). Theoretical elemental content (%) C 63 H 41C, 91.39; H, 4.99; N, 1.69. Found (%): C, 91.43; H, 5.02; N, 1.67.

[0211] [Synthesis Example 10] Preparation of Compound 90

[0212]

[0213] According to the method of Example 1, replacing starting material c-1 with equimolar of c-90, Compound 90 (9.82 g) was obtained with solid purity > 99.89% by HPLC. Mass m / z: 637.2419 (theoretical value: 637.2406). Theoretical elemental content (%) C 48 H 31 N2O2: C, 88.26; H, 4.27; N, 3.49. Found (%): C, 88.29; H, 4.23; N, 3.52.

[0214] [Synthesis Example 11] Preparation of Compound 98

[0215]

[0216] According to the method of Example 1, replacing starting material a-1 with equimolar of a-98, starting material b-1 with equimolar of b-98, starting material c-1 with equimolar of c-98, and starting material d-1 with equimolar of d-98, Compound 98 (11.56 g) was obtained with solid purity > 99.82% by HPLC. Mass m / z: 802.2640 (theoretical value: 802.2620). Theoretical elemental content (%) C 59 H 34 N2O2: C, 88.26; H, 4.27; N, 3.49. Found (%): C, 88.29; H, 4.23; N, 3.52.

[0217] [Synthesis Example 12] Preparation of Compound 105

[0218]

[0219] According to the method of Example 1, replacing starting material a-1 with equimolar of a-105, starting material b-1 with equimolar of b-7, starting material c-1 with equimolar of b-1, and starting material d-1 with equimolar of d-105, Compound 105 (9.70 g) was obtained with solid purity > 99.97% by HPLC. Mass m / z: 629.2647 (theoretical value: 629.2657). Theoretical elemental content (%) C 47 H 27D4NO: C, 88.58; H, 6.81; N, 2.15. Found: C, 88.62; H, 6.77; N, 2.20.

[0220] [Synthesis Example 13] Preparation of Compound 120

[0221]

[0222] According to the method of Example 1, replacing raw material a-1 with equimolar a-120, raw material b-1 with equimolar b-120, and raw material c-1 with equimolar b-7, Compound 120 (10.02 g) was obtained with solid purity > 99.98% by HPLC. Mass spectrum m / z: 650.3265 (theoretical value: 650.3253). Theoretical elemental content (%) C 48 H 22 D 11 NO: C, 88.58; H, 6.81; N, 2.15. Found: C, 88.62; H, 6.77; N, 2.20.

[0223] [Synthesis Example 14] Preparation of Compound 123

[0224]

[0225] According to the method of Example 1, replacing raw material a-1 with equimolar a-123, and raw material c-1 with equimolar b-1, Compound 123 (11.31 g) was obtained with solid purity > 99.94% by HPLC. Mass spectrum m / z: 763.2892 (theoretical value: 763.2875). Theoretical elemental content (%) C 58 H 37 NO: C, 91.19; H, 4.88; N, 1.83. Found: C, 91.25; H, 4.91; N, 1.77.

[0226] [Synthesis Example 15] Preparation of Compound 130

[0227]

[0228] According to the method of Example 1, replacing raw material a-1 with equimolar a-130, and raw material c-1 with equimolar b-1, Compound 130 (9.30 g) was obtained with solid purity > 99.99% by HPLC. Mass spectrum m / z: 588.2213 (theoretical value: 588.2202). Theoretical elemental content (%) C 43 H 28N2O: C, 87.73; H, 4.79; N, 4.76. Found (mass %): C, 87.69; H, 4.81; N, 4.79.

[0229] [Synthesis Example 16] Preparation of compound 146

[0230]

[0231] According to the method of Example 1, replacing raw material a-1 with an equal mole of a-146, raw material b-1 with an equal mole of b-1, and raw material c-1 with an equal mole of b-1, compound 146 (10.47 g) was obtained, which had a solid purity of > 99.96% as detected by HPLC. Mass spectrum m / z: 688.2533 (theoretical value: 688.2515). Theoretical elemental content (%) C 51 H 32 N2O: C, 88.93; H, 4.68; N, 4.07. Found (mass %): C, 88.97; H, 4.71; N, 4.05.

[0232] [Synthesis Example 17] Preparation of compound 173

[0233]

[0234] Preparation of intermediate a-173:

[0235] Raw material e-173 (42.03 g, 150.00 mmol), B2Pin2 (41.90 g, 165.00 mmol), KOAc (29.44 g, 300.00 mmol), Pd(dppf)Cl2 (1.61 g, 2.20 mmol), DMF (750 mL) were added to a reaction bottle. After nitrogen degassing three times, the reaction was heated for 2 hours; after the reaction was completed, the reaction mixture was cooled to room temperature, distilled water was added thereto, and then extracted with dichloromethane, and the organic layer was dried with anhydrous magnesium sulfate, the solvent was removed by rotary evaporation, recrystallized with ethyl acetate, and dried to obtain intermediate a-173 (43.69 g, yield 89%), which had a purity of > 99.86% as detected by HPLC. Mass spectrum m / z: 327.2399 (theoretical value: 327.2387).

[0236] Preparation of compound 173:

[0237] According to the method of Example 1, replacing raw material a-1 with an equal mole of intermediate a-173, raw material b-1 with an equal mole of b-7, and raw material c-1 with an equal mole of b-1, compound 173 (9.02 g) was obtained, which had a solid purity of > 99.99% as detected by HPLC. Mass spectrum m / z: 570.2702 (theoretical value: 570.2689). Theoretical elemental content (%) C42 H 22 D7NO: C, 88.39; H, 6.36; N, 2.45. Found (%): C, 88.43; H, 6.41; N, 2.39.

[0238] [Synthesis Example 18] Preparation of Compound 176

[0239]

[0240] According to the method of Example 1, replacing raw material a-1 with an equal mole of a-176, raw material b-1 with an equal mole of b-7, and raw material c-1 with an equal mole of c-176, Compound 176 (9.57 g) was obtained with a solid purity of > 99.98% by HPLC. Mass spectrum m / z: 613.2392 (theoretical value: 613.2406). Theoretical elemental content (%) C 46 H 31 NO: C, 90.02; H, 5.09; N, 2.28. Found (%): C, 89.97; H, 5.11; N, 2.33.

[0241] [Synthesis Example 19] Preparation of Compound 192

[0242]

[0243] According to the method of Example 1, replacing raw material a-1 with an equal mole of a-30, and raw material c-1 with an equal mole of b-30, Compound 192 (10.89 g) was obtained with a solid purity of > 99.94% by HPLC. Mass spectrum m / z: 735.2571 (theoretical value: 735.2562). Theoretical elemental content (%) C 56 H 33 NO: C, 91.40; H, 4.52; N, 1.90. Found (%): C, 91.36; H, 4.55; N, 1.87.

[0244] [Synthesis Example 20] Preparation of Compound 196

[0245]

[0246] According to the method of Example 1, replacing raw material a-1 with an equal mole of a-196, raw material b-1 with an equal mole of b-30, and raw material c-1 with an equal mole of b-1, Compound 196 (10.49 g) was obtained with a solid purity of > 99.96% by HPLC. Mass spectrum m / z: 689.2711 (theoretical value: 689.2719). Theoretical elemental content (%) C 52 H 35C, 90.54; H, 5.11; N, 2.03. Found (%): C, 90.59; H, 5.08; N, 1.99.

[0247] [Synthesis Example 21] Preparation of compound 197

[0248]

[0249] According to the method of Example 1, replacing raw material a-1 with equimolar a-197, 7 raw material c-1 with equimolar b-30, compound 197 (10.64 g) was obtained with solid purity > 99.97% detected by HPLC. Mass spectrum m / z: 690.2687 (theoretical value: 690.2671). Theoretical elemental content (%) C 51 H 34 N2O: C, 88.67; H, 4.96; N, 4.06. Found (%): C, 88.61; H, 5.01; N, 4.11.

[0250] [Synthesis Example 22] Preparation of compound 201

[0251]

[0252] According to the method of Example 1, replacing raw material b-1 with equimolar b-30, raw material c-1 with equimolar c-98, and raw material d-1 with equimolar d-201, compound 201 (9.59 g) was obtained with solid purity > 99.98% detected by HPLC. Mass spectrum m / z: 614.2367 (theoretical value: 614.2358). Theoretical elemental content (%) C 45 H 30 N2O: C, 87.92; H, 4.92; N, 4.56. Found (%): C, 87.89; H, 4.87; N, 4.61.

[0253] [Synthesis Example 23] Preparation of compound 250

[0254]

[0255] According to the method of Example 1, replacing raw material a-1 with equimolar a-250, raw material b-1 with equimolar b-30, and raw material c-1 with equimolar b-30, compound 250 (12.04 g) was obtained with solid purity > 99.92% detected by HPLC. Mass spectrum m / z: 835.2863 (theoretical value: 835.2875). Theoretical elemental content (%) C 64 H 37C, 90.69; H, 5.88; N, 1.60. Found: C, 90.72; H, 5.92; N, 1.56.

[0256] [Synthesis Example 24] Preparation of Compound 269

[0257]

[0258] According to the method of Example 1, substituting starting material a-1 with an equivalent of a-269, starting material b-1 with an equivalent of b-1, starting material c-1 with an equivalent of b-1, and starting material d-1 with an equivalent of d-269, Compound 269 (10.50 g) was obtained with a solid purity of > 99.97% by HPLC. Mass spectrum m / z: 690.2685 (theoretical value: 690.2671). Theoretical elemental content (%) C 51 H 34 N2O: C, 88.67; H, 4.96; N, 4.06. Found: C, 88.71; H, 4.93; N, 4.10.

[0259] [Synthesis Example 25] Preparation of Compound 281

[0260]

[0261] According to the method of Example 1, substituting starting material a-1 with an equivalent of a-281, starting material b-1 with an equivalent of b-60, starting material c-1 with an equivalent of b-60, and starting material d-1 with an equivalent of d-281, Compound 281 (12.41 g) was obtained with a solid purity of > 99.91% by HPLC. Mass spectrum m / z: 873.3987 (theoretical value: 873.3971). Theoretical elemental content (%) C 66 H 51 NO: C, 90.69; H, 5.88; N, 1.60. Found: C, 90.72; H, 5.92; N, 1.56.

[0262] [Synthesis Example 26] Preparation of Compound 283

[0263]

[0264] According to the method of Example 1, substituting starting material a-1 with an equivalent of a-283, starting material c-1 with an equivalent of b-1, and starting material d-1 with an equivalent of d-283, Compound 283 (12.15 g) was obtained with a solid purity of > 99.93% by HPLC. Mass spectrum m / z: 843.2609 (theoretical value: 843.2596). Theoretical elemental content (%) C 62 H 37NOS: C, 88.23; H, 4.42; N, 1.66. Found (%): C, 88.19; H, 4.38; N, 1.72.

[0265] [Synthesis Example 27] Preparation of compound 307

[0266]

[0267] According to the method of Example 1, replacing starting material a-1 with an equivalent of a-283, starting material b-1 with an equivalent of b-1, starting material c-1 with an equivalent of b-64, and starting material d-1 with an equivalent of d-283, compound 307 (9.56 g) was obtained with a solid purity of > 99.98% as measured by HPLC. Mass spectrum m / z: 604.1961 (theoretical value: 604.1973). Theoretical elemental content (%) C 43 H 28 N2S: C, 85.40; H, 4.67; N, 4.63. Found (%): C, 85.37; H, 4.73; N, 4.57.

[0268] [Synthesis Example 28] Preparation of compound 432

[0269]

[0270] According to the method of Example 1, replacing starting material a-1 with an equivalent of a-432, starting material b-1 with an equivalent of b-7, starting material c-1 with an equivalent of b-64, and starting material d-1 with an equivalent of d-432, compound 432 (12.70 g) was obtained with a solid purity of > 99.75% as measured by HPLC. Mass spectrum m / z: 893.3101 (theoretical value: 893.3116). Theoretical elemental content (%) C 67 H 43 NS: C, 90.00; H, 4.85; N, 1.57. Found (%): C, 89.96; H, 4.90; N, 1.61.

[0271] [Synthesis Example 29] Preparation of compound 439

[0272]

[0273] According to the method of Example 1, replacing intermediate B-1 with an equivalent of B-201, starting material c-1 with an equivalent of c-56, and starting material d-1 with an equivalent of d-432, compound 439 (10.95 g) was obtained with a solid purity of > 99.95% as measured by HPLC. Mass spectrum m / z: 729.2509 (theoretical value: 729.2490). Theoretical elemental content (%) C 54 H35 NS: C, 88.86; H, 4.83; N, 1.92. Found ( % ) : C, 88.91; H, 4.77; N, 1.89.

[0274] [Synthesis Example 30] Preparation of compound 444

[0275]

[0276] According to the method of Example 1, the starting material a-1 was replaced with equimolar a-444, the starting material b-1 was replaced with equimolar c-56, and the starting material d-1 was replaced with equimolar d-432 to obtain compound 444 (11.77 g) with a solid purity of > 99.94% detected by HPLC. Mass spectrum m / z: 805.2791 (theoretical value: 805.2803). Theoretical elemental content (%) C 60 H 39 NS: C, 89.41; H, 4.88; N, 1.74. Found ( % ) : C, 89.37; H, 4.92; N, 1.77.

[0277] [Synthesis Example 31] Preparation of compound 2-1

[0278]

[0279] Synthesis intermediate M-2-1:

[0280] Under the protection of nitrogen, m-2-1 (9.31 g, 100.00 mmol), n-2-1 (20.71 g, 100.00 mmol), Pd2(dba)3 (0.93 g, 1.00 mmol), BINAP (1.88 g, 3.00 mmol), sodium tert-butoxide (19.22 g, 200.00 mmol), and 450 mL of toluene solvent were sequentially added into a reaction bottle, stirred and dissolved, and the reaction was refluxed under the protection of nitrogen for 7 hours. After the reaction was completed, it was cooled to room temperature, filtered through diatomite to obtain a filtrate, and then the solvent was concentrated by reduced pressure distillation, and recrystallized with methanol to obtain intermediate M-2-1 (18.42 g, yield 84%) with a solid purity of > 99.66% detected by HPLC. Mass spectrum m / z: 219.1060 (theoretical value: 219.1048).

[0281] Synthesis of compound 2-1:

[0282] To a reaction flask, under nitrogen protection, were added q-2-1 (33.75 g, 60.00 mmol), intermediate M-2-1 (13.16 g, 60.00 mmol), Pd2(dba)3(0.82 g, 0.90 mmol), BINAP (1.68 g, 2.7 mmol), sodium tert-butoxide (17.30 g, 180.00 mmol), and 400 mL of toluene solvent, stirred to dissolve, and refluxed for 8 hours under nitrogen protection. After the reaction was completed, it was cooled to room temperature, filtered through diatomite to obtain a filtrate, then the solvent was concentrated by reduced pressure distillation, recrystallized with ethyl acetate, and finally compound 2-1 (34.48 g, yield 82%) was obtained, with a solid purity of > 99.72% detected by HPLC. Mass spectrum m / z: 700.2858 (theoretical value: 700.2878). Theoretical elemental content (%) 53 H 36 N2: C, 90.83; H, 5.18; N, 4.00. Measured elemental content (%): C, 90.79; H, 5.16; N, 4.04.

[0283] [Synthesis Example 32] Preparation of compound 2-17

[0284]

[0285] Using the same preparation method as in Synthesis Example 31, except that m-2-1 was replaced with an equal molar amount of m-2-17, n-2-1 was replaced with an equal molar amount of n-2-17, and q-2-1 was replaced with an equal molar amount of q-2-17, compound 2-17 (38.06 g) was synthesized, with a solid purity of > 99.67% detected by HPLC. Mass spectrum m / z: 802.3380 (theoretical value: 802.3348). Theoretical elemental content (%) 61 H 42 N2: C, 91.24; H, 5.27; N, 3.49. Measured elemental content (%): C, 91.19; H, 5.22; N, 3.51.

[0286] [Synthesis Example 33] Preparation of compound 2-33

[0287]

[0288] Using the same preparation method as in Synthesis Example 31, except that m-2-1 was replaced with an equal molar amount of m-2-17, n-2-1 was replaced with an equal molar amount of n-2-33, and q-2-1 was replaced with an equal molar amount of q-2-17, compound 2-33 (39.91 g) was synthesized, with a solid purity of > 99.65% detected by HPLC. Mass spectrum m / z: 842.3629 (theoretical value: 842.3657). Theoretical elemental content (%)64 H 46 N2: C, 91.18; H, 5.50; N, 3.32. Found (mass %): C, 91.23; H, 5.52; N, 3.29.

[0289] [Synthesis Example 34] Preparation of compound 2-41

[0290]

[0291] Using the same preparation method as in Synthesis Example 31, except that m-2-1 was replaced with equimolar of m-2-17, n-2-1 was replaced with equimolar of n-2-41, and q-2-1 was replaced with equimolar of q-2-17, compound 2-41 (44.86 g) was synthesized, which had a solid purity of > 99.39% as detected by HPLC. Mass m / z: 966.3942 (theoretical value: 966.3974). Theoretical elemental content (%) C 74 H 50 N2: C, 91.89; H, 5.21; N, 2.90. Found (mass %): C, 91.93; H, 5.19; N, 2.95.

[0292] [Synthesis Example 35] Preparation of compound 2-64

[0293]

[0294] Using the same preparation method as in Synthesis Example 31, except that m-2-1 was replaced with equimolar of m-2-64, n-2-1 was replaced with equimolar of n-2-64, and q-2-1 was replaced with equimolar of q-2-64, compound 2-64 (42.02 g) was synthesized, which had a solid purity of > 99.44% as detected by HPLC. Mass m / z: 912.4425 (theoretical value: 912.4443). Theoretical elemental content (%) C 69 H 56 N2: C, 90.75; H, 6.18; N, 3.07. Found (mass %): C, 90.72; H, 6.21; N, 3.03.

[0295] [Synthesis Example 36] Preparation of compound 2-91

[0296]

[0297] Using the same preparation method as in synthesis example 31, except that m-2-1 was replaced with equimolar of m-2-116, n-2-1 was replaced with equimolar of n-2-33, q-2-1 was replaced with equimolar of q-2-91, compound 2-116 (44.12 g) was synthesized, with solid purity > 99.68% by HPLC. Mass spectrum m / z: 918.3950 (theoretical value: 918.3974). Theoretical elemental content (%) C 70 H 50 N2: C, 91.47; H, 5.48; N, 3.05. Found elemental content (%) : C, 91.53; H, 5.51; N, 3.00.

[0298] [Synthesis Example 37] Preparation of compound 2-96

[0299]

[0300] Using the same preparation method as in synthesis example 31, except that m-2-1 was replaced with equimolar of m-2-96, n-2-1 was replaced with equimolar of n-2-96, q-2-1 was replaced with equimolar of q-2-91, compound 2-96 (44.89 g) was synthesized, with solid purity > 99.61% by HPLC. Mass spectrum m / z: 1010.4622 (theoretical value: 1010.4600). Theoretical elemental content (%) C 77 H 58 N2: C, 91.45; H, 5.78; N, 2.77. Found elemental content (%) : C, 91.46; H, 5.80; N, 2.74.

[0301] [Synthesis Example 38] Preparation of compound 2-99

[0302]

[0303] Using the same preparation method as in synthesis example 31, except that m-2-1 was replaced with equimolar of m-2-99, n-2-1 was replaced with equimolar of n-2-99, q-2-1 was replaced with equimolar of q-2-91, compound 2-99 (47.26 g) was synthesized, with solid purity > 99.53% by HPLC. Mass spectrum m / z: 966.3988 (theoretical value: 966.3974). Theoretical elemental content (%) C 74 H 50 N2: C, 91.89; H, 5.21; N, 2.90. Found elemental content (%) : C, 91.85; H, 5.25; N, 2.92.

[0304] [Synthesis Example 39] Preparation of compound 2-116

[0305]

[0306] Using the same preparation method as in Synthesis Example 31, except that n-2-1 was replaced with an equivalent molar amount of n-2-136, q-2-1 was replaced with an equivalent molar amount of q-2-136, compound 2-136 (46.39 g) was synthesized, and the solid purity was > 99.63% as determined by HPLC. Mass spectrum m / z: 842.3685 (theoretical value: 842.3661). Theoretical elemental content (%) C 75 H 62 N2: C, 90.87; H, 6.30; N, 2.83. Measured elemental content (%) C, 90.84; H, 6.27; N, 2.86.

[0307] [Synthesis Example 40] Preparation of compound 2-136

[0308]

[0309] Using the same preparation method as in Synthesis Example 31, except that n-2-1 was replaced with an equivalent molar amount of n-2-136, q-2-1 was replaced with an equivalent molar amount of q-2-136, compound 2-136 (46.39 g) was synthesized, and the solid purity was > 99.63% as determined by HPLC. Mass spectrum m / z: 842.3685 (theoretical value: 842.3661). Theoretical elemental content (%) C 64 H 46 N2: C, 91.18; H, 5.50; N, 3.32. Measured elemental content (%) C, 91.15; H, 5.52; N, 3.28.

[0310] [Synthesis Example 41] Preparation of compound 2-145

[0311]

[0312] Using the same preparation method as in Synthesis Example 31, except that n-2-1 was replaced with an equivalent molar amount of n-2-145, q-2-1 was replaced with an equivalent molar amount of q-2-145, compound 2-145 (41.63 g) was synthesized, and the solid purity was > 99.73% as determined by HPLC. Mass spectrum m / z: 900.4458 (theoretical value: 900.4443). Theoretical elemental content (%) C 68 H 56 N2: C, 90.63; H, 6.26; N, 3.11. Measured elemental content (%) C, 90.66; H, 6.22; N, 3.15.

[0313] Preparation of compound 2-150

[0314]

[0315] Preparation of q-2-150:

[0316] Under nitrogen protection, raw material q-2-17 (56.25 g, 100.00 mmol), raw material p-2-150 (15.64 g, 100.00 mmol), K2CO3 (27.64 g, 200.00 mmol), Pd(PPh3)4 (1.16 g, 1.00 mmol) and 400 mL of a mixed solvent of toluene / ethanol / water (2:1:1) were added to a reaction bottle. After nitrogen degassing for three times, the reaction was heated to reflux for 3 hours; after the reaction was completed, the reaction mixture was cooled to room temperature, and the filter cake was extracted and washed with ethanol, and finally the filter cake was recrystallized with toluene to obtain q-2-150 (48.72 g, yield 82%), and the HPLC purity was ≥99.66%. Mass spectrum m / z: 593.1935 (theoretical value: 593.1910).

[0317] Preparation of 2-150:

[0318] Using the same preparation method as in synthetic example 31, except that n-2-1 was replaced by an equal amount of n-2-150, q-2-1 was replaced by an equal amount of q-2-150, compound 2-150 (39.46 g) was synthesized, and the solid purity was ≥99.71% detected by HPLC. Mass spectrum m / z: 842.3668 (theoretical value: 842.3661). Theoretical elemental content (%) 64 H 46 N2: C, 91.18; H, 5.50; N, 3.32. Found elemental content (%): C, 91.15; H, 5.55; N, 3.28.

[0319] Preparation of compound 2-164

[0320]

[0321] Using the same preparation method as in synthetic example 31, except that m-2-1 was replaced by an equal amount of m-2-164, n-2-1 was replaced by an equal amount of n-2-150, and q-2-1 was replaced by an equal amount of q-2-164, compound 2-164 (41.70 g) was synthesized, and the solid purity was ≥99.67% detected by HPLC. Mass spectrum m / z: 882.3956 (theoretical value: 882.3974). Theoretical elemental content (%) 67 H 50N2: C, 91.12; H, 5.71; N, 3.17. Found (mass %): C, 91.15; H, 5.67; N, 3.15.

[0322] [Synthesis Example 44] Preparation of compound 2-170

[0323]

[0324] Using the same preparation method as in Synthesis Example 31, except that m-2-1 was replaced with an equivalent molar amount of m-2-170, n-2-1 was replaced with an equivalent molar amount of n-2-170, and q-2-1 was replaced with an equivalent molar amount of q-2-164, compound 2-170 (42.42 g) was synthesized, which had a solid purity of > 99.62% as determined by HPLC. Mass m / z: 910.4269 (theoretical value: 910.4287). Theoretical elemental content (%) C 69 H 54 N2: C, 90.95; H, 5.97; N, 3.07. Found (mass %): C, 90.90; H, 5.95; N, 3.04.

[0325] [Synthesis Example 45] Preparation of compound 2-206

[0326]

[0327] Using the same preparation method as in Synthesis Example 31, except that n-2-1 was replaced with an equivalent molar amount of n-2-206, and q-2-1 was replaced with an equivalent molar amount of q-2-206, compound 2-206 (44.37 g) was synthesized, which had a solid purity of > 99.69% as determined by HPLC. Mass m / z: 948.4456 (theoretical value: 948.4443). Theoretical elemental content (%) C 72 H 56 N2: C, 91.10; H, 5.95; N, 2.95. Found (mass %): C, 91.14; H, 5.92; N, 2.99.

[0328] [Synthesis Example 46] Preparation of compound 2-254

[0329]

[0330] Using the same preparation method as in Synthesis Example 31, except that n-2-1 was replaced with an equivalent molar amount of n-2-206, and q-2-1 was replaced with an equivalent molar amount of q-2-206, compound 2-206 (44.37 g) was synthesized, which had a solid purity of > 99.69% as determined by HPLC. Mass m / z: 948.4456 (theoretical value: 948.4443). Theoretical elemental content (%) C60 H 44 N2: C, 90.87; H, 5.59; N, 3.53. Found (%,): C, 90.84; H, 5.62; N, 3.55.

[0331] [Synthesis Example 47] Preparation of compound 2-278

[0332]

[0333] Using the same preparation method as Synthesis Example 31, except that m-2-1 was replaced with an equivalent molar amount of m-2-278, n-2-1 was replaced with an equivalent molar amount of n-2-278, and q-2-1 was replaced with an equivalent molar amount of q-2-17, compound 2-278 (46.19 g) was synthesized, which had a solid purity of > 99.60% as determined by HPLC. Mass m / z: 1005.5051 (theoretical value: 1005.5070). Theoretical elemental content (%) C 76 H 55 D5N2: C, 90.71; H, 6.51; N, 2.78. Found (%,): C, 90.67; H, 6.55; N, 2.77.

[0334] [Synthesis Example 48] Preparation of compound 2-282

[0335]

[0336] Using the same preparation method as Synthesis Example 31, except that m-2-1 was replaced with an equivalent molar amount of m-2-17, n-2-1 was replaced with an equivalent molar amount of n-2-282, and q-2-1 was replaced with an equivalent molar amount of q-2-282, compound 2-282 (45.49 g) was synthesized, which had a solid purity of > 99.74% as determined by HPLC. Mass m / z: 969.4225 (theoretical value: 969.4131). Theoretical elemental content (%) C 74 H 43 D5N2: C, 91.61; H, 5.51; N, 2.89. Found (%,): C, 91.64; H, 5.53; N, 2.86.

[0337] [Synthesis Example 49] Preparation of compound 2-299

[0338]

[0339] Using the same preparation method as in Synthesis Example 31, except that m-2-1 was replaced with equimolar of m-2-299, n-2-1 was replaced with equimolar of n-2-299, and q-2-1 was replaced with equimolar of q-2-299, compound 2-299 (42.28 g) was synthesized, which was > 99.52% in solid purity by HPLC. Mass m / z: 946.4240 (theoretical value: 946.4225). Theoretical elemental content (%) C 72 H 46 D4N2: C, 91.30; H, 5.75; N, 2.96. Found elemental content (%): C, 91.35; H, 5.72; N, 2.93.

[0340] [Synthesis Example 50] Preparation of compound 2-368

[0341]

[0342] Using the same preparation method as in Synthesis Example 31, except that m-2-1 was replaced with equimolar of m-2-164, n-2-1 was replaced with equimolar of n-2-368, and q-2-1 was replaced with equimolar of q-2-368, compound 2-368 (45.60 g) was synthesized, which was > 99.60% in solid purity by HPLC. Mass m / z: 1012.4677 (theoretical value: 1012.4695). Theoretical elemental content (%) C 77 H 52 D4N2: C, 91.27; H, 5.97; N, 2.76. Found elemental content (%): C, 91.30; H, 5.94; N, 2.75.

[0343] After the compound of the present application synthesized in the synthesis example was purified by high-purity sublimation using a conventionally known method, an organic electroluminescent device was produced according to the following procedure.

[0344] [Device Example 1]

[0345] Transparent substrate / Anode (ITO (15 nm) / Ag (150 nm) / ITO (15 nm)) / Hole injection layer (HT-1: P-1 = 97:3 mass ratio, thickness of 10 nm) / Hole transport layer (HT-1, thickness of 120 nm) / Emission layer (RH: RD = 98:2 mass ratio, thickness of 20 nm) / Hole blocking layer (compound 1 of the present application, thickness of 30 nm) / Electron transport layer (ET-1: Liq = 1:1 mass ratio, thickness of 30 nm) / Electron injection layer (Yb, thickness of 1 nm) / Cathode (Mg: Ag = 1:9 mass ratio, thickness of 12 nm) / Cover layer (CP-1, thickness of 70 nm).

[0346] Specific preparation process:

[0347] First, the ITO / Ag / ITO evaporated glass substrate was washed in distilled water for 2 times, ultrasonic washing for 30 minutes, and then washed with distilled water for 2 times, ultrasonic washing for 10 minutes. After washing with distilled water, the substrate was dried on a hot plate heated to 120°C, and then transferred to a plasma cleaning machine for 5 minutes. The substrate was then transferred to an evaporation machine.

[0348] P-1 and HT-1 were evaporated on the ITO / Ag / ITO substrate as a hole injection layer using a vacuum evaporation device, the mass ratio of HT-1 to P-1 was 97:3, and the evaporation thickness was 10 nm. HT-1 was evaporated on the hole injection layer as a hole transport layer, the evaporation thickness was 120 nm, and then the light-emitting layer was evaporated on the hole transport layer, RH was used as the host material, RD was used as the dopant material, the mass ratio of RH to RD was 98:2, and the evaporation thickness was 20 nm. Then, the compound 1 of the present application was evaporated on the light-emitting layer as a hole blocking layer, the evaporation thickness was 30 nm, and then ET-1 and Liq were evaporated on the hole blocking layer as an electron transport layer, the mass ratio of ET-1 to Liq was 1:1, and the evaporation thickness was 30 nm. Yb was evaporated to form an electron injection layer, the evaporation thickness was 1 nm, and then Mg:Ag was evaporated as a cathode, the mass ratio of Mg to Ag was 1:9, and the evaporation thickness was 12 nm. Then, CP-1 was evaporated on the cathode as a cover layer, the evaporation thickness was 70 nm, thereby preparing an organic electroluminescent device.

[0349]

[0350] [Device Examples 2-30]

[0351] The compound 7, compound 22, compound 30, compound 51, compound 56, compound 60, compound 64, compound 71, compound 90, compound 98, compound 105, compound 120, compound 123, compound 130, compound 146, compound 173, compound 176, compound 192, compound 196, compound 197, compound 201, compound 250, compound 269, compound 281, compound 283, compound 307, compound 432, compound 439, and compound 444 of the present application were used instead of compound 1 in Device Example 1 as a hole blocking layer, and the other preparation steps were the same as those in Device Example 1, thereby preparing organic electroluminescent devices 2-30.

[0352] [Comparative Device Examples 1-4]

[0353] Comparative Device 1 to 4 were prepared in the same manner as Device Example 1, except that Comparative Compound 1, Comparative Compound 2, Comparative Compound 3, Comparative Compound 4 were used instead of Compound 1 in Device Example 1 as a hole blocking layer.

[0354] [Device Example 31]

[0355] The following organic electroluminescent devices were prepared by the preparation method of Device Example 1.

[0356] Transparent substrate / Anode (ITO (15 nm) / Ag (150 nm) / ITO (15 nm)) / Hole injection layer (HT-1: P-1 = 97:3 mass ratio, thickness of 10 nm) / Hole transport layer (HT-1, thickness of 120 nm) / Emission layer (RH:RD = 98:2 mass ratio, thickness of 20 nm) / Hole blocking layer (HB-1, thickness of 30 nm) / Electron transport layer (Compound 1 of the present application: Liq = 1:1 mass ratio, thickness of 30 nm) / Electron injection layer (Yb, thickness of 1 nm) / Cathode (Mg:Ag = 1:9 mass ratio, thickness of 12 nm) / Cover layer (CP-1, thickness of 70 nm).

[0357] [Device Examples 32 to 60]

[0358] Organic electroluminescent devices 32 to 60 were prepared in the same manner as Device Example 31, except that Compound 7, Compound 22, Compound 30, Compound 51, Compound 56, Compound 60, Compound 64, Compound 71, Compound 90, Compound 98, Compound 105, Compound 120, Compound 123, Compound 130, Compound 146, Compound 173, Compound 176, Compound 192, Compound 196, Compound 197, Compound 201, Compound 250, Compound 269, Compound 281, Compound 283, Compound 307, Compound 432, Compound 439, Compound 444 of the present application were used instead of Compound 1 in Device Example 31 as an electron transport layer.

[0359] [Comparative Device Examples 5 to 8]

[0360] Comparative Devices 5 to 8 were prepared in the same manner as Device Example 31, except that Comparative Compound 1, Comparative Compound 2, Comparative Compound 3, Comparative Compound 4 were used instead of Compound 1 in Device Example 31 as an electron transport layer.

[0361] [Device Example 61]

[0362] The following organic electroluminescent devices were prepared by the preparation method of Device Example 1.

[0363] Transparent substrate / anode (ITO (15 nm) / Ag (150 nm) / ITO (15 nm)) / hole injection layer (HT-1: P-1 = 97:3 mass ratio, thickness 10 nm) / hole transport layer (compound 2-33 of the present application, thickness 70 nm) / light-emitting layer (RH: RD = 98:2 mass ratio, thickness 20 nm) / hole blocking layer (compound 1 of the present application, thickness 30 nm) / electron transport layer (ET-1: Liq = 1:1 mass ratio, thickness 30 nm) / electron injection layer (Yb, thickness 1 nm) / cathode (Mg: Ag = 1:9 mass ratio, thickness 12 nm) / cover layer (CP-1, thickness 70 nm).

[0364] [Device Examples 62 to 80]

[0365] Instead of compound 2-33 in Device Example 61 as the hole transport layer and compound 1 as the hole blocking layer, the following combinations were used, and the other preparation steps were the same as in Device Example 61, to prepare organic electroluminescent devices 62 to 80:

[0366] Compound 2-145, compound 22; compound 2-206, compound 30; compound 2-41, compound 51; compound 2-164, compound 56; compound 2-96, compound 60; compound 2-99, compound 64; compound 2-250, compound 90; compound 2-278, compound 105; compound 2-282, compound 120; compound 2-368, compound 123; compound 2-301, compound 146; compound 2-64, compound 196; compound 2-116, compound 197; compound 2-17, compound 201; compound 2-91, compound 250; compound 2-254, compound 269; compound 2-1, compound 281; compound 2-136, compound 439; compound 2-170, compound 444.

[0367] [Comparative Device Examples 9 to 18]

[0368] Instead of compound 2-33 in Device Example 61 as the hole transport layer and compound 1 as the hole blocking layer, the following combinations were used, and the other preparation steps were the same as in Device Example 61, to prepare comparative devices 9 to 18:

[0369] Compound 2-1, comparative compound 1; compound 2-91, comparative compound 2; compound 2-164, comparative compound 3; compound 2-301, comparative compound 4; compound 2-33, HB-1; comparative compound 6, compound 1; comparative compound 6, compound 90; comparative compound 7, compound 196; comparative compound 7, compound 269; HT-1, compound 1.

[0370] [Device Example 81]

[0371] The following organic electroluminescent devices were produced by the production method of Device Example 1.

[0372] Transparent substrate / anode (ITO (15 nm) / Ag (150 nm) / ITO (15 nm)) / hole injection layer (HT-1: P-1 = 97:3 mass ratio, thickness of 10 nm) / hole transport layer (HT-1, thickness of 120 nm) / light-emitting layer (RH: RD = 98:2 mass ratio, thickness of 20 nm) / electron transport layer (ET-1: Liq = 1:1 mass ratio, thickness of 30 nm) / electron injection layer (Yb, thickness of 1 nm) / cathode (Mg: Ag = 1:9 mass ratio, thickness of 12 nm) / cover layer (compound 1 of the present application, thickness of 70 nm).

[0373] [Device Examples 82-90]

[0374] Organic electroluminescent devices 82-90 were produced by replacing compound 1 in Device Example 81 with compound 1, compound 30, compound 56, compound 123, compound 130, compound 146, compound 192, compound 196, compound 250, and compound 439 as the cover layer, and the other production steps were the same as those of Device Example 81.

[0375] [Comparative Device Example 19]

[0376] Comparative device 19 was produced by replacing compound 1 in Device Example 81 with comparative compound 5 as the cover layer, and the other production steps were the same as those of Device Example 81.

[0377] A combined IVL test system consisting of test software, a computer, a K2400 digital source meter produced by Keithley Corporation, USA, and a PR788 spectral scanning luminance meter produced by Photo Research Corporation, USA was used to test the driving voltage and luminous efficiency of the organic electroluminescent devices. The M6000 OLED lifetime test system produced by McScience Corporation was used to test the lifetime. The test environment was atmospheric environment, and the temperature was room temperature. The test results of the luminous characteristics of the organic electroluminescent devices obtained in Device Examples 1-60 of the present application and Comparative Device Examples 1-8 are shown in Table 1 below. The test results of the luminous characteristics of the organic electroluminescent devices obtained in Device Examples 61-80 of the present application and Comparative Device Examples 9-18 are shown in Table 2 below. The test results of the luminous characteristics of the organic electroluminescent devices obtained in Device Examples 81-90 of the present application and Comparative Device Example 19 are shown in Table 3 below.

[0378] Table 1:

[0379]

[0380]

[0381]

[0382] From the results of Table 1, it can be seen that the compound containing a fused aromatic ring provided by the present application has high electron mobility, which can improve the recombination probability of electrons and holes in the light-emitting layer; at the same time, it has a high triplet energy level, which can effectively block the escape of holes to the side of the electron transport layer, prevent the recombination of holes and electrons at the interface, and thus reduce the driving voltage of the organic electroluminescent device, improve the luminous efficiency, and prolong the service life.

[0383] Table 2:

[0384]

[0385]

[0386] From the results of Table 2, it can be seen that when the compound containing a fused aromatic ring provided by the present application is used as a hole blocking layer and the triarylamine derivative is used as a hole transport layer, the carrier mobility and energy level of the two are well matched, showing excellent synergistic effect. Compared with comparative device examples 9-18, when the two are matched, the carrier transport is balanced, the exciton can effectively recombine in the light-emitting layer, the exciton is prevented from emitting at the interface, and the organic electroluminescent device shows low driving voltage, high luminous efficiency, and long service life.

[0387] Table 3:

[0388]

[0389] According to the results of Table 3, the compound containing a fused aromatic ring provided by the present application has a high refractive index and a high glass transition temperature. When it is applied to the cover layer of the organic electroluminescent device, it can effectively improve the light extraction efficiency of the organic electroluminescent device, and thus improve the luminous efficiency of the device and prolong the service life.

[0390] It should be noted that the present application is particularly described with individual embodiments, and for those skilled in the art, a number of improvements and modifications can be made to the present application without departing from the principles of the present application, and these improvements and modifications also fall within the scope of protection of the present application.

Claims

1. A compound comprising a fused aromatic ring, characterized in that The compound containing a fused aromatic ring has a structure shown in Formula 1: In Formula 1, A is selected from any one of the following groups: R6 and R7 are independently selected from any one of substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, and substituted or unsubstituted pyridyl; The R8 is independently selected from any one of hydrogen, deuterium, substituted or unsubstituted methyl; The R9, R 10 Any one independently selected from substituted or unsubstituted C1-C6 alkyl groups; R6-R 10 The "substituted" group is selected from any one of deuterium, methyl, ethyl, n-propyl, n-butyl, isopropyl, isobutyl, sec-butyl and tert-butyl; The n2 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8, the n3 is independently selected from 0, 1, 2, 3, 4, 5, 6 or 7, the p3 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8, the p4 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10, and the p5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13 or 14; R4 is independently selected from any one of hydrogen, deuterium, cyano, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted phenyl, and substituted or unsubstituted pyridyl; The n2 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; when n2 is greater than 1, two or more R4 are the same or different from each other, or two adjacent R4 form a substituted or unsubstituted benzene ring; The "substituted" group in the substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted phenyl, substituted or unsubstituted pyridyl, or substituted or unsubstituted benzene ring in R4 is selected from deuterium; The E1 and E2 are independently selected from any one of the following groups: The R5 is independently selected from any one of hydrogen and deuterium; The m1 is independently selected from 0, 1, 2, 3, 4, 5, 6, the m2 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8, the m3 is independently selected from 0, 1, 2, 3 or 4, the m4 is independently selected from 0, 1 or 2, the m5 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; described Any one selected from the following groups: Said Y is independently selected from an O atom or a S atom; The L1 is selected from any one of a single bond, a substituted or unsubstituted phenylene group; the "substituted" group is selected from deuterium; Said L2 is selected from a single bond; Provided that the compound is not:

2. The compound comprising a fused aromatic ring according to claim 1, characterized in that The A is selected from any one of the following groups: The R4 is independently selected from hydrogen and deuterium.

3. The compound comprising a fused aromatic ring according to claim 1, characterized in that: The E1 and E2 are independently selected from any one of the following groups:

4. The compound comprising a fused aromatic ring according to claim 1, characterized in that: described Any one selected from the following groups:

5. A compound comprising a fused aromatic ring, characterized in that The compound containing a fused aromatic ring is selected from any one of the following structures:

6. An organic electroluminescent device comprising an anode, a cathode, and an organic layer, wherein the organic layer is located between the anode and the cathode or outside at least one of the electrodes, and the organic layer comprises any one or more of the compounds containing a fused aromatic ring according to any one of claims 1 to 5.

7. The organic electroluminescent device according to claim 6, characterized in that: The organic layer comprises at least one of a hole blocking layer, an electron transport layer or a capping layer, and the at least one of the hole blocking layer, the electron transport layer or the capping layer comprises any one or more of the compounds containing a condensed aromatic ring according to any one of claims 1 to 5.

8. The organic electroluminescent device according to claim 7, characterized in that: The organic layer further comprises a hole transport layer, wherein the hole transport layer comprises a triarylamine derivative represented by Formula 2: The Ara and Arb are independently selected from any one of the following groups: The Rd is independently selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl; or two adjacent Rd can be connected to form a substituted or unsubstituted ring; The Re is independently selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl; or two Re may be connected to form a substituted or unsubstituted ring; Said d1 is independently selected from 0, 1, 2, 3, 4 or 5, said d2 is independently selected from 0, 1, 2, 3 or 4, and said d3 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; The Arc is selected from any one of a substituted or unsubstituted C6-C30 aryl group and a substituted or unsubstituted C2-C30 heteroaryl group; The Ra is independently selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl; or Arc is directly bonded to Lc. When directly bonded to Lc, Arc is selected from a single bond; The Rb is independently selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl; or two adjacent Rb can be connected to form a substituted or unsubstituted ring; The Rc is independently selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl; or two adjacent Rc may be connected to form a substituted or unsubstituted ring; b1 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8, b2 is selected from 0, 1, 2 or 3, and b3 is selected from 0, 1, 2, 3 or 4; The La to Ld are independently selected from any one of a single bond, a substituted or unsubstituted C6 to C30 arylene group, and a substituted or unsubstituted C2 to C30 heteroarylene group; The term "substituted" refers to being independently monosubstituted or polysubstituted by the following groups: deuterium, C1-C12 alkyl, C3-C12 cycloalkyl, C6-C30 aryl, C2-C30 heteroaryl.

9. The organic electroluminescent device according to claim 8, characterized in that: The hole transport layer comprises any one of the structures shown in Formula 2-1 to Formula 2-3: The Rc is independently selected from hydrogen, deuterium, or any of the following substituted or unsubstituted groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, benzocyclopropyl, benzocyclobutyl, benzocyclopentyl, benzocyclohexyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, fluorenyl, dibenzofuranyl, dibenzothiophenyl, and carbazolyl; The "substituted" group is selected from any one or more of deuterium, C1-C12 alkyl, C3-C12 cycloalkyl, and C6-C18 aryl; The b2 is independently selected from 0, 1, 2 or 3, the b3 is selected from 0, 1, 2, 3 or 4, and the b4 is selected from 0, 1 or 2.

10. The organic electroluminescent device according to claim 8, characterized in that: The Ara and Arb are independently selected from any one of the following groups:

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