An organic compound containing carbazole and an organic electroluminescent device thereof

Abstract

The present invention provides an organic compound containing carbazole and an organic electroluminescent device thereof, and relates to the field of organic electroluminescent materials. In order to solve the problems of high driving voltage, low luminous efficiency and short life of organic electroluminescent devices in the prior art, the present invention provides an organic compound containing carbazole with excellent performance and an organic electroluminescent device thereof. The organic compound provided by the present invention has suitable HOMO and LUMO energy levels and a relatively high triplet energy level, can match the adjacent functional layer, improve the charge transfer rate, block the holes from escaping to the electron transport layer side, effectively improve the recombination rate of excitons in the light-emitting layer, and when it is applied to the light-emitting layer or hole blocking layer of the organic electroluminescent device, the light-emitting efficiency and life of the device can be significantly improved, and the driving voltage can be reduced.

Description

Technical Field

[0001] The invention relates to the field of organic electroluminescent materials, and in particular to an organic compound containing carbazole and an organic electroluminescent device thereof. Background Art

[0002] Compared with other traditional devices, organic electroluminescent devices (OLEDs) have the advantages of active luminescence, low energy consumption, high resolution, large color gamut, ultra-thin thickness and flexibility, and have become the focus of current research and development.

[0003] Organic electroluminescent materials can be divided into two types according to the principle of luminescence: electroluminescent and electrophosphorescent. The internal quantum efficiency of fluorescent materials does not exceed 25%, and the external quantum efficiency is generally less than 5%. The internal quantum efficiency of phosphorescent materials can theoretically reach 100%, and the external quantum efficiency can reach 20%. However, phosphorescent guest materials may cause triplet-triplet annihilation and concentration quenching under high current density, causing device life attenuation. Therefore, phosphorescent guest materials are usually doped into suitable host materials to form a host-guest doping system to optimize energy transfer and maximize luminous efficiency and life. The phosphorescent host material can be selected as a premixed material of a hole-type host and an electron-type host. Under electrical excitation, electrons and holes recombine on the host to form excitons. The excitons are transferred from the host to the phosphorescent guest through energy transfer, and then emit light through the phosphorescent guest radiation transition. Therefore, the selection of host materials is crucial to improving device efficiency, life, and improving efficiency roll-off.

[0004] However, the current phosphorescent host materials have unbalanced carrier transmission in the light-emitting layer due to the mismatch between the HOMO energy level and LUMO energy level with the energy levels of the adjacent functional layer materials, as well as obvious differences in carrier transport. Excitons cannot be effectively recombined in the light-emitting layer, resulting in efficiency roll-off. Therefore, it is urgent to develop a host material with excellent performance to improve the luminous efficiency of organic electroluminescent devices and extend the service life of the devices. Summary of the invention

[0005] In order to solve the above problems, the present invention provides an organic compound containing carbazole and an organic electroluminescent device thereof, which can improve the luminous efficiency of the organic electroluminescent device, improve the efficiency roll-off, and extend the service life of the device.

[0006] Specifically, the present invention provides an organic compound containing carbazole, which is represented by Formula 1:

[0007]

[0008] The A is selected from the structure represented by Formula 1-a or Formula 1-b;

[0009] In Formula 1-a and Formula 1-b, the T is independently selected from CH or N atoms;

[0010] The ring E1 is selected from any one of the following structures:

[0011]

[0012] The ring E2 is selected from any one of the following structures:

[0013]

[0014] The V is independently selected from CH or N atoms, and at least one V in each group is selected from N atoms;

[0015] The R1 is independently selected from any one of hydrogen, deuterium, cyano, nitro, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl; or two adjacent R1 are connected to form a substituted or unsubstituted ring;

[0016] The R4 is independently selected from any one of hydrogen, deuterium, cyano, nitro, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl;

[0017] The n0 is independently selected from 0, 1, 2, 3 or 4, the n1 is independently selected from 0, 1, 2, 3, 4, 5 or 6, the n2 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8, the n3 is independently selected from 0, 1 or 2; the n4 is independently selected from 0, 1, 2, 3, 4 or 5, the n5 is independently selected from 0, 1, 2, 3, 4, 5, 6 or 7;

[0018] Ar0 is selected from any one of hydrogen, deuterium, cyano, nitro, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl;

[0019] The X is independently selected from any one of O, S, and N(R5); the Y is independently selected from CH or N;

[0020] The R2 is independently selected from any one of hydrogen, deuterium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl;

[0021] The R3 and R5 are independently selected from any one of hydrogen, deuterium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl; or two adjacent R3 are connected to form a substituted or unsubstituted ring;

[0022] The m1 is selected from 0, 1, 2 or 3, and the m2 is independently selected from 0, 1, 2, 3, 4 or 5;

[0023] The L1 is selected from any one of a single bond, a substituted or unsubstituted C6-C30 arylene group, and a substituted or unsubstituted C2-C30 heteroarylene group;

[0024] The L2 and L3 are independently selected from a single bond, or selected from any one or a combination of the following groups:

[0025]

[0026] The R 10 Any one independently selected from hydrogen, deuterium, cyano, nitro, halogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl; or two adjacent R10 are connected to form a substituted or unsubstituted C3-C7 aliphatic ring;

[0027] The R 11 , R 12 independently selected from any one of hydrogen, deuterium, cyano, nitro, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl; or R 11 , R 12 are connected to form a substituted or unsubstituted ring;

[0028] The b1 is independently selected from 1, 2, 3 or 4, the b2 is independently selected from 1 or 2, and the b3 is independently selected from 1, 2 or 3.

[0029] The present invention also provides 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 anode and the cathode, and the organic layer comprises any one or more of the organic compounds containing carbazole described in the present invention.

[0030] Beneficial Effects

[0031] The organic compound provided by the present invention has suitable HOMO and LUMO energy levels, can match the adjacent functional layer, is conducive to charge transfer, can adjust the carrier transfer balance in the light-emitting layer, widen the carrier recombination area, and improve the exciton recombination rate. At the same time, the organic compound has a suitable triplet energy level, further blocking the hole from escaping to one side of the electron transport layer, reducing the probability of excitons emitting light at the interface of the light-emitting layer, avoiding energy loss, and can improve the luminous efficiency of the organic electroluminescent device and improve the efficiency roll-off; at the same time, the organic compound has a higher glass transition temperature, can form a better amorphous film, and improve the life of the device. In addition, the organic compound has a high refractive index, and when used in the covering layer of the organic electroluminescent device, it can improve the light extraction efficiency, and the luminous efficiency of the organic electroluminescent device is significantly improved. DETAILED DESCRIPTION

[0032] The following will be clearly and completely described in conjunction with the technical solutions of the embodiments of the present invention. Obviously, the described embodiments are only a part of the embodiments of the present invention, rather than all the embodiments. After reading the present invention, modifications of various equivalent forms of the present invention by those skilled in the art all fall within the scope defined by the present invention.

[0033] In the compounds of the present invention, any atom not designated as a particular isotope includes any stable isotope of that atom, and includes the atom in both its natural isotopic abundance and unnatural abundance.

[0034] In the manual, Refers to the portion that is connected to another substituent. Can be attached to any optional position of the attached group / fragment. express And so on.

[0035] In the present invention, when the position of a substituent on an aromatic ring is not fixed, it means that it can be connected to any of the corresponding optional positions of the aromatic ring. For example, Can be expressed Can be expressed Can be expressed And so on.

[0036] The halogen described in the present invention may include fluorine, chlorine, bromine and iodine.

[0037] The alkyl group described in the present invention refers to a monovalent group after removing a hydrogen atom from an alkane molecule, and may be a straight-chain alkyl group or a branched-chain alkyl group, preferably having 1 to 12 carbon atoms, more preferably 1 to 8 carbon atoms, and particularly preferably 1 to 6 carbon atoms. Examples may include methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, isobutyl, sec-butyl, n-pentyl, isopentyl, n-hexyl, etc., but are not limited thereto.

[0038] The alkenyl group of the present invention refers to a monovalent group after removing a hydrogen atom from an olefin molecule, and may be a straight-chain alkenyl group or a branched alkenyl group, preferably having 2 to 15 carbon atoms, more preferably 2 to 12 carbon atoms, and particularly preferably 2 to 6 carbon atoms. Specific examples may include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, styryl, etc., but are not limited thereto.

[0039] The cycloalkyl group of the present invention refers to a monovalent group after removing a hydrogen atom from a cyclic alkane molecule, preferably having 3 to 12 carbon atoms, more preferably 3 to 10 carbon atoms, and particularly preferably 3 to 6 carbon atoms. Examples may include cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantyl, norbornane, etc., but are not limited thereto.

[0040] The aryl group of the present invention refers to a monovalent group after removing a hydrogen atom from the aromatic carbon nucleus of an aromatic hydrocarbon molecule, and may be a monocyclic aryl group, a polycyclic aryl group or a condensed 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. Examples may include phenyl, biphenyl, terphenyl, quaterphenyl, naphthyl, anthracenyl, phenanthrenyl, pyrenyl, fluoranthenyl, triphenylene, 1,2-triphenylene, 2,3-triphenylene, 3,4-triphenylene, peryl, 1-phenylnaphthyl, 2-phenylnaphthyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9-methyl-9-phenylfluorenyl, 9,9'-spirofluorenyl, benzofluorenyl, etc., but are not limited thereto.

[0041] The heteroaryl group described in the present invention refers to a monovalent group obtained by replacing one or more aromatic carbon atoms in an aromatic hydrocarbon molecule with a heteroatom, wherein the heteroatom includes but is not limited to oxygen, sulfur, selenium, 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. Examples may include pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, thienyl, pyrrolyl, oxazolyl, thiazolyl, imidazolyl, bipyridyl, bipyrimidinyl, phenylpyridyl, phenylpyrimidinyl, quinolyl, isoquinolyl, benzoquinolyl, benzoisoquinolyl, quinazolinyl, quinoxalinyl, benzoquinazolinyl, benzoquinoxalinyl, o-phenanthroline, naphthyridinyl, indolyl, benzothienyl, benzofuranyl, N-heterobenzothienyl, N-heterobenzofuranyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, oxadiazolyl, thiadiazolyl, triazolyl , benzoxadiazolyl, benzothiadiazolyl, benzotriazolyl, dibenzofuranyl, N-heterodibenzofuranyl, benzodibenzofuranyl, dibenzothiophenyl, N-heterodibenzothiophenyl, benzodibenzothiophenyl, dibenzoxazolyl, dibenzimidazolyl, dibenzothiazolyl, carbazolyl, N-heterocarbazolyl, benzocarbazolyl, indenocarbazolyl, indolcarbazolyl, benzofuranocarbazolyl, benzothiophenocarbazolyl, acridinyl, 9,10-dihydroacridinyl, phenoxazinyl, phenothiazinyl, phenoxathiol, spirofluorenyloxanthracene, spirofluorenylthioanthracene, and the like, but are not limited thereto.

[0042] The arylene group in the present invention refers to an aryl group having two bonding positions, i.e., a divalent group. Except that each of them is a divalent group, the above description of the aryl group is applicable.

[0043] The heteroarylene group in the present invention means a heteroaryl group having two bonding positions, i.e., a divalent group. Except that each of them is a divalent group, the above description of the heteroaryl group is applicable.

[0044] The silyl group described in the present invention refers to a monovalent group formed by removing a hydrogen atom from a silane molecule, and can be represented by the group described by -Si(Rs)(Rs)(Rs), wherein Rs is selected from hydrogen, deuterium, cyano, halogen, or any one or more of the alkyl, cycloalkyl, aryl, and heteroaryl groups described above, preferably having 1 to 30 carbon atoms, preferably having 1 to 25 carbon atoms, more preferably having 1 to 22 carbon atoms, and most preferably having 1 to 18 carbon atoms. Examples may include trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, dimethylethylsilyl, dimethyl-tert-butylsilyl, diethylmethylsilyl, tricyclopropylsilyl, tricyclobutylsilyl, triphenylsilyl, triphenylsilyl, etc., but are not limited thereto.

[0045] The term "substituted..." as used herein, such as "substituted alkyl, substituted cycloalkyl, substituted aryl, substituted heteroaryl, substituted arylene, substituted heteroarylene, substituted silyl" refers to independently being mono- or poly-substituted by the following groups: deuterium, tritium, cyano, nitro, hydroxyl, halogen atom, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted substituted or unsubstituted C6~C30 aryl, substituted or unsubstituted C2~C30 heteroaryl, substituted or unsubstituted C1~C12 alkoxy, substituted or unsubstituted C1~C12 alkylthio, substituted or unsubstituted C1~C12 alkylamino, substituted or unsubstituted C6~C30 aryloxy, substituted or unsubstituted C6~C30 arylamino, etc., but not limited to these, when there are two or more substituents, two adjacent substituents can be connected to form a ring. Preferably, the following radicals are monosubstituted or polysubstituted: deuterium, fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, trifluoromethyl, deuterated methyl, ethyl, isopropyl, tert-butyl, deuterated tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cyclopentadienyl, cyclohexadienyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, triphenylsilyl, phenyl, biphenyl, terphenyl, naphthyl, deuterated phenyl, deuterated biphenyl, deuterated terphenyl, deuterated naphthalene The invention also includes but is not limited to phenyl, anthracene, phenanthryl, triphenylene, peryl, pyrenyl, benzyl, tert-butyl substituted phenyl, adamantyl substituted phenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9-methyl-9-phenylfluorenyl, 9,9'-spirobifluorenyl, diphenylamino, pyridyl, pyrimidinyl, triazine, carbazolyl, acridinyl, furanyl, thienyl, benzofuranyl, benzothiophenyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, dibenzofuranyl, dibenzothiophenyl, phenothiazinyl, phenoxazinyl, indolyl and the like, but are not limited thereto.

[0046] In the present invention, "adjacent groups are connected to form a ring" means that adjacent groups are combined with each other and optionally aromatized to form a substituted or unsubstituted aromatic ring, heteroaromatic ring, aliphatic ring or aliphatic heterocycle. The aromatic ring preferably has 6 to 30 carbon atoms, preferably 6 to 18 carbon atoms, more preferably 6 to 12 carbon atoms; the heteroaromatic ring preferably has 2 to 30 carbon atoms, preferably 2 to 18 carbon atoms, more preferably 2 to 12 carbon atoms; the aliphatic ring preferably has 3 to 12 carbon atoms, preferably 3 to 7 carbon atoms, more preferably 5 to 7 carbon atoms; the aliphatic heterocycle preferably has 2 to 12 carbon atoms, preferably 2 to 7 carbon atoms, more preferably 2 to 7 carbon atoms; the heteroatoms in the heteroaromatic ring and aliphatic heterocycle are preferably, but not limited to, O, S, N, Si, and P. More preferably, the aromatic ring is preferably a benzene ring, a naphthalene ring, an anthracene ring, and a phenanthrene ring, but not limited thereto; the aliphatic ring is preferably a cyclopropane ring, a cyclobutane ring, a cyclopentane ring, a cyclohexane ring, a cycloheptane ring, a cyclobutene ring, a cyclopentene ring, and a cyclohexene ring, but not limited thereto; the heteroaromatic ring is preferably a pyridine ring, a pyrimidine ring, a quinoline ring, an isoquinoline ring, a benzofuran ring, and a benzothiophene ring, but not limited thereto; the aliphatic heterocyclic ring is preferably a piperidine ring, a furan ring, and a thiophene ring, but not limited thereto.

[0047] The "adjacent groups" refer to two substituents on two directly connected atoms, a substituent arranged to be closest in space to the corresponding substituent, and another substituent on the atom with the corresponding substituent. For example, two substituents substituted at the ortho position of a benzene ring or two substituents on the same carbon atom in an aliphatic ring can be considered to be "adjacent" to each other; as shown in the following examples:

[0048]

[0049] In the present invention, the ring formed by connection can be a three-membered ring, a four-membered ring, a five-membered ring, a six-membered ring, a seven-membered ring, an eight-membered ring, a condensed ring, a spiro ring, etc., for example, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopentene, cyclohexene, benzene, naphthalene, phenanthrene, triphenylene, pyridine, pyrimidine, quinoline, isoquinoline, quinazoline, quinoxaline, fluorene, dibenzofuran, dibenzothiophene, carbazole, etc., but are not limited thereto.

[0050] The present invention provides an organic compound containing carbazole, which is represented by Formula 1:

[0051]

[0052] The A is selected from the structure represented by Formula 1-a or Formula 1-b;

[0053] In Formula 1-a and Formula 1-b, the T is independently selected from CH or N atoms;

[0054] The ring E1 is selected from any one of the following structures:

[0055]

[0056] The ring E2 is selected from any one of the following structures:

[0057]

[0058]

[0059] The V is independently selected from CH or N atoms, and at least one V in each group is selected from N atoms;

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

[0061] The R4 is independently selected from any one of hydrogen, deuterium, cyano, nitro, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl;

[0062] The n0 is independently selected from 0, 1, 2, 3 or 4, the n1 is independently selected from 0, 1, 2, 3, 4, 5 or 6, the n2 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8, the n3 is independently selected from 0, 1 or 2; the n4 is independently selected from 0, 1, 2, 3, 4 or 5, the n5 is independently selected from 0, 1, 2, 3, 4, 5, 6 or 7;

[0063] Ar0 is selected from any one of hydrogen, deuterium, cyano, nitro, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl;

[0064] The X is independently selected from any one of O, S, and N(R5); the Y is independently selected from CH or N;

[0065] The R2 is independently selected from any one of hydrogen, deuterium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl;

[0066] The R3 and R5 are independently selected from any one of hydrogen, deuterium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl; or two adjacent R3 are connected to form a substituted or unsubstituted ring;

[0067] The m1 is selected from 0, 1, 2 or 3, and the m2 is independently selected from 0, 1, 2, 3, 4 or 5;

[0068] The L1 is selected from any one of a single bond, a substituted or unsubstituted C6-C30 arylene group, and a substituted or unsubstituted C2-C30 heteroarylene group;

[0069] The L2 and L3 are independently selected from a single bond, or selected from any one or a combination of the following groups:

[0070]

[0071] The R 10 Any one independently selected from hydrogen, deuterium, cyano, nitro, halogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl; or two adjacent R10 are connected to form a substituted or unsubstituted C3-C7 aliphatic ring;

[0072] The R 11 , R 12 independently selected from any one of hydrogen, deuterium, cyano, nitro, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl; or R 11 , R 12 are connected to form a substituted or unsubstituted ring;

[0073] The b1 is independently selected from 1, 2, 3 or 4, the b2 is independently selected from 1 or 2, and the b3 is independently selected from 1, 2 or 3.

[0074] In the present application, a preferred embodiment is that the compound of formula 1 is selected from any one of the following formulas 2-1 to 2-6:

[0075]

[0076] Among them, in Chemical Formula 2-1 to Chemical Formula 2-6,

[0077] The definitions of A, L1, L2, L3, X, Y, R2, R3, m1, and m2 are the same as those in Formula 1.

[0078] More preferably, R2 is independently selected from any one of hydrogen, deuterium, cyano, halogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, trifluoromethyl, trimethylsilyl, triethylsilyl, deuterated methyl, deuterated ethyl, deuterated n-propyl, deuterated isopropyl, deuterated n-butyl, deuterated isobutyl, deuterated tert-butyl, adamantyl, and norbornyl.

[0079] Preferably, the A is independently selected from any one of the following groups:

[0080]

[0081]

[0082]

[0083]

[0084] The definitions of R1, R4, and Ar0 are the same as those in Formula 1-a and Formula 1-b;

[0085] The n0 is independently selected from 0, 1, 2, 3 or 4, the n1 is independently selected from 0, 1, 2, 3, 4, 5 or 6, the n2 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8, the n3 is independently selected from 0, 1 or 2, the n4 is independently selected from 0, 1, 2 or 3, the n5 is independently selected from 0, 1, 2, 3, 4 or 5, and the n6 is independently selected from 0, 1, 2, 3, 4, 5, 6 or 7.

[0086] More preferably, R1 and R4 are independently selected from hydrogen, deuterium, cyano, nitro, halogen; any one of the following groups which are unsubstituted or substituted with deuterium: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, trimethylsilyl, triethylsilyl, triphenylsilyl, trifluoromethyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantyl, norbornane, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, Methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, fluorine-substituted phenyl, trifluoromethyl-substituted phenyl, cyano-substituted phenyl, trimethylsilyl-substituted phenyl, methyl-substituted biphenyl, ethyl-substituted biphenyl, isopropyl-substituted biphenyl, tert-butyl-substituted biphenyl, fluorine-substituted biphenyl, trifluoromethyl-substituted biphenyl, cyano-substituted biphenyl, trimethylsilyl-substituted biphenyl, pyridyl, pyrimidinyl, quinolyl, isoquinolyl, o-phenanthroline, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl.

[0087] Preferably, Ar0 is independently selected from hydrogen, deuterium, cyano, nitro, halogen, any one of the following groups which are unsubstituted or substituted with deuterium: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, trimethylsilyl, triethylsilyl, triphenylsilyl, trifluoromethyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantyl, norbornane, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, methyl substituted phenyl, ethyl substituted phenyl, isopropyl substituted phenyl, tert-butyl substituted phenyl, fluorine substituted phenyl, trifluoromethyl substituted phenyl, cyano substituted phenyl substituted phenyl, trimethylsilyl-substituted phenyl, naphthyl-substituted phenyl, 9,9-dimethylfluorenyl-substituted phenyl, benzofuran-substituted phenyl, benzothiophene-substituted phenyl, dibenzofuran-substituted phenyl, dibenzothiophene-substituted phenyl, methyl-substituted biphenyl, ethyl-substituted biphenyl, isopropyl-substituted biphenyl, tert-butyl-substituted biphenyl, fluorine-substituted biphenyl, trifluoromethyl-substituted biphenyl, cyano-substituted biphenyl, trimethylsilyl-substituted biphenyl, methyl-substituted naphthyl, tert-butyl-substituted naphthyl, phenyl-substituted naphthyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, pyridyl, pyrimidinyl, quinolyl, isoquinolyl, o-phenanthroline, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene.

[0088] Preferably, the Any one selected from the following groups:

[0089]

[0090]

[0091]

[0092] The R3 is independently selected from any one of hydrogen, deuterium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl;

[0093] The R3' is independently selected from any one of hydrogen, deuterium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl;

[0094] The R5 is independently selected from any one of hydrogen, deuterium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl;

[0095] The m2 is independently selected from 0, 1, 2, 3, 4 or 5, the m3 is independently selected from 0, 1, 2, 3 or 4, the m4 is independently selected from 0, 1, 2 or 3, the m5 is independently selected from 0, 1 or 2, the m6 is independently selected from 0, 1, 2, 3, 4, 5 or 6, the m7 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8, and the m8 is independently selected from 0, 1, 2, 3, 4, 5, 6 or 7.

[0096] More preferably, R3, R3', and R5 are independently selected from hydrogen, deuterium, cyano, halogen, any one of the following groups which are unsubstituted or substituted with deuterium: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, trimethylsilyl, triethylsilyl, triphenylsilyl, trifluoromethyl, cyclopropyl, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantyl, norbornyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, methyl substituted phenyl, ethyl substituted phenyl, isopropyl substituted phenyl, tert-butyl substituted phenyl, fluorine substituted phenyl, trifluoromethyl substituted phenyl, cyano substituted phenyl, trimethylsilyl-substituted phenyl, naphthyl-substituted phenyl, 9,9-dimethylfluorenyl-substituted phenyl, benzofuran-substituted phenyl, benzothiophene-substituted phenyl, dibenzofuran-substituted phenyl, dibenzothiophene-substituted phenyl, methyl-substituted biphenyl, ethyl-substituted biphenyl, isopropyl-substituted biphenyl, tert-butyl-substituted biphenyl, fluorine-substituted biphenyl, trifluoromethyl-substituted biphenyl, cyano-substituted biphenyl, trimethylsilyl-substituted biphenyl, methyl-substituted naphthyl, tert-butyl-substituted naphthyl, phenyl-substituted naphthyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, pyridyl, pyrimidinyl, quinolyl, isoquinolyl, o-phenanthroline, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene.

[0097] Preferably, L1 is selected from a single bond or any one of the following groups:

[0098]

[0099]

[0100] The R6 and R7 are independently selected from any one of hydrogen, deuterium, cyano, nitro, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl;

[0101] The R8 is independently selected from any one of hydrogen, deuterium, cyano, nitro, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl; or two adjacent R8 are connected to form any one of the following ring structures:

[0102]

[0103] The R9 is independently selected from any one of hydrogen, deuterium, cyano, nitro, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl;

[0104] Said a1 is independently selected from 0, 1, 2, 3 or 4, said a2 is independently selected from 0, 1, 2 or 3, said a3 is independently selected from 0, 1 or 2, said a4 is independently selected from 0, 1, 2, 3, 4, 5 or 6, said a5 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8, and said a6 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10.

[0105] More preferably, L1 is selected from a single bond or any one of the following groups:

[0106]

[0107]

[0108] The R6 and R7 are independently selected from hydrogen, deuterium, cyano, nitro, halogen, any one of the following groups which are unsubstituted or substituted with deuterium: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, trimethylsilyl, triethylsilyl, triphenylsilyl, trifluoromethyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantyl, norbornane, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, methyl substituted phenyl, ethyl substituted Phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, fluorine-substituted phenyl, trifluoromethyl-substituted phenyl, cyano-substituted phenyl, trimethylsilyl-substituted phenyl, methyl-substituted biphenyl, ethyl-substituted biphenyl, isopropyl-substituted biphenyl, tert-butyl-substituted biphenyl, fluorine-substituted biphenyl, trifluoromethyl-substituted biphenyl, cyano-substituted biphenyl, trimethylsilyl-substituted biphenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, pyridyl, pyrimidinyl, quinolyl, isoquinolyl, o-phenanthroline, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl.

[0109] The a1 is independently selected from 0, 1, 2, 3 or 4, the a2 is independently selected from 0, 1, 2 or 3, the a3 is independently selected from 0, 1 or 2, the a4 is independently selected from 0, 1, 2, 3, 4, 5 or 6, the a5 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8, and the a7 is independently selected from 0, 1, 2, 3, 4 or 5.

[0110] Preferably, L2 and L3 are independently selected from a single bond or any one of the following groups:

[0111]

[0112] The R 10 , R 11 independently selected from hydrogen, deuterium, cyano, nitro, halogen, substituted or unsubstituted any one of the following groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, adamantyl, norbornyl, trimethylsilyl, triethylsilyl;

[0113] The b1 is independently selected from 0, 1, 2, 3 or 4, the b2 is independently selected from 0, 1, 2 or 3, the b3 is independently selected from 0, 1 or 2, the b4 is independently selected from 0, 1, 2, 3, 4, 5 or 6, the b5 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8, and the b6 is selected from 0, 1, 2, 3, 4 or 5.

[0114] Most preferably, the organic compound is selected from any one of the following structures:

[0115]

[0116]

[0117]

[0118]

[0119]

[0120]

[0121]

[0122]

[0123]

[0124]

[0125]

[0126]

[0127]

[0128]

[0129]

[0130]

[0131]

[0132]

[0133]

[0134]

[0135]

[0136]

[0137]

[0138]

[0139]

[0140]

[0141]

[0142]

[0143] Some specific structural forms of the compound of formula 1 described in the present invention are listed above, but the present invention is not limited to these listed chemical structures, and all compounds based on the structure shown in formula 1 and having substituents as defined above should be included.

[0144] In addition, the present invention also provides an organic electroluminescent device, comprising an anode, a cathode and an organic layer, wherein the organic layer comprises the compound of formula 1 of the present invention.

[0145] Preferably, the organic layer is located between the anode and the cathode or outside at least one of the anode and the cathode, and the organic layer comprises the compound of formula 1 of the present invention.

[0146] Specifically, the organic layer between the anode and the cathode may include at least one of a hole transport layer, a hole injection layer, a light-emitting auxiliary layer, a light-emitting layer, an electron transport layer, a hole blocking layer, and an electron injection layer, but is not limited thereto. The organic layer located outside at least one of the anode and the cathode includes at least one of a covering layer and a sealing layer, but is not limited thereto.

[0147] More preferably, the organic layer is located between the anode and the cathode, and the organic layer comprises at least one of a light-emitting layer, an electron transport layer, and a hole blocking layer, and at least one of the light-emitting layer, the electron transport layer, and the hole blocking layer comprises the compound of formula 1 of the present invention.

[0148] More preferably, the organic layer is located between the anode and the cathode, and the organic layer comprises a light-emitting layer, and the light-emitting layer comprises the compound of formula 1 of the present invention.

[0149] Further preferably, the light-emitting layer comprises a host material and a guest material, and the host material comprises the compound of formula 1 of the present invention.

[0150] More preferably, the organic layer is located between the anode and the cathode, the organic layer comprises an electron transport layer, and the electron transport layer comprises the compound of Formula 1 of the present invention.

[0151] More preferably, the organic layer is located between the anode and the cathode, the organic layer comprises a hole blocking layer, and the hole blocking layer comprises the compound of formula 1 of the present invention.

[0152] Preferably, the organic electroluminescent device of the present invention comprises a stacked organic electroluminescent device, the stacked organic electroluminescent device comprises two or more adjacent light-emitting units, a charge generation layer is comprised between two adjacent light-emitting units, and the charge generation layer comprises the compound of formula 1 of the present invention.

[0153] As the anode of the present invention, a transmissive electrode, a reflective electrode or a semi-transmissive electrode can be selected. When the anode is a transmissive electrode, the anode material can be selected from indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO) or any combination thereof; when the anode is a semi-transmissive electrode or a reflective electrode, the anode material can be selected from magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag) or any combination thereof.

[0154] As the hole injection layer of the present invention, a material with good hole acceptance ability is preferred. Materials such as metal porphyrins, oligothiophenes, arylamines, hexanitrile hexaazatriphenylenes, quinacridones, and perylene materials can be selected. Specific examples may include 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene (HAT-CN), copper phthalocyanine (CuPC), 4,4',4"-tris(N,N-2-naphthylphenylamino)triphenylamine (2-TNATA), 4,4',4"-tris(N-3-methylphenyl-N-phenylamino)triphenylamine (m-MTDATA), 2,3,5,6-tetrafluoro-7,7',8,8'-tetracyanodimethyl-p-benzoquinone (F4-TCNQ), etc., but are not limited thereto.

[0155] As the hole transport layer of the present invention, a material with high hole mobility is preferred. Materials such as diphenylamine compounds, fluorene compounds, carbazole compounds, and biphenyl diamine compounds can be selected. Specific examples may include N, N'-diphenyl-N, N'-(1-naphthyl)-1, 1'-biphenyl-4, 4'-diamine (NPB), N, N'-diphenyl-N, N'-di(2-naphthyl)-1, 1'-biphenyl-4, 4'-diamine (β-NPB), N, N, N', N'-tetra- 1-naphthyl[1,1'-biphenyl]-4,4'-diamine (α-TNB), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (TPD), 4,4'-cyclohexylbis[N,N-di(4-methylphenyl)aniline] (TAPC), 4,4',4"-tris(carbazol-9-yl)triphenylamine (TCTA), etc., but not limited thereto.

[0156] As the light-emitting layer material of the present invention, red, green or blue light-emitting materials can be used, which usually contain guest (doped) materials and host materials. The guest material can be a simple fluorescent material or a phosphorescent material, or a combination of fluorescent and phosphorescent materials. The host material of the light-emitting layer not only needs to have bipolar charge transfer properties, but also needs an appropriate energy level to effectively transfer the excitation energy to the guest light-emitting material. This type of material can be selected from materials such as distyryl aryl derivatives, isobutylene derivatives, carbazole derivatives, triarylamine derivatives, anthracene derivatives and pyrene derivatives. Specific examples may include 4,4'-bis(9-carbazole)biphenyl (CBP), 9-(4-tert-butylphenyl)-3,6-bis(triphenylsilyl)-9H-carbazole (CZSi), 9 , 9'-(2,6-pyridinediyldi-3,1-phenylene)bis-9H-carbazole (26DCZPPY), 9,9'-diphenyl-9H,9'H-3,3'-bicarbazole (BCzPh), 4,4'-bis(carbazole-9-yl)-2,2'-dimethylbiphenyl (CDBP), 1,3-bis(N-carbazolyl)benzene (MCP), 9,10-di(2-naphthyl)anthracene (ADN), 2-tert-butyl-9,10-di(2-naphthyl)anthracene (TBADN), etc., but not limited thereto. The compound of formula 1 of the present invention is preferred.

[0157] The guest material can be selected from metal complexes (such as iridium complexes, platinum complexes, osmium complexes, rhodium complexes, etc.), anthracene derivatives, pyrene derivatives, perylene derivatives and the like. Specific examples include bis(2-(naphthalene-2-yl)pyridine)(acetylacetonate)iridium (Ir(npy)2acac), bis(2-phenylpyridine)iridium acetylacetonate (Ir(ppy)2(acac)), tris[2-(3-methyl-2-pyridyl)phenyl]iridium (Ir (3mppy)3), bis(2-benzo[H]quinoline-C2,N')(acetylacetonate)iridium (Ir(bzq)2(acac)), bis(1-phenyl-isoquinoline)(acetylacetonate)iridium (Ir(piq)2(acac)), 2,5,8,11-tetra-tert-butylperylene (TBPe), rubrene, 1,4-bis(4-(9H-carbazole-9-yl)phenylvinyl)benzene (BCzSB), etc., but not limited to these.

[0158] As the electron transport layer material of the present invention, a material with high electron mobility is preferred. Specific examples may include quinoline, imidazole, o-phenanthroline, triazole, metal chelate, azabenzene derivative, diazaanthracene derivative, silicon-containing heterocyclic compound, boron-containing heterocyclic compound, cyano, benzimidazole and other materials, but are not limited thereto, and the compound of formula 1 of the present invention is preferred.

[0159] As the hole blocking layer material of the present invention, preferably a material having good electron transport ability and hole blocking ability can be selected, and metal complexes, quinoline derivatives, imidazole derivatives, o-phenanthroline derivatives, triazole derivatives, azobenzene derivatives, etc. can be selected, and specific examples may include bis(2-methyl-8-hydroxyquinoline-N1,O8)-(1,1'-biphenyl-4-hydroxy)aluminum (BAlq), 1,3,5-tri(N-phenyl-2-benzimidazole)benzene (TPBi), 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 3,3'-[5'-[3-(3-pyridyl)phenyl][1,1':3',1"-terphenyl]-3,3"-diyl]bipyridine (TmPyPB), etc., but not limited thereto. Preferably, the compound of formula 1 of the present invention.

[0160] As the electron injection layer material of the present invention, preferably a material with a low work function. Specific examples may include: metal, alkali metal, alkaline earth metal, alkali metal halide, alkaline earth metal halide, alkali metal oxide, alkaline earth metal oxide, alkali metal salt, alkaline earth metal salt, metal complex, etc. Examples may include Li, Ca, Sr, LiF, CsF, CaF2, BaO, Li2CO3, CaCO3, Li2C2O4, Cs2C2O4, CsAlF4, LiOx, Yb, Tb, 8-hydroxyquinoline cesium, tris (8-hydroxyquinoline) aluminum, etc., but are not limited thereto.

[0161] As the cathode of the present invention, a transmissive electrode, a semi-reflective electrode or a reflective electrode can be selected. When the cathode is a transmissive electrode, the cathode material 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 cathode material can be selected from Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF / Ca, LiF / Al, Mo, Ti, including compounds thereof or mixtures thereof (e.g., a mixture of Ag and Mg), but not limited thereto.

[0162] The organic layer of the organic electroluminescent device can be deposited by vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) method, etc. When the vacuum deposition method is used, the vacuum deposition conditions vary depending on the compound.

[0163] The organic electroluminescent device of the present invention is mainly used in the field of information display technology and the field of lighting. In terms of information display, it is widely used in various information displays, such as mobile phones, tablet computers, flat-screen TVs, smart watches, VR, vehicle-mounted systems, digital cameras, wearable devices, etc.

[0164] The production of the organic electroluminescent device is specifically described in the following examples. However, the following examples are only used to illustrate the present specification, and the scope of the present specification is not limited to the examples.

[0165] At the same time, the present invention also provides a method for preparing the compound of formula 1, and the specific synthetic route is as follows, but is not limited thereto:

[0166] When A is a structure of formula 1-a and L is not a single bond, the compound of formula 1 is prepared by synthetic route 1:

[0167] [Route 1]

[0168] When A is a structure of formula 1-a and L is a single bond, the compound of formula 1 is prepared by synthetic route 2:

[0169] [Route 2]

[0170] When A is a structure of formula 1-b and L is not a single bond, the compound of formula 1 is prepared by synthetic route 3:

[0171] [Route 3]

[0172] When A is a structure of formula 1-b and L is a single bond, the compound of formula 1 is prepared by synthetic route 4:

[0173] [Route 4]

[0174] There is no particular restriction on the sources of the raw material A, raw material B, raw material C and raw material D, and they may be commercially available products or prepared by commonly used methods in the art.

[0175] For example, raw material D can be prepared by the following synthetic route:

[0176]

[0177]

[0178] When M is the same as M', the above groups can be introduced simultaneously in one step.

[0179] The M1 is The Xa, Xb, Xc, Xd, Xe, Xf and Xg are independently selected from any one of Cl, Br and I.

[0180] Description of raw materials, reagents and characterization equipment:

[0181] The present invention has no particular limitation on the sources of the raw materials used in the following examples, and the raw materials may be commercially available products or prepared by methods well known to those skilled in the art.

[0182] Mass spectrometry was performed using a British Waters G2-Si quadrupole tandem time-of-flight high-resolution mass spectrometer, with chloroform as the solvent;

[0183] The elemental analysis was performed using a Vario EL cube organic element analyzer from Elementar, Germany, with a sample mass of 5 to 10 mg.

[0184] Synthesis Example 1: Preparation of Intermediate D16

[0185]

[0186] Under nitrogen protection, a16 (39.93 g, 260 mmol), b16 (66.02 g, 260 mmol) were added to the reaction bottle, 1000 mL of DMF was added, and then KOAC (35.33 g, 360 mmol) was added. After nitrogen replaced the air three times, Pd (dppf) Cl2 (1.90 g, 2.6 mmol) was added, and the mixture was heated and stirred for 5 hours. After the reaction was completed, the mixed solution was cooled to room temperature, distilled water was added, and then extracted with dichloromethane (300 mL × 3 times), the organic phase was separated, and dried over anhydrous magnesium sulfate. The crude product was purified with n-hexane: ethyl acetate = 10: 1 (v / v) to obtain M16 (50.98 g, 80%), HPLC purity ≧ 99.88%, mass spectrum m / z: (measured value: 245.1235; theoretical value: 245.1223).

[0187] Under nitrogen protection, c16 (27.03 g, 100 mmol), M16 (49.02 g, 200 mmol) were added to the reaction bottle, 750 mL of toluene / ethanol / water (V toluene: V ethanol: V water = 2:1:1) was added, and then K2CO3 (20.73 g, 150 mmol) was added. After nitrogen replaced the air three times, Pd(PPh3)4 (1.16 g, 1 mmol) was added, and the mixture was stirred and refluxed for 8 hours. After the reaction was completed, the mixed solution was cooled to room temperature, 100 mL of water was added and filtered, and the filtered solid was recrystallized from toluene to obtain compound N16 (21.85 g, yield 63%). HPLC purity ≧ 98.55%. Mass spectrum m / z: (measured value: 346.0502, theoretical value: 346.0509).

[0188] Under nitrogen protection, N16 (20.81 g, 60 mmol), b16 (15.24 g, 60 mmol), 300 mL 1,4-dioxane, and then KOAC (7.36 g, 75 mmol) were added to the reaction bottle. After nitrogen replaced the air three times, Pd (dppf) Cl2 (0.44 g, 0.6 mmol) was added, and the mixture was heated and stirred for 7 hours. After the reaction was completed, the mixed solution was cooled to room temperature, distilled water was added, and then extracted with dichloromethane (300 mL × 3 times), the organic phase was separated, and dried with anhydrous magnesium sulfate. The crude product was purified with n-hexane: ethyl acetate = 8: 1 (v / v) to obtain D16 (22.35 g, 82%), HPLC purity ≧ 99.90%, mass spectrum m / z: (measured value: 454.2056; theoretical value: 454.2064).

[0189] Referring to the synthesis method of intermediate D16, the raw materials a and c in Table 1 were used to replace a16 and c16 in the synthesis step of intermediate D16 in equal moles to synthesize the intermediate compounds shown in Table 1 below:

[0190] Table 1:

[0191]

[0192]

[0193] Synthesis Example 2: Preparation of Compound 5

[0194]

[0195] Under nitrogen protection, A5 (6.52 g, 30 mmol), D'5 (14.97 g, 30 mmol), potassium tert-butoxide (5.05 g, 45 mmol) were added to the reaction flask, and then 200 mL of toluene was added to dissolve it. After nitrogen replaced the air 3 times, Pd2(dba)3 (0.27 g, 0.3 mmol) and X-Phos (0.29 g, 0.6 mmol) were added, and the mixture was heated to reflux for 9 hours. After the reaction was completed, the reaction solution was cooled to room temperature, the solvent was concentrated by vacuum distillation, the filter cake was filtered and then rinsed with ethanol, and the obtained filter cake was recrystallized with ethyl acetate to obtain compound 5 (15.09 g, yield 74%). HPLC purity ≧99.91%. Mass spectrum m / z: 679.2268 (theoretical value: 679.2260). Theoretical element content (%) C 48 H 29 N3O2: C, 84.81; H, 4.30; N, 6.18. Measured element content (%): C, 84.84; H, 4.32; N, 6.15.

[0196] Synthesis Example 3: Preparation of Compound 8

[0197]

[0198] Under nitrogen protection, A8 (10.86 g, 50 mmol), B8 (9.57 g, 50 mmol), sodium tert-butoxide (7.21 g, 75 mmol) were added to the reaction flask, and then 300 mL of toluene was added to dissolve it. After nitrogen replaced the air 3 times, Pd2(dba)3 (0.46 g, 0.5 mmol) and X-Phos (0.48 g, 1.0 mmol) were added and heated to reflux for 5 hours. After the reaction was completed, the reaction solution was cooled to room temperature, the solvent was concentrated by vacuum distillation, the filter cake was filtered and then rinsed with ethanol, and the obtained filter cake was recrystallized with ethyl acetate to obtain intermediate C8 (12.29 g, 75%). HPLC purity ≧99.83%. Mass spectrum m / z: (measured value: 327.0807, theoretical value: 327.0815).

[0199] Under nitrogen protection, C8 (9.83 g, 30 mmol), D8 (13.15 g, 30 mmol), potassium carbonate (6.22 g, 45 mmol) were added to the reaction flask, and then 400 mL of toluene / ethanol / water mixed solvent (V toluene: V ethanol: V water = 2:1:1) was added. After nitrogen replaced the air 3 times, tetrakis(triphenylphosphine)palladium (0.35 g, 0.3 mmol) was added, and the mixture was heated and refluxed for 10 hours. After the reaction was completed, the reaction solution was cooled to room temperature, distilled water was added, suction filtered, and the filter cake was washed with water and methanol in turn. The crude product was recrystallized from toluene to obtain compound 8 (13.95 g, yield 77%). HPLC purity ≧99.96%. Mass spectrum m / z (measured value: 603.1955, theoretical value: 603.1947). Theoretical element content (%) C 42 H 25 N3O2: C, 83.56; H, 4.17; N, 6.96. Measured element content (%): C, 83.54; H, 4.18; N, 6.93.

[0200] Synthesis Example 4: Preparation of Compound 9

[0201]

[0202] Referring to the synthesis of compound 8, B9 was used to replace B8 in an equal molar amount to synthesize compound 9 (13.83 g); HPLC purity ≧99.98%. Mass spectrum m / z: (measured value: 603.1958, theoretical value: 603.1947). Theoretical element content (%) C 42 H 25N3O2: C, 83.56; H, 4.17; N, 6.96. Measured element content (%): C, 83.53; H, 4.15; N, 6.99.

[0203] Synthesis Example 5: Preparation of Compound 16

[0204]

[0205] Referring to the synthesis of compound 8, B16 was substituted for B8 and D16 for D8 in equal molar amounts to synthesize compound 16 (14.82 g); HPLC purity ≧99.90%. Mass spectrum m / z: (measured value: 659.2587, theoretical value: 659.2573). Theoretical element content (%) C 46 H 33 N3O2: C, 83.74; H, 5.04; N, 6.37. Measured element content (%): C, 83.76; H, 5.08; N, 6.34.

[0206] Synthesis Example 6: Preparation of Compound 22

[0207]

[0208] Referring to the synthesis of compound 8, an equal molar amount of A22 was used to replace A8 to synthesize compound 22 (14.11 g); HPLC purity ≧99.97%. Mass spectrum m / z: (measured value: 603.1931, theoretical value: 603.1947). Theoretical element content (%) C 42 H 25 N3O2: C, 83.56; H, 4.17; N, 6.96. Measured element content (%): C, 83.58; H, 4.14; N, 6.94.

[0209] Synthesis Example 7: Preparation of Compound 32

[0210]

[0211] Referring to the synthesis of compound 8, an equal molar amount of A5 was used to replace A8 to synthesize compound 32 (14.29 g); HPLC purity ≧99.98%. Mass spectrum m / z: (measured value: 603.1963, theoretical value: 603.1947). Theoretical element content (%) C 42 H 25 N3O2: C, 83.56; H, 4.17; N, 6.96. Measured element content (%): C, 83.53; H, 4.19; N, 6.95.

[0212] Synthesis Example 8: Preparation of Compound 38

[0213]

[0214] Referring to the synthesis of compound 8, D38 was substituted for D8 in an equal molar amount to synthesize compound 38 (17.21 g); HPLC purity ≧99.94%. Mass spectrum m / z: (measured value: 755.2561, theoretical value: 755.2573). Theoretical element content (%) C 54 H 33 N3O2: C, 85.81; H, 4.40; N, 5.56. Measured element content (%): C, 85.84; H, 4.43; N, 5.54.

[0215] Synthesis Example 9: Preparation of Compound 52

[0216]

[0217] Referring to the synthesis of compound 8, equimolar amounts of A5 were used to replace A8, B52 to replace B8, and D52 to replace D8 to synthesize compound 52 (16.93 g); HPLC purity ≧99.90%. Mass spectrum m / z: (measured value: 763.3083, theoretical value: 763.3075). Theoretical element content (%) C 54 H 25 D8N3O2: C, 84.90; H, 5.41; N, 5.50. Measured element content (%): C, 84.93; H, 5.45; N, 5.47.

[0218] Synthesis Example 10: Preparation of Compound 54

[0219]

[0220] Referring to the synthesis of compound 8, D54 was used in place of D8 in an equal molar amount to synthesize compound 54 (20.13 g); HPLC purity ≧99.88%. Mass spectrum m / z: (measured value: 907.3185, theoretical value: 907.3199). Theoretical element content (%) C 66 H 41 N3O2: C, 87.30; H, 4.55; N, 4.63. Measured element content (%): C, 87.32; H, 4.54; N, 4.60.

[0221] Synthesis Example 11: Preparation of Compound 63

[0222]

[0223] Referring to the synthesis of compound 8, D8 was replaced by an equal molar amount of D63 to synthesize compound 63 (14.85 g); HPLC purity ≧99.97%. Mass spectrum m / z: (measured value: 635.1482, theoretical value: 635.1490). Theoretical element content (%) C 42 H 25 N3S2: C, 79.34; H, 3.96; N, 6.61. Measured element content (%): C, 79.30; H, 3.98; N, 6.60.

[0224] Synthesis Example 12: Preparation of Compound 64

[0225]

[0226] Referring to the synthesis of compound 8, B9 was substituted for B8, and D63 was substituted for D8 in equal molar amounts to synthesize compound 64 (15.04 g); HPLC purity ≧99.96%. Mass spectrum m / z: (measured value: 635.1496, theoretical value: 635.1490). Theoretical element content (%) C 42 H 25 N3S2: C, 79.34; H, 3.96; N, 6.61. Measured element content (%): C, 79.36; H, 3.95; N, 6.64.

[0227] Synthesis Example 13: Preparation of Compound 91

[0228]

[0229] Referring to the synthesis of compound 8, A5 was substituted for A8, and D91 was substituted for D8 in equal molar amounts to synthesize compound 91 (17.25 g); HPLC purity ≧99.87%. Mass spectrum m / z: (measured value: 789.2039, theoretical value: 789.2021). Theoretical element content (%) C 52 H 31 N5S2: C, 79.06; H, 3.96; N, 8.87. Measured element content (%): C, 79.05; H, 3.94; N, 8.85.

[0230] Synthesis Example 14: Preparation of Compound 98

[0231]

[0232] Referring to the synthesis of compound 8, B98 was substituted with an equal molar amount of B8 to synthesize compound 98 (15.27 g); HPLC purity ≧99.93%. Mass spectrum m / z: (measured value: 679.2268, theoretical value: 679.2260). Theoretical element content (%) C 48 H29 N3O2: C, 84.81; H, 4.30; N, 6.18. Measured element content (%): C, 84.82; H, 4.33; N, 6.20.

[0233] Synthesis Example 15: Preparation of Compound 101

[0234]

[0235] Referring to the synthesis of compound 8, B8 was replaced by an equal molar amount of B101 to synthesize compound 101 (15.52 g); HPLC purity ≧99.93%. Mass spectrum m / z: (measured value: 679.2270, theoretical value: 679.2260). Theoretical element content (%) C 48 H 29 N3O2: C, 84.81; H, 4.30; N, 6.18. Measured element content (%): C, 84.80; H, 4.27; N, 6.16.

[0236] Synthesis Example 16: Preparation of Compound 121

[0237]

[0238] Referring to the synthesis of compound 8, equimolar amounts of A5 were used to replace A8 and B98 to replace B8 to synthesize compound 121 (15.68 g); HPLC purity ≧99.92%. Mass spectrum m / z: (measured value: 679.2252, theoretical value: 679.2260). Theoretical element content (%) C 48 H 29 N3O2: C, 84.81; H, 4.30; N, 6.18. Measured element content (%): C, 84.83; H, 4.33; N, 6.16.

[0239] Synthesis Example 17: Preparation of Compound 136

[0240]

[0241] Referring to the synthesis of compound 8, equimolar amounts of A22 were used to replace A8, B136 to replace B8, and D63 to replace D8 to synthesize compound 136 (16.63 g); HPLC purity ≧99.91%. Mass spectrum m / z: (measured value: 711.1809, theoretical value: 711.1803). Theoretical element content (%) C 48 H 29 N3S2: C, 80.98; H, 4.11; N, 5.90. Measured element content (%): C, 80.95; H, 4.12; N, 5.93.

[0242] Synthesis Example 18: Preparation of Compound 174

[0243]

[0244] Referring to the synthesis of compound 8, A22 was used to replace A8, and B174 was used to replace B8 in equal molar amounts to synthesize compound 174 (17.22 g); HPLC purity ≧99.91%. Mass spectrum m / z: (measured value: 755.2557, theoretical value: 755.2573). Theoretical element content (%) C 54 H 33 N3O2: C, 85.81; H, 4.40; N, 5.56. Measured element content (%): C, 85.80; H, 4.44; N, 5.55.

[0245] Synthesis Example 19: Preparation of Compound 175

[0246]

[0247] Referring to the synthesis of compound 8, B175 was used to replace B8 in an equal molar amount to synthesize compound 175 (15.28 g); HPLC purity ≧99.96%. Mass spectrum m / z: (measured value: 653.2113, theoretical value: 653.2103). Theoretical element content (%) C 46 H 27 N3O2: C, 84.51; H, 4.16; N, 6.43. Measured element content (%): C, 84.54; H, 4.17; N, 6.40.

[0248] Synthesis Example 20: Preparation of Compound 185

[0249]

[0250] Referring to the synthesis of compound 8, B185 was used to replace B8 in an equal molar amount to synthesize compound 185 (16.02 g); HPLC purity ≧99.93%. Mass spectrum m / z: (measured value: 703.2272, theoretical value: 703.2260). Theoretical element content (%) C 50 H 29 N3O2: C, 85.33; H, 4.15; N, 5.97. Measured element content (%): C, 85.30; H, 4.17; N, 5.95.

[0251] Synthesis Example 21: Preparation of Compound 194

[0252]

[0253] Referring to the synthesis of compound 8, A22 was substituted for A8, and B194 was substituted for B8 in equal molar amounts to synthesize compound 194 (16.15 g); HPLC purity ≧99.86%. Mass spectrum m / z: (measured value: 719.2587, theoretical value: 719.2573). Theoretical element content (%) C 51 H 33 N3O2: C, 85.10; H, 4.62; N, 5.84. Measured element content (%): C, 85.13; H, 4.61; N, 5.87.

[0254] Synthesis Example 22: Preparation of Compound 199

[0255]

[0256] Referring to the synthesis of compound 8, A5 was substituted for A8, and B199 was substituted for B8 in equal molar amounts to synthesize compound 199 (16.11 g); HPLC purity ≧99.94%. Mass spectrum m / z: (measured value: 693.2040, theoretical value: 693.2052). Theoretical element content (%) C 48 H 27 N3O3: C, 83.10; H, 3.92; N, 6.06. Measured element content (%): C, 83.11; H, 3.95; N, 6.03.

[0257] Synthesis Example 23: Preparation of Compound 208

[0258]

[0259] Referring to the synthesis of compound 8, A5 was substituted for A8, and B208 was substituted for B8 in equal molar amounts to synthesize compound 208 (14.13 g); HPLC purity ≧99.97%. Mass spectrum m / z: (measured value: 604.1891, theoretical value: 604.1899). Theoretical element content (%) C 41 H 24 N4O2: C, 81.44; H, 4.00; N, 9.27. Measured element content (%): C, 81.47; H, 4.02; N, 9.25.

[0260] Synthesis Example 24: Preparation of Compound 220

[0261]

[0262] Referring to the synthesis of compound 8, B220 was used to replace B8 in an equal molar amount to synthesize compound 220 (16.33 g); HPLC purity ≧99.92%. Mass spectrum m / z: (measured value: 729.2422, theoretical value: 729.2416). Theoretical element content (%) C 52 H 31 N3O2: C, 85.58; H, 4.28; N, 5.76. Measured element content (%): C, 85.55; H, 4.30; N, 5.73.

[0263] Synthesis Example 25: Preparation of Compound 225

[0264]

[0265] Referring to the synthesis of compound 8, B225 was substituted with an equal molar amount of B8 to synthesize compound 225 (15.22 g); HPLC purity ≧99.91%. Mass spectrum m / z: (measured value: 705.2150, theoretical value: 705.2165). Theoretical element content (%) C 48 H 27 N5O2: C, 81.69; H, 3.86; N, 9.92. Measured element content (%): C, 81.67; H, 3.88; N, 9.90.

[0266] Synthesis Example 26: Preparation of Compound 280

[0267]

[0268] Referring to the synthesis of compound 8, equimolar amounts of A22 were used to replace A8, B280 to replace B8, and D280 to replace D8 to synthesize compound 280 (15.07 g); HPLC purity ≧99.89%. Mass spectrum m / z: (measured value: 679.1878, theoretical value: 679.1864). Theoretical element content (%) C 43 H 29 N5S2: C, 75.97; H, 4.30; N, 10.30. Measured element content (%): C, 75.95; H, 4.33; N, 10.28.

[0269] Synthesis Example 27: Preparation of Compound 289

[0270]

[0271] Referring to the synthesis of compound 8, equimolar amounts of A5 were used to replace A8, B289 to replace B8, and D63 to replace D8 to synthesize compound 289 (15.84 g); HPLC purity ≧99.90%. Mass spectrum m / z: (measured value: 712.1740, theoretical value: 712.1755). Theoretical element content (%) C 47 H 28 N4S2: C, 79.19; H, 3.96; N, 7.86. Measured element content (%): C, 79.21; H, 3.94; N, 7.83.

[0272] Synthesis Example 28: Preparation of Compound 304

[0273]

[0274] Referring to the synthesis of compound 8, an equal amount of A304 was used to replace A8 to synthesize compound 304 (15.08 g); HPLC purity ≧99.95%. Mass spectrum m / z: (measured value: 653.2110, theoretical value: 653.2103). Theoretical element content (%) C 46 H 27 N3O2: C, 84.51; H, 4.16; N, 6.43. Measured element content (%): C, 84.52; H, 4.12; N, 6.45.

[0275] Synthesis Example 29: Preparation of Compound 307

[0276]

[0277] Referring to the synthesis of compound 5, an equal amount of A307 was used to replace A5, and an equal amount of D'307 was used to replace D'5 to synthesize compound 307 (15.78 g); HPLC purity ≧99.90%. Mass spectrum m / z: (measured value: 731.2309, theoretical value: 731.2321). Theoretical element content (%) C 50 H 29 N5O2: C, 82.06; H, 3.99; N, 9.57. Measured element content (%): C, 82.02; H, 3.95; N, 9.60.

[0278] Synthesis Example 30: Preparation of Compound 313

[0279]

[0280] Referring to the synthesis of compound 8, an equal molar amount of A313 was used to replace A8 to synthesize compound 313 (14.92 g); HPLC purity ≧99.91%. Mass spectrum m / z: (measured value: 653.2109, theoretical value: 653.2103). Theoretical element content (%) C 46 H 27 N3O2: C, 84.51; H, 4.16; N, 6.43. Measured element content (%): C, 84.53; H, 4.15; N, 6.46.

[0281] Synthesis Example 31: Preparation of Compound 327

[0282]

[0283] Referring to the synthesis of compound 8, an equal amount of A307 was used to replace A8 to synthesize compound 327 (15.47 g); HPLC purity ≧99.93%. Mass spectrum m / z: (measured value: 653.2115, theoretical value: 653.2103). Theoretical element content (%) C 46 H 27 N3O2: C, 84.51; H, 4.16; N, 6.43. Measured element content (%): C, 84.50; H, 4.13; N, 6.41.

[0284] Synthesis Example 32: Preparation of Compound 345

[0285]

[0286] Referring to the synthesis of compound 8, A345 was substituted for A8 and B345 for B8 in equal molar amounts to synthesize compound 345 (15.53 g); HPLC purity ≧99.90%. Mass spectrum m / z: (measured value: 707.2529, theoretical value: 707.2511). Theoretical element content (%) C 50 H 25 D4N3O2: C, 84.84; H, 4.70; N, 5.94. Measured element content (%): C, 84.87; H, 4.72; N, 5.90.

[0287] Synthesis Example 33: Preparation of Compound 399

[0288]

[0289] Referring to the synthesis of compound 8, B9 was substituted for B8 and D399 for D8 in equal molar amounts to synthesize compound 399 (19.56 g); HPLC purity ≧99.86%. Mass spectrum m / z: (measured value: 907.3189, theoretical value: 907.3199). Theoretical element content (%) C66 H 41 N3O2: C, 87.30; H, 4.55; N, 4.63. Measured element content (%): C, 87.28; H, 4.57; N, 4.60.

[0290] Synthesis Example 34: Preparation of Compound 417

[0291]

[0292] Under nitrogen protection, C417 (9.83 g, 30 mmol), D8 (13.15 g, 30 mmol), K3PO4 (9.55 g, 45 mmol) were added to the reaction bottle, and then 400 mL of toluene / ethanol / water mixed solvent (V toluene: V ethanol: V water = 2:1:1) was added. After nitrogen replaced the air 3 times, Pd(PPh3)4 (0.58 g, 0.5 mmol) was added, and the mixture was heated and refluxed for 6 hours. After the reaction was completed, the reaction solution was cooled to room temperature, distilled water was added, filtered, and the filter cake was washed with water and methanol in turn. The crude product was recrystallized from toluene to obtain compound 417 (13.76 g, yield 76%). HPLC purity ≧ 99.95%. Mass spectrum m / z (measured value: 603.1935, theoretical value: 603.1947). Theoretical element content (%) C 42 H 25 N3O2: C, 83.56; H, 4.17; N, 6.96. Measured element content (%): C, 83.57; H, 4.14; N, 6.93.

[0293] Synthesis Example 35: Preparation of Compound 419

[0294]

[0295] Under nitrogen protection, A419 (16.86 g, 50 mmol), B8 (9.57 g, 50 mmol), K2CO3 (10.37 g, 75 mmol) were added to the reaction bottle, and then 300 mL of tetrahydrofuran and 100 mL of water were added to dissolve it. After nitrogen replaced the air 3 times, Pd (PPh3) 4 (0.87 g, 0.75 mmol) was added and heated to reflux for 7.5 hours. After the reaction was completed, the reaction solution was cooled to room temperature, distilled water was added, extracted with dichloromethane (300 mL × 3 times), and the liquid was separated by standing. The organic phase was collected and dried with anhydrous magnesium sulfate, filtered, and the filtrate was concentrated by vacuum distillation. The temperature was lowered for crystallization, suction filtered, and the obtained solid was recrystallized with toluene to obtain intermediate C419 (14.54 g, 72%). HPLC purity ≧ 99.85%. Mass spectrum m / z: (measured value: 403.1114, theoretical value: 403.1128).

[0296] Under nitrogen protection, C419 (12.12 g, 30 mmol), D8 (13.15 g, 30 mmol), K3PO4 (9.55 g, 45 mmol) were added to the reaction bottle, and then 400 mL of toluene / ethanol / water mixed solvent (V toluene: V ethanol: V water = 2:1:1) was added. After nitrogen replaced the air 3 times, Pd (dppf) Cl2 (0.37 g, 0.5 mmol) was added, and the mixture was heated and refluxed for 8 hours. After the reaction was completed, the reaction solution was cooled to room temperature, distilled water was added, filtered, and the filter cake was washed with water and methanol in turn. The crude product was recrystallized from toluene to obtain compound 419 (15.30 g, yield 75%). HPLC purity ≧ 99.92%. Mass spectrum m / z (measured value: 679.2265, theoretical value: 679.2260). Theoretical element content (%) C 48 H 29 N3O2: C, 84.81; H, 4.30; N, 6.18. Measured element content (%): C, 84.78; H, 4.33; N, 6.16.

[0297] Synthesis Example 36: Preparation of Compound 434

[0298]

[0299] Referring to the synthesis of compound 419, an equal amount of A434 was used to replace A419 to synthesize compound 434 (15.27 g); HPLC purity ≧99.95%. Mass spectrum m / z: (measured value: 679.2272, theoretical value: 679.2260). Theoretical element content (%) C 48 H 29 N3O2: C, 84.81; H, 4.30; N, 6.18. Measured element content (%): C, 84.83; H, 4.27; N, 6.19.

[0300] Synthesis Example 37: Preparation of Compound 446

[0301]

[0302] Referring to the synthesis of compound 419, B8 was replaced by an equal molar amount of B98 to synthesize compound 446 (16.72 g); HPLC purity ≧99.92%. Mass spectrum m / z: (measured value: 755.2561, theoretical value: 755.2573). Theoretical element content (%) C 54 H 33 N3O2: C, 85.81; H, 4.40; N, 5.56. Measured element content (%): C, 85.82; H, 4.38; N, 5.59.

[0303] Synthesis Example 38: Preparation of Compound 480

[0304]

[0305] Referring to the synthesis of compound 419, A480 was substituted for A419 and B480 for B8 in equal molar amounts to synthesize compound 480 (16.95 g); HPLC purity ≧99.88%. Mass spectrum m / z: (measured value: 769.2370, theoretical value: 769.2365). Theoretical element content (%) C 54 H 31 N3O3: C, 84.25; H, 4.06; N, 5.46. Measured element content (%): C, 84.22; H, 4.09; N, 5.45.

[0306] Synthesis Example 39: Preparation of Compound 488

[0307]

[0308] Referring to the synthesis of compound 419, B208 was used to replace B8 in an equal molar amount to synthesize compound 488 (15.50 g); HPLC purity ≧99.95%. Mass spectrum m / z: (measured value: 680.2220, theoretical value: 680.2212). Theoretical element content (%) C 47 H 28 N4O2: C, 82.92; H, 4.15; N, 8.23. Measured element content (%): C, 82.90; H, 4.18; N, 8.24.

[0309] Synthesis Example 40: Preparation of Compound 540

[0310]

[0311] Referring to the synthesis of compound 419, an equal amount of A540 was used to replace A8, and an equal amount of D63 was used to replace D8 to synthesize compound 540 (16.42 g); HPLC purity ≧99.94%. Mass spectrum m / z: (measured value: 711.1815, theoretical value: 711.1803). Theoretical element content (%) C 48 H 29 N3S2: C, 80.98; H, 4.11; N, 5.90. Measured element content (%): C, 80.96; H, 4.09; N, 5.93.

[0312] Synthesis Example 41: Preparation of Compound 594

[0313]

[0314] Referring to the synthesis of compound 419, A594 was used to replace A8 and B9 to replace B8 in equal molar amounts to synthesize compound 594 (16.38 g); HPLC purity ≧99.90%. Mass spectrum m / z: (measured value: 729.2428, theoretical value: 729.2416). Theoretical element content (%) C 52 H 31 N3O2: C, 85.58; H, 4.28; N, 5.76. Measured element content (%): C, 85.55; H, 4.30; N, 5.78.

[0315] Synthesis Example 42: Preparation of Compound 649

[0316]

[0317] Referring to the synthesis of compound 419, an equal amount of A649 was used to replace A8, an equal amount of B649 was used to replace B8, and an equal amount of D63 was used to replace D8 to synthesize compound 649 (17.27 g); HPLC purity ≧99.87%. Mass spectrum m / z: (measured value: 811.2122, theoretical value: 811.2116).

[0318] Theoretical element content (%) C 56 H 33 N3S2: C, 82.83; H, 4.10; N, 5.17. Measured element content (%): C, 82.85; H, 4.13; N, 5.15.

[0319] Synthesis Example 43: Preparation of Compound 673

[0320]

[0321] Referring to the synthesis of compound 8, D8 was replaced by an equal molar amount of D673 to synthesize compound 673 (17.62 g); HPLC purity ≧99.95%. Mass spectrum m / z: (measured value: 753.2880, theoretical value: 753.2892. Theoretical element content (%) C 54 H 35 N5: C, 86.03; H, 4.68; N, 9.29. Measured element content (%): C, 86.06; H, 4.65; N, 9.31.

[0322] Synthesis Example 44: Preparation of Compound 784

[0323]

[0324] Referring to the synthesis of compound 8, an equal amount of A784 was used to replace A8, and an equal amount of D63 was used to replace D8 to synthesize compound 784 (14.88 g); HPLC purity ≧99.97%. Mass spectrum m / z: (measured value: 636.1455, theoretical value: 636.1442. Theoretical element content (%) C 41 H 24 N4S2: C, 77.33; H, 3.80; N, 8.80. Measured element content (%): C, 77.35; H, 3.76; N, 8.84.

[0325] Device Example:

[0326] Test conditions: A joint IVL test system consisting of test software, computer, K2400 digital source meter produced by Keithley Company of the United States and PR788 spectrum scanning luminance meter produced by Photo Research Company of the United States was used to test the driving voltage and luminous efficiency of organic electroluminescent devices. The life of organic electroluminescent devices was tested using the M6000 OLED life test system produced by McScience Company.

[0327] The test environment is atmospheric environment, the temperature is room temperature; at 10mA / cm 2 The driving voltage, luminous efficiency and the time required for the brightness to decrease to 95% of the initial brightness (T95) were measured at a current density of 1.5 %.

[0328] Test preparation: Wash the ITO (10nm) / Ag (100nm) / ITO (10nm) glass substrate or ITO glass substrate in distilled water twice, ultrasonically wash for 30 minutes, and then repeatedly wash it with distilled water twice, ultrasonically wash for 10 minutes. After the distilled water washing is completed, use isopropanol, acetone, and methanol solvents to ultrasonically wash in sequence, dry it on a hot plate heated to 120°C, and transfer the dried substrate to a plasma cleaner for washing for 5 minutes.

[0329] The functional layer compounds required for preparing organic electroluminescent devices are as follows:

[0330]

[0331]

[0332] Device Example 1: Preparation of red organic electroluminescent device

[0333] The cleaned ITO (10 nm) / Ag (100 nm) / ITO (10 nm) glass substrate was transferred to an evaporator, and then HI-1 and HT-1 with a film thickness of 10 nm were evaporated on the glass substrate as a hole injection layer (the mass ratio of HI-1 to HT-1 was 3:97), HT-1 with a film thickness of 120 nm was evaporated on the hole injection layer as a hole transport layer, HT-2 with a film thickness of 60 nm was vacuum-deposited on the hole transport layer as a luminescent auxiliary layer, and a luminescent layer with a film thickness of 20 nm was vacuum-deposited on the luminescent auxiliary layer, wherein the luminescent layer contained the compound 5 of the present invention as the first host material, RH-1 as the second host material, and RD- 1 as a doping material (the mass ratio of compound 1, RH-1 and RD-1 is 49:49:2), then ET-2 with a thickness of 5 nm is evaporated on the light-emitting layer as a hole blocking layer, ET-1 and Liq with a thickness of 30 nm are vacuum evaporated on the hole blocking layer as an electron transport layer (the mass ratio of ET-1 to Liq is 1:1), Yb with a thickness of 1 nm is evaporated on the electron transport layer as an electron injection layer, and then Mg:Ag (the mass ratio of Mg to Ag is 1:9) alloy with a thickness of 15 nm is evaporated on the electron injection layer as a cathode, and then CP-1 with a thickness of 70 nm is evaporated on the cathode as a covering layer, thereby preparing an organic electroluminescent device.

[0334] Device Example 2 to Device Example 42: Preparation of Red Organic Electroluminescent Device

[0335] Compound 8, compound 9, compound 16, compound 22, compound 32, compound 38, compound 52, compound 54, compound 63, compound 64, compound 91, compound 98, compound 101, compound 121, compound 136, compound 174, compound 175, compound 185, compound 194, compound 199, compound 208, compound 220, compound 225, compound 280, compound 289, compound 304, compound 307, compound 313, compound 327, compound 345, compound 399, compound 417, compound 419, compound 434, compound 446, compound 480, compound 540, compound 594, compound 649 and compound 673 of the present invention are used to replace compound 5 in device embodiment 1 as the first host material, except that an organic electroluminescent device is prepared by the same preparation method as device embodiment 1.

[0336] Comparative Examples 1 to 3: Preparation of red organic electroluminescent devices

[0337] An organic electroluminescent device was prepared by the same preparation method as in Device Example 1 except that Compound D-1, Compound D-2 and Compound D-9 were used to replace Compound 5 in Device Example 1 as the first host material.

[0338] Table 2: Test results of luminescent properties of organic electroluminescent devices 1 to 42 and organic electroluminescent devices obtained in comparative examples 1 to 2

[0339]

[0340]

[0341] According to the results in Table 2 of the present invention, when the organic compound containing carbazole provided by the present invention is applied to the light-emitting layer of an organic electroluminescent device, the driving voltage can be reduced, and the light-emitting efficiency and the life of the device can be significantly improved.

[0342] Device Example 43: Preparation of Blue Light Organic Electroluminescent Device

[0343] The cleaned ITO glass substrate was transferred to an evaporator, and HI-1 and HT-1 with a film thickness of 10 nm were evaporated on the ITO glass substrate as a hole injection layer (the mass ratio of HI-1 to HT-1 was 3:97), HT-1 with a film thickness of 120 nm was evaporated on the hole injection layer as a hole transport layer, HT-3 with a film thickness of 5 nm was vacuum evaporated on the hole transport layer as a light-emitting auxiliary layer, and a light-emitting layer with a film thickness of 20 nm was vacuum evaporated on the light-emitting auxiliary layer, and the light-emitting layer contained BH-1 as a main material , BD-1 is used as a doping material (the mass ratio of BH-1 to BD-1 is 98:2), and then 5 nm of the compound 5 of the present invention is vacuum evaporated on the light-emitting layer as a hole blocking layer, 30 nm of ET-1 and Liq are evaporated on the hole blocking layer as an electron transport layer (the mass ratio of ET-1 to Liq is 1:1), on the electron transport layer, LiF with a film thickness of 1 nm is evaporated as an electron injection layer, and then Al with a film thickness of 130 nm is evaporated on the electron injection layer as a cathode, thereby preparing an organic electroluminescent device.

[0344] Device Examples 44 to 85: Preparation of Blue Organic Electroluminescent Devices

[0345] Organic electroluminescent devices were prepared by the same preparation method as in Device Example 43, except that the compounds of the present invention in Table 3 were used to replace Compound 5 in Device Example 43 as hole blocking layer materials.

[0346] Comparative Examples 4-5:

[0347] An organic electroluminescent device was prepared by the same preparation method as in Device Example 43, except that Compound D-3 and Compound D-4 were used to replace Compound 5 in Device Example 43 as the hole blocking layer material.

[0348] Table 3: Test results of luminescent properties of organic electroluminescent devices 43 to 85 and organic electroluminescent devices obtained in comparative examples 3 to 4

[0349]

[0350]

[0351] According to the results in Table 3 of the present invention, when the organic compound containing carbazole provided by the present invention is applied to the hole blocking layer of an organic electroluminescent device, the driving voltage can be reduced, and the luminous efficiency and life of the device can be significantly improved.

[0352] Device Example 86: Preparation of Blue Light Organic Electroluminescent Device

[0353] The cleaned ITO glass substrate was transferred to an evaporation machine, and HI-1 and HT-1 with a film thickness of 10 nm were evaporated on the ITO glass substrate as a hole injection layer (the mass ratio of HI-1 to HT-1 was 3:97), HT-1 with a film thickness of 120 nm was evaporated on the hole injection layer as a hole transport layer, HT-3 with a film thickness of 5 nm was vacuum evaporated on the hole transport layer as a light-emitting auxiliary layer, and a light-emitting layer with a film thickness of 20 nm was vacuum evaporated on the light-emitting auxiliary layer, the light-emitting layer comprising BH-1 as a main material and BD-1 as a doping material (the mass ratio of BH-1 to BD-1 was 3:97). The method comprises the following steps: vacuum evaporating 5 nm of ET2 on the light-emitting layer as a hole blocking layer, vacuum evaporating 30 nm of ET-1 and Liq on the hole blocking layer as an electron transport layer (the mass ratio of ET-1 to Liq is 1:1), and on the electron transport layer, 1 nm of Yb is evaporated as an electron injection layer, and then 15 nm of Mg:Ag (the mass ratio of Mg to Ag is 1:9) alloy is evaporated on the electron injection layer as a cathode, and then 70 nm of the compound of the present invention 5 is evaporated on the cathode as a covering layer, thereby preparing an organic electroluminescent device.

[0354] Device Examples 87 to 110: Preparation of Blue Organic Electroluminescent Devices

[0355] Organic electroluminescent devices were prepared by the same preparation method as Device Example 86, except that the compounds of the present invention in Table 4 were used to replace Compound 5 in Device Example 53 as the covering layer material.

[0356] Comparative Examples 6 to 9:

[0357] An organic electroluminescent device was prepared by the same preparation method as Device Example 86, except that Compound D-5, Compound D-6, Compound D-7 and Compound D-8 were used to replace Compound 5 in Device Example 86 as the covering layer material.

[0358] Table 4: Test results of luminescent properties of organic electroluminescent devices 85-110 and organic electroluminescent devices obtained in comparative examples 6-9

[0359]

[0360] According to the results in Table 4, compared with the comparative example, when the organic compound containing carbazole provided by the present invention is applied to the covering layer of the organic electroluminescent device, the luminous efficiency and life of the organic electroluminescent device are significantly improved.

[0361] It should be noted that the present invention is particularly described using individual embodiments. However, without departing from the principles of the present invention, a person skilled in the art may make various improvements in form or detail to the present invention, and these improvements also fall within the scope of protection of the present invention.

Claims

1. An organic compound containing carbazole, characterized in that The structure of the organic compound is represented by Formula 1: The A is selected from the structure represented by Formula 1-a or Formula 1-b; In Formula 1-a and Formula 1-b, the T is independently selected from CH or N atoms; The ring E1 is selected from any one of the following structures: The ring E2 is selected from any one of the following structures: The V is independently selected from CH or N atoms, and at least one V in each group is selected from N atoms; The R1 is independently selected from any one of hydrogen, deuterium, cyano, nitro, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl; or two adjacent R1 are connected to form a substituted or unsubstituted ring; The R4 is independently selected from any one of hydrogen, deuterium, cyano, nitro, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl; The n0 is independently selected from 0, 1, 2, 3 or 4, the n1 is independently selected from 0, 1, 2, 3, 4, 5 or 6, the n2 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8, the n3 is independently selected from 0, 1 or 2; the n4 is independently selected from 0, 1, 2, 3, 4 or 5, the n5 is independently selected from 0, 1, 2, 3, 4, 5, 6 or 7; Ar0 is selected from any one of hydrogen, deuterium, cyano, nitro, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl; The X is independently selected from any one of O, S, and N(R5); the Y is independently selected from CH or N; The R2 is independently selected from any one of hydrogen, deuterium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl; The R3 and R5 are independently selected from any one of hydrogen, deuterium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl; or two adjacent R3 are connected to form a substituted or unsubstituted ring; The m1 is selected from 0, 1, 2 or 3, and the m2 is independently selected from 0, 1, 2, 3, 4 or 5; The L1 is selected from any one of a single bond, a substituted or unsubstituted C6-C30 arylene group, and a substituted or unsubstituted C2-C30 heteroarylene group; The L2 and L3 are independently selected from a single bond, or selected from any one or a combination of the following groups: The R 10 Any one independently selected from hydrogen, deuterium, cyano, nitro, halogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl; or two adjacent R 10 They are connected to form a substituted or unsubstituted C3-C7 aliphatic ring; The R 11 , R 12 independently selected from any one of hydrogen, deuterium, cyano, nitro, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl; or R 11 , R 12 are connected to form a substituted or unsubstituted ring; The b1 is independently selected from 1, 2, 3 or 4, the b2 is independently selected from 1 or 2, and the b3 is independently selected from 1, 2 or 3.

2. The carbazole-containing organic compound according to claim 1, characterized in that The A is independently selected from any one of the following groups: The definitions of R1, R4, and Ar0 are the same as those in Formula 1-a and Formula 1-b; The n0 is independently selected from 0, 1, 2, 3 or 4, the n1 is independently selected from 0, 1, 2, 3, 4, 5 or 6, the n2 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8, the n3 is independently selected from 0, 1 or 2, the n4 is independently selected from 0, 1, 2 or 3, the n5 is independently selected from 0, 1, 2, 3, 4 or 5, and the n6 is independently selected from 0, 1, 2, 3, 4, 5, 6 or 7.

3. The carbazole-containing organic compound according to claim 1, characterized in that The compound of formula 1 is selected from any one of the following formulas 2-1 to 2-6: The definitions of A, L1, L2, L3, X, Y, R2, R3, m1, and m2 are the same as those in Formula 1.

4. The carbazole-containing organic compound according to claim 1, characterized in that Said Any one selected from the following groups: The R3 is independently selected from any one of hydrogen, deuterium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl; The R3' is independently selected from any one of hydrogen, deuterium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl; The R5 is independently selected from any one of hydrogen, deuterium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl; The m2 is independently selected from 0, 1, 2, 3, 4 or 5, the m3 is independently selected from 0, 1, 2, 3 or 4, the m4 is independently selected from 0, 1, 2 or 3, the m5 is independently selected from 0, 1 or 2, the m6 is independently selected from 0, 1, 2, 3, 4, 5 or 6, the m7 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8, and the m8 is independently selected from 0, 1, 2, 3, 4, 5, 6 or 7.

5. The carbazole-containing organic compound according to claim 1, characterized in that The L1 is selected from a single bond or any one of the following groups: The R6 and R7 are independently selected from any one of hydrogen, deuterium, cyano, nitro, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl; The R8 is independently selected from any one of hydrogen, deuterium, cyano, nitro, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl; or two adjacent R8 are connected to form any one of the following ring structures: The R9 is independently selected from any one of hydrogen, deuterium, cyano, nitro, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl; Said a1 is independently selected from 0, 1, 2, 3 or 4, said a2 is independently selected from 0, 1, 2 or 3, said a3 is independently selected from 0, 1 or 2, said a4 is independently selected from 0, 1, 2, 3, 4, 5 or 6, said a5 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8, and said a6 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10.

6. The carbazole-containing organic compound according to claim 1, characterized in that The L2 and L3 are independently selected from a single bond or any one of the following groups: The R 10 , R 11 independently selected from hydrogen, deuterium, cyano, nitro, halogen, substituted or unsubstituted any one of the following groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, adamantyl, norbornyl, trimethylsilyl, triethylsilyl; The b1 is independently selected from 0, 1, 2, 3 or 4, the b2 is independently selected from 0, 1, 2 or 3, the b3 is independently selected from 0, 1 or 2, the b4 is independently selected from 0, 1, 2, 3, 4, 5 or 6, the b5 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8, and the b6 is selected from 0, 1, 2, 3, 4 or 5.

7. The carbazole-containing organic compound according to claim 1, characterized in that The organic compound is selected from any one of the following structures:

8. 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 anode and the cathode, characterized in that: The organic layer contains one or more of the carbazole-containing organic compounds according to any one of claims 1 to 7.

9. The organic electroluminescent device according to claim 8, characterized in that: The organic layer is located between the anode and the cathode, and the organic layer includes at least one of a light-emitting layer, an electron transport layer, and a hole blocking layer, and at least one of the light-emitting layer, the electron transport layer, and the hole blocking layer includes one or more of the organic compounds containing carbazole according to any one of claims 1 to 7.

10. The organic electroluminescent device according to claim 8, characterized in that: The organic layer is located outside at least one of the anode and the cathode. The organic layer comprises a covering layer. The covering layer comprises one or more of the carbazole-containing organic compounds according to any one of claims 1 to 7.

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