Aza-carbazole compound and organic electroluminescent device thereof

Abstract

The invention provides an aza-carbazole compound and an organic electroluminescent device thereof, and relates to the technical field of organic electroluminescent materials. The aza-carbazole compound shown in the formula 1 has excellent properties such as relatively good electron transport performance, relatively good thermal stability, relatively good film-forming property and relatively high triplet state energy level, and can be used as a light-emitting main body material in the organic electroluminescent device, so that the performance of the device is effectively improved, and the application prospect is wide. The luminous efficiency of the device is improved; and the service life of the device is prolonged. Secondly, the aza-carbazole compound shown in the formula 1 serves as a hole blocking material or an electron transport material in the organic electroluminescent device, the voltage and efficiency of the device are effectively improved, and the service life of the device is effectively prolonged. In addition, the aza-carbazole compound of the formula 1 is used as an n-type charge generation material in the laminated organic electroluminescent device, so that the efficiency of the device is improved, and the service life of the device is prolonged.

Description

Technical Field

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

[0002] Organic light-emitting devices (OLEDs) have attracted widespread attention in recent years due to their good application prospects in the field of flat panel displays. Compared with traditional display technologies, OLEDs have the advantages of self-luminescence, high resolution, high brightness, fast response speed, low power consumption, wide viewing angle, and flexible display. Therefore, they are widely used in mobile phones, TVs, computers, cameras, car displays and other fields, showing unparalleled visual experience and strong market competitiveness.

[0003] Organic electroluminescence has gone through decades, and its device structure has developed from a single-layer structure to today's multi-layer structure. The existing device structure usually includes a cathode, an anode, and a functional layer located between the two electrodes, thus forming a device structure model similar to a "sandwich". Among them, the functional layers between the electrodes mainly include a hole injection layer (HIL), a hole transport layer (HTL), a light-emitting layer (EML), a hole blocking layer (HBL), an electron transport layer (ETL), an electron injection layer (EIL), etc. In addition, there is a charge generation layer (CGL) between the two light-emitting units, and a cover layer (CPL) is introduced on the outside of the cathode and / or anode of the OLED. Organic electroluminescence is an organic semiconductor device that converts electrical energy into light energy. From the working principle, OLED is a dual-injection device, that is, electrons and holes are injected from the cathode and anode respectively, and transported through the hole transport layer and the electron transport layer respectively to reach the light-emitting layer, where they recombine to produce excitons, and the excitons transition to emit light.

[0004] Although OLED technology has made great breakthroughs after continuous development, there are still many problems to be solved, such as reducing the device driving voltage, improving the luminous efficiency, extending the life span, etc. Therefore, it is urgent to develop organic electroluminescent materials with better performance. Summary of the invention

[0005] In view of the problems existing in the prior art, the present invention provides an azacarbazole compound and an organic electroluminescent device thereof.

[0006] The present invention provides an azacarbazole compound represented by the following formula 1:

[0007]

[0008] Wherein, the ring A and the ring B are independently selected from a substituted or unsubstituted C6-C30 aromatic ring, a substituted or unsubstituted 6-30-membered nitrogen-containing heteroaromatic ring, and at least one is a substituted or unsubstituted 6-30-membered nitrogen-containing heteroaromatic ring;

[0009] The Ar1 and Ar2 are independently selected from the following groups:

[0010] The ring C is selected from a substituted or unsubstituted C6-C30 aromatic ring, a substituted or unsubstituted 6-30-membered nitrogen-containing heteroaromatic ring;

[0011] The R0 is selected from one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C6-C60 fused polycyclic group, substituted or unsubstituted C2-C60 heteroaryl;

[0012] Ar is selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C6-C60 fused polycyclic group, substituted or unsubstituted C2-C60 heteroaryl, or the N atom corresponding to Ar is the connection site with L;

[0013] The R's are the same or different and are selected from one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C6-C60 fused polycyclic group, substituted or unsubstituted C2-C60 heteroaryl;

[0014] The i is selected from an integer of 0 to 3;

[0015] The L, L1, and L2 are independently selected from a single bond, a substituted or unsubstituted C6-C60 arylene group, a substituted or unsubstituted C6-C60 condensed polycyclic group, and a substituted or unsubstituted C2-C60 heteroarylene group.

[0016] In addition, the present invention also provides an organic electroluminescent device, wherein the organic electroluminescent device contains the above-mentioned azacarbazole compound of the present invention.

[0017] Beneficial effects: The azacarbazole compound of formula 1 of the present invention has excellent properties such as good electron transport performance, good thermal stability, good film forming properties and high triplet energy level. In an organic electroluminescent device, it is used as a luminescent host material to effectively improve the performance of the device, improve the luminous efficiency of the device and extend the service life of the device. Secondly, the azacarbazole compound of formula 1 of the present invention is used as a hole blocking material or an electron transport material in an organic electroluminescent device, which effectively improves the voltage, efficiency and life of the device. In addition, the azacarbazole compound of formula 1 of the present invention is used as an n-type charge generating material in a stacked organic electroluminescent device to improve the efficiency and life of the device. DETAILED DESCRIPTION

[0018] The present invention is further explained below in conjunction with specific embodiments. It should be understood that these embodiments are only used to illustrate the present invention and are not used to limit the scope of the present invention. After reading the present invention, various equivalent forms of modifications to the present invention by those skilled in the art all fall within the scope of protection required by this application.

[0019] In the compounds of this specification, any atom not designated as a specific isotope is included as any stable isotope of the atom, and includes atoms in both their natural isotopic abundance and unnatural abundance. In the present invention, "H", "hydrogen", "hydrogen atom" refers to isotopes with different neutron numbers, including protium, deuterium, and tritium.

[0020] In the present specification, the halogen includes fluorine, chlorine, bromine and iodine.

[0021] In the present specification, when the position of a substituent on a ring is not fixed, it means that it can be attached to any of the corresponding optional positions of the ring.

[0022] For example, Can be expressed Can be expressed Can be expressed And so on.

[0023] In this specification, when a substituent or a bond at a connection site runs through two or more rings, it indicates that it can be connected to any of the two or more rings, specifically, it can be connected to any of the corresponding optional sites of the ring. For example, Can be expressed Can be expressed And so on.

[0024] In this specification, "two adjacent groups are bonded to form a ring" means that the adjacent groups are bonded to each other and optionally aromatized to form a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocycle. The hydrocarbon ring can be an aliphatic hydrocarbon ring or an aromatic hydrocarbon ring. The heterocycle can include an aliphatic heterocycle or an aromatic heterocycle. The aliphatic hydrocarbon ring can be a saturated aliphatic hydrocarbon ring or an unsaturated aliphatic hydrocarbon ring, and the aliphatic heterocycle can be a saturated aliphatic heterocycle or an unsaturated aliphatic heterocycle. The hydrocarbon ring and the heterocycle can be monocyclic or polycyclic groups. In addition, the ring formed by the combination of adjacent groups can be connected to another ring to form a spiro structure. The following example is shown:

[0025]

[0026] In the present specification, 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, etc., for example, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopentene, cyclohexene, adamantane, norbornane, benzene, naphthalene, phenanthrene, triphenylene, pyridine, pyrimidine, quinoline, isoquinoline, quinazoline, quinoxaline, fluorene, dibenzofuran, dibenzothiophene, carbazole, etc., but are not limited thereto.

[0027] In this specification, the "integer selected from 0 to M" refers to any one of the integers selected from 0 to M, including 0, 1, 2...M-2, M-1, M. For example, the "integer i selected from 0 to 3" means i is selected from 0, 1, 2 or 3. And so on.

[0028] In this specification, the "unsubstituted ZZ group" in the "substituted or unsubstituted ZZ group" means that the hydrogen atom of the "ZZ group" is not replaced by a substituent. For example, the "unsubstituted aryl group" in the "substituted or unsubstituted C6-C60 aryl group" means that the hydrogen atom of the "aryl group" is not replaced by a substituent. And so on.

[0029] In this specification, "CXX to CYY" in "ZZ group of substituted or unsubstituted CXX to CYY" means the number of carbon atoms in the unsubstituted "ZZ group". When the "ZZ group" has a substituent, the number of carbon atoms of the substituent is not included. For example, "C6 to C60" in "C6 to C60 aryl group of substituted or unsubstituted" means the number of carbon atoms in the unsubstituted "aryl group". When the "aryl group" has a substituent, the number of carbon atoms in the substituent is not included. And so on.

[0030] In this specification, the "substituted" in the "substituted or unsubstituted" means that at least one hydrogen atom on the group is replaced by a substituent. When multiple hydrogens are replaced by multiple substituents, the multiple substituents may be the same or different. The position of the hydrogen replaced by the above-mentioned substituent may be any position. The substituent represented by the "substituted" in the above-mentioned "substituted or unsubstituted" includes the following groups, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted C3~C15 heterocyclic group, substituted or unsubstituted C1~C15 alkyl, substituted or unsubstituted C3~C15 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6~C30 aryl, substituted or unsubstituted C6~C30 fused polycyclic group, substituted or unsubstituted C2~C30 heteroaryl, etc. Preferred are the following groups: deuterium, tritium, halogen, cyano, nitro, methyl, ethyl, propyl, butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, bornyl, isobornyl, fencyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl, phenyl, biphenyl, terphenyl, naphthyl, phenanthrenyl, triphenylene, anthracenyl, pyrenyl, fluoranthenyl, The invention also includes benzocyclopropanyl, benzocyclobutanyl, benzocyclobutenyl, dihydroindenyl, indenyl, tetrahydronaphthyl, dihydronaphthyl, benzocycloheptanyl, fluorenyl, benzofluorenyl, benzofuranyl, dibenzofuranyl, benzothiophenyl, dibenzothiophenyl, indolyl, carbazolyl, benzoxazolyl, benzothiazolyl, benzimidazolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, etc. In addition, each of the above substituents may be substituted or unsubstituted, and two adjacent substituents may be bonded to form a ring.

[0031] In this specification, the alkyl group refers to a hydrocarbon group formed by losing a hydrogen atom in an alkane molecule, and the alkyl group includes a straight-chain alkyl group and a branched-chain alkyl group. Examples of the alkyl group may include methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, etc., but are not limited thereto. A chain alkyl group containing more than three carbon atoms includes its isomers, such as a propyl group including a n-propyl group and an isopropyl group, a butyl group including a n-butyl group, a sec-butyl group, an isobutyl group and a tert-butyl group, and so on. The number of carbon atoms in the alkyl group is 1 to 30, preferably 1 to 20, preferably 1 to 15, and more preferably 1 to 10.

[0032] In this specification, the cycloalkyl group refers to a hydrocarbon group formed by removing a hydrogen atom from a cycloalkane molecule, and the cycloalkyl group includes a monocyclic cycloalkyl group, a polycyclic cycloalkyl group, and a bridged ring cycloalkyl group. Examples of the cycloalkyl group may include cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornane, and camphenyl, but are not limited thereto. The cycloalkyl group has 3 to 30 carbon atoms, preferably 3 to 20, preferably 3 to 15, and more preferably 3 to 10.

[0033] In this specification, the "silyl group" refers to -Si(R t )3 groups, wherein each R t The same or different groups are selected from the following groups: hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C6-C60 fused polycyclic group, substituted or unsubstituted C2-C60 heteroaryl, etc. Preferably, each R t the same or different selected from the following groups: hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted cyclopropane, substituted or unsubstituted cyclobutane, substituted or unsubstituted cyclopentane, substituted or unsubstituted cyclohexane, substituted or unsubstituted cycloheptane, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornene The alkyl radicals include substituted or unsubstituted phenyl radicals, substituted or unsubstituted biphenyl radicals, substituted or unsubstituted naphthyl radicals, substituted or unsubstituted dihydroindenyl radicals, substituted or unsubstituted indenyl radicals, substituted or unsubstituted tetrahydronaphthyl radicals, substituted or unsubstituted dihydronaphthyl radicals, substituted or unsubstituted benzocyclobutane radicals, substituted or unsubstituted benzocyclobutenyl radicals, substituted or unsubstituted benzocyclopropane radicals, substituted or unsubstituted pyridyl radicals, substituted or unsubstituted pyrimidyl radicals, substituted or unsubstituted pyrazinyl radicals, substituted or unsubstituted pyridazinyl radicals, etc., but are not limited thereto. Examples may include trimethylsilyl radicals, triethylsilyl radicals, triisopropylsilyl radicals, tri-tert-butylsilyl radicals, dimethylethylsilyl radicals, dimethylisopropylsilyl radicals, dimethyltert-butylsilyl radicals, tricyclopentylsilyl radicals, tricyclohexylsilyl radicals, triphenylsilyl radicals, tribiphenylsilyl radicals, tripyridylsilyl radicals, etc., but are not limited thereto.

[0034] In this specification, the aryl group refers to a general term for a monovalent group remaining after removing a hydrogen atom from the aromatic carbon of an aromatic compound molecule. The aryl group includes a monocyclic aryl group, a polycyclic aryl group, a condensed aryl group, or a combination thereof. Examples of the aryl group may include phenyl, biphenyl, terphenyl, quaterphenyl, pentphenyl, naphthyl, phenanthrenyl, anthracenyl, triphenylene, pyrene, The aryl group may be 6 to 60 carbon atoms, preferably 6 to 30 carbon atoms, preferably 6 to 25 carbon atoms, preferably 6 to 18 carbon atoms, and more preferably 6 to 12 carbon atoms.

[0035] In this specification, the fused polycyclic group refers to a monovalent group including at least two rings, in which at least one aromatic ring and at least one non-aromatic ring are fused to each other. Examples of the fused polycyclic group may include benzocyclopropane, benzocyclobutane, benzocyclobutenyl, dihydroindenyl, indenyl, tetrahydronaphthyl, dihydronaphthyl, benzocycloheptyl, benzocycloheptenyl, etc., but are not limited thereto. The number of carbon atoms in the fused polycyclic group is 6 to 60, preferably 6 to 30, preferably 6 to 25, preferably 6 to 18, and more preferably 6 to 12.

[0036] In this specification, the heteroaryl group refers to a general term for a group in which one or more carbon atoms in an aryl group are replaced by a heteroatom, and the heteroatom includes, but is not limited to, oxygen, sulfur, nitrogen, phosphorus, boron, silicon and the like. The heteroaryl group includes a monocyclic heteroaryl group, a condensed ring heteroaryl group or a combination thereof. Examples of the heteroaryl group may include benzoxazolyl, naphthoxazolyl, phenanthroxazolyl, anthraxazolyl, tribenzoxazolyl, pyridoxazolyl, pyrimidoxazolyl, triazineoxazolyl, benzothiazolyl, benzimidazolyl, benzofuranyl, dibenzofuranyl, benzodibenzofuranyl, benzothienyl, dibenzothienyl, benzodibenzothienyl, indolyl, carbazolyl, benzocarbazolyl, azacarbazolyl, azabenzocarbazolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, etc., but are not limited thereto. The number of carbon atoms in the heteroaryl group may be 2 to 60, preferably 2 to 30, preferably 2 to 25, and more preferably 2 to 18.

[0037] In this specification, the arylene group refers to the general term for a divalent group remaining after two hydrogen atoms are removed from the aromatic carbon of an aromatic compound molecule. The arylene group includes a monocyclic arylene group, a polycyclic arylene group, a condensed ring arylene group, or a combination thereof. Examples of the arylene group may include phenylene, biphenylene, terphenylene, quaterphenylene, pentphenylene, naphthylene, phenanthrenyl, anthracene, triphenylene, pyrene ... The arylene group may include, but is not limited to, fluoranthene, fluoranthene, benzofluorenyl, spiroanthracenefluorenyl, etc. The number of carbon atoms in the arylene group is 6 to 60, preferably 6 to 30, preferably 6 to 25, preferably 6 to 18, and more preferably 6 to 10.

[0038] In this specification, the sub-condensed polycyclic group refers to a divalent group including at least two rings, in which at least one aromatic ring and at least one non-aromatic ring are fused to each other. Examples of the condensed polycyclic group may include benzocyclopropene, benzocyclobutene, benzocyclobutene, indenylene, indenylene, tetrahydronaphthylene, dihydronaphthylene, benzocycloheptylene, benzocycloheptenylene, etc., but are not limited thereto. The number of carbon atoms in the condensed polycyclic group is 6 to 60, preferably 6 to 30, preferably 6 to 25, preferably 6 to 18, and more preferably 6 to 12.

[0039] In this specification, the sub-heteroaryl group refers to a divalent group in which at least one carbon atom in the sub-aryl group is replaced by a heteroatom. The heteroatom is selected from oxygen, sulfur, nitrogen, phosphorus, boron, silicon, etc., but is not limited thereto. The sub-heteroaryl group includes a monocyclic sub-heteroaryl group, a polycyclic sub-heteroaryl group, a condensed ring sub-heteroaryl group, or a combination thereof. Examples of the sub-heteroaryl group may include pyridyl, pyrimidyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, quinoxalyl, o-phenanthroline, benzofuranyl, dibenzofuranyl, benzodibenzofuranyl, benzothienyl, dibenzothienyl, benzodibenzothienyl, carbazolyl, benzocarbazolyl, azacarbazolyl, azabenzocarbazolyl, etc., but are not limited thereto. The heteroarylene group has 2 to 60 carbon atoms, preferably 2 to 30 carbon atoms, preferably 2 to 25 carbon atoms, and more preferably 2 to 18 carbon atoms.

[0040] The present invention provides an azacarbazole compound represented by the following formula 1:

[0041]

[0042] Wherein, the ring A and the ring B are independently selected from a substituted or unsubstituted C6-C30 aromatic ring, a substituted or unsubstituted 6-30-membered nitrogen-containing heteroaromatic ring, and at least one is a substituted or unsubstituted 6-30-membered nitrogen-containing heteroaromatic ring;

[0043] The Ar1 and Ar2 are independently selected from the following groups:

[0044] The ring C is selected from a substituted or unsubstituted C6-C30 aromatic ring, a substituted or unsubstituted 6-30-membered nitrogen-containing heteroaromatic ring;

[0045] The R0 is selected from one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C6-C60 fused polycyclic group, substituted or unsubstituted C2-C60 heteroaryl;

[0046] Ar is selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C6-C60 fused polycyclic group, substituted or unsubstituted C2-C60 heteroaryl, or the N atom corresponding to Ar is the connection site with L;

[0047] The R's are the same or different and are selected from one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C6-C60 fused polycyclic group, substituted or unsubstituted C2-C60 heteroaryl;

[0048] The i is selected from an integer of 0 to 3;

[0049] The L, L1, and L2 are independently selected from a single bond, a substituted or unsubstituted C6-C60 arylene group, a substituted or unsubstituted C6-C60 condensed polycyclic group, and a substituted or unsubstituted C2-C60 heteroarylene group.

[0050] Preferably, the azacarbazole compound of Formula 1 is selected from at least one of the structures shown below:

[0051]

[0052] Preferably, the Ring A and Ring B in are independently selected from one of the following groups:

[0053]

[0054] The V's are the same or different and are selected from C(Rv) or N, and at least one V in ring A or ring B is selected from N, and the Rv's are the same or different and are selected from one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C6-C60 fused polycyclic group, substituted or unsubstituted C2-C60 heteroaryl, or two adjacent Rv's are bonded to each other to form a substituted or unsubstituted ring.

[0055] Preferably, the Ring A and Ring B in are independently selected from one of the groups shown below, and at least one of Ring A or Ring B is a nitrogen-containing heterocycle,

[0056]

[0057]

[0058] The m1 is selected from integers of 0 to 4, the m2 is selected from integers of 0 to 3, the m3 is selected from integers of 0 to 2, the m4 is selected from integers of 0 to 6, the m5 is selected from integers of 0 to 5, the m6 is selected from integers of 0 to 8, and the m7 is selected from integers of 0 to 7;

[0059] The R v the same or different selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 fused polycyclic group, substituted or unsubstituted C2-C30 heteroaryl, or two adjacent R v They are bonded to each other to form a substituted or unsubstituted ring.

[0060] Preferably, the R vthe same or different selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted cyclopropanyl, substituted or unsubstituted cyclobutanyl, substituted or unsubstituted cyclopentanyl, substituted or unsubstituted cyclohexanyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted anthracenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted benzocyclopropanyl, substituted or unsubstituted benzocyclobutanyl, substituted or unsubstituted benzocyclobutenyl, substituted or unsubstituted indanyl, substituted or unsubstituted substituted indenyl, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted dihydronaphthyl, substituted or unsubstituted benzocycloheptanyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted benzofluorenyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted indolyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted benzoxadiazolyl , substituted or unsubstituted benzothiadiazolyl, substituted or unsubstituted benzotriazolyl, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted benzothiazolyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, or two adjacent R v They are bonded to each other to form a substituted or unsubstituted ring.

[0061] Preferably, the Ring C in is selected from one of the following groups,

[0062]

[0063] The E's are the same or different and are selected from C(Re) or N, and the Re's are the same or different and are selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C6-C60 fused polycyclic group, substituted or unsubstituted C2-C60 heteroaryl, or two adjacent Re's are bonded to each other to form a substituted or unsubstituted ring.

[0064] Preferably, the Ring C in is selected from one of the following groups,

[0065]

[0066]

[0067]

[0068] The n1 is selected from an integer of 0 to 4, the n2 is selected from an integer of 0 to 3, the n3 is selected from an integer of 0 to 2, the n4 is selected from an integer of 0 to 6, the n5 is selected from an integer of 0 to 5, the n6 is selected from an integer of 0 to 8, and the n7 is selected from an integer of 0 to 7;

[0069] The R e the same or different selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 fused polycyclic group, substituted or unsubstituted C2-C30 heteroaryl, or two adjacent R e They are bonded to each other to form a substituted or unsubstituted ring.

[0070] Preferably, the R ethe same or different selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted cyclopropanyl, substituted or unsubstituted cyclobutanyl, substituted or unsubstituted cyclopentanyl, substituted or unsubstituted cyclohexanyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted anthracenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted benzocyclopropanyl, substituted or unsubstituted benzocyclobutanyl, substituted or unsubstituted benzocyclobutenyl, substituted or unsubstituted indanyl, substituted or unsubstituted substituted indenyl, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted dihydronaphthyl, substituted or unsubstituted benzocycloheptanyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted benzofluorenyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted indolyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted benzoxadiazolyl , substituted or unsubstituted benzothiadiazolyl, substituted or unsubstituted benzotriazolyl, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted benzothiazolyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, or two adjacent R e bonded to each other to form a substituted or unsubstituted ring;

[0071] The R0 is selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted cyclopropane, substituted or unsubstituted cyclobutane, substituted or unsubstituted cyclopentane, substituted or unsubstituted cyclohexane, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted anthracenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted benzocyclopropanyl, substituted or unsubstituted benzocyclobutanyl, substituted or unsubstituted benzocyclobutenyl, substituted or unsubstituted indanyl, substituted or unsubstituted indenyl, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted dihydronaphthyl, substituted or unsubstituted benzocycloheptanyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted benzofluorenyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted indolyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted benzo The invention can be selected from the group consisting of oxadiazolyl, substituted or unsubstituted benzothiadiazolyl, substituted or unsubstituted benzotriazolyl, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted benzothiazolyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted quinolyl and substituted or unsubstituted isoquinolyl.

[0072] Preferably, the One selected from the following groups,

[0073]

[0074] Preferably, L is selected from a single bond, one of the following groups or a combination thereof,

[0075]

[0076] The Q is the same or different and is selected from C or N;

[0077] Each of the R1 and R2 is the same or different and is selected from one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 fused polycyclic group, substituted or unsubstituted C2-C30 heteroaryl, or two adjacent R1 and R2 are bonded to each other to form a substituted or unsubstituted ring;

[0078] The X is selected from O, S, C(R x )2 or N(R x ), the R x the same or different selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 fused polycyclic group, substituted or unsubstituted C2-C30 heteroaryl, or two adjacent R x bonded to each other to form a substituted or unsubstituted ring;

[0079] The L 01 , L 02 independently selected from a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted benzocyclobutene, a substituted or unsubstituted benzocyclobutenylene, a substituted or unsubstituted indenylene, a substituted or unsubstituted dihydroindenylene, a substituted or unsubstituted dihydronaphthylene, a substituted or unsubstituted tetrahydronaphthylene, a substituted or unsubstituted pyridylene, a substituted or unsubstituted pyrimidylene, a substituted or unsubstituted pyrazinylene, and a substituted or unsubstituted pyridazinylene;

[0080] b and c are selected from integers of 0 to 4, and a is selected from integers of 0 to 6;

[0081] When a is 2 or more, each unit in the brackets is the same or different.

[0082] Preferably, L is selected from a single bond, one of the following groups or a combination thereof,

[0083]

[0084]

[0085] b and c are selected from integers of 0 to 4, b1 and c1 are selected from integers of 0 to 3, b2 and c2 are selected from integers of 0 to 2, c3 is selected from integers of 0 to 6, c4 is selected from integers of 0 to 8, and c5 is selected from integers of 0 to 10;

[0086] Each of the R1 and R2 is the same or different and is selected from one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 fused polycyclic group, substituted or unsubstituted C2-C30 heteroaryl, or two adjacent R1 and R2 are bonded to each other to form a substituted or unsubstituted ring;

[0087] The R c The same or different ones are selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 fused polycyclic group, substituted or unsubstituted C2-C30 heteroaryl;

[0088] The R x the same or different selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 fused polycyclic group, substituted or unsubstituted C2-C30 heteroaryl, or two adjacent R x They are bonded to each other to form a substituted or unsubstituted ring.

[0089] Preferably, L is selected from a single bond, one of the following groups or a combination thereof,

[0090]

[0091]

[0092] b and c are selected from integers of 0 to 4, b1 and c1 are selected from integers of 0 to 3, b2 and c2 are selected from integers of 0 to 2, c3 is selected from integers of 0 to 6, c4 is selected from integers of 0 to 8, and c5 is selected from integers of 0 to 10;

[0093] Each of R1 and R2 is the same or different and is selected from one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 fused polycyclic group, substituted or unsubstituted C2-C30 heteroaryl;

[0094] The R c The same or different ones are selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 fused polycyclic group, substituted or unsubstituted C2-C30 heteroaryl;

[0095] The R x The same or different ones are selected from one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 fused polycyclic group, substituted or unsubstituted C2-C30 heteroaryl.

[0096] Preferably, each of R1 and R2 is the same or different and is selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted cyclopropane, substituted or unsubstituted cyclobutane, substituted or unsubstituted cyclopentane, substituted or unsubstituted cyclohexane, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted anthracenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted benzocyclopropanyl, substituted or unsubstituted benzocyclobutanyl, substituted or unsubstituted benzocyclobutenyl, substituted or unsubstituted substituted or unsubstituted indenyl, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted dihydronaphthyl, substituted or unsubstituted benzocycloheptanyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted benzofluorenyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted indolyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted substituted or unsubstituted benzoxadiazolyl, substituted or unsubstituted benzothiadiazolyl, substituted or unsubstituted benzotriazolyl, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted benzothiazolyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl;

[0097] The R c the same or different selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted cyclopropane, substituted or unsubstituted cyclobutane, substituted or unsubstituted cyclopentane, substituted or unsubstituted cyclohexane, substituted or unsubstituted adamantane substituted or unsubstituted norbornyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted anthracenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted benzocyclopropanyl, substituted or unsubstituted benzocyclobutanyl, substituted or unsubstituted benzocyclobutenyl, substituted or unsubstituted indanyl, substituted or unsubstituted indenyl, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted dihydronaphthyl, substituted or unsubstituted benzocycloheptanyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted benzofluorenyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted indolyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted benzo oxadiazolyl, substituted or unsubstituted benzothiadiazolyl, substituted or unsubstituted benzotriazolyl, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted benzothiazolyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl;

[0098] The R xthe same or different selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted cyclopropane, substituted or unsubstituted cyclobutane, substituted or unsubstituted cyclopentane, substituted or unsubstituted cyclohexane, substituted or unsubstituted adamantane substituted or unsubstituted norbornyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted anthracenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted benzocyclopropanyl, substituted or unsubstituted benzocyclobutanyl, substituted or unsubstituted benzocyclobutenyl, substituted or unsubstituted indanyl, substituted or unsubstituted indenyl, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted dihydronaphthyl, substituted or unsubstituted benzocycloheptanyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted benzofluorenyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted indolyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted benzo The invention can be selected from the group consisting of oxadiazolyl, substituted or unsubstituted benzothiadiazolyl, substituted or unsubstituted benzotriazolyl, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted benzothiazolyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted quinolyl and substituted or unsubstituted isoquinolyl.

[0099] Preferably, L1 and L2 are independently selected from a single bond or a group as shown below:

[0100]

[0101] The Gs are the same or different and are selected from C or N;

[0102] The R3 are the same or different and are selected from one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 fused polycyclic group, substituted or unsubstituted C2-C30 heteroaryl, or two adjacent R3 are bonded to each other to form a substituted or unsubstituted ring;

[0103] The d is selected from an integer of 0 to 4, and the e is selected from an integer of 0 to 4;

[0104] When d is 2 or more, each unit in the brackets is the same or different.

[0105] Preferably, L1 and L2 are independently selected from a single bond, one of the following groups or a combination thereof:

[0106]

[0107] The e is selected from an integer of 0 to 4, the e1 is selected from an integer of 0 to 3, the e2 is selected from an integer of 0 to 2, the e3 is selected from an integer of 0 to 6, the e4 is selected from an integer of 0 to 8, and the e5 is selected from an integer of 0 to 10;

[0108] The R3 are the same or different and are selected from one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 fused polycyclic group, substituted or unsubstituted C2-C30 heteroaryl, or two adjacent R3 are bonded to each other to form a substituted or unsubstituted ring;

[0109] The R e The same or different ones are selected from one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 fused polycyclic group, substituted or unsubstituted C2-C30 heteroaryl.

[0110] Preferably, the R3 are the same or different and are selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted cyclopropane, substituted or unsubstituted cyclobutane, substituted or unsubstituted cyclopentane, substituted or unsubstituted cyclohexane, substituted or unsubstituted adamantane. substituted or unsubstituted norbornyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted anthracenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted benzocyclopropanyl, substituted or unsubstituted benzocyclobutanyl, substituted or unsubstituted benzocyclobutenyl, substituted or unsubstituted indanyl, substituted or unsubstituted indenyl, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted dihydronaphthyl, substituted or unsubstituted benzocycloheptanyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted benzofluorenyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted indolyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted benzoxadiazolyl, substituted or unsubstituted benzo Thiadiazolyl, substituted or unsubstituted benzotriazolyl, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted benzothiazolyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, or two adjacent R3 are bonded to each other to form a substituted or unsubstituted ring;

[0111] The R ethe same or different selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted cyclopropane, substituted or unsubstituted cyclobutane, substituted or unsubstituted cyclopentane, substituted or unsubstituted cyclohexane, substituted or unsubstituted adamantane substituted or unsubstituted norbornyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted anthracenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted benzocyclopropanyl, substituted or unsubstituted benzocyclobutanyl, substituted or unsubstituted benzocyclobutenyl, substituted or unsubstituted indanyl, substituted or unsubstituted indenyl, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted dihydronaphthyl, substituted or unsubstituted benzocycloheptanyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted benzofluorenyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted indolyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted benzo The invention can be selected from the group consisting of oxadiazolyl, substituted or unsubstituted benzothiadiazolyl, substituted or unsubstituted benzotriazolyl, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted benzothiazolyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted quinolyl and substituted or unsubstituted isoquinolyl.

[0112] Preferably, Ar is selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted cyclopropane, substituted or unsubstituted cyclobutane, substituted or unsubstituted cyclopentane, substituted or unsubstituted cyclohexane, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted anthracenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted benzocyclopropanyl, substituted or unsubstituted benzocyclobutanyl, substituted or unsubstituted benzocyclobutenyl, substituted or unsubstituted dihydroindanyl, substituted or unsubstituted indenyl, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted dihydronaphthyl, substituted or unsubstituted benzocycloheptanyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted benzofluorenyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted indolyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted benzoxadiazolyl, substituted or unsubstituted benzothiadiazolyl, substituted or unsubstituted benzotriazolyl, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted benzo The compound is selected from the group consisting of thiazolyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted spirofluoreneoxanthracene, substituted or unsubstituted spirofluorenethioxanthracene, substituted or unsubstituted spirofluoreneazaanthracenyl, substituted or unsubstituted spiroanthracenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted triazine, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, or the N atom corresponding to Ar is the connection site with L.

[0113] Preferably, the R is the same or different and is selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted cyclopropane, substituted or unsubstituted cyclobutane, substituted or unsubstituted cyclopentane, substituted or unsubstituted cyclohexane, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornane, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted anthracenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted benzocyclopropane, substituted or unsubstituted benzocyclobutane, substituted or unsubstituted benzocyclobutenyl, substituted or unsubstituted dihydro indenyl, substituted or unsubstituted indenyl, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted dihydronaphthyl, substituted or unsubstituted benzocycloheptanyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted benzofluorenyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted indolyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted The invention further comprises one of substituted or unsubstituted benzoxadiazolyl, substituted or unsubstituted benzothiadiazolyl, substituted or unsubstituted benzotriazolyl, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted benzothiazolyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted quinolyl and substituted or unsubstituted isoquinolyl.

[0114] Preferably, the azacarbazole compound represented by Formula 1 is selected from at least one of the structures shown below:

[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] Some specific chemical structures of the azacarbazole compounds of Formula 1 of the present invention are listed above, but the present invention is not limited to these listed chemical structures, and all the chemical structures based on the structure of Formula 1 and having substituents as defined above should be included.

[0143] In addition, the present invention also provides an organic electroluminescent device, wherein the organic electroluminescent device contains the above-mentioned azacarbazole compound of the present invention.

[0144] Preferably, the organic electroluminescent device comprises an anode, a cathode and an organic layer located between the anode and the cathode, and the organic layer contains the above-mentioned azacarbazole compound of the present invention.

[0145] Preferably, the organic layer includes a light-emitting region, and the light-emitting region contains the above-mentioned azacarbazole compound of the present invention.

[0146] Preferably, the light-emitting region comprises a host material, and the host material comprises the above-mentioned azacarbazole compound of the present invention.

[0147] Preferably, the organic layer comprises an electron transporting region, and the electron transporting region contains the azacarbazole compound of the present invention.

[0148] Preferably, the electron transport region comprises at least one of a hole blocking layer and an electron transport layer, and at least one of the hole blocking layer and the electron transport layer contains the above-mentioned azacarbazole compound of the present invention.

[0149] Preferably, the electron transport region comprises a hole blocking layer, and the hole blocking layer contains the above-mentioned azacarbazole compound of the present invention.

[0150] Preferably, the electron transport region comprises an electron transport layer, and the electron transport layer contains the azacarbazole compound of the present invention.

[0151] Preferably, the organic layer includes a charge generating layer, and the charge generating layer contains the azacarbazole compound of the present invention.

[0152] Preferably, the charge generation layer comprises an n-type charge generation layer and a p-type charge generation layer, and the n-type charge generation layer contains the azacarbazole compound of the present invention.

[0153] Preferably, the organic electroluminescent device comprises an anode, a cathode, an organic layer between the anode and the cathode, and a covering layer, wherein the covering layer is located outside the cathode and / or outside the anode, and the covering layer contains the above-mentioned azacarbazole compound of the present invention.

[0154] The functional layer of the organic electroluminescent device of the present invention may contain at least one of the following functional layers: hole injection layer, hole transport layer, luminescence auxiliary layer, electron blocking layer, luminescent layer, hole blocking layer, electron transport layer, electron injection layer, charge generation layer, covering layer, etc. All functional layers with hole injection and / or transport properties, electron injection and / or transport properties, luminescent properties, charge generation properties, or light extraction properties should be included. Each functional layer may be composed of a single-layer thin film or a multi-layer thin film, and each thin film may be composed of only one material or a plurality of materials.

[0155] The present invention has no particular limitation on the materials of the thin films in the organic electroluminescent device, and materials known in the art can be used. The organic functional layers of the organic electroluminescent device mentioned above and the electrodes on both sides of the device are introduced below:

[0156] In this specification, the anode has the function of injecting holes, and the anode material needs to have a high work function. The anode includes but is not limited to the materials described below, metals or their alloys, metal oxides, laminated materials, etc. Specific examples may include aluminum (Al), copper (Cu), gold (Au), silver (Ag), platinum (Pt), indium tin oxide (ITO), indium tin oxide / silver / indium tin oxide (ITO / Ag / ITO), etc., but are not limited thereto.

[0157] In this specification, the cathode has the function of injecting electrons, and the cathode material needs to have a low work function. The cathode includes but is not limited to the materials described below, metals or their alloys, laminated materials, etc. Specific examples may include aluminum (Al), magnesium (Mg), silver (Ag), tin (Sn), lead (Pb), ytterbium silver alloy (Yb:Ag), magnesium:silver (Mg:Ag), lithium aluminum alloy (Li:Al), etc., but are not limited thereto.

[0158] In this specification, the hole injection layer has the function of reducing the hole injection barrier between the anode and the hole transport layer. The hole injection material includes but is not limited to the following materials, metal oxides, phthalocyanine compounds, aromatic amine compounds, low molecular weight organic compounds such as conjugated organic materials containing polycyano groups, polymer materials, etc. Specific examples may include tungsten trioxide (WO3), silver oxide (AgO), molybdenum trioxide (MoO3), copper phthalocyanine (CuPc), N4,N4,N4',N4'-tetrakis (4-methoxyphenyl)-[1,1'-biphenyl]-4,4'-diamine (MeO-TPD), 4,4',4"-tri[2-naphthylphenyl]-[1,1'-biphenyl]-4,4'-diamine (MeO-TPD),

[0063] amino] triphenylamine (2-TNATA), 4,4',4"-tris(N-3-methylphenyl-N-phenylamino)triphenylamine (m-MTDATA), 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene (HAT-CN), 2,3,5,6-tetrafluoro-7,7',8,8'-tetracyanodimethyl-p-benzoquinone (F4-TCNQ), poly(3,4-ethylenedioxythiophene) / poly(styrene sulfonic acid) (PEDOT / PSS), etc., but are not limited thereto.

[0159] In this specification, the hole transport layer has the function of injecting holes and balancing carriers. The hole transport layer includes but is not limited to the following materials, aromatic amine derivatives, carbazole derivatives, polymers, etc. Specific examples may include N4,N4-di([1,1'-biphenyl]-4-yl)-N4'-(1-naphthyl)-N4'-phenyl-[1,1'-biphenyl]-4,4'-diamine, N,N,N',N'-tetraphenylbiphenyl diamine (BPBPA), N,N'-diphenyl-N,N'-(1-naphthyl)-1,1'-biphenyl-4,4'-diamine (NPB), N,N'-di(2-naphthyl)-N,N'-diphenyl-1,4-phenylenediamine (β-NPP), N,N'-di(naphthalene-2-yl)-N,N'-di(phenyl)biphenyl-4,4'-diamine (β-NPB), N 4 ,N 4 '-Bis([1,1'-biphenyl]-4-yl)-N 4 ,N 4 '-Diphenyl-[1,1'-biphenyl]-4,4'-diamine (TPD10), 4,4'-cyclohexylbis[N,N-bis(4-methylphenyl)aniline] (TAPC), N,N'-diphenyl-N,N'-bis(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine (TPD), 4,4',4"-tri(carbazole-9-yl)triphenylamine (TCTA), poly(4-vinyltriphenylamine) (PVTPA), etc., but are not limited thereto.

[0160] In this specification, the light-emitting layer includes a main material and a doping material, and the light-emitting material can be a red light-emitting material, a green light-emitting material, a blue light-emitting material or a combination thereof. The doping ratio of the main material and the doping material can be different according to the materials used. Generally, the doping ratio of the doping material is 0.01% to 20%, preferably 0.1% to 15%, and more preferably 1% to 10%.

[0161] The host material of the light-emitting layer not only needs to have bipolar charge transport properties, but also needs an appropriate energy level to effectively transfer the excitation energy to the guest light-emitting material. The host material can be one material or more than two materials. The azacarbazole compound of Formula 1 of the present invention is preferred. The azacarbazole compound of Formula 1 of the present invention can be used as a host material alone or in combination with a p-type host material and / or an n-type host material. When used in combination with a p-type host material and / or an n-type host material, the weight ratio of the azacarbazole compound of Formula 1 of the present invention to the p-type host material and / or the n-type host material is 1:99 to 99:1, preferably 20:80 to 80:20. The main material includes but is not limited to the following materials, heterocyclic compounds, aromatic amine compounds, fused aromatic ring derivatives, metal complexes, silicon-containing compounds, etc. Specific examples may include 9-(4-(naphthalene-2-yl)phenyl)-10-phenylanthracene, 9-(4-(dibenzo[b,d]furan-1-yl)phenyl)-7-phenyl-7,9-dihydrobenzo[g]indol[2,3-b]carbazole, 9,9'-di([1,1'-biphenyl]-4-yl)-9H,9'H-3,3'-bicarbazole, 2,7-bis(9H-carbazole-9-yl)-9,9-dimethylfluorene (DMFL-CBP), 2,7-bis(carbazole-9-yl)-9,9-dimethylfluorene (DMFL-CBP), 2,7-bis(carbazole-1 ... -9-yl)-9,9-spirobifluorene (Spiro-2CBP), 3,3'-bis(N-carbazole)-1,1'-biphenyl (mCBP), 4,4'-bis(N-carbazole)-1,1'-biphenyl (CBP), 3,3'-bis(dibenzothiophene-4-yl)-1,1'-biphenyl (m-BPDBT), 9,10-di-2-naphthothracene (AND), 1,4-bis(9-phenyl-9H-fluorene-9-yl)benzene (pDPFB), tris(8-hydroxyquinoline)aluminum (Alq3), 9-(4-tert-butylphenyl)-3,6-bis(triphenylsilyl)-9H-carbazole (CzSi), etc., but are not limited thereto.

[0162] The doping material may be a fluorescent material, a phosphorescent material, a TADF material or a combination thereof. The doping material includes but is not limited to the following materials, metal complexes, aromatic amine derivatives, styrylamine compounds, fused aromatic compounds, heterocyclic compounds, etc. Specific examples may include N1, N6-bis (6- (tert-butyl) dibenzo [b, d] furan-4-yl) -N1, N6- di-o-tolylpyrene-1, 6-diamine, tris [2- (2, 4-difluorophenyl) pyridine] iridium (Ir (Fppy) 3), bis (3, 5-difluoro-2- (2-pyridyl) phenyl- (2-carboxypyridyl) iridium (FIrPic), acetylacetonate di (2-phenylpyridine) ... r(ppy)2(acac)), tris(2-phenylpyridine)iridium (Ir(ppy)3), tris[2-phenyl-4-methylquinoline)]iridium (Ir(Mphq)3), tris[2-(4-n-hexylphenyl)quinoline)iridium (Hex-Ir(phq)3), bis(1-phenyl-isoquinoline)(acetylacetonate)iridium (Ir(piq)2(acac)), tris(1-phenyl-isoquinoline)iridium (Ir(piq)3), bis(2-phenylquinoline)(2,2,6,6-tetramethylheptane-3,5-diacid)iridium (Ir(dpm)PQ2), bis(phenylisoquinoline)(2,2,6,6-tetramethylheptane-3,5-diacid)iridium (Ir(dpm)(piq)2), bis(2-methyldibenzo[F,H]quinoxaline)(acetylacetonate)iridium (Ir(MDQ)2(acac) )), tris(2-(3,5-dimethylphenyl)quinoline-C2,N')iridium (Ir(dmpq)3), 1,4-bis(4-(9H-carbazole-9-yl)phenylvinyl)benzene (BCzSB), 2,5,8,11-tetra-tert-butylperylene (TBPe), 4-(dicyanomethylidene)-2-methyl-6-(4-dimethylaminophenylvinyl)-4H-pyran (DCM), etc., but are not limited thereto.

[0163] In this specification, the hole blocking layer has the function of blocking holes in the light-emitting layer and improving the binding rate of electrons and holes. The hole blocking layer material may include imidazole derivatives, phenanthroline derivatives, triazole derivatives, rare earth complexes, oxazole derivatives, triazine derivatives, etc., such as 1,3,5-tris (N-phenyl-2-benzimidazole) benzene (TPBi), 4,7-diphenyl-1,10-phenanthroline (Bphen), 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), bis (8-hydroxy-2-methylquinoline) - (4-phenylphenoxy) aluminum (BAlq), etc., but not limited thereto. The azacarbazole compound of formula 1 of the present invention is preferred.

[0164] In this specification, the electron transport layer has the function of injecting electrons and balancing carriers. The electron transport layer includes but is not limited to the following materials, metal complexes, heteroaromatic compounds, etc. Specific examples may include 2-[4-(9,10-dinaphthalene-2-anthracen-2-yl)phenyl]-1-phenyl-1H-benzimidazole, 8-hydroxyquinoline aluminum (Alq3), tris(4-methyl-8-hydroxyquinoline)aluminum (Almq3), 2-(4-biphenyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (PBD), 1,3,5-tris(N-phenyl-2-benzimidazole)benzene (TPBi), 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 1,3,5-tris[(3-pyridyl)-phenyl]benzene (TmPyPB), etc., but are not limited thereto. The azacarbazole compound of formula 1 of the present invention is preferred.

[0165] In this specification, the electron injection layer has the function of reducing the electron injection barrier between the cathode and the electron transport layer. The electron injection layer material includes but is not limited to the following materials, metals, metal compounds, metal oxides, etc. Specific examples may include lithium (Li), ytterbium (Yb), lithium fluoride (LiF), 8-hydroxyquinoline lithium (Liq), cesium fluoride (CsF), cesium carbonate (Cs2CO3), etc., but are not limited thereto.

[0166] In this specification, the charge generation layer serves to connect the two light-emitting units, generate electrons and holes under the action of an external electric field, and transport them to the locations of the first light-emitting layer and the second light-emitting layer through the transport layer, and recombine with the charges injected by the electrode to emit photons. The charge generation layer generally includes an n-type charge generation layer and a p-type charge generation layer. The n-type charge generation layer material is not limited to the following materials, metal compounds, heterocyclic compounds, etc. Specific examples may include tris (8-hydroxyquinoline) aluminum (Alq3), 4,7-diphenyl-1,10-phenanthroline (Bphen), C 60 etc., preferably the azacarbazole compound of Formula 1 of the present invention. In addition, in addition to the above materials, the n-type charge generating material may further include a doping material, the doping material includes but is not limited to the following materials, alkali metals, alkaline earth metals, alkali metal compounds, alkaline earth metal compounds, etc., and specific examples may include lithium (Li), ytterbium (Yb), magnesium (Mg), potassium (K), lithium fluoride (LiF), etc.

[0167] In this specification, the cover layer has the function of coupling out the light trapped in the device. The cover layer material includes but is not limited to the following materials, metal compounds, aromatic amine derivatives, carbazole derivatives, etc. Specific examples may include tris (8-hydroxyquinoline) aluminum (Alq3), N, N'-diphenyl-N, N'-(1-naphthyl)-1, 1'-biphenyl-4, 4'-diamine (NPB), N, N, N', N'-tetrakis (4-methoxyphenyl) benzidine (MeO-TPD), 4, 4'-bis (9-carbazole) biphenyl (CBP), etc. The azacarbazole compound of formula 1 of the present invention is preferred.

[0168] There is no particular limitation on the method for preparing the thin films in the organic electroluminescent device of the present invention, and vacuum evaporation, sputtering, spin coating, spray coating, screen printing, laser transfer, etc. may be used, but are not limited thereto.

[0169] 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.

[0170] Synthesis Example

[0171] Raw materials and reagents: The present invention has no particular restrictions on the raw materials or reagents used in the following synthetic examples, and they can be commercially available products or prepared by preparation methods well known to those skilled in the art. The raw materials and reagents used in the present invention are all reagent-grade.

[0172] Instruments: G2-Si quadrupole tandem time-of-flight high-resolution mass spectrometer (Waters, UK); Vario ELcube organic element analyzer (Elementar, Germany).

[0173] There is no particular limitation on the preparation method of the azacarbazole compound represented by Formula 1 of the present invention, and conventional methods known to those skilled in the art can be used, such as carbon-carbon coupling reaction, carbon-nitrogen coupling reaction, etc. The azacarbazole compound represented by Formula 1 of the present invention can be prepared, for example, by the synthetic route shown below.

[0174]

[0175] The Xn is a halogen, for example, Xn are the same or different and are selected from Cl, Br, and I.

[0176] Synthesis Example 1:

[0177]

[0178] Under nitrogen protection, a-4 (8.11 g, 30.00 mmol), b-4 (15.77 g, 66.00 mmol), potassium carbonate (12.44 g, 90.00 mmol), tetrakistriphenylphosphine palladium (346 mg, 0.30 mmol) and tetrahydrofuran (200 ml) were added to the reaction bottle and stirred for 8 hours under reflux. After the reaction was completed, it was cooled to room temperature, water was added, extracted with dichloromethane, the organic phases were combined, dried with anhydrous magnesium sulfate, the solvent was removed under reduced pressure, and recrystallized with ethyl acetate / petroleum ether (8:1) to obtain A-4 (10.93 g, 73%); HPLC purity ≥99.86%.

[0179] Under nitrogen protection, d-4 (11.77 g, 70.00 mmol), e-4 (13.40 g, 70.00 mmol), sodium tert-butoxide (10.09 g, 105.00 mmol), tridibenzylideneacetone dipalladium (641 mg, 0.70 mmol), tri-tert-butylphosphine (283 mg, 1.40 mmol), toluene (550 ml) were added to the reaction bottle, and the mixture was reacted for 6 hours under reflux. After the reaction was completed, the mixture was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic phases were combined, dried with anhydrous magnesium sulfate, the solvent was removed under reduced pressure, and the mixture was recrystallized with toluene to obtain D-4 (14.83 g, 76%); HPLC purity ≥ 99.91%.

[0180] Under nitrogen protection, D-4 (13.94 g, 50.00 mmol), biboronic acid pinacol ester (15.24 g, 60.00 mmol), potassium acetate (9.81 g, 100.00 mmol), Pd (dppf) Cl2 (366 mg, 0.50 mmol), DMF (350 mL) were added to the reaction bottle, and the mixture was reacted for 7 hours under reflux. After the reaction was completed, the mixture was cooled to room temperature, water was added, and then extracted with dichloromethane. The organic phases were combined, dried with anhydrous magnesium sulfate, the solvent was removed under reduced pressure, and recrystallized with ethyl acetate / petroleum ether (4:1) to obtain E-4 (13.88 g, 75%); HPLC purity ≥ 99.90%.

[0181] Under nitrogen protection, E-4 (11.11 g, 30.00 mmol), A-4 (12.47 g, 25.00 mmol), potassium carbonate (6.91 g, 50.00 mmol), tetrakistriphenylphosphine palladium (289 mg, 0.25 mmol) and tetrahydrofuran (300 ml) were added to the reaction bottle and stirred for 12 hours under reflux conditions. After the reaction was completed, it was cooled to room temperature, water was added, extracted with dichloromethane, the organic phases were combined, dried with anhydrous magnesium sulfate, the solvent was removed under reduced pressure, and recrystallized from toluene to obtain compound 4 (13.78 g, 78%); HPLC purity ≥99.97%. Mass spectrum m / z: 706.2364 (theoretical value: 706.2369). Theoretical element content (%) C 49 H 30 N4O2: C, 83.27; H, 4.28; N, 7.93. Measured element content (%): C, 83.24; H, 4.25; N, 7.97.

[0182] Synthesis Example 2:

[0183]

[0184] According to the preparation method of Synthesis Example 1, b-4 and e-4 were replaced by equimolar amounts of b-14 and e-14, respectively, to obtain compound 14 (13.43 g); HPLC purity ≥ 99.95%. Mass spectrum m / z: 706.2363 (theoretical value: 706.2369). Theoretical element content (%) C 49 H 30 N4O2: C, 83.27; H, 4.28; N, 7.93. Measured element content (%): C, 83.29; H, 4.24; N, 7.96.

[0185] Synthesis Example 3:

[0186]

[0187] According to the preparation method of Synthesis Example 1, b-4 was replaced with an equal molar amount of b-16 to obtain Compound 16 (16.11 g); HPLC purity ≥ 99.96%. Mass spectrum m / z: 858.2988 (theoretical value: 858.2995). Theoretical element content (%) C 61 H 38 N4O2: C, 85.29; H, 4.46; N, 6.52. Measured element content (%): C, 85.25; H, 4.48; N, 6.55.

[0188] Synthesis Example 4:

[0189]

[0190] According to the preparation method of Synthesis Example 1, b-4 was replaced with an equal molar amount of b-17 to obtain Compound 17 (13.29 g); HPLC purity ≥ 99.95%. Mass spectrum m / z: 708.2268 (theoretical value: 708.2274). Theoretical element content (%) C 47 H 28 N6O2: C, 79.65; H, 3.98; N, 11.86. Measured element content (%): C, 79.68; H, 3.95; N, 11.82.

[0191] Synthesis Example 5:

[0192]

[0193] According to the preparation method of Synthesis Example 1, b-4 was replaced with an equal molar amount of b-24 to obtain Compound 24 (14.93 g); HPLC purity ≥ 99.95%. Mass spectrum m / z: 806.2689 (theoretical value: 806.2682). Theoretical element content (%) C 57 H 34 N4O2: C, 84.84; H, 4.25; N, 6.94. Measured element content (%): C, 84.81; H, 4.28; N, 6.97.

[0194] Synthesis Example 6:

[0195]

[0196] According to the preparation method of Synthesis Example 1, e-4 was replaced with an equal molar amount of e-29 to obtain compound 29 (15.66 g); HPLC purity ≥ 99.97%. Mass spectrum m / z: 782.2686 (theoretical value: 782.2682). Theoretical element content (%) C 55 H 34 N4O2: C, 84.38; H, 4.38; N, 7.16. Measured element content (%): C, 84.35; H, 4.36; N, 7.18.

[0197] Synthesis Example 7:

[0198]

[0199] Under nitrogen protection, c-46 (27.61 g, 100.00 mmol), biboric acid pinacol ester (30.47 g, 120.00 mmol), potassium acetate (19.63 g, 200.00 mmol), Pd (dppf) Cl2 (366 mg, 0.50 mmol), DMF (500 mL) were added to the reaction bottle and reacted for 8 hours under reflux conditions. After the reaction was completed, it was cooled to room temperature, water was added, and then extracted with dichloromethane, the organic phases were combined, dried with anhydrous magnesium sulfate, the solvent was removed under reduced pressure, and recrystallized with toluene / ethanol (5:1) to obtain b-46 (23.27 g, 72%); HPLC purity ≥ 99.88%.

[0200] According to the preparation method of Synthesis Example 1, b-4 and e-4 were replaced by equimolar amounts of b-46 and e-29, respectively, to obtain compound 46 (14.36 g); HPLC purity ≥ 99.95%. Mass spectrum m / z: 786.2498 (theoretical value: 786.2492). Theoretical element content (%) C 51 H 30 N8O2: C, 77.85; H, 3.84; N, 14.24. Measured element content (%): C, 77.81; H, 3.82; N, 14.28.

[0201] Synthesis Example 8:

[0202]

[0203] According to the preparation method of Synthesis Example 1, b-4, d-4, and e-4 were replaced by equimolar amounts of b-68, d-68, and e-68, respectively, to obtain compound 68 (15.11 g); HPLC purity ≥ 99.97%. Mass spectrum m / z: 784.2593 (theoretical value: 784.2587). Theoretical element content (%) C 53 H 32 N6O2: C, 81.11; H, 4.11; N, 10.71. Measured element content (%): C, 81.14; H, 4.15; N, 10.68.

[0204] Synthesis Example 9:

[0205]

[0206] According to the preparation method of Synthesis Example 1, d-4 was replaced with an equal molar amount of d-73 to obtain compound 73 (13.45 g); HPLC purity ≥ 99.96%. Mass spectrum m / z: 707.2328 (theoretical value: 707.2321). Theoretical element content (%) C 48 H 29N5O2: C, 81.45; H, 4.13; N, 9.89. Measured element content (%): C, 81.48; H, 4.17; N, 9.85.

[0207] Synthesis Example 10:

[0208]

[0209] According to the preparation method of Synthesis Example 1, b-4 and d-4 were replaced by equimolar amounts of b-82 and d-82, respectively, to obtain compound 82 (11.09 g); HPLC purity ≥ 99.97%. Mass spectrum m / z: 554.1748 (theoretical value: 554.1743). Theoretical element content (%) C 37 H 22 N4O2: C, 80.13; H, 4.00; N, 10.10. Measured element content (%): C, 80.11; H, 4.03; N, 10.08.

[0210] Synthesis Example 11:

[0211]

[0212] According to the preparation method of Synthesis Example 1, b-4, d-4, and e-4 were replaced by equimolar amounts of b-82, d-95, and e-29, respectively, to obtain compound 95 (12.77 g); HPLC purity ≥ 99.97%. Mass spectrum m / z: 630.2049 (theoretical value: 630.2056). Theoretical element content (%) C 43 H 26 N4O2: C, 81.89; H, 4.16; N, 8.88. Measured element content (%): C, 81.86; H, 4.18; N, 8.86.

[0213] Synthesis Example 12:

[0214]

[0215] According to the preparation method of Synthesis Example 1, b-4 and e-4 were replaced by equimolar amounts of b-82 and e-29, respectively, to obtain compound 96 (12.93 g); HPLC purity ≥ 99.98%. Mass spectrum m / z: 630.2060 (theoretical value: 630.2056). Theoretical element content (%) C 43 H 26 N4O2: C, 81.89; H, 4.16; N, 8.88. Measured element content (%): C, 81.87; H, 4.18; N, 8.86.

[0216] Synthesis Example 13:

[0217]

[0218] According to the preparation method of Synthesis Example 1, b-4, d-4, and e-4 were replaced by equimolar amounts of b-82, d-82, and e-99, respectively, to obtain compound 99 (12.61 g); HPLC purity ≥ 99.96%. Mass spectrum m / z: 630.2051 (theoretical value: 630.2056). Theoretical element content (%) C 43 H 26 N4O2: C, 81.89; H, 4.16; N, 8.88. Measured element content (%): C, 81.87; H, 4.19; N, 8.85.

[0219] Synthesis Example 14:

[0220]

[0221] According to the preparation method of Synthesis Example 1, b-4 and e-4 were replaced by equimolar amounts of b-82 and e-108, respectively, to obtain compound 108 (11.67 g); HPLC purity ≥ 99.95%. Mass spectrum m / z: 630.2048 (theoretical value: 630.2056). Theoretical element content (%) C 43 H 26 N4O2: C, 81.89; H, 4.16; N, 8.88. Measured element content (%): C, 81.85; H, 4.18; N, 8.86.

[0222] Synthesis Example 15:

[0223]

[0224] According to the preparation method of Synthesis Example 1, b-4 and e-4 were replaced by equimolar amounts of b-82 and e-109, respectively, to obtain compound 109 (12.53 g); HPLC purity ≥ 99.97%. Mass spectrum m / z: 634.2313 (theoretical value: 634.2307). Theoretical element content (%) C 43 H 22 D4N4O2: C, 81.37; H, 4.76; N, 8.83. Measured element content (%): C, 81.34; H, 4.78; N, 8.86.

[0225] Synthesis Example 16:

[0226]

[0227] According to the preparation method of Synthesis Example 1, b-4 and e-4 were replaced by equimolar amounts of b-82 and e-121, respectively, to obtain compound 121 (14.14 g); HPLC purity ≥ 99.97%. Mass spectrum m / z: 706.2361 (theoretical value: 706.2369). Theoretical element content (%) C 49 H 30 N4O2: C, 83.27; H, 4.28; N, 7.93. Measured element content (%): C, 83.25; H, 4.25; N, 7.96.

[0228] Synthesis Example 17:

[0229]

[0230] Under nitrogen protection, d-4 (4.20 g, 25.00 mmol), A-4 (12.47 g, 25.00 mmol), sodium tert-butoxide (2.88 g, 30.00 mmol), tridibenzylideneacetone dipalladium (229 mg, 0.25 mmol), tri-tert-butylphosphine (101 mg, 0.50 mmol), toluene (300 ml) were added to the reaction bottle, and the mixture was reacted under reflux for 8 hours. After the reaction was completed, the mixture was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic phases were combined, dried with anhydrous magnesium sulfate, the solvent was removed under reduced pressure, and the mixture was recrystallized with toluene to obtain compound 136 (12.14 g, 77%); HPLC purity ≥99.94%. Mass spectrum m / z: 630.2047 (theoretical value: 630.2056). Theoretical element content (%) C 43 H 26 N4O2: C, 81.89; H, 4.16; N, 8.88. Measured element content (%): C, 81.85; H, 4.19; N, 8.84.

[0231] Synthesis Example 18:

[0232]

[0233] According to the preparation method of Synthesis Example 1, b-4 was replaced with an equal molar amount of b-141 to obtain Compound 141 (13.76 g); HPLC purity ≥ 99.97%. Mass spectrum m / z: 706.2362 (theoretical value: 706.2369). Theoretical element content (%) C 49 H 30 N4O2: C, 83.27; H, 4.28; N, 7.93. Measured element content (%): C, 83.24; H, 4.26; N, 7.97.

[0234] Synthesis Example 19:

[0235]

[0236] According to the preparation method of Synthesis Example 1, b-4, d-4, and e-4 were replaced by equimolar amounts of b-161, d-82, and e-161, respectively, to obtain Compound 161 (15.07 g); HPLC purity ≥ 99.96%. Mass spectrum m / z: 782.2688 (theoretical value: 782.2682). Theoretical element content (%) C 55 H 34 N4O2: C, 84.38; H, 4.38; N, 7.16. Measured element content (%): C, 84.35; H, 4.35; N, 7.19.

[0237] Synthesis Example 20:

[0238]

[0239] According to the preparation method of Synthesis Example 1, b-4 and e-4 were replaced by equimolar amounts of b-190 and e-29, respectively, to obtain compound 190 (12.49 g); HPLC purity ≥ 99.95%. Mass spectrum m / z: 632.1969 (theoretical value: 632.1961). Theoretical element content (%) C 41 H 24 N6O2: C, 77.84; H, 3.82; N, 13.28. Measured element content (%): C, 77.88; H, 3.85; N, 13.25.

[0240] Synthesis Example 21:

[0241]

[0242] According to the preparation method of Synthesis Example 1, b-4 and e-4 were replaced by equimolar amounts of b-201 and e-29, respectively, to obtain Compound 201 (11.74 g); HPLC purity ≥ 99.94%. Mass spectrum m / z: 634.1860 (theoretical value: 634.1866). Theoretical element content (%) C 39 H 22 N8O2: C, 73.81; H, 3.49; N, 17.66. Measured element content (%): C, 73.85; H, 3.44; N, 17.69.

[0243] Synthesis Example 22:

[0244]

[0245] According to the preparation method of Synthesis Example 1, b-4, d-4, and e-4 were replaced by equimolar amounts of b-82, d-227, and e-29, respectively, to obtain Compound 227 (11.86 g); HPLC purity ≥ 99.95%. Mass spectrum m / z: 632.1969 (theoretical value: 632.1961). Theoretical element content (%) C 41 H 24 N6O2: C, 77.84; H, 3.82; N, 13.28. Measured element content (%): C, 77.87; H, 3.86; N, 13.24.

[0246] Synthesis Example 23:

[0247]

[0248] According to the preparation method of Synthesis Example 1, b-4, d-4, and e-4 were replaced by equimolar amounts of b-82, d-236, and e-29, respectively, to obtain Compound 236 (12.91 g); HPLC purity ≥ 99.96%. Mass spectrum m / z: 680.2218 (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, 82.96; H, 4.12; N, 8.26.

[0249] Synthesis Example 24:

[0250]

[0251] According to the preparation method of Synthesis Example 1, b-4, d-4, and e-4 were replaced by equimolar amounts of b-82, d-240, and e-29, respectively, to obtain Compound 240 (13.70 g); HPLC purity ≥ 99.95%. Mass spectrum m / z: 730.2376 (theoretical value: 730.2369). Theoretical element content (%) C 51 H 30 N4O2: C, 83.82; H, 4.14; N, 7.67. Measured element content (%): C, 83.85; H, 4.17; N, 7.63.

[0252] Synthesis Example 25:

[0253]

[0254] According to the preparation method of Synthesis Example 1, b-4 and d-4 were replaced by equimolar amounts of b-141 and d-256, respectively, to obtain Compound 256 (14.95 g); HPLC purity ≥ 99.95%. Mass spectrum m / z: 806.2675 (theoretical value: 806.2682). Theoretical element content (%) C 57 H 34 N4O2: C, 84.84; H, 4.25; N, 6.94. Measured element content (%): C, 84.88; H, 4.21; N, 6.97.

[0255] Synthesis Example 26:

[0256]

[0257] According to the preparation method of Synthesis Example 1, b-4 and d-4 were replaced by equimolar amounts of b-259 and d-95, respectively, to obtain Compound 259 (14.15 g); HPLC purity ≥ 99.96%. Mass spectrum m / z: 754.2361 (theoretical value: 754.2369). Theoretical element content (%) C 53 H 30 N4O2: C, 84.33; H, 4.01; N, 7.42. Measured element content (%): C, 84.30; H, 4.05; N, 7.46.

[0258] Synthesis Example 27:

[0259]

[0260] According to the preparation method of Synthesis Example 1, b-4 and e-4 were replaced by equimolar amounts of b-266 and e-29, respectively, to obtain Compound 266 (13.85 g); HPLC purity ≥ 99.96%. Mass spectrum m / z: 730.2361 (theoretical value: 730.2369). Theoretical element content (%) C 51 H 30 N4O2: C, 83.82; H, 4.14; N, 7.67. Measured element content (%): C, 83.86; H, 4.17; N, 7.63.

[0261] Synthesis Example 28:

[0262]

[0263] According to the preparation method of Synthesis Example 1, a-4, b-4, and e-4 were replaced by equimolar a-273, b-82, and e-29, respectively, to obtain compound 273 (12.52 g); HPLC purity ≥ 99.97%. Mass spectrum m / z: 633.2238 (theoretical value: 633.2244). Theoretical element content (%) C 43 H 23 D3N4O2: C, 81.50; H, 4.61; N, 8.84. Measured element content (%): C, 81.52; H, 4.64; N, 8.81.

[0264] Synthesis Example 29:

[0265]

[0266] According to the preparation method of Synthesis Example 1, a-4, b-4, and d-4 were replaced by equimolar a-277, b-82, and d-82, respectively, to obtain compound 277 (11.79 g); HPLC purity ≥ 99.95%. Mass spectrum m / z: 596.2219 (theoretical value: 596.2212). Theoretical element content (%) C 40 H 28 N4O2: C, 80.52; H, 4.73; N, 9.39. Measured element content (%): C, 80.56; H, 4.76; N, 9.35.

[0267] Synthesis Example 30:

[0268]

[0269] According to the preparation method of Synthesis Example 1, b-4, d-4, and e-4 were replaced by equimolar amounts of b-291, d-68, and e-29, respectively, to obtain Compound 291 (12.19 g); HPLC purity ≥ 99.95%. Mass spectrum m / z: 658.2360 (theoretical value: 658.2369). Theoretical element content (%) C 45 H 30 N4O2: C, 82.05; H, 4.59; N, 8.51. Measured element content (%): C, 82.08; H, 4.54; N, 8.54.

[0270] Synthesis Example 31:

[0271]

[0272] According to the preparation method of Synthesis Example 1, b-4 and e-4 were replaced by equimolar amounts of b-292 and e-29, respectively, to obtain compound 292 (12.76 g); HPLC purity ≥ 99.96%. Mass spectrum m / z: 680.1968 (theoretical value: 680.1961). Theoretical element content (%) C 45 H 24 N6O2: C, 79.40; H, 3.55; N, 12.35. Measured element content (%): C, 79.44; H, 3.53; N, 12.32.

[0273] Synthesis Example 32:

[0274]

[0275] According to the preparation method of Synthesis Example 1, b-4, d-4, and e-4 were replaced by equimolar amounts of b-82, d-296, and e-29, respectively, to obtain Compound 296 (13.46 g); HPLC purity ≥ 99.96%. Mass spectrum m / z: 706.2376 (theoretical value: 706.2369). Theoretical element content (%) C 49 H 30 N4O2: C, 83.27; H, 4.28; N, 7.93. Measured element content (%): C, 83.24; H, 4.25; N, 7.97.

[0276] Synthesis Example 33:

[0277]

[0278] According to the preparation method of Synthesis Example 1, b-4, d-4, and e-4 were replaced by equimolar amounts of b-82, d-82, and e-318, respectively, to obtain compound 318 (13.10 g); HPLC purity ≥ 99.97%. Mass spectrum m / z: 680.2218 (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, 82.94; H, 4.12; N, 8.25.

[0279] Synthesis Example 34:

[0280]

[0281] According to the preparation method of Synthesis Example 1, b-4, d-4, and e-4 were replaced by equimolar amounts of b-161, d-95, and e-342, respectively, to obtain compound 342 (14.38 g); HPLC purity ≥ 99.95%. Mass spectrum m / z: 756.2530 (theoretical value: 756.2525). Theoretical element content (%) C 53 H 32 N4O2: C, 84.11; H, 4.26; N, 7.40. Measured element content (%): C, 84.14; H, 4.22; N, 7.43.

[0282] Synthesis Example 35:

[0283]

[0284] According to the preparation method of Synthesis Example 1, d-4 and e-4 were replaced by equimolar d-82 and e-359, respectively, to obtain compound 359 (14.33 g); HPLC purity ≥ 99.96%. Mass spectrum m / z: 756.2532 (theoretical value: 756.2525). Theoretical element content (%) C 53 H 32 N4O2: C, 84.11; H, 4.26; N, 7.40. Measured element content (%): C, 84.15; H, 4.23; N, 7.43.

[0285] Synthesis Example 36:

[0286]

[0287] According to the preparation method of Synthesis Example 1, b-4, d-4, and e-4 were replaced by equimolar amounts of b-383, d-68, and e-383, respectively, to obtain compound 383 (13.14 g); HPLC purity ≥ 99.95%. Mass spectrum m / z: 682.2124 (theoretical value: 682.2117). Theoretical element content (%) C 45 H 26 N6O2: C, 79.17; H, 3.84; N, 12.31. Measured element content (%): C, 79.13; H, 3.88; N, 12.34.

[0288] Synthesis Example 37:

[0289]

[0290] According to the preparation method of Synthesis Example 1, b-4, d-4, and e-4 were replaced by equimolar amounts of b-82, d-82, and e-398, respectively, to obtain compound 398 (12.28 g); HPLC purity ≥ 99.96%. Mass spectrum m / z: 654.2063 (theoretical value: 654.2056). Theoretical element content (%) C 45 H 26 N4O2: C, 82.55; H, 4.00; N, 8.56. Measured element content (%): C, 82.52; H, 4.04; N, 8.52.

[0291] Synthesis Example 38:

[0292]

[0293] According to the preparation method of Synthesis Example 1, b-4 and e-4 were replaced by equimolar amounts of b-141 and e-428, respectively, to obtain compound 428 (15.13 g); HPLC purity ≥ 99.95%. Mass spectrum m / z: 806.2675 (theoretical value: 806.2682). Theoretical element content (%) C 57 H 34 N4O2: C, 84.84; H, 4.25; N, 6.94. Measured element content (%): C, 84.89; H, 4.22; N, 6.91.

[0294] Synthesis Example 39:

[0295]

[0296] According to the preparation method of Synthesis Example 1, b-4, d-4, and e-4 were replaced by equimolar amounts of b-82, d-68, and e-461, respectively, to obtain compound 461 (12.16 g); HPLC purity ≥ 99.96%. Mass spectrum m / z: 631.2015 (theoretical value: 631.2008). Theoretical element content (%) C 42 H 25 N5O2: C, 79.86; H, 3.99; N, 11.09. Measured element content (%): C, 79.89; H, 3.96; N, 11.05.

[0297] Synthesis Example 40:

[0298]

[0299] According to the preparation method of Synthesis Example 1, b-4 and e-4 were replaced by equimolar amounts of b-161 and e-477, respectively, to obtain compound 477 (13.27 g); HPLC purity ≥ 99.95%. Mass spectrum m / z: 707.2329 (theoretical value: 707.2321). Theoretical element content (%) C 48 H 29 N5O2: C, 81.45; H, 4.13; N, 9.89. Measured element content (%): C, 81.48; H, 4.17; N, 9.85.

[0300] Synthesis Example 41:

[0301]

[0302] According to the preparation method of Synthesis Example 1, b-4 and e-4 were replaced by equimolar amounts of b-82 and e-525, respectively, to obtain compound 525 (12.57 g); HPLC purity ≥ 99.97%. Mass spectrum m / z: 644.1853 (theoretical value: 644.1848). Theoretical element content (%) C 43 H 24 N4O3: C, 80.11; H, 3.75; N, 8.69. Measured element content (%): C, 80.14; H, 3.77; N, 8.66.

[0303] Synthesis Example 42:

[0304]

[0305] According to the preparation method of Synthesis Example 1, d-4 and e-4 were replaced by equimolar d-95 and e-600, respectively, to obtain compound 600 (12.24 g); HPLC purity ≥ 99.96%. Mass spectrum m / z: 812.2253 (theoretical value: 812.2246). Theoretical element content (%) C 55 H 32 N4O2S: C, 81.26; H, 3.97; N, 6.89. Measured element content (%): C, 81.29; H, 3.94; N, 6.85.

[0306] Synthesis Example 43:

[0307]

[0308] According to the preparation method of Synthesis Example 1, b-4, d-4, and e-4 were replaced by equimolar amounts of b-82, d-82, and e-619, respectively, to obtain compound 619 (13.32 g); HPLC purity ≥ 99.95%. Mass spectrum m / z: 719.2329 (theoretical value: 719.2321). Theoretical element content (%) C 49 H 29 N5O2: C, 81.76; H, 4.06; N, 9.73. Measured element content (%): C, 81.71; H, 4.08; N, 9.77.

[0309] Synthesis Example 44:

[0310]

[0311] According to the preparation method of Synthesis Example 1, b-4 and e-4 were replaced by equimolar amounts of b-161 and e-644, respectively, to obtain compound 644 (15.43 g); HPLC purity ≥ 99.94%. Mass spectrum m / z: 822.2987 (theoretical value: 822.2995). Theoretical element content (%) C 58 H 38 N4O2: C, 84.65; H, 4.65; N, 6.81. Measured element content (%): C, 84.62; H, 4.62; N, 6.85.

[0312] Synthesis Example 45:

[0313]

[0314] According to the preparation method of Synthesis Example 1, b-4, d-4, and e-4 were replaced by equimolar amounts of b-82, d-95, and e-654, respectively, to obtain compound 654 (15.06 g); HPLC purity ≥ 99.96%. Mass spectrum m / z: 792.2531 (theoretical value: 792.2525). Theoretical element content (%) C 56 H 32 N4O2: C, 84.83; H, 4.07; N, 7.07. Measured element content (%): C, 84.87; H, 4.04; N, 7.09.

[0315] Synthesis Example 46:

[0316]

[0317] Under nitrogen protection, d-667 (22.18 g, 77.00 mmol), e-4 (13.40 g, 70.00 mmol), potassium carbonate (19.35 g, 140.00 mmol), tetrakistriphenylphosphine palladium (809 mg, 0.70 mmol) and tetrahydrofuran (350 ml) were added to the reaction bottle and stirred for 8 hours under reflux. After the reaction was completed, it was cooled to room temperature, water was added, and it was extracted with dichloromethane. The organic phases were combined and dried with anhydrous magnesium sulfate, the solvent was removed under reduced pressure, and it was crystallized with toluene to obtain D-667 (18.38 g, 74%); HPLC purity ≥99.85%.

[0318] According to the preparation method of Synthesis Example 1, D-4 and A-4 were replaced by equimolar amounts of D-667 and A-82, respectively, to obtain compound 667 (12.30 g); HPLC purity ≥ 99.97%. Mass spectrum m / z: 630.2061 (theoretical value: 630.2056). Theoretical element content (%) C 43 H 26 N4O2: C, 81.89; H, 4.16; N, 8.88. Measured element content (%): C, 81.87; H, 4.19; N, 8.85.

[0319] Synthesis Example 47:

[0320]

[0321] According to the preparation method of Synthesis Example 46, d-4 and e-4 were replaced by equimolar d-729 and e-342, respectively, to obtain compound 729 (12.74 g); HPLC purity ≥ 99.96%. Mass spectrum m / z: 680.2219 (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, 82.96; H, 4.12; N, 8.27.

[0322] Device Embodiment

[0323] In the present invention, the ITO or ITO / Ag / ITO anode is ultrasonically cleaned twice with 5% glass cleaning solution for 20 minutes each time, and then ultrasonically cleaned twice with deionized water for 10 minutes each time. Acetone and isopropyl ketone are ultrasonically cleaned for 20 minutes in sequence, and dried at 120°C. The organic materials are all sublimated, and the purity is above 99.99%.

[0324] The test software, computer, K2400 digital source meter produced by Keithley Company of the United States and PR788 spectrum scanning luminance meter produced by PhotoResearch Company of the United States are combined into a joint IVL test system to test the driving voltage, luminous efficiency and CIE color coordinates of organic electroluminescent devices. The life test adopts the M6000 OLED life test system of McScience Company. The test environment is atmospheric environment and the temperature is room temperature.

[0325] Example 1: Preparation of organic electroluminescent device 1

[0326] CuPc was vacuum-deposited on the ITO anode as a hole injection layer with a thickness of 10 nm; HT-1 was vacuum-deposited on the hole injection layer as a hole transport layer with a thickness of 28 nm; compound 4 and GH-1 of the present invention were vacuum-deposited on the hole transport layer at a ratio of 1:1 (wt%), and the dopant GD-1 was vacuum-deposited at a doping amount of 8 wt% based on the total amount of the main body and the dopant to form a light-emitting layer with a thickness of 35 nm; BAlq was vacuum-deposited on the light-emitting layer as a hole blocking layer with a thickness of 10 nm; Alq3 was vacuum-deposited on the hole blocking layer as an electron transport layer with a thickness of 35 nm; LiF was vacuum-deposited on the electron transport layer as an electron injection layer with a thickness of 0.5 nm; Al was vacuum-deposited on the electron injection layer as a cathode with a thickness of 150 nm.

[0327] Examples 2 to 20: Preparation of organic electroluminescent devices 2 to 20

[0328] The compound 4 in the light-emitting layer of Example 1 is replaced by compound 14, compound 17, compound 68, compound 73, compound 82, compound 95, compound 96, compound 99, compound 121, compound 141, compound 161, compound 190, compound 236, compound 296, compound 318, compound 398, compound 461, compound 525, and compound 654, respectively, and the other steps are the same to obtain organic electroluminescent devices 2 to 20.

[0329] Comparative Examples 1-2: Preparation of Comparative Organic Electroluminescent Devices 1-2

[0330] The compound 4 in the light-emitting layer of Example 1 was replaced by R-1 and R-2 respectively, and the other steps were the same to obtain comparative organic electroluminescent devices 1-2.

[0331]

[0332] The test results of the luminescent characteristics of the organic electroluminescent devices prepared in Examples 1 to 20 of the present invention and Comparative Examples 1 to 2 are shown in Table 1.

[0333] Table 1 Test data of luminescence characteristics of organic electroluminescent devices

[0334]

[0335]

[0336] Example 21: Preparation of organic electroluminescent device 21

[0337] CuPc was vacuum-deposited on the ITO anode as a hole injection layer with a thickness of 10 nm; β-NPB was vacuum-deposited on the hole injection layer as a hole transport layer with a thickness of 28 nm; Compound 4 and RH-1 of the present invention were vacuum-deposited on the hole transport layer at a ratio of 1:1 (wt%), and the dopant Ir(MDQ)2(acac) was vacuum-deposited at a doping amount of 6 wt% based on the total amount of the host and the dopant to form a light-emitting layer with a thickness of 35 nm; BAlq was vacuum-deposited on the light-emitting layer as a hole blocking layer with a thickness of 10 nm; Almq3 was vacuum-deposited on the hole blocking layer as an electron transport layer with a thickness of 35 nm; LiF was vacuum-deposited on the electron transport layer as an electron injection layer with a thickness of 0.5 nm; Al was vacuum-deposited on the electron injection layer as a cathode with a thickness of 150 nm.

[0338] Examples 22 to 40: Preparation of organic electroluminescent devices 22 to 40

[0339] The compound 4 in the light-emitting layer of Example 21 is replaced by compound 16, compound 24, compound 29, compound 95, compound 96, compound 99, compound 108, compound 201, compound 227, compound 240, compound 266, compound 291, compound 342, compound 359, compound 428, compound 477, compound 600, compound 644, and compound 667, respectively, and the other steps are the same to obtain organic electroluminescent devices 22 to 40.

[0340] Comparative Examples 3-4: Preparation of Comparative Organic Electroluminescent Devices 3-4

[0341] The compound 4 in the light-emitting layer of Example 21 was replaced by R-1 and R-2 respectively, and the other steps were the same to obtain comparative organic electroluminescent devices 3 to 4.

[0342]

[0343] The test results of the luminescent characteristics of the organic electroluminescent devices prepared in Examples 21 to 40 of the present invention and Comparative Examples 3 to 4 are shown in Table 2.

[0344] Table 2 Test data of luminescence characteristics of organic electroluminescent devices

[0345]

[0346]

[0347] It can be seen from Table 1 and Table 2 that when the azacarbazole compound of Formula 1 of the present invention is used as a light-emitting host material in an organic electroluminescent device, the device has a higher light-emitting efficiency and a longer service life.

[0348] Example 41: Preparation of organic electroluminescent device 41

[0349] CuPc was vacuum evaporated on the ITO anode as a hole injection layer with a thickness of 10 nm; TPD10 was vacuum evaporated on the hole injection layer as a hole transport layer with a thickness of 30 nm; CBP:Ir(dpm)(piq)2=94:6(wt%) was vacuum evaporated on the hole transport layer as a light-emitting layer with a thickness of 35 nm; the compound 4 of the present invention was vacuum evaporated on the light-emitting layer as a hole blocking layer with a thickness of 10 nm; Alq3 was vacuum evaporated on the hole blocking layer as an electron transport layer with a thickness of 40 nm; LiF was vacuum evaporated on the electron transport layer as an electron injection layer with a thickness of 0.5 nm; Al was vacuum evaporated on the electron injection layer as a cathode with a thickness of 150 nm.

[0350] Examples 42 to 60: Preparation of organic electroluminescent devices 42 to 60

[0351] The compound 4 in the hole blocking layer of Example 41 is replaced with compound 17, compound 29, compound 68, compound 82, compound 95, compound 96, compound 99, compound 121, compound 141, compound 161, compound 190, compound 256, compound 273, compound 296, compound 318, compound 359, compound 461, compound 525, and compound 619, respectively, and the other steps are the same to obtain organic electroluminescent devices 42 to 60.

[0352] Comparative Examples 5-6: Preparation of Comparative Organic Electroluminescent Devices 5-6

[0353] The compound 4 in the hole blocking layer of Example 41 was replaced by R-3 and R-4 respectively, and the other steps were the same to obtain comparative organic electroluminescent devices 5 to 6.

[0354]

[0355] The test results of the luminescent characteristics of the organic electroluminescent devices prepared in Examples 41 to 60 of the present invention and Comparative Examples 5 to 6 are shown in Table 3.

[0356] Table 3 Test data of luminescence characteristics of organic electroluminescent devices

[0357]

[0358]

[0359] It can be seen from Table 3 that when the azacarbazole compound of Formula 1 of the present invention is used as a hole blocking material in an organic electroluminescent device, the device has a lower driving voltage, a higher luminous efficiency and a longer service life.

[0360] Example 61: Preparation of organic electroluminescent device 61

[0361] CuPc was vacuum evaporated on the ITO anode as a hole injection layer with a thickness of 10 nm; β-NPP was vacuum evaporated on the hole injection layer as a hole transport layer with a thickness of 30 nm; mCBP:Ir(dpm)PQ2=95:5(wt%) was vacuum evaporated on the hole transport layer as a light-emitting layer with a thickness of 35 nm; BCP was vacuum evaporated on the light-emitting layer as a hole blocking layer with a thickness of 10 nm; Compound 4 of the present invention was vacuum evaporated on the hole blocking layer as an electron transport layer with a thickness of 40 nm; LiF was vacuum evaporated on the electron transport layer as an electron injection layer with a thickness of 0.5 nm; Al was vacuum evaporated on the electron injection layer as a cathode with a thickness of 150 nm.

[0362] Examples 62-80: Preparation of organic electroluminescent devices 62-80

[0363] The compound 4 in the electron transport layer of Example 61 is replaced by compound 17, compound 46, compound 68, compound 73, compound 82, compound 95, compound 96, compound 99, compound 109, compound 121, compound 136, compound 190, compound 259, compound 277, compound 292, compound 383, compound 461, compound 477, and compound 729, respectively, and the other steps are the same to obtain organic electroluminescent devices 62 to 80.

[0364] Comparative Examples 7-8: Preparation of Comparative Organic Electroluminescent Devices 7-8

[0365] The compound 4 in the electron transport layer of Example 61 was replaced by R-3 and R-4 respectively, and the other steps were the same to obtain comparative organic electroluminescent devices 7 to 8.

[0366]

[0367] The test results of the luminescent characteristics of the organic electroluminescent devices prepared in Examples 61 to 80 of the present invention and Comparative Examples 7 to 8 are shown in Table 4.

[0368] Table 4 Test data of luminescence characteristics of organic electroluminescent devices

[0369]

[0370]

[0371] It can be seen from Table 4 that when the azacarbazole compound of Formula 1 of the present invention is used as an electron transport material in an organic electroluminescent device, the device has a lower driving voltage, a higher luminous efficiency and a longer service life.

[0372] Example 81: Preparation of organic electroluminescent device 81

[0373] HAT-CN was vacuum evaporated on the ITO anode as a hole injection layer with a thickness of 5 nm; BPBPA was vacuum evaporated on the hole injection layer as a first hole transport layer with a thickness of 50 nm; BH-1:BD-1=94:6 (wt%) was vacuum evaporated on the first hole transport layer to form a first light-emitting layer with a thickness of 30 nm; ET-1 was vacuum evaporated on the first light-emitting layer as a first electron transport layer with a thickness of 25 nm; Compound 4 of the present invention was vacuum evaporated on the first electron transport layer as an n-type charge generation layer with a thickness of 15 nm; HAT-CN was vacuum-deposited on the layer as a p-type charge generation layer with a thickness of 15 nm; BPBPA was vacuum-deposited on the p-type charge generation layer as a second hole transport layer with a thickness of 45 nm; BH-1:BD-1=94:6 (wt%) was vacuum-deposited on the second hole transport layer to form a second light-emitting layer with a thickness of 30 nm; ET-1 was vacuum-deposited on the second light-emitting layer as a second electron transport layer with a thickness of 30 nm; LiF was vacuum-deposited on the second electron transport layer as an electron injection layer with a thickness of 1.2 nm; Al was vacuum-deposited on the electron injection layer as a cathode with a thickness of 150 nm.

[0374] Examples 82-95: Preparation of organic electroluminescent devices 82-95

[0375] The compound 4 in the n-type charge generation layer in Example 81 is replaced by compound 17, compound 29, compound 68, compound 73, compound 82, compound 95, compound 96, compound 99, compound 121, compound 141, compound 161, compound 190, compound 296, and compound 318, respectively, and the other steps are the same to obtain organic electroluminescent devices 82 to 95.

[0376] Comparative Example 9: Preparation of Comparative Organic Electroluminescent Device 9

[0377] The compound 4 in the n-type charge generation layer in Example 81 was replaced by R-5, and the other steps were the same to obtain a comparative organic electroluminescent device 9.

[0378]

[0379] The test results of the luminescent characteristics of the organic electroluminescent devices prepared in Examples 81 to 95 of the present invention and Comparative Example 9 are shown in Table 5.

[0380] Table 5 Luminescence characteristics test data of organic electroluminescent devices

[0381]

[0382]

[0383] It can be seen from Table 5 that the azacarbazole compound of Formula 1 of the present invention is used as an n-type charge generating material in a stacked organic electroluminescent device, and the device has a higher luminous efficiency and a longer service life.

[0384] 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 azacarbazole compound, characterized in that It is represented by the following formula 1: Wherein, the ring A and the ring B are independently selected from a substituted or unsubstituted C6-C30 aromatic ring, a substituted or unsubstituted 6-30-membered nitrogen-containing heteroaromatic ring, and at least one is a substituted or unsubstituted 6-30-membered nitrogen-containing heteroaromatic ring; The Ar1 and Ar2 are independently selected from the following groups: The ring C is selected from a substituted or unsubstituted C6-C30 aromatic ring, a substituted or unsubstituted 6-30-membered nitrogen-containing heteroaromatic ring; The R0 is selected from one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C6-C60 fused polycyclic group, substituted or unsubstituted C2-C60 heteroaryl; Ar is selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C6-C60 fused polycyclic group, substituted or unsubstituted C2-C60 heteroaryl, or the N atom corresponding to Ar is the connection site with L; The R's are the same or different and are selected from one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C6-C60 fused polycyclic group, substituted or unsubstituted C2-C60 heteroaryl; The i is selected from an integer of 0 to 3; The L, L1, and L2 are independently selected from a single bond, a substituted or unsubstituted C6-C60 arylene group, a substituted or unsubstituted C6-C60 condensed polycyclic group, and a substituted or unsubstituted C2-C60 heteroarylene group.

2. The azacarbazole compound according to claim 1, characterized in that Said Ring A and Ring B in are independently selected from one of the following groups: The V's are the same or different and are selected from C(Rv) or N, and at least one V in ring A or ring B is selected from N, and the Rv's are the same or different and are selected from one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C6-C60 fused polycyclic group, substituted or unsubstituted C2-C60 heteroaryl, or two adjacent Rv's are bonded to each other to form a substituted or unsubstituted ring.

3. The azacarbazole compound according to claim 1, characterized in that Said Ring A and Ring B in are independently selected from one of the groups shown below, and at least one of Ring A or Ring B is a nitrogen-containing heterocycle, The m1 is selected from integers of 0 to 4, the m2 is selected from integers of 0 to 3, the m3 is selected from integers of 0 to 2, the m4 is selected from integers of 0 to 6, the m5 is selected from integers of 0 to 5, the m6 is selected from integers of 0 to 8, and the m7 is selected from integers of 0 to 7; The R v the same or different selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 fused polycyclic group, substituted or unsubstituted C2-C30 heteroaryl, or two adjacent R v They are bonded to each other to form a substituted or unsubstituted ring.

4. The azacarbazole compound according to claim 1, characterized in that Said Ring C in is selected from one of the following groups, The E's are the same or different and are selected from C(Re) or N, and the Re's are the same or different and are selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C6-C60 fused polycyclic group, substituted or unsubstituted C2-C60 heteroaryl, or two adjacent Re's are bonded to each other to form a substituted or unsubstituted ring.

5. The azacarbazole compound according to claim 1, characterized in that Said Ring C in is selected from one of the following groups, The n1 is selected from an integer of 0 to 4, the n2 is selected from an integer of 0 to 3, the n3 is selected from an integer of 0 to 2, the n4 is selected from an integer of 0 to 6, the n5 is selected from an integer of 0 to 5, the n6 is selected from an integer of 0 to 8, and the n7 is selected from an integer of 0 to 7; The R e the same or different selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 fused polycyclic group, substituted or unsubstituted C2-C30 heteroaryl, or two adjacent R e They are bonded to each other to form a substituted or unsubstituted ring.

6. The azacarbazole compound according to claim 1, characterized in that The L is selected from a single bond, one of the following groups or a combination thereof, The Q is the same or different and is selected from C or N; Each of the R1 and R2 is the same or different and is selected from one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 fused polycyclic group, substituted or unsubstituted C2-C30 heteroaryl, or two adjacent R1 and R2 are bonded to each other to form a substituted or unsubstituted ring; The X is selected from O, S, C(R x )2 or N(R x ), the R x the same or different selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 fused polycyclic group, substituted or unsubstituted C2-C30 heteroaryl, or two adjacent R x bonded to each other to form a substituted or unsubstituted ring; The L 01 , L 02 independently selected from a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted benzocyclobutene, a substituted or unsubstituted benzocyclobutenylene, a substituted or unsubstituted indenylene, a substituted or unsubstituted dihydroindenylene, a substituted or unsubstituted dihydronaphthylene, a substituted or unsubstituted tetrahydronaphthylene, a substituted or unsubstituted pyridylene, a substituted or unsubstituted pyrimidylene, a substituted or unsubstituted pyrazinylene, and a substituted or unsubstituted pyridazinylene; b and c are selected from integers of 0 to 4, and a is selected from integers of 0 to 6; When a is 2 or more, each unit in the brackets is the same or different.

7. The azacarbazole compound according to claim 1, characterized in that The L is selected from a single bond, one of the following groups or a combination thereof, b and c are selected from integers of 0 to 4, b1 and c1 are selected from integers of 0 to 3, b2 and c2 are selected from integers of 0 to 2, c3 is selected from integers of 0 to 6, c4 is selected from integers of 0 to 8, and c5 is selected from integers of 0 to 10; Each of the R1 and R2 is the same or different and is selected from one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 fused polycyclic group, substituted or unsubstituted C2-C30 heteroaryl, or two adjacent R1 and R2 are bonded to each other to form a substituted or unsubstituted ring; The R c The same or different ones are selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 fused polycyclic group, substituted or unsubstituted C2-C30 heteroaryl; The R x the same or different selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 fused polycyclic group, substituted or unsubstituted C2-C30 heteroaryl, or two adjacent R x They are bonded to each other to form a substituted or unsubstituted ring.

8. The azacarbazole compound according to claim 1, characterized in that The L1 and L2 are independently selected from a single bond or the following groups: The Gs are the same or different and are selected from C or N; The R3 are the same or different and are selected from one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 fused polycyclic group, substituted or unsubstituted C2-C30 heteroaryl, or two adjacent R3 are bonded to each other to form a substituted or unsubstituted ring; The d is selected from an integer of 0 to 4, and the e is selected from an integer of 0 to 4; When d is 2 or more, each unit in the brackets is the same or different.

9. The azacarbazole compound according to claim 1, characterized in that The azacarbazole compound represented by Formula 1 is selected from at least one of the structures shown below:

10. An organic electroluminescent device, characterized in that: The organic electroluminescent device contains the azacarbazole compound according to any one of claims 1 to 9.

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