CN115974806A

CN115974806A - Heterocyclic compound and organic electroluminescent device thereof

Info

Publication number: CN115974806A
Application number: CN202211582277.0A
Authority: CN
Inventors: 郭建华; 刘喜庆; 董秀芹
Original assignee: Changchun Hyperions Technology Co Ltd
Current assignee: Changchun Hyperions Technology Co Ltd
Priority date: 2022-12-09
Filing date: 2022-12-09
Publication date: 2023-04-18
Anticipated expiration: 2042-12-09
Also published as: CN115974806B

Abstract

The invention provides a heterocyclic compound and an organic electroluminescent device thereof, and relates to the technical field of organic electroluminescent materials. The heterocyclic compound shown in the formula 1 has better photoelectric property, is used as a luminescent main body material, an electron transmission material or a covering layer material in an organic electroluminescent device, has excellent performance, specifically shows that the driving voltage is reduced, the luminous efficiency is increased, the service life is prolonged, and is an excellent organic electroluminescent material.

Description

Heterocyclic compound and organic electroluminescent device thereof

Technical Field

The invention relates to the technical field of organic electroluminescent materials, in particular to a heterocyclic compound and an organic electroluminescent device thereof.

Background

An OLED (Organic Light-Emitting Diode) is generally called an "Organic Light-Emitting Diode", and is an electroluminescent device. The OLED is a third generation display technology following the CRT and LCD, and the OLED attracts attention due to its characteristics of high color contrast, fast response speed, light weight, low power consumption, high contrast, and flexibility, and is now gradually replacing the LCD as the mainstream display technology of the mobile terminal.

Under the action of an external electric field, electrons generated by the cathode of the OLED and holes generated by the anode of the OLED are respectively injected into the light emitting layer, the electrons and the holes meet and are combined to form excitons in the light emitting layer, and the excitons are attenuated to emit photons so as to generate visible light. The color of the emitted light is different due to the different luminescent materials and compositions. By selecting different organic luminescent materials, red light, green light and blue light can be obtained, and colorization is realized.

OLEDs can be classified into four types, i.e., a single-layer device, a double-layer device, a triple-layer device, and a multi-layer device, according to the structure. A single-layer device is characterized in that an organic layer capable of emitting light is connected between the cathode and the anode of the device, and the stability of the device is poor. The double-layer device is based on a single-layer device, and a hole transport layer or an electron transport layer is added on two sides of the luminescent layer, so that the voltage-current characteristic of the device is improved, and the luminous efficiency of the device is improved. The three-layer device structure simultaneously uses a hole transport layer and an electron transport layer, and has the advantage that excitons are confined in the light emitting layer, thereby improving the efficiency of the device. The multilayer device structure is formed by adding an injection layer and a barrier layer on the basis of a three-layer device structure, the performance of the multilayer device structure is a better structure, and the multilayer device structure can well play the role of each layer.

OLED materials mainly include carrier injection/transport materials, light emitting materials, and light extraction materials. The carrier injection/transport material mainly includes an electron transport region material and a hole transport region material. The electron transport region material mainly includes a hole blocking material, an electron transport material, an electron injection material, and the like. The hole transport region material mainly includes a hole injection material, a hole transport material, an electron blocking material, and the like. The luminescent material mainly comprises a red light host/guest material, a green light host/guest material, a blue light host/guest material and the like. With the optimization of device structures, the variety of materials is continuously increasing. Among them, a light-emitting host material, an electron transporting region material, or a light extraction material plays an important role in an organic electroluminescent device.

To date, a large number of OLED materials are researched and developed to promote the development of OLEDs, but the performance of most OLED materials cannot meet the industrial requirements, so that the performance of organic electroluminescent devices is poor, and therefore, it is important to research and develop new OLED materials meeting the industrial requirements.

Disclosure of Invention

Aiming at the problems in the prior art, the invention provides a heterocyclic compound and an organic electroluminescent device thereof.

The present invention provides a heterocyclic compound represented by the following formula 1,

wherein, the ring A is selected from one of a substituted or unsubstituted benzene ring and a substituted or unsubstituted benzene ring, and the substituent group in the substituted or unsubstituted is selected from one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl and substituted or unsubstituted C3-C25 lipo-heterocyclic group;

ar is selected from the group shown as follows,

the ring B is selected from substituted or unsubstituted C10-C30 aromatic ring, substituted or unsubstituted 10-30 membered heteroaromatic ring containing 1N, and fused C3-C20 substituted or unsubstituted alicyclic ring and C10-C30 aromatic ringOne of a condensed ring of a cyclic ring, a substituted or unsubstituted C3 to C20 alicyclic ring, and a 10 to 30-membered heteroaromatic ring;

said X is₁Selected from O or S;

said R is₁One selected from the group consisting of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C20 fused ring group of an alicyclic ring and a C6-C30 aromatic ring, substituted or unsubstituted C3-C20 fused ring group of an alicyclic ring and a C2-C30 heteroaromatic ring, and substituted or unsubstituted C3-C20 lipoheterocyclic group;

Ar is₁、Ar₂Independently selected from the group shown below,

the ring C is selected from one of a substituted or unsubstituted C6-C30 aromatic ring, a substituted or unsubstituted C2-C30 heteroaromatic ring, a substituted or unsubstituted fused ring of a C3-C20 alicyclic ring and a C6-C30 aromatic ring, and a substituted or unsubstituted fused ring of a C3-C20 alicyclic ring and a C2-C30 heteroaromatic ring;

w is selected from N or C (Rw), and the Rw is selected from one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C20 fused ring group of alicyclic ring and C6-C30 aromatic ring, substituted or unsubstituted C3-C20 fused ring group of alicyclic ring and C2-C30 heteroaromatic ring, and substituted or unsubstituted C3-C20 lipoheterocyclic group;

said X is₂Selected from O, S, N (R)_x2) Said R is_x2Selected from hydrogen, deuterium, tritium, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, and substituted or unsubstituted C3-C20 alicyclic ring and C6-C30 aromatic ring fused together One of a cyclic group, a condensed cyclic group of a substituted or unsubstituted C3 to C20 alicyclic ring and a C2 to C30 heteroaromatic ring, and a substituted or unsubstituted C3 to C20 alicyclic heterocyclic group;

said R is₂One selected from the group consisting of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C20 fused ring group of an alicyclic ring and a C6-C30 aromatic ring, substituted or unsubstituted C3-C20 fused ring group of an alicyclic ring and a C2-C30 heteroaromatic ring, and substituted or unsubstituted C3-C20 alicyclic ring group;

l, L₁、L₂Independently selected from a single bond, a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted C2-C30 heteroarylene group, a substituted or unsubstituted C3-C20 fused ring sub-group of an alicyclic ring and an aromatic ring of C6-C30, a substituted or unsubstituted C3-C20 alicyclic ring and a fused ring sub-group of a heteroaromatic ring of C2-C30, wherein the substituent in the substituted or unsubstituted group is selected from one of hydrogen, deuterium, tritium, halogen, cyano, nitro, a substituted or unsubstituted C1-C25 alkyl group, a substituted or unsubstituted C3-C25 cycloalkyl group, a substituted or unsubstituted C3-C25 alicyclic heterocyclic group, or two adjacent substituents are bonded to each other to form a substituted or unsubstituted ring.

In addition, the present invention provides an organic electroluminescent device comprising the heterocyclic compound of the present invention described above.

Has the beneficial effects that: the heterocyclic compound shown in the formula 1 has better photoelectric property and stability, is an excellent electronic type main body material, can effectively transmit electrons when being used in a device, balances the electrons and holes in a light-emitting layer, effectively limits the electrons and the holes in the light-emitting layer to be combined to form excitons to emit light, improves the performance of the device, and particularly shows that the driving voltage is reduced, the light-emitting efficiency is improved, and the service life is prolonged.

In addition, the heterocyclic compound of formula 1 of the present invention is used in an organic electroluminescent device as an electron transport material or a capping layer material, and the device also shows excellent properties, and is an excellent organic electroluminescent material.

Detailed Description

The invention is further illustrated by the following examples which are intended to be illustrative only and not to be limiting as to the scope of the invention which is to be given the full breadth of the appended claims and any and all modifications thereof which would occur to one skilled in the art upon reading the present specification and which fall within the scope of the appended claims.

In the compounds of the present invention, any atom not designated as a particular isotope is included as any stable isotope of that atom and includes atoms in both their natural isotopic abundance and unnatural abundance.

The halogen in the invention comprises fluorine, chlorine, bromine and iodine.

The integer selected from 0 to M refers to any one of the integers selected from 0 to M, and comprises 0,1,2 \8230M-2, M-1, M. For example, the expression "r1 is an integer selected from 0 to 3" means that r1 is selected from 0,1,2 or 3. And so on.

In the present invention, "unsubstituted ZZ group" in "substituted or unsubstituted ZZ group" means that the hydrogen atom of "ZZ group" is not replaced by a substituent. For example, the "unsubstituted aryl group" in the "substituted or unsubstituted C6 to C30 aryl group" means that the hydrogen atom of the "aryl group" is not replaced by a substituent. And so on.

In the present invention, "CXX to CYY" in "a substituted or unsubstituted ZZ group of CXX to CYY" represents the number of carbon atoms in the unsubstituted "ZZ group," and when the "ZZ group" has a substituent, the number of carbon atoms of the substituent is not included. For example, "C6 to C30" in "substituted or unsubstituted C6 to C30 aryl" represents the number of carbon atoms in the unsubstituted "aryl", and when the "aryl" has a substituent, the number of carbon atoms in the substituent is not included. "C3 to C20" in the "fused ring group of a substituted or unsubstituted C3 to C20 alicyclic ring and a C6 to C30 aromatic ring" represents the number of carbon atoms in the unsubstituted "alicyclic ring", and when the "alicyclic ring" has a substituent, the number of carbon atoms of the substituent is not included; "C6 to C30" represent the number of carbon atoms in an unsubstituted "aromatic ring", and when the "aromatic ring" has a substituent, the number of carbon atoms does not include the substituent. And so on.

In the present invention, when the position of a substituent on an aromatic ring is not fixed, it means that it can be attached to any of the corresponding optional positions of the aromatic ring. For example, in the case of a liquid,

can signify->

And so on.

In the present invention, "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 heterocyclic ring. The hydrocarbon ring may be an aliphatic hydrocarbon ring or an aromatic hydrocarbon ring. The heterocyclic ring may include an aliphatic heterocyclic ring or an aromatic heterocyclic ring. The aliphatic hydrocarbon ring may be a saturated aliphatic hydrocarbon ring or an unsaturated aliphatic hydrocarbon ring, and the aliphatic heterocyclic ring may be a saturated aliphatic heterocyclic ring or an unsaturated aliphatic heterocyclic ring. The hydrocarbon rings and heterocycles may be monocyclic or polycyclic groups. In addition, a ring formed by combining adjacent groups may be connected to another ring to form a spiro structure. As exemplified below:

in the present invention, the ring to be connected may be a three-membered ring, a four-membered ring, a five-membered ring, a six-membered ring, a seven-membered ring, a fused ring, etc., such as cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopentene, cyclohexene, benzene, naphthalene, phenanthrene, triphenylene, pyridine, pyrimidine, quinoline, fluorene, furan, thiophene, carbazole, etc., but not limited thereto.

The azabenzene ring of the present invention represents that carbon at any position of the benzene ring may be replaced by nitrogen, and may contain 1N, 2N, or 3N, for example.

The term "substituted" in the "substituted or unsubstituted" as used herein means that at least one hydrogen atom on the group is replaced with a substituent. When a plurality of hydrogens is replaced with a plurality of substituents, the plurality of substituents may be the same or different. The position of the hydrogen replaced by the substituent may be any position. The substituent represented by "substituted" in the above "substituted or unsubstituted" includes deuterium, tritium, cyano, halogen, nitro, silyl, alkoxy, aryloxy, heterocyclic group, alkyl group, cycloalkyl group, aryl group, heteroaryl group, fused ring group of an alicyclic ring and an aromatic ring, fused ring group of an alicyclic ring and a heteroaromatic ring, and the like. The following groups are preferred: deuterium, tritium, cyano, halogen, nitro, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, bornanyl, isobornyl, fenchyl, phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, anthracenyl, pyrenyl, cyclohexyl, and mixtures thereof,

Examples of the group include a group selected from the group consisting of a fluoro group, a benzocyclopropyl group, a benzocyclobutane group, an indanyl group, a tetrahydronaphthyl group, a benzocycloheptane group, a benzocyclooctane group, a benzocyclobutene group, an indenyl group, a dihydronaphthyl group, a fluorenyl group, a spirobifluorenyl group, a pyridyl group, a pyrimidyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolyl group, an isoquinolyl group, a quinazolinyl group, a quinoxalinyl group, a benzoquinolyl group, a benzisoquinolyl group, a phenanthrolinyl group, an oxazolyl group, a benzoxazolyl group, a thiazolyl group, a benzothiazolyl group, an imidazolyl group, a benzimidazolyl group, a benzofuranyl group, a dibenzofuranyl group, a benzothienyl group, an indolyl group, a carbazolyl group and the like. Further, each of the above substituents may be substituted or unsubstituted. Two adjacent substituents may be bonded to form a ring.

The alkyl refers to a hydrocarbon group formed by subtracting one hydrogen atom from an alkane molecule. The alkyl group may be a straight chain alkyl group or a branched chain alkyl group. When the number of carbon atoms of the chain alkyl group in the present invention is three or more, isomers thereof are included, and for example, a propyl group includes an n-propyl group and an isopropyl group; the butyl group includes n-butyl, isobutyl, sec-butyl, and tert-butyl. The alkyl group has 1 to 20 carbon atoms, preferably 1 to 15 carbon atoms, preferably 1 to 10 carbon atoms, and more preferably 1 to 6 carbon atoms. And so on. Examples of the alkyl group include, but are not limited to, the groups described below, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, and the like, but are not limited thereto.

The cycloalkyl group in the present invention refers to a hydrocarbon group in which one hydrogen atom is omitted from a cycloalkane molecule. The cycloalkyl group includes monocyclic cycloalkyl, polycyclic cycloalkyl, bridged cycloalkyl. The cycloalkyl group has carbon atoms of C3 to C20, preferably C3 to C15, and more preferably C3 to C10. Examples of the cycloalkyl group include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, bornanyl, fenchyl, isobaranyl, and the like, as described below.

The aryl group in the invention refers to a general term of univalent groups left after a hydrogen atom is removed from an aromatic nucleus carbon of an aromatic compound molecule. The aryl group includes monocyclic aryl groups, polycyclic aryl groups, fused ring aryl groups, or combinations thereof. The aryl group has 6 to 30, preferably 6 to 25, and more preferably 6 to 20 carbon atoms. Examples of the aryl group include, but are not limited to, the groups described below , phenyl radical , biphenyl radical , 3. Biphenyl radical , 4. Biphenyl radical , naphthyl radical , phenanthryl radical , anthracenyl group , triphenylene radical , fluorenyl radicals , benzofluorenyl radicals , spirobifluorene group , benzospirobifluorenyl radicals , pyrenyl group , fluoranthenyl ,

And the like, but are not limited thereto.

The heteroaryl group in the present invention refers to a monovalent group in which at least one carbon atom in an aryl group is substituted with a heteroatom. The heteroatom is selected from O, S, N, si, B, P, etc., but is not limited thereto. The number of ring atoms of the heteroaryl group may be 5 to 40, preferably 6 to 30, and further preferably 10 to 30; the carbon number of the heteroaryl group may be C2 to C30, more preferably C2 to C25, and still more preferably C3 to C20. Examples of such heteroaryl groups include, but are not limited to, the groups described below , oxazolyl radical , benzoxazolyl radical , naphthoxazolyl radical , phenanthrooxazolyl group , anthraxazolyl group , tribenzoxazolyl radical , pyridooxazolyl radical , pyrimidooxazolyl group , triazinooxazolyl radical , quinolonooxazolyl radical , isoquinolooxazolyl radical , quinazolinooxazolyl groups , quinoxalinooxazolyl radical , pyridyl oxazolyl radicals , thiazolyl radical , benzothiazolyl radical , naphthothiazolyl radicals , phenanthro thiazolyl , anthrathiazolyl groups , triphenylene benzothiazolyl group , pyridinothiazolyl , pyrimido-thiazolyl group , triazinothiazolyl , quinolinothiazolyl , isoquinolothiazolyl , thiazolidino thiazolyl , imidazolyl group , benzimidazolyl radicals , naphthoimidazolyl radical , phenanthroimidazolyl , anthrabenzimidazolyl radicals , triphenylbenzimidazolyl group , pyridoimidazolyl , pyrimido-imidazolyl , triazinoimidazolyl group , quinolinoimidazolyl group , isoquinolino imidazolyl , quinoxalinoimidazolyl , quinazolinimidazolyl , furyl radical , benzofuranyl radical , naphthofuryl group , phenanthrofuranyl , anthrafuranofuranyl radical , triphenylene benzofuranyl , dibenzofuranyl radical , thienyl radical , benzothienyl , naphthothienyl radical , phenanthro thienyl radical , anthrathienothienyl radicals , triphenylthienylene , dibenzothienyl radical , indolyl radical , naphthoindolyl radical , phenanthroindolyl , anthra-indolyl group , triphenylene indole group , carbazolyl group , pyridinyl group , pyrimidinyl radicals , pyrazinyl radical , pyridazinyl radical , triazine radical , quinolyl radicals , isoquinolinyl radicals , quinazolinyl radical , quinoxalinyl , naphthyridinyl group , phenanthroline radical , benzoquinolinyl radicals , benzisoquinolinyl and the like , but is not limited thereto. .

The condensed ring group of the alicyclic ring and the aromatic ring as described in the present invention is a generic name of a monovalent group obtained by condensing an alicyclic ring and an aromatic ring together and then removing one hydrogen atom. The alicyclic ring has from C3 to C20, preferably from C3 to C15, more preferably from C3 to C10, and still more preferably from C3 to C8, in carbon atoms. The aromatic ring has C6 to C30, preferably C6 to C25, preferably C6 to C18, more preferably C6 to C12, and still more preferably C6 to C10. Examples of the condensed ring group of the alicyclic and aromatic rings include, but are not limited to, the groups described below, benzocyclopropane, benzocyclobutane, indanyl, tetrahydronaphthyl, benzocycloheptane, benzocyclobutene, indenyl, dihydronaphthyl, benzocycloheptenyl, and the like, but are not limited thereto.

The fused ring group of an alicyclic ring and a heteroaromatic ring as used herein refers to a general term for a monovalent group obtained by fusing an alicyclic ring and a heteroaromatic ring together and then removing one hydrogen atom. The alicyclic ring has from C3 to C20, preferably from C3 to C15, and more preferably from C3 to C10, in carbon number. The heteroaromatic ring has from C2 to C30, preferably from C2 to C25, preferably from C2 to C18, preferably from C2 to C12, more preferably from C2 to C10 carbon atoms. Examples of the fused cyclic group of the alicyclic and aromatic rings include, but are not limited to, a pyridocyclobutyl group, a pyridocyclopentane group, a pyridocyclohexyl group, a pyridocycloheptyl group, a pyridocyclopentenyl group, a pyridocyclohexenyl group, a pyrimidocyclopentanyl group, a pyrimidocyclocyclohexyl group, a pyrimidocycloheptanyl group, a pyrimidocyclopentenyl group, a pyrimidocyclohexenyl group and the like, as described below, but are not limited thereto.

The alicyclic group described in the present invention includes cycloalkyl, cycloalkenyl, cycloalkyne, and the like, preferably having 3 to 25 carbon atoms, more preferably 3 to 20 carbon atoms, particularly preferably 3 to 15 carbon atoms, preferably 5 to 10 carbon atoms, and most preferably 5 to 7 carbon atoms, and examples may include cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornane, cyclopropene, cyclobutene, cyclopentene, cyclohexene, cycloheptene, and the like, but are not limited thereto.

The term "alicyclic heterocyclic group" as used herein refers to a divalent group formed by removing one hydrogen atom from an alicyclic heterocyclic hydrocarbon molecule, and the heteroatom is selected from the group consisting of O, S, N, si, B, P, and the like, but is not limited thereto. The aliphatic heterocyclic group has 2 to 20, preferably 2 to 15, preferably 2 to 10, and preferably 2 to 6 carbon atoms. Examples of such aliphatic heterocyclic groups include, but are not limited to, the groups described below, furyl, tetrahydrofuryl, thienyl, tetrahydrothienyl, and the like.

The term "arylene" as used herein refers to a general term for a monovalent group remaining after a hydrogen atom is removed from an aromatic core carbon of an aromatic compound molecule. The arylene group includes monocyclic arylene, polycyclic arylene, fused ring arylene, or combinations thereof. The arylene group has a carbon number of C6 to C60, preferably C6 to C30, preferably C6 to C25, preferably C6 to C20, and more preferably C6 to C18. Examples of the arylene group include, but are not limited to, the groups described below, phenylene, biphenylene, terphenylene, quaterphenylene, pentabiphenylene, naphthylene, phenanthrylene, anthracylene, triphenylene, pyrenylene, fluorenylene, benzofluorenylene, dibenzofluorenylene, naphthofluorenylene, spirobifluorenylene, and the like, but are not limited thereto.

The heteroarylene group refers to a divalent group in which at least one carbon atom in the arylene group is substituted with a heteroatom. The heteroatom is selected from O, S, N, si, B, P, etc., but is not limited thereto. The heteroarylene includes a monocyclic heteroarylene, a polycyclic heteroarylene, a fused ring heteroarylene, or a combination thereof. The heteroarylene group has from C2 to C30, preferably from C2 to C25, and preferably from C2 to C20, in carbon number. Examples of the heteroarylene group include, but are not limited to, a pyridylene group, a pyrimidylene group, a pyrazinylene group, a pyridazinylene group, a triazinylene group, a quinolylene group, a quinazolinylene group, a naphthyrylene group, a phenanthroline group, a benzoquinolylene group and the like, as described below, but are not limited thereto.

The term "subfused cyclic group of an alicyclic ring and an aromatic ring" as used herein means a general term in which an alicyclic ring and an aromatic ring are fused together, two hydrogen atoms are removed, and a divalent group remains. The alicyclic ring has from C3 to C20, preferably from C3 to C15, and more preferably from C3 to C8, in carbon number. The number of carbon atoms of the aromatic ring is C6-C30, preferably C6-C20, preferably C6-C18, preferably C6-C10. Examples of the condensed-ene ring group of the alicyclic and aromatic rings include, but are not limited to, benzocyclobutene-ene group, dihydroindenyl group, tetrahydronaphthyl group, benzocycloheptanyl group, benzocyclobutene-ene group, indenyl group, dihydronaphthyl group, benzocycloheptylene group, naphthocyclopentyl group, naphthocyclohexenyl group, etc., as described below, but are not limited thereto.

The term "condensed ring group of an alicyclic ring and a heteroaromatic ring" as used herein means a general term in which two hydrogen atoms are removed after the alicyclic ring and the heteroaromatic ring are condensed together to leave a divalent group. The alicyclic ring has from C3 to C20, preferably from C3 to C15, and more preferably from C3 to C8, in carbon number. The heteroaromatic ring has from C2 to C30, preferably from C2 to C20, preferably from C2 to C18, preferably from C2 to C10 carbon atoms. Examples of the condensed-cyclic group of the alicyclic and heteroaromatic rings include, but are not limited to, a pyridocyclopropanylene group, a pyridocyclobutaneylene group, a pyridocyclopentanylene group, a pyridocyclohexanylene group, a pyridocyclopentenylene group, a pyridocyclohexenylene group, and the like, but are not limited thereto.

The aryl group in the invention is a general name of a monovalent group left after one hydrogen atom is removed from an aromatic nucleus carbon of an aromatic compound molecule. The aryl group includes monocyclic aryl groups, polycyclic aryl groups, fused ring aryl groups, or combinations thereof. The aryl group has a carbon number of C6 to C30, preferably C6 to C25, and preferably C6 to C20. Examples of the aryl group include, but are not limited to, the groups described below , phenyl radical , biphenyl radical , 3. Biphenyl radical , 4. Biphenyl radical , naphthyl radical , phenanthryl radical , anthracenyl group , triphenylene radical , fluorenyl radicals , benzofluorenyl radicals , spirobifluorene group , benzospirobifluorenyl radicals , pyrenyl group , fluoranthenyl ,

And the like, but is not limited thereto.

The heteroaryl group in the present invention refers to a monovalent group in which at least one carbon atom in the aryl group is substituted with a heteroatom. The heteroatom is selected from O, S, N, si, B, P, etc., but is not limited thereto. The carbon number of the heteroaryl group is C2 to C30, more preferably C2 to C25, and still more preferably C3 to C20. Examples of such heteroaryl groups include, but are not limited to, the groups described below , oxazolyl radical , benzoxazolyl radical , naphthoxazolyl radical , phenanthrooxazolyl group , anthraxazolyl group , tribenzoxazolyl radical , pyridooxazolyl radical , pyrimidooxazolyl group , triazinooxazolyl radical , quinoxalazolyl radical , isoquinolooxazolyl radical , quinazolinooxazolyl groups , quinoxalinooxazolyl radical , pyridyl oxazolyl radicals , thiazolyl radical , benzothiazolyl radical , naphthothiazolyl radicals , phenanthro thiazolyl , anthrathiazolyl groups , triphenylbenzothiazolyl group , pyridinothiazolyl group , pyrimido thiazolyl group , triazinothiazolyl , quinolinothiazolyl , isoquinolothiazolyl , thiazolidino thiazolyl , imidazolyl group , benzimidazolyl radicals , naphthoimidazolyl radical , phenanthroimidazolyl , anthrabenzimidazolyl radicals , triphenylbenzimidazolyl group , pyridoimidazolyl , pyrimido-imidazolyl , triazinoimidazolyl group , quinolinoimidazolyl group , isoquinolino imidazolyl , quinoxalinoimidazolyl , quinazolinimidazolyl , furyl radical , benzofuranyl radical , naphthofuryl group , phenanthrofuranyl , anthrafuranofuranyl radical , triphenylene benzofuranyl , dibenzofuranyl radical , thienyl radical , benzothienyl , naphthothienyl radical , phenanthro thienyl radical , anthrathienothienyl radicals , triphenylthienylene , dibenzothienyl radical , indolyl radical , naphthoindolyl radical , phenanthroindolyl , anthra-indolyl group , triphenylene indole group , carbazolyl group , pyridinyl group , pyrimidinyl radicals , pyrazinyl radical , pyridazinyl radical , triazine radical , quinolyl radicals , isoquinolinyl radicals , quinazolinyl radical , quinoxalinyl , naphthyridinyl group , phenanthroline radical , benzoquinolinyl radicals , benzisoquinolinyl and the like , but is not limited thereto. .

ar is selected from the group shown as follows,

the ring B is selected from one of substituted or unsubstituted C10-C30 aromatic ring, substituted or unsubstituted 10-30 membered heteroaromatic ring containing 1N, substituted or unsubstituted fused ring of C3-C20 alicyclic ring and C10-C30 aromatic ring, and substituted or unsubstituted fused ring of C3-C20 alicyclic ring and 10-30 membered heteroaromatic ring;

said X is₁Selected from O or S;

said R is₁Selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30The aromatic group of (a), a substituted or unsubstituted heteroaryl group of (C2 to C30), a condensed ring group of a substituted or unsubstituted alicyclic ring of (C3 to C20) and an aromatic ring of (C6 to C30), a condensed ring group of a substituted or unsubstituted alicyclic ring of (C3 to C20) and a heteroaromatic ring of (C2 to C30), or a substituted or unsubstituted aliphatic heterocyclic group of (C3 to C20);

Ar is₁、Ar₂Independently selected from the group shown below,

said X is₂Selected from O, S, N (R)_x2) Said R is_x2One selected from the group consisting of hydrogen, deuterium, tritium, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C3-C20 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a substituted or unsubstituted fused ring group of a C3-C20 alicyclic ring and a C6-C30 aromatic ring, a substituted or unsubstituted fused ring group of a C3-C20 alicyclic ring and a C2-C30 heteroaromatic ring, and a substituted or unsubstituted C3-C20 lipoheterocyclic group;

Said R is₂Selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstitutedOne of a substituted C2-C30 heteroaryl group, a substituted or unsubstituted fused ring group of a C3-C20 alicyclic ring and a C6-C30 aromatic ring, a substituted or unsubstituted fused ring group of a C3-C20 alicyclic ring and a C2-C30 heteroaromatic ring, and a substituted or unsubstituted C3-C20 alicyclic heterocyclic group;

Preferably, the ring A is selected from the group shown below,

the X is the same or different and is selected from C (Rx) or N, and at most 3X are selected from N, and the Rx is the same or different and is selected from one of hydrogen, deuterium, tritium, halogen, cyano-group, nitro-group, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl and substituted or unsubstituted C3-C20 lipo-heterocyclic group.

Preferably, the ring A is selected from one of the following groups,

r1 is an integer from 1 to 3, and r2 is an integer from 1 to 2;

the Rx is the same or different and is selected from one of hydrogen, deuterium, tritium, halogen, cyano-group, nitro-group, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl and substituted or unsubstituted C3-C15 lipo-heterocyclic group.

Preferably, the ring A is selected from one of the following groups,

r1 is an integer from 1 to 3, and r2 is an integer from 1 to 2;

the Rx are the same or different and are one selected from the group consisting of 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 cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, and substituted or unsubstituted norbornyl.

Preferably, the

One selected from the group shown below,

the z is selected from C (Rz) or N, wherein at most 1 of the groups is N, and the Rz is selected from one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring fused ring group, substituted or unsubstituted C3-C20 alicyclic and C2-C30 heteroaromatic ring fused ring group, or substituted or unsubstituted C3-C20 alicyclic ring fused ring group, or two adjacent Rz are bonded to each other to form a substituted or unsubstituted ring.

Preferably, the

One selected from the group shown below,

n1 is an integer from 1 to 6, and n2 is an integer from 1 to 4; n3 is an integer from 1 to 8, and n4 is an integer from 1 to 3; n5 is an integer from 1 to 2, n6 is an integer from 1 to 5, and n7 is an integer from 1 to 7;

the Rz is the same or different and is selected from one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C2-C25 heteroaryl, substituted or unsubstituted C3-C15 alicyclic ring and C6-C25 aromatic ring fused ring group, substituted or unsubstituted C3-C15 alicyclic ring and C2-C25 heteroaromatic ring fused ring group, substituted or unsubstituted C3-C15 alicyclic ring fused ring group, or two adjacent Rz are mutually bonded to form a substituted or unsubstituted ring.

Preferably, said R₁The same or different is selected from the group consisting of 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 cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, and a substituted or unsubstituted cyclohexyl group, a substituted or unsubstituted adamantyl group, a substituted or unsubstituted bornyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted triphenylene group, a one of substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidyl, substituted or unsubstituted triazinyl, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted benzocyclobutanyl, substituted or unsubstituted dihydroindenyl, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted benzocycloheptanyl, substituted or unsubstituted benzocyclobutenyl, substituted or unsubstituted indenyl, substituted or unsubstituted dihydronaphthyl, substituted or unsubstituted benzocycloheptenyl;

Said R is_zThe same or different groups are selected from 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 cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, substituted or unsubstituted bornyl, 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 pyridyl, substituted or unsubstituted pyrimidyl, substituted or unsubstituted triazinyl, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted quinazolinyl, and the likeOne of an azolyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted benzocyclopropane group, a substituted or unsubstituted benzocyclobutane group, a substituted or unsubstituted indanyl group, a substituted or unsubstituted tetrahydronaphthyl group, a substituted or unsubstituted benzocycloheptane group, a substituted or unsubstituted indenyl group, a substituted or unsubstituted dihydronaphthyl group, and a substituted or unsubstituted benzocycloheptenyl group.

Preferably, the

One selected from the group shown below,

the v is the same or different and is selected from C (Rv) or N, the Rv is the same or different and is selected from one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C20 fused ring group of alicyclic ring and C6-C30 aromatic ring, substituted or unsubstituted C3-C20 alicyclic ring and C2-C30 heteroaromatic ring, substituted or unsubstituted C3-C20 alicyclic ring group, or two adjacent Rv are mutually bonded to form a substituted or unsubstituted ring.

Preferably, the

Is selected from one of the groups shown below>

M1 is an integer from 1 to 6, and m2 is an integer from 1 to 4; m3 is an integer from 1 to 8, and m4 is an integer from 1 to 3; m5 is an integer from 1 to 2, m6 is an integer from 1 to 5, and m7 is an integer from 1 to 7;

the Rv is the same or different and is selected from one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C2-C25 heteroaryl, substituted or unsubstituted C3-C15 alicyclic ring and C6-C25 aromatic ring fused ring group, substituted or unsubstituted C3-C15 alicyclic ring and C2-C25 heteroaromatic ring fused ring group, and substituted or unsubstituted C3-C15 lipoheterocyclic group.

Preferably, said R₂The same or different is selected from the group consisting of 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 cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, substituted or unsubstituted bornyl, 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 pyridyl, substituted or unsubstituted pyrimidyl, substituted or unsubstituted triazinyl, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinylOne of substituted or unsubstituted benzocyclobutane, substituted or unsubstituted dihydroindenyl, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted benzocycloheptanyl, substituted or unsubstituted benzocyclobutene, substituted or unsubstituted indenyl, substituted or unsubstituted dihydronaphthyl, and substituted or unsubstituted benzocycloheptenyl;

Said X₂Selected from O, S, N (R)_x2) Said R is_x2The same or different species are selected from the group consisting of hydrogen, deuterium, tritium, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, substituted or unsubstituted bornyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidyl, substituted or unsubstituted triazinyl, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted benzocyclofluoroalkyl, substituted or unsubstituted benzocyclobutanyl, substituted or unsubstituted indanyl, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted benzocycloheptanyl, substituted or unsubstituted dihydroindenyl, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted benzocycloheptanyl, substituted or unsubstituted benzocyclobutenyl, substituted or unsubstituted heptanyl, substituted or unsubstituted dihydroindenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthryl;

Said R is_vThe same or different is selected from the group consisting of 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 cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, substituted or unsubstituted cyano, nitro, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, and substituted or unsubstituted cyclohexylOr one of unsubstituted bornyl, 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 pyridyl, substituted or unsubstituted pyrimidyl, substituted or unsubstituted triazinyl, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted benzocyclopropanyl, substituted or unsubstituted benzocyclobutanyl, substituted or unsubstituted indanyl, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted benzocycloheptanyl, substituted or unsubstituted benzocyclobutenyl, substituted or unsubstituted indenyl, substituted or unsubstituted dihydronaphthyl, and substituted or unsubstituted benzocycloheptenyl.

Preferably, the L is selected from a single bond or one of the groups shown below,

e1 is selected from an integer of 1 to 4, and e2 is selected from an integer of 1 to 6;

the Y is same or different and is selected from CH or N, each aromatic ring contains at most two N, the Ry is same or different and is selected from one of hydrogen, deuterium, tritium, halogen, cyano-group, nitro-group, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl and substituted or unsubstituted C3-C20 lipoheterocyclic group, or two adjacent Ry are mutually bonded to form a substituted or unsubstituted ring.

e1 is selected from an integer of 1 to 4, and e2 is selected from an integer of 1 to 6; e3 is an integer from 1 to 3, and e4 is an integer from 1 to 2; e5 is selected from an integer of 1 to 8, and e6 is selected from an integer of 1 to 10;

the Ry is same or different and is selected from one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl and substituted or unsubstituted C3-C15 lipoheterocyclic radical;

and Ry0 is the same or different and is one selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C2-C25 heteroaryl, substituted or unsubstituted C3-C15 alicyclic ring and C6-C25 aromatic ring fused ring group, substituted or unsubstituted C3-C15 alicyclic ring and C2-C25 heteroaromatic ring fused ring group, and substituted or unsubstituted C3-C15 lipoheterocyclic group.

Preferably, the Ry is the same or different and is one selected from the group consisting of 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 cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, and substituted or unsubstituted norbornyl;

the Ry0 s are the same or different and are selected from one of 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 cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted benzocyclopropyl, substituted or unsubstituted benzocyclobutenyl, substituted or unsubstituted indanyl, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted benzocyclobutenyl, substituted or unsubstituted indenyl, and substituted or unsubstituted dihydronaphthyl.

Preferably, said L₁、L₂Independently selected from a single bond or one of the groups shown as follows,

the Q is the same or different and is selected from C (Rq) or N, the Rq is the same or different and is selected from one of hydrogen, deuterium, tritium, halogen, cyano-group, nitro-group, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl and substituted or unsubstituted C3-C20 lipoheterocyclic group, or two adjacent Rq are mutually bonded to form a substituted or unsubstituted ring.

f1 is an integer from 1 to 4, and f2 is an integer from 1 to 6; f3 is an integer from 1 to 3, and f4 is an integer from 1 to 2; f5 is selected from an integer of 1-5, f6 is selected from an integer of 1-8, and f7 is selected from an integer of 1-10;

the Rq is the same or different and is selected from one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl and substituted or unsubstituted C3-C15 lipoheterocyclic radical;

and Rq0 is one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C2-C25 heteroaryl, substituted or unsubstituted C3-C15 fused ring group of alicyclic ring and C6-C25 aromatic ring, substituted or unsubstituted C3-C15 fused ring group of alicyclic ring and C2-C25 heteroaromatic ring, and substituted or unsubstituted C3-C15 lipoheterocyclic group.

Preferably, the Rq is the same or different and is one selected from the group consisting of 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 cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, and substituted or unsubstituted norbornyl;

the Rq0 is the same or different and is selected from one of 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 cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted benzocyclopropyl, substituted or unsubstituted benzocyclobutenyl, substituted or unsubstituted indanyl, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted benzocyclobutenyl, substituted or unsubstituted indenyl, and substituted or unsubstituted dihydronaphthyl.

Preferably, the heterocyclic compound of formula 1 is selected from at least one of the structures shown below,

some specific chemical structures of the heterocyclic compounds represented by formula 1 of the present invention are listed above, but the present invention is not limited to these listed chemical structures, and any substituent group as defined above based on the structure represented by formula 1 should be included.

The present invention also provides an organic electroluminescent device comprising the heterocyclic compound of formula 1 of the present invention as described above.

Preferably, the organic electroluminescent device includes an anode, a cathode, and at least one of an organic layer and a capping layer, the organic layer being located between the anode and the cathode, the capping layer being located outside the anode or the cathode, the at least one of the organic layer and the capping layer containing the heterocyclic compound of formula 1 of the present invention as described above.

Preferably, the organic electroluminescent device includes an anode, a cathode, and an organic layer between the anode and the cathode, the organic layer containing the heterocyclic compound of formula 1 of the present invention as described above.

Preferably, the organic layer includes at least one of a light emitting layer and an electron transport region, and at least one of the light emitting layer and the electron transport region includes the heterocyclic compound of formula 1 of the present invention.

Preferably, the organic layer includes a light emitting layer containing the heterocyclic compound of formula 1 of the present invention described above.

Preferably, the light emitting layer contains a host material and a dopant material, and the host material contains the heterocyclic compound of formula 1 of the present invention.

Preferably, the organic layer includes an electron transport region containing the heterocyclic compound of formula 1 of the present invention as described above.

Preferably, the electron transport region includes at least one of a hole blocking layer, an electron transport layer, and an electron injection layer, and the at least one of the hole blocking layer, the electron transport layer, and the electron injection layer contains the heterocyclic compound of formula 1 of the present invention.

Preferably, the organic electroluminescent device comprises an anode, a cathode, an organic layer and a covering layer, wherein the organic layer is positioned between the anode and the cathode, the covering layer is positioned on the outer side of the anode or the cathode, and the covering layer contains the heterocyclic compound of the invention.

The functional layer of the organic electroluminescent device of the present invention may contain at least one of a hole injection layer, a hole transport layer, a light emission auxiliary layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, a capping layer, and the like. All functional layers having hole injecting and/or transporting properties, electron injecting and/or transporting properties, light emitting properties or light extracting properties are included. Each functional layer may be composed of a single layer film or a plurality of layers of films, and each layer of film may be composed of only one material or a plurality of materials.

The material of each thin film in the organic electroluminescent device of the present invention is not particularly limited, and those known in the art can be used. The organic functional layers of the organic electroluminescent device and the electrodes on both sides of the device are described below:

the hole injection material of the invention needs to have the properties of better hole injection capability, more proper HOMO energy level and the like so as to reduce the interface potential barrier between the anode and the hole transport layer and improve the hole injection capability. The hole injection layer includes, but is not limited to, aromatic amine derivatives, metal oxides, phthalocyanine metal complexes, polycyano conjugated organics, polymers, and the like. Specific examples may include N, N' -bis [ 4-di (m-tolyl) aminophenyl group]-N, N ' -diphenylbenzidine (DNTPD), 4',4 "-tris (N- (1-naphthyl) -N-phenylamino) triphenylamine (1-TNATA), 4',4" -tris (N, N-2-naphthylphenylamino) triphenylamine (2-TNATA), molybdenum trioxide (MoO)₃) Vanadium pentoxide (V)₂O₅) Copper phthalocyanine (CuPC), oxytitanium phthalocyanine (TiOPC), 1,4,5,8,9, 11-hexaazabenzonitrile (HAT-CN), 2,3,5, 6-tetrafluoro-7, 7', 8' -tetracyanoldimethylp-benzoquinone (F4-TCNQ), poly (4-vinyltriphenylamine) (PVTPA), and the like, but are not limited thereto.

The hole transport material of the present invention needs to have high hole mobility and good stability to facilitate the injection of holes. The hole transport layer includes, but is not limited to, materials such as arylamine derivatives, carbazole derivatives, polymers, and the like. Specific examples may include N, N ' -diphenyl-N, N ' -di (2-naphthyl) -1,1' -biphenyl-4, 4' -diamine (. Beta. -NPB), N ' -tetra-1-naphthyl [1,1' -biphenyl ] -4,4' -diamine (. Alpha. -TNB), N ' -diphenyl-N, N ' - (1-naphthyl) -1,1' -biphenyl-4, 4' -diamine (NPB), N, N ' -bis (3-methylphenyl) -N, N ' -diphenyl- [1,1' -biphenyl ] -4,4' -diamine (TPD), 4' -cyclohexylbis [ N, N-bis (4-methylphenyl) aniline ] (TAPC), 1,3, 5-tris (9-carbazolyl) benzene (TCB), 4',4 ″ -tris (carbazol-9-yl) triphenylamine (TCTA), polyvinylcarbazole (PVC) and the like, but are not limited thereto.

The electron blocking material of the present invention needs to have a good hole transport ability and an electron blocking ability in order to effectively transport holes and confine electrons. The electron blocking layer includes, but is not limited to, materials described below, aromatic amine derivatives, carbazole derivatives, and the like. Specific examples may include N, N-bis ([ 1,1' -biphenyl ] -4-yl) - (9H-carbazol-9-yl) - [1,1' -biphenyl ] -4-amine, N- (4 ' - (9H-carbazol-9-yl) - [1,1' -biphenyl ] -4-N- ([ 1,1' -biphenyl ] -4-yl) -9, 9-dimethyl-9H-fluoren-2-amine, N ' -bis (naphthalen-1-yl) -N, N ' -diphenyl-benzidine (NPD), and the like, but are not limited thereto.

The light-emitting layer comprises a host 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 host material and the dopant material may vary depending on the material used, and the doping ratio of the dopant material is usually 0.01% to 20%, preferably 0.1% to 15%, and more preferably 1% to 10%.

The host material of the light-emitting layer needs to have a bipolar charge transport property and also needs to have an appropriate energy level to efficiently transfer excitation energy to the guest light-emitting material. The host material may be one material, or two or more materials. The heterocyclic compounds of formula 1 according to the invention are preferred. The heterocyclic compound of formula 1 of the present invention may be used alone as a host material, or in combination with a p-type host material as an n-type host material, and when used in combination with a p-type host material, the weight ratio of the heterocyclic compound of formula 1 of the present invention to the p-type host material is 1. The host material includes, but is not limited to, bicarbazole-based compounds, biphenylocarbazole-based compounds, binaphthocarbazole-based compounds, indolocarbazole-based compounds, indolophenylcarbazoles-based compounds, indenocarbazole-based compounds, benzofurocarbazoles-based compounds, benzothienocarbazoles-based compounds, carbazoles-based compounds, furans-based compounds, thiophenes-based compounds, oxazoles-based compounds, thiazoles-based compounds, imidazoles-based compounds and other heterocyclic compounds, aromatic amine compounds, fused aromatic ring derivatives, metal complexes, silicon-containing compounds and the like, and specific examples thereof may include 9,9' -diphenyl-H, 9' H-3,3' -bicarbazole, 9' -bis ([ 1,1' -biphenyl-9H, 9' H-3,3' -bicarbazole ]-4-yl) -9H,9' Bicarbazole, 9' -bis ([ 1,1' -biphenyl)]-3-yl) -9H,9' Bicarbazole, 9' -bis ([ 1,1' -biphenyl)]-2-yl) -9H,9 'Bicarbazole, 9- ([ 1,1' -biphenyl]-4-yl) -9 '-phenyl-9H, 9' H-3,3 '-Bicarbazole, 9- ([ 1,1' -Biphenyl ]]-3-yl) -9 '-phenyl-9H, 9' H-3,3 '-Bicarbazole, 9- ([ 1,1' -Biphenyl ]Benzene (III)]-2-yl) -9' -phenyl-9H, 9' H-3,3' -bicarbazole, 9' -bis ([ 1,1':4',1' -triphenyl group)]-4-yl) -9H,9', 9' -bis (naphthalen-1-yl) -9H,9'H-3,3' -bicarbazole, 9 '-bis (naphthalen-2-yl) -9H,9' H-3,3 '-bicarbazole, 9' -biphenyl-9H,9 'H-3,3' -bicarbazole-6-carbonitrile (BCzSCN), 5, 7-diphenyl-5, 7-dihydroindolo [2,3-b ] C]Carbazole, 5, 7-bis (1, 1' -biphenyl-4-yl) -5, 7-indolino [2,3-b ]]Carbazole, 5, 7-bis (1, 1' -biphenyl-3-yl) -5, 7-indolino [2,3-b ]]Carbazole, 5, 7-bis (1, 1' -biphenyl-2-yl) -5, 7-indolino [2,3-b ]]Carbazole, 5- (1, 1' -biphenyl-4-yl) -7-phenyl-5, 7-indolino [2,3-b]Carbazole, 5- (1, 1' -biphenyl-3-yl) -7-phenyl-5, 7-indolino [2,3-b]Carbazole, 5- (1, 1' -biphenyl-2-yl) -7-phenyl-5, 7-indolino [2,3-b]Carbazole, 5, 7-bis (1, 1]Carbazole, 5, 7-dinaphthalen-1-yl-5, 7-indolino [2,3-b ] ]Carbazole, 5, 7-dinaphthalen-2-yl-5, 7-indolino [2,3-b ]]Carbazole, 5, 11-diphenyl-5, 11-indolino [3,2-b ]]Carbazole, 5, 11-bis (1, 1' -biphenyl-4-yl) -5, 11-indolino [3,2-b ]]Carbazole, 5- (1, 1' -biphenyl-4-yl) -11-phenyl-5, 11-indolino [3,2-b ]]Carbazole, 5, 11-dinaphthalen-1-yl-5, 11-indolino [3,2-b ]]Carbazole, 5, 11-bis (4- (naphthyl) phenyl) -5, 11-indolino [3,2-b ]]Carbazole, 9- (5- (3- (9H-carbazol-9-yl) phenyl) pyridin-3-yl) -9H-carbazole (CPPyC), 4 '-bis (carbazol-9-yl) -2,2' -dimethylbiphenyl (CDBP), 1, 3-bis (N-carbazolyl) benzene (MCP), 9-dimethyl-N, N-diphenyl-7- (4- (1-phenyl-1H-benzo [ d ] b]Imidazol-2-yl) phenyl) -9H-fluoren-2-amine (EFIN), 10- (4' - (diphenylamino) biphenyl-4-yl) acridin-9 (10H) -one (ADBP), tris [4- (pyrenyl) -phenyl]Amine (TPyPA), 9, 10-di (2-naphthyl) Anthracene (ADN), 2-tert-butyl-9, 10-di (2-naphthyl) anthracene (TBADN), 1- (7- [9,9' -bianthracene]-10-yl-9, 9-dioctyl-9H-fluoren-2-yl) pyrene (BAnF 8 Pye), 9 '-tetrakis (4-methylphenyl) -2,2' -bi-9H-fluorene (BDAF), tris (6-fluoro-8-hydroxyquinoline) aluminium (6 FAlq)₃) Tris (8-hydroxyquinoline) aluminum (Alq)₃) Bis (10-hydroxybenzo [ H ]]Quinoline) beryllium (BeBq)₂) Bis (8-hydroxyquinoline) zinc (Znq) ₂) Etc., but are not limited thereto.

The dopant material may be a fluorescent material, a phosphorescent material, a TADF material, or a combination thereof. Doping materials include, but are not limited to, the followingMaterials, metal complexes, aromatic amine derivatives, styrylamine compounds, fused aromatic compounds, heterocyclic compounds, and the like. Specific examples may include bis [ 4-tert-butyl-2 ',6' -difluoro-2, 3' -bipyridine]Iridium (acetylacetonate) (FK 306), bis (2- (2-hydroxyphenyl) -pyridine) beryllium (Bepp)₂) Bis (3, 4, 5-trifluoro-2- (2-pyridyl) phenyl- (2-carboxypyridyl) iridium (Ir (tfpd)₂pic), bis (2- (naphthalen-2-yl) pyridine) (acetylacetone) iridium (Ir (npy)₂acac), tris [ 2-phenyl-4-methylquinoline)]Iridium (Ir (Mphq)₃) Bis (2-phenylpyridine) iridium acetylacetonate (Ir (ppy)₂(acac)), tris [2- (3-methyl-2-pyridyl) phenyl]Iridium (Ir (3 mppy)₃) Bis (2-benzo [ H ]]quinoline-C2, N') (acetylacetonato) iridium (Ir (bzq)₂(acac)), tris (2- (3, 5-dimethylphenyl) quinoline-C2, N') iridium (Ir (dmpq)₃) Bis (1-phenyl-isoquinoline) (acetylacetonate) iridium (Ir (piq)₂(acac)), tris [ 5-hexyl-2- (1-isoquinolinyl) phenyl]Iridium (Hex-Ir (piq)₃) Octaethylporphyrin platinum (PtOEP) 4,4' - [1, 4-phenylenedi- (1E) -2, 1-ethenediyl]Bis [ N, N-diphenylaniline ](DSA-Ph), 1' -bis (3, 5-bis (trifluoromethyl) phenyl) -9,9' -dianthracene (Ban- (3, 5) -CF 3), N, N, N ', N ' -tetrakis (4-methylphenyl) - [9,9' -dianthracene]10,10' -diamine (BA-TTB), 1' -bis (3, 5-bis (trifluoromethyl) phenyl) -9,9' -bianthryl (Ban- (3, 5) -CF 3), 2,5,8, 11-tetra-tert-butylperylene (TBPe), N1, N6-bis (dibenzofuran-4-yl) -N1, N6-di-m-tolylpyrene-1, 6-diamine, rubrene, 9- (9-phenylcarbazol-3-yl) -10- (naphthalen-1-yl) (PCAN), 1, 4-bis (4- (9H-carbazol-9-yl) styryl) benzene (BCzSB), 1' - (4, 4' - (4-phenyl-4H-1, 2, 4-triazole-3, 5-diyl) bis (4, 1-phenylene)) bis (1H-phenoxazine) (2Z-TAZ), 2, 5-bis (4- (1H-benzoxazin-1-yl) phenyl) -1,3, 4-oxadiazole (2 PXZ-OXD), (E) -2- (2-tert-butyl-6- (2, 6-trimethyl-2, 4,5, 6-tetrahydro-1H-pyrrolo [3,2,1-IJ ], (E) -2, 6-trimethyl-2, 6-t-yl) phenyl]]Quinolin-8-yl) vinyl) -4H-pyran-4-alkylene) malononitrile (DCQTB), and the like, but is not limited thereto.

The hole blocking layer provided by the invention has the effects of blocking holes in the light-emitting layer and improving the combination rate of electrons and holes. The hole blocking layer includes, but is not limited to, materials described below, metal complexes, heteroaromatic compounds, and the like. Specific examples may include bis (2-methyl-8-hydroxyquinoline-N1, O8) - (1, 1' -biphenyl-4-hydroxy) aluminum (BAlq), 1,3, 5-tris (N-phenyl-2-benzimidazole) benzene (TPBi), 2, 9-bis (naphthalen-2-yl) -4, 7-diphenyl-1, 10-phenanthroline (NBphen), 2, 9-dimethyl-4, 7-diphenyl-1, 10-phenanthroline (BCP), and the like, but are not limited thereto.

The electron transport material of the present invention needs to have high electron mobility and good stability to facilitate electron injection. The electron transport layer includes, but is not limited to, materials described below, heteroaromatic compounds, metal complexes, polymers, and the like. Specific examples may include 2, 9-bis (naphthalen-2-yl) -4, 7-diphenyl-1, 10-phenanthroline (NBphen), 1,3, 5-tris (4-pyridin-3-ylphenyl) benzene (TpPyPB), 3- (biphenyl-4-yl) -4-phenyl-5- (4-tert-butylphenyl) -1,2, 4-Triazole (TAZ), 2- (4- (9, 10-bis (naphthalen-2-yl) anthracen-2-yl) phenyl) -1-phenyl-1H-phenanthrene [9,10-d]Imidazole (ADN-PAimi), 1, 3-bis (N, N-tert-butyl-phenyl) -1,3, 4-oxadiazole (OXD-7), 8-hydroxyquinoline aluminum (Alq)₃) Tris (4-methyl-8-quinolinolato) aluminum (Al (4-Mq)₃) Bis (10-hydroxybenzo [ h ]]Quinoline) beryllium (Bepq)₂) Bis (10-hydroxybenzo [ h ]]Quinoline) beryllium (BeBq)₂) Bis (8-hydroxyquinoline) zinc (II) (Znq), poly [ (9, 9-dioctylfluorene-2, 7-diyl) -co- (2, 2 '-bipyridine-6, 6' -diyl)](PF-BPy), etc., but are not limited thereto. The heterocyclic compounds of formula 1 according to the invention are preferred.

The electron injection material of the invention needs to have the properties of better hole injection capability, more proper energy level and the like so as to reduce the interface barrier between the cathode and the electron transport layer and improve the electron injection capability. The electron injection layer material includes, but is not limited to, materials, metals, metal compounds, metal oxides, and the like as described below. Specific examples may include lithium (Li), lithium fluoride (LiF), sodium fluoride (NaF), lithium 8-hydroxyquinoline (Liq), cesium carbonate (Cs) ₂CO₃) Rubidium acetate (CH)₃COORb), lithium oxide (Li)₂O), etc., but are not limited thereto.

The cladding layer of the present invention has the effect of coupling out light trapped within the device. The capping layer material includes, but is not limited to, a metal compound, an aromatic amine derivative, a carbazole derivative, and the like as described below. Specific examples may include 8-hydroxyquinoline aluminum (Alq)₃) N, N '-di (naphthalene-1-yl) -N, N'Bis (phenyl) -2,2 '-dimethylbenzidine (NPD), 4' -bis (9-Carbazole) Biphenyl (CBP), and the like. The heterocyclic compounds of formula 1 according to the invention are preferred.

The anode of the present invention is required to have a high work function in order to improve the hole injection efficiency. The anode includes, but is not limited to, materials such as metal oxides, combinations of metals and oxides, metals or alloys thereof, layered materials, and the like. Specific examples may include Indium Tin Oxide (ITO), indium Zinc Oxide (IZO), aluminum (Al), titanium (Ti) gold (Au), platinum (Pt), copper (Cu), silver (Ag), indium tin oxide/silver/indium tin oxide (ITO/Ag/ITO), and the like, but are not limited thereto.

The cathode of the present invention is required to have a low work function in order to improve the electron injection efficiency. The cathode includes, but is not limited to, materials described below, metals or alloys thereof, laminates, and the like. Specific examples may include aluminum (Al), silver (Ag), calcium (Ca), indium (In), magnesium: silver (Mg: ag), etc., but are not limited thereto.

The method for preparing each layer of thin film in the organic electroluminescent device of the present invention is not particularly limited, and vacuum evaporation, sputtering, spin coating, spray coating, screen printing, laser transfer printing, and the like may be used, but is not limited thereto.

The organic electroluminescent device is mainly applied to the technical field of information display and the field of illumination, and is widely applied to various information displays in the aspect of information display, such as mobile phones, tablet computers, flat televisions, smart watches, VRs, vehicle-mounted systems, digital cameras, wearable equipment and the like.

Synthetic examples

Raw materials and reagents: the starting materials and reagents used in the following synthetic examples are not particularly limited, and may be commercially available products or prepared by methods known to those skilled in the art. The raw materials and reagents used in the invention are all pure reagents.

The instrument comprises: G2-Si quadrupole tandem time-of-flight high resolution mass spectrometer (waters, uk); a Vario EL cube type organic element analyzer (Elementar Co., ltd., germany).

The method for preparing the heterocyclic compound represented by formula 1 of the present invention is not particularly limited, and conventional methods well known to those skilled in the art may be employed. For example, carbon-carbon coupling reaction, etc., the heterocyclic compound represented by formula 1 of the present invention can be prepared, for example, by the following synthetic route.

The Xn is halogen, for example, the Xn is the same or different and is selected from Cl, br and I.

In addition, the order of the above-mentioned reactions may be changed to obtain the heterocyclic compound represented by formula 1 of the present invention.

Synthesis example 1: synthesis of Compound 18

Synthesis of intermediate A-18:

under the protection of nitrogen, a-18 (54.07g, 200.00mmol), pinacol diboron (111.73g, 440.00mmol) and CH are added into a reaction bottle₃COOK(51.03g,520.00mmol)、Pd(dppf)Cl₂(0.88g, 1.20mmol) and 1500ml of THF were reacted under reflux for 7 hours. After the reaction, the reaction mixture was cooled to room temperature, water was added, a filter cake was obtained by suction filtration, and dried in a vacuum oven, and the crude product was isolated and purified by a silica gel column (n-hexane: ethyl acetate = 1) to obtain an intermediate a-18 (58.32 g, yield 80%); HPLC purity is more than or equal to 99.75 percent.

Synthesis of intermediate B-18:

a-18 (60.14g, 165.00mmol), b-18 (82.24g, 300.00mmol) and Na were added to a reaction flask under the protection of nitrogen₂CO₃(47.70g,450.00mmol)、Pd(PPh₃)₄(3.47g, 3.00mmol) and 1200ml of 1, 4-dioxane, were reacted under reflux for 8 hours. After the reaction was completed, it was cooled to room temperature, water was added thereto, extraction was performed with methylene chloride, and the organic layer was extracted with anhydrous MgSO₄Drying, removal of solvent under reduced pressure, and recrystallization from toluene/petroleum ether =4 1 gave intermediate B-18 (56.13 g, yield 75%); HPLC purity is more than or equal to 99.67 percent.

Synthesis of intermediate C-18:

under the protection of nitrogen, B-18 (49.90g, 100.00mmol), pinacol diboron (27.93g, 110.00mmol) and K are added into a reaction bottle₂CO₃(17.97g,130.00mmol)、Pd(dppf)Cl₂(0.37g, 0.500mmol) and 850ml of THF were reacted under reflux for 6.5 hours. After the reaction was completed, cooling to room temperature, adding water, suction-filtering to obtain a filter cake, and recrystallizing with toluene/n-hexane = 5; HPLC purity is more than or equal to 99.86%.

Synthesis of compound 18:

under the protection of nitrogen, C-18 (19.49g, 33.00mmol), C-18 (9.73g, 30.00mmol) and Na were added into a reaction flask₂CO₃(4.77g,45.00mmol)、Pd(OAc)₂(0.07g,0.30mmol)、P(t-Bu)₃(0.06g, 0.30mmol) and 300ml of THF were reacted under reflux for 8.5 hours. After the reaction was completed, it was cooled to room temperature, water was added thereto, extraction was performed with chloroform, and the organic layer was extracted with anhydrous MgSO₄Drying, removal of the solvent under reduced pressure and recrystallization from toluene gave compound 18 (15.50, 73% yield); the HPLC purity is more than or equal to 99.91 percent. Mass spectrum m/z:707.2216 (theoretical value: 707.2209). Theoretical element content (%) C₄₉H₂₉N₃O₃: c,83.15; h,4.13; and N,5.94. Measured elemental content (%): c,83.12; h,4.15; and N,5.90.

Synthesis example 2: synthesis of Compound 20

According to the preparation method of synthetic example 1, b-18 and c-18 were replaced with equimolar b-20 and c-20, respectively, to obtain compound 20 (16.78 g) having a solid purity of 99.89% or more by HPLC. Mass spectrum m/z:860.2796 (theoretical value: 860.2787). Theoretical element content (%) C ₆₀H₃₆N₄O₃: c,83.70; h,4.21; n,6.51. Measured elemental content (%): c,83.74; h,4.23; and N,6.47.

Synthetic example 3: synthesis of Compound 53

According to the preparation method of synthetic example 1, b-18 and c-18 were replaced with equimolar b-53 and c-53, respectively, to obtain compound 53 (14.73 g) having a solid purity of 99.93% or more by HPLC. Mass spectrum m/z:681.2044 (theoretical value: 681.2052). Theoretical element content (%) C₄₇H₂₇N₃O₃: c,82.80; h,3.99; and N,6.16. Measured elemental content (%): c,82.83; h,3.95; n,6.14.

Synthetic example 4: synthesis of Compound 64

According to the preparation method of synthetic example 1, b-18 and c-18 were replaced with equimolar b-64 and c-64, respectively, to obtain compound 64 (12.66 g) with a solid purity of 99.89% or more by HPLC. Mass spectrum m/z:611.1442 (theoretical value: 611.1454). Theoretical element content (%) C₃₅H₁₇N₉O₃: c,68.74; h,2.80; n,20.61. Measured elemental content (%): c,68.71; h,2.84; and N,20.64.

Synthetic example 5: synthesis of Compound 89

According to the preparation method of Synthesis example 1, b-18 and c-18 were replaced with equimolar b-89 and c-89, respectively, to obtain Compound 89 (13.67 g) with a solid purity of 99.92% or more by HPLC. Mass spectrum m/z:701.1652 (theoretical value: 701.1634). Theoretical element content (%) C ₄₃H₂₃N₇O₂S: c,73.60; h,3.30; and N,13.97. Measured elemental content (%): c,73.63; h,3.34; and N,13.94.

Synthetic example 6: synthesis of Compound 113

According to the preparation method of synthetic example 1, b-18 and c-18 were replaced with equimolar b-113 and c-113, respectively, to obtain compound 113 (12.94 g) having a solid purity of 99.94% or more by HPLC. Mass spectrum m/z:607.1652 (theoretical value: 607.1644). Theoretical element content (%) C₃₉H₂₁N₅O₃: c,77.09; h,3.48; n,11.53. Measured elemental content (%): c,77.12; h,3.45; n,11.50.

Synthetic example 7: synthesis of Compound 123

According to the preparation method of Synthesis example 1, compound 123 (13.24 g) was obtained by replacing a-18, b-18 and c-18 with equimolar a-123, b-53 and c-113, respectively, and the solid purity by HPLC analysis was 99.91% or more. Mass spectrum m/z:630.1685 (theoretical value: 630.1692). Theoretical element content (%) C₄₂H₂₂N₄O₃: c,79.99; h,3.52; and N,8.88. Measured elemental content (%): c,79.95; h,3.50; and N,8.91.

Synthesis example 8: synthesis of Compound 128

According to the preparation method of synthetic example 1, a-18, b-18 and c-18 were replaced with equimolar a-128, b-128 and c-128, respectively, to obtain compound 128 (15.52 g), which was found to have a solid purity of 99.95% or more by HPLC. Mass spectrum m/z:760.2236 (theoretical value: 760.2223). Theoretical element content (%) C ₅₀H₂₈N₆O₃: c,78.94; h,3.71; n,11.05. Measured elemental content (%): c,78.97; h,3.74; and N,11.02.

Synthetic example 9: synthesis of Compound 130

According to the preparation method of synthetic example 1, b-18 and c-18 were replaced with equimolar b-130 and c-128, respectively, to obtain compound 130 (16.95 g) having a solid purity of 99.90% or more by HPLC. Mass spectrum m/z:859.2594 (theoretical value: 859.2583). Theoretical element content (%) C₅₉H₃₃N₅O₃: c,82.41; h,3.87; and N,8.14. Measured elemental content (%): c,82.37; h,3.84; and N,8.17.

Synthetic example 10: synthesis of Compound 144

According to the preparation method of synthetic example 1, b-18 and c-18 were replaced with equimolar b-144 and c-128, respectively, to obtain 144 (18.37 g) as a compound having a solid purity of 99.88% or more by HPLC. Mass spectrum m/z:957.2971 (theoretical value: 957.2991). Theoretical element content (%) C₆₉H₃₉N₃O₃: c,86.50; h,4.10; n,4.39. Measured elemental content (%): c,86.53; h,4.14; n,4.36.

Synthetic example 11: synthesis of Compound 148

According to the preparation method of synthetic example 1, b-18 and c-18 were replaced with equimolar b-53 and c-128, respectively, to obtain compound 148 (13.08 g) having a solid purity of 99.97% or more by HPLC. Mass spectrum m/z:605.1730 (theoretical value: 605.1739). Theoretical element content (%) C ₄₁H₂₃N₃O₃: c,81.31; h,3.83; and N,6.94. Measured elemental content (%): c,81.34; h,3.81; and N,6.98.

Synthetic example 12: synthesis of Compound 151

According to the preparation method of synthetic example 1, b-18 and c-18 were replaced with equimolar b-128 and c-151, respectively, to obtain 151 (17.05 g) having a solid purity of 99.90% or more by HPLC. Mass spectrum m/z:757.2358 (theoretical value: 757.2365). Theoretical element content (%) C₅₃H₃₁N₃O₃: c,84.00; h,4.12; n,5.54. Measured elemental content (%): c,84.04; h,4.15; and N,5.50.

Synthetic example 13: synthesis of Compound 152

According to the preparation method of synthetic example 1, b-18 and c-18 were replaced with equimolar b-152 and c-151, respectively, to obtain compound 152 (19.03 g) having a solid purity of 99.93% or more by HPLC. Mass spectrum m/z:857.2689 (theoretical value: 857.2678). Theoretical element content (%) C₆₁H₃₅N₃O₃: c,85.40; h,4.11; and N,4.90. Measured elemental content (%): c,85.43; h,4.07; and N,4.94.

Synthesis example 14: synthesis of Compound 160

According to the preparation method of synthetic example 1, a-18, b-18 and c-18 were replaced with equimolar a-128, b-160 and c-151, respectively, to obtain compound 160 (18.45 g) with a solid purity of 99.95% or more by HPLC. Mass spectrum m/z:960.2858 (theoretical value: 960.2849). Theoretical element content (%) C ₆₆H₃₆N₆O₃: c,82.49; h,3.78; n,8.74. Measured elemental content (%): c,82.47; h,3.81; n,8.78.

Synthetic example 15: synthesis of Compound 176

According to the preparation method of synthetic example 1, b-18 and c-18 were replaced with equimolar b-176 and c-128, respectively, to obtain compound 176 (16.78 g) having a solid purity of 99.96% or more by HPLC. Mass spectrum m/z:755.2467 (theoretical value: 755.2460). Theoretical element content (%) C₅₅H₃₃NO₃: c,87.40; h,4.40; n,1.85. Measured elemental content (%): c,87.36; h,4.37; n,1.88.

Synthetic example 16: synthesis of Compound 191

According to the preparation method of synthetic example 1, compound 191 (16.34 g) was obtained by replacing b-18 and c-18 with equimolar b-191 and c-191, respectively, and the solid purity was 99.94% or more by HPLC. Mass spectrum m/z:777.1958 (theoretical value: 777.1947). Theoretical element content (%) C₄₉H₂₇N₇O₂S: c,75.66; h,3.50; and N,12.60. Measured elemental content (%): c,75.63; h,3.52; and N,12.64.

Synthetic example 17: synthesis of Compound 205

According to the preparation method of Synthesis example 1, compound 205 (17.41 g) was obtained by replacing b-18 and c-18 with equimolar b-205 and c-191, respectively, and the solid purity by HPLC analysis was 99.97% or more. Mass spectrum m/z:805.1694 (theoretical value: 805.1680). Theoretical element content (%) C ₅₃H₃₁N₃S₃: c,78.98; h,3.88; and N,5.21. Measured elemental content (%): c,78.94; h,3.85; and N,5.18.

Synthetic example 18: synthesis of Compound 218

Synthesis of intermediate C-151:

following the same procedure as that for the preparation of intermediate C-18 in Synthesis example 1, b-18 was replaced with equimolar b-128 to give intermediate C-151 (46.65g, 79%) having a solid purity of 99.90% or more by HPLC. Mass spectrum m/z:590.2388 (theoretical value: 590.2377).

Synthesis of intermediate D-218:

under the protection of nitrogen, C-151 (45.47g, 77.00mmol), raw material d-218 (13.40g, 70.00mmol) and Pd (PPh) are added into a reaction bottle₃)₄(0.24g，0.21mmol)、K₂CO₃(14.51g, 105.00mmol) and 210mL of toluene, 70mL of ethanol, 70mL of water, the mixture was stirred, and the reactant system was heated to reflux for 5 hours. After the reaction is finished, cooling to room temperature, performing suction filtration to obtain a filter cake, washing the filter cake with ethanol, and finally, adding toluene/methanol =7:1 recrystallisation to give intermediate D-218 (31.00 g, 77% yield); HPLC purity is more than or equal to 99.74 percent.

Synthesis of intermediate E-218:

d-218 (28.75g, 50.00mmol), pinacol diboron (13.97g, 55.00mmol) and K were added to a reaction flask under nitrogen protection₂CO₃(10.37g,75.00mmol)、Pd(dppf)Cl₂(0.18g, 0.25mmol) and 250ml of THF were reacted under reflux for 8 hours. After the reaction was finished, cooling to room temperature, adding water, performing suction filtration to obtain a filter cake, and recrystallizing with toluene/ethanol = 10; the HPLC purity is more than or equal to 99.85 percent.

Synthesis of compound 218:

under the protection of nitrogen, E-218 (22.00g, 33.00mmol), c-151 (9.89g, 30.00mmol) and Na were added into a reaction flask₂CO₃(4.77g,45.00mmol)、Pd(OAc)₂(0.07g,0.30mmol)、P(t-Bu)₃(0.06g, 0.30mmol) and 120ml of THF were reacted under reflux for 9 hours. After the reaction is finished, cooling to room temperature, adding water, and extracting with chloroformCollecting organic layer, and adding anhydrous MgSO₄Drying, removal of the solvent under reduced pressure and recrystallization from toluene gave compound 218 (17.76 g, 71% yield); HPLC purity is more than or equal to 99.89%. Mass spectrum m/z:833.2669 (theoretical value: 833.2678). Theoretical element content (%) C₅₉H₃₅N₃O₃: c,84.98; h,4.23; and N,5.04. Measured elemental content (%): c,84.95; h,4.26; and N,5.01.

Synthetic example 19: synthesis of Compound 220

According to the preparation method of synthetic example 18, b-128, d-218 and c-151 were replaced with equimolar amounts of b-220, d-220 and c-220, respectively, to give compound 220 (16.46 g) having a solid purity of 99.92% or more by HPLC. Mass spectrum m/z:806.2302 (theoretical value: 806.2318). Theoretical element content (%) C₅₆H₃₀N₄O₃: c,83.36; h,3.75; and N,6.94. Measured elemental content (%): c,83.39; h,3.72; and N,6.98.

Synthesis example 20: synthesis of Compound 226

According to the preparation method of synthetic example 18, b-128 and c-151 were replaced with equimolar b-53 and c-128, respectively, to give compound 226 (14.93 g) with a solid purity of 99.95% or more by HPLC. Mass spectrum m/z:681.2043 (theoretical value: 681.2052). Theoretical element content (%) C ₄₇H₂₇N₃O₃: c,82.80; h,3.99; and N,6.16. Measured elemental content (%): c,82.83; h,3.95; and N,6.18.

Synthetic example 21: synthesis of Compound 229

According to the preparation method of synthetic example 18, b-128, d-218 and c-151 were replaced with equimolar amounts of b-191, d-229 and c-113, respectively, to give 229 (17.30 g) with a solid purity of 99.92% or more by HPLC. Mass spectrum m/z:835.2570 (theoretical value: 835.2583). Theoretical element content (%) C₅₇H₃₃N₅O₃: c,81.90; h,3.98; and N,8.38. Measured elemental content (%): c,81.94; h,3.95; n,8.41.

Synthetic example 22: synthesis of Compound 233

According to the preparation method of synthetic example 18, c-151 was replaced with equimolar c-233, respectively, to obtain compound 233 (16.35 g) having a solid purity of 99.91% or more by HPLC. Mass spectrum m/z:757.2381 (theoretical value: 757.2365). Theoretical element content (%) C₅₃H₃₁N₃O₃: c,84.00; h,4.12; n,5.54. Measured elemental content (%): c,84.04; h,4.10; n,5.51.

Synthetic example 23: synthesis of Compound 235

According to the preparation method of synthetic example 18, b-128, d-218 and c-151 were replaced with equimolar b-235, d-229 and c-235, respectively, to give compound 235 (17.27 g) with a solid purity of 99.94% or more by HPLC. Mass spectrum m/z:858.2643 (theoretical value: 858.2631). Theoretical element content (%) C ₆₀H₃₄N₄O₃: c,83.90; h,3.99; and N,6.52. Measured elemental content (%): c,83.87; h,3.94; and N,6.55.

Synthetic example 24: synthesis of Compound 236

According to the preparation method of synthetic example 18, b-128 was replaced with equimolar b-236, respectively, to obtain compound 236 (14.90 g) having a solid purity of 99.97% or more by HPLC. Mass spectrum m/z:689.2563 (theoretical value: 689.2555). Theoretical element content (%) C₄₇H₁₉D₈N₃O₃: c,81.84; h,5.11; and N,6.09. Measured elemental content (%): c,81.81; h,5.15; and N,6.06.

Synthetic example 25: synthesis of Compound 242

According to the preparation method of Synthesis example 18, compound 242 (15.41 g) was obtained by replacing a-18, b-128 and c-151 with equimolar a-242, b-53 and c-128, respectively, and the solid purity by HPLC analysis was 99.96% or more. Mass spectrum m/z:684.2252 (theoretical value: 684.2241). Theoretical element content (%) C₄₇H₂₄D₃N₃O₃: c,82.44; h,4.42; n,6.14. Measured elemental content (%): c,82.47; h,4.46; and N,6.11.

Synthetic example 26: synthesis of Compound 243

According to the preparation method of synthetic example 18, b-128, d-218, cAnd (5) replacing 151 with equimolar b-53, d-243 and c-128 to obtain a compound 243 (14.81 g), wherein the purity of the solid is more than or equal to 99.93 percent by HPLC detection. Mass spectrum m/z:685.2315 (theoretical value: 685.2303). Theoretical element content (%) C ₄₇H₂₃D₄N₃O₃: c,82.32; h,4.56; and N,6.13. Measured elemental content (%): c,82.28; h,4.59; and N,6.10.

Synthesis example 27: synthesis of Compound 253

According to the preparation method of synthetic example 18, b-128, d-218 and c-151 were replaced with equimolar amounts of b-53, d-253 and c-253, respectively, to give compound 253 (14.51 g) with a solid purity of 99.90% or more by HPLC. Mass spectrum m/z:690.2607 (theoretical value: 690.2617). Theoretical element content (%) C₄₇H₁₈D₉N₃O₃: c,81.72; h,5.25; and N,6.08. Measured elemental content (%): c,81.75; h,5.21; and N,6.04.

Synthetic example 28: synthesis of Compound 261

According to the preparation method of synthetic example 18, b-128, d-218 and c-151 were replaced with equimolar amounts of b-53, d-229 and c-261, respectively, to obtain compound 261 (14.73 g) having a solid purity of 99.93% or more by HPLC. Mass spectrum m/z:732.2152 (theoretical value: 732.2161). Theoretical element content (%) C₅₀H₂₈N₄O₃: c,81.95; h,3.85; and N,7.65. Measured elemental content (%): c,81.98; h,3.89; and N,7.62.

Synthetic example 29: synthesis of Compound 266

According to the preparation method of synthetic example 18, b-128, d-218 and c-151 were replaced with equimolar amounts of b-53, d-266 and c-128, respectively, to give compound 266 (14.94 g) having a solid purity of 99.97% or more by HPLC. Mass spectrum m/z:721.2350 (theoretical value: 721.2365). Theoretical element content (%) C ₅₀H₃₁N₃O₃: c,83.20; h,4.33; and N,5.82. Measured elemental content (%): c,83.24; h,4.30; and N,5.86.

Synthesis example 30: synthesis of Compound 276

According to the preparation method of synthetic example 18, b-128, d-218 and c-151 were replaced with equimolar amounts of b-276, d-276 and c-128, respectively, to give compound 276 (18.81 g) having a solid purity of 99.92% or more by HPLC. Mass spectrum m/z:965.2549 (theoretical value: 965.2535). Theoretical element content (%) C₆₇H₃₉N₃OS₂: c,83.29; h,4.07; and N,4.35. Measured elemental content (%): c,83.26; h,4.11; n,4.32.

Synthetic example 31: synthesis of Compound 280

According to the preparation method of synthetic example 18, b-128, d-218 and c-151 were replaced with equimolar b-280, d-280 and c-280, respectively, to give compound 280 (20.20 g) having a solid purity of 99.94% or more by HPLC. Mass spectrum m/z:989.2715 (theoretical value: 989.2721). Theoretical element content (%) C₆₄H₄₂F₃N₃OS₂: c,77.63; h,4.28; and N,4.24. Measured elemental content (%): c,77.66; h,4.25; and N,4.20.

Synthetic example 32: synthesis of Compound 303

According to the preparation method of Synthesis example 18, a-18, b-128 and c-151 were replaced with equimolar a-128, b-303 and c-128, respectively, to give compound 303 (14.75 g) with a solid purity of 99.97% or more by HPLC. Mass spectrum m/z:682.2014 (theoretical value: 682.2005). Theoretical element content (%) C ₄₆H₂₆N₄O₃: c,80.92; h,3.84; and N,8.21. Measured elemental content (%): c,80.95; h,3.80; and N,8.24.

Synthetic example 33: synthesis of Compound 309

According to the preparation method of synthetic example 18, b-128, c-151 and d-218 were replaced with equimolar b-309, d-229 and c-220, respectively, to obtain compound 309 (14.95 g) with a solid purity of 99.97% or more by HPLC. Mass spectrum m/z:711.1676 (theoretical value: 711.1691). Theoretical element content (%) C₄₉H₂₉NOS₂: c,82.67; h,4.11; and N,1.97. Measured elemental content (%): c,82.69; h,4.15; n,1.94.

Synthesis example 34: synthesis of Compound 310

According to the preparation method of synthetic example 18, b-128, d-218 and c-151 were replaced with equimolar amounts of b-310, d-229 and c-310, respectively, to give compound 310 (15.06 g), which was found to have a solid purity of 99.91% or more by HPLC. Mass spectrum m/z:797.2351 (theoretical value: 797.2366). Theoretical element content (%) C₅₇H₃₂FNO₃: c,85.81; h,4.04; n,1.76. Measured elemental content (%): c,85.85; h,4.01; n,1.79.

Synthetic example 35: synthesis of Compound 357

According to the preparation method of synthetic example 18, b-128 and c-151 were replaced with equimolar b-357 and c-191, respectively, to obtain 357 (16.26 g) as a compound having a solid purity of 99.96% or more by HPLC. Mass spectrum m/z:847.2784 (theoretical value: 847.2770). Theoretical element content (%) C ₅₉H₃₇N₅S: c,83.56; h,4.40; and N,8.26. Measured elemental content (%): c,83.60; h,4.35; and N,8.29.

Synthetic example 36: synthesis of Compound 371

According to the preparation method of Synthesis example 18, C-151, d-218, and C-151 were replaced with equimolar amounts of C-371, d-371, and C-371, respectively, to give compound 371 (15.20 g) with a solid purity of 99.95% or more by HPLC. Mass spectrum m/z:703.2280 (theoretical value: 703.2293). Theoretical element content (%) C₄₇H₃₃N₃O₂S: c,80.20; h,4.73; and N,5.97. Measured elemental content (%): c,80.24; h,4.78; and N,5.93.

Synthetic example 37: synthesis of Compound 381

According to the preparation method of synthetic example 18, b-128, d-218 and c-151 were replaced with equimolar b-176, d-229 and c-381, respectively, to give compound 381 (15.72 g) with a solid purity of 99.97% or more by HPLC. Mass spectrum m/z:782.2555 (theoretical value: 782.2569). Theoretical element content (%) C₅₆H₃₄N₂O₃: c,85.91; h,4.38; and N,3.58. Measured elemental content (%): c,85.96; h,4.34; and N,3.62.

Synthetic example 38: synthesis of Compound 392

According to the preparation method of synthetic example 18, b-18 was replaced with equimolar b-392, and c-151 was replaced with equimolar c-392 to give compound 392 (18.31 g) having a solid purity of 99.94% or more by HPLC. Mass spectrum m/z:871.3036 (theoretical value: 871.3021). Theoretical element content (%) C ₆₃H₄₁N₃S: c,86.77; h,4.74; and N,4.82. Measured elemental content (%): c,86.72; h,4.79; and N,4.86.

Synthetic example 39: synthesis of Compound 397

According to the preparation method of synthetic example 18, compound 397 (13.03 g) was obtained by replacing a-18, b-128, d-218 and c-151 with equimolar a-397, b-397, d-229 and c-397, respectively, and the solid purity was 99.96% or more as determined by HPLC. Mass spectrum m/z:638.1221 (theoretical value: 638.1235). Theoretical element content (%) C₄₀H₂₂N₄OS₂: c,75.21; h,3.47; n,8.77. Measured elemental content (%): c,75.25; h,3.43; and N,8.81.

Synthetic example 40: synthesis of Compound 404

According to the preparation method of synthetic example 18, b-128, d-218 and c-151 were replaced with equimolar b-397, d-229 and c-404, respectively, to obtain compound 404 (12.16 g) with a solid purity of 99.92% or more by HPLC. Mass spectrum m/z:654.1021 (theoretical value: 654.1007). Theoretical element content (%) C₄₀H₂₂N₄S₃: c,73.37; h,3.39; n,8.56. Measured elemental content (%): c,73.40; h,3.34; and N,8.60.

Synthesis example 41: synthesis of Compound 426

According to the preparation method of synthetic example 18, b-128, d-218 and c-151 were replaced with equimolar amounts of b-426, d-229 and c-426, respectively, to give compound 426 (17.12 g) having a solid purity of 99.89% or more by HPLC. Mass spectrum m/z:851.2368 (theoretical value: 851.2355). Theoretical element content (%) C ₅₇H₃₃N₅O₂S: c,80.36; h,3.90; n,8.22. Measured elemental content (%): c,80.33; h,3.92; and N,8.25.

Synthesis example 42: synthesis of Compound 436

According to the preparation method of Synthesis example 18, a-18, b-128, c-151 and d-218 were replaced with equimolar a-436, b-436, c-436 and d-229, respectively, to obtain 436 (16.45 g) having a solid purity of 99.96% or more by HPLC. Mass spectrum m/z:817.1815 (theoretical value: 817.1800). Theoretical element content (%) C₄₉H₂₅F₆N₃O₃: c,71.97; h,3.08; and N,5.14. Measured elemental content (%): c,71.94; h,3.12; and N,5.16.

Synthetic example 43: synthesis of Compound 444

According to the preparation method of synthetic example 18, a-18, b-128, c-151 and d-218 were replaced with equimolar a-397, b-444, c-444 and d-229, respectively, to obtain compound 444 (17.58 g) with a solid purity of 99.93% or more by HPLC. Mass spectrum m/z:836.1943 (theoretical value: 836.1956). Theoretical element content (%) C₅₈H₃₂N₂OS₂: c,83.23; h,3.85; and N,3.35. Measured elemental content (%): c,83.28; h,3.81; and N,3.40.

Synthetic example 44: synthesis of Compound 476

According to the preparation method of synthetic example 18, b-128, d-218 and c-151 were replaced with equimolar amounts of b-53, d-476 and c-220, respectively, to give a compound 476 (16.82 g) having a solid purity of 99.97% or more by HPLC. Mass spectrum m/z:757.2353 (theoretical value: 757.2365). Theoretical element content (%) C ₅₃H₃₁N₃O₃: c,84.00; h,4.12; and N,5.54. Measured elemental content (%): c,84.05; h,4.08; and N,5.57.

Synthetic example 45: synthesis of Compound 482

According to the preparation method of synthetic example 18, b-128, d-218 and c-151 were replaced with equimolar amounts of b-482, d-482 and c-482, respectively, to obtain Compound 482 (18.52 g) having a solid purity of 99.94% or more by HPLC. Mass spectrum m/z:933.2998 (theoretical value: 933.2991). Theoretical element content (%) C₆₇H₃₉N₃O₃: c,86.15; h,4.21; and N,4.50. Measured elemental content (%): c,86.17; h,4.17; n,4.52.

Synthesis example 46: synthesis of Compound 685

According to the preparation method of synthetic example 18, a-18, b-128, d-218 and c-151 were replaced with equimolar a-685, b-685, d-685 and c-685, respectively, to give compound 685 (16.66 g) with a solid purity of 99.88% or more by HPLC. Mass spectrum m/z:760.2351 (theoretical value: 760.2333). Theoretical element content (%) C₅₁H₂₈DN₅O₃: c,80.51; h,3.97; and N,9.21. Measured elemental content (%): c,80.55; h,3.94; and N,9.26.

Synthetic example 47: synthesis of Compound 691

According to the preparation method of Synthesis example 18, b-128, d-218 and c-151 were replaced with equimolar amounts of b-691, d-691 and c-691, respectively, to give compound 691 (18.01 g) with a solid purity of 99.96% or more by HPLC. Mass spectrum m/z:869.3630 (theoretical value: 869.3617). Theoretical element content (%) C ₆₁H₄₇N₃O₃: c,84.21; h,5.45; and N,4.83. Measured elemental content (%): c,84.25; h,5.41; and N,4.86.

Synthetic example 48: synthesis of Compound 697

According to the preparation method of synthetic example 18, b-128, d-218 and c-151 were replaced with equimolar b-303, d-482 and c-697, respectively, to give compound 697 (16.10 g) with a solid purity of 99.94% or more by HPLC. Mass spectrum m/z:755.2476 (theoretical value: 755.2460). Theoretical element content (%) C₅₅H₃₃NO₃: c,87.40; h,4.40; n,1.85. Measured elemental content (%): c,87.44; h,4.37N,1.89.

Synthetic example 49: synthesis of Compound 710

According to the preparation method of synthetic example 18, a-18, b-128, d-218 and c-151 were replaced with equimolar a-710, b-53, d-685 and e-710, respectively, to obtain compound 710 (15.64 g), which had a solid purity of 99.88% or more as determined by HPLC. Mass spectrum m/z:759.2255 (theoretical value: 759.2270). Theoretical element content (%) C₅₁H₂₉N₅O₃: c,80.62; h,3.85; n,9.22. Measured elemental content (%):C,80.66；H,3.81；N,9.25。

synthetic example 50: synthesis of Compound 712

According to the preparation method of synthetic example 18, compound 712 (19.02 g) was obtained by replacing a-18, b-128, d-218, and c-151 with equimolar a-712, b-712, d-712, and c-712, respectively, and the solid purity was 99.89% or more by HPLC. Mass spectrum m/z:919.2162 (theoretical value: 919.2150). Theoretical element content (%) C ₆₂H₃₇N₃S₃: c,80.93; h,4.05; n,4.57. Measured elemental content (%): c,80.96; h,4.01; n,4.61.

Synthetic example 51: synthesis of Compound 718

According to the preparation method of synthetic example 18, b-128, d-218 and c-151 were replaced with equimolar amounts of b-718, d-685 and c-718, respectively, to give compound 718 (16.00 g), which was determined to have a solid purity of 99.95% or more by HPLC. Mass spectrum m/z:795.2247 (theoretical value: 795.2232). Theoretical element content (%) C₅₇H₃₃NO₂S: c,86.01; h,4.18; n,1.76. Measured elemental content (%): c,86.05; h,4.14; and N,1.80.

Synthesis example 52: synthesis of Compound 745

According to the preparation method of synthetic example 18, compound 745 (16.46 g) was obtained by replacing b-128, d-218, and c-151 with equimolar b-53, d-476, and e-745, respectively, and the solid purity was 99.85% or more by HPLC. Mass spectrum m/z:807.2541 (theoretical value: 807.2522). Theoretical element content (%) C₅₇H₃₃N₃O₃：C,84.74；H,4.12; and N,5.20. Measured elemental content (%): c,84.79; h,4.08; and N,5.24.

Synthetic example 53: synthesis of Compound 751

According to the preparation method of Synthesis example 18, compound 751 (15.75 g) was obtained by substituting a-18, b-128, d-218 and c-151 with equimolar a-751, b-53, d-685 and e-751, respectively, and the solid purity by HPLC analysis was 99.90% or more. Mass spectrum m/z:749.2130 (theoretical value: 749.2115). Theoretical element content (%) C ₅₁H₂₈FN₃O₃: c,81.70; h,3.76; and N,5.60. Measured elemental content (%): c,81.73; h,3.72; and N,5.65.

Synthetic example 54: synthesis of Compound 769

According to the preparation method of synthetic example 18, b-128, d-218 and c-151 were replaced with equimolar b-53, d-769 and c-128, respectively, to give 769 (18.01 g) as a solid having a purity of 99.92% or more by HPLC. Mass spectrum m/z:833.2662 (theoretical value: 833.2678). Theoretical element content (%) C₅₉H₃₅N₃O₃: c,84.98; h,4.23; and N,5.04. Measured elemental content (%): c,84.94; h,4.28; and N,5.01.

Synthetic example 55: synthesis of Compound 809

According to the preparation method of synthetic example 18, b-128, d-218 and c-151 were replaced with equimolar b-809, d-809 and c-809, respectively, to give compound 809 (15.54 g) with a solid purity of 99.91% or more by HPLC. Mass spectrum m/z:761.2192 (theoretical value: 761.2175). Theoretical element content (%) C₄₉H₂₇N₇O₃: c,77.26; h,3.57; n,12.87. Measured elemental content (%): c,77.30; h,3.52; and N,12.91.

Synthetic example 56: synthesis of Compound 880

According to the preparation method of synthetic example 18, b-128, d-218 and c-151 were replaced with equimolar amounts of b-880, d-880 and c-220, respectively, to give compound 880 (16.86 g) with a solid purity of 99.93% or more by HPLC. Mass spectrum m/z:781.2130 (theoretical value: 781.2114). Theoretical element content (%) C ₅₃H₂₇N₅O₃: c,81.42; h,3.48; and N,8.96. Measured elemental content (%): c,81.47; h,3.43; and N,9.00.

Synthetic example 57: synthesis of Compound 912

According to the preparation method of synthetic example 18, a-18, b-128 and d-218 were replaced with equimolar a-912, b-912 and d-912, respectively, to give compound 912 (18.15 g), which had a solid purity of 99.84% or more by HPLC. Mass spectrum m/z:917.2332 (theoretical value: 917.2346). Theoretical element content (%) C₆₀H₃₇F₂N₃OS₂: c,78.50; h,4.06; n,4.58. Measured elemental content (%): c,78.54; h,4.01; and N,4.61.

Synthetic example 58: synthesis of Compound 919

According to the preparation method of synthetic example 18, b-128, d-218 and c-151 were replaced with equimolar amounts of b-357, d-919 and c-191, respectively, to obtain compound 924 (17.74 g) with a solid purity of 99.89% or more by HPLC. Mass spectrum m/z:897.2941(theoretical value: 897.2926). Theoretical element content (%) C₆₃H₃₉N₅S: c,84.25; h,4.38; and N,7.80. Measured elemental content (%): c,84.28; h,4.36; and N,7.84.

Synthetic example 59: synthesis of Compound 924

According to the preparation method of synthetic example 18, b-128 and d-218 were replaced with equimolar b-303 and d-912, respectively, to obtain 924 (16.68 g) which was found to have a solid purity of 99.97% or more by HPLC. Mass spectrum m/z:805.2602 (theoretical value: 805.2617). Theoretical element content (%) C ₅₉H₃₅NO₃: c,87.93; h,4.38; n,1.74. Measured elemental content (%): c,87.96; h,4.33; n,1.78.

Synthesis example 60: synthesis of Compound 932

According to the preparation method of synthetic example 18, b-128 and d-218 were replaced with equimolar b-53 and d-932, respectively, to obtain compound 932 (14.76 g) having a solid purity of 99.95% or more by HPLC. Mass spectrum m/z:682.2022 (theoretical value: 682.2005). Theoretical element content (%) C₄₆H₂₆N₄O₃: c,80.92; h,3.84; n,8.21. Measured elemental content (%): c,80.96; h,3.80; and N,8.24.

Synthetic example 61: synthesis of Compound 955

According to the preparation method of Synthesis example 18, b-128 and d-218 were replaced with equimolar b-955 and d-955, respectively, to obtain compound 955 (17.85 g) with a solid purity of 99.91% or more by HPLC. Mass spectrum m/z:837.2470 (theoretical value: 837.2488). Theory of the inventionElement content (%) C₅₅H₃₁N₇O₃: c,78.84; h,3.73; n,11.70. Measured elemental content (%): c,78.80; h,3.78; n,11.66.

Synthesis example 62: synthesis of Compound 1018

According to the preparation method of synthetic example 18, a-18, b-128, d-218 and c-151 were replaced with equimolar amounts of a-128, e-685, d-1018 and c-233, respectively, to give compound 1018 (16.18 g) with a solid purity of 99.84% or more by HPLC. Mass spectrum m/z:817.1732 (theoretical value: 817.1718). Theoretical element content (%) C ₅₁H₂₇N₇OS₂: c,74.89; h,3.33; n,11.99. Measured elemental content (%): c,74.86; h,3.35; n,11.97.

Synthetic example 63: synthesis of Compound 1047

According to the preparation method of synthetic example 18, a-18, b-128 and d-218 were replaced with equimolar a-1047, b-1047 and d-1047, respectively, to give compound 1047 (14.13 g) with a solid purity of 99.95% or more by HPLC. Mass spectrum m/z:736.2713 (theoretical value: 736.2726). Theoretical element content (%) C₅₂H₃₆N₂O₃: c,84.76; h,4.92; and N,3.80. Measured elemental content (%): c,84.72; h,4.95; n,3.84.

Device embodiments

In the invention, the ITO/Ag/ITO or ITO glass substrate is ultrasonically cleaned for 2 times and 20 minutes each time by 5% glass cleaning solution, and then is ultrasonically cleaned for 2 times and 10 minutes each time by deionized water. Ultrasonic cleaning with acetone and isopropanol for 20 min, and oven drying at 120 deg.C. The organic materials are sublimated, and the purity of the organic materials is over 99.99 percent.

The driving voltage, the luminous efficiency and the CIE color coordinates of the organic electroluminescent device were measured by combining test software, a computer, a K2400 digital source meter manufactured by Keithley, USA, and a PR788 spectral scanning luminance meter manufactured by Photo Research, USA into a combined IVL test system. The lifetime was measured using the M6000 OLED lifetime test system from McScience. The environment of the test is atmospheric environment, and the temperature is room temperature.

Example 1: preparation of organic electroluminescent device 1

HAT-CN is evaporated on the ITO anode in vacuum to be used as a hole injection layer, and the thickness is 5nm; vacuum evaporating beta-NPB on the hole injection layer to form a hole transport layer with the thickness of 65nm; E-BETA-1 is vacuum evaporated on the hole transfer layer to be used as an electron blocking layer, and the thickness is 10nm; GH-1 and the compound 18 of the invention were vacuum evaporated on the electron blocking layer at a ratio of 1₂(acac) vapor-depositing in a doping amount of 8wt% based on the total amount of the host and the dopant to form a light-emitting layer having a thickness of 28nm; vacuum evaporating AND-PAimi, liq =50 (wt%) as an electron transport layer on the light emitting layer, wherein the thickness of the electron transport layer is 35nm; evaporating LiF on the electron transport layer in vacuum to form an electron injection layer, wherein the evaporation thickness is 1.1nm; al was vacuum-evaporated on the electron injection layer as a cathode with a thickness of 150nm.

Examples 2 to 41: preparation of organic electroluminescent devices 2 to 41

The compounds 18 in the light-emitting layer in example 1 were replaced with the compounds 53, 64, 89, 113, 123, 128, 148, 151, 176, 191, 205, 218, 220, 226, 229, 233, 242, 243, 261, 276, 303, 309, 357, 392, 404, 426, 444, 476, 482, 691, 697, 712, 718, 730, 751, 769, 880, 924, 932 and 1018, respectively, and other steps were repeated in the same manner to obtain organic electroluminescent devices 2 to 41.

Comparative examples 1 to 2: preparation of comparative organic electroluminescent devices 1 to 2

Comparative organic electroluminescent devices 1 to 2 were obtained by replacing the compound 18 in the light-emitting layer of example 1 with R-1 and R-2, respectively, and the other steps were the same.

The results of the test of the light emitting characteristics of the organic electroluminescent devices prepared in examples 1 to 41 of the present invention and comparative examples 1 to 2 are shown in table 1.

Table 1 test data of light emitting characteristics of organic electroluminescent device

As can be seen from table 1, the organic electroluminescent device of the present invention has lower driving voltage, higher luminous efficiency, longer service life, and more excellent device performance than the comparative devices 1 to 2.

Example 42: preparation of organic electroluminescent device 42

HAT-CN is evaporated on the ITO anode in vacuum to be used as a hole injection layer, and the thickness is 6 nm; evaporating alpha-TNB on the hole injection layer in vacuum to form a hole transport layer with the thickness of 60nm; E-BETA-2 is vacuum evaporated on the hole transfer layer to be used as an electron blocking layer, and the thickness is 15 nm; RH-1 and inventive compound 18 were vacuum evaporated on the electron blocking layer at a ratio of 1₃Performing evaporation with a doping amount of 6wt% based on the total amount of the host and the dopant to form a light emitting layer with a thickness of 35 nm; vacuum evaporating AND-PAimi, liq =50 (wt%) as an electron transport layer on the light emitting layer, wherein the thickness of the electron transport layer is 41 nm; evaporating LiF on the electron transport layer in vacuum to form an electron injection layer, wherein the evaporation thickness is 1.1 nm; vacuum evaporating Al as cathode on the electron injection layer with thickness of 15 0 nm。

Examples 43 to 81: preparation of organic electroluminescent devices 43 to 81

The compound 18 in the light-emitting layer in example 42 was replaced with the compound 20, the compound 113, the compound 144, the compound 148, the compound 151, the compound 152, the compound 160, the compound 176, the compound 191, the compound 205, the compound 218, the compound 226, the compound 229, the compound 235, the compound 236, the compound 253, the compound 280, the compound 303, the compound 309, the compound 310, the compound 371, the compound 381, the compound 397, the compound 426, the compound 436, the compound 476, the compound 482, the compound 685, the compound 697, the compound 710, the compound 745, the compound 769, the compound 809, the compound 880, the compound 912, the compound 919, the compound 924, the compound 955 and the compound 1047, respectively, and other steps were carried out in the same manner, whereby organic electroluminescent devices 43 to 81 were obtained.

Comparative examples 3 to 4: preparation of comparative organic electroluminescent devices 3 to 4

Comparative organic electroluminescent devices 3 to 4 were obtained by replacing the compound 18 in the light-emitting layer of example 42 with R-1 and R-2, respectively, in the same manner as in the other steps.

The results of the test of the light emitting characteristics of the organic electroluminescent devices prepared in examples 42 to 81 of the present invention and comparative examples 3 to 4 are shown in table 2.

Table 2 light emitting characteristic test data of organic electroluminescent device

As can be seen from table 2, the organic electroluminescent device of the present invention has lower driving voltage, higher luminous efficiency, longer service life, and more excellent device performance than the comparative devices 3 to 4.

The heterocyclic compound of formula 1 of the present invention is an electron-type host material, and as can be seen from tables 1 and 2, the heterocyclic compound of the present invention has good photoelectric properties and good stability, and when used in a device, the heterocyclic compound can effectively transmit electrons, balance electrons and holes in a light-emitting layer, effectively limit the electrons and holes in the light-emitting layer, and combine them to form excitons to emit light, so that the driving voltage of the device is reduced, the light-emitting efficiency is improved, and the service life is prolonged.

Example 82: preparation of organic electroluminescent device 82

Carrying out vacuum evaporation on the ITO anode to form DNTPD as a hole injection layer with the thickness of 65nm; vacuum evaporating TPD on the hole injection layer to form a hole transport layer with the thickness of 32nm; vacuum evaporating MCP (Hex-Ir) (piq) on the hole transport layer₃(5% by weight), forming a light-emitting layer having a thickness of 32nm; the compound 18 of the invention is vacuum evaporated on the luminescent layer to be used as an electron transport layer, and the thickness is 35nm; vacuum evaporating LiF on the electron transport layer to form an electron injection layer, wherein the evaporation thickness is 0.5nm; al is vacuum-evaporated on the electron injection layer to form a cathode with a thickness of 200nm.

Examples 83 to 98: preparation of organic electroluminescent devices 83 to 98

In the same manner as in the other steps except for replacing the compound 18 in the electron transport layer in example 82 with the compound 151, the compound 176, the compound 191, the compound 205, the compound 218, the compound 226, the compound 266, the compound 309, the compound 357, the compound 476, the compound 691, the compound 697, the compound 718, the compound 769, the compound 880, and the compound 932, organic electroluminescent devices 83 to 98 were obtained.

Comparative examples 5 to 6: preparation of comparative organic electroluminescent devices 5 to 6

Comparative organic electroluminescent devices 5 to 6 were obtained by changing the compound 18 in the electron transport layer of example 82 to R-1 and R-2, respectively, and the other steps were the same.

The results of the test of the light emitting characteristics of the organic electroluminescent devices of examples 82 to 98 of the present invention and comparative examples 5 to 6 are shown in table 3.

Table 3 test data of light emitting characteristics of organic electroluminescent device

As can be seen from table 3, the organic electroluminescent device of the present invention has lower driving voltage, higher luminous efficiency, longer service life, and more excellent device performance than the comparative devices 5 to 6. This shows that the heterocyclic compound of formula 1 of the present invention has a good electron transport property, can transport electrons efficiently, and the LUMO level thereof is more matched with the functional layers on both sides thereof, and the structure is more stable, thereby reducing the driving voltage of the device, improving the light emitting efficiency, and prolonging the service life.

Example 99: preparation of organic electroluminescent device 99

Vacuum evaporating 1-TNATA on the ITO/Ag/ITO anode to form a hole injection layer with the thickness of 61 nm; vacuum evaporating beta-NPB on the hole injection layer to form a hole transport layer with the thickness of 30nm; vacuum evaporating TBAND: BD-1 (2% by weight) on the hole transport layer to form a light-emitting layer with a thickness of 30nm; vacuum evaporation of Alq on the light-emitting layer₃As an electron transport layer, the thickness is 32 nm; evaporating LiF on the electron transport layer in vacuum to form an electron injection layer, wherein the evaporation thickness is 1.0 nm; vacuum evaporating Mg, ag =1 (wt%) as a cathode, on the electron injection layer, and the thickness of the cathode is 15 nm; the compound 113 of the present invention was vacuum-deposited on the cathode as a covering layer to a thickness of 60 nm.

Examples 100 to 106: preparation of organic electroluminescent devices 100 to 106

The same procedures were carried out except for changing the compound 113 in the electric clad layer of example 99 to the compounds 128, 176, 205, 218, 226, 309 and 697, respectively, to obtain organic electroluminescent devices 100 to 106.

Comparative examples 7 to 8: preparation of comparative organic electroluminescent devices 7 to 8

Comparative organic electroluminescent devices 7 to 8 were obtained by changing the compound 113 in the covering layer of example 99 to R-1 and R-2, respectively, and the other steps were the same.

The results of the test of the light emitting characteristics of the organic electroluminescent devices prepared in examples 99 to 106 of the present invention and comparative examples 7 to 8 are shown in table 4.

Table 4 test data of light emitting characteristics of organic electroluminescent device

As can be seen from table 4, the organic electroluminescent device of the present invention has higher luminous efficiency, longer service life, and more excellent device performance than the comparative devices 7 to 8. This is because the heterocyclic compound of formula 1 of the present invention, when applied to the cap layer, can efficiently couple out light trapped in the device and can prevent external water and oxygen from entering the device, thereby improving the light-emitting efficiency of the device and extending the lifetime thereof.

It is to be understood that the present invention has been particularly shown and described with reference to particular embodiments thereof, but that various changes in form and details may be made therein by those skilled in the art without departing from the spirit and scope of the invention.

Claims

1. A heterocyclic compound represented by the following formula 1,

Ar is selected from the group shown as follows,

the ring B is selected from one of substituted or unsubstituted C10-C30 aromatic ring, substituted or unsubstituted 10-30 membered heteroaromatic ring containing 1N, substituted or unsubstituted condensed ring of C3-C20 alicyclic ring and C10-C30 aromatic ring, and substituted or unsubstituted condensed ring of C3-C20 alicyclic ring and 10-30 membered heteroaromatic ring;

said X₁Selected from O or S;

ar is₁、Ar₂Independently selected from the group shown below,

the ring C is selected from substituted or unsubstituted C6-C30 aromatic ring, substituted or unsubstituted C2-C30 heteroaromatic ring, substituted or unsubstituted C3-C20 alicyclic ring and C6-C30 aromatic ring condensed ring, substituted or unsubstituted C3 One of a fused ring of an alicyclic ring of about C20 and a heteroaromatic ring of about C2 to about C30;

w is selected from N or C (Rw), and Rw is selected from one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C20 fused ring group of aliphatic ring and C6-C30 aromatic ring, substituted or unsubstituted C3-C20 fused ring group of aliphatic ring and C2-C30 heteroaromatic ring, and substituted or unsubstituted C3-C20 lipoheterocyclic group;

said R is₂One selected from the group consisting of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C20 fused ring group of an alicyclic ring and a C6-C30 aromatic ring, substituted or unsubstituted C3-C20 fused ring group of an alicyclic ring and a C2-C30 heteroaromatic ring, and substituted or unsubstituted C3-C20 lipoheterocyclic group;

L, L₁、L₂Independently selected from a single bond, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C2-C30 heteroarylene, substituted or unsubstituted C3-C20 alicyclic ring and C6-C30 aromatic ring subfused cyclic group, substituted or unsubstituted C3-C20 alicyclic ring and C2-C30 heteroaromatic ring subfused cyclic group, wherein the substituent in the substituent is selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstitutedOr one of a substituted or unsubstituted C1-C25 alkyl group, a substituted or unsubstituted C3-C25 cycloalkyl group, a substituted or unsubstituted C3-C25 heterocycloaliphatic group, or two adjacent substituents may be bonded to each other to form a substituted or unsubstituted ring.

2. The heterocyclic compound according to claim 1, wherein the ring A is selected from the group consisting of groups represented by,

3. The heterocyclic compound according to claim 2, wherein the ring A is one selected from the group consisting of groups represented by,

R1 is an integer from 1 to 3, and r2 is an integer from 1 to 2;

4. The heterocyclic compound according to claim 1, characterized in that the heterocyclic compound is

One selected from the group shown below,

5. The heterocyclic compound according to claim 1, characterized in that the heterocyclic compound is

One selected from the group shown below,

the v is the same or different and is selected from C (Rv) or N, the Rv is the same or different and is selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring fused ring group, substituted or unsubstituted C3-C20 alicyclic and C2-C30 heteroaromatic ring fused ring group, or two adjacent Rv are bonded to each other to form a substituted or unsubstituted ring.

6. The heterocyclic compound according to claim 1, wherein L is one selected from the group consisting of a single bond and a group represented by the following,

the Y is same or different and is selected from CH or N, each aromatic ring contains at most two N, the Ry is same or different and is selected from one of hydrogen, deuterium, tritium, halogen, cyano-group, nitro-group, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C3-C20 lipo-heterocyclic group, or two adjacent Ry are mutually bonded to form a substituted or unsubstituted ring.

7. The heterocyclic compound according to claim 6, wherein L is selected from a single bond or one of the groups represented by the following,

the Ry is the same or different and is selected from one of hydrogen, deuterium, tritium, halogen, cyano-group, nitro-group, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl and substituted or unsubstituted C3-C15 lipo-heterocyclic group;

and Ry0 is one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C2-C25 heteroaryl, substituted or unsubstituted C3-C15 fused ring group of alicyclic ring and C6-C25 aromatic ring, substituted or unsubstituted C3-C15 fused ring group of alicyclic ring and C2-C25 heteroaromatic ring, and substituted or unsubstituted C3-C15 lipoheterocyclic group.

8. The heterocyclic compound of claim 1, wherein L is ₁、L₂Independently selected from a single bond or one of the groups shown as follows,

the Q is the same or different and is selected from C (Rq) or N, the Rq is the same or different and is selected from one of hydrogen, deuterium, tritium, halogen, cyano-group, nitro-group, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C3-C20 lipoheterocyclic group, or two adjacent Rq are mutually bonded to form a substituted or unsubstituted ring.

9. The heterocyclic compound according to claim 1, characterized in that the heterocyclic compound of formula 1 is at least one selected from the following structures,

10. an organic electroluminescent element comprising the heterocyclic compound according to any one of claims 1 to 9.