CN118900577B

CN118900577B - Organic electroluminescent device

Info

Publication number: CN118900577B
Application number: CN202410946355.3A
Authority: CN
Inventors: 刘喜庆; 孙敬; 孙月; 杜明珠
Original assignee: Changchun Hyperions Technology Co Ltd
Current assignee: Changchun Hyperions Technology Co Ltd
Priority date: 2024-07-15
Filing date: 2024-07-15
Publication date: 2025-09-19
Anticipated expiration: 2044-07-15
Also published as: CN118900577A

Abstract

本发明提供了一种有机电致发光器件，涉及有机电致发光技术领域。本发明的有机电致发光器件，包括阳极、阴极和位于阳极和阴极之间的有机物层，所述有机物层包含发光层，所述发光层包含主体材料和掺杂材料，所述主体材料含有式1所示的咔唑化合物。本发明的发光层中主体材料含有式1的咔唑化合物的有机电致发光器件，显示出优异的光电性能，具体表现为，发光效率较高以及使用寿命较长，尤其是，空穴传输区域还包含式2的星型化合物的有机电致发光器件，其光电性能改善的更加明显，是一种具有改善性能的有机电致发光器件。The present invention provides an organic electroluminescent device, relating to the technical field of organic electroluminescence. The organic electroluminescent device of the present invention comprises an anode, a cathode, and an organic layer located between the anode and the cathode. The organic layer comprises a light-emitting layer, the light-emitting layer comprising a host material and a dopant material, the host material comprising a carbazole compound represented by Formula 1. The organic electroluminescent device of the present invention, wherein the host material in the light-emitting layer comprises the carbazole compound represented by Formula 1, exhibits excellent photoelectric performance, specifically, high luminous efficiency and long service life. In particular, the organic electroluminescent device wherein the hole transport region further comprises the star-shaped compound represented by Formula 2 exhibits even more significantly improved photoelectric performance, resulting in an organic electroluminescent device with improved performance.

Description

Organic electroluminescent device

Technical Field

The invention relates to the technical field of organic electroluminescence, in particular to an organic electroluminescent device.

Background

Organic Light Emitting Diodes (OLEDs) are also known as organic electroluminescent devices. The organic electroluminescent device is a device using an organic material as an active light emitting layer under the action of an electric field. Compared with the traditional Liquid Crystal Display (LCD), the OLED has more advantages such as self-luminescence, high response speed, low power consumption, high contrast ratio, ultra-thin and ultra-light, wide viewing angle, flexible display realization and the like, and is a very ideal new generation flat panel display technology. The OLED display technology is widely applied to smart phones, VR, wearable devices, televisions, tablet computers, intelligent automobiles and the like, and has wide overall market prospect.

The OLED device is like a sandwich structure and comprises electrode material film layers and organic functional materials clamped between different electrode film layers, and various functional materials are mutually overlapped together according to purposes to form the OLED light-emitting device. An OLED generally comprises an anode, a cathode and an organic layer formed between the two electrodes. The organic layer of the OLED may comprise a hole transporting region, a light emitting region, an electron transporting region, etc., and in addition, a capping layer (CPL) may be introduced outside the cathode and/or anode of the OLED. Under the action of an externally applied electric field, holes injected by the anode and electrons injected by the cathode migrate and recombine in the organic layer, and energy is transferred to the luminescent material, so that the luminescent material is excited to form excitons, the excitons are attenuated by radiation when the excited state returns to the ground state, and the attenuated energy is emitted in a light mode, so that the aim of luminescence is fulfilled.

In recent years, organic electroluminescent devices have been greatly advanced in performance, but some devices still have problems such as low luminous efficiency, short lifetime, etc., and generally, a host material/dopant mixed system can be used as a light emitting layer to improve the performance of the device, however, the choice of host material is critical, and thus further intensive research is required to obtain an organic electroluminescent device having improved performance.

Disclosure of Invention

Aiming at the problems in the prior art, the invention provides an organic electroluminescent device.

The invention provides an organic electroluminescent device, comprising an anode, a cathode and an organic layer positioned between the anode and the cathode, wherein the organic layer comprises a luminescent layer, the luminescent layer comprises a host material and a doping material, the host material comprises a carbazole compound shown in a formula 1,

Ar ₁、Ar₂ is independently selected from the group shown below,

The ring A is selected from one of a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted 6-30 membered nitrogen-containing heteroaromatic ring;

the X is selected from O, S;

The R is the same or different and is selected from one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C6-C60 condensed polycyclic group and substituted or unsubstituted C2-C60 heteroaryl;

T is an integer from 0 to 2;

ar is selected from one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C6-C60 fused polycyclic group and substituted or unsubstituted C2-C60 heteroaryl, or Ar is directly connected with L;

The R ₁ is the same or different and is selected from one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C12 aryl, substituted or unsubstituted C6-C60 condensed polycyclic group and substituted or unsubstituted C2-C60 heteroaryl;

m is an integer from 0 to 4;

The R ₀ is the same or different and is selected from one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C6-C60 condensed polycyclic group and substituted or unsubstituted C2-C60 heteroaryl;

s is an integer of 0 to 3;

The L, L ₁、L₂ is independently selected from one or a combination of single bond, substituted or unsubstituted arylene of C6-C60, substituted or unsubstituted sub-condensed polycyclic group of C6-C60, and substituted or unsubstituted heteroarylene of C2-C60.

The organic electroluminescent device with the host material containing the carbazole compound of formula 1 in the luminescent layer has the advantages of excellent photoelectric performance, and particularly high luminous efficiency and long service life, and particularly, the hole transport region also contains the star-shaped compound of formula 2, so that the photoelectric performance of the organic electroluminescent device is improved more obviously, and the organic electroluminescent device with improved performance is provided.

Detailed Description

The present application is further illustrated below in conjunction with specific embodiments, it being understood that these embodiments are meant to be illustrative of the application and not limiting the scope of the application, and that modifications of the application, which are all equivalent to those skilled in the art to which the application pertains, are within the scope of the application as claimed.

In the compounds of the present specification, any atom not designated as a particular isotope is included as any stable isotope of that atom, and includes atoms in both its natural isotopic abundance and non-natural abundance. In the present invention, "H", "hydrogen" and "hydrogen atom" refer to isotopes having different neutron numbers, including protium, deuterium and tritium.

In the specification, halogen includes fluorine, chlorine, bromine and iodine.

In this specification, when a substituent is not fixed in position on a ring, it means that it can be attached to any of the corresponding selectable positions of the ring.

For example, the number of the cells to be processed,Can representCan representCan represent And so on.

In this specification, "adjacent two groups are bonded to form a ring" means that a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocyclic ring is formed by bonding adjacent groups to each other and optionally aromatizing. The hydrocarbon ring may be an aliphatic hydrocarbon ring or an aromatic hydrocarbon ring. The heterocycle may include aliphatic or aromatic heterocycles. 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 ring and the heterocyclic ring may be a single ring or a polycyclic group. In addition, a ring formed by bonding adjacent groups may be linked to another ring to form a spiro structure. As exemplified below:

In the present specification, the ring formed by the connection may be a three-membered ring, a four-membered ring, a five-membered ring, a six-membered ring, a seven-membered ring, an eight-membered ring, a condensed ring or the like, for example, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopentene, cyclohexene, adamantane, norbornane, benzene, naphthalene, phenanthrene, triphenylene, pyridine, pyrimidine, quinoline, isoquinoline, quinazoline, quinoxaline, fluorene, dibenzofuran, dibenzothiophene, carbazole or the like, but is not limited thereto.

In the present specification, the "integer selected from 0~M" means that the value is selected from any one of integers of 0~M, including 0,1, 2..m-2, M-1, M. For example, "s is an integer from 0 to 3" means that s is 0,1,2 or 3. And so on.

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

In the present specification, "CXX to CYY" in the "substituted or unsubstituted CXX to CYY ZZ group" 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 C60" in the "substituted or unsubstituted C6 to C60 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. And so on.

In the present specification, "substituted" in the "substituted or unsubstituted" means that at least one hydrogen atom on a group is replaced with a substituent. When a plurality of hydrogens are replaced with a plurality of substituents, the plurality of substituents may be the same or different. The position of the hydrogen substituted with the substituent may be any position. The substituents represented by "substituted" in the above "substituted or unsubstituted" include the following groups, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted C3 to C15 heterocyclic group, substituted or unsubstituted C1 to C15 alkyl group, substituted or unsubstituted C3 to C15 cycloalkyl group, substituted or unsubstituted silyl group, substituted or unsubstituted C6 to C30 aryl group, substituted or unsubstituted C6 to C30 condensed polycyclic group, substituted or unsubstituted C2 to C30 heteroaryl group, and the like. Preferred are deuterium, tritium, halogen, cyano, nitro, methyl, ethyl, propyl, butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, camphene, isobornenyl, fenchyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl, phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylyl, anthracenyl, pyrenyl,A group, a fluoranthenyl group, a benzocyclopropanyl group, a benzocyclobutanyl group, a benzocyclobutenyl group, a indanyl group, an indenyl group, a tetrahydronaphthyl group, a dihydronaphthyl group, a benzocycloheptanyl group, a fluorenyl group, a benzofluorenyl group, a benzofuranyl group, a pyridofuranyl group, a naphtofuranyl group, a dibenzofuranyl group, a benzothienyl group, a pyridothienyl group, a naphtothienyl group, a dibenzothienyl group, an indolyl group, a carbazolyl group, a pyridyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolyl group, an isoquinolyl group, and the like. In addition, each of the above substituents may be substituted or unsubstituted, and two adjacent substituents may be bonded to form a ring.

In the present specification, the alkyl group refers to a hydrocarbon group in which one hydrogen atom is omitted from an alkane molecule, and the alkyl group includes a linear alkyl group and a branched alkyl group. Examples of the alkyl group may include, but are not limited to, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, and the like. Chain alkyl groups containing three or more carbon atoms include isomers thereof, such as propyl groups including n-propyl, isopropyl, butyl groups including n-butyl, sec-butyl, isobutyl, and tert-butyl, and so forth. The number of carbon atoms of the alkyl group is1 to 30, preferably 1 to 20, preferably 1 to 15, and more preferably 1 to 10.

In the present specification, the cycloalkyl group refers to a hydrocarbon group in which one hydrogen atom is omitted from a cycloparaffin molecule, and the cycloalkyl group includes a monocyclic cycloalkyl group, a polycyclic cycloalkyl group, and a bridged cycloalkyl group. Examples of the cycloalkyl group may include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, camphenethyl, and the like. The number of carbon atoms of the cycloalkyl group is 3 to 30, preferably 3 to 20, preferably 3 to 15, more preferably 3 to 10.

In the present specification, the "silyl group" means —si (R _t)₃ groups, wherein each R _t is the same or different and is selected from the group consisting of: hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C6-C60 fused polycyclic group, substituted or unsubstituted C2-C60 heteroaryl, and the like, preferably, each R _t is the same or different and 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 pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted cycloheptyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted indanyl, substituted or unsubstituted indenyl, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted dihydronaphthyl, substituted or unsubstituted benzocyclobutenyl, substituted or unsubstituted benzocyclopropenyl, substituted or unsubstituted pyridinyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, and the like, and may be included in the examples, but not limited thereto, triisopropylsilyl, tri-t-butylsilyl, dimethylethylsilyl, dimethylisopropylsilyl, dimethylt-butylsilyl, tricyclopentylsilyl, tricyclohexylsilyl, triphenylsilyl, terphenylsilyl, tripyridylsilyl, and the like, but is not limited thereto.

In the present specification, the aryl group refers to a generic term for monovalent groups remaining after one hydrogen atom is removed from the aromatic nucleus carbon of an aromatic compound molecule. The aryl group comprises a monocyclic aryl group, a polycyclic aryl group, a fused ring aryl group, or a combination thereof. Examples of the aryl group may include phenyl, biphenyl, terphenyl, tetraphenyl, naphthyl, phenanthryl, triphenylenyl, anthracenyl, pyrenyl, perylenyl,A group, a fluoranthenyl group, a fluorenyl group, a benzofluorenyl group, and the like, but is not limited thereto. The number of carbon atoms of the aryl group is 6 to 60, preferably 6 to 30, preferably 6 to 25, preferably 6 to 18, and more preferably 6 to 12.

In the present specification, the condensed polycyclic group means a monovalent group comprising at least two rings in which at least one aromatic ring and at least one non-aromatic ring are condensed with each other. Examples of the condensed polycyclic group may include, but are not limited to, benzocyclopropane group, benzocyclobutane group, benzocyclobutene group, indanyl group, indenyl group, tetrahydronaphthyl group, dihydronaphthyl group, benzocycloheptane group, benzocycloheptenyl group, and the like. The fused polycyclic group has 6 to 60, preferably 6 to 30, preferably 6 to 25, preferably 6 to 18, and more preferably 6 to 12 carbon atoms.

In the present specification, the heteroaryl group refers to a generic term for a group in which one or more carbon atoms in an aryl group are replaced with a heteroatom including, but not limited to, oxygen, sulfur, nitrogen, phosphorus, boron, silicon, and the like. The heteroaryl comprises a monocyclic heteroaryl, a fused ring heteroaryl, or a combination thereof. Pyrazinothioyl, pyridazinothioyl, triazinothioyl, quinolinothioyl, isoquinolothioyl, quinazolinothioyl, quinoxalinothioyl azaphenanthrothioyl, azaanthracene benzothiophenyl, azatriphenylene benzothiophenyl, dibenzothiophenyl, benzodibenzothiophenyl, indolyl, azatriphenylene, azatrithiol, dibenzotrithiol, benzothiophenyl, dibenzotrityl, benzothiophenyl, dibenzoindolyl, dibenzotrityl, benzothienyl, dibenzoyl, benzothienyl pyrazinothioyl, pyridazinothioyl, triazinothioyl, quinolinothioyl, isoquinolothioyl, quinazolinothioyl, quinoxalinothioyl, azaphenanthrothioyl, azaanthracene othioyl, azatriphenylolthenyl, dibenzothienyl, benzodibenzothienyl, indolyl, benzodithioenyl, quinazolinothioyl, quinoxalinothioyl, azaphenanthrothioyl, azanthioyl, azatriphenylolthienyl, benzodithioenyl, indolyl, and the like azaindolyl, benzindolyl, naphthaindolyl, phenanthroindolyl, pyridoindolyl, carbazolyl, benzocarbazolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, spirofluorenyloxy, spirofluorenylthio-anthracene, spirofluorenyloxy and the like, but is not limited thereto. The number of carbon atoms of the heteroaryl group may be 2 to 60, preferably 2 to 30, preferably 2 to 25, and more preferably 3 to 18.

In the present specification, the arylene group refers to a generic term for a divalent group remaining after two hydrogen atoms are removed from the aromatic nucleus carbon of an aromatic compound molecule. The arylene group includes a monocyclic arylene group, a polycyclic arylene group, a fused ring arylene group, or a combination thereof. Examples of the arylene group may include phenylene, biphenylene, terphenylene, tetraphenylene, pentachenylene, naphthylene, phenanthrylene, fluorenylene, benzofluorenylene, and the like, but are not limited thereto. The number of carbon atoms of the arylene group is 6 to 60, preferably 6 to 30, preferably 6 to 25, preferably 6 to 18, more preferably 6 to 10.

In the present specification, the sub-condensed polycyclic group means a divalent group comprising at least two rings in which at least one aromatic ring and at least one non-aromatic ring are condensed with each other. Examples of the condensed polycyclic group may include, but are not limited to, a benzocyclopropylene group, a benzocyclobutylene group, a benzocyclobutenyl group, a indanylene group, an indenylene group, a tetrahydronaphthalenyl group, a dihydronaphthalenyl group, a benzocycloheptylene group, a benzocycloheptenyl group, and the like. The fused polycyclic group has 6 to 60, preferably 6 to 30, preferably 6 to 25, preferably 6 to 18, and more preferably 6 to 12 carbon atoms.

In the present specification, the heteroarylene group means a divalent group in which at least one carbon atom in the arylene group is substituted with a hetero atom. The hetero atom is selected from oxygen, sulfur, nitrogen, phosphorus, boron, silicon, and the like, but is not limited thereto. The heteroarylene includes a monocyclic heteroarylene, a polycyclic heteroarylene, a fused ring heteroarylene, or a combination thereof. Indolylene, carbazolylene, benzocarbazolylene, and a pyridylene group, a pyrimidinylene group, a pyrazinylene group, a indolylene, carbazolylene, benzocarbazolylene, pyridylene, pyrimidinylene, pyrazinylene, and pyridazinylene, triazinylene, quinolinylene, isoquinolylene, quinoxalinylene, and the like, but is not limited thereto. The number of carbon atoms of the heteroarylene group is 2 to 60, preferably 2 to 30, preferably 2 to 25, and more preferably 3 to 18.

Ar ₁、Ar₂ is independently selected from the group shown below,

the X is selected from O, S;

T is an integer from 0 to 2;

m is an integer from 0 to 4;

s is an integer of 0 to 3;

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

Preferably, the saidRing A of (a) is selected from one of the groups shown below,

The G is the same or different and is selected from CH or N;

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

N ₁ is an integer of 0-4, n ₂ is an integer of 0-6, n ₃ is an integer of 0-8, and n ₄ is an integer of 0-2.

N ₁ is an integer of 0 to 4, n ₂ is an integer of 0 to 6, n ₃ is an integer of 0 to 8, n ₄ is an integer of 0 to 2, n ₅ is an integer of 0 to 3, n ₆ is an integer of 0 to 5, and n ₇ is an integer of 0 to 7.

Preferably, the method comprises the steps of, the R _g groups are the same or different and are selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutylalkyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexenyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted anthryl, substituted or unsubstituted pyrenyl substituted or unsubstituted benzocyclopropane group, substituted or unsubstituted benzocyclobutane group, substituted or unsubstituted benzocyclobutene group, substituted or unsubstituted indanyl group, substituted or unsubstituted indenyl group, substituted or unsubstituted tetrahydronaphthyl group, substituted or unsubstituted dihydronaphthyl group, substituted or unsubstituted benzocycloheptane group, substituted or unsubstituted fluorenyl group, substituted or unsubstituted benzofluorenyl group, substituted or unsubstituted benzofuranyl group, substituted or unsubstituted dibenzofuranyl group, substituted or unsubstituted benzothienyl group, substituted or unsubstituted dibenzothiophenyl group, substituted or unsubstituted indolyl group, substituted or unsubstituted carbazolyl group, substituted or unsubstituted benzoxadiazolyl group, substituted or unsubstituted benzothiadiazolyl group, substituted or unsubstituted benzotriazolyl group, substituted or unsubstituted pyridyl group, one of a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted pyridazinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinolinyl group, or two adjacent R _g groups are bonded to each other to form a substituted or unsubstituted ring.

Preferably, the method comprises the steps of, the R is the same or different and is selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted cyclopropane, substituted or unsubstituted cyclobutane, substituted or unsubstituted cyclopentane, substituted or unsubstituted cyclohexenyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornane, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted anthryl, substituted or unsubstituted pyrene substituted or unsubstituted benzocyclopropane, substituted or unsubstituted benzocyclobutane, substituted or unsubstituted benzocyclobutene, substituted or unsubstituted indanyl, substituted or unsubstituted indenyl, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted dihydronaphthyl, substituted or unsubstituted benzocycloheptane, substituted or unsubstituted fluorenyl, substituted or unsubstituted benzofluorenyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted indolyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted benzoxadiazolyl, substituted or unsubstituted benzothiadiazolyl, substituted or unsubstituted benzotriazolyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted pyridazinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinolinyl group.

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

Each R ₂、R₃ is the same or different and is selected from one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 condensed polycyclic group, substituted or unsubstituted C2-C30 heteroaryl, or two adjacent R ₂、R₃ are bonded with each other to form a substituted or unsubstituted ring;

the Y is selected from O, S, C (R _y)₂ or N (R _y), and the R _y is the same or different and is selected from one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 condensed polycyclic group and substituted or unsubstituted C2-C30 heteroaryl, or two adjacent R _y are mutually bonded to form a substituted or unsubstituted ring;

the E is the same or different and is selected from CH or N;

The L ₀₁、L₀₂ is independently selected from one of single bond, substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted benzocyclobutene, substituted or unsubstituted indenylene, substituted or unsubstituted indanylene, substituted or unsubstituted dihydronaphtalenyl, substituted or unsubstituted tetrahydronaphtalenyl, substituted or unsubstituted pyridylene, substituted or unsubstituted pyrimidylene, substituted or unsubstituted pyrazinylene and substituted or unsubstituted pyridazinylene, wherein k and f are integers from 0 to 4, and e is an integer from 0 to 7;

when e is 2 or more, each unit in brackets is the same or different.

The k and f are selected from integers of 0-4, the k ₁、f₁ is selected from integers of 0-3, the k ₂、f₂ is selected from integers of 0-2, the k ₃ is selected from integers of 0-6, the k ₄ is selected from integers of 0-8, and the k ₅ is selected from integers of 0-10;

The R _k is the same or different and is selected from one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 condensed polycyclic group and substituted or unsubstituted C2-C30 heteroaryl;

The R _y is the same or different and is selected from one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 condensed polycyclic group, substituted or unsubstituted C2-C30 heteroaryl, or two adjacent R _y are bonded with each other to form a substituted or unsubstituted ring.

Preferably, the method comprises the steps of, each R ₂、R₃ is the same or different and is selected from the group consisting of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted cyclopropanyl, substituted or unsubstituted cyclobutylalkyl, substituted or unsubstituted cyclopentylalkyl, substituted or unsubstituted cyclohexenyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted pyrenyl substituted or unsubstituted benzocyclopropane group, substituted or unsubstituted benzocyclobutane group, substituted or unsubstituted benzocyclobutene group, substituted or unsubstituted indanyl group, substituted or unsubstituted indenyl group, substituted or unsubstituted tetrahydronaphthyl group, substituted or unsubstituted dihydronaphthyl group, substituted or unsubstituted benzocycloheptane group, substituted or unsubstituted fluorenyl group, substituted or unsubstituted benzofluorenyl group, substituted or unsubstituted benzofuranyl group, substituted or unsubstituted dibenzofuranyl group, substituted or unsubstituted benzothienyl group, substituted or unsubstituted dibenzothiophenyl group, substituted or unsubstituted indolyl group, substituted or unsubstituted carbazolyl group, substituted or unsubstituted benzoxadiazolyl group, substituted or unsubstituted benzothiadiazolyl group, substituted or unsubstituted benzotriazolyl group, substituted or unsubstituted pyridyl group, one of a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted pyridazinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinolinyl group, or two adjacent R ₂、R₃ groups are bonded to each other to form a substituted or unsubstituted ring;

The R _k groups are the same or different and are selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutylalkyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexenyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted anthryl, substituted or unsubstituted pyrenyl substituted or unsubstituted benzocyclopropane, substituted or unsubstituted benzocyclobutane, substituted or unsubstituted benzocyclobutene, substituted or unsubstituted indanyl, substituted or unsubstituted indenyl, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted dihydronaphthyl, substituted or unsubstituted benzocycloheptane, substituted or unsubstituted fluorenyl, substituted or unsubstituted benzofluorenyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted indolyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted benzoxadiazolyl, substituted or unsubstituted benzothiadiazolyl, substituted or unsubstituted benzotriazolyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, one of a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted pyridazinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinolinyl group;

The R _y is selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutanyl, substituted or unsubstituted cyclopentanyl, substituted or unsubstituted cyclohexenyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted benzocyclopropanyl substituted or unsubstituted benzocyclobutanyl, substituted or unsubstituted benzocyclobutenyl, substituted or unsubstituted indanyl, substituted or unsubstituted indenyl, substituted or unsubstituted tetrahydronaphthyl substituted or unsubstituted dihydronaphthyl, substituted or unsubstituted benzocycloheptyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted benzofluorenyl, substituted or unsubstituted benzofuranyl substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted indolyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted benzoxadiazolyl, substituted or unsubstituted benzothiadiazolyl, substituted or unsubstituted benzotriazole, substituted or unsubstituted pyridinyl, substituted or unsubstituted pyrimidinyl, one of a substituted or unsubstituted pyrazinyl, a substituted or unsubstituted pyridazinyl, a substituted or unsubstituted triazinyl, a substituted or unsubstituted quinolinyl, a substituted or unsubstituted isoquinolinyl, or two adjacent R _y are bonded to each other to form a substituted or unsubstituted ring.

Preferably, L ₁、L₂ is independently selected from a single bond or a group as shown below,

The F are the same or different and are selected from CH or N;

The R ₄ is the same or different and is selected from one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 condensed polycyclic group, substituted or unsubstituted C2-C30 heteroaryl, or two adjacent R ₄ are bonded with each other to form a substituted or unsubstituted ring;

s is an integer of 0-4, and h is an integer of 0-4;

When h is 2 or more, each unit in brackets is the same or different.

Preferably, L ₁、L₂ is independently selected from a single bond, one of the groups shown below, or a combination thereof,

S is selected from an integer of 0-4, s ₁ is selected from an integer of 0-3, s ₂ is selected from an integer of 0-2, s ₃ is selected from an integer of 0-6, s ₄ is selected from an integer of 0-8, and s ₅ is selected from an integer of 0-10;

the R _s is the same or different and is selected from one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 condensed polycyclic group and substituted or unsubstituted C2-C30 heteroaryl.

Preferably, the method comprises the steps of, the R ₄ groups are the same or different and are selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutylalkyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexenyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted anthryl, substituted or unsubstituted pyrenyl substituted or unsubstituted benzocyclopropane group, substituted or unsubstituted benzocyclobutane group, substituted or unsubstituted benzocyclobutene group, substituted or unsubstituted indanyl group, substituted or unsubstituted indenyl group, substituted or unsubstituted tetrahydronaphthyl group, substituted or unsubstituted dihydronaphthyl group, substituted or unsubstituted benzocycloheptane group, substituted or unsubstituted fluorenyl group, substituted or unsubstituted benzofluorenyl group, substituted or unsubstituted benzofuranyl group, substituted or unsubstituted dibenzofuranyl group, substituted or unsubstituted benzothienyl group, substituted or unsubstituted dibenzothiophenyl group, substituted or unsubstituted indolyl group, substituted or unsubstituted carbazolyl group, substituted or unsubstituted benzoxadiazolyl group, substituted or unsubstituted benzothiadiazolyl group, substituted or unsubstituted benzotriazolyl group, substituted or unsubstituted pyridyl group, one of a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted pyridazinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinolinyl group, or two adjacent R ₄ groups are bonded to each other to form a substituted or unsubstituted ring;

The R _s groups are the same or different and are selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutylalkyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexenyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted anthryl, substituted or unsubstituted pyrenyl substituted or unsubstituted benzocyclopropane, substituted or unsubstituted benzocyclobutane, substituted or unsubstituted benzocyclobutene, substituted or unsubstituted indanyl, substituted or unsubstituted indenyl, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted dihydronaphthyl, substituted or unsubstituted benzocycloheptane, substituted or unsubstituted fluorenyl, substituted or unsubstituted benzofluorenyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted indolyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted benzoxadiazolyl, substituted or unsubstituted benzothiadiazolyl, substituted or unsubstituted benzotriazolyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted pyridazinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinolinyl group.

Preferably, ar is selected from one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 fused polycyclic group, substituted or unsubstituted C2-C30 heteroaryl, or Ar is directly connected with L.

Preferably, the method comprises the steps of, the Ar is selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted cyclopropanyl, substituted or unsubstituted cyclobutanyl, substituted or unsubstituted cyclopentylalkyl, substituted or unsubstituted cyclohexenyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted benzocyclopropanyl substituted or unsubstituted benzocyclobutenyl, substituted or unsubstituted indanyl, substituted or unsubstituted indenyl, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted dihydronaphthyl, substituted or unsubstituted benzocycloheptyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted benzofluorenyl, substituted or unsubstituted benzofuranyl substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted indolyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted spirofluorenyloxyanthracenyl, substituted or unsubstituted spirofluorenylthioanthracenyl, substituted or unsubstituted spirofluorenazaanthracenyl, substituted or unsubstituted spiroanthracenyl, substituted or unsubstituted benzoxadiazolyl, substituted or unsubstituted benzobisoxazolyl, A substituted or unsubstituted benzothiadiazolyl group, a substituted or unsubstituted benzotriazolyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted pyridazinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinolinyl group, or Ar is directly attached to L.

Preferably, when Ar is directly attached to L, the Ar is a single bond.

Preferably, the method comprises the steps of, the R ₁ groups are the same or different and are selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted cyclopropanyl, substituted or unsubstituted cyclobutylalkyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexenyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted benzocyclopropanyl, substituted or unsubstituted benzocyclobutanyl, substituted or unsubstituted benzocyclobutenyl, substituted or unsubstituted indanyl a substituted or unsubstituted indenyl group, a substituted or unsubstituted tetrahydronaphthyl group, a substituted or unsubstituted dihydronaphthyl group, a substituted or unsubstituted benzocycloheptyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted benzoxadiazolyl group, a substituted or unsubstituted benzothiadiazolyl group, a substituted or unsubstituted benzotriazolyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted pyridazinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinolinyl group.

Preferably, the method comprises the steps of, the R ₀ groups are the same or different and are selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutylalkyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexenyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted anthryl, substituted or unsubstituted pyrenyl substituted or unsubstituted benzocyclopropane group, substituted or unsubstituted benzocyclobutane group, substituted or unsubstituted benzocyclobutene group, substituted or unsubstituted indanyl group, substituted or unsubstituted indenyl group, substituted or unsubstituted tetrahydronaphthyl group, substituted or unsubstituted dihydronaphthyl group, substituted or unsubstituted benzocycloheptane group, substituted or unsubstituted fluorenyl group, substituted or unsubstituted benzofluorenyl group, substituted or unsubstituted benzofuranyl group, substituted or unsubstituted dibenzofuranyl group, substituted or unsubstituted benzothienyl group, substituted or unsubstituted dibenzothiophenyl group, substituted or unsubstituted indolyl group, substituted or unsubstituted carbazolyl group, substituted or unsubstituted benzoxadiazolyl group, substituted or unsubstituted benzothiadiazolyl group, substituted or unsubstituted benzotriazolyl group, substituted or unsubstituted pyridyl group, one of a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted pyridazinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted quinolinyl group, and a substituted or unsubstituted isoquinolinyl group.

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

The above list some specific chemical structures of the carbazole compound shown in formula 1 of the present invention, but the present invention is not limited to these chemical structures, and substituents are included in the carbazole compound as defined above, even when the carbazole compound is based on the structure shown in formula 1.

Preferably, the host material satisfies the following condition that the energy gap (Eg) is 2.6 eV≤3.0 eV.

Preferably, the organic electroluminescent device further comprises a hole transport region between the anode and the light emitting layer, the hole transport region comprising a star compound of formula 2,

Ar ₁₀～Ar₆₀ is independently selected from one of substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C6-C60 condensed polycyclic group and substituted or unsubstituted C2-C60 heteroaryl;

the L ₁₀～L₆₀ is independently selected from one or a combination of single bond, substituted or unsubstituted arylene of C6-C60, substituted or unsubstituted sub-condensed polycyclic group of C6-C60, substituted or unsubstituted heteroarylene of C2-C60;

The R ₁₀ is the same or different and is selected from one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C6-C20 condensed polycyclic group and substituted or unsubstituted C2-C20 heteroaryl;

And a is an integer from 0 to 3.

Preferably, the star-shaped compound of the formula 2 is selected from at least one of the structures shown below,

Preferably, ar ₁₀～Ar₆₀ is independently selected from one of the groups shown below,

B ₁ is an integer of 0-5, and b ₂ is an integer of 0-4;

Each R ₅、R₅₀ is the same or different and is selected from one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 condensed polycyclic group, substituted or unsubstituted C2-C30 heteroaryl, or two adjacent R ₅、R₅₀ are bonded with each other to form a substituted or unsubstituted ring;

the Q is selected from C (R _q)₂, O, S or N (R _q), and the R _q is the same or different and is selected from one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 condensed polycyclic group and substituted or unsubstituted C2-C30 heteroaryl, or two adjacent R _q are mutually bonded to form a substituted or unsubstituted ring.

B ₁ is an integer of 0-5, b ₂ is an integer of 0-4, b ₃ is an integer of 0-7, b ₄ is an integer of 0-9, b ₅ is an integer of 0-3, b ₆ is an integer of 0-2, b ₇ is an integer of 0-6, b ₈ is an integer of 0-8, and b ₉ is an integer of 0-10;

the R _q is the same or different and is selected from one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 condensed polycyclic group and substituted or unsubstituted C2-C30 heteroaryl;

The R _b is the same or different and is selected from one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 condensed polycyclic group, substituted or unsubstituted C2-C30 heteroaryl, or two adjacent R _b are bonded with each other to form a substituted or unsubstituted ring.

Preferably, the method comprises the steps of, each R ₅、R₅₀ is the same or different and is selected from the group consisting of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted cyclopropanyl, substituted or unsubstituted cyclobutylalkyl, substituted or unsubstituted cyclopentylalkyl, substituted or unsubstituted cyclohexenyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted pyrenyl substituted or unsubstituted benzocyclopropane group, substituted or unsubstituted benzocyclobutane group, substituted or unsubstituted benzocyclobutene group, substituted or unsubstituted indanyl group, substituted or unsubstituted indenyl group, substituted or unsubstituted tetrahydronaphthyl group, substituted or unsubstituted dihydronaphthyl group, substituted or unsubstituted benzocycloheptane group, substituted or unsubstituted fluorenyl group, substituted or unsubstituted benzofluorenyl group, substituted or unsubstituted benzofuranyl group, substituted or unsubstituted dibenzofuranyl group, substituted or unsubstituted benzothienyl group, substituted or unsubstituted dibenzothiophenyl group, substituted or unsubstituted indolyl group, substituted or unsubstituted carbazolyl group, substituted or unsubstituted benzoxadiazolyl group, substituted or unsubstituted benzothiadiazolyl group, substituted or unsubstituted benzotriazolyl group, substituted or unsubstituted pyridyl group, one of a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted pyridazinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinolinyl group, or two adjacent R ₅、R₅₀ groups are bonded to each other to form a substituted or unsubstituted ring;

The R _q is selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutanyl, substituted or unsubstituted cyclopentanyl, substituted or unsubstituted cyclohexenyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted benzocyclopropanyl substituted or unsubstituted benzocyclobutanyl, substituted or unsubstituted benzocyclobutenyl, substituted or unsubstituted indanyl, substituted or unsubstituted indenyl, substituted or unsubstituted tetrahydronaphthyl substituted or unsubstituted dihydronaphthyl, substituted or unsubstituted benzocycloheptyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted benzofluorenyl, substituted or unsubstituted benzofuranyl substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted indolyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted benzoxadiazolyl, substituted or unsubstituted benzothiadiazolyl, substituted or unsubstituted benzotriazole, substituted or unsubstituted pyridinyl, substituted or unsubstituted pyrimidinyl, one of a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted pyridazinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinolinyl group;

The R _b groups are the same or different and are selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutylalkyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexenyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted anthryl, substituted or unsubstituted pyrenyl substituted or unsubstituted benzocyclopropane, substituted or unsubstituted benzocyclobutane, substituted or unsubstituted benzocyclobutene, substituted or unsubstituted indanyl, substituted or unsubstituted indenyl, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted dihydronaphthyl, substituted or unsubstituted benzocycloheptane, substituted or unsubstituted fluorenyl, substituted or unsubstituted benzofluorenyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted indolyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted benzoxadiazolyl, substituted or unsubstituted benzothiadiazolyl, substituted or unsubstituted benzotriazolyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, one of a substituted or unsubstituted pyrazinyl, a substituted or unsubstituted pyridazinyl, a substituted or unsubstituted triazinyl, a substituted or unsubstituted quinolinyl, a substituted or unsubstituted isoquinolinyl, or two adjacent R _b are bonded to each other to form a substituted or unsubstituted ring.

Preferably, L ₁₀～L₆₀ is independently selected from a single bond or a group as shown below,

The R ₆ is the same or different and is selected from one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 condensed polycyclic group, substituted or unsubstituted C2-C30 heteroaryl, or two adjacent R ₆ are bonded with each other to form a substituted or unsubstituted ring;

the W is the same or different and is selected from CH or N;

d ₁ is an integer of 0-4, and c is an integer of 0-3;

When c is 2 or more, each unit in brackets is the same or different.

Preferably, L ₁₀～L₆₀ is independently selected from a single bond, one of the groups shown below, or a combination thereof,

The d ₁ is selected from an integer of 0-4, the d ₂ is selected from an integer of 0-3, the d ₃ is selected from an integer of 0-2, the d ₄ is selected from an integer of 0-6, the d ₅ is selected from an integer of 0-8, and the d ₆ is selected from an integer of 0-10;

The R ₆ is the same or different and is selected from one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 condensed polycyclic group, substituted or unsubstituted C2-C30 heteroaryl, or two adjacent R ₆ are bonded with each other to form a substituted or unsubstituted ring;

The R _d is the same or different and is selected from one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 condensed polycyclic group and substituted or unsubstituted C2-C30 heteroaryl.

Preferably, the method comprises the steps of, the R ₆ groups are the same or different and are selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutylalkyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexenyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted anthryl, substituted or unsubstituted pyrenyl substituted or unsubstituted benzocyclopropane group, substituted or unsubstituted benzocyclobutane group, substituted or unsubstituted benzocyclobutene group, substituted or unsubstituted indanyl group, substituted or unsubstituted indenyl group, substituted or unsubstituted tetrahydronaphthyl group, substituted or unsubstituted dihydronaphthyl group, substituted or unsubstituted benzocycloheptane group, substituted or unsubstituted fluorenyl group, substituted or unsubstituted benzofluorenyl group, substituted or unsubstituted benzofuranyl group, substituted or unsubstituted dibenzofuranyl group, substituted or unsubstituted benzothienyl group, substituted or unsubstituted dibenzothiophenyl group, substituted or unsubstituted indolyl group, substituted or unsubstituted carbazolyl group, substituted or unsubstituted benzoxadiazolyl group, substituted or unsubstituted benzothiadiazolyl group, substituted or unsubstituted benzotriazolyl group, substituted or unsubstituted pyridyl group, one of a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted pyridazinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinolinyl group, or two adjacent R ₆ groups are bonded to each other to form a substituted or unsubstituted ring;

The R _d groups are the same or different and are selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutylalkyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexenyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted anthryl, substituted or unsubstituted pyrenyl substituted or unsubstituted benzocyclopropane, substituted or unsubstituted benzocyclobutane, substituted or unsubstituted benzocyclobutene, substituted or unsubstituted indanyl, substituted or unsubstituted indenyl, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted dihydronaphthyl, substituted or unsubstituted benzocycloheptane, substituted or unsubstituted fluorenyl, substituted or unsubstituted benzofluorenyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted indolyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted benzoxadiazolyl, substituted or unsubstituted benzothiadiazolyl, substituted or unsubstituted benzotriazolyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted pyridazinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinolinyl group.

Preferably, the method comprises the steps of, the R ₁₀ groups are the same or different and are selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutylalkyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexenyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted anthryl, substituted or unsubstituted pyrenyl substituted or unsubstituted benzocyclopropane group, substituted or unsubstituted benzocyclobutane group, substituted or unsubstituted benzocyclobutene group, substituted or unsubstituted indanyl group, substituted or unsubstituted indenyl group, substituted or unsubstituted tetrahydronaphthyl group, substituted or unsubstituted dihydronaphthyl group, substituted or unsubstituted benzocycloheptane group, substituted or unsubstituted fluorenyl group, substituted or unsubstituted benzofluorenyl group, substituted or unsubstituted benzofuranyl group, substituted or unsubstituted dibenzofuranyl group, substituted or unsubstituted benzothienyl group, substituted or unsubstituted dibenzothiophenyl group, substituted or unsubstituted indolyl group, substituted or unsubstituted carbazolyl group, substituted or unsubstituted benzoxadiazolyl group, substituted or unsubstituted benzothiadiazolyl group, substituted or unsubstituted benzotriazolyl group, substituted or unsubstituted pyridyl group, A substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted pyridazinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinolinyl group.

Preferably, the star compound of formula 2 is selected from at least one of the structures shown below,

The specific chemical structures of the star-shaped compound shown in the formula 2 are listed above, but the invention is not limited to the chemical structures, and substituents are all included on the basis of the structure shown in the formula 2.

The functional layer of the organic electroluminescent device of the present invention may contain at least one of a hole transport region, a light emitting region, an electron transport region, a capping layer, and the like as described below. Any functional layer having hole injection and/or transport properties, electron injection and/or transport properties, light emitting properties or light extraction properties should be included. Each functional layer may be formed of a single film or a plurality of films, and each film may be formed of only one material or a plurality of materials.

The material of each layer of thin film in the organic electroluminescent device is not particularly limited, and materials known in the art can be used. The following describes each organic functional layer of the above-mentioned organic electroluminescent device and the electrodes on both sides of the device, respectively:

In the specification, the anode needs a material having a relatively high work function in order to inject holes into the organic layer. The anode includes, but is not limited to, materials, metals or alloys thereof, metal oxides, laminates, and the like as described below. Specific examples may include aluminum (Al), silver (Ag), platinum (Pt), palladium (Pd), copper (Cu), nickel (Ni), indium Tin Oxide (ITO), zinc oxide (ZnO), indium tin oxide/silver/indium tin oxide (ITO/Ag/ITO), and the like, but are not limited thereto.

In this specification, the cathode needs to have a low work function in order to inject electrons into the organic layer. The cathode includes, but is not limited to, materials, metals or alloys thereof, laminates, and the like as described below. Specific examples may include aluminum (Al), magnesium (Mg), silver (Ag), gold (Au), tin (Sn), strontium (Sr), samarium (Sm), magnesium: silver (Mg: ag), and the like, but are not limited thereto.

The hole injection layer has the effects of reducing ITO surface roughness, reducing internal defects of devices, reducing hole injection potential barriers and the like. The hole injection material includes, but is not limited to, materials such as metal oxides, phthalocyanine compounds, arylamine compounds, low molecular organic compounds such as polycyano-containing conjugated organic materials, high molecular materials, and the like, and specific examples may include silver oxide (AgO), molybdenum trioxide (MoO ₃), copper phthalocyanine (CuPc), 4',4 "-tris (N- (naphthalen-1-yl) -N-phenyl-amino) triphenylamine (1-TNATA), 4',4" -tris [ 2-naphthylphenylamino ] triphenylamine (2-TNATA), 4',4 "-tris (N-3-methylphenyl-N-phenylamino) triphenylamine (m-MTDATA), N ' -diphenyl-N, N ' -bis- [4- (N, N-diphenylamine) phenyl ] benzidine (NPNPB), 1,4,5,8,9,11-hexaazabenzonitrile (HAT-CN), 4',4" - ((1 e,1' e,1 "e) -cyclopropan-1, 2, 3-trisilylene tris (cyanomethane subunit)) tris (2, 3,5, 6-tetrafluorobenzonitrile), poly (3, 4-ethylenedioxythiophene)/poly (styrenesulfonic acid) (PEDOT/PSS), and the like, but is not limited thereto.

In this specification, the hole transport layer has the effect of improving the transport efficiency of holes in the device and blocking electrons in the light emitting layer. The hole transport layer includes, but is not limited to, materials such as aromatic amine derivatives, carbazole derivatives, polymers, and the like. Specific examples may include N, N '-tetrabiphenyl-diamine, N' -diphenyl-N, N '- (1-naphthyl) -1,1' -biphenyl-4, 4 '-diamine (NPB), N' -bis (naphthalen-2-yl) -N, N '-bis (phenyl) biphenyl-4, 4' -diamine (. Beta. -NPB), 4 '-cyclohexylbis [ N, N-bis (4-methylphenyl) aniline ] (TAPC), N, N' -diphenyl-N, N '-bis (3-methylphenyl) -1,1' -biphenyl-4, 4 '-diamine (TPD), 2, 7-tetrakis (diphenylamino) -9, 9-spirobifluorene (spira-TAD), 1,3, 5-tris (9-carbazolyl) benzene (TCB), 4',4 "-tris (carbazol-9-yl) triphenylamine (TCTA), poly (4-vinyl triphenylamine) (PVTPA), and the like, but are not limited thereto. Preferred are the star compounds of formula 2 of the present invention.

In this specification, the light emitting layer includes a host material and a doping material, and the light emitting material may 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 doping material may vary depending on the material used, and the doping ratio of the doping 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 bipolar charge transport properties and also needs to have an appropriate energy level to efficiently transfer excitation energy to the guest light emitting material. The main material may be one material or two or more materials. The carbazole compound of formula 1 of the present invention is preferred. The carbazole 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 or an n-type host material, and when used in combination with a p-type host material or an n-type host material, the carbazole compound of formula 1 of the present invention and the p-type host material or the n-type host material have a weight ratio of 1:99 to 99:1, preferably 20:80 to 80:20. The host material includes, but is not limited to, materials described below, heterocyclic compounds, aromatic amine compounds, fused aromatic ring derivatives, metal complexes, siliceous compounds, AND the like, AND specific examples may include 2- (10-phenylanthracen-9-yl) dibenzo [ b, d ] furan, 2, 7-bis (9H-carbazol-9-yl) -9, 9-dimethylfluorene (DMFL-CBP), 2, 7-bis (carbazol-9-yl) -9, 9-spirobifluorene (Spiro-2 CBP), 3 '-bis (N-carbazole) -1,1' -biphenyl (mCBP), 3 '-bis (dibenzothiophen-4-yl) -1,1' -biphenyl (m-BPDBT), 9, 10-bis-2-naphthacene (AND), 9, 10-bis (naphth-1-yl) anthracene, 1, 4-bis (9-phenyl-9H-fluoren-9-yl) benzene (pDPFB), tris (8-hydroxyquinoline) aluminum (Alq ₃), 9- (4-phenyl) -3, 6-bis (3-phenyltris (34-phenyl3, 34-silyl), AND the like.

The doping material may be a fluorescent doping material, a phosphorescent doping material, or a combination thereof. Doping materials include, but are not limited to, materials such as metal complexes, aromatic amine derivatives, styrylamine compounds, fused aromatic compounds, heterocyclic compounds, and the like. Specific examples of phosphorescent dopant materials may include tris [2- (2, 4-difluorophenyl) pyridine ] iridium (Ir (Fppy) ₃), bis (3, 5-difluoro-2- (2-pyridyl) phenyl- (2-carboxypyridyl) iridium (FIrPic), bis (2-phenylpyridine) iridium acetylacetonate (Ir (ppy) ₂ (acac)), tris (2-phenylpyridine) iridium (Ir (ppy) ₃), tris [ 2-phenyl-4-methylquinoline) ] iridium (Ir (Mphq) ₃), bis (1-phenyl-isoquinoline) (acetylacetonate) iridium (Ir (piq) ₂ (acac)), tris (1-phenyl-isoquinoline) iridium (Ir (piq) ₃), bis [9, 9-dimethyl-2- (2-quinolinyl) -9H-fluoren-3-yl ] (2, 4-pentanedione) iridium (Ir (flq) ₂ (acac)). Specific examples of the fluorescent doping material may include N ¹,N¹,N⁶,N⁶ -tetraphenylpyrene-1, 6-diamine, 2,5,8, 11-tetra-tert-butylperylene (TBPe), 1, 4-bis (4- (9H-carbazol-9-yl) styryl) benzene (BCzSB), 4' -bis [4- (di-p-tolylamino) styryl ] biphenyl (DPAVBi), coumarin 545T, 4- (dicyanomethylene) -2-methyl-6- (4-dimethylaminostyryl) -4H-pyran (DCM), and the like, but are not limited thereto.

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

In this specification, the electron transport layer has the effect of improving the transport efficiency of electrons in the device and blocking holes in the light emitting layer. The electron transport layer includes, but is not limited to, materials, metal complexes, heteroaromatic compounds, and the like as described below. Specific examples may include, but are not limited to, 2, 4-bis (4- (naphthalen-1-yl) phenyl) -6- (4- (pyridin-3-yl) phenyl) pyrimidine, 8-hydroxyquinoline aluminum (Alq ₃), tris (4-methyl-8-hydroxyquinoline) aluminum (Almq), 2, 5-bis- (4-naphthyl) -1,3, 4-oxadiazole (BND), 1,3, 5-tris (N-phenyl-2-benzimidazole) benzene (TPBi), 3- (biphenyl-4-yl) -5- (4-tert-butylphenyl) -4-phenyl-4H-1, 2, 4-Triazole (TAZ), 2, 9-dimethyl-4, 7-diphenyl-1, 10-phenanthroline (BCP), 1,3, 5-tris [ (3-pyridyl) -phenyl ] benzene (TmPyPB), and the like.

In the present specification, the electron injection layer serves to reduce an electron injection barrier between the cathode and the organic layer, and thus to effectively inject electrons into the organic layer. The electron injection layer material includes, but is not limited to, materials as described below, metals, metal compounds, metal oxides, and the like. Specific examples may include lithium (Li), lithium fluoride (LiF), 8-hydroxyquinoline lithium (Liq), sodium fluoride (NaF), lithium oxide (Li ₂ O), cesium carbonate (Cs ₂CO₃), and the like, but are not limited thereto.

In this specification, the cover layer has the effect of coupling out light trapped within the device. The capping layer materials include, but are not limited to, materials such as metal compounds, aromatic amine derivatives, carbazole derivatives, and the like. Specific examples may include N, N-diphenyl-N, N ' - (1-naphthyl) -1,1' -biphenyl-4, 4' -diamine (NPB), N4' -tetrakis (4-methoxyphenyl) - [1,1' -biphenyl ] -4,4' -diamine (MeO-TPD), 4' -bis (9-Carbazole) Biphenyl (CBP), tris (8-hydroxyquinoline) aluminum (Alq ₃), and the like.

The method for producing the thin films of each layer in the organic electroluminescent device of the present invention is not particularly limited, and vacuum deposition, sputtering, spin coating, spray coating, screen printing, laser transfer, etc. may be used, but are 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, VR, vehicle-mounted systems, digital cameras, wearable devices and the like.

Synthetic examples

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

Instrument G2-Si quadrupole tandem time-of-flight high resolution mass spectrometer (waters, uk) Vario EL cube organic element analyzer (Elementar, germany).

The method for producing the carbazole compound represented by formula 1 of the present invention is not particularly limited, and conventional methods known to those skilled in the art can be employed. For example, the carbazole compound represented by formula 1 of the present invention can be produced by the synthetic route shown below, for example, by a carbon-carbon coupling reaction, a carbon-nitrogen coupling reaction, and the like.

The method for preparing the star compound represented by formula 2 of the present invention is not particularly limited, and conventional methods known to those skilled in the art can be employed. For example, the star compound represented by the formula 2 of the present invention can be produced by the synthetic route shown below.

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

Synthesis example 1:

To the flask were added n-14 (16.22 g,60 mmol), m-14 (31.42 g,132 mmol), potassium carbonate (21.56 g,156 mmol), palladium tetraphenylphosphine (693 mg,0.6 mmol) and tetrahydrofuran (380 ml) under nitrogen atmosphere, and stirred under reflux for 10 hours. After the reaction, cooling to room temperature, adding water, extracting with dichloromethane, combining organic phases, drying with anhydrous magnesium sulfate, removing the solvent under reduced pressure, and recrystallizing with ethyl acetate to obtain C-14 (22.66 g, 76%), wherein the HPLC purity is not less than 99.84%.

A-14 (10.03 g,60 mmol), b-14 (11.49 g,60 mmol), sodium t-butoxide (6.92 g,72 mmol), dibenzylideneacetone dipalladium (275 mg,0.3 mmol), tri-t-butylphosphine (121 mg,0.6 mmol), toluene (500 ml) were added to the reaction flask under nitrogen, and reacted under reflux for 5 hours. After the reaction, cooling to room temperature, adding water, extracting with dichloromethane, combining organic phases, drying with anhydrous magnesium sulfate, removing the solvent under reduced pressure, recrystallizing the crude product with toluene to obtain A-14 (13.50 g, 81%), wherein the HPLC purity is not less than 99.90%.

A-14 (11.11 g,40 mmol), pinacol diboronate (12.19 g,48 mmol), potassium acetate (7.85 g,80 mmol), pd (dppf) Cl ₂ (146 mg,0.2 mmol), DMF (300 mL) were added to the flask under nitrogen and reacted for 8 hours under reflux. After the reaction, cooling to room temperature, adding water, extracting with dichloromethane, mixing the organic phases, drying with anhydrous magnesium sulfate, removing the solvent under reduced pressure, and recrystallizing with ethyl acetate/petroleum ether (3:1) to obtain B-14 (10.93 g, 74%), wherein the HPLC purity is not less than 99.89%.

To the reaction flask were added B-14 (8.86 g,24 mmol), C-14 (9.94 g,20 mmol), potassium carbonate (5.53 g,40 mmol), palladium tetraphenylphosphine (231 mg,0.2 mmol) and tetrahydrofuran (250 ml) under nitrogen atmosphere, and stirred under reflux for 15 hours. After the reaction, cooling to room temperature, adding water, extracting with dichloromethane, combining organic phases, drying with anhydrous magnesium sulfate, removing the solvent under reduced pressure, and recrystallizing with toluene to obtain compound 14 (11.12 g, 79%), wherein the HPLC purity is not less than 99.96%. Mass spectrum m/z 703.2506 (theory: 703.2511). Theoretical element content (%) C ₅₂H₃₃NO₂:C, 88.74, H,4.73, N,1.99. The measured element contents (%) were C,88.77, H,4.75, N,1.95.

Synthesis example 2:

According to the preparation method of synthetic example 1, m-14 was replaced with equimolar m-26 to give compound 26 (11.90 g), with HPLC purity of 99.94% or more. Mass spectrum m/z 803.2817 (theory: 803.2824). Theoretical element content (%) C ₆₀H₃₇NO₂:C, 89.64, H,4.64, N,1.74. Measured element contents (%) are C,89.67; H,4.62; N,1.78.

Synthesis example 3:

According to the preparation method of synthetic example 1, m-14 was replaced with equimolar m-53 to give compound 53 (12.97 g), with HPLC purity of 99.95% or more. Mass spectrum m/z 887.2675 (theory: 887.2680). Theoretical element content (%) C ₆₄H₄₁NS₂:C, 86.55, H,4.65, N,1.58. The measured element contents (%) were C,86.59, H,4.68, N,1.54.

Synthesis example 4:

According to the preparation method of synthetic example 1, m-14 and b-14 were replaced with equimolar m-61 and b-61, respectively, to give compound 61 (10.67 g), and the HPLC purity was not less than 99.98%. Mass spectrum m/z 627.2194 (theory: 627.2198). Theoretical element content (%) C ₄₆H₂₉NO₂:C, 88.01, H,4.66, N,2.23. The measured element contents (%) were C,88.04; H,4.63; N,2.25.

Synthesis example 5:

According to the preparation method of synthetic example 1, m-14 and b-14 are replaced by m-61 and b-66 with equimolar amounts respectively, to obtain compound 66 (10.49 g), and the HPLC purity is not less than 99.96%. Mass spectrum m/z 631.2454 (theory: 631.2449). Theoretical element content (%) C ₄₆H₂₅D₄NO₂:C, 87.45, H,5.26, N,2.22. The measured element contents (%) are C,87.43, H,5.24, N,2.25.

Synthesis example 6:

According to the preparation method of synthetic example 1, m-14 and b-14 were replaced with equimolar m-75 and b-61, respectively, to give compound 75 (10.39 g), and HPLC purity was not less than 99.97%. Mass spectrum m/z 629.2108 (theory: 629.2103). Theoretical element content (%) C ₄₄H₂₇N₃O₂:C, 83.92, H,4.32, N,6.67. The measured element contents (%) are C,83.95; H,4.36; N,6.64.

Synthesis example 7:

According to the preparation method of synthetic example 1, m-14 and b-14 were replaced with equimolar m-76 and b-61, respectively, to give compound 76 (10.45 g), and the HPLC purity was not less than 99.95%. Mass spectrum m/z 629.2107 (theory: 629.2103). Theoretical element content (%) C ₄₄H₂₇N₃O₂:C, 83.92, H,4.32, N,6.67. The measured element contents (%) are C,83.95, H,4.35, N,6.64.

Synthesis example 8:

According to the preparation method of synthetic example 1, m-14 and b-14 are replaced by m-77 and b-61 in equimolar amounts, respectively, to obtain compound 77 (10.41 g), and HPLC purity is not less than 99.96%. Mass spectrum m/z 629.2109 (theory: 629.2103). Theoretical element content (%) C ₄₄H₂₇N₃O₂:C, 83.92, H,4.32, N,6.67. The measured element contents (%) were C,83.94; H,4.34; N,6.63.

Synthesis example 9:

according to the preparation method of synthetic example 1, m-14 and b-14 are replaced by m-78 and b-61 in equimolar amounts, respectively, to give compound 78 (10.48 g), and the HPLC purity is not less than 99.95%. Mass spectrum m/z 629.2107 (theory: 629.2103). Theoretical element content (%) C ₄₄H₂₇N₃O₂:C, 83.92, H,4.32, N,6.67. Measured element contents (%) are C,83.96; H,4.34; N,6.64.

Synthesis example 10:

According to the preparation method of synthetic example 1, m-14 and b-14 are replaced by m-76 and b-62 with equimolar amounts respectively, to obtain compound 79 (10.38 g), and HPLC purity is not less than 99.96%. Mass spectrum m/z 629.2109 (theory: 629.2103). Theoretical element content (%) C ₄₄H₂₇N₃O₂:C, 83.92, H,4.32, N,6.67. The measured element contents (%) were C,83.95; H,4.29; N,6.69.

Synthesis example 11:

According to the preparation method of synthetic example 1, m-14 and b-14 are replaced by m-90 and b-61 in equimolar amounts respectively, so as to obtain compound 90 (10.29 g), and the HPLC purity is more than or equal to 99.94%. Mass spectrum m/z 627.2191 (theory: 627.2198). Theoretical element content (%) C ₄₆H₂₉NO₂:C, 88.01, H,4.66, N,2.23. Measured element contents (%) are C,88.05; H,4.62; N,2.25.

Synthesis example 12:

according to the preparation method of synthetic example 1, m-14 and b-14 are replaced by m-93 and b-61 in equimolar amounts respectively, to obtain compound 93 (10.53 g), and HPLC purity is not less than 99.96%. Mass spectrum m/z 627.2193 (theory: 627.2198). Theoretical element content (%) C ₄₆H₂₉NO₂:C, 88.01, H,4.66, N,2.23. The measured element contents (%) are C,88.04; H,4.68; N,2.21.

Synthesis example 13:

According to the preparation method of synthetic example 1, m-14 and b-14 were replaced with equimolar m-97 and b-61, respectively, to give compound 97 (10.66 g), and HPLC purity was not less than 99.97%. Mass spectrum m/z 627.2202 (theory: 627.2198). Theoretical element content (%) C ₄₆H₂₉NO₂:C, 88.01, H,4.66, N,2.23. Measured element contents (%) are C,88.05; H,4.64; N,2.21.

Synthesis example 14:

According to the preparation method of synthetic example 1, m-14 and b-14 are replaced by m-101 and b-61 in equimolar amounts respectively to obtain compound 101 (10.80 g), and HPLC purity is not less than 99.98%. Mass spectrum m/z 627.2195 (theory: 627.2198). Theoretical element content (%) C ₄₆H₂₉NO₂:C, 88.01, H,4.66, N,2.23. The measured element contents (%) are C,88.03, H,4.64, N,2.27.

Synthesis example 15:

According to the preparation method of synthetic example 1, m-14 and b-14 are replaced by m-101 and b-104 with equimolar amounts respectively, to obtain compound 104 (10.52 g), and HPLC purity is not less than 99.97%. Mass spectrum m/z 627.2194 (theory: 627.2198). Theoretical element content (%) C ₄₆H₂₉NO₂:C, 88.01, H,4.66, N,2.23. The measured element contents (%) were C,88.04; H,4.64; N,2.27.

Synthesis example 16:

According to the preparation method of synthetic example 1, m-14 and b-14 were replaced with equimolar m-109 and b-61, respectively, to give compound 109 (10.51 g), and the HPLC purity was not less than 99.96%. Mass spectrum m/z 627.2192 (theory: 627.2198). Theoretical element content (%) C ₄₆H₂₉NO₂:C, 88.01, H,4.66, N,2.23. Measured element contents (%) are C,88.05; H,4.62; N,2.25.

Synthesis example 17:

According to the preparation method of synthetic example 1, m-14, a-14 and b-14 were replaced with equimolar m-76, a-151 and b-61, respectively, to give compound 119 (10.46 g) with an HPLC purity of 99.95% or more. Mass spectrum m/z 679.2013 (theory: 679.2008). Theoretical element content (%) C ₄₆H₂₅N₅O₂:C, 81.28, H,3.71, N,10.30. Measured element contents (%) were C,81.24; H,3.74; N,10.33.

Synthesis example 18:

According to the preparation method of synthetic example 1, m-14, a-14 and b-14 are replaced by m-77, a-145 and b-61 with equimolar amounts respectively, to obtain compound 120 (11.01 g), and the HPLC purity is not less than 99.96%. Mass spectrum m/z 705.2411 (theory: 705.2416). Theoretical element content (%) C ₅₀H₃₁N₃O₂:C, 85.09, H,4.43, N,5.95. Measured element contents (%) are C,85.06; H,4.46; N,5.98.

Synthesis example 19:

according to the preparation method of synthetic example 1, m-14 and b-14 were replaced with equimolar m-129 and b-61, respectively, to give compound 129 (10.44 g), and HPLC purity was not less than 99.94%. Mass spectrum m/z 629.2109 (theory: 629.2103). Theoretical element content (%) C ₄₄H₂₇N₃O₂:C, 83.92, H,4.32, N,6.67. The measured element contents (%) were C,83.95; H,4.34; N,6.63.

Synthesis example 20:

According to the preparation method of synthetic example 1, m-14, a-14 and b-14 were replaced with equimolar m-61, a-149 and b-61, respectively, to give compound 149 (12.13 g) having an HPLC purity of 99.97% or more. Mass spectrum m/z 739.3455 (theory: 739.3450). Theoretical element content (%) C ₅₄H₄₅NO₂:C, 87.65, H,6.13, N,1.89. Measured element contents (%) are C,87.63; H,6.17; N,1.86.

Synthesis example 21:

According to the preparation method of synthetic example 1, m-14, a-14 and b-14 were replaced with equimolar m-61, a-153 and b-61, respectively, to give compound 153 (11.06 g) with an HPLC purity of 99.95% or more. Mass spectrum m/z 699.2587 (theory: 699.2594). Theoretical element content (%) C ₄₉H₃₇NO₂ Si: C,84.09; H,5.33; N,2.00. The measured element contents (%) were C,84.04; H,5.36; N,2.04.

Synthesis example 22:

According to the preparation method of Synthesis example 1, b-14 was replaced with equimolar b-61 to obtain compound 165 (13.26 g), and the HPLC purity was not less than 99.97%. Mass spectrum m/z 779.2819 (theory: 779.2824). Theoretical element content (%) C ₅₈H₃₇NO₂:C, 89.32, H,4.78, N,1.80. Measured element contents (%) are C,89.36; H,4.76; N,1.82.

Synthesis example 23:

According to the preparation method of synthetic example 1, m-14 and b-14 are replaced by m-175 and b-61 in equimolar amounts, respectively, to obtain compound 175 (12.82 g), and HPLC purity is not less than 99.96%. Mass spectrum m/z 781.2724 (theory: 781.2729). Theoretical element content (%) C ₅₆H₃₅N₃O₂:C, 86.02, H,4.51, N,5.37. Measured element contents (%) are C,86.06; H,4.54; N,5.33.

Synthesis example 24:

According to the preparation method of synthetic example 1, m-14 and b-14 were replaced with equimolar m-176 and b-61, respectively, to give compound 176 (12.79 g), and the HPLC purity was not less than 99.97%. Mass spectrum m/z 781.2723 (theory: 781.2729). Theoretical element content (%) C ₅₆H₃₅N₃O₂:C, 86.02, H,4.51, N,5.37. Measured element contents (%) are C,86.05, H,4.55, N,5.34.

Synthesis example 25:

According to the preparation method of synthetic example 1, m-14 and b-14 were replaced with equimolar m-179 and b-61, respectively, to give compound 179 (12.81 g), and HPLC purity was not less than 99.97%. Mass spectrum m/z 781.2736 (theory: 781.2729). Theoretical element content (%) C ₅₆H₃₅N₃O₂:C, 86.02, H,4.51, N,5.37. Measured element contents (%) are C,86.06; H,4.55; N,5.33.

Synthesis example 26:

According to the preparation method of synthetic example 1, m-14 and b-14 are replaced by m-181 and b-61 with equimolar amounts respectively, so as to obtain compound 181 (12.23 g), and HPLC purity is not less than 99.94%. Mass spectrum m/z 783.2627 (theory: 783.2634). Theoretical element content (%) C ₅₄H₃₃N₅O₂:C, 82.74, H,4.24, N,8.93. The measured element contents (%) were C,82.71, H,4.22, N,8.97.

Synthesis example 27:

According to the preparation method of synthetic example 1, m-14 and b-14 are replaced by m-186 and b-61 in equimolar amounts respectively to obtain compound 186 (13.10 g), and the HPLC purity is not less than 99.97%. Mass spectrum m/z 779.2820 (theory: 779.2824). Theoretical element content (%) C ₅₈H₃₇NO₂:C, 89.32, H,4.78, N,1.80. Measured element contents (%) are C,89.35; H,4.74; N,1.83.

Synthesis example 28:

According to the preparation method of synthetic example 1, m-14 and b-14 are replaced by m-200 and b-61 in equimolar amounts respectively, so as to obtain compound 200 (10.19 g), wherein the HPLC purity is more than or equal to 99.94%. Mass spectrum m/z 727.2517 (theory: 727.2511). Theoretical element content (%) C ₅₄H₃₃NO₂:C, 89.11, H,4.57, N,1.92. Measured element contents (%) are C,89.16; H,4.54; N,1.96.

Synthesis example 29:

According to the preparation method of synthetic example 1, m-14 and b-14 are replaced by m-205 and b-61 in equimolar amounts, respectively, to obtain compound 205 (11.08 g), and the HPLC purity is not less than 99.97%. Mass spectrum m/z 659.1736 (theory: 659.1741). Theoretical element content (%) C ₄₆H₂₉NS₂:C, 83.73, H,4.43, N,2.12. Measured element contents (%) are C,83.69; H,4.46; N,2.16.

Synthesis example 30:

According to the preparation method of synthetic example 1, m-14 and b-14 are replaced by m-218 and b-61 with equimolar amounts respectively, to obtain compound 218 (10.32 g), wherein the HPLC purity is not less than 99.96%. Mass spectrum m/z 661.1641 (theory: 661.1646). Theoretical element content (%) C ₄₄H₂₇N₃S₂:C, 79.85, H,4.11, N,6.35. The measured element contents (%) were C,79.82, H,4.14, N,6.33.

Synthesis example 31:

According to the preparation method of synthetic example 1, m-14 and b-14 were replaced with equimolar m-223 and b-61, respectively, to give compound 223 (9.82 g), and HPLC purity was not less than 99.94%. Mass spectrum m/z 663.1559 (theory: 663.1551). Theoretical element content (%) C ₄₂H₂₅N₅S₂:C, 75.99, H,3.80, N,10.55. Measured element contents (%) are C,75.94; H,3.84; N,10.58.

Synthesis example 32:

According to the preparation method of synthetic example 1, m-14 and b-14 are replaced by m-232 and b-61 with equimolar amounts respectively, to obtain compound 232 (11.07 g), and HPLC purity is not less than 99.96%. Mass spectrum m/z 659.1736 (theory: 659.1741). Theoretical element content (%) C ₄₆H₂₉NS₂:C, 83.73, H,4.43, N,2.12. Measured element contents (%) are C,83.70; H,4.46; N,2.15.

Synthesis example 33:

According to the preparation method of synthetic example 1, m-14 and b-14 are replaced by m-61 and b-289 with equimolar amounts respectively, to obtain compound 289 (11.82 g), and HPLC purity is not less than 99.97%. Mass spectrum m/z 703.2516 (theory: 703.2511). Theoretical element content (%) C ₅₂H₃₃NO₂:C, 88.74, H,4.73, N,1.99. The measured element contents (%) were C,88.77, H,4.75, N,1.95.

Synthesis example 34:

According to the preparation method of synthetic example 1, m-14 and b-14 are replaced by m-76 and b-289 with equimolar amounts respectively, to obtain compound 303 (11.43 g), and HPLC purity is not less than 99.96%. Mass spectrum m/z 705.2410 (theory: 705.2416). Theoretical element content (%) C ₅₀H₃₁N₃O₂:C, 85.09, H,4.43, N,5.95. Measured element contents (%) are C,85.06; H,4.46; N,5.98.

Synthesis example 35:

According to the preparation method of C-14 in synthetic example 1, m-14 is changed to equimolar m-338 to obtain C-338 (23.17 g, 73%); HPLC purity is not less than 99.82%.

A-14 (3.34 g,20 mmol), C-338 (10.58 g,20 mmol), sodium t-butoxide (2.31 g,24 mmol), dibenzylideneacetone dipalladium (183mg, 0.2 mmol), tri-t-butylphosphine (81 mg,0.4 mmol), toluene (250 ml) were added to the reaction flask under nitrogen and reacted under reflux for 7 hours. After the reaction, cooling to room temperature, adding water, extracting with dichloromethane, combining organic phases, drying with anhydrous magnesium sulfate, removing the solvent under reduced pressure, recrystallizing the crude product with toluene to obtain a compound 338 (10.95 g, 83%), wherein the HPLC purity is not less than 99.95%. Mass spectrum m/z 659.1736 (theory: 659.1741). Theoretical element content (%) C ₄₆H₂₉NS₂:C, 83.73, H,4.43, N,2.12. Measured element contents (%) are C,83.70; H,4.41; N,2.17.

Synthesis example 36:

According to the preparation method of synthetic example 1, m-14 and b-14 were replaced with equimolar m-61 and b-352, respectively, to give compound 352 (10.43 g), with HPLC purity of 99.96% or more. Mass spectrum m/z 677.2359 (theory: 677.2355). Theoretical element content (%) C ₅₀H₃₁NO₂:C, 88.60, H,4.61, N,2.07. The measured element contents (%) are C,88.64; H,4.64; N,2.03.

Synthesis example 37:

According to the preparation method of synthetic example 1, m-14 and b-14 are replaced by m-77 and b-388 in equimolar amounts, respectively, to give compound 373 (10.32 g) with an HPLC purity of 99.95% or more. Mass spectrum m/z 679.2265 (theory: 679.2260). Theoretical element content (%) C ₄₈H₂₉N₃O₂:C, 84.81, H,4.30, N,6.18. The measured element contents (%) are C,84.85, H,4.33, N,6.14.

Synthesis example 38:

According to the preparation method of synthetic example 1, m-14 and b-14 are replaced by m-205 and b-388 in equimolar amounts respectively to obtain compound 388 (10.65 g), and HPLC purity is not less than 99.95%. Mass spectrum m/z 709.1892 (theory: 709.1898). Theoretical element content (%) C ₅₀H₃₁NS₂:C, 84.59, H,4.40, N,1.97. The measured element contents (%) were C,84.55; H,4.43; N,1.94.

Synthesis example 39:

According to the preparation method of synthetic example 1, m-14 and b-14 are replaced by m-61 and b-413 in equimolar amounts respectively, to obtain compound 413 (10.01 g), and HPLC purity is not less than 99.97%. Mass spectrum m/z 641.1987 (theory: 641.1991). Theoretical element content (%) C ₄₆H₂₇NO₃:C, 86.10, H,4.24, N,2.18. The measured element contents (%) are C,86.13, H,4.27, N,2.14.

Synthesis example 40:

According to the preparation method of synthetic example 1, m-14 and b-14 are replaced by m-101 and b-415 with equimolar amounts respectively, to obtain compound 415 (9.88 g), and HPLC purity is not less than 99.97%. Mass spectrum m/z 641.1996 (theory: 641.1991). Theoretical element content (%) C ₄₆H₂₇NO₃:C, 86.10, H,4.24, N,2.18. The measured element contents (%) are C,86.14, H,4.27, N,2.14.

Synthesis example 41:

According to the preparation method of synthetic example 1, m-14 and b-14 are replaced by m-431 and b-415 with equimolar amounts respectively, to obtain compound 431 (11.91 g), and HPLC purity is not less than 99.95%. Mass spectrum m/z 793.2624 (theory: 793.2617). Theoretical element content (%) C ₅₈H₃₅NO₃:C, 87.75, H,4.44, N,1.76. The measured element contents (%) were C,87.79, H,4.41, N,1.73.

Synthesis example 42:

According to the preparation method of synthetic example 1, m-14 and b-14 are replaced by m-478 and b-415 with equal mole respectively, to obtain compound 478 (12.25 g), and HPLC purity is greater than or equal to 99.94%. Mass spectrum m/z 827.2059 (theory: 827.2065). Theoretical element content (%) C ₅₆H₃₃N₃OS₂:C, 81.23, H,4.02, N,5.07. The measured element contents (%) were C,81.27; H,4.05; N,5.04.

Synthesis example 43:

According to the preparation method of synthetic example 1, m-14 and b-14 are replaced by m-61 and b-486 with equimolar amounts respectively, to obtain compound 486 (9.98 g), and the HPLC purity is not less than 99.96%. Mass spectrum m/z 657.1757 (theory: 657.1762). Theoretical element content (%) C ₄₆H₂₇NO₂ S: C,83.99; H,4.14; N,2.13. The measured element contents (%) were C,83.94; H,4.17; N,2.16.

Synthesis example 44:

According to the preparation method of synthetic example 1, m-14 and b-14 are replaced by m-101 and b-534 with equimolar amounts respectively, to obtain compound 534 (10.75 g), and HPLC purity is not less than 99.95%. Mass spectrum m/z 716.2469 (theory: 716.2464). Theoretical element content (%) C ₅₂H₃₂N₂O₂:C, 87.13, H,4.50, N,3.91. Measured element contents (%) are C,87.10, H,4.53, N,3.96.

Synthesis example 45:

According to the preparation method of synthetic example 1, m-14 and b-14 are replaced by m-61 and b-547 respectively in equimolar amounts to obtain compound 547 (12.04 g), and HPLC purity is not less than 99.95%. Mass spectrum m/z 791.2818 (theory: 791.2824). Theoretical element content (%) C ₅₉H₃₇NO₂:C, 89.48, H,4.71, N,1.77. Measured element contents (%) are C,89.45; H,4.74; N,1.73.

Synthesis example 46:

according to the preparation method of synthetic example 1, m-14 and b-14 are replaced by m-61 and b-563 with equimolar amounts respectively to obtain compound 563 (9.43 g), and HPLC purity is not less than 99.96%. Mass spectrum m/z 628.2142 (theory: 628.2151). Theoretical element content (%) C ₄₅H₂₈N₂O₂:C, 85.97, H,4.49, N,4.46. The measured element contents (%) are C,85.93, H,4.45 and N,4.49.

Synthesis example 47:

According to the preparation method of synthetic example 1, m-14 and b-14 are replaced by m-61 and b-578 in equimolar amounts, respectively, to give compound 578 (9.19 g) with HPLC purity of 99.94% or more. Mass spectrum m/z 629.2111 (theory: 629.2103). Theoretical element content (%) C ₄₄H₂₇N₃O₂:C, 83.92, H,4.32, N,6.67. Measured element contents (%) are C,83.96; H,4.37; N,6.62.

Synthesis example 48:

According to the preparation method of synthetic example 1, m-14 and b-14 are replaced by m-205 and b-602 with equimolar amounts respectively, so as to obtain compound 602 (10.91 g), wherein the HPLC purity is greater than or equal to 99.95%. Mass spectrum m/z 736.2013 (theory: 736.2007). Theoretical element content (%) C ₅₁H₃₂N₂S₂:C, 83.12, H,4.38, N,3.80. The measured element contents (%) were C,83.16, H,4.33, N,3.84.

Synthesis example 49:

A-657 (18.95 g,66 mmol), b-14 (11.49 g,60 mmol), potassium carbonate (16.58 g,120 mmol), palladium tetraphenylphosphine (346 mg,0.3 mmol) and tetrahydrofuran (300 ml) were added to the reaction flask under nitrogen, and stirred under reflux for 7 hours. After the reaction, cooling to room temperature, adding water, extracting with dichloromethane, combining organic phases, drying with anhydrous magnesium sulfate, removing the solvent under reduced pressure, crystallizing with toluene to obtain A-657 (16.56 g, 78%), wherein the HPLC purity is not less than 99.87%.

According to the preparation method of synthetic example 1, A-14 and C-14 are replaced by equimolar A-657 and C-61 respectively to obtain a compound 657 (9.79 g), and the HPLC purity is more than or equal to 99.97%. Mass spectrum m/z 627.2193 (theory: 627.2198). Theoretical element content (%) C ₄₆H₂₉NO₂:C, 88.01, H,4.66, N,2.23. Measured element contents (%) are C,88.05; H,4.62; N,2.26.

Synthesis example 50:

According to the preparation method of Synthesis example 49, b-14 and C-61 were replaced with equimolar amounts of b-61 and C-101, respectively, to give compound 710 (10.27 g), and the HPLC purity was not less than 99.95%. Mass spectrum m/z 703.2518 (theory: 703.2511). Theoretical element content (%) C ₅₂H₃₃NO₂:C, 88.74, H,4.73, N,1.99. Measured element contents (%) are C,88.78; H,4.77; N,1.96.

Synthesis example 51:

To the flask were added d-10 (9.03 g,40 mmol), e-10 (12.85 g,40 mmol), sodium tert-butoxide (5.76 g,60 mmol), pd (dppf) Cl ₂ (292 mg,0.4 mmol) and toluene (250 ml) under nitrogen and stirred under reflux for 7 hours. After the reaction, cooling to room temperature, adding water, extracting with dichloromethane, combining the organic phases, drying over anhydrous magnesium sulfate, removing the solvent under reduced pressure, and recrystallizing with toluene/methanol (4:1) to obtain D-10 (14.36 g, 77%); HPLC purity is not less than 99.87%.

To the reaction flask were added D-10 (9.33 g,20 mmol), f-10 (6.77 g,40 mmol), sodium t-butoxide (4.61 g,48 mmol), pd ₂(dba)₃ (183mg, 0.2 mmol), tri-t-butylphosphine (81 mg,0.4 mmol) and toluene (150 ml) under nitrogen protection, and the mixture was reacted under reflux for 6 hours. After the reaction, cooling to room temperature, adding water, extracting with dichloromethane, combining organic phases, drying with anhydrous magnesium sulfate, removing the solvent under reduced pressure, and recrystallizing with toluene to obtain compound 2-10 (11.71 g, 80%), wherein the HPLC purity is not less than 99.97%. Mass spectrum m/z 731.3305 (theory: 731.3300). Theoretical element content (%) C ₅₄H₄₁N₃:C, 88.61, H,5.65, N,5.74. The measured element contents (%) are C,88.65; H,5.63; N,5.71.

Synthesis example 52:

According to the preparation method of synthetic example 51, e-10 and f-10 were replaced with equimolar e-10 and f-10, respectively, to give compound 2-130 (14.03 g), and HPLC purity was not less than 99.95%. Mass spectrum m/z 887.4235 (theory: 887.4239). Theoretical element content (%) C ₆₆H₅₃N₃:C, 89.25, H,6.02, N,4.73. Measured element contents (%) are C,89.22; H,6.05; N,4.75.

Synthesis example 53:

According to the preparation method of Synthesis example 51, e-10 was replaced with equimolar e-148 to give Compound 2-148 (11.82 g), with HPLC purity of 99.95% or more. Mass spectrum m/z 757.3452 (theory: 757.3457). Theoretical element content (%) C ₅₆H₄₃N₃:C, 88.74, H,5.72, N,5.54. Measured element contents (%) are C,88.76, H,5.74, N,5.51.

Device embodiment

In the invention, the ITO anode is ultrasonically cleaned by 5% glass cleaning solution for 2 times each for 20 minutes, and then ultrasonically cleaned by deionized water for 2 times each for 10 minutes. Sequentially using acetone and isopropyl alcohol for ultrasonic cleaning for 20 minutes and drying at 120 ℃. The organic materials are sublimated, and the purity is over 99.99 percent.

Test software, a computer, a K2400 digital source list manufactured by Keithley company in U.S. and a PR788 spectrum scanning luminance meter manufactured by Photo Research company in U.S. are combined into a combined IVL test system to test the driving voltage, luminous efficiency and CIE color coordinates of the organic electroluminescent device. Life testing an M6000 OLED life test system from MCSCIENCE was used. The environment tested was atmospheric and the temperature was room temperature.

Example 1 preparation of organic electroluminescent device 1

The compound 14 and RH-1 of the present invention were vacuum-evaporated on the hole injection layer at a ratio of 1:1 (wt%) and the dopant Ir (flq) ₂ (acac) was vacuum-evaporated on the hole injection layer at a doping amount of 6wt% based on the total amount of the host and the dopant to form a light-emitting layer at a thickness of 33nm, vacuum-evaporated BCP on the light-emitting layer as a hole blocking layer at a thickness of 5nm, vacuum-evaporated Alq ₃ on the hole blocking layer as an electron transport layer at a thickness of 25nm, vacuum-evaporated LiF on the electron transport layer as an electron injection layer at a thickness of 1.0nm, and vacuum-evaporated Al on the electron injection layer as a cathode at a thickness of 150nm.

Examples 2 to 20 preparation of organic electroluminescent devices 2 to 20

The light-emitting layers of example 1 were each replaced with a compound 26, a compound 53, a compound 90, a compound 93, a compound 97, a compound 104, a compound 109, a compound 149, a compound 153, a compound 165, a compound 200, a compound 205, a compound 232, a compound 338, a compound 352, a compound 413, a compound 431, a compound 547, and a compound 710, respectively, and the other steps were the same, to obtain organic electroluminescent devices 2 to 20.

Comparative examples 1-2 preparation of comparative organic electroluminescent devices 1-2

And (3) respectively replacing the compound 14 in the light-emitting layer of the embodiment 1 with R-1 and R-2, and obtaining the comparative organic electroluminescent devices 1-2 in the same steps.

The results of the luminescence characteristic test of the organic electroluminescent devices prepared in examples 1 to 20 and comparative examples 1 to 2 according to the present invention are shown in table 1.

Table 1 light emission characteristic test data of organic electroluminescent device

Example 21 preparation of organic electroluminescent device 21

Vacuum-evaporating 2-TNATA as a hole injection layer with a thickness of 60nm, vacuum-evaporating HT-1 as a hole transport layer with a thickness of 35nm on the hole injection layer, vacuum-evaporating the compounds 75 and RH-2 according to the invention with a ratio of 1:1 (wt%) on the hole transport layer, and evaporating a dopant Ir (piq) ₃ 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 33nm, vacuum-evaporating BCP as a hole blocking layer with a thickness of 5nm on the light-emitting layer, vacuum-evaporating Alq ₃ as an electron transport layer with a thickness of 25nm on the hole blocking layer, vacuum-evaporating LiF as an electron injection layer with a thickness of 1.0nm on the electron transport layer, vacuum-evaporating Al as a cathode on the electron injection layer with a thickness of 150nm.

Examples 22 to 40 preparation of organic electroluminescent devices 22 to 40

The organic electroluminescent devices 22 to 40 were obtained by changing the light-emitting layer of example 1 from the light-emitting layer 75 to the light-emitting layer 76, 77, 78, 79, 119, 120, 129, 175, 176, 179, 181, 218, 223, 303, 373, 478, 563, 578, 602, and the other steps were the same.

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

The compound 75 in the light-emitting layer of example 21 was changed to R-1 and R-2, respectively, and the other steps were the same, to obtain comparative organic electroluminescent devices 3 to 4.

The results of the luminescence characteristics of the organic electroluminescent devices prepared in examples 21 to 40 and comparative examples 3 to 4 according to the present invention are shown in table 2.

Table 2 light emission characteristic test data of organic electroluminescent device

As can be seen from tables 1 and 2, the organic electroluminescent device having the carbazole compound of formula 1 in the light emitting layer has better performance, and is particularly characterized by higher light emitting efficiency and longer service life.

Example 41 preparation of organic electroluminescent device 41

Vacuum-evaporating 2-TNATA as a hole injection layer with a thickness of 65nm, vacuum-evaporating the compound 2-1 of the invention as a hole transport layer with a thickness of 45nm on the hole injection layer, vacuum-evaporating the compound 14 and GH-1 of the invention at a ratio of 1:1 (wt%) on the hole transport layer, and evaporating a dopant Ir (ppy) ₂ (acac) with a doping amount of 8wt% based on the total amount of the host and the dopant to form a light-emitting layer with a thickness of 33nm, vacuum-evaporating BAlq as a hole blocking layer with a thickness of 5nm on the light-emitting layer, vacuum-evaporating Almq ₃ as an electron transport layer with a thickness of 40nm on the hole blocking layer, vacuum-evaporating LiF as an electron injection layer with an evaporation thickness of 1.1nm on the hole transport layer, vacuum-evaporating Al as a cathode with a thickness of 150nm on the electron injection layer.

Examples 42 to 60 preparation of organic electroluminescent devices 42 to 60

Compound 14 in the light-emitting layer of example 41 was replaced with compound 61, compound 66, compound 93, compound 97, compound 101, compound 104, compound 109, compound 165, compound 186, compound 205, compound 232, compound 289, compound 388, compound 413, compound 415, compound 486, compound 534, compound 547, and compound 657, respectively;

The compound 2-1 in the hole transport layer of example 41 was changed to 2-9, 2-20, 2-6, 2-15, 2-51, 2-7, 2-19, 2-2, 2-22, 2-29, 2-26, 2-10, 2-91, 2-116, 2-130, 2-152, 2-148, 2-192, and 2-208, respectively, and the other steps were the same, to obtain an organic electroluminescent device 42-60.

Comparative examples 5 to 8 preparation of comparative organic electroluminescent devices 5 to 8

And (3) changing the compound 2-1 in the hole transport layer of the embodiment 41 into NPB, and changing the compound 14 in the light-emitting layer of the embodiment 41 into the compound 14, the compound 388, the compound 486 and the compound 657 respectively, wherein other steps are the same, so as to obtain the comparative organic electroluminescent devices 5-8.

The results of the luminescence characteristics of the organic electroluminescent devices prepared in examples 41 to 60 and comparative examples 5 to 8 according to the present invention are shown in Table 3.

Table 3 light emission characteristics test data of organic electroluminescent device

Example 61 preparation of organic electroluminescent device 61

2-TNATA was vacuum-evaporated as a hole injection layer on an ITO anode to a thickness of 65nm, 2-57 of the present invention was vacuum-evaporated as a hole transport layer on the hole injection layer to a thickness of 45nm, 75 and GH-2 of the present invention were vacuum-evaporated at a ratio of 1:1 (wt%) on the hole transport layer, and Ir (ppy) ₃ was vacuum-evaporated at a doping amount of 8wt% based on the total amount of the host and the dopant to form a light-emitting layer to a thickness of 33nm, BAlq was vacuum-evaporated as a hole blocking layer to a thickness of 5nm, almq ₃ was vacuum-evaporated as an electron transport layer to a thickness of 40nm, liF was vacuum-evaporated as an electron injection layer on the electron transport layer to a thickness of 1.1nm, and Al was vacuum-evaporated as a cathode on the electron injection layer to a thickness of 150nm.

Examples 62 to 80 preparation of organic electroluminescent devices 62 to 80

Compound 75 in the light-emitting layer of example 61 was replaced with compound 76, compound 77, compound 78, compound 79, compound 119, compound 120, compound 129, compound 175, compound 176, compound 179, compound 181, compound 218, compound 223, compound 303, compound 373, compound 478, compound 563, compound 578, compound 602, respectively;

The compound 2-57 in the hole transport layer of example 61 was changed to compound 2-15, compound 2-36, compound 2-61, compound 2-16, compound 2-20, compound 2-19, compound 2-9, compound 2-6, compound 2-7, compound 2-10, compound 2-1, compound 2-134, compound 2-156, compound 2-21, compound 2-141, compound 2-216, compound 2-2, compound 2-79, compound 2-121, respectively, and the other steps were the same, to obtain an organic electroluminescent device 62-80.

Comparative examples 9 to 12 preparation of comparative organic electroluminescent devices 9 to 12

And (3) changing the compounds 2-57 in the hole transport layer of the embodiment 61 into NPB, and changing the compound 75 in the light-emitting layer of the embodiment 61 into the compound 129, the compound 478, the compound 578 and the compound 602 respectively, wherein other steps are the same, so as to obtain the comparative organic electroluminescent devices 9-12.

The results of the luminescence characteristics of the organic electroluminescent devices prepared in examples 61 to 80 and comparative examples 9 to 12 according to the present invention are shown in Table 4.

Table 4 light emission characteristics test data of organic electroluminescent device

As can be seen from tables 3 and 4, the organic electroluminescent device having the carbazole compound of formula 1 in the light emitting layer and the star compound of formula 2 in the hole transporting layer has better performance, and is particularly characterized by higher luminous efficiency and longer service life.

It should be noted that while the invention has been particularly described with reference to individual embodiments, those skilled in the art may make various modifications in form or detail without departing from the principles of the invention, which modifications are also within the scope of the invention.

Claims

1. An organic electroluminescent device, comprising an anode, a cathode, and an organic layer located between the anode and the cathode, wherein the organic layer comprises a light-emitting layer, the light-emitting layer comprises a host material and a dopant material, the host material comprises a carbazole compound represented by Formula 1,

Ar ₁ and Ar ₂ are independently selected from the following groups:

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

Said X is selected from O and S;

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

The t is selected from an integer of 0 to 2;

Ar is selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C6-C60 fused polycyclic group, substituted or unsubstituted C2-C60 heteroaryl; or Ar is directly connected to L;

The _R1s are the same or different and are selected from one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C12 aryl, substituted or unsubstituted C6-C60 fused polycyclic group, and substituted or unsubstituted C2-C60 heteroaryl;

The m is an integer selected from 0 to 4;

The R ₀ are the same or different and are selected from one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C6-C60 fused polycyclic group, and substituted or unsubstituted C2-C60 heteroaryl;

The s is an integer selected from 0 to 3;

The L, L ₁ and L ₂ are independently selected from a single bond, a substituted or unsubstituted C6-C60 arylene group, a substituted or unsubstituted C6-C60 condensed polycyclic group, a substituted or unsubstituted C2-C60 heteroarylene group or a combination thereof.

2. The organic electroluminescent device according to claim 1, wherein Ring A in is selected from one of the groups shown below,

The G's are the same or different and are selected from CH or N;

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

The _n1 is selected from an integer of 0 to 4, the _n2 is selected from an integer of 0 to 6, the _n3 is selected from an integer of 0 to 8, and the _n4 is selected from an integer of 0 to 2.

3. The organic electroluminescent device according to claim 1, wherein Ring A in is selected from one of the groups shown below,

The _n1 is selected from an integer of 0 to 4, the _n2 is selected from an integer of 0 to 6, the _n3 is selected from an integer of 0 to 8, the _n4 is selected from an integer of 0 to 2, the _n5 is selected from an integer of 0 to 3, the _n6 is selected from an integer of 0 to 5, and the _n7 is selected from an integer of 0 to 7.

4. The organic electroluminescent device according to claim 1, wherein L is selected from a single bond, one of the following groups, or a combination thereof:

Each of R ₂ and R ₃ is the same or different and is selected from one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 fused polycyclic group, substituted or unsubstituted C2-C30 heteroaryl, or two adjacent R ₂ and R ₃ are bonded to each other to form a substituted or unsubstituted ring;

The Y is selected from O, S, C(R _y ) ₂ or N(R _y ), the R _{y s} are the same or different and are selected from one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 fused polycyclic group, substituted or unsubstituted C2-C30 heteroaryl, or two adjacent R _{y s} are bonded to each other to form a substituted or unsubstituted ring;

The E's are the same or different and are selected from CH or N;

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

The k and f are selected from integers of 0 to 4, and the e is selected from integers of 0 to 7;

When e is 2 or more, each unit in the brackets is the same or different.

5. The organic electroluminescent device according to claim 1, wherein _L1 and _L2 are independently selected from a single bond or a group as shown below:

The F's are the same or different and are selected from CH or N;

The _R4s are the same or different and are selected from one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 fused polycyclic group, substituted or unsubstituted C2-C30 heteroaryl, or two adjacent _R4s are bonded to each other to form a substituted or unsubstituted ring;

The s is selected from an integer of 0 to 4, and the h is selected from an integer of 0 to 4;

When h is 2 or more, each unit in the brackets is the same or different.

6. The organic electroluminescent device according to claim 1, wherein the carbazole compound of Formula 1 is selected from at least one of the following structures:

7 . The organic electroluminescent device according to claim 1 , wherein the host material satisfies the following condition: 2.6 eV ≤ energy gap (Eg) ≤ 3.0 eV.

8. The organic electroluminescent device according to claim 1, characterized in that the organic electroluminescent device further comprises a hole transport region, wherein the hole transport region is located between the anode and the light-emitting layer, and the hole transport region contains the star-shaped compound of formula 2,

Ar ₁₀ to Ar ₆₀ are independently selected from a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C6-C60 fused polycyclic group, or a substituted or unsubstituted C2-C60 heteroaryl group;

The L ₁₀ to L ₆₀ are independently selected from a single bond, a substituted or unsubstituted C6-C60 arylene group, a substituted or unsubstituted C6-C60 fused polycyclic group, a substituted or unsubstituted C2-C60 heteroarylene group, or a combination thereof;

The _R10 are the same or different and are selected from one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C6-C20 fused polycyclic group, and substituted or unsubstituted C2-C20 heteroaryl;

The a is selected from integers of 0-3.

9. The organic electroluminescent device according to claim 8, wherein Ar ₁₀ to Ar ₆₀ are independently selected from one of the following groups:

The _b1 is selected from an integer of 0 to 5, and the _b2 is selected from an integer of 0 to 4;

Each of R ₅ and R ₅₀ is the same or different and is selected from one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 fused polycyclic group, and substituted or unsubstituted C2-C30 heteroaryl, or two adjacent R ₅ and R ₅₀ are bonded to each other to form a substituted or unsubstituted ring;

The Q is selected from C(R _q ) ₂ , O, S or N(R _q ), and the R _{q s} are the same or different and are selected from one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 fused polycyclic group, substituted or unsubstituted C2-C30 heteroaryl, or two adjacent R _{q s} are bonded to each other to form a substituted or unsubstituted ring.

10. The organic electroluminescent device according to claim 8, wherein the star-shaped compound of formula 2 is selected from at least one of the following structures: