Carbazole compound and organic electroluminescent device thereof

Abstract

The invention relates to the technical field of organic electroluminescent materials, in particular to a carbazole compound and an organic electroluminescent device thereof. The carbazole compound provided by the invention has a relatively high hole transport rate, and when the carbazole compound is applied to a hole transport region of the organic electroluminescent device, the luminous efficiency of the organic electroluminescent device is improved, and the service life of the organic electroluminescent device is prolonged; moreover, the carbazole compound provided by the invention has a relatively large conjugate plane, can adjust carrier transport balance in a luminescent layer, broaden a carrier recombination region and improve the exciton recombination rate, and can improve the luminescent efficiency of the organic electroluminescent device and improve the efficiency roll-off when being applied to the luminescent layer of the organic electroluminescent device. And the preparation method has good application effect and industrialization prospect, and can be applied to various fields such as display, illumination, business, medicine and the like.

Description

Technical Field

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

[0002] Organic Light-Emitting Diode (OLED), as a device that converts electrical energy into light energy, can achieve high-resolution and full-color display. It has the advantages of fast response speed, rich colors, and large visualization angle. It has great application prospects in the fields of display and efficient lighting.

[0003] OLED is an electroluminescent device based on organic materials. Its basic structure is similar to a sandwich, consisting of two electrodes and multiple organic layers sandwiched between or outside the electrodes. According to their functions, the organic layers can be divided into electron injection layer, electron transport layer, hole blocking layer, light-emitting layer, electron blocking layer, hole transport layer, hole injection layer and covering layer. After applying voltage to both ends of the device, under the action of the external electric field, holes and electrons are injected into the organic material respectively, meet and recombine in the organic layer to form excitons, release energy, and transfer energy to the organic material molecules, so that they transition from the ground state energy level to the excited state. Since the excited state is very unstable, the excited molecules undergo radiation transition from the excited state to the ground state, and energy is generated in the form of light. Although OLED has made great achievements after decades of research and development, there are still many problems, such as the hole transport layer has a low hole mobility and HOMO value, and cannot effectively recombine with electrons; the stability and durability of the covering layer material are insufficient, and the light extraction rate is low, which affects the luminous efficiency of the device; the luminous efficiency of the luminous layer material is low, etc. These factors lead to low luminous efficiency of the device and shortened life. Therefore, it is urgent to develop OLED materials with higher performance and greater stability to further promote the development of OLED.

[0004] In recent years, in order to further improve the luminous efficiency and service life of organic electroluminescent devices, stacked organic electroluminescent devices have attracted more and more attention from academia and industry due to their excellent current efficiency, luminous brightness and service life. In stacked organic electroluminescent devices, multiple light-emitting units are connected by a charge generation layer, which plays a very important role. Therefore, selecting, designing and preparing suitable charge generation layer materials are the key to improving the performance of stacked devices. Summary of the invention

[0005] The object of the present invention is to provide a carbazole compound and an organic electroluminescent device thereof. When the carbazole compound provided by the present invention is applied to the hole transport region, the light-emitting layer, the charge generation layer or the covering layer of the organic electroluminescent device, an organic electroluminescent device with high efficiency and long life can be developed, thereby solving the problems of low luminous efficiency and short service life of the organic electroluminescent device in the prior art.

[0006] Specifically, the present invention provides a carbazole compound having the general formula shown in Structural Formula 1,

[0007]

[0008] Wherein, the Ar 1 Any one selected from the following groups or their combinations:

[0009]

[0010] The v are identically or differently selected from C(R 3 ) or a N atom, and v at the bonding site is selected from C;

[0011] The ring A is selected from 3 Substituted or unsubstituted: any one of a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a pyridine ring, a pyrimidine ring, a pyrazine ring, a pyridazine ring, a triazine ring, a quinoline ring, an isoquinoline ring, a quinazoline ring, a quinoxaline ring, a phenanthroline ring, and a pyrananthracene ring;

[0012] The ring B is selected from R 3 Substituted or unsubstituted: any one of benzene ring, naphthalene ring, anthracene ring, and phenanthrene ring;

[0013] The ring D is selected from R 3 Substituted or unsubstituted C3-C12 alicyclic group;

[0014] The R 3 is independently selected from any one of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C12 alicyclic and C6-C30 aromatic fused ring; said a 2 is independently selected from 0, 1, 2, 3 or 4; said a 3 is independently selected from 0, 1 or 2; said a 4 is independently selected from 0, 1, 2 or 3; said a 5 are independently selected from 0, 1, 2, 3, 4, 5, 6 or 7;

[0015] The Y is selected from an O atom, a S atom or a N(R 5 );

[0016] The R 5 Any one selected from hydrogen, deuterium, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 alicyclic group, substituted or unsubstituted C6-C30 aryl group, fused ring group of substituted or unsubstituted C3-C12 alicyclic ring and C6-C30 aromatic ring, substituted or unsubstituted C2-C30 heteroaryl group;

[0017] The Ar 2 A group selected from the group shown in formula 1-1;

[0018] The z are identically or differently selected from C(R 4 ) or N atoms, and at least one z is selected from N atoms, and the z at the bonding site is selected from C;

[0019] The R 4 Any one independently selected from hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C12 alicyclic group, substituted or unsubstituted C3-C12 alicyclic and C6-C30 aromatic ring fused ring group;

[0020] The R 1 , R 2 independently selected from any one of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C12 alicyclic group, fused ring group of substituted or unsubstituted C3-C12 alicyclic and C6-C30 aromatic ring, substituted or unsubstituted C2-C30 heteroaryl, or the two adjacent R 1 Between the two R 2 are connected to each other to form a substituted or unsubstituted ring, and the two adjacent R 1 Between the two R 2 They do not form a ring at the same time;

[0021] The x are selected from CH or N atoms the same or differently, and the x at the bonding site is selected from C;

[0022] The 1 is selected from 0, 1, 2, 3 or 4; said n 2 Selected from 0, 1, 2, 3 or 4;

[0023] The L is selected from the following groups:

[0024]

[0025] The t is identically or differently selected from C(R 6 ) or a N atom, t at the bonding site is selected from C;

[0026] The R 6 The same or different R is selected from any one of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 alicyclic, substituted or unsubstituted C6-C30 aryl, fused ring of substituted or unsubstituted C3-C12 alicyclic and C6-C30 aromatic ring, or two adjacent R 6 are connected to each other to form a substituted or unsubstituted benzene ring, naphthalene ring, anthracene ring, phenanthrene ring, furan ring, thiophene ring, indole ring, indenyl, oxazole ring, thiazole ring, imidazole ring, pyridine ring, pyrimidine ring, pyrazine ring, pyridazine ring, triazine ring, quinoline ring, isoquinoline ring, quinazoline ring, quinoxaline ring, azaphenanthren ring, azaanthracene ring, or any one of an alicyclic ring; the c 1 Select from 1, 2, 3, 4 or 5;

[0027] The L 1 Any one selected from a single bond, the following groups or their combinations:

[0028]

[0029] The u are identically or differently selected from C(R 7 ) or a N atom, and u at the bonding site is selected from C;

[0030] The ring G is selected from R 7 Substituted or unsubstituted: any one of a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a pyridine ring, a pyrimidine ring, a pyrazine ring, a pyridazine ring, a triazine ring, a quinoline ring, an isoquinoline ring, a quinazoline ring, a quinoxaline ring, a phenanthroline ring, and a pyrananthracene ring;

[0031] The ring E is selected from R 7 Substituted or unsubstituted: any one of benzene ring, naphthalene ring, anthracene ring, and phenanthrene ring;

[0032] The ring F is selected from R 7 Substituted or unsubstituted C3-C12 alicyclic group;

[0033] The R 7 The same or different selected from any one of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C12 alicyclic group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C3-C12 alicyclic and C6-C30 aromatic ring fused ring group; the d 1 Independently selected from 1, 2, 3, 4 or 5; said d 2 is independently selected from 0, 1, 2, 3 or 4; said d 3is independently selected from 0, 1, 2 or 3; said d 4 is independently selected from 0, 1 or 2; said d 5 Independently selected from 0, 1, 2, 3, 4, 5 or 6;

[0034] The Y 2 is selected from an O atom, a S atom or a N(R 8 );

[0035] The R 8 Any one selected from hydrogen, deuterium, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C12 alicyclic group, substituted or unsubstituted C6-C30 aryl group, fused ring group of substituted or unsubstituted C3-C12 alicyclic ring and C6-C30 aromatic ring, substituted or unsubstituted C2-C30 heteroaryl group;

[0036] The L 2 Any one selected from a single bond, the following groups or their combinations:

[0037]

[0038] The w are identically or differently selected from C(R 10 ) or a N atom, and w at the bonding site is selected from C;

[0039] The ring J is selected from R 10 Substituted or unsubstituted: any one of a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a pyridine ring, a pyrimidine ring, a pyrazine ring, a pyridazine ring, a triazine ring, a quinoline ring, an isoquinoline ring, a quinazoline ring, a quinoxaline ring, a phenanthroline ring, and a pyrananthracene ring;

[0040] The ring H is selected from R 10 Substituted or unsubstituted: any one of benzene ring, naphthalene ring, anthracene ring, and phenanthrene ring;

[0041] The ring K is selected from R 10 Substituted or unsubstituted C3-C12 alicyclic group;

[0042] The complaint Y 3 is selected from an O atom, a S atom or a N(R 9 );

[0043] The R 9 Any one selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C12 alicyclic group, substituted or unsubstituted C6-C30 aryl group, fused ring group of substituted or unsubstituted C3-C12 alicyclic ring and C6-C30 aromatic ring, substituted or unsubstituted C2-C30 heteroaryl group, etc., which are the same or different;

[0044] The R 10 The same or different ones are selected from any one of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 alicyclic group, substituted or unsubstituted C6-C30 aryl group, fused ring group of substituted or unsubstituted C3-C12 alicyclic ring and C6-C30 aromatic ring, substituted or unsubstituted C2-C30 heteroaryl group; the e 1 Independently selected from 1, 2, 3, 4 or 5; said e 2 is independently selected from 0, 1, 2, 3 or 4; said e 3 is independently selected from 0, 1, 2 or 3; said e 4 independently selected from 0, 1 or 2;

[0045] The R 11 , R 12 Any one independently selected from hydrogen, deuterium, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 alicyclic group, substituted or unsubstituted C6-C30 aryl group, fused ring group of substituted or unsubstituted C3-C12 alicyclic ring and C6-C30 aromatic ring, substituted or unsubstituted C2-C30 heteroaryl group.

[0046] The present invention also provides an organic electroluminescent device, comprising an anode, an organic layer and a cathode, wherein the organic layer is located between the anode and the cathode or outside one or more electrodes of the anode and the cathode, and the organic layer contains the carbazole compound of the present invention.

[0047] Beneficial effects: The carbazole compounds provided by the present invention have a high hole transfer rate. When applied to the hole transfer region of an organic electroluminescent device, the luminous efficiency and service life of the organic electroluminescent device are improved; and the carbazole compounds provided by the present invention have a large conjugated plane, which can adjust the carrier transfer balance in the light-emitting layer, broaden the carrier recombination region, and increase the exciton recombination rate. When applied to the light-emitting layer of an organic electroluminescent device, the luminous efficiency of the organic electroluminescent device can be improved, the efficiency roll-off can be improved, and the service life of the device can be increased. DETAILED DESCRIPTION

[0048] The present invention is further explained below in conjunction with specific embodiments. It should be understood that these embodiments are only used to illustrate the present invention and are not used to limit the scope of the present invention. After reading the present invention, various equivalent forms of modifications to the present invention by those skilled in the art all fall within the scope of protection required by this application.

[0049] In the compounds of the present invention, any atom not designated as a particular isotope includes any stable isotope of that atom, and includes atoms in both their natural isotopic abundance and unnatural abundance. Taking hydrogen as an example, all naturally occurring compounds contain about 0.0156 atomic % deuterium per hydrogen atom.

[0050] In the present invention, the use of "H" and "hydrogen" means that the hydrogen atoms in the chemical structure contain no more than natural abundance of deuterium atoms or tritium atoms, for example, no more than 0.0156 atomic % of deuterium. "D" and "deuterium" mean that the abundance of deuterium content is above natural abundance, for example, any value exceeding 0.1 atomic %, exceeding 1 atomic %, exceeding 10 atomic %, for example, about 95 atomic % of which is deuterium. "T" and "tritium" mean that the abundance of tritium content is above natural abundance, for example, any value exceeding 0.1 atomic %, exceeding 1 atomic %, exceeding 10 atomic %, for example, about 95% of which is tritium. In the present invention, the omitted hydrogen represents "H" or "hydrogen".

[0051] Examples of the halogen according to the present invention may include a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom.

[0052] The "C1-C15" in the "substituted or unsubstituted C1-C15 alkyl" of the present invention refers to the number of carbon atoms in the unsubstituted "alkyl", excluding the number of carbon atoms in the substituent. The "C6-C30" in the "substituted or unsubstituted C6-C30 aryl" refers to the number of carbon atoms in the unsubstituted "aryl", excluding the number of carbon atoms in the substituent. And so on.

[0053] The alkyl group described in the present invention refers to a monovalent group formed by missing a hydrogen atom from an alkane molecule. The number of carbon atoms of the alkyl group is C1 to C15, preferably C1 to C10. Examples of the alkyl group include, but are not limited to, the following groups: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, etc.

[0054] The chain alkyl group with more than three carbon atoms described in the present invention includes its isomers, for example, propyl group includes n-propyl group and isopropyl group, butyl group includes n-butyl group, sec-butyl group, isobutyl group and tert-butyl group, and so on.

[0055] The aryl group described in the present invention refers to a monovalent group formed by removing a hydrogen atom from the aromatic carbon nucleus of an aromatic hydrocarbon molecule. The aryl group includes a monocyclic aryl group, a polycyclic aryl group, and a condensed ring aryl group. The number of carbon atoms of the aryl group is C6 to C30, preferably C6 to C20, further preferably C6 to C15, and further preferably C6 to C12. Examples of the aryl group include, but are not limited to, the following groups, phenyl, biphenyl, terphenyl, quaterphenyl, pentaphenyl, naphthyl, indenyl, dihydroindenyl, dihydronaphthyl, tetrahydronaphthyl, phenanthryl, triphenylene, anthracenyl, pyrenyl, fluorenyl, spirobifluorenyl, spiroanthracenyl, benzofluorenyl, benzospirobifluorenyl, etc.

[0056] The alicyclic group described in the present invention refers to an aliphatic hydrocarbon having 3 to 12 carbon atoms, which may be completely unsaturated or partially unsaturated. For example, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopentene, cyclohexene, cycloheptene, etc., but not limited thereto. Multiple monocyclic hydrocarbons can also be connected in a variety of ways: two rings in a molecule can share a carbon atom to form a spirocycle; two carbon atoms on the ring can be connected by a carbon bridge to form a bridged ring; several rings can also be connected to each other to form a cage structure, such as adamantane, norbornane, camphane, etc., but not limited thereto.

[0057] The fused ring group of an alicyclic ring and an aromatic ring of the present invention refers to a general term for a monovalent group after an alicyclic ring and an aromatic ring are fused together and a hydrogen atom is removed. Examples of the fused ring group of an alicyclic ring and an aromatic ring may include dihydroindenyl, indenyl, tetrahydronaphthyl, dihydronaphthyl, benzocyclopropane, benzocyclobutane, benzocyclobutenyl, benzocycloheptane, benzocycloheptenyl, etc., but are not limited thereto. The carbon number of the alicyclic ring is C3 to C12, preferably C3 to C10. The carbon number of the aromatic ring is C6 to C30, preferably C6 to C18, and more preferably C6 to C12.

[0058] The heteroaryl group described in the present invention refers to a monovalent group in which at least one aromatic carbon atom in the aromatic group is replaced by a heteroatom. The number of carbon atoms of the heteroaryl group is C2 to C30, preferably C2 to C15, and preferably C2 to C10. The heteroatom includes, but is not limited to, the following atoms, O, S, N, Si, B, P, etc. The heteroaryl group includes a monocyclic heteroaryl group and a condensed ring heteroaryl group. Examples of the heteroaryl group include, but are not limited to, the following groups, pyridyl, pyrimidyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, furanyl, benzofuranyl, dibenzofuranyl, benzodibenzofuranyl, thienyl, benzothienyl, dibenzothienyl, benzodibenzothienyl, carbazolyl, etc.

[0059] The arylene group described in the present invention refers to a divalent group formed by removing two hydrogen atoms from the aromatic carbon nucleus in an aromatic hydrocarbon molecule. The number of carbon atoms of the arylene group is C6 to C30, preferably C6 to C20, and more preferably C6 to C10. The arylene group includes a monocyclic arylene group, a polycyclic arylene group, a condensed ring arylene group, or a combination thereof. Examples of the arylene group include, but are not limited to, the following groups, phenylene, biphenylene, terphenylene, naphthylene, anthracene, phenanthrenyl, triphenylene, perylene, pyrenyl, indenyl, fluorenyl, benzofluorenyl, dibenzofluorenyl, spirobifluorenyl, benzospirobifluorenyl, etc.

[0060] The sub-fused ring group of the alicyclic ring and the aromatic ring described in the present invention refers to the general term for the divalent group left after the alicyclic ring and the aromatic ring are fused together and two hydrogen atoms are removed. Examples of the sub-fused ring of the alicyclic ring and the aromatic ring may include indenylene, indenylene, tetrahydronaphthylene, dihydronaphthylene, benzocyclopropanediylene, benzocyclobutanediylene, benzocyclobutenylene, naphthocyclopentanediylene, etc., but are not limited thereto. The carbon number of the alicyclic ring is C3 to C15, preferably C3 to C10. The carbon number of the aromatic ring is C6 to C30, preferably C6 to C18.

[0061] The heteroarylene group described in the present invention refers to a divalent group in which at least one carbon atom in the arylene group is replaced by a heteroatom. The number of carbon atoms of the heteroarylene group is C2 to C30, preferably C2 to C20, and preferably C2 to C10. The heteroatoms include, but are not limited to, the atoms shown below, O, S, N, Si, B, P, etc. The heteroarylene group includes a monocyclic heteroarylene group, a polycyclic heteroarylene group, a condensed ring heteroarylene group, or a combination thereof. Examples of the heteroarylene group include, but are not limited to, the groups described below, pyridylene, pyrimidylene, quinolylene, isoquinolylene, furylene, benzofuranylene, dibenzofuranylene, benzodibenzofuranylene, thienylene, benzothienylene, dibenzothienylene, benzodibenzothienylene, etc.

[0062] The term "substituted or unsubstituted" as used herein means not substituted or substituted by one or more substituents selected from the group consisting of a deuterium atom, a halogen atom, an amino group, a cyano group, a nitro group, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C3-C30 cycloalkenyl group, a substituted or unsubstituted C3-C30 heterocycloalkyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C6-C60 aryloxy group, a substituted or unsubstituted C2-C60 heteroaryl group, or a substituted or unsubstituted silyl group, preferably a deuterium atom, a halogen atom, a cyano group, a nitro group, a C1-C12 alkyl group, a C3-C30 cycloalkyl group, a substituted or unsubstituted C3-C30 cycloalkenyl group, a substituted or unsubstituted C3-C30 heterocycloalkyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C6-C60 aryloxy group, a substituted or unsubstituted C2-C60 heteroaryl group, or a substituted or unsubstituted silyl group. C12 cycloalkyl, C3-C12 cycloalkenyl, C3-C12 heterocycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, substituted or unsubstituted silyl, when substituted by multiple substituents, the multiple substituents are the same or different from each other; preferably, it means not substituted or substituted by one or more substituents selected from the group consisting of: deuterium atom, fluorine atom, cyano group, methyl, trifluoromethyl, deuterated methyl, ethyl, deuterated ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, deuterated tert-butyl, cyclopropane, methyl substituted cyclopropane, ethyl substituted cyclopropane, deuterated cyclopropane, cyclobutane, methyl substituted cyclopropane butanyl, ethyl-substituted cyclobutanyl, deuterated cyclobutanyl, cyclopentanyl, methyl-substituted cyclopentanyl, ethyl-substituted cyclopentanyl, deuterated cyclopentanyl, cyclohexanyl, methyl-substituted cyclohexanyl, ethyl-substituted cyclohexanyl, n-propyl-substituted cyclohexanyl, n-butyl-substituted cyclohexanyl, cyclohexane-substituted cyclohexanyl, deuterated cyclohexanyl, cycloheptanyl, cyclopentenyl, methyl-substituted cyclopentenyl, ethyl-substituted cyclopentenyl, cyclohexenyl, cycloheptenyl, adamantyl, methyl-substituted adamantyl, ethyl-substituted adamantyl, deuterated adamantyl, norbornanyl, methyl-substituted norbornanyl, ethyl-substituted norbornanyl, deuterated norbornanyl, tetrahydropyrrole The invention also includes but is not limited to: 1,2-dimethyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1

[0063] In the present invention, when a substituent or a bond at a connection site runs through two or more rings, it indicates that it can be connected to any of the two or more rings, specifically, it can be connected to any of the corresponding optional sites of the rings. For example, Can be expressed Can be expressed And so on.

[0064] In this specification, when the position of a substituent on a ring is not fixed, it means that it can be attached to any of the corresponding optional positions of the ring. For example, Can be expressed Can be expressed Can be expressed And so on.

[0065] In the present invention, "two adjacent groups can be connected to each other to form a substituted or unsubstituted ring" means that the adjacent groups are combined with each other and optionally aromatized to form a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocycle. The hydrocarbon ring can be an aliphatic hydrocarbon ring or an aromatic hydrocarbon ring. The heterocycle can include an aliphatic heterocycle or an aromatic heterocycle. The aliphatic hydrocarbon ring can be a saturated aliphatic hydrocarbon ring or an unsaturated aliphatic hydrocarbon ring, and the aliphatic heterocycle can be a saturated aliphatic heterocycle or an unsaturated aliphatic heterocycle. The hydrocarbon ring and the heterocycle can be monocyclic or polycyclic groups. In addition, the ring formed by the combination of adjacent groups can be connected to another ring to form a spiro structure. The following examples are shown:

[0066]

[0067] In the present invention, the ring formed by connection can be an aromatic ring system, an aliphatic ring system or a ring system formed by the fusion of the two. The ring formed by connection can be a three-membered ring, a four-membered ring, a five-membered ring, a six-membered ring, a spiro ring or a fused ring, such as benzene, naphthalene, indene, cyclopentene, cyclopentane, cyclopentane acene, cyclohexene, cyclohexane, cyclohexane acene, pyridine, quinoline, isoquinoline, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, phenanthrene or pyrene, but is not limited thereto.

[0068] The present invention provides a carbazole compound having the general formula shown in Structural Formula 1,

[0069]

[0070] Wherein, the Ar 1 Any one selected from the following groups or combinations thereof:

[0071]

[0072] The v are identically or differently selected from C(R 3) or a N atom, and v at the bonding site is selected from C;

[0073] The ring A is selected from 3 Substituted or unsubstituted: any one of a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a pyridine ring, a pyrimidine ring, a pyrazine ring, a pyridazine ring, a triazine ring, a quinoline ring, an isoquinoline ring, a quinazoline ring, a quinoxaline ring, a phenanthroline ring, and a pyrananthracene ring;

[0074] The ring B is selected from R 3 Substituted or unsubstituted: any one of benzene ring, naphthalene ring, anthracene ring, and phenanthrene ring;

[0075] The ring D is selected from R 3 Substituted or unsubstituted C3-C12 alicyclic group;

[0076] The R 3 is independently selected from any one of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C12 alicyclic and C6-C30 aromatic fused ring; said a 2 is independently selected from 0, 1, 2, 3 or 4; said a 3 is independently selected from 0, 1 or 2; said a 4 is independently selected from 0, 1, 2 or 3; said a 5 are independently selected from 0, 1, 2, 3, 4, 5, 6 or 7;

[0077] The Y is selected from an O atom, a S atom or a N(R 5 );

[0078] The R 5 Any one selected from hydrogen, deuterium, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 alicyclic group, substituted or unsubstituted C6-C30 aryl group, fused ring group of substituted or unsubstituted C3-C12 alicyclic ring and C6-C30 aromatic ring, substituted or unsubstituted C2-C30 heteroaryl group;

[0079] The Ar 2 A group selected from the group shown in formula 1-1;

[0080] The z are identically or differently selected from C(R 4 ) or N atoms, and at least one z is selected from N atoms, and the z at the bonding site is selected from C;

[0081] The R 4Any one independently selected from hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C12 alicyclic group, substituted or unsubstituted C3-C12 alicyclic and C6-C30 aromatic ring fused ring group;

[0082] The R 1 , R 2 independently selected from any one of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C12 alicyclic group, fused ring group of substituted or unsubstituted C3-C12 alicyclic and C6-C30 aromatic ring, substituted or unsubstituted C2-C30 heteroaryl, or the two adjacent R 1 Between the two R 2 are connected to each other to form a substituted or unsubstituted ring, and the two adjacent R 1 Between the two R 2 They do not form a ring at the same time;

[0083] The x are selected from CH or N atoms the same or differently, and the x at the bonding site is selected from C;

[0084] The 1 is selected from 0, 1, 2, 3 or 4; said n 2 Selected from 0, 1, 2, 3 or 4;

[0085] The L is selected from the following groups:

[0086]

[0087] The t is identically or differently selected from C(R 6 ) or a N atom, t at the bonding site is selected from C;

[0088] The R 6 The same or different R is selected from any one of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 alicyclic, substituted or unsubstituted C6-C30 aryl, fused ring of substituted or unsubstituted C3-C12 alicyclic and C6-C30 aromatic ring, or two adjacent R 6 are connected to each other to form a substituted or unsubstituted benzene ring, naphthalene ring, anthracene ring, phenanthrene ring, furan ring, thiophene ring, indole ring, indenyl, oxazole ring, thiazole ring, imidazole ring, pyridine ring, pyrimidine ring, pyrazine ring, pyridazine ring, triazine ring, quinoline ring, isoquinoline ring, quinazoline ring, quinoxaline ring, azaphenanthren ring, azaanthracene ring, or any one of an alicyclic ring; the c 1 Select from 1, 2, 3, 4 or 5;

[0089] The L 1 Any one selected from a single bond, the following groups or their combinations:

[0090]

[0091] The u are identically or differently selected from C(R 7 ) or a N atom, and u at the bonding site is selected from C;

[0092] The ring G is selected from R 7 Substituted or unsubstituted: any one of a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a pyridine ring, a pyrimidine ring, a pyrazine ring, a pyridazine ring, a triazine ring, a quinoline ring, an isoquinoline ring, a quinazoline ring, a quinoxaline ring, a phenanthroline ring, and a pyrananthracene ring;

[0093] The ring E is selected from R 7 Substituted or unsubstituted: any one of benzene ring, naphthalene ring, anthracene ring, and phenanthrene ring;

[0094] The ring F is selected from R 7 Substituted or unsubstituted C3-C12 alicyclic group;

[0095] The R 7 The same or different selected from any one of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C12 alicyclic group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C3-C12 alicyclic and C6-C30 aromatic ring fused ring group; the d 1 Independently selected from 1, 2, 3, 4 or 5; said d 2 is independently selected from 0, 1, 2, 3 or 4; said d 3 is independently selected from 0, 1, 2 or 3; said d 4 is independently selected from 0, 1 or 2; said d 5 Independently selected from 0, 1, 2, 3, 4, 5 or 6;

[0096] The Y 2 is selected from an O atom, a S atom or a N(R 8 );

[0097] The R 8 Any one selected from hydrogen, deuterium, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C12 alicyclic group, substituted or unsubstituted C6-C30 aryl group, fused ring group of substituted or unsubstituted C3-C12 alicyclic ring and C6-C30 aromatic ring, substituted or unsubstituted C2-C30 heteroaryl group;

[0098] The L2 Any one selected from a single bond, the following groups or their combinations:

[0099]

[0100] The w are identically or differently selected from C(R 10 ) or a N atom, and w at the bonding site is selected from C;

[0101] The ring J is selected from R 10 Substituted or unsubstituted: any one of a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a pyridine ring, a pyrimidine ring, a pyrazine ring, a pyridazine ring, a triazine ring, a quinoline ring, an isoquinoline ring, a quinazoline ring, a quinoxaline ring, a phenanthroline ring, and a pyrananthracene ring;

[0102] The ring H is selected from R 10 Substituted or unsubstituted: any one of benzene ring, naphthalene ring, anthracene ring, and phenanthrene ring;

[0103] The ring K is selected from R 10 Substituted or unsubstituted C3-C12 alicyclic group;

[0104] The complaint Y 3 is selected from an O atom, a S atom or a N(R 9 );

[0105] The R 9 Any one selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C12 alicyclic group, substituted or unsubstituted C6-C30 aryl group, fused ring group of substituted or unsubstituted C3-C12 alicyclic ring and C6-C30 aromatic ring, substituted or unsubstituted C2-C30 heteroaryl group, etc., which are the same or different;

[0106] The R 10 The same or different ones are selected from any one of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 alicyclic group, substituted or unsubstituted C6-C30 aryl group, fused ring group of substituted or unsubstituted C3-C12 alicyclic ring and C6-C30 aromatic ring, substituted or unsubstituted C2-C30 heteroaryl group; the e 1 Independently selected from 1, 2, 3, 4 or 5; said e 2 is independently selected from 0, 1, 2, 3 or 4; said e 3 is independently selected from 0, 1, 2 or 3; said e 4 independently selected from 0, 1 or 2;

[0107] The R 11 , R 12Any one independently selected from hydrogen, deuterium, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 alicyclic group, substituted or unsubstituted C6-C30 aryl group, fused ring group of substituted or unsubstituted C3-C12 alicyclic ring and C6-C30 aromatic ring, substituted or unsubstituted C2-C30 heteroaryl group.

[0108] Preferably, the Ar 2 Any one selected from the following groups:

[0109]

[0110]

[0111] The R 4 independently selected from hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted following groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, dihydroindenyl, indenyl, tetrahydronaphthyl, dihydronaphthyl, any one or more of silyl, in the case of being substituted by multiple substituents, the multiple substituents are the same or different; said b is independently selected from 0, 1, 2, 3, 4, 5 or 6; said b 1 is independently selected from 0, 1, 2, 3, 4 or 5; said b 2 is independently selected from 0, 1, 2, 3 or 4; said b 3 is independently selected from 0, 1, 2 or 3; said b 4 Independently selected from 0, 1 or 2.

[0112] Preferably, the Ar 1 Any one selected from the following groups or combinations thereof:

[0113]

[0114] The R 3 , R 15 The same or different selected from hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted following groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, octyl, phenyl, biphenyl, naphthyl, dihydroindenyl, indenyl, tetrahydronaphthyl, dihydronaphthyl, anthracenyl, phenanthrenyl, triphenylene, silyl any one or more, in the case of being substituted by multiple substituents, the multiple substituents are the same or different from each other;

[0115] The R 5any one selected from hydrogen, deuterium, substituted or unsubstituted groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthryl, triphenylene, indenyl, tetrahydronaphthyl, benzocyclopropyl, benzocyclobutane, benzocyclopentyl, benzocyclohexyl, silyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, benzofuranyl, benzothiophenyl, indolyl, dibenzofuranyl, dibenzothiophenyl, benzoxazolyl, benzothiazolyl, benzimidazolyl;

[0116] The a 1 is independently selected from 0, 1, 2, 3, 4 or 5; said a 2 is independently selected from 0, 1, 2, 3 or 4; said a 3 is independently selected from 0, 1 or 2; said a 4 is independently selected from 0, 1, 2 or 3; said a 5 is independently selected from 0, 1, 2, 3, 4, 5, 6 or 7; said a 6 is independently selected from 0, 1, 2, 3, 4, 5 or 6; said a 7 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; 8 Independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10.

[0117] Preferably, L is selected from any one of the following groups or combinations thereof:

[0118]

[0119]

[0120] The R 6 , R 13 The same or different selected from hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, adamantyl, norbornane, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, indenyl, tetrahydronaphthyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, silyl or any combination thereof;

[0121] The R 11any one selected from hydrogen, deuterium, substituted or unsubstituted groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthryl, triphenylene, indenyl, tetrahydronaphthyl, benzocyclopropyl, benzocyclobutane, benzocyclopentyl, benzocyclohexyl, silyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, benzofuranyl, benzothiophenyl, indolyl, dibenzofuranyl, dibenzothiophenyl, benzoxazolyl, benzothiazolyl, benzimidazolyl;

[0122] The R 16 , R 17 Any one independently selected from hydrogen, deuterium, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 alicyclic group, substituted or unsubstituted C6-C30 aryl group, fused ring group of substituted or unsubstituted C3-C12 alicyclic ring and C6-C30 aromatic ring, substituted or unsubstituted C2-C30 heteroaryl group;

[0123] The c 1 is selected from 0, 1, 2, 3 or 4; said c 2 is selected from 0, 1, 2 or 3; said c 3 is selected from 0, 1 or 2; said c 4 is selected from 0, 1, 2, 3, 4, 5 or 6; said c 5 Selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8.

[0124] Further preferably, the L is selected from any one of the following groups or combinations thereof:

[0125]

[0126]

[0127] Preferably, the L 1 Any one selected from a single bond, the following groups or their combinations:

[0128]

[0129]

[0130] The R 7 , R 14the same or different selected from hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, adamantyl, norbornane, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, indenyl, tetrahydronaphthyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, silyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl or any combination thereof;

[0131] The R 8 any one selected from hydrogen, deuterium, substituted or unsubstituted groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthryl, triphenylene, indenyl, tetrahydronaphthyl, benzocyclopropyl, benzocyclobutane, benzocyclopentyl, benzocyclohexyl, silyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, benzofuranyl, benzothiophenyl, indolyl, dibenzofuranyl, dibenzothiophenyl, benzoxazolyl, benzothiazolyl, benzimidazolyl;

[0132] The d 1 is independently selected from 0, 1, 2, 3 or 4; said d 2 is independently selected from 0, 1, 2 or 3; said d 3 is independently selected from 0, 1 or 2; said d 4 is independently selected from 0, 1, 2, 3, 4, 5 or 6; said d 5 Independently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8.

[0133] Preferably, the L 2 Any one selected from a single bond, the following groups or their combinations:

[0134]

[0135]

[0136] The R 10 , R 15the same or different selected from hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, adamantyl, norbornane, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, indenyl, tetrahydronaphthyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, silyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl or any combination thereof;

[0137] The R 9 any one selected from hydrogen, deuterium, substituted or unsubstituted groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthryl, triphenylene, indenyl, tetrahydronaphthyl, benzocyclopropyl, benzocyclobutane, benzocyclopentyl, benzocyclohexyl, silyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, benzofuranyl, benzothiophenyl, indolyl, dibenzofuranyl, dibenzothiophenyl, benzoxazolyl, benzothiazolyl, benzimidazolyl;

[0138] The R 11 , R 12 the same or different selected from hydrogen, deuterium, substituted or unsubstituted groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthryl, triphenylene, indenyl, tetrahydronaphthyl, benzocyclopropyl, benzocyclobutane, benzocyclopentyl, benzocyclohexyl, silyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, benzofuranyl, benzothiophenyl, indolyl, dibenzofuranyl, dibenzothiophenyl, benzoxazolyl, benzothiazolyl, benzimidazolyl;

[0139] The 1 is independently selected from 0, 1, 2, 3 or 4; said e 2 is independently selected from 0, 1, 2 or 3; said e 3 is independently selected from 0, 1 or 2; said e 4 is independently selected from 0, 1, 2, 3, 4, 5 or 6; said e 5 Independently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8.

[0140] Preferably, the Any one selected from the following groups:

[0141]

[0142] The R 1 , R 2 independently selected from hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, indenyl, tetrahydronaphthyl, benzocyclopropyl, benzocyclobutane, benzocyclopentyl, benzocyclohexyl, silyl, pyridyl, pyrimidyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, carbazolyl or any combination thereof;

[0143] The 1 is selected from 0, 1, 2, 3 or 4; said n 2 is selected from 0, 1, 2, 3 or 4; said n 3 is selected from 0, 1, 2 or 3; said n 4 is selected from 0, 1 or 2; said n 5 is selected from 0, 1, 2, 3, 4, 5 or 6; said n 6 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; said n 7 is selected from 0, 1, 2, 3, 4 or 5; said n 8 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10.

[0144] Most preferably, the carbazole compound represented by Formula 1 is selected from any one of the chemical structures shown below:

[0145]

[0146]

[0147]

[0148]

[0149]

[0150]

[0151]

[0152]

[0153]

[0154]

[0155]

[0156]

[0157]

[0158]

[0159]

[0160]

[0161]

[0162]

[0163]

[0164]

[0165]

[0166]

[0167]

[0168]

[0169]

[0170]

[0171]

[0172]

[0173]

[0174]

[0175] Some specific chemical structures of the carbazole compounds of structural formula 1 of the present invention are listed above, but the present invention is not limited to these listed chemical structures, and all carbazole compounds based on structural formula 1 and having substituents as defined above should be included.

[0176] Furthermore, the present invention also provides an organic electroluminescent device, comprising an anode, an organic layer and a cathode, wherein the organic layer is located between the anode and the cathode or outside one or more electrodes of the anode and the cathode, and the organic layer contains the carbazole compound represented by Formula 1 of the present invention.

[0177] Preferably, the organic layer is located between the anode and the cathode, and the organic layer includes at least one of a hole transport region, a light emitting layer, and an electron transport region, and at least one of the hole transport region or the light emitting layer contains the carbazole compound represented by Formula 1 of the present invention.

[0178] Preferably, the organic layer is located between the anode and the cathode, the organic layer includes at least one layer of a hole transport region, two or more light-emitting layers, a charge generation layer, and an electron transport region, the charge generation layer is located between two light-emitting layers, and the charge generation layer contains the carbazole compound shown in Formula 1 of the present invention.

[0179] Preferably, the organic layer comprises a hole transport region, a light emitting layer, an electron transport region and a covering layer, and the covering layer contains the carbazole compound represented by Formula 1 of the present invention.

[0180] Preferably, the hole transport region comprises at least one of a hole injection layer, a hole transport layer, and an electron blocking layer, the hole injection layer is located between the anode and the cathode, the hole transport layer is located between the hole injection layer and the cathode, the electron blocking layer is located between the hole transport layer and the cathode, and at least one of the hole injection layer, the hole transport layer, and the electron blocking layer contains the carbazole compound represented by Formula 1 of the present invention.

[0181] Preferably, the hole transport region comprises a hole transport layer, and the hole transport layer contains the carbazole compound represented by Formula 1 of the present invention.

[0182] Preferably, the hole transport layer comprises a first hole transport layer and a second hole transport layer, the second hole transport layer is located between the first hole transport layer and the cathode, and the first hole transport layer contains the carbazole compound represented by Formula 1 of the present invention.

[0183] Preferably, the hole transport layer comprises a first hole transport layer and a second hole transport layer, the second hole transport layer is located between the first hole transport layer and the cathode, and the second hole transport layer contains the carbazole compound represented by Formula 1 of the present invention.

[0184] Preferably, the hole transport layer comprises a first hole transport layer and a second hole transport layer, the second hole transport layer is located between the first hole transport layer and the cathode, and the first hole transport layer and the second hole transport layer contain the carbazole compound represented by Formula 1 of the present invention.

[0185] Preferably, the hole transport layer comprises a first hole transport layer, a second hole transport layer and a third hole transport layer, the second hole transport layer is located between the first hole transport layer and the cathode, the third hole transport layer is located between the second hole transport layer and the cathode, and at least one of the first hole transport layer, the second hole transport layer and the third hole transport layer contains the carbazole compound represented by Formula 1 of the present invention.

[0186] Preferably, the hole transport layer comprises a first hole transport layer, a second hole transport layer and a third hole transport layer, the second hole transport layer is located between the first hole transport layer and the cathode, the third hole transport layer is located between the second hole transport layer and the cathode, and the first hole transport layer contains the carbazole compound represented by Formula 1 of the present invention.

[0187] Preferably, the hole transport layer comprises a first hole transport layer, a second hole transport layer and a third hole transport layer, the second hole transport layer is located between the first hole transport layer and the cathode, the third hole transport layer is located between the second hole transport layer and the cathode, and the second hole transport layer contains the carbazole compound represented by Formula 1 of the present invention.

[0188] Preferably, the hole transport layer comprises a first hole transport layer, a second hole transport layer and a third hole transport layer, the second hole transport layer is located between the first hole transport layer and the cathode, the third hole transport layer is located between the second hole transport layer and the cathode, and the third hole transport layer contains the carbazole compound represented by Formula 1 of the present invention.

[0189] Preferably, the thickness of the hole transport layer is 30 nm to 200 nm.

[0190] Preferably, the thickness of the first hole transport layer is 30 nm to 200 nm, and the thickness of the second hole transport layer is 3 nm to 100 nm.

[0191] Preferably, the thickness of the first hole transport layer is 60 nm to 180 nm.

[0192] Further preferably, the thickness of the first hole transport layer is 80 nm to 140 nm.

[0193] More preferably, the thickness of the first hole transport layer is 100 nm to 120 nm.

[0194] Preferably, the second hole transport layer has a thickness of 5 nm to 90 nm.

[0195] Further preferably, the thickness of the second hole transport layer is 40nm to 80nm (red light); the thickness of the second hole transport layer is 20nm to 60nm (green light); and the thickness of the second hole transport layer is 5nm to 30nm (blue light).

[0196] More preferably, the thickness of the second hole transport layer is 50nm to 70nm (red light); the thickness of the second hole transport layer is 30nm to 50nm (green light); the thickness of the second hole transport layer is 5nm to 25nm (blue light).

[0197] Preferably, the thickness of the third hole transport layer is 5 nm to 150 nm.

[0198] More preferably, the thickness of the third hole transport layer is 10 nm to 100 nm.

[0199] Preferably, the organic electroluminescent device described in the present invention is a single-layer organic electroluminescent device or a stacked organic electroluminescent device. The single-layer organic electroluminescent device is an organic electroluminescent device containing one light-emitting unit, and the stacked organic electroluminescent device is an organic electroluminescent device formed by connecting N (N≥2) independent light-emitting units in series through a charge generation layer.

[0200] Preferably, the organic electroluminescent device of the present invention is a single-layer organic electroluminescent device, wherein an anode, one or more organic layers and a cathode are sequentially stacked on a substrate.

[0201] Preferably, the organic electroluminescent device described in the present invention is a stacked organic electroluminescent device, wherein a first light-emitting unit emitting light of a first color, an Nth light-emitting unit emitting light of an Nth color, and a charge generation layer for uniformly controlling the charge between the first light-emitting unit and the Nth light-emitting unit are formed between the anode and the cathode, and an n-type charge generation layer and a p-type charge generation layer are included between adjacent light-emitting units.

[0202] Preferably, the organic layer includes a hole transport region, two or more light-emitting layers, an electron transport region and a covering layer, and an n-type charge generation layer and a p-type charge generation layer are arranged in the middle of each light-emitting layer, and the p-type charge generation layer contains the carbazole compound shown in Formula 1 of the present invention.

[0203] Preferably, the p-type charge generation layer contains the carbazole compound represented by Formula 1 of the present invention, or the p-type charge generation layer can be formed by doping the carbazole compound represented by Formula 1 of the present invention with other materials.

[0204] The organic electroluminescent device of the present invention is usually formed on a substrate. The substrate may be any substrate that does not change when forming the electrode or the organic layer, for example, a substrate of glass, quartz, plastic, polymer film, silicon, etc. When the substrate is opaque, the electrode opposite thereto is preferably transparent or translucent.

[0205] The present invention has no particular limitation on the materials of the thin films in the organic electroluminescent device, and materials known in the art can be used. The organic layer of the organic electroluminescent device mentioned above and the electrodes on both sides of the device are introduced respectively as follows:

[0206] The anode is made of a conductor with a high work function to facilitate hole injection, such as a metal, metal oxide and / or a conductive polymer. The metal is nickel, platinum, vanadium, chromium, copper, zinc, gold, silver or their alloys; the metal oxide is zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide; the combination of metal and oxide is ZnO and Al or SnO 2 and Sb or ITO and Ag; the conductive polymer is selected from poly(3-methylthiophene), poly(3,4-(ethylene-1,2-dioxy)thiophene), polypyrrole and polyaniline, but is not limited thereto.

[0207] The hole injection material of the present invention is preferably a material capable of reducing the interface barrier between the anode and the hole transport layer. Materials such as those described below, polycyano conjugated organics, radialene compounds, phthalocyanine metal complexes, carbazole compounds, polymers, etc. Specific examples may include metal porphyrins, oligothiophenes, organic materials based on arylamines, organic materials based on hexanitrile hexaazatriphenylene, organic materials based on quinacridone, organic materials based on perylene, anthraquinone, and polyaniline-based and polythiophene-based conductive polymers, carbazole compounds shown in Formula 1 of the present invention, etc., but are not limited thereto, and may also include other compounds capable of p-doping.

[0208] The hole transport material of the present invention is preferably a material that can receive holes from the anode or the hole injection layer and transport the holes to the light-emitting layer, and has a material with high hole mobility and a material with good stability. The hole transport material of the present invention is located between the anode and the light-emitting layer, or between the hole injection layer and the light-emitting layer when the hole injection layer exists, and can be a single-layer structure or a multi-layer structure. As the hole transport layer material, for example, aromatic amine compounds, carbazole derivatives, anthracene derivatives, polymers, etc. can be used. Specific examples may include 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (TPD), 4-phenyl-4'-(9-phenylfluoren-9-yl)triphenylamine (BAFLP), 4,4'-bis[N-(9,9-dimethylfluoren-2-yl)-N-phenylamino]biphenyl (DFLDPBi), 4,4',4"-tris(N,N-diphenylamino)triphenylamine (TDATA), 4,4',4"-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (MTDATA), and 4,4'-bis[N-(spiro)triphenylamine (TDATA). -9,9'-bifluorene-2-yl)-N-phenylamino] biphenyl (BSPB), 4,4'-di(9-carbazolyl) biphenyl (CBP), 9-[4-(9-carbazolyl) phenyl]-10-phenylanthracene (CzPA), 9-phenyl-3-[4-(10-phenyl-9-anthracenyl) phenyl]-9H-carbazole (PCzPA), 2-tert-butyl-9,10-di(2-naphthyl) anthracene (t-BuDNA), 9,10-di(2-naphthyl) anthracene (DNA), 9,10-diphenylanthracene (DPAnth), poly(N-vinylcarbazole) (PVK), poly(4-vinyltriphenylamine) (PVTPA), the carbazole compound represented by Formula 1 of the present invention, etc., but are not limited thereto. The carbazole compound represented by Formula 1 of the present invention is preferred.

[0209] The triplet state (T1) energy level of the preferred material of the electron blocking layer described in the present invention is higher than the T1 energy level of the main material in the light-emitting layer, which can play a role in blocking the energy loss of the light-emitting layer material; the HOMO energy level of the electron blocking layer material is between the HOMO energy level of the hole transport layer material and the HOMO energy level of the main material of the light-emitting layer, which is conducive to the injection of holes from the positive electrode into the light-emitting layer, and at the same time, the electron blocking layer material is required to have a high hole mobility, which is conducive to hole transport and reduces the application power of the device; the LUMO energy level of the electron blocking layer material is higher than the LUMO energy level of the main material of the light-emitting layer, which plays a role in electron blocking, that is, the electron blocking layer material is required to have a wide bandgap width (Eg). The electron blocking layer material that meets the above conditions can be a triarylamine derivative, a fluorene derivative, a spirofluorene derivative, a dibenzofuran derivative, a carbazole derivative, etc. For example, N4, N4-bis([1,1'-biphenyl]-4-yl)-N4'-phenyl N4'-[1,1':4',1"-terphenyl]-4-yl-[1,1'-biphenyl]-4,4'-diamine; spirofluorene derivatives, such as N-([1,1'-diphenyl]-4-yl)-N-(9,9-dimethyl-9H-furan-2-yl)-9,9'-spirobifluorene-2-amine; dibenzofuran derivatives, such as N,N-di([1,1'-biphenyl]-4-yl)-3'-(dibenzo[b,d]furan-4-yl)-[1,1'-biphenyl]-4-amine, the carbazole compound shown in Formula 1 of the present invention, etc., but are not limited thereto. The carbazole compound shown in Formula 1 of the present invention is preferred.

[0210] The light-emitting layer of the present invention may contain only the guest material, or may be in the form of the guest material dispersed in the host material, wherein the host material may be composed of one or more materials.

[0211] As the main material of the light-emitting layer of the present invention, it is preferred to use a substance having a higher LUMO than the guest material and a lower HOMO than the guest material, for example, it may include fused aromatic ring derivatives, heterocyclic compounds, etc., such as 9,10-di(2-naphthyl)anthracene (ADN), 10,10'-bis(biphenyl-4-yl)-9,9'-bianthracene (BANE), 1,3,5-tri(pyrene-1-yl)benzene (TPB 3), 1,3,5-tri(carbazole-9-yl)benzene (TCP), 14,4',4"-tri(carbazole-9-yl)triphenylamine (TCTA), 4,4'-bis(carbazole-9-yl)-2,2'-dimethylbiphenyl (CDBP), 4,4'-bis(carbazole-9-yl)biphenyl (CBP), 9-[4-(10-phenyl-9-anthracenyl)phenyl]-9H-carbazole (CzPA), 3,6-diphenyl-9-[4-(10-phenyl-9-anthracenyl)phenyl]-9H-carbazole (DPCzPA), 9,10 ... (3,5-diphenylphenyl) anthracene (DPPA), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (TPD), 4,4'-bis[N-(9,9-dimethylfluorene-2-yl)-N-phenylamino] biphenyl (DFLDPBi), 4,4'-bis[N-(spiro-9,9'-bifluorene-2-yl)-N-phenylamino] biphenyl (BSPB), the carbazole compound represented by Formula 1 of the present invention, etc., but not limited thereto. The carbazole compound represented by Formula 1 of the present invention is preferred.

[0212] As the guest material of the light-emitting layer of the present invention, aromatic amine derivatives, fused aromatic ring derivatives, heterocyclic derivatives, metal complexes, etc., for example, 4,4'-bis(4-(9H-carbazole-9-yl)phenylvinyl)biphenyl (BSB 4 ), 4,4'-bis[4-(diphenylamino)phenylvinyl]biphenyl (BDAVBi), 10,10'-bis(3,5-bis(trifluoromethyl)phenyl)-9,9'-bianthracene (Ban-(3,5)-CF 3 ), 5,6,11,12-tetraphenyl tetracene (Rubrene), tris[2-(3-methyl-2-pyridyl)phenyl]iridium (Ir(3mppy) 3 ), bis(2-(naphthalene-2-yl)pyridine)(acetylacetonate)iridium(III)(Ir(npy) 2 acac), tris(2-phenylpyridine)iridium(III)(Ir(ppy) 3 ), bis[2-(4',6'-difluorophenyl)pyridine-N,C2']iridium(III)picolinate (FIrpic), bis[2-(3',5'bistrifluoromethylphenyl)pyridine-N,C2']iridium(III)picolinate (Ir(CF3ppy) 2 (pic)), bis[2-(4',6'-difluorophenyl)pyridine-N,C2']iridium(III) acetylacetonate (FIracac), etc., but not limited thereto.

[0213] The hole blocking layer material of the present invention needs to have good hole blocking ability so as to block holes in the light-emitting layer, such as the following materials, imidazole derivatives, phenanthroline derivatives, metal complexes, triazine derivatives, etc. Specific examples may include 1,3,5-tri(N-phenyl-2-benzimidazole)benzene (TPBi), 2-(naphthalene-2-yl)-4,7-diphenyl-1,10-phenanthroline (HNBphen), 4,7-diphenyl-1,10-phenanthroline (Bphen), 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), bis(2-methyl-8-hydroxyquinoline-N1,O8)-(1,1'-biphenyl-4-hydroxy)aluminum (BAlq), 2-(9,9-dimethyl-9H-fluorene-2-yl)4-(9,9-diphenyl-9H-fluorene-4-yl)-6-phenyl-1,3,5-triazine, etc., but are not limited thereto.

[0214] The electron transport layer material of the present invention preferably has a material with high electron mobility and good stability. It can be a single-layer structure or a multi-layer structure. For example: metal complexes such as aluminum complexes, beryllium complexes, zinc complexes, imidazole derivatives, benzimidazole derivatives, azine derivatives, carbazole derivatives, phenanthroline derivatives and other heteroaromatic compounds, polymer compounds, etc., but not limited thereto. Specific examples may include 2-(4-(9,10-di(naphthalene-2-yl)anthracen-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole, 2-(naphthalene-2-yl)-4,7-diphenyl-1,10-phenanthroline (HNBphen), 2,9-(dimethyl)-4,7-biphenyl-1,10-phenanthroline (BCP), 3,3'-[5'-[3-(3-pyridyl)phenyl](TmPyPB), 1,4-bis(4-(4,6-diphenyl-1,3,5-triazine-2-yl)phenyl)naphthalene, 2-(3-(phenanthren-9-yl)-5-(pyridin-3-yl)phenyl)-4, 6-diphenyl-1,3,5-triazine, 1,3,5-tris(4-(pyridin-4-yl)quinolin-2-yl)benzene (TPyQB), 2,5-di-(4-naphthyl)-1,3,4-oxadiazole (BND), 3-(biphenyl-4-yl)-4-phenyl-5-(4-tert-butylphenyl)-1,2,4-triazole (TAZ), bis(2-methyl-8-hydroxyquinolinato)(4-phenylphenol)aluminum(III) (BAlq), lithium 8-hydroxyquinolinate (LiQ), tris(8-hydroxyquinolinato)aluminum(III) (abbreviation: Alq), bathophenanthroline (abbreviation: BPhen), etc., but are not limited thereto.

[0215] The electron injection layer material of the present invention is preferably a material that can reduce the interface barrier between the cathode and the electron transport layer. For example, metals, alkali metals, alkaline earth metals, alkali metal halides, alkaline earth metal halides, alkali metal oxides, alkaline earth metal oxides, alkali metal salts, alkaline earth metal salts, metal complexes, and other substances with high electron injection properties. Examples include Li, Ca, Sr, LiF, CsF, CaF 2 、BaO、Li 2 CO 3 、CaCO 3 , Li 2 C 2 O 4 , Cs 2 C 2 O 4 , CsAlF 4 , LiOx, Yb, Tb, 8-hydroxyquinoline cesium, tris(8-hydroxyquinoline)aluminum, etc. In addition, a plurality of these compounds may be used in combination.

[0216] As the negative electrode material, a material having a relatively low work function may be used, and a metal, a metal oxide, a conductive polymer or the like may be used. Specific examples of the negative electrode material may be, but are not limited to: a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or an alloy thereof; a multilayer structure material such as LiF / Al or LiO 2 / Al; and the like, but not limited thereto.

[0217] The anode and cathode of the present invention can be formed of a transmissive conductive material, a semi-transmissive reflective conductive material, or a reflective conductive material. Depending on the type of material forming the anode and cathode, the organic electroluminescent device can be a top-emitting type, a bottom-emitting type, or a double-sided emitting type.

[0218] The cover layer of the present invention may be a single-layer structure composed of a single substance, or a single-layer structure or a multi-layer structure composed of different substances. The cover layer material may be an organic or inorganic substance with an appropriate refractive index, such as a metal halide, oxide, nitride, nitrogen oxide, sulfide, selenide, aromatic compound, heteroaromatic compound, aromatic amine compound, etc. Specific examples may include LiF, CsF, MgF 2 , CaF 2 、CsCl、CuI、V 2 O 5 , WO 3 、MoO 3 、TiO 2 、ZrO、ZnO、SiO 2 , tris(8-hydroxyquinoline)aluminum(III) (Alq 3), N,N'-diphenyl-N,N'-(1-naphthyl)-1,1'-biphenyl-4,4'-diamine (NPB), 4,4'-di(9-carbazole)biphenyl (CBP), the carbazole compound represented by Formula 1 of the present invention, etc., but not limited thereto. The carbazole compound represented by Formula 1 of the present invention is preferred.

[0219] The n-type charge generation material of the present invention can be selected from the following materials or one of their combinations: tris-(8-hydroxyquinolinate)aluminum (Alq3), 2-biphenyl-4-yl-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (PBD), spiro-PBD, quinoline lithium (Liq), 1,3,5-tris(N-phenylbenzimidazol-2-yl)benzene (TPBi), bis(2-methyl-8-quinolinate-N1,O8)-(1,1'-biphenyl-4-phenolate)aluminum (BAlq), 4,7-diphenyl-1,10-phenanthroline (Bphen), 2,9-bis(naphthalene-2-yl)-4,7-diphenyl-1,10-phenanthroline (NBphen), 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline ( BCP), 3-(4-biphenyl)-4-phenyl-5-tert-butylphenyl-1,2,4-triazole (TAZ), 4-(naphthalene-1-yl)-3,5-diphenyl-4H-1,2,4-triazole (NTAZ), 1,3,5-tris(p-pyridin-3-yl-phenyl)benzene (TpPyPB), 2,4,6-tris(3'-(pyridin-3-yl)biphenyl-3-yl)1,3,5-triazine (TmPPPyTz), poly[9,9-bis(3'-((N,N-dimethyl)-N-ethylammonium)-propyl)-2,7-fluorene]-alternate-2,7-(9,9-dioctylfluorene)] (PFNBr), triphenylquinoxaline (TPQ) and diphenyl-4-triphenylsilyl-phenylphosphine oxide (TSPO1), but are not limited thereto. In addition, an auxiliary n-type charge generation material may also be included. For example, the auxiliary n-type charge generation material may be an alkali metal such as, but not limited to, Li, Cs, K, Rb, Na, or Fr, or an alkaline earth metal such as, but not limited to, Be, Mg, Ca, Sr, Ba, or Ra.

[0220] The p-type charge generation material of the present invention may include one of the following materials or a combination thereof: 4,4',4"-tris(3-methylphenylamino)triphenylamine (MTDATA), 4,4',4"-tris(N,N-diphenyl-amino)triphenylamine (NATA), 4,4',4"-tris(N-(naphthalene-1-yl)-N-phenyl-amino)triphenylamine (1T-NATA), 4,4',4"-tris(N-(naphthalene-2-yl)-N-phenyl-amino)triphenylamine (2T-NATA), copper phthalocyanine (CuPc), tris(4-carbazolyl-9-yl-phenyl)amine (TCTA), N,N'-diphenyl-N,N'-bis(1-naphthyl)-1,1'-biphenyl The invention also includes, but is not limited to, 1,4,5,8,9,11-hexaazatriphenylene hexacarbonitrile (dipyrazino[2,3-f:2'3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile) (HAT-CN), 1,3,5-tris[4-(diphenylamino)phenyl]benzene (TDAPB), poly(3,4-ethylenedioxythiophene)polystyrenesulfonate (PEDOT / PSS) and N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazole-3-yl)phenyl)-9H-fluorene-2-amine, the carbazole compound represented by Formula 1 of the present invention, etc., but is not limited thereto, and the carbazole compound represented by Formula 1 of the present invention is preferred.

[0221] There is no particular restriction on the preparation method of each thin film in the organic electroluminescent device of the present invention, and vacuum evaporation, sputtering, spin coating, spray coating, screen printing, laser transfer, etc. can be used, but are not limited thereto. There is no particular restriction on the film thickness of each layer. Generally speaking, if the film thickness is too thin, defects such as pinholes are easily generated. On the contrary, if it is too thick, a high driving voltage is required and the efficiency is deteriorated. Therefore, it is usually 5nm to 10μm, and more preferably 10nm to 0.2μm.

[0222] The organic electroluminescent device of the present invention is mainly used in technical fields such as information display, lighting, commerce, and medicine. In terms of information display, it is widely used in various information displays, such as tablet computers, televisions, mobile phones, smart watches, digital cameras, VR, vehicle systems, wearable devices, lighting equipment, etc.

[0223] Synthesis Example

[0224] Raw materials and reagents: The present invention has no particular restrictions on the raw materials or reagents used in the following synthetic examples, and they can be commercially available products or prepared by preparation methods well known to those skilled in the art. The raw materials and reagents used in the present invention are all reagent-grade.

[0225] Instruments: G2-Si quadrupole tandem time-of-flight high-resolution mass spectrometer (Waters, UK); Vario ELcube organic element analyzer (Elementar, Germany).

[0226] There is no particular limitation on the preparation method of the carbazole compound of structural formula 1 of the present invention, and conventional methods known to those skilled in the art can be used, such as carbon-nitrogen coupling reaction, carbon-carbon coupling reaction, etc. For example, the carbazole compound of structural formula 1 of the present invention can be prepared by the synthetic route shown below.

[0227] Synthesis route:

[0228]

[0229] The X 1 , X 2 is a halogen atom, for example, which may be the same or different and is selected from the halogen atoms described below, I, Br, Cl.

[0230] Synthesis Example 1: Preparation of Intermediate b-491

[0231]

[0232] Under nitrogen protection, m-491 (15.14 g, 90.00 mmol), n-491 (24.08 g, 90.00 mmol), palladium acetate (0.22 g, 1.00 mmol), sodium tert-butyl alcohol (12.97 g, 135.00 mmol), tri-tert-butylphosphine (2.00 mL, 0.5 M in toluene solution) and toluene (450 mL) were added to the reaction bottle in sequence, the mixture was stirred, and the above system was heated to reflux for 7.5 h. After the reaction was completed, it was cooled to room temperature, water was added, extracted with dichloromethane, the organic phase was dried with anhydrous magnesium sulfate, filtered, the solvent was removed under reduced pressure, and recrystallized with toluene / ethanol = 10:1 to obtain b-491 (21.72 g, yield 68%), and the solid purity was ≥99.86% by HPLC. Mass spectrum m / z: 354.8386 (theoretical value: 354.8370).

[0233] According to the above synthesis method, other intermediates required for the present invention are synthesized, and the relevant raw materials are shown in Table 1:

[0234] Table 1:

[0235]

[0236] Synthesis Example 2: Preparation of Intermediate c-167

[0237]

[0238] Under nitrogen protection, p-167 (11.23 g, 70.00 mmol), q-167 (14.56 g, 70.00 mmol), tetrakistriphenylphosphine palladium (0.81 g, 0.70 mmol), potassium carbonate (19.35 g, 140 mmol) and 350 mL of toluene / ethanol / water (2:1:1) mixed solvent were added to the reaction bottle in sequence, the mixture was stirred, and the above system was heated to reflux for 4 hours; after the reaction was completed, it was cooled to room temperature, the filter cake was filtered, and the filter cake was washed with ethanol, and finally the filter cake was recrystallized with toluene / methanol = 6:1 to obtain c-167 (13.31 g, yield 78%); HPLC purity ≥ 99.76%. Mass spectrum m / z: 243.0744 (theoretical value: 243.0753).

[0239] According to the above synthesis method, other intermediates required for the present invention are synthesized, and the relevant raw materials are shown in Table 2:

[0240] Table 2:

[0241]

[0242]

[0243] Synthesis Example 3: Preparation of Compound 3

[0244]

[0245] Preparation of intermediate A-4:

[0246] Under nitrogen protection, a-4 (5.59 g, 60.00 mmol), b-4 (19.33 g, 60.00 mmol), palladium acetate (0.16 g, 0.60 mmol), sodium tert-butoxide (11.53 g, 120.00 mmol), tri-tert-butylphosphine (1.4 mL, 0.5 M in toluene solution) and toluene (300 mL) were added to the reaction bottle in sequence, the mixture was stirred, and the above system was heated to reflux for reaction for 4.5 h. After the reaction was completed, it was cooled to room temperature, water was added, extracted with ethyl acetate, the organic phase was dried with anhydrous magnesium sulfate, filtered, the solvent was removed under reduced pressure, and recrystallized with toluene / ethanol = 7:1 to obtain A-4 (15.85 g, yield 79%), and the solid purity was ≥99.85% by HPLC. Mass spectrum m / z: 334.135 (theoretical value: 334.147).

[0247] Preparation of compound 4:

[0248] Under nitrogen protection, A-4 (13.38 g, 40.00 mmol), c-4 (11.37 g, 40.00 mmol), tridibenzylideneacetone dipalladium (0.37 g, 0.40 mmol), sodium tert-butoxide (7.69 g, 80.00 mmol), tri-tert-butylphosphine (1.6 mL, 0.5 M in toluene solution) and toluene (150 mL) were added to the reaction bottle in sequence, the mixture was stirred, and the above system was heated to reflux for 5.5 h. After the reaction was completed, it was cooled to room temperature, water was added, extracted with dichloromethane, the organic phase was dried with anhydrous magnesium sulfate, filtered, the solvent was removed under reduced pressure, and recrystallized from toluene to obtain compound 4 (15.27 g, yield 71%), and the solid purity was ≥99.95% by HPLC. Mass spectrum m / z: 537.2214 (theoretical value: 537.2205). Theoretical element content (%) C 39 H 27 N 3 :C, 87.12;H, 5.06;N, 7.82. Measured element content (%): C, 87.14;H, 5.03;N, 7.87.

[0249] Synthesis Example 4: Preparation of Compound 89

[0250]

[0251] According to the same preparation method as in Synthesis Example 3, a-4 was replaced by an equal molar amount of a-89, and c-4 was replaced by an equal molar amount of c-89 to obtain compound 89 (17.92 g). The solid purity was ≥ 99.94% as determined by HPLC. Mass spectrum m / z: 613.2503 (theoretical value: 613.2518). Theoretical element content (%) C 45 H 31 N 3 :C, 88.06;H, 5.09;N, 6.85. Measured element content (%): C, 88.07;H, 5.07;N, 6.86.

[0252] Synthesis Example 5: Preparation of Compound 123

[0253]

[0254] According to the same preparation method as in Synthesis Example 3, a-4 was replaced by an equal molar amount of a-123, b-4 was replaced by an equal molar amount of b-123, and c-4 was replaced by an equal molar amount of c-123 to obtain compound 123 (16.88 g). The solid purity was ≥ 99.96% as determined by HPLC. Mass spectrum m / z: 664.2637 (theoretical value: 664.2627). Theoretical element content (%) C 48 H 32 N4 :C, 86.72;H, 4.85;N, 8.43. Measured element content (%): C, 86.70;H, 4.86;N, 8.44.

[0255] Synthesis Example 6: Preparation of Compound 128

[0256]

[0257] According to the same preparation method as in Synthesis Example 3, a-4 was replaced by an equal molar amount of a-89, and c-4 was replaced by an equal molar amount of c-128 to obtain compound 128 (15.91 g). The solid purity was ≥ 99.97% as determined by HPLC. Mass spectrum m / z: 537.2216 (theoretical value: 537.2205). Theoretical element content (%) C 39 H 27 N 3 :C, 87.12;H, 5.06;N, 7.82. Measured element content (%): C, 87.15;H, 5.02;N, 7.83.

[0258] Synthesis Example 7: Preparation of Compound 167

[0259]

[0260] According to the same preparation method as in Synthesis Example 3, a-4 was replaced by an equal molar amount of a-89, and c-4 was replaced by an equal molar amount of c-167 to obtain compound 167 (17.30 g). The solid purity was ≥ 99.93% as determined by HPLC. Mass spectrum m / z: 617.2761 (theoretical value: 617.2769). Theoretical element content (%) C 45 H 27 D 4 N 3 :C, 87.49;H, 5.71;N, 6.80. Measured element content (%): C, 87.46;H, 5.72;N, 6.82.

[0261] Synthesis Example 8: Preparation of Compound 174

[0262]

[0263] According to the same preparation method as in Synthesis Example 3, a-4 was replaced by an equal molar amount of a-174, and c-4 was replaced by an equal molar amount of c-174 to obtain compound 174 (19.48 g). The solid purity was ≥ 99.96% as determined by HPLC. Mass spectrum m / z: 685.2927 (theoretical value: 685.2913). Theoretical element content (%) C 48 H 39 N3 Si: C, 84.05; H, 5.73; N, 6.13. Measured element content (%): C, 84.07; H, 5.75; N, 6.10.

[0264] Synthesis Example 9: Preparation of Compound 183

[0265]

[0266] According to the same preparation method as in Synthesis Example 3, a-4 was replaced by an equal molar amount of a-89, b-4 was replaced by an equal molar amount of b-183, and c-4 was replaced by an equal molar amount of c-183 to obtain compound 183 (20.04 g). The solid purity was ≥ 99.95% as determined by HPLC. Mass spectrum m / z: 725.3762 (theoretical value: 725.3770). Theoretical element content (%) C 53 H 47 N 3 :C, 87.69;H, 6.53;N, 5.79. Measured element content (%): C, 87.68;H, 6.55;N, 5.78.

[0267] Synthesis Example 10: Preparation of Compound 207

[0268]

[0269] According to the same preparation method as in Synthesis Example 3, a-4 was replaced by an equal molar amount of a-207, b-4 was replaced by an equal molar amount of b-123, and c-4 was replaced by an equal molar amount of c-128 to obtain Compound 207 (17.43 g). The solid purity was ≥ 99.97% as determined by HPLC. Mass spectrum m / z: 613.2531 (theoretical value: 613.2518). Theoretical element content (%) C 45 H 31 N 3 :C, 88.06;H, 5.09;N, 6.85. Measured element content (%): C, 88.03;H, 5.08;N, 6.81.

[0270] Synthesis Example 11: Preparation of Compound 222

[0271]

[0272] According to the same preparation method as in Synthesis Example 3, b-4 was replaced by an equal molar amount of b-123, and c-4 was replaced by an equal molar amount of c-222 to obtain Compound 222 (16.06 g). The solid purity was ≥ 99.94% as determined by HPLC. Mass spectrum m / z: 587.2350 (theoretical value: 587.2361). Theoretical element content (%) C43 H 29 N 3 :C, 87.88;H, 4.97;N, 7.15. Measured element content (%): C, 87.85;H, 4.94;N, 7.18.

[0273] Synthesis Example 12: Preparation of Compound 228

[0274]

[0275] According to the same preparation method as in Synthesis Example 3, b-4 was replaced by an equal molar amount of b-228, and c-4 was replaced by an equal molar amount of c-228 to obtain Compound 228 (17.47 g). The solid purity was ≥ 99.99% as determined by HPLC. Mass spectrum m / z: 689.2841 (theoretical value: 689.2831). Theoretical element content (%) C 51 H 35 N 3 :C, 88.79;H, 5.11;N, 6.09. Measured element content (%): C, 88.81;H, 5.09;N, 6.12.

[0276] Synthesis Example 13: Preparation of Compound 231

[0277]

[0278] According to the same preparation method as in Synthesis Example 3, a-4 was replaced with an equal molar amount of a-231 to obtain Compound 231 (16.87 g). The solid purity was ≥ 99.98% as determined by HPLC. Mass spectrum m / z: 577.2508 (theoretical value: 577.2518). Theoretical element content (%) C 42 H 31 N 3 :C, 87.32;H, 5.41;N, 7.27. Measured element content (%): C, 87.35;H, 5.43;N, 7.22.

[0279] Synthesis Example 14: Preparation of Compound 251

[0280]

[0281] According to the same preparation method as in Synthesis Example 3, a-4 was replaced by an equal molar amount of a-251, and c-4 was replaced by an equal molar amount of c-222 to obtain Compound 251 (19.81 g). The solid purity was ≥ 99.95% as determined by HPLC. Mass spectrum m / z: 687.2688 (theoretical value: 687.2674). Theoretical element content (%) C 51 H 33 N3 :C, 89.05;H, 4.84;N, 6.11. Measured element content (%): C, 89.03;H, 4.87;N, 6.10.

[0282] Synthesis Example 15: Preparation of Compound 357

[0283]

[0284] According to the same preparation method as in Synthesis Example 3, b-4 was replaced by an equal molar amount of b-357, and c-4 was replaced by an equal molar amount of c-357 to obtain compound 357 (14.48 g). The solid purity was ≥ 99.96% as determined by HPLC. Mass spectrum m / z: 538.2157 (theoretical value: 538.2157). Theoretical element content (%) C 38 H 26 N 4 :C, 84.73;H, 4.87;N, 10.40. Measured element content (%): C, 84.70;H, 4.88;N, 10.41.

[0285] Synthesis Example 16: Preparation of Compound 372

[0286]

[0287] According to the same preparation method as in Synthesis Example 3, a-4 was replaced by an equal molar amount of a-372, b-4 was replaced by an equal molar amount of b-123, and c-4 was replaced by an equal molar amount of c-372 to obtain compound 372 (17.60 g). The solid purity was ≥ 99.97% as determined by HPLC. Mass spectrum m / z: 619.2765 (theoretical value: 619.2784). Theoretical element content (%) C 44 H 25 D 5 N 3 :C, 85.27;H, 5.69;N, 9.04. Measured element content (%): C, 85.28;H, 5.67;N, 9.07.

[0288] Synthesis Example 17: Preparation of Compound 419

[0289]

[0290] According to the same preparation method as in Synthesis Example 3, a-4 was replaced by an equal molar amount of a-419, b-4 was replaced by an equal molar amount of b-419, and c-4 was replaced by an equal molar amount of c-419 to obtain compound 419 (19.82 g). The solid purity was ≥ 99.94% as determined by HPLC. Mass spectrum m / z: 707.3063 (theoretical value: 707.3049). Theoretical element content (%) C 50 H 37 N 5 :C, 84.84;H, 5.27;N, 9.89. Measured element content (%): C, 84.86;H, 5.55;N, 9.89.

[0291] Synthesis Example 18: Preparation of Compound 465

[0292]

[0293] According to the same preparation method as in Synthesis Example 3, a-4 was replaced by an equal molar amount of a-465, b-4 was replaced by an equal molar amount of b-465, and c-4 was replaced by an equal molar amount of c-465 to obtain compound 465 (18.49 g). The solid purity was ≥ 99.96% as determined by HPLC. Mass spectrum m / z: 669.3135 (theoretical value: 669.3144). Theoretical element content (%) C 49 H 39 N 3 :C, 87.86;H, 5.87;N, 6.27. Measured element content (%): C, 87.83;H, 5.89;N, 6.28.

[0294] Synthesis Example 19: Preparation of Compound 491

[0295]

[0296] According to the same preparation method as in Synthesis Example 3, a-4 was replaced by an equal molar amount of a-491, b-4 was replaced by an equal molar amount of b-491, and c-4 was replaced by an equal molar amount of c-491 to obtain Compound 491 (22.78 g). The solid purity was ≥ 99.92% as determined by HPLC. Mass spectrum m / z: 790.3081 (theoretical value: 790.3096). Theoretical element content (%) C 58 H 38 N 4 :C, 88.07;H, 4.84;N, 7.08. Measured element content (%): C, 88.09;H, 4.85;N, 7.05.

[0297] Synthesis Example 20: Preparation of Compound 500

[0298]

[0299] According to the same preparation method as in Synthesis Example 3, a-4 was replaced by an equal molar amount of a-500, b-4 was replaced by an equal molar amount of b-500, and c-4 was replaced by an equal molar amount of c-491 to obtain Compound 500 (19.85 g). The solid purity was ≥ 99.98% as determined by HPLC. Mass spectrum m / z: 729.3153 (theoretical value: 729.3144). Theoretical element content (%) C 54 H 39 N 3 :C, 88.86;H, 5.39;N, 5.76. Measured element content (%): C, 88.87;H, 5.05;N, 5.79.

[0300] Synthesis Example 21: Preparation of Compound 518

[0301]

[0302] According to the same preparation method as in Synthesis Example 3, a-4 was replaced by an equal molar amount of a-518, b-4 was replaced by an equal molar amount of b-518, and c-4 was replaced by an equal molar amount of c-518 to obtain Compound 518 (21.57 g). The solid purity was ≥ 99.93% as determined by HPLC. Mass spectrum m / z: 766.3420 (theoretical value: 766.3430). Theoretical element content (%) C 53 H 38 D 4 N 4 Si: C, 82.99; H, 6.04; N, 7.30. Measured element content (%): C, 82.97; H, 6.08; N, 7.29.

[0303] Synthesis Example 22: Preparation of Compound 561

[0304]

[0305] According to the same preparation method as in Synthesis Example 3, a-4 was replaced by an equal molar amount of a-89, b-4 was replaced by an equal molar amount of b-500, and c-4 was replaced by an equal molar amount of c-89 to obtain Compound 561 (19.59 g). The solid purity was ≥ 99.95% as determined by HPLC. Mass spectrum m / z: 689.2815 (theoretical value: 689.2831). Theoretical element content (%) C 51 H 35 N 3 :C, 88.79;H, 5.11;N, 6.09. Measured element content (%): C, 88.77;H, 5.14;N, 6.07.

[0306] Synthesis Example 23: Preparation of Compound 595

[0307]

[0308] According to the same preparation method as in Synthesis Example 3, a-4 was replaced by an equal molar amount of a-595, b-4 was replaced by an equal molar amount of b-595, and c-4 was replaced by an equal molar amount of c-491 to obtain Compound 595 (19.40 g). The solid purity was ≥ 99.97% as determined by HPLC. Mass spectrum m / z: 689.2843 (theoretical value: 689.2831). Theoretical element content (%) C 51 H 35 N 3 :C, 88.79;H, 5.11;N, 6.09. Measured element content (%): C, 88.76;H, 5.15;N, 6.08.

[0309] Synthesis Example 24: Preparation of Compound 759

[0310]

[0311] According to the same preparation method as in Synthesis Example 3, a-4 was replaced by an equal molar amount of a-89, b-4 was replaced by an equal molar amount of b-759, and c-4 was replaced by an equal molar amount of c-222 to obtain compound 759 (19.99 g). The solid purity was ≥ 99.96% as determined by HPLC. Mass spectrum m / z: 745.3448 (theoretical value: 745.3457). Theoretical element content (%) C 55 H 43 N 3 :C, 88.56;H, 5.81;N, 5.63. Measured element content (%): C, 88.52;H, 5.84;N, 5.64.

[0312] Synthesis Example 25: Preparation of Compound 767

[0313]

[0314] According to the same preparation method as in Synthesis Example 3, a-4 was replaced by an equal molar amount of a-89, b-4 was replaced by an equal molar amount of b-767, and c-4 was replaced by an equal molar amount of c-767 to obtain compound 767 (19.85 g). The solid purity was ≥ 99.94% as determined by HPLC. Mass spectrum m / z: 729.2793 (theoretical value: 729.2780). Theoretical element content (%) C 53 H 35 N 3O: C, 87.22; H, 4.83; N, 5.76. Measured element content (%): C, 87.25; H, 4.82; N, 5.74.

[0315] Synthesis Example 26: Preparation of Compound 845

[0316]

[0317] According to the same preparation method as in Synthesis Example 3, a-4 was replaced by an equal molar amount of a-845, b-4 was replaced by an equal molar amount of b-845, and c-4 was replaced by an equal molar amount of c-845 to obtain Compound 845 (15.22 g). The solid purity was ≥ 99.92% as determined by HPLC. Mass spectrum m / z: 543.2455 (theoretical value: 543.2471). Theoretical element content (%) C 38 H 21 D 5 N 4 :C, 83.95;H, 5.75;N, 10.31. Measured element content (%): C, 83.92;H, 5.73;N, 10.36.

[0318] Synthesis Example 27: Preparation of Compound 895

[0319]

[0320] According to the same preparation method as in Synthesis Example 3, a-4 was replaced by an equal molar amount of a-89, b-4 was replaced by an equal molar amount of b-895, and c-4 was replaced by an equal molar amount of c-174 to obtain compound 895 (18.83 g). The solid purity was ≥ 99.98% as determined by HPLC. Mass spectrum m / z: 635.3187 (theoretical value: 635.3177). Theoretical element content (%) C 46 H 25 D 8 N 3 :C, 86.89;H, 6.50;N, 6.61. Measured element content (%): C, 86.85;H, 6.48;N, 6.63.

[0321] Synthesis Example 28: Preparation of Compound 906

[0322]

[0323] According to the same preparation method as in Synthesis Example 3, a-4 was replaced by an equal molar amount of a-89, b-4 was replaced by an equal molar amount of b-906, and c-4 was replaced by an equal molar amount of c-174 to obtain compound 906 (18.85 g). The solid purity was ≥ 99.97% as determined by HPLC. Mass spectrum m / z: 663.2661 (theoretical value: 663.2674). Theoretical element content (%) C 49 H 33 N 3 :C, 88.66;H, 5.01;N, 6.33. Measured element content (%): C, 88.63;H, 5.02;N, 6.35.

[0324] Synthesis Example 29: Preparation of Compound 922

[0325]

[0326] According to the same preparation method as in Synthesis Example 3, a-4 was replaced by an equal molar amount of a-89, b-4 was replaced by an equal molar amount of b-922, and c-4 was replaced by an equal molar amount of c-922 to obtain compound 922 (21.80 g). The solid purity was ≥ 99.95% as determined by HPLC. Mass spectrum m / z: 789.3159 (theoretical value: 789.3144). Theoretical element content (%) C 59 H 39 N 3 :C, 89.70;H, 4.98;N, 5.32. Measured element content (%): C, 89.74;H, 4.93;N, 5.33.

[0327] Synthesis Example 30: Preparation of Compound 926

[0328]

[0329] According to the same preparation method as in Synthesis Example 3, a-4 was replaced by an equal molar amount of a-926, b-4 was replaced by an equal molar amount of b-926, and c-4 was replaced by an equal molar amount of c-926 to obtain Compound 926 (20.23 g). The solid purity was ≥ 99.96% as determined by HPLC. Mass spectrum m / z: 754.2741 (theoretical value: 754.2733). Theoretical element content (%) C 54 H 34 N 4 O: C, 85.92; H, 4.54; N, 7.42. Measured element content (%): C, 85.94; H, 4.51; N, 7.43.

[0330] Synthesis Example 31: Preparation of Compound 942

[0331]

[0332] According to the same preparation method as in Synthesis Example 3, a-4 was replaced by an equal molar amount of a-942, b-4 was replaced by an equal molar amount of b-942, and c-4 was replaced by an equal molar amount of c-942 to obtain Compound 942 (19.67 g). The solid purity was ≥ 99.93% as determined by HPLC. Mass spectrum m / z: 744.2873 (theoretical value: 744.2889). Theoretical element content (%) C 53 H 36 N 4 O: C, 85.46; H, 4.87; N, 7.52. Measured element content (%): C, 85.45; H, 4.86; N, 7.54.

[0333] Synthesis Example 32: Preparation of Compound 964

[0334]

[0335] According to the same preparation method as in Synthesis Example 3, a-4 was replaced by an equal molar amount of a-89, b-4 was replaced by an equal molar amount of b-964, and c-4 was replaced by an equal molar amount of c-128 to obtain compound 964 (19.87 g). The solid purity was ≥ 99.98% as determined by HPLC. Mass spectrum m / z: 689.2847 (theoretical value: 689.2831). Theoretical element content (%) C 51 H 35 N 3 :C, 88.79;H, 5.11;N, 6.09. Measured element content (%): C, 88.76;H, 5.15;N, 6.08.

[0336] Device Embodiment

[0337] In the present invention, the ITO glass substrate is ultrasonically cleaned twice with 5% glass cleaning liquid, each time for 20 minutes, and then ultrasonically cleaned twice with deionized water, each time for 10 minutes. Acetone and isopropyl ketone are ultrasonically cleaned for 20 minutes in sequence, and dried at 120°C. The organic materials are all sublimated, and the purity is above 99.99%.

[0338] The test software, computer, K2400 digital source meter produced by Keithley Company of the United States and PR788 spectrum scanning luminance meter produced by PhotoResearch Company of the United States are combined into a joint IVL test system to test the luminous efficiency of organic electroluminescent devices. The life test adopts the M6000 OLED life test system of McScience Company. The test environment is atmospheric environment and the temperature is room temperature.

[0339] The device is prepared by vacuum evaporation system, which is completed by continuous evaporation under uninterrupted vacuum conditions. The materials used are placed in different evaporation source quartz crucibles, and the temperature of the evaporation source can be controlled separately. The thermal evaporation rate of organic materials is generally set at 0.1nm / s, and the evaporation rate of electrode metals is 0.4~0.6nm / s. The processed glass substrate is placed in the OLED vacuum coating machine. During the film production process, the system vacuum should be maintained at 5×10 -5 Pa, the organic layer and the metal electrode are evaporated separately by replacing the mask plate, the evaporation speed is detected by Inficon's SQM160 quartz crystal film thickness detector, and the film thickness is detected by a quartz crystal oscillator.

[0340] Example 1: Preparation of organic electroluminescent device 1

[0341] On a glass substrate, ITO is used as an anode; 60 nm of 2-TNATA is vacuum-deposited on the anode to form a hole injection layer; 90 nm of the compound 4 of the present invention is vacuum-deposited on the hole injection layer to form a hole transport layer; 35 nm of CBP:RD-1 (mixed in a mass ratio of 96%:4%) is vacuum-deposited on the hole transport layer to form a light-emitting layer; 10 nm of HB-1 is vacuum-deposited on the light-emitting layer to form a hole blocking layer; 36 nm of ET-1:LiQ (mixed in a mass ratio of 1:1) is vacuum-deposited on the hole blocking layer to form an electron transport layer; 1.0 nm of LiF is vacuum-deposited on the electron transport layer to form an electron injection layer; and 120 nm of Al is vacuum-deposited on the electron injection layer to form a cathode.

[0342] Examples 2 to 30: Preparation of organic electroluminescent devices 2 to 30

[0343] The compound 4 in the hole transport layer of Example 1 was replaced by compound 89, compound 123, compound 128, compound 167, compound 174, compound 183, compound 207, compound 222, compound 228, compound 231, compound 251, compound 357, compound 372, compound 419, compound 465, compound 491, compound 500, compound 518, compound 561, compound 595, compound 759, compound 767, compound 845, compound 895, compound 906, compound 922, compound 926, compound 942, and compound 964, respectively, and the other steps were the same to obtain organic electroluminescent devices 2 to 30.

[0344] Comparative Examples 1 to 3: Preparation of Comparative Organic Electroluminescent Devices 1 to 3

[0345] The compound 4 in the hole transport layer of Example 1 was replaced by R-1, R-2, and R-3 respectively, and the other steps were the same to obtain comparative organic electroluminescent devices 1 to 3.

[0346]

[0347]

[0348] The test results of the luminescent characteristics of the organic electroluminescent devices prepared in Examples 1 to 30 of the present invention and Comparative Examples 1 to 3 are shown in Table 1.

[0349] Table 1 Test data of luminescence characteristics of organic electroluminescent devices

[0350]

[0351]

[0352] Note: T95 refers to the current density of 10mA / cm 2 Under the condition, the time taken for the device brightness to decay to 95%;

[0353] It can be concluded from Table 1 that, compared with Comparative Examples 1 to 3, when the carbazole compound represented by Formula 1 of the present invention is used in the hole transport layer of the organic electroluminescent device, the efficiency of the organic electroluminescent device is effectively improved, and the service life of the device is improved, which further indicates that the compound of the present invention has excellent hole transport ability.

[0354] Example 31: Preparation of organic electroluminescent device 31

[0355] ITO is used as an anode on a glass substrate; 28nm of NPB:HI-1 (mixed in a mass ratio of 96%:4%) is vacuum evaporated on the anode to form a hole injection layer; 55nm of compound NPB is vacuum evaporated on the hole injection layer to form a first hole transport layer; the compound 4 of the present invention is vacuum evaporated on the first hole transport layer as a second hole transport layer with a thickness of 35nm; 32nm of BH-1:BD-1 (mixed in a mass ratio of 97%:3%) is vacuum evaporated on the second hole transport layer to form a light-emitting layer; 35nm of ET-1:LiQ (mixed in a mass ratio of 1:1) is vacuum evaporated on the light-emitting layer to form an electron transport layer; 1.0nm of LiF is vacuum evaporated on the electron transport layer to form an electron injection layer; 120nm of Al is vacuum evaporated on the electron injection layer to form a cathode.

[0356] Examples 32 to 60: Preparation of organic electroluminescent devices 32 to 60

[0357] The compound 4 in the second hole transport layer of Example 31 was replaced by compound 89, compound 123, compound 128, compound 167, compound 174, compound 183, compound 207, compound 222, compound 228, compound 231, compound 251, compound 357, compound 372, compound 419, compound 465, compound 491, compound 500, compound 518, compound 561, compound 595, compound 759, compound 767, compound 845, compound 895, compound 906, compound 922, compound 926, compound 942, and compound 964, respectively, and the other steps were the same to obtain organic electroluminescent devices 32 to 60.

[0358] Comparative Examples 4-5: Preparation of Comparative Organic Electroluminescent Devices 4-5

[0359] The compound 4 in the second hole transport layer of Example 31 was replaced by R-4 and R-5 respectively, and the other steps were the same to obtain comparative organic electroluminescent devices 4 to 5.

[0360]

[0361]

[0362] The test results of the luminescent characteristics of the organic electroluminescent devices prepared in Examples 31 to 60 of the present invention and Comparative Examples 4 to 5 are shown in Table 2.

[0363] Table 2 Test data of luminescence characteristics of organic electroluminescent devices

[0364]

[0365]

[0366] Note: T95 refers to the current density of 10mA / cm 2 Under the condition, the time taken for the device brightness to decay to 95%;

[0367] It can be seen from the results in Table 2 that when the carbazole compound represented by Formula 1 of the present invention is applied to an organic electroluminescent device and is used as a second hole transport layer material in the hole transport region, the performance of the device is significantly improved compared with Comparative Examples 4 to 5, showing the advantages of high luminous efficiency and long service life, indicating that it has a good synergistic effect.

[0368] Example 61: Preparation of organic electroluminescent device 61

[0369] On a glass substrate, ITO / Ag / ITO is used as an anode; 30 nm of NPB:HI-1 (mixed in a mass ratio of 97%:3%) is vacuum-deposited on the anode to form a hole injection layer; 85 nm of NPB is vacuum-deposited on the hole injection layer to form a hole transport layer; 38 nm of the present compound 89:RH-1:RD-1 (mixed in a mass ratio of 48:48:4) is vacuum-deposited on the hole transport layer to form a light-emitting layer; 30 nm of ET-2:LiQ (mixed in a mass ratio of 1:1) is vacuum-deposited on the light-emitting layer to form an electron transport layer; 1.0 nm of LiF is vacuum-deposited on the electron transport layer to form an electron injection layer; 10 nm of Mg and Ag (mass ratio of 1:9) are vacuum-deposited on the electron injection layer to form a cathode, and 70 nm of CPL is vacuum-deposited on the cathode to form a covering layer.

[0370] Examples 62-80: Preparation of organic electroluminescent devices 62-80

[0371] The compound 89 in the light-emitting layer of Example 61 is replaced by compound 123, compound 128, compound 167, compound 174, compound 183, compound 207, compound 228, compound 231, compound 251, compound 357, compound 372, compound 465, compound 561, compound 595, compound 759, compound 767, compound 906, compound 926, and compound 942, respectively, and the other steps are the same to obtain organic electroluminescent devices 62 to 80.

[0372] Comparative Examples 6 to 8: Preparation of Comparative Organic Electroluminescent Devices 6 to 8

[0373] The compound 89 in the light-emitting layer of Example 61 was replaced by R-6, R-7, and R-8 respectively, and the other steps were the same to obtain comparative organic electroluminescent devices 6 to 8.

[0374]

[0375] The test results of the luminescent characteristics of the organic electroluminescent devices prepared in Examples 61 to 80 of the present invention and Comparative Examples 6 to 8 are shown in Table 3.

[0376] Table 3 Test data of luminescence characteristics of organic electroluminescent devices

[0377]

[0378] Note: T95 refers to the current density of 10mA / cm 2 Under the condition, the time taken for the device brightness to decay to 95%;

[0379] It can be seen from the results in Table 3 that when the carbazole compounds of the present invention are applied to the main material of the light-emitting layer of an organic electroluminescent device, the luminous efficiency and service life of the device are greatly improved. In summary, the carbazole compounds provided by the present invention are a class of OLED materials with excellent performance and have good application prospects.

[0380] It should be noted that the present invention is particularly described using individual embodiments. However, without departing from the principles of the present invention, a person skilled in the art may make various improvements in form or detail to the present invention, and these improvements also fall within the scope of protection of the present invention.

Claims

1. A carbazole compound, characterized in that Having the general formula shown in Structural Formula 1, Wherein, Ar1 is selected from any one of the following groups or their combinations: The v is selected from C(R3) or N atoms the same or differently, and the v at the bonding site is selected from C; The ring A is selected from any one of a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a pyridine ring, a pyrimidine ring, a pyrazine ring, a pyridazine ring, a triazine ring, a quinoline ring, an isoquinoline ring, a quinazoline ring, a quinoxaline ring, an azaphenanthren ring, and an azaanthracene ring, which are substituted or unsubstituted by R3; The ring B is selected from any one of a benzene ring, a naphthalene ring, an anthracene ring, and a phenanthrene ring substituted or unsubstituted by R3; The ring D is selected from a C3-C12 alicyclic group substituted or unsubstituted by R3; The R3 is independently selected from any one of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C12 alicyclic and C6-C30 aromatic fused ring; a2 is independently selected from 0, 1, 2, 3 or 4; a3 is independently selected from 0, 1 or 2; a4 is independently selected from 0, 1, 2 or 3; a5 is independently selected from 0, 1, 2, 3, 4, 5, 6 or 7; Said Y is selected from an O atom, a S atom or N(R5); The R5 is selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 alicyclic group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C3-C12 alicyclic and C6-C30 aromatic ring fused ring group, substituted or unsubstituted C2-C30 heteroaryl group; The Ar2 is selected from the group shown in formula 1-1; The z are identically or differently selected from C (R4) or N atoms, and at least one z is selected from N atoms, and the z at the bonding site is selected from C; The R4 is independently selected from any one of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C12 alicyclic group, substituted or unsubstituted C3-C12 alicyclic and C6-C30 aromatic ring fused ring group; The R1 and R2 are independently selected from any one of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C12 alicyclic group, fused ring group of substituted or unsubstituted C3-C12 alicyclic ring and C6-C30 aromatic ring, substituted or unsubstituted C2-C30 heteroaryl, or the two adjacent R1s and two R2s are connected to each other to form a substituted or unsubstituted ring, and the two adjacent R1s and two R2s do not form a ring at the same time; The x are selected from CH or N atoms the same or differently, and the x at the bonding site is selected from C; The n1 is selected from 0, 1, 2, 3 or 4; the n2 is selected from 0, 1, 2, 3 or 4; The L is selected from the following groups: The t is selected from C(R6) or N atoms the same or differently, and the t at the bonding site is selected from C; The R6 is identically or differently selected from any one of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 alicyclic group, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C12 alicyclic and C6-C30 aromatic ring fused ring, or two adjacent R6 are connected to each other to form a substituted or unsubstituted: benzene ring, naphthalene ring, anthracene ring, phenanthrene ring, furan ring, thiophene ring, indole ring, indenyl, oxazole ring, thiazole ring, imidazole ring, pyridine ring, pyrimidine ring, pyrazine ring, pyridazine ring, triazine ring, quinoline ring, isoquinoline ring, quinazoline ring, quinoxaline ring, azaphenanthren ring, azaanthracene ring, alicyclic ring; the c1 is selected from 1, 2, 3, 4 or 5; The L1 is selected from a single bond, a group as shown below or any one of their combinations: The u is selected from C(R7) or N atoms the same or differently, and the u at the bonding site is selected from C; The ring G is selected from any one of a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a pyridine ring, a pyrimidine ring, a pyrazine ring, a pyridazine ring, a triazine ring, a quinoline ring, an isoquinoline ring, a quinazoline ring, a quinoxaline ring, an azaphenanthren ring, and an azaanthracene ring, which are substituted or unsubstituted by R7; The ring E is selected from any one of a benzene ring, a naphthalene ring, an anthracene ring, and a phenanthrene ring substituted or unsubstituted by R7; The ring F is selected from a C3-C12 alicyclic group substituted or unsubstituted by R7; The R7 is the same or different and is selected from any one of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C12 alicyclic group, substituted or unsubstituted C6-C30 aryl group, fused ring group of substituted or unsubstituted C3-C12 alicyclic ring and C6-C30 aromatic ring; the d1 is independently selected from 1, 2, 3, 4 or 5; the d2 is independently selected from 0, 1, 2, 3 or 4; the d3 is independently selected from 0, 1, 2 or 3; the d4 is independently selected from 0, 1 or 2; the d5 is independently selected from 0, 1, 2, 3, 4, 5 or 6; Said Y2 is selected from an O atom, a S atom or N(R8); The R8 is selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C12 alicyclic group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C3-C12 alicyclic and C6-C30 aromatic ring fused ring group, substituted or unsubstituted C2-C30 heteroaryl group; The L2 is selected from a single bond, a group as shown below or any one of their combinations: The w are identically or differently selected from C(R 10 ) or a N atom, and w at the bonding site is selected from C; The ring J is selected from R 10 Substituted or unsubstituted: any one of a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a pyridine ring, a pyrimidine ring, a pyrazine ring, a pyridazine ring, a triazine ring, a quinoline ring, an isoquinoline ring, a quinazoline ring, a quinoxaline ring, a phenanthroline ring, and a pyrananthracene ring; The ring H is selected from R 10 Substituted or unsubstituted: any one of benzene ring, naphthalene ring, anthracene ring, and phenanthrene ring; The ring K is selected from R 10 Substituted or unsubstituted C3-C12 alicyclic group; Said Y3 is selected from an O atom, a S atom or N(R9); The R9 is identically or differently selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C12 alicyclic group, substituted or unsubstituted C6-C30 aryl group, fused ring group of substituted or unsubstituted C3-C12 alicyclic ring and C6-C30 aromatic ring, substituted or unsubstituted C2-C30 heteroaryl group; The R 10 The same or different ones are selected from any one of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 alicyclic group, substituted or unsubstituted C6-C30 aryl group, fused ring group of substituted or unsubstituted C3-C12 alicyclic ring and C6-C30 aromatic ring, substituted or unsubstituted C2-C30 heteroaryl group; the e1 is independently selected from 1, 2, 3, 4 or 5; the e2 is independently selected from 0, 1, 2, 3 or 4; the e3 is independently selected from 0, 1, 2 or 3; the e4 is independently selected from 0, 1 or 2; The R 11 , R 12 Any one independently selected from hydrogen, deuterium, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 alicyclic group, substituted or unsubstituted C6-C30 aryl group, fused ring group of substituted or unsubstituted C3-C12 alicyclic ring and C6-C30 aromatic ring, substituted or unsubstituted C2-C30 heteroaryl group.

2. The carbazole compound according to claim 1, characterized in that The Ar2 is selected from any one of the following groups: The R4 is independently selected from hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted following groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutane, cyclopentanyl, cyclohexanyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, dihydroindenyl, indenyl, tetrahydronaphthyl, dihydronaphthyl, silyl, any one or more thereof; when substituted by multiple substituents, the multiple substituents are the same or different; the b is independently selected from 0, 1, 2, 3, 4, 5 or 6; the b1 is independently selected from 0, 1, 2, 3, 4 or 5; the b2 is independently selected from 0, 1, 2, 3 or 4; the b3 is independently selected from 0, 1, 2 or 3; the b4 is independently selected from 0, 1 or 2.

3. The carbazole compound according to claim 1, characterized in that The Ar1 is selected from any one of the following groups or their combinations: R3, R 15 The same or different selected from hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted following groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, octyl, phenyl, biphenyl, naphthyl, dihydroindenyl, indenyl, tetrahydronaphthyl, dihydronaphthyl, anthracenyl, phenanthrenyl, triphenylene, silyl any one or more, in the case of being substituted by multiple substituents, the multiple substituents are the same or different from each other; The R5 is selected from hydrogen, deuterium, substituted or unsubstituted groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthryl, triphenylene, indenyl, tetrahydronaphthyl, benzocyclopropyl, benzocyclobutane, benzocyclopentyl, benzocyclohexyl, silyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, benzofuranyl, benzothiophenyl, indolyl, dibenzofuranyl, dibenzothiophenyl, benzoxazolyl, benzothiazolyl, benzimidazolyl; Said a1 is independently selected from 0, 1, 2, 3, 4 or 5; said a2 is independently selected from 0, 1, 2, 3 or 4; said a3 is independently selected from 0, 1 or 2; said a4 is independently selected from 0, 1, 2 or 3; said a5 is independently selected from 0, 1, 2, 3, 4, 5, 6 or 7; said a6 is independently selected from 0, 1, 2, 3, 4, 5 or 6; said a7 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; said a8 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10.

4. The carbazole compound according to claim 1, characterized in that The L is selected from any one of the following groups or their combinations: R6, R 13 The same or different selected from hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, adamantyl, norbornane, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, indenyl, tetrahydronaphthyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, silyl or any combination thereof; The R 11 any one selected from hydrogen, deuterium, substituted or unsubstituted groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthryl, triphenylene, indenyl, tetrahydronaphthyl, benzocyclopropyl, benzocyclobutane, benzocyclopentyl, benzocyclohexyl, silyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, benzofuranyl, benzothiophenyl, indolyl, dibenzofuranyl, dibenzothiophenyl, benzoxazolyl, benzothiazolyl, benzimidazolyl; The R 16 , R 17 Any one independently selected from hydrogen, deuterium, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 alicyclic group, substituted or unsubstituted C6-C30 aryl group, fused ring group of substituted or unsubstituted C3-C12 alicyclic ring and C6-C30 aromatic ring, substituted or unsubstituted C2-C30 heteroaryl group; The c1 is selected from 0, 1, 2, 3 or 4; the c2 is selected from 0, 1, 2 or 3; the c3 is selected from 0, 1 or 2; the c4 is selected from 0, 1, 2, 3, 4, 5 or 6; the c5 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8.

5. The carbazole compound according to claim 1, characterized in that The L1 is selected from a single bond, a group as shown below or any one of their combinations: R7, R 14 the same or different selected from hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, adamantyl, norbornane, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, indenyl, tetrahydronaphthyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, silyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl or any combination thereof; The R8 is selected from hydrogen, deuterium, substituted or unsubstituted groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthryl, triphenylene, indenyl, tetrahydronaphthyl, benzocyclopropyl, benzocyclobutane, benzocyclopentyl, benzocyclohexyl, silyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, benzofuranyl, benzothiophenyl, indolyl, dibenzofuranyl, dibenzothiophenyl, benzoxazolyl, benzothiazolyl, benzimidazolyl; The d1 is independently selected from 0, 1, 2, 3 or 4; the d2 is independently selected from 0, 1, 2 or 3; the d3 is independently selected from 0, 1 or 2; the d4 is independently selected from 0, 1, 2, 3, 4, 5 or 6; the d5 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8.

6. The carbazole compound according to claim 1, characterized in that The L2 is selected from a single bond, a group as shown below or any one of their combinations: The R 10 , R 15 the same or different selected from hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, adamantyl, norbornane, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, indenyl, tetrahydronaphthyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, silyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl or any combination thereof; The R9 is selected from hydrogen, deuterium, substituted or unsubstituted methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthryl, triphenylene, indenyl, tetrahydronaphthyl, benzocyclopropyl, benzocyclobutane, benzocyclopentyl, benzocyclohexyl, silyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, benzofuranyl, benzothiophenyl, indolyl, dibenzofuranyl, dibenzothiophenyl, benzoxazolyl, benzothiazolyl, benzimidazolyl; The R 11 , R 12 the same or different selected from hydrogen, deuterium, substituted or unsubstituted groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthryl, triphenylene, indenyl, tetrahydronaphthyl, benzocyclopropyl, benzocyclobutane, benzocyclopentyl, benzocyclohexyl, silyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, benzofuranyl, benzothiophenyl, indolyl, dibenzofuranyl, dibenzothiophenyl, benzoxazolyl, benzothiazolyl, benzimidazolyl; The e1 is independently selected from 0, 1, 2, 3 or 4; the e2 is independently selected from 0, 1, 2 or 3; the e3 is independently selected from 0, 1 or 2; the e4 is independently selected from 0, 1, 2, 3, 4, 5 or 6; the e5 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8.

7. The carbazole compound according to claim 1, characterized in that The carbazole compound represented by Formula 1 is selected from any one of the following chemical structures:

8. An organic electroluminescent device, comprising an anode, an organic layer and a cathode, wherein the organic layer is located between the anode and the cathode or outside one or more of the anode and the cathode, characterized in that: The organic layer contains the carbazole compound according to any one of claims 1 to 7.

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

10. The organic electroluminescent device according to claim 8, characterized in that: The organic layer is located between the anode and the cathode, and includes at least one layer of a hole transport region, two or more light-emitting layers, a charge generation layer, and an electron transport region. The charge generation layer is located between two light-emitting layers, and the charge generation layer contains the carbazole compound described in any one of claims 1 to 7.

Images