CN115093414A - Carbazole derivative and organic light-emitting element containing carbazole derivative - Google Patents

Carbazole derivative and organic light-emitting element containing carbazole derivative Download PDF

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CN115093414A
CN115093414A CN202210823478.9A CN202210823478A CN115093414A CN 115093414 A CN115093414 A CN 115093414A CN 202210823478 A CN202210823478 A CN 202210823478A CN 115093414 A CN115093414 A CN 115093414A
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CN115093414B (en
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曹建华
张海威
杨美跃
李留洋
李程辉
王振宇
唐伟
姜坤
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Shanghai 800 Million Spacetime Advanced Material Co ltd
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Abstract

The invention relates to the technical field of organic electroluminescent materials, in particular to a carbazole derivative and application thereof. The structural formula of the carbazole derivative is shown as a formula (I); the compound shown in the formula (I) has a condensed carbazole structure, and can obviously reduce the driving voltage, improve the luminous efficiency and prolong the service life when being applied to an organic electroluminescent element,
Figure DDA0003745398700000011

Description

Carbazole derivative and organic light-emitting element containing carbazole derivative
Technical Field
The invention relates to the technical field of organic electroluminescent materials, in particular to a carbazole derivative and application thereof in an organic light-emitting element.
Background
In general, the organic light emitting phenomenon refers to a phenomenon in which light is emitted when electric energy is applied to an organic substance; that is, when an organic layer is disposed between an anode and a cathode, if a voltage is applied between the two electrodes, holes are injected from the anode into the organic layer, and electrons are injected from the cathode into the organic layer; when the injected holes and electrons meet, excitons are formed, and when the excitons transition to a ground state, light and heat are emitted.
In recent years, the organic electroluminescent display technology has matured, and some products have entered the market, but many problems still need to be solved in the industrialization process. In particular, various organic materials used for manufacturing elements have many problems which are not solved, such as carrier injection and transmission performance, electroluminescent performance of the materials, service life, color purity, matching between various materials and between various electrodes, and the like; especially, the light Emitting efficiency and the service life of the light Emitting element do not meet the practical requirements, which greatly limits the development of organic light-Emitting Diode (OLED) technology. The metal complex phosphorescent material utilizing triplet state luminescence has high luminescence efficiency, and green and red materials thereof meet the use requirements, but the metal complex phosphorescent material requires a phosphorescent material or a hole material with high triplet state energy level to be matched with the metal complex phosphorescent material. Therefore, the development of phosphorescent or hole materials having a high triplet energy level is an urgent need for the development of current OLEDs.
Under the current technological development, improvements are also needed, both for fluorescent materials and for phosphorescent materials, in particular in terms of operating voltage, efficiency and lifetime for use in organic electroluminescent elements and in terms of thermal stability during sublimation.
In view of this, the invention is particularly proposed.
Disclosure of Invention
In order to overcome the above-described problems of the conventional techniques and to further improve the characteristics of the organic electroluminescent element, development of a more stable and effective substance which can be used as a phosphorescent material or a hole-forming material in the organic electroluminescent element is continuously required.
The invention aims to provide a carbazole derivative which can improve the thermal stability and the carrier transport capacity of materials, and an organic electroluminescent element prepared by using the carbazole derivative can obviously reduce the driving voltage, improve the luminous efficiency and prolong the service life.
The invention also aims to provide application of the compound.
Specifically, the invention provides the following technical scheme:
the invention provides a carbazole derivative, the structural formula of which is shown as the formula (I):
Figure BDA0003745398680000011
wherein the content of the first and second substances,
L 1 selected from single bond, substituted or unsubstituted C 6 -C 60 Arylene, or substituted or unsubstituted C 2 -C 60 A heteroarylene group;
X 1 、X 2 、X 3 、X 4 、X 5 each independently is N or CR 5 ；
n is an integer of 0 to 5;
R 1 、R 2 、R 3 、R 4 、R 5 identical or different from hydrogen, deuterium, fluorine, hydroxyl, nitrile, nitro, carboxyl orIts carboxylate, sulfonic acid group or its sulfonate, phosphoric acid group or its phosphate, C 1 -C 40 Alkyl radical, C 1 -C 40 Alkoxy radical, C 2 -C 40 Alkenyl radical, C 1 -C 40 Alkylthio radical, C 1 -C 40 Alkoxy radical, C 3 -C 40 Cycloalkyl radical, C 1 -C 40 Alkyl sulfoxide group, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 6 -C 60 Aryl sulfoxide group, substituted or unsubstituted C 3 -C 40 Silyl, substituted or unsubstituted boron group, substituted or unsubstituted amine group, substituted or unsubstituted aryl phosphine group, substituted or unsubstituted phosphine oxide group, or substituted or unsubstituted C 2 -C 60 Heterocyclic aryl groups;
Ar 1 selected from substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 A condensed ring aryl group, or substituted or unsubstituted C 2 -C 60 Heterocyclic aryl groups.
Preferably, X is 1 、X 2 、X 3 、X 4 、X 5 Each independently is CR 5 。
Preferably, said R is 1 、R 2 、R 3 、R 4 、R 5 Each independently selected from the group consisting of hydrogen, deuterium, fluorine, nitrile, phenyl, biphenylyl, terphenylyl, naphthyl, phenanthryl, triphenylene, carbazole, dibenzofuran, or dibenzothiophene.
Preferably, n is 0, 1 or 2.
Preferably, Ar is 1 A group selected from: benzene, naphthalene, anthracene, benzanthracene, phenanthrene, pyrene,
Figure BDA0003745398680000022
Perylene, fluoranthene, tetracene, pentacene, benzopyrene, biphenyl, idobenzene, terphenylBiphenyl, tetrabiphenyl, terphenyl, fluorene, spirobifluorene, dihydrophenanthrene, dihydropyrene, tetrahydropyrene, cis-or trans-indenofluorene, cis-or trans-indenocarbazole, cis-or trans-indolocarbazole, triindene, isotridecyl, spirotriindene, spiroisotridecyl, furan, benzofuran, isobenzofuran, dibenzofuran, thiophene, benzothiophene, isobenzothiophene, dibenzothiophene, pyrrole, indole, isoindole, carbazole, pyridine, quinoline, isoquinoline, acridine, phenanthridine, benzo [5,6 ] anthracene]Quinoline, benzo [6,7 ]]Quinoline, benzo [7,8 ]]Quinoline, phenothiazine, phenoxazine, pyrazole, indazole, imidazole, benzimidazole, naphthoimidazole, phenanthroimidazole, pyridoimidazole, pyrazinoimidazole, quinoxaloimidazole, oxazole, benzoxazole, naphthooxazole, anthraoxazole, phenanthroixazole, isoxazole, 1, 2-thiazole, 1, 3-thiazole, benzothiazole, pyridazine, hexaazatriphenylene, benzopyridazine, pyrimidine, benzopyrimidine, quinoxaline, 1, 5-diaza-thracene, 2, 7-diaza, 2, 3-diaza-pyrene, 1, 6-diaza-pyrene, 1, 8-diaza-pyrene, 4,5,9, 10-tetraazaperylene, pyrazine, phenazine, phenoxazine, phenothiazine, fluorescent red ring, naphthyridine, azacarbazole, benzocarbazine, carboline, phenanthroline, 1,2, 3-triazole, 1,2, 4-triazole, benzotriazole, 1,2, 3-oxadiazole, 1,2, 4-oxadiazole, 1,2, 5-oxadiazole, 1,3, 4-oxadiazole, 1,2, 3-thiadiazole, 1,2, 4-thiadiazole, 1,2, 5-thiadiazole, 1,3, 4-thiadiazole, 1,3, 5-triazine, 1,2, 4-triazine, 1,2, 3-triazine, tetrazole, 1,2,4, 5-tetrazine, 1,2,3, 4-tetrazine, 1,2,3, 5-tetrazine, purine, pteridine, indolizine, quinazoline, and benzothiadiazole, or a group derived from a combination of these systems.
Further, said Ar 1 Selected from the group consisting of groups represented by II-1 to II-17:
Figure BDA0003745398680000021
wherein the content of the first and second substances,
Z 1 、Z 2 each independently selected from the group consisting of hydrogen, deuterium, halogen, hydroxy, nitrile, nitro, amino, amidino, hydrazine, hydrazone, and carboxyRadical or carboxylate thereof, sulfonic acid group or sulfonate thereof, phosphoric acid group or phosphate thereof, C 1 -C 40 Alkyl radical, C 2 -C 40 Alkenyl radical, C 2 -C 40 Alkynyl, C 1 -C 40 Alkoxy radical, C 3 -C 40 Cycloalkyl radical, C 3 -C 40 Cycloalkenyl radical, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 An arylthioether group, or a substituted or unsubstituted C 2 -C 60 Heterocyclic aryl groups;
x1 represents an integer of 1 to 4; x2 represents an integer of 1 to 3; x3 represents 1 or 2; x4 represents an integer of 1 to 6; x5 represents an integer of 1 to 5;
T 1 representation O, S, CR ’ R' or NAr ’ ；
R ’ R' are each independently selected from hydrogen, deuterium, C 1 ～C 40 Alkyl of (C) 1 ～C 40 With heteroalkyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Arylamino, or substituted or unsubstituted C 2 -C 60 Group consisting of heterocyclic aryl radicals, R ’ And R "may be optionally joined or fused to form one or more additional substituted or unsubstituted rings, with or without one or more heteroatoms N, P, B, O or S in the formed ring; preferably, R ’ R' is methyl, phenyl or fluorenyl;
Ar ’ is selected from the group consisting of C 1 ～C 40 Alkyl of (C) 1 ～C 40 Heteroalkyl of (a), C 3 ～C 40 Cycloalkyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Condensed ring aryl, substituted or unsubstituted C 6 -C 60 Arylamino, or substituted or unsubstituted C 2 -C 60 Heterocyclic aryl groups; preferably, Ar ’ Is methyl, ethyl, phenyl, biphenyl or naphthyl;
Figure BDA0003745398680000031
represents Ar 1 And L 1 The connecting key of (2).
Preferably, in the above compound, L is 1 Selected from the group consisting of the following groups III-1 to III-15:
Figure BDA0003745398680000032
wherein the content of the first and second substances,
Z 11 、Z 12 each independently selected from the group consisting of hydrogen, deuterium, hydrogen, halogen, hydroxy, nitrile, nitro, amino, amidino, hydrazine, hydrazone, carboxy or carboxylate thereof, sulfonic or sulfonate thereof, phosphoric or phosphate thereof, C 1 -C 40 Alkyl radical, C 2 -C 40 Alkenyl radical, C 2 -C 40 Alkynyl, C 1 -C 40 Alkoxy radical, C 3 -C 40 Cycloalkyl radical, C 3 -C 40 Cycloalkenyl radical, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 An arylthioether group, or a substituted or unsubstituted C 2 -C 60 Heterocyclic aryl groups;
Z 13 represents substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 An arylsulfonyl ether group, or a substituted or unsubstituted C 2 -C 60 One or more of a heterocyclic aryl group;
y1 represents an integer of 1 to 4; y2 represents an integer of 1 to 6; y3 represents an integer of 1 to 3; y4 represents an integer of 1 to 5;
T 3 represents an oxygen atom or a sulfur atom;
Figure BDA0003745398680000033
representL 1 And Ar 1 Or a linking bond of N.
In the present invention, the term "substituted or unsubstituted" means a compound selected from the group consisting of hydrogen, deuterium, a halogen atom, a hydroxyl group, a nitrile group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxyl group or a carboxylate thereof, a sulfonic acid group or a sulfonate thereof, a phosphoric acid group or a phosphate thereof, and C 1 -C 60 Alkyl radical, C 2 -C 60 Alkenyl radical, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy radical, C 3 -C 60 Cycloalkyl, C 3 -C 60 Cycloalkenyl radical, C 6 -C 60 Aryl radical, C 6 -C 60 Aryloxy radical, C 6 -C 60 An arylthioether group and C 2 -C 60 The heterocyclic aryl group may be substituted or unsubstituted with 1 or more substituents, or may be substituted or unsubstituted with substituents formed by connecting 2 or more substituents among the above-exemplified substituents.
Preferably, the compound is selected from compounds represented by the following formulae M470 to M622:
Figure BDA0003745398680000041
Figure BDA0003745398680000051
Figure BDA0003745398680000061
Figure BDA0003745398680000071
Figure BDA0003745398680000081
Figure BDA0003745398680000091
Figure BDA0003745398680000101
Figure BDA0003745398680000111
wherein G-is selected from O-, S-or one of the following structures:
Figure BDA0003745398680000112
and represents a bond.
The present invention also provides a method for preparing the carbazole derivative described above, as shown in scheme 1:
in the case of the scheme 1,
Figure BDA0003745398680000121
in scheme 1, the symbols used are as defined in formula (I), and Y is 1 、Y 2 、Y 3 、Y 4 Each independently selected from Cl, Br, I or OTf;
the raw materials for synthesizing the compound shown in the formula (I) can be purchased from commercial sources, the method principle, the operation process, the conventional post treatment, the column purification, the recrystallization purification and other means are well known by the synthesis personnel in the field, and the synthesis process can be completely realized to obtain the target product.
In particular, the compounds of formula (I) are represented by the formula 3-R 1 Substituted-5-halogenated carbazoles I-0 and R 2 Carrying out substitution reaction on the radical acetylene to prepare an intermediate I-1; carrying out a ring closure reaction on the intermediate I-1 to prepare an intermediate I-2; carrying out halogenation reaction on the carbazole intermediate I-2 to obtain I-3; carrying out coupling reaction on the intermediate I-3 and carbazole or carboline to prepare an intermediate I-4; intermediate I-4 with Ar 1 -(L 1 )n-Y 4 Carrying out a coupling reaction to prepare the compound of formula (I). Intermediate Ar 1 -(L 1 )n-Y 4 Prepared by palladium-catalyzed or base-catalyzed coupling reactions.
As palladium catalysts which may be used in the palladium-catalyzed coupling reaction, there may be selected: pd (P- t Bu 3 ) 2 、Pd(PPh 3 ) 4 、Pd 2 (dba) 3 、Pd 2 (dba) 3 CHCl 3 、PdCl 2 (PPh 3 ) 2 、PdCl 2 (CH 3 CN) 2 、Pd(OAc) 2 、Pd(acac) 2 、Pd/C、PdCl 2 、[Pd(allyl)Cl] 2 And the like, or a mixture of two or more thereof is used.
In addition, the base used in the palladium-catalyzed coupling reaction or base-catalyzed coupling reaction may be selected from: sodium tert-butoxide, potassium tert-butoxide, sodium hydride, lithium hydride, sodium tert-amylate, sodium ethoxide, sodium methoxide, sodium carbonate, potassium carbonate, cesium carbonate, lithium, potassium hydride, triethylamine, cesium fluoride, and the like, and mixtures of one or two or more thereof.
The coupling reaction may be carried out in an organic solvent, wherein the organic solvent may be selected from: ether solvents such as diethyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, 1, 4-dioxane, ethylene glycol ethyl ether, ethylene glycol diethyl ether, ethylene glycol methyl ether, diethylene glycol diethyl ether, or anisole, aromatic hydrocarbon solvents such as benzene, toluene, or xylene, chlorobenzene, dichlorobenzene, N-dimethylformamide, N-dimethylacetamide, N-methylpyrrolidone, dimethyl sulfoxide, and sulfolane, and one or a mixture of two or more thereof may be used.
The invention also provides an organic electroluminescent material, the raw material of which comprises the carbazole derivative; the organic electroluminescent material comprising the compound of the present invention has a carrier transport ability.
The invention also provides application of the heterocyclic compound in preparation of an organic electroluminescent element.
The present invention also provides an organic electroluminescent element comprising: the organic light-emitting diode comprises a first electrode, a second electrode, a sealing layer and more than one organic layer arranged between the first electrode and the second electrode; the material of at least one of the organic layer or the capping layer includes the carbazole derivative described above.
The organic electroluminescent element includes a cathode, an anode, and at least one light-emitting layer. In addition to these layers, it may also comprise further layers, for example in each case one or more hole-injecting, hole-transporting, hole-blocking, electron-transporting, electron-injecting, exciton-blocking, electron-blocking and/or charge-generating layers. An intermediate layer having, for example, exciton blocking function can likewise be introduced between the two light-emitting layers. However, it should be noted that each of these layers need not be present. The organic electroluminescent device described herein may include one light emitting layer, or it may include a plurality of light emitting layers. That is, a plurality of light-emitting compounds capable of emitting light are used in the light-emitting layer. Particularly preferred are systems with three light-emitting layers, wherein the three layers can exhibit blue, green and red light emission. If more than one light-emitting layer is present, at least one of these layers comprises the carbazole derivative of the invention according to the invention.
Further, the organic electroluminescent element according to the invention does not comprise a separate hole injection layer and/or hole transport layer and/or hole blocking layer and/or electron transport layer, i.e. the light-emitting layer is directly adjacent to the electron blocking layer or hole transport layer or the anode and/or the light-emitting layer is directly adjacent to the electron transport layer or electron injection layer or the cathode.
In the other layers of the organic electroluminescent element according to the invention, in particular in the hole-injecting and hole-transporting layer and in the electron-injecting and electron-transporting layer, all materials can be used in the manner conventionally used according to the prior art. The person skilled in the art will thus be able to use all materials known for organic electroluminescent elements in combination with the light-emitting layer according to the invention without inventive effort.
Preference is furthermore given to organic electroluminescent elements in which one or more layers are applied by means of a sublimation process in which the temperature in a vacuum sublimation apparatus is below 10 -5 Pa, preferably less than 10 -6 Pa is applied by vapor deposition. However, the initial pressure may also be even lower, e.g. below 10 -7 Pa。
Preference is likewise given to organic electroluminescent elements in which one or more layers are applied by means of an organic vapor deposition method or by means of carrier gas sublimation, where 10 -5 The material is applied under a pressure between Pa and 1 Pa. A particular example of this method is the organic vapour jet printing method, in which the material is applied directly through a nozzle and is therefore structured.
Preference is furthermore given to organic electroluminescent elements in which one or more layers are produced from solution, for example by spin coating, or by means of any desired printing method, for example screen printing, flexographic printing, offset printing, photoinitiated thermal imaging, thermal transfer, ink-jet printing or nozzle printing. Soluble compounds, for example, are obtained by appropriate substitution of a compound of formula (I). These methods are also particularly suitable for oligomers, dendrimers and polymers. Furthermore, hybrid methods are possible, in which, for example, one or more layers are applied from solution and one or more further layers are applied by vapor deposition.
These methods are generally known to those skilled in the art, and they can be applied to an organic electroluminescent element comprising the compound according to the present invention without inventive labor.
The invention therefore also relates to a method for producing an organic electroluminescent element according to the invention, at least one layer being applied by means of a sublimation method, and/or at least one layer being applied by means of an organic vapor deposition method or by means of carrier gas sublimation, and/or at least one layer being applied from solution by spin coating or by means of a printing method.
Furthermore, the present invention relates to a composition comprising at least one carbazole derivative of the present invention indicated above. The same preferences as indicated above for the organic electroluminescent elements apply to the compounds according to the invention. In particular, the compounds may furthermore preferably comprise further compounds. The processing of the compounds according to the invention from the liquid phase, for example by spin coating or by printing methods, requires the preparation of the compounds according to the invention. These formulations may be, for example, solutions, dispersions or emulsions. For this purpose, it may be preferred to use a mixture of two or more solvents. Suitable and preferred solvents are, for example, toluene, anisole, o-xylene, m-or p-xylene, methyl benzoate, mesitylene, tetralin, o-dimethoxybenzene, tetrahydrofuran, methyltetrahydrofuran, tetrahydropyran, chlorobenzene, dioxane, phenoxytoluene, in particular 3-phenoxytoluene, (-) -fenchytone, 1,2,3, 5-tetramethylbenzene, 1,2,4, 5-tetramethylbenzene, 1-methylnaphthalene, 2-methylbenzothiazole, 2-phenoxyethanol, 2-pyrrolidone, 3-methylanisole, 4-methylanisole, 3, 4-dimethylanisole, 3, 5-dimethylanisole, acetophenone, alpha-terpineol, benzothiazole, butyl benzoate, cumene, cyclohexanol, cyclohexanone, 4-methylanisole, toluene, xylene, acetone, xylene, or mixtures of the like, or mixtures of the, Cyclohexylbenzene, decalin, dodecylbenzene, ethyl benzoate, indane, methyl benzoate, 1-methylpyrrolidone, p-cymene, phenetole, 1, 4-diisopropylbenzene, dibenzyl ether, diethylene glycol butyl methyl ether, triethylene glycol butyl methyl ether, diethylene glycol dibutyl ether, triethylene glycol dimethyl ether, diethylene glycol monobutyl ether, tripropylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, 2-isopropylnaphthalene, pentylbenzene, hexylbenzene, heptylbenzene, octylbenzene, 1-bis (3, 4-dimethylphenyl) ethane, or a mixture of these solvents.
Preferably, the organic layer includes a hole injection layer, a hole transport layer, a hole blocking layer, a light emitting layer, an electron transport layer, an electron injection layer, or an electron blocking layer.
The invention also provides a consumer product comprising the organic electroluminescent element.
In addition, the starting materials used in the present invention are commercially available unless otherwise specified, and any range recited herein includes any value between the endpoints and any subrange between the endpoints or any value between the endpoints.
The invention has the following beneficial effects:
the carbazole derivative shown in the formula (I) provided by the invention has a high triplet state energy level, increases the conjugation of a carbazole parent nucleus, improves the thermal stability of the material and the capability of transporting carriers, and can obviously reduce the driving voltage, improve the luminous efficiency and prolong the service life when the carbazole derivative is applied to an organic electroluminescent element.
Drawings
Fig. 1 shows a schematic diagram of an organic light emitting device 100. The illustrations are not necessarily drawn to scale. The device 100 may include a substrate 101, an anode 102, a hole injection layer 103, a hole transport layer 104, an electron blocking layer 105, a light emitting layer 106, a hole blocking layer 107, an electron transport layer 108, an electron injection layer 109, a cathode 110, and a capping layer (CPL) 111. The device 100 may be fabricated by sequentially depositing the described layers.
Fig. 2 shows a schematic diagram of an organic light emitting device 200 with two light emitting layers. The device comprises a substrate 201, an anode 202, a hole injection 203, a hole transport layer 204, a first light emitting layer 205, an electron transport layer 206, a charge generation layer 207, a hole injection layer 208, a hole transport layer 209, a second light emitting layer 210, an electron transport layer 211, an electron injection layer 212, and a cathode 213. The device 200 may be prepared by sequentially depositing the described layers. Since the most common OLED devices have one light emitting layer, while device 200 has a first light emitting layer and a second light emitting layer, the light emitting peak shapes of the first light emitting layer and the second light emitting layer may be overlapping or cross-overlapping or non-overlapping. In the corresponding layers of device 200, materials similar to those described with respect to device 100 may be used. Fig. 2 provides one example of how some layers may be added from the structure of device 100.
Detailed Description
The following examples are intended to illustrate the invention but are not intended to limit the scope of the invention.
In the description of the present invention, "a plurality" means two or more unless otherwise specified; the terms "upper", "lower", and the like, indicate orientations or positional relationships based on the orientations or positional relationships shown in the drawings, and are only for convenience in describing the present invention and simplifying the description, but do not indicate or imply that the referred devices or elements must have a specific orientation, be constructed and operated in a specific orientation, and thus, should not be construed as limiting the present invention.
The experimental procedures used in the following examples are conventional unless otherwise specified. The experimental raw materials and the related equipments used in the following examples are commercially available unless otherwise specified, and the percentages are by mass unless otherwise specified.
The following test instruments and methods for performance testing of OLED materials and devices were used in the examples as follows:
OLED element performance detection conditions:
luminance and chromaticity coordinates: testing by using a spectrum scanner Photoresearch PR-715;
current density and lighting voltage: testing using a digital source table Keithley 2420;
power efficiency: tested using NEWPORT 1931-C.
Example 1
A method for preparing compound M473, comprising the steps of:
the first step is as follows: preparation of intermediate Int-1
Figure BDA0003745398680000141
20.0mmol of 5-bromo-3-chlorocarbazole (reactant 1) was dissolved in 40mL of toluene and 20mL of triethylamine, and under the protection of nitrogen, 22.0mmol of trimethylsilylacetylene (reactant 2), 4.0mmol of cuprous iodide, and 2.0mmol of PdCl were added 2 (PPh 3 ) 2 Heating reflux reaction is carried out for 24 hours, the temperature is reduced to room temperature, decompression concentration is carried out to dryness, and residues are separated and purified by a silica gel column to obtain a compound Int-1, a white solid, and the yield is 42%.
The second step: preparation of intermediate Int-2
Figure BDA0003745398680000151
Under the protection of nitrogen, 20.0mmol of Int-1 is dissolved in 80mL of nitromethane and 20mL of THF, 60.0mmol of copper bromide and 10.0mmol of anhydrous potassium phosphate are added, the mixture is stirred at room temperature for 12 hours, 20mL of concentrated hydrochloric acid and 20mL of dichloromethane are added, the mixture is stirred for 1 hour, an organic phase is separated, dried, filtered, concentrated under reduced pressure to dryness, and a residue is separated and purified by a silica gel column to obtain the compound Int-2 with yield of 84%.
Preparation of Compound B-1
Figure BDA0003745398680000152
Referring to the above-mentioned similar synthetic method, compound B-1 is prepared by replacing trimethylsilylacetylene in the first step only with aryl acetylene or alkyl acetylene or the like substituted acetylene, e.g., phenyl acetylene.
The third step: preparation of intermediate Int-3
Figure BDA0003745398680000153
Under the protection of nitrogen, 20.0mmol of Int-2 is dissolved in 50mL of glacial acetic acid, 7.7mmol of potassium iodate and 13.1mmol of potassium iodide are added, the mixture is heated to reflux and stirred for reaction for 2 hours, the mixture is cooled to room temperature and filtered, a filter cake is washed by water and saturated sodium bisulfite aqueous solution, and the white solid Int-3 is obtained after silica gel column separation and purification, and the yield is 92%.
The fourth step: preparation of intermediate Int-4
Figure BDA0003745398680000154
Under the protection of nitrogen, 10.0mmol of Int-3 is dissolved in 60mL of xylene, 12.0mmol of carbazole, 25.0mmol of anhydrous potassium carbonate, 1.0mmol of cuprous iodide and 2.5mmol of N, N' -dimethylethylenediamine are added, the temperature is raised to reflux and stirred for reaction for 5 hours, the mixture is cooled to room temperature, the filtration is carried out, a filter cake is washed by dichloromethane, the filtrate is decompressed, concentrated and dried, and is separated and purified by a silica gel column, so that yellow solid Int-4 is obtained, and the yield is 81%.
The fifth step: preparation of intermediate Int-5
Figure BDA0003745398680000161
Under the protection of nitrogen, 20.0mmol of Int-4 is dissolved in 60mL of toluene, and 30.0mmol of sodium tert-butoxide and 0.2mmol of Pd are added 2 (dba) 3 And 0.04mL of a 10% tri-tert-butylphosphine toluene solution, heating to 100 ℃, stirring for reaction for 12 hours, cooling to room temperature, adding 50mL of water, extracting with EA, drying the organic phase, filtering, concentrating under reduced pressure to dryness, dispersing and filtering with n-hexane to obtain Int-5 as a yellow solid, with yield: 87 percent.
And a sixth step: preparation of intermediate Int-6
Figure BDA0003745398680000162
Under the protection of nitrogen, 10.0mmol of intermediate Int-5 is dissolved in 40mL of dry DMSO, 12.0mmol of 65% sodium hydride solid is added, stirring reaction is carried out for 30 minutes, 12.0mmol of 2-chloro-4-biphenyl-6-phenyl-1, 3, 5-triazine (reactant 3) is added, the temperature is increased to 45 ℃, stirring reaction is carried out for 12 hours, the temperature is reduced to room temperature, the reaction solution is poured into 150mL of ice water, filtration is carried out, a filter cake is washed by water and ethanol, and separation and purification are carried out by a silica gel column, so that yellow solid Int-6 is obtained, and the yield is 85%.
The seventh step: preparation of Compound M473
Figure BDA0003745398680000163
10.0mmol of intermediate Int-6 was dissolved in 60mL of THF and 10mL of triethylamine, 0.5g of 5% palladium on carbon solid was added, hydrogen was introduced to 0.1MPa, the reaction was stirred at room temperature for 12 hours, filtered, the cake was washed with THF, the filtrate was concentrated under reduced pressure to dryness, separated and purified by a silica gel column, and recrystallized from toluene/THF to give M473 as a yellow solid in 95% yield, MS (MALDI-TOF): 662.2 m/z358[M+H] + ； 1 HNMR(δ、CDCl 3 )：8.36～8.32(2H,m)；8.18～8.13(2H,m)；8.07～8.05(1H,m)；7.95～7.92(2H,m)；7.90～7.86(3H,m)；7.83～7.81(1H,d)；7.78～7.70(3H,m)；7.68～7.63(2H,m)；7.59～7.56(1H,m)；7.53～7.44(6H,m)；7.42～7.38(2H,m)；7.34～7.30(2H,m)。
With reference to the above synthetic method, the following compounds shown in table 1 were prepared:
TABLE 1
Figure BDA0003745398680000164
Figure BDA0003745398680000171
Figure BDA0003745398680000181
Figure BDA0003745398680000191
Example 2
A process for the preparation of compound M522 comprising the steps of:
the first step is as follows: preparation of intermediate Int-7
Figure BDA0003745398680000192
Under the protection of nitrogen, 20.0mmol of Int-5 (reactant 1), 22.0mmol of phenylboronic acid (reactant 2), 45.0mmol of anhydrous potassium carbonate, 0.01mmol of Pd0132, 40mL of toluene, 20mL of ethanol and 20mL of water are mixed, heated to reflux, stirred and reacted for 12 hours, cooled to room temperature, 50mL of water is added, EA is used for extraction, an organic phase is dried, filtered, concentrated under reduced pressure and dried, and silica gel column separation and purification are carried out to obtain yellow solid Int-7, wherein the yield is as follows: and 90 percent.
With reference to the analogous synthetic procedures described above, the following compounds were prepared:
Figure BDA0003745398680000201
the second step is that: preparation of Compound M522
Figure BDA0003745398680000202
Under the protection of nitrogen, 10.0mmol of intermediate Int-7 is dissolved in 40mL of dry DMSO, 12.0mmol of 65% sodium hydride solid is added, stirring reaction is carried out for 30 minutes, 12.0mmol of 2-chloro-4-naphthyl-6-phenyl-1, 3, 5-triazine (reactant 3) is added, the temperature is increased to 45 ℃, stirring reaction is carried out for 12 hours, the temperature is reduced to room temperature, the reaction solution is poured into 150mL of ice water, filtration is carried out, a filter cake is washed by water and ethanol, separation and purification are carried out by a silica gel column, and toluene/THF recrystallization is carried out to obtain yellow solid M522, the yield is 87%, and MS (MALDI-TOF): 712.2509[ M + H ] M/z] + ； 1 HNMR(δ、CDCl 3 )：8.94(1H,s)；8.58～8.50(5H,m)；8.43～8.41(1H,m)；8.22～8.15(3H,m)；8.04～8.02(1H,d)；7.91～7.82(6H,m)；7.69～7.67(1H,m)；7.63～7.56(3H,m)；7.53～7.44(6H,m)；7.39～7.36(1H,m)；7.33～7.29(1H,m)。
With reference to the above synthetic method, the following compounds shown in table 2 were prepared:
TABLE 2
Figure BDA0003745398680000203
Figure BDA0003745398680000211
Figure BDA0003745398680000221
Figure BDA0003745398680000231
Example 3
The preparation method of the compound M566, taking G as O as an example, comprises the following steps:
the first step is as follows: preparation of intermediate Int-8
Figure BDA0003745398680000232
Referring to the synthesis method of the sixth step of example 1, only 2-chloro-4-biphenyl-6-phenyl-1, 3, 5-triazine in the sixth step of example 1 was replaced with 2-chloro-4- (dibenzo [ b, d ] furan-4-yl) -6-phenyl-1, 3, 5-triazine (reactant 2), and separated and purified using a silica gel column to obtain Int-8 as a yellow solid in yield: 84 percent.
The second step is that: preparation of Compound M566 (G: O)
Figure BDA0003745398680000233
Under the protection of nitrogen, 10.0mmol of intermediate Int-8 is dissolved in 50mL of dry toluene, and 11.0mmol of carbazole (reactant 3), 15.0mmol of sodium tert-butoxide, 1.0mmol of cuprous iodide and 0.1mmol of Pd are added 2 (dba) 3 And 0.05mL of a 10% solution of tributyl phosphonium in toluene, warmed to 100 ℃ and stirred for 12 hours, cooled to room temperature, added with 50mL of water, filtered, washed with water and ethanol, separated and purified by a silica gel column, and recrystallized from methylene chloride/THF to give M566 as a yellow solid with a yield of 87%, MS (MALDI-TOF): 841.2732[ M + H ] M/z] + ； 1 HNMR(δ、CDCl 3 )：8.54(1H,s)；8.35～8.32(2H,m)；8.19～8.14(3H,m)；8.12～8.05(2H,m)；8.01～7.98(2H,m)；7.95～7.82(5H,m)；7.69～7.66(2H,m)；7.60～7.58(2H,m)；7.55～7.48(7H,m)；7.38～7.32(3H,m)；7.21～7.15(3H,m)。
Preparation of Compound B-2
Figure BDA0003745398680000234
Under the protection of nitrogen, 10.0mmol of intermediate Int-5 is dissolved in 50mL of dry xylene, and 20.0mmol of carbazole, 15.0mmol of sodium tert-butoxide, 1.0mmol of cuprous iodide and 0.1mmol of Pd are added 2 (dba) 3 And 0.02mL of 10% toluene solution of phosphorus tri-tert-butyl, heating to 110 ℃, stirring for reaction for 12 hours, cooling to room temperature, adding 50mL of water, extracting with ethyl acetate, drying the organic phase, filtering, concentrating the filtrate under reduced pressure, dispersing the residue with 50mL of dichloromethane, filtering, separating and purifying the filtrate with a silica gel column, and recrystallizing with dichloromethane/THF to obtain the compound B-2 with the yield of 75%.
With reference to the analogous synthetic procedures described above, the following compounds shown in table 3 were prepared:
TABLE 3
Figure BDA0003745398680000241
Example 4
A process for the preparation of compound M573, comprising the steps of:
the first step is as follows: preparation of intermediate Int-9
Figure BDA0003745398680000242
10.0mmol of intermediate Int-5 (reaction 1) was dissolved in 40mL of THF and 10mL of triethylamine, 0.2g of 5% palladium/carbon was added, hydrogen was introduced to 0.1MPa, the reaction was stirred at room temperature for 12 hours, filtered, the cake was washed with THF, the filtrate was concentrated under reduced pressure to dryness, separated and purified by a silica gel column, and recrystallized from toluene/THF to obtain compound Int-9 in 100% yield.
The second step is that: preparation of Compound M573
Figure BDA0003745398680000251
Under the protection of nitrogen, 10.0mmol of intermediate Int-9 is dissolved in 50mL of dry xylene, and 12.0mmol of 2- ([1,1' -biphenyl) is added]-4-yl) -4- (2-bromophenyl) -6-phenyl-1, 3, 5-triazine (reaction 2), 15.0mmol sodium tert-butoxide, 0.1mmol Pd 2 (dba) 3 And 0.2mmol of XPhos, heated to 110 ℃, stirred to react for 12 hours, cooled to room temperature, added with 50mL of water, filtered, washed with water and ethanol, separated and purified by a silica gel column, and recrystallized from dichloromethane/THF to obtain a yellow solid M573 with a yield of 86%, MS (MALDI-TOF): 738.2663[ M + H ] M/z] + ； 1 HNMR(δ、CDCl 3 )：8.35～8.32(2H,m)；8.19～8.14(2H,m)；8.09～8.05(1H,m)；7.95～7.86(7H,m)；7.83～7.79(2H,m)；7.74～7.68(4H,m)；7.64～7.56(2H,m)；7.53～7.44(7H,m)；7.39～7.36(1H,m)；7.23～7.18(3H,m)。
With reference to the above synthetic method, the following compounds shown in table 4 were prepared:
TABLE 4
Figure BDA0003745398680000252
Figure BDA0003745398680000261
Figure BDA0003745398680000271
Figure BDA0003745398680000281
In the above examples 1 to 4, — G — is selected from — _ O —, — _ S —, or one of the following structures:
Figure BDA0003745398680000282
and represents a bond.
Example 5
An OLED element, as shown in fig. 1, the OLED element of this embodiment is a top emission light element, and includes a substrate 101, an anode layer 102 disposed on the substrate 101, a hole injection layer 103 disposed on the anode layer 102, a hole transport layer 104 disposed on the hole injection layer 103, an electron blocking layer 105 disposed on the hole transport layer 104, an organic light emitting layer 106 disposed on the electron blocking layer 105, an electron transport layer 107 disposed on the organic light emitting layer 106, an electron injection layer 108 disposed on the electron transport layer 107, a cathode layer 109 disposed on the electron injection layer 108, and a capping layer 110 disposed on the cathode 109, and the method for manufacturing the OLED element includes the following steps:
1) the glass substrate coated with the ITO conductive layer is subjected to ultrasonic treatment in a cleaning agent for 30 minutes, washed in deionized water, subjected to ultrasonic treatment in an acetone/ethanol mixed solvent for 30 minutes, baked to be completely dry in a clean environment, irradiated by an ultraviolet light cleaning machine for 10 minutes, and bombarded on the surface by a low-energy cation beam.
2) Placing the processed ITO glass substrate in a vacuum chamber, and vacuumizing to 1 × 10 -5 ～9×10 -3 Pa, depositing silver on the ITO film as anode layer to obtain a deposited film with a thickness of
Figure BDA0003745398680000291
Continuing to respectively evaporate compounds HI01 and F4TCNQ as hole injection layers, wherein F4TCNQ is 3% of HI01 by mass, and the thickness of the evaporated film is
Figure BDA0003745398680000292
3) The compound HTM102 is continuously deposited on the hole injection layer to form a hole transport layer, and the deposition film has a thickness of
Figure BDA0003745398680000293
4) Continuously depositing a compound EBL on the hole injection layer to form an electron blocking layer with a thickness of
Figure BDA0003745398680000294
5) The compound of the invention with formula (I) as a host material and RD08 as a doping material are continuously evaporated on the electron blocking layer, RD08 is 3% of the mass of the compound with formula (I), and the organic light-emitting layer obtained by evaporation is used as an organic light-emitting layer of the element, and the film thickness of the organic light-emitting layer is the same as that of the organic light-emitting layer
Figure BDA0003745398680000295
6) And continuously evaporating a layer of LiQ and ET01 on the organic light-emitting layer as an electron transport layer of the element, wherein ET01 is 50% of the mass of the LiQ, and the thickness of the evaporated film is
Figure BDA0003745398680000296
7) Continuously evaporating a layer of LiF on the electron transport layer to form an electron injection layer, wherein the thickness of the evaporated film is
Figure BDA0003745398680000297
8) Depositing a transparent cathode layer with Mg and Ag as elements on the electron injection layer at a mass ratio of 1:10 and a thickness of the deposited film
Figure BDA0003745398680000298
9) Depositing a CPL layer as element on the transparent cathode layer by vapor deposition to a thickness of
Figure BDA0003745398680000299
The OLED element provided by the invention is obtained.
The compound used in example 5 above has the following structure:
Figure BDA00037453986800002910
example 6
An organic electroluminescent device 200 is shown in fig. 2 and comprises a substrate 201, an anode 202, a hole injection 203, a hole transport layer 204, a first light emitting layer 205, an electron transport layer 206, a charge generation layer 207, a hole injection layer 208, a hole transport layer 209, a second light emitting layer 210, an electron transport layer 211, an electron injection layer 212, and a cathode 213.
Comparative example 1
Following the same procedure as in example 5, the compound (formula I) in step 5) was replaced with HS01 to give comparative element 1;
Figure BDA00037453986800002911
comparative example 2
Following the same procedure as in example 3, the compound (formula I) in step 5) was replaced with HS02 to give comparative element 2;
Figure BDA0003745398680000301
the organic electroluminescent element prepared by the above process was subjected to the following performance tests:
the driving voltage and current efficiency of the organic electroluminescent element prepared in example 5 and comparative examples 1 and 2 and the lifetime of the element were measured using a digital source meter and a luminance meter. Specifically, the voltage was raised at a rate of 0.1V per second, and it was determined that the luminance of the organic electroluminescent element reached 1000cd/m 2 The current density is measured at the same time as the driving voltage; the ratio of the brightness to the current density is the current efficiency; the LT 90% lifetime test is as follows: using a luminance meter at 1000cd/m 2 At luminance, the luminance decay of the organic electroluminescent element was measured to be 900cd/m while maintaining a constant current 2 Time in hours. The data listed in table 5 are relative data compared to comparative element 1.
TABLE 5
Figure BDA0003745398680000302
Figure BDA0003745398680000311
Figure BDA0003745398680000321
Figure BDA0003745398680000331
As can be seen from table 5, the driving voltage of the device prepared by the compound of the present invention is lower than that of HS01 under the same brightness, the current efficiency is improved significantly, which is up to 1.2 times that of the comparative device, and the LT 90% lifetime of the device is greatly improved.
The compound HS01 in comparative example 1 is different from the compound of the present invention in that the plane conjugation ability of benzocarbazole is weak, the transport of holes and electrons is unbalanced, the ability to accept holes is stronger than the ability to accept electrons, and this imbalance of transport affects the formation of excitons in the light-emitting layer, resulting in high voltage, low efficiency, and reduced lifetime. The carbazole bonded on the basis of the benzocarbazole of the compound improves the conjugation capability of a mother nucleus, so that the compound has excellent performances on molecular film formation and charge transmission, the charge transmission in an element is more balanced, and the element performance is improved.
Compared with the compound of the invention, the compound HS02 in the comparative example 2 is distinguished in that HS02 is naphthocarbazole, although the planar conjugation ability is enhanced, the planar conjugation ability is weak compared with the carbazole compound of the invention, and another carbazole ring is incorporated to form a large conjugated fused ring structure, so that the carbazole compound is excellent in molecular film formation and charge transmission, the charge transmission in the element is more balanced, and the element performance, especially LT 90% life, is greatly higher than that of a comparative element, so that the carbazole derivative of the invention is an organic electroluminescent material with excellent performance.
Although the invention has been described in detail hereinabove with respect to a general description and specific embodiments thereof, it will be apparent to those skilled in the art that modifications or improvements may be made thereto based on the invention. Accordingly, such modifications and improvements are intended to be within the scope of the invention as claimed.

Claims (10)

1. A carbazole derivative having a structural formula represented by formula (I):
Figure FDA0003745398670000011
wherein the content of the first and second substances,
L 1 selected from single bond, substituted or unsubstituted C 6 -C 60 Arylene, or selected from substituted or unsubstituted C 2 -C 60 A heteroarylene group;
n is an integer of 0 to 5;
X 1 、X 2 、X 3 、X 4 、X 5 each independently is N or CR 5 ；
R 1 、R 2 、R 3 、R 4 、R 5 The same or different compounds are selected from hydrogen, deuterium, fluorine, hydroxyl, nitrile, nitro, carboxyl or carboxylate thereof, sulfonic acid or sulfonate thereof, phosphoric acid or phosphate thereof, C 1 -C 40 Alkyl radical, C 1 -C 40 Alkoxy radical, C 2 -C 40 Alkenyl radical, C 1 -C 40 Alkylthio radical, C 1 -C 40 Alkoxy radical, C 3 -C 40 Cycloalkyl radical, C 1 -C 40 Alkyl sulfoxide radical, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 6 -C 60 Aryl sulfoxide radical, substituted or unsubstituted C 3 -C 40 Silyl, substituted or unsubstituted boron group, substituted or unsubstituted amine group, substituted or unsubstituted arylphosphino, substituted or unsubstituted phosphinoxide group,Or substituted or unsubstituted C 2 -C 60 Heterocyclic aryl groups;
Ar 1 selected from substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 A condensed ring aryl group, or substituted or unsubstituted C 2 -C 60 Heterocyclic aryl groups.
2. The carbazole derivative according to claim 1, wherein X is 1 、X 2 、X 3 、X 4 、X 5 Each independently is CR 5 ；
n is 0, 1 or 2;
R 1 、R 2 、R 3 、R 4 、R 5 each independently selected from the group consisting of hydrogen, deuterium, fluorine, nitrile, phenyl, biphenylyl, terphenylyl, naphthyl, phenanthryl, triphenylene, carbazole, dibenzofuran, or dibenzothiophene;
Ar 1 a group selected from: benzene, naphthalene, anthracene, benzanthracene, phenanthrene, pyrene,
Figure FDA0003745398670000022
Perylene, fluoranthene, tetracene, pentacene, benzopyrene, biphenyl, terphenyl, quaterphenyl, terphenyl, fluorene, spirobifluorene, dihydrophenanthrene, dihydropyrene, tetrahydropyrene, cis-or trans-indenofluorene, cis-or trans-indenocarbazole, cis-or trans-indolocarbazole, triindene, isotridendene, spirotriindene, spiroisotridendene, furan, benzofuran, isobenzofuran, dibenzofuran, thiophene, benzothiophene, isobenzothiophene, dibenzothiophene, pyrrole, indole, isoindole, carbazole, pyridine, quinoline, isoquinoline, acridine, phenanthridine, benzo [5,6 ] benzo]Quinoline, benzo [6,7 ]]Quinoline, benzo [7,8 ]]Quinoline, phenothiazine, phenoxazine, pyrazole, indazole, imidazole, benzimidazole, naphthoimidazole, phenanthroimidazole, pyridoimidazole, pyrazinoimidazole, quinoxaloimidazole, oxazole, benzoxazole, naphthooxazole, anthraoxazole, phenanthroimidazole, isoxazole, 1, 2-thiazole, naphthoxazine, benzoxazole, naphthoxazine, phenanthroimidazole, benzoxazole, naphthoxazine, benzoxazole, phenoxazine, and optionally substituted naphthoxazine,1, 3-thiazole, benzothiazole, pyridazine, hexaazatriphenylene, benzopyridazine, pyrimidine, benzopyrimidine, quinoxaline, 1, 5-diazaanthracene, 2, 7-diazapyrene, 2, 3-diazapyrene, 1, 6-diazapyrene, 1, 8-diazapyrene, 4,5,9, 10-tetraazaperylene, pyrazine, phenazine, phenoxazine, phenothiazine, fluorescent red ring, naphthyridine, azacarbazole, benzocarbazine, carboline, phenanthroline, 1,2, 3-triazole, 1,2, 4-triazole, benzotriazole, 1,2, 3-oxadiazole, 1,2, 4-oxadiazole, 1,2, 5-oxadiazole, 1,3, 4-oxadiazole, 1,2, 3-thiadiazole, 1,2, 4-thiadiazole, 1,2, 5-thiadiazole, 1,3, 4-thiadiazole, 1,3, 5-triazine, 1,2, 4-triazine, 1,2, 3-triazine, tetrazole, 1,2,4, 5-tetrazine, 1,2,3, 4-tetrazine, 1,2,3, 5-tetrazine, purine, pteridine, indolizine, quinazoline, and benzothiadiazole, or groups derived from combinations of these systems.
3. The carbazole derivative according to claim 1, wherein Ar is 1 Selected from the group consisting of groups represented by II-1 to II-17:
Figure FDA0003745398670000021
Figure FDA0003745398670000031
wherein the content of the first and second substances,
Z 1 、Z 2 each independently selected from the group consisting of hydrogen, deuterium, halogen, hydroxy, nitrile, nitro, amino, amidino, hydrazine, hydrazone, carboxy or carboxylate thereof, sulfonic or sulfonate thereof, phosphoric or phosphate thereof, C 1 -C 40 Alkyl radical, C 2 -C 40 Alkenyl radical, C 2 -C 40 Alkynyl, C 1 -C 40 Alkoxy radical, C 3 -C 40 Cycloalkyl radical, C 3 -C 40 Cycloalkenyl radical, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 An aryloxy group,Substituted or unsubstituted C 6 -C 60 An arylthioether group, or a substituted or unsubstituted C 2 -C 60 Heterocyclic aryl groups;
x1 represents an integer of 1 to 4; x2 represents an integer of 1 to 3; x3 represents 1 or 2; x4 represents an integer of 1 to 6; x5 represents an integer of 1 to 5;
T 1 represents O, S, CR 'R "or NAr';
r 'and R' are each independently selected from hydrogen, deuterium, C 1 ～C 40 Alkyl of (C) 1 ～C 40 With heteroalkyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Arylamino, or substituted or unsubstituted C 2 -C 60 Heterocyclic aryl groups, R' and R "may optionally be joined or fused to form one or more additional substituted or unsubstituted rings, with or without one or more heteroatoms N, P, B, O or S in the formed rings; preferably, R', R "are methyl, phenyl or fluorenyl;
ar' is selected from C 1 ～C 40 Alkyl of (C) 1 ～C 40 Heteroalkyl of (a), C 3 ～C 40 Cycloalkyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Condensed ring aryl, substituted or unsubstituted C 6 -C 60 Arylamino, or substituted or unsubstituted C 2 -C 60 Heterocyclic aryl groups; preferably, Ar' is methyl, ethyl, phenyl, biphenyl or naphthyl;
Figure FDA0003745398670000041
represents Ar 1 And L 1 The connecting key of (2).
4. The carbazole derivative according to claim 1, wherein L is 1 Selected from the group consisting of the following groups III-1 to III-15:
Figure FDA0003745398670000042
wherein the content of the first and second substances,
Z 11 、Z 12 each independently selected from the group consisting of hydrogen, deuterium, hydrogen, halogen, hydroxy, nitrile, nitro, amino, amidino, hydrazine, hydrazone, carboxy or carboxylate thereof, sulfonic or sulfonate thereof, phosphoric or phosphate thereof, C 1 -C 40 Alkyl radical, C 2 -C 40 Alkenyl radical, C 2 -C 40 Alkynyl, C 1 -C 40 Alkoxy radical, C 3 -C 40 Cycloalkyl radical, C 3 -C 40 Cycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 An arylthioether group, or a substituted or unsubstituted C 2 -C 60 Heterocyclic aryl groups;
Z 13 represents substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 An arylthioether group, or a substituted or unsubstituted C 2 -C 60 One or more of a heterocyclic aryl group;
y1 represents an integer of 1 to 4; y2 represents an integer of 1 to 6; y3 represents an integer of 1 to 3; y4 represents an integer of 1 to 5;
T 3 represents an oxygen atom or a sulfur atom;
Figure FDA0003745398670000051
represents L 1 And Ar 1 Or a nitrogen linkage.
5. The carbazole derivative according to any one of claims 1 to 4, wherein the carbazole derivative is selected from compounds represented by the following formulae M470-M622:
Figure FDA0003745398670000052
Figure FDA0003745398670000061
Figure FDA0003745398670000071
Figure FDA0003745398670000081
Figure FDA0003745398670000091
Figure FDA0003745398670000101
Figure FDA0003745398670000111
Figure FDA0003745398670000121
wherein G-is selected from O-, S-or one of the following structures:
Figure FDA0003745398670000122
and represents a bond.
6. An organic electroluminescent material characterized in that its raw material comprises the carbazole derivative as recited in any one of claims 1 to 5.
7. Use of the carbazole derivative as claimed in any one of claims 1 to 5 for producing an organic electroluminescent element.
8. An organic electroluminescent element, characterized by comprising: the organic light-emitting diode comprises a first electrode, a second electrode, a capping layer and more than one organic layer arranged between the first electrode and the second electrode; the material of at least one of the organic layer or the capping layer includes the carbazole derivative as recited in any one of claims 1 to 5.
9. The organic electroluminescent element according to claim 8, wherein the organic layer comprises a hole injection layer, a hole transport layer, a hole blocking layer, a light emitting layer, an electron transport layer, an electron injection layer, or an electron blocking layer.
10. A consumer product comprising the organic electroluminescent element according to claim 8 or 9.
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