CN112442041A - Carbazole derivative and application thereof - Google Patents

Carbazole derivative and application thereof Download PDF

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CN112442041A
CN112442041A CN202011324583.5A CN202011324583A CN112442041A CN 112442041 A CN112442041 A CN 112442041A CN 202011324583 A CN202011324583 A CN 202011324583A CN 112442041 A CN112442041 A CN 112442041A
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CN112442041B (en
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曹建华
戴雄
谢佩
李程辉
程友文
白爽
王学涛
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Beijing Bayi Space LCD Technology Co Ltd
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Abstract

The invention relates to the technical field of materials for organic electroluminescent elements, in particular to carbazole derivatives and application thereof; the structure of the carbazole derivative is shown as a formula (I); the carbazole derivative has higher triplet state energy level and high glass transition temperature, is suitable for being used as a material for an organic electroluminescent element, and the material for the organic electroluminescent element containing the carbazole derivative has the characteristics of low starting voltage, high luminous efficiency and high brightness. In addition, the carbazole derivative of the present invention hasExcellent thermal stability and film forming property, and can be used in materials for organic electroluminescent elements, display devices, and lighting devices, and can prolong the service life thereof, thereby reducing the manufacturing cost of the materials for organic electroluminescent elements, display devices, and lighting devices.
Figure 1

Description

Carbazole derivative and application thereof
Technical Field
The invention relates to the technical field of materials for organic electroluminescent elements, in particular to carbazole derivatives and application thereof.
Background
In recent years, organic electroluminescent display technologies have become mature, and some products have already entered the market, but in the course of industrialization, many problems still need to be solved, especially for various organic materials used for manufacturing devices, there are many problems that are still unsolved, such as carrier injection and transport properties, electroluminescent properties of materials, service life, color purity, matching between various materials and between various electrodes, and the like. Especially, the light emitting element has not yet achieved practical requirements in terms of luminous efficiency and service life, which greatly limits the development of OLED technology.
Organic electroluminescence is largely divided into fluorescence and phosphorescence, but according to the spin quantum statistical theory, the probability of singlet excitons and triplet excitons is 1:3, i.e., the theoretical limit of fluorescence from radiative transition of singlet excitons is 25%, and the theoretical limit of fluorescence from radiative transition of triplet excitons is 75%. It is urgent to use 75% of the energy of triplet excitons. Forrest et al discovered in 1997 that the phosphorescence electroluminescence phenomenon breaks through the limit of 25% efficiency of the quantum efficiency of the organic electroluminescence material, and arouses people to pay extensive attention to the metal complex phosphorescence material. Since then, much research has been conducted on phosphorescent materials.
The present invention has been made in view of the above circumstances.
Disclosure of Invention
In order to solve the above problems of the prior art, the present invention provides a novel carbazole derivative that is a raw material of a material for an organic electroluminescent element, and that can provide a material for an organic electroluminescent element and an organic electroluminescent element that have a reduced activation voltage, a high light emission efficiency, and an improved luminance.
In order to achieve the purpose, the invention adopts the following technical scheme:
a carbazole derivative, wherein the structure of the carbazole derivative is shown as formula (I):
Figure BDA0002793911670000021
wherein R is1～R13Same or different, selected from hydrogen, deuterium, having C1～C40Straight chain alkyl of (2) having C1～C40Linear heteroalkyl group of (A) having C3～C40A branched or cyclic alkyl group having C3～C40A branched or cyclic heteroalkyl group of (A) having C2～C40Alkenyl or alkynyl group of (A), an aromatic ring system or a heteroaromatic ring system having 5 to 60 carbon atoms, R1～R13Each of which may be substituted by one or more groups R, and wherein two or more adjacent substituent groups may optionally be joined or fused to form a mono-or polycyclic aliphatic, aromatic or heteroaromatic ring system;
Ar1is selected from the group consisting of having C1～C40Straight chain alkyl of (2) having C1～C40Linear heteroalkyl group of (A) having C3～C40A branched or cyclic alkyl group having C3～C40A branched or cyclic heteroalkyl group of (A) having C2～C40Alkenyl or alkynyl groups of (a), aromatic or heteroaromatic ring systems having 5 to 60 carbon atoms, which ring systems may be substituted by one or more radicals R;
each occurrence of R is the same or different and is selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a nitrile group, a nitro group, and N (Ar)2)2、N(R14)2、C(＝O)Ar2、C(＝O)R14、P(＝O)(Ar2)2Having a structure of C1～C40Straight chain alkyl of (2) having C1～C40Linear heteroalkyl group of (A) having C3～C40A branched or cyclic alkyl group having C3～C40A branched or cyclic heteroalkyl group of (A) having C2～C40Alkenyl or alkynyl groups of (A), aromatic or heteroaromatic ring systems having from 5 to 80 carbon atoms, aryloxy or heteroaryloxy groups having from 5 to 60 carbon atoms, each of the R groups being optionally substituted by one or more radicals R14Substituted, or combinations of these systems, wherein one or more non-adjacent-CH2The radicals may be substituted by R14C＝CR14、C≡C、Si(R14)2、Ge(R14)2、Sn(R14)2、C＝O、C＝S、C＝Se、C＝NR14、P(＝O)(R14)、SO、SO2、NR14O, S or CONR14And in which one or more hydrogen atoms are replaced by deuterium atoms, halogen atoms, nitrile groups or nitro groups, where two or more adjacent substituents R may optionally be joined or fused to form a mono-or polycyclic, aliphatic, aromatic or heteroaromatic ring system which may be interrupted by one or more radicals R14Substitution;
R14each occurrence of the same or different is selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a nitrile group, a nitro group, and N (Ar)2)2、N(R15)2、C(＝O)Ar2、C(＝O)R15、P(＝O)(Ar2)2Having a structure of C1～C40Straight chain alkyl of (2) having C1～C40Linear heteroalkyl group of (A) having C3～C40A branched or cyclic alkyl group having C3～C40A branched or cyclic heteroalkyl group of (A) having C2～C40One of alkenyl or alkynyl, aromatic or heteroaromatic ring system having 5 to 60 carbon atoms, aryloxy or heteroaryloxy having 5 to 60 carbon atoms, R14Each group of (1) may beOne or more radicals R15Substituted, or combinations of these systems, wherein one or more non-adjacent-CH2The radicals may be substituted by R15C＝CR15、C≡C、Si(R15)2、Ge(R15)2、Sn(R15)2、C＝O、C＝S、C＝Se、C＝NR15、P(＝O)(R15)、SO、SO2、NR15O, S or CONR15And wherein one or more hydrogen atoms may be replaced by deuterium atoms, halogen atoms, nitrile groups or nitro groups, wherein two or more adjacent substituents R14Aliphatic, aromatic or heteroaromatic ring systems which may optionally be joined or fused to form a single ring or multiple rings and which may be interrupted by one or more radicals R15Substitution;
Ar2identical or different at each occurrence and selected from aromatic or heteroaromatic ring systems having from 5 to 30 carbon atoms which may be substituted by one or more nonaromatic radicals R15Substitution; two groups Ar here bonded to the same nitrogen or phosphorus atom2Can also be selected from N (R) through a single bond15)、C(R15)2Oxygen or sulfur bridging groups;
R15selected from hydrogen atom, deuterium atom, fluorine atom, nitrile group, having C1～C20An aliphatic hydrocarbon group, an aromatic ring or a heteroaromatic ring system having 5 to 30 carbon atoms, wherein R15Wherein one or more hydrogen atoms may be replaced by deuterium atoms, halogen atoms, or nitrile groups, wherein two or more adjacent substituents R15They can form mono-or polycyclic aliphatic, aromatic or heteroaromatic ring systems with one another.
Aromatic or heteroaromatic ring systems in the sense of the present invention are intended to be taken to mean systems which do not necessarily contain only aryl or heteroaryl groups, but in which a plurality of aryl or heteroaryl groups may also be linked by non-aromatic units, for example C, N, O or an S atom. Thus, for example, as with systems in which two or more aryl groups are linked by, for example, a short alkyl group, systems such as fluorene, 9' -spirobifluorene, 9-diarylfluorene, triarylamine, diaryl ether, and the like are also considered to refer to aromatic ring systems in the sense of the present invention.
Aryl in the sense of the present invention contains 5 to 60 carbon atoms and heteroaryl in the sense of the present invention contains 5 to 60 carbon atoms and at least one heteroatom, with the proviso that the sum of carbon atoms and heteroatoms is at least 5; the heteroatom is preferably selected from N, O or S. Aryl or heteroaryl herein is considered to mean a simple aromatic ring, i.e. benzene, naphthalene, etc., or a simple heteroaromatic ring, such as pyridine, pyrimidine, thiophene, etc., or a fused aryl or heteroaryl group, such as anthracene, phenanthrene, quinoline, isoquinoline, etc. Aromatic rings, such as biphenyl, which are connected to one another by single bonds, are, in contrast, not referred to as aryl or heteroaryl groups, but rather as aromatic ring systems.
Containing 1 to 40 carbon atoms and in which the individual hydrogen atoms or-CH2The aliphatic hydrocarbon radicals or alkyl or alkenyl or alkynyl radicals which may also be substituted by the abovementioned radicals are preferably to be understood as meaning the following radicals: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, neopentyl, cyclopentyl, n-hexyl, neohexyl, cyclohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, cyclohexenyl, heptenyl, cycloheptenyl, octenyl, cyclooctenyl, ethynyl, propynyl, butynyl, pentynyl, hexynyl, heptynyl or octynyl. The alkoxy group, preferably an alkoxy group having 1 to 40 carbon atoms, is considered to mean a methoxy group, a trifluoromethoxy group, an ethoxy group, a n-propoxy group, an isopropoxy group, a n-butoxy group, an isobutoxy group, a sec-butoxy group, a tert-butoxy group, a n-pentyloxy group, a sec-pentyloxy group, a 2-methylbutyloxy group, a n-hexyloxy group, a cyclohexyloxy group, a n-heptyloxy group, a cycloheptyloxy group, a n-octyloxy group, a cyclooctyloxy group, a 2-ethylhexyloxy group, a pentafluoroethoxy group and a 2,2, 2-. The heteroalkyl group is preferably an alkyl group having 1 to 40 carbon atoms, meaning a hydrogen atom or-CH alone2The radical which may be substituted by an oxygen, sulfur or halogen atom, is understood to mean an alkoxy, alkylthio, fluorinated alkoxy or fluorinated alkylthio radical, in particular a methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, methylthio, ethylthio radicalN-propylthio, isopropylthio, n-butylthio, isobutylthio, sec-butylthio, tert-butylthio, trifluoromethylthio, trifluoromethoxy, pentafluoroethoxy, pentafluoroethylthio, 2,2, 2-trifluoroethoxy, 2,2, 2-trifluoroethylthio, vinyloxy, vinylthio, propenyloxy, propenylthio, butenylthio, butenyloxy, pentenyloxy, pentenylthio, cyclopentenyloxy, cyclopentenylthio, hexenyloxy, hexenylthio, cyclohexenyloxy, cyclohexenylthio, ethynyloxy, ethynylthio, propynyloxy, propynylthio, butynyloxy, butynylthio, pentynyloxy, pentynylthio, hexynyloxy, hexynylthio.
In general, the cycloalkyl, cycloalkenyl groups according to the invention may be cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptyl, cycloheptenyl, where one or more-CH may be present2The radicals may be replaced by the radicals mentioned above; furthermore, one or more hydrogen atoms may also be replaced by deuterium atoms, halogen atoms, or nitrile groups.
The aromatic or heteroaromatic ring atoms according to the invention may in each case also be substituted by the abovementioned radicals R14Substituted aromatic or heteroaromatic ring systems, in particular radicals derived from: benzene, naphthalene, anthracene, benzanthracene, phenanthrene, pyrene,
Figure BDA0002793911670000051
Perylene, fluoranthene, tetracene, pentacene, benzopyrene, biphenyl, 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 ] indole, perylene, anthracene, phenanthrene, perylene]Quinoline, benzo [6,7 ]]Quinoline, benzo [7,8 ]]Quinoline, phenothiazine, phenoxazine, pyrazole, indazole, imidazole, benzimidazole, naphthoimidazole, phenanthroimidazole, pyridoimidazole, pyrazinoimidazole, quinoxalineBenzimidazole, oxazole, benzoxazole, naphthooxazole, anthraoxazole, phenanthrooxazole, isoxazole, 1, 2-thiazole, 1, 3-thiazole, benzothiazole, pyridazine, hexaazatriphenylene, benzopyridazine, pyrimidine, benzopyrimidine, quinoxaline, 1, 5-diazahnthracene, 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, isoxazole, 1, 2-thiazole, 1, 3-thiazole, 4-diazapyrene, 4-pyrene, 4, phenanthroline, phenanthr, 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 and benzothiadiazole or groups derived from combinations of these systems.
Further, said R1～R13The same or different, selected from one of hydrogen, deuterium, aromatic ring system or heteroaromatic ring system with 5-60 carbon atoms, wherein R is1～R13Each of which may be substituted by one or more groups R, and wherein two or more adjacent substituent groups may optionally be joined or fused to form a mono-or polycyclic aliphatic, aromatic or heteroaromatic ring system;
further, the structure of the carbazole derivative mainly comprises the following CJHK 018-CJHK 194:
Figure BDA0002793911670000061
Figure BDA0002793911670000071
Figure BDA0002793911670000081
Figure BDA0002793911670000091
Figure BDA0002793911670000101
Figure BDA0002793911670000111
Figure BDA0002793911670000121
Figure BDA0002793911670000131
Figure BDA0002793911670000141
wherein, T is1、T2Each independently selected from-O-, -S-, or any of the following structures:
Figure BDA0002793911670000142
Figure BDA0002793911670000151
and represents a bond.
Further, said R1～R13Identical or different, selected from hydrogen, deuterium;
ar is1Selected from aromatic or heteroaromatic ring systems having 5 to 60 carbon atoms, which ring systems may be substituted by one or more radicals R;
the present invention provides an application of the carbazole derivative in an organic element.
Meanwhile, the invention also provides application of the carbazole derivative in an organic element as a luminescent layer material, a hole transport layer material, a hole barrier layer material or an encapsulation layer material.
Further, the organic element is an organic electroluminescent element, an organic field effect transistor or an organic thin film solar cell.
An organic electroluminescent element comprising a first electrode, a second electrode and a plurality of organic layers located between the first electrode and the second electrode, at least one of the organic layers comprising the carbazole derivative.
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 layers, hole-transporting layers, hole-blocking layers, electron-transporting layers, electron-injecting layers, exciton-blocking layers, electron-blocking layers 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 element 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, according to the invention, the carbazole derivative described in the invention.
In the other layers of the organic electroluminescent element according to the invention, in particular in the hole transport layer and in the hole blocking layer and the thin-film encapsulation layer, all materials can be used in the manner generally 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.
Further, the following organic electroluminescence is preferableOptical element, one or more layers being applied by means of a sublimation process, in which the temperature is lower than 10 ℃ in a vacuum sublimation device-5Pa, preferably less than 10-6Pa is applied by vapor deposition. However, the initial pressure may also be even lower, e.g. below 10-7Pa。
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 10-5The 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 obtained by appropriate substitution. 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.
Further, the organic layer may further include one or more selected from an electron injection layer, an electron transport layer, a hole blocking layer, an electron blocking layer, a hole transport layer, a hole injection layer, a light emitting layer, and a light refraction layer.
The organic electroluminescent element of the present invention may be either a top emission light element or a bottom emission light element. The structure and the production method of the organic electroluminescent element of the present invention are not limited. The organic electroluminescent element prepared by the compound can reduce the starting voltage and improve the luminous efficiency and brightness.
A display device includes the organic electroluminescent element.
An illumination device comprising the organic electroluminescent element.
The material for organic devices of the present invention contains the carbazole derivative of the present invention. The material for organic devices may be composed of the compound of the present invention alone or may contain other compounds.
The carbazole derivative of the present invention contained in the material for an organic electroluminescent element of the present invention can be used as a host material. In this case, the material for an organic electroluminescent element of the present invention may contain another compound as a dopant.
The material for an organic electroluminescent element of the present invention can also be used as a material for a hole transport layer, an enhancement layer, a light-emitting layer, an electron transport layer, a charge generation layer, an electron blocking layer, an encapsulation layer, or a photorefractive layer.
Compared with the prior art, the invention has the beneficial effects that: the carbazole derivative has higher triplet state energy level and high glass transition temperature, is suitable for being used as a material for an organic electroluminescent element, and the material for the organic electroluminescent element containing the carbazole derivative has the characteristics of low starting voltage, high luminous efficiency and high brightness. The carbazole derivative of the present invention has excellent thermal stability and film-forming properties, and can be used in a material for an organic electroluminescent element, a display device, and a lighting device, and can prolong the service life thereof, thereby reducing the production cost of the material for an organic electroluminescent element, the display device, and the lighting device.
Drawings
FIG. 1 is a schematic view of a bottom emission example of an organic electroluminescent device of the present invention;
FIG. 2 is a schematic view showing an example of top emission of an organic electroluminescent device of the present invention;
in the figure: 1. a substrate; 2. an anode; 3. a hole injection layer; 4. a hole transporting/electron blocking layer; 5. a light emitting layer; 6. a hole blocking/electron transporting layer; 7. an electron injection layer; 8. and a cathode.
Detailed Description
The following examples are intended to illustrate the invention but are not intended to limit the scope of the invention.
In order to make the objects, technical solutions and advantages of the present invention more apparent, the technical solutions of the present invention will be described in detail below. It is to be understood that the described embodiments are merely exemplary of the invention, and not restrictive of the full scope of the invention. All other embodiments, which can be derived by a person skilled in the art from the examples given herein without any inventive step, are within the scope of the present invention.
The following examples illustrate the performance of OLED materials and devices as follows:
OLED element performance detection conditions:
luminance and chromaticity coordinates: testing with a photosresearch PR-715 spectrum scanner;
current density and lighting voltage: testing using a digital source table Keithley 2420;
power efficiency: tested using NEWPORT 1931-C;
and (3) life test: LTS-1004AC service life testing device
Example 1
The preparation method of the intermediate Int-2 comprises the following steps:
the first step is as follows: preparation of Compound Int-1
Figure BDA0002793911670000181
0.9mol of 1-bromocarbazole, 1.1mol of 1, 8-dibromonaphthalene and 2000mL of xylene are mixed, and 1.2mol of sodium tert-butoxide and 4.5mmol of Pd are added under the protection of nitrogen2(dba)3CHCl3And 2.0mL of 10% toluene solution of tri-tert-butylphosphine, heating to 110 ℃, stirring for reaction for 15 hours, cooling to room temperature, adding 200mL of water for dilution, extracting with toluene, collecting the organic phase, drying, filtering, concentrating the filtrate under reduced pressure to dryness, and recrystallizing with ethanol to obtain the intermediate Int-2, a yellow solid, with a yield of 72%.
The second step is that: preparation of intermediate Int-2
Figure BDA0002793911670000191
0.5mol of intermediate Int-1 is dissolved in 2000mL of dry toluene, 0.55mol of parachloroaniline and 1.5mol of sodium tert-butoxide are added under the protection of nitrogen, and 2.5mmol of Pd are added2(dba)3CHCl3And 1.0mL of a 10% solution of tri-tert-butylphosphine in toluene, warmed to 100 ℃, stirred to react for 16 hours, cooled to room temperature, diluted with 100mL of water, extracted with toluene, the organic phase collected, dried, filtered, and the filtrate concentrated to dryness under reduced pressure, purified by separation with a silica gel column, and recrystallized with ethanol to give the intermediate Int-2, a yellow solid, yield 66%, ms (esi): 416.2,416.3.
Example 2
The preparation method of the intermediate Int-4 comprises the following steps:
the first step is as follows: preparation of Compound Int-3
Figure BDA0002793911670000192
Dissolving 0.75mol of 1-aminocarbazole in 2200mL of dry toluene, adding 0.5mol of 1, 8-dibromonaphthalene and 0.75mol of sodium tert-butoxide under the protection of nitrogen, and then adding 2.5mmol of Pd2(dba)3And 5.0mmol of Xantphos, heating to 100 ℃, stirring for reaction for 12 hours, cooling to room temperature, adding 100mL of water for dilution, extracting with toluene, collecting an organic phase, drying, filtering, concentrating the filtrate under reduced pressure to dryness, separating and purifying by using a silica gel column, and recrystallizing by using ethanol to obtain an intermediate Int-3, namely a white solid, wherein the yield is 75%.
The second step is that: preparation of Compound Int-4
Figure BDA0002793911670000201
0.5mol of intermediate Int-3 is dissolved in 2000mL of dry xylene, and 0.75mol of sodium tert-butoxide and 2.0mmol of Pd are added under nitrogen protection2(dba)3CHCl3And 1.0mL of 10% tritertineAnd (3) heating the solution of the butyl phosphorus and toluene to 100 ℃, stirring the solution to react for 12 hours, cooling the solution to room temperature, adding 200mL of water to dilute the solution, extracting the solution with toluene, collecting an organic phase, drying the organic phase, filtering the solution, concentrating the filtrate under reduced pressure to dryness, and recrystallizing the filtrate with ethanol to obtain an intermediate Int-4 which is a yellow solid and has the yield of 56 percent, and MS (ESI): 306.1.
example 3
Preparation of Compound CJHK021, with T1The compound CJHK021-1, which is N-phenyl, is exemplified by:
Figure BDA0002793911670000202
10.0mmol of intermediate Int-2 is dissolved in 60mL of toluene, and 12.0mmol of N-phenyl-3-carbazole boronic acid (PC-boronic acid), 24.0mmol of anhydrous potassium carbonate and 0.01mmol of Pd (PPh) are added under the protection of nitrogen3)4Heating the catalyst, refluxing and stirring for reaction for 12 hours, cooling to room temperature, adding 50mL of water for dilution, extracting with dichloromethane, collecting the lower organic phase, drying, filtering, concentrating the filtrate under reduced pressure to dryness, and separating and purifying the solid by using a silica gel column to obtain the compound CJHK021-1, a yellow solid with the yield of 86%.
MS and of compound CJHK021-11The HNMR test results are as follows:
MS(MALDI-TOF)：m/z 624.2455[M+H]+；1HNMR(δ、CDCl3)：8.19～8.15(3H,m)；7.98～7.96(1H,d)；7.72～7.65(4H,m)；7.58～7.51(7H,m)；7.44～7.31(8H,m)；7.26～7.22(4H,m)；7.16～7.14(1H,m)；7.06～7.04(1H,m)。
example 4
Preparation of CJHK020 to CJHK049 referring to the preparation of CJHK021-1 in example 3, the 9-phenylcarbazole-3-boronic acid in example 3 was replaced with only different organic boronic acids, and other experimental parameters were routinely adjusted to prepare CJHK020 to CJHK 049.
Example 5
Preparation of compound CJHK 085:
Figure BDA0002793911670000211
10.0mmol of intermediate Int-4 was dissolved in 60mL of toluene, and 12.0mmol of 2- (3-bromophenyl) -4, 6-diphenyl-1, 3, 5-triazine, 15.0mmol of sodium tert-butoxide, 0.1mmol of Pd were added under nitrogen protection2(dba)3CHCl3And 0.02mL of 10% toluene solution of phosphorus tri-t-butoxide, heated to 100 deg.C, stirred for reaction for 12 hours, cooled to room temperature, diluted with 100mL of water, filtered, the filter cake washed with water, ethanol, and recrystallized from toluene-THF to give compound CJHK085 as a yellow solid in 87% yield.
MS and of compound CJHK0851The HNMR test results are as follows:
MS(MALDI-TOF)：m/z 614.2362[M+H]+；1HNMR(δ、CDCl3)：8.79～8.75(4H,m)；8.38～8.36(1H,d)；8.19～8.16(2H,m)；7.82～7.77(2H,m)；7.59～7.33(13H,m)；7.24～7.18(2H,m)；7.09～7.02(2H,m)；6.98～6.96(1H,m)。
example 6
Preparation of CJHK018 to CJHK019, CJHK084, CJHK086 to CJHK088, CJHK090 to CJHK102, CJHK147 to CJK149 and CJHK186 to CJHK194 referring to the preparation method of the compound CJHK085 in example 5, the compounds CJHK018 to CJHK019, CJHK084, CJHK086 to CJHK088, CJHK090 to CJHK102, CJHK147 to CJK149 and CJ 186 to CJHK194 were prepared by replacing only the halide intermediates with different substituents for 2- (3-bromophenyl) -4, 6-diphenyl-1, 3, 5-triazine in example 5 and by performing routine adjustment of other experimental parameters.
Example 7
Preparation of compound CJHK 063:
Figure BDA0002793911670000221
10.0mmol of intermediate Int-4 is dissolved in 60mL of dry THF, cooled to 0 ℃ in an ice water bath under the protection of nitrogen, 11.0mmol of 65% sodium hydride solid is added in portions, stirred for reaction for 1 hour, 11.0mmol of 2-chloro-4- (2-naphthyl) -6-phenyl-1, 3, 5-triazine is added, the mixture is heated to room temperature and stirred for reaction for 24 hours, 50mL of water is added for dilution, extraction is carried out by ethyl acetate, an organic phase is collected, dried and filtered, a filtrate is concentrated under reduced pressure and dried, and is separated and purified by a silica gel column to obtain a compound HK063, a yellow solid with the yield of 92%.
MS and of compound CJHK0631The HNMR test results are as follows:
MS(MALDI-TOF)：m/z 588.2204[M+H]+；1HNMR(δ、CDCl3)：8.93(1H,s)；8.57～8.51(4H,m)；8.22～8.20(1H,d)；8.09～7.96(4H,m)；7.63～7.55(4H,m)；7.49～7.35(6H,m)；7.15～7.09(3H,m)；7.06～7.04(2H,m)。
example 8
Preparation of the compounds CJHK 060-CJHK 062, CJHK 064-CJHK 083, CJHK089, CJHK 165-CJHK 185 referring to the preparation method of example 7, the compounds CJHK 060-CJHK 062, CJHK 064-CJHK 083, CJHK089, CJHK 165-CJCJCJCJCJCJCJ 185 in the compound formula I were prepared by replacing 2-chloro-4- (2-naphthyl) -6-phenyl-1, 3, 5-triazine in example 7 with different halides and performing general adjustment of other experimental parameters.
Example 9
The preparation method of the compound CJHK160 comprises the following steps:
by T1Is C (CH)3)2Compound CJHK160-1 of (a):
the first step is as follows: preparation of Compound Int-6
Figure BDA0002793911670000231
10.0mmol of intermediate Int-5 (prepared by the synthesis method of reference example 1) was dissolved in 80mL of dry THF, cooled to-80 ℃ in an ice water bath under the protection of nitrogen, 4.8mL of 2.5M n-butyllithium n-hexane solution was added dropwise, stirred for 1 hour, 15.0mmol of trimethyl borate was added dropwise, stirred for 1 hour, warmed to room temperature, 50mL of dilute hydrochloric acid aqueous solution was added dropwise, stirred for 30 minutes, extracted with ethyl acetate, the organic phase was collected, dried, filtered, the filtrate was concentrated under reduced pressure to dryness, dispersed with petroleum ether, and filtered to obtain intermediate Int-6, a yellow solid, with a yield of 78%.
The second step is that: preparation of Compound Int-7
Figure BDA0002793911670000232
10.0mmol of intermediate Int-6 prepared in the previous step was dissolved in 60mL of toluene, and 8.6mmol of p-bromoiodobenzene, 20.0mmol of anhydrous sodium carbonate and 0.01mmol of Pd (PPh) were added under nitrogen protection3)4And heating the catalyst, refluxing and stirring for reacting for 8 hours, cooling to room temperature, adding 50mL of water for diluting, extracting with dichloromethane, collecting a lower organic phase, drying, filtering, concentrating the filtrate under reduced pressure to dryness, and separating and purifying the solid by using a silica gel column to obtain an intermediate Int-7 which is a white solid with the yield of 84%.
The third step: compound CJHK160-1 (T)1Is C (CH)3)2) Preparation of
Figure BDA0002793911670000241
10.0mmol of the intermediate Int-7 prepared in the previous step was dissolved in 80mL of toluene, and 9.0mmol of N- ([1, 1' -biphenyl) was added under nitrogen protection]-2-yl) -9, 9-dimethyl-9H-fluoren-2-amine, 15.0mmol of sodium tert-butoxide, 0.1mmol of Pd2(dba)3CHCl3And 0.01mL of 10% toluene solution of phosphorus tri-t-butoxide, heating to 100 deg.C, stirring for 12 hours, cooling to room temperature, diluting with 100mL of water, extracting with ethyl acetate, collecting the organic phase, drying, filtering, concentrating the filtrate under reduced pressure to dryness, and recrystallizing with toluene-THF to give the compound CJHK160-1 as a yellow solid in 82% yield.
MS and of Compound CJHK160-11The HNMR test results are as follows:
MS(MALDI-TOF)：m/z 818.3551[M+H]+；1HNMR(δ、CDCl3)：8.29～8.26(1H,d)；8.19(1H,s)；8.01～7.98(3H,m)；7.90～7.88(1H,m)；7.82～7.71(7H,m)；7.69～7.48(8H,m)；7.40～7.29(9H,m)；7.24～7.21(2H,m)；7.17～7.12(2H,m)；7.08～7.02(3H,m)；1.66(6H,s)。
example 10
Preparation of the compounds CJHK050 to CJHK059, CJHK103 to CJHK146, CJHK150 to CJHK164 referring to the preparation method of the compound CJHK160-1 in example 9, the compounds CJHK050 to CJHK050, CJCJ 103 to CJHK146, CJHK150 to CJHK164 were prepared by replacing only the different oncotic amine intermediates for N- ([1, 1' -biphenyl ] -2-yl) -9, 9-dimethyl-9H-fluoren-2-amine of the third step in example 9, or replacing the intermediate Int-7 of the third step in example 9 with different halides, with other experimental parameters being routinely adjusted.
Comparative example 1
The following compound a was used as a green host material, the following compound B was used as a green dopant material, the compound C was used as a hole injection material, the compound D was used as a hole transport material, the compound G was used as an electron transport dopant material, and LiQ was used as an electron transport host material.
Figure BDA0002793911670000251
Compound C
Figure BDA0002793911670000253
/D
Figure BDA0002793911670000254
/A+B(5％)
Figure BDA0002793911670000255
/LiQ+G(50％)
Figure BDA0002793911670000256
/LiF
Figure BDA0002793911670000257
Al (2nm) was sequentially deposited on ITO glass by an EL deposition apparatus manufactured by SNU to produce a green light element, and an organic electroluminescent element as a green light was produced.
Test example 1
The organic electroluminescent element was prepared according to the method of comparative example 1 by replacing compound a in comparative example 1 with the compounds CJHK018 to CJHK194 of the present invention.
The results of measuring the properties of the obtained organic electroluminescent element are shown in Table 1, wherein the driving voltage (V), the current efficiency (LE), the color Coordinate (CIE), and the full width at half maximum (FWHM) were measured at a current density of 10mA/cm2Conditions were obtained and the voltage, LE, FWHM and LT 90% were normalized to the reference.
TABLE 1 test results of device Properties
Figure BDA0002793911670000252
Figure BDA0002793911670000261
As can be seen from Table 1, the driving voltage of the device prepared from the compound of the present invention was substantially equivalent to that of the device prepared from comparative example 1, but it was 2000cd/cm2The element lifetime under the initial condition was greatly improved, and CJHK059-1(T1 is N-phenyl) in particular exhibited good current efficiency and element lifetime.
The properties of some compounds in CJHK 018-CJHK 194 are listed in Table 1, and the properties of other compounds are substantially identical to the structures of the compounds listed in the Table, and are not listed due to space limitation.
Test example 2
The organic electroluminescent element was prepared according to the method of comparative example 1 by replacing compound D in comparative example 1 with the compounds CJHK018 to CJHK194 of the present invention.
The results of measuring the properties of the obtained element are shown in Table 2, in which the driving voltage (V), the current efficiency (LE), the color Coordinate (CIE), and the full width at half maximum (FWHM) were measured at a current density of 10mA/cm2Conditions were obtained and the voltage, LE, FWHM and LT 90% were normalized to the reference.
TABLE 2 test results of device Properties
Figure BDA0002793911670000262
As can be seen from the results of the device performance test of Table 2, the devices fabricated with the compound of the present invention showed significantly lower driving voltage, higher current efficiency, and initial luminance of 2000cd/cm at the device, compared to the devices fabricated with comparative example 1, especially CJHK160-1 and CJHK021-12The LT 90% lifetime improvement is evident for the initial condition.
The properties of only some of the compounds CJHK 018-CJHK 194 are listed in Table 2, and the properties of other compounds are substantially identical to the structures of the compounds listed in the Table, and are not listed any more due to space limitation.
As shown in fig. 1 and fig. 2, which are a schematic view of a bottom emission example of the organic electroluminescent device of the present invention and a schematic view of a top emission example of the organic electroluminescent device, respectively, the organic compound prepared by the present invention is contained in the light-emitting layer 5 or the hole transport layer 4.
Although the invention has been described in detail hereinabove by way of general description, specific embodiments and experiments, it will be apparent to those skilled in the art that many modifications and improvements can 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 structure represented by formula (I):
Figure FDA0002793911660000011
wherein R is1～R13Same or different, selected from hydrogen, deuterium, having C1～C40Straight chain alkyl of (2) having C1～C40Linear heteroalkyl group of (A) having C3～C40A branched or cyclic alkyl group having C3～C40A branched or cyclic heteroalkyl group of (A) having C2～C40Alkenyl or alkynyl group of (A), an aromatic ring system or a heteroaromatic ring system having 5 to 60 carbon atoms, R1～R13Each of which may be substituted by one or more groups R, and wherein two or more adjacent substituent groups may optionally be joined or fused to form a mono-or polycyclic aliphatic, aromatic or heteroaromatic ring system;
Ar1is selected from the group consisting of having C1～C40Straight chain alkyl of (2) having C1～C40Linear heteroalkyl group of (A) having C3～C40A branched or cyclic alkyl group having C3～C40A branched or cyclic heteroalkyl group of (A) having C2～C40Alkenyl or alkynyl groups of (a), aromatic or heteroaromatic ring systems having 5 to 60 carbon atoms, which ring systems may be substituted by one or more radicals R;
each occurrence of R is the same or different and is selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a nitrile group, a nitro group, and N (Ar)2)2、N(R14)2、C(＝O)Ar2、C(＝O)R14、P(＝O)(Ar2)2Having a structure of C1～C40Straight chain alkyl of (2) having C1～C40Linear heteroalkyl group of (A) having C3～C40A branched or cyclic alkyl group having C3～C40A branched or cyclic heteroalkyl group of (A) having C2～C40Alkenyl or alkynyl groups of (A), aromatic or heteroaromatic ring systems having from 5 to 80 carbon atoms, aryloxy or heteroaryloxy groups having from 5 to 60 carbon atoms, each of the R groups being optionally substituted by one or more radicals R14Substituted, or combinations of these systems, wherein one or more non-adjacent-CH2The radicals may be substituted by R14C＝CR14、C≡C、Si(R14)2、Ge(R14)2、Sn(R14)2、C＝O、C＝S、C＝Se、C＝NR14、P(＝O)(R14)、SO、SO2、NR14O, S or CONR14And in which one or more hydrogen atoms are replaced by deuterium atoms, halogen atoms, nitrile groups or nitro groups, where two or more adjacent substituents R may optionally be joined or fused to form a mono-or polycyclic, aliphatic, aromatic or heteroaromatic ring system which may be interrupted by one or more radicals R14Substitution;
R14each occurrence of the same or different is selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a nitrile group, a nitro group, and N (Ar)2)2、N(R15)2、C(＝O)Ar2、C(＝O)R15、P(＝O)(Ar2)2Having a structure of C1～C40Straight chain alkyl of (2) having C1～C40Linear heteroalkyl group of (A) having C3～C40A branched or cyclic alkyl group having C3～C40A branched or cyclic heteroalkyl group of (A) having C2～C40One of alkenyl or alkynyl, aromatic or heteroaromatic ring system having 5 to 60 carbon atoms, aryloxy or heteroaryloxy having 5 to 60 carbon atoms, R14Each radical in (a) may be substituted by one or more radicals R15Substituted, or combinations of these systems, wherein one or more non-adjacent-CH2The radicals may be substituted by R15C＝CR15、C≡C、Si(R15)2、Ge(R15)2、Sn(R15)2、C＝O、C＝S、C＝Se、C＝NR15、P(＝O)(R15)、SO、SO2、NR15O, S or CONR15And wherein one or more hydrogen atoms may be replaced by deuterium atoms, halogen atoms, nitrile groups or nitro groups, wherein two or more adjacent substituents R14Aliphatic, aromatic or heteroaromatic ring systems which may optionally be joined or fused to form a single ring or multiple rings and which may be interrupted by one or more radicals R15Substitution;
Ar2identical or different at each occurrence and selected from aromatic or heteroaromatic ring systems having from 5 to 30 carbon atoms, which may be substituted by oneOr a plurality of nonaromatic radicals R15Substitution; two groups Ar here bonded to the same nitrogen or phosphorus atom2Can also be selected from N (R) through a single bond15)、C(R15)2Oxygen or sulfur bridging groups;
R15selected from hydrogen atom, deuterium atom, fluorine atom, nitrile group, having C1～C20An aliphatic hydrocarbon group, an aromatic ring or a heteroaromatic ring system having 5 to 30 carbon atoms, wherein R15Wherein one or more hydrogen atoms may be replaced by deuterium atoms, halogen atoms, or nitrile groups, wherein two or more adjacent substituents R15They can form mono-or polycyclic aliphatic, aromatic or heteroaromatic ring systems with one another.
2. The carbazole derivative according to claim 1, wherein R is1～R13The same or different, selected from one of hydrogen, deuterium, aromatic ring system or heteroaromatic ring system with 5-60 carbon atoms, wherein R is1～R13Each of which may be substituted by one or more groups R, and wherein two or more adjacent substituent groups may optionally be joined or fused to form a mono-or polycyclic aliphatic, aromatic or heteroaromatic ring system;
ar is1Selected from aromatic or heteroaromatic ring systems having 5 to 60 carbon atoms, which ring systems may be substituted by one or more radicals R;
each occurrence of R is the same or different and is selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a nitrile group, a nitro group, and N (Ar)2)2、N(R14)2、C(＝O)Ar2、C(＝O)R14、P(＝O)(Ar2)2Having a structure of C1～C40Straight chain alkyl of (2) having C1～C40Linear heteroalkyl group of (A) having C3～C40A branched or cyclic alkyl group having C3～C40A branched or cyclic heteroalkyl group of (A) having C2～C40Alkenyl or alkynyl groups, aromatic or heteroaromatic ring systems having 5 to 80 carbon atoms, aryloxy groups having 5 to 60 carbon atomsOne of a aryl or heteroaryloxy group, each of the R groups being optionally substituted with one or more radicals R14Substituted, or combinations of these systems, wherein one or more non-adjacent-CH2The radicals may be substituted by R14C＝CR14、C≡C、Si(R14)2、Ge(R14)2、Sn(R14)2、C＝O、C＝S、C＝Se、C＝NR14、P(＝O)(R14)、SO、SO2、NR14O, S or CONR14And in which one or more hydrogen atoms are replaced by deuterium atoms, halogen atoms, nitrile groups or nitro groups, where two or more adjacent substituents R may optionally be joined or fused to form a mono-or polycyclic, aliphatic, aromatic or heteroaromatic ring system which may be interrupted by one or more radicals R14Substitution;
R14each occurrence of the same or different is selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a nitrile group, a nitro group, and N (Ar)2)2、N(R15)2、C(＝O)Ar2、C(＝O)R15、P(＝O)(Ar2)2Having a structure of C1～C40Straight chain alkyl of (2) having C1～C40Linear heteroalkyl group of (A) having C3～C40A branched or cyclic alkyl group having C3～C40A branched or cyclic heteroalkyl group of (A) having C2～C40One of alkenyl or alkynyl, aromatic or heteroaromatic ring system having 5 to 60 carbon atoms, aryloxy or heteroaryloxy having 5 to 60 carbon atoms, R14Each radical in (a) may be substituted by one or more radicals R15Substituted, or combinations of these systems, wherein one or more non-adjacent-CH2The radicals may be substituted by R15C＝CR15、C≡C、Si(R15)2、Ge(R15)2、Sn(R15)2、C＝O、C＝S、C＝Se、C＝NR15、P(＝O)(R15)、SO、SO2、NR15O, S or CONR15And wherein one or more hydrogen atoms may be replaced by deuterium atoms, halogen atoms, nitrile groups or nitro groups, which are substituted by deuterium atoms, halogen atoms, nitrile groups or nitro groupsTwo or more adjacent substituents R14Aliphatic, aromatic or heteroaromatic ring systems which may optionally be joined or fused to form a single ring or multiple rings and which may be interrupted by one or more radicals R15Substitution;
Ar2identical or different at each occurrence and selected from aromatic or heteroaromatic ring systems having from 5 to 30 carbon atoms which may be substituted by one or more nonaromatic radicals R15Substitution; two groups Ar here bonded to the same nitrogen or phosphorus atom2Can also be selected from N (R) through a single bond15)、C(R15)2Oxygen or sulfur bridging groups;
R15selected from hydrogen atom, deuterium atom, fluorine atom, nitrile group, having C1～C20An aliphatic hydrocarbon group, an aromatic ring or a heteroaromatic ring system having 5 to 30 carbon atoms, wherein R15Wherein one or more hydrogen atoms may be replaced by deuterium atoms, halogen atoms, or nitrile groups, wherein two or more adjacent substituents R15They can form mono-or polycyclic aliphatic, aromatic or heteroaromatic ring systems with one another.
3. The carbazole derivative according to claim 1 or 2, wherein the structure of the carbazole derivative mainly includes the following CJHK018 to CJHK 194:
Figure FDA0002793911660000041
Figure FDA0002793911660000051
Figure FDA0002793911660000061
Figure FDA0002793911660000071
Figure FDA0002793911660000081
Figure FDA0002793911660000091
Figure FDA0002793911660000101
Figure FDA0002793911660000111
Figure FDA0002793911660000121
wherein, T is1、T2Each independently selected from-O-, -S-, or any of the following structures:
Figure FDA0002793911660000131
and represents a bond.
4. The carbazole derivative according to claim 1, wherein R is1～R13Identical or different, selected from hydrogen, deuterium;
ar is1Selected from aromatic or heteroaromatic ring systems having 5 to 60 carbon atoms, which ring systems may be substituted by one or more radicals R;
each occurrence of R is the same or different and is selected from a hydrogen atom, a deuterium atom, a halogen atom, a nitrile group, a nitrateRadical, N (Ar)2)2、N(R14)2、C(＝O)Ar2、C(＝O)R14、P(＝O)(Ar2)2Having a structure of C1～C40Straight chain alkyl of (2) having C1～C40Linear heteroalkyl group of (A) having C3～C40A branched or cyclic alkyl group having C3～C40A branched or cyclic heteroalkyl group of (A) having C2～C40Alkenyl or alkynyl groups of (A), aromatic or heteroaromatic ring systems having from 5 to 80 carbon atoms, aryloxy or heteroaryloxy groups having from 5 to 60 carbon atoms, each of the R groups being optionally substituted by one or more radicals R14Substituted, or combinations of these systems, wherein one or more non-adjacent-CH2The radicals may be substituted by R14C＝CR14、C≡C、Si(R14)2、Ge(R14)2、Sn(R14)2、C＝O、C＝S、C＝Se、C＝NR14、P(＝O)(R14)、SO、SO2、NR14O, S or CONR14And in which one or more hydrogen atoms are replaced by deuterium atoms, halogen atoms, nitrile groups or nitro groups, where two or more adjacent substituents R may optionally be joined or fused to form a mono-or polycyclic, aliphatic, aromatic or heteroaromatic ring system which may be interrupted by one or more radicals R14Substitution;
R14each occurrence of the same or different is selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a nitrile group, a nitro group, and N (Ar)2)2、N(R15)2、C(＝O)Ar2、C(＝O)R15、P(＝O)(Ar2)2Having a structure of C1～C40Straight chain alkyl of (2) having C1～C40Linear heteroalkyl group of (A) having C3～C40A branched or cyclic alkyl group having C3～C40A branched or cyclic heteroalkyl group of (A) having C2～C40One of alkenyl or alkynyl, aromatic or heteroaromatic ring system having 5 to 60 carbon atoms, aryloxy or heteroaryloxy having 5 to 60 carbon atoms, R14Each radical in (a) may be substituted by one or more radicals R15Substituted, or combinations of these systems, wherein one or more non-adjacent-CH2The radicals may be substituted by R15C＝CR15、C≡C、Si(R15)2、Ge(R15)2、Sn(R15)2、C＝O、C＝S、C＝Se、C＝NR15、P(＝O)(R15)、SO、SO2、NR15O, S or CONR15And wherein one or more hydrogen atoms may be replaced by deuterium atoms, halogen atoms, nitrile groups or nitro groups, wherein two or more adjacent substituents R14Aliphatic, aromatic or heteroaromatic ring systems which may optionally be joined or fused to form a single ring or multiple rings and which may be interrupted by one or more radicals R15Substitution;
Ar2identical or different at each occurrence and selected from aromatic or heteroaromatic ring systems having from 5 to 30 carbon atoms which may be substituted by one or more nonaromatic radicals R15Substitution; two groups Ar here bonded to the same nitrogen or phosphorus atom2Can also be selected from N (R) through a single bond15)、C(R15)2Oxygen or sulfur bridging groups;
R15selected from hydrogen atom, deuterium atom, fluorine atom, nitrile group, having C1～C20An aliphatic hydrocarbon group, an aromatic ring or a heteroaromatic ring system having 5 to 30 carbon atoms, wherein R15Wherein one or more hydrogen atoms may be replaced by deuterium atoms, halogen atoms, or nitrile groups, wherein two or more adjacent substituents R15They can form mono-or polycyclic aliphatic, aromatic or heteroaromatic ring systems with one another.
5. Use of the carbazole derivative according to any one of claims 1 to 4 in an organic element.
6. Use of a carbazole derivative as claimed in any one of claims 1 to 4 as a light-emitting layer material, a hole transport layer material, a hole blocking layer material or an encapsulation layer material in an organic device.
7. Use according to claim 5 or 6, wherein the organic element is an organic electroluminescent element, an organic field effect transistor or an organic thin film solar cell.
8. An organic electroluminescent element comprising a first electrode, a second electrode, and a plurality of organic layers between the first electrode and the second electrode, wherein at least one of the organic layers contains the carbazole derivative according to any one of claims 1 to 4.
9. A display device comprising the organic electroluminescent element according to claim 8.
10. A lighting device comprising the organic electroluminescent element according to claim 8.
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