CN113061133B - Carbazole derivative, use thereof, organic electroluminescent element, display device, and lighting device - Google Patents

Carbazole derivative, use thereof, organic electroluminescent element, display device, and lighting device Download PDF

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CN113061133B
CN113061133B CN202110309102.1A CN202110309102A CN113061133B CN 113061133 B CN113061133 B CN 113061133B CN 202110309102 A CN202110309102 A CN 202110309102A CN 113061133 B CN113061133 B CN 113061133B
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carbazole derivative
organic electroluminescent
electroluminescent element
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曹建华
戴雄
唐怡杰
侯斌
王学涛
白爽
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Beijing Bayi Space LCD Technology Co Ltd
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Abstract

The present invention relates to a series of carbazole derivatives, applications thereof, and organic electroluminescent elements, display devices, and lighting devices containing the carbazole derivatives. The carbazole derivative has a structural formula shown in a formula (I), has high stability and triplet state energy level, is suitable for being used as a material for an organic electroluminescent element, and has the characteristics of low starting voltage, high luminous efficiency and high brightness.
Figure DDA0002989088860000011

Description

Carbazole derivative, use thereof, organic electroluminescent element, display device, and lighting device
Technical Field
The invention belongs to the technical field of materials for organic electroluminescent elements, and particularly relates to a carbazole derivative and application thereof, and an organic electroluminescent element, a display device and a lighting device containing the carbazole derivative.
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 in 1997 discovered that the phosphorescence electroluminescence phenomenon breaks through the limitation 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 having a structural formula represented by formula (I):
Figure BDA0002989088840000021
wherein any two adjacent groups W1、W2、W3、W4Represents a group of the following formula (II),
Figure BDA0002989088840000022
wherein Z, identically or differently at each occurrence, denotes CR9Or N, and ^ indicates the corresponding adjacent group W in formula I1And W2、W2And W3Or W3And W4；
T1Represents a single bond, O, S, NAr2Or CR10R11；
R1～R11Same 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～R11Each 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;
Ar1、Ar2same or different, 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)3)2、N(R12)2、C(＝O)Ar3、C(＝O)R12、P(＝O)(Ar3)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 atomsEach of the R groups may be substituted by one or more radicals R12Substituted, or combinations of these systems, wherein one or more non-adjacent-CH2The radicals may be substituted by R12C＝CR12、C≡C、Si(R12)2、Ge(R12)2、Sn(R12)2、C＝O、C＝S、C＝Se、C＝NR12、P(＝O)(R12)、SO、SO2、NR12O, S or CONR12And 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 R12Substitution;
R12each 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)3)2、N(R13)2、C(＝O)Ar3、C(＝O)R13、P(＝O)(Ar3)2Having a structure of C1～C40Straight chain alkyl of (2) having C1～C40Linear heteroalkyl group of (C)3～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, R12Each radical in (a) may be substituted by one or more radicals R13Substituted, or combinations of these systems, wherein one or more non-adjacent-CH2The radical may be represented by R13C＝CR13、C≡C、Si(R13)2、Ge(R13)2、Sn(R13)2、C＝O、C＝S、C＝Se、C＝NR13、P(＝O)(R13)、SO、SO2、NR13O, S or CONR13And wherein one or more hydrogen atoms may be replaced by deuterium atoms, halogen atoms, nitrile groups or nitro groups, two or more of whichAdjacent substituent R12Aliphatic, 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 R13Substitution;
Ar3identical 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 R13Substitution; two groups Ar here bonded to the same nitrogen or phosphorus atom3Can also be selected from N (R) through a single bond13)、C(R13)2Oxygen or sulfur bridging groups;
R13selected from hydrogen atoms, deuterium atoms, fluorine atoms, nitrile groups, having C1～C20An aliphatic hydrocarbon group, an aromatic ring or a heteroaromatic ring system having 5 to 30 carbon atoms, wherein R13Wherein one or more hydrogen atoms may be replaced by deuterium atoms, halogen atoms or nitrile groups, wherein two or more adjacent substituents R13They 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-trifluoroethoxy group. The heteroalkyl group is preferably an alkyl group having 1 to 40 carbon atoms, meaning a hydrogen atom or-CH alone2The radicals-which may be substituted by oxygen, sulfur or halogen atoms-are understood to mean alkoxy, alkylthio, fluorinated alkoxy, fluorinated alkylthio, in particular methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, isobutylthio, sec-butylthio, tert-butylthio, trifluoromethylthio, trifluoromethoxy, pentafluoroethoxy, pentafluoroethylthio, 2,2, 2-trifluoroethoxy, 2,2, 2-trifluoroethylthio, vinyloxy, propenyloxy, propenylthio, butenylthio, butenyloxy, pentenylthio, cyclopentenyloxy, cyclopentenylthio, hexenyloxy, hexenylthio, cyclohexenyloxy, cyclohexenylthio, ethynyloxy, propenylthio, butenyloxy, cyclohexenylthio, ethynyloxy, Ethynylthio, propynyloxy, propynylthio, butynyloxy, butynylthio, pentynyloxy, propargyloxy, and the like,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 R13Substituted aromatic or heteroaromatic ring systems, in particular radicals derived from: benzene, naphthalene, anthracene, benzanthracene, phenanthrene, pyrene,
Figure BDA0002989088840000051
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, 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-oxaOxadiazoles, 1,2, 5-oxadiazoles, 1,3, 4-oxadiazoles, 1,2, 3-thiadiazoles, 1,2, 4-thiadiazoles, 1,2, 5-thiadiazoles, 1,3, 4-thiadiazoles, 1,3, 5-triazines, 1,2, 4-triazines, 1,2, 3-triazines, tetrazoles, 1,2,4, 5-tetrazines, 1,2,3, 4-tetrazines, 1,2,3, 5-tetrazines, purines, pteridines, indolizines and benzothiadiazoles or groups derived from combinations of these systems.
Further, said R1～R8Identical or different, from hydrogen or deuterium, wherein each radical may be substituted by one or more radicals R;
further, said R9～R11Same or different, selected from hydrogen, deuterium, having C1～C40A straight-chain alkyl group of (A), an aromatic or heteroaromatic ring system having 5 to 60 carbon atoms, or R10And R11Optionally joined or fused to form a mono-or polycyclic aliphatic, aromatic or heteroaromatic ring system;
further, said Ar1、Ar2Selected from aromatic or heteroaromatic ring systems having 5 to 60 carbon atoms, which ring systems may be substituted by one or more radicals R.
Further, the carbazole derivative mainly comprises the following CJHL 017-CJHL 238:
Figure BDA0002989088840000061
Figure BDA0002989088840000071
Figure BDA0002989088840000081
Figure BDA0002989088840000091
Figure BDA0002989088840000101
Figure BDA0002989088840000111
Figure BDA0002989088840000121
Figure BDA0002989088840000131
Figure BDA0002989088840000141
Figure BDA0002989088840000151
Figure BDA0002989088840000161
Figure BDA0002989088840000171
Figure BDA0002989088840000181
an application of the carbazole derivative in materials for organic elements.
Further, the carbazole derivative is a material for an organic electroluminescent element, a material for an organic field effect transistor, or a material for an organic thin film solar cell.
Further, the carbazole derivative is applied to a luminescent layer material, a hole transport/hole barrier layer material or an encapsulation layer material.
An organic electroluminescent element comprising a first electrode, a second electrode and a plurality of organic layers disposed 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 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.
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.
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 10-5Pa, preferably less than 10-6Pa is applied by vapor deposition. However, the initial pressure may also be even lower, e.g. below 10-7Pa。
Also preferred is an organic electroluminescent element in which,applying one or more layers by means of an organic vapour deposition method or by means of carrier gas sublimation, wherein 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, are obtained by appropriate substitution of the compounds of formula (I) of the present invention. 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. In addition, the carbazole derivative of the present invention has excellent thermal stability and film forming properties, and can be applied to a material for an organic electroluminescent element, a display device, and a lighting device, and can prolong the service life thereof, thereby reducing the manufacturing cost of the material for an organic electroluminescent element, the display device, and the lighting device.
Drawings
In order to more clearly illustrate the embodiments of the present invention or the technical solutions in the prior art, the drawings used in the description of the embodiments or the prior art will be briefly described below, it is obvious that the drawings in the following description are only some embodiments of the present invention, and for those skilled in the art, other drawings can be obtained according to the drawings without creative efforts.
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 of an example of top emission of the organic electroluminescent device of the present invention.
Reference numerals
1-substrate, 2-anode, 3-hole injection layer, 4-hole transport/electron blocking layer, 5-luminescent layer, 6-hole transport/electron transport layer, 7-electron injection layer and 8-cathode.
Detailed Description
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: an LTS-1004AC life test apparatus was used.
Example 1
The preparation method of the intermediate A comprises the following steps:
the first step is as follows: preparation of Compound Int-1
Figure BDA0002989088840000211
0.10mol of 1-methylcarbazole, 0.15mol of pyridine and 200mL of dichloromethane are added dropwise at the temperature of below 5 ℃ with 0.12mol of trifluoroacetic anhydride, the mixture is stirred for reaction for 2 hours, 100mL of 1N dilute hydrochloric acid aqueous solution is added, an organic phase is separated, the organic phase is washed with water, the organic phase is collected, dried and filtered, filtrate is concentrated under reduced pressure to be dry, and the organic phase is separated and purified by a silica gel column to obtain a compound Int-1 with the yield of 96%.
The second step is that: preparation of Compound Int-2
Figure BDA0002989088840000212
0.10mol of the intermediate Int-1 prepared in the first step is dispersed in 200mL of carbon tetrachloride, 0.11mol of NBS and 5mg of azobisisobutyronitrile are added, the mixture is heated, refluxed, stirred and reacted for 5 hours, the mixture is cooled to room temperature, filtered, filtrate is washed by saturated sodium bisulfite aqueous solution, organic phase is dried, the mixture is concentrated under reduced pressure and then is separated and purified by a silica gel column, and light yellow intermediate Int-2 is obtained with the yield of 92%.
The third step: preparation of Compound Int-3
Figure BDA0002989088840000221
56.0mmol of the intermediate Int-2 prepared in the second step is dissolved in 100mL of triethyl phosphite, heated, refluxed, stirred, reacted for 3 hours, cooled to room temperature, concentrated under reduced pressure to dryness, and separated and purified by a silica gel column to obtain the intermediate Int-3 with a yield of 86%.
The fourth step: preparation of Compound Int-4
Figure BDA0002989088840000222
Dissolving 50.0mmol of intermediate Int-3 in 150mL of dry THF, cooling to-25 ℃ under the protection of nitrogen, adding 55.0mmol of sodium hydride in batches, stirring for reaction for 10 minutes, dropwise adding a solution of 55.0mmol of ketone dissolved in THF, heating to room temperature, stirring for reaction for 5 hours, dropwise adding 50mL of water for dilution, extracting with ethyl acetate, collecting an organic phase, drying, filtering, concentrating the filtrate under reduced pressure to dryness, and separating and purifying by using a silica gel column to obtain intermediate Int-4 with the yield of 90-96%.
The fifth step: preparation of intermediate Int-5
Figure BDA0002989088840000223
20.0mmol of the intermediate Int-4 prepared in the fourth step is dissolved in 120mL of 1, 2-dichloroethane, 4.0mmol of anhydrous ferric chloride is added, the temperature is raised to 50 ℃, the mixture is stirred and reacts for 12 hours, the mixture is cooled to room temperature, 20mL of 1N dilute hydrochloric acid aqueous solution is added, an organic phase is separated, the organic phase is washed by water, dried and filtered, the filtrate is concentrated to be dry, and is separated and purified by a silica gel column, so that the intermediate Int-5 is obtained, and the yield is 90%.
And a sixth step: preparation of intermediate A
Figure BDA0002989088840000231
50.0mmol of intermediate Int-5 prepared in the fifth step was dissolved in 80mL of DMF, 20mL of water and 4g (0.1mol) of sodium hydroxide were added, the mixture was stirred under reflux at elevated temperature for 2 hours, cooled to room temperature, 100mL of 2N dilute aqueous hydrochloric acid was added, the mixture was filtered, and the filter cake was washed with water and ethanol, and then recrystallized from toluene-THF to give intermediate A in 98% yield.
The following compounds were prepared in a similar manner to the synthesis described above:
Figure BDA0002989088840000232
Figure BDA0002989088840000241
example 2
The preparation method of the intermediate B comprises the following steps:
the first step is as follows: preparation of Compound Int-6
Figure BDA0002989088840000251
0.12mol of carbazole-4-boronic acid pinacol ester and 0.10mol of 1-halogenated ketone are dissolved in 160mL of THF and 80mL of water, and 0.40mol of anhydrous sodium carbonate and 1.2g of Pd (PPh) are added under the protection of nitrogen3)4Heating the catalyst, refluxing, stirring and reacting for 15 hours, cooling to room temperature, adding 50mL of water for dilution, extracting with ethyl acetate, collecting an organic phase, drying, filtering, concentrating the filtrate under reduced pressure to dryness, and separating and purifying by using a silica gel columnThe compound Int-6 is obtained with a yield of 82-90%.
The second step: preparation of Compound Int-7
Figure BDA0002989088840000252
Dissolving 55.0mmol of methoxymethyl triphenyl phosphonium chloride in 150mL of dry THF, cooling to-25 ℃ under the protection of nitrogen, adding 60.0mmol of potassium tert-butoxide in batches, stirring for reaction for 10 minutes, heating to room temperature, stirring for reaction for 30 minutes, adding 50.0mmol of intermediate Int-6, stirring for reaction for 1 hour at room temperature, heating for reflux reaction for 5 hours, cooling to room temperature, concentrating under reduced pressure to dryness, adding 200mL of toluene and 60.0mmol of anhydrous magnesium chloride, heating for reflux for 30 minutes, cooling to room temperature, filtering, concentrating the filtrate under reduced pressure to dryness, separating and purifying by using a silica gel column to obtain intermediate Int-7 with the yield of 90-95%.
The third step: preparation of Compound B
Figure BDA0002989088840000253
Dissolving 40.0mmol of intermediate Int-7 in 150mL of dichloromethane, cooling to 0 ℃ in an ice water bath under the protection of nitrogen, adding 80.0mmol of trifluoromethanesulfonic acid, stirring for reaction for 2 hours, adding 150mL of saturated sodium carbonate aqueous solution, heating and refluxing for 30 minutes, cooling to room temperature, filtering, washing a filter cake with water and ethanol, and separating and purifying with a silica gel column to obtain an intermediate B.
The following compounds were prepared in a similar manner to the synthesis described above:
Figure BDA0002989088840000261
Figure BDA0002989088840000271
Figure BDA0002989088840000281
example 3
Preparation of compound CJHL 192:
Figure BDA0002989088840000282
10.0mmol of intermediate B13 is dissolved in 80mL of dry THF, the temperature is reduced to 0 ℃ by an ice water bath under the protection of nitrogen, 11.0mmol of 65% sodium hydride solid is added, stirring reaction is carried out for 1 hour, 11.0mmol of 2-chloro-4, 6-diphenyl-1, 3, 5-triazine is added, stirring reaction is carried out for 24 hours, 50mL of water is added for dilution, extraction is carried out by ethyl acetate, an organic phase is collected, drying and filtration are carried out, filtrate is concentrated under reduced pressure to be dry, and separation and purification are carried out by a silica gel column to obtain a compound CJHL192 with white solid yield of 74%.
MS and of compound CJHL1921The HNMR test results are as follows:
MS(MALDI-TOF)：m/z 589.2046[M+H]+；1HNMR(δ、CDCl3)：9.06(s,1H)；8.68～8.66(d,1H)；8.35～8.28(m,5H)；8.08(s,1H)；7.93～7.90(m,2H)；7.73～7.71(d,1H)；7.63～7.57(m,3H)；7.45～7.35(m,9H)；7.18～7.16(m,1H)。
the following compounds were prepared in a similar manner to the synthesis described above:
Figure BDA0002989088840000283
Figure BDA0002989088840000291
Figure BDA0002989088840000301
example 4
Preparation of compound CJHL 103:
Figure BDA0002989088840000302
15.0mmol of intermediate A4 was dissolved in 80mL of dry toluene, 16.5mmol of 2- (3-bromophenyl) -4, 6-diphenyl-1, 3, 5-triazine (CAS:864377-31-1) and 22.5mmol of sodium tert-butoxide were added under nitrogen, and 0.1mmol of Pd was added2(dba)3CHCl3And 0.02mL of 10% tri-tert-butylphosphine toluene solution, heating to 100 ℃, stirring for reaction for 15 hours, cooling to room temperature, adding 50mL of water for dilution, extracting with ethyl acetate, collecting an organic phase, drying, filtering, concentrating the filtrate under reduced pressure to dryness, and separating and purifying by using a silica gel column to obtain a compound CJHL103 which is a yellow solid and has the yield of 78%.
MS and of compound CJHL1031The HNMR test results are as follows:
MS(MALDI-TOF)：m/z 740.2830[M+H]+；1HNMR(δ、CDCl3)：8.90～8.88(d,1H)；8.81～8.78(m,4H)；8.50～8.48(d,1H)；8.32～8.29(m,1H)；8.21(s,1H)；8.18～8.16(d,1H)；8.03(s,1H)；7.93～7.90(m,3H)；7.55～7.50(m,4H)；7.48～7.40(m,4H)；7.36～7.25(m,5H)；7.22～7.17(m,5H)；7.05～6.99(m,2H)。
in a similar synthetic process as described above, the following compounds were prepared:
Figure BDA0002989088840000311
Figure BDA0002989088840000321
preparation of organic electroluminescent element
Comparative example 1
The following compound a was used as a green host material, the following compound B was used as a green dopant, compound C was used as a hole injection material, compound D was used as a hole transport material, compound E was used as a red dopant, compound F was used as a red dopant, compound G was used as an electron transport dopant, and LiQ was used as an electron transport host material.
Figure BDA0002989088840000331
The compound
Figure BDA0002989088840000332
Figure BDA0002989088840000333
An organic electroluminescent element as a green light was produced by sequentially depositing an EL deposition machine manufactured by DOV on ITO glass to produce a green light element.
Will have a chemical formula
Figure BDA0002989088840000334
Figure BDA0002989088840000335
An organic electroluminescent element was prepared as a red light by depositing an EL evaporator manufactured by DOV on ITO glass in this order.
Test example 1
The green organic electroluminescent device was prepared according to the method of comparative example 1 by replacing compound a with the compounds CJHL017 to CJHL238 of the present invention.
The results of measuring the properties of the obtained green organic electroluminescent element are shown in Table 1, in which the driving voltage (V), the current efficiency (LE), the color Coordinate (CIE), the full width at half maximum (FWHM) were 10mA/cm in current density of the element2Conditions were obtained and the voltage, LE, FWHM and LT 90% were normalized to the reference.
TABLE 1 Green light element Performance test results
Figure BDA0002989088840000341
As is clear from Table 1, the green light emitting device produced from the organic material of the present invention has a low driving voltage, a high current efficiency, a good color purity, and an initial emission luminance of 2000cd/cm in comparison with the device produced in comparative example 12Under the initial conditions, the service life of the element using the compound of the invention as a green light host material is greatly improved.
The properties of some compounds in CJHL017 to CJHL238 are listed in Table 1, and the properties of other compounds are basically consistent with the structures of the compounds listed in the Table, and are not listed due to limited space.
The red light element was prepared according to the method of comparative example 1, in which the aforementioned compound E was replaced with the compounds CJHL017 to CJHL238 of the present invention, and in addition,
Figure BDA0002989088840000342
Figure BDA0002989088840000343
the results of the performance test of the obtained device are shown in Table 2, wherein the driving voltage (V), current efficiency (LE), color Coordinate (CIE), full width at half maximum (FWHM) were obtained under the condition that the current density of the device was 10mA/cm2, and the voltage, LE, FWHM and LT 90% were subjected to data normalization processing with respect to the reference device.
TABLE 2 Red light element Performance test results
Figure BDA0002989088840000344
Figure BDA0002989088840000351
As can be seen from the performance test results of the red light device in Table 2, the device prepared from the organic material of the present invention has significantly lower driving voltage, high current efficiency and good color purity of light emission compared to the red light device prepared in comparative example 1. At an initial brightness of the element of2000cd/cm2As the initial condition, the LT 90% lifetime of the element using the compound of the present invention as a red host material was 1.1 times to 2.7 times that of the comparative element.
In Table 2, only some of the properties of the compounds in CJHL017 to CJHL238 are listed, 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 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 carbazole derivative prepared in the present invention is contained in the light-emitting layer 5.
The above description is only for the specific embodiments of the present invention, but the scope of the present invention is not limited thereto, and any person skilled in the art can easily conceive of the changes or substitutions within the technical scope of the present invention, and all the changes or substitutions should be covered within the scope of the present invention. Therefore, the protection scope of the present invention shall be subject to the protection scope of the claims.

Claims (9)

1. A carbazole derivative having a structure represented by formula (I):
Figure FDA0003638326750000011
wherein any two adjacent groups W1、W2、W3、W4Represents a group of the following formula (II),
Figure FDA0003638326750000012
wherein Z, identically or differently at each occurrence, denotes CR9Or N, and ^ indicates the corresponding adjacent group W in formula I1And W2、W2And W3Or W3And W4；
T1Represents O or NAr2；
The R is1～R9Same or different, selected from hydrogen, deuterium, with C1～C40One of a linear alkyl group, an aromatic ring system or a heteroaromatic ring system having 5 to 60 carbon atoms;
ar is1、Ar2Selected from aromatic or heteroaromatic ring systems having 5 to 60 carbon atoms.
2. The carbazole derivative according to claim 1, wherein the carbazole derivative includes the following structures CJHL017 to CJHL 238:
Figure FDA0003638326750000013
Figure FDA0003638326750000021
Figure FDA0003638326750000031
Figure FDA0003638326750000041
Figure FDA0003638326750000051
Figure FDA0003638326750000061
Figure FDA0003638326750000071
Figure FDA0003638326750000081
Figure FDA0003638326750000091
Figure FDA0003638326750000101
Figure FDA0003638326750000111
Figure FDA0003638326750000121
Figure FDA0003638326750000131
3. the carbazole derivative according to claim 1, wherein R is1～R8Identical or different, selected from hydrogen or deuterium;
R9same or different, selected from hydrogen, deuterium, having C1～C40The linear alkyl group of (1), and an aromatic or heteroaromatic ring system having 5 to 60 carbon atoms.
4. Use of the carbazole derivative according to any one of claims 1 to 3 in a material for an organic element.
5. The use according to claim 4, wherein the carbazole derivative is a material for an organic electroluminescent element, a material for an organic field effect transistor, or a material for an organic thin-film solar cell.
6. Use according to claim 5, wherein the carbazole derivative is used in a light-emitting layer material, a hole transporting/hole blocking layer material or an encapsulation layer material.
7. An organic electroluminescent element comprising a first electrode, a second electrode, and a plurality of organic layers disposed 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 3.
8. A display device comprising the organic electroluminescent element according to claim 7.
9. A lighting device comprising the organic electroluminescent element according to claim 7.
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