CN112480128A - Carbazole derivative and application thereof - Google Patents

Carbazole derivative and application thereof Download PDF

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CN112480128A
CN112480128A CN202011324549.8A CN202011324549A CN112480128A CN 112480128 A CN112480128 A CN 112480128A CN 202011324549 A CN202011324549 A CN 202011324549A CN 112480128 A CN112480128 A CN 112480128A
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曹建华
朱波
侯斌
李程辉
王学涛
吕永清
赵佳
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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 a carbazole derivative 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 has good thermal stability and film-forming property, and can be applied to materials for organic electroluminescent elements and organic electricsThe life of an electroluminescent element, a display device, and a lighting device can be prolonged, and the production costs of a material for an organic electroluminescent element, a display device, and a lighting device can be reduced.
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Description

Carbazole derivative and application thereof
Technical Field
The invention relates to the technical field of materials for organic electroluminescent elements, in particular to a carbazole derivative 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 BDA0002793914570000021
wherein R is1～R16Same 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～R16Each 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;
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)1)2、N(R17)2、C(＝O)Ar1、C(＝O)R17、P(＝O)(Ar1)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 80 carbon atoms, aryloxy or heteroaryloxy having 5 to 60 carbon atoms, R groupEach radical in (a) may be substituted by one or more radicals R17Substituted, or combinations of these systems, wherein one or more non-adjacent-CH2The radicals may be substituted by R17C＝CR17、C≡C、Si(R17)2、Ge(R17)2、Sn(R17)2、C＝O、C＝S、C＝Se、C＝NR17、P(＝O)(R17)、SO、SO2、NR17O, S or CONR17And 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 R17Substitution;
R17each 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)1)2、N(R18)2、C(＝O)Ar1、C(＝O)R18、P(＝O)(Ar1)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, R17Each radical in (a) may be substituted by one or more radicals R18Substituted, or combinations of these systems, wherein one or more non-adjacent-CH2The radicals may be substituted by R18C＝CR18、C≡C、Si(R18)2、Ge(R18)2、Sn(R18)2、C＝O、C＝S、C＝Se、C＝NR18、P(＝O)(R18)、SO、SO2、NR18O, S or CONR18And wherein one or more hydrogen atoms may be replaced by deuterium atoms, halogen atoms, nitrile groups or nitro groups, with two or more adjacent substitutionsRadical R17Aliphatic, 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 R18Substitution;
Ar1identical 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 R18Substitution; two groups Ar here bonded to the same nitrogen or phosphorus atom1Can also be selected from N (R) through a single bond18)、C(R18)2Oxygen or sulfur bridging groups;
R18selected 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 R18Wherein one or more hydrogen atoms may be replaced by deuterium atoms, halogen atoms, or nitrile groups, wherein two or more adjacent substituents R18They 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-. Heteroalkyl is preferably alkyl having 1 to 40 carbon atoms, meaning that the individual hydrogen atoms or-CH 2-groups may be substituted by oxygen, sulfur, halogen atoms, and is 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, vinylthio, propenyloxy, propenylthio, butenylthio, butenyloxy, pentenyloxy, pentenylthio, cyclopentenyloxy, wherein the individual hydrogen atoms or-CH 2-groups may be replaced by oxygen, sulfur, halogen atoms, and to give alkoxy, alkylthio, fluoro, sec-alkylthio, tert-, Cyclopentenylthio, hexenyloxy, hexenylthio, cyclohexenyloxy, cyclohexenylthio, ethynyloxy, ethynylthio, propynyloxy, propynylthio, butynyloxy, butynylthio, pentynyloxy, pentynylthio, hexynyloxyAlkyl, 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 R18Substituted aromatic or heteroaromatic ring systems, in particular radicals derived from: benzene, naphthalene, anthracene, benzanthracene, phenanthrene, pyrene,
Figure BDA0002793914570000051
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-oxadiazole, 1,2, 5-oxadiazole1,3, 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～R16The same or different, selected from one of hydrogen, deuterium, aromatic ring system or heteroaromatic ring system with 5-60 carbon atoms, wherein R is1～R16Each 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 carbazole derivative mainly comprises the following structures CJHK 342-CJHK 485:
Figure BDA0002793914570000061
Figure BDA0002793914570000071
Figure BDA0002793914570000081
Figure BDA0002793914570000091
Figure BDA0002793914570000101
Figure BDA0002793914570000111
Figure BDA0002793914570000121
wherein, T is1Selected from-O-, -S-, or any of the following structures:
Figure BDA0002793914570000131
and represents a bond.
Further, said R1～R16The same or different, selected from hydrogen, deuterium, and one of aromatic ring system or heteroaromatic ring system having 5 to 60 carbon atoms.
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.
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。
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: an LTS-1004AC life test apparatus was used.
Example 1
The preparation method of the compound CJHK350 comprises the following steps:
the first step is as follows: preparation of Compound Int-1
Figure BDA0002793914570000161
0.9mol of 8-bromo-3, 4-dihydronaphthalene-1 (2H) -ketone, 1.0mol of phenylhydrazine hydrochloride and 2000mL of absolute ethanol, heating, refluxing, stirring, reacting for 12 hours, cooling to room temperature, concentrating under reduced pressure, diluting with 300mL of water, extracting with ethyl acetate, collecting an organic phase, drying, filtering, concentrating the filtrate under reduced pressure, and separating and purifying by using a silica gel column to obtain the compound Int-1 with the yield of 94%.
The second step is that: preparation of Compound Int-2
Figure BDA0002793914570000171
0.5mol of the intermediate Int-1 prepared in the first step is dispersed in 2000mL of xylene, the temperature is raised to 100 ℃, 1.5mol of solid manganese dioxide is added in batches, the mixture is stirred and reacted for 16 hours, the mixture is cooled to room temperature, the mixture is filtered, filtrate is concentrated to dryness, and the filtrate is separated and purified by a silica gel column to obtain the intermediate Int-2 as yellow solid with the yield of 92%.
The third step: preparation of Compound Int-3
Figure BDA0002793914570000172
50.0mmol of the intermediate Int-2 prepared in the second step is dissolved in 200mL of xylene, 55.0mmol of 1-bromo-6-chlorocarbazole, 0.5mmol of cuprous iodide and 120.0mmol of sodium tert-butoxide are added under the protection of nitrogen, and 0.2mmol of Pd is added2(dba)3And 1.0mL of a 10% tri-tert-butylphosphine toluene solution, heating to 110 ℃, stirring for reaction for 16 hours, cooling to room temperature, adding 50mL of water for dilution, extracting with dichloromethane, 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 yellow solid intermediate Int-3 with the yield of 72%.
The fourth step: preparation of compound CJHK350
Figure BDA0002793914570000173
10.0mmol of the intermediate Int-3 prepared in the third step was dissolved in 60mL of THF, 12.0mmol of (3- (4, 6-diphenyl-1, 3, 5-triazin-2-yl) phenyl) boronic acid and 0.2mg of Pd132 catalyst were added, 25.0mmol of anhydrous potassium carbonate and 20mL of water were added, the mixture was refluxed for 12 hours under stirring, 50mL of water was added for dilution, extraction was performed with dichloromethane, the organic phase was collected, dried, filtered, the filtrate was concentrated under reduced pressure to dryness, and then separated and purified by silica gel column to obtain CJHK350 as a yellow solid with a yield of 74%.
MS and of compound CJHK3501The HNMR test results are as follows:
MS(MALDI-TOF)：m/z 688.2519[M+H]+；1HNMR(δ、CDCl3)：8.96(1H,s)；8.65(1H,s)；8.35～8.31(4H,m)；8.13～8.04(3H,m)；7.97～7.84(6H,m)；7.55～7.53(1H,d)；7.46～7.41(3H,m)；7.39～7.32(9H,m)；7.28～7.25(1H,m)。
example 2
Preparation of the compounds CJHK 342-CJHK 349 and CJHK 351-CJHK 385 referring to the preparation method of example 1, only the (3- (4, 6-diphenyl-1, 3, 5-triazin-2-yl) phenyl) boronic acid of the fourth step in example 1 was replaced with a different organic boronic acid, and the other experimental parameters were routinely adjusted to prepare the compounds CJHK 342-CJHK 349 and CJHK 351-CJHK 385.
Example 3
The preparation method of the compound CJHK393 comprises the following steps:
the first step is as follows: preparation of Compound Int-4
Figure BDA0002793914570000181
10.0mmol of intermediate Int-30 (prepared by replacing phenylhydrazine hydrochloride in the first step with p-chlorophenylhydrazine hydrochloride in reference to the preparation method of example 1) was dissolved in 60mL of dry THF, the temperature was reduced to-80 ℃ by a liquid nitrogen bath under the protection of nitrogen, 4.8mL of 2.5M n-butyllithium n-hexane solution was added dropwise, the reaction was stirred for 1 hour, 15.0mmol of trimethyl borate was added dropwise, the reaction was stirred for 1 hour, the temperature was raised to room temperature, 50mL of dilute aqueous hydrochloric acid solution was added dropwise, the reaction was stirred for 30 minutes, extraction was performed with ethyl acetate, an organic phase was collected, dried, filtered, the filtrate was concentrated under reduced pressure to dryness, and the intermediate Int-4 was dispersed with petroleum ether and filtered to obtain a yellow solid with a yield of 73%.
The second step is that: preparation of compound CJHK393
Figure BDA0002793914570000191
10.0mmol of the intermediate Int-4 prepared in the previous step was dissolved in 60mL of toluene, and 8.6mmol of 2-chloro-4, 6-diphenyl-1, 3, 5-triazine, 20.0mmol of anhydrous potassium 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 a compound CJHK393 with yellow solid yield of 75%.
MS and of compound CJHK3931The HNMR test results are as follows:
MS(MALDI-TOF)：m/z 612.2204[M+H]+；1HNMR(δ、CDCl3)：9.32(1H,s)；8.34～8.30(4H,m)；8.18～8.13(7H,m)；7.98～7.95(2H,m)；7.87～7.83(2H,m)；7.45～7.41(5H,m)；7.35～7.29(4H,m)。
example 4
Preparation of the compounds CJHK 386-CJHK 392, CJHK 394-CJHK 452 and CJHK 465-CJHK 470, referring to the preparation method of example 3, only the 2-chloro-4, 6-diphenyl-1, 3, 5-triazine of the second step in example 3 was replaced with different halides, and other experimental parameters were routinely adjusted to prepare the compounds CJHK 386-CJHK 392, CJHK 394-CJHK 452 and CJHK 465-CJHK 470.
Example 5
The preparation method of the compound CJHK478 comprises the following steps:
the first step is as follows: preparation of intermediate Int-5
Figure BDA0002793914570000201
15.0mmol of intermediate Int-4 was dissolved in 80mL of dry toluene, 16.5mmol of p-bromoiodobenzene and 30.0mmol of anhydrous sodium carbonate were added under nitrogen protection, and 0.1mmol of Pd (PPh) was added4And 40mL of ethanol and 40mL of water, heating, refluxing, stirring, reacting for 8 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 an intermediate Int-5, namely a yellow solid with the yield of 77%.
The second step is that: preparation of Compound CJHK478
Figure BDA0002793914570000202
12.0mmol of the intermediate Int-5 prepared in the previous step was dissolved in 60mL of toluene, and 10.0mmol 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, 0.01mmol of Pd2(dba)3CHCl3The catalyst and 0.2mL of 10% toluene solution of tri-tert-butylphosphine were heated to 90 deg.C and stirred to react for 12 hours, cooled to room temperature, diluted with 50mL of water, extracted with dichloromethane, the organic phase was collected, dried, filtered, the filtrate was concentrated to dryness under reduced pressure, and then purified by silica gel column separation to obtain CJHK478 as a yellow solid with a yield of 74%.
MS and of compound CJHK4781The HNMR test results are as follows:
MS(MALDI-TOF)：m/z 816.3394[M+H]+；1HNMR(δ、CDCl3)：8.52～8.43(6H,m)；8.34～8.27(4H,m)；7.93～7.85(4H,m)；7.72～7.64(4H,m)；7.52～7.41(3H,m)；7.38～7.28(7H,m)；7.25～7.21(3H,m)；7.17～7.12(2H,m)；7.08～7.04(2H,m)；1.66(6H,s)。
example 6
Preparation of the compounds CJHK 471-CJHK 477 and CJHK 479-CJHK 485 referring to the preparation method of example 5, the compounds CJHK 471-CJHK 477 and CJHK 479-CJHK 485 were prepared by replacing only N- ([1,1' -biphenyl ] -2-yl) -9, 9-dimethyl-9H-fluoren-2-amine of the second step in example 5 with different organic amines and performing general adjustment of other experimental parameters.
Example 7
The preparation method of the compound CJHK462 comprises the following steps:
the first step is as follows: preparation of intermediate Int-6
Figure BDA0002793914570000211
15.0mmol of intermediate Int-31 (prepared by replacing phenylhydrazine hydrochloride in the first step with o-chlorophenylhydrazine hydrochloride with reference to the preparation method of example 1) was dissolved in 80mL of dry toluene, 12.5mmol of 3-bromocarbazole and 30.0mmol of anhydrous sodium carbonate were added under nitrogen protection, and 0.1mmol of Pd (PPh) was added4And 40mL of ethanol and 40mL of water, heating, refluxing, stirring, reacting for 8 hours, cooling to room temperature, adding 50mL of water for dilution, extracting with dichloromethane, 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 an intermediate Int-6, namely a yellow solid with the yield of 72%.
The second step is that: preparation of Compound CJHK462
Figure BDA0002793914570000212
Dissolving 10.0mmol of intermediate Int-6 in 60mL of dry THF, cooling to 0 ℃ with ice water bath under the protection of nitrogen, adding 11.0mmol of 65% sodium hydride solid, stirring for reaction for 1 hour, adding 11.0mmol of 2-chloro-4, 6-diphenyl-1, 3, 5-triazine, stirring for reaction for 24 hours, adding 50mL of water for dilution, extracting with ethyl acetate, collecting the organic phase, drying, filtering, concentrating the filtrate under reduced pressure to dryness, and separating and purifying with a silica gel column to obtain a compound CJ HK462, a yellow solid with a yield of 86%.
MS and of compound CJHK4621The HNMR test results are as follows:
MS(MALDI-TOF)：m/z 777.2784[M+H]+；1HNMR(δ、CDCl3)：8.97(1H,s)；8.62(1H,s)；8.50～8.42(10H,m)；8.25～8.18(3H,m)；8.13～8.08(3H,m)；7.94～7.88(2H,m)；7.56～7.51(2H,m)；7.45～7.39(9H,m)；7.34～7.32(1H,m)。
example 8
Preparation of the compounds CJHK 453-CJHK 461, CJHK463 and CJHK464 referring to the preparation method of example 7, the compounds CJHK 453-CJHK 461, CJHK463 and CJHK464 of the formula I were prepared by replacing 2-chloro-4, 6-diphenyl-1, 3, 5-triazine of the second step in example 7 with different halides and by performing general adjustment of other experimental parameters.
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 BDA0002793914570000221
Compound C
Figure BDA0002793914570000222
/D
Figure BDA0002793914570000223
/A+B(5％)
Figure BDA0002793914570000224
/LiQ+G(50％)
Figure BDA0002793914570000231
/LiF
Figure BDA0002793914570000232
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 CJHK342 to CJHK485 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 BDA0002793914570000233
As can be seen from Table 1, the driving voltage of the device prepared from the compound of the present invention was substantially the same as that of the device prepared from comparative example 1, but it was 2000cd/cm2The element lifetime under the initial condition is greatly improved, and CJHK350 particularly has good performance in terms of current efficiency and element lifetime.
The properties of only some of the compounds of CJHK 342-CJHK 485 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 one by one 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 CJHK342 to CJHK485 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 BDA0002793914570000241
As can be seen from the results of the device performance tests in Table 2, the compounds of the present invention produced devices, especially CJHK428 (T) compared to the devices produced in comparative example 11N-phenyl) and CJHK478 with similar current efficiency but initial luminance of 2000cd/cm2The LT 90% lifetime in the initial condition was 1.6 and 1.3 times, respectively.
The properties of only some of the compounds CJHK 342-CJHK 485 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 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 FDA0002793914560000011
wherein R is1～R16Same 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～C40Branched or cyclic hetero ofAlkyl radical, having C2～C40Alkenyl or alkynyl group of (A), an aromatic ring system or a heteroaromatic ring system having 5 to 60 carbon atoms, R1～R16Each 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;
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)1)2、N(R17)2、C(＝O)Ar1、C(＝O)R17、P(＝O)(Ar1)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 R17Substituted, or combinations of these systems, wherein one or more non-adjacent-CH2The radicals may be substituted by R17C＝CR17、C≡C、Si(R17)2、Ge(R17)2、Sn(R17)2、C＝O、C＝S、C＝Se、C＝NR17、P(＝O)(R17)、SO、SO2、NR17O, S or CONR17And 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 R17Substitution;
R17each 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)1)2、N(R18)2、C(＝O)Ar1、C(＝O)R18、P(＝O)(Ar1)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, R17Each radical in (a) may be substituted by one or more radicals R18Substituted, or combinations of these systems, wherein one or more non-adjacent-CH2The radicals may be substituted by R18C＝CR18、C≡C、Si(R18)2、Ge(R18)2、Sn(R18)2、C＝O、C＝S、C＝Se、C＝NR18、P(＝O)(R18)、SO、SO2、NR18O, S or CONR18And 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 R17Aliphatic, 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 R18Substitution;
Ar1identical 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 R18Substitution; two groups Ar here bonded to the same nitrogen or phosphorus atom1Can also be selected from N (R) through a single bond18)、C(R18)2Oxygen or sulfur bridging groups;
R18selected 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 R18Wherein one or more hydrogen atoms may be replaced by deuterium atoms, halogen atoms, or nitrile groups, wherein two or more adjacent substituents R18Can form a single or multiple ring with one anotherAliphatic, aromatic or heteroaromatic ring systems.
2. The carbazole derivative according to claim 1, wherein R is1～R16The same or different, selected from one of hydrogen, deuterium, aromatic ring system or heteroaromatic ring system with 5-60 carbon atoms, wherein R is1～R16Each 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;
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)1)2、N(R17)2、C(＝O)Ar1、C(＝O)R17、P(＝O)(Ar1)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 R17Substituted, or combinations of these systems, wherein one or more non-adjacent-CH2The radicals may be substituted by R17C＝CR17、C≡C、Si(R17)2、Ge(R17)2、Sn(R17)2、C＝O、C＝S、C＝Se、C＝NR17、P(＝O)(R17)、SO、SO2、NR17O, S or CONR17And 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 R17Substitution;
R17each 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)1)2、N(R18)2、C(＝O)Ar1、C(＝O)R18、P(＝O)(Ar1)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, R17Each radical in (a) may be substituted by one or more radicals R18Substituted, or combinations of these systems, wherein one or more non-adjacent-CH2The radicals may be substituted by R18C＝CR18、C≡C、Si(R18)2、Ge(R18)2、Sn(R18)2、C＝O、C＝S、C＝Se、C＝NR18、P(＝O)(R18)、SO、SO2、NR18O, S or CONR18And 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 R17Aliphatic, 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 R18Substitution;
Ar1identical 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 R18Substitution; two groups Ar here bonded to the same nitrogen or phosphorus atom1Can also be selected from N (R) through a single bond18)、C(R18)2Oxygen or sulfur bridging groups;
R18selected from hydrogen atom, deuterium atom, fluorine atom, nitrile group, having C1～C20An aliphatic hydrocarbon group, an aromatic ring having 5 to 30 carbon atomsOr a heteroaromatic ring system, wherein R18Wherein one or more hydrogen atoms may be replaced by deuterium atoms, halogen atoms, or nitrile groups, wherein two or more adjacent substituents R18They can form mono-or polycyclic aliphatic, aromatic or heteroaromatic ring systems with one another.
3. The carbazole derivative according to claim 1 or 2, characterized in that the carbazole derivative mainly includes the following structures CJHK342 to CJHK 485:
Figure FDA0002793914560000041
Figure FDA0002793914560000051
Figure FDA0002793914560000061
Figure FDA0002793914560000071
Figure FDA0002793914560000081
Figure FDA0002793914560000091
Figure FDA0002793914560000101
Figure FDA0002793914560000111
wherein, T is1Selected from-O-, -S-, or any of the following structures:
Figure FDA0002793914560000112
and represents a bond.
4. The carbazole derivative according to claim 1, wherein R is1～R16The same or different, selected from hydrogen, deuterium, and one of aromatic ring system or heteroaromatic ring system having 5 to 60 carbon atoms.
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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