CN114907352A - Carbazole derivative and application thereof - Google Patents
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- CN114907352A CN114907352A CN202210478400.8A CN202210478400A CN114907352A CN 114907352 A CN114907352 A CN 114907352A CN 202210478400 A CN202210478400 A CN 202210478400A CN 114907352 A CN114907352 A CN 114907352A
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Abstract
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 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.
Description
Technical Field
The invention belongs to the technical field of organic electroluminescent materials, and particularly relates to a carbazole derivative and application thereof in an organic electroluminescent element, a display device and a lighting device.
Background
In recent years, organic electroluminescent display technologies have become mature, and some products have 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 performance, electroluminescent performance of materials, service life, color purity, matching between various materials and between various electrodes, and the like. Especially, the light emitting device has not yet achieved practical requirements in terms of luminous efficiency and lifetime, 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 transitions of singlet excitons is 25%, and the theoretical limit of fluorescence from radiative transitions 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 carbazole derivative that is used as a raw material of a material for an organic electroluminescent element, and provides 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):
wherein, X 1 、X 2 Each independently represents N or CR 7 Or two radicals X adjacent to each other 1 And X 2 Represents a group of the following formula (II);
z, identically or differently at each occurrence, denotes CR 0 Or N;
a represents, identically or differently on each occurrence, CR 8 Or N, and "^" indicates the adjacent group X in formula (I) 1 And X 2 ；
Ar 1 Selected from the group consisting of substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 2 -C 60 Heterocyclic aryl groups;
l is selected from substituted or unsubstituted C 6 -C 60 Arylene, substituted or unsubstituted C 2 -C 60 Heterocyclylene aryl;
R 0 、R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 each independently selected from the group consisting of: hydrogen, deuterium, fluorine, nitrile group, having C 1 ～C 40 Straight chain alkyl of (2) having C 1 ～C 40 Linear heteroalkyl group of (A) having C 3 ～C 40 A branched or cyclic alkyl group of (2), having C 3 ～C 40 A branched or cyclic heteroalkyl group of (A) having C 2 ～C 40 Alkenyl or alkynyl ofSubstituted or unsubstituted C 6 -C 60 Aryl or substituted or unsubstituted C 2 -C 60 Heterocyclic aryl groups, and any two or more substituents that are adjacent may optionally be joined or fused to form a substituted or unsubstituted ring, with or without N, O, S, Si, P, or B in the ring.
Aryl in the sense of the present invention contains 6 to 60 carbon atoms and heteroaryl in the sense of the present invention contains 2 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 groups herein encompass monocyclic groups and polycyclic ring systems. Polycyclic rings can have two carbons that are two contiguous rings or two or more rings in common, referred to as "fused," where at least one of the rings is aromatic, e.g., the other rings can be cycloalkyls, cycloalkenyls, aryls, heterocyclics, and/or heteroaryls. In addition, multiple aryl or heteroaryl groups may also be linked by non-aromatic units such as C, N, O or S atoms, for example, as with systems in which two or more aryl groups are linked by, for example, a short alkyl group, such as fluorene, 9' -spirobifluorene, 9-diarylfluorene, triarylamine, diaryl ether, dibenzofuran, or dibenzothiophene, and the like.
The alkyl group used in the present invention means a monovalent functional group obtained by removing one hydrogen atom from a linear or branched saturated hydrocarbon having 1 to 40 carbon atoms. As non-limiting examples thereof, there are methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, isopentyl, hexyl and the like. Heteroalkyl means a hydrogen atom or-CH on an alkyl group 2 -substituted by at least one heteroatom selected from halogen, nitrile, N, O, S or silicon, as non-limiting examples difluoromethyl, trifluoromethyl, trifluoroethyl, pentafluoroethyl, nitrile, acetonitrile, methoxymethyl, methoxyethyl, trimethylsilyl, triisopropylsilyl and the like.
The alkenyl group used in the present invention means a monovalent functional group obtained by removing one hydrogen atom from a linear or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and having one or more carbon-carbon double bonds. As non-limiting examples thereof, there are vinyl, allyl, isopropenyl, 2-butenyl, and the like.
The alkynyl group used in the present invention means a monovalent functional group obtained by removing one hydrogen atom from a linear or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and having one or more carbon-carbon triple bonds. As non-limiting examples thereof, there are ethynyl, 2-propynyl and the like.
In general, the cycloalkyl group, cycloalkenyl group according to the present invention means a monovalent functional group obtained by removing one hydrogen atom from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms. As non-limiting examples thereof, there may be mentioned cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, norbornyl, adamantyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptyl, cycloheptenyl, and the like, wherein one or more-CH groups 2 The 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 heterocycloalkyl group used in the present invention refers to a monovalent functional group obtained by removing one hydrogen atom from a non-aromatic hydrocarbon having a nuclear number of 3 to 40. In this case, more than one carbon, preferably 1 to 3 carbons, in the ring is substituted with a heteroatom such as N, O or S. As non-limiting examples thereof, there are tetrahydrofuran, tetrahydrothiophene, morpholine, piperazine and the like.
As used herein, "a combination thereof" or "group" means that one or more members of the applicable list are combined to form a known or chemically stable arrangement that one of ordinary skill in the art can envision from the applicable list. For example, alkyl and deuterium can be combined to form a partially or fully deuterated alkyl; halogen and alkyl groups may be combined to form haloalkyl substituents, such as trifluoromethyl and the like; and halogen, alkyl, and aryl groups may be combined to form haloaralkyl groups.
Further, the structure of the carbazole derivative is selected from the group consisting of the following formulas I-1 to I-18:
further, said Ar 1 Selected from substituted or unsubstitutedC of (A) 2 -C 60 A heterocyclic aryl group.
Further, L is selected from the group consisting of substituted or unsubstituted C 6 -C 60 Arylene, substituted or unsubstituted C 2 -C 60 Heterocyclylene aryl.
Further, each of said R 0 、R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 Each occurrence, which is the same or different, is independently selected from the group consisting of: hydrogen, deuterium, substituted or unsubstituted C 6 -C 60 Aryl or substituted or unsubstituted C 2 -C 60 The heterocyclic aryl group, and any adjacent two or more substituents may be optionally joined or fused to form a substituted or unsubstituted ring with or without N, O, S, Si, P, or B in the ring.
Further, the heteroaryl is selected from the group consisting of the following groups II-1 to II-17:
wherein the content of the first and second substances,
Z 1 、Z 2 each independently selected from the group consisting of hydrogen, deuterium, halogen, hydroxy, nitrile, nitro, amino, amidino, hydrazine, hydrazone, carboxy or carboxylate thereof, sulfonic or sulfonate thereof, phosphoric or phosphate thereof, C 1 -C 40 Alkyl radical, C 2 -C 40 Alkenyl radical, C 2 -C 40 Alkynyl, C 1 -C 40 Alkoxy radical, C 3 -C 40 Cycloalkyl radical, C 3 -C 40 Cycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 An arylthioether group, or a substituted or unsubstituted C 2 -C 60 Heterocyclic aryl groups;
x1 represents an integer of 1 to 4; x2 represents an integer of 1 to 3; x3 represents 1 or 2; x4 represents an integer of 1 to 6; x5 represents an integer of 1 to 5;
T 1 represents O, S, CR 'R "or NAr';
r 'and R' are each independently selected from hydrogen, deuterium, C 1 ～C 40 Alkyl of (C) 1 ～C 40 With heteroalkyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Arylamino, or substituted or unsubstituted C 2 -C 60 Heterocyclic aryl, R 'and R' may optionally be joined or fused to form one or more additional substituted or unsubstituted rings, with or without one or more heteroatoms N, P, B, O or S in the ring so formed; preferably, R', R "are methyl, phenyl or fluorenyl;
ar' is selected from C 1 ～C 40 Alkyl of (C) 1 ～C 40 Heteroalkyl of (a), C 3 ～C 40 Cycloalkyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Condensed ring aryl, substituted or unsubstituted C 6 -C 60 Arylamino, or substituted or unsubstituted C 2 -C 60 Heterocyclic aryl groups; preferably, Ar ’ Is methyl, ethyl, phenyl, biphenyl or naphthyl;
Further, said Ar is 1 Selected from the group consisting of the following groups III-1 to III-13:
wherein, T 2 Selected from O or S;
R 14 、R 15 each independently selected from hydrogen, deuterium, substituted or unsubstituted C 6 ～C 60 Aryl, substitutedOr unsubstituted C 2 ～C 60 Heteroaryl groups;
R 16 selected from hydrogen, deuterium, C 1 ～C 40 Alkyl, substituted or unsubstituted C 6 -C 60 Aryl, or substituted or unsubstituted C 2 -C 60 Heteroaryl groups; r 16 One or more to saturated substitutions;
denotes Ar 1 The bond of the substituent to L.
According to an embodiment of the invention, said R 14 、R 15 Each independently selected from the group consisting of phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, naphthalene-substituted phenyl, phenanthrene-substituted phenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, dibenzofuran-substituted phenyl, dibenzothiophene-substituted phenyl, phenyl-substituted carbazolyl, naphthyl-substituted carbazolyl, biphenyl-substituted carbazolyl, 9-phenylcarbazolyl, benzonaphthofuranyl, benzonaphthothiophenyl, or phenyl-substituted benzocarbazolyl;
according to an embodiment of the invention, R 16 Is hydrogen or deuterium.
Further, the L is selected from a single bond, phenylene, pyridylene or naphthalenediyl.
Further, said R 0 、R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 Each independently selected from the group consisting of hydrogen, phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, naphthalene-substituted phenyl, phenanthrene-substituted phenyl, dibenzofuranyl, dibenzothienyl, carbazolyl, dibenzofuran-substituted phenyl, dibenzothiophene-substituted phenyl, phenyl-substituted carbazolyl, naphthyl-substituted carbazolyl, biphenyl-substituted carbazolyl, 9-phenylcarbazolyl, benzonaphthofuranyl, benzonaphthothienyl, or phenyl-substituted benzocarbazolyl, and any two or more adjacent substituents may be optionally joined or fused to form a five-membered heterocyclic ring, a five-membered carbocyclic ring, a six-membered heterocyclic ring, or a six-membered carbocyclic ring.
Further, the carbazole derivative is one of the following structures represented by N151 to N426:
wherein, T 3 Each is independently selected from-O-, -S-, or one of the following structures:
and represents a bond.
In another aspect, the invention provides a process for the preparation of a compound of formula (I), as exemplified in scheme 1 below:
scheme 1:
in scheme 1, the symbols used are as defined in formula (I), and X is Cl, Br, I or OTf;
specifically, the compound of formula (I) is prepared from compound C having a parent nucleus structure and compound D containing an acceptor substituent by palladium-catalyzed or base-catalyzed coupling reaction.
As palladium catalysts which can be used for the palladium-catalyzed coupling reaction, there may be selected: pd (P- t Bu 3 ) 2 、Pd(PPh 3 ) 4 、Pd 2 (dba) 3 、Pd 2 (dba) 3 CHCl 3 、PdCl 2 (PPh 3 ) 2 、PdCl 2 (CH 3 CN) 2 、Pd(OAc) 2 、Pd(acac) 2 、Pd/C、PdCl 2 、[Pd(allyl)Cl] 2 And the like, or a mixture of two or more thereof is used.
In addition, the base used in the palladium-catalyzed coupling reaction or base-catalyzed coupling reaction may be selected from: sodium tert-butoxide, potassium tert-butoxide, sodium hydride, lithium hydride, sodium tert-amylate, sodium ethoxide, sodium methoxide, sodium carbonate, potassium carbonate, cesium carbonate, lithium, potassium hydride, triethylamine, cesium fluoride, and the like, and mixtures of one or two or more thereof.
The coupling reaction may be carried out in an organic solvent, wherein the organic solvent may be selected from: ether solvents such as diethyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, 1, 4-dioxane, ethylene glycol ethyl ether, ethylene glycol diethyl ether, ethylene glycol methyl ether, diethylene glycol diethyl ether, or anisole, aromatic hydrocarbon solvents such as benzene, toluene, or xylene, chlorobenzene, dichlorobenzene, N-dimethylformamide, N-dimethylacetamide, N-methylpyrrolidone, dimethyl sulfoxide, and sulfolane, and one or a mixture of two or more thereof may be used.
In addition, the compound of formula D can be prepared using conventional organic reactions or can be obtained commercially.
In addition, the present invention provides an organic electroluminescent element comprising a first electrode, a second electrode, a capping layer and at least one organic layer interposed between the first electrode and the second electrode, wherein at least one of the organic layer or the capping layer comprises 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 light-emitting layer and the thin-film encapsulation layer, all materials can be used in the manner conventionally used according to the prior art. The person skilled in the art will thus be able to use all materials known for organic electroluminescent elements in combination with the light-emitting layer according to the invention without inventive effort.
Preference is furthermore given to organic electroluminescent elements in which one or more layers are applied by means of a sublimation process in which the temperature in a vacuum sublimation apparatus is below 10 -5 Pa, preferably less than 10 -6 Pa is applied by vapor deposition. However, the initial pressure may also be even lower, e.g. below 10 -7 Pa。
Preference is likewise given to organic electroluminescent elements in which one or more layers are applied by means of an organic vapor deposition method or by means of carrier gas sublimation, where 10 -5 The material is applied under a pressure between Pa and 1 Pa. A particular example of this method is the organic vapour jet printing method, in which the material is applied directly through a nozzle and is therefore structured.
Preference is furthermore given to organic electroluminescent elements in which one or more layers are produced from solution, for example by spin coating, or by means of any desired printing method, for example screen printing, flexographic printing, offset printing, photoinitiated thermal imaging, thermal transfer, ink-jet printing or nozzle printing. Soluble compounds, for example, are obtained by appropriate substitution of a compound of formula (I). These methods are also particularly suitable for oligomers, dendrimers and polymers. Furthermore, hybrid methods are possible, in which, for example, one or more layers are applied from solution and one or more further layers are applied by vapor deposition.
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 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, a capping layer, or a photorefractive layer.
The present invention also relates to mixtures comprising at least one compound of the formula (I) or the preferred embodiments described above and at least one further compound. If the compounds according to the invention are used as matrix materials, the further compounds can be fluorescent or phosphorescent emitters. The mixture may then additionally comprise other materials as additional matrix materials. The invention also relates to the use of the compounds according to the invention in electronic components. Preferably, the compounds according to the invention are used in an electron transport layer or as matrix material in a light-emitting layer, as mentioned above and below. The compounds according to the invention and the electronic components obtainable therefrom, in particular organic electroluminescent components, differ from the prior art by one or more of the following surprising advantages:
1. the electronic components obtainable using the compounds of the present invention exhibit very high stability and very long life as compared with those obtainable using conventional compounds.
2. The electronic components obtainable using the compounds of the invention exhibit high efficiencies, in particular high luminous efficiencies and high external quantum efficiencies.
3. The compounds of the present invention provide low operating voltages.
4. The compounds according to the invention can be processed using conventional methods, whereby cost advantages can also be achieved.
5. The films obtainable using the compounds of the invention exhibit excellent quality, especially with regard to the uniformity of the film.
6. The compounds of the invention can be produced in a very rapid and easy manner using conventional methods, so that cost advantages can also be achieved.
These advantages mentioned above are not accompanied by a weakening of other electronic properties.
It should be noted that variations of the embodiments described in the present invention fall within the scope of the invention. Each feature disclosed in this specification may be replaced by alternative features serving the same, equivalent or similar purpose, unless expressly excluded. Thus, unless expressly stated otherwise, each feature disclosed in this specification is intended to be an example of a generic series of equivalent or similar features.
All features of the invention may be combined with each other in any manner, unless specified features and/or steps are mutually exclusive. This applies in particular to the preferred features of the invention. Also, features that are not necessarily combined may be used separately (and not in combination). It should furthermore be pointed out that many features, in particular features of preferred embodiments of the invention, are inventive per se and should not be considered as only part of an embodiment of the invention. Independent protection may be sought for these features in addition to or in lieu of each and every invention that is presently claimed.
The teachings of the technical actions disclosed in the present invention can be extracted and combined with other embodiments. The present invention is explained in more detail by the following examples, but is not intended to be limited thereby. Based on the description, one skilled in the art will be able to carry out the invention within the full scope of the disclosure and, without inventive effort, be able to prepare and use other compounds of the invention in electronic components or use the methods of the invention.
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 shows a schematic diagram of an organic light emitting device 100. The illustrations are not necessarily drawn to scale. The device 100 may include a substrate 101, an anode 102, a hole injection layer 103, a hole transport layer 104, an electron blocking layer 105, a light emitting layer 106, a hole blocking layer 107, an electron transport layer 108, an electron injection layer 109, a cathode 110, and a capping layer (CPL) 111. The device 100 may be fabricated by sequentially depositing the described layers.
Fig. 2 shows a schematic diagram of an organic light emitting device 200 with two light emitting layers. The device includes a substrate 201, an anode 202, a hole injection 203, a hole transport layer 204, a first light emitting layer 205, an electron transport layer 206, a charge generation layer 207, a hole injection layer 208, a hole transport layer 209, a second light emitting layer 210, an electron transport layer 211, an electron injection layer 212, and a cathode 213. The device 200 may be prepared by sequentially depositing the described layers. Since the most common OLED devices have one light emitting layer, while device 200 has a first light emitting layer and a second light emitting layer, the light emitting peak shapes of the first light emitting layer and the second light emitting layer may be overlapping or cross-overlapping or non-overlapping. In the corresponding layers of device 200, materials similar to those described with respect to device 100 may be used. Fig. 2 provides one example of how some layers may be added from the structure of device 100.
Detailed Description
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
A process for the preparation of compound N169, comprising the steps of:
the first step is as follows: preparation of intermediate Int-1
20.0mmol of 1-bromo-11H-benzo [ a ]]Carbazole, 22.0mmol of 4-chloro-9H-carbazole-3-boronic acid pinacol ester, 40.0mmol of potassium phosphate, 0.1mmol of Pd (PPh) 3 ) 4 Adding 60mL of toluene, 30mL of ethanol and 30mL of water into the catalyst, heating to reflux and stirring for reaction for 8 hours under the protection of nitrogen, cooling to room temperature, adding 50mL of water for dilution, extracting with toluene, drying an organic phase, filtering, concentrating the filtrate under reduced pressure to dryness, and separating and purifying by using a silica gel column to obtain a yellow solid Int-1 with yield: 86 percent.
The second step is that: preparation of intermediate A1
15.0mmol of compound Int-1 are dissolved in 80mL of dry xylene, under nitrogen protection, 22.5mmol of sodium tert-butoxide and 0.1mmol of Pd are added 2 (dba) 3 CHCl 3 And 0.02mL of a 10% solution of tri-tert-butylphosphine in toluene, heating to 110 ℃, stirring for reaction for 15 hours, cooling to room temperature, diluting with 50mL of water, extracting with dichloromethane, 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 compound A1, a yellow solid, yield: 75 percent.
With reference to the analogous synthetic procedures described above, the following compounds were prepared:
the third step: preparation of Compound N169
10.0mmol of Compound A1 dissolved in 50mL dry DMF under nitrogen protectionCooling to 0 ℃ by using an ice water bath, adding 12.0mmol of 65% sodium hydride solid in batches, stirring for reaction for 1 hour, adding 12.0mmol of 2-biphenyl-4-chloro-6-phenyl-1, 3, 5-triazine, heating to 50 ℃, stirring for reaction for 12 hours, pouring the reaction liquid into 250mL of ice water, filtering, washing a filter cake by using water and ethanol, and separating and purifying by using a silica gel column to obtain a compound N169, namely a yellow solid, wherein the yield is as follows: 82%, MS (MALDI-TOF): m/z 688.2509[ M + H ]] + 。
With reference to the analogous synthetic methods described above, the following compounds were prepared:
example 2
Preparation of compound N307:
10.0mmol of compound A1 was dissolved in 60mL dry xylene, 12.0mmol of 4-biphenyl-2- (2-bromophenyl) quinazoline and 15.0mmol of sodium tert-butoxide were added under nitrogen protection, and 0.1mmol of Pd was added 2 (dba) 3 CHCl 3 And 0.02mL of 10% tri-tert-butylphosphine toluene solution, heating to 110 ℃, stirring for reaction for 15 hours, cooling to room temperature, adding 50mL of water for dilution, extracting with dichloromethane, 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 the compound N307, a yellow solid, yield: 84%, MS (MALDI-TOF): m/z 737.2713[ M + H ]] + 。
With reference to the analogous synthetic procedures described above, the following compounds were prepared:
t in examples 1 and 2 above 3 Each is independently selected from-O-, -S-, or one of the following structures:
and represents a bond.
Preparation of organic electroluminescent element
Comparative example 1
The following compound C was used as a hole injection material, compound D as a hole transport material, compound E as a red light host material, compound F as a red light dopant material, compound G as an electron transport dopant material, and LiQ as an electron transport host material.
Compound C
/D
/E+F(3％)
/LiQ+G(30％)
/LiF
/Mg+Ag(65％)
/NPB
The OLED comparative element 1 was fabricated by sequentially depositing ITO glass on an EL evaporator manufactured by DOV.
Comparative example 2
An OLED element was prepared according to the method of comparative example 1, wherein the aforementioned compound E was replaced with compound H, having the structure:
test example 1
An OLED element was prepared in accordance with the method of comparative example 1, wherein the aforementioned Compound E was replaced with any one or more of the Compounds N151 to N426 of the present invention to prepare an organic electroluminescent element,
the element structure is as follows: ITO/Al/C
/D
/[ N151 to N426 ] any one or more]+F(3％)
/LiQ+G(30％)
/LiF
/Mg+Ag(65％)
/NPB
The organic electroluminescent element prepared by the above process was subjected to the following performance tests:
the driving voltage and current efficiency of the organic electroluminescent elements prepared in test example 1, comparative example 1 and comparative example 2, and the lifetime of the elements were measured at the same luminance using a digital source meter and a luminance meter. Specifically, the voltage was raised at a rate of 0.1V per second, and it was determined that the luminance of the organic electroluminescent element reached 1000cd/m 2 The current density is measured at the same time as the driving voltage; the ratio of the brightness to the current density is the current efficiency; the LT 90% lifetime test is as follows: using a luminance meter at 1000cd/m 2 At luminance, the luminance decay of the organic electroluminescent element was measured to be 900cd/m while maintaining a constant current 2 Time in hours.
TABLE 1 test results of the performance of each element
As is clear from Table 1, when the compound of the present invention is used as a host material for an organic electroluminescent element, the current efficiency can be increased to 23.0cd/A or more, and the life is significantly increased, and the compound is a host material having good performance.
Compared with the compound of the invention, the compound E in the comparative example 1 is characterized in that the compound E is formed by connecting two carbazoles through a single bond, and the compound of the invention is connected with the carbazole through naphthocarbazole, so that the plane conjugation capability is enhanced, the transmission of molecules to holes and electrons is more balanced, and the formation of excitons in a light-emitting layer is facilitated, therefore, the efficiency is improved, and the service life is greatly improved.
The compound H in comparative example 2 is different from the compound of the present invention in that naphtho-two indoles form a large planar structure, and although the planar conjugation ability is not very different, steric hindrance is very large due to the obstruction of the large planar structure, which is not favorable for close packing of molecules and doped materials. And the carbazole is connected outside the planes of the two naphtho indoles to effectively extend the conjugated plane, so that the molecular film forming and charge transmission performance are excellent, and the charge transmission in the device is more balanced. It is thus understood that the carbazole derivative of the present invention can achieve more excellent performance and a longer lifetime when used as a host material.
The properties of only some of the compounds in N151 to N426 are listed in Table 1, and the properties of other compounds are substantially consistent with the data of the compounds listed in the Table, and are not listed any more due to space limitation.
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 appended claims.
Claims (10)
1. A carbazole derivative having a structure represented by formula (I):
wherein, X 1 、X 2 Each independentlyRepresents N or CR 7 Or two radicals X adjacent to each other 1 And X 2 Represents a group of the following formula (II);
z, identically or differently at each occurrence, denotes CR 0 Or N;
a represents, identically or differently on each occurrence, CR 8 Or N, and "^" indicates the adjacent group X in formula (I) 1 And X 2 ；
Ar 1 Selected from substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 2 -C 60 Heterocyclic aryl groups;
l is selected from substituted or unsubstituted C 6 -C 60 Arylene, substituted or unsubstituted C 2 -C 60 Heterocyclylene aryl;
R 0 、R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 each independently selected from the group consisting of: hydrogen, deuterium, fluorine, nitrile group, having C 1 ～C 40 Straight chain alkyl of (2) having C 1 ～C 40 Linear heteroalkyl group of (A) having C 3 ～C 40 A branched or cyclic alkyl group of (2), having C 3 ～C 40 A branched or cyclic heteroalkyl group of (A) having C 2 ～C 40 Alkenyl or alkynyl, substituted or unsubstituted C 6 -C 60 Aryl or substituted or unsubstituted C 2 -C 60 The heterocyclic aryl group, and any adjacent two or more substituents may be optionally joined or fused to form a substituted or unsubstituted ring with or without N, O, S, Si, P, or B in the ring.
2. The carbazole derivative according to claim 1, wherein the carbazole derivative has a structure selected from the group consisting of the following formulas I-1 to I-18:
Ar 1 selected from substituted or unsubstituted C 2 -C 60 A heterocyclic aryl group;
l is selected from substituted or unsubstituted C 6 -C 60 Arylene, substituted or unsubstituted C 2 -C 60 Heterocyclylene aryl;
each R 0 、R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 Each occurrence, which is the same or different, is independently selected from the group consisting of: hydrogen, deuterium, substituted or unsubstituted C 6 -C 60 Aryl or substituted or unsubstituted C 2 -C 60 The heterocyclic aryl group, and any adjacent two or more substituents may be optionally joined or fused to form a substituted or unsubstituted ring with or without N, O, S, Si, P, or B in the ring.
3. The carbazole derivative according to claim 1 or 2, wherein the heteroaryl group is selected from the group consisting of the following groups II-1 to II-17:
wherein the content of the first and second substances,
Z 1 、Z 2 each independently selected from the group consisting of hydrogen, deuterium, halogen, hydroxy, nitrile, nitro, amino, amidino, hydrazine, hydrazone, carboxy or carboxylate thereof, sulfonic or sulfonate thereof, phosphoric or phosphate thereof, C 1 -C 40 Alkyl radical, C 2 -C 40 Alkenyl radical, C 2 -C 40 Alkynyl, C 1 -C 40 Alkoxy radical, C 3 -C 40 Cycloalkyl radical, C 3 -C 40 Cycloalkenyl, substituted or unsubstitutedC 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 An arylthioether group, or a substituted or unsubstituted C 2 -C 60 Heterocyclic aryl groups;
x1 represents an integer of 1 to 4; x2 represents an integer of 1 to 3; x3 represents 1 or 2; x4 represents an integer of 1 to 6; x5 represents an integer of 1 to 5;
T 1 represents O, S, CR 'R "or NAr';
r 'and R' are each independently selected from hydrogen, deuterium, C 1 ～C 40 Alkyl of (C) 1 ～C 40 With heteroalkyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Arylamino, or substituted or unsubstituted C 2 -C 60 Heterocyclic aryl, R 'and R' may optionally be joined or fused to form one or more additional substituted or unsubstituted rings, with or without one or more heteroatoms N, P, B, O or S in the ring so formed; preferably, R', R "are methyl, phenyl or fluorenyl;
ar' is selected from C 1 ～C 40 Alkyl of (C) 1 ～C 40 Heteroalkyl of (a), C 3 ～C 40 Cycloalkyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Condensed ring aryl, substituted or unsubstituted C 6 -C 60 Arylamino, or substituted or unsubstituted C 2 -C 60 Heterocyclic aryl groups; preferably, Ar' is methyl, ethyl, phenyl, biphenyl or naphthyl;
4. The carbazole derivative according to any one of claims 1 to 3, wherein Ar is Ar 1 Selected from the group consisting of the following groups III-1 to III-13Group (2):
wherein, T 2 Selected from O or S;
R 14 、R 15 each independently selected from hydrogen, deuterium, substituted or unsubstituted C 6 ～C 60 Aryl, substituted or unsubstituted C 2 ～C 60 Heteroaryl groups;
R 16 selected from hydrogen, deuterium, C 1 ～C 40 Alkyl, substituted or unsubstituted C 6 -C 60 Aryl, or substituted or unsubstituted C 2 -C 60 Heteroaryl groups; r 16 One or more to saturated substitutions;
denotes Ar 1 The bond of the substituent to L.
5. The carbazole derivative according to any one of claims 1 to 4, wherein R is 14 、R 15 Each independently selected from the group consisting of phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, naphthalene-substituted phenyl, phenanthrene-substituted phenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, dibenzofuran-substituted phenyl, dibenzothiophene-substituted phenyl, phenyl-substituted carbazolyl, naphthyl-substituted carbazolyl, biphenyl-substituted carbazolyl, 9-phenylcarbazolyl, benzonaphthofuranyl, benzonaphthothiophenyl, or phenyl-substituted benzocarbazolyl;
R 16 is hydrogen or deuterium.
6. The carbazole derivative according to claim 1, wherein L is selected from a single bond, a phenylene group, a pyridylene group, or a naphthalenediyl group;
R 0 、R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 each independently selected from hydrogenPhenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, naphthalene-substituted phenyl, phenanthrene-substituted phenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, dibenzofuran-substituted phenyl, dibenzothiophene-substituted phenyl, phenyl-substituted carbazolyl, naphthyl-substituted carbazolyl, biphenyl-substituted carbazolyl, 9-phenylcarbazolyl, benzonaphthofuranyl, benzonaphthothiophenyl, or phenyl-substituted benzocarbazolyl, and any two or more adjacent substituents may be optionally joined or fused to form a five-membered heterocyclic ring, a five-membered carbocyclic ring, a six-membered heterocyclic ring, or a six-membered carbocyclic ring.
7. The carbazole derivative according to any one of claims 1 to 6, wherein the carbazole derivative is one of the following structures represented by N151 to N426:
wherein, T 3 -is selected from-O-, -S-, or one of the following structures:
and represents a bond.
8. An organic electroluminescent element comprising a first electrode, a second electrode, a capping layer and at least one organic layer interposed between the first electrode and the second electrode, wherein at least one of the organic layer or the capping layer comprises the carbazole derivative according to any one of claims 1 to 7.
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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