CN113698410A - Organic compound, preparation method thereof and electron transport material - Google Patents
Organic compound, preparation method thereof and electron transport material Download PDFInfo
- Publication number
- CN113698410A CN113698410A CN202110947364.0A CN202110947364A CN113698410A CN 113698410 A CN113698410 A CN 113698410A CN 202110947364 A CN202110947364 A CN 202110947364A CN 113698410 A CN113698410 A CN 113698410A
- Authority
- CN
- China
- Prior art keywords
- compound
- mixture
- organic compound
- catalyst
- solvent
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains three hetero rings
- C07D487/16—Peri-condensed systems
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/16—Electron transporting layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
Landscapes
- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The embodiment of the application discloses an organic compound, a preparation method thereof and an electron transport material; the organic compound has the following molecular structural formula:
wherein, the R1 group and the R2 group are respectively independent aromatic compounds with the carbon number less than 15 or heterocyclic compounds containing nitrogen atoms; the organic compound provided by the application can form an amorphous film structure, has a large conjugated plane configuration, is favorable for electron flow, and improves the transmission rate of an electron transmission material, so that the luminous efficiency is improved, and the display effect is improved.
Description
Technical Field
The application relates to the technical field of display, in particular to an organic compound, a preparation method thereof and an electron transport material.
Background
The glass transition temperature of most of the electron transport materials used in current electroluminescent devices, such as bathophenanthroline (BPhen), Bathocuproine (BCP) and 1,3, 5-tris [ (3-pyridyl) -3-phenyl ] benzene (TmPyPB), is low, typically less than 85 ℃. When the electroluminescent device is operated, joule heat generated can cause degradation or change of molecular structure of bathophenanthroline (BPhen), Bathocuproine (BCP) and 1,3, 5-tris [ (3-pyridyl) -3-phenyl ] benzene (TmPyPB), thereby causing the problems of reduction of electron transport rate of the device and serious reduction of luminous efficiency and service life.
Disclosure of Invention
The embodiment of the application provides an organic compound, a preparation method thereof and an electron transport material, so as to solve the technical problem that the electron transport rate of a light-emitting device is low at the present stage.
The application provides an organic compound having the following molecular structural formula:
wherein the R1 group and the R2 group are each independently an aromatic compound having less than 15 carbon atoms or a heterocyclic compound containing a nitrogen atom.
In the organic compounds of the present application, the aromatic compound includes any one of the following molecular structural formulas:
in the organic compound of the present application, the heterocyclic compound containing a nitrogen atom includes any one of the following molecular structural formulas:
accordingly, embodiments of the present application also provide a method for preparing an organic compound, including:
mixing a first compound and a first solvent to obtain a first mixture;
mixing the second compound with the first solvent to obtain a second mixture;
adding the second mixture into the first mixture, and reacting to obtain a third compound;
mixing the first catalyst, the second catalyst and the second solvent to obtain a third mixture;
dissolving the third compound and the fourth compound in a second solvent to obtain a fourth mixture;
mixing the fourth mixture with the third mixture, and reacting to obtain a target product;
wherein the molecular structural formula of the first compound is
The molecular structural formula of the second compound is
The molecular structural formula of the fourth compound is
Wherein, in the molecular structural formula of the fourth compound, the R1 group and the R2 group are respectively and independently an aromatic compound with the carbon number less than 15 or a heterocyclic compound containing a nitrogen atom.
In the method for preparing an organic compound of the present application, the third compound includes the following molecular structural formula:
in the method for producing an organic compound of the present application, in the step of mixing the first catalyst with the second catalyst and the second solvent to obtain the third mixture, the second solvent includes tetrahydrofuran, and the second catalyst includes titanium tetrachloride;
wherein a ratio of the volume of the second solvent to the volume of the second catalyst is 400: 13.
in the method for preparing an organic compound, the step of mixing the first catalyst, the second catalyst, and the second solvent to obtain a third mixture includes:
adding the first catalyst into a second solvent, and then adding the second catalyst to form a third mixture;
wherein the first catalyst comprises zinc.
In the method for producing an organic compound of the present application, the ratio of the amount of the substance of the third compound to the amount of the substance of the fourth compound is 1: 1.
In the method for producing an organic compound of the present application, the ratio of the amount of the substance of the first compound to the amount of the substance of the second compound is 4: 5.
In addition, the embodiment of the application also provides an electron transport material which comprises the organic compound.
Has the advantages that: the application provides a device with
The organic compound can form an amorphous film structure, thereby being beneficial to electron flow and improving the electron mobility of the electron transport material; moreover, the molecular structure of the organic compound has a large conjugated plane configuration, which is beneficial to improving the transmission rate of the electron transmission material, thereby improving the luminous efficiency of the luminescent device; in addition, the organic compound has deeper HOMO energy level and LUMO energy level, and improves the thermal stability and luminous efficiency of the organic light-emitting device, thereby further improving the display effect.
Drawings
In order to more clearly illustrate the technical solutions in the embodiments of the present invention, the drawings needed to be used in the description of the embodiments will be briefly introduced below, and it is obvious that the drawings in the following description are only some embodiments of the present invention, and it is obvious for those skilled in the art to obtain other drawings based on these drawings without creative efforts.
FIG. 1 is a block flow diagram of a process for the preparation of organic compounds as described in the examples herein;
fig. 2 is a schematic view of the layer structure of the light emitting device described in the embodiment of the present application.
Detailed Description
The technical solutions in the embodiments of the present application will be clearly and completely described below with reference to the drawings in the embodiments of the present application, and it is obvious that the described embodiments are only a part of the embodiments of the present application, and not all of the embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present application.
The embodiment of the application provides an organic compound, a preparation method thereof and an electron transport material. The following are detailed below. It should be noted that the following description of the embodiments is not intended to limit the preferred order of the embodiments. In addition, in the description of the present application, the term "including" means "including but not limited to". The terms first, second, third and the like are used merely as labels, and do not impose numerical requirements or an established order. Various embodiments of the invention may exist in a range of versions; it is to be understood that the description in the form of a range is merely for convenience and brevity and should not be construed as an inflexible limitation on the scope of the invention; accordingly, the described range descriptions should be considered to have specifically disclosed all the possible sub-ranges as well as individual numerical values within that range. For example, it is contemplated that the description of a range from 1 to 6 has specifically disclosed sub-ranges such as, for example, from 1 to 3, from 1 to 4, from 1 to 5, from 2 to 4, from 2 to 6, from 3 to 6, etc., as well as individual numbers within a range such as, for example, 1, 2, 3, 4, 5, and 6, as applicable regardless of the range. In addition, whenever a numerical range is indicated herein, it is meant to include any number (fractional or integer) recited within the indicated range.
In the organic light emitting device, the electron transport material has the functions of balancing carriers, enhancing electron injection, reducing working voltage, blocking excitons and the like. The electron transport material used in conventional electroluminescent devices is typically Alq3 (aluminum 8-hydroxyquinoline), but the electron mobility ratio of Alq3 is low (approximately l0-6cm2/Vs), making the electron transport and hole transport of the device unbalanced. With the commercialization and application of electroluminescent devices, there is a desire for Electroluminescent (ETL) materials with higher transmission efficiency and better performance.
The electron transport materials, such as bathophenanthroline (BPhen), Bathocuproine (BCP) and TmPyPB, which are used more frequently at present, can substantially meet the market demand of organic electroluminescent panels, but have lower glass transition temperature, generally less than 85 ℃, and the generated joule heat can cause the degradation of molecules and the change of molecular structure when the device is operated, so that the panel efficiency is lower and the thermal stability is poorer. Meanwhile, the molecular structure is symmetrical regularly and is easy to crystallize after a long time. After the electron transport material is crystallized, the charge transition mechanism between molecules is different from the amorphous film mechanism in normal operation, so that the electron transport performance is reduced, the electron and hole mobility of the whole device is unbalanced, the exciton formation efficiency is greatly reduced, and the exciton formation is concentrated at the interface of the electron transport layer and the light emitting layer, so that the efficiency and the service life of the device are seriously reduced. In order to solve the above technical problem, the present application proposes the following solutions.
The embodiment of the application provides an organic compound, which has the following molecular structural formula:
wherein the R1 group and the R2 group are each independently an aromatic compound having not more than 14 carbon atoms or a heterocyclic compound containing a nitrogen atom.
The organic compound provided by the embodiment of the application has a large conjugated plane configuration with multiple benzene rings and multiple heterocyclic rings, and is favorable for improving the electron transmission rate of an electron transmission material, and the organic compound has low symmetry of a plane structure, so that the formed material is not easy to crystallize, has an amorphous film structure and high stability, is favorable for electron flow in the material, improves the electron mobility of the material and has good thermal stability, and finally improves the luminous efficiency and the display effect of an organic light-emitting device prepared from the organic compound and prolongs the service life of the light-emitting device.
The technical solution of the present application will now be described with reference to specific embodiments.
The organic compound has the following molecular structural formula:
wherein, in the R1 group and the R2 group, the R1 group and the R2 group are each independently an aromatic compound having less than 15 carbon atoms or a heterocyclic compound containing a nitrogen atom.
In this embodiment, the aromatic compound may include the following molecular structural formula:
In the embodiment, the R1 group and the R2 group which belong to aromatic compounds are introduced, and the R1 group and the R2 group have benzene rings, so that the organic compound has a larger plane conjugated configuration, and further, the transmission speed of electrons on the material made of the organic compound is higher, and the electron mobility is higher. Since the carrier balance of an electron transport material such as an organic light emitting diode has a great influence on its efficiency and stability, the mobility of the existing hole transport material is higher than that of the electron transport material by an amount of 1 to 2. Therefore, the organic compound with higher electron mobility in this embodiment is beneficial to carrier balance, thereby improving the efficiency of the device.
In this embodiment, the heterocyclic compound containing a nitrogen atom may include any one of the following molecular structural formulas:
In the embodiment, by introducing the R1 group and the R2 group having a planar nitrogenated heterocyclic structure, the electron transport capability of the organic compound is improved by the R1 group and the R2 group by utilizing the electron-donating conjugation effect of the benzene ring and the property that the nitrogen atom can increase the pi electron cloud density of a conjugated system, so that the electron mobility is higher.
In this embodiment, the R1 group and the R2 group may be aromatic compounds having the same structure and less than 15 carbon atoms, for example, the molecular structural formula of the organic compound is
In this embodiment, the R1 group and the R2 group can be heterocyclic compounds containing nitrogen atoms with the same structure, for example, the molecular structural formula of the organic compound is
In this embodiment, the R1 group and the R2 group may be aromatic compounds with different structures and carbon number less than 15, for example, the molecular structural formula of the organic compound is
In this embodiment, the R1 group and the R2 group may be heterocyclic compounds containing nitrogen atoms with different structures, for example, the molecular structural formula of the organic compound is
In this embodiment, one of the R1 group and the R2 group may be an aromatic compound having less than 15 carbon atoms, and the other may be a clathrateHeterocyclic compounds containing nitrogen atoms, e.g. organic compounds having the molecular formula
In this example, the structural formula of the organic compound is:
In this example, the HOMO electrochemical level of the organic compound M1 was-5.50 eV, and the LUMO electrochemical level was-1.96 eV. The HOMO electrochemical energy level of the organic compound M2 is-5.73 eV, and the LUMO electrochemical energy level is-2.21 eV. The HOMO electrochemical energy level of the organic compound M3 is-5.53 eV, and the LUMO electrochemical energy level is-1.96 eV. It can be seen that, taking the above three structures as examples, the characterization parameters of the organic compounds can be used for the transport material. In this embodiment, the organic compounds M1, M2, and M3 have a deeper HOMO level and a deeper LUMO level, the deeper LUMO level is favorable for injecting electrons from the cathode to reduce the turn-on voltage, and the deeper HOMO level can limit holes injected from the anode to the light-emitting layer, thereby improving the carrier recombination efficiency.
According to the embodiment of the application, the R1 group and the R2 group are introduced, so that the organic compound used for manufacturing the electron transport material has a larger conjugated plane configuration, the symmetry of the molecular structure of the organic compound is reduced, the organic compound can form an amorphous film, the electron donating conjugation effect of a benzene ring and the property that nitrogen atoms can increase the pi electron cloud density of a conjugated system are utilized, the electron mobility in the electron transport material prepared from the organic compound is further improved, the electron mobility is improved, and the display effect is finally improved.
This embodiment also provides a method for preparing an organic compound, which is used to prepare the organic compound, as shown in fig. 1, and the method for preparing the organic compound includes:
s10, mixing the first compound A with a first solvent to obtain a first mixture;
s20, mixing the second compound B with the first solvent to obtain a second mixture;
s30, adding the second mixture into the first mixture, and reacting to obtain a third compound C;
s40, mixing the first catalyst, the second catalyst and the second solvent to obtain a third mixture;
s50, dissolving the third compound C and the fourth compound D in a second solvent to obtain a fourth mixture;
s60, mixing the fourth mixture with the third mixture, and reacting to obtain a target product;
wherein the molecular structural formula of the first compound A is
The molecular structural formula of the second compound B is
The molecular structural formula of the fourth compound D is
Wherein, in the molecular structural formula of the fourth compound D, the R1 group and the R2 group are each independently an aromatic compound having less than 15 carbon atoms or a heterocyclic compound containing a nitrogen atom.
The technical solution of the present application will now be described with reference to specific embodiments.
The preparation method of the organic compound comprises the following steps:
s10, mixing the first compound A and the first solvent to obtain a first mixture.
In this embodiment, the molecular structural formula of the first compound a is
The first solvent is Dichloromethane (DCM).
In this embodiment, the first compound a and the first solvent are mixed at room temperature.
And S20, mixing the second compound B with the first solvent to obtain a second mixture.
In this embodiment, the molecular structural formula of the second compound B is
The first solvent is Dichloromethane (DCM).
In this embodiment, the second compound B is mixed with the first solvent at room temperature.
And S30, adding the second mixture into the first mixture, and reacting to obtain a third compound C.
In this embodiment, the molecular structural formula of the third compound C is
In this embodiment, the second mixture is dropped into the first mixture at room temperature, and after the reaction is completed at room temperature, the mixture is filtered by suction, and then the filter cake is rinsed with Dichloromethane (DCM), so as to obtain a third compound C.
And S40, mixing the first catalyst, the second catalyst and the second solvent to obtain a third mixture.
In this embodiment, the first catalyst is zinc powder, the second catalyst is titanium tetrachloride, the second solvent is tetrahydrofuran, and the ratio of the volume of the titanium tetrachloride to the volume of the tetrahydrofuran is 400: 13. In this embodiment, tetrahydrofuran is used as a solvent, zinc powder and titanium tetrachloride are used as catalysts, and the zinc powder, titanium tetrachloride and tetrahydrofuran are mixed and premixed to form a catalytic system suitable for the reaction of the third compound C and the fourth compound D, so that the reaction rate of the third compound C and the fourth compound D in the catalytic system is higher and the reaction is more complete.
In this embodiment, the zinc powder, tetrahydrofuran, and titanium tetrachloride were mixed under an Ar atmosphere at a temperature of 10 ℃ or less, stirred and heated to room temperature, and then heated under reflux to obtain a third mixture.
In this embodiment, the zinc powder is first added to tetrahydrofuran, and then titanium tetrachloride is added to form a third mixture, so that the zinc powder forms a suspension in a tetrahydrofuran solvent, and when titanium tetrachloride is subsequently added, the tetrahydrofuran can protect the zinc powder from being oxidized by the heat of reaction, thereby forming a stable and efficient catalytic system.
S50, dissolving the third compound C and the fourth compound D in a second solvent to obtain a fourth mixture; wherein the molecular structural formula of the fourth compound D is
The R1 group and the R2 group are each independently an aromatic compound having less than 15 carbon atoms or a heterocyclic compound containing a nitrogen atom.
In this embodiment, the aromatic compound having less than 15 carbon atoms includes:
In this embodiment, the heterocyclic compound containing a nitrogen atom includes:
in the embodiment, by introducing the heterocyclic compound with a planar nitrogenated heterocyclic structure, the electron-donating conjugation effect of the benzene ring and the property that nitrogen atoms can increase the pi electron cloud density of a conjugated system are utilized, so that the electron transport capability of the organic compound is improved by the R1 group and the R2 group, and the electron mobility is higher.
In this embodiment, the ratio of the amount of the third compound C to the amount of the fourth compound D is 1:1, and in this embodiment, when the organic compound is prepared by reacting the third compound C and the fourth compound D, the reaction conversion rate is higher and the material waste is less when the ratio of the amounts of the third compound C and the fourth compound D is 1:1, which can be determined according to the molecular structural formulas of the third compound C and the fourth compound D and the number of the reactive groups.
In this embodiment, the ratio of the amount of the substance of the first compound a to the amount of the substance of the second compound B is 4:5, and in this embodiment, when the third compound C is prepared from the first compound a and the second compound B, the amount of the substance of the second compound B is set to be excessive, so that the first compound a is sufficiently converted into the third compound C, and thus more large-plane conjugated configurations are obtained, and the yield of the third compound C is improved.
And S60, mixing the fourth mixture with the third mixture, and reacting to obtain a target product.
In this embodiment, the target product is the organic compound described in this embodiment, and its molecular structural formula is:
in this embodiment, the fourth mixture is slowly added dropwise to the third mixture, then the mixed reaction solution of the fourth mixture and the third mixture is heated and refluxed until the consumption of the carbonyl compound is detected by thin layer chromatography TLC, the reaction solution is cooled to room temperature, the reaction is quenched with an aqueous potassium carbonate solution, then the organic layer is extracted with Dichloromethane (DCM) and concentrated, and the obtained crude substance is purified by flash chromatography to obtain the target product.
In this embodiment, a third compound C having a planar large conjugated configuration and an asymmetric structure is prepared by reacting a first compound a with a second compound B, and then the third compound C is reacted with a fourth compound D to introduce an aromatic group or a nitrogen-containing heterocycle having a benzene ring on the basis of the planar large conjugated configuration of the third compound C, thereby further increasing the planar large conjugated configuration of the organic compound and increasing the pi electron cloud density of the conjugated system, thereby greatly increasing the electron transport capability and the electron mobility of the organic compound.
In this example, the reaction scheme for the preparation of the organic compound M1 is as follows:
in this embodiment, the steps of the method for preparing the organic compound M1 can be exemplified by:
a250 mL three-necked flask was charged with 5.67g (20mmol) of the first compound A and 100mL of dichloromethane DCM in this order, and a mixed solution of 4.05g (N, N' -carbonyldiimidazole, 25mmol) of the second compound B and 100mL of dichloromethane was added dropwise at room temperature. After the addition, the reaction is carried out for 2 hours at room temperature, then, the filtration is carried out, and the filter cake is leached by dichloromethane, thus obtaining a third compound C.
To a three-necked flask equipped with a magnetic stirrer, 1.6g (24mmol) of zinc powder and 40mL of tetrahydrofuran THF were charged under Ar atmosphere. The mixture was cooled to-5 ℃ and TiCl41.3mL (12mmol) was added slowly via syringe, the temperature being kept below 10 ℃. The suspended mixture was warmed to room temperature and stirred for 0.5h, then heated to reflux for 2.5 h. The third compound C6.19g (20mmol) and the fourth compound D3.72g (20mmol) were dissolved in 15mL THF, then slowly added dropwise to the suspended mixture, and after addition the reaction mixture was heated to reflux until the carbonyl compound was consumed (monitored by thin layer chromatography TLC) (about 14 h). After cooling, the reaction was quenched with 10% aqueous K2CO3 solution and extracted with CH2Cl 2. The organic layer was collected and concentrated and the crude material was purified by flash chromatography to afford the desired product M1.
In this example, the reaction scheme for the preparation of the organic compound M2 is as follows:
in this embodiment, the steps of the method for preparing the organic compound M2 can be exemplified by:
a250 mL three-necked flask was charged with 5.67g (20mmol) of the first compound A and 100mL of Dichloromethane (DCM) in this order, and a mixed solution of 4.05g (N, N' -carbonyldiimidazole, 25mmol) of the second compound B and 100mL of dichloromethane was added dropwise at room temperature. After the addition, the reaction is carried out for 2 hours at room temperature, then, the filtration is carried out, and the filter cake is leached by dichloromethane, thus obtaining a third compound C.
To a three-necked flask equipped with a magnetic stirrer, 1.6g (24mmol) of zinc powder and 40mL of tetrahydrofuran THF were charged under Ar atmosphere. The mixture was cooled to-5 ℃ and TiCl41.3mL (12mmol) was added slowly via syringe, the temperature being kept below 10 ℃. The suspended mixture was warmed to room temperature and stirred for 0.5h, then heated to reflux for 2.5 h. The third compound C6.19g (20mmol) and the fourth compound D4.64g (20mmol) were dissolved in 15mL THF, then added slowly dropwise to the suspended mixture, and after addition the reaction mixture was heated to reflux until the carbonyl compound was consumed (monitored by thin layer chromatography TLC) (about 14 h). After cooling, the reaction was quenched with 10% aqueous K2CO3 solution and extracted with CH2Cl 2. The organic layer was collected and concentrated and the crude material was purified by flash chromatography to afford the desired product M2.
In this example, the reaction scheme for the preparation of the organic compound M3 is as follows:
in this embodiment, the steps of the method for preparing the organic compound M3 can be exemplified by:
a250 mL three-necked flask was charged with 5.67g (20mmol) of the first compound A and 100mL of dichloromethane DCM in this order, and a mixed solution of 4.05g (N, N' -carbonyldiimidazole, 25mmol) of the second compound B and 100mL of dichloromethane was added dropwise at room temperature. After the addition, the reaction is carried out for 2 hours at room temperature, then, the filtration is carried out, and the filter cake is leached by dichloromethane, thus obtaining a third compound C.
To a three-necked flask equipped with a magnetic stirrer, 1.6g (24mmol) of zinc powder and 40mL of tetrahydrofuran THF were charged under Ar atmosphere. The mixture was cooled to-5 ℃ and TiCl41.3mL (12mmol) was added slowly via syringe, the temperature being kept below 10 ℃. The suspended mixture was warmed to room temperature and stirred for 0.5h, then heated to reflux for 2.5 h. The third compound C6.19g (20mmol) and the fourth compound D5.68g (20mmol) were dissolved in 15mL THF, then slowly added dropwise to the suspended mixture, and after addition the reaction mixture was heated to reflux until the carbonyl compound was consumed (monitored by thin layer chromatography TLC) (about 14 h). After cooling, the reaction was quenched with 10% aqueous K2CO3 solution and extracted with CH2Cl 2. The organic layer was collected and concentrated and the crude material was purified by flash chromatography to afford the desired product M3.
The embodiment of the present application provides a liquid crystal display device having
The organic compound can form an amorphous film structure, thereby being beneficial to electron flow and improving the electron mobility of the electron transport material; moreover, the molecular structure of the organic compound has a large conjugated plane configuration, which is beneficial to improving the transmission rate of the electron transmission material, thereby improving the luminous efficiency of the luminescent device; in addition, the organic compound has deeper HOMO energy level and LUMO energy level, and improves the thermal stability and luminous efficiency of the organic light-emitting device, thereby further improving the display effect.
The embodiment of the application also provides an electron transport material, which comprises a structural molecular formula of
The organic compound of (1).
In this embodiment, please refer to any one of the embodiments of the organic compound and any one of the embodiments of the method for manufacturing the organic compound for the structure of the organic compound, which is not described herein again.
In the present example, taking the organic compound M1, the organic compound M2, and the organic compound M3 as examples, the HOMO level and the LUMO level thereof were measured and the level difference was calculated, and the data thereof are shown in table 1.
| HOMO(eV) | LUMO(eV) | Eg(eV) | |
| Compound M1 | -5.50 | -1.96 | 3.54 |
| Compound M2 | -5.73 | -2.21 | 3.52 |
| Compound M3 | -5.53 | -1.96 | 3.57 |
TABLE 1
In this example, the blue electroluminescent devices prepared by using the organic compounds M1, M2 and M3 as electron transport materials were tested, and the same tests were performed using the electroluminescent devices of the prior art using 1,3, 5-tris [ (3-pyridyl) -3-phenyl ] benzene (BPhen) as an electron transport material as a control, and the test results are shown in table 2.
| Device with a metal layer | Electron transport material | Drive voltage (V) | E/CIEy | LT95(H) |
| Device 1 | Compound M1 | 3.82 | 153.5 | 78 |
| Device 2 | Compound M2 | 3.78 | 149.1 | 76 |
| Device 3 | Compound M3 | 3.76 | 152.4 | 74 |
| Control group | BPhen | 3.89 | 144.2 | 65 |
TABLE 2
As can be seen from the data in tables 1 and 2, the driving voltage of the electron transport material made of the organic compound M1 was 3.82V, the blue light efficiency E was 153.5, and the LT95 period (the time period when 95% of the initial luminance was reached) was 78H. The electron transporting material made of the organic compound M2 had a driving voltage of 3.78V, a blue light efficiency E of 149.1, and an LT95 period (a period of time when 95% of the initial luminance is reached) of 76H. The electron transporting material made of the organic compound M3 had a driving voltage of 3.76V, a blue light efficiency E of 152.4, and an LT95 period (a period of time when 95% of the initial luminance is reached) of 74H.
The test data of the light emitting device prepared by using 1,3, 5-tri [ (3-pyridyl) -3-phenyl ] benzene (BPhen) as the electron transport material in the prior art are as follows: the driving voltage was 3.89V, the blue light efficiency E was 144.2, and the LT95 period (the time period when 95% of the initial luminance was reached) was 65H.
By comparing the photoelectric parameters of the electron transport material prepared from the organic compound M1, the organic compound M2, the organic compound M3, and bathophenanthroline (BPhen) in the prior art in the embodiment of the present application, it can be seen that the electron transport material prepared from the organic compound provided in the embodiment of the present application has a lower driving voltage, a higher blue light efficiency, a longer service life, and a comprehensive performance superior to that of the conventional electron transport material.
The embodiment of the application also provides a light-emitting device, wherein the light-emitting device 100 comprises the electron transport material, and the electron transport material comprises the organic compound or the organic compound prepared according to the preparation method of the organic compound.
The technical solution of the present invention will now be described with reference to specific embodiments.
As shown in fig. 2, the light emitting device 100 includes a hole injection layer 110, a hole transport layer 120 on the hole injection layer 110, an electron blocking layer 130 on the hole transport layer 120, a light emitting material layer 140 on the electron blocking layer 130, a hole blocking layer 150 on the light emitting material layer 140, an electron transport layer 160 on the hole blocking layer 150, and an electron injection layer 170 on the electron transport layer 160.
In this embodiment, the material in the Light Emitting material layer 540 may be an Organic Light Emitting semiconductor (OLED) or a Quantum Dot Light Emitting diode (QLED), which is not limited herein.
In the present embodiment, the hole transport layer 520 includes an electron transport material as described above, and the electron transport material includes an organic compound as described above. The organic compound is matched with the hole transport layer 520, and the hole transport efficiency can be improved more.
The organic compound, the preparation method thereof, and the electron transport material provided in the examples of the present application are described in detail above, and the principles and embodiments of the present application are explained herein by applying specific examples, and the descriptions of the above examples are only used to help understand the method and the core ideas of the present application; meanwhile, for those skilled in the art, according to the idea of the present application, there may be variations in the specific embodiments and the application scope, and in summary, the content of the present specification should not be construed as a limitation to the present application.
Claims (10)
1. An organic compound having the following molecular structure:
wherein the R1 group and the R2 group are each independently an aromatic compound having less than 15 carbon atoms or a heterocyclic compound containing a nitrogen atom.
2. The organic compound of claim 1, wherein the aromatic compound comprises any one of the following molecular structural formulas:
3. the organic compound according to claim 1, wherein the heterocyclic compound containing a nitrogen atom comprises any one of the following molecular structural formulas:
4. a method for producing an organic compound, comprising:
mixing a first compound and a first solvent to obtain a first mixture;
mixing the second compound with the first solvent to obtain a second mixture;
adding the second mixture into the first mixture, and reacting to obtain a third compound;
mixing the first catalyst, the second catalyst and the second solvent to obtain a third mixture;
dissolving the third compound and the fourth compound in a second solvent to obtain a fourth mixture;
mixing the fourth mixture with the third mixture, and reacting to obtain a target product;
wherein the molecular structural formula of the first compound is
The molecular structural formula of the second compound is
The molecular structural formula of the fourth compound is
Wherein, in the molecular structural formula of the fourth compound, the R1 group and the R2 group are respectively and independently an aromatic compound with the carbon number less than 15 or a heterocyclic compound containing a nitrogen atom.
5. The method of claim 4, wherein the third compound comprises the following molecular formula:
6. the method according to claim 5, wherein in the step of mixing the first catalyst with a second catalyst and a second solvent to obtain a third mixture, the second solvent comprises tetrahydrofuran, and the second catalyst comprises titanium tetrachloride;
wherein a ratio of the volume of the second solvent to the volume of the second catalyst is 400: 13.
7. the method according to claim 6, wherein the step of mixing the first catalyst, the second catalyst, and the second solvent to obtain a third mixture comprises:
adding the first catalyst into a second solvent, and then adding the second catalyst to form a third mixture;
wherein the first catalyst comprises zinc.
8. The method according to claim 4, wherein a ratio of the amount of the third compound to the amount of the fourth compound is 1: 1.
9. The method according to any one of claims 5 to 8, wherein a ratio of the amount of the substance of the first compound to the amount of the substance of the second compound is 4: 5.
10. An electron transport material comprising the organic compound according to any one of claims 1 to 3.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202110947364.0A CN113698410A (en) | 2021-08-18 | 2021-08-18 | Organic compound, preparation method thereof and electron transport material |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202110947364.0A CN113698410A (en) | 2021-08-18 | 2021-08-18 | Organic compound, preparation method thereof and electron transport material |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN113698410A true CN113698410A (en) | 2021-11-26 |
Family
ID=78653402
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202110947364.0A Pending CN113698410A (en) | 2021-08-18 | 2021-08-18 | Organic compound, preparation method thereof and electron transport material |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN113698410A (en) |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112079841A (en) * | 2020-09-22 | 2020-12-15 | 武汉天马微电子有限公司 | Organic compound, electroluminescent material and application thereof |
| CN113248504A (en) * | 2021-05-20 | 2021-08-13 | 武汉华星光电技术有限公司 | Electron transport material, preparation method thereof and organic light-emitting diode |
-
2021
- 2021-08-18 CN CN202110947364.0A patent/CN113698410A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112079841A (en) * | 2020-09-22 | 2020-12-15 | 武汉天马微电子有限公司 | Organic compound, electroluminescent material and application thereof |
| CN113248504A (en) * | 2021-05-20 | 2021-08-13 | 武汉华星光电技术有限公司 | Electron transport material, preparation method thereof and organic light-emitting diode |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP1794256B1 (en) | New compound and organic light emitting device using the same(2) | |
| KR101470055B1 (en) | Organic electroluminescence device using the triphenylene derivative | |
| CN105884830B (en) | A kind of bipolarity OLED phosphorescent light body materials and the luminescent device comprising the material | |
| EP2272828B1 (en) | Organic electroluminescent device | |
| CN106898699B (en) | A kind of organic electroluminescence device | |
| CN112979687B (en) | Thermal activation delay fluorescent material and preparation method and application thereof | |
| WO2019174650A1 (en) | Compound having benzene core, preparation method therefor and uses thereof on organic electroluminescent device | |
| CN109761879B (en) | Organic blue fluorescent material, preparation method thereof and organic electroluminescent device | |
| CN109575038A (en) | A kind of compound of the fluorenes of xanthene containing spiral shell and its application on organic electroluminescence device | |
| US20200259088A1 (en) | Electroluminescent compound, thermally activated delayed fluorescence material, and application thereof | |
| CN102703058B (en) | Novel electroluminescence material and application thereof | |
| KR101548076B1 (en) | Organic electroluminescence device using the triphenylene derivative | |
| CN116156980A (en) | Organic electroluminescent device and application thereof | |
| CN116332933A (en) | Condensed ring organic compound, luminous composition and organic electroluminescent device | |
| CN116113294A (en) | Organic electroluminescent device and application thereof | |
| CN113698410A (en) | Organic compound, preparation method thereof and electron transport material | |
| CN111423330B (en) | Aromatic amine derivative based on spirofluorene and application thereof | |
| US20200227648A1 (en) | Compound and its application | |
| US20240032419A1 (en) | Electron transport material and fabricating method thereof, and organic light-emitting diode | |
| CN111116657A (en) | Organic heterocyclic luminescent material and application thereof in OLED device | |
| CN110194720A (en) | A kind of compound, organic photoelectric device and electronic equipment | |
| CN109651346A (en) | A kind of naphthalene heterocyclic compound and its application | |
| CN108358950A (en) | A kind of new Organic Electro Luminescent Materials, preparation method and application | |
| CN115260203B (en) | Quinoxaline phenazine luminescent material and application thereof | |
| EP4130007A1 (en) | Hole transport material and synthesis method therefor |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20211126 |
|
| RJ01 | Rejection of invention patent application after publication |