CN117164570A - Electron transport material, preparation method thereof and organic electroluminescent device - Google Patents
Electron transport material, preparation method thereof and organic electroluminescent device Download PDFInfo
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Abstract
The invention relates to the technical field of organic electroluminescent devices, in particular to an electron transport material, a preparation method thereof and an organic electroluminescent device. The electron transport material is selected from the group consisting of compounds represented by the following formula 1:the electron transport material takes 9-phenyl-9 dibenzofuran fluorene ring as a mother nucleus, the fluorene ring is bonded with cyano biphenyl substituted triazine group through chemical bond or arylene or heteroarylene, wherein, the 9-phenyl-9 dibenzofuranThe fluorene-based environment-friendly material can protect molecules from space torsion, and avoid poor film forming property of the device caused by molecular stacking; the triazine group and the cyano group have strong electron-withdrawing property, which is favorable for electron transmission and enhances the recombination of electrons and holes in the light-emitting layer, thereby improving the light-emitting efficiency of the device; the cyano group is bonded to the triazine group through the biphenyl to increase conjugation, which is more beneficial to adjusting energy level, reducing injection potential barrier, reducing driving voltage, and simultaneously is beneficial to balanced distribution of electrons in molecules, thereby further improving luminous efficiency of the device.
Description
Technical Field
The invention relates to the technical field of organic electroluminescent devices, in particular to an electron transport material, a preparation method thereof and an organic electroluminescent device.
Background
Compared with the traditional display and illumination technology, the organic light-emitting diode (OLED) has obvious advantages such as no need of a backlight source, light weight, low energy consumption, high response speed, flexibility, clearness in displaying moving images, no smear and the like, and can meet the performance requirements of people on an information display system in multiple aspects.
The OLED specifically includes electrode material layers and organic functional materials sandwiched between different electrode layers, including: a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer. The electron transport layer is a key component in the OLED structure and is responsible for adjusting the injection speed and injection amount of electrons, but the electron mobility of the common organic material is lower, the hole mobility is higher, and the unbalance of electrons and holes in the device is caused, so that the efficiency and the stability of the device are reduced.
In recent years, research on organic electron transport materials has been conducted, but research on an electron transport material having high mobility so that an OLED prepared therefrom has performance advantages of high light emitting efficiency and low driving voltage has been still a urgent need for a solution by those skilled in the art.
In view of this, the present invention has been made.
Disclosure of Invention
The invention aims to provide an electron transport material, a preparation method thereof and an organic electroluminescent device. The electron transport material provided by the embodiment of the invention can improve the luminous efficiency of the organic electroluminescent device and reduce the driving voltage.
The invention is realized in the following way:
in a first aspect, embodiments of the present invention provide an electron transport material selected from the group consisting of compounds represented by formula 1 below:
wherein L is independently selected from any one of the group of functional groups formed by a chemical bond, phenyl, biphenyl, terphenyl, naphthyl, phenylnaphthyl, dimethylfluorenyl, phenanthryl, pyridyl, dibenzofuranyl, dibenzothienyl, phenyldibenzofuranyl, phenyldibenzothienyl, naphthalenyl dibenzofuranyl, naphthalenyl dibenzothienyl, and 9-phenylcarbazolyl;
ar is independently selected from any one of the groups shown in the following structural formulas:
in a second aspect, an embodiment of the present invention provides a method for preparing an electron transport material, where the electron transport material is synthesized according to the following synthesis route:
wherein Hal and Hal 1 Selected from halogen.
In a third aspect, an embodiment of the present invention provides an organic electroluminescent device, which includes an electron transport layer, where the electron transport layer is prepared by using the electron transport material.
The invention has the following beneficial effects: the electron transport material provided by the embodiment of the invention takes the 9-phenyl-9 dibenzofuranyl fluorene ring as a mother nucleus, and the fluorene ring is bonded with a cyano biphenyl substituted triazine group through a chemical bond or arylene or heteroarylene, wherein the 9-phenyl-9 dibenzofuranyl fluorene has the effect of ensuring the space torsion of molecules, so that the poor film forming property of the device caused by molecular stacking is avoided; the triazine group and the cyano group have strong electron-withdrawing property, which is favorable for electron transmission and enhances the recombination of electrons and holes in the light-emitting layer, thereby improving the light-emitting efficiency of the device; the cyano group is bonded to the triazine group through the biphenyl to increase conjugation, which is more beneficial to adjusting energy level, reducing injection potential barrier, reducing driving voltage, and simultaneously is beneficial to balanced distribution of electrons in molecules, thereby further improving luminous efficiency of the device.
Drawings
In order to more clearly illustrate the technical solutions of the embodiments of the present invention, the drawings that are needed in the embodiments will be briefly described below, it being understood that the following drawings only illustrate some embodiments of the present invention and therefore should not be considered as limiting the scope, and other related drawings may be obtained according to these drawings without inventive effort for a person skilled in the art.
FIG. 1 is a nuclear magnetic resonance hydrogen spectrum of a compound 7 provided in example 1 of the present invention;
FIG. 2 is a nuclear magnetic resonance spectrum of a compound 52 according to example 2 of the present invention;
FIG. 3 is a nuclear magnetic resonance hydrogen spectrum of the compound 215 according to example 3 of the present invention;
FIG. 4 is a nuclear magnetic resonance spectrum of a compound 390 according to example 4 of the present invention;
FIG. 5 is a nuclear magnetic resonance hydrogen spectrum of a compound 579 provided in example 5 of the present invention;
FIG. 6 is a nuclear magnetic resonance hydrogen spectrum of the compound 585 provided in example 6 of the present invention;
FIG. 7 is a nuclear magnetic resonance hydrogen spectrum of a compound 592 provided in example 1 of the present invention.
Detailed Description
In order to make the objects, technical solutions and advantages of the embodiments of the present invention more clear, the technical solutions of the embodiments of the present invention will be clearly and completely described below. The specific conditions are not noted in the examples and are carried out according to conventional conditions or conditions recommended by the manufacturer. The reagents or apparatus used were conventional products commercially available without the manufacturer's attention.
An embodiment of the present invention provides an electron transport material selected from the group consisting of compounds represented by the following formula 1:
wherein L is independently selected from any one of the group of functional groups formed by a chemical bond, phenyl, biphenyl, terphenyl, naphthyl, phenylnaphthyl, dimethylfluorenyl, phenanthryl, pyridyl, dibenzofuranyl, dibenzothienyl, phenyldibenzofuranyl, phenyldibenzothienyl, naphthalenyl dibenzofuranyl, naphthalenyl dibenzothienyl, and 9-phenylcarbazolyl; preferably, L is selected from any one of a bond, phenyl or biphenyl.
Ar is independently selected from any one of the groups shown in the following structural formulas:
preferably, ar is independently selected from any one of the groups represented by the following structural formulas:
in the above structural formula, the ligation site is represented by.
Further, the electron transport material is selected from any one of the compounds represented by the following structural formulas:
wherein R represents hydrogen or cyano. The electron transport material is selected from any one of the compounds shown in the following structural formulas:
more specifically, the electron transport material is selected from any one of the compounds represented by the following structural formulas:
the 9-phenyl-9 dibenzofuranyl fluorene environmental protection evidence molecule space torsion in the electron transport material provided by the embodiment of the invention avoids poor film forming property of the device caused by molecule stacking; the triazine group and the cyano group have strong electron-withdrawing property, which is favorable for electron transmission and enhances the recombination of electrons and holes in the light-emitting layer, thereby improving the light-emitting efficiency of the device; the cyano group is bonded to the triazine group through the biphenyl to increase conjugation, which is more beneficial to adjusting energy level, reducing injection potential barrier, reducing driving voltage, and simultaneously is beneficial to balanced distribution of electrons in molecules, thereby further improving luminous efficiency of the device.
In a second aspect, an embodiment of the present invention provides a method for preparing the above-mentioned electron transport material, where the electron transport material is synthesized according to the following synthesis route:
wherein, hal and Hal 1 Selected from halogen, for example, selected from any one of Cl, br and I.
Specifically, the first step: under the protection of nitrogen, the reactant 1 (1.0 eq), the reactant 2 (1.1-1.3 eq), the palladium catalyst (0.05-0.1 eq) and the potassium acetate (2.0-3.0 eq) are dissolved in a mixed solvent of N, N-Dimethylformamide (DMF), and the temperature is raised to 85-95 ℃ for reaction for 8-12h. The solvent was removed using a rotary evaporator, the residue was stirred with dichloromethane, filtered, and purified by column chromatography to give intermediate 1.
And a second step of: under the protection of nitrogen, adding an intermediate 1 (1.0 eq), a reactant 3 (1.1-1.3 eq), a palladium catalyst (0.01-0.02 eq) and a phosphine ligand (0.02-0.05 eq) into a mixed solvent of toluene, ethanol and water (volume ratio of 2-4:1:1) respectively, heating to 80-100 ℃, reacting for 8-12H, cooling to room temperature, adding H2O, filtering after solid precipitation is finished, drying a filter cake, heating and dissolving the obtained solid by toluene, and filtering the obtained solid by methanol for a silica gel funnel while the solid is hot: dichloromethane (volume ratio of 1:40-60) was used as developing agent, the solvent was removed from the filtrate by a rotary evaporator, and the obtained solid was dried to obtain the compound represented by chemical formula 1.
Wherein the palladium catalyst comprises Pd 2 (dba) 3 、Pd(PPh 3 ) 4 、PdCl 2 、PdCl 2 (dppf)、Pd(OAc) 2 、Pd(PPh 3 ) 2 Cl 2 And NiCl 2 (dppf);
the phosphine ligand may be selected from P (t-Bu) 3 、X-phos、PET 3 、PMe 3 、PPh 3 、KPPh 2 And P (t-Bu) 2 Any one of Cl;
the base may be: k (K) 2 CO 3 ，K 3 PO 4 ，Na 2 CO 3 ，CsF，Cs 2 CO 3 Or any of t-BuONa.
In a third aspect, an embodiment of the present invention further provides an organic electroluminescent device, including an anode, a cathode, and an organic thin film layer disposed between the anode and the cathode, the organic thin film layer including an electron transport layer, and the compound represented by formula 1 prepared according to the present invention is used as a material of the electron transport layer to prepare the electron transport layer according to one embodiment of the present specification.
The organic thin film layer may specifically include any one or a combination of at least two of a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting auxiliary layer, a light emitting layer, a hole blocking layer, an electron injection layer, and a capping layer.
The anode is made of a conductor such as a metal, metal oxide, and/or conductive polymer that has a higher work function to aid in hole injection. The metal can be nickel, platinum, vanadium, chromium, copper, zinc, gold, silver or alloys thereof; the metal oxide can be zinc oxide, indium Tin Oxide (ITO) or indium zinc oxide; the combination of metal and oxide can be ZnO and A1 or SnO 2 Sb or ITO and Ag; the conductive polymer may be selected from poly (3-methylthiophene), poly (3, 4- (ethylene-1, 2-dioxy) thiophene), polypyrrole and polyaniline, but is not limited thereto.
The hole injection layer and the hole transport layer efficiently inject or transport holes from the anode between the electrodes to which an electric field has been applied, and preferably have high hole injection efficiency and efficiently transport the injected holes. Therefore, a substance having a small ionization potential, a large hole mobility, and excellent stability, and which is less likely to cause impurities that become traps during production and use, is preferable. The hole injection layer is preferably a p-doped hole injection layer; the hole transport material may be selected from arylamine derivatives, conductive polymers, block copolymers having both conjugated and non-conjugated portions, and the like.
A light-emitting auxiliary layer (multi-layer hole transporting layer) is interposed between the hole transporting layer and the light-emitting layer, and functions to smoothly move holes from the anode to the light-emitting layer and block electrons from the cathode.
The light-emitting layer is preferably a compound which emits light by excitation by recombination of holes and electrons, and is preferably a compound which can form a stable thin film shape and exhibits high light-emitting efficiency in a solid state. The light emitting layer may be a single layer or multiple layers and may include a host material and a dopant material. The amounts of the host material and the dopant material to be used may be determined in accordance with the respective material characteristics. The doping method may be realized by co-evaporation with the host material, or may be formed by simultaneous evaporation after mixing with the host material.
The electron transport layer and the electron injection layer efficiently transport or inject electrons from the anode and cathode between the electrodes to which an electric field has been applied. An impurity substance which has a large electron affinity, a large electron mobility, and excellent stability and is not likely to cause a trap is preferable.
The anode is a substance capable of injecting electrons with good efficiency, and the same material as that of the anode can be selected. If a low work function metal is chosen that facilitates efficient electron injection, it is often necessary to dope trace amounts of lithium, cesium or magnesium to avoid its instability in the atmosphere.
There is no particular limitation on the materials of the other layers in the oled device except that the electron transport layer disclosed in the present invention includes formula 1.
The features and capabilities of the present invention are described in further detail below in connection with the examples.
Example 1
The embodiment of the invention provides a preparation method of an electron transport material (compound 7), which is synthesized by referring to the following synthesis paths:
the method comprises the following steps: />
Under nitrogen, reactants 1-7 (20 mmol, CAS:2237935-99-6), reactants 2-7 (25 mmol), pd (PPh) 3 ) 4 (1.0 mmol) and potassium acetate (4.0 mmol) were dissolved in a mixed solvent of DMF, and the temperature was raised to 90℃for 10 hours. UsingThe solvent was removed by rotary evaporator, and the residue was stirred with methylene chloride, filtered and purified by column chromatography to give intermediate 1-7 (mass 8.02g, yield: 75%, test value MS (ESI, M/Z): [ M+H ]] + = 534.59, mass spectrometer model Waters XEVO TQD, low precision, test with ESI source).
Under nitrogen, intermediate 1-7 (20 mmol), reactant 3-7 (25 mmol, CAS: 2260561-71-3), pd (PPh 3 ) 2 Cl 2 (0.2 mmol) and X-phos (0.4 mmol), K 2 CO 3 (4.0 mmol) was added to a mixed solvent of toluene, ethanol and water (150 mL:50 mL), the temperature was raised to 95℃and the mixture was reacted for 10 hours, cooled to room temperature, and H was added 2 And O, filtering after the solid is separated out, drying a filter cake, heating and dissolving the obtained solid by using toluene, and passing through a silica gel funnel while the solid is hot by using methanol: dichloromethane (volume ratio of 1:4) was used as a developing agent, the solvent was removed from the filtrate by a rotary evaporator, and the obtained solid was dried to obtain compound 7 (mass: 8.31g, yield: 56%).
Characterization: the nuclear magnetic resonance hydrogen spectrum of (1) compound 7 is shown in FIG. 1.
(2) HPLC purity: > 99.8%.
(3) Elemental analysis: theoretical value: c,85.92; h,4.35; n,7.56; o,2.16; test value: c,85.84; h,4.41; n,7.58; o,2.19.
(4)MS(ESI，m/Z):[M+H] + ＝741.89。
Example 2
The embodiment of the invention provides a preparation method of an electron transport material (compound 52), which is synthesized by referring to the following synthesis paths:
the method comprises the following steps:
the synthesis method and the amount provided in this example were the same as those of the synthetic compound 7 provided in example 1, except that the reactants 1 to 7 and 3 to 7 were replaced with the reactants 1 to 52 (CAS: 2767222-21-7) and the reactants 3 to 52 (CAS: 2817692-03-6), respectively, to obtain the compound 52 (mass 10..62g, yield: 63%).
Characterization: the nuclear magnetic resonance hydrogen spectrum of (1) compound 52 is shown in fig. 2.
(2) HPLC purity: > 99.8%.
(3) Elemental analysis: theoretical value: c,85.59; h,4.19; n,8.32; o,1.90; test value: c,85.56; h,4.24; n,8.33; o,1.93.
(4)MS(ESI，m/Z):[M+H] + ＝843.05。
Example 3
The embodiment of the invention provides a preparation method of an electron transport material (compound 215), which is synthesized by referring to the following synthesis paths:
the method comprises the following steps:
the synthesis method and the amount of the compound (7) provided in this example were the same as those of the compound (7) provided in example 1, except that the reactants (1-7) and (3-7) were replaced with the reactants (1-215) (CAS: 2883197-30-4) and the reactants (3-215) (CAS: 2883453-96-9), respectively, to give the compound (215) (mass: 10.79g, yield: 66%).
Characterization: the nuclear magnetic resonance hydrogen spectrum of (1) compound 215 is shown in fig. 3.
(2) HPLC purity: > 99.8%.
(3) Elemental analysis: theoretical value: c,86.74; h,4.44; n,6.86; o,1.96; test value: c,86.68; h,4.49; n,6.88; o,2.00.
(4)MS(ESI，m/Z):[M+H] + ＝817.10。
Example 4
The embodiment of the invention provides a preparation method of an electron transport material (compound 390), which is synthesized by referring to the following synthesis paths:
the method comprises the following steps:
the synthesis method and the amount provided in this example were the same as those of the synthetic compound 7 provided in example 1, except that the reactants 1 to 7 and 3 to 7 were replaced with the reactants 1 to 390 (CAS: 2237936-00-2) and the reactants 3 to 390 (CAS: 2506373-46-0), respectively, to obtain a compound 390 (mass: 12.34g, yield: 69%).
Characterization: the nuclear magnetic resonance hydrogen spectrum of (1) compound 390 is shown in fig. 4.
(2) HPLC purity: > 99.8%.
(3) Elemental analysis: theoretical value: c,87.42; h,4.51; n,6.27; o,1.79; test value: c,87.39; h,4.55; n,6.28; o,1.81.
(4)MS(ESI，m/Z):[M+H] + ＝894.08。
Example 5
The embodiment of the invention provides a preparation method of an electron transport material (compound 579), which is synthesized by referring to the following synthesis paths:
the method comprises the following steps:
the synthesis method and the amount of the compound 579 provided in this example were the same as those of the compound 7 provided in example 1, except that the reactants 1 to 7 and the reactants 3 to 7 were replaced with the reactants 1 to 579 (CAS: 2359605-29-9) and the reactants 3 to 579 (CAS: 2763214-56-6), respectively, to obtain the compound 579 (mass: 11.33g, yield: 60%).
Characterization: the nuclear magnetic resonance hydrogen spectrum of the compound 579 shown in FIG. 5.
(2) HPLC purity: > 99.8%.
(3) Elemental analysis: theoretical value: c,87.87; h,4.49; n,5.94; o,1.70; test value: c,87.82; h,4.53; n,5.96; o,1.73.
(4)MS(ESI，m/Z):[M+H] + ＝944.16。
Example 6
The embodiment of the invention provides a preparation method of an electron transport material (compound 585), which is synthesized by referring to the following synthesis route:
the method comprises the following steps:
the synthesis method and the amount provided in this example are the same as those of the compound 7 provided in example 1, except that the reactants 1 to 7 and the reactants 3 to 7 are replaced with the reactants 1 to 52 and the reactants 3 to 585 (CAS: 2857863-24-0), respectively, to obtain the compound 585. (mass 10.09g, yield: 54%).
Characterization: the nuclear magnetic resonance hydrogen spectrum of (1) compound 585 is shown in fig. 6.
(2) HPLC purity: > 99.8%.
(3) Elemental analysis: theoretical value: c,87.53; h,4.75; n,6.00; o,1.71; test value: c,87.48; h,4.79; n,6.01; o,1.74.
(4)MS(ESI，m/Z):[M+H] + ＝934.15。
Example 7
The embodiment of the invention provides a preparation method of an electron transport material (compound 592), which is synthesized by referring to the following synthesis paths:
the method comprises the following steps:
the synthesis method and the amount of the compound were the same as those of the compound 7 of example 1 except that the reactants 1 to 7 and the reactants 3 to 7 were replaced with the reactants 1 to 592 (CAS: 2237935-98-5) and the reactants 3 to 592 (CAS: 2498901-93-0), respectively, to obtain the compound 592. (mass 10.28g, yield: 51%).
Characterization: the nuclear magnetic resonance hydrogen spectrum of compound 592 is shown in fig. 7.
(2) HPLC purity: > 99.8%.
(3) Elemental analysis: theoretical value: c,85.86; h,4.20; n,8.34; o,1.59; test value: c,85.82; h,4.24; n,8.35; o,1.62.
(4)MS(ESI，m/Z):[M+H] + ＝1008.18。
Examples 8 to 158
The synthesis of the following compounds was accomplished with reference to the synthesis methods of examples 1 to 7, using a mass spectrometer model Waters XEVO TQD, with low accuracy, using ESI source, and with mass spectrometry values as shown in table 1 below.
Table 1 mass spectra of examples 8-158
Further, since other compounds of the present invention can be obtained by referring to the synthetic methods of the above-mentioned examples, they are not exemplified herein.
The organic electron transport material and the organic electroluminescent device according to the present invention will be described in detail with reference to specific examples.
Device example 1
The embodiment provides a method for preparing an organic electroluminescent device, wherein the structure of the prepared OLED device is as follows: ITO anode/HIL/HTL/Prime/EML/HBL/ETL/EIL/cathode/light extraction layer. The method comprises the following steps:
a. ITO anode: the thickness of the coating is equal toThe ITO (indium tin oxide) -Ag-ITO (indium tin oxide) glass substrate is washed for 2 times in distilled water, ultrasonic wave is used for washing for 30min, then distilled water is used for repeatedly washing for 2 times, ultrasonic wave is used for washing for 10min, methanol, acetone and isopropanol are used for ultrasonic wave washing (5 min for washing each time) in sequence after washing is finished, drying is carried out, then the glass substrate is transferred into a plasma washer for washing for 5min, and then the glass substrate is sent into an evaporation machine, the substrate is used as an anode, and other functional layers are sequentially evaporated on the substrate.
b. HIL (hole injection layer): to be used forThe vacuum evaporation of the hole injection layer materials HT and P-dopant is performed, and the chemical formulas are shown below. The evaporation rate ratio of HT to P-dock is 97:3, and the thickness is 10nm. .
c. HTL (hole transport layer): to be used forIs used as a hole transport layer, and HT of 120nm is vacuum deposited on the hole injection layer.
d. Prime (light-emitting auxiliary layer): to be used forIs used as the light-emitting auxiliary layer, and Prime of 5nm is vacuum deposited on the hole transport layer.
e. EML (light emitting layer): then on the light-emitting auxiliary layer toThe Host material (Host) and the Dopant material (Dopant) having a thickness of 30nm were vacuum-deposited as light-emitting layers, and the chemical formulas of Host and Dopant are shown below. Wherein the evaporation rate ratio of Host to Dopant is 98:2.
f. HBL (hole blocking layer): to be used forThe hole blocking layer HB having a thickness of 5nm was vacuum deposited.
g. ETL (electron transport layer): to be used forIs used as an electron transport layer, and compound 7 and Liq having a thickness of 30nm are vacuum-deposited. Wherein the evaporation rate ratio of the compound 7 to the Liq is 50:50.
h. EIL (electron injection layer): to be used forIs steamed in (2)Plating rate, evaporating Yb film layer by 1.0nm to form an electron injection layer.
i. And (3) cathode: to be used forThe vapor deposition rate ratio of magnesium and silver is 13nm, and the vapor deposition rate ratio is 1:9, so that the OLED device is obtained.
j. Light extraction layer: to be used forCPL with a thickness of 70nm was vacuum deposited on the cathode as a light extraction layer.
K. And packaging the evaporated substrate. Firstly, a gluing device is adopted to carry out a coating process on a cleaned cover plate by UV glue, then the coated cover plate is moved to a lamination working section, a substrate subjected to vapor deposition is placed at the upper end of the cover plate, and finally the substrate and the cover plate are bonded under the action of a bonding device, and meanwhile, the UV glue is cured by illumination.
Device examples 2-158:
the organic electroluminescent devices of application examples 2 to 158 were prepared according to the preparation method of the organic electroluminescent device provided in device example 1 above, except that compound 7 in device example 1 was replaced with the corresponding compound in examples 2 to 158, respectively, to form an electron transport layer.
Device comparative examples 1-14:
the organic electroluminescent devices of comparative examples 1 to 14 were prepared according to the preparation method of the organic electroluminescent device provided in device example 1 above, except that compound 7 in device example 1 was replaced with comparative compounds 1 to 14, respectively, to form an electron transport layer.
Wherein, the structural formula of the comparative compounds 1-14 is as follows:
the organic electroluminescent devices obtained in the above device examples 1 to 158 and device comparative examples 1 to 14 were characterized in terms of driving voltage, BI value and luminous efficiency at a luminance of 1000 (nits), and the test results are shown in table 2 below:
TABLE 2
Note that: bi=light emission efficiency/CIEy in table 2, the light emission efficiency is affected by chromaticity in the blue OLED device.
As can be seen from Table 2, the OLED devices (device examples 1-158) prepared by using the compound having a specific structural formula provided in the examples of the present invention as an electron transporting material and the OLED devices prepared by using the conventional materials provided in the device comparative examples 1-14 have a driving voltage reduced by 0.05-0.27eV compared to the organic electroluminescent devices of the comparative examples, and light-emitting efficiency improved by 4% -17% compared to the device example 1 provided in the comparative example, and BI value improved.
The difference between the comparison compound 4 and the compound 66 is that whether the biphenyl group is substituted by cyano or not, and a strong electron withdrawing group is introduced to the biphenyl group, so that the electron distribution is more balanced, mobility is improved, the prepared organic electroluminescent device is remarkably improved in light-emitting efficiency, the light-emitting efficiency of the comparison compound 4 is improved by 11% as shown in table 2, meanwhile, the driving voltage is reduced by 0.12eV, and the device performance in the field is remarkably improved.
The difference between the comparison compound 5 and the compound 119 is that the cyano group is different in position, the cyano group in the comparison compound 5 is linked to the dibenzofuran group through the phenyl group, and the cyano group in the compound 119 is introduced to the triazine group through the biphenyl group, so that the charge distribution of the compound 119 is more balanced, the molecular polarization degree is easily increased in the comparison compound 5, the mobility is slowed down, and the luminous efficiency of the comparison compound 119 is improved by 8% as shown in the table 2.
Compared with the compound 120, the introduction of dibenzofuran in the fluorene ring of the comparative compound 6 is beneficial to electron transfer, meanwhile, uneven charge distribution in molecules is reduced, bipolar of the molecules is avoided, electron transfer capacity is enhanced, luminous efficiency of the device is improved, and the luminous efficiency of the compound 120 is improved by 13% compared with that of the comparative compound 6 as shown in table 2.
The above description is only of the preferred embodiments of the present invention and is not intended to limit the present invention, but various modifications and variations can be made to the present invention by those skilled in the art. Any modification, equivalent replacement, improvement, etc. made within the spirit and principle of the present invention should be included in the protection scope of the present invention.
Claims (10)
1. An electron transport material, characterized in that it is selected from the group consisting of compounds represented by the following formula 1:
wherein L is independently selected from any one of the group of functional groups formed by a chemical bond, phenyl, biphenyl, terphenyl, naphthyl, phenylnaphthyl, dimethylfluorenyl, phenanthryl, pyridyl, dibenzofuranyl, dibenzothienyl, phenyldibenzofuranyl, phenyldibenzothienyl, naphthalenyl dibenzofuranyl, naphthalenyl dibenzothienyl, and 9-phenylcarbazolyl;
ar is independently selected from any one of the groups shown in the following structural formulas:
2. the electron transport material according to claim 1, wherein L is independently selected from any one of a group of functional groups formed by a chemical bond, a phenyl group, and a biphenyl group.
3. The electron transport material according to claim 1, wherein Ar is independently selected from any one of the groups represented by the following structural formulas:
4. the electron transport material according to claim 1, wherein the electron transport material is selected from any one of the compounds represented by the following structural formulas:
wherein R represents hydrogen or cyano.
5. The electron transport material according to claim 1, wherein the electron transport material is selected from any one of the compounds represented by the following structural formulas:
6. the sub-transport material according to any one of claims 1 to 5, wherein the electron transport material is selected from any one of the compounds represented by the following structural formulas:
7. a method of producing an electron transport material according to claim 1, wherein the electron transport material is synthesized according to the following synthesis route:
wherein Hal and Hal 1 Selected from halogen.
8. The process according to claim 7, wherein Hal and Hal 1 Selected from any one of Cl, br and I.
9. The method of manufacturing according to claim 7, comprising: mixing the reactant 1, the reactant 2 and the palladium catalyst for reaction, wherein the reaction temperature is 85-95 ℃ and the reaction time is 8-12h;
preferably, the palladium catalyst comprises Pd 2 (dba) 3 、Pd(PPh 3 ) 4 、PdCl 2 、PdCl 2 (dppf)、Pd(OAc) 2 、Pd(PPh 3 ) 2 Cl 2 And NiCl 2 (dppf);
preferably, the molar ratio of the reactant 1, the reactant 2 and the palladium catalyst is 1:1.1-1.3:0.05-0.1;
preferably, it comprises: mixing the intermediate 1, the reactant 3, the palladium catalyst and the phosphine ligand for reaction, wherein the reaction temperature is 80-100 ℃ and the reaction time is 8-12h;
preferably, the phosphine ligand is selected from P (t-Bu) 3 、X-phos、PET 3 、PMe 3 、PPh 3 、KPPh 2 And P (t-Bu) 2 Any one of Cl;
preferably, the molar ratio of the intermediate 1, the reactant 3, the palladium catalyst and the phosphine ligand is 1:1.1-1.3:0.01-0.02:0.02-0.05.
10. An organic electroluminescent device comprising an electron transport layer prepared from the electron transport material of claim 1.
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