CN112321521B - Electron transport material, organic electroluminescent device and display device - Google Patents

Electron transport material, organic electroluminescent device and display device Download PDF

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CN112321521B
CN112321521B CN202011226685.3A CN202011226685A CN112321521B CN 112321521 B CN112321521 B CN 112321521B CN 202011226685 A CN202011226685 A CN 202011226685A CN 112321521 B CN112321521 B CN 112321521B
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electron transport
organic electroluminescent
reaction
water
electroluminescent device
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CN112321521A (en
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邢其锋
丰佩川
孙伟
胡灵峰
陈跃
陈雪波
马艳
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Yantai Jingshi Materials Genomic Engineering Research Institute
Yantai Xianhua Chem Tech Co ltd
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Yantai Xianhua Chem Tech Co ltd
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Abstract

The invention discloses an electron transport material with a general formula I, which can be used as an electron transport layer of an organic electroluminescent device in a display device. The electron transport material has a matrix structure of diversified fused heterocycles, high bond energy among atoms, good thermal stability, strong transition capability of electrons, and can be used as an electron transport layer material to effectively reduce the driving voltage of an organic electroluminescent device, improve the current efficiency of the organic electroluminescent device and prolong the service life of the organic electroluminescent device, and is favorable for intermolecular solid-state accumulation.

Description

Electron transport material, organic electroluminescent device and display device
Technical Field
The invention relates to the technical field of light-emitting display, in particular to an electron transport material, an organic electroluminescent device and a display device.
Background
Electroluminescence (EL) refers to a phenomenon in which a light emitting material emits light when excited by current and voltage under the action of an electric field, and is a light emitting process in which electric energy is directly converted into light energy. The organic electroluminescent display (hereinafter referred to as OLED) has a series of advantages of self-luminescence, low-voltage dc driving, full curing, wide viewing angle, light weight, simple composition and process, etc., and compared with the liquid crystal display, the organic electroluminescent display does not need a backlight source, and has a large viewing angle, low power, a response speed 1000 times that of the liquid crystal display, and a manufacturing cost lower than that of the liquid crystal display with the same resolution. Therefore, the organic electroluminescent device has very wide application prospect.
With the continuous advance of the OLED technology in the two fields of lighting and display, people pay more attention to the research on efficient organic materials affecting the performance of OLED devices, and an organic electroluminescent device with good efficiency and long service life is generally the result of the optimized matching of device structures and various organic materials, which provides great opportunities and challenges for chemists to design and develop functional materials with various structures.
Organic electroluminescent materials have many advantages over inorganic luminescent materials, such as: the processing performance is good, a film can be formed on any substrate by an evaporation or spin coating method, and flexible display and large-area display can be realized; the optical properties, electrical properties, stability, etc. of the materials can be adjusted by changing the structure of the molecules, the choice of the materials has a large space, and in the most common OLED device structure, the following organic materials are generally included: a hole injection material, a hole transport material, an electron transport material, and light emitting materials (dyes or doped guest materials) and corresponding host materials of each color. Currently, electron transport materials, as an important functional material, have a direct influence on the mobility of electrons and ultimately affect the luminous efficiency of OLEDs. However, the electron transport materials currently used in OLEDs have low electron transfer rates and poor energy level matching with adjacent layers, which severely limits the light emitting efficiency of OLEDs and the display function of OLED display devices.
Disclosure of Invention
The invention provides an electron transport material, an organic electroluminescent device and a display device, in order to improve the luminous efficiency and prolong the service life of the organic electroluminescent device.
The electron transport material has a structure shown as a formula (I):
Figure BDA0002763821870000021
wherein, the first and the second end of the pipe are connected with each other,
Ar 1 -Ar 3 is selected from C 6 -C 30 Aryl or C 3 -C 30 The heteroaryl of (a), wherein each hydrogen atom of the aryl may be independently substituted by Ra;
L 1 selected from chemical bonds, C 6 -C 30 Arylene group of (A) or (C) 3 -C 30 The heteroarylene group of (a), wherein the hydrogen atoms on the arylene and heteroarylene groups, independently of each other, may be substituted with Ra;
L 2 selected from substituted or unsubstituted naphthyl, dibenzofuranyl or dibenzothiophenyl;
Z 1 -Z 5 selected from CR or N, R is selected from hydrogen and C 6 -C 30 Arylene group of (A) or (C) 3 -C 30 The heteroarylene group of (a);
ra is independently selected from deuterium, halogen, nitro, cyano, C 1 -C 4 Alkyl, phenyl, biphenyl, terphenyl or naphthyl.
Preferably, ar is 1 -Ar 3 Selected from one of the following unsubstituted or substituted by Ra: phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, fluorenyl, 9-dimethylfluorenyl, spirofluorenyl, dibenzofuranyl, dibenzothiopheneAn aza-dibenzofuranyl group, an aza-dibenzothiophenyl group; l is a radical of an alcohol 1 A subunit selected from the group consisting of a bond, unsubstituted or substituted with Ra: benzene, biphenyl, terphenyl, naphthalene, phenanthrene, triphenylene, fluorene, pyridine, pyridazine, pyrimidine, pyrazine, quinoline, isoquinoline, quinazoline, quinoxaline, cinnoline, naphthyridine, triazine, pyridopyrazine, furan, benzofuran, dibenzofuran, aza-dibenzofuran, thienylene, benzothiophene, dibenzothiophene, aza-dibenzothiophene, 9-dimethylfluorene, spirofluorene, arylamine, or carbazole; r is selected from hydrogen, cyano, the following unsubstituted or substituted by Ra: phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, fluorenyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, cinnolinyl, naphthyridinyl, triazinyl, pyridopyrazinyl, furanyl, benzofuranyl, dibenzofuranyl, aza-dibenzofuranyl, thienyl, benzothienyl, dibenzothienyl, aza-dibenzothienyl, 9-dimethylfluorenyl, arylamino, or carbazolyl.
The invention also discloses a specific structure of the electron transport material shown in the formula A1-A50:
Figure BDA0002763821870000031
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Figure BDA0002763821870000041
/>
Figure BDA0002763821870000051
the electron transport material has a matrix structure of an s-triphenyl system, high bond energy among atoms, good thermal stability, strong transition capability of electrons, and is beneficial to solid-state accumulation among molecules, and the electron transport material can be used as an electron transport layer material to effectively reduce the driving voltage of an organic electroluminescent device, improve the current efficiency of the organic electroluminescent device and prolong the service life of the organic electroluminescent device; the electron transport material is applied in an electron transport layer, has a proper energy level with the adjacent layers, is beneficial to the injection and the migration of electrons, and can effectively reduce the rising and falling voltage; the electron transport material has a larger conjugate plane, is beneficial to molecular accumulation, shows good thermodynamic stability, and shows long service life in an organic electroluminescent device.
The present invention also provides an organic electroluminescent device comprising at least an anode electrode, a hole transport layer, a light emitting layer, an electron transport layer and a cathode electrode, wherein the electron transport layer is at least one selected from the above-mentioned compounds, and in the present invention, there is no particular limitation in the kind and structure of the organic electroluminescent device as long as the electron transport material provided by the present invention can be used. The organic electroluminescent device of the present invention may be a light-emitting device having a top emission structure, and examples thereof include a light-emitting device comprising an anode, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, and a transparent or translucent cathode in this order on a substrate. The organic electroluminescent element of the present invention may be a light-emitting element having a bottom emission structure, and may include a structure in which a transparent or translucent anode, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, and a cathode are sequentially provided on a substrate. The organic electroluminescent element of the present invention may be a light-emitting element having a double-sided light-emitting structure, and may include a structure in which a transparent or translucent anode, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, and a transparent or translucent cathode are sequentially provided on a substrate.
Drawings
Fig. 1 is a schematic structural diagram of a typical organic electroluminescent device of the organic electroluminescent device according to the present invention, which is shown from bottom to top: a substrate 1, a reflective anode electrode 2, a hole injection layer 3, a hole transport layer 4, a light emitting layer 5, an electron transport layer 6, an electron injection layer 7, and a cathode electrode 8.
For convenience, the organic electroluminescent device of the present invention will be described below with reference to fig. 1, but this is not intended to limit the scope of the present invention in any way. It is understood that all organic electroluminescent devices capable of using the electron transport material of the present invention are within the scope of the present invention.
In the present invention, the substrate 1 is not particularly limited, and conventional substrates used in organic electroluminescent devices in the related art, such as glass, polymer materials, glass with TFT components, polymer materials, and the like, may be used.
In the present invention, the reflective anode electrode 2 is not particularly limited, and may be selected from Indium Tin Oxide (ITO), indium Zinc Oxide (IZO), tin dioxide (SnO) known in the art 2 ) The hole injection layer 3 in the present invention is not particularly limited, and may be made of a hole injection layer material known in the art, for example, a Hole Transport Material (HTM) is selected as a host material, and a p-type dopant is added, and the type of the p-type dopant is not particularly limited, and various p-type dopants known in the art may be used, for example, the following p-type dopants may be used:
Figure BDA0002763821870000071
in the present invention, the hole transport layer 4 is not particularly limited, and at least one of Hole Transport Materials (HTM) well known in the art may be selected, for example, the material for the hole injection layer host and the material for the hole transport layer may be selected from at least one of the following HT-1 to HT-32 compounds:
Figure BDA0002763821870000072
/>
Figure BDA0002763821870000081
in the present invention, the light emitting material in the light emitting layer 5 is not particularly limited, and any light emitting material known to those skilled in the art may be used, for example, the light emitting material may include a host material and a light emitting dye. The host material may be selected from at least one of the following GPH-1 to GPH-80 compounds:
Figure BDA0002763821870000082
/>
Figure BDA0002763821870000091
/>
Figure BDA0002763821870000101
/>
Figure BDA0002763821870000111
the light-emitting layer 5 preferably contains a phosphorescent dopant, and the dopant may be at least one selected from the following compounds RPD-1 to RPD-28, and the amount of the dopant is not particularly limited and may be an amount known to those skilled in the art.
Figure BDA0002763821870000112
Figure BDA0002763821870000121
/>
In the present invention, the electron transport layer 6 comprises at least one of the electron transport materials of the present invention, and the electron transport layer 6 may also comprise a combination of at least one of the electron transport materials of the present invention with at least one of the following known electron transport materials ET-1 to ET-57:
Figure BDA0002763821870000122
/>
Figure BDA0002763821870000131
/>
Figure BDA0002763821870000141
the electron injection layer 7 is not particularly limited, and electron injection materials known in the art may be used, and for example, may include, but are not limited to, liQ, liF, naCl, csF, li in the prior art 2 O、Cs 2 CO 3 At least one of BaO, na, li, ca and the like.
The cathode electrode 8 is not particularly limited and may be selected from, but not limited to, a magnesium silver mixture, liF/Al, ITO, al, and other metals, metal mixtures, oxides, and the like.
The method of preparing the organic electroluminescent device of the present invention is not particularly limited, and any method known in the art may be employed, for example:
(1) Cleaning a reflective anode electrode 2 on an OLED device substrate 1 for top emission, respectively performing steps of medicine washing, water washing, hair brushing, high-pressure water washing, air knife and the like in a cleaning machine, and then performing heat treatment;
(2) A hole injection layer 3 is vacuum evaporated on the reflecting anode electrode 2, the main material of the hole injection layer is HTM, and the hole injection layer contains P-type dopant (P-dopant) and has the thickness of 10-50nm;
(3) Vacuum evaporating Hole Transport Material (HTM) as a hole transport layer 4 on the hole injection layer 3, wherein the thickness is 80-150nm;
(4) Vacuum evaporating a light-emitting layer 5 on the hole transport layer 4, wherein the light-emitting layer contains a host material (GPH) and a guest material (RPD) and has a thickness of 20-50nm;
(5) Vacuum evaporation of an Electron Transport Material (ETM) as an electron transport layer 6 on the light emitting layer 5;
(6) Vacuum evaporating electron injection material on the electron transport layer 6 as an electron injection layer 7;
(7) A cathode material is vacuum-deposited on the electron injection layer 7 as a cathode electrode 8.
The third aspect of the present invention provides a display device comprising the above organic electroluminescent device, and the display device of the present invention includes, but is not limited to, a display, a television, a tablet computer, a mobile communication terminal, and the like.
Detailed Description
The present invention is described below with reference to examples, which are provided for illustration only and are not intended to limit the scope of the present invention.
1. Synthesis of electron transport materials
Example 1, synthesis of A1
Into a reaction flask were charged 100mmol of 1, 4-dibromonaphthalene, 100mmol of 4-cyanophenylboronic acid, 41.4g of potassium carbonate (300 mmol), 800ml of Tetrahydrofuran (THF), 200ml of water and Pd (PPh) 3 ) 4 Reacting at 60 deg.C for 12h, stopping reaction after reaction, cooling the reaction product to room temperature, adding water, filtering, washing with water, recrystallizing the obtained solid with toluene, and purifying to obtain white powder M1, wherein Pd (PPh) 3 ) 4 The addition amount of (A) is 1mol% of 1, 4-dibromonaphthalene;
into a reaction flask were charged 100mmol of M1, 120mmol of pinacol diboron, 41.4g of potassium carbonate (300 mmol), 800ml of dioxane, and 1mol% of Pd (dppf) 2 Cl 2 Reacting at 80 deg.C for 12 hr, stopping reaction after reaction, cooling to room temperature, adding water, filtering, washing with water, recrystallizing with toluene to obtain white powder M2, wherein Pd (dppf) 2 Cl 2 The addition amount of (2) is 1mol% of M4;
into a reaction flask were charged 100mmol of 1- (3-chloro-5-bromophenyl) -3, 5-diphenyltriazine, 100mmol of M2, 41.4g of potassium carbonate (300 mmol), 800ml of Tetrahydrofuran (THF), 200ml of water and Pd (PPh) 3 ) 4 In aReacting at 60 deg.C for 12h, stopping reaction after reaction, cooling the reaction product to room temperature, adding water, filtering, washing with water, recrystallizing the obtained solid with toluene, and purifying to obtain white powder M3, wherein Pd (PPh) 3 ) 4 The addition amount of (a) is 1mol% of 1- (3-chloro-5-bromophenyl) -3, 5-diphenyltriazine;
a reaction flask was charged with 100mmol of M3, 100mmol of 9, 9-dimethyl-2-fluorenylboronic acid, 41.4g of potassium carbonate (300 mmol), 800ml of Tetrahydrofuran (THF), 200ml of water and Pd (PPh) 3 ) 4 Reacting at 60 deg.C for 12h, stopping reaction after reaction, cooling reactant to room temperature, adding water, filtering, washing with water, recrystallizing the obtained solid with toluene, and purifying to obtain white powder A1, wherein Pd (PPh) 3 ) 4 Is added in an amount of 1mol% based on M3.
The hydrogen spectrum of A1 is characterized as follows:
1 H NMR(400MHz,Chloroform)δ9.00(s,2H),8.48(s,1H),8.40(d,J＝8.8Hz,3H),8.36–8.34(m,3H),8.30–8.04(m,3H),8.04–7.82(m,8H),7.78(s,1H),7.58(s,1H),7.34(d,J＝6.4Hz,4H),7.26(d,J＝13.6Hz,4H),1.69(s,6H).
the reaction scheme is as follows:
Figure BDA0002763821870000171
example 2, synthesis of A6
Into a reaction flask were charged 100mmol of 1, 4-dibromonaphthalene, 100mmol of 4-cyanophenylboronic acid, 41.4g of potassium carbonate (300 mmol), 800ml of Tetrahydrofuran (THF), 200ml of water and Pd (PPh) 3 ) 4 Reacting at 60 deg.C for 12h, stopping reaction after reaction, cooling reactant to room temperature, adding water, filtering, washing with water, recrystallizing the obtained solid with toluene, and purifying to obtain white powder M1, wherein Pd (PPh) 3 ) 4 The addition amount of (A) is 1mol% of 1, 4-dibromonaphthalene;
100mmol of M1, 120mmol of pinacol diborate, 41.4g of potassium carbonate (300 mmol), 800ml of dioxane and 1mol% ofPd(dppf) 2 Cl 2 Reacting at 80 deg.C for 12h, stopping reaction after reaction, cooling the reaction product to room temperature, adding water, filtering, washing with water, recrystallizing the obtained solid with toluene, and purifying to obtain white powder M2, wherein, pd (dppf) 2 Cl 2 The addition amount of (2) is 1mol% of M4;
into a reaction flask were charged 100mmol of 1- (3-chloro-5-bromophenyl) -3, 5-diphenyltriazine, 100mmol of M2, 41.4g of potassium carbonate (300 mmol), 800ml of Tetrahydrofuran (THF), 200ml of water and Pd (PPh) 3 ) 4 Reacting at 60 deg.C for 12h, stopping reaction after reaction, cooling the reaction product to room temperature, adding water, filtering, washing with water, recrystallizing the obtained solid with toluene, and purifying to obtain white powder M3, wherein Pd (PPh) 3 ) 4 The adding amount of the compound is 1mol percent of 1- (3-chloro-5-bromophenyl) -3, 5-diphenyl triazine;
into a reaction flask were charged 100mmol of M3, 100mmol of 3-pyridylboronic acid, 41.4g of potassium carbonate (300 mmol), 800ml of Tetrahydrofuran (THF), 200ml of water and Pd (PPh) 3 ) 4 Reacting at 60 deg.C for 12h, stopping reaction, cooling to room temperature, adding water, filtering, washing with water, recrystallizing the obtained solid with toluene, and purifying to obtain white powder A6, wherein Pd (PPh) 3 ) 4 Is added in an amount of 1mol% based on M3.
The hydrogen spectrum of A6 is characterized as follows:
1 H NMR(400MHz,Chloroform)δ9.24(s,1H),9.00(s,2H),8.70(s,1H),8.44(d,J＝14.4Hz,2H),8.34(d,J＝12.0Hz,5H),8.24(s,1H),7.93(s,2H),7.84(s,2H),7.48(d,J＝10.0Hz,7H),7.33(s,1H),7.27(s,1H).
the reaction scheme is as follows:
Figure BDA0002763821870000181
synthesis of examples 3, A11
100mmol of 2-bromo-4-cyanophenol, 100mmol of 2-fluoro-4-chlorobenzeneboronic acid, 41.4g of potassium carbonate (300 mmol) and 800m of potassium carbonate were charged in a reaction flaskl of Tetrahydrofuran (THF), 200ml of water and Pd (PPh) 3 ) 4 Reacting at 60 deg.C for 12h, stopping reaction after reaction, cooling reactant to room temperature, adding water, filtering, washing with water, recrystallizing the obtained solid with toluene, and purifying to obtain white powder M1, wherein Pd (PPh) 3 ) 4 The addition amount of (a) is 1mol% of 2-bromo-4-cyanophenol;
adding 100mmol of M1, 300ml of DMF and 41.4g of potassium carbonate (300 mmol) into a reaction bottle, reacting at 140 ℃ for 12 hours, stopping the reaction after the reaction is finished, cooling the reaction product to room temperature, adding water, filtering, washing with water, and recrystallizing and purifying the obtained solid with toluene to obtain white powder M2;
into a reaction flask were charged 100mmol of M2, 120mmol of pinacol diboron, 41.4g of potassium carbonate (300 mmol), 800ml of dioxane, and 1mol% of Pd (dppf) 2 Cl 2 Reacting at 80 deg.C for 12h, stopping reaction after reaction, cooling the reaction product to room temperature, adding water, filtering, washing with water, recrystallizing the obtained solid with toluene, and purifying to obtain white powder M3, wherein, pd (dppf) 2 Cl 2 The addition amount of (b) is 1mol% of M2;
into a reaction flask were charged 100mmol of M3, 100mmol of 1, 4-dibromonaphthalene, 41.4g of potassium carbonate (300 mmol), 800ml of Tetrahydrofuran (THF), 200ml of water and Pd (PPh) 3 ) 4 Reacting at 60 deg.C for 12h, stopping reaction after reaction, cooling the reaction product to room temperature, adding water, filtering, washing with water, recrystallizing the obtained solid with toluene, and purifying to obtain white powder M4, wherein Pd (PPh) 3 ) 4 The addition amount of (b) is 1mol% of M3;
into a reaction flask were charged 100mmol of M4, 120mmol of pinacol diboron, 41.4g of potassium carbonate (300 mmol), 800ml of dioxane, and 1mol% Pd (dppf) 2 Cl 2 Reacting at 80 deg.C for 12h, stopping reaction after reaction, cooling the reaction product to room temperature, adding water, filtering, washing with water, recrystallizing the obtained solid with toluene, and purifying to obtain white powder M5, wherein Pd (PPh) 3 ) 4 The addition amount of (2) is 1mol% of M4;
into a reaction flask were charged 100mmol of 1- (3-chloro-5-bromophenyl) -3, 5-diphenyltriazine, 100mmol of phenylboronic acid, 41.4g of potassium carbonate (300 mmol), 800ml of Tetrahydrofuran (THF), 200ml of water and Pd (PPh) 3 ) 4 Reacting at 60 deg.C for 12h, stopping reaction, cooling to room temperature, adding water, filtering, washing with water, recrystallizing the obtained solid with toluene, and purifying to obtain white powder M6, wherein Pd (PPh) 3 ) 4 The addition amount of (a) is 1mol% of 1- (3-chloro-5-bromophenyl) -3, 5-diphenyltriazine;
into a reaction flask were added 100mmol of M5, 100mmol of M6, 41.4g of potassium carbonate (300 mmol), 800ml of Tetrahydrofuran (THF), 200ml of water and Pd (PPh) 3 ) 4 Reacting at 60 deg.C for 12h, stopping reaction after reaction, cooling the reaction product to room temperature, adding water, filtering, washing with water, recrystallizing the obtained solid with toluene, and purifying to obtain white powder A11, wherein Pd (PPh) 3 ) 4 Is added in an amount of 1mol% based on M6.
The hydrogen spectrum characterization results for a11 are as follows:
1 HNMR(400MHz,Chloroform)δ9.09(s,1H),9.00(s,2H),8.48(t,J＝8.0Hz,2H),8.36(s,1H),8.26(q,J＝12.4Hz,2H),8.08(s,1H),8.00(d,J＝7.2Hz,2H),7.77(d,J＝12.0Hz,4H),7.69(d,J＝13.2Hz,4H),7.61(s,1H),7.57(s,1H),7.52–7.41(m,7H),7.40(d,J＝6.8Hz,2H),7.33(s,1H),7.27(s,1H).
the reaction scheme is as follows:
Figure BDA0002763821870000201
example 4, synthesis of A14
Into a reaction flask were charged 100mmol of 1, 4-dibromonaphthalene, 100mmol of 4-cyanophenylboronic acid, 41.4g of potassium carbonate (300 mmol), 800ml of Tetrahydrofuran (THF), 200ml of water and Pd (PPh) 3 ) 4 Reacting at 60 deg.C for 12h, stopping reaction, cooling to room temperature, adding water, filtering, washing with water, recrystallizing the obtained solid with toluene, and purifying to obtain white solidPowder M1, wherein Pd (PPh) 3 ) 4 The addition amount of (A) is 1mol% of 1, 4-dibromonaphthalene;
into a reaction flask were charged 100mmol of M1, 120mmol of pinacol diboron, 41.4g of potassium carbonate (300 mmol), 800ml of dioxane, and 1mol% of Pd (dppf) 2 Cl 2 Reacting at 80 deg.C for 12h, stopping reaction after reaction, cooling the reaction product to room temperature, adding water, filtering, washing with water, recrystallizing the obtained solid with toluene, and purifying to obtain white powder M2, wherein, pd (dppf) 2 Cl 2 The addition amount of (2) is 1mol% of M1;
into a reaction flask were charged 100mmol of 1- (3-chloro-5-bromophenyl) -3, 5-diphenyltriazine, 100mmol of M2, 41.4g of potassium carbonate (300 mmol), 800ml of Tetrahydrofuran (THF), 200ml of water and Pd (PPh) 3 ) 4 Reacting at 60 deg.C for 12h, stopping reaction after reaction, cooling reactant to room temperature, adding water, filtering, washing with water, recrystallizing the obtained solid with toluene, and purifying to obtain white powder M3, wherein Pd (PPh) 3 ) 4 The addition amount of (a) is 1mol% of 1- (3-chloro-5-bromophenyl) -3, 5-diphenyltriazine;
into a reaction flask were charged 100mmol of M3, 100mmol of 3-pyridylboronic acid, 41.4g of potassium carbonate (300 mmol), 800ml of Tetrahydrofuran (THF), 200ml of water and Pd (PPh) 3 ) 4 Reacting at 60 deg.C for 12h, stopping reaction, cooling to room temperature, adding water, filtering, washing with water, recrystallizing the obtained solid with toluene, and purifying to obtain white powder A14, wherein Pd (PPh) 3 ) 4 Is added in an amount of 1mol% based on M3.
The hydrogen spectrum of a14 is characterized as follows:
1 H NMR(400MHz,Chloroform)δ9.70(s,2H),9.15–8.82(m,6H),8.46(d,J＝13.2Hz,6H),8.36(s,1H),8.26(s,1H),8.06(s,1H),7.76(d,J＝12.0Hz,6H),7.56(s,2H),7.52–7.40(m,8H),7.40(s,1H),7.34(s,1H),7.25(s,1H).
the reaction scheme is as follows:
Figure BDA0002763821870000221
example 5, synthesis of A19
Into a reaction flask were charged 100mmol of 3, 5-dicyano-bromobenzene, 120mmol of pinacol diboron, 41.4g of potassium carbonate (300 mmol), 800ml of dioxane, and 1mol% of Pd (dppf) 2 Cl 2 Reacting at 80 deg.C for 12 hr, stopping reaction after reaction, cooling to room temperature, adding water, filtering, washing with water, recrystallizing with toluene to obtain white powder M1, wherein Pd (dppf) 2 Cl 2 Is 1mol% of 3, 5-dicyano-bromobenzene;
into a reaction flask were charged 100mmol of 1, 4-dibromonaphthalene, 100mmol of M1, 41.4g of potassium carbonate (300 mmol), 800ml of Tetrahydrofuran (THF), 200ml of water and Pd (PPh) 3 ) 4 Reacting at 60 deg.C for 12h, stopping reaction after reaction, cooling reactant to room temperature, adding water, filtering, washing with water, recrystallizing the obtained solid with toluene, and purifying to obtain white powder M2, wherein Pd (PPh) 3 ) 4 The addition amount of (A) is 1mol% of 1, 4-dibromonaphthalene;
into a reaction flask were charged 100mmol of M2, 120mmol of pinacol diboron, 41.4g of potassium carbonate (300 mmol), 800ml of dioxane, and 1mol% of Pd (dppf) 2 Cl 2 Reacting at 80 deg.C for 12h, stopping reaction after reaction, cooling reactant to room temperature, adding water, filtering, washing with water, recrystallizing the obtained solid with toluene, and purifying to obtain white powder M3, wherein Pd (PPh) 3 ) 4 The addition amount of (b) is 1mol% of M2;
into a reaction flask were charged 100mmol of 1- (3-chloro-5-bromophenyl) -3, 5-diphenyltriazine, 100mmol of 1-naphthylboronic acid, 41.4g of potassium carbonate (300 mmol), 800ml of Tetrahydrofuran (THF), 200ml of water and Pd (PPh) 3 ) 4 Reacting at 60 deg.C for 12h, stopping reaction after reaction, cooling the reaction product to room temperature, adding water, filtering, washing with water, recrystallizing the obtained solid with toluene, and purifying to obtain white powder M4, wherein Pd (PPh) 3 ) 4 Is added in an amount of 1-, (1mol% of 3-chloro-5-bromophenyl) -3, 5-diphenyltriazine;
into a reaction flask were added 100mmol of M3, 100mmol of M4, 41.4g of potassium carbonate (300 mmol), 800ml of Tetrahydrofuran (THF), 200ml of water and Pd (PPh) 3 ) 4 Reacting at 60 deg.C for 12h, stopping reaction, cooling to room temperature, adding water, filtering, washing with water, recrystallizing the obtained solid with toluene, and purifying to obtain white powder A19, wherein Pd (PPh) 3 ) 4 Is added in an amount of 1mol% based on M4.
The hydrogen spectrum of a19 is characterized as follows:
1 H NMR(400MHz,Chloroform)δ9.00(s,2H),8.95(s,1H),8.50(s,1H),8.45(d,J＝8.0Hz,2H),8.35(d,J＝7.6Hz,6H),8.24(s,1H),8.07(s,1H),7.89(s,1H),7.78(d,J＝8.0Hz,2H),7.50(s,1H),7.40(s,1H),7.34(d,J＝8.0Hz,3H),7.27(s,2H).
the reaction scheme is as follows:
Figure BDA0002763821870000231
example 6 Synthesis of A21
Into a reaction flask were charged 100mmol of 1, 4-dibromonaphthalene, 100mmol of 4-cyanophenylboronic acid, 41.4g of potassium carbonate (300 mmol), 800ml of Tetrahydrofuran (THF), 200ml of water and Pd (PPh) 3 ) 4 Reacting at 60 deg.C for 12h, stopping reaction after reaction, cooling reactant to room temperature, adding water, filtering, washing with water, recrystallizing the obtained solid with toluene, and purifying to obtain white powder M1, wherein Pd (PPh) 3 ) 4 The addition amount of (A) is 1mol% of 1, 4-dibromonaphthalene;
into a reaction flask were charged 100mmol of M1, 120mmol of pinacol diboron, 41.4g of potassium carbonate (300 mmol), 800ml of dioxane, and 1mol% Pd (dppf) 2 Cl 2 Reacting at 80 deg.C for 12h, stopping reaction after reaction, cooling the reaction product to room temperature, adding water, filtering, washing with water, recrystallizing the obtained solid with toluene, and purifying to obtain white powder M2, wherein, pd (dppf) 2 Cl 2 The addition amount of (2) is 1mol% of M4;
into a reaction flask were charged 100mmol of 1- (3-chloro-5-bromophenyl) -3-phenyl-5-naphthyltriazine, 100mmol of M2, 41.4g of potassium carbonate (300 mmol), 800ml of Tetrahydrofuran (THF), 200ml of water and Pd (PPh) 3 ) 4 Reacting at 60 deg.C for 12h, stopping reaction after reaction, cooling the reaction product to room temperature, adding water, filtering, washing with water, recrystallizing the obtained solid with toluene, and purifying to obtain white powder M3, wherein Pd (PPh) 3 ) 4 The adding amount of the compound is 1mol percent of 1- (3-chloro-5-bromophenyl) -3, 5-diphenyl triazine;
100mmol of M3 and 100mmol of (4- (1-phenyl-1H-benzo [ d ]) were charged into a reaction flask]Imidazol-2-yl) phenyl) boronic acid, 41.4g potassium carbonate (300 mmol), 800ml Tetrahydrofuran (THF), 200ml water and Pd (PPh) 3 ) 4 Reacting at 60 deg.C for 12h, stopping reaction, cooling to room temperature, adding water, filtering, washing with water, recrystallizing the obtained solid with toluene, and purifying to obtain white powder A21, wherein Pd (PPh) 3 ) 4 Is added in an amount of 1mol% based on M3.
The hydrogen spectrum of a21 is characterized as follows:
1 H NMR(400MHz,Chloroform)δ9.09(s,1H),9.00(s,1H),8.72–8.46(m,3H),8.34–8.26(m,5H),8.08(s,1H),7.99(dd,J＝12.8,8.4Hz,4H),7.86–7.77(m,3H),7.70(s,1H),7.62(d,J＝8.0Hz,4H),7.58–7.40(m,6H),7.38(s,1H),7.34–7.23(m,6H).
the reaction scheme is as follows:
Figure BDA0002763821870000251
2. preparation of organic electroluminescent device
Carrying out ultrasonic treatment on the glass plate coated with the ITO transparent conductive layer in a commercial cleaning agent, washing in deionized water, carrying out ultrasonic oil removal in an acetone-ethanol mixed solvent, baking in a clean environment until the water is completely removed, cleaning by using ultraviolet light and ozone, and bombarding the surface by using low-energy solar beams;
placing the glass substrate with the anode in a vacuum chamber, and vacuumizing to less than 10 DEG -5 And (3) vacuum evaporating a hole injection layer on the anode layer film by using the Torr, wherein the material of the hole injection layer is HT-4 and a p-type dopant (p-dopant) with the mass ratio of 3%, the evaporation rate is 0.1nm/s, the evaporation film thickness is 10nm, and the material of the hole injection layer and the p-type dopant are as follows:
Figure BDA0002763821870000252
vacuum evaporating a hole transport material HT-5 material on the hole injection layer to form a hole transport layer, wherein the evaporation rate is 0.1nm/s, and the evaporation film thickness is 80nm;
a luminescent layer is evaporated on the hole transport layer in vacuum, the luminescent layer comprises a main material GHP-16 and a dye material RPD-1, evaporation is carried out by a multi-source co-evaporation method, wherein the evaporation rate of the main material GHP-16 is adjusted to be 0.1nm/s, the evaporation rate of the dye RPD-1 is 3% of the evaporation rate of the main material, and the total thickness of the evaporation film is 30nm;
vacuum evaporating an Electron Transport Layer (ETL) on the light emitting layer, wherein the electron transport layer is the electron transport material prepared in the embodiments 1-6, and LiF with the thickness of 0.5nm is vacuum evaporated on the Electron Transport Layer (ETL) to be used as an electron injection layer, wherein the evaporation rate is 0.1nm/s, and the evaporation film thickness is 10nm; and finally, performing vacuum evaporation on the electron injection layer to form an aluminum layer with the thickness of 150nm as a cathode electrode of the organic electroluminescent device, wherein the evaporation rate is 1nm/s, and the evaporation film thickness is 50nm.
Comparative example 1
The electron transport material of the organic electroluminescent device is replaced by ET-2, and the rest is unchanged.
Comparative example 2
The electron transport material of the organic electroluminescent device is replaced by the substance with the following structure, and the rest is unchanged,
Figure BDA0002763821870000261
the organic electroluminescent devices of examples 1 to 6 and comparative example 1 were subjected to the following performance measurements:
measuring the driving voltage and current efficiency of the organic electroluminescent device and the lifetime of the device at the same brightness by using a digital source meter and a luminance meter, specifically, increasing the voltage at a rate of 0.1V per second, and measuring that the brightness of the organic electroluminescent device reaches 5000cd/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 life test of LT95 is as follows: using a luminance meter at 5000cd/m 2 At luminance, the luminance drop of the organic electroluminescent device was measured to be 4750cd/m while maintaining a constant current 2 Time in hours. The results are shown in Table 1.
TABLE 1 organic electroluminescent device Properties
Required luminance (cd/m) 2 ) Driving voltage/V Current efficiency (cd/A) Lifetime (LT 95)/h
Example 1 5000.00 4.0 41.5 280
Example 2 5000.00 4.1 42.3 275
Example 3 5000.00 4.1 42.4 270
Example 4 5000.00 3.9 41.7 285
Example 5 5000.00 4.1 42.0 280
Example 6 5000.00 3.9 42.8 285
Comparative example 1 5000.00 4.5 37.6 190
Comparative example 2 5000.00 4.2 39.5 255
As can be seen from Table 1, the compounds A1, A6, A11, A14, A19 and A21 prepared by the method are used for the electron transport material of the organic electroluminescent device, can effectively reduce the driving voltage, improve the current efficiency and prolong the service life of the device, and are electron transport materials with good performance.
The above description is only for the purpose of illustrating the preferred embodiments of the present invention and is not to be construed as limiting the invention, and any modifications, equivalents, improvements and the like that fall within the spirit and principle of the present invention are intended to be included therein.

Claims (4)

1. An electron transport material having a structure represented by formulas A11 and A14:
Figure FDA0004059175770000011
2. an organic electroluminescent device comprising an anode electrode, a hole transport layer, a light-emitting layer, an electron transport layer and a cathode electrode, wherein the electron transport layer comprises at least one of the electron transport materials of claim 1.
3. The organic electroluminescent device of claim 2, wherein the electron transport layer further comprises at least one transport material of the formula ET-1 to ET-57, wherein the structures of the formulae ET-1 to ET-57 are as follows,
Figure FDA0004059175770000012
/>
Figure FDA0004059175770000021
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Figure FDA0004059175770000031
Figure FDA0004059175770000041
/>
4. a display device comprising the organic electroluminescent element according to claim 2 or 3.
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