CN112125892A - Compound, electron transport material and organic electroluminescent device - Google Patents

Compound, electron transport material and organic electroluminescent device Download PDF

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CN112125892A
CN112125892A CN202010905494.3A CN202010905494A CN112125892A CN 112125892 A CN112125892 A CN 112125892A CN 202010905494 A CN202010905494 A CN 202010905494A CN 112125892 A CN112125892 A CN 112125892A
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邢其锋
丰佩川
单鸿斌
胡灵峰
陈跃
陈雪波
马艳
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Yantai Xianhua Chem Tech Co ltd
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Abstract

The application provides a compound of general formula (I) which can be used in an electron transport material. The compound has a parent structure of asymmetrically substituted dibenzoheterocycle, high bond energy among atoms, good thermal stability, favorable solid-state accumulation among molecules, strong transition capability of electrons, and can effectively reduce organic electroluminescence when used as an electron transmission materialThe optical device drives voltage, improves the current efficiency and prolongs the service life. The present application also provides an organic electroluminescent device and a display device comprising the compound of formula (I).
Figure DDA0002661275490000011

Description

Compound, electron transport material and organic electroluminescent device
Technical Field
The present disclosure relates to the field of organic light emitting display technologies, and in particular, to an electron transport material and an organic electroluminescent device including the same.
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 property, the electrical property, the stability and the like of the material can be adjusted by changing the structure of molecules, and the selection of the material has a large space. In the most common OLED device structures, the following classes of organic materials are typically included: hole injection materials, hole transport materials, electron transport materials, and light emitting materials (dyes or doped guest materials) and corresponding host materials of each color. At present, as an important functional material, an electron transport material has a direct influence on the mobility of electrons, and ultimately influences the luminous efficiency of an OLED. 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.
KR20180061075A reports an ET (electron transport) structure of a disubstituted dibenzoheterocycle, and the material has good performance as an ET material, but through research, the mobility of the material has room for improvement, and the film forming property is poor. Aiming at the improvement of the mobility and the film forming property of the materials, the structure of the invention is designed and invented.
Disclosure of Invention
An object of the embodiments of the present application is to provide an electron transport material to improve the working efficiency and prolong the service life of an organic electroluminescent device.
A first aspect of the present application provides a compound of general formula (I):
Figure BDA0002661275470000021
wherein the content of the first and second substances,
R1-R6each independently selected from hydrogen, deuterium, C1-C6Alkyl of (C)6-C30Aryl or C3-C30The hydrogen atoms on the aryl and heteroaryl groups may each independently be substituted by Ra, R1-R3Wherein two adjacent groups can be linked to form a ring, and R5And R6Can be connected into a ring;
a is selected from C6-C30Aryl or C3-C30The hydrogen atoms on the aryl and heteroaryl groups, each independently, may be substituted with Ra;
y is selected from O, S, CR7R8，R7And R8Each independently selected from C1-C6Alkyl of (C)5-C20Cycloalkyl of, C6-C30Aryl or C3-C30The hydrogen atoms on the aryl and heteroaryl groups may each independently be substituted by Ra, R7And R8Can be connected into a ring;
X1-X4each independently selected from CR9Or N, R9Selected from hydrogen, deuterium, C1-C6Alkyl of (C)6-C30Aryl or C3-C30The hydrogen atoms on the aryl and heteroaryl groups may each independently be replaced by Ra, and adjacent R9Can be connected into a ring;
L1and L2Each independently selected from the group consisting of a bond, C6-C30Arylene group of (A) or (C)3-C30The heteroarylene group of (a), wherein the hydrogen atoms on the arylene and heteroarylene groups, independently of each other, may be substituted with Ra;
each heteroatom on the heteroaryl or the heteroarylene is independently selected from O, S, N;
each Ra is independently selected from deuterium, halogen, nitro, cyano, C1-C4Alkyl, phenyl, biphenyl, terphenyl or naphthyl.
A second aspect of the present application provides an electron transport material comprising at least one of the compounds provided herein.
A third aspect of the present application provides an organic electroluminescent device comprising at least one of the electron transport materials provided herein.
A fourth aspect of the present application provides a display apparatus comprising an organic electroluminescent device as provided herein.
The compound provided by the application has an asymmetric parent structure substituting a dibenzoheterocycle, has high bond energy among atoms, good thermal stability, is favorable for solid-state accumulation among molecules, and has strong transition capability of electrons. When the organic electroluminescent material is used as an electron transport material, the organic electroluminescent material has a proper energy level between adjacent layers, is beneficial to the injection and migration of electrons, can effectively reduce the driving voltage, has a high electron migration rate, and can realize good luminous efficiency in an organic electroluminescent device. The organic electroluminescent device comprises the compound as an electron transport material, so that the driving voltage can be effectively reduced, the luminous efficiency is improved, and the service life of the organic electroluminescent device is prolonged. The display device provided by the application has an excellent display effect.
Of course, not all advantages described above need to be achieved at the same time in the practice of any one product or method of the present application.
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In order to more clearly illustrate the embodiments of the present application or the technical solutions in the prior art, the drawings needed to be used in the description of the embodiments or the prior art will be briefly described below, it is obvious that the drawings in the following description are only one embodiment of the present application, and other embodiments can be obtained by those skilled in the art according to the drawings.
Fig. 1 is a schematic structural view of a typical organic electroluminescent device.
Detailed Description
The technical solutions in the present application will be described clearly and completely with reference to the accompanying drawings, and it is to be understood that the described embodiments are only a part of the embodiments of the present application, and not all of the embodiments. All other embodiments obtained by a person of ordinary skill in the art based on the embodiments in this application are within the scope of protection of this application.
A first aspect of the present application provides a compound of general formula (I):
Figure BDA0002661275470000041
wherein the content of the first and second substances,
R1-R6each independently selected from hydrogen, deuterium, C1-C6Alkyl of (C)6-C30Aryl or C3-C30The hydrogen atoms on the aryl and heteroaryl groups may each independently be substituted by Ra, R1-R3Wherein two adjacent groups can be linked to form a ring, and R5And R6Can be connected into a ring;
a is selected from C6-C30Aryl or C3-C30The hydrogen atoms on the aryl and heteroaryl groups, each independently, may be substituted with Ra;
y is selected from O, S, CR7R8，R7And R8Each independently selected from C1-C6Alkyl of (C)5-C20Cycloalkyl of, C6-C30Aryl or C3-C30The hydrogen atoms on the aryl and heteroaryl groups may each independently be substituted by Ra, R7And R8Can be connected into a ring;
X1-X4each independently selected from CR9Or N, R9Selected from hydrogen, deuterium, C1-C6Alkyl of (C)6-C30Aryl or C3-C30The hydrogen atoms on the aryl and heteroaryl groups may each independently be replaced by Ra, and adjacent R9Can be connected into a ring;
L1and L2Each independently selected from the group consisting of a bond, C6-C30Arylene group of (A) or (C)3-C30A heteroarylene group of (a), saidThe hydrogen atoms on the arylene and heteroarylene groups each independently may be substituted with Ra;
each heteroatom on the heteroaryl or the heteroarylene is independently selected from O, S, N;
each Ra is independently selected from deuterium, halogen, nitro, cyano, C1-C4Alkyl, phenyl, biphenyl, terphenyl or naphthyl.
Preferably, R1-R6Each independently selected from hydrogen, deuterium, C1-C6Alkyl of (C)6-C18Aryl or C3-C18The hydrogen atoms on the aryl and heteroaryl groups, each independently, may be substituted with Ra;
preferably, A is selected from C6-C18Aryl or C3-C18The hydrogen atoms on the aryl and heteroaryl groups, each independently, may be substituted with Ra;
preferably, R7And R8Each independently selected from C1-C6Alkyl of (C)5-C18Cycloalkyl of, C6-C18Aryl or C3-C18The hydrogen atoms on the aryl and heteroaryl groups, each independently, may be substituted with Ra;
preferably, R9Selected from hydrogen, deuterium, C1-C6Alkyl of (C)6-C30Aryl or C3-C30The hydrogen atoms on the aryl and heteroaryl groups, each independently, may be substituted with Ra;
preferably, L1And L2Each independently selected from the group consisting of a bond, C6-C18Arylene group of (A) or (C)3-C18The heteroarylene group of (a), wherein the hydrogen atoms on the arylene and heteroarylene groups, independently of each other, may be substituted with Ra.
More preferably, said R1-R6Each independently selected from hydrogen, deuterium, methyl, ethyl, isopropyl, the following groups unsubstituted or substituted with Ra: phenyl, biphenyl, terphenyl, naphthyl,Phenanthryl, triphenylene, fluorenyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, cinnolinyl, naphthyridinyl, triazinyl, pyridopyrazinyl, furyl, benzofuryl, dibenzofuryl, aza-dibenzofuryl, thienyl, benzothienyl, dibenzothienyl, aza-dibenzothienyl, 9-dimethylfluorenyl, arylamine, carbazolyl.
More preferably, said a is selected from the following groups 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, carbazolyl.
More preferably, said R7And R8Each independently selected from methyl, ethyl, cyclopentyl, cyclohexyl, the following groups unsubstituted or substituted with 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, carbazolyl.
More preferably, said R9Selected from hydrogen, deuterium, methyl, ethyl, cyclopentyl, cyclohexyl, the following groups 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, azaazanyl-dibenzofuranyl, thienyl, benzothienyl, dibenzothienyl, aza-dibenzothienyl, 9-dimethylfluorenyl, arylamino, carbazolyl.
More preferably, said L1And L2Each independently selected from the group consisting of a bond, a subunit of the following compounds 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, carbazole.
For example, the compound of formula (I) is selected from the following compounds:
Figure BDA0002661275470000061
in a second aspect, the present application provides an electron transport material comprising at least one of the above compounds of the present application.
Fig. 1 shows a schematic diagram of a typical organic electroluminescent device, in which 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 are sequentially disposed from bottom to top.
It is to be understood that fig. 1 schematically illustrates the structure of a typical organic electroluminescent device, and the present application is not limited to this structure, and the electron transport material of the present application may be used in any type of organic electroluminescent device. For example, the organic electroluminescent device may further include an electron blocking layer, a hole blocking layer, a light extraction layer, and the like. In practice, these layers may be added or omitted as the case may be.
The compound adopted by the electron transport material has a parent structure which asymmetrically replaces a dibenzo heterocycle, has high bond energy among atoms, good thermal stability, is beneficial to solid-state accumulation among molecules, has strong transition capability of electrons, and can 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 when used as an electron transport layer material.
The derivative of the asymmetrically substituted dibenzoheterocycle is applied to an electron transport layer, has a proper energy level with an adjacent layer, is favorable for injection and migration of electrons, can effectively reduce driving voltage, has high electron migration rate, and can realize good luminous efficiency in an organic electroluminescent device. The compound provided by the application has a larger conjugated plane, is beneficial to molecular accumulation, shows good thermodynamic stability, and shows a long service life in an organic electroluminescent device.
Meanwhile, the preparation process of the asymmetrically substituted dibenzoheterocycle derivative is simple and feasible, and raw materials are easy to obtain, so that the method is suitable for industrial production.
In a third aspect, the present application provides an organic electroluminescent device comprising at least one of the electron transport materials provided herein as an electron transport layer. In the present application, there is no particular limitation on the kind and structure of the organic electroluminescent device, and there may be different types and structures of organic electroluminescent devices known in the art as long as the electron transport material provided herein can be used.
The organic electroluminescent device of the present application 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 device of the present application may be a light-emitting device 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 device of the present application may be a light-emitting device 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.
In the organic electroluminescent device of the present application, various materials used for the layer in the prior art may be used for the other layers in addition to the electron transport layer comprising the electron transport material provided herein.
For convenience, the organic electroluminescent device of the present application is described below with reference to fig. 1, but this is not meant to limit the scope of the present application in any way. It is understood that all organic electroluminescent devices capable of using the electron transport material of the present application are within the scope of the present application.
In the present application, the substrate 1 is not particularly limited, and conventional substrates used in organic electroluminescent devices in the related art, for example, glass, polymer materials, glass with TFT elements, polymer materials, and the like may be used.
In the present application, the reflective anode electrode 2 is not particularly limited, and may be selected from Indium Tin Oxide (ITO), Indium Zinc Oxide (IZO), and tin dioxide (SnO) known in the art2) Transparent conductive materials such as zinc oxide (ZnO), metal materials such as silver and its alloys, aluminum and its alloys, organic conductive materials such as PEDOT (poly-3, 4-ethylenedioxythiophene), multilayer structures of the above materials, and the like may be used.
In the present application, the material of the hole injection layer 3 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 the hole injection material.
In the present application, the hole injection layer 3 may further include a p-type dopant, the type of which is not particularly limited, and various p-type dopants known in the art may be employed, for example, the following p-type dopants may be employed:
Figure BDA0002661275470000081
in the present application, the amount of the p-type dopant is not particularly limited and may be an amount well known to those skilled in the art.
In the present application, the hole transport layer 4 is not particularly limited, and at least one of Hole Transport Materials (HTM) 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-31 compounds:
Figure BDA0002661275470000091
Figure BDA0002661275470000101
in the present application, the light emitting material in the light emitting layer 5 is not particularly limited, and various light emitting materials 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 BDA0002661275470000102
Figure BDA0002661275470000111
Figure BDA0002661275470000121
Figure BDA0002661275470000131
in a preferred embodiment of the present application, the light-emitting layer 5 employs the technique of phosphorescent electroluminescence. The light-emitting layer 5 contains a phosphorescent dopant, and the dopant may be at least one selected from the following compounds RPD-1 to RPD-28. The amount of the dopant is not particularly limited and may be an amount well known to those skilled in the art.
Figure BDA0002661275470000132
Figure BDA0002661275470000141
In the present application, the electron transport layer 6 comprises at least one of the electron transport materials of the present application, and the electron transport layer 6 may also comprise a combination of at least one of the electron transport materials of the present application and at least one of the following known electron transport materials ET-1 to ET-57:
Figure BDA0002661275470000142
Figure BDA0002661275470000151
Figure BDA0002661275470000161
Figure BDA0002661275470000171
in the present application, the electron transport layer 6 may further include an n-type dopant, the kind of the n-type dopant is not particularly limited, and various n-type dopants known in the art may be employed, for example, the following n-type dopants may be employed:
Figure BDA0002661275470000172
in the present application, the amount of the n-type dopant is not particularly limited and may be an amount well known to those skilled in the art.
In the present application, 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 art2O、Cs2CO3At least one of BaO, Na, Li, Ca and the like.
In the present application, the cathode electrode 8 is not particularly limited, and may be selected from, but not limited to, magnesium silver mixture, LiF/Al, ITO, Al, and other metals, metal mixtures, oxides, and the like.
A fourth aspect of the present application provides a display apparatus comprising an organic electroluminescent device as provided herein. The display device includes, but is not limited to, a display, a television, a tablet computer, a mobile communication terminal, etc.
The method for preparing the organic electroluminescent device of the present application is not particularly limited, and any method known in the art may be used, for example, the present application may be prepared by the following preparation method:
(1) cleaning a reflective anode electrode 2 on an OLED device substrate 1 for top emission, respectively carrying out steps of medicinal washing, water washing, hairbrush, high-pressure water washing, air knife and the like in a cleaning machine, and then carrying out heat treatment;
(2) vacuum evaporating a hole injection layer 3 on the reflecting anode electrode 2, wherein the hole injection layer 3 contains a main body material and a p-type dopant;
(3) vacuum evaporating a hole transport material on the hole injection layer 3 to form a hole transport layer 4;
(4) a luminescent layer 5 is evaporated on the hole transport layer 4 in vacuum, wherein the luminescent layer 5 comprises a host material and a guest material;
(5) vacuum evaporating an electron transport material on the luminescent layer 5 to form an electron transport layer 6;
(6) vacuum evaporating electron injection material selected from LiQ, LiF, NaCl, CsF, and Li on the electron transport layer 6 as electron injection layer 72O、Cs2CO3One or a combination of more of materials such as BaO, Na, Li, Ca and the like;
(7) a cathode material is vacuum-deposited on the electron injection layer 7 as a cathode electrode 8.
The above description has been made only of the structure of a typical organic electroluminescent device and a method for manufacturing the same, and it should be understood that the present application is not limited to this structure. The electron transport material of the present application can be used for an organic electroluminescent device of any structure, and the organic electroluminescent device can be manufactured by any manufacturing method known in the art.
The method for synthesizing the compound of the present application is not particularly limited, and the synthesis can be carried out by any method known to those skilled in the art. The following illustrates the synthesis of the compounds of the present application.
Synthetic examples
Synthesis of compound a 1:
Figure BDA0002661275470000181
into a reaction flask were charged 100mmol of 2-iodo-3-bromophenol, 100mmol of 2-fluoro-4-chlorobenzeneboronic acid, 41.4g of potassium carbonate (300mmol), 800ml of Tetrahydrofuran (THF) and 200ml of water, and 1 mol% of tetrakis (triphenylphosphine) palladium (Pd (PPh) was added3)4). The reaction was carried out at 120 ℃ for 12 h. After the reaction was completed, the reaction was stopped, and the reaction mixture was cooled to room temperature, water was added, the organic phase was concentrated to obtain a white solid, which was filtered and washed with water, and the obtained solid was recrystallized from toluene to obtain a white powder M1. Wherein, Pd (PPh)3)4The amount of (A) added was 1 mol% based on 2-bromo-4-chlorophenol.
100mmol of M1, 300ml of Dimethylformamide (DMF), 41.4g of potassium carbonate (300mmol) were added to a reaction flask and reacted at 120 ℃ for 12 hours. After the reaction, water was added to precipitate a solid, which was then filtered to obtain intermediate M2.
100mmol of M2, 110mmol of pinacol diboron, 41.4g of potassium acetate (300mmol), 800ml of dioxane and 1 mol% of dichloro [1,1' -bis (diphenylphosphino) ferrocene are added to a reaction flask]Palladium (Pd (dppf) Cl2). The reaction was carried out at 100 ℃ for 12 h. After the reaction was completed, the reaction was stopped, and the reaction was cooled to room temperature, water was added, the organic phase was separated, concentrated to obtain a white solid, which was filtered and washed with water, and the obtained solid was recrystallized from toluene to obtain a white powder M3. Wherein Pd (dppf) Cl2Was added in an amount of 1 mol% based on M2.
Into a reaction flask were charged 100mmol of 2-chloro-4, 6-diphenyltriazine, 100mmol of M3, 41.4g of potassium carbonate (300mmol), 800ml of THF and 200ml of water, and 1 mol% of Pd (PPh) was added3)4. The reaction was carried out at 120 ℃ for 12 h. After the reaction was completed, the reaction was stopped, and the reaction mixture was cooled to room temperature, water was added, the organic phase was concentrated to obtain a white solid, which was filtered and washed with water, and the obtained solid was recrystallized from toluene to obtain a white powder M4. Wherein, Pd (PPh)3)4Was added in an amount of 1 mol% based on M3.
Into a reaction flask were charged 100mmol of 4- (4-cyanophenyl) phenylboronic acid, 100mmol of M4, 41.4g of potassium carbonate (300mmol), 800ml of THF and 200ml of water, and 1 mol% of Pd (PPh) was added3)4. The reaction was carried out at 120 ℃ for 12 h. After the reaction was completed, the reaction was stopped, and the reaction mixture was cooled to room temperature, water was added, the organic phase was concentrated to obtain a white solid, which was filtered and washed with water, and the obtained solid was recrystallized from toluene to obtain a white powder a 1. Wherein, Pd (PPh)3)4Was added in an amount of 1 mol% based on M4.
1H NMR(400MHz,Chloroform)8.36(s,1H),7.99(s,1H),7.96(d,J＝12.4Hz,4H),7.80–7.63(m,5H),7.53(s,2H),7.48(d,J＝12.0Hz,4H),7.25-6.96(m,5H).
Synthesis of compound a 6:
Figure BDA0002661275470000191
into a reaction flask were charged 100mmol of 2-iodo-3-bromophenol, 100mmol of 2-fluoro-4-chlorobenzeneboronic acid, 41.4g of potassium carbonate (300mmol), 800ml of THF and 200ml of water, and 1 mol% of Pd (PPh) was added3)4. The reaction was carried out at 120 ℃ for 12 h. Stopping the reaction after the reaction is finished, and reactingThe reaction was cooled to room temperature, water was added, the organic phase was concentrated to give a white solid, which was filtered, washed with water and the resulting solid was purified by recrystallization from toluene to give white powder M1. Wherein, Pd (PPh)3)4The amount of (A) added was 1 mol% based on 2-bromo-4-chlorophenol.
100mmol of M1, 300ml of DMF, 41.4g of potassium carbonate (300mmol) were added to a reaction flask and reacted at 120 ℃ for 12 hours. After the reaction, water was added to precipitate a solid, which was then filtered to obtain intermediate M2.
100mmol of M2, 110mmol of pinacol diborate, 41.4g of potassium acetate (300mmol), 800ml of dioxane and 1 mol% of Pd (dppf) Cl were charged in a reaction flask2. The reaction was carried out at 100 ℃ for 12 h. After the reaction was completed, the reaction was stopped, and the reaction was cooled to room temperature, water was added, the organic phase was separated, concentrated to obtain a white solid, which was filtered and washed with water, and the obtained solid was recrystallized from toluene to obtain a white powder M3. Wherein Pd (dppf) Cl2Was added in an amount of 1 mol% based on M2.
Into a reaction flask were charged 100mmol of 2-chloro-4, 6-diphenyltriazine, 100mmol of M3, 41.4g of potassium carbonate (300mmol), 800ml of THF and 200ml of water, and 1 mol% of Pd (PPh) was added3)4. The reaction was carried out at 120 ℃ for 12 h. After the reaction was completed, the reaction was stopped, and the reaction mixture was cooled to room temperature, water was added, the organic phase was concentrated to obtain a white solid, which was filtered and washed with water, and the obtained solid was recrystallized from toluene to obtain a white powder M4. Wherein, Pd (PPh)3)4Was added in an amount of 1 mol% based on M3.
100mmol of 2-cyano-7-bromo-9, 9-dimethylfluorene, 110mmol of pinacol diboron, 41.4g of potassium acetate (300mmol), 800ml of dioxane and 1 mol% of Pd (dppf) Cl were charged in a reaction flask2. The reaction was carried out at 100 ℃ for 12 h. After the reaction was completed, the reaction was stopped, and the reaction was cooled to room temperature, water was added, the organic phase was separated, concentrated to obtain a white solid, which was filtered and washed with water, and the obtained solid was recrystallized from toluene to obtain a white powder M5. Wherein Pd (dppf) Cl2The amount of (A) added was 1 mol% of 2-cyano-7-bromo-9, 9-dimethylfluorene.
In a reaction bottle100mmol of M5, 100mmol of M4, 41.4g of potassium carbonate (300mmol), 800ml of THF and 200ml of water are added, and 1 mol% of Pd (PPh) is added3)4. The reaction was carried out at 120 ℃ for 12 h. After the reaction was completed, the reaction was stopped, and the reaction mixture was cooled to room temperature, water was added, the organic phase was concentrated to obtain a white solid, which was filtered and washed with water, and the obtained solid was recrystallized from toluene to obtain a white powder a 6. Wherein, Pd (PPh)3)4Was added in an amount of 1 mol% based on M4.
1H NMR(400MHz,Chloroform)8.36(s,1H),8.19–8.04(m,3H),8.00(s,1H),7.99(d,J＝9.6Hz,2H),7.90–7.62(m,8H),7.55–7.52(m,2H),7.48(d,J＝12.0Hz,4H),1.69(s,6H).
Synthesis of compound a 12:
Figure BDA0002661275470000201
into a reaction flask were charged 100mmol of methyl 2-borate-5-chlorobenzoate, 100mmol of 2-bromoiodobenzene, 41.4g of potassium carbonate (300mmol), 800ml of THF and 200ml of water, and 1 mol% of Pd (PPh) was added3)4. The reaction was carried out at 120 ℃ for 12 h. After the reaction was completed, the reaction was stopped, and the reaction mixture was cooled to room temperature, water was added, the organic phase was concentrated to obtain a white solid, which was filtered and washed with water, and the obtained solid was recrystallized from toluene to obtain a white powder M1. Wherein, Pd (PPh)3)4The amount of addition of (a) is 1 mol% of 2-bromoiodobenzene.
100mmol of M1 and 200ml of THF are added into a reaction flask, 220mmol of methyl magnesium bromide is added dropwise at 0 ℃, and the temperature is raised to room temperature for reaction for 12 hours after the dropwise addition. After the reaction was completed, water was added, the organic phase was separated and concentrated to obtain intermediate M2.
100mmol of M2 and 200ml of trifluoromethanesulfonic anhydride were added to a reaction flask, heated to 120 ℃ and reacted for 12 hours. After the reaction, water was added to precipitate a solid, which was then filtered and dried to obtain intermediate M3.
100mmol of M3, 110mmol of pinacol diborate, 41.4g of potassium acetate (300mmol), 800ml of dioxane and 1 mol% of Pd (dppf) were charged into a reaction flask)Cl2. The reaction was carried out at 100 ℃ for 12 h. After the reaction was completed, the reaction was stopped, and the reaction was cooled to room temperature, water was added, the organic phase was separated, concentrated to obtain a white solid, which was filtered and washed with water, and the obtained solid was recrystallized from toluene to obtain a white powder M4. Wherein Pd (dppf) Cl2Was added in an amount of 1 mol% based on M5.
Into a reaction flask were charged 100mmol of 2-chloro-4, 6-diphenyltriazine, 100mmol of M4, 41.4g of potassium carbonate (300mmol), 800ml of THF and 200ml of water, and 1 mol% of Pd (PPh) was added3)4. The reaction was carried out at 120 ℃ for 12 h. After the reaction was completed, the reaction was stopped, and the reaction mixture was cooled to room temperature, water was added, the organic phase was concentrated to obtain a white solid, which was filtered and washed with water, and the obtained solid was recrystallized from toluene to obtain a white powder M5. Wherein, Pd (PPh)3)4Was added in an amount of 1 mol% based on M4.
Into a reaction flask were charged 100mmol of 3- (3-cyanophenyl) phenylboronic acid, 100mmol of M5, 41.4g of potassium carbonate (300mmol), 800ml of THF and 200ml of water, and 1 mol% of Pd (PPh) was added3)4. The reaction was carried out at 120 ℃ for 12 h. After the reaction was completed, the reaction was stopped, and the reaction mixture was cooled to room temperature, water was added, the organic phase was concentrated to obtain a white solid, which was filtered and washed with water, and the obtained solid was recrystallized from toluene to obtain a white powder a 12. Wherein, Pd (PPh)3)4Was added in an amount of 1 mol% based on M5.
1H NMR(400MHz,Chloroform)8.36(s,1H),8.28–7.98(m,4H),7.77(dd,J＝12.8,8.8Hz,6H),7.69(d,J＝8.0Hz,4H),7.61(s,1H),7.50-7.43(m,6H),1.69(s,6H).
Synthesis of compound a 21:
Figure BDA0002661275470000221
into a reaction flask were charged 100mmol of 2-iodo-3-bromophenol, 100mmol of 2-fluoro-4-chlorobenzeneboronic acid, 41.4g of potassium carbonate (300mmol), 800ml of THF and 200ml of water, and 1 mol% of Pd (PPh) was added3)4. The reaction was carried out at 120 ℃ for 12 h. Stopping the reaction after the reaction is finishedAnd the reaction was cooled to room temperature, water was added, the organic phase was concentrated to give a white solid, which was filtered, washed with water, and the resulting solid was purified by recrystallization from toluene to give white powder M1. Wherein, Pd (PPh)3)4The amount of (A) added was 1 mol% based on 2-bromo-4-chlorophenol.
100mmol of M1, 300ml of DMF, 41.4g of potassium carbonate (300mmol) were added to a reaction flask and reacted at 120 ℃ for 12 hours. After the reaction, water was added to precipitate a solid, which was then filtered to obtain intermediate M2.
100mmol of M2, 110mmol of pinacol diborate, 41.4g of potassium acetate (300mmol), 800ml of dioxane and 1 mol% of Pd (dppf) Cl were charged in a reaction flask2. The reaction was carried out at 100 ℃ for 12 h. After the reaction was completed, the reaction was stopped, and the reaction was cooled to room temperature, water was added, the organic phase was separated, concentrated to obtain a white solid, which was filtered and washed with water, and the obtained solid was recrystallized from toluene to obtain a white powder M3. Wherein Pd (dppf) Cl2Was added in an amount of 1 mol% based on M2.
Into a reaction flask were added 100mmol of 2-bromopyridine, 100mmol of M3, 41.4g of potassium carbonate (300mmol), 800ml of THF and 200ml of water, and 1 mol% Pd (PPh) was added3)4. The reaction was carried out at 120 ℃ for 12 h. After the reaction was completed, the reaction was stopped, and the reaction mixture was cooled to room temperature, water was added, the organic phase was concentrated to obtain a white solid, which was filtered and washed with water, and the obtained solid was recrystallized from toluene to obtain a white powder M4. Wherein, Pd (PPh)3)4Was added in an amount of 1 mol% based on M3.
100mmol of M4, 110mmol of pinacol diborate, 41.4g of potassium acetate (300mmol), 800ml of dioxane and 1 mol% of Pd (dppf) Cl were charged in a reaction flask2. The reaction was carried out at 100 ℃ for 12 h. After the reaction was completed, the reaction was stopped, and the reaction was cooled to room temperature, water was added, the organic phase was separated, concentrated to obtain a white solid, which was filtered and washed with water, and the obtained solid was recrystallized from toluene to obtain a white powder M5. Wherein Pd (dppf) Cl2Was added in an amount of 1 mol% based on M4.
100mmol of 3-iodine-5-bromochlorobenzene, 105mmol of phenylboronic acid,41.4g of potassium acetate (300mmol), 800ml of dioxane, and 1 mol% of Pd (dppf) Cl2. The reaction was carried out at 100 ℃ for 12 h. After the reaction was completed, the reaction was stopped, and the reaction was cooled to room temperature, water was added, the organic phase was separated, concentrated to obtain a white solid, which was filtered and washed with water, and the obtained solid was recrystallized from toluene to obtain a white powder M6. Wherein Pd (dppf) Cl2The amount of the compound (A) added is 1 mol% of 3-iodo-5-bromochlorobenzene.
Into a reaction flask were charged 100mmol of M6, 100mmol of 4-cyanophenylboronic acid, 41.4g of potassium carbonate (300mmol), 800ml of THF and 200ml of water, and 1 mol% of Pd (PPh) was added3)4. The reaction was carried out at 120 ℃ for 12 h. After the reaction was completed, the reaction was stopped, and the reaction mixture was cooled to room temperature, water was added, the organic phase was concentrated to obtain a white solid, which was filtered and washed with water, and the obtained solid was recrystallized from toluene to obtain a white powder M7. Wherein, Pd (PPh)3)4Was added in an amount of 1 mol% based on M6.
Into a reaction flask were charged 100mmol of M7, 100mmol of M5, 41.4g potassium carbonate (300mmol), 800ml THF and 200ml water, and 1 mol% Pd (PPh) was added3)4. The reaction was carried out at 120 ℃ for 12 h. After the reaction was completed, the reaction was stopped, and the reaction mixture was cooled to room temperature, water was added, the organic phase was concentrated to obtain a white solid, which was filtered and washed with water, and the obtained solid was recrystallized from toluene to obtain a white powder a 21. Wherein, Pd (PPh)3)4Was added in an amount of 1 mol% based on M7.
1H NMR(400MHz,Chloroform)8.37(s,1H),8.28–8.08(m,4H),8.00–7.91(m,4H),7.62(d,J＝8.4Hz,2H),7.64–7.25(m,5H),7.39(d,J＝12.0Hz,2H),7.39(d,J＝10.0Hz,2H),7.14(s,1H),6.90(s,1H).
Synthesis of compound a 25:
Figure BDA0002661275470000231
into a reaction flask were charged 100mmol of 2-iodo-3-bromophenylthiol, 100mmol of 2-fluoro-4-chlorobenzeneboronic acid, 41.4g of potassium carbonate (300mmol), 800ml of THF and 200ml of water, and added1 mol% Pd (PPh)3)4. The reaction was carried out at 120 ℃ for 12 h. After the reaction was completed, the reaction was stopped, and the reaction mixture was cooled to room temperature, water was added, the organic phase was concentrated to obtain a white solid, which was filtered and washed with water, and the obtained solid was recrystallized from toluene to obtain a white powder M1. Wherein, Pd (PPh)3)4The amount of (A) added was 1 mol% based on 2-bromo-4-chlorophenol.
100mmol of M1, 300ml of DMF, 41.4g of potassium carbonate (300mmol) were added to a reaction flask and reacted at 120 ℃ for 12 hours. After the reaction, water was added to precipitate a solid, which was then filtered to obtain intermediate M2.
100mmol of M2, 110mmol of pinacol diborate, 41.4g of potassium acetate (300mmol), 800ml of dioxane and 1 mol% of Pd (dppf) Cl were charged in a reaction flask2. The reaction was carried out at 100 ℃ for 12 h. After the reaction was completed, the reaction was stopped, and the reaction was cooled to room temperature, water was added, the organic phase was separated, concentrated to obtain a white solid, which was filtered and washed with water, and the obtained solid was recrystallized from toluene to obtain a white powder M3. Wherein Pd (dppf) Cl2Was added in an amount of 1 mol% based on M2.
Into a reaction flask were charged 100mmol of 2-chloro-3-phenylquinoxaline, 100mmol of phenylboronic acid, 41.4g of potassium carbonate (300mmol), 800ml of THF and 200ml of water, and 1 mol% of Pd (PPh) was added3)4. The reaction was carried out at 120 ℃ for 12 h. After the reaction was completed, the reaction was stopped, and the reaction mixture was cooled to room temperature, water was added, the organic phase was concentrated to obtain a white solid, which was filtered and washed with water, and the obtained solid was recrystallized from toluene to obtain a white powder M4. Wherein, Pd (PPh)3)4Is added in an amount of 1 mol% based on the 2-chloro-3-phenylquinoxaline.
Into a reaction flask were charged 100mmol of M3, 100mmol of M4, 41.4g potassium carbonate (300mmol), 800ml THF and 200ml water, and 1 mol% Pd (PPh) was added3)4. The reaction was carried out at 120 ℃ for 12 h. After the reaction was completed, the reaction was stopped, and the reaction mixture was cooled to room temperature, water was added, the organic phase was concentrated to obtain a white solid, which was filtered and washed with water, and the obtained solid was recrystallized from toluene to obtain a white powder M5. Wherein, Pd (PPh)3)4Is addedThe amount was 1 mol% of M4.
Into a reaction flask were added 100mmol of 4-cyano-1, 1 '-biphenyl-4' -boronic acid, 100mmol of M5, 41.4g of potassium carbonate (300mmol), 800ml of THF and 200ml of water, and 1 mol% of Pd (PPh) was added3)4. The reaction was carried out at 120 ℃ for 12 h. After the reaction was completed, the reaction was stopped, and the reaction mixture was cooled to room temperature, water was added, the organic phase was concentrated to obtain a white solid, which was filtered and washed with water, and the obtained solid was recrystallized from toluene to obtain a white powder a 25. Wherein, Pd (PPh)3)4Was added in an amount of 1 mol% based on M5.
1H NMR(400MHz,Chloroform)8.86(s,2H),8.36(s,1H),8.03(dd,J＝12.8,8.6Hz,3H),7.99(t,J＝12.0Hz,3H),7.97(dd,J＝10.8,8.0Hz,4H),7.84-7.67(m,5H),7.59(s,1H),7.50(s,2H),7.31(d,J＝12.0Hz,4H),7.25(s,2H).
Synthesis of compound a 26:
Figure BDA0002661275470000251
into a reaction flask were charged 100mmol of methyl 2-borate benzoate, 100mmol of 2-bromo-4-chlorophenol, 41.4g of potassium carbonate (300mmol), 800ml of THF and 200ml of water, and 1 mol% of Pd (PPh) was added3)4. The reaction was carried out at 120 ℃ for 12 h. After the reaction was completed, the reaction was stopped, and the reaction mixture was cooled to room temperature, water was added, the organic phase was concentrated to obtain a white solid, which was filtered and washed with water, and the obtained solid was recrystallized from toluene to obtain a white powder M1. Wherein, Pd (PPh)3)4The amount of (A) added was 1 mol% based on 2-bromo-4-chlorophenol.
100mmol of M1 and 200ml of THF are added into a reaction flask, 220mmol of methyl magnesium bromide is added dropwise at 0 ℃, and the temperature is raised to room temperature for reaction for 12 hours after the dropwise addition. After the reaction was completed, water was added, the organic phase was separated and concentrated to obtain intermediate M2.
100mmol of M2 and 200ml of trifluoromethanesulfonic anhydride were added to a reaction flask, heated to 120 ℃ and reacted for 12 hours. After the reaction, water was added to precipitate a solid, which was then filtered and dried to obtain intermediate M3.
100mmol of M3, 110mmol of pinacol diborate, 41.4g of potassium acetate (300mmol), 800ml of dioxane and 1 mol% of Pd (dppf) Cl were charged in a reaction flask2. The reaction was carried out at 100 ℃ for 12 h. After the reaction was completed, the reaction was stopped, and the reaction was cooled to room temperature, water was added, the organic phase was separated, concentrated to obtain a white solid, which was filtered and washed with water, and the obtained solid was recrystallized from toluene to obtain a white powder M4. Wherein Pd (dppf) Cl2Was added in an amount of 1 mol% based on M3.
Into a reaction flask were charged 100mmol of 2-iodo-3-bromophenol, 100mmol of 2-fluoro-4-chlorobenzeneboronic acid, 41.4g of potassium carbonate (300mmol), 800ml of THF and 200ml of water, and 1 mol% of Pd (PPh) was added3)4. The reaction was carried out at 120 ℃ for 12 h. After the reaction was completed, the reaction was stopped, and the reaction mixture was cooled to room temperature, water was added, the organic phase was concentrated to obtain a white solid, which was filtered and washed with water, and the obtained solid was recrystallized from toluene to obtain a white powder M1'. Wherein, Pd (PPh)3)4The amount of (A) added was 1 mol% based on 2-bromo-4-chlorophenol.
100mmol of M1, 300ml of DMF, 41.4g of potassium carbonate (300mmol) were added to a reaction flask and reacted at 120 ℃ for 12 hours. After the reaction, water was added to precipitate a solid, which was then filtered to obtain intermediate M2'.
Into a reaction flask were charged 100mmol of M2', 100mmol of M4, 41.4g of potassium carbonate (300mmol), 800ml of THF and 200ml of water, and 1 mol% of Pd (PPh) was added3)4. The reaction was carried out at 120 ℃ for 12 h. After the reaction was completed, the reaction was stopped, and the reaction mixture was cooled to room temperature, water was added, the organic phase was concentrated to obtain a white solid, which was filtered and washed with water, and the obtained solid was recrystallized from toluene to obtain a white powder M5. Wherein, Pd (PPh)3)4Was added in an amount of 1 mol% based on M4.
Into a reaction flask were charged 100mmol of M5, 100mmol of 3-cyanophenylboronic acid, 41.4g of potassium carbonate (300mmol), 800ml of THF and 200ml of water, and 1 mol% of Pd (PPh) was added3)4. The reaction was carried out at 120 ℃ for 12 h. Stopping reaction after the reaction is finished, cooling the reactant to room temperature, adding water, concentrating an organic phase to obtain a white solid, filtering, washing with water to obtainThe solid of (2) was purified by recrystallization from toluene to give M6 as a white powder. Wherein, Pd (PPh)3)4Was added in an amount of 1 mol% based on M5.
Adding 100mmol of M6, 300ml of dichloromethane and 20ml of triethylamine into a reaction bottle, cooling to 0 ℃, dropwise adding 110mmol of trifluoromethanesulfonic anhydride, stirring at normal temperature, and reacting for 12 h. After the reaction is finished, water is added, an organic phase is separated, concentrated and dried to obtain an intermediate M7, wherein the OTf group in M7 is trifluoromethanesulfonic group.
100mmol of M7, 110mmol of pinacol diborate, 41.4g of potassium acetate (300mmol), 800ml of dioxane and 1 mol% of Pd (dppf) Cl were charged in a reaction flask2. The reaction was carried out at 100 ℃ for 12 h. After the reaction was completed, the reaction was stopped, and the reaction was cooled to room temperature, water was added, the organic phase was separated, concentrated to obtain a white solid, which was filtered and washed with water, and the obtained solid was recrystallized from toluene to obtain a white powder M8. Wherein Pd (dppf) Cl2Was added in an amount of 1 mol% based on M7.
Into a reaction flask were added 100mmol of M8, 100mmol of 2-chloro-4, 6-di-phenyltriazine, 41.4g potassium carbonate (300mmol), 800ml THF and 200ml water, and 1 mol% Pd (PPh) was added3)4. The reaction was carried out at 120 ℃ for 12 h. After the reaction was completed, the reaction was stopped, and the reaction mixture was cooled to room temperature, water was added, the organic phase was concentrated to obtain a white solid, which was filtered and washed with water, and the obtained solid was recrystallized from toluene to obtain a white powder a 26. Wherein, Pd (PPh)3)4Was added in an amount of 1 mol% based on M5.
1H NMR(400MHz,Chloroform)8.36(s,2H),8.12–7.94(m,4H),7.90(s,2H),7.87–7.73(m,4H),7.69(s,1H),7.62–7.55(m,4H),7.48(d,J＝12.0Hz,8H),7.34(s,1H),7.24(s,1H),1.69(s,6H).
Synthesis of compound a 27:
Figure BDA0002661275470000271
100mmol of 3-bromonaphtho [2,3-b ] benzofuran and 300ml of DMF (N-iodosuccinimide) (100mmol) were charged in a reaction flask, and reacted at 120 ℃ for 12 hours. After the reaction, water was added to precipitate a solid, which was then filtered to obtain intermediate M1.
100mmol of M1, 110mmol of pinacol diborate, 41.4g of potassium acetate (300mmol), 800ml of dioxane and 1 mol% of Pd (dppf) Cl were charged in a reaction flask2. The reaction was carried out at 100 ℃ for 12 h. After the reaction was completed, the reaction was stopped, and the reaction was cooled to room temperature, water was added, the organic phase was separated, concentrated to obtain a white solid, which was filtered and washed with water, and the obtained solid was recrystallized from toluene to obtain a white powder M3. Wherein Pd (dppf) Cl2Was added in an amount of 1 mol% based on M2.
Into a reaction flask were charged 100mmol of M2, 100mmol of 2-chloro-4-phenylquinazoline, 41.4g potassium carbonate (300mmol), 800ml THF and 200ml water, and 1 mol% Pd (PPh) was added3)4. The reaction was carried out at 120 ℃ for 12 h. After the reaction was completed, the reaction was stopped, and the reaction mixture was cooled to room temperature, water was added, the organic phase was concentrated to obtain a white solid, which was filtered and washed with water, and the obtained solid was recrystallized from toluene to obtain a white powder M3. Wherein, Pd (PPh)3)4Was added in an amount of 1 mol% based on M2.
Into a reaction flask were charged 100mmol of M3, 100mmol of 4- (4-cyanophenyl) -1-naphthalene-4-boronic acid, 41.4g of potassium carbonate (300mmol), 800ml of THF and 200ml of water, and 1 mol% of Pd (PPh) was added3)4. The reaction was carried out at 120 ℃ for 12 h. After the reaction was completed, the reaction was stopped, and the reaction mixture was cooled to room temperature, water was added, the organic phase was concentrated to obtain a white solid, which was filtered and washed with water, and the obtained solid was recrystallized from toluene to obtain a white powder a 27. Wherein, Pd (PPh)3)4Was added in an amount of 1 mol% based on M3.
1H NMR(400MHz,Chloroform)8.99(d,J＝12.0Hz,2H),7.99(s,1H),7.95(d,J＝8.8Hz,3H),7.92(d,J＝8.4Hz,3H),7.87–7.72(m,6H),7.56(d,J＝13.6Hz,3H),7.48(d,J＝10.0Hz,4H),7.33-7.21(m,4H).
Synthesis of compound a 28:
Figure BDA0002661275470000281
into a reaction flask were charged 100mmol of 2-iodo-3-bromophenylthiol, 100mmol of 2-fluoro-4-chlorobenzeneboronic acid, 41.4g of potassium carbonate (300mmol), 800ml of THF and 200ml of water, and 1 mol% of Pd (PPh) was added3)4. The reaction was carried out at 120 ℃ for 12 h. After the reaction was completed, the reaction was stopped, and the reaction mixture was cooled to room temperature, water was added, the organic phase was concentrated to obtain a white solid, which was filtered and washed with water, and the obtained solid was recrystallized from toluene to obtain a white powder M1. Wherein, Pd (PPh)3)4The amount of (A) added was 1 mol% based on 2-bromo-4-chlorophenol.
100mmol of M1, 300ml of DMF, 41.4g of potassium carbonate (300mmol) were added to a reaction flask and reacted at 120 ℃ for 12 hours. After the reaction, water was added to precipitate a solid, which was then filtered to obtain intermediate M2.
100mmol of M2, 110mmol of pinacol diborate, 41.4g of potassium acetate (300mmol), 800ml of dioxane and 1 mol% of Pd (dppf) Cl were charged in a reaction flask2. The reaction was carried out at 100 ℃ for 12 h. After the reaction was completed, the reaction was stopped, and the reaction was cooled to room temperature, water was added, the organic phase was separated, concentrated to obtain a white solid, which was filtered and washed with water, and the obtained solid was recrystallized from toluene to obtain a white powder M3. Wherein Pd (dppf) Cl2Was added in an amount of 1 mol% based on M2.
Into a reaction flask were charged 100mmol of 2-iodo-3-bromophenol, 100mmol of 2-fluoro-4-chlorobenzeneboronic acid, 41.4g of potassium carbonate (300mmol), 800ml of THF and 200ml of water, and 1 mol% of Pd (PPh) was added3)4. The reaction was carried out at 120 ℃ for 12 h. After the reaction was completed, the reaction was stopped, and the reaction mixture was cooled to room temperature, water was added, the organic phase was concentrated to obtain a white solid, which was filtered and washed with water, and the obtained solid was recrystallized from toluene to obtain a white powder M4. Wherein, Pd (PPh)3)4The amount of (A) added was 1 mol% based on 2-bromo-4-chlorophenol.
100mmol of M4, 300ml of DMF, 41.4g of potassium carbonate (300mmol) were added to a reaction flask and reacted at 120 ℃ for 12 hours. After the reaction, water was added to precipitate a solid, which was then filtered to obtain intermediate M5.
100mmol of M5, 110mmol of pinacol diborate, 41.4g of potassium acetate (300mmol), 800ml of dioxane and 1 mol% of Pd (dppf) Cl were charged in a reaction flask2. The reaction was carried out at 100 ℃ for 12 h. After the reaction was completed, the reaction was stopped, and the reaction was cooled to room temperature, water was added, the organic phase was separated, concentrated to obtain a white solid, which was filtered and washed with water, and the obtained solid was recrystallized from toluene to obtain a white powder M3. Wherein Pd (dppf) Cl2Was added in an amount of 1 mol% based on M6.
Into a reaction flask were charged 100mmol of 2-chloro-3-phenylquinoxaline, 100mmol of M6, 41.4g of potassium carbonate (300mmol), 800ml of THF and 200ml of water, and 1 mol% of Pd (PPh) was added3)4. The reaction was carried out at 120 ℃ for 12 h. After the reaction was completed, the reaction was stopped, and the reaction mixture was cooled to room temperature, water was added, the organic phase was concentrated to obtain a white solid, which was filtered and washed with water, and the obtained solid was recrystallized from toluene to obtain a white powder M7. Wherein, Pd (PPh)3)4Is added in an amount of 1 mol% based on the 2-chloro-3-phenylquinoxaline.
Into a reaction flask were charged 100mmol of M3, 100mmol of M7, 41.4g potassium carbonate (300mmol), 800ml THF and 200ml water, and 1 mol% Pd (PPh) was added3)4. The reaction was carried out at 120 ℃ for 12 h. After the reaction was completed, the reaction was stopped, and the reaction mixture was cooled to room temperature, water was added, the organic phase was concentrated to obtain a white solid, which was filtered and washed with water, and the obtained solid was recrystallized from toluene to obtain a white powder M8. Wherein, Pd (PPh)3)4Was added in an amount of 1 mol% based on M3.
Into a reaction flask were added 100mmol of 4-cyanophenylboronic acid, 100mmol of M8, 41.4g of potassium carbonate (300mmol), 800ml of THF and 200ml of water, and 1 mol% of Pd (PPh) was added3)4. The reaction was carried out at 120 ℃ for 12 h. After the reaction was completed, the reaction was stopped, and the reaction mixture was cooled to room temperature, water was added, the organic phase was concentrated to obtain a white solid, which was filtered and washed with water, and the obtained solid was recrystallized from toluene to obtain a white powder a 28. Wherein, Pd (PPh)3)4Was added in an amount of 1 mol% based on M8.1H NMR(400MHz,Chloroform)8.38(s,1H),8.15(d, J ═ 10.0Hz,2H),8.02(d, J ═ 7.6Hz,3H),7.99 to 7.91(m,4H),7.84(s,1H),7.79 to 7.62(m,5H),7.58(d, J ═ 10.0Hz,4H),7.51(d, J ═ 8.0Hz,3H),7.32(s,1H). example 1, 1H
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;
then, the glass substrate with the anode is placed in a vacuum chamber and is vacuumized to be less than 10 DEG-5And (3) vacuum evaporating a hole injection layer on the anode layer film, wherein the hole injection layer is made of HT-11 and 3% of p-type dopant (p-1) by mass, 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 BDA0002661275470000301
then, a hole transport material HT-5 material is vacuum evaporated on the hole injection layer to form a hole transport layer, wherein the evaporation rate is 0.1nm/s, the evaporation film thickness is 80nm, and the hole transport layer is made of the following materials:
Figure BDA0002661275470000302
then, a luminescent layer is evaporated on the hole transport layer in vacuum, the luminescent layer comprises a host 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 host 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 host material, the total film thickness of evaporation is 30nm, and the host material and the guest material are respectively the following materials:
Figure BDA0002661275470000303
then, an electron transporting layer containing an electron transporting material a1 was vacuum-evaporated over the light emitting layer. Wherein, the evaporation rate is 0.1nm/s, the evaporation film thickness is 30nm, and the selected electron transport material A1 has the following formula:
Figure BDA0002661275470000304
then, carrying out vacuum evaporation on the LiF with the thickness of 0.5nm as an electron injection layer on the electron transport layer, wherein the evaporation rate is 0.1nm/s, and the evaporation film thickness is 10 nm;
then, an Al layer having a thickness of 150nm was vacuum-evaporated on the electron injection layer as a cathode electrode of the organic electroluminescent device, wherein the evaporation rate was 1nm/s and the evaporation film thickness was 50 nm.
Examples 2 to 8
The procedure was as in example 1 except that A6, A12, A21, A25, A26, A27 and A28 were used in place of A1. See table 1 for details.
Comparative example 1
The procedure was as in example 1 except that ET-2 was used in place of A1.
Figure BDA0002661275470000311
Comparative example 2
The procedure was as in example 1 except that A1 was replaced with R.
Figure BDA0002661275470000312
The organic electroluminescent device prepared by the above process was subjected to the following performance measurement:
the driving voltage and current efficiency and the lifetime of the organic electroluminescent devices prepared in examples 1 to 8 and comparative examples 1 to 2 were measured at the same luminance using a digital source meter and a luminance meter, specifically, the voltage was increased at a rate of 0.1V per second, and the luminance of the organic electroluminescent device reached 5000 cd/ionm2The 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/m2The luminance drop of the organic electroluminescent device was measured to be 4750cd/m by maintaining a constant current at luminance2Time in hours.
Table 1 organic electroluminescent device performance results
Figure BDA0002661275470000321
As can be seen from Table 1, the compounds A1, A6, A12, A21, A25, A26, A27 and A28 prepared by the method are used for an electron transport material of an 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 preferred embodiment of the present application and is not intended to limit the scope of the present application. Any modification, equivalent replacement, improvement and the like made within the spirit and principle of the present application are included in the protection scope of the present application.

Claims (11)

1. A compound of the general formula (I):
Figure FDA0002661275460000011
wherein the content of the first and second substances,
R1-R6each independently selected from hydrogen, deuterium, C1-C6Alkyl of (C)6-C30Aryl or C3-C30The hydrogen atoms on the aryl and heteroaryl groups may each independently be substituted by Ra, R1-R3Wherein two adjacent groups can be linked to form a ring, and R5And R6Can be connected into a ring;
a is selected from C6-C30Aryl or C3-C30The hydrogen atoms on the aryl and heteroaryl groups, each independently, may be substituted with Ra;
y is selected from O, S, CR7R8，R7And R8Each independently selected from C1-C6Alkyl of (C)5-C20Cycloalkyl of, C6-C30Aryl or C3-C30The hydrogen atoms on the aryl and heteroaryl groups may each independently be substituted by Ra, R7And R8Can be connected into a ring;
X1-X4each independently selected from CR9Or N, R9Selected from hydrogen, deuterium, C1-C6Alkyl of (C)6-C30Aryl or C3-C30The hydrogen atoms on the aryl and heteroaryl groups may each independently be replaced by Ra, and adjacent R9Can be connected into a ring;
L1and L2Each independently selected from the group consisting of a bond, C6-C30Arylene group of (A) or (C)3-C30The heteroarylene group of (a), wherein the hydrogen atoms on the arylene and heteroarylene groups, independently of each other, may be substituted with Ra;
each heteroatom on the heteroaryl or the heteroarylene is independently selected from O, S, N;
each Ra is independently selected from deuterium, halogen, nitro, cyano, C1-C4Alkyl, phenyl, biphenyl, terphenyl or naphthyl.
2. The compound according to claim 1, wherein,
R1-R6each independently selected from hydrogen, deuterium, C1-C6Alkyl of (C)6-C18Aryl or C3-C18The hydrogen atoms on the aryl and heteroaryl groups, each independently, may be substituted with Ra;
a is selected from C6-C18Aryl or C3-C18Heteroaryl of (a), aThe hydrogen atoms on the aryl and heteroaryl groups may each independently be replaced by Ra;
R7and R8Each independently selected from C1-C6Alkyl of (C)5-C18Cycloalkyl of, C6-C18Aryl or C3-C18The hydrogen atoms on the aryl and heteroaryl groups, each independently, may be substituted with Ra;
R9selected from hydrogen, deuterium, C1-C6Alkyl of (C)6-C30Aryl or C3-C30The hydrogen atoms on the aryl and heteroaryl groups, each independently, may be substituted with Ra;
L1and L2Each independently selected from the group consisting of a bond, C6-C18Arylene group of (A) or (C)3-C18The heteroarylene group of (a), wherein the hydrogen atoms on the arylene and heteroarylene groups, independently of each other, may be substituted with Ra.
3. A compound according to claim 1, wherein R is1-R6Each independently selected from hydrogen, deuterium, methyl, ethyl, isopropyl, the following groups unsubstituted or substituted with 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, carbazolyl.
4. A compound according to claim 1, wherein a is selected from 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, carbazolyl.
5. A compound according to claim 1, wherein R is7And R8Each independently selected from methyl, ethyl, cyclopentyl, cyclohexyl, the following groups unsubstituted or substituted with 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, carbazolyl.
6. A compound according to claim 1, wherein R is9Selected from hydrogen, deuterium, methyl, ethyl, cyclopentyl, cyclohexyl, the following groups 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, carbazolyl.
7. The compound according to claim 1, wherein said L1And L2Each independently selected from the group consisting of a bond, a subunit of the following compounds unsubstituted or substituted with Ra: benzene, biphenyl, terphenyl, naphthalene, phenanthrene, triphenylene, fluorene, pyridine, pyridazine, pyrimidine, pyrazine, quinoline, isoquinoline, quinazoline, quinoxaline, cinnoline, naphthyridineTriazine, pyridopyrazine, furan, benzofuran, dibenzofuran, aza-dibenzofuran, thienylene, benzothiophene, dibenzothiophene, aza-dibenzothiophene, 9-dimethylfluorene, spirofluorene, arylamine, carbazole.
8. The compound according to claim 1, wherein the compound is selected from the following compounds:
Figure FDA0002661275460000031
Figure FDA0002661275460000041
9. an electron transport material comprising at least one of the compounds of any one of claims 1-8.
10. An organic electroluminescent device comprising at least one of the electron transport materials of claim 9.
11. A display device comprising the organic electroluminescent device according to claim 10.
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