Compound containing anthrene structure and application thereof in organic electroluminescent device
阅读说明：本技术 一种含有蒽烯结构化合物及其在有机电致发光器件的应用 (Compound containing anthrene structure and application thereof in organic electroluminescent device ) 是由 叶中华 李崇 王芳 庞羽佳 张兆超 于 2018-08-27 设计创作，主要内容包括：本发明公开了一种含有蒽烯结构的化合物及其应用,属于半导体技术领域。本发明提供的化合物的结构如通式(1)所示：<Image he="495" wi="513" file="DDA0001778611420000011.GIF" imgContent="drawing" imgFormat="GIF" orientation="portrait" inline="no"></Image>通式(1)。本发明还公开了上述化合物的应用。本发明的化合物以蒽烯为核心,具有较高的载流子迁移率,具有良好的载流子平衡能力。同时具有较高的玻璃化温度和分子热稳定性,合适的HOMO和LUMO能级。该化合物作为发光层主体材料,能够产生三线态-三线态耦合作用,有效提高了三线态的利用率。基于此化合物的器件结构,可有效提升OLED器件的效率和寿命。(The invention discloses a compound containing an anthrene structure and application thereof, belonging to the technical field of semiconductors. The structure of the compound provided by the invention is shown as a general formula (1): general formula (1). The invention also discloses application of the compound. The compounds of the invention are based on anthrenesThe material has high carrier mobility and good carrier balance capability. Meanwhile, the glass transition temperature and the molecular thermal stability are higher, and the HOMO and LUMO energy levels are suitable. The compound is used as a luminescent layer main body material, can generate a triplet state-triplet state coupling effect, and effectively improves the utilization rate of a triplet state. The device structure based on the compound can effectively improve the efficiency and the service life of an OLED device.)
1. A compound containing an anthrene structure, characterized in that the structure of the compound is shown in the general formula (1):
in the general formula (1), Z1～Z10Each independently represents a nitrogen atom or C-R; r, equal or different, is hydrogen, fluorine, cyano, C1-20Straight chain alkyl group of (1), C3-20Branched alkyl of C1-20Linear heteroalkyl of (2), C3-20A branched heteroalkyl, substituted or unsubstituted C3-20Cycloalkyl of, C1-10Alkoxy, substituted or unsubstituted C6-30One of an aryl group, a substituted or unsubstituted 5-30 membered heteroaryl group containing one or more heteroatoms;
L1and L2Each independently represents a single bond, substituted or unsubstituted C6～30One of an arylene group of (a), a substituted or unsubstituted 5-30 membered heteroarylene group containing one or more heteroatoms;
Ar1、Ar2each independently represents substituted or unsubstituted C6-30One of an aryl group, a substituted or unsubstituted 5-30 membered heteroaryl group containing one or more heteroatoms;
wherein said substitutable group is optionally selected from cyano, halogen, C1-20Alkyl of (C)6-30One or more of aryl, 5-30 membered heteroaryl containing one or more heteroatoms;
the heteroatom is selected from an oxygen atom, a sulfur atom or a nitrogen atom.
2. The compound of claim 1, characterized in thatIn the general formula (1), L1And L2Each independently represents a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted anthrylene group, a substituted or unsubstituted phenanthrylene group, a substituted or unsubstituted pyridylene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted benzofuranylene group, or a substituted or unsubstituted benzothienylene group;
ar is1、Ar2And R each independently represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted isobenzofuranyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted isoquinolyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted isobenzothiophenyl group, a substituted or unsubstituted isoquinolyl group, a general formula (2), a general formula (3), a general formula (4), or a general formula (5);
x in the general formula (2) and the general formula (3)1、X2、X3Each independently represents a single bond, an oxygen atom, a sulfur atom, -C (R)4)(R5)-、-Si(R6)(R7)-、
R1～R3each independently represents a hydrogen atom, substituted or unsubstituted C6-30An aryl group of (a), a substituted or unsubstituted 5-to 30-membered heteroaryl group containing one or more heteroatoms; r1～R3The linkage with the general formula (2) or the general formula (3) may be a single bond substituted linkageAnd then, can also be a ring-in-ring connection;
z is the same or different and represents a nitrogen atom or C-H; z at the attachment site is represented as a carbon atom;
x is the same or different and represents a nitrogen atom or C-R9；
The R is4～R8Are each independently represented by C1-20Alkyl, substituted or unsubstituted C6-30An aryl group of (a), a substituted or unsubstituted 5-to 30-membered heteroaryl group containing one or more heteroatoms;
the R is9Represented by hydrogen atom, cyano group, halogen, C1-20Alkyl of (C)2-20Alkenyl of (a), substituted or unsubstituted C6-30An aryl group of (a), a substituted or unsubstituted 5-to 30-membered heteroaryl group containing one or more heteroatoms; two or more adjacent R9Can be bonded to each other to form a ring;
wherein said substitutable group is optionally selected from cyano, halogen, C1-20Alkyl of (C)6-30One or more of aryl, 5-30 membered heteroaryl containing one or more heteroatoms;
the heteroatom is selected from an oxygen atom, a sulfur atom or a nitrogen atom.
3. The compound of claim 2, wherein R in formula (2) or formula (3)1～R3Independently represent a hydrogen atom, a structure represented by general formula (6), general formula (7) or general formula (8);
said Y is1、Y2、Y3Each independently represents an oxygen atom, a sulfur atom, -C (R)10)(R11)-、-Si(R12)(R13)-、
wherein represents a site of formula (6), formula (7), formula (8) and formula (2) or formula (3) in parallel ring connection;
the Y represents a nitrogen atom or C-H;
the R is10～R14Are each independently represented by C1-20Alkyl, substituted or unsubstituted C6-30An aryl group of (a), a substituted or unsubstituted 5-to 30-membered heteroaryl group containing one or more heteroatoms;
wherein said substitutable group is optionally selected from cyano, halogen, C1-20Alkyl of (C)6-30One or more of aryl, 5-30 membered heteroaryl containing one or more heteroatoms;
the heteroatom is selected from an oxygen atom, a sulfur atom or a nitrogen atom.
4. The compound according to claim 3, wherein in the general formula (1), R represents one of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, methoxy or ethoxy;
the R is4～R8、R10～R14Each independently represents methyl, ethyl, propyl, isopropyl, tert-butyl, pentyl, phenyl, naphthyl, biphenyl or pyridyl;
the R is9Represented by a hydrogen atom, a fluorine atom, a cyano group, a methyl group, an ethyl group, a propyl group, an isopropyl group, a tert-butyl group, a pentyl group, a phenyl group, a naphthyl group, a biphenyl group or a pyridyl group;
the substituent of the substitutable group is one or more selected from fluorine atom, cyano group, methyl group, ethyl group, propyl group, isopropyl group, tertiary butyl group, amyl group, phenyl group, naphthyl group, biphenyl group, pyridyl group or furyl group.
5. The compound according to claim 1, wherein the structure of the general formula (1) represents a specific representation, but not limited thereto:
6. An organic electroluminescent device comprising functional layers, characterized in that at least one of the functional layers contains a compound containing an anthrene structure according to any one of claims 1 to 5.
7. An organic electroluminescent device according to claim 6, comprising a hole transport layer, wherein the material of the hole transport layer is the compound containing an anthrene structure according to any one of claims 1 to 5.
8. The organic electroluminescent device according to claim 6, comprising a light-emitting layer, wherein the host material of the light-emitting layer is the compound containing an anthrene structure according to any one of claims 1 to 5.
9. The organic electroluminescent device as claimed in claim 8, wherein the light-emitting layer further comprises a fluorescent light-emitting material.
10. A lighting or display element comprising the organic electroluminescent device according to any one of claims 6to 9.
Technical Field
The invention relates to a compound containing an anthrene structure and application thereof, belonging to the technical field of semiconductors.
Background
The Organic Light Emission Diodes (OLED) device technology can be used for manufacturing novel display products and novel lighting products, is expected to replace the existing liquid crystal display and fluorescent lamp lighting, and has wide application prospect. The OLED light-emitting device is like a sandwich structure and comprises electrode material film layers and organic functional materials clamped between different electrode film layers, and various different functional materials are mutually overlapped together according to purposes to form the OLED light-emitting device. When voltage is applied to electrodes at two ends of the OLED light-emitting device and positive and negative charges in the organic layer functional material film layer are acted through an electric field, the positive and negative charges are further compounded in the light-emitting layer, and OLED electroluminescence is generated.
Currently, the OLED display technology is already applied in the fields of smart phones, tablet computers, and the like, and is further expanded to the large-size application field of televisions, and the like, but compared with the actual product application requirements, the performance of the OLED device, such as light emitting efficiency, service life, and the like, needs to be further improved. Current research into improving the performance of OLED light emitting devices includes: the driving voltage of the device is reduced, the luminous efficiency of the device is improved, the service life of the device is prolonged, and the like. In order to realize the continuous improvement of the performance of the OLED device, not only the innovation of the structure and the manufacturing process of the OLED device but also the continuous research and innovation of the photoelectric functional material of the OLED are required to create the functional material of the OLED with higher performance.
The photoelectric functional materials of the OLED applied to the OLED device can be divided into two categories from the aspect of application, namely charge injection transmission materials and luminescent materials. Further, the charge injection transport material may be classified into an electron injection transport material, an electron blocking material, a hole injection transport material, and a hole blocking material, and the light emitting material may be classified into a host light emitting material and a doping material.
In order to fabricate a high-performance OLED light-emitting device, various organic functional materials are required to have good photoelectric properties, for example, as a charge transport material, good carrier mobility, high glass transition temperature, etc. are required, as a host material of a light-emitting layer, good bipolar, appropriate HOMO/LUMO energy level, etc. are required.
The OLED photoelectric functional material film layer for forming the OLED device at least comprises more than two layers of structures, the OLED device structure applied in industry comprises a hole injection layer, a hole transmission layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transmission layer, an electron injection layer and other various film layers, namely the photoelectric functional material applied to the OLED device at least comprises a hole injection material, a hole transmission material, a light emitting material, an electron transmission material and the like, and the material type and the matching form have the characteristics of richness and diversity. In addition, for the collocation of OLED devices with different structures, the used photoelectric functional material has stronger selectivity, and the performance of the same material in the devices with different structures can be completely different.
Currently, the efficiency and lifetime of blue light devices, especially deep blue light devices, are a problem in OLED research, and especially the difference between the lifetime of blue light devices and the lifetimes of green and red light devices is large. The main reason is that on one hand, the driving of the blue light device is larger than high, and the material is easy to generate membrane phase separation under the action of heat; in addition, since the energy of blue light is high, the stability of the material is lowered, and the material is easily decomposed. The blue light material mainly comprises fluorescence and phosphorescence, and although the blue phosphorescence material has high device efficiency, the blue phosphorescence material has the characteristics of high material cost, poor service life and the like, so that the blue light material is restricted to be applied to devices. Currently, the mainstream device manufacturers use fluorescent materials for blue light devices, and although the efficiency of the fluorescent materials is low, the service life of the fluorescent materials is long. The traditional fluorescent material cannot emit light due to the influence of spin forbidden resistance, and the theoretical limit of external quantum efficiency of the device is 5%; and the TTA material, including TTA host and TTA doping material, can utilize triplet-triplet coupling effect to raise the theoretical limit value of external quantum efficiency of the device to 12.5%. Therefore, the development of high-efficiency and high-stability blue-light TTA host materials is an important direction in the field of blue-light devices.
Therefore, aiming at the industrial application requirements of the current OLED device and the requirements of different functional film layers and photoelectric characteristics of the OLED device, a more suitable OLED functional material or material combination with higher performance needs to be selected to realize the comprehensive characteristics of high efficiency, long service life and low voltage of the device. In terms of the actual demand of the current OLED display lighting industry, the development of the current OLED material is far from enough, and lags behind the requirements of panel manufacturing enterprises, and it is very important to develop a higher-performance organic functional material as a material enterprise.
Disclosure of Invention
The invention aims to provide a compound with an anthrene structure. The compound takes the anthrene as a core, has higher glass transition temperature and molecular thermal stability, effectively ensures the stability of the material, and prevents the phase separation of material films and the decomposition of the material when the device works for a long time. In addition, the material has higher S1 (singlet state energy level), T1 is more than or equal to 0.5S1, and the material has good TTA effect, can fully utilize triplet state energy, and improves the external quantum efficiency of the device. The material also has proper HOMO and LUMO energy levels and carrier mobility, can be well matched with EB and ET materials in device energy level, and reduces device driving, thereby reducing the thermal efficiency of devices and prolonging the service life of the devices.
The organic electroluminescent device can be applied to illumination or display elements, so that the current efficiency, the power efficiency and the external quantum efficiency of the device are greatly improved; meanwhile, the service life of the device is obviously prolonged, and the OLED luminescent device has a good application effect and a good industrialization prospect.
The technical scheme for solving the technical problems is as follows: a lighting or display element comprising an organic electroluminescent device as described above.
The technical scheme for solving the technical problems is as follows:
the invention provides a compound taking anthrene as a core, which has a structure shown in a general formula (1):
in the general formula (1), Z1～Z10Each independently represents a nitrogen atom or C-R;
L1and L2Each independently represents a single bond, substituted or unsubstituted C6～30One of an arylene group of (a), a substituted or unsubstituted 5-30 membered heteroarylene group containing one or more heteroatoms;
r, equal or different, is hydrogen, fluorine, cyano, C1-20Straight chain alkyl group of (1), C3-20Branched alkyl of C1-20Linear heteroalkyl of (2), C3-20A branched heteroalkyl, substituted or unsubstituted C3-20Cycloalkyl of, C1-10Alkoxy, substituted or unsubstituted C6-30One of an aryl group, a substituted or unsubstituted 5-30 membered heteroaryl group containing one or more heteroatoms;
Ar1、Ar2each independently represents substituted or unsubstituted C6-30One of an aryl group, a substituted or unsubstituted 5-30 membered heteroaryl group containing one or more heteroatoms;
wherein said substitutable group is optionally selected from cyano, halogen, C1-20Alkyl of (C)6-30One or more of aryl, 5-30 membered heteroaryl containing one or more heteroatoms;
the heteroatom is selected from an oxygen atom, a sulfur atom or a nitrogen atom.
Further, in the general formula (1), L1、L2Each independently represents a single bond, substituted orUnsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, substituted or unsubstituted anthrylene, substituted or unsubstituted phenanthrylene, substituted or unsubstituted pyridylene, substituted or unsubstituted fluorenylene, substituted or unsubstituted carbazolyl, substituted or unsubstituted benzofuranylene, substituted or unsubstituted benzothienylene;
ar is1、Ar2And R independently represent a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted isobenzofuranyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted isoquinolyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted isobenzothiophenyl group, a substituted or unsubstituted isoquinolyl group, a general formula (2), a general formula (3), a general formula (4) or a general formula (5);
x in the general formula (2) and the general formula (3)1、X2、X3Each independently represents a single bond, an oxygen atom, a sulfur atom, -C (R)4)(R5)-、-Si(R6)(R7)-、
R1～R3each independently represents a hydrogen atom, substituted or unsubstituted C6-30An aryl group of (a), a substituted or unsubstituted 5-to 30-membered heteroaryl group containing one or more heteroatoms; r1～R3The connection mode with the general formula (2) or the general formula (3) can be single bond substitution connection or ring combination connection;
z is the same or different and represents a nitrogen atom or C-H; z at the attachment site is represented as a carbon atom;
x is the same or different and represents a nitrogen atom or C-R9；
The R is4～R8Are each independently represented by C1-20Alkyl, substituted or unsubstituted C6-30An aryl group of (a), a substituted or unsubstituted 5-to 30-membered heteroaryl group containing one or more heteroatoms;
the R is9Represented by hydrogen atom, cyano group, halogen, C1-20Alkyl of (C)2-20Alkenyl of (a), substituted or unsubstituted C6-30An aryl group of (a), a substituted or unsubstituted 5-to 30-membered heteroaryl group containing one or more heteroatoms; two or more adjacent R9Can be bonded to each other to form a ring;
wherein said substitutable group is optionally selected from cyano, halogen, C1-20Alkyl of (C)6-30One or more of aryl, 5-30 membered heteroaryl containing one or more heteroatoms;
the heteroatom is selected from an oxygen atom, a sulfur atom or a nitrogen atom.
Further, in the general formula (2) or the general formula (3), R1～R3Independently represent a hydrogen atom, a structure represented by general formula (6), general formula (7) or general formula (8);
said Y is1、Y2、Y3Each independently represents an oxygen atom, a sulfur atom, -C (R)10)(R11)-、-Si(R12)(R13)-、
wherein represents a site of formula (6), formula (7), formula (8) and formula (2) or formula (3) in parallel ring connection;
the Y represents a nitrogen atom or C-H;
the R is10～R14Are each independently represented by C1-20Alkyl, substituted or unsubstituted C6-30An aryl group of (a), a substituted or unsubstituted 5-to 30-membered heteroaryl group containing one or more heteroatoms;
wherein said substitutable group is optionally selected from cyano, halogen, C1-20Alkyl of (C)6-30One or more of aryl, 5-30 membered heteroaryl containing one or more heteroatoms;
the heteroatom is selected from an oxygen atom, a sulfur atom or a nitrogen atom.
Further, in the general formula (1), Ar1、Ar2And R independently represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted terphenyl group. Substituted or unsubstituted anthryl, substituted or unsubstituted phenanthryl, substituted or unsubstituted naphthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted 9,9, -spirobifluorenyl, substituted or unsubstituted
Further, in the general formula (1), R represents one of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, methoxy or ethoxy;
the R is4～R8、R10～R14Each independently represents methyl, ethyl, propyl, isopropyl, tert-butyl, pentyl, phenyl, naphthyl, biphenyl or pyridyl;
the R is9Represented by a hydrogen atom, a fluorine atom, a cyano group, a methyl group, an ethyl group, a propyl group, an isopropyl group, a tert-butyl group, a pentyl group, a phenyl group, a naphthyl group, a biphenyl group or a pyridyl group;
the substituent of the substitutable group is one or more selected from fluorine atom, cyano group, methyl group, ethyl group, propyl group, isopropyl group, tertiary butyl group, amyl group, phenyl group, naphthyl group, biphenyl group, pyridyl group or furyl group.
Further, the structure of the general formula (1) represents a specific representation, but not limited thereto:
The invention provides an organic electroluminescent device which comprises functional layers, wherein at least one functional layer contains the compound containing the anthrene structure.
Further, the organic electroluminescent device comprises a hole transport layer, wherein the material of the hole transport layer is the compound containing the anthrene structure.
Further, the organic electroluminescent device comprises a light-emitting layer, and the host material of the light-emitting layer is the compound containing the anthrene structure.
Further, a luminescent layer in the organic electroluminescent device also comprises a fluorescent luminescent material.
The invention also relates to a lighting or display element comprising an organic electroluminescent device as described above.
The invention has the beneficial effects that:
1. the compound is an anthrene structure compound, and due to the introduction of double bonds, the hole mobility of the material is effectively improved, and the hole mobility and the electron mobility are more matched. When the compound is used as a host material and matched with a blue fluorescent material, the compound area of the current carrier can be far away from one side of the hole transport layer/the electron blocking layer. On one hand, the carrier recombination region of the device can be improved, and the quenching probability of triplet excitons is reduced; in addition, the accumulation of holes in the hole transport layer/the electron blocking layer can be effectively prevented, and the service life of the device is prolonged.
2. The compound takes the anthrene as a core, has higher glass transition temperature and molecular thermal stability, effectively ensures the stability of the material, and prevents the phase separation of material films and the decomposition of the material when the device works for a long time. Meanwhile, the material has proper HOMO and LUMO energy levels and carrier mobility, can be well matched with EB and ET materials in device energy level, and reduces the driving voltage of the device.
3. The compound takes the anthrene as a core, has higher S1 singlet state energy level, has T1 of more than or equal to 0.5S1, has good TTA function, can fully utilize triplet state energy, and improves the external quantum efficiency of the device.
Drawings
FIG. 1 is a schematic diagram of a device structure to which the compound of the present invention is applied, wherein the components represented by the respective reference numerals are as follows:
1. transparent substrate layer, 2, ITO anode layer, 3, hole injection layer, 4, hole transport layer a, 5, hole transport layer b, 6, luminescent layer, 7, electron transport layer, 8, electron injection layer, 9, cathode reflection electrode layer.
Detailed Description
The principles and features of this invention are described below in conjunction with the following drawings, which are set forth by way of illustration only and are not intended to limit the scope of the invention.
Synthesis of intermediate C
(1) Under the protection of nitrogen, adding the raw material A and proper amount of toluene, and then adding palladium acetate (Pd (OAc)2) And silver oxide (Ag)2O), heating and refluxing for 36 hours, then cooling to room temperature, filtering the reaction solution, carrying out rotary evaporation on the filtrate, and passing through a silica gel column to obtain an intermediate B; the molar ratio of the raw material A to the palladium acetate is 1: 0.01-1: 0.1, the molar ratio of the raw material A to the silver oxide is 1: 1-1: 3, and 60-80ml of methyl acetate is added into 0.01mol of the toluene solventBenzene.
(2) Under the protection of nitrogen, adding the intermediate B and a proper amount of toluene, then adding carbon tetrachloride and triphenylphosphine, heating and refluxing for 24 hours, then cooling to room temperature, filtering the reaction solution, carrying out rotary evaporation on the filtrate, and passing through a silica gel column to obtain an intermediate C; the molar ratio of the intermediate B to carbon tetrachloride is 1: 1-1: 2, the molar ratio of the intermediate B to triphenyl phosphine is 1: 0.01-1: 0.1, and 60-80ml of toluene is added into 0.01mol of the intermediate B.
Synthesis of intermediate D:
(1) under the protection of nitrogen, adding the intermediate C and the raw material B, then adding a proper amount of mixed solvent of toluene, ethanol and water in a volume ratio of 1:1:1, then adding triphenylphosphine and dichlorotriphenylphosphine palladium, heating and refluxing for reaction for 20 hours, then cooling to room temperature, filtering the reaction solution, separating the filtrate to remove a water layer, carrying out rotary evaporation on an organic layer, and passing through a silica gel column to obtain an intermediate D; the molar ratio of the intermediate C to the raw material B is 1: 1.05-1: 1.0, the molar ratio of the intermediate C to the triphenyl phosphine is 1: 0.001-1: 0.01, the molar ratio of the intermediate C to the dichlorotriphenyl phosphine palladium is 1: 0.001-1: 0.01, and the dosage of the mixed solvent is 0.01mol, and 100 ml of organic solvent is added into the intermediate B.
Synthesis of a final product:
(1) under the protection of nitrogen, adding the intermediate D and the raw material C, then adding a proper amount of mixed solvent of toluene, ethanol and water in a volume ratio of 1:1:1, then adding triphenylphosphine and dichlorotriphenylphosphine palladium, heating and refluxing for reaction for 20 hours, then cooling to room temperature, filtering the reaction solution, separating the filtrate to remove a water layer, carrying out rotary evaporation on an organic layer, and passing through a silica gel column to obtain an intermediate D; the molar ratio of the intermediate D to the raw material C is 1: 1.05-1: 1.0, the molar ratio of the intermediate D to triphenylphosphine is 1: 0.001-1: 0.01, the molar ratio of the intermediate D to dichlorotriphenylphosphine palladium is 1: 0.001-1: 0.01, and the amount of the mixed solvent is that 100 ml of organic solvent is added into 0.01mol of the intermediate D.
The synthesis of the intermediate D comprises two steps: synthesizing an intermediate C from the raw material A and carbon tetrachloride; the intermediate C and the raw material B are subjected to coupling reaction to generate an intermediate D, and the specific structure is shown in Table 1.
TABLE 1
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