WO2020199996A1 - Substituted 1,3,5-triazine compound, composition and application thereof - Google Patents

Substituted 1,3,5-triazine compound, composition and application thereof Download PDF

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WO2020199996A1
WO2020199996A1 PCT/CN2020/081035 CN2020081035W WO2020199996A1 WO 2020199996 A1 WO2020199996 A1 WO 2020199996A1 CN 2020081035 W CN2020081035 W CN 2020081035W WO 2020199996 A1 WO2020199996 A1 WO 2020199996A1
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independently
compound
substituted
alkyl group
element content
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PCT/CN2020/081035
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王悦
李成龙
张佐伦
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吉林省元合电子材料有限公司
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Priority to KR1020217035151A priority Critical patent/KR102663374B1/en
Priority to JP2021560344A priority patent/JP7236772B2/en
Publication of WO2020199996A1 publication Critical patent/WO2020199996A1/en

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Definitions

  • the invention relates to a substituted 1,3,5-triazine compound, composition and application thereof.
  • Pope et al. first reported the phenomenon of organic electroluminescence. They observed the blue light emitted by anthracene when a high voltage of 400 volts was applied on both sides of an anthracene single crystal (see M. Pope, H. Kallmann and P. Magnante, J. Chem. Phys., 1963, 38, 2042). However, because single crystals are difficult to grow and the device drive voltage is high, the processes they use have almost no practical use. Until 1987, CWTang et al.
  • the device obtains green light emission with a brightness of up to 1000 cd/m 2 under a driving voltage of 10V, and the device efficiency is 1.5 lm/W (see CWTang and SAVan Slyke, Appl. Phys. Lett., 1987, 51, 913). This breakthrough has enabled organic electroluminescence research to be carried out rapidly and deeply in the world.
  • phosphorescent materials generally use precious metals such as iridium and platinum, which are expensive.
  • precious metals such as iridium and platinum
  • they still have chemical instability, and the device has problems such as large efficiency roll-off under high current density.
  • An OLED device that uses cheap and stable organic small molecule materials and can achieve high-efficiency light emission is extremely important.
  • organic electroluminescence technology has received extensive research and attention in the scientific and industrial circles.
  • Organic small molecule optoelectronic materials are widely used as high-performance materials because of their clear structure, easy modification, simple purification and processing.
  • traditional fluorescent dye molecules often have very high fluorescence quantum yields, but their doped OLED devices are limited by the internal quantum efficiency of 25%, and the external quantum efficiency is generally lower than 5%, which is lower than the efficiency of phosphorescent devices.
  • red dye DCM see CWTang, SAVan Slyke, and CH Chen, J. Appl.
  • fluorescent OLED devices that can break through the 25% internal quantum efficiency limit mainly adopt a delayed fluorescence mechanism, which can effectively utilize the triplet excited state energy in the device.
  • TTA Triplet-Triplet Annihilation, triplet-triple annihilation
  • TADF Thermally Activated Delayed Fluorescence
  • the TTA mechanism is a mechanism that uses the fusion of two triplet excitons to generate singlet excitons to increase the generation rate of singlet excitons, but the maximum internal quantum efficiency of the device is only 40% to 62.5%.
  • the TADF mechanism uses organic small molecular materials with a small singlet-triplet energy level difference ( ⁇ EST).
  • the triplet excitons can be converted into singlet through the reverse intersystem crossing (RISC) process under ambient thermal energy.
  • RISC reverse intersystem crossing
  • the mechanism of heavy state excitons In theory, the quantum efficiency of the device can reach 100%.
  • TADF molecules are mainly used as guest materials doped in wide-bandgap host materials to achieve high-efficiency thermally activated delayed fluorescence (see Q. Zhang, J. Li, K. Shizu, S.
  • TADF material Because it can simultaneously use singlet and triplet excitons to emit light, the performance of the electroluminescent device of TADF material is significantly improved compared with traditional fluorescent devices. In addition, compared with traditional phosphorescent materials, TADF materials are inexpensive, which is more conducive to their commercial promotion and application. At present, TADF molecules of various light colors have been synthesized from deep blue to near-infrared light emission, and the performance of some devices is comparable to traditional phosphorescent devices. Traditional single-molecule TADF materials generally consist of donor (D) and acceptor (A) units.
  • Exciplex luminescence is a charge transfer excited state luminescence behavior between a donor molecule and an acceptor molecule. Its luminescence comes from the electrons between the LUMO orbital of the acceptor molecule and the HOMO orbital of the donor molecule. Jump. Since the HOMO and LUMO orbitals of the exciplex are concentrated on the donor and acceptor molecules, the corresponding singlet and triplet energy level differences tend to be smaller compared with single-molecule TADF materials.
  • exciplexes can also achieve efficient thermally activated delayed fluorescence emission.
  • Donor molecules and acceptor molecules can not only form exciplexes as a light-emitting layer to emit light, but also serve as hole transport and electron transport layers, respectively, which simplifies the structure of the device to a certain extent.
  • the molecular interface between the donor and acceptor can also produce exciplex luminescence similar to the planar heterojunction (PN) (see: Advanced Materials, 2016, 28 , 239-244).
  • PN planar heterojunction
  • Electroluminescent devices prepared with excimer complexes as co-hosts have many advantages such as low turn-on, high efficiency, and low roll-off, and have become a hot topic in current research (see: Advanced Functional Materials, 2015, 25, 361-366).
  • CN108218836A discloses two tris (phenyl/pyridine-benzimidazole) benzene/pyridine compounds (E1 and E2) as shown below. These two compounds can be used as electron acceptors and electron donors to construct a light-emitting layer. Similar materials can also be used as electron transport in electroluminescent devices.
  • E1 or E2 is used as an electron acceptor and an electron donor to construct a light-emitting layer, while E1 or E2 is used as an electron transport material, the efficiency of the prepared light-emitting device is low, and the stability of the device is poor.
  • the molecule as an electron acceptor material can be combined with some electron donor materials as the host material of the electroluminescence device, and the material can also be used as an electron transport layer for the electroluminescence device at the same time.
  • CN106946859A discloses a series of triazine compounds substituted with bisbenzimidazole and its derivatives, and points out that these compounds can be used as hole blocking layers and electron transport layers in electroluminescent devices, and these compounds can be used as light extraction layers or electron transport layers.
  • the layer is used in electroluminescent devices, which can improve the efficiency of the device to a certain extent.
  • CBP 4,4'-dicarbazole biphenyl
  • CN102593374B discloses the following three compounds (TPT-07, TBT-07 and TBT-14) as the electron transport layer and host material for the preparation of electroluminescent devices. However, the efficiency of the prepared light-emitting device is low.
  • the problem to be solved by the present invention is the deficiency of existing electron acceptor materials and electron transport materials, and provides a 1,3,5-triazine compound, composition and application thereof.
  • the 1,3,5-triazine compound of the present invention can not only be used as an electron transport material for preparing the electron transport layer of an electroluminescent device, but also can be used as an electron acceptor material, and a combination of it and an electron donor material can be used as The host material of the electroluminescent device, the electroluminescent device prepared therefrom has the advantages of higher efficiency and longer life; furthermore, the 1,3,5-triazine compound is used as the electron transport layer at the same time as The combination of the electron acceptor material and the electron donor material constructs a light-emitting layer, and the prepared electroluminescent device has the advantages of better high efficiency, longer life and the like.
  • the present invention solves the above technical problems through the following technical solutions.
  • the present invention provides a 1,3,5-triazine compound as shown in formula I,
  • R 1 , R 2 , R 3 , R 4 and R 5 are independently R; the rest (ie, R 1 , R 2 , R 3 , R 4 and R 5 are not R
  • R 1 , R 2 , R 3 , R 4 and R 5 are independently R
  • R 3 is independently R
  • R 1 , R 2 , R 4 and R 5 Is not R
  • R 2 and R 4 are independently R, R 1 , R 3 and R 5 Not R
  • R Y1 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 and R 15 are independently hydrogen, deuterium, halogen, cyano, C 1 ⁇ C 10 alkane group, with one or more substituents R a-1 is C 1 ⁇ C 10 alkyl group, C 1 ⁇ C 10 alkyl group -O-, with one or more R a-2 substituted C 1 ⁇ C 10 alkyl group -O-, C 6 ⁇ C 14 aryl group, substituted with one or more R a-3 substituted C 6 ⁇ C 14 aryl, 5-6 membered monocyclic heteroaryl, substituted with one or more R a-4 Substituted 5-6 membered monocyclic heteroaryl or The heteroatoms in the 5-6 membered monocyclic heteroaryl group and the 5-6 membered monocyclic heteroaryl group substituted by one or more Ra -4 The definition is as follows: the hetero
  • R is independently
  • n1 and n2 are independently 1, 2, 3 or 4; n3 is 1, 2 or 3;
  • R 1-1 , R 2-1 , R 1-2 , R 2-2 , R 1-3 , R 1-4 , R 2-3 are independently hydrogen, deuterium, halogen, cyano, C 1 ⁇ C 10 alkyl group, C 1 ⁇ C 10 alkyl group substituted by one or more R b-1 , C 1 ⁇ C 10 alkyl group-O-, C 1 ⁇ C 10 substituted by one or more R b-2 alkyl -O-, C 6 ⁇ C 14 aryl group, substituted with one or more R b-3 is unsubstituted C 6 ⁇ C 14 aryl, 5-6 membered monocyclic heteroaryl, substituted with one or more R b -4 substituted 5-6 membered monocyclic heteroaryl or The heteroatoms in the 5-6 membered monocyclic heteroaryl group and the 5-6 membered monocyclic heteroaryl group substituted by one or more R b-4 The definition is as follows: heteroatoms are selected from one or more of N,
  • heteroatom is N, and the number of heteroatoms is 1 to 3; when R c-1 and R c-2 are independently multiple, they are the same or different;
  • R a-1 , R a-2 , R a-3 , R a-4 , R b-1 , R b-2 , R b-3 , R b-4 , R c-1 and R c-2 are independent Ground is the following substituents: deuterium, halogen, cyano, trifluoromethyl, C 1 -C 6 alkyl or C 1 -C 6 alkyl-O-.
  • the definitions of certain substituents in the 1,3,5-triazine compound represented by formula I can be as follows, and the definitions of unmentioned substituents are as described in any of the above schemes .
  • R 1-1 , R 2-1 , R 1-2 , R 2-2 , R 1-3 , R 1-4 , R 2-3 , R Y1 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 and R 15 are independently halogens, and the halogens (such as fluorine, chlorine, bromine or iodine) are independently fluorine.
  • R Y1 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 and R 15 are independently C 1 to C 10 alkyl, substituted with one or more substituents
  • R a-1 is C 1 ⁇ C 10 alkyl group, C 1 ⁇ C 10 alkyl group by one or more -O- R a-2 substituted by C 1 ⁇ C 10 alkyl
  • the C 1 ⁇ C 10 alkyl group is independently a C 1 ⁇ C 6 alkyl group (for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, butyl, isobutyl, pentyl or hexyl group), preferably a C 1 ⁇ C 4 alkyl group (e.g. methyl, ethyl, n-propyl, iso
  • R Y1 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 and R 15 are independently C 6 ⁇ C 14
  • the C 6 ⁇ C 14 aryl group is independently a C 6 ⁇ C 10 aryl group; for example, phenyl or naphthyl .
  • R Y1 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 and R 15 are independently 5-6 yuan unit
  • the C 1 ⁇ C 12 heteroaryl group is independently a heteroatom selected from N, the number of heteroatoms 1 to 3; preferably pyridyl.
  • R 1-1 , R 2-1 , R 1-2 , R 2-2 , R 1-3 , R 1-4 and R 2-3 are independently C 1 ⁇ C 10 alkyl group, C 1 ⁇ C 10 alkyl group substituted by one or more R b-1 , C 1 ⁇ C 10 alkyl group-O- or C 1 ⁇ C substituted by one or more R b-2
  • the C 1 ⁇ C 10 alkyl is independently C 1 ⁇ C 6 alkyl (for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl group, sec-butyl, isobutyl, pentyl or hexyl), preferably a C 1 ⁇ C 4 alkyl group (e.g. methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butoxy , I
  • R 1-1 , R 2-1 , R 1-2 , R 2-2 , R 1-3 , R 1-4 and R 2-3 are independently C 6 ⁇ In a C 14 aryl group or a C 6 ⁇ C 14 aryl group substituted by one or more R b-3 , the C 6 ⁇ C 14 aryl group is independently a C 6 ⁇ C 10 aryl group; for example, phenyl or Naphthyl.
  • R 1-1 , R 2-1 , R 1-2 , R 2-2 , R 1-3 , R 1-4 and R 2-3 are independently 5-6
  • the C 1 ⁇ C 12 heteroaryl group is independently a heteroatom selected from N, hetero The number of atoms is 1 to 3; preferably pyridyl.
  • said 5-6 membered monocyclic heteroaryl group is independently a 5-6 membered monocyclic heteroaryl group or a 5-6 membered monocyclic heteroaryl group substituted with one or more R c-2 , said 5-6 membered monocyclic heteroaryl group is independently
  • the heteroatom is selected from N, and the number of heteroatoms is 1 to 2; preferably, it is pyridyl.
  • R 6 and R 11 are the same, R 7 and R 12 are the same, R 8 and R 13 are the same, R 9 and R 14 are the same, and R 10 and R 15 are the same.
  • R is independently located on the benzene ring and The ortho, meta or para position of the connection site; preferably, when the number of R is 2, they are independently located on the benzene ring and The meta position of the connection site.
  • said halogen e.g. fluorine, chlorine, bromine or iodine
  • Ra -1 , Ra -2 , Ra -3 , Ra -4 , R b-1 , R b-2 , R b-3 , R b-4 , R c-1 and R c-2 are independently C 1 ⁇ C 6 alkyl or C 1 ⁇ C 6 alkyl-O-, the C 1 ⁇ C 6 alkyl or C 1 ⁇ C 6 alkyl
  • the C 1 ⁇ C 6 alkyl group in -O- for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, sec-butyl, isobutyl, pentyl or hexyl
  • the ground is a C 1 -C 4 alkyl group (such as methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl or tert-buty
  • the number of R c-1 and R c-2 is 1, 2, or 3 independently.
  • R Y1 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 and R 15 are independently selected by one or more
  • a C 1 ⁇ C 10 alkyl group substituted by Ra-1 or a C 1 ⁇ C 10 alkyl group-O- substituted by one or more Ra -2 the substituted C 1 ⁇ C 10 alkyl group or substituted C 1 ⁇ C 10 alkyl group substituted with -O- in the C 1 ⁇ C 10 alkyl group is independently trifluoromethyl.
  • R 1-1 , R 2-1 , R 1-2 , R 2-2 , R 1-3 , R 1-4 and R 2-3 are independently Or more C 1 ⁇ C 10 alkyl substituted by R b-1 or C 1 ⁇ C 10 alkyl-O- substituted by one or more R b-2 , the substituted C 1 ⁇ C 10 alkyl or substituted C 1 ⁇ C 10 alkyl group substituted with -O- in the C 1 ⁇ C 10 alkyl group is independently trifluoromethyl.
  • R 1-1 , R 1-2 , R 1-3 and R 1-4 are independently hydrogen, deuterium, C 1 ⁇ C 10 alkyl group, and one or more R b-1 is substituted with C 1 ⁇ C 10 alkyl group, C 6 ⁇ C 14 aryl group, substituted with one or more R b-3 is unsubstituted C 6 ⁇ C 14 aryl, 5-6 membered monocyclic heteroaryl, 5-6 membered monocyclic heteroaryl substituted by one or more R b-4 or R 2-1 , R 2-2 and R 2-3 are independently hydrogen.
  • R Y1 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 and R 15 are independently hydrogen, deuterium, halogen , cyano, C 1 ⁇ C 10 alkyl group, with one or more substituents R a-1 is C 1 ⁇ C 10 alkyl group, C 6 ⁇ C 14 aryl group by one or more of the substituents R a-3 C 6 ⁇ C 14 aryl group; preferably hydrogen, deuterium, halo, cyano, C 1 ⁇ C 10 alkyl group by one or more substituents R a-1 is C 1 ⁇ C 10 alkyl group.
  • R is
  • R 1 , R 2 , R 3 , R 4 and R 5 are independently R; the rest are independently R Y1 ; R Y1 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14, and R 15 are independently hydrogen, deuterium, halogen, cyano, C 1 ⁇ C 10 alkyl, and one or more R a-1 a-substituted C 1 ⁇ C 10 alkyl group, C 6 ⁇ C 14 aryl group by one or more R a-3 substituted C 6 ⁇ C 14 aryl group;
  • R 6 and R 11 are the same, R 7 and R 12 are the same, R 8 and R 13 are the same, R 9 and R 14 are the same, and R 10 and R 15 are the same;
  • R is independently
  • R 1-1 , R 1-2 , R 1-3 and R 1-4 are independently hydrogen, deuterium, C 1 ⁇ C 10 alkyl, C 1 ⁇ C 10 substituted by one or more R b-1 alkyl group, C 6 ⁇ C 14 aryl group, substituted with one or more R b-3 is unsubstituted C 6 ⁇ C 14 aryl, 5-6 membered monocyclic heteroaryl, substituted with one or more R b-4 5-6 membered monocyclic heteroaryl group or R 2-1 , R 2-2 and R 2-3 are independently hydrogen.
  • R is the same.
  • one of R 1 , R 2 , R 3 , R 4 and R 5 is R; the rest are independently R Y1 ; or, R 2 and R 4 are independently R ; The rest are independently R Y1 ;
  • R 2 and R 4 are independently R, R 2 and R 4 are the same or different, for example the same.
  • R Y1 is independently hydrogen.
  • one of R 1 , R 2 , R 3 , R 4 and R 5 is R; the rest are independently R Y1 ; or, R 2 and R 4 are independently R ; The rest are independently R Y1 , and R Y1 are independently hydrogen.
  • R 8 and R 13 are independently hydrogen, halogen, C 1 ⁇ C 10 alkyl group, or by one or more substituents R a-1 is C 1 ⁇ C 10 alkyl group;
  • Ra -1 is independently halogen, such as fluorine
  • the C 1 -C 10 alkyl group substituted with one or more Ra -1 is trifluoromethyl.
  • R 6 , R 7 , R 9 , R 10 , R 11 , R 12 , R 14 and R 15 are independently hydrogen.
  • R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 and R 15 are independently hydrogen, halogen, C 1 ⁇ C 10 alkyl groups, or C 1 ⁇ C 10 alkyl groups substituted by one or more Ra -1 ;
  • R 8 and R 13 are independently hydrogen, halogen, C 1 ⁇ C 10 alkyl group, or by one or more substituents R a-1 is C 1 ⁇ C 10 alkyl group;
  • R 6, R 7, R 9 , R 10 , R 11 , R 12 , R 14 and R 15 are independently hydrogen;
  • R a-1 is independently halogen, such as fluorine; for another example, the C 1 to C 10 alkyl group substituted by one or more R a-1 is trifluoromethyl;
  • R 1-1 , R 2-1 , R 1-2 , R 2-2 , R 1-3 , R 1-4 , R 2-3 are independently hydrogen, C 6 ⁇ C 14 aryl group, substituted with one or more R b-3 is unsubstituted C 6 ⁇ C 14 aryl, 5-6 membered monocyclic heteroaryl, or
  • R 1-1, R 1-2, R 1-3, R 1-4 are independently hydrogen, C 6 ⁇ C 14 aryl group, substituted with one or more R b-3 is unsubstituted C 6 ⁇ C 14 Aryl, 5-6 membered monocyclic heteroaryl, or
  • R 2-1 , R 2-2 and R 2-3 are independently hydrogen.
  • R 1-1 , R 1-2 , R 1-3 , and R 1-4 are independently hydrogen, C 6 ⁇ C 14 aryl, and one or more R b- 3- substituted C 6 ⁇ C 14 aryl, 5-6 membered monocyclic heteroaryl, or
  • R b-3 is independently halogen, trifluoromethyl, or C 1 -C 6 alkyl.
  • R 2-1 , R 2-2 and R 2-3 are independently hydrogen.
  • one of R 1 , R 2 , R 3 , R 4 and R 5 is R; the rest are independently R Y1 ; or, R 2 and R 4 are independently R ; The rest are independently R Y1 , and R Y1 are independently hydrogen;
  • R is independently
  • R 2 and R 4 are independently R, R 2 and R 4 are the same or different;
  • R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 and R 15 are independently hydrogen, halogen, C 1 to C 10 alkyl, or one or more R a-1 is substituted with C 1 ⁇ C 10 alkyl group; R a-1 independently halogen;
  • R 1-1 , R 2-1 , R 1-2 , R 2-2 , R 1-3 , R 1-4 , R 2-3 are independently hydrogen, C 6 ⁇ C 14 aryl, and one or Multiple R b-3 substituted C 6 ⁇ C 14 aryl groups, 5-6 membered monocyclic heteroaryl groups, or R b-3 is independently halogen, trifluoromethyl or C 1 ⁇ C 6 alkyl;
  • R 2 and R 4 are independently R, R 2 and R 4 are the same;
  • R 8 and R 13 are independently hydrogen, halogen, C 1 ⁇ C 10 alkyl group, or by one or more substituents R a-1 is C 1 ⁇ C 10 alkyl group;
  • R a-1 is independently halogen
  • R 6 , R 7 , R 9 , R 10 , R 11 , R 12 , R 14 and R 15 are independently hydrogen;
  • R 1-1, R 1-2, R 1-3 , R 1-4 are independently hydrogen, C 6 ⁇ C 14 aryl group, substituted with one or more R b-3 is unsubstituted C 6 ⁇ C 14 aryl group , 5-6 membered monocyclic heteroaryl, or
  • R b-3 is independently halogen, trifluoromethyl or C 1 ⁇ C 6 alkyl
  • R 2-1 , R 2-2 and R 2-3 are independently hydrogen.
  • the 1,3,5-triazine compound represented by formula I is any one of the following compounds:
  • the compound of formula I of the present invention can be prepared according to conventional chemical synthesis methods in the art, and the steps and conditions can refer to the steps and conditions of similar reactions in the art.
  • the present invention provides a preparation method of 1,3,5-triazine compound as shown in formula I, which may include any of the following schemes:
  • R 1'and R 2' have the same definitions as R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and R 10 , R 1-1 , R 2- 1.
  • R 1-2 , R 2-2 , R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , n1, n2 and n3 are as defined above Said, m1 and m2 are 0, 1, 2, 3 or 4 independently.
  • the present invention provides an application of a 1,3,5-triazine compound as shown in formula I as an electronic material.
  • the electronic material is used as an electron transport material and/or electron acceptor material; preferably an electron transport material and/or electron acceptor material in an organic electroluminescence device.
  • the invention provides an application of a 1,3,5-triazine compound represented by formula I in the field of organic electroluminescence devices.
  • the 1,3,5-triazine compound represented by formula I is used to prepare the electron transport layer, the hole blocking layer and the light emitting layer in an organic electroluminescent device One or more of.
  • the present invention provides an organic electroluminescent composition, which includes an electron donor material and the 1,3,5-triazine compound represented by formula I.
  • the electron donor material in the organic electroluminescence composition may be a conventional phenyl or naphthylcarbazole electron donor material in the art; the benzene
  • the phenyl or naphthylcarbazole type electron donor material preferably contains 2-3 phenylcarbazole or naphthylcarbazole group structures; the phenyl or naphthylcarbazole type electron donor material preferably Any of the following compounds:
  • the molar ratio of the 1,3,5-triazine compound shown in formula I and the electron donor material can be a conventional molar ratio in the art (for example, a conventional excitation in the art).
  • the molar ratio of the electron acceptor material to the electron donor material in the matrix composite), preferably, the 1,3,5-triazine compound shown in formula I and the electron donor material The molar ratio is 3:1 to 1:3; more preferably 1:1.
  • the organic electroluminescent composition may also include a doped luminescent material; the doped luminescent material may be a conventional doped luminescent material in the field, such as fluorescent light. Materials and/or phosphorescent luminescent materials (also called phosphorescent complex luminescent materials).
  • the mass percentage of the doped luminescent material in the organic electroluminescent composition can be a conventional mass percentage in the art.
  • the doped luminescent material is a fluorescent luminescent material
  • the The mass percentage of the doped luminescent material in the composition is preferably 0.5WT%-2.0WT% (for example, 1WT%); when the doped luminescent material is a phosphorescent luminescent material, the doped luminescent material
  • the mass percentage of the heteroluminescent material in the composition is preferably 5.0 WT% to 15.0 WT% (for example, 10 WT%).
  • the phosphorescent luminescent material in the doped luminescent material, may be a conventional phosphorescent luminescent material in the art. In the present invention, it is preferably any of the following compounds:
  • Ra 1 , Ra 3 , Rb 1 , Rb 3 , Rd 1 , Rd 3 , Re 4 , Re 5 , Re 6 , Rf 7 , Rf 8 , Rf 9 , Rb 10-1 , Rb 10-2 , Re 10 -1 , Re 10-2 , Rf 10-1 and Rf 10-2 are independently H or a linear or branched alkyl group containing 1-5 C;
  • Ra 2 , Rb 2 and Rd 2 are independently H, a linear or branched alkyl group containing 1 to 5 C, a phenyl group, or a phenyl substituted with a linear or branched chain alkyl group of 1 to 5 C;
  • the phosphorescent luminescent material in the doped luminescent material, is IrPPy 3
  • the fluorescent luminescent material in the doped luminescent material, may be a conventional fluorescent luminescent material in the art. In the present invention, it is preferably any of the following compounds:
  • Rg 11-1 , Rg 11-2 , Rh 11-1 , and Rh 11-2 are independently linear or branched alkyl groups containing 1-5 C;
  • Rg 12-1 , Rg 12-2 , Rh 13-1 , Rh 13-2 , Rh 13-3 and Rh 13-4 represent linear or branched alkyl groups containing 1-5 C, F or CF 3 ;
  • Rm 22-1 , Rn 25-1 , Ro 28-11 and Rp 33-1 are linear or branched alkyl groups containing 1-4 Cs.
  • the fluorescent luminescent material in the doped luminescent material, is
  • the present invention provides an application of the above-mentioned organic electroluminescent composition as an organic electroluminescent material.
  • the organic electroluminescent material is used to prepare the light-emitting layer in an organic electroluminescent device.
  • the present invention provides an organic electroluminescent device, which contains the organic electroluminescent composition as described above.
  • the organic electroluminescent composition is a light-emitting layer (the light-emitting principle of the light-emitting layer is based on the exciplex formed by electron donor molecules and electron acceptor molecules, namely molecules formed by Exciplex Charge transfer between excited states).
  • the organic electroluminescent device further includes a substrate, and an anode layer, an organic light-emitting functional layer, and a cathode layer sequentially formed on the substrate;
  • the organic light-emitting functional layer includes
  • the light-emitting layer as described above may also include any one or a combination of a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer, and an electron injection layer; preferably
  • the electron transport material in the electron transport layer has the same structure as the 1,3,5-triazine compound in the organic electroluminescence composition.
  • the invention provides an application of the organic electroluminescence device in an organic electroluminescence display or an organic electroluminescence illumination light source.
  • the number of the "substituted" can be one or more; when there are more than one, it can be 2, 3 or 4.
  • the “substitution” when the number of the "substitution" is multiple, the “substitution” may be the same or different.
  • the position of "substitution" can be any position unless otherwise specified.
  • the hydrogen or H is a hydrogen element in natural abundance, that is, a mixture of isotopes protium, deuterium and tritium, in which the abundance of protium is 99.98%.
  • the deuterium is D or 2 H, which is also called deuterium.
  • the abundance of deuterium at the deuterium substitution site is greater than 99%.
  • the term "containing” or “including (including)” can be open, semi-closed, and closed. In other words, the term also includes “substantially consisting of” or “consisting of”.
  • C 1 -C 6 alkyl refers to an alkyl group as defined below having a total of 1, 2, 3, 4, 5, or 6 carbon atoms.
  • the total number of carbon atoms in the simplified notation does not include carbons that may be present in the substituents of the group.
  • the numerical range defined in the substituents such as 0 to 4, 1-4, 1 to 3, etc., indicates an integer within the range, for example, 1-6 is 0, 1, 2, 3, 4, 5, 6.
  • halogen means fluorine, chlorine, bromine or iodine.
  • alkyl is meant to include branched and straight-chain chains with the specified number of carbon atoms Saturated aliphatic hydrocarbon group. For example, C 1 ⁇ C 10 . As defined in "C 1 -C 6 alkyl", it includes groups having 1, 2, 3, 4, 5, or 6 carbon atoms in a linear or branched structure.
  • the C 1 ⁇ C 6 alkyl groups are each independently methyl, ethyl, propyl, butyl, pentyl or hexyl; wherein, propyl is C 3 alkyl (including the same Isomers, such as n-propyl or isopropyl); butyl is C 4 alkyl (including isomers, such as n-butyl, sec-butyl, isobutyl or tert-butyl); pentyl is C 5 alkyl (including isomers, such as n-pentyl, 1-methyl-butyl, 1-ethyl-propyl, 2-methyl-1-butyl, 3-methyl-1- butyl, isopentyl, tert-pentyl or neopentyl); for the hexyl group C 6 alkyl group (including isomers, e.g. n-hexyl or isohexyl).
  • aryl refers to a monocyclic or polycyclic group having 6-14 ring atoms and zero heteroatoms provided in the aromatic ring system (E.g., bicyclic or tricyclic) 4n+2 aromatic ring system (e.g., having 6, 10, or 14 shared p electrons in a cyclic array) group ("C 6 ⁇ C 14 aryl) ").
  • aromatic ring system E.g., bicyclic or tricyclic
  • 4n+2 aromatic ring system e.g., having 6, 10, or 14 shared p electrons in a cyclic array
  • Examples of the aforementioned aryl unit include phenyl, naphthyl, phenanthryl, or anthracenyl.
  • heteroaryl refers to having ring carbon atoms and 1-4 ring heteroatoms provided in the aromatic ring system (where each hetero Atoms independently selected from nitrogen, oxygen and sulfur) 5-6 membered monocyclic or polycyclic (for example, bicyclic or tricyclic) 4n+2 aromatic ring system group ("5-6 member Heteroaryl").
  • Heteroaryl groups within the scope of this definition include but are not limited to: acridinyl, carbazolyl, cinnolinyl, quinoxalinyl, pyrazolyl, indolyl, benzotriazolyl, furyl, thienyl , Benzothienyl, benzofuranyl, quinolinyl, isoquinolinyl, oxazolyl, isoxazolyl, indolyl, pyrazinyl, pyridazinyl, pyridinyl, pyrimidinyl, pyrrolyl, Tetrahydroquinoline.
  • part refers to specific fragments or functional groups in a molecule.
  • the chemical moiety is generally considered to be a chemical entity embedded or attached to a molecule.
  • the present invention adopts traditional methods of mass spectrometry and elemental analysis, and the steps and conditions can refer to the conventional operating steps and conditions in the art.
  • the present invention adopts standard nomenclature and standard laboratory procedures and techniques of analytical chemistry, synthetic organic chemistry and optics. In some cases, standard techniques are used for chemical synthesis, chemical analysis, and performance testing of light-emitting devices.
  • the compounds of the present invention may contain unnatural proportions of atomic isotopes on one or more of the atoms constituting the compound.
  • compounds can be labeled with radioisotopes, such as deuterium ( 2 H). All changes in the isotopic composition of the compounds of the present invention, whether radioactive or not, are included in the scope of the present invention.
  • the reagents and raw materials used in the present invention are all commercially available.
  • the positive progress effect of the present invention is that: the substituted 1,3,5-triazine compound represented by formula I provided by the present invention has good electron accepting ability and electron transport ability; and has good thermal stability.
  • Such compounds can be used in the field of organic electroluminescence. It can be used alone as an electron transport layer or hole blocking layer, or combined with an electron donor material to form a composite host material, and used alone in an organic electroluminescent device.
  • This composite host material can be combined with some light-emitting materials (Including phosphorescent and fluorescent materials) Doping constructs the light-emitting layer of organic electroluminescent materials. Therefore, this material can be simultaneously used as a functional material in the light-emitting layer and electron transport layer/hole blocking layer of electroluminescent devices.
  • the electron transport layer and the electron acceptor material in the light-emitting layer belong to the same molecule.
  • the electrons enter the light-emitting layer from the electron transport layer there is no customer service barrier, which is beneficial to reduce the driving voltage and efficiency roll-off of the light-emitting device, and improve the efficiency and life of the device.
  • the molecular ion mass determined by mass spectrometry analysis is: 501.00 (calculated value: 501.20); theoretical element content (%) C 34 H 23 N 5 : C, 81.42; H, 4.62; N, 13.96; measured element content (%): C, 81.25; H, 4.60; N, 14.22.
  • the above analysis results show that the obtained product is the target product.
  • Example 1 According to the synthesis of Example 1, the steps were the same, and the compound 4-formylphenylboronic acid was used instead of the compound 2-formylphenylboronic acid to obtain 0.523 g of a white compound (yield 66.7%).
  • the molecular ion mass determined by mass spectrometry was 501.12 ( Calculated value: 501.20); theoretical element content (%) C 34 H 23 N 5 : C, 81.42; H, 4.62; N, 13.96; measured element content (%): C, 81.37; H, 4.60; N, 14.28 .
  • the above analysis results show that the obtained product is the target product.
  • Example 1 According to the synthesis of Example 1, the steps were the same, and the compound 3-formylphenylboronic acid was used instead of the compound 2-formylphenylboronic acid to obtain 0.632g of a white compound (yield 80.6%).
  • the molecular ion mass determined by mass spectrometry was 501.04( Calculated value: 501.20); theoretical element content (%) C 34 H 23 N 5 : C, 81.42; H, 4.62; N, 13.96; measured element content (%): C, 81.45; H, 4.65; N, 14.02 .
  • the above analysis results show that the obtained product is the target product.
  • the molecular ion mass determined by mass spectrometry analysis is: 501.12 (calculated value: 501.20); theoretical element content (%) C 34 H 23 N 5 : C, 81.42; H, 4.62; N, 13.96; measured element content (%): C, 81.35; H, 4.67; N, 14.03.
  • the above analysis results show that the obtained product is the target product.
  • Example 4 According to the synthesis of Example 4, the steps are the same, and the compound N-(3-bromophenyl)-1,2-phenylenediamine is substituted for the compound N-(4-bromophenyl)-1,2-phenylenediamine to obtain White compound 638 mg (yield 85.0%).
  • the molecular ion mass determined by mass spectrometry analysis is: 501.08 (calculated value: 501.20); theoretical element content (%) C 34 H 23 N 5 : C, 81.42; H, 4.62; N, 13.96; measured element content (%): C, 81.35; H, 4.55; N, 14.12.
  • the above analysis results show that the obtained product is the target product.
  • Example 4 According to the synthesis of Example 4, the steps are the same, and the compound N-(2-bromophenyl)-1,2-phenylenediamine is substituted for the compound N-(4-bromophenyl)-1,2-phenylenediamine to obtain 0.523g of white compound (yield 66.7%), the molecular ion mass determined by mass spectrometry analysis is: 501.32 (calculated value: 501.20); theoretical element content (%) C 34 H 23 N 5 : C, 81.42; H, 4.62; N, 13.96; Measured element content (%): C, 81.38; H, 4.57; N, 14.02. The above analysis results show that the obtained product is the target product.
  • Example 1 According to the synthesis of Example 1, the steps were the same, and the compound N-(3-pyridyl)-1,2-phenylenediamine was used instead of the compound o-aminodiphenylamine to obtain 0.553g of white compound (yield 70.5%), which was confirmed by mass spectrometry
  • the molecular ion mass of is: 502.28 (calculated value: 502.19); theoretical element content (%) C 33 H 22 N 6 : C, 78.87; H, 4.41; N, 16.72, measured element content (%): C, 78.95 ; H, 4.33; N, 16.85.
  • the above analysis results show that the obtained product is the target product.
  • Example 1 According to the synthesis of Example 1, the steps were the same, and the compound N-(4-pyridyl)-1,2-phenylenediamine was used instead of the compound o-aminodiphenylamine to obtain 0.356g of white compound (yield 45.4%), which was confirmed by mass spectrometry
  • the molecular ion mass of is: 502.31 (calculated value: 502.19); theoretical element content (%) C 33 H 22 N 6 : C, 78.87; H, 4.41; N, 16.72, measured element content (%): C, 78.95 ; H, 4.61; N, 16.63.
  • the above analysis results show that the obtained product is the target product.
  • Example 3 According to the synthesis of Example 3, the steps were the same, and the compound N-(3-pyridyl)-1,2-phenylenediamine was used instead of the compound o-aminodiphenylamine to obtain 0.435g of white compound (yield 55.5%), which was confirmed by mass spectrometry
  • the molecular ion mass of is: 502.20 (calculated value: 502.19); theoretical element content (%) C 33 H 22 N 6 : C, 78.87; H, 4.41; N, 16.72, measured element content (%): C, 78.85 ; H, 4.41; N, 16.83.
  • the above analysis results show that the obtained product is the target product.
  • Example 3 According to the synthesis of Example 3, the steps were the same, the compound N-(4-pyridyl)-1,2-phenylenediamine was used instead of the compound o-aminodiphenylamine to obtain 0.398g of white compound (yield 50.8%), which was confirmed by mass spectrometry
  • the molecular ion mass of is: 502.18 (calculated value: 502.19); theoretical element content (%) C 33 H 22 N 6 : C, 78.87; H, 4.41; N, 16.72, measured element content (%): C, 78.88 ; H, 4.49; N, 16.81.
  • the above analysis results show that the obtained product is the target product.
  • Example 2 According to the synthesis of Example 2, the steps are the same, the compound N-(3-pyridyl)-1,2-phenylenediamine is used instead of the compound o-aminodiphenylamine to obtain 0.444g of white compound (yield 56.6%), which is confirmed by mass spectrometry
  • the molecular ion mass of is: 502.08 (calculated value: 502.19); theoretical element content (%) C 33 H 22 N 6 : C, 78.87; H, 4.41; N, 16.72, measured element content (%): C, 78.98 ; H, 4.28; N, 16.77.
  • the above analysis results show that the obtained product is the target product.
  • Example 2 According to the synthesis of Example 2, the steps were the same, and the compound N-(4-pyridyl)-1,2-phenylenediamine was used instead of the compound o-aminodiphenylamine to obtain 0.466g of white compound (yield 59.4%), which was confirmed by mass spectrometry
  • the molecular ion mass of is: 502.18 (calculated value: 502.19); theoretical element content (%) C 33 H 22 N 6 : C, 78.87; H, 4.41; N, 16.72, measured element content (%): C, 78.95 ; H, 4.61; N, 16.83.
  • the above analysis results show that the obtained product is the target product.
  • Example 6 According to the synthesis of Example 6, the steps were the same, and the compound 3-aldehyde pyridine was used instead of the compound benzaldehyde to obtain 0.425 g of a white compound (yield 54.2%).
  • the molecular ion mass determined by mass spectrometry was 502.13 (calculated value: 502.19). );
  • Theoretical element content (%) C 33 H 22 N 6 C, 78.87; H, 4.41; N, 16.72, the measured element content (%): C, 78.89; H, 4.21; N, 16.93.
  • the above analysis results show that the obtained product is the target product.
  • Example 6 According to the synthesis of Example 6, the steps were the same, and the compound 4-aldehyde pyridine was used instead of the compound benzaldehyde to obtain 0.289 g of a white compound (yield 36.9%).
  • the molecular ion mass determined by mass spectrometry was 502.22 (calculated value: 502.29). );
  • Theoretical element content (%) C 33 H 22 N 6 C, 78.87; H, 4.41; N, 16.72, the measured element content (%): C, 78.89; H, 4.22; N, 16.90.
  • the above analysis results show that the obtained product is the target product.
  • Example 5 According to the synthesis of Example 5, the steps were the same, and the compound 3-aldehyde pyridine was used instead of the compound benzaldehyde to obtain 0.333 g of the white compound (yield 42.5%).
  • the mass of the molecular ion determined by mass spectrometry was 502.22 (calculated value: 502.29). );
  • Theoretical element content (%) C 33 H 22 N 6 C, 78.87; H, 4.41; N, 16.72, the measured element content (%): C, 78.86; H, 4.40; N, 16.81.
  • the above analysis results show that the obtained product is the target product.
  • Example 5 According to the synthesis of Example 5, the steps were the same, and the compound 4-aldehyde pyridine was used instead of the compound benzaldehyde to obtain 0.259 g of the white compound (yield 33.0%).
  • the mass of the molecular ion determined by mass spectrometry was: 502.23 (calculated value: 502.29) );
  • Theoretical element content (%) C 33 H 22 N 6 C, 78.87; H, 4.41; N, 16.72, the measured element content (%): C, 78.87; H, 4.51; N, 16.87.
  • the above analysis results show that the obtained product is the target product.
  • Example 4 According to the synthesis of Example 4, the steps were the same, and the compound 3-aldehyde pyridine was used instead of the compound benzaldehyde to obtain 0.295 g of a white compound (yield 37.7%).
  • the molecular ion mass determined by mass spectrometry was 502.15 (calculated value: 502.19). );
  • Theoretical element content (%) C 33 H 22 N 6 C, 78.87; H, 4.41; N, 16.72, the measured element content (%): C, 78.75; H, 4.21; N, 16.73.
  • the above analysis results show that the obtained product is the target product.
  • Example 4 According to the synthesis of Example 4, the steps were the same, and the compound 4-aldehyde pyridine was used instead of the compound benzaldehyde to obtain 0.318 g of a white compound (yield 40.6%).
  • the molecular ion mass determined by mass spectrometry analysis was: 502.18 (calculated value: 502.19) );
  • Theoretical element content (%) C 33 H 22 N 6 C, 78.87; H, 4.41; N, 16.72, the measured element content (%): C, 78.88; H, 4.42; N, 16.84.
  • the above analysis results show that the obtained product is the target product.
  • Example 1 According to the synthesis of Example 1, the steps are the same, and the compound N 1 -(2-fluorophenyl)-1,2-phenylenediamine is used instead of the compound o-aminodiphenylamine to obtain 0.523 g of a white compound (yield 68.2%), mass spectrum
  • the molecular ion mass determined by analysis is: 519.28 (calculated value: 519.19); theoretical element content (%) C 34 H 22 FN 5 : C, 78.60; H, 4.27; F, 3.66; N, 13.48, measured element content ( %): C, 78.55; H, 4.24; F, 3.69; N, 13.41.
  • the above analysis results show that the obtained product is the target product.
  • Example 1 According to the synthesis of Example 1, the steps were the same, and the compound N 1 -(3-fluorophenyl)-1,2-phenylenediamine was used instead of the compound o-aminodiphenylamine to obtain 0.512 g of white compound (yield 65.6%), mass spectrum
  • the molecular ion mass determined by analysis is: 519.33 (calculated value: 519.19); theoretical element content (%) C 34 H 22 FN 5 : C,78.60; H, 4.27; F, 3.66; N, 13.48, measured element content ( %): C, 78.57; H, 4.26; F, 3.71; N, 13.43.
  • the above analysis results show that the obtained product is the target product.
  • Example 1 According to the synthesis of Example 1, the steps were the same, and the compound N 1 -(4-fluorophenyl)-1,2-phenylenediamine was used instead of the o-aminodiphenylamine compound to obtain 0.502 g of a white compound (yield 64.4%), mass spectrum
  • the molecular ion mass determined by analysis is: 519.09 (calculated value: 519.19); theoretical element content (%) C 34 H 22 FN 5 : C, 78.60; H, 4.27; F, 3.66; N, 13.48, measured element content ( %): C, 78.55; H, 4.24; F, 3.69; N, 13.41.
  • the above analysis results show that the obtained product is the target product.
  • Example 3 According to the synthesis of Example 3, the steps were the same, and the compound N 1 -(2-fluorophenyl)-1,2-phenylenediamine was used instead of the o-aminodiphenylamine compound to obtain 0.488 g of the white compound (yield 62.6%).
  • Mass spectrum The molecular ion mass determined by analysis is: 519.29 (calculated value: 519.19); theoretical element content (%) C 34 H 22 FN 5 : C, 78.60; H, 4.27; F, 3.66; N, 13.48, measured element content ( %): C, 78.57; H, 4.23; F, 3.68; N, 13.40.
  • the above analysis results show that the obtained product is the target product.
  • Example 3 According to the synthesis of Example 3, the steps were the same, the compound N 1 -(3-fluorophenyl)-1,2-phenylenediamine was used instead of the compound o-aminodiphenylamine to obtain 0.532g of a white compound (yield 68.2%), mass spectrum
  • the molecular ion mass determined by analysis is: 519.11 (calculated value: 519.19); theoretical element content (%) C 34 H 22 FN 5 : C,78.60; H, 4.27; F, 3.66; N, 13.48, measured element content ( %): C, 78.66; H, 4.34; F, 3.79; N, 13.51.
  • the above analysis results show that the obtained product is the target product.
  • Example 3 According to the synthesis of Example 3, the steps were the same, and the compound N 1 -(4-fluorophenyl)-1,2-phenylenediamine was used instead of the compound o-aminodiphenylamine to obtain 0.449 g of a white compound (yield 57.6%), mass spectrum
  • the molecular ion mass determined by analysis is: 519.05 (calculated value: 519.19); theoretical element content (%) C 34 H 22 FN 5 : C,78.60; H, 4.27; F, 3.66; N, 13.48, measured element content ( %): C, 78.75; H, 4.34; F, 3.60; N, 13.43.
  • the above analysis results show that the obtained product is the target product.
  • Example 2 According to the synthesis of Example 2, the steps are the same, and the compound N 1 -(2-fluorophenyl)-1,2-phenylenediamine is used instead of the compound o-aminodiphenylamine to obtain 0.439 g of a white compound (yield 56.7%), mass spectrum
  • the molecular ion mass determined by analysis is: 519.11 (calculated value: 519.19); theoretical element content (%) C 34 H 22 FN 5 : C,78.60; H, 4.27; F, 3.66; N, 13.48, measured element content ( %): C, 78.55; H, 4.24; F, 3.69; N, 13.41.
  • the above analysis results show that the obtained product is the target product.
  • Example 2 According to the synthesis of Example 2, the steps are the same, the compound N 1 -(3-fluorophenyl)-1,2-phenylenediamine is used instead of the compound o-aminodiphenylamine to obtain 0.429 g of a white compound (yield 55.0%), mass spectrum
  • the molecular ion mass determined by analysis is: 519.13 (calculated value: 519.19); theoretical element content (%) C 34 H 22 FN 5 : C, 78.60; H, 4.27; F, 3.66; N, 13.48, measured element content ( %): C, 78.66; H, 4.34; F, 3.64; N, 13.45.
  • the above analysis results show that the obtained product is the target product.
  • Example 3 According to the synthesis of Example 3, the steps were the same, and the compound N 1 -(4-fluorophenyl)-1,2-phenylenediamine was used instead of the compound o-aminodiphenylamine to obtain 0.563 g of a white compound (yield 72.2%), mass spectrum
  • the molecular ion mass determined by analysis is: 519.22 (calculated value: 519.19); theoretical element content (%) C 34 H 22 FN 5 : C,78.60; H, 4.27; F, 3.66; N, 13.48, measured element content ( %): C, 78.57; H, 4.22; F, 3.67; N, 13.51.
  • the above analysis results show that the obtained product is the target product.
  • Example 1 According to the synthesis of Example 1, the steps were the same, and the compound N 1 -(3,5-difluorophenyl)-1,2-phenylenediamine was used instead of the compound o-aminodiphenylamine to obtain 0.537g of a white compound (yield 66.7%) ), the molecular ion mass determined by mass spectrometry analysis is: 537.28 (calculated value: 537.18); theoretical element content (%) C 34 H 21 F 2 N 5 : C, 75.97; H, 3.94; F, 7.07; N, 13.03 , Measured element content (%): C, 76.07; H, 3.99; F, 7.17; N, 13.08. The above analysis results show that the obtained product is the target product.
  • Example 3 According to the synthesis of Example 3, the steps are the same, the compound N 1 -(3,5-difluorophenyl)-1,2-phenylenediamine is used instead of the compound o-aminodiphenylamine to obtain 0.454g of a white compound (yield 56.2%) ), the molecular ion mass determined by mass spectrometry analysis is: 537.20 (calculated value: 537.18); theoretical element content (%) C 34 H 21 F 2 N 5 : C, 75.97; H, 3.94; F, 7.07; N, 13.03 , Measured element content (%): C, 76.00; H, 4.10; F, 7.07; N, 13.18. The above analysis results show that the obtained product is the target product.
  • Example 2 According to the synthesis of Example 2, the steps were the same, and the compound N 1 -(3,5-difluorophenyl)-1,2-phenylenediamine was used instead of the compound o-aminodiphenylamine to obtain 0.390g of a white compound (yield 48.3%) ), the molecular ion mass determined by mass spectrometry analysis is: 537.09 (calculated value: 537.18); theoretical element content (%) C 34 H 21 F 2 N 5 : C, 75.97; H, 3.94; F, 7.07; N, 13.03 , Measured element content (%): C, 75.99; H, 3.92; F, 7.09; N, 13.13. The above analysis results show that the obtained product is the target product.
  • Example 6 According to the synthesis of Example 6, the steps were the same, and the compound 2-fluorobenzaldehyde was used instead of the compound benzaldehyde to obtain 0.392 g of a white compound (yield 50.2%).
  • the mass of molecular ion determined by mass spectrometry was 519.24 (calculated value: 519.19) );
  • Theoretical element content (%) C 34 H 22 FN 5 C, 78.60; H, 4.27; F, 3.66; N, 13.48, measured element content (%): C, 78.55; H, 4.29; F, 3.69; N, 13.33.
  • the above analysis results show that the obtained product is the target product.
  • Example 5 According to the synthesis of Example 5, the steps were the same, and the compound 2-fluorobenzaldehyde was used instead of the compound benzaldehyde to obtain 0.353 g of a white compound (yield 45.3%).
  • the molecular ion mass determined by mass spectrometry was 519.15 (calculated value: 519.19) );
  • Theoretical element content (%) C 34 H 22 FN 5 C, 78.60; H, 4.27; F, 3.66; N, 13.48, the measured element content (%): C, 78.66; H, 4.22; F, 3.69; N, 13.59.
  • the above analysis results show that the obtained product is the target product.
  • Example 4 According to the synthesis of Example 4, the steps were the same, and the compound 2-fluorobenzaldehyde was substituted for the compound benzaldehyde to obtain 0.357 g of a white compound (yield 45.8%).
  • the mass of molecular ion determined by mass spectrometry was 519.22 (calculated value: 519.19) );
  • Theoretical element content (%) C 34 H 22 FN 5 C, 78.60; H, 4.27; F, 3.66; N, 13.48, measured element content (%): C, 78.59; H, 4.32; F, 3.77; N, 13.61.
  • the above analysis results show that the obtained product is the target product.
  • Example 6 According to the synthesis of Example 6, the steps were the same, and the compound 3-fluorobenzaldehyde was used instead of the compound benzaldehyde to obtain 0.405 g of a white compound (yield 51.9%).
  • the molecular ion mass determined by mass spectrometry was 519.15 (calculated value: 519.19) );
  • Theoretical element content (%) C 34 H 22 FN 5 C, 78.60; H, 4.27; F, 3.66; N, 13.48, measured element content (%): C, 78.62; H, 4.28; F, 3.69; N, 13.59.
  • the above analysis results show that the obtained product is the target product.
  • Example 5 According to the synthesis of Example 5, the steps were the same, and the compound 3-fluorobenzaldehyde was substituted for the compound benzaldehyde to obtain 0.416 g of a white compound (yield 53.3%).
  • the mass of the molecular ion determined by mass spectrometry was 519.28 (calculated value: 519.19) );
  • Theoretical element content (%) C 34 H 22 FN 5 C, 78.60; H, 4.27; F, 3.66; N, 13.48, measured element content (%): C, 78.67; H, 4.42; F, 3.47; N, 13.41.
  • the above analysis results show that the obtained product is the target product.
  • Example 4 According to the synthesis of Example 4, the steps were the same, and the compound 3-fluorobenzaldehyde was used instead of the compound benzaldehyde to obtain 0.523 g of a white compound (yield 66.7%).
  • the molecular ion mass determined by mass spectrometry was 519.22 (calculated value: 519.19) );
  • Theoretical element content (%) C 34 H 22 FN 5 C, 78.60; H, 4.27; F, 3.66; N, 13.48, the measured element content (%): C, 78.57; H, 4.22; F, 3.67; N, 13.51.
  • the above analysis results show that the obtained product is the target product.
  • Example 6 According to the synthesis of Example 6, the steps were the same, and the compound 4-fluorobenzaldehyde was substituted for the compound benzaldehyde to obtain 0.435 g of a white compound (yield 55.8%).
  • the mass of the molecular ion determined by mass spectrometry was 519.25 (calculated value: 519.19) );
  • Theoretical element content (%) C 34 H 22 FN 5 C, 78.60; H, 4.27; F, 3.66; N, 13.48, the measured element content (%): C, 78.57; H, 4.22; F, 3.67; N, 13.51.
  • the above analysis results show that the obtained product is the target product.
  • Example 5 According to the synthesis of Example 5, the steps were the same, and the compound 4-fluorobenzaldehyde was used instead of the compound benzaldehyde to obtain 0.472 g of a white compound (yield 60.5%).
  • the molecular ion mass determined by mass spectrometry was 519.10 (calculated value: 519.19) );
  • Theoretical element content (%) C 34 H 22 FN 5 C, 78.60; H, 4.27; F, 3.66; N, 13.48, measured element content (%): C, 78.58; H, 4.22; F, 3.87; N, 13.51.
  • the above analysis results show that the obtained product is the target product.
  • Example 4 According to the synthesis of Example 4, the steps were the same, and the compound 4-fluorobenzaldehyde was substituted for the compound benzaldehyde to obtain 0.416 g of a white compound (yield 53.4%).
  • the molecular ion mass determined by mass spectrometry was 519.14 (calculated value: 519.19) );
  • Theoretical element content (%) C 34 H 22 FN 5 C, 78.60; H, 4.27; F, 3.66; N, 13.48, the measured element content (%): C, 78.77; H, 4.12; F, 3.87; N, 13.51.
  • the above analysis results show that the obtained product is the target product.
  • Example 6 According to the synthesis of Example 6, the steps were the same, and the compound 3,5-difluorobenzaldehyde was used instead of the compound benzaldehyde to obtain 0.361 g of a white compound (yield 44.9%).
  • the molecular ion mass determined by mass spectrometry was 537.33 (calculated value) Is: 537.18); theoretical element content (%) C 34 H 21 F 2 N 5 : C, 75.97; H, 3.94; F, 7.07; N, 13.03, measured element content (%): C, 76.07; H, 3.99 ; F,7.17; N,13.08.
  • the above analysis results show that the obtained product is the target product.
  • Example 5 According to the synthesis of Example 5, the steps were the same, and the compound 3,5-difluorobenzaldehyde was used instead of the compound benzaldehyde to obtain 0.382g of a white compound (yield 47.5%).
  • the molecular ion mass determined by mass spectrometry was 537.19 (calculated value) Is: 537.18); theoretical element content (%) C 34 H 21 F 2 N 5 : C, 75.97; H, 3.94; F, 7.07; N, 13.03, measured element content (%): C, 75.87; H, 4.12 ; F, 7.07; N, 13.18.
  • the above analysis results show that the obtained product is the target product.
  • Example 4 According to the synthesis of Example 4, the steps are the same, and the compound 3,5-difluorobenzaldehyde is used instead of the compound benzaldehyde to obtain 0.425g of white compound (yield 52.8%).
  • the mass of molecular ion determined by mass spectrometry is 537.09 (calculated value) Is: 537.18); theoretical element content (%) C 34 H 21 F 2 N 5 : C, 75.97; H, 3.94; F, 7.07; N, 13.03, measured element content (%): C, 76.11; H, 3.89 ; F, 7.25; N, 13.18.
  • the above analysis results show that the obtained product is the target product.
  • Example 7 According to the synthesis of Example 7, the steps are the same, and the compound 2-chloro-4,6-bis(4-fluorophenyl)-1,3,5-triazine is used instead of the compound 2-chloro-4,6-diphenyl -1,3,5-triazine, 0.553g of white compound was obtained (yield 51.2%), the molecular ion mass determined by mass spectrometry was 538.25 (calculated value: 538.17); theoretical element content (%) C 33 H 20 F 2 N 6 : C, 73.60; H, 3.74; F, 7.06; N, 15.60, measured element content (%): C, 73.58; H, 3.81; F, 7.16; N, 15.77. The above analysis results show that the obtained product is the target product.
  • Example 8 According to the synthesis of Example 8, the steps are the same, and the compound 2-chloro-4,6-bis(4-fluorophenyl)-1,3,5-triazine is used instead of the compound 2-chloro-4,6-diphenyl -1,3,5-triazine, 0.657g of white compound was obtained (yield 60.8%), the molecular ion mass determined by mass spectrometry analysis was: 538.32 (calculated value: 538.17); theoretical element content (%) C 33 H 20 F 2 N 6 : C, 73.60; H, 3.74; F, 7.06; N, 15.60, measured element content (%): C, 73.49; H, 3.83; F, 7.11; N, 15.53. The above analysis results show that the obtained product is the target product.
  • Example 9 According to the synthesis of Example 9, the steps are the same, and the compound 2-chloro-4,6-bis(4-fluorophenyl)-1,3,5-triazine is used instead of the compound 2-chloro-4,6-diphenyl -1,3,5-triazine, 0.619g of white compound was obtained (yield 57.3%), the molecular ion mass determined by mass spectrometry analysis was: 538.33 (calculated value: 538.17); theoretical element content (%) C 33 H 20 F 2 N 6 : C, 73.60; H, 3.74; F, 7.06; N, 15.60, measured element content (%): C, 73.59; H, 3.77; F, 7.26; N, 15.58. The above analysis results show that the obtained product is the target product.
  • Example 10 According to the synthesis of Example 10, the steps are the same, and the compound 2-chloro-4,6-bis(4-fluorophenyl)-1,3,5-triazine is used instead of the compound 2-chloro-4,6-diphenyl -1,3,5-triazine, 0.511g of white compound was obtained (yield 47.3%), the molecular ion mass determined by mass spectrometry analysis was: 538.09 (calculated value: 538.17); theoretical element content (%) C 33 H 20 F 2 N 6 : C, 73.60; H, 3.74; F, 7.06; N, 15.60, measured element content (%): C, 73.55; H, 3.80; F, 7.14; N, 15.77. The above analysis results show that the obtained product is the target product.
  • Example 11 According to the synthesis of Example 11, the steps are the same, and the compound 2-chloro-4,6-bis(4-fluorophenyl)-1,3,5-triazine is used instead of the compound 2-chloro-4,6-diphenyl -1,3,5-triazine to obtain 0.597g of white compound (yield 55.3%), the molecular ion mass determined by mass spectrometry analysis is: 538.30 (calculated value: 538.17); theoretical element content (%) C 33 H 20 F 2 N 6 : C, 73.60; H, 3.74; F, 7.06; N, 15.60, measured element content (%): C, 73.47; H, 3.59; F, 7.21; N, 15.46. The above analysis results show that the obtained product is the target product.
  • Example 12 According to the synthesis of Example 12, the steps are the same, and the compound 2-chloro-4,6-bis(4-fluorophenyl)-1,3,5-triazine is used instead of the compound 2-chloro-4,6-diphenyl -1,3,5-triazine, 0.517g of white compound was obtained (yield 47.9%), the mass of molecular ion determined by mass spectrometry was 538.22 (calculated value: 538.17); theoretical element content (%) C 33 H 20 F 2 N 6 : C, 73.60; H, 3.74; F, 7.06; N, 15.60, measured element content (%): C, 73.60; H, 3.77; F, 7.16; N, 15.49.
  • the above analysis results show that the obtained product is the target product.
  • the molecular ion mass determined by mass spectrometry analysis is: 693.15 (calculated value: 693.26); theoretical element content (%) C 47 H 31 N 7 : C, 81.36; H, 4.50; N, 14.13; measured element content (%): C, 81.25; H, 4.60; N, 14.22.
  • the above analysis results show that the obtained product is the target product.
  • the molecular ion mass determined by mass spectrometry analysis is: 693.18 (calculated value: 693.26); theoretical element content (%) C 47 H 31 N 7 : C, 81.36; H, 4.50; N, 14.13; measured element content (%): C, 81.50; H, 4.65; N, 14.03.
  • the above analysis results show that the obtained product is the target product.
  • Example 49 According to the synthesis of Example 49, the steps were the same, and the compound N-(3-pyridyl)-1,2-phenylenediamine was used instead of the compound o-aminodiphenylamine to obtain 0.716g of white compound (yield 68.9%), which was confirmed by mass spectrometry
  • the molecular ion mass of is: 695.33 (calculated value: 695.25); theoretical element content (%) C 45 H 29 N 9 : C,77.68; H, 4.20; N, 18.12, measured element content (%): C,77.77 ; H, 4.15; N, 18.35.
  • the above analysis results show that the obtained product is the target product.
  • Example 49 According to the synthesis of Example 49, the steps were the same, the compound N-(4-pyridyl)-1,2-phenylenediamine was used instead of the compound o-aminodiphenylamine to obtain 0.557g of white compound (yield 53.6%), which was confirmed by mass spectrometry
  • the molecular ion mass of is: 695.33 (calculated value: 695.25); theoretical element content (%) C 45 H 29 N 9 : C,77.68; H, 4.20; N, 18.12, measured element content (%): C,77.73 ; H, 4.17; N, 18.19.
  • the above analysis results show that the obtained product is the target product.
  • Example 50 According to the synthesis of Example 50, the steps were the same, and the compound 3-aldehyde pyridine was used instead of the compound benzaldehyde to obtain 0.474 g of a white compound (yield 45.6%).
  • the molecular ion mass determined by mass spectrometry was 695.46 (calculated value: 695.25) );
  • Theoretical element content (%) C 45 H 29 N 9 C, 77.68; H, 4.20; N, 18.12, the measured element content (%): C, 77.70; H, 4.14; N, 18.28.
  • the above analysis results show that the obtained product is the target product.
  • Example 50 According to the synthesis of Example 50, the steps were the same, and the compound 4-aldehyde pyridine was used instead of the compound benzaldehyde to obtain 0.547 g (yield of 52.6%) of a white compound.
  • the molecular ion mass determined by mass spectrometry was 695.24 (calculated value: 695.25) );
  • Theoretical element content (%) C 45 H 29 N 9 C, 77.68; H, 4.20; N, 18.12, the measured element content (%): C, 77.73; H, 4.11; N, 18.20.
  • the above analysis results show that the obtained product is the target product.
  • Example 49 According to the synthesis of Example 49, the steps are the same, using compound N 1 ,N 1 '- ⁇ 5-bromo-1,3-bis(2-fluorophenyl) ⁇ bis(1,2-phenylenediamine) instead of compound N 1 ,N 1 '-(5-bromo-1,3-diphenyl)bis(1,2-phenylenediamine), 0.504g of white compound (yield 46.2%) is obtained, and the molecular ion mass determined by mass spectrometry is : 729.33 (calculated value: 729.25); theoretical element content (%) C 47 H 29 F 2 N 7 : C, 77.35; H, 4.01; F, 5.21; N, 13.44, measured element content (%): C, 77.42; H, 4.07; F, 5.31; N, 13.52.
  • the above analysis results show that the obtained product is the target product.
  • Example 49 According to the synthesis of Example 49, the steps are the same, using compound N 1 ,N 1 '- ⁇ 5-bromo-1,3-bis(2-fluorophenyl) ⁇ bis(1,2-phenylenediamine) instead of compound N 1 ,N 1 '-(5-bromo-1,3-diphenyl)bis(1,2-phenylenediamine), 0.560g of white compound (yield 51.4%) was obtained, and the molecular ion mass determined by mass spectrometry was : 729.11 (calculated value: 729.25); theoretical element content (%) C 47 H 29 F 2 N 7 : C, 77.35; H, 4.01; F, 5.21; N, 13.44, measured element content (%): C, 77.33; H, 4.11; F, 5.23; N, 13.56.
  • the above analysis results show that the obtained product is the target product.
  • Example 49 According to the synthesis of Example 49, the steps are the same, using compound N 1 ,N 1 '- ⁇ 5-bromo-1,3-bis(2-fluorophenyl) ⁇ bis(1,2-phenylenediamine) instead of compound N 1 ,N 1 '-(5-bromo-1,3-diphenyl)bis(1,2-phenylenediamine), 0.597g of white compound (yield 54.8%) was obtained, and the molecular ion mass determined by mass spectrometry was : 729.23 (calculated value: 729.25); theoretical element content (%) C 47 H 29 F 2 N 7 : C, 77.35; H, 4.01; F, 5.21; N, 13.44, measured element content (%): C, 77.51; H, 4.12; F, 5.16; N, 13.50.
  • the above analysis results show that the obtained product is the target product.
  • Example 50 According to the synthesis of Example 50, the steps were the same, and the compound 2-fluorobenzaldehyde was substituted for the compound benzaldehyde to obtain 0.560 g of a white compound (yield 51.4%).
  • the molecular ion mass determined by mass spectrometry was 729.31 (calculated value: 729.25) ); theoretical element content (%) C 47 H 29 F 2 N 7 : C, 77.35; H, 4.01; F, 5.21; N, 13.44, measured element content (%): C, 77.46; H, 4.26; F, 5.22; N, 13.47.
  • the above analysis results show that the obtained product is the target product.
  • Example 50 According to the synthesis of Example 50, the steps were the same, and the compound 3-fluorobenzaldehyde was substituted for the compound benzaldehyde to obtain 0.517 g of a white compound (yield 47.4%).
  • the molecular ion mass determined by mass spectrometry was 729.51 (calculated value: 729.25) );
  • the above analysis results show that the obtained product is the target product.
  • Example 50 According to the synthesis of Example 50, the procedure was the same, and the compound 4-fluorobenzaldehyde was substituted for the compound benzaldehyde to obtain 0.577 g of a white compound (yield 52.8%).
  • the molecular ion mass determined by mass spectrometry was 729.25 (calculated value: 729.25) );
  • the above analysis results show that the obtained product is the target product.
  • Example 49 According to the synthesis of Example 49, the steps are the same, and the compound 2-chloro-4,6-bis(4-fluorophenyl)-1,3,5-triazine is used instead of the compound 2-chloro-4,6-diphenyl -1,3,5-triazine to obtain 0.511 g of a white compound (yield 46.6%).
  • the molecular ion mass determined by mass spectrometry analysis is: 729.50 (calculated value: 729.25); theoretical element content (%) C 47 H 29 F 2 N 7 : C, 77.35; H, 4.01; F, 5.21; N, 13.44, measured element content (%): C, 77.42; H, 3.99; F, 5.21; N, 13.40.
  • the above analysis results show that the obtained product is the target product.
  • Example 50 According to the synthesis of Example 50, the steps are the same, and the compound 2-chloro-4,6-bis(4-fluorophenyl)-1,3,5-triazine is used instead of the compound 2-chloro-4,6-diphenyl -1,3,5-triazine, 0.573g of white compound was obtained (yield 52.3%), the molecular ion mass determined by mass spectrometry analysis was 729.33 (calculated value: 729.25); theoretical element content (%) C 47 H 29 F 2 N 7 : C, 77.35; H, 4.01; F, 5.21; N, 13.44, measured element content (%): C, 77.42; H, 4.12; F, 5.18; N, 13.33.
  • the above analysis results show that the obtained product is the target product.
  • Example 51 According to the synthesis of Example 51, the steps are the same, and the compound 2-chloro-4,6-bis(4-fluorophenyl)-1,3,5-triazine is used instead of the compound 2-chloro-4,6-diphenyl -1,3,5-triazine, 0.502g of white compound was obtained (yield 45.8%), the molecular ion mass determined by mass spectrometry analysis was: 731.17 (calculated value: 731.24); theoretical element content (%) C 45 H 27 F 2 N 9 : C, 73.86; H, 3.72; F, 5.19; N, 17.23, measured element content (%): C, 73.93; H, 3.88; F, 5.21; N, 17.25. The above analysis results show that the obtained product is the target product.
  • Example 52 According to the synthesis of Example 52, the steps are the same, and the compound 2-chloro-4,6-bis(4-fluorophenyl)-1,3,5-triazine is used instead of the compound 2-chloro-4,6-diphenyl -1,3,5-triazine, 0.505g of white compound was obtained (yield 46.1%), the molecular ion mass determined by mass spectrometry analysis was: 731.11 (calculated value: 731.24); theoretical element content (%) C 45 H 27 F 2 N 9 : C, 73.86; H, 3.72; F, 5.19; N, 17.23, measured element content (%): C, 73.90; H, 3.88; F, 5.22; N, 17.31. The above analysis results show that the obtained product is the target product.
  • Example 53 According to the synthesis of Example 53, the steps are the same, and the compound 2-chloro-4,6-bis(4-fluorophenyl)-1,3,5-triazine is used instead of the compound 2-chloro-4,6-diphenyl -1,3,5-triazine, 0.523g of white compound was obtained (yield 66.7%), the molecular ion mass determined by mass spectrometry was 731.24 (calculated value: 731.24); theoretical element content (%) C 45 H 27 F 2 N 9 : C, 73.86; H, 3.72; F, 5.19; N, 17.23, measured element content (%): C, 73.86; H, 3.72; F, 5.19; N, 17.23.
  • the above analysis results show that the obtained product is the target product.
  • Example 54 According to the synthesis of Example 54, the steps are the same, and the compound 2-chloro-4,6-bis(4-fluorophenyl)-1,3,5-triazine is used instead of the compound 2-chloro-4,6-diphenyl -1,3,5-triazine to obtain 0.771g of white compound (yield 52.8%), the molecular ion mass determined by mass spectrometry analysis is: 731.33 (calculated value: 731.24); theoretical element content (%) C 45 H 27 F 2 N 9 : C, 73.86; H, 3.72; F, 5.19; N, 17.23, measured element content (%): C, 73.96H, 3.88; F, 5.21; N, 17.25.
  • the above analysis results show that the obtained product is the target product.
  • Example 55 According to the synthesis of Example 55, the steps are the same, and the compound 2-chloro-4,6-bis(4-fluorophenyl)-1,3,5-triazine is used instead of the compound 2-chloro-4,6-diphenyl -1,3,5-triazine, 0.744g white compound was obtained (yield 48.6%), the molecular ion mass determined by mass spectrometry analysis was 765.12 (calculated value: 765.23); theoretical element content (%) C 47 H 27 F 4 N 7 : C, 73.72; H, 3.55; F, 9.92; N, 12.80, measured element content (%): C, 73.68; H, 3.46; F, 9.80; N, 12.79. The above analysis results show that the obtained product is the target product.
  • Example 56 According to the synthesis of Example 56, the steps are the same, and the compound 2-chloro-4,6-bis(4-fluorophenyl)-1,3,5-triazine is used instead of the compound 2-chloro-4,6-diphenyl -1,3,5-triazine, 0.635g of white compound was obtained (yield 41.5%), the molecular ion mass determined by mass spectrometry analysis was 765.23 (calculated value: 765.23); theoretical element content (%) C 47 H 27 F 4 N 7 : C, 73.72; H, 3.55; F, 9.92; N, 12.80, measured element content (%): C, 73.68; H, 3.66; F, 9.81; N, 12.77. The above analysis results show that the obtained product is the target product.
  • Example 57 According to the synthesis of Example 57, the steps are the same, and the compound 2-chloro-4,6-bis(4-fluorophenyl)-1,3,5-triazine is used instead of the compound 2-chloro-4,6-diphenyl -1,3,5-triazine, 0.786g of white compound was obtained (yield 51.4%), the molecular ion mass determined by mass spectrometry analysis was 765.20 (calculated value: 765.23); theoretical element content (%) C 47 H 27 F 4 N 7 : C, 73.72; H, 3.55; F, 9.92; N, 12.80, measured element content (%): C, 73.68; H, 3.47; F, 9.88; N, 12.76. The above analysis results show that the obtained product is the target product.
  • Example 58 According to the synthesis of Example 58, the steps are the same, and the compound 2-chloro-4,6-bis(4-fluorophenyl)-1,3,5-triazine is used instead of the compound 2-chloro-4,6-diphenyl -1,3,5-triazine, 0.770g of white compound was obtained (yield 50.3%), the molecular ion mass determined by mass spectrometry was 765.12 (calculated value: 765.23); theoretical element content (%) C 47 H 27 F 4 N 7 : C, 73.72; H, 3.55; F, 9.92; N, 12.80, measured element content (%): C, 73.86; H, 3.39; F, 9.79; N, 12.77.
  • the above analysis results show that the obtained product is the target product.
  • Example 59 According to the synthesis of Example 59, the steps are the same, and the compound 2-chloro-4,6-bis(4-fluorophenyl)-1,3,5-triazine is used instead of the compound 2-chloro-4,6-diphenyl -1,3,5-triazine, 0.762g of white compound (yield 49.8%) was obtained.
  • the molecular ion mass determined by mass spectrometry analysis was 765.34 (calculated value: 765.23); theoretical element content (%) C 47 H 27 F 4 N 7 : C, 73.72; H, 3.55; F, 9.92; N, 12.80, measured element content (%): C, 73.62; H, 3.57; F, 9.88; N, 12.93.
  • the above analysis results show that the obtained product is the target product.
  • Example 60 According to the synthesis of Example 60, the steps are the same, and the compound 2-chloro-4,6-bis(4-fluorophenyl)-1,3,5-triazine is used instead of the compound 2-chloro-4,6-diphenyl -1,3,5-triazine, 0.808g of white compound was obtained (yield 52.8%), the molecular ion mass determined by mass spectrometry analysis was 765.44 (calculated value: 765.23); theoretical element content (%) C 47 H 27 F 4 N 7 : C, 73.72; H, 3.55; F, 9.92; N, 12.80, measured element content (%): C, 73.68; H, 3.63; F, 9.94; N, 12.77. The above analysis results show that the obtained product is the target product.
  • Example 29 According to the synthesis of Example 29, the steps are the same, and the compound 2-chloro-4,6-bis(4-fluorophenyl)-1,3,5-triazine is used instead of the compound 2-chloro-4,6-diphenyl -1,3,5-triazine, 0.606g of white compound was obtained (yield 52.9%), the molecular ion mass determined by mass spectrometry analysis was: 573.22 (calculated value: 573.16); theoretical element content (%) C 34 H 19 F 4 N 5 : C, 71.20; H, 3.34; F, 13.25; N, 12.21, measured element content (%): C, 71.24; H, 3.33; F, 13.36N, 12.31. The above analysis results show that the obtained product is the target product.
  • Example 1 According to the synthesis of Example 1, the steps were the same, and the compound N 1 -(3-trifluoromethylphenyl)-1,2-phenylenediamine was used instead of the compound o-aminodiphenylamine to obtain 0.498g of a white compound (yield 58.3%) ), the molecular ion mass determined by mass spectrometry analysis is: 569.32 (calculated value: 569.18); theoretical element content (%) C 35 H 22 F 3 N 5 : C, 73.80; H, 3.89; F, 10.01; N, 12.30 Measured element content (%): C, 73.77; H, 3.92; F, 10.11; N, 12.35. The above analysis results show that the obtained product is the target product.
  • Example 3 According to the synthesis of Example 3, the steps were the same, and the compound N 1 -(3-trifluoromethylphenyl)-1,2-phenylenediamine was used instead of the compound o-aminodiphenylamine to obtain 0.532g of a white compound (yield 53.2%) ), the molecular ion mass determined by mass spectrometry analysis is: 569.12 (calculated value: 569.18); theoretical element content (%) C 35 H 22 F 3 N 5 : C, 73.80; H, 3.89; F, 10.01; N, 12.30 Measured element content (%): C, 73.87; H, 3.91; F, 10.10; N, 12.31. The above analysis results show that the obtained product is the target product.
  • Example 2 According to the synthesis of Example 2, the steps were the same, and the compound N 1 -(3-trifluoromethylphenyl)-1,2-phenylenediamine was used instead of the compound o-aminodiphenylamine to obtain 0.527 g of a white compound (yield 61.7%) ), the molecular ion mass determined by mass spectrometry analysis is: 569.33 (calculated value: 569.18); theoretical element content (%) C 35 H 22 F 3 N 5 : C, 73.80; H, 3.89; F, 10.01; N, 12.30 Measured element content (%): C, 73.91; H, 3.88; F, 10.06; N, 12.27. The above analysis results show that the obtained product is the target product.
  • Example 1 According to the synthesis of Example 1, the steps are the same, and the compound N 1 -(3,5-bis(trifluoromethyl)phenyl)-1,2-phenylenediamine is substituted for the compound o-aminodiphenylamine to obtain 0.524g of a white compound (Yield 54.8%), the molecular ion mass determined by mass spectrometry analysis is: 637.22 (calculated value: 637.17); theoretical element content (%) C 36 H 21 F 6 N 5 : C, 67.82; H, 3.32; F, 17.88; N, 10.98, measured element content (%): C, 67.77; H, 3.35; F, 17.90; N, 10.87.
  • the above analysis results show that the obtained product is the target product.
  • Example 3 According to the synthesis of Example 3, the steps are the same, the compound N 1 -(3,5-bis(trifluoromethyl)phenyl)-1,2-phenylenediamine is substituted for the compound o-aminodiphenylamine to obtain 0.524g of a white compound (Yield 54.8%), the molecular ion mass determined by mass spectrometry analysis is: 637.20 (calculated value: 637.17); theoretical element content (%) C 36 H 21 F 6 N 5 : C, 67.82; H, 3.32; F, 17.88; N, 10.98, measured element content (%): C, 67.87; H, 3.45; F, 17.82; N, 10.97.
  • the above analysis results show that the obtained product is the target product.
  • Example 2 According to the synthesis of Example 2, the steps are the same, and the compound N 1 -(3,5-bis(trifluoromethyl)phenyl)-1,2-phenylenediamine is substituted for the compound o-aminodiphenylamine to obtain 0.585g of a white compound (Yield 61.2%), the molecular ion mass determined by mass spectrometry analysis is: 637.15 (calculated value: 637.17); theoretical element content (%) C 36 H 21 F 6 N 5 : C, 67.82; H, 3.32; F, 17.88; N, 10.98, measured element content (%): C, 67.87; H, 3.36; F, 17.89; N, 10.94.
  • the above analysis results show that the obtained product is the target product.
  • Example 4 According to the synthesis of Example 4, the steps were the same, and the compound 3-trifluoromethylbenzaldehyde was used instead of the compound benzaldehyde to obtain 0.500 g of a white compound (yield 58.6%).
  • the molecular ion mass determined by mass spectrometry was 569.19 (calculated value) Is: 569.18); theoretical element content (%) C 35 H 22 F 3 N 5 : C, 73.80; H, 3.89; F, 10.01; N, 12.30; measured element content (%): C, 73.88; H, 3.83 ; F, 10.14; N, 12.34.
  • the above analysis results show that the obtained product is the target product.
  • Example 6 According to the synthesis of Example 6, the steps are the same, and the compound 3-trifluoromethylbenzaldehyde is used instead of the compound benzaldehyde to obtain 0.523g of a white compound (yield 66.7%).
  • the molecular ion mass determined by mass spectrometry is 569.33 (calculated value) Is: 569.18); theoretical element content (%) C 35 H 22 F 3 N 5 : C, 73.80; H, 3.89; F, 10.01; N, 12.30; measured element content (%): C, 73.91; H, 3.88 ; F, 10.06; N, 12.27.
  • the above analysis results show that the obtained product is the target product.
  • Example 5 According to the synthesis of Example 5, the steps were the same, and the compound 3-trifluoromethylbenzaldehyde was used instead of the compound benzaldehyde to obtain 0.516g of a white compound (yield 60.4%).
  • the mass of the molecular ion determined by mass spectrometry was 569.23 (calculated value) Is: 569.18); theoretical element content (%) C 35 H 22 F 3 N 5 : C, 73.80; H, 3.89; F, 10.01; N, 12.30; measured element content (%): C, 73.82; H, 3.85 ; F, 10.14; N, 12.33.
  • the above analysis results show that the obtained product is the target product.
  • Example 5 According to the synthesis of Example 5, the steps are the same, and the compound 3,5-bis(trifluoromethyl)benzaldehyde is used instead of the compound benzaldehyde to obtain 0.454g of white compound (yield 47.5%).
  • the mass of the molecular ion determined by mass spectrometry is : 637.21 (calculated value: 637.17); theoretical element content (%) C 36 H 21 F 6 N 5 : C, 67.82; H, 3.32; F, 17.88; N, 10.98, measured element content (%): C, 67.85; H, 3.30; F, 17.90; N, 10.92.
  • the above analysis results show that the obtained product is the target product.
  • Example 9 According to the synthesis of Example 9, the steps are the same, and the compound 2-chloro-4,6-bis(4-trifluoromethylphenyl)-1,3,5-triazine is used instead of the compound 2-chloro-4,6- Diphenyl-1,3,5-triazine, 0.532g of white compound (yield 55.6%) was obtained.
  • the molecular ion mass determined by mass spectrometry analysis was 638.18 (calculated value: 638.17); theoretical element content (%) C 35 H 20 F 6 N 6 : C, 65.83; H, 3.16; F, 17.85; N, 13.16, measured element content (%): C, 65.85; H, 3.10; F, 17.86; N, 13.12.
  • the above analysis results show that the obtained product is the target product.
  • Example 49 According to the synthesis of Example 49, the steps were the same, and the compound 2-chloro-4,6-bis(4-trifluoromethylphenyl)-1,3,5-triazine was used instead of the compound 2-chloro-4,6- Diphenyl-1,3,5-triazine, 0.511g of white compound (yield 46.6%) was obtained.
  • the molecular ion mass determined by mass spectrometry analysis was 829.24 (calculated value: 829.24); theoretical element content (%) C 49 H 29 F 6 N 7 : C, 70.92; H, 3.52; F, 13.74; N, 11.82, measured element content (%): C, 70.95; H, 3.54; F, 13.77; N, 11.90.
  • the above analysis results show that the obtained product is the target product.
  • Example 51 According to the synthesis of Example 51, the steps were the same, and the compound 2-chloro-4,6-bis(4-trifluoromethylphenyl)-1,3,5-triazine was used instead of the compound 2-chloro-4,6- Diphenyl-1,3,5-triazine, 0.419g of white compound was obtained (yield 33.6%), the molecular ion mass determined by mass spectrometry analysis was: 831.24 (calculated value: 831.23); theoretical element content (%) C 47 H 27 F 6 N 9 : C, 67.87; H, 3.27; F, 13.70; N, 15.16, measured element content (%): C, 67.86; H, 3.29; F, 13.72; N, 15.14. The above analysis results show that the obtained product is the target product.
  • Example 53 According to the synthesis of Example 53, the steps were the same, and the compound 2-chloro-4,6-bis(4-trifluoromethylphenyl)-1,3,5-triazine was used instead of the compound 2-chloro-4,6- Diphenyl-1,3,5-triazine, 0.446g of white compound was obtained (yield 35.8%), the molecular ion mass determined by mass spectrometry analysis was 831.20 (calculated value: 831.23); theoretical element content (%) C 47 H 27 F 6 N 9 : C, 67.87; H, 3.27; F, 13.70; N, 15.16, measured element content (%): C, 67.89; H, 3.33; F, 13.74; N, 15.18.
  • the above analysis results show that the obtained product is the target product.
  • Example 56 According to the synthesis of Example 56, the steps are the same, 2-chloro-4,6-bis(4-trifluoromethylphenyl)-1,3,5-triazine instead of the compound 2-chloro-4,6-diphenyl Yl-1,3,5-triazine, N-(3-trifluoromethylphenyl)-1,2-phenylenediamine instead of compound N-(3-fluorophenyl)-1,2-phenylenediamine , Obtain 0.583g of white compound (yield 40.3%), the molecular ion mass determined by mass spectrometry analysis is: 965.21 (calculated value: 965.21); theoretical element content (%) C 51 H 27 F 12 N 7 : C, 63.42; H, 2.82; F, 23.61; N, 10.15, measured element content (%): C, 63.45; H, 2.90; F, 23.63; N, 10.22. The above analysis results show that the obtained product is the target
  • Example 29 According to the synthesis of Example 29, the steps are the same, and the compound 2-chloro-4,6-bis(4-trifluoromethylphenyl)-1,3,5-triazine is used instead of the compound 2-chloro-4,6- Diphenyl-1,3,5-triazine, N-(3,5-bis(trifluoromethyl)phenyl)-1,2-phenylenediamine instead of compound N-(3-fluorophenyl)- 1,2-Phenylenediamine, 0.594g of white compound (yield 51.2%) was obtained, the molecular ion mass determined by mass spectrometry analysis was: 773.18 (calculated value: 773.14); theoretical element content (%) C 38 H 19 F 12 N 5 : C, 59.00; H, 2.48; F, 29.47; N, 9.05, measured element content (%): C, 59.08; H, 2.53; F, 29.55; N, 9.12. The above analysis results show that the obtained product is
  • Example 49 According to the synthesis of Example 49, the steps are the same, using the compound N 1 , N 1 '- ⁇ 5-bromo-1,3-bis(2-trifluoromethylphenyl) ⁇ bis(1,2-phenylenediamine) Instead of compound N 1 , N 1 '(5-bromo-1,3-diphenyl)bis(1,2-phenylenediamine), 0.599g of white compound (yield 48.2%) was obtained, and the molecular ion was confirmed by mass spectrometry.
  • the above analysis results show that the obtained product is the target product.
  • Example 59 According to the synthesis of Example 59, the steps are the same, and the compound 2-chloro-4,6-bis(4-fluorophenyl)-1,3,5-triazine is used instead of the compound 2-chloro-4,6-diphenyl -1,3,5-triazine, the compound 3-trifluoromethylbenzaldehyde was substituted for the compound benzaldehyde to obtain 0.640g of a white compound (yield 44.2%).
  • the molecular ion mass determined by mass spectrometry was 965.23 (calculated value) Is: 965.21); theoretical element content (%) C 51 H 27 F 12 N 7 : C, 63.42; H, 2.82; F, 23.61; N, 10.15, measured element content (%): C, 63.48; H, 2.90 ; F, 23.66; N, 10.21.
  • the above analysis results show that the obtained product is the target product.
  • Example 19 According to the synthesis of Example 19, the steps were the same, and the compound N 1 -(2-isopropylphenyl)benzene-1,2-diamine was used instead of the compound N 1 -(2-fluorophenyl)benzene-1,2- Diamine, 0.523 g of white compound was obtained (yield 37.9%).
  • the molecular ion mass determined by mass spectrometry analysis is: 543.26 (calculated value: 543.24); theoretical element content (%) C 37 H 29 N 5 : C, 81.74; H, 5.38; N, 12.88; measured element content (%): C, 81.75; H, 5.37; N, 12.88.
  • the above analysis results show that the obtained product is the target product.
  • Example 20 According to the synthesis of Example 20, the steps are the same, and the compound N 1 -(3-isopropylphenyl)benzene-1,2-diamine is used instead of the compound N 1 -(3-fluorophenyl)benzene-1,2- Diamine, 0.503 g of a white compound was obtained (yield 36.9%).
  • the molecular ion mass determined by mass spectrometry analysis is: 543.27 (calculated value: 543.24); theoretical element content (%) C 37 H 29 N 5 : C, 81.74; H, 5.38; N, 12.88; measured element content (%): C, 81.75; H, 5.37; N, 12.88.
  • the above analysis results show that the obtained product is the target product.
  • Example 21 According to the synthesis of Example 21, the steps are the same, and the compound N 1 -(4-isopropylphenyl)benzene-1,2-diamine is substituted for the compound N 1 -(4-fluorophenyl)benzene-1,2- Diamine, 0.423 g of a white compound was obtained (yield 37.0%).
  • the molecular ion mass determined by mass spectrometry analysis is: 543.27 (calculated value: 543.24); theoretical element content (%) C 37 H 29 N 5 : C, 81.74; H, 5.38; N, 12.88; measured element content (%): C, 81.75; H, 5.37; N, 12.88.
  • the above analysis results show that the obtained product is the target product.
  • Example 22 According to the synthesis of Example 22, the steps were the same, and the compound N 1 -(2-isopropylphenyl)benzene-1,2-diamine was used instead of the compound N 1 -(2-fluorophenyl)benzene-1,2- Diamine, 0.523 g of white compound was obtained (yield 37.9%).
  • the molecular ion mass determined by mass spectrometry analysis is: 543.26 (calculated value: 543.24); theoretical element content (%) C 37 H 29 N 5 : C, 81.74; H, 5.38; N, 12.88; measured element content (%): C, 81.75; H, 5.37; N, 12.88.
  • the above analysis results show that the obtained product is the target product.
  • Example 23 According to the synthesis of Example 23, the steps were the same, and the compound N 1 -(3-isopropylphenyl)benzene-1,2-diamine was used instead of the compound N 1 -(3-fluorophenyl)benzene-1,2- Diamine, 0.578 g of a white compound was obtained (yield 33.9%).
  • the molecular ion mass determined by mass spectrometry analysis is: 543.27 (calculated value: 543.24); theoretical element content (%) C 37 H 29 N 5 : C, 81.74; H, 5.38; N, 12.88; measured element content (%): C, 81.75; H, 5.37; N, 12.88.
  • the above analysis results show that the obtained product is the target product.
  • Example 24 According to the synthesis of Example 24, the steps were the same, and the compound N 1 -(4-isopropylphenyl)benzene-1,2-diamine was used instead of the compound N 1 -(4-fluorophenyl)benzene-1,2- Diamine, 0.513 g of a white compound was obtained (yield 36.9%).
  • the molecular ion mass determined by mass spectrometry analysis is: 543.29 (calculated value: 543.24); theoretical element content (%) C 37 H 29 N 5 : C, 81.74; H, 5.38; N, 12.88; measured element content (%): C, 81.75; H, 5.37; N, 12.88.
  • the above analysis results show that the obtained product is the target product.
  • Example 25 According to the synthesis of Example 25, the steps are the same, and the compound N 1 -(2-isopropylphenyl)benzene-1,2-diamine is used instead of the compound N 1 -(2-fluorophenyl)benzene-1,2- Diamine, 0.523 g of white compound was obtained (yield 37.9%).
  • the molecular ion mass determined by mass spectrometry analysis is: 543.27 (calculated value: 543.24); theoretical element content (%) C 37 H 29 N 5 : C, 81.74; H, 5.38; N, 12.88; measured element content (%): C, 81.75; H, 5.37; N, 12.88.
  • the above analysis results show that the obtained product is the target product.
  • Example 26 According to the synthesis of Example 26, the steps are the same, and the compound N 1 -(3-isopropylphenyl)benzene-1,2-diamine is substituted for the compound N 1 -(3-fluorophenyl)benzene-1,2- Diamine, 0.423 g of a white compound was obtained (yield 37.7%).
  • the molecular ion mass determined by mass spectrometry analysis is: 543.29 (calculated value: 543.24); theoretical element content (%) C 37 H 29 N 5 : C, 81.74; H, 5.38; N, 12.88; measured element content (%): C, 81.75; H, 5.37; N, 12.88.
  • the above analysis results show that the obtained product is the target product.
  • Example 27 According to the synthesis of Example 27, the steps were the same, and the compound N 1 -(4-isopropylphenyl)benzene-1,2-diamine was used instead of the compound N 1 -(4-fluorophenyl)benzene-1,2- Diamine, 0.523 g of a white compound (yield 32.9%) was obtained.
  • the molecular ion mass determined by mass spectrometry analysis is: 543.28 (calculated value: 543.24); theoretical element content (%) C 37 H 29 N 5 : C, 81.74; H, 5.38; N, 12.88; measured element content (%): C, 81.75; H, 5.37; N, 12.88.
  • the above analysis results show that the obtained product is the target product.
  • Example 28 According to the synthesis of Example 28, the steps are the same, and the compound N 1 -(3,5-diisopropylphenyl)benzene-1,2-diamine is used instead of the compound N 1 -(3,5-fluorophenyl)benzene -1,2-diamine, 0.523 g of a white compound was obtained (yield 37.9%).
  • the molecular ion mass determined by mass spectrometry analysis is: 585.26 (calculated value: 585.29); theoretical element content (%) C 40 H 35 N 5 : C, 82.02; H, 6.02; N, 11.96; measured element content (%): C, 82.05; H, 6.07; N, 11.88.
  • the above analysis results show that the obtained product is the target product.
  • Example 29 According to the synthesis of Example 29, the steps are the same, and the compound N 1 -(3,5-diisopropylphenyl)benzene-1,2-diamine is used instead of the compound N 1 -(3,5-fluorophenyl)benzene -1,2-diamine, 0.520 g of white compound was obtained (yield 35.9%).
  • the molecular ion mass determined by mass spectrometry analysis is: 585.26 (calculated value: 585.29); theoretical element content (%) C 40 H 35 N 5 : C, 82.02; H, 6.02; N, 11.96; measured element content (%): C, 82.05; H, 6.07; N, 11.88.
  • the above analysis results show that the obtained product is the target product.
  • Example 30 According to the synthesis of Example 30, the steps are the same, and the compound N 1 -(3,5-diisopropylphenyl)benzene-1,2-diamine is used instead of the compound N 1 -(3,5-fluorophenyl)benzene -1,2-diamine, 0.527 g of white compound was obtained (yield 35.9%).
  • the molecular ion mass determined by mass spectrometry analysis is: 585.27 (calculated value: 585.29); theoretical element content (%) C 40 H 35 N 5 : C, 82.02; H, 6.02; N, 11.96; measured element content (%): C, 82.05; H, 6.07; N, 11.88.
  • the above analysis results show that the obtained product is the target product.
  • Example 31 According to the synthesis of Example 31, the procedure was the same, and the compound 2-isopropylbenzaldehyde was used instead of the compound 2-fluorobenzaldehyde to obtain 0.507 g of a white compound (yield 37.8%).
  • the molecular ion mass determined by mass spectrometry analysis is: 543.27 (calculated value: 543.24); theoretical element content (%) C 37 H 29 N 5 : C, 81.74; H, 5.38; N, 12.88; measured element content (%): C, 81.75; H, 5.37; N, 12.88.
  • the above analysis results show that the obtained product is the target product.
  • Example 32 According to the synthesis of Example 32, the procedure was the same, and the compound 2-isopropylbenzaldehyde was substituted for the compound 2-fluorobenzaldehyde to obtain 0.523 g of a white compound (yield 37.6%).
  • the molecular ion mass determined by mass spectrometry analysis is: 543.27 (calculated value: 543.24); theoretical element content (%) C 37 H 29 N 5 : C, 81.74; H, 5.38; N, 12.88; measured element content (%): C, 81.75; H, 5.37; N, 12.88.
  • the above analysis results show that the obtained product is the target product.
  • Example 33 According to the synthesis of Example 33, the procedure was the same, and the compound 2-isopropylbenzaldehyde was used instead of the compound 2-fluorobenzaldehyde to obtain 0.523 g of a white compound (yield 30.9%).
  • the molecular ion mass determined by mass spectrometry analysis is: 543.26 (calculated value: 543.24); theoretical element content (%) C 37 H 29 N 5 : C, 81.74; H, 5.38; N, 12.88; measured element content (%): C, 81.75; H, 5.37; N, 12.88.
  • the above analysis results show that the obtained product is the target product.
  • Example 34 According to the synthesis of Example 34, the steps were the same, and the compound 3-isopropylbenzaldehyde was used instead of the compound 3-fluorobenzaldehyde to obtain 0.523 g of a white compound (yield 37.9%).
  • the molecular ion mass determined by mass spectrometry analysis is: 543.21 (calculated value: 543.24); theoretical element content (%) C 37 H 29 N 5 : C, 81.74; H, 5.38; N, 12.88; measured element content (%): C, 81.75; H, 5.37; N, 12.88.
  • the above analysis results show that the obtained product is the target product.
  • Example 35 According to the synthesis of Example 35, the steps were the same, and the compound 3-isopropylbenzaldehyde was used instead of the compound 3-fluorobenzaldehyde to obtain 0.423 g of a white compound (yield 37.2%).
  • the molecular ion mass determined by mass spectrometry analysis is: 543.29 (calculated value: 543.24); theoretical element content (%) C 37 H 29 N 5 : C, 81.74; H, 5.38; N, 12.88; measured element content (%): C, 81.75; H, 5.37; N, 12.88.
  • the above analysis results show that the obtained product is the target product.
  • Example 36 According to the synthesis of Example 36, the procedure was the same, and the compound 3-isopropylbenzaldehyde was substituted for the compound 3-fluorobenzaldehyde to obtain 0.479 g of a white compound (yield 37.1%).
  • the molecular ion mass determined by mass spectrometry analysis is: 543.23 (calculated value: 543.24); theoretical element content (%) C 37 H 29 N 5 : C, 81.74; H, 5.38; N, 12.88; measured element content (%): C, 81.75; H, 5.37; N, 12.88.
  • the above analysis results show that the obtained product is the target product.
  • Example 37 According to the synthesis of Example 37, the procedure was the same, and the compound 4-isopropylbenzaldehyde was used instead of the compound 4-fluorobenzaldehyde to obtain 0.523 g of a white compound (yield 37.9%).
  • the molecular ion mass determined by mass spectrometry analysis is: 543.28 (calculated value: 543.24); theoretical element content (%) C 37 H 29 N 5 : C, 81.74; H, 5.38; N, 12.88; measured element content (%): C, 81.75; H, 5.37; N, 12.88.
  • the above analysis results show that the obtained product is the target product.
  • Example 38 According to the synthesis of Example 38, the procedure was the same, and the compound 4-isopropylbenzaldehyde was used instead of the compound 4-fluorobenzaldehyde to obtain 0.523 g of a white compound (yield 37.9%).
  • the molecular ion mass determined by mass spectrometry analysis is: 543.22 (calculated value: 543.24); theoretical element content (%) C 37 H 29 N 5 : C, 81.74; H, 5.38; N, 12.88; measured element content (%): C, 81.75; H, 5.37; N, 12.88.
  • the above analysis results show that the obtained product is the target product.
  • Example 39 According to the synthesis of Example 39, the procedure was the same, and the compound 4-isopropylbenzaldehyde was substituted for the compound 4-fluorobenzaldehyde to obtain 0.521 g of a white compound (yield 37.4%).
  • the molecular ion mass determined by mass spectrometry analysis is: 543.26 (calculated value: 543.24); theoretical element content (%) C 37 H 29 N 5 : C, 81.74; H, 5.38; N, 12.88; measured element content (%): C, 81.75; H, 5.37; N, 12.88.
  • the above analysis results show that the obtained product is the target product.
  • Example 40 According to the synthesis of Example 40, the steps were the same, and the compound 3,5-diisopropylbenzaldehyde was substituted for the compound 3,5-difluorobenzaldehyde to obtain 0.514 g of a white compound (yield 31.4%).
  • the molecular ion mass determined by mass spectrometry analysis is: 585.26 (calculated value: 585.29); theoretical element content (%) C 40 H 35 N 5 : C, 82.02; H, 6.02; N, 11.96; measured element content (%): C, 82.05; H, 6.07; N, 11.88.
  • the above analysis results show that the obtained product is the target product.
  • Example 41 According to the synthesis of Example 41, the steps are the same, and the compound 3,5-diisopropylbenzaldehyde is used instead of the compound 3,5-difluorobenzaldehyde to obtain 0.520 g of a white compound (yield 30.5%).
  • the molecular ion mass determined by mass spectrometry analysis is: 585.27 (calculated value: 585.29); theoretical element content (%) C 40 H 35 N 5 : C, 82.02; H, 6.02; N, 11.96; measured element content (%): C, 82.05; H, 6.07; N, 11.88.
  • the above analysis results show that the obtained product is the target product.
  • Example 42 According to the synthesis of Example 42, the steps were the same, and the compound 3,5-diisopropylbenzaldehyde was used instead of the compound 3,5-difluorobenzaldehyde to obtain 0.523 g of a white compound (yield 37.9%).
  • the molecular ion mass determined by mass spectrometry analysis is: 585.27 (calculated value: 585.29); theoretical element content (%) C 40 H 35 N 5 : C, 82.02; H, 6.02; N, 11.96; measured element content (%): C, 82.05; H, 6.07; N, 11.88.
  • the above analysis results show that the obtained product is the target product.
  • Example 55 According to the synthesis of Example 55, the steps were the same, and the compound N 1 -(2-isopropylphenyl)benzene-1,2-diamine was used instead of the compound N 1 -(2-fluorophenyl)benzene-1,2- Diamine, 0.529 g of a white compound was obtained (yield 27.2%).
  • the molecular ion mass determined by mass spectrometry analysis is: 777.30 (calculated value: 777.36); theoretical element content (%) C 53 H 43 N 7 : C, 81.83; H, 5.57; N, 12.60; measured element content (%): C, 81.85; H, 5.57; N, 12.58.
  • the above analysis results show that the obtained product is the target product.
  • Example 56 According to the synthesis of Example 56, the steps are the same, and the compound N 1 -(3-isopropylphenyl)benzene-1,2-diamine is used instead of the compound N 1 -(3-fluorophenyl)benzene-1,2- Diamine, 0.579 g of a white compound (yield 24.2%) was obtained.
  • the molecular ion mass determined by mass spectrometry analysis is: 777.34 (calculated value: 777.36); theoretical element content (%) C 53 H 43 N 7 : C, 81.83; H, 5.57; N, 12.60; measured element content (%): C, 81.85; H, 5.57; N, 12.58.
  • the above analysis results show that the obtained product is the target product.
  • Example 57 According to the synthesis of Example 57, the steps are the same, and the compound N 1 -(4-isopropylphenyl)benzene-1,2-diamine is used instead of the compound N 1 -(4-fluorophenyl)benzene-1,2- Diamine, 0.529 g of a white compound was obtained (yield 27.2%).
  • the molecular ion mass determined by mass spectrometry analysis is: 777.30 (calculated value: 777.36); theoretical element content (%) C 53 H 43 N 7 : C, 81.83; H, 5.57; N, 12.60; measured element content (%): C, 81.85; H, 5.57; N, 12.58.
  • the above analysis results show that the obtained product is the target product.
  • Example 58 According to the synthesis of Example 58, the procedure was the same, and the compound 2-isopropylbenzaldehyde was used instead of the compound 2-fluorobenzaldehyde to obtain 0.529 g of a white compound (yield 27.2%).
  • the molecular ion mass determined by mass spectrometry analysis is: 777.32 (calculated value: 777.36); theoretical element content (%) C 53 H 43 N 7 : C, 81.83; H, 5.57; N, 12.60; measured element content (%): C, 81.85; H, 5.57; N, 12.58.
  • the above analysis results show that the obtained product is the target product.
  • Example 59 According to the synthesis of Example 59, the steps were the same, and the compound 3-isopropylbenzaldehyde was used instead of the compound 3-fluorobenzaldehyde to obtain 0.529 g of a white compound (yield 27.2%).
  • the molecular ion mass determined by mass spectrometry analysis is: 777.30 (calculated value: 777.36); theoretical element content (%) C 53 H 43 N 7 : C, 81.83; H, 5.57; N, 12.60; measured element content (%): C, 81.85; H, 5.57; N, 12.58.
  • the above analysis results show that the obtained product is the target product.
  • Example 60 According to the synthesis of Example 60, the steps were the same, and the compound 4-isopropylbenzaldehyde was used instead of the compound 4-fluorobenzaldehyde to obtain 0.629 g of a white compound (yield 29.2%).
  • the molecular ion mass determined by mass spectrometry analysis is: 777.32 (calculated value: 777.36); theoretical element content (%) C 53 H 43 N 7 : C, 81.83; H, 5.57; N, 12.60; measured element content (%): C, 81.85; H, 5.57; N, 12.58.
  • the above analysis results show that the obtained product is the target product.
  • Example 61 According to the synthesis of Example 61, the steps were the same, and the compound 2-chloro-4,6-bis(4-isopropylphenyl)-1,3,5-triazine was used instead of the compound 2-chloro-4,6-di (4-Fluorophenyl)-1,3,5-triazine, 0.529 g of a white compound (yield 27.2%) was obtained.
  • the molecular ion mass determined by mass spectrometry analysis is: 777.30 (calculated value: 777.36); theoretical element content (%) C 53 H 43 N 7 : C, 81.83; H, 5.57; N, 12.60; measured element content (%): C, 81.85; H, 5.57; N, 12.58.
  • the above analysis results show that the obtained product is the target product.
  • Example 62 According to the synthesis of Example 62, the steps were the same, and the compound 2-chloro-4,6-bis(4-isopropylphenyl)-1,3,5-triazine was used instead of the compound 2-chloro-4,6-di (4-Fluorophenyl)-1,3,5-triazine, 0.509 g of a white compound (yield 27.7%) was obtained.
  • the molecular ion mass determined by mass spectrometry analysis is: 777.32 (calculated value: 777.36); theoretical element content (%) C 53 H 43 N 7 : C, 81.83; H, 5.57; N, 12.60; measured element content (%): C, 81.85; H, 5.57; N, 12.58.
  • the above analysis results show that the obtained product is the target product.
  • Example 63 According to the synthesis of Example 63, the steps were the same, and the compound 2-chloro-4,6-bis(4-isopropylphenyl)-1,3,5-triazine was used instead of the compound 2-chloro-4,6-di (4-Fluorophenyl)-1,3,5-triazine, 0.529 g of a white compound (yield 27.2%) was obtained.
  • the molecular ion mass determined by mass spectrometry analysis is: 779.30 (calculated value: 779.35); theoretical element content (%) C 51 H 41 N 9 : C, 78.54; H, 5.30; N, 16.16; measured element content (%): C, 78.55; H, 5.37; N, 16.08.
  • the above analysis results show that the obtained product is the target product.
  • Example 64 According to the synthesis of Example 64, the steps were the same, and the compound 2-chloro-4,6-bis(4-isopropylphenyl)-1,3,5-triazine was used instead of the compound 2-chloro-4,6-di (4-Fluorophenyl)-1,3,5-triazine, 0.428 g of a white compound (yield 25.6%) was obtained.
  • the molecular ion mass determined by mass spectrometry analysis is: 779.32 (calculated value: 779.35); theoretical element content (%) C 51 H 41 N 9 : C, 78.54; H, 5.30; N, 16.16; measured element content (%): C, 78.55; H, 5.37; N, 16.08.
  • the above analysis results show that the obtained product is the target product.
  • Example 65 According to the synthesis of Example 65, the steps were the same, and the compound 2-chloro-4,6-bis(4-isopropylphenyl)-1,3,5-triazine was used instead of the compound 2-chloro-4,6-di (4-Fluorophenyl)-1,3,5-triazine, 0.529 g of a white compound (yield 27.2%) was obtained.
  • the molecular ion mass determined by mass spectrometry analysis is: 779.30 (calculated value: 779.35); theoretical element content (%) C 51 H 41 N 9 : C, 78.54; H, 5.30; N, 16.16; measured element content (%): C, 78.55; H, 5.37; N, 16.08.
  • the above analysis results show that the obtained product is the target product.
  • Example 66 According to the synthesis of Example 66, the steps were the same, and the compound 2-chloro-4,6-bis(4-isopropylphenyl)-1,3,5-triazine was used instead of the compound 2-chloro-4,6-di (4-Fluorophenyl)-1,3,5-triazine, 0.427 g of a white compound (yield 25.7%) was obtained.
  • the molecular ion mass determined by mass spectrometry analysis is: 779.37 (calculated value: 779.35); theoretical element content (%) C 51 H 41 N 9 : C, 78.54; H, 5.30; N, 16.16; measured element content (%): C, 78.55; H, 5.37; N, 16.08.
  • the above analysis results show that the obtained product is the target product.
  • Example 67 According to the synthesis of Example 67, the steps were the same, and the compound 2-chloro-4,6-bis(4-isopropylphenyl)-1,3,5-triazine was used instead of the compound 2-chloro-4,6-di (4-Fluorophenyl)-1,3,5-triazine, using compound N 1 -(2-isopropylphenyl)benzene-1,2-diamine instead of compound N 1 -(2-fluorophenyl) ) Benzene-1,2-diamine gave 0.529 g of white compound (yield 27.2%).
  • the molecular ion mass determined by mass spectrometry analysis is: 861.42 (calculated value: 861.45); theoretical element content (%): C 59 H 55 N 7 : C, 82.20; H, 6.43; N, 11.37; measured element content (%) : C, 82.25; H, 6.47; N, 11.28.
  • the above analysis results show that the obtained product is the target product.
  • Example 68 According to the synthesis of Example 68, the steps are the same, and the compound 2-chloro-4,6-bis(4-isopropylphenyl)-1,3,5-triazine is used instead of the compound 2-chloro-4,6-di (4-Fluorophenyl)-1,3,5-triazine, using compound N 1 -(3-isopropylphenyl)benzene-1,2-diamine instead of compound N 1 -(3-fluorophenyl) ) Benzene-1,2-diamine to obtain 0.565 g of a white compound (yield 28.2%).
  • the molecular ion mass determined by mass spectrometry analysis is: 861.41 (calculated value: 861.45); theoretical element content (%): C 59 H 55 N 7 : C, 82.20; H, 6.43; N, 11.37; measured element content (%) : C, 82.25; H, 6.48; N, 11.27.
  • the above analysis results show that the obtained product is the target product.
  • Example 69 According to the synthesis of Example 69, the steps were the same, and the compound 2-chloro-4,6-bis(4-isopropylphenyl)-1,3,5-triazine was used instead of the compound 2-chloro-4,6-di (4-Fluorophenyl)-1,3,5-triazine, using compound N 1 -(4-isopropylphenyl)benzene-1,2-diamine instead of compound N 1 -(4-fluorophenyl) ) Benzene-1,2-diamine gave 0.529 g of white compound (yield 27.2%).
  • the molecular ion mass determined by mass spectrometry analysis is: 861.41 (calculated value: 861.45); theoretical element content (%): C 59 H 55 N 7 : C, 82.20; H, 6.43; N, 11.37; measured element content (%) : C, 82.25; H, 6.47; N, 11.28.
  • the above analysis results show that the obtained product is the target product.
  • Example 70 According to the synthesis of Example 70, the steps were the same, and the compound 2-chloro-4,6-bis(4-isopropylphenyl)-1,3,5-triazine was used instead of the compound 2-chloro-4,6-di (4-Fluorophenyl)-1,3,5-triazine, using the compound 2-isopropyl-benzaldehyde instead of the compound 2-fluorobenzaldehyde to obtain 0.417 g of a white compound (yield 28.2%).
  • the molecular ion mass determined by mass spectrometry analysis is: 861.42 (calculated value: 861.45); theoretical element content (%): C 59 H 55 N 7 : C, 82.20; H, 6.43; N, 11.37; measured element content (%) : C, 82.25; H, 6.47; N, 11.28.
  • the above analysis results show that the obtained product is the target product.
  • Example 71 According to the synthesis of Example 71, the steps were the same, and the compound 2-chloro-4,6-bis(4-isopropylphenyl)-1,3,5-triazine was used instead of the compound 2-chloro-4,6-di (4-Fluorophenyl)-1,3,5-triazine, using the compound 3-isopropylbenzaldehyde instead of the compound 3-fluoro-benzaldehyde to obtain 0.629 g of a white compound (yield 25.8%).
  • the molecular ion mass determined by mass spectrometry analysis is: 861.47 (calculated value: 861.45); theoretical element content (%): C 59 H 55 N 7 : C, 82.20; H, 6.43; N, 11.37; measured element content (%) : C, 82.25; H, 6.47; N, 11.28.
  • the above analysis results show that the obtained product is the target product.
  • Example 72 According to the synthesis of Example 72, the steps were the same, and the compound 2-chloro-4,6-bis(4-isopropylphenyl)-1,3,5-triazine was used instead of the compound 2-chloro-4,6-di (4-Fluorophenyl)-1,3,5-triazine, using the compound 4-isopropylbenzaldehyde instead of the compound 4-fluorobenzaldehyde to obtain 0.529 g of a white compound (yield 27.2%).
  • the molecular ion mass determined by mass spectrometry analysis is: 861.42 (calculated value: 861.45); theoretical element content (%): C 59 H 55 N 7 : C, 82.20; H, 6.43; N, 11.37; measured element content (%) : C, 82.25; H, 6.47; N, 11.28.
  • the above analysis results show that the obtained product is the target product.
  • Example 73 According to the synthesis of Example 73, the steps were the same, and the compound 2-chloro-4,6-bis(4-isopropylphenyl)-1,3,5-triazine was used instead of the compound 2-chloro-4,6-di (4-Fluorophenyl)-1,3,5-triazine, using compound N 1 -(3,5-diisopropylphenyl)benzene-1,2-diamine instead of compound N 1 -(3, 5-difluorophenyl)benzene-1,2-diamine gave 0.417 g of a white compound (yield 28.3%).
  • the molecular ion mass determined by mass spectrometry analysis is: 669.42 (calculated value: 669.38); theoretical element content (%): C 46 H 47 N 5 : C, 82.47; H, 7.07; N, 10.45; measured element content (%) : C, 82.45; H, 7.07; N, 10.48.
  • the above analysis results show that the obtained product is the target product.
  • Example 55 According to the synthesis of Example 55, the steps were the same, and the compound N 1 -(2-methylphenyl)benzene-1,2-diamine was used instead of the compound N 1 -(2-fluorophenyl)benzene-1,2-diamine. Amine, 0.509 g of a white compound was obtained (yield 27.7%).
  • the molecular ion mass determined by mass spectrometry analysis is: 721.32 (calculated value: 721.30); theoretical element content (%) C 49 H 35 N 7 : C, 81.53; H, 4.89; N, 13.58; measured element content (%): C, 81.55; H, 4.87; N, 13.58.
  • the above analysis results show that the obtained product is the target product.
  • Example 56 According to the synthesis of Example 56, the steps are the same, and the compound N 1 -(3-methylphenyl)benzene-1,2-diamine is used instead of the compound N 1 -(3-fluorophenyl)benzene-1,2-diamine Amine, 0.644 g of a white compound was obtained (yield 25.9%).
  • the molecular ion mass determined by mass spectrometry analysis is: 721.31 (calculated value: 721.30); theoretical element content (%) C 49 H 35 N 7 : C, 81.53; H, 4.89; N, 13.58; measured element content (%): C, 81.55; H, 4.87; N, 13.58.
  • the above analysis results show that the obtained product is the target product.
  • Example 57 According to the synthesis of Example 57, the steps are the same, and the compound N 1 -(4-methylphenyl)benzene-1,2-diamine is used instead of the compound N 1 -(4-fluorophenyl)benzene-1,2-diamine.
  • Amine, 0.519 g of a white compound was obtained (yield 27.7%).
  • the molecular ion mass determined by mass spectrometry analysis is: 721.32 (calculated value: 721.30); theoretical element content (%) C 49 H 35 N 7 : C, 81.53; H, 4.89; N, 13.58; measured element content (%): C, 81.55; H, 4.87; N, 13.58.
  • the above analysis results show that the obtained product is the target product.
  • Example 58 According to the synthesis of Example 58, the procedure was the same, and the compound 2-methylbenzaldehyde was substituted for the compound 2-fluorobenzaldehyde to obtain 0.479 g of a white compound (yield 25.7%).
  • the molecular ion mass determined by mass spectrometry analysis is: 721.37 (calculated value: 721.30); theoretical element content (%) C 49 H 35 N 7 : C, 81.53; H, 4.89; N, 13.58; measured element content (%): C, 81.55; H, 4.87; N, 13.58.
  • the above analysis results show that the obtained product is the target product.
  • Example 59 According to the synthesis of Example 59, the procedure was the same, and the compound 3-methylbenzaldehyde was used instead of the compound 3-fluorobenzaldehyde to obtain 0.509 g of a white compound (yield 27.5%).
  • the molecular ion mass determined by mass spectrometry analysis is: 721.32 (calculated value: 721.30); theoretical element content (%) C 49 H 35 N 7 : C, 81.53; H, 4.89; N, 13.58; measured element content (%): C, 81.55; H, 4.87; N, 13.58.
  • the above analysis results show that the obtained product is the target product.
  • Example 60 According to the synthesis of Example 60, the steps were the same, and the compound 4-methylbenzaldehyde was substituted for the compound 4-fluorobenzaldehyde to obtain 0.578 g of a white compound (yield 23.8%).
  • the molecular ion mass determined by mass spectrometry analysis is: 721.32 (calculated value: 721.30); theoretical element content (%) C 49 H 35 N 7 : C, 81.53; H, 4.89; N, 13.58; measured element content (%): C, 81.55; H, 4.87; N, 13.58.
  • the above analysis results show that the obtained product is the target product.
  • Example 61 According to the synthesis of Example 61, the steps were the same, and the compound 2-chloro-4,6-bis(4-methylphenyl)-1,3,5-triazine was used instead of the compound 2-chloro-4,6-bis( 4-fluorophenyl)-1,3,5-triazine gave 0.529 g of a white compound (yield 27.2%).
  • the molecular ion mass determined by mass spectrometry analysis is: 721.32 (calculated value: 721.30); theoretical element content (%) C 49 H 35 N 7 : C, 81.53; H, 4.89; N, 13.58; measured element content (%): C, 81.55; H, 4.87; N, 13.58.
  • the above analysis results show that the obtained product is the target product.
  • Example 62 According to the synthesis of Example 62, the steps were the same, and the compound 2-chloro-4,6-bis(4-methylphenyl)-1,3,5-triazine was used instead of the compound 2-chloro-4,6-bis( 4-fluorophenyl)-1,3,5-triazine gave 0.479 g of a white compound (yield 25.4%).
  • the molecular ion mass determined by mass spectrometry analysis is: 721.30 (calculated value: 721.30); theoretical element content (%) C 49 H 35 N 7 : C, 81.53; H, 4.89; N, 13.58; measured element content (%): C, 81.55; H, 4.87; N, 13.58.
  • the above analysis results show that the obtained product is the target product.
  • Example 63 According to the synthesis of Example 63, the steps were the same, and the compound 2-chloro-4,6-bis(4-methylphenyl)-1,3,5-triazine was used instead of the compound 2-chloro-4,6-bis( 4-fluorophenyl)-1,3,5-triazine, 0.529 g of a white compound was obtained (yield 27.2%).
  • the molecular ion mass determined by mass spectrometry analysis is: 723.30 (calculated value: 723.29); theoretical element content (%) C 47 H 33 N 9 : C, 77.99; H, 4.60; N, 17.42; measured element content (%): C, 77.95; H, 4.67; N, 17.38.
  • the above analysis results show that the obtained product is the target product.
  • Example 64 According to the synthesis of Example 64, the steps were the same, and the compound 2-chloro-4,6-bis(4-methylphenyl)-1,3,5-triazine was used instead of the compound 2-chloro-4,6-bis( 4-fluorophenyl)-1,3,5-triazine, 0.439 g of a white compound was obtained (yield 26.2%).
  • the molecular ion mass determined by mass spectrometry analysis is: 723.31 (calculated value: 723.29); theoretical element content (%) C 47 H 33 N 9 : C, 77.99; H, 4.60; N, 17.42; measured element content (%): C, 77.95; H, 4.67; N, 17.38.
  • the above analysis results show that the obtained product is the target product.
  • Example 65 According to the synthesis of Example 65, the steps were the same, and the compound 2-chloro-4,6-bis(4-methylphenyl)-1,3,5-triazine was used instead of the compound 2-chloro-4,6-bis( 4-fluorophenyl)-1,3,5-triazine to obtain 0.529 g of a white compound (yield 27.1%).
  • the molecular ion mass determined by mass spectrometry analysis is: 723.30 (calculated value: 723.29); theoretical element content (%) C 47 H 33 N 9 : C, 77.99; H, 4.60; N, 17.42; measured element content (%): C, 77.95; H, 4.67; N, 17.38.
  • the above analysis results show that the obtained product is the target product.
  • Example 66 According to the synthesis of Example 66, the steps were the same, and the compound 2-chloro-4,6-bis(4-methylphenyl)-1,3,5-triazine was used instead of the compound 2-chloro-4,6-bis( 4-fluorophenyl)-1,3,5-triazine, 0.671 g of a white compound was obtained (yield 28.3%).
  • the molecular ion mass determined by mass spectrometry analysis is: 723.30 (calculated value: 723.29); theoretical element content (%) C 47 H 33 N 9 : C, 77.99; H, 4.60; N, 17.42; measured element content (%): C, 77.95; H, 4.67; N, 17.38.
  • the above analysis results show that the obtained product is the target product.
  • Example 67 According to the synthesis of Example 67, the steps were the same, and the compound 2-chloro-4,6-bis(4-methylphenyl)-1,3,5-triazine was used instead of the compound 2-chloro-4,6-bis( 4-fluorophenyl)-1,3,5-triazine, using compound N 1 -(2-methylphenyl)benzene-1,2-diamine instead of compound N 1 -(2-fluorophenyl)benzene -1,2-Diamine to obtain 0.529 g of a white compound (yield 27.2%).
  • the molecular ion mass determined by mass spectrometry analysis is: 749.36 (calculated value: 749.33); theoretical element content (%) C 51 H 39 N 7 : C, 81.68; H, 5.24; N, 13.07; measured element content (%): C, 81.65; H, 5.27; N, 13.08.
  • the above analysis results show that the obtained product is the target product.
  • Example 68 According to the synthesis of Example 68, the steps were the same, and the compound 2-chloro-4,6-bis(4-methylphenyl)-1,3,5-triazine was used instead of the compound 2-chloro-4,6-bis( 4-fluorophenyl)-1,3,5-triazine, using compound N 1 -(3-methylphenyl)benzene-1,2-diamine instead of compound N 1 -(3-fluorophenyl)benzene -1,2-Diamine to obtain 0.679 g of a white compound (yield 29.7%).
  • the molecular ion mass determined by mass spectrometry analysis is: 749.32 (calculated value: 749.33); theoretical element content (%) C 51 H 39 N 7 : C, 81.68; H, 5.24; N, 13.07; measured element content (%): C, 81.65; H, 5.27; N, 13.08.
  • the above analysis results show that the obtained product is the target product.
  • Example 69 According to the synthesis of Example 69, the steps were the same, and the compound 2-chloro-4,6-bis(4-methylphenyl)-1,3,5-triazine was used instead of the compound 2-chloro-4,6-bis( 4-fluorophenyl)-1,3,5-triazine, using compound N 1 -(4-methylphenyl)benzene-1,2-diamine instead of compound N 1 -(4-fluorophenyl)benzene -1,2-Diamine to obtain 0.508 g of a white compound (yield 24.7%).
  • the molecular ion mass determined by mass spectrometry analysis is: 749.31 (calculated value: 749.33); theoretical element content (%) C 51 H 39 N 7 : C, 81.68; H, 5.24; N, 13.07; measured element content (%): C, 81.65; H, 5.27; N, 13.08.
  • the above analysis results show that the obtained product is the target product.
  • Example 70 According to the synthesis of Example 70, the steps were the same, and the compound 2-chloro-4,6-bis(4-methylphenyl)-1,3,5-triazine was used instead of the compound 2-chloro-4,6-bis( 4-fluorophenyl)-1,3,5-triazine, using the compound 2-methylbenzaldehyde instead of the compound 2-fluorobenzaldehyde to obtain 0.679 g of a white compound (yield 29.7%).
  • the molecular ion mass determined by mass spectrometry analysis is: 749.31 (calculated value: 749.33); theoretical element content (%) C 51 H 39 N 7 : C, 81.68; H, 5.24; N, 13.07; measured element content (%): C, 81.65; H, 5.27; N, 13.08.
  • the above analysis results show that the obtained product is the target product.
  • Example 71 According to the synthesis of Example 71, the steps were the same, and the compound 2-chloro-4,6-bis(4-methylphenyl)-1,3,5-triazine was used instead of the compound 2-chloro-4,6-bis( 4-fluorophenyl)-1,3,5-triazine, the compound 3-methylbenzaldehyde was substituted for the compound 3-fluorobenzaldehyde to obtain 0.577 g of a white compound (yield 26.5%).
  • the molecular ion mass determined by mass spectrometry analysis is: 749.37 (calculated value: 749.33); theoretical element content (%) C 51 H 39 N 7 : C, 81.68; H, 5.24; N, 13.07; measured element content (%): C, 81.65; H, 5.27; N, 13.08.
  • the above analysis results show that the obtained product is the target product.
  • Example 72 According to the synthesis of Example 72, the steps were the same, and the compound 2-chloro-4,6-bis(4-methylphenyl)-1,3,5-triazine was used instead of the compound 2-chloro-4,6-bis( 4-fluorophenyl)-1,3,5-triazine, using the compound 4-methylbenzaldehyde instead of the compound 4-fluorobenzaldehyde to obtain 0.792 g of a white compound (yield 23.7%).
  • the molecular ion mass determined by mass spectrometry analysis is: 749.31 (calculated value: 749.33); theoretical element content (%) C 51 H 39 N 7 : C, 81.68; H, 5.24; N, 13.07; measured element content (%): C, 81.65; H, 5.27; N, 13.08.
  • the above analysis results show that the obtained product is the target product.
  • Example 73 According to the synthesis of Example 73, the steps were the same, and the compound 2-chloro-4,6-bis(4-methylphenyl)-1,3,5-triazine was used instead of the compound 2-chloro-4,6-bis( 4-fluorophenyl)-1,3,5-triazine, using compound N 1 -(3,5-dimethylphenyl)benzene-1,2-diamine instead of compound N 1 -(3,5- Difluorophenyl)benzene-1,2-diamine gave 0.679 g of a white compound (yield 29.7%).
  • the molecular ion mass determined by mass spectrometry analysis is: 557.29 (calculated value: 557.26); theoretical element content (%) C 38 H 31 N 5 : C, 81.84; H, 5.60; N, 12.56; measured element content (%): C, 81.85; H, 5.67; N, 12.48.
  • the above analysis results show that the obtained product is the target product.
  • Example 1 According to the synthesis of Example 1, the steps are the same, the compound N 1 -([1,1'-biphenyl]-2-yl)benzene-1,2-diamine is substituted for the compound o-aminodiphenylamine to obtain 0.435g of a white compound (Yield 31.3%).
  • the molecular ion mass determined by mass spectrometry analysis is: 577.25 (calculated value: 577.23); theoretical element content (%) C 40 H 27 N 5 : C, 83.17; H, 4.71; N, 12.12; measured element content (%): C, 83.18; H, 4.72; N, 12.10.
  • the above analysis results show that the obtained product is the target product.
  • Example 2 According to the synthesis of Example 2, the steps are the same, and the compound N 1 -([1,1'-biphenyl]-2-yl)benzene-1,2-diamine is substituted for the compound o-aminodiphenylamine to obtain 0.467g of a white compound (Yield 31.6%).
  • the molecular ion mass determined by mass spectrometry analysis is: 577.28 (calculated value: 577.23); theoretical element content (%) C 40 H 27 N 5 : C, 83.17; H, 4.71; N, 12.12; measured element content (%): C, 83.18; H, 4.72; N, 12.10.
  • the above analysis results show that the obtained product is the target product.
  • Example 3 According to the synthesis of Example 3, the steps are the same, the compound N 1 -([1,1'-biphenyl]-2-yl)benzene-1,2-diamine is substituted for the compound o-aminodiphenylamine to obtain 0.438 g of a white compound (Yield 32.7%).
  • the molecular ion mass determined by mass spectrometry analysis is: 577.29 (calculated value: 577.23); theoretical element content (%) C 40 H 27 N 5 : C, 83.17; H, 4.71; N, 12.12; measured element content (%): C, 83.18; H, 4.72; N, 12.10.
  • the above analysis results show that the obtained product is the target product.
  • Example 4 According to the synthesis of Example 4, the steps were the same, and the compound [1,1'-biphenyl]-2-carbaldehyde was used instead of the compound benzaldehyde to obtain 0.503 g of a white compound (yield 35.4%).
  • the molecular ion mass determined by mass spectrometry analysis is: 577.32 (calculated value: 577.23); theoretical element content (%) C 40 H 27 N 5 : C, 83.17; H, 4.71; N, 12.12; measured element content (%): C, 83.18; H, 4.72; N, 12.10.
  • the above analysis results show that the obtained product is the target product.
  • Example 5 According to the synthesis of Example 5, the steps were the same, and the compound [1,1'-biphenyl]-2-carbaldehyde was used instead of the compound benzaldehyde to obtain 0.468 g of a white compound (yield 30.3%).
  • the molecular ion mass determined by mass spectrometry analysis is: 577.31 (calculated value: 577.23); theoretical element content (%) C 40 H 27 N 5 : C, 83.17; H, 4.71; N, 12.12; measured element content (%): C, 83.18; H, 4.72; N, 12.10.
  • the above analysis results show that the obtained product is the target product.
  • Example 6 According to the synthesis of Example 6, the steps were the same, and the compound [1,1'-biphenyl]-2-carbaldehyde was used instead of the compound benzaldehyde to obtain 0.538 g of a white compound (yield 38.3%).
  • the molecular ion mass determined by mass spectrometry analysis is: 577.30 (calculated value: 577.23); theoretical element content (%) C 40 H 27 N 5 : C, 83.17; H, 4.71; N, 12.12; measured element content (%): C, 83.18; H, 4.72; N, 12.10.
  • the above analysis results show that the obtained product is the target product.
  • Example 1 According to the synthesis of Example 1, the steps are the same, the compound N 1 -([1,1'-biphenyl]-3-yl)benzene-1,2-diamine is substituted for the compound o-aminodiphenylamine to obtain 0.492g of a white compound (Yield 34.6%).
  • the molecular ion mass determined by mass spectrometry analysis is: 577.28 (calculated value: 577.23); theoretical element content (%) C 40 H 27 N 5 : C, 83.17; H, 4.71; N, 12.12; measured element content (%): C, 83.18; H, 4.72; N, 12.10.
  • the above analysis results show that the obtained product is the target product.
  • Example 2 According to the synthesis of Example 2, the steps are the same, the compound N 1 -([1,1'-biphenyl]-3-yl)benzene-1,2-diamine is substituted for the compound o-aminodiphenylamine to obtain 0.448g of a white compound (Yield 32.8%).
  • the molecular ion mass determined by mass spectrometry analysis is: 577.28 (calculated value: 577.23); theoretical element content (%) C 40 H 27 N 5 : C, 83.17; H, 4.71; N, 12.12; measured element content (%): C, 83.18; H, 4.72; N, 12.10.
  • the above analysis results show that the obtained product is the target product.
  • Example 3 According to the synthesis of Example 3, the steps are the same, the compound N 1 -([1,1'-biphenyl]-3-yl)benzene-1,2-diamine is substituted for the compound o-aminodiphenylamine to obtain 0.523g of a white compound (Yield 31.2%).
  • the molecular ion mass determined by mass spectrometry analysis is: 577.21 (calculated value: 577.23); theoretical element content (%) C 40 H 27 N 5 : C, 83.17; H, 4.71; N, 12.12; measured element content (%): C, 83.18; H, 4.72; N, 12.10.
  • the above analysis results show that the obtained product is the target product.
  • Example 4 According to the synthesis of Example 4, the steps were the same, and the compound [1,1'-biphenyl]-3-carbaldehyde was substituted for the compound benzaldehyde to obtain 0.495 g of a white compound (yield 33.1%).
  • the molecular ion mass determined by mass spectrometry analysis is: 577.20 (calculated value: 577.23); theoretical element content (%) C 40 H 27 N 5 : C, 83.17; H, 4.71; N, 12.12; measured element content (%): C, 83.18; H, 4.72; N, 12.10.
  • the above analysis results show that the obtained product is the target product.
  • Example 5 According to the synthesis of Example 5, the steps were the same, and the compound [1,1'-biphenyl]-3-carbaldehyde was used instead of the compound benzaldehyde to obtain 0.441 g of a white compound (yield 32.1%).
  • the molecular ion mass determined by mass spectrometry analysis is: 577.28 (calculated value: 577.23); theoretical element content (%) C 40 H 27 N 5 : C, 83.17; H, 4.71; N, 12.12; measured element content (%): C, 83.18; H, 4.72; N, 12.10.
  • the above analysis results show that the obtained product is the target product.
  • Example 6 According to the synthesis of Example 6, the steps are the same, using [1,1'-biphenyl]-3-carbaldehyde instead of the compound benzaldehyde to obtain 0.438 g of a white compound (yield 32.4%).
  • the molecular ion mass determined by mass spectrometry analysis is: 577.25 (calculated value: 577.23); theoretical element content (%) C 40 H 27 N 5 : C, 83.17; H, 4.71; N, 12.12; measured element content (%): C, 83.18; H, 4.72; N, 12.10.
  • the above analysis results show that the obtained product is the target product.
  • Example 1 According to the synthesis of Example 1, the steps are the same, and the compound N 1 -([1,1'-biphenyl]-4-yl)benzene-1,2-diamine is substituted for the compound o-aminodiphenylamine to obtain 0.413g of a white compound (Yield 35.6%).
  • the molecular ion mass determined by mass spectrometry analysis is: 577.30 (calculated value: 577.23); theoretical element content (%) C 40 H 27 N 5 : C, 83.17; H, 4.71; N, 12.12; measured element content (%): C, 83.18; H, 4.72; N, 12.10.
  • the above analysis results show that the obtained product is the target product.
  • Example 2 According to the synthesis of Example 2, the steps are the same, and the compound N 1 -([1,1'-biphenyl]-4-yl)benzene-1,2-diamine is substituted for the compound o-aminodiphenylamine to obtain 0.448g of a white compound (Yield 31.3%).
  • the molecular ion mass determined by mass spectrometry analysis is: 577.26 (calculated value: 577.23); theoretical element content (%) C 40 H 27 N 5 : C, 83.17; H, 4.71; N, 12.12; measured element content (%): C, 83.18; H, 4.72; N, 12.10.
  • the above analysis results show that the obtained product is the target product.
  • Example 3 According to the synthesis of Example 3, the steps are the same, and the compound N 1 -([1,1'-biphenyl]-4-yl)benzene-1,2-diamine is substituted for the compound o-aminodiphenylamine to obtain 0.458g of a white compound (Yield 33.8%).
  • the molecular ion mass determined by mass spectrometry analysis is: 577.28 (calculated value: 577.23); theoretical element content (%) C 40 H 27 N 5 : C, 83.17; H, 4.71; N, 12.12; measured element content (%): C, 83.18; H, 4.72; N, 12.10.
  • the above analysis results show that the obtained product is the target product.
  • Example 4 According to the synthesis of Example 4, the steps were the same, and the compound [1,1'-biphenyl]-4-carbaldehyde was used instead of the compound benzaldehyde to obtain 0.531 g of a white compound (yield 36.7%).
  • the molecular ion mass determined by mass spectrometry analysis is: 577.29 (calculated value: 577.23); theoretical element content (%) C 40 H 27 N 5 : C, 83.17; H, 4.71; N, 12.12; measured element content (%): C, 83.18; H, 4.72; N, 12.10.
  • the above analysis results show that the obtained product is the target product.
  • Example 5 According to the synthesis of Example 5, the steps were the same, and [1,1'-biphenyl]-4-carbaldehyde was used instead of the compound benzaldehyde to obtain 0.538 g of a white compound (yield 34.3%).
  • the molecular ion mass determined by mass spectrometry analysis is: 577.31 (calculated value: 577.23); theoretical element content (%) C 40 H 27 N 5 : C, 83.17; H, 4.71; N, 12.12; measured element content (%): C, 83.18; H, 4.72; N, 12.10.
  • the above analysis results show that the obtained product is the target product.
  • Example 6 According to the synthesis of Example 6, the steps are the same, using [1,1'-biphenyl]-4-carbaldehyde instead of the compound benzaldehyde to obtain 0.527 g of a white compound (yield 36.7%).
  • the molecular ion mass determined by mass spectrometry analysis is: 577.25 (calculated value: 577.23); theoretical element content (%) C 40 H 27 N 5 : C, 83.17; H, 4.71; N, 12.12; measured element content (%): C, 83.18; H, 4.72; N, 12.10.
  • the above analysis results show that the obtained product is the target product.
  • the specific device preparation process is as follows: transparent ITO glass is used as the base material for the preparation of the device, and then ultrasonically treated with 5% ITO lotion for 30 minutes, followed by distilled water (2 times ), acetone (2 times), isopropanol (2 times) ultrasonic washing, and finally the ITO glass is stored in isopropanol. Before each use, carefully wipe the surface of the ITO glass with an acetone cotton ball and an isopropyl alcohol cotton ball, rinse it with isopropyl alcohol and dry it, and then treat it with plasma for 5 minutes. The device is prepared by vacuum coating equipment using vacuum evaporation process.
  • the deposition rate is determined by Sainz Film Thickness Meter using vacuum evaporation process.
  • Various organic layers, LiF electron injection layers and metal Al electrodes are sequentially deposited on the ITO glass (see the following effect examples for specific device structures).
  • the current, voltage, brightness, luminescence spectrum and other characteristics of the device are tested simultaneously with PR 650 spectral scanning luminance meter and Keithley K 2400 digital source meter system.
  • the performance test of the device is carried out in anhydrous and oxygen-free glove box.
  • HATCN is used as the hole injection layer
  • DBBA is used as the first hole transport layer
  • TCTA is used as the second hole
  • the transport layer is used.
  • TCTA is mixed with the compound 1-171 of the present invention as a host material (the weight mixing ratio of TCTA and compound 1-171 is 1:1), and the compound 1-171 of the present invention is used as a host material. Used as an electronic transmission material.
  • the structure of the organic electroluminescent device is [ITO/HATCN(5nm)/DBBA(60nm)/TCTA(10nm)/TCTA:n+10wt%IrPPy 3 /n(30nm)/LiF(1nm)/Al(100nm) )].
  • n represents the compound number: 1-171.
  • the compound used in the host material is the same as that used in the electron transport layer, and IrPPy 3 is used as the doped luminescent material (the weight ratio doping concentration is 10WT%).
  • Table 1-1 The results of the effect examples are shown in Table 1-1.
  • HATCN was used as the hole injection layer
  • DBBA was used as the first hole transport layer
  • TCTA was used as the second hole transport layer Use
  • TCTA is mixed with 3P-T2T, E1 or E2 as the host material.
  • the two materials are mixed in a weight ratio of 1:1, and IrPPy 3 doped luminescent material is used (the weight ratio doping concentration is 10WT%), 3P-T2T, E1 or E2 are used as electron transport materials at the same time.
  • Comparative Examples 1-1 to 3-1 organic electroluminescent device structure is [ITO/HATCN (5nm)/DBBA (60nm)/TCTA (10nm)/TCTA: 3P-T2T or E1 or E2+10wt% IrPPy 3 / 3P-T2T or E1 or E2(30nm)/LiF(1nm)/Al(100nm)].
  • HATCN was used as the hole injection layer
  • DBBA was used as the first hole transport layer
  • TCTA was used as the second hole transport layer
  • TBT-07, TBT-14, ET85, 1, 3, 4, 130, 135, 150, 160, 165, and 170 are used as electron transport layer (ETL) materials, respectively. Used as a host material in the light-emitting layer.
  • ETL electron transport layer
  • Comparative Examples 4-1 to 15-1 organic electroluminescent device structure is [ITO/HATCN(5nm)/DBBA(60nm)/TCTA(10nm)/n+10wt%IrPPy 3 /n(30nm)/LiF(1nm) )/Al(100nm)].
  • n represents the compound number.
  • the compound used in the host material is the same as that used in the electron transport layer, and IrPPy 3 is used as the doped luminescent material (the weight ratio doping concentration is 10WT%).
  • Table 2-1 The results of the comparative example are shown in Table 2-1.
  • Test data of the device of the embodiment under the condition of a drive current density of 10 mA/cm 2 (constant current drive mode) (device life T90 represents the time it takes for the device brightness to decay to 90% of the initial brightness).
  • Test data of the comparative example device under the condition of a drive current density of 10 mA/cm 2 (constant current drive mode) (device life T90 represents the time it takes for the device brightness to decay to 90% of the initial brightness).
  • the 1,3,5-triazine compound of the present invention is used as the electron transport layer, and at the same time as the electron acceptor material and the electron donor material to construct the light emitting layer.
  • luminance organic electroluminescent device up to 8310cd / m 2 -8960cd / m 2 ; the current efficiency of up to 79cd / a-91cd / a; device life up to 1023 hours -1299 hours (T90).
  • the brightness of the organic electroluminescent device prepared by using the above compound as the electron transport layer and at the same time as the electron acceptor material to construct the light emitting layer is 5082cd/m 2 -5810cd/m 2 ; Current efficiency is 52cd/A-57cd/A; device lifetime is 410 hours-690 hours (T90).
  • HATCN is used as the hole injection layer
  • DBBA is used as the first hole transport layer
  • TCTA is used as the second hole
  • the transport layer is used.
  • TCTA is mixed with the compound 1-171 of the present invention as a host material (the weight mixing ratio of TCTA and compound 1-171 is 1:1), and TPBI is used as an electron transport material.
  • the structure of the organic electroluminescent device is [ITO/HATCN(5nm)/DBBA(60nm)/TCTA(10nm)/TCTA:n+10wt%IrPPy 3 /TPBI(30nm)/LiF(1nm)/Al(100nm) )].
  • n represents the compound number: 1-171.
  • the compound used in the host material is the same as that used in the electron transport layer, and IrPPy 3 is used as the doped luminescent material (the weight ratio doping concentration is 10WT%).
  • Table 1-2 The results of the effect examples are shown in Table 1-2.
  • HATCN was used as the hole injection layer
  • DBBA was used as the first hole transport layer
  • TCTA was used as the second hole transport layer Use
  • TCTA is mixed with one of 3P-T2T, E1, E2, TBT-07, TBT-14 and ET85 as the host material in the light-emitting layer, the two materials are mixed in a weight ratio of 1:1, and IrPPy 3 doped light-emitting material. (Weight ratio doping concentration is 10WT%)
  • TPBI is used as an electron transport material.
  • Organic electroluminescent device structure is [ITO/HATCN (5nm)/DBBA (60nm)/TCTA (10nm)/TCTA: 3P-T2T, E1, E2, TBT-07, TBT -14 or ET85+10wt% IrPPy 3 /TPBI(30nm)/LiF(1nm)/Al(100nm)].
  • HATCN was used as the hole injection layer
  • DBBA was used as the first hole transport layer
  • TCTA was used as the second hole transport layer
  • Compounds 1, 3 , 4 , 130, 135, 150, 160, 165 and 170 in the layer are used as host materials
  • IrPPy 3 is used as doped luminescent material (weight ratio doping concentration is 10WT%)
  • TPBI is used as electron Use of transmission materials.
  • Comparative Examples 7-2 to 15-2 organic electroluminescent device structures are [ITO/HATCN(5nm)/DBBA(60nm)/TCTA(10nm)/n+10wt%IrPPy 3 /TPBI(30nm)/LiF(1nm) )/Al(100nm)].
  • the results of the comparative example are shown in Table 2-2.
  • Test data of the device of the embodiment under the condition of a driving current density of 10 mA/cm 2 (constant current driving mode) (device life T90 represents the time it takes for the device brightness to decay to 90% of the initial brightness).
  • Test data of the comparative example device under the condition of a drive current density of 10 mA/cm 2 (constant current drive mode) (device life T90 represents the time it takes for the device brightness to decay to 90% of the initial brightness).
  • the 1,3,5-triazine compound of the present invention is used as the electron acceptor material and the electron donor material to construct the light emitting layer, and the prepared organic electroluminescent device is Brightness can reach 7087cd/m 2 -7981cd cd/m 2 ; current efficiency can reach 72cd/A-83cd/A; device life can reach 827 hours -985 hours (T90).
  • the organic electroluminescent device prepared by using the 1,3,5-triazine compound of the present invention as the electron acceptor material and the electron donor material to construct the light emitting layer is prepared by the light emitting layer constructed with the above compound Compared with the organic electroluminescent device, the brightness is increased by 22.6%-57%, the current efficiency is increased by 14%-73%, and the life of the device is increased by 23%-140%.
  • HATCN is used as the hole injection layer
  • DBBA is used as the first hole transport layer
  • TCTA is used as the second hole
  • the transport layer is used
  • TCTA is used as the host material in the light-emitting layer
  • compound 1-171 is used as the electron transport material.
  • Effect Example The structure of the organic electroluminescent device is [ITO/HATCN(5nm)/DBBA(60nm)/TCTA(10nm)/TCTA+10wt%IrPPy 3 /n(30nm)/LiF(1nm)/Al(100nm)] .
  • n represents the compound number: 1-171.
  • the compound used in the host material is the same as that used in the electron transport layer, and IrPPy 3 is used as the doped luminescent material (the weight ratio doping concentration is 10WT%).
  • the results of the effect examples are shown in Table 1-3.
  • HATCN was used as the hole injection layer
  • DBBA was used as the first hole transport layer
  • TCTA was used as the second hole transport layer Use
  • TCTA as the host material in the light-emitting layer
  • IrPPy 3 doped light-emitting material weight ratio doping concentration of 10WT%
  • 3P-T2T, E1, E2, TBT-07, TBT-14 and ET85 are used as Use of electronic transmission materials.
  • Comparative Examples 1-3 to 6-3 organic electroluminescent device structure is [ITO/HATCN (5nm)/DBBA (60nm)/TCTA (10nm)/TCTA+10wt% IrPPy 3 /3P-T2T, E1, E2, TBT-07, TBT-14 or ET85(30nm)/LiF(1nm)/Al(100nm)].
  • the results of the comparative example are shown in Table 2-3.
  • Test data of the device of the embodiment under the condition of a driving current density of 10 mA/cm 2 (constant current driving mode) (device life T90 represents the time it takes for the device brightness to decay to 90% of the initial brightness).
  • Test data of the comparative example device under the condition of a driving current density of 10 mA/cm 2 (constant current driving mode) (device life T90 represents the time it takes for the device brightness to decay to 90% of the initial brightness).
  • the brightness of the organic electroluminescent device prepared by using the 1,3,5-triazine compound of the present invention as the electron transport layer can reach 6371cd/m 2 -7069cd/ m 2 ; current efficiency can reach 65cd/A-75cd/A; device lifetime can reach 746 hours-877 hours (T90).
  • the organic electroluminescent device prepared by using the compound in the above comparative example as the electron transport layer has a brightness of 4862cd/m 2 -5196cd/m 2 and a current efficiency of 50cd/ A-56cd/A; device life is 361 hours -496 hours (T90).
  • the 1,3,5-triazine compound of the present invention is compared with the above-mentioned existing compounds, and the brightness of the organic electroluminescent device prepared as the electron transport layer is increased by 22.6%-45.4%, and the current efficiency Increased by 16%-50%; device life increased by 50%-143%.
  • HATCN is used as the hole injection layer
  • DBBA is used as the first hole transport layer
  • TCTA is used as the second hole
  • the transport layer is used.
  • TCTA is mixed with the compound 1-171 of the present invention as a host material (the weight mixing ratio of TCTA and compound 1-171 is 1:1), and the compound 1-179 of the present invention is used as a host material. Used as an electronic transmission material.
  • the structure of the organic electroluminescent device is [ITO/HATCN(5nm)/DBBA(60nm)/TCTA(10nm)/TCTA:n+1wt%DPh2AAN/n(30nm)/LiF(1nm)/Al(100nm) ].
  • n represents the compound number: 1-171.
  • the compound used in the host material is the same as the compound used in the electron transport layer, and DPh2AAN is used as the doped luminescent material (weight ratio doping concentration is 1WT%).
  • the results of the effect examples are shown in Table 1-5.
  • HATCN was used as the hole injection layer
  • DBBA was used as the first hole transport layer
  • TCTA was used as the second hole transport layer Use
  • TCTA is mixed with 3P-T2T, E1 or E2 as the host material in the light-emitting layer, the two materials are mixed in a weight ratio of 1:1
  • DPh2AAN doped luminescent material is used (weight ratio doping concentration is 1WT%)
  • 3P -T2T, E1 or E2 are used as electron transport materials respectively.
  • Comparative Examples 1-1 to 3-1 organic electroluminescent device structure is [ITO/HATCN (5nm)/DBBA (60nm)/TCTA (10nm)/TCTA: 3P-T2T or E1 or E2+10wt%DPh2AAN/3P -T2T or E1 or E2(30nm)/LiF(1nm)/Al(100nm)].
  • Test data of the device of the embodiment under the condition of a driving current density of 10 mA/cm 2 (constant current driving mode) (device life T90 represents the time it takes for the brightness of the device to decay to 90% of the initial brightness).
  • Test data of the comparative example device under the condition of a driving current density of 10 mA/cm 2 (constant current driving mode) (device life T90 represents the time it takes for the device brightness to decay to 90% of the initial brightness).
  • the 1,3,5-triazine compound of the present invention is used as the electron transport layer, and at the same time as the electron acceptor material and the electron donor material to construct the light emitting layer, the prepared
  • the brightness of the electroluminescent device can reach 3501cd/m 2 -3900cd/m 2 ; the current efficiency can reach 54cd/A-62cd/A; the lifetime of the device can reach 910 hours -990 hours (T90).
  • the brightness of the organic electroluminescent device prepared by using the above compound as the electron transport layer and at the same time as the electron acceptor material to construct the light-emitting layer is 2350cd/m 2 -2571cd/m 2 ;
  • the current efficiency is 39cd/A-41cd/A;
  • the device life is 402 hours-462 hours (T90).
  • HATCN is used as the hole injection layer
  • DBBA is used as the first hole transport layer
  • TCTA is used as the second hole
  • the transport layer is used.
  • TCTA is mixed with the compound 1-171 of the present invention as a host material (the weight mixing ratio of TCTA and compound 1-179 is 1:1), and TPBI is used as an electron transport material.
  • the structure of the organic electroluminescent device is [ITO/HATCN(5nm)/DBBA(60nm)/TCTA(10nm)/TCTA:n+1wt%DPh2AAN/TPBI(30nm)/LiF(1nm)/Al(100nm) ].
  • n represents the compound number: 1-179
  • DPh2AAN is used as a doped luminescent material (weight ratio doping concentration is 1WT%).
  • Table 1-5 The results of the effect examples are shown in Table 1-5.
  • HATCN was used as the hole injection layer
  • DBBA was used as the first hole transport layer
  • TCTA was used as the second hole transport layer Use
  • TCTA is mixed with 3P-T2T, E1 or E2 as the host material in the light-emitting layer, the two materials are mixed in a weight ratio of 1:1
  • DPh2AAN doped luminescent material is used (weight ratio doping concentration is 1WT%)
  • TPBI Used as an electronic transmission material.
  • Comparative Examples 1-5 to 3-5 organic electroluminescent device structure is [ITO/HATCN (5nm)/DBBA (60nm)/TCTA (10nm)/TCTA: 3P-T2T or E1 or E2+10wt%DPh2AAN/TPBI (30nm)/LiF(1nm)/Al(100nm)].
  • Test data of the device of the embodiment under the condition of a driving current density of 10 mA/cm 2 (constant current driving mode) (device life T90 represents the time it takes for the device brightness to decay to 90% of the initial brightness).
  • Test data of the comparative example device under the condition of a driving current density of 10 mA/cm 2 (constant current driving mode) (device life T90 represents the time it takes for the device brightness to decay to 90% of the initial brightness).
  • the 1,3,5-triazine compound of the present invention is used as the electron acceptor material and the electron donor material to construct the light emitting layer, and the brightness of the organic electroluminescent device prepared is It can reach 3205cd/m 2 -3600cd/m 2 ; current efficiency can reach 47cd/A-56cd/A; device life can reach 650 hours -750 hours (T90).
  • the organic electroluminescent device prepared by using the above compound as the electron acceptor material to construct the luminescent layer has a brightness of 2032cd/m 2 -2205cd/m 2 and a current efficiency of 34cd/A -38cd/A; device lifetime is 342 hours -375 hours (T90).
  • the 1,3,5-triazine compound of the present invention is used as an electron acceptor material to construct a light-emitting layer, and the brightness of the organic electroluminescent device prepared by using the 1,3,5-triazine compound of the present invention is increased by 45%-77. %, the current efficiency is increased by 23.7% to 64.7%; the device life is increased by 73% to 119%.
  • the mother nucleus of the 1,3,5-triazine compound shown in formula I of the present invention is a benzene ring linked by a single bond
  • the molecular structure of a triazine and one or more benzimidazoles is relatively complicated, and it is mainly manifested in: (1) A triazine heterocycle and one or more benzimidazole heterocycles constitute a complex compound heterocyclic system; (2) A triazine derivative and one or more benzenes are linked by a single bond on the periphery of a benzene ring
  • the molecular conformational structure of this molecule is very complicated; (3) Triazine derivatives and benzimidazole derivatives are both electron-deficient groups, and triazine derivatives are stronger than benzimidazole derivatives Due to the lack of electrons, this molecule will have certain intramolecular charge transfer characteristics.
  • the molecular weight of the target molecule can be adjusted in a larger range by introducing different substituent groups, and thus the molecular weight of the target molecule can be adjusted in a wider range.
  • the sublimation temperature of the target molecule is adjusted within the range (200-450°C), which is advantageous for selecting matching materials that are close to the sublimation temperature of the target product.
  • a good electron transport material may not necessarily be a good host material.
  • As a good host material it should generally have balanced and good electron and hole transport properties.
  • the properties of the host material also depend on the carrier transport properties of the matched doped luminescent material and the overall carrier transport properties of the doped film after doping. For example, if a host material dominated by electron transport is matched with a doped material with a certain hole transport ability, it is possible to obtain better results, and if it is matched with a doped material with a certain electron transport ability, it is possible to obtain a poor effect. .
  • the carrier transport performance of the composite film obtained after the host/guest doping is often not a simple superposition of the two separate properties.
  • the carrier transport performance of the doped composite film is difficult to accurately predict, and specific experiments must be conducted.
  • the analysis and verification party can obtain the ideal matching combination.
  • the host material composed of the two-component electron donor and electron acceptor will be more complicated, and its performance is also difficult to accurately infer based on experience.
  • the existing compounds E1, E2 or 3P-T2T are used as one of the electron transport material and the host material of the light-emitting layer at the same time, or only as one of the host materials of the light-emitting layer.
  • the efficiency and lifetime of the prepared organic electroluminescent device are not significantly improved.
  • CN102593374B discloses the compound TPT-07 as an electron transport layer, or as an electron transport layer, it is used as a host material for the preparation of electroluminescent devices. However, the efficiency of the prepared light-emitting device is still low.
  • the compound of the present invention when used as a combination of electron acceptor material and electron donor material, when used as the host material of the light-emitting layer, under the same driving current density,
  • the brightness, efficiency and lifetime of the prepared organic electroluminescent device are significantly higher than that of the materials disclosed in the prior art; further, when the compound of the present invention is used as an electron transport layer, it is used as an electron acceptor material and an electron donor material at the same time
  • the light-emitting layer is constructed, and the organic electroluminescent device prepared under the same driving current density can obtain better brightness, efficiency and lifetime.
  • the stability of the device has the most obvious technical effect advantage.

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Abstract

Disclosed are a substituted 1,3,5-triazine compound, composition and application thereof. The present invention provides a 1,3,5-triazine compound represented by formula I. The 1,3,5-triazine compound in the present invention can be used not only an electron transport material, but also an electron acceptor material. The compound can be used for preparing an electron transport layer or is used in combination with a composition of an electron donor material to serve as the main material of an electroluminescent device, so that the electroluminescent device obtained by preparation has advantages such as high efficiency and long service life. Furthermore, while being used as an electron transport layer, the 1,3,5-triazine compound is used in combination with a composition of an electron donor material as an electron acceptor material to construct a light-emitting layer, so that the electroluminescent device obtained by preparation has advantages such as better efficiency and longer service life.

Description

一种取代的1,3,5-三嗪化合物、组合物及其应用A substituted 1,3,5-triazine compound, composition and application thereof
本申请要求申请日为2019/3/29的中国专利申请2019102530823的优先权。本申请引用上述中国专利申请的全文。This application claims the priority of the Chinese patent application 2019102530823 whose filing date is 2019/3/29. This application quotes the full text of the aforementioned Chinese patent application.
技术领域Technical field
本发明涉及一种取代的1,3,5-三嗪化合物、组合物及其应用。The invention relates to a substituted 1,3,5-triazine compound, composition and application thereof.
背景技术Background technique
二十世纪六十年代初，Pope等人最早报道了有机电致发光现象，他们在蒽单晶两侧施加四百伏的高压时观察到了蒽发出的蓝光(见M.Pope,H.Kallmann and P.Magnante,J.Chem.Phys.,1963,38,2042)。但是由于单晶难于生长，器件驱动电压很高，他们所采用的工艺几乎没有实际用途。直到1987年，美国Kodak公司的C.W.Tang等人采用超薄膜技术以空穴传输效果较好的芳香胺作为空穴传输层，以8-羟基喹啉的铝配合物作为发光层，以氧化铟锡(ITO)薄膜和金属合金分别作为阳极和阴极，制备了发光器件。该器件在10V驱动电压下得到了亮度高达1000cd/m 2的绿光发射，器件的效率为1.5lm/W(见C.W.Tang and S.A.VanSlyke，Appl.Phys.Lett.，1987，51，913)。这一突破性进展使得有机电致发光研究在世界范围内迅速深入地开展起来。 In the early 1960s, Pope et al. first reported the phenomenon of organic electroluminescence. They observed the blue light emitted by anthracene when a high voltage of 400 volts was applied on both sides of an anthracene single crystal (see M. Pope, H. Kallmann and P. Magnante, J. Chem. Phys., 1963, 38, 2042). However, because single crystals are difficult to grow and the device drive voltage is high, the processes they use have almost no practical use. Until 1987, CWTang et al. of Kodak Corporation of the United States used ultra-thin film technology to use aromatic amines with better hole transport effects as the hole transport layer, 8-hydroxyquinoline aluminum complexes as the light-emitting layer, and indium tin oxide ( ITO) film and metal alloy were used as anode and cathode respectively to prepare light-emitting devices. The device obtains green light emission with a brightness of up to 1000 cd/m 2 under a driving voltage of 10V, and the device efficiency is 1.5 lm/W (see CWTang and SAVan Slyke, Appl. Phys. Lett., 1987, 51, 913). This breakthrough has enabled organic electroluminescence research to be carried out rapidly and deeply in the world.
1998年美国普林斯顿大学的Forrest等人研究发现，使用一般有机材料或采用荧光染料掺杂技术制备的有机发光器件，由于受自旋守恒的量子力学跃迁规律约束，其最大发光内量子效率为25％。他们将磷光染料八乙基卟啉铂(PtOEP)掺杂于主体发光材料中，制备出外量子效率为4％，内量子效率达23％的发光器件，从而开辟了磷光电致发光的新领域(见M.A.Baldo，D.F.O'Brienetal.，Nature，1998，395，151)。但一方面磷光材料普遍使用铱铂等贵金属，价格昂贵，另一方面对于深蓝光磷光材料来说其仍存在着化学不稳定性，器件在高电流密度下效率滚降较大等问题，所以开发一种使用廉价稳定的有机小分子材料而又能实现高效率发光的OLED器件显得极为重要。In 1998, Forrest et al. of Princeton University in the United States found that organic light-emitting devices prepared using general organic materials or using fluorescent dye doping technology are restricted by the quantum mechanical transition law of spin conservation, and their maximum luminous internal quantum efficiency is 25% . They doped the phosphorescent dye octaethyl porphyrin platinum (PtOEP) into the host luminescent material to prepare a light-emitting device with an external quantum efficiency of 4% and an internal quantum efficiency of 23%, thus opening up a new field of phosphorescent photoluminescence ( See MA Baldo, DFO'Brienetal., Nature, 1998, 395, 151). However, on the one hand, phosphorescent materials generally use precious metals such as iridium and platinum, which are expensive. On the other hand, for deep blue phosphorescent materials, they still have chemical instability, and the device has problems such as large efficiency roll-off under high current density. An OLED device that uses cheap and stable organic small molecule materials and can achieve high-efficiency light emission is extremely important.
新材料在有机电致发光器件中的应用是推动电致发光技术不断进步并进入实用化阶段的必需手段。近年来，人们对新材料的开发投入了巨大的财力和精力，大量性能优良的材料使有机电致发光取得了一些突破性进展(见U.S.Pat.No.5,150,006；5,141,671；5,073,446；5,061,569；5,059,862；5,059,861；5,047,687；4,950,950；5,104,740；5,227,252；5,256,945；5,069,975；5,122,711；5,554,450；5,683,823；5,593,788；5,645,948；5,451,343；5,623,080；5,395,862)。The application of new materials in organic electroluminescence devices is a necessary means to promote the continuous progress of electroluminescence technology and enter the practical stage. In recent years, people have invested huge financial resources and energy in the development of new materials, and a large number of materials with excellent performance have made some breakthroughs in organic electroluminescence (see USPat. No. 5,150,006; 5,141,671; 5,073,446; 5,061,569; 5,059,862; 5,059,861; 5,047,687; 4,950,950; 5,104,740; 5,227,252; 5,256,945; 5,069,975; 5,122,711; 5,554,450; 5,683,823; 5,593,788; 5,645,948; 5,451,343; 5,623,080; 5,395,862).
近年来，随着在全色显示和固态白光照明领域展示出巨大的应用前景，有机电致发光技术在科研界以及产业界都得到了广泛的研究和关注。有机小分子光电材料因其结构明确、易于修饰、提纯加工简单等优点而被大量的用来开发作为高性能材料。目前来说，传统荧光染料分子往往具有很高的荧光量子产率，但其掺杂OLED器件由于受限于25％的内量子效率，外量子效率普遍低于5％，与磷光器件的效率还有很大差距。如红光染料DCM(见C.W.Tang,S.A.VanSlyke,and C.H.Chen,J.Appl.Phys., 1989,65,3610；U.S.Pat.No.5,908,581)，器件效率<10cd/A；绿光染料喹吖啶酮(见U.S.Pat.No.5,227,252；5，593,788；CN1482127A；CN1219778；CN1660844)，器件效率<20cd/A等。In recent years, with the display of huge application prospects in the field of full-color display and solid-state white light lighting, organic electroluminescence technology has received extensive research and attention in the scientific and industrial circles. Organic small molecule optoelectronic materials are widely used as high-performance materials because of their clear structure, easy modification, simple purification and processing. At present, traditional fluorescent dye molecules often have very high fluorescence quantum yields, but their doped OLED devices are limited by the internal quantum efficiency of 25%, and the external quantum efficiency is generally lower than 5%, which is lower than the efficiency of phosphorescent devices. There is a big gap. Such as the red dye DCM (see CWTang, SAVan Slyke, and CH Chen, J. Appl. Phys., 1989, 65, 3610; USPat. No. 5,908, 581), the device efficiency <10cd/A; the green dye quinacrine Pyridone (see USPat. No. 5,227,252; 5,593,788; CN1482127A; CN1219778; CN1660844), device efficiency <20cd/A, etc.
目前能实现突破25％的内量子效率限制的荧光OLED器件主要采用了延迟荧光机制，其能有效利用器件内的三重激发态能量。其机制主要有两类，一类是TTA(Triplet-Triplet Annihilation，三重态-三重态湮灭)机制(见D.Kondakov,T.D.Pawlik,T.K.Hatwar,and J.P.Spindler，J.Appl.Phys.,2009,106,124510)。另一类是TADF(Thermally Activated Delayed Fluorescence，热活化延迟荧光)机制(见H.Uoyama,K.Goushi,K.Shizu,H.Nomura,C.Adachi，Nature.,2012,492,234)。TTA机制是利用两个三重态激子融合产生单重态激子，提高单重态激子生成比率的机制，但其器件最大内量子效率只有40％～62.5％。TADF机制是利用具有较小单重态-三重态能级差(ΔEST)的有机小分子材料，其三重态激子在环境热能下可通过反向系间窜越(RISC)这一过程转化为单重态激子的机制。理论上其器件内量子效率能达到100％。通常情况下，TADF分子主要作为客体材料掺杂在宽禁带主体材料中实现高效率的热活化延迟荧光(见Q.Zhang,J.Li,K.Shizu,S.Huang,S.Hirata,H.Miyazaki,C.Adachi,J.Am.Chem.Soc.2012,134,14706；H.Uoyama,K.Goushi,K.Shizu,H.Nomura,C.Adachi,Nature.,2012,492,234；T.Nishimoto,T.Yasuda,S.Y.Lee,R.Kondo,C.Adachi,Mater.Horiz.,2014,1,264)。At present, fluorescent OLED devices that can break through the 25% internal quantum efficiency limit mainly adopt a delayed fluorescence mechanism, which can effectively utilize the triplet excited state energy in the device. There are two main types of mechanisms, one is TTA (Triplet-Triplet Annihilation, triplet-triple annihilation) mechanism (see D. Kondakov, TDPawlik, TK Hatwar, and JP Spindler, J. Appl. Phys., 2009, 106,124510). The other is the TADF (Thermally Activated Delayed Fluorescence) mechanism (see H. Uoyama, K. Goushi, K. Shizu, H. Nomura, C. Adachi, Nature., 2012, 492, 234). The TTA mechanism is a mechanism that uses the fusion of two triplet excitons to generate singlet excitons to increase the generation rate of singlet excitons, but the maximum internal quantum efficiency of the device is only 40% to 62.5%. The TADF mechanism uses organic small molecular materials with a small singlet-triplet energy level difference (ΔEST). The triplet excitons can be converted into singlet through the reverse intersystem crossing (RISC) process under ambient thermal energy. The mechanism of heavy state excitons. In theory, the quantum efficiency of the device can reach 100%. Under normal circumstances, TADF molecules are mainly used as guest materials doped in wide-bandgap host materials to achieve high-efficiency thermally activated delayed fluorescence (see Q. Zhang, J. Li, K. Shizu, S. Huang, S. Hirata, H .Miyazaki,C.Adachi,J.Am.Chem.Soc.2012,134,14706; H.Uoyama,K.Goushi,K.Shizu,H.Nomura,C.Adachi,Nature.,2012,492,234; T. Nishimoto, T. Yasuda, SY Lee, R. Kondo, C. Adachi, Mater. Horiz., 2014, 1, 264).
由于能够同时利用单线态和三线态激子进行发光，TADF材料的电致发光器件性能与传统荧光器件相比有着显著提升。此外，与传统磷光材料相比，TADF材料价格低廉，更有利于其商业化的推广与应用。目前，从深蓝光到近红外发光，各种光色的TADF分子被合成出来，部分器件性能已经可以和传统的磷光器件相媲美。传统的单分子TADF材料，一般由给体(D)和受体(A)单元两部分组成。通过精心地分子设计使HOMO和LUMO轨道分别集中在给体和受体两端以获得较小的单线态三线态能级差，并以此来实现有效地反向系间窜越，从而实现高效的TADF发光。另外，激基复合物(Exciplex)发光是一种给体分子与受体分子之间的电荷转移激发态发光行为，其发光源于受体分子的LUMO轨道与给体分子HOMO轨道之间的电子跃迁。由于激基复合物的HOMO和LUMO轨道分别集中在给体和受体两个分子上，相应的单线态和三线态能级差与单分子TADF材料相比往往会更小。与单分子TADF材料相比，激基复合物也可以实现高效的热活化延迟荧光发射。给体分子和受体分子不仅可以形成激基复合物作为发光层进行发光，还可以分别充当空穴传输和电子传输层，这在一定程度上简化了器件的结构。除了通过掺杂形成激基复合物进行发光外，在给体与受体的分子界面处也可以产生类似于平面异质结(P-N)的激基复合物发光(见：Advanced Materials,2016,28，239-244)。以激基复合物作为共主体制备的电致发光器件具有低开启、高效率、低滚降等诸多优点也成为了目前研究的热门(见：Advanced Functional Materials,2015,25,361-366)。Because it can simultaneously use singlet and triplet excitons to emit light, the performance of the electroluminescent device of TADF material is significantly improved compared with traditional fluorescent devices. In addition, compared with traditional phosphorescent materials, TADF materials are inexpensive, which is more conducive to their commercial promotion and application. At present, TADF molecules of various light colors have been synthesized from deep blue to near-infrared light emission, and the performance of some devices is comparable to traditional phosphorescent devices. Traditional single-molecule TADF materials generally consist of donor (D) and acceptor (A) units. Through careful molecular design, the HOMO and LUMO orbitals are concentrated on both ends of the donor and acceptor respectively to obtain a smaller singlet triplet energy level difference, and thus to achieve effective reverse intersystem crossing, thereby achieving efficient TADF glows. In addition, Exciplex luminescence is a charge transfer excited state luminescence behavior between a donor molecule and an acceptor molecule. Its luminescence comes from the electrons between the LUMO orbital of the acceptor molecule and the HOMO orbital of the donor molecule. Jump. Since the HOMO and LUMO orbitals of the exciplex are concentrated on the donor and acceptor molecules, the corresponding singlet and triplet energy level differences tend to be smaller compared with single-molecule TADF materials. Compared with single-molecule TADF materials, exciplexes can also achieve efficient thermally activated delayed fluorescence emission. Donor molecules and acceptor molecules can not only form exciplexes as a light-emitting layer to emit light, but also serve as hole transport and electron transport layers, respectively, which simplifies the structure of the device to a certain extent. In addition to the formation of exciplex by doping to emit light, the molecular interface between the donor and acceptor can also produce exciplex luminescence similar to the planar heterojunction (PN) (see: Advanced Materials, 2016, 28 , 239-244). Electroluminescent devices prepared with excimer complexes as co-hosts have many advantages such as low turn-on, high efficiency, and low roll-off, and have become a hot topic in current research (see: Advanced Functional Materials, 2015, 25, 361-366).
CN108218836A公开了两个如下所示的三(苯基/吡啶-苯并咪唑)苯/吡啶化合物(E1和E2)，这两个化合物可以作为电子受体与电子给体复合构造发光层，同时这类材料也可以作为电子传输用于电致发光器件。CN108218836A discloses two tris (phenyl/pyridine-benzimidazole) benzene/pyridine compounds (E1 and E2) as shown below. These two compounds can be used as electron acceptors and electron donors to construct a light-emitting layer. Similar materials can also be used as electron transport in electroluminescent devices.
Figure PCTCN2020081035-appb-000001
Figure PCTCN2020081035-appb-000001
但是，由于E1或E2作为电子受体与电子给体复合构造发光层，同时E1或E2作为电子传输材料，制备得到的发光器件的效率偏低，同时器件稳定性较差。However, since E1 or E2 is used as an electron acceptor and an electron donor to construct a light-emitting layer, while E1 or E2 is used as an electron transport material, the efficiency of the prepared light-emitting device is low, and the stability of the device is poor.
现有技术(ACS Appl.Mater.Interfaces 2018,10,2151-2157；ACS Appl.Mater.Interfaces 2018,10,24090-24098)公开了如下所示的分子3P-T2T。The prior art (ACS Appl.Mater.Interfaces 2018, 10, 2151-2157; ACS Appl.Mater.Interfaces 2018, 10, 24090-24098) discloses the molecule 3P-T2T as shown below.
Figure PCTCN2020081035-appb-000002
Figure PCTCN2020081035-appb-000002
该分子作为电子受体材料可以与一些电子给体材料复合作为电致发光器件的主体材料，同时这个材料还可以同时作为电子传输层用于电致发光器件。但是，由3P-T2T分子与一些电子给体材料复合作为电致发光器件的主体材料，同时3P-T2T分子作为电子传输层，制备得到的发光器件的稳定性较差。The molecule as an electron acceptor material can be combined with some electron donor materials as the host material of the electroluminescence device, and the material can also be used as an electron transport layer for the electroluminescence device at the same time. However, the combination of 3P-T2T molecules and some electron donor materials as the host material of the electroluminescent device, and the 3P-T2T molecule as the electron transport layer, the stability of the prepared light emitting device is poor.
CN106946859A公开一系列双苯并咪唑及其衍生物取代的三嗪化合物，并指出这些化合物可以在电致发光器件中作为空穴阻挡层和电子传输层使用，这些化合物可作为光取出层或者电子传输层用于电致发光器件，可以一定程度上提高器件的效率。但是，由于采用单一的4,4’-二咔唑联苯(CBP)为主体材料，CBP的电子传输能力较差，因此器件效率仍较低。CN106946859A discloses a series of triazine compounds substituted with bisbenzimidazole and its derivatives, and points out that these compounds can be used as hole blocking layers and electron transport layers in electroluminescent devices, and these compounds can be used as light extraction layers or electron transport layers. The layer is used in electroluminescent devices, which can improve the efficiency of the device to a certain extent. However, due to the use of a single 4,4'-dicarbazole biphenyl (CBP) as the host material, the electron transport capability of CBP is poor, so the device efficiency is still low.
CN102593374B公开了如下所示的三个化合物(TPT-07、TBT-07和TBT-14)单独作为电子传输层、主体材料用于制备电致发光器件。但是，制备得到的发光器件的效率偏低。CN102593374B discloses the following three compounds (TPT-07, TBT-07 and TBT-14) as the electron transport layer and host material for the preparation of electroluminescent devices. However, the efficiency of the prepared light-emitting device is low.
Figure PCTCN2020081035-appb-000003
Figure PCTCN2020081035-appb-000003
因此，与单分子TADF材料相比，目前激基复合物的器件性能仍有待提高。Therefore, compared with single-molecule TADF materials, the current device performance of exciplex still needs to be improved.
发明内容Summary of the invention
本发明所要解决的问题是现有的电子受体材料、电子传输材料不足的缺陷，而提供了一种1,3,5-三嗪类化合物、组合物及其应用。本发明的1,3,5-三嗪类化合物不仅可作为电子传输材料用于制备电致发光器件的电子传输层，还可作为电子受体材料，其与电子给体材料的组合物可作为电致发光器件的主体材料，由此制备得到的电致发光器件具有较高效率、较长寿命等优点；进一步地由该1,3,5-三嗪类化合物作为电子传输层的同时，作为电子受体材料与电子给体材料的组合物构建发光层，制备得到的电致发光器件具有更优的高效率、更长的寿命等优点。The problem to be solved by the present invention is the deficiency of existing electron acceptor materials and electron transport materials, and provides a 1,3,5-triazine compound, composition and application thereof. The 1,3,5-triazine compound of the present invention can not only be used as an electron transport material for preparing the electron transport layer of an electroluminescent device, but also can be used as an electron acceptor material, and a combination of it and an electron donor material can be used as The host material of the electroluminescent device, the electroluminescent device prepared therefrom has the advantages of higher efficiency and longer life; furthermore, the 1,3,5-triazine compound is used as the electron transport layer at the same time as The combination of the electron acceptor material and the electron donor material constructs a light-emitting layer, and the prepared electroluminescent device has the advantages of better high efficiency, longer life and the like.
本发明是通过下述技术方案来解决上述技术问题的。The present invention solves the above technical problems through the following technical solutions.
本发明提供了一种如式I所示的1,3,5-三嗪类化合物，The present invention provides a 1,3,5-triazine compound as shown in formula I,
Figure PCTCN2020081035-appb-000004
Figure PCTCN2020081035-appb-000004
其中，R 1、R 2、R 3、R 4和R 5中的1个或2个独立地为R；余者(即R 1、R 2、R 3、R 4和R 5中不为R的取代基；例如，当R 1、R 2、R 3、R 4和R 5中的1个独立地为R、且R 3独立地为R时，R 1、R 2、R 4和R 5不为R，或者，当R 1、R 2、R 3、R 4和R 5中的2个独立地为R、且R 2和R 4独立地为R时，R 1、R 3和R 5不为R)独立地为R Y1； Among them, one or two of R 1 , R 2 , R 3 , R 4 and R 5 are independently R; the rest (ie, R 1 , R 2 , R 3 , R 4 and R 5 are not R For example, when one of R 1 , R 2 , R 3 , R 4 and R 5 is independently R, and R 3 is independently R, R 1 , R 2 , R 4 and R 5 Is not R, or, when two of R 1 , R 2 , R 3 , R 4 and R 5 are independently R, and R 2 and R 4 are independently R, R 1 , R 3 and R 5 Not R) independently R Y1 ;
R Y1、R 6、R 7、R 8、R 9、R 10、R 11、R 12、R 13、R 14和R 15独立地为氢、氘、卤素、氰基、C 1～C 10烷基、被一个或多个R a-1取代的C 1～C 10烷基、C 1～C 10烷基-O-、被一个或多个R a-2取代的C 1～C 10烷基-O-、C 6～C 14芳基、被一个或多个R a-3取代的C 6～C 14芳基、5-6元单环杂芳基、被一个或多个R a-4取代的5-6元单环杂芳基或
Figure PCTCN2020081035-appb-000005
所述的5-6元单环杂芳基和被一个或多个R a-4取代的5-6元单环杂芳基里的“5-6元单环杂芳基”中杂原子的定义如下：杂原子选自N、O和S中的一种或多种，杂原子数为1～4个；当R a-1、R a-2、R a-3和R a-4独立地为多个时，相同或不同；其中，
Figure PCTCN2020081035-appb-000006
为
Figure PCTCN2020081035-appb-000007
与
Figure PCTCN2020081035-appb-000008
通过单键连接； R Y1 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 and R 15 are independently hydrogen, deuterium, halogen, cyano, C 1 ～C 10 alkane group, with one or more substituents R a-1 is C 1 ~ C 10 alkyl group, C 1 ~ C 10 alkyl group -O-, with one or more R a-2 substituted C 1 ~ C 10 alkyl group -O-, C 6 ~ C 14 aryl group, substituted with one or more R a-3 substituted C 6 ~ C 14 aryl, 5-6 membered monocyclic heteroaryl, substituted with one or more R a-4 Substituted 5-6 membered monocyclic heteroaryl or
Figure PCTCN2020081035-appb-000005
The heteroatoms in the 5-6 membered monocyclic heteroaryl group and the 5-6 membered monocyclic heteroaryl group substituted by one or more Ra -4 The definition is as follows: the heteroatom is selected from one or more of N, O and S, and the number of heteroatoms is 1 to 4; when Ra -1 , Ra -2 , Ra -3 and Ra -4 are independent When there are multiple places, they are the same or different; among them,
Figure PCTCN2020081035-appb-000006
for
Figure PCTCN2020081035-appb-000007
versus
Figure PCTCN2020081035-appb-000008
Connect via a single key;
R独立地为
Figure PCTCN2020081035-appb-000009
R is independently
Figure PCTCN2020081035-appb-000009
n1和n2独立地为1、2、3或4；n3为1、2或3；n1 and n2 are independently 1, 2, 3 or 4; n3 is 1, 2 or 3;
R 1-1、R 2-1、R 1-2、R 2-2、R 1-3、R 1-4、R 2-3独立地为氢、氘、卤素、氰基、C 1～C 10烷基、被一个或多个R b-1取代的C 1～C 10烷基、C 1～C 10烷基-O-、被一个或多个R b-2取代的C 1～C 10烷基-O-、C 6～C 14芳基、被一个或多个R b-3取代的C 6～C 14芳基、5-6元单环杂芳基、被一个或多个R b-4取代的5-6元单环杂芳基或
Figure PCTCN2020081035-appb-000010
所述的5-6元单环杂芳基和被一个或多个R b-4取代的5-6元单环杂芳基里的“5-6元单环杂芳基”中杂原子的定义如下：杂原子选自N、O和S中的一种或多种，杂原子数为1～4个；当R b-1、R b-2、R b-3和R b-4独立地为多个时，为相同或不同；其中，
Figure PCTCN2020081035-appb-000011
为
Figure PCTCN2020081035-appb-000012
与
Figure PCTCN2020081035-appb-000013
通过单键连接； R 1-1 , R 2-1 , R 1-2 , R 2-2 , R 1-3 , R 1-4 , R 2-3 are independently hydrogen, deuterium, halogen, cyano, C 1 ～C 10 alkyl group, C 1 ～C 10 alkyl group substituted by one or more R b-1 , C 1 ～C 10 alkyl group-O-, C 1 ～C 10 substituted by one or more R b-2 alkyl -O-, C 6 ~ C 14 aryl group, substituted with one or more R b-3 is unsubstituted C 6 ~ C 14 aryl, 5-6 membered monocyclic heteroaryl, substituted with one or more R b -4 substituted 5-6 membered monocyclic heteroaryl or
Figure PCTCN2020081035-appb-000010
The heteroatoms in the 5-6 membered monocyclic heteroaryl group and the 5-6 membered monocyclic heteroaryl group substituted by one or more R b-4 The definition is as follows: heteroatoms are selected from one or more of N, O and S, and the number of heteroatoms is 1 to 4; when R b-1 , R b-2 , R b-3 and R b-4 are independent When there are multiple places, they are the same or different; among them,
Figure PCTCN2020081035-appb-000011
for
Figure PCTCN2020081035-appb-000012
versus
Figure PCTCN2020081035-appb-000013
Connect via a single key;
Figure PCTCN2020081035-appb-000014
独立地为苯基、被一个或多个R c-1取代的苯基、5-6元单环杂芳基、或、被一个或多个R c-2取代的5-6元单环杂芳基；所述的5-6元单环杂芳基和被一个或多个R c-2取代的5-6元单环杂芳基里的“5-6元单环杂芳基”中杂原子的定义如下：杂原子为N，杂原子个数为1～3个；当R c-1和R c-2独立地为多个时，相同或不同；
Figure PCTCN2020081035-appb-000014
Independently is phenyl, phenyl substituted with one or more R c-1 , 5-6 membered monocyclic heteroaryl, or, 5-6 membered monocyclic heterocyclic substituted with one or more R c-2 Aryl; the 5-6 membered monocyclic heteroaryl group and the 5-6 membered monocyclic heteroaryl group substituted by one or more R c-2 in the "5-6 membered monocyclic heteroaryl group" The definition of heteroatom is as follows: heteroatom is N, and the number of heteroatoms is 1 to 3; when R c-1 and R c-2 are independently multiple, they are the same or different;
R a-1、R a-2、R a-3、R a-4、R b-1、R b-2、R b-3、R b-4、R c-1和R c-2独立地为如下取代基：氘、卤素、氰基、三氟甲基、C 1～C 6烷基或C 1～C 6烷基-O-。 R a-1 , R a-2 , R a-3 , R a-4 , R b-1 , R b-2 , R b-3 , R b-4 , R c-1 and R c-2 are independent Ground is the following substituents: deuterium, halogen, cyano, trifluoromethyl, C 1 -C 6 alkyl or C 1 -C 6 alkyl-O-.
本发明中，所述的如式I所示的1,3,5-三嗪类化合物中某些取代基的定义可如下所述，未提及的取代基的定义均如上任一方案所述。In the present invention, the definitions of certain substituents in the 1,3,5-triazine compound represented by formula I can be as follows, and the definitions of unmentioned substituents are as described in any of the above schemes .
在本发明的某一实施方案中，R 1-1、R 2-1、R 1-2、R 2-2、R 1-3、R 1-4、R 2-3、R Y1、R 6、R 7、R 8、R 9、R 10、R 11、R 12、R 13、R 14和R 15独立地为卤素中，所述的卤素(例如氟、氯、溴或碘)独立地为氟。 In a certain embodiment of the present invention, R 1-1 , R 2-1 , R 1-2 , R 2-2 , R 1-3 , R 1-4 , R 2-3 , R Y1 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 and R 15 are independently halogens, and the halogens (such as fluorine, chlorine, bromine or iodine) are independently fluorine.
在本发明的某一实施方案中，R Y1、R 6、R 7、R 8、R 9、R 10、R 11、R 12、R 13、R 14和R 15独立地为C 1～C 10烷基、被一个或多个R a-1取代的C 1～C 10烷基、C 1～C 10烷基-O-或被一个或多个R a-2取代的C 1～C 10烷基-O-中，所述的C 1～C 10烷基独立地为C 1～C 6烷基(例如甲基、乙基、正丙基、异丙基、正丁基、叔丁基、仲丁基、异丁基、戊基或己基)，较佳地为C 1～C 4的烷基(例如甲基、乙基、正丙基、异丙基、正丁基、仲丁基、异丁基或叔丁基)，更佳地为甲基或异丙基。 In a certain embodiment of the present invention, R Y1 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 and R 15 are independently C 1 to C 10 alkyl, substituted with one or more substituents R a-1 is C 1 ~ C 10 alkyl group, C 1 ~ C 10 alkyl group by one or more -O- R a-2 substituted by C 1 ~ C 10 alkyl In the group-O-, the C 1 ～C 10 alkyl group is independently a C 1 ～C 6 alkyl group (for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, butyl, isobutyl, pentyl or hexyl group), preferably a C 1 ~ C 4 alkyl group (e.g. methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, Isobutyl or tert-butyl), more preferably methyl or isopropyl.
在本发明的某一实施方案中，R Y1、R 6、R 7、R 8、R 9、R 10、R 11、R 12、R 13、R 14和R 15独立地为C 6～C 14芳基或被一个或多个R a-3取代的C 6～C 14芳基中，所述的C 6～C 14芳基独立地为C 6～C 10芳基；例如苯基或萘基。 In a certain embodiment of the present invention, R Y1 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 and R 15 are independently C 6 ～C 14 In an aryl group or a C 6 ～C 14 aryl group substituted with one or more Ra -3 , the C 6 ～C 14 aryl group is independently a C 6 ～C 10 aryl group; for example, phenyl or naphthyl .
在本发明的某一实施方案中，R Y1、R 6、R 7、R 8、R 9、R 10、R 11、R 12、R 13、R 14和R 15独立地为5-6元单环杂芳基或被一个或多个R a-4取代的5-6元单环杂芳基中，所述的C 1～C 12杂芳基独立地为杂原子选自N，杂原子数为1～3个；较佳地为吡啶基。 In a certain embodiment of the invention, R Y1 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 and R 15 are independently 5-6 yuan unit In a ring heteroaryl group or a 5-6 membered monocyclic heteroaryl group substituted by one or more Ra -4 , the C 1 ～C 12 heteroaryl group is independently a heteroatom selected from N, the number of heteroatoms 1 to 3; preferably pyridyl.
在本发明的某一实施方案中，R 1-1、R 2-1、R 1-2、R 2-2、R 1-3、R 1-4和R 2-3独立地为C 1～C 10烷基、被一个或多个R b-1取代的C 1～C 10烷基、C 1～C 10烷基-O-或被一个或多个R b-2取代的C 1～C 10烷基-O-中， 所述的C 1～C 10烷基独立地为C 1～C 6烷基(例如甲基、乙基、正丙基、异丙基、正丁基、叔丁基、仲丁基、异丁基、戊基或己基)，较佳地为C 1～C 4的烷基(例如甲基、乙基、正丙基、异丙基、正丁基、仲丁基、异丁基或叔丁基)，更佳地为甲基或异丙基。 In a certain embodiment of the present invention, R 1-1 , R 2-1 , R 1-2 , R 2-2 , R 1-3 , R 1-4 and R 2-3 are independently C 1 ～ C 10 alkyl group, C 1 ～C 10 alkyl group substituted by one or more R b-1 , C 1 ～C 10 alkyl group-O- or C 1 ～C substituted by one or more R b-2 In 10 alkyl-O-, the C 1 ～C 10 alkyl is independently C 1 ～C 6 alkyl (for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl group, sec-butyl, isobutyl, pentyl or hexyl), preferably a C 1 ~ C 4 alkyl group (e.g. methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butoxy , Isobutyl or tert-butyl), more preferably methyl or isopropyl.
在本发明的某一实施方案中，R 1-1、R 2-1、R 1-2、R 2-2、R 1-3、R 1-4和R 2-3独立地为C 6～C 14芳基或被一个或多个R b-3取代的C 6～C 14芳基中，所述的C 6～C 14芳基独立地为C 6～C 10芳基；例如苯基或萘基。 In a certain embodiment of the present invention, R 1-1 , R 2-1 , R 1-2 , R 2-2 , R 1-3 , R 1-4 and R 2-3 are independently C 6 ～ In a C 14 aryl group or a C 6 ～C 14 aryl group substituted by one or more R b-3 , the C 6 ～C 14 aryl group is independently a C 6 ～C 10 aryl group; for example, phenyl or Naphthyl.
在本发明的某一实施方案中，R 1-1、R 2-1、R 1-2、R 2-2、R 1-3、R 1-4和R 2-3独立地为5-6元单环杂芳基或被一个或多个R b-4取代的5-6元单环杂芳基中，所述的C 1～C 12杂芳基独立地为杂原子选自N，杂原子数为1～3个；较佳地为吡啶基。 In a certain embodiment of the invention, R 1-1 , R 2-1 , R 1-2 , R 2-2 , R 1-3 , R 1-4 and R 2-3 are independently 5-6 In the 5-6 membered monocyclic heteroaryl group substituted by one or more R b-4 , the C 1 ～C 12 heteroaryl group is independently a heteroatom selected from N, hetero The number of atoms is 1 to 3; preferably pyridyl.
在本发明的某一实施方案中，当
Figure PCTCN2020081035-appb-000015
独立地为苯基时，
Figure PCTCN2020081035-appb-000016
独立地为
Figure PCTCN2020081035-appb-000017
(例如
Figure PCTCN2020081035-appb-000018
Figure PCTCN2020081035-appb-000019
)。 In an embodiment of the present invention, when
Figure PCTCN2020081035-appb-000015
When independently phenyl,
Figure PCTCN2020081035-appb-000016
Independently
Figure PCTCN2020081035-appb-000017
(E.g
Figure PCTCN2020081035-appb-000018
Figure PCTCN2020081035-appb-000019
).
在本发明的某一实施方案中，
Figure PCTCN2020081035-appb-000020
独立地为5-6元单环杂芳基或被一个或多个R c-2取代的5-6元单环杂芳基中，所述的5-6元单环杂芳基独立地为杂原子选自N，杂原子数为1～2个；较佳地为吡啶基。 In a certain embodiment of the invention,
Figure PCTCN2020081035-appb-000020
Is independently a 5-6 membered monocyclic heteroaryl group or a 5-6 membered monocyclic heteroaryl group substituted with one or more R c-2 , said 5-6 membered monocyclic heteroaryl group is independently The heteroatom is selected from N, and the number of heteroatoms is 1 to 2; preferably, it is pyridyl.
在本发明的某一实施方案中，R 6和R 11相同，R 7和R 12相同，R 8和R 13相同，R 9和R 14相同，R 10和R 15相同。 In a certain embodiment of the present invention, R 6 and R 11 are the same, R 7 and R 12 are the same, R 8 and R 13 are the same, R 9 and R 14 are the same, and R 10 and R 15 are the same.
在本发明的某一实施方案中，R独立地位于所在苯环与
Figure PCTCN2020081035-appb-000021
连接位点的邻位、间位或对位；较佳地，当R的个数为2个时，独立地位于所在苯环与
Figure PCTCN2020081035-appb-000022
连接位点的间位。 In an embodiment of the present invention, R is independently located on the benzene ring and
Figure PCTCN2020081035-appb-000021
The ortho, meta or para position of the connection site; preferably, when the number of R is 2, they are independently located on the benzene ring and
Figure PCTCN2020081035-appb-000022
The meta position of the connection site.
在本发明的某一实施方案中，R a-1、R a-2、R a-3、R a-4、R b-1、R b-2、R b-3、R b-4、R c-1和R c-2独立地为卤素中，所述的卤素(例如氟、氯、溴或碘)独立地为氟。 In a certain embodiment of the present invention, Ra -1 , Ra -2 , Ra -3 , Ra -4 , R b-1 , R b-2 , R b-3 , R b-4 , Where R c-1 and R c-2 are independently halogen, said halogen (e.g. fluorine, chlorine, bromine or iodine) is independently fluorine.
在本发明的某一实施方案中，R a-1、R a-2、R a-3、R a-4、R b-1、R b-2、R b-3、R b-4、R c-1和R c-2独立地为C 1～C 6烷基或C 1～C 6烷基-O-中，所述的C 1～C 6烷基或C 1～C 6烷基-O-中的C 1～C 6烷基(例如甲基、乙基、正丙基、异丙基、正丁基、叔丁基、仲丁基、异丁基、戊基或己基)独立地为C 1～C 4的烷基(例如甲基、乙基、正丙基、异丙基、正丁基、仲丁基、异丁基或叔丁基)，更佳地为甲基或异丙基。 In a certain embodiment of the present invention, Ra -1 , Ra -2 , Ra -3 , Ra -4 , R b-1 , R b-2 , R b-3 , R b-4 , R c-1 and R c-2 are independently C 1 ～C 6 alkyl or C 1 ～C 6 alkyl-O-, the C 1 ～ C 6 alkyl or C 1 ～C 6 alkyl The C 1 ～C 6 alkyl group in -O- (for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, sec-butyl, isobutyl, pentyl or hexyl) is independent The ground is a C 1 -C 4 alkyl group (such as methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl or tert-butyl), more preferably methyl or Isopropyl.
在本发明的某一实施方案中，R a-1、R a-2、R a-3、R a-4、R b-1、R b-2、R b-3、R b-4、R c-1和R c-2的个数独立地为1、2或3。 In a certain embodiment of the present invention, Ra -1 , Ra -2 , Ra -3 , Ra -4 , R b-1 , R b-2 , R b-3 , R b-4 , The number of R c-1 and R c-2 is 1, 2, or 3 independently.
在本发明的某一实施方案中，当R Y1、R 6、R 7、R 8、R 9、R 10、R 11、R 12、R 13、R 14和R 15独立地为被一个或多个R a-1取代的C 1～C 10烷基或被一个或多个R a-2取代的C 1～C 10烷基-O-时，所述的取代的C 1～C 10烷基或取代的C 1～C 10烷基-O-中的取代的C 1～C 10烷基独立地为三氟甲基。 In an embodiment of the present invention, when R Y1 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 and R 15 are independently selected by one or more When a C 1 ～C 10 alkyl group substituted by Ra-1 or a C 1 ～C 10 alkyl group-O- substituted by one or more Ra -2 , the substituted C 1 ～C 10 alkyl group or substituted C 1 ~ C 10 alkyl group substituted with -O- in the C 1 ~ C 10 alkyl group is independently trifluoromethyl.
在本发明的某一实施方案中，当R 1-1、R 2-1、R 1-2、R 2-2、R 1-3、R 1-4和R 2-3独立地为被一个或多个R b-1取代的C 1～C 10烷基或被一个或多个R b-2取代的C 1～C 10烷基-O-时，所述的取代的C 1～C 10烷基或取代的C 1～C 10烷基-O-中的取代的C 1～C 10烷基独立地为三氟甲基。 In a certain embodiment of the present invention, when R 1-1 , R 2-1 , R 1-2 , R 2-2 , R 1-3 , R 1-4 and R 2-3 are independently Or more C 1 ～C 10 alkyl substituted by R b-1 or C 1 ～C 10 alkyl-O- substituted by one or more R b-2 , the substituted C 1 ～C 10 alkyl or substituted C 1 ~ C 10 alkyl group substituted with -O- in the C 1 ~ C 10 alkyl group is independently trifluoromethyl.
在本发明的某一实施方案中，R 1-1、R 1-2、R 1-3和R 1-4独立地为氢、氘、C 1～C 10烷基、被一个或多个R b-1取代的C 1～C 10烷基、C 6～C 14芳基、被一个或多个R b-3取代的C 6～C 14芳基、5-6元单环杂芳基、被一个或多个R b-4取代的5-6元单环杂芳基或
Figure PCTCN2020081035-appb-000023
R 2-1、R 2-2和R 2-3独立地为氢。 In a certain embodiment of the present invention, R 1-1 , R 1-2 , R 1-3 and R 1-4 are independently hydrogen, deuterium, C 1 ～C 10 alkyl group, and one or more R b-1 is substituted with C 1 ~ C 10 alkyl group, C 6 ~ C 14 aryl group, substituted with one or more R b-3 is unsubstituted C 6 ~ C 14 aryl, 5-6 membered monocyclic heteroaryl, 5-6 membered monocyclic heteroaryl substituted by one or more R b-4 or
Figure PCTCN2020081035-appb-000023
R 2-1 , R 2-2 and R 2-3 are independently hydrogen.
在本发明的某一实施方案中，
Figure PCTCN2020081035-appb-000024
独立地为
Figure PCTCN2020081035-appb-000025
Figure PCTCN2020081035-appb-000026
Figure PCTCN2020081035-appb-000027
较佳地为
Figure PCTCN2020081035-appb-000028
Figure PCTCN2020081035-appb-000029
Figure PCTCN2020081035-appb-000030
In a certain embodiment of the invention,
Figure PCTCN2020081035-appb-000024
Independently
Figure PCTCN2020081035-appb-000025
Figure PCTCN2020081035-appb-000026
Figure PCTCN2020081035-appb-000027
Preferably
Figure PCTCN2020081035-appb-000028
Figure PCTCN2020081035-appb-000029
Figure PCTCN2020081035-appb-000030
在本发明的某一实施方案中，
Figure PCTCN2020081035-appb-000031
独立地为
Figure PCTCN2020081035-appb-000032
Figure PCTCN2020081035-appb-000033
Figure PCTCN2020081035-appb-000034
较佳地为
Figure PCTCN2020081035-appb-000035
Figure PCTCN2020081035-appb-000036
Figure PCTCN2020081035-appb-000037
In a certain embodiment of the invention,
Figure PCTCN2020081035-appb-000031
Independently
Figure PCTCN2020081035-appb-000032
Figure PCTCN2020081035-appb-000033
Figure PCTCN2020081035-appb-000034
Preferably
Figure PCTCN2020081035-appb-000035
Figure PCTCN2020081035-appb-000036
Figure PCTCN2020081035-appb-000037
在本发明的某一实施方案中，
Figure PCTCN2020081035-appb-000038
独立地为
Figure PCTCN2020081035-appb-000039
In a certain embodiment of the invention,
Figure PCTCN2020081035-appb-000038
Independently
Figure PCTCN2020081035-appb-000039
在本发明的某一实施方案中，R Y1、R 6、R 7、R 8、R 9、R 10、R 11、R 12、R 13、R 14和R 15独立地为氢、氘、卤素、氰基、C 1～C 10烷基、被一个或多个R a-1取代的C 1～C 10烷基、C 6～C 14芳基或被一个或多个R a-3取代的C 6～C 14芳基；较佳地为氢、氘、卤素、氰基、C 1～C 10烷基或被一个或多个R a-1取代的C 1～C 10烷基。 In a certain embodiment of the invention, R Y1 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 and R 15 are independently hydrogen, deuterium, halogen , cyano, C 1 ~ C 10 alkyl group, with one or more substituents R a-1 is C 1 ~ C 10 alkyl group, C 6 ~ C 14 aryl group by one or more of the substituents R a-3 C 6 ~ C 14 aryl group; preferably hydrogen, deuterium, halo, cyano, C 1 ~ C 10 alkyl group by one or more substituents R a-1 is C 1 ~ C 10 alkyl group.
在本发明的某一实施方案中，R为
Figure PCTCN2020081035-appb-000040
In a certain embodiment of the invention, R is
Figure PCTCN2020081035-appb-000040
在本发明的某一实施方案中，R 1、R 2、R 3、R 4和R 5中的1个或2个独立地为R；余者独立地为R Y1；R Y1、R 6、R 7、R 8、R 9、R 10、R 11、R 12、R 13、R 14和R 15独立地为氢、氘、卤素、氰基、C 1～C 10烷基、被一个或多个R a-1取代的C 1～C 10烷基、C 6～C 14芳基或被一个或多个R a-3取代的C 6～C 14芳基； In a certain embodiment of the present invention, one or two of R 1 , R 2 , R 3 , R 4 and R 5 are independently R; the rest are independently R Y1 ; R Y1 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14, and R 15 are independently hydrogen, deuterium, halogen, cyano, C 1 ～C 10 alkyl, and one or more R a-1 a-substituted C 1 ~ C 10 alkyl group, C 6 ~ C 14 aryl group by one or more R a-3 substituted C 6 ~ C 14 aryl group;
R 6和R 11相同，R 7和R 12相同，R 8和R 13相同，R 9和R 14相同，R 10和R 15相同； R 6 and R 11 are the same, R 7 and R 12 are the same, R 8 and R 13 are the same, R 9 and R 14 are the same, and R 10 and R 15 are the same;
R独立地为
Figure PCTCN2020081035-appb-000041
R is independently
Figure PCTCN2020081035-appb-000041
R 1-1、R 1-2、R 1-3和R 1-4独立地为氢、氘、C 1～C 10烷基、被一个或多个R b-1取代的C 1～C 10烷基、C 6～C 14芳基、被一个或多个R b-3取代的C 6～C 14芳基、5-6元单环杂芳基、被一个或多个R b-4取代的5-6元单环杂芳基或
Figure PCTCN2020081035-appb-000042
R 2-1、R 2-2和R 2-3独立地为氢。 R 1-1 , R 1-2 , R 1-3 and R 1-4 are independently hydrogen, deuterium, C 1～ C 10 alkyl, C 1 ～C 10 substituted by one or more R b-1 alkyl group, C 6 ~ C 14 aryl group, substituted with one or more R b-3 is unsubstituted C 6 ~ C 14 aryl, 5-6 membered monocyclic heteroaryl, substituted with one or more R b-4 5-6 membered monocyclic heteroaryl group or
Figure PCTCN2020081035-appb-000042
R 2-1 , R 2-2 and R 2-3 are independently hydrogen.
在本发明的某一实施方案中，当R 1、R 2、R 3、R 4和R 5中的2个独立地为R时，R相同。 In a certain embodiment of the present invention, when two of R 1 , R 2 , R 3 , R 4 and R 5 are independently R, R is the same.
在本发明的某一实施方案中，R 1、R 2、R 3、R 4和R 5中的1个为R；余者独立地为R Y1；或者，R 2和R 4独立地为R；余者独立地为R Y1；例如当R 2和R 4独立地为R时，R 2和R 4相同或不同，又例如相同。 In a certain embodiment of the present invention, one of R 1 , R 2 , R 3 , R 4 and R 5 is R; the rest are independently R Y1 ; or, R 2 and R 4 are independently R ; The rest are independently R Y1 ; For example, when R 2 and R 4 are independently R, R 2 and R 4 are the same or different, for example the same.
在本发明的某一实施方案中，R Y1独立地为氢。 In a certain embodiment of the invention, R Y1 is independently hydrogen.
在本发明的某一实施方案中，R 1、R 2、R 3、R 4和R 5中的1个为R；余者独立地为R Y1；或者，R 2和R 4独立地为R；余者独立地为R Y1，R Y1独立地为氢。 In a certain embodiment of the present invention, one of R 1 , R 2 , R 3 , R 4 and R 5 is R; the rest are independently R Y1 ; or, R 2 and R 4 are independently R ; The rest are independently R Y1 , and R Y1 are independently hydrogen.
在本发明的某一实施方案中，R 8和R 13独立地为氢、卤素、C 1～C 10烷基、或被一个或多个R a-1取 代的C 1～C 10烷基； In certain embodiments of the present invention, R 8 and R 13 are independently hydrogen, halogen, C 1 ~ C 10 alkyl group, or by one or more substituents R a-1 is C 1 ~ C 10 alkyl group;
例如，R a-1独立地为卤素，例如氟； For example, Ra -1 is independently halogen, such as fluorine;
又例如，所述的被一个或多个R a-1取代的C 1～C 10烷基为三氟甲基。 For another example, the C 1 -C 10 alkyl group substituted with one or more Ra -1 is trifluoromethyl.
在本发明的某一实施方案中，R 6、R 7、R 9、R 10、R 11、R 12、R 14和R 15独立地为氢。 In a certain embodiment of the invention, R 6 , R 7 , R 9 , R 10 , R 11 , R 12 , R 14 and R 15 are independently hydrogen.
在本发明的某一实施方案中，
Figure PCTCN2020081035-appb-000043
与
Figure PCTCN2020081035-appb-000044
相同或不同，例如相同。 In a certain embodiment of the invention,
Figure PCTCN2020081035-appb-000043
versus
Figure PCTCN2020081035-appb-000044
The same or different, such as the same.
在本发明的某一实施方案中，R 6、R 7、R 8、R 9、R 10、R 11、R 12、R 13、R 14和R 15独立地为氢、卤素、C 1～C 10烷基、或被一个或多个R a-1取代的C 1～C 10烷基； In a certain embodiment of the present invention, R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 and R 15 are independently hydrogen, halogen, C 1 ～C 10 alkyl groups, or C 1 ～C 10 alkyl groups substituted by one or more Ra -1 ;
例如，R 8和R 13独立地为氢、卤素、C 1～C 10烷基、或被一个或多个R a-1取代的C 1～C 10烷基；R 6、R 7、R 9、R 10、R 11、R 12、R 14和R 15独立地为氢； For example, R 8 and R 13 are independently hydrogen, halogen, C 1 ~ C 10 alkyl group, or by one or more substituents R a-1 is C 1 ~ C 10 alkyl group; R 6, R 7, R 9 , R 10 , R 11 , R 12 , R 14 and R 15 are independently hydrogen;
和/或，R a-1独立地为卤素，例如氟；又例如，所述的被一个或多个R a-1取代的C 1～C 10烷基为三氟甲基； And/or, R a-1 is independently halogen, such as fluorine; for another example, the C 1 to C 10 alkyl group substituted by one or more R a-1 is trifluoromethyl;
和/或，
Figure PCTCN2020081035-appb-000045
与
Figure PCTCN2020081035-appb-000046
相同或不同，例如相同。 and / or,
Figure PCTCN2020081035-appb-000045
versus
Figure PCTCN2020081035-appb-000046
The same or different, such as the same.
在本发明的某一实施方案中，R 1-1、R 2-1、R 1-2、R 2-2、R 1-3、R 1-4、R 2-3独立地为氢、C 6～C 14芳基、被一个或多个R b-3取代的C 6～C 14芳基、5-6元单环杂芳基、或
Figure PCTCN2020081035-appb-000047
In a certain embodiment of the present invention, R 1-1 , R 2-1 , R 1-2 , R 2-2 , R 1-3 , R 1-4 , R 2-3 are independently hydrogen, C 6 ~ C 14 aryl group, substituted with one or more R b-3 is unsubstituted C 6 ~ C 14 aryl, 5-6 membered monocyclic heteroaryl, or
Figure PCTCN2020081035-appb-000047
例如，R 1-1、R 1-2、R 1-3、R 1-4独立地为氢、C 6～C 14芳基、被一个或多个R b-3取代的C 6～C 14芳基、5-6元单环杂芳基、或
Figure PCTCN2020081035-appb-000048
For example, R 1-1, R 1-2, R 1-3, R 1-4 are independently hydrogen, C 6 ~ C 14 aryl group, substituted with one or more R b-3 is unsubstituted C 6 ~ C 14 Aryl, 5-6 membered monocyclic heteroaryl, or
Figure PCTCN2020081035-appb-000048
R 2-1、R 2-2、R 2-3独立地为氢。 R 2-1 , R 2-2 and R 2-3 are independently hydrogen.
在本发明的某一实施方案中，R 1-1、R 1-2、R 1-3、R 1-4独立地为氢、C 6～C 14芳基、被一个或多个R b- 3取代的C 6～C 14芳基、5-6元单环杂芳基、或
Figure PCTCN2020081035-appb-000049
In a certain embodiment of the present invention, R 1-1 , R 1-2 , R 1-3 , and R 1-4 are independently hydrogen, C 6 ～C 14 aryl, and one or more R b- 3- substituted C 6 ～C 14 aryl, 5-6 membered monocyclic heteroaryl, or
Figure PCTCN2020081035-appb-000049
例如，R b-3独立地为卤素、三氟甲基或C 1～C 6烷基。 For example, R b-3 is independently halogen, trifluoromethyl, or C 1 -C 6 alkyl.
在本发明的某一实施方案中，R 2-1、R 2-2、R 2-3独立地为氢。 In a certain embodiment of the invention, R 2-1 , R 2-2 and R 2-3 are independently hydrogen.
在本发明的某一实施方案中，R 1、R 2、R 3、R 4和R 5中的1个为R；余者独立地为R Y1；或者，R 2和R 4独立地为R；余者独立地为R Y1，R Y1独立地为氢； In a certain embodiment of the present invention, one of R 1 , R 2 , R 3 , R 4 and R 5 is R; the rest are independently R Y1 ; or, R 2 and R 4 are independently R ; The rest are independently R Y1 , and R Y1 are independently hydrogen;
R独立地为
Figure PCTCN2020081035-appb-000050
R is independently
Figure PCTCN2020081035-appb-000050
当R 2和R 4独立地为R时，R 2和R 4相同或不同； When R 2 and R 4 are independently R, R 2 and R 4 are the same or different;
R 6、R 7、R 8、R 9、R 10、R 11、R 12、R 13、R 14和R 15独立地为氢、卤素、C 1～C 10烷基、或被一个或多个R a-1取代的C 1～C 10烷基；R a-1独立地为卤素； R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 and R 15 are independently hydrogen, halogen, C 1 to C 10 alkyl, or one or more R a-1 is substituted with C 1 ~ C 10 alkyl group; R a-1 independently halogen;
Figure PCTCN2020081035-appb-000051
与
Figure PCTCN2020081035-appb-000052
相同或不同；
Figure PCTCN2020081035-appb-000051
versus
Figure PCTCN2020081035-appb-000052
The same or different
R 1-1、R 2-1、R 1-2、R 2-2、R 1-3、R 1-4、R 2-3独立地为氢、C 6～C 14芳基、被一个或多个R b-3取代的C 6～C 14芳基、5-6元单环杂芳基、或
Figure PCTCN2020081035-appb-000053
R b-3独立地为卤素、三氟甲基或C 1～C 6烷基； R 1-1 , R 2-1 , R 1-2 , R 2-2 , R 1-3 , R 1-4 , R 2-3 are independently hydrogen, C 6 ～C 14 aryl, and one or Multiple R b-3 substituted C 6 ～C 14 aryl groups, 5-6 membered monocyclic heteroaryl groups, or
Figure PCTCN2020081035-appb-000053
R b-3 is independently halogen, trifluoromethyl or C 1 ～C 6 alkyl;
例如，当R 2和R 4独立地为R时，R 2和R 4相同； For example, when R 2 and R 4 are independently R, R 2 and R 4 are the same;
R 8和R 13独立地为氢、卤素、C 1～C 10烷基、或被一个或多个R a-1取代的C 1～C 10烷基； R 8 and R 13 are independently hydrogen, halogen, C 1 ~ C 10 alkyl group, or by one or more substituents R a-1 is C 1 ~ C 10 alkyl group;
R a-1独立地为卤素； R a-1 is independently halogen;
R 6、R 7、R 9、R 10、R 11、R 12、R 14和R 15独立地为氢； R 6 , R 7 , R 9 , R 10 , R 11 , R 12 , R 14 and R 15 are independently hydrogen;
Figure PCTCN2020081035-appb-000054
与
Figure PCTCN2020081035-appb-000055
相同；
Figure PCTCN2020081035-appb-000054
versus
Figure PCTCN2020081035-appb-000055
the same;
R 1-1、R 1-2、R 1-3、R 1-4独立地为氢、C 6～C 14芳基、被一个或多个R b-3取代的C 6～C 14芳基、5-6元单环杂芳基、或
Figure PCTCN2020081035-appb-000056
 R 1-1, R 1-2, R 1-3 , R 1-4 are independently hydrogen, C 6 ~ C 14 aryl group, substituted with one or more R b-3 is unsubstituted C 6 ~ C 14 aryl group , 5-6 membered monocyclic heteroaryl, or
Figure PCTCN2020081035-appb-000056
R b-3独立地为卤素、三氟甲基或C 1～C 6烷基； R b-3 is independently halogen, trifluoromethyl or C 1 ～C 6 alkyl;
R 2-1、R 2-2、R 2-3独立地为氢。 R 2-1 , R 2-2 and R 2-3 are independently hydrogen.
在本发明的某一实施方案中，所述的如式I所示的1,3,5-三嗪类化合物为如下任何一个化合物：In a certain embodiment of the present invention, the 1,3,5-triazine compound represented by formula I is any one of the following compounds:
Figure PCTCN2020081035-appb-000057
Figure PCTCN2020081035-appb-000057
Figure PCTCN2020081035-appb-000058
Figure PCTCN2020081035-appb-000058
Figure PCTCN2020081035-appb-000059
Figure PCTCN2020081035-appb-000059
Figure PCTCN2020081035-appb-000060
Figure PCTCN2020081035-appb-000060
Figure PCTCN2020081035-appb-000061
Figure PCTCN2020081035-appb-000061
Figure PCTCN2020081035-appb-000062
Figure PCTCN2020081035-appb-000062
Figure PCTCN2020081035-appb-000063
Figure PCTCN2020081035-appb-000063
Figure PCTCN2020081035-appb-000064
Figure PCTCN2020081035-appb-000064
Figure PCTCN2020081035-appb-000065
Figure PCTCN2020081035-appb-000065
本发明所述式I化合物可按照本领域常规的化学合成方法制备得到，其步骤和条件可参考本领域类似反应的步骤和条件。The compound of formula I of the present invention can be prepared according to conventional chemical synthesis methods in the art, and the steps and conditions can refer to the steps and conditions of similar reactions in the art.
本发明提供了一种如式I所示的1,3,5-三嗪化合物的制备方法，其可包括如下任一方案：The present invention provides a preparation method of 1,3,5-triazine compound as shown in formula I, which may include any of the following schemes:
方案一，合成路线如下所示：Scheme 1, the synthetic route is as follows:
Figure PCTCN2020081035-appb-000066
Figure PCTCN2020081035-appb-000066
方案二，合成路线如下所示：Scheme two, the synthetic route is as follows:
Figure PCTCN2020081035-appb-000067
Figure PCTCN2020081035-appb-000067
方案三，合成路线如下所示：Scheme three, the synthetic route is as follows:
Figure PCTCN2020081035-appb-000068
Figure PCTCN2020081035-appb-000068
方案四，合成路线如下所示：Scheme 4, the synthetic route is as follows:
Figure PCTCN2020081035-appb-000069
Figure PCTCN2020081035-appb-000069
其中，R 1’和R 2’的定义同R 1、R 2、R 3、R 4、R 5、R 6、R 7、R 8、R 9和R 10，R 1-1、R 2-1、R 1-2、R 2-2、R 1、R 2、R 3、R 4、R 5、R 6、R 7、R 8、R 9、R 10、n1、n2和n3的定义如上所述，m1和m2独立地为0、 1、2、3或4。 Among them, R 1'and R 2'have the same definitions as R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and R 10 , R 1-1 , R 2- 1. R 1-2 , R 2-2 , R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , n1, n2 and n3 are as defined above Said, m1 and m2 are 0, 1, 2, 3 or 4 independently.
本发明提供了一种如式I所示的1,3,5-三嗪类化合物作为电子材料的应用。The present invention provides an application of a 1,3,5-triazine compound as shown in formula I as an electronic material.
在本发明的某一实施方案中，所述的电子材料作为电子传输材料和/或电子受体材料；较佳地为有机电致发光器件中的电子传输材料和/或电子受体材料。In an embodiment of the present invention, the electronic material is used as an electron transport material and/or electron acceptor material; preferably an electron transport material and/or electron acceptor material in an organic electroluminescence device.
本发明提供了一种如式I所示的1,3,5-三嗪类化合物在有机电致发光器件领域中的应用。The invention provides an application of a 1,3,5-triazine compound represented by formula I in the field of organic electroluminescence devices.
在本发明的某一实施方案中，所述的如式I所示的1,3,5-三嗪类化合物用于制备有机电致发光器件中的电子传输层、空穴阻挡层和发光层中的一种或多种。In an embodiment of the present invention, the 1,3,5-triazine compound represented by formula I is used to prepare the electron transport layer, the hole blocking layer and the light emitting layer in an organic electroluminescent device One or more of.
本发明提供了一种有机电致发光组合物，其包括电子给体材料和所述的如式I所示的1,3,5-三嗪类化合物。The present invention provides an organic electroluminescent composition, which includes an electron donor material and the 1,3,5-triazine compound represented by formula I.
在本发明的某一实施方案中，所述的有机电致发光组合物中的所述电子给体材料可为本领域常规的苯基或萘基咔唑类电子给体材料；所述的苯基或萘基咔唑类电子给体材料较佳地为含有2-3个苯基咔唑或者萘基咔唑基结构；所述的苯基或萘基咔唑类电子给体材料较佳地为如下任一化合物：In an embodiment of the present invention, the electron donor material in the organic electroluminescence composition may be a conventional phenyl or naphthylcarbazole electron donor material in the art; the benzene The phenyl or naphthylcarbazole type electron donor material preferably contains 2-3 phenylcarbazole or naphthylcarbazole group structures; the phenyl or naphthylcarbazole type electron donor material preferably Any of the following compounds:
Figure PCTCN2020081035-appb-000070
Figure PCTCN2020081035-appb-000071
Figure PCTCN2020081035-appb-000072
例如
Figure PCTCN2020081035-appb-000073
Figure PCTCN2020081035-appb-000070
Figure PCTCN2020081035-appb-000071
Figure PCTCN2020081035-appb-000072
E.g
Figure PCTCN2020081035-appb-000073
本发明中，所述的如式I所示的1,3,5-三嗪类化合物与所述的电子给体材料的摩尔比可为本领域常规的摩尔比(例如本领域中常规的激基复合物中电子受体材料与电子给体材料的摩尔比)，较佳地，所述的如式I所示的1,3,5-三嗪类化合物与所述的电子给体材料的摩尔比为3:1至1:3；更佳地为1:1。In the present invention, the molar ratio of the 1,3,5-triazine compound shown in formula I and the electron donor material can be a conventional molar ratio in the art (for example, a conventional excitation in the art). The molar ratio of the electron acceptor material to the electron donor material in the matrix composite), preferably, the 1,3,5-triazine compound shown in formula I and the electron donor material The molar ratio is 3:1 to 1:3; more preferably 1:1.
在本发明的某一实施方案中，所述的有机电致发光组合物中还可包括掺杂发光材料；所述的掺杂发光材料可为本领域中常规的掺杂发光材料，例如荧光发光材料和/或磷光发光材料(又称磷光配合物发光材料)。In an embodiment of the present invention, the organic electroluminescent composition may also include a doped luminescent material; the doped luminescent material may be a conventional doped luminescent material in the field, such as fluorescent light. Materials and/or phosphorescent luminescent materials (also called phosphorescent complex luminescent materials).
本发明中，所述的掺杂发光材料在所述的有机电致发光组合物中的质量百分比可为本领域常规的质量百分比，当所述的掺杂发光材料为荧光发光材料时，所述的掺杂发光材料在所述的组合物中的质量百分比较佳地为0.5WT％-2.0WT％(例如1WT％)；当所述的掺杂发光材料为磷光发光材料时，所述的掺杂发光材料在所述的组合物中的质量百分比较佳地为5.0WT％-15.0WT％(例如10WT％)。In the present invention, the mass percentage of the doped luminescent material in the organic electroluminescent composition can be a conventional mass percentage in the art. When the doped luminescent material is a fluorescent luminescent material, the The mass percentage of the doped luminescent material in the composition is preferably 0.5WT%-2.0WT% (for example, 1WT%); when the doped luminescent material is a phosphorescent luminescent material, the doped luminescent material The mass percentage of the heteroluminescent material in the composition is preferably 5.0 WT% to 15.0 WT% (for example, 10 WT%).
在本发明的某一实施方案中，所述的掺杂发光材料中，所述的磷光发光材料可为本领域中常规的磷光发光材料，本发明中较佳地为如下任一化合物：In an embodiment of the present invention, in the doped luminescent material, the phosphorescent luminescent material may be a conventional phosphorescent luminescent material in the art. In the present invention, it is preferably any of the following compounds:
Figure PCTCN2020081035-appb-000074
Figure PCTCN2020081035-appb-000074
其中，Ra 1、Ra 3、Rb 1、Rb 3、Rd 1、Rd 3、Re 4、Re 5、Re 6、Rf 7、Rf 8、Rf 9、Rb 10-1、Rb 10-2、Re 10-1、Re 10-2、Rf 10-1和Rf 10-2独立地为H或含有1-5个C的直链或支链烷基； Among them, Ra 1 , Ra 3 , Rb 1 , Rb 3 , Rd 1 , Rd 3 , Re 4 , Re 5 , Re 6 , Rf 7 , Rf 8 , Rf 9 , Rb 10-1 , Rb 10-2 , Re 10 -1 , Re 10-2 , Rf 10-1 and Rf 10-2 are independently H or a linear or branched alkyl group containing 1-5 C;
Ra 2、Rb 2和Rd 2独立地为H、含有1-5个C的直链或支链烷基、苯基或1-5个C的直链或支链烷基取代的苯基； Ra 2 , Rb 2 and Rd 2 are independently H, a linear or branched alkyl group containing 1 to 5 C, a phenyl group, or a phenyl substituted with a linear or branched chain alkyl group of 1 to 5 C;
Figure PCTCN2020081035-appb-000075
独立地为含有1-2个N的六元芳香杂环。
Figure PCTCN2020081035-appb-000075
It is independently a six-membered aromatic heterocyclic ring containing 1-2 N.
在本发明的某一实施方案中，所述的掺杂发光材料中，所述的磷光发光材料为IrPPy 3
Figure PCTCN2020081035-appb-000076
In an embodiment of the present invention, in the doped luminescent material, the phosphorescent luminescent material is IrPPy 3
Figure PCTCN2020081035-appb-000076
在本发明的某一实施方案中，所述的掺杂发光材料中，所述的荧光发光材料可为本领域中常规的荧光发光材料，本发明中较佳地为如下任一化合物：In an embodiment of the present invention, in the doped luminescent material, the fluorescent luminescent material may be a conventional fluorescent luminescent material in the art. In the present invention, it is preferably any of the following compounds:
Figure PCTCN2020081035-appb-000077
Figure PCTCN2020081035-appb-000077
Figure PCTCN2020081035-appb-000078
Figure PCTCN2020081035-appb-000078
其中，Rg 11-1、Rg 11-2、Rh 11-1、Rh 11-2独立地为含有1-5个C的直链或支链烷基； Wherein, Rg 11-1 , Rg 11-2 , Rh 11-1 , and Rh 11-2 are independently linear or branched alkyl groups containing 1-5 C;
Rg 12-1、Rg 12-2、Rh 13-1、Rh 13-2、Rh 13-3和Rh 13-4代表含有1-5个C的直链或支链烷基、F或CF 3； Rg 12-1 , Rg 12-2 , Rh 13-1 , Rh 13-2 , Rh 13-3 and Rh 13-4 represent linear or branched alkyl groups containing 1-5 C, F or CF 3 ;
Ri 14-1、Ri 14-2、Ri 15-1、Ri 15-2、Rj 16-1、Rj 16-2、Rj 17-1、Rj 17-2、Rk 18-1、Rk 18-2、Rk 18-3、Rk 18-4、Rk 19-1、Rk 19-2、Rk 19-3、Rk 19-4、Rl 20-1、Rl 20-2、Rl 20-3、Rl 20-4、Rm 23-1、Rm 24-1、Rn 26-1、Rn 27-1、Ro 29-1、Ro 30-1、Ro 32-1、Rp 34-1、Rp 35-1、Rp 36-1和Rp 37-1独立地为含有1-5个C的直链或支链烷基、环己烷或异丙基苯； Ri 14-1 , Ri 14-2 , Ri 15-1 , Ri 15-2 , Rj 16-1 , Rj 16-2 , Rj 17-1 , Rj 17-2 , Rk 18-1 , Rk 18-2 , Rk 18-3 , Rk 18-4 , Rk 19-1 , Rk 19-2 , Rk 19-3 , Rk 19-4 , Rl 20-1 , Rl 20-2 , Rl 20-3 , Rl 20-4 , Rm 23-1 , Rm 24-1 , Rn 26-1 , Rn 27-1 , Ro 29-1 , Ro 30-1 , Ro 32-1 , Rp 34-1 , Rp 35-1 , Rp 36-1 and Rp 37-1 is independently a linear or branched alkyl group containing 1-5 C, cyclohexane or cumene;
Rm 22-1、Rn 25-1、Ro 28-11和Rp 33-1为含有1-4个C的直链或支链烷基。 Rm 22-1 , Rn 25-1 , Ro 28-11 and Rp 33-1 are linear or branched alkyl groups containing 1-4 Cs.
在本发明的某一实施方案中，所述的掺杂发光材料中，所述的荧光发光材料为In an embodiment of the present invention, in the doped luminescent material, the fluorescent luminescent material is
Figure PCTCN2020081035-appb-000079
Figure PCTCN2020081035-appb-000079
本发明提供了一种如上所述的有机电致发光组合物作为有机电致发光材料的应用。The present invention provides an application of the above-mentioned organic electroluminescent composition as an organic electroluminescent material.
在本发明的某一实施方案中，所述的有机电致发光材料用于制备有机电致发光器件中的发光层。In an embodiment of the present invention, the organic electroluminescent material is used to prepare the light-emitting layer in an organic electroluminescent device.
本发明提供了一种有机电致发光器件，其含如上所述的有机电致发光组合物。The present invention provides an organic electroluminescent device, which contains the organic electroluminescent composition as described above.
在本发明的某一实施方案中，所述的有机电致发光组合物为发光层(发光层的发光原理是基于电子给体分子与电子受体分子形成的激基复合物即Exciplex形成的分子间电荷转移激发态)。In an embodiment of the present invention, the organic electroluminescent composition is a light-emitting layer (the light-emitting principle of the light-emitting layer is based on the exciplex formed by electron donor molecules and electron acceptor molecules, namely molecules formed by Exciplex Charge transfer between excited states).
在本发明的某一实施方案中，所述有机电致发光器件中还包括基板，以及依次形成在基板上的阳极层、有机发光功能层和阴极层；所述的有机发光功能层中，包括含如上所述的发光层，还可包括空穴注入层、空穴传输层、电子阻挡层、空穴阻挡层、电子传输层和电子注入层中的任意一种或者多种的组合；较佳地，所述的电子传输层中的电子传输材料与所述的有机电致发光组合物中的1,3,5-三嗪类化合物的结构相同。In an embodiment of the present invention, the organic electroluminescent device further includes a substrate, and an anode layer, an organic light-emitting functional layer, and a cathode layer sequentially formed on the substrate; the organic light-emitting functional layer includes The light-emitting layer as described above may also include any one or a combination of a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer, and an electron injection layer; preferably In particular, the electron transport material in the electron transport layer has the same structure as the 1,3,5-triazine compound in the organic electroluminescence composition.
本发明提供了一种所述的有机电致发光器件在有机电致发光显示器或有机电致发光照明光源中的应用。The invention provides an application of the organic electroluminescence device in an organic electroluminescence display or an organic electroluminescence illumination light source.
本领域技术人员可以理解，根据本领域中使用的惯例，本申请描述基团的结构式中所使用的
Figure PCTCN2020081035-appb-000080
是指，相应的基团通过该位点与化合物I中的其它片段、基团进行连接。 Those skilled in the art can understand that according to the conventions used in the art, the structural formula of the group described in this application is used
Figure PCTCN2020081035-appb-000080
It means that the corresponding group is connected to other fragments and groups in Compound I through this site.
本发明中，如无特殊说明，所述的“取代”的个数可为一个或多个；当为多个时，可为2个、3个或4个。In the present invention, unless otherwise specified, the number of the "substituted" can be one or more; when there are more than one, it can be 2, 3 or 4.
本发明中，当所述的“取代”的个数为多个时，所述的“取代”可相同或不同。In the present invention, when the number of the "substitution" is multiple, the "substitution" may be the same or different.
本发明中，“取代”的位置，如未做特别说明，位置可为任意。In the present invention, the position of "substitution" can be any position unless otherwise specified.
本发明中，如无特殊说明，所述的氢或H为自然丰度下的氢元素，即同位素氕、氘和氚的混合物，其中为氕的丰度为99.98％。In the present invention, unless otherwise specified, the hydrogen or H is a hydrogen element in natural abundance, that is, a mixture of isotopes protium, deuterium and tritium, in which the abundance of protium is 99.98%.
本发明中，所述的氘为D或 2H，也被称为重氢。 In the present invention, the deuterium is D or 2 H, which is also called deuterium.
本发明中，氘取代位点的氘的丰度大于99％。In the present invention, the abundance of deuterium at the deuterium substitution site is greater than 99%.
术语说明Term Description
除非另外定义，否则本文中所用的全部技术与科学术语均具有如本发明所属领域的普通技术人员通常理解的相同含义。Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by those of ordinary skill in the art to which the present invention belongs.
如本文所用，术语“含有”或“包括(包含)”可以是开放式、半封闭式和封闭式的。换言之，所述术语也包括“基本上由…构成”、或“由…构成”。As used herein, the term "containing" or "including (including)" can be open, semi-closed, and closed. In other words, the term also includes "substantially consisting of" or "consisting of".
基团定义Group definition
可在参考文献(包括Carey and Sundberg"ADVANCED ORGANIC CHEMISTRY 4TH ED."Vols.A(2000)and B(2001),Plenum Press,New York)中找到对标准化学术语的定义。Definitions of standard chemical terms can be found in references (including Carey and Sundberg "ADVANCED ORGANIC CHEMISTRY 4TH ED." Vols.A (2000) and B (2001), Plenum Press, New York).
在本说明书中，可由本领域技术人员选择基团及其取代基以提供稳定的结构部分和化合物。当通过从左向右书写的常规化学式描述取代基时，该取代基也同样包括从右向左书写结构式时所得到的在化学上等同的取代基。In this specification, groups and their substituents can be selected by those skilled in the art to provide stable structural parts and compounds. When a substituent is described by a conventional chemical formula written from left to right, the substituent also includes chemically equivalent substituents obtained when the structural formula is written from right to left.
本文所用的章节标题仅用于组织文章的目的，而不应被解释为对所述主题的限制。本申请中引用的所有文献或文献部分包括但不限于专利、专利申请、文章、书籍、操作手册和论文，均通过引用方式整体并入本文。The chapter headings used in this article are only for the purpose of organizing the article, and should not be construed as a limitation on the subject. All documents or document parts cited in this application, including but not limited to patents, patent applications, articles, books, operating manuals, and theses, are incorporated herein by reference in their entirety.
在本文中定义的某些化学基团前面通过简化符号来表示该基团中存在的碳原子总数。例如，C 1-C 6烷基是指具有总共1、2、3、4、5或6个碳原子的如下文所定义的烷基。简化符号中的碳原子总数不包括可能存在于所述基团的取代基中的碳。 Certain chemical groups defined herein are preceded by simplified symbols to indicate the total number of carbon atoms present in the group. For example, C 1 -C 6 alkyl refers to an alkyl group as defined below having a total of 1, 2, 3, 4, 5, or 6 carbon atoms. The total number of carbon atoms in the simplified notation does not include carbons that may be present in the substituents of the group.
在本文中，取代基中定义的数值范围如0至4、1-4、1至3等表明该范围内的整数，如1-6为0、1、2、3、4、5、6。In this context, the numerical range defined in the substituents, such as 0 to 4, 1-4, 1 to 3, etc., indicates an integer within the range, for example, 1-6 is 0, 1, 2, 3, 4, 5, 6.
除前述以外，当用于本申请的说明书及权利要求书中时，除非另外特别指明，否则以下术语具有如下所示的含义。In addition to the foregoing, when used in the specification and claims of this application, unless otherwise specified, the following terms have the following meanings.
在本申请中，术语“卤素”是指氟、氯、溴或碘。In this application, the term "halogen" means fluorine, chlorine, bromine or iodine.
在本申请中，作为基团或是其它基团的一部分(例如用在卤素取代的烷基等基团中)，术语“烷基”意指包括具有指定碳原子数目的支链和直链的饱和脂族烃基。例如，C 1～C 10。如在“C 1～C 6烷基”中定义为包括在直链或者支链结构中具有1、2、3、4、5、或者6个碳原子的基团。例如，本发明中，所述的C 1～C 6烷基各自独立地为甲基、乙基、丙基、丁基、戊基或己基；其中，丙基为C 3烷基(包括同分异构体，例如正丙基或异丙基)；丁基为C 4烷基(包括同分异构体，例如正丁基、仲丁基、异丁基或叔丁基)；戊基为C 5烷基(包括同分异构体，例如正戊基、1-甲基-丁基、1-乙基-丙基、2-甲基-1-丁基、3-甲基-1-丁基、异戊基、叔戊基或新戊基)；己基为C 6烷基(包括同分异构体，例如正己基或异己基)。 In this application, as a group or part of another group (for example, as used in halogen-substituted alkyl groups and the like), the term "alkyl" is meant to include branched and straight-chain chains with the specified number of carbon atoms Saturated aliphatic hydrocarbon group. For example, C 1 ～C 10 . As defined in "C 1 -C 6 alkyl", it includes groups having 1, 2, 3, 4, 5, or 6 carbon atoms in a linear or branched structure. For example, in the present invention, the C 1 ～C 6 alkyl groups are each independently methyl, ethyl, propyl, butyl, pentyl or hexyl; wherein, propyl is C 3 alkyl (including the same Isomers, such as n-propyl or isopropyl); butyl is C 4 alkyl (including isomers, such as n-butyl, sec-butyl, isobutyl or tert-butyl); pentyl is C 5 alkyl (including isomers, such as n-pentyl, 1-methyl-butyl, 1-ethyl-propyl, 2-methyl-1-butyl, 3-methyl-1- butyl, isopentyl, tert-pentyl or neopentyl); for the hexyl group C 6 alkyl group (including isomers, e.g. n-hexyl or isohexyl).
在本申请中，作为基团或是其它基团的一部分，术语“芳基”是指具有6-14个环原子以及提供在芳香族环系统中的零个杂原子单环的或多环的(例如，二环的或三环的)4n+2芳香族环系统(例如，在循环阵列中具有6，10，或14个共享的p电子)的基团(“C 6～C 14芳基”)。上述芳基单元的实例包括苯基、萘基、菲基、或者蒽基。 In this application, as a group or part of another group, the term "aryl" refers to a monocyclic or polycyclic group having 6-14 ring atoms and zero heteroatoms provided in the aromatic ring system (E.g., bicyclic or tricyclic) 4n+2 aromatic ring system (e.g., having 6, 10, or 14 shared p electrons in a cyclic array) group ("C 6 ～C 14 aryl) "). Examples of the aforementioned aryl unit include phenyl, naphthyl, phenanthryl, or anthracenyl.
在本申请中，作为基团或是其它基团的一部分，术语“杂芳基”是指具有环碳原子以及提供在该芳香族环系统中的1-4个环杂原子(其中每个杂原子独立地选自氮、氧以及硫)的5-6元单环的或多环的(例如，二环的或三环的)4n+2芳香族环系统的基团(“5-6元杂芳基”)。在此定义范围内的杂芳基包括但不限于：吖啶基、咔唑基、噌啉基、喹喔啉基、吡唑基、吲哚基、苯并三唑基、呋喃基、噻吩基、苯并噻吩基、苯并呋喃基、喹啉基、异喹啉基、噁唑基、异噁唑基、吲哚基、吡嗪基、哒嗪基、 吡啶基、嘧啶基、吡咯基、四氢喹啉。In this application, as a group or part of other groups, the term "heteroaryl" refers to having ring carbon atoms and 1-4 ring heteroatoms provided in the aromatic ring system (where each hetero Atoms independently selected from nitrogen, oxygen and sulfur) 5-6 membered monocyclic or polycyclic (for example, bicyclic or tricyclic) 4n+2 aromatic ring system group ("5-6 member Heteroaryl"). Heteroaryl groups within the scope of this definition include but are not limited to: acridinyl, carbazolyl, cinnolinyl, quinoxalinyl, pyrazolyl, indolyl, benzotriazolyl, furyl, thienyl , Benzothienyl, benzofuranyl, quinolinyl, isoquinolinyl, oxazolyl, isoxazolyl, indolyl, pyrazinyl, pyridazinyl, pyridinyl, pyrimidinyl, pyrrolyl, Tetrahydroquinoline.
本文所用术语“部分”、“结构部分”、“化学部分”、“基团”、“化学基团”是指分子中的特定片段或官能团。化学部分通常被认为是嵌入或附加到分子上的化学实体。The terms "part", "structural part", "chemical part", "group", and "chemical group" as used herein refer to specific fragments or functional groups in a molecule. The chemical moiety is generally considered to be a chemical entity embedded or attached to a molecule.
除非另有规定，本文使用的所有技术术语和科学术语具有要求保护主题所属领域的标准含义。倘若对于某术语存在多个定义，则以本文定义为准。Unless otherwise specified, all technical and scientific terms used herein have standard meanings in the field to which the subject matter belongs. If there are multiple definitions for a term, the definition herein shall prevail.
应该理解，在本发明中使用的单数形式，如“一种”，包括复数指代，除非另有规定。此外，术语“包括”是开放性限定并非封闭式，即包括本发明所指明的内容，但并不排除其他方面的内容。It should be understood that the singular form used in the present invention, such as "a", includes plural designations, unless otherwise specified. In addition, the term "including" is open-ended and not closed-ended, that is, includes the content specified in the present invention, but does not exclude other aspects.
除非另有说明，本发明采用质谱、元素分析的传统方法，各步骤和条件可参照本领域常规的操作步骤和条件。Unless otherwise specified, the present invention adopts traditional methods of mass spectrometry and elemental analysis, and the steps and conditions can refer to the conventional operating steps and conditions in the art.
除非另有指明，本发明采用分析化学、有机合成化学和光学的标准命名及标准实验室步骤和技术。在某些情况下，标准技术被用于化学合成、化学分析、发光器件性能检测。Unless otherwise specified, the present invention adopts standard nomenclature and standard laboratory procedures and techniques of analytical chemistry, synthetic organic chemistry and optics. In some cases, standard techniques are used for chemical synthesis, chemical analysis, and performance testing of light-emitting devices.
本发明的化合物可以在一个或多个构成该化合物的原子上包含非天然比例的原子同位素。例如，可用放射性同位素标记化合物，比如氘( 2H)。本发明的化合物的所有同位素组成的变换，无论放射性与否，都包括在本发明的范围之内。 The compounds of the present invention may contain unnatural proportions of atomic isotopes on one or more of the atoms constituting the compound. For example, compounds can be labeled with radioisotopes, such as deuterium ( 2 H). All changes in the isotopic composition of the compounds of the present invention, whether radioactive or not, are included in the scope of the present invention.
在不违背本领域常识的基础上，上述各优选条件，可任意组合，即得本发明各较佳实例。On the basis of not violating common knowledge in the field, the above-mentioned preferred conditions can be combined arbitrarily to obtain preferred embodiments of the present invention.
本发明所用试剂和原料均市售可得。The reagents and raw materials used in the present invention are all commercially available.
本发明的积极进步效果在于：本发明提供的所述如式I所示的取代的1,3,5-三嗪化合物具有良好的接受电子能力和电子传输能力；且具有良好的热稳定性。该类化合物可被用于有机电致发光领域。其可以单独使用作为电子传输层或空穴阻挡层使用，或与电子给体材料的组合物，复合形成复合主体材料，单独用于有机电致发光器件，这种复合主体材料可以与一些发光材料(包括磷光和荧光材料)掺杂构造有机电致发光材料的发光层。因此这种材料可以同时作为功能材料在电致发光器件的发光层及电子传输层/空穴阻挡层中应用，其优势在于电子传输层与发光层中的电子受体材料属于相同的分子，这样电子从电子传输层中进入到发光层中时无需客服势垒，因此有利于降低发光器件的驱动电压及效率滚降、提高器件的效率和寿命。The positive progress effect of the present invention is that: the substituted 1,3,5-triazine compound represented by formula I provided by the present invention has good electron accepting ability and electron transport ability; and has good thermal stability. Such compounds can be used in the field of organic electroluminescence. It can be used alone as an electron transport layer or hole blocking layer, or combined with an electron donor material to form a composite host material, and used alone in an organic electroluminescent device. This composite host material can be combined with some light-emitting materials (Including phosphorescent and fluorescent materials) Doping constructs the light-emitting layer of organic electroluminescent materials. Therefore, this material can be simultaneously used as a functional material in the light-emitting layer and electron transport layer/hole blocking layer of electroluminescent devices. Its advantage is that the electron transport layer and the electron acceptor material in the light-emitting layer belong to the same molecule. When electrons enter the light-emitting layer from the electron transport layer, there is no customer service barrier, which is beneficial to reduce the driving voltage and efficiency roll-off of the light-emitting device, and improve the efficiency and life of the device.
具体实施方式detailed description
下面通过实施例的方式进一步说明本发明，但并不因此将本发明限制在所述的实施例范围之中。下列实施例中未注明具体条件的实验方法，按照常规方法和条件，或按照商品说明书选择。The present invention will be further explained by way of examples below, but the present invention is not limited to the scope of the described examples. In the following examples, the experimental methods without specific conditions are selected according to conventional methods and conditions, or according to the product specification.
实施例1Example 1
Figure PCTCN2020081035-appb-000081
Figure PCTCN2020081035-appb-000081
2-氯-4,6-二苯基-1,3,5-三嗪4.02g(15mmol)，2-甲酰基苯硼酸2.70g(18mmol)，碳酸钾3.73g(27mmol)加入到250mL双口瓶中，加入THF 100mL，H 2O 20mL，氮气条件下加入催化剂四(三苯基膦)钯，回流12h。用二氯甲烷/水洗涤反应液，有机相旋去溶剂后，柱层析提纯，得白色固体中间体(3.58g，产率70.8％)。 2-Chloro-4,6-diphenyl-1,3,5-triazine 4.02g (15mmol), 2-formylphenylboronic acid 2.70g (18mmol), potassium carbonate 3.73g (27mmol) added to 250mL double mouth Into the bottle, add 100 mL of THF, 20 mL of H 2 O, add catalyst tetrakis (triphenylphosphine) palladium under nitrogen, and reflux for 12 hours. The reaction solution was washed with dichloromethane/water, the organic phase was rotated to remove the solvent, and then purified by column chromatography to obtain a white solid intermediate (3.58 g, yield 70.8%).
10mL水溶解NaHSO 3(2.36g，22.6mmol)，加入中间体0.510g(1.51mmol)，常温搅拌5h。然后加入邻氨基二苯胺0.333g(1.81mmol)，加入20mL乙醇，氮气保护下回流12h。冷却到室温后过滤，得到白色粗产品。用二氯甲烷柱层析得到白色固体产品0.630g(产率83.5％)。质谱分析确定的分子离子质量为：501.00(计算值为：501.20)；理论元素含量(％)C 34H 23N 5：C,81.42；H,4.62；N,13.96；实测元素含量(％)：C,81.25；H,4.60；N,14.22。上述分析结果表明，获得的产物为目标产品。 Dissolve NaHSO 3 (2.36 g, 22.6 mmol) in 10 mL of water, add 0.510 g (1.51 mmol) of the intermediate, and stir at room temperature for 5 hours. Then add 0.333 g (1.81 mmol) of o-aminodiphenylamine, add 20 mL of ethanol, and reflux for 12 h under nitrogen protection. After cooling to room temperature, it was filtered to obtain a white crude product. The white solid product 0.630 g (yield 83.5%) was obtained by methylene chloride column chromatography. The molecular ion mass determined by mass spectrometry analysis is: 501.00 (calculated value: 501.20); theoretical element content (%) C 34 H 23 N 5 : C, 81.42; H, 4.62; N, 13.96; measured element content (%): C, 81.25; H, 4.60; N, 14.22. The above analysis results show that the obtained product is the target product.
实施例2Example 2
Figure PCTCN2020081035-appb-000082
Figure PCTCN2020081035-appb-000082
依照实施例1的合成，步骤相同，用化合物4-甲酰基苯硼酸代替化合物2-甲酰基苯硼酸，得到白色化合物0.523g(产率66.7％)，质谱分析确定的分子离子质量为：501.12(计算值为：501.20)；理论元素含量(％)C 34H 23N 5：C,81.42；H,4.62；N,13.96；实测元素含量(％)：C,81.37；H,4.60；N,14.28。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 1, the steps were the same, and the compound 4-formylphenylboronic acid was used instead of the compound 2-formylphenylboronic acid to obtain 0.523 g of a white compound (yield 66.7%). The molecular ion mass determined by mass spectrometry was 501.12 ( Calculated value: 501.20); theoretical element content (%) C 34 H 23 N 5 : C, 81.42; H, 4.62; N, 13.96; measured element content (%): C, 81.37; H, 4.60; N, 14.28 . The above analysis results show that the obtained product is the target product.
实施例3Example 3
Figure PCTCN2020081035-appb-000083
Figure PCTCN2020081035-appb-000083
依照实施例1的合成，步骤相同，用化合物3-甲酰基苯硼酸代替化合物2-甲酰基苯硼酸，得到白色化合物0.632g(产率80.6％)，质谱分析确定的分子离子质量为：501.04(计算值为：501.20)；理论元素含量(％)C 34H 23N 5：C,81.42；H,4.62；N,13.96；实测元素含量(％)：C,81.45；H,4.65；N,14.02。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 1, the steps were the same, and the compound 3-formylphenylboronic acid was used instead of the compound 2-formylphenylboronic acid to obtain 0.632g of a white compound (yield 80.6%). The molecular ion mass determined by mass spectrometry was 501.04( Calculated value: 501.20); theoretical element content (%) C 34 H 23 N 5 : C, 81.42; H, 4.62; N, 13.96; measured element content (%): C, 81.45; H, 4.65; N, 14.02 . The above analysis results show that the obtained product is the target product.
实施例4Example 4
Figure PCTCN2020081035-appb-000084
Figure PCTCN2020081035-appb-000084
10mL水溶解NaHSO 3(4.70g，45.0mmol)，加入苯甲醛0.350g(3.30mmol)，常温搅拌5h，然后加入N-(4-溴苯基)-1,2-苯二胺0.786g(3.00mmol)，加入20mL乙醇，氮气保护下回流12h。冷却到室温后过滤，得到白色固体粗产品1.43g(产率94.7％)。 Dissolve NaHSO 3 (4.70g, 45.0mmol) in 10mL of water, add 0.350g (3.30mmol) of benzaldehyde, stir at room temperature for 5h, and then add 0.786g (3.00 of N-(4-bromophenyl)-1,2-phenylenediamine) mmol), add 20mL ethanol, and reflux for 12h under nitrogen protection. After cooling to room temperature, it was filtered to obtain 1.43 g of a crude white solid product (yield 94.7%).
将上述粗产品0.696g(2.00mmol)，联硼酸频那醇酯1.02g(4.00mmol)，干燥的醋酸钾1.96g(20.0mmol)，以及干燥的1,4-二氧六环120mL于250mL双口瓶中，在氮气保护条件下加入催化剂[1,1'-双(二苯基膦基)二茂铁]二氯化钯150mg(0.20mmol)，回流24h。冷却到室温后，过滤除去醋酸钾，滤液除去二氧六环后用二氯甲烷/水洗涤，有机相除去有机溶剂后，用二氯甲烷做展开剂柱层析，得到白色固体中间体745mg(产率93.6％)。The above crude product 0.696g (2.00mmol), 1.02g (4.00mmol) of pinacol biborate, 1.96g (20.0mmol) of dried potassium acetate, and 120mL of dried 1,4-dioxane in 250mL of dioxane In the mouth flask, add 150 mg (0.20 mmol) of palladium dichloride catalyst [1,1'-bis(diphenylphosphino)ferrocene] dichloride under nitrogen protection, and reflux for 24 hours. After cooling to room temperature, potassium acetate was removed by filtration, and the filtrate was washed with dichloromethane/water after removing dioxane. After removing the organic solvent from the organic phase, column chromatography was performed with dichloromethane as a developing solvent to obtain a white solid intermediate 745mg ( Yield 93.6%).
将上述白色中间体594mg(1.50mmol)，2-氯-4,6-二苯基-1,3,5-三嗪1.00g(1.65mmol)，碳酸钾440mg(4.5mmol)加入到100mL双口瓶中，加入THF 25mL，H 2O 3mL，氮气条件下加入催化剂四(三苯基膦)钯25.0mg，回流12h。用二氯甲烷/水洗涤反应液，有机相旋去溶剂后，柱层析提纯，得白色固体化合物550mg(产率73.2％)。质谱分析确定的分子离子质量为：501.12(计算值为：501.20)；理论元素含量(％)C 34H 23N 5：C,81.42；H,4.62；N,13.96；实测元素含量(％)：C,81.35；H,4.67；N,14.03。上述分析结果表明，获得的产物为目标产品。 Add 594mg (1.50mmol) of the above white intermediate, 1.00g (1.65mmol) of 2-chloro-4,6-diphenyl-1,3,5-triazine, and 440mg (4.5mmol) of potassium carbonate to 100mL double mouth Add 25 mL of THF, 3 mL of H 2 O to the bottle, add 25.0 mg of tetrakis (triphenylphosphine) palladium catalyst under nitrogen conditions, and reflux for 12 hours. The reaction solution was washed with dichloromethane/water, and the organic phase was rotated to remove the solvent, and then purified by column chromatography to obtain 550 mg of a white solid compound (yield 73.2%). The molecular ion mass determined by mass spectrometry analysis is: 501.12 (calculated value: 501.20); theoretical element content (%) C 34 H 23 N 5 : C, 81.42; H, 4.62; N, 13.96; measured element content (%): C, 81.35; H, 4.67; N, 14.03. The above analysis results show that the obtained product is the target product.
实施例5Example 5
Figure PCTCN2020081035-appb-000085
Figure PCTCN2020081035-appb-000085
依照实施例4的合成，步骤相同，用化合物N-(3-溴苯基)-1,2-苯二胺代替化合物N-(4-溴苯基)-1,2-苯二胺，得到白色化合物638mg(产率85.0％)。质谱分析确定的分子离子质量为：501.08(计算值为：501.20)；理论元素含量(％)C 34H 23N 5：C,81.42；H,4.62；N,13.96；实测元素含量(％)：C,81.35；H,4.55；N,14.12。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 4, the steps are the same, and the compound N-(3-bromophenyl)-1,2-phenylenediamine is substituted for the compound N-(4-bromophenyl)-1,2-phenylenediamine to obtain White compound 638 mg (yield 85.0%). The molecular ion mass determined by mass spectrometry analysis is: 501.08 (calculated value: 501.20); theoretical element content (%) C 34 H 23 N 5 : C, 81.42; H, 4.62; N, 13.96; measured element content (%): C, 81.35; H, 4.55; N, 14.12. The above analysis results show that the obtained product is the target product.
实施例6Example 6
Figure PCTCN2020081035-appb-000086
Figure PCTCN2020081035-appb-000086
依照实施例4的合成，步骤相同，用化合物N-(2-溴苯基)-1,2-苯二胺代替化合物N-(4-溴苯基)-1,2-苯二胺，得到白色化合物0.523g(产率66.7％)，质谱分析确定的分子离子质量为：501.32(计算值为：501.20)；理论元素含量(％)C 34H 23N 5：C,81.42；H,4.62；N,13.96；实测元素含量(％)：C,81.38；H,4.57；N,14.02。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 4, the steps are the same, and the compound N-(2-bromophenyl)-1,2-phenylenediamine is substituted for the compound N-(4-bromophenyl)-1,2-phenylenediamine to obtain 0.523g of white compound (yield 66.7%), the molecular ion mass determined by mass spectrometry analysis is: 501.32 (calculated value: 501.20); theoretical element content (%) C 34 H 23 N 5 : C, 81.42; H, 4.62; N, 13.96; Measured element content (%): C, 81.38; H, 4.57; N, 14.02. The above analysis results show that the obtained product is the target product.
实施例7Example 7
Figure PCTCN2020081035-appb-000087
Figure PCTCN2020081035-appb-000087
依照实施例1的合成，步骤相同，用化合物N-(3-吡啶基)-1,2-苯二胺代替化合物邻氨基二苯胺，得到白色化合物0.553g(产率70.5％)，质谱分析确定的分子离子质量为：502.28(计算值为：502.19)；理论元素含量(％)C 33H 22N 6：C，78.87；H，4.41；N，16.72，实测元素含量(％)：C，78.95；H，4.33；N，16.85。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 1, the steps were the same, and the compound N-(3-pyridyl)-1,2-phenylenediamine was used instead of the compound o-aminodiphenylamine to obtain 0.553g of white compound (yield 70.5%), which was confirmed by mass spectrometry The molecular ion mass of is: 502.28 (calculated value: 502.19); theoretical element content (%) C 33 H 22 N 6 : C, 78.87; H, 4.41; N, 16.72, measured element content (%): C, 78.95 ; H, 4.33; N, 16.85. The above analysis results show that the obtained product is the target product.
实施例8Example 8
Figure PCTCN2020081035-appb-000088
Figure PCTCN2020081035-appb-000088
依照实施例1的合成，步骤相同，用化合物N-(4-吡啶基)-1,2-苯二胺代替化合物邻氨基二苯胺，得到白色化合物0.356g(产率45.4％)，质谱分析确定的分子离子质量为：502.31(计算值为：502.19)；理论元素含量(％)C 33H 22N 6：C，78.87；H，4.41；N，16.72，实测元素含量(％)：C，78.95；H，4.61；N，16.63。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 1, the steps were the same, and the compound N-(4-pyridyl)-1,2-phenylenediamine was used instead of the compound o-aminodiphenylamine to obtain 0.356g of white compound (yield 45.4%), which was confirmed by mass spectrometry The molecular ion mass of is: 502.31 (calculated value: 502.19); theoretical element content (%) C 33 H 22 N 6 : C, 78.87; H, 4.41; N, 16.72, measured element content (%): C, 78.95 ; H, 4.61; N, 16.63. The above analysis results show that the obtained product is the target product.
实施例9Example 9
Figure PCTCN2020081035-appb-000089
Figure PCTCN2020081035-appb-000089
依照实施例3的合成，步骤相同，用化合物N-(3-吡啶基)-1,2-苯二胺代替化合物邻氨基二苯胺，得到白色化合物0.435g(产率55.5％)，质谱分析确定的分子离子质量为：502.20(计算值为：502.19)；理论元素含量(％)C 33H 22N 6：C，78.87；H，4.41；N，16.72，实测元素含量(％)：C，78.85；H，4.41；N，16.83。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 3, the steps were the same, and the compound N-(3-pyridyl)-1,2-phenylenediamine was used instead of the compound o-aminodiphenylamine to obtain 0.435g of white compound (yield 55.5%), which was confirmed by mass spectrometry The molecular ion mass of is: 502.20 (calculated value: 502.19); theoretical element content (%) C 33 H 22 N 6 : C, 78.87; H, 4.41; N, 16.72, measured element content (%): C, 78.85 ; H, 4.41; N, 16.83. The above analysis results show that the obtained product is the target product.
实施例10Example 10
Figure PCTCN2020081035-appb-000090
Figure PCTCN2020081035-appb-000090
依照实施例3的合成，步骤相同，用化合物N-(4-吡啶基)-1,2-苯二胺代替化合物邻氨基二苯胺，得到白色化合物0.398g(产率50.8％)，质谱分析确定的分子离子质量为：502.18(计算值为：502.19)；理论元素含量(％)C 33H 22N 6：C，78.87；H，4.41；N，16.72，实测元素含量(％)：C，78.88；H，4.49；N，16.81。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 3, the steps were the same, the compound N-(4-pyridyl)-1,2-phenylenediamine was used instead of the compound o-aminodiphenylamine to obtain 0.398g of white compound (yield 50.8%), which was confirmed by mass spectrometry The molecular ion mass of is: 502.18 (calculated value: 502.19); theoretical element content (%) C 33 H 22 N 6 : C, 78.87; H, 4.41; N, 16.72, measured element content (%): C, 78.88 ; H, 4.49; N, 16.81. The above analysis results show that the obtained product is the target product.
实施例11Example 11
Figure PCTCN2020081035-appb-000091
Figure PCTCN2020081035-appb-000091
依照实施例2的合成，步骤相同，用化合物N-(3-吡啶基)-1,2-苯二胺代替化合物邻氨基二苯胺，得到白色化合物0.444g(产率56.6％)，质谱分析确定的分子离子质量为：502.08(计算值为：502.19)；理论元素含量(％)C 33H 22N 6：C，78.87；H，4.41；N，16.72，实测元素含量(％)：C，78.98；H，4.28；N，16.77。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 2, the steps are the same, the compound N-(3-pyridyl)-1,2-phenylenediamine is used instead of the compound o-aminodiphenylamine to obtain 0.444g of white compound (yield 56.6%), which is confirmed by mass spectrometry The molecular ion mass of is: 502.08 (calculated value: 502.19); theoretical element content (%) C 33 H 22 N 6 : C, 78.87; H, 4.41; N, 16.72, measured element content (%): C, 78.98 ; H, 4.28; N, 16.77. The above analysis results show that the obtained product is the target product.
实施例12Example 12
Figure PCTCN2020081035-appb-000092
Figure PCTCN2020081035-appb-000092
依照实施例2的合成，步骤相同，用化合物N-(4-吡啶基)-1,2-苯二胺代替化合物邻氨基二苯胺，得到白色化合物0.466g(产率59.4％)，质谱分析确定的分子离子质量为：502.18(计算值为：502.19)；理论元素含量(％)C 33H 22N 6：C，78.87；H，4.41；N，16.72，实测元素含量(％)：C，78.95；H，4.61；N，16.83。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 2, the steps were the same, and the compound N-(4-pyridyl)-1,2-phenylenediamine was used instead of the compound o-aminodiphenylamine to obtain 0.466g of white compound (yield 59.4%), which was confirmed by mass spectrometry The molecular ion mass of is: 502.18 (calculated value: 502.19); theoretical element content (%) C 33 H 22 N 6 : C, 78.87; H, 4.41; N, 16.72, measured element content (%): C, 78.95 ; H, 4.61; N, 16.83. The above analysis results show that the obtained product is the target product.
实施例13Example 13
Figure PCTCN2020081035-appb-000093
Figure PCTCN2020081035-appb-000093
依照实施例6的合成，步骤相同，用化合物3-醛基吡啶代替化合物苯甲醛，得到白色化合物0.425g(产率54.2％)，质谱分析确定的分子离子质量为：502.13(计算值为：502.19)；理论元素含量(％)C 33H 22N 6：C，78.87；H，4.41；N，16.72，实测元素含量(％)：C，78.89；H，4.21；N，16.93。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 6, the steps were the same, and the compound 3-aldehyde pyridine was used instead of the compound benzaldehyde to obtain 0.425 g of a white compound (yield 54.2%). The molecular ion mass determined by mass spectrometry was 502.13 (calculated value: 502.19). ); Theoretical element content (%) C 33 H 22 N 6 : C, 78.87; H, 4.41; N, 16.72, the measured element content (%): C, 78.89; H, 4.21; N, 16.93. The above analysis results show that the obtained product is the target product.
实施例14Example 14
Figure PCTCN2020081035-appb-000094
Figure PCTCN2020081035-appb-000094
依照实施例6的合成，步骤相同，用化合物4-醛基吡啶代替化合物苯甲醛，得到白色化合物0.289g(产率36.9％)，质谱分析确定的分子离子质量为：502.22(计算值为：502.19)；理论元素含量(％)C 33H 22N 6：C，78.87；H，4.41；N，16.72，实测元素含量(％)：C，78.89；H，4.22；N，16.90。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 6, the steps were the same, and the compound 4-aldehyde pyridine was used instead of the compound benzaldehyde to obtain 0.289 g of a white compound (yield 36.9%). The molecular ion mass determined by mass spectrometry was 502.22 (calculated value: 502.29). ); Theoretical element content (%) C 33 H 22 N 6 : C, 78.87; H, 4.41; N, 16.72, the measured element content (%): C, 78.89; H, 4.22; N, 16.90. The above analysis results show that the obtained product is the target product.
实施例15Example 15
Figure PCTCN2020081035-appb-000095
Figure PCTCN2020081035-appb-000095
依照实施例5的合成，步骤相同，用化合物3-醛基吡啶代替化合物苯甲醛，得到白色化合物0.333g(产率42.5％)，质谱分析确定的分子离子质量为：502.22(计算值为：502.19)；理论元素含量(％)C 33H 22N 6：C，78.87；H，4.41；N，16.72，实测元素含量(％)：C，78.86；H，4.40；N，16.81。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 5, the steps were the same, and the compound 3-aldehyde pyridine was used instead of the compound benzaldehyde to obtain 0.333 g of the white compound (yield 42.5%). The mass of the molecular ion determined by mass spectrometry was 502.22 (calculated value: 502.29). ); Theoretical element content (%) C 33 H 22 N 6 : C, 78.87; H, 4.41; N, 16.72, the measured element content (%): C, 78.86; H, 4.40; N, 16.81. The above analysis results show that the obtained product is the target product.
实施例16Example 16
Figure PCTCN2020081035-appb-000096
Figure PCTCN2020081035-appb-000096
依照实施例5的合成，步骤相同，用化合物4-醛基吡啶代替化合物苯甲醛，得到白色化合物0.259g(产率33.0％)，质谱分析确定的分子离子质量为：502.23(计算值为：502.19)；理论元素含量(％)C 33H 22N 6：C，78.87；H，4.41；N，16.72，实测元素含量(％)：C，78.87；H，4.51；N，16.87。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 5, the steps were the same, and the compound 4-aldehyde pyridine was used instead of the compound benzaldehyde to obtain 0.259 g of the white compound (yield 33.0%). The mass of the molecular ion determined by mass spectrometry was: 502.23 (calculated value: 502.29) ); Theoretical element content (%) C 33 H 22 N 6 : C, 78.87; H, 4.41; N, 16.72, the measured element content (%): C, 78.87; H, 4.51; N, 16.87. The above analysis results show that the obtained product is the target product.
实施例17Example 17
Figure PCTCN2020081035-appb-000097
Figure PCTCN2020081035-appb-000097
依照实施例4的合成，步骤相同，用化合物3-醛基吡啶代替化合物苯甲醛，得到白色化合物0.295g(产率37.7％)，质谱分析确定的分子离子质量为：502.15(计算值为：502.19)；理论元素含量(％) C 33H 22N 6：C，78.87；H，4.41；N，16.72，实测元素含量(％)：C，78.75；H，4.21；N，16.73。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 4, the steps were the same, and the compound 3-aldehyde pyridine was used instead of the compound benzaldehyde to obtain 0.295 g of a white compound (yield 37.7%). The molecular ion mass determined by mass spectrometry was 502.15 (calculated value: 502.19). ); Theoretical element content (%) C 33 H 22 N 6 : C, 78.87; H, 4.41; N, 16.72, the measured element content (%): C, 78.75; H, 4.21; N, 16.73. The above analysis results show that the obtained product is the target product.
实施例18Example 18
Figure PCTCN2020081035-appb-000098
Figure PCTCN2020081035-appb-000098
依照实施例4的合成，步骤相同，用化合物4-醛基吡啶代替化合物苯甲醛，得到白色化合物0.318g(产率40.6％)，质谱分析确定的分子离子质量为：502.18(计算值为：502.19)；理论元素含量(％)C 33H 22N 6：C，78.87；H，4.41；N，16.72，实测元素含量(％)：C，78.88；H，4.42；N，16.84。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 4, the steps were the same, and the compound 4-aldehyde pyridine was used instead of the compound benzaldehyde to obtain 0.318 g of a white compound (yield 40.6%). The molecular ion mass determined by mass spectrometry analysis was: 502.18 (calculated value: 502.19) ); Theoretical element content (%) C 33 H 22 N 6 : C, 78.87; H, 4.41; N, 16.72, the measured element content (%): C, 78.88; H, 4.42; N, 16.84. The above analysis results show that the obtained product is the target product.
实施例19Example 19
Figure PCTCN2020081035-appb-000099
Figure PCTCN2020081035-appb-000099
依照实施例1的合成，步骤相同，用化合物N 1-(2-氟苯基)-1,2-苯二胺代替化合物邻氨基二苯胺，得到白色化合物0.523g(产率68.2％)，质谱分析确定的分子离子质量为：519.28(计算值为：519.19)；理论元素含量(％)C 34H 22FN 5：C,78.60；H,4.27；F,3.66；N,13.48，实测元素含量(％)：C,78.55；H,4.24；F,3.69；N,13.41。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 1, the steps are the same, and the compound N 1 -(2-fluorophenyl)-1,2-phenylenediamine is used instead of the compound o-aminodiphenylamine to obtain 0.523 g of a white compound (yield 68.2%), mass spectrum The molecular ion mass determined by analysis is: 519.28 (calculated value: 519.19); theoretical element content (%) C 34 H 22 FN 5 : C, 78.60; H, 4.27; F, 3.66; N, 13.48, measured element content ( %): C, 78.55; H, 4.24; F, 3.69; N, 13.41. The above analysis results show that the obtained product is the target product.
实施例20Example 20
Figure PCTCN2020081035-appb-000100
Figure PCTCN2020081035-appb-000100
依照实施例1的合成，步骤相同，用化合物N 1-(3-氟苯基)-1,2-苯二胺代替化合物邻氨基二苯胺，得到白色化合物0.512g(产率65.6％)，质谱分析确定的分子离子质量为：519.33(计算值为：519.19)；理论元素含量(％)C 34H 22FN 5：C,78.60；H,4.27；F,3.66；N,13.48，实测元素含量(％)：C,78.57；H,4.26；F,3.71；N,13.43。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 1, the steps were the same, and the compound N 1 -(3-fluorophenyl)-1,2-phenylenediamine was used instead of the compound o-aminodiphenylamine to obtain 0.512 g of white compound (yield 65.6%), mass spectrum The molecular ion mass determined by analysis is: 519.33 (calculated value: 519.19); theoretical element content (%) C 34 H 22 FN 5 : C,78.60; H, 4.27; F, 3.66; N, 13.48, measured element content ( %): C, 78.57; H, 4.26; F, 3.71; N, 13.43. The above analysis results show that the obtained product is the target product.
实施例21Example 21
Figure PCTCN2020081035-appb-000101
Figure PCTCN2020081035-appb-000101
依照实施例1的合成，步骤相同，用化合物N 1-(4-氟苯基)-1,2-苯二胺代替化合物邻氨基二苯胺，得到白色化合物0.502g(产率64.4％)，质谱分析确定的分子离子质量为：519.09(计算值为：519.19)；理论元素含量(％)C 34H 22FN 5：C,78.60；H,4.27；F,3.66；N,13.48，实测元素含量(％)：C,78.55；H,4.24；F,3.69；N,13.41。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 1, the steps were the same, and the compound N 1 -(4-fluorophenyl)-1,2-phenylenediamine was used instead of the o-aminodiphenylamine compound to obtain 0.502 g of a white compound (yield 64.4%), mass spectrum The molecular ion mass determined by analysis is: 519.09 (calculated value: 519.19); theoretical element content (%) C 34 H 22 FN 5 : C, 78.60; H, 4.27; F, 3.66; N, 13.48, measured element content ( %): C, 78.55; H, 4.24; F, 3.69; N, 13.41. The above analysis results show that the obtained product is the target product.
实施例22Example 22
Figure PCTCN2020081035-appb-000102
Figure PCTCN2020081035-appb-000102
依照实施例3的合成，步骤相同，用化合物N 1-(2-氟苯基)-1,2-苯二胺代替化合物邻氨基二苯胺，得到白色化合物0.488g(产率62.6％)，质谱分析确定的分子离子质量为：519.29(计算值为：519.19)；理论元素含量(％)C 34H 22FN 5：C,78.60；H,4.27；F,3.66；N,13.48，实测元素含量(％)：C,78.57；H,4.23；F,3.68；N,13.40。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 3, the steps were the same, and the compound N 1 -(2-fluorophenyl)-1,2-phenylenediamine was used instead of the o-aminodiphenylamine compound to obtain 0.488 g of the white compound (yield 62.6%). Mass spectrum The molecular ion mass determined by analysis is: 519.29 (calculated value: 519.19); theoretical element content (%) C 34 H 22 FN 5 : C, 78.60; H, 4.27; F, 3.66; N, 13.48, measured element content ( %): C, 78.57; H, 4.23; F, 3.68; N, 13.40. The above analysis results show that the obtained product is the target product.
实施例23Example 23
Figure PCTCN2020081035-appb-000103
Figure PCTCN2020081035-appb-000103
依照实施例3的合成，步骤相同，用化合物N 1-(3-氟苯基)-1,2-苯二胺代替化合物邻氨基二苯胺，得到白色化合物0.532g(产率68.2％)，质谱分析确定的分子离子质量为：519.11(计算值为：519.19)；理论元素含量(％)C 34H 22FN 5：C,78.60；H,4.27；F,3.66；N,13.48，实测元素含量(％)：C,78.66；H,4.34；F,3.79；N,13.51。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 3, the steps were the same, the compound N 1 -(3-fluorophenyl)-1,2-phenylenediamine was used instead of the compound o-aminodiphenylamine to obtain 0.532g of a white compound (yield 68.2%), mass spectrum The molecular ion mass determined by analysis is: 519.11 (calculated value: 519.19); theoretical element content (%) C 34 H 22 FN 5 : C,78.60; H, 4.27; F, 3.66; N, 13.48, measured element content ( %): C, 78.66; H, 4.34; F, 3.79; N, 13.51. The above analysis results show that the obtained product is the target product.
实施例24Example 24
Figure PCTCN2020081035-appb-000104
Figure PCTCN2020081035-appb-000104
依照实施例3的合成，步骤相同，用化合物N 1-(4-氟苯基)-1,2-苯二胺代替化合物邻氨基二苯胺，得到白色化合物0.449g(产率57.6％)，质谱分析确定的分子离子质量为：519.05(计算值为：519.19)；理论元素含量(％)C 34H 22FN 5：C,78.60；H,4.27；F,3.66；N,13.48，实测元素含量(％)：C,78.75；H,4.34；F,3.60；N,13.43。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 3, the steps were the same, and the compound N 1 -(4-fluorophenyl)-1,2-phenylenediamine was used instead of the compound o-aminodiphenylamine to obtain 0.449 g of a white compound (yield 57.6%), mass spectrum The molecular ion mass determined by analysis is: 519.05 (calculated value: 519.19); theoretical element content (%) C 34 H 22 FN 5 : C,78.60; H, 4.27; F, 3.66; N, 13.48, measured element content ( %): C, 78.75; H, 4.34; F, 3.60; N, 13.43. The above analysis results show that the obtained product is the target product.
实施例25Example 25
Figure PCTCN2020081035-appb-000105
Figure PCTCN2020081035-appb-000105
依照实施例2的合成，步骤相同，用化合物N 1-(2-氟苯基)-1,2-苯二胺代替化合物邻氨基二苯胺，得到白色化合物0.439g(产率56.7％)，质谱分析确定的分子离子质量为：519.11(计算值为：519.19)；理论元素含量(％)C 34H 22FN 5：C,78.60；H,4.27；F,3.66；N,13.48，实测元素含量(％)：C,78.55；H,4.24；F,3.69；N,13.41。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 2, the steps are the same, and the compound N 1 -(2-fluorophenyl)-1,2-phenylenediamine is used instead of the compound o-aminodiphenylamine to obtain 0.439 g of a white compound (yield 56.7%), mass spectrum The molecular ion mass determined by analysis is: 519.11 (calculated value: 519.19); theoretical element content (%) C 34 H 22 FN 5 : C,78.60; H, 4.27; F, 3.66; N, 13.48, measured element content ( %): C, 78.55; H, 4.24; F, 3.69; N, 13.41. The above analysis results show that the obtained product is the target product.
实施例26Example 26
Figure PCTCN2020081035-appb-000106
Figure PCTCN2020081035-appb-000106
依照实施例2的合成，步骤相同，用化合物N 1-(3-氟苯基)-1,2-苯二胺代替化合物邻氨基二苯胺，得到白色化合物0.429g(产率55.0％)，质谱分析确定的分子离子质量为：519.13(计算值为：519.19)；理论元素含量(％)C 34H 22FN 5：C,78.60；H,4.27；F,3.66；N,13.48，实测元素含量(％)：C,78.66；H,4.34；F,3.64；N,13.45。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 2, the steps are the same, the compound N 1 -(3-fluorophenyl)-1,2-phenylenediamine is used instead of the compound o-aminodiphenylamine to obtain 0.429 g of a white compound (yield 55.0%), mass spectrum The molecular ion mass determined by analysis is: 519.13 (calculated value: 519.19); theoretical element content (%) C 34 H 22 FN 5 : C, 78.60; H, 4.27; F, 3.66; N, 13.48, measured element content ( %): C, 78.66; H, 4.34; F, 3.64; N, 13.45. The above analysis results show that the obtained product is the target product.
实施例27Example 27
Figure PCTCN2020081035-appb-000107
Figure PCTCN2020081035-appb-000107
依照实施例3的合成，步骤相同，用化合物N 1-(4-氟苯基)-1,2-苯二胺代替化合物邻氨基二苯胺，得到白色化合物0.563g(产率72.2％)，质谱分析确定的分子离子质量为：519.22(计算值为：519.19)； 理论元素含量(％)C 34H 22FN 5：C,78.60；H,4.27；F,3.66；N,13.48，实测元素含量(％)：C,78.57；H,4.22；F,3.67；N,13.51。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 3, the steps were the same, and the compound N 1 -(4-fluorophenyl)-1,2-phenylenediamine was used instead of the compound o-aminodiphenylamine to obtain 0.563 g of a white compound (yield 72.2%), mass spectrum The molecular ion mass determined by analysis is: 519.22 (calculated value: 519.19); theoretical element content (%) C 34 H 22 FN 5 : C,78.60; H, 4.27; F, 3.66; N, 13.48, measured element content ( %): C, 78.57; H, 4.22; F, 3.67; N, 13.51. The above analysis results show that the obtained product is the target product.
实施例28Example 28
Figure PCTCN2020081035-appb-000108
Figure PCTCN2020081035-appb-000108
依照实施例1的合成，步骤相同，用化合物N 1-(3,5-二氟苯基)-1,2-苯二胺代替化合物邻氨基二苯胺，得到白色化合物0.537g(产率66.7％)，质谱分析确定的分子离子质量为：537.28(计算值为：537.18)；理论元素含量(％)C 34H 21F 2N 5：C,75.97；H,3.94；F,7.07；N,13.03，实测元素含量(％)：C,76.07；H,3.99；F,7.17；N,13.08。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 1, the steps were the same, and the compound N 1 -(3,5-difluorophenyl)-1,2-phenylenediamine was used instead of the compound o-aminodiphenylamine to obtain 0.537g of a white compound (yield 66.7%) ), the molecular ion mass determined by mass spectrometry analysis is: 537.28 (calculated value: 537.18); theoretical element content (%) C 34 H 21 F 2 N 5 : C, 75.97; H, 3.94; F, 7.07; N, 13.03 , Measured element content (%): C, 76.07; H, 3.99; F, 7.17; N, 13.08. The above analysis results show that the obtained product is the target product.
实施例29Example 29
Figure PCTCN2020081035-appb-000109
Figure PCTCN2020081035-appb-000109
依照实施例3的合成，步骤相同，用化合物N 1-(3,5-二氟苯基)-1,2-苯二胺代替化合物邻氨基二苯胺，得到白色化合物0.454g(产率56.2％)，质谱分析确定的分子离子质量为：537.20(计算值为：537.18)；理论元素含量(％)C 34H 21F 2N 5：C,75.97；H,3.94；F,7.07；N,13.03，实测元素含量(％)：C,76.00；H,4.10；F,7.07；N,13.18。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 3, the steps are the same, the compound N 1 -(3,5-difluorophenyl)-1,2-phenylenediamine is used instead of the compound o-aminodiphenylamine to obtain 0.454g of a white compound (yield 56.2%) ), the molecular ion mass determined by mass spectrometry analysis is: 537.20 (calculated value: 537.18); theoretical element content (%) C 34 H 21 F 2 N 5 : C, 75.97; H, 3.94; F, 7.07; N, 13.03 , Measured element content (%): C, 76.00; H, 4.10; F, 7.07; N, 13.18. The above analysis results show that the obtained product is the target product.
实施例30Example 30
Figure PCTCN2020081035-appb-000110
Figure PCTCN2020081035-appb-000110
依照实施例2的合成，步骤相同，用化合物N 1-(3,5-二氟苯基)-1,2-苯二胺代替化合物邻氨基二苯胺，得到白色化合物0.390g(产率48.3％)，质谱分析确定的分子离子质量为：537.09(计算值为：537.18)；理论元素含量(％)C 34H 21F 2N 5：C,75.97；H,3.94；F,7.07；N,13.03，实测元素含量(％)：C,75.99；H,3.92；F,7.09；N,13.13。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 2, the steps were the same, and the compound N 1 -(3,5-difluorophenyl)-1,2-phenylenediamine was used instead of the compound o-aminodiphenylamine to obtain 0.390g of a white compound (yield 48.3%) ), the molecular ion mass determined by mass spectrometry analysis is: 537.09 (calculated value: 537.18); theoretical element content (%) C 34 H 21 F 2 N 5 : C, 75.97; H, 3.94; F, 7.07; N, 13.03 , Measured element content (%): C, 75.99; H, 3.92; F, 7.09; N, 13.13. The above analysis results show that the obtained product is the target product.
实施例31Example 31
Figure PCTCN2020081035-appb-000111
Figure PCTCN2020081035-appb-000111
依照实施例6的合成，步骤相同，用化合物2-氟苯甲醛代替化合物苯甲醛，得到白色化合物0.392g(产率50.2％)，质谱分析确定的分子离子质量为：519.24(计算值为：519.19)；理论元素含量(％)C 34H 22FN 5：C,78.60；H,4.27；F,3.66；N,13.48，实测元素含量(％)：C,78.55；H,4.29；F,3.69；N,13.33。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 6, the steps were the same, and the compound 2-fluorobenzaldehyde was used instead of the compound benzaldehyde to obtain 0.392 g of a white compound (yield 50.2%). The mass of molecular ion determined by mass spectrometry was 519.24 (calculated value: 519.19) ); Theoretical element content (%) C 34 H 22 FN 5 : C, 78.60; H, 4.27; F, 3.66; N, 13.48, measured element content (%): C, 78.55; H, 4.29; F, 3.69; N, 13.33. The above analysis results show that the obtained product is the target product.
实施例32Example 32
Figure PCTCN2020081035-appb-000112
Figure PCTCN2020081035-appb-000112
依照实施例5的合成，步骤相同，用化合物2-氟苯甲醛代替化合物苯甲醛，得到白色化合物0.353g(产率45.3％)，质谱分析确定的分子离子质量为：519.15(计算值为：519.19)；理论元素含量(％)C 34H 22FN 5：C,78.60；H,4.27；F,3.66；N,13.48，实测元素含量(％)：C,78.66；H,4.22；F,3.69；N,13.59。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 5, the steps were the same, and the compound 2-fluorobenzaldehyde was used instead of the compound benzaldehyde to obtain 0.353 g of a white compound (yield 45.3%). The molecular ion mass determined by mass spectrometry was 519.15 (calculated value: 519.19) ); Theoretical element content (%) C 34 H 22 FN 5 : C, 78.60; H, 4.27; F, 3.66; N, 13.48, the measured element content (%): C, 78.66; H, 4.22; F, 3.69; N, 13.59. The above analysis results show that the obtained product is the target product.
实施例33Example 33
Figure PCTCN2020081035-appb-000113
Figure PCTCN2020081035-appb-000113
依照实施例4的合成，步骤相同，用化合物2-氟苯甲醛代替化合物苯甲醛，得到白色化合物0.357g(产率45.8％)，质谱分析确定的分子离子质量为：519.22(计算值为：519.19)；理论元素含量(％)C 34H 22FN 5：C,78.60；H,4.27；F,3.66；N,13.48，实测元素含量(％)：C,78.59；H,4.32；F,3.77；N,13.61。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 4, the steps were the same, and the compound 2-fluorobenzaldehyde was substituted for the compound benzaldehyde to obtain 0.357 g of a white compound (yield 45.8%). The mass of molecular ion determined by mass spectrometry was 519.22 (calculated value: 519.19) ); Theoretical element content (%) C 34 H 22 FN 5 : C, 78.60; H, 4.27; F, 3.66; N, 13.48, measured element content (%): C, 78.59; H, 4.32; F, 3.77; N, 13.61. The above analysis results show that the obtained product is the target product.
实施例34Example 34
Figure PCTCN2020081035-appb-000114
Figure PCTCN2020081035-appb-000114
依照实施例6的合成，步骤相同，用化合物3-氟苯甲醛代替化合物苯甲醛，得到白色化合物0.405g(产率51.9％)，质谱分析确定的分子离子质量为：519.15(计算值为：519.19)；理论元素含量(％)C 34H 22FN 5：C,78.60；H,4.27；F,3.66；N,13.48，实测元素含量(％)：C,78.62；H,4.28；F,3.69；N,13.59。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 6, the steps were the same, and the compound 3-fluorobenzaldehyde was used instead of the compound benzaldehyde to obtain 0.405 g of a white compound (yield 51.9%). The molecular ion mass determined by mass spectrometry was 519.15 (calculated value: 519.19) ); Theoretical element content (%) C 34 H 22 FN 5 : C, 78.60; H, 4.27; F, 3.66; N, 13.48, measured element content (%): C, 78.62; H, 4.28; F, 3.69; N, 13.59. The above analysis results show that the obtained product is the target product.
实施例35Example 35
Figure PCTCN2020081035-appb-000115
Figure PCTCN2020081035-appb-000115
依照实施例5的合成，步骤相同，用化合物3-氟苯甲醛代替化合物苯甲醛，得到白色化合物0.416g(产率53.3％)，质谱分析确定的分子离子质量为：519.28(计算值为：519.19)；理论元素含量(％)C 34H 22FN 5：C,78.60；H,4.27；F,3.66；N,13.48，实测元素含量(％)：C,78.67；H,4.42；F,3.47；N,13.41。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 5, the steps were the same, and the compound 3-fluorobenzaldehyde was substituted for the compound benzaldehyde to obtain 0.416 g of a white compound (yield 53.3%). The mass of the molecular ion determined by mass spectrometry was 519.28 (calculated value: 519.19) ); Theoretical element content (%) C 34 H 22 FN 5 : C, 78.60; H, 4.27; F, 3.66; N, 13.48, measured element content (%): C, 78.67; H, 4.42; F, 3.47; N, 13.41. The above analysis results show that the obtained product is the target product.
实施例36Example 36
Figure PCTCN2020081035-appb-000116
Figure PCTCN2020081035-appb-000116
依照实施例4的合成，步骤相同，用化合物3-氟苯甲醛代替化合物苯甲醛，得到白色化合物0.523g(产率66.7％)，质谱分析确定的分子离子质量为：519.22(计算值为：519.19)；理论元素含量(％)C 34H 22FN 5：C,78.60；H,4.27；F,3.66；N,13.48，实测元素含量(％)：C,78.57；H,4.22；F,3.67；N,13.51。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 4, the steps were the same, and the compound 3-fluorobenzaldehyde was used instead of the compound benzaldehyde to obtain 0.523 g of a white compound (yield 66.7%). The molecular ion mass determined by mass spectrometry was 519.22 (calculated value: 519.19) ); Theoretical element content (%) C 34 H 22 FN 5 : C, 78.60; H, 4.27; F, 3.66; N, 13.48, the measured element content (%): C, 78.57; H, 4.22; F, 3.67; N, 13.51. The above analysis results show that the obtained product is the target product.
实施例37Example 37
Figure PCTCN2020081035-appb-000117
Figure PCTCN2020081035-appb-000117
依照实施例6的合成，步骤相同，用化合物4-氟苯甲醛代替化合物苯甲醛，得到白色化合物0.435g(产率55.8％)，质谱分析确定的分子离子质量为：519.25(计算值为：519.19)；理论元素含量(％) C 34H 22FN 5：C,78.60；H,4.27；F,3.66；N,13.48，实测元素含量(％)：C,78.57；H,4.22；F,3.67；N,13.51。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 6, the steps were the same, and the compound 4-fluorobenzaldehyde was substituted for the compound benzaldehyde to obtain 0.435 g of a white compound (yield 55.8%). The mass of the molecular ion determined by mass spectrometry was 519.25 (calculated value: 519.19) ); Theoretical element content (%) C 34 H 22 FN 5 : C, 78.60; H, 4.27; F, 3.66; N, 13.48, the measured element content (%): C, 78.57; H, 4.22; F, 3.67; N, 13.51. The above analysis results show that the obtained product is the target product.
实施例38Example 38
Figure PCTCN2020081035-appb-000118
Figure PCTCN2020081035-appb-000118
依照实施例5的合成，步骤相同，用化合物4-氟苯甲醛代替化合物苯甲醛，得到白色化合物0.472g(产率60.5％)，质谱分析确定的分子离子质量为：519.10(计算值为：519.19)；理论元素含量(％)C 34H 22FN 5：C,78.60；H,4.27；F,3.66；N,13.48，实测元素含量(％)：C,78.58；H,4.22；F,3.87；N,13.51。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 5, the steps were the same, and the compound 4-fluorobenzaldehyde was used instead of the compound benzaldehyde to obtain 0.472 g of a white compound (yield 60.5%). The molecular ion mass determined by mass spectrometry was 519.10 (calculated value: 519.19) ); Theoretical element content (%) C 34 H 22 FN 5 : C, 78.60; H, 4.27; F, 3.66; N, 13.48, measured element content (%): C, 78.58; H, 4.22; F, 3.87; N, 13.51. The above analysis results show that the obtained product is the target product.
实施例39Example 39
Figure PCTCN2020081035-appb-000119
Figure PCTCN2020081035-appb-000119
依照实施例4的合成，步骤相同，用化合物4-氟苯甲醛代替化合物苯甲醛，得到白色化合物0.416g(产率53.4％)，质谱分析确定的分子离子质量为：519.14(计算值为：519.19)；理论元素含量(％)C 34H 22FN 5：C,78.60；H,4.27；F,3.66；N,13.48，实测元素含量(％)：C,78.77；H,4.12；F,3.87；N,13.51。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 4, the steps were the same, and the compound 4-fluorobenzaldehyde was substituted for the compound benzaldehyde to obtain 0.416 g of a white compound (yield 53.4%). The molecular ion mass determined by mass spectrometry was 519.14 (calculated value: 519.19) ); Theoretical element content (%) C 34 H 22 FN 5 : C, 78.60; H, 4.27; F, 3.66; N, 13.48, the measured element content (%): C, 78.77; H, 4.12; F, 3.87; N, 13.51. The above analysis results show that the obtained product is the target product.
实施例40Example 40
Figure PCTCN2020081035-appb-000120
Figure PCTCN2020081035-appb-000120
依照实施例6的合成，步骤相同，用化合物3,5-二氟苯甲醛代替化合物苯甲醛，得到白色化合物0.361g(产率44.9％)，质谱分析确定的分子离子质量为：537.33(计算值为：537.18)；理论元素含量(％)C 34H 21F 2N 5：C,75.97；H,3.94；F,7.07；N,13.03，实测元素含量(％)：C,76.07；H,3.99；F,7.17；N,13.08。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 6, the steps were the same, and the compound 3,5-difluorobenzaldehyde was used instead of the compound benzaldehyde to obtain 0.361 g of a white compound (yield 44.9%). The molecular ion mass determined by mass spectrometry was 537.33 (calculated value) Is: 537.18); theoretical element content (%) C 34 H 21 F 2 N 5 : C, 75.97; H, 3.94; F, 7.07; N, 13.03, measured element content (%): C, 76.07; H, 3.99 ; F,7.17; N,13.08. The above analysis results show that the obtained product is the target product.
实施例41Example 41
Figure PCTCN2020081035-appb-000121
Figure PCTCN2020081035-appb-000121
依照实施例5的合成，步骤相同，用化合物3,5-二氟苯甲醛代替化合物苯甲醛，得到白色化合物0.382g(产率47.5％)，质谱分析确定的分子离子质量为：537.19(计算值为：537.18)；理论元素含量(％)C 34H 21F 2N 5：C,75.97；H,3.94；F,7.07；N,13.03，实测元素含量(％)：C,75.87；H,4.12；F,7.07；N,13.18。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 5, the steps were the same, and the compound 3,5-difluorobenzaldehyde was used instead of the compound benzaldehyde to obtain 0.382g of a white compound (yield 47.5%). The molecular ion mass determined by mass spectrometry was 537.19 (calculated value) Is: 537.18); theoretical element content (%) C 34 H 21 F 2 N 5 : C, 75.97; H, 3.94; F, 7.07; N, 13.03, measured element content (%): C, 75.87; H, 4.12 ; F, 7.07; N, 13.18. The above analysis results show that the obtained product is the target product.
实施例42Example 42
Figure PCTCN2020081035-appb-000122
Figure PCTCN2020081035-appb-000122
依照实施例4的合成，步骤相同，用化合物3,5-二氟苯甲醛代替化合物苯甲醛，得到白色化合物0.425g(产率52.8％)，质谱分析确定的分子离子质量为：537.09(计算值为：537.18)；理论元素含量(％)C 34H 21F 2N 5：C,75.97；H,3.94；F,7.07；N,13.03，实测元素含量(％)：C,76.11；H,3.89；F,7.25；N,13.18。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 4, the steps are the same, and the compound 3,5-difluorobenzaldehyde is used instead of the compound benzaldehyde to obtain 0.425g of white compound (yield 52.8%). The mass of molecular ion determined by mass spectrometry is 537.09 (calculated value) Is: 537.18); theoretical element content (%) C 34 H 21 F 2 N 5 : C, 75.97; H, 3.94; F, 7.07; N, 13.03, measured element content (%): C, 76.11; H, 3.89 ; F, 7.25; N, 13.18. The above analysis results show that the obtained product is the target product.
实施例43Example 43
Figure PCTCN2020081035-appb-000123
Figure PCTCN2020081035-appb-000123
依照实施例7的合成，步骤相同，用化合物2-氯-4,6-二(4-氟苯基)-1,3,5-三嗪代替化合物2-氯-4,6-二苯基-1,3,5-三嗪，得到白色化合物0.553g(产率51.2％)，质谱分析确定的分子离子质量为：538.25(计算值为：538.17)；理论元素含量(％)C 33H 20F 2N 6：C,73.60；H,3.74；F,7.06；N,15.60，实测元素含量(％)：C,73.58；H,3.81；F,7.16；N,15.77。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 7, the steps are the same, and the compound 2-chloro-4,6-bis(4-fluorophenyl)-1,3,5-triazine is used instead of the compound 2-chloro-4,6-diphenyl -1,3,5-triazine, 0.553g of white compound was obtained (yield 51.2%), the molecular ion mass determined by mass spectrometry was 538.25 (calculated value: 538.17); theoretical element content (%) C 33 H 20 F 2 N 6 : C, 73.60; H, 3.74; F, 7.06; N, 15.60, measured element content (%): C, 73.58; H, 3.81; F, 7.16; N, 15.77. The above analysis results show that the obtained product is the target product.
实施例44Example 44
Figure PCTCN2020081035-appb-000124
Figure PCTCN2020081035-appb-000124
依照实施例8的合成，步骤相同，用化合物2-氯-4,6-二(4-氟苯基)-1,3,5-三嗪代替化合物2-氯-4,6-二苯基-1,3,5-三嗪，得到白色化合物0.657g(产率60.8％)，质谱分析确定的分子离子质量为：538.32(计算值为：538.17)；理论元素含量(％)C 33H 20F 2N 6：C,73.60；H,3.74；F,7.06；N,15.60，实测元素含量(％)：C,73.49；H,3.83；F,7.11；N,15.53。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 8, the steps are the same, and the compound 2-chloro-4,6-bis(4-fluorophenyl)-1,3,5-triazine is used instead of the compound 2-chloro-4,6-diphenyl -1,3,5-triazine, 0.657g of white compound was obtained (yield 60.8%), the molecular ion mass determined by mass spectrometry analysis was: 538.32 (calculated value: 538.17); theoretical element content (%) C 33 H 20 F 2 N 6 : C, 73.60; H, 3.74; F, 7.06; N, 15.60, measured element content (%): C, 73.49; H, 3.83; F, 7.11; N, 15.53. The above analysis results show that the obtained product is the target product.
实施例45Example 45
Figure PCTCN2020081035-appb-000125
Figure PCTCN2020081035-appb-000125
依照实施例9的合成，步骤相同，用化合物2-氯-4,6-二(4-氟苯基)-1,3,5-三嗪代替化合物2-氯-4,6-二苯基-1,3,5-三嗪，得到白色化合物0.619g(产率57.3％)，质谱分析确定的分子离子质量为：538.33(计算值为：538.17)；理论元素含量(％)C 33H 20F 2N 6：C,73.60；H,3.74；F,7.06；N,15.60，实测元素含量(％)：C,73.59；H,3.77；F,7.26；N,15.58。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 9, the steps are the same, and the compound 2-chloro-4,6-bis(4-fluorophenyl)-1,3,5-triazine is used instead of the compound 2-chloro-4,6-diphenyl -1,3,5-triazine, 0.619g of white compound was obtained (yield 57.3%), the molecular ion mass determined by mass spectrometry analysis was: 538.33 (calculated value: 538.17); theoretical element content (%) C 33 H 20 F 2 N 6 : C, 73.60; H, 3.74; F, 7.06; N, 15.60, measured element content (%): C, 73.59; H, 3.77; F, 7.26; N, 15.58. The above analysis results show that the obtained product is the target product.
实施例46Example 46
Figure PCTCN2020081035-appb-000126
Figure PCTCN2020081035-appb-000126
依照实施例10的合成，步骤相同，用化合物2-氯-4,6-二(4-氟苯基)-1,3,5-三嗪代替化合物2-氯-4,6-二苯基-1,3,5-三嗪，得到白色化合物0.511g(产率47.3％)，质谱分析确定的分子离子质量为：538.09(计算值为：538.17)；理论元素含量(％)C 33H 20F 2N 6：C,73.60；H,3.74；F,7.06；N,15.60，实测元素含量(％)：C,73.55；H,3.80；F,7.14；N,15.77。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 10, the steps are the same, and the compound 2-chloro-4,6-bis(4-fluorophenyl)-1,3,5-triazine is used instead of the compound 2-chloro-4,6-diphenyl -1,3,5-triazine, 0.511g of white compound was obtained (yield 47.3%), the molecular ion mass determined by mass spectrometry analysis was: 538.09 (calculated value: 538.17); theoretical element content (%) C 33 H 20 F 2 N 6 : C, 73.60; H, 3.74; F, 7.06; N, 15.60, measured element content (%): C, 73.55; H, 3.80; F, 7.14; N, 15.77. The above analysis results show that the obtained product is the target product.
实施例47Example 47
Figure PCTCN2020081035-appb-000127
Figure PCTCN2020081035-appb-000127
依照实施例11的合成，步骤相同，用化合物2-氯-4,6-二(4-氟苯基)-1,3,5-三嗪代替化合物2-氯-4,6-二苯基-1,3,5-三嗪，得到白色化合物0.597g(产率55.3％)，质谱分析确定的分子离子质量为：538.30(计算值为：538.17)；理论元素含量(％)C 33H 20F 2N 6：C,73.60；H,3.74；F,7.06；N,15.60，实测元素含量(％)：C,73.47；H,3.59；F,7.21；N,15.46。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 11, the steps are the same, and the compound 2-chloro-4,6-bis(4-fluorophenyl)-1,3,5-triazine is used instead of the compound 2-chloro-4,6-diphenyl -1,3,5-triazine to obtain 0.597g of white compound (yield 55.3%), the molecular ion mass determined by mass spectrometry analysis is: 538.30 (calculated value: 538.17); theoretical element content (%) C 33 H 20 F 2 N 6 : C, 73.60; H, 3.74; F, 7.06; N, 15.60, measured element content (%): C, 73.47; H, 3.59; F, 7.21; N, 15.46. The above analysis results show that the obtained product is the target product.
实施例48Example 48
Figure PCTCN2020081035-appb-000128
Figure PCTCN2020081035-appb-000128
依照实施例12的合成，步骤相同，用化合物2-氯-4,6-二(4-氟苯基)-1,3,5-三嗪代替化合物2-氯-4,6-二苯基-1,3,5-三嗪，得到白色化合物0.517g(产率47.9％)，质谱分析确定的分子离子质量为：538.22(计算值为：538.17)；理论元素含量(％)C 33H 20F 2N 6：C,73.60；H,3.74；F,7.06；N,15.60，实测元素含量(％)：C,73.60；H,3.77；F,7.16；N,15.49。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 12, the steps are the same, and the compound 2-chloro-4,6-bis(4-fluorophenyl)-1,3,5-triazine is used instead of the compound 2-chloro-4,6-diphenyl -1,3,5-triazine, 0.517g of white compound was obtained (yield 47.9%), the mass of molecular ion determined by mass spectrometry was 538.22 (calculated value: 538.17); theoretical element content (%) C 33 H 20 F 2 N 6 : C, 73.60; H, 3.74; F, 7.06; N, 15.60, measured element content (%): C, 73.60; H, 3.77; F, 7.16; N, 15.49. The above analysis results show that the obtained product is the target product.
实施例49Example 49
Figure PCTCN2020081035-appb-000129
Figure PCTCN2020081035-appb-000129
2-氯-4,6-二苯基-1,3,5-三嗪4.02g(15mmol)，3,5-二甲酰基苯硼酸3.20g(18mmol)，碳酸钾3.73g(27mmol)加入到250mL双口瓶中，加入THF 100mL，H 2O 20mL，氮气条件下加入催化剂四(三苯基膦)钯，回流12h。用二氯甲烷/水洗涤反应液，有机相旋去溶剂后，柱层析提纯，得白色固体中间体(4.50g，产率82.2％)。 2-Chloro-4,6-diphenyl-1,3,5-triazine 4.02g (15mmol), 3,5-diformylbenzeneboronic acid 3.20g (18mmol), potassium carbonate 3.73g (27mmol) were added to Add 100 mL of THF and 20 mL of H 2 O to a 250 mL double-necked flask. Add the catalyst tetrakis (triphenylphosphine) palladium under nitrogen and reflux for 12 h. The reaction solution was washed with dichloromethane/water, the organic phase was rotated to remove the solvent, and then purified by column chromatography to obtain a white solid intermediate (4.50 g, yield 82.2%).
10mL水溶解NaHSO 3 4.70g(45.0mmol)，加入中间体0.550g(1.51mmol)，常温搅拌5h。然后加入邻氨基二苯胺0.611g(3.32mmol)，加入20mL乙醇，氮气保护下回流24h。冷却到室温后过滤，得到白色粗产品。用二氯甲烷柱层析得到白色固体产品(0.704g产率67.3％)。质谱分析确定的分子离子 质量为：693.15(计算值为：693.26)；理论元素含量(％)C 47H 31N 7：C,81.36；H,4.50；N,14.13；实测元素含量(％)：C,81.25；H,4.60；N,14.22。上述分析结果表明，获得的产物为目标产品。 Dissolve 4.70 g (45.0 mmol) of NaHSO 3 in 10 mL of water, add 0.550 g (1.51 mmol) of intermediate, and stir at room temperature for 5 hours. Then 0.611 g (3.32 mmol) of o-aminodiphenylamine was added, 20 mL of ethanol was added, and refluxed under nitrogen protection for 24 hours. After cooling to room temperature, it was filtered to obtain a white crude product. A white solid product was obtained by methylene chloride column chromatography (0.704 g, yield 67.3%). The molecular ion mass determined by mass spectrometry analysis is: 693.15 (calculated value: 693.26); theoretical element content (%) C 47 H 31 N 7 : C, 81.36; H, 4.50; N, 14.13; measured element content (%): C, 81.25; H, 4.60; N, 14.22. The above analysis results show that the obtained product is the target product.
实施例50Example 50
Figure PCTCN2020081035-appb-000130
Figure PCTCN2020081035-appb-000130
10mL水溶解NaHSO 3 4.70g(45.0mmol)，加入苯甲醛0.398g(3.75mmol)，常温搅拌5h，然后加入N1,N 1’-(5-溴-1,3-苯基)双(1,2-苯二胺)0.552g(1.50mmol)，加入20mL乙醇，氮气保护下回流24h。冷却到室温后过滤，得到白色固体粗产品0.700g(产率86.4％)。 Dissolve NaHSO 3 4.70g (45.0mmol) in 10mL of water, add 0.398g (3.75mmol) of benzaldehyde, stir at room temperature for 5h, and then add N1,N 1 '-(5-bromo-1,3-phenyl)bis(1, 2-phenylenediamine) 0.552 g (1.50 mmol), 20 mL of ethanol was added, and refluxed for 24 hours under nitrogen protection. After cooling to room temperature, it was filtered to obtain 0.700 g of a white solid crude product (yield 86.4%).
将上述粗产品1.08g(2.00mmol)，联硼酸频那醇酯1.02g(4.00mmol)，干燥的醋酸钾1.96g(20.0mmol)，以及干燥的1,4-二氧六环120mL于250mL双口瓶中，在氮气保护条件下加入催化剂[1,1'-双(二苯基膦基)二茂铁]二氯化钯150mg(0.20mmol)，回流24h。冷却到室温后，过滤除去醋酸钾，滤液除去二氧六环后用二氯甲烷/水洗涤，有机相除去有机溶剂后，用二氯甲烷做展开剂柱层析，得到白色固体中间体972mg(产率82.6％)。The above crude product 1.08g (2.00mmol), 1.02g (4.00mmol) of pinacol biborate, 1.96g (20.0mmol) of dried potassium acetate, and 120mL of dried 1,4-dioxane in 250mL of dioxane In the mouth flask, add 150 mg (0.20 mmol) of palladium dichloride catalyst [1,1'-bis(diphenylphosphino)ferrocene] dichloride under nitrogen protection, and reflux for 24 hours. After cooling to room temperature, potassium acetate was removed by filtration. The filtrate was washed with dichloromethane/water after removing dioxane. After removing the organic solvent from the organic phase, column chromatography was performed with dichloromethane as a developing solvent to obtain a white solid intermediate 972mg The yield is 82.6%).
将上述白色中间体882mg(1.50mmol)，2-氯-4,6-二苯基-1,3,5-三嗪1.00g(1.65mmol)，碳酸钾440mg(4.5mmol)加入到100mL双口瓶中，加入THF 25mL，H 2O 3mL，氮气条件下加入催化剂四(三苯基膦)钯25.0mg，回流12h。用二氯甲烷/水洗涤反应液，有机相旋去溶剂后，柱层析提纯，得白色固体化合物643mg(产率61.8％)。质谱分析确定的分子离子质量为：693.18(计算值为：693.26)；理论元素含量(％)C 47H 31N 7：C,81.36；H,4.50；N,14.13；实测元素含量(％)：C,81.50；H,4.65；N,14.03。上述分析结果表明，获得的产物为目标产品。 Add 882mg (1.50mmol) of the above white intermediate, 1.00g (1.65mmol) of 2-chloro-4,6-diphenyl-1,3,5-triazine, and 440mg (4.5mmol) of potassium carbonate to 100mL double mouth Add 25 mL of THF, 3 mL of H 2 O to the bottle, add 25.0 mg of tetrakis (triphenylphosphine) palladium catalyst under nitrogen conditions, and reflux for 12 hours. The reaction solution was washed with dichloromethane/water, and the organic phase was rotated to remove the solvent, and then purified by column chromatography to obtain 643 mg of a white solid compound (yield 61.8%). The molecular ion mass determined by mass spectrometry analysis is: 693.18 (calculated value: 693.26); theoretical element content (%) C 47 H 31 N 7 : C, 81.36; H, 4.50; N, 14.13; measured element content (%): C, 81.50; H, 4.65; N, 14.03. The above analysis results show that the obtained product is the target product.
实施例51Example 51
Figure PCTCN2020081035-appb-000131
Figure PCTCN2020081035-appb-000131
依照实施例49的合成，步骤相同，用化合物N-(3-吡啶基)-1,2-苯二胺代替化合物邻氨基二苯胺，得到白色化合物0.716g(产率68.9％)，质谱分析确定的分子离子质量为：695.33(计算值为：695.25)；理论元素含量(％)C 45H 29N 9：C,77.68；H,4.20；N,18.12，实测元素含量(％)：C,77.77；H,4.15；N,18.35。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 49, the steps were the same, and the compound N-(3-pyridyl)-1,2-phenylenediamine was used instead of the compound o-aminodiphenylamine to obtain 0.716g of white compound (yield 68.9%), which was confirmed by mass spectrometry The molecular ion mass of is: 695.33 (calculated value: 695.25); theoretical element content (%) C 45 H 29 N 9 : C,77.68; H, 4.20; N, 18.12, measured element content (%): C,77.77 ; H, 4.15; N, 18.35. The above analysis results show that the obtained product is the target product.
实施例52Example 52
Figure PCTCN2020081035-appb-000132
Figure PCTCN2020081035-appb-000132
依照实施例49的合成，步骤相同，用化合物N-(4-吡啶基)-1,2-苯二胺代替化合物邻氨基二苯胺，得到白色化合物0.557g(产率53.6％)，质谱分析确定的分子离子质量为：695.33(计算值为：695.25)；理论元素含量(％)C 45H 29N 9：C,77.68；H,4.20；N,18.12，实测元素含量(％)：C,77.73；H,4.17；N,18.19。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 49, the steps were the same, the compound N-(4-pyridyl)-1,2-phenylenediamine was used instead of the compound o-aminodiphenylamine to obtain 0.557g of white compound (yield 53.6%), which was confirmed by mass spectrometry The molecular ion mass of is: 695.33 (calculated value: 695.25); theoretical element content (%) C 45 H 29 N 9 : C,77.68; H, 4.20; N, 18.12, measured element content (%): C,77.73 ; H, 4.17; N, 18.19. The above analysis results show that the obtained product is the target product.
实施例53Example 53
Figure PCTCN2020081035-appb-000133
Figure PCTCN2020081035-appb-000133
依照实施例50的合成，步骤相同，用化合物3-醛基吡啶代替化合物苯甲醛，得到白色化合物0.474g(产率45.6％)，质谱分析确定的分子离子质量为：695.46(计算值为：695.25)；理论元素含量(％)C 45H 29N 9：C,77.68；H,4.20；N,18.12，实测元素含量(％)：C,77.70；H,4.14；N,18.28。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 50, the steps were the same, and the compound 3-aldehyde pyridine was used instead of the compound benzaldehyde to obtain 0.474 g of a white compound (yield 45.6%). The molecular ion mass determined by mass spectrometry was 695.46 (calculated value: 695.25) ); Theoretical element content (%) C 45 H 29 N 9 : C, 77.68; H, 4.20; N, 18.12, the measured element content (%): C, 77.70; H, 4.14; N, 18.28. The above analysis results show that the obtained product is the target product.
实施例54Example 54
Figure PCTCN2020081035-appb-000134
Figure PCTCN2020081035-appb-000134
依照实施例50的合成，步骤相同，用化合物4-醛基吡啶代替化合物苯甲醛，得到白色化合物0.547g(产率52.6％)，质谱分析确定的分子离子质量为：695.24(计算值为：695.25)；理论元素含量(％)C 45H 29N 9：C,77.68；H,4.20；N,18.12，实测元素含量(％)：C,77.73；H,4.11；N,18.20。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 50, the steps were the same, and the compound 4-aldehyde pyridine was used instead of the compound benzaldehyde to obtain 0.547 g (yield of 52.6%) of a white compound. The molecular ion mass determined by mass spectrometry was 695.24 (calculated value: 695.25) ); Theoretical element content (%) C 45 H 29 N 9 : C, 77.68; H, 4.20; N, 18.12, the measured element content (%): C, 77.73; H, 4.11; N, 18.20. The above analysis results show that the obtained product is the target product.
实施例55Example 55
Figure PCTCN2020081035-appb-000135
Figure PCTCN2020081035-appb-000135
依照实施例49的合成，步骤相同，用化合物N 1,N 1’-{5-溴-1,3-二(2-氟苯基)}双(1,2-苯二胺)代替化合物N 1,N 1’-(5-溴-1,3-二苯基)双(1,2-苯二胺)，得到白色化合物0.504g(产率46.2％)，质谱分析确定的分子离子质量为：729.33(计算值为：729.25)；理论元素含量(％)C 47H 29F 2N 7：C,77.35；H,4.01；F,5.21；N,13.44，实测元素含量(％)：C,77.42；H,4.07；F,5.31；N,13.52。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 49, the steps are the same, using compound N 1 ,N 1 '-{5-bromo-1,3-bis(2-fluorophenyl)}bis(1,2-phenylenediamine) instead of compound N 1 ,N 1 '-(5-bromo-1,3-diphenyl)bis(1,2-phenylenediamine), 0.504g of white compound (yield 46.2%) is obtained, and the molecular ion mass determined by mass spectrometry is : 729.33 (calculated value: 729.25); theoretical element content (%) C 47 H 29 F 2 N 7 : C, 77.35; H, 4.01; F, 5.21; N, 13.44, measured element content (%): C, 77.42; H, 4.07; F, 5.31; N, 13.52. The above analysis results show that the obtained product is the target product.
实施例56Example 56
Figure PCTCN2020081035-appb-000136
Figure PCTCN2020081035-appb-000136
依照实施例49的合成，步骤相同，用化合物N 1,N 1’-{5-溴-1,3-二(2-氟苯基)}双(1,2-苯二胺)代替化合物N 1,N 1’-(5-溴-1,3-二苯基)双(1,2-苯二胺)，得到白色化合物0.560g(产率51.4％)，质谱分析确定的分子离子质量为：729.11(计算值为：729.25)；理论元素含量(％)C 47H 29F 2N 7：C,77.35；H,4.01；F,5.21；N,13.44，实测元素含量(％)：C,77.33；H,4.11；F,5.23；N,13.56。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 49, the steps are the same, using compound N 1 ,N 1 '-{5-bromo-1,3-bis(2-fluorophenyl)}bis(1,2-phenylenediamine) instead of compound N 1 ,N 1 '-(5-bromo-1,3-diphenyl)bis(1,2-phenylenediamine), 0.560g of white compound (yield 51.4%) was obtained, and the molecular ion mass determined by mass spectrometry was : 729.11 (calculated value: 729.25); theoretical element content (%) C 47 H 29 F 2 N 7 : C, 77.35; H, 4.01; F, 5.21; N, 13.44, measured element content (%): C, 77.33; H, 4.11; F, 5.23; N, 13.56. The above analysis results show that the obtained product is the target product.
实施例57Example 57
Figure PCTCN2020081035-appb-000137
Figure PCTCN2020081035-appb-000137
依照实施例49的合成，步骤相同，用化合物N 1,N 1’-{5-溴-1,3-二(2-氟苯基)}双(1,2-苯二胺)代替化合物N 1,N 1’-(5-溴-1,3-二苯基)双(1,2-苯二胺)，得到白色化合物0.597g(产率54.8％)，质谱分析确定的分子离子质量为：729.23(计算值为：729.25)；理论元素含量(％)C 47H 29F 2N 7：C,77.35；H,4.01；F,5.21；N,13.44，实测元素含量(％)：C,77.51；H,4.12；F,5.16；N,13.50。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 49, the steps are the same, using compound N 1 ,N 1 '-{5-bromo-1,3-bis(2-fluorophenyl)}bis(1,2-phenylenediamine) instead of compound N 1 ,N 1 '-(5-bromo-1,3-diphenyl)bis(1,2-phenylenediamine), 0.597g of white compound (yield 54.8%) was obtained, and the molecular ion mass determined by mass spectrometry was : 729.23 (calculated value: 729.25); theoretical element content (%) C 47 H 29 F 2 N 7 : C, 77.35; H, 4.01; F, 5.21; N, 13.44, measured element content (%): C, 77.51; H, 4.12; F, 5.16; N, 13.50. The above analysis results show that the obtained product is the target product.
实施例58Example 58
Figure PCTCN2020081035-appb-000138
Figure PCTCN2020081035-appb-000138
依照实施例50的合成，步骤相同，用化合物2-氟苯甲醛代替化合物苯甲醛，得到白色化合物0.560g(产率51.4％)，质谱分析确定的分子离子质量为：729.31(计算值为：729.25)；理论元素含量(％)C 47H 29F 2N 7：C,77.35；H,4.01；F,5.21；N,13.44，实测元素含量(％)：C,77.46；H,4.26；F,5.22；N,13.47。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 50, the steps were the same, and the compound 2-fluorobenzaldehyde was substituted for the compound benzaldehyde to obtain 0.560 g of a white compound (yield 51.4%). The molecular ion mass determined by mass spectrometry was 729.31 (calculated value: 729.25) ); theoretical element content (%) C 47 H 29 F 2 N 7 : C, 77.35; H, 4.01; F, 5.21; N, 13.44, measured element content (%): C, 77.46; H, 4.26; F, 5.22; N, 13.47. The above analysis results show that the obtained product is the target product.
实施例59Example 59
Figure PCTCN2020081035-appb-000139
Figure PCTCN2020081035-appb-000139
依照实施例50的合成，步骤相同，用化合物3-氟苯甲醛代替化合物苯甲醛，得到白色化合物0.517g(产率47.4％)，质谱分析确定的分子离子质量为：729.51(计算值为：729.25)；理论元素含量(％)C 47H 29F 2N 7：C,77.35；H,4.01；F,5.21；N,13.44，实测元素含量(％)：C,77.55；H,4.07；F,5.40；N,13.24。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 50, the steps were the same, and the compound 3-fluorobenzaldehyde was substituted for the compound benzaldehyde to obtain 0.517 g of a white compound (yield 47.4%). The molecular ion mass determined by mass spectrometry was 729.51 (calculated value: 729.25) ); Theoretical element content (%) C 47 H 29 F 2 N 7 : C, 77.35; H, 4.01; F, 5.21; N, 13.44, measured element content (%): C, 77.55; H, 4.07; F, 5.40; N, 13.24. The above analysis results show that the obtained product is the target product.
实施例60Example 60
Figure PCTCN2020081035-appb-000140
Figure PCTCN2020081035-appb-000140
依照实施例50的合成，步骤相同，用化合物4-氟苯甲醛代替化合物苯甲醛，得到白色化合物0.577g(产率52.8％)，质谱分析确定的分子离子质量为：729.25(计算值为：729.25)；理论元素含量(％)C 47H 29F 2N 7：C,77.35；H,4.01；F,5.21；N,13.44，实测元素含量(％)：C,77.35；H,4.01；F,5.21；N,13.44。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 50, the procedure was the same, and the compound 4-fluorobenzaldehyde was substituted for the compound benzaldehyde to obtain 0.577 g of a white compound (yield 52.8%). The molecular ion mass determined by mass spectrometry was 729.25 (calculated value: 729.25) ); Theoretical element content (%) C 47 H 29 F 2 N 7 : C, 77.35; H, 4.01; F, 5.21; N, 13.44, the measured element content (%): C, 77.35; H, 4.01; F, 5.21; N, 13.44. The above analysis results show that the obtained product is the target product.
实施例61Example 61
Figure PCTCN2020081035-appb-000141
Figure PCTCN2020081035-appb-000141
依照实施例49的合成，步骤相同，用化合物2-氯-4,6-二(4-氟苯基)-1,3,5-三嗪代替化合物2-氯-4,6-二苯基-1,3,5-三嗪，得到白色化合物0.511g(产率46.6％)，质谱分析确定的分子离子质量为： 729.50(计算值为：729.25)；理论元素含量(％)C 47H 29F 2N 7：C,77.35；H,4.01；F,5.21；N,13.44，实测元素含量(％)：C,77.42；H,3.99；F,5.21；N,13.40。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 49, the steps are the same, and the compound 2-chloro-4,6-bis(4-fluorophenyl)-1,3,5-triazine is used instead of the compound 2-chloro-4,6-diphenyl -1,3,5-triazine to obtain 0.511 g of a white compound (yield 46.6%). The molecular ion mass determined by mass spectrometry analysis is: 729.50 (calculated value: 729.25); theoretical element content (%) C 47 H 29 F 2 N 7 : C, 77.35; H, 4.01; F, 5.21; N, 13.44, measured element content (%): C, 77.42; H, 3.99; F, 5.21; N, 13.40. The above analysis results show that the obtained product is the target product.
实施例62Example 62
Figure PCTCN2020081035-appb-000142
Figure PCTCN2020081035-appb-000142
依照实施例50的合成，步骤相同，用化合物2-氯-4,6-二(4-氟苯基)-1,3,5-三嗪代替化合物2-氯-4,6-二苯基-1,3,5-三嗪，得到白色化合物0.573g(产率52.3％)，质谱分析确定的分子离子质量为：729.33(计算值为：729.25)；理论元素含量(％)C 47H 29F 2N 7：C,77.35；H,4.01；F,5.21；N,13.44，实测元素含量(％)：C,77.42；H,4.12；F,5.18；N,13.33。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 50, the steps are the same, and the compound 2-chloro-4,6-bis(4-fluorophenyl)-1,3,5-triazine is used instead of the compound 2-chloro-4,6-diphenyl -1,3,5-triazine, 0.573g of white compound was obtained (yield 52.3%), the molecular ion mass determined by mass spectrometry analysis was 729.33 (calculated value: 729.25); theoretical element content (%) C 47 H 29 F 2 N 7 : C, 77.35; H, 4.01; F, 5.21; N, 13.44, measured element content (%): C, 77.42; H, 4.12; F, 5.18; N, 13.33. The above analysis results show that the obtained product is the target product.
实施例63Example 63
Figure PCTCN2020081035-appb-000143
Figure PCTCN2020081035-appb-000143
依照实施例51的合成，步骤相同，用化合物2-氯-4,6-二(4-氟苯基)-1,3,5-三嗪代替化合物2-氯-4,6-二苯基-1,3,5-三嗪，得到白色化合物0.502g(产率45.8％)，质谱分析确定的分子离子质量为：731.17(计算值为：731.24)；理论元素含量(％)C 45H 27F 2N 9：C,73.86；H,3.72；F,5.19；N,17.23，实测元素含量(％)：C,73.93；H,3.88；F,5.21；N,17.25。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 51, the steps are the same, and the compound 2-chloro-4,6-bis(4-fluorophenyl)-1,3,5-triazine is used instead of the compound 2-chloro-4,6-diphenyl -1,3,5-triazine, 0.502g of white compound was obtained (yield 45.8%), the molecular ion mass determined by mass spectrometry analysis was: 731.17 (calculated value: 731.24); theoretical element content (%) C 45 H 27 F 2 N 9 : C, 73.86; H, 3.72; F, 5.19; N, 17.23, measured element content (%): C, 73.93; H, 3.88; F, 5.21; N, 17.25. The above analysis results show that the obtained product is the target product.
实施例64Example 64
Figure PCTCN2020081035-appb-000144
Figure PCTCN2020081035-appb-000144
依照实施例52的合成，步骤相同，用化合物2-氯-4,6-二(4-氟苯基)-1,3,5-三嗪代替化合物2-氯-4,6-二苯基-1,3,5-三嗪，得到白色化合物0.505g(产率46.1％)，质谱分析确定的分子离子质量为：731.11(计算值为：731.24)；理论元素含量(％)C 45H 27F 2N 9：C,73.86；H,3.72；F,5.19；N,17.23，实测元素含量(％)：C,73.90；H,3.88；F,5.22；N,17.31。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 52, the steps are the same, and the compound 2-chloro-4,6-bis(4-fluorophenyl)-1,3,5-triazine is used instead of the compound 2-chloro-4,6-diphenyl -1,3,5-triazine, 0.505g of white compound was obtained (yield 46.1%), the molecular ion mass determined by mass spectrometry analysis was: 731.11 (calculated value: 731.24); theoretical element content (%) C 45 H 27 F 2 N 9 : C, 73.86; H, 3.72; F, 5.19; N, 17.23, measured element content (%): C, 73.90; H, 3.88; F, 5.22; N, 17.31. The above analysis results show that the obtained product is the target product.
实施例65Example 65
Figure PCTCN2020081035-appb-000145
Figure PCTCN2020081035-appb-000145
依照实施例53的合成，步骤相同，用化合物2-氯-4,6-二(4-氟苯基)-1,3,5-三嗪代替化合物2-氯-4,6-二苯基-1,3,5-三嗪，得到白色化合物0.523g(产率66.7％)，质谱分析确定的分子离子质量为：731.24(计算值为：731.24)；理论元素含量(％)C 45H 27F 2N 9：C,73.86；H,3.72；F,5.19；N,17.23，实测元素含量(％)：C,73.86；H,3.72；F,5.19；N,17.23。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 53, the steps are the same, and the compound 2-chloro-4,6-bis(4-fluorophenyl)-1,3,5-triazine is used instead of the compound 2-chloro-4,6-diphenyl -1,3,5-triazine, 0.523g of white compound was obtained (yield 66.7%), the molecular ion mass determined by mass spectrometry was 731.24 (calculated value: 731.24); theoretical element content (%) C 45 H 27 F 2 N 9 : C, 73.86; H, 3.72; F, 5.19; N, 17.23, measured element content (%): C, 73.86; H, 3.72; F, 5.19; N, 17.23. The above analysis results show that the obtained product is the target product.
实施例66Example 66
Figure PCTCN2020081035-appb-000146
Figure PCTCN2020081035-appb-000146
依照实施例54的合成，步骤相同，用化合物2-氯-4,6-二(4-氟苯基)-1,3,5-三嗪代替化合物2-氯-4,6-二苯基-1,3,5-三嗪，得到白色化合物0.771g(产率52.8％)，质谱分析确定的分子离子质量为：731.33(计算值为：731.24)；理论元素含量(％)C 45H 27F 2N 9：C,73.86；H,3.72；F,5.19；N,17.23，实测元素含量(％)：C,73.96H,3.88；F,5.21；N,17.25。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 54, the steps are the same, and the compound 2-chloro-4,6-bis(4-fluorophenyl)-1,3,5-triazine is used instead of the compound 2-chloro-4,6-diphenyl -1,3,5-triazine to obtain 0.771g of white compound (yield 52.8%), the molecular ion mass determined by mass spectrometry analysis is: 731.33 (calculated value: 731.24); theoretical element content (%) C 45 H 27 F 2 N 9 : C, 73.86; H, 3.72; F, 5.19; N, 17.23, measured element content (%): C, 73.96H, 3.88; F, 5.21; N, 17.25. The above analysis results show that the obtained product is the target product.
实施例67Example 67
Figure PCTCN2020081035-appb-000147
Figure PCTCN2020081035-appb-000147
依照实施例55的合成，步骤相同，用化合物2-氯-4,6-二(4-氟苯基)-1,3,5-三嗪代替化合物2-氯-4,6-二苯基-1,3,5-三嗪，得到白色化合物0.744g(产率48.6％)，质谱分析确定的分子离子质量为：765.12(计算值为：765.23)；理论元素含量(％)C 47H 27F 4N 7：C,73.72；H,3.55；F,9.92；N,12.80，实测元素含量(％)：C,73.68；H,3.46；F,9.80；N,12.79。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 55, the steps are the same, and the compound 2-chloro-4,6-bis(4-fluorophenyl)-1,3,5-triazine is used instead of the compound 2-chloro-4,6-diphenyl -1,3,5-triazine, 0.744g white compound was obtained (yield 48.6%), the molecular ion mass determined by mass spectrometry analysis was 765.12 (calculated value: 765.23); theoretical element content (%) C 47 H 27 F 4 N 7 : C, 73.72; H, 3.55; F, 9.92; N, 12.80, measured element content (%): C, 73.68; H, 3.46; F, 9.80; N, 12.79. The above analysis results show that the obtained product is the target product.
实施例68Example 68
Figure PCTCN2020081035-appb-000148
Figure PCTCN2020081035-appb-000148
依照实施例56的合成，步骤相同，用化合物2-氯-4,6-二(4-氟苯基)-1,3,5-三嗪代替化合物2-氯-4,6-二苯基-1,3,5-三嗪，得到白色化合物0.635g(产率41.5％)，质谱分析确定的分子离子质量为：765.23(计算值为：765.23)；理论元素含量(％)C 47H 27F 4N 7：C,73.72；H,3.55；F,9.92；N,12.80，实测元素含量(％)：C,73.68；H,3.66；F,9.81；N,12.77。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 56, the steps are the same, and the compound 2-chloro-4,6-bis(4-fluorophenyl)-1,3,5-triazine is used instead of the compound 2-chloro-4,6-diphenyl -1,3,5-triazine, 0.635g of white compound was obtained (yield 41.5%), the molecular ion mass determined by mass spectrometry analysis was 765.23 (calculated value: 765.23); theoretical element content (%) C 47 H 27 F 4 N 7 : C, 73.72; H, 3.55; F, 9.92; N, 12.80, measured element content (%): C, 73.68; H, 3.66; F, 9.81; N, 12.77. The above analysis results show that the obtained product is the target product.
实施例69Example 69
Figure PCTCN2020081035-appb-000149
Figure PCTCN2020081035-appb-000149
依照实施例57的合成，步骤相同，用化合物2-氯-4,6-二(4-氟苯基)-1,3,5-三嗪代替化合物2-氯-4,6-二苯基-1,3,5-三嗪，得到白色化合物0.786g(产率51.4％)，质谱分析确定的分子离子质量为：765.20(计算值为：765.23)；理论元素含量(％)C 47H 27F 4N 7：C,73.72；H,3.55；F,9.92；N,12.80，实测元素含量(％)：C,73.68；H,3.47；F,9.88；N,12.76。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 57, the steps are the same, and the compound 2-chloro-4,6-bis(4-fluorophenyl)-1,3,5-triazine is used instead of the compound 2-chloro-4,6-diphenyl -1,3,5-triazine, 0.786g of white compound was obtained (yield 51.4%), the molecular ion mass determined by mass spectrometry analysis was 765.20 (calculated value: 765.23); theoretical element content (%) C 47 H 27 F 4 N 7 : C, 73.72; H, 3.55; F, 9.92; N, 12.80, measured element content (%): C, 73.68; H, 3.47; F, 9.88; N, 12.76. The above analysis results show that the obtained product is the target product.
实施例70Example 70
Figure PCTCN2020081035-appb-000150
Figure PCTCN2020081035-appb-000150
依照实施例58的合成，步骤相同，用化合物2-氯-4,6-二(4-氟苯基)-1,3,5-三嗪代替化合物2-氯-4,6-二苯基-1,3,5-三嗪，得到白色化合物0.770g(产率50.3％)，质谱分析确定的分子离子质量为：765.12(计算值为：765.23)；理论元素含量(％)C 47H 27F 4N 7：C,73.72；H,3.55；F,9.92；N,12.80，实测元素含量(％)：C,73.86；H,3.39；F,9.79；N,12.77。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 58, the steps are the same, and the compound 2-chloro-4,6-bis(4-fluorophenyl)-1,3,5-triazine is used instead of the compound 2-chloro-4,6-diphenyl -1,3,5-triazine, 0.770g of white compound was obtained (yield 50.3%), the molecular ion mass determined by mass spectrometry was 765.12 (calculated value: 765.23); theoretical element content (%) C 47 H 27 F 4 N 7 : C, 73.72; H, 3.55; F, 9.92; N, 12.80, measured element content (%): C, 73.86; H, 3.39; F, 9.79; N, 12.77. The above analysis results show that the obtained product is the target product.
实施例71Example 71
Figure PCTCN2020081035-appb-000151
Figure PCTCN2020081035-appb-000151
依照实施例59的合成，步骤相同，用化合物2-氯-4,6-二(4-氟苯基)-1,3,5-三嗪代替化合物2-氯-4,6-二苯基-1,3,5-三嗪，得到白色化合物0.762g(产率49.8％)，质谱分析确定的分子离子质量为：765.34(计算值为：765.23)；理论元素含量(％)C 47H 27F 4N 7：C,73.72；H,3.55；F,9.92；N,12.80，实测元素含量(％)：C,73.62；H,3.57；F,9.88；N,12.93。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 59, the steps are the same, and the compound 2-chloro-4,6-bis(4-fluorophenyl)-1,3,5-triazine is used instead of the compound 2-chloro-4,6-diphenyl -1,3,5-triazine, 0.762g of white compound (yield 49.8%) was obtained. The molecular ion mass determined by mass spectrometry analysis was 765.34 (calculated value: 765.23); theoretical element content (%) C 47 H 27 F 4 N 7 : C, 73.72; H, 3.55; F, 9.92; N, 12.80, measured element content (%): C, 73.62; H, 3.57; F, 9.88; N, 12.93. The above analysis results show that the obtained product is the target product.
实施例72Example 72
Figure PCTCN2020081035-appb-000152
Figure PCTCN2020081035-appb-000152
依照实施例60的合成，步骤相同，用化合物2-氯-4,6-二(4-氟苯基)-1,3,5-三嗪代替化合物2-氯-4,6-二苯基-1,3,5-三嗪，得到白色化合物0.808g(产率52.8％)，质谱分析确定的分子离子质量为：765.44(计算值为：765.23)；理论元素含量(％)C 47H 27F 4N 7：C,73.72；H,3.55；F,9.92；N,12.80，实测元素含量(％)：C,73.68；H,3.63；F,9.94；N,12.77。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 60, the steps are the same, and the compound 2-chloro-4,6-bis(4-fluorophenyl)-1,3,5-triazine is used instead of the compound 2-chloro-4,6-diphenyl -1,3,5-triazine, 0.808g of white compound was obtained (yield 52.8%), the molecular ion mass determined by mass spectrometry analysis was 765.44 (calculated value: 765.23); theoretical element content (%) C 47 H 27 F 4 N 7 : C, 73.72; H, 3.55; F, 9.92; N, 12.80, measured element content (%): C, 73.68; H, 3.63; F, 9.94; N, 12.77. The above analysis results show that the obtained product is the target product.
实施例73Example 73
Figure PCTCN2020081035-appb-000153
Figure PCTCN2020081035-appb-000153
依照实施例29的合成，步骤相同，用化合物2-氯-4,6-二(4-氟苯基)-1,3,5-三嗪代替化合物2-氯-4,6-二苯基-1,3,5-三嗪，得到白色化合物0.606g(产率52.9％)，质谱分析确定的分子离子质量为：573.22(计算值为：573.16)；理论元素含量(％)C 34H 19F 4N 5:C,71.20；H,3.34；F,13.25；N,12.21，实测元素含量(％)：C,71.24；H,3.33；F,13.36N,12.31。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 29, the steps are the same, and the compound 2-chloro-4,6-bis(4-fluorophenyl)-1,3,5-triazine is used instead of the compound 2-chloro-4,6-diphenyl -1,3,5-triazine, 0.606g of white compound was obtained (yield 52.9%), the molecular ion mass determined by mass spectrometry analysis was: 573.22 (calculated value: 573.16); theoretical element content (%) C 34 H 19 F 4 N 5 : C, 71.20; H, 3.34; F, 13.25; N, 12.21, measured element content (%): C, 71.24; H, 3.33; F, 13.36N, 12.31. The above analysis results show that the obtained product is the target product.
实施例74Example 74
Figure PCTCN2020081035-appb-000154
Figure PCTCN2020081035-appb-000154
依照实施例1的合成，步骤相同，用化合物N 1-(3-三氟甲基苯基)-1,2-苯二胺代替化合物邻氨基二苯胺，得到白色化合物0.498g(产率58.3％)，质谱分析确定的分子离子质量为：569.32(计算值为：569.18)；理论元素含量(％)C 35H 22F 3N 5：C,73.80；H,3.89；F,10.01；N,12.30；实测元素含量(％)：C,73.77；H,3.92；F,10.11；N,12.35。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 1, the steps were the same, and the compound N 1 -(3-trifluoromethylphenyl)-1,2-phenylenediamine was used instead of the compound o-aminodiphenylamine to obtain 0.498g of a white compound (yield 58.3%) ), the molecular ion mass determined by mass spectrometry analysis is: 569.32 (calculated value: 569.18); theoretical element content (%) C 35 H 22 F 3 N 5 : C, 73.80; H, 3.89; F, 10.01; N, 12.30 Measured element content (%): C, 73.77; H, 3.92; F, 10.11; N, 12.35. The above analysis results show that the obtained product is the target product.
实施例75Example 75
Figure PCTCN2020081035-appb-000155
Figure PCTCN2020081035-appb-000155
依照实施例3的合成，步骤相同，用化合物N 1-(3-三氟甲基苯基)-1,2-苯二胺代替化合物邻氨基二苯胺，得到白色化合物0.532g(产率53.2％)，质谱分析确定的分子离子质量为：569.12(计算值为：569.18)；理论元素含量(％)C 35H 22F 3N 5：C,73.80；H,3.89；F,10.01；N,12.30；实测元素含量(％)：C,73.87；H,3.91；F,10.10；N,12.31。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 3, the steps were the same, and the compound N 1 -(3-trifluoromethylphenyl)-1,2-phenylenediamine was used instead of the compound o-aminodiphenylamine to obtain 0.532g of a white compound (yield 53.2%) ), the molecular ion mass determined by mass spectrometry analysis is: 569.12 (calculated value: 569.18); theoretical element content (%) C 35 H 22 F 3 N 5 : C, 73.80; H, 3.89; F, 10.01; N, 12.30 Measured element content (%): C, 73.87; H, 3.91; F, 10.10; N, 12.31. The above analysis results show that the obtained product is the target product.
实施例76Example 76
Figure PCTCN2020081035-appb-000156
Figure PCTCN2020081035-appb-000156
依照实施例2的合成，步骤相同，用化合物N 1-(3-三氟甲基苯基)-1,2-苯二胺代替化合物邻氨基二苯胺，得到白色化合物0.527g(产率61.7％)，质谱分析确定的分子离子质量为：569.33(计算值为：569.18)；理论元素含量(％)C 35H 22F 3N 5：C,73.80；H,3.89；F,10.01；N,12.30；实测元素含量(％)：C,73.91；H,3.88；F,10.06；N,12.27。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 2, the steps were the same, and the compound N 1 -(3-trifluoromethylphenyl)-1,2-phenylenediamine was used instead of the compound o-aminodiphenylamine to obtain 0.527 g of a white compound (yield 61.7%) ), the molecular ion mass determined by mass spectrometry analysis is: 569.33 (calculated value: 569.18); theoretical element content (%) C 35 H 22 F 3 N 5 : C, 73.80; H, 3.89; F, 10.01; N, 12.30 Measured element content (%): C, 73.91; H, 3.88; F, 10.06; N, 12.27. The above analysis results show that the obtained product is the target product.
实施例77Example 77
Figure PCTCN2020081035-appb-000157
Figure PCTCN2020081035-appb-000157
依照实施例1的合成，步骤相同，用化合物N 1-(3,5-二(三氟甲基)苯基)-1,2-苯二胺代替化合物邻氨基二苯胺，得到白色化合物0.524g(产率54.8％)，质谱分析确定的分子离子质量为：637.22(计算值为：637.17)；理论元素含量(％)C 36H 21F 6N 5：C,67.82；H,3.32；F,17.88；N,10.98，实测元素含量(％)：C,67.77；H,3.35；F,17.90；N,10.87。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 1, the steps are the same, and the compound N 1 -(3,5-bis(trifluoromethyl)phenyl)-1,2-phenylenediamine is substituted for the compound o-aminodiphenylamine to obtain 0.524g of a white compound (Yield 54.8%), the molecular ion mass determined by mass spectrometry analysis is: 637.22 (calculated value: 637.17); theoretical element content (%) C 36 H 21 F 6 N 5 : C, 67.82; H, 3.32; F, 17.88; N, 10.98, measured element content (%): C, 67.77; H, 3.35; F, 17.90; N, 10.87. The above analysis results show that the obtained product is the target product.
实施例78Example 78
Figure PCTCN2020081035-appb-000158
Figure PCTCN2020081035-appb-000158
依照实施例3的合成，步骤相同，用化合物N 1-(3,5-二(三氟甲基)苯基)-1,2-苯二胺代替化合物邻氨基二苯胺，得到白色化合物0.524g(产率54.8％)，质谱分析确定的分子离子质量为：637.20(计算值为：637.17)；理论元素含量(％)C 36H 21F 6N 5：C,67.82；H,3.32；F,17.88；N,10.98，实测元素含量(％)：C,67.87；H,3.45；F,17.82；N,10.97。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 3, the steps are the same, the compound N 1 -(3,5-bis(trifluoromethyl)phenyl)-1,2-phenylenediamine is substituted for the compound o-aminodiphenylamine to obtain 0.524g of a white compound (Yield 54.8%), the molecular ion mass determined by mass spectrometry analysis is: 637.20 (calculated value: 637.17); theoretical element content (%) C 36 H 21 F 6 N 5 : C, 67.82; H, 3.32; F, 17.88; N, 10.98, measured element content (%): C, 67.87; H, 3.45; F, 17.82; N, 10.97. The above analysis results show that the obtained product is the target product.
实施例79Example 79
Figure PCTCN2020081035-appb-000159
Figure PCTCN2020081035-appb-000159
依照实施例2的合成，步骤相同，用化合物N 1-(3,5-二(三氟甲基)苯基)-1,2-苯二胺代替化合物邻氨基二苯胺，得到白色化合物0.585g(产率61.2％)，质谱分析确定的分子离子质量为：637.15(计算值为：637.17)；理论元素含量(％)C 36H 21F 6N 5：C,67.82；H,3.32；F,17.88；N,10.98，实测元素含量(％)：C,67.87；H,3.36；F,17.89；N,10.94。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 2, the steps are the same, and the compound N 1 -(3,5-bis(trifluoromethyl)phenyl)-1,2-phenylenediamine is substituted for the compound o-aminodiphenylamine to obtain 0.585g of a white compound (Yield 61.2%), the molecular ion mass determined by mass spectrometry analysis is: 637.15 (calculated value: 637.17); theoretical element content (%) C 36 H 21 F 6 N 5 : C, 67.82; H, 3.32; F, 17.88; N, 10.98, measured element content (%): C, 67.87; H, 3.36; F, 17.89; N, 10.94. The above analysis results show that the obtained product is the target product.
实施例80Example 80
Figure PCTCN2020081035-appb-000160
Figure PCTCN2020081035-appb-000160
依照实施例4的合成，步骤相同，用化合物3-三氟甲基苯甲醛代替化合物苯甲醛，得到白色化合物0.500g(产率58.6％)，质谱分析确定的分子离子质量为：569.19(计算值为：569.18)；理论元素含 量(％)C 35H 22F 3N 5：C,73.80；H,3.89；F,10.01；N,12.30；实测元素含量(％)：C,73.88；H,3.83；F,10.14；N,12.34。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 4, the steps were the same, and the compound 3-trifluoromethylbenzaldehyde was used instead of the compound benzaldehyde to obtain 0.500 g of a white compound (yield 58.6%). The molecular ion mass determined by mass spectrometry was 569.19 (calculated value) Is: 569.18); theoretical element content (%) C 35 H 22 F 3 N 5 : C, 73.80; H, 3.89; F, 10.01; N, 12.30; measured element content (%): C, 73.88; H, 3.83 ; F, 10.14; N, 12.34. The above analysis results show that the obtained product is the target product.
实施例81Example 81
Figure PCTCN2020081035-appb-000161
Figure PCTCN2020081035-appb-000161
依照实施例6的合成，步骤相同，用化合物3-三氟甲基苯甲醛代替化合物苯甲醛，得到白色化合物0.523g(产率66.7％)，质谱分析确定的分子离子质量为：569.33(计算值为：569.18)；理论元素含量(％)C 35H 22F 3N 5：C,73.80；H,3.89；F,10.01；N,12.30；实测元素含量(％)：C,73.91；H,3.88；F,10.06；N,12.27。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 6, the steps are the same, and the compound 3-trifluoromethylbenzaldehyde is used instead of the compound benzaldehyde to obtain 0.523g of a white compound (yield 66.7%). The molecular ion mass determined by mass spectrometry is 569.33 (calculated value) Is: 569.18); theoretical element content (%) C 35 H 22 F 3 N 5 : C, 73.80; H, 3.89; F, 10.01; N, 12.30; measured element content (%): C, 73.91; H, 3.88 ; F, 10.06; N, 12.27. The above analysis results show that the obtained product is the target product.
实施例82Example 82
Figure PCTCN2020081035-appb-000162
Figure PCTCN2020081035-appb-000162
依照实施例5的合成，步骤相同，用化合物3-三氟甲基苯甲醛代替化合物苯甲醛，得到白色化合物0.516g(产率60.4％)，质谱分析确定的分子离子质量为：569.23(计算值为：569.18)；理论元素含量(％)C 35H 22F 3N 5：C,73.80；H,3.89；F,10.01；N,12.30；实测元素含量(％)：C,73.82；H,3.85；F,10.14；N,12.33。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 5, the steps were the same, and the compound 3-trifluoromethylbenzaldehyde was used instead of the compound benzaldehyde to obtain 0.516g of a white compound (yield 60.4%). The mass of the molecular ion determined by mass spectrometry was 569.23 (calculated value) Is: 569.18); theoretical element content (%) C 35 H 22 F 3 N 5 : C, 73.80; H, 3.89; F, 10.01; N, 12.30; measured element content (%): C, 73.82; H, 3.85 ; F, 10.14; N, 12.33. The above analysis results show that the obtained product is the target product.
实施例83Example 83
Figure PCTCN2020081035-appb-000163
Figure PCTCN2020081035-appb-000163
依照实施例5的合成，步骤相同，用化合物3,5-二(三氟甲基)苯甲醛代替化合物苯甲醛，得到白色化合物0.454g(产率47.5％)，质谱分析确定的分子离子质量为：637.21(计算值为：637.17)；理论元素含量(％)C 36H 21F 6N 5：C,67.82；H,3.32；F,17.88；N,10.98，实测元素含量(％)：C,67.85；H,3.30；F,17.90；N,10.92。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 5, the steps are the same, and the compound 3,5-bis(trifluoromethyl)benzaldehyde is used instead of the compound benzaldehyde to obtain 0.454g of white compound (yield 47.5%). The mass of the molecular ion determined by mass spectrometry is : 637.21 (calculated value: 637.17); theoretical element content (%) C 36 H 21 F 6 N 5 : C, 67.82; H, 3.32; F, 17.88; N, 10.98, measured element content (%): C, 67.85; H, 3.30; F, 17.90; N, 10.92. The above analysis results show that the obtained product is the target product.
实施例84Example 84
Figure PCTCN2020081035-appb-000164
Figure PCTCN2020081035-appb-000164
依照实施例9的合成，步骤相同，用化合物2-氯-4,6-二(4-三氟甲基苯基)-1,3,5-三嗪代替化合物2-氯-4,6-二苯基-1,3,5-三嗪，得到白色化合物0.532g(产率55.6％)，质谱分析确定的分子离子质量为：638.18(计算值为：638.17)；理论元素含量(％)C 35H 20F 6N 6：C,65.83；H,3.16；F,17.85；N,13.16，实测元素含量(％)：C,65.85；H,3.10；F,17.86；N,13.12。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 9, the steps are the same, and the compound 2-chloro-4,6-bis(4-trifluoromethylphenyl)-1,3,5-triazine is used instead of the compound 2-chloro-4,6- Diphenyl-1,3,5-triazine, 0.532g of white compound (yield 55.6%) was obtained. The molecular ion mass determined by mass spectrometry analysis was 638.18 (calculated value: 638.17); theoretical element content (%) C 35 H 20 F 6 N 6 : C, 65.83; H, 3.16; F, 17.85; N, 13.16, measured element content (%): C, 65.85; H, 3.10; F, 17.86; N, 13.12. The above analysis results show that the obtained product is the target product.
实施例85Example 85
Figure PCTCN2020081035-appb-000165
Figure PCTCN2020081035-appb-000165
依照实施例49的合成，步骤相同，用化合物2-氯-4,6-二(4-三氟甲基苯基)-1,3,5-三嗪代替化合物2-氯-4,6-二苯基-1,3,5-三嗪，得到白色化合物0.511g(产率46.6％)，质谱分析确定的分子离子质量为：829.24(计算值为：829.24)；理论元素含量(％)C 49H 29F 6N 7：C,70.92；H,3.52；F,13.74；N,11.82，实测元素含量(％)：C,70.95；H,3.54；F,13.77；N,11.90。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 49, the steps were the same, and the compound 2-chloro-4,6-bis(4-trifluoromethylphenyl)-1,3,5-triazine was used instead of the compound 2-chloro-4,6- Diphenyl-1,3,5-triazine, 0.511g of white compound (yield 46.6%) was obtained. The molecular ion mass determined by mass spectrometry analysis was 829.24 (calculated value: 829.24); theoretical element content (%) C 49 H 29 F 6 N 7 : C, 70.92; H, 3.52; F, 13.74; N, 11.82, measured element content (%): C, 70.95; H, 3.54; F, 13.77; N, 11.90. The above analysis results show that the obtained product is the target product.
实施例86Example 86
Figure PCTCN2020081035-appb-000166
Figure PCTCN2020081035-appb-000166
依照实施例51的合成，步骤相同，用化合物2-氯-4,6-二(4-三氟甲基苯基)-1,3,5-三嗪代替化合物2-氯-4,6-二苯基-1,3,5-三嗪，得到白色化合物0.419g(产率33.6％)，质谱分析确定的分子离子质量为：831.24(计算值为：831.23)；理论元素含量(％)C 47H 27F 6N 9：C,67.87；H,3.27；F,13.70；N,15.16，实测元素含量(％)：C,67.86；H,3.29；F,13.72；N,15.14。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 51, the steps were the same, and the compound 2-chloro-4,6-bis(4-trifluoromethylphenyl)-1,3,5-triazine was used instead of the compound 2-chloro-4,6- Diphenyl-1,3,5-triazine, 0.419g of white compound was obtained (yield 33.6%), the molecular ion mass determined by mass spectrometry analysis was: 831.24 (calculated value: 831.23); theoretical element content (%) C 47 H 27 F 6 N 9 : C, 67.87; H, 3.27; F, 13.70; N, 15.16, measured element content (%): C, 67.86; H, 3.29; F, 13.72; N, 15.14. The above analysis results show that the obtained product is the target product.
实施例87Example 87
Figure PCTCN2020081035-appb-000167
Figure PCTCN2020081035-appb-000167
依照实施例53的合成，步骤相同，用化合物2-氯-4,6-二(4-三氟甲基苯基)-1,3,5-三嗪代替化合物2-氯-4,6-二苯基-1,3,5-三嗪，得到白色化合物0.446g(产率35.8％)，质谱分析确定的分子离子质量为：831.20(计算值为：831.23)；理论元素含量(％)C 47H 27F 6N 9：C,67.87；H,3.27；F,13.70；N,15.16，实测元素含量(％)：C,67.89；H,3.33；F,13.74；N,15.18。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 53, the steps were the same, and the compound 2-chloro-4,6-bis(4-trifluoromethylphenyl)-1,3,5-triazine was used instead of the compound 2-chloro-4,6- Diphenyl-1,3,5-triazine, 0.446g of white compound was obtained (yield 35.8%), the molecular ion mass determined by mass spectrometry analysis was 831.20 (calculated value: 831.23); theoretical element content (%) C 47 H 27 F 6 N 9 : C, 67.87; H, 3.27; F, 13.70; N, 15.16, measured element content (%): C, 67.89; H, 3.33; F, 13.74; N, 15.18. The above analysis results show that the obtained product is the target product.
实施例88Example 88
Figure PCTCN2020081035-appb-000168
Figure PCTCN2020081035-appb-000168
依照实施例56的合成，步骤相同，2-氯-4,6-二(4-三氟甲基苯基)-1,3,5-三嗪代替化合物2-氯-4,6-二苯基-1,3,5-三嗪，N-(3-三氟甲基苯基)-1,2-苯二胺代替化合物N-(3-氟苯基)-1,2-苯二胺，得到白色化合物0.583g(产率40.3％)，质谱分析确定的分子离子质量为：965.21(计算值为：965.21)；理论元素含量(％)C 51H 27F 12N 7：C,63.42；H,2.82；F,23.61；N,10.15，实测元素含量(％)：C,63.45；H,2.90；F,23.63；N,10.22。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 56, the steps are the same, 2-chloro-4,6-bis(4-trifluoromethylphenyl)-1,3,5-triazine instead of the compound 2-chloro-4,6-diphenyl Yl-1,3,5-triazine, N-(3-trifluoromethylphenyl)-1,2-phenylenediamine instead of compound N-(3-fluorophenyl)-1,2-phenylenediamine , Obtain 0.583g of white compound (yield 40.3%), the molecular ion mass determined by mass spectrometry analysis is: 965.21 (calculated value: 965.21); theoretical element content (%) C 51 H 27 F 12 N 7 : C, 63.42; H, 2.82; F, 23.61; N, 10.15, measured element content (%): C, 63.45; H, 2.90; F, 23.63; N, 10.22. The above analysis results show that the obtained product is the target product.
实施例89Example 89
Figure PCTCN2020081035-appb-000169
Figure PCTCN2020081035-appb-000169
依照实施例29的合成，步骤相同，用化合物2-氯-4,6-二(4-三氟甲基苯基)-1,3,5-三嗪代替化合物2-氯-4,6-二苯基-1,3,5-三嗪，N-(3,5-二(三氟甲基)苯基)-1,2-苯二胺代替化合物N-(3-氟苯基)-1,2-苯二胺，得到白色化合物0.594g(产率51.2％)，质谱分析确定的分子离子质量为：773.18(计算值为：773.14)；理论元素含量(％)C 38H 19F 12N 5:C,59.00；H,2.48；F,29.47；N,9.05，实测元素含量(％)：C,59.08；H,2.53；F,29.55；N,9.12。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 29, the steps are the same, and the compound 2-chloro-4,6-bis(4-trifluoromethylphenyl)-1,3,5-triazine is used instead of the compound 2-chloro-4,6- Diphenyl-1,3,5-triazine, N-(3,5-bis(trifluoromethyl)phenyl)-1,2-phenylenediamine instead of compound N-(3-fluorophenyl)- 1,2-Phenylenediamine, 0.594g of white compound (yield 51.2%) was obtained, the molecular ion mass determined by mass spectrometry analysis was: 773.18 (calculated value: 773.14); theoretical element content (%) C 38 H 19 F 12 N 5 : C, 59.00; H, 2.48; F, 29.47; N, 9.05, measured element content (%): C, 59.08; H, 2.53; F, 29.55; N, 9.12. The above analysis results show that the obtained product is the target product.
实施例90Example 90
Figure PCTCN2020081035-appb-000170
Figure PCTCN2020081035-appb-000170
依照实施例49的合成，步骤相同，用化合物N 1,N 1’-{5-溴-1,3-二(2-三氟甲基苯基)}双(1,2-苯二胺)代替化合物N 1,N 1’(5-溴-1,3-二苯基)双(1,2-苯二胺)，得到白色化合物0.599g(产率48.2％)，质谱分析确定的分子离子质量为：829.25(计算值为：829.24)；理论元素含量(％)C 49H 29F 6N 7：C,70.92；H,3.52；F,13.74；N,11.82，实测元素含量(％)：C,70.93；H,3.55；F,13.77；N,11.80。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 49, the steps are the same, using the compound N 1 , N 1 '-{5-bromo-1,3-bis(2-trifluoromethylphenyl)}bis(1,2-phenylenediamine) Instead of compound N 1 , N 1 '(5-bromo-1,3-diphenyl)bis(1,2-phenylenediamine), 0.599g of white compound (yield 48.2%) was obtained, and the molecular ion was confirmed by mass spectrometry. Mass: 829.25 (calculated value: 829.24); theoretical element content (%) C 49 H 29 F 6 N 7 : C,70.92; H,3.52; F,13.74; N,11.82, measured element content (%): C, 70.93; H, 3.55; F, 13.77; N, 11.80. The above analysis results show that the obtained product is the target product.
实施例91Example 91
Figure PCTCN2020081035-appb-000171
Figure PCTCN2020081035-appb-000171
依照实施例59的合成，步骤相同，用化合物2-氯-4,6-二(4-氟苯基)-1,3,5-三嗪代替化合物2-氯-4,6-二苯基-1,3,5-三嗪，用化合物3-三氟甲基苯甲醛代替化合物苯甲醛，得到白色化合物0.640g(产率44.2％)，质谱分析确定的分子离子质量为：965.23(计算值为：965.21)；理论元素含量(％)C 51H 27F 12N 7：C,63.42；H,2.82；F,23.61；N,10.15，实测元素含量(％)：C,63.48；H,2.90；F,23.66；N,10.21。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 59, the steps are the same, and the compound 2-chloro-4,6-bis(4-fluorophenyl)-1,3,5-triazine is used instead of the compound 2-chloro-4,6-diphenyl -1,3,5-triazine, the compound 3-trifluoromethylbenzaldehyde was substituted for the compound benzaldehyde to obtain 0.640g of a white compound (yield 44.2%). The molecular ion mass determined by mass spectrometry was 965.23 (calculated value) Is: 965.21); theoretical element content (%) C 51 H 27 F 12 N 7 : C, 63.42; H, 2.82; F, 23.61; N, 10.15, measured element content (%): C, 63.48; H, 2.90 ; F, 23.66; N, 10.21. The above analysis results show that the obtained product is the target product.
实施例92Example 92
Figure PCTCN2020081035-appb-000172
Figure PCTCN2020081035-appb-000172
依照实施例19的合成，步骤相同，用化合物N 1-(2-异丙基苯基)苯-1,2-二胺代替化合物N 1-(2-氟苯基)苯-1,2-二胺，得到白色化合物0.523g(产率37.9％)。质谱分析确定的分子离子质量为：543.26(计算值为：543.24)；理论元素含量(％)C 37H 29N 5：C,81.74；H,5.38；N,12.88；实测元素含量(％)：C,81.75；H,5.37；N,12.88。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 19, the steps were the same, and the compound N 1 -(2-isopropylphenyl)benzene-1,2-diamine was used instead of the compound N 1 -(2-fluorophenyl)benzene-1,2- Diamine, 0.523 g of white compound was obtained (yield 37.9%). The molecular ion mass determined by mass spectrometry analysis is: 543.26 (calculated value: 543.24); theoretical element content (%) C 37 H 29 N 5 : C, 81.74; H, 5.38; N, 12.88; measured element content (%): C, 81.75; H, 5.37; N, 12.88. The above analysis results show that the obtained product is the target product.
实施例93Example 93
Figure PCTCN2020081035-appb-000173
Figure PCTCN2020081035-appb-000173
依照实施例20的合成，步骤相同，用化合物N 1-(3-异丙基苯基)苯-1,2-二胺代替化合物N 1-(3-氟苯基)苯-1,2-二胺，得到白色化合物0.503g(产率36.9％)。质谱分析确定的分子离子质量为：543.27(计算值为：543.24)；理论元素含量(％)C 37H 29N 5：C,81.74；H,5.38；N,12.88；实测元素含量(％)：C,81.75；H,5.37；N,12.88。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 20, the steps are the same, and the compound N 1 -(3-isopropylphenyl)benzene-1,2-diamine is used instead of the compound N 1 -(3-fluorophenyl)benzene-1,2- Diamine, 0.503 g of a white compound was obtained (yield 36.9%). The molecular ion mass determined by mass spectrometry analysis is: 543.27 (calculated value: 543.24); theoretical element content (%) C 37 H 29 N 5 : C, 81.74; H, 5.38; N, 12.88; measured element content (%): C, 81.75; H, 5.37; N, 12.88. The above analysis results show that the obtained product is the target product.
实施例94Example 94
Figure PCTCN2020081035-appb-000174
Figure PCTCN2020081035-appb-000174
依照实施例21的合成，步骤相同，用化合物N 1-(4-异丙基苯基)苯-1,2-二胺代替化合物N 1-(4-氟苯基)苯-1,2-二胺，得到白色化合物0.423g(产率37.0％)。质谱分析确定的分子离子质量为：543.27(计算值为：543.24)；理论元素含量(％)C 37H 29N 5：C,81.74；H,5.38；N,12.88；实测元素含量(％)：C,81.75；H,5.37；N,12.88。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 21, the steps are the same, and the compound N 1 -(4-isopropylphenyl)benzene-1,2-diamine is substituted for the compound N 1 -(4-fluorophenyl)benzene-1,2- Diamine, 0.423 g of a white compound was obtained (yield 37.0%). The molecular ion mass determined by mass spectrometry analysis is: 543.27 (calculated value: 543.24); theoretical element content (%) C 37 H 29 N 5 : C, 81.74; H, 5.38; N, 12.88; measured element content (%): C, 81.75; H, 5.37; N, 12.88. The above analysis results show that the obtained product is the target product.
实施例95Example 95
Figure PCTCN2020081035-appb-000175
Figure PCTCN2020081035-appb-000175
依照实施例22的合成，步骤相同，用化合物N 1-(2-异丙基苯基)苯-1,2-二胺代替化合物N 1-(2-氟苯基)苯-1,2-二胺，得到白色化合物0.523g(产率37.9％)。质谱分析确定的分子离子质量为：543.26(计算值为：543.24)；理论元素含量(％)C 37H 29N 5：C,81.74；H,5.38；N,12.88；实测元素含量(％)：C,81.75；H,5.37；N,12.88。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 22, the steps were the same, and the compound N 1 -(2-isopropylphenyl)benzene-1,2-diamine was used instead of the compound N 1 -(2-fluorophenyl)benzene-1,2- Diamine, 0.523 g of white compound was obtained (yield 37.9%). The molecular ion mass determined by mass spectrometry analysis is: 543.26 (calculated value: 543.24); theoretical element content (%) C 37 H 29 N 5 : C, 81.74; H, 5.38; N, 12.88; measured element content (%): C, 81.75; H, 5.37; N, 12.88. The above analysis results show that the obtained product is the target product.
实施例96Example 96
Figure PCTCN2020081035-appb-000176
Figure PCTCN2020081035-appb-000176
依照实施例23的合成，步骤相同，用化合物N 1-(3-异丙基苯基)苯-1,2-二胺代替化合物N 1-(3-氟苯基)苯-1,2-二胺，得到白色化合物0.578g(产率33.9％)。质谱分析确定的分子离子质量为：543.27(计算值为：543.24)；理论元素含量(％)C 37H 29N 5：C,81.74；H,5.38；N,12.88；实测元素含量(％)：C,81.75；H,5.37；N,12.88。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 23, the steps were the same, and the compound N 1 -(3-isopropylphenyl)benzene-1,2-diamine was used instead of the compound N 1 -(3-fluorophenyl)benzene-1,2- Diamine, 0.578 g of a white compound was obtained (yield 33.9%). The molecular ion mass determined by mass spectrometry analysis is: 543.27 (calculated value: 543.24); theoretical element content (%) C 37 H 29 N 5 : C, 81.74; H, 5.38; N, 12.88; measured element content (%): C, 81.75; H, 5.37; N, 12.88. The above analysis results show that the obtained product is the target product.
实施例97Example 97
Figure PCTCN2020081035-appb-000177
Figure PCTCN2020081035-appb-000177
依照实施例24的合成，步骤相同，用化合物N 1-(4-异丙基苯基)苯-1,2-二胺代替化合物N 1-(4-氟苯基)苯-1,2-二胺，得到白色化合物0.513g(产率36.9％)。质谱分析确定的分子离子质量为：543.29(计算值为：543.24)；理论元素含量(％)C 37H 29N 5：C,81.74；H,5.38；N,12.88；实测元素含量(％)：C,81.75；H,5.37；N,12.88。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 24, the steps were the same, and the compound N 1 -(4-isopropylphenyl)benzene-1,2-diamine was used instead of the compound N 1 -(4-fluorophenyl)benzene-1,2- Diamine, 0.513 g of a white compound was obtained (yield 36.9%). The molecular ion mass determined by mass spectrometry analysis is: 543.29 (calculated value: 543.24); theoretical element content (%) C 37 H 29 N 5 : C, 81.74; H, 5.38; N, 12.88; measured element content (%): C, 81.75; H, 5.37; N, 12.88. The above analysis results show that the obtained product is the target product.
实施例98Example 98
Figure PCTCN2020081035-appb-000178
Figure PCTCN2020081035-appb-000178
依照实施例25的合成，步骤相同，用化合物N 1-(2-异丙基苯基)苯-1,2-二胺代替化合物N 1-(2-氟苯基)苯-1,2-二胺，得到白色化合物0.523g(产率37.9％)。质谱分析确定的分子离子质量为：543.27(计算值为：543.24)；理论元素含量(％)C 37H 29N 5：C,81.74；H,5.38；N,12.88；实测元素含量(％)：C,81.75；H,5.37；N,12.88。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 25, the steps are the same, and the compound N 1 -(2-isopropylphenyl)benzene-1,2-diamine is used instead of the compound N 1 -(2-fluorophenyl)benzene-1,2- Diamine, 0.523 g of white compound was obtained (yield 37.9%). The molecular ion mass determined by mass spectrometry analysis is: 543.27 (calculated value: 543.24); theoretical element content (%) C 37 H 29 N 5 : C, 81.74; H, 5.38; N, 12.88; measured element content (%): C, 81.75; H, 5.37; N, 12.88. The above analysis results show that the obtained product is the target product.
实施例99Example 99
Figure PCTCN2020081035-appb-000179
Figure PCTCN2020081035-appb-000179
依照实施例26的合成，步骤相同，用化合物N 1-(3-异丙基苯基)苯-1,2-二胺代替化合物N 1-(3-氟苯基)苯-1,2-二胺，得到白色化合物0.423g(产率37.7％)。质谱分析确定的分子离子质量为：543.29(计算值为：543.24)；理论元素含量(％)C 37H 29N 5：C,81.74；H,5.38；N,12.88；实测元素含量(％)：C,81.75；H,5.37；N,12.88。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 26, the steps are the same, and the compound N 1 -(3-isopropylphenyl)benzene-1,2-diamine is substituted for the compound N 1 -(3-fluorophenyl)benzene-1,2- Diamine, 0.423 g of a white compound was obtained (yield 37.7%). The molecular ion mass determined by mass spectrometry analysis is: 543.29 (calculated value: 543.24); theoretical element content (%) C 37 H 29 N 5 : C, 81.74; H, 5.38; N, 12.88; measured element content (%): C, 81.75; H, 5.37; N, 12.88. The above analysis results show that the obtained product is the target product.
实施例100Example 100
Figure PCTCN2020081035-appb-000180
Figure PCTCN2020081035-appb-000180
依照实施例27的合成，步骤相同，用化合物N 1-(4-异丙基苯基)苯-1,2-二胺代替化合物N 1-(4-氟苯基)苯-1,2-二胺，得到白色化合物0.523g(产率32.9％)。质谱分析确定的分子离子质量为：543.28(计算值为：543.24)；理论元素含量(％)C 37H 29N 5：C,81.74；H,5.38；N,12.88；实测元素含量(％)：C,81.75；H,5.37；N,12.88。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 27, the steps were the same, and the compound N 1 -(4-isopropylphenyl)benzene-1,2-diamine was used instead of the compound N 1 -(4-fluorophenyl)benzene-1,2- Diamine, 0.523 g of a white compound (yield 32.9%) was obtained. The molecular ion mass determined by mass spectrometry analysis is: 543.28 (calculated value: 543.24); theoretical element content (%) C 37 H 29 N 5 : C, 81.74; H, 5.38; N, 12.88; measured element content (%): C, 81.75; H, 5.37; N, 12.88. The above analysis results show that the obtained product is the target product.
实施例101Example 101
Figure PCTCN2020081035-appb-000181
Figure PCTCN2020081035-appb-000181
依照实施例28的合成，步骤相同，用化合物N 1-(3,5-二异丙基苯基)苯-1,2-二胺代替化合物N 1-(3，5-氟苯基)苯-1,2-二胺，得到白色化合物0.523g(产率37.9％)。质谱分析确定的分子离子质量为：585.26(计算值为：585.29)；理论元素含量(％)C 40H 35N 5：C,82.02；H,6.02；N,11.96；实测元素含量(％)：C,82.05；H,6.07；N,11.88。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 28, the steps are the same, and the compound N 1 -(3,5-diisopropylphenyl)benzene-1,2-diamine is used instead of the compound N 1 -(3,5-fluorophenyl)benzene -1,2-diamine, 0.523 g of a white compound was obtained (yield 37.9%). The molecular ion mass determined by mass spectrometry analysis is: 585.26 (calculated value: 585.29); theoretical element content (%) C 40 H 35 N 5 : C, 82.02; H, 6.02; N, 11.96; measured element content (%): C, 82.05; H, 6.07; N, 11.88. The above analysis results show that the obtained product is the target product.
实施例102Example 102
Figure PCTCN2020081035-appb-000182
Figure PCTCN2020081035-appb-000182
依照实施例29的合成，步骤相同，用化合物N 1-(3,5-二异丙基苯基)苯-1,2-二胺代替化合物N 1-(3，5-氟苯基)苯-1,2-二胺，得到白色化合物0.520g(产率35.9％)。质谱分析确定的分子离子质量为：585.26(计算值为：585.29)；理论元素含量(％)C 40H 35N 5：C,82.02；H,6.02；N,11.96；实测元素含量(％)：C,82.05；H,6.07；N,11.88。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 29, the steps are the same, and the compound N 1 -(3,5-diisopropylphenyl)benzene-1,2-diamine is used instead of the compound N 1 -(3,5-fluorophenyl)benzene -1,2-diamine, 0.520 g of white compound was obtained (yield 35.9%). The molecular ion mass determined by mass spectrometry analysis is: 585.26 (calculated value: 585.29); theoretical element content (%) C 40 H 35 N 5 : C, 82.02; H, 6.02; N, 11.96; measured element content (%): C, 82.05; H, 6.07; N, 11.88. The above analysis results show that the obtained product is the target product.
实施例103Example 103
Figure PCTCN2020081035-appb-000183
Figure PCTCN2020081035-appb-000183
依照实施例30的合成，步骤相同，用化合物N 1-(3,5-二异丙基苯基)苯-1,2-二胺代替化合物N 1-(3，5-氟苯基)苯-1,2-二胺，得到白色化合物0.527g(产率35.9％)。质谱分析确定的分子离子质量为：585.27(计算值为：585.29)；理论元素含量(％)C 40H 35N 5：C,82.02；H,6.02；N,11.96；实测元素含量(％)：C,82.05；H,6.07；N,11.88。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 30, the steps are the same, and the compound N 1 -(3,5-diisopropylphenyl)benzene-1,2-diamine is used instead of the compound N 1 -(3,5-fluorophenyl)benzene -1,2-diamine, 0.527 g of white compound was obtained (yield 35.9%). The molecular ion mass determined by mass spectrometry analysis is: 585.27 (calculated value: 585.29); theoretical element content (%) C 40 H 35 N 5 : C, 82.02; H, 6.02; N, 11.96; measured element content (%): C, 82.05; H, 6.07; N, 11.88. The above analysis results show that the obtained product is the target product.
实施例104Example 104
Figure PCTCN2020081035-appb-000184
Figure PCTCN2020081035-appb-000184
依照实施例31的合成，步骤相同，用化合物2-异丙基苯甲醛代替化合物2-氟苯甲醛，得到白色化合物0.507g(产率37.8％)。质谱分析确定的分子离子质量为：543.27(计算值为：543.24)；理论元素含量(％)C 37H 29N 5：C,81.74；H,5.38；N,12.88；实测元素含量(％)：C,81.75；H,5.37；N,12.88。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 31, the procedure was the same, and the compound 2-isopropylbenzaldehyde was used instead of the compound 2-fluorobenzaldehyde to obtain 0.507 g of a white compound (yield 37.8%). The molecular ion mass determined by mass spectrometry analysis is: 543.27 (calculated value: 543.24); theoretical element content (%) C 37 H 29 N 5 : C, 81.74; H, 5.38; N, 12.88; measured element content (%): C, 81.75; H, 5.37; N, 12.88. The above analysis results show that the obtained product is the target product.
实施例105Example 105
Figure PCTCN2020081035-appb-000185
Figure PCTCN2020081035-appb-000185
依照实施例32的合成，步骤相同，用化合物2-异丙基苯甲醛代替化合物2-氟苯甲醛，得到白色化合物0.523g(产率37.6％)。质谱分析确定的分子离子质量为：543.27(计算值为：543.24)；理论元素含量(％)C 37H 29N 5：C,81.74；H,5.38；N,12.88；实测元素含量(％)：C,81.75；H,5.37；N,12.88。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 32, the procedure was the same, and the compound 2-isopropylbenzaldehyde was substituted for the compound 2-fluorobenzaldehyde to obtain 0.523 g of a white compound (yield 37.6%). The molecular ion mass determined by mass spectrometry analysis is: 543.27 (calculated value: 543.24); theoretical element content (%) C 37 H 29 N 5 : C, 81.74; H, 5.38; N, 12.88; measured element content (%): C, 81.75; H, 5.37; N, 12.88. The above analysis results show that the obtained product is the target product.
实施例106Example 106
Figure PCTCN2020081035-appb-000186
Figure PCTCN2020081035-appb-000186
依照实施例33的合成，步骤相同，用化合物2-异丙基苯甲醛代替化合物2-氟苯甲醛，得到白色化合物0.523g(产率30.9％)。质谱分析确定的分子离子质量为：543.26(计算值为：543.24)；理论元素含量(％)C 37H 29N 5：C,81.74；H,5.38；N,12.88；实测元素含量(％)：C,81.75；H,5.37；N,12.88。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 33, the procedure was the same, and the compound 2-isopropylbenzaldehyde was used instead of the compound 2-fluorobenzaldehyde to obtain 0.523 g of a white compound (yield 30.9%). The molecular ion mass determined by mass spectrometry analysis is: 543.26 (calculated value: 543.24); theoretical element content (%) C 37 H 29 N 5 : C, 81.74; H, 5.38; N, 12.88; measured element content (%): C, 81.75; H, 5.37; N, 12.88. The above analysis results show that the obtained product is the target product.
实施例107Example 107
Figure PCTCN2020081035-appb-000187
Figure PCTCN2020081035-appb-000187
依照实施例34的合成，步骤相同，用化合物3-异丙基苯甲醛代替化合物3-氟苯甲醛，得到白色化合物0.523g(产率37.9％)。质谱分析确定的分子离子质量为：543.21(计算值为：543.24)；理论元素含量(％)C 37H 29N 5：C,81.74；H,5.38；N,12.88；实测元素含量(％)：C,81.75；H,5.37；N,12.88。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 34, the steps were the same, and the compound 3-isopropylbenzaldehyde was used instead of the compound 3-fluorobenzaldehyde to obtain 0.523 g of a white compound (yield 37.9%). The molecular ion mass determined by mass spectrometry analysis is: 543.21 (calculated value: 543.24); theoretical element content (%) C 37 H 29 N 5 : C, 81.74; H, 5.38; N, 12.88; measured element content (%): C, 81.75; H, 5.37; N, 12.88. The above analysis results show that the obtained product is the target product.
实施例108Example 108
Figure PCTCN2020081035-appb-000188
Figure PCTCN2020081035-appb-000188
依照实施例35的合成，步骤相同，用化合物3-异丙基苯甲醛代替化合物3-氟苯甲醛，得到白色化合物0.423g(产率37.2％)。质谱分析确定的分子离子质量为：543.29(计算值为：543.24)；理论元素含量(％)C 37H 29N 5：C,81.74；H,5.38；N,12.88；实测元素含量(％)：C,81.75；H,5.37；N,12.88。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 35, the steps were the same, and the compound 3-isopropylbenzaldehyde was used instead of the compound 3-fluorobenzaldehyde to obtain 0.423 g of a white compound (yield 37.2%). The molecular ion mass determined by mass spectrometry analysis is: 543.29 (calculated value: 543.24); theoretical element content (%) C 37 H 29 N 5 : C, 81.74; H, 5.38; N, 12.88; measured element content (%): C, 81.75; H, 5.37; N, 12.88. The above analysis results show that the obtained product is the target product.
实施例109Example 109
Figure PCTCN2020081035-appb-000189
Figure PCTCN2020081035-appb-000189
依照实施例36的合成，步骤相同，用化合物3-异丙基苯甲醛代替化合物3-氟苯甲醛，得到白色化合物0.479g(产率37.1％)。质谱分析确定的分子离子质量为：543.23(计算值为：543.24)；理论元素含量(％)C 37H 29N 5：C,81.74；H,5.38；N,12.88；实测元素含量(％)：C,81.75；H,5.37；N,12.88。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 36, the procedure was the same, and the compound 3-isopropylbenzaldehyde was substituted for the compound 3-fluorobenzaldehyde to obtain 0.479 g of a white compound (yield 37.1%). The molecular ion mass determined by mass spectrometry analysis is: 543.23 (calculated value: 543.24); theoretical element content (%) C 37 H 29 N 5 : C, 81.74; H, 5.38; N, 12.88; measured element content (%): C, 81.75; H, 5.37; N, 12.88. The above analysis results show that the obtained product is the target product.
实施例110Example 110
Figure PCTCN2020081035-appb-000190
Figure PCTCN2020081035-appb-000190
依照实施例37的合成，步骤相同，用化合物4-异丙基苯甲醛代替化合物4-氟苯甲醛，得到白色化合物0.523g(产率37.9％)。质谱分析确定的分子离子质量为：543.28(计算值为：543.24)；理论元素含量(％)C 37H 29N 5：C,81.74；H,5.38；N,12.88；实测元素含量(％)：C,81.75；H,5.37；N,12.88。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 37, the procedure was the same, and the compound 4-isopropylbenzaldehyde was used instead of the compound 4-fluorobenzaldehyde to obtain 0.523 g of a white compound (yield 37.9%). The molecular ion mass determined by mass spectrometry analysis is: 543.28 (calculated value: 543.24); theoretical element content (%) C 37 H 29 N 5 : C, 81.74; H, 5.38; N, 12.88; measured element content (%): C, 81.75; H, 5.37; N, 12.88. The above analysis results show that the obtained product is the target product.
实施例111Example 111
Figure PCTCN2020081035-appb-000191
Figure PCTCN2020081035-appb-000191
依照实施例38的合成，步骤相同，用化合物4-异丙基苯甲醛代替化合物4-氟苯甲醛，得到白色化合物0.523g(产率37.9％)。质谱分析确定的分子离子质量为：543.22(计算值为：543.24)；理论元素含量(％)C 37H 29N 5：C,81.74；H,5.38；N,12.88；实测元素含量(％)：C,81.75；H,5.37；N,12.88。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 38, the procedure was the same, and the compound 4-isopropylbenzaldehyde was used instead of the compound 4-fluorobenzaldehyde to obtain 0.523 g of a white compound (yield 37.9%). The molecular ion mass determined by mass spectrometry analysis is: 543.22 (calculated value: 543.24); theoretical element content (%) C 37 H 29 N 5 : C, 81.74; H, 5.38; N, 12.88; measured element content (%): C, 81.75; H, 5.37; N, 12.88. The above analysis results show that the obtained product is the target product.
实施例112Example 112
Figure PCTCN2020081035-appb-000192
Figure PCTCN2020081035-appb-000192
依照实施例39的合成，步骤相同，用化合物4-异丙基苯甲醛代替化合物4-氟苯甲醛，得到白色化合物0.521g(产率37.4％)。质谱分析确定的分子离子质量为：543.26(计算值为：543.24)；理论元素含量(％)C 37H 29N 5：C,81.74；H,5.38；N,12.88；实测元素含量(％)：C,81.75；H,5.37；N,12.88。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 39, the procedure was the same, and the compound 4-isopropylbenzaldehyde was substituted for the compound 4-fluorobenzaldehyde to obtain 0.521 g of a white compound (yield 37.4%). The molecular ion mass determined by mass spectrometry analysis is: 543.26 (calculated value: 543.24); theoretical element content (%) C 37 H 29 N 5 : C, 81.74; H, 5.38; N, 12.88; measured element content (%): C, 81.75; H, 5.37; N, 12.88. The above analysis results show that the obtained product is the target product.
实施例113Example 113
Figure PCTCN2020081035-appb-000193
Figure PCTCN2020081035-appb-000193
依照实施例40的合成，步骤相同，用化合物3,5-二异丙基苯甲醛代替化合物3,5-二氟苯甲醛，得到白色化合物0.514g(产率31.4％)。质谱分析确定的分子离子质量为：585.26(计算值为：585.29)；理论元素含量(％)C 40H 35N 5：C,82.02；H,6.02；N,11.96；实测元素含量(％)：C,82.05；H,6.07；N,11.88。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 40, the steps were the same, and the compound 3,5-diisopropylbenzaldehyde was substituted for the compound 3,5-difluorobenzaldehyde to obtain 0.514 g of a white compound (yield 31.4%). The molecular ion mass determined by mass spectrometry analysis is: 585.26 (calculated value: 585.29); theoretical element content (%) C 40 H 35 N 5 : C, 82.02; H, 6.02; N, 11.96; measured element content (%): C, 82.05; H, 6.07; N, 11.88. The above analysis results show that the obtained product is the target product.
实施例114Example 114
Figure PCTCN2020081035-appb-000194
Figure PCTCN2020081035-appb-000194
依照实施例41的合成，步骤相同，用化合物3,5-二异丙基苯甲醛代替化合物3,5-二氟苯甲醛，得到白色化合物0.520g(产率30.5％)。质谱分析确定的分子离子质量为：585.27(计算值为：585.29)；理论元素含量(％)C 40H 35N 5：C,82.02；H,6.02；N,11.96；实测元素含量(％)：C,82.05；H,6.07；N,11.88。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 41, the steps are the same, and the compound 3,5-diisopropylbenzaldehyde is used instead of the compound 3,5-difluorobenzaldehyde to obtain 0.520 g of a white compound (yield 30.5%). The molecular ion mass determined by mass spectrometry analysis is: 585.27 (calculated value: 585.29); theoretical element content (%) C 40 H 35 N 5 : C, 82.02; H, 6.02; N, 11.96; measured element content (%): C, 82.05; H, 6.07; N, 11.88. The above analysis results show that the obtained product is the target product.
实施例115Example 115
Figure PCTCN2020081035-appb-000195
Figure PCTCN2020081035-appb-000195
依照实施例42的合成，步骤相同，用化合物3,5-二异丙基苯甲醛代替化合物3,5-二氟苯甲醛，得到白色化合物0.523g(产率37.9％)。质谱分析确定的分子离子质量为：585.27(计算值为：585.29)；理论元素含量(％)C 40H 35N 5：C,82.02；H,6.02；N,11.96；实测元素含量(％)：C,82.05；H,6.07；N,11.88。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 42, the steps were the same, and the compound 3,5-diisopropylbenzaldehyde was used instead of the compound 3,5-difluorobenzaldehyde to obtain 0.523 g of a white compound (yield 37.9%). The molecular ion mass determined by mass spectrometry analysis is: 585.27 (calculated value: 585.29); theoretical element content (%) C 40 H 35 N 5 : C, 82.02; H, 6.02; N, 11.96; measured element content (%): C, 82.05; H, 6.07; N, 11.88. The above analysis results show that the obtained product is the target product.
实施例116Example 116
Figure PCTCN2020081035-appb-000196
Figure PCTCN2020081035-appb-000196
依照实施例55的合成，步骤相同，用化合物N 1-(2-异丙基苯基)苯-1,2-二胺代替化合物N 1-(2-氟苯基)苯-1,2-二胺，得到白色化合物0.529g(产率27.2％)。质谱分析确定的分子离子质量为：777.30(计算值为：777.36)；理论元素含量(％)C 53H 43N 7：C,81.83；H,5.57；N,12.60；实测元素含量(％)：C,81.85；H,5.57；N,12.58。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 55, the steps were the same, and the compound N 1 -(2-isopropylphenyl)benzene-1,2-diamine was used instead of the compound N 1 -(2-fluorophenyl)benzene-1,2- Diamine, 0.529 g of a white compound was obtained (yield 27.2%). The molecular ion mass determined by mass spectrometry analysis is: 777.30 (calculated value: 777.36); theoretical element content (%) C 53 H 43 N 7 : C, 81.83; H, 5.57; N, 12.60; measured element content (%): C, 81.85; H, 5.57; N, 12.58. The above analysis results show that the obtained product is the target product.
实施例117Example 117
Figure PCTCN2020081035-appb-000197
Figure PCTCN2020081035-appb-000197
依照实施例56的合成，步骤相同，用化合物N 1-(3-异丙基苯基)苯-1,2-二胺代替化合物N 1-(3-氟苯基)苯-1,2-二胺，得到白色化合物0.579g(产率24.2％)。质谱分析确定的分子离子质量为：777.34(计算值为：777.36)；理论元素含量(％)C 53H 43N 7：C,81.83；H,5.57；N,12.60；实测元素含量(％)：C,81.85；H,5.57；N,12.58。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 56, the steps are the same, and the compound N 1 -(3-isopropylphenyl)benzene-1,2-diamine is used instead of the compound N 1 -(3-fluorophenyl)benzene-1,2- Diamine, 0.579 g of a white compound (yield 24.2%) was obtained. The molecular ion mass determined by mass spectrometry analysis is: 777.34 (calculated value: 777.36); theoretical element content (%) C 53 H 43 N 7 : C, 81.83; H, 5.57; N, 12.60; measured element content (%): C, 81.85; H, 5.57; N, 12.58. The above analysis results show that the obtained product is the target product.
实施例118Example 118
Figure PCTCN2020081035-appb-000198
Figure PCTCN2020081035-appb-000198
依照实施例57的合成，步骤相同，用化合物N 1-(4-异丙基苯基)苯-1,2-二胺代替化合物N 1-(4-氟苯基)苯-1,2-二胺，得到白色化合物0.529g(产率27.2％)。质谱分析确定的分子离子质量为：777.30(计算值为：777.36)；理论元素含量(％)C 53H 43N 7：C,81.83；H,5.57；N,12.60；实测元素含量(％)：C,81.85；H,5.57；N,12.58。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 57, the steps are the same, and the compound N 1 -(4-isopropylphenyl)benzene-1,2-diamine is used instead of the compound N 1 -(4-fluorophenyl)benzene-1,2- Diamine, 0.529 g of a white compound was obtained (yield 27.2%). The molecular ion mass determined by mass spectrometry analysis is: 777.30 (calculated value: 777.36); theoretical element content (%) C 53 H 43 N 7 : C, 81.83; H, 5.57; N, 12.60; measured element content (%): C, 81.85; H, 5.57; N, 12.58. The above analysis results show that the obtained product is the target product.
实施例119Example 119
Figure PCTCN2020081035-appb-000199
Figure PCTCN2020081035-appb-000199
依照实施例58的合成，步骤相同，用化合物2-异丙基苯甲醛代替化合物2-氟苯甲醛，得到白色化合物0.529g(产率27.2％)。质谱分析确定的分子离子质量为：777.32(计算值为：777.36)；理论元素含量(％)C 53H 43N 7：C,81.83；H,5.57；N,12.60；实测元素含量(％)：C,81.85；H,5.57；N,12.58。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 58, the procedure was the same, and the compound 2-isopropylbenzaldehyde was used instead of the compound 2-fluorobenzaldehyde to obtain 0.529 g of a white compound (yield 27.2%). The molecular ion mass determined by mass spectrometry analysis is: 777.32 (calculated value: 777.36); theoretical element content (%) C 53 H 43 N 7 : C, 81.83; H, 5.57; N, 12.60; measured element content (%): C, 81.85; H, 5.57; N, 12.58. The above analysis results show that the obtained product is the target product.
实施例120Example 120
Figure PCTCN2020081035-appb-000200
Figure PCTCN2020081035-appb-000200
依照实施例59的合成，步骤相同，用化合物3-异丙基苯甲醛代替化合物3-氟苯甲醛，得到白色化合物0.529g(产率27.2％)。质谱分析确定的分子离子质量为：777.30(计算值为：777.36)；理论元素含量(％)C 53H 43N 7：C,81.83；H,5.57；N,12.60；实测元素含量(％)：C,81.85；H,5.57；N,12.58。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 59, the steps were the same, and the compound 3-isopropylbenzaldehyde was used instead of the compound 3-fluorobenzaldehyde to obtain 0.529 g of a white compound (yield 27.2%). The molecular ion mass determined by mass spectrometry analysis is: 777.30 (calculated value: 777.36); theoretical element content (%) C 53 H 43 N 7 : C, 81.83; H, 5.57; N, 12.60; measured element content (%): C, 81.85; H, 5.57; N, 12.58. The above analysis results show that the obtained product is the target product.
实施例121Example 121
Figure PCTCN2020081035-appb-000201
Figure PCTCN2020081035-appb-000201
依照实施例60的合成，步骤相同，用化合物4-异丙基苯甲醛代替化合物4-氟苯甲醛，得到白色化合物0.629g(产率29.2％)。质谱分析确定的分子离子质量为：777.32(计算值为：777.36)；理论元素含量(％)C 53H 43N 7：C,81.83；H,5.57；N,12.60；实测元素含量(％)：C,81.85；H,5.57；N,12.58。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 60, the steps were the same, and the compound 4-isopropylbenzaldehyde was used instead of the compound 4-fluorobenzaldehyde to obtain 0.629 g of a white compound (yield 29.2%). The molecular ion mass determined by mass spectrometry analysis is: 777.32 (calculated value: 777.36); theoretical element content (%) C 53 H 43 N 7 : C, 81.83; H, 5.57; N, 12.60; measured element content (%): C, 81.85; H, 5.57; N, 12.58. The above analysis results show that the obtained product is the target product.
实施例122Example 122
Figure PCTCN2020081035-appb-000202
Figure PCTCN2020081035-appb-000202
依照实施例61的合成，步骤相同，用化合物2-氯-4,6-二(4-异丙基苯基)-1,3,5-三嗪代替化合物2-氯-4,6-二(4-氟苯基)-1,3,5-三嗪，得到白色化合物0.529g(产率27.2％)。质谱分析确定的分子离子质量为：777.30(计算值为：777.36)；理论元素含量(％)C 53H 43N 7：C,81.83；H,5.57；N,12.60；实测元素含量(％)：C,81.85；H,5.57；N,12.58。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 61, the steps were the same, and the compound 2-chloro-4,6-bis(4-isopropylphenyl)-1,3,5-triazine was used instead of the compound 2-chloro-4,6-di (4-Fluorophenyl)-1,3,5-triazine, 0.529 g of a white compound (yield 27.2%) was obtained. The molecular ion mass determined by mass spectrometry analysis is: 777.30 (calculated value: 777.36); theoretical element content (%) C 53 H 43 N 7 : C, 81.83; H, 5.57; N, 12.60; measured element content (%): C, 81.85; H, 5.57; N, 12.58. The above analysis results show that the obtained product is the target product.
实施例123Example 123
Figure PCTCN2020081035-appb-000203
Figure PCTCN2020081035-appb-000203
依照实施例62的合成，步骤相同，用化合物2-氯-4,6-二(4-异丙基苯基)-1,3,5-三嗪代替化合物2-氯-4,6-二(4-氟苯基)-1,3,5-三嗪，得到白色化合物0.509g(产率27.7％)。质谱分析确定的分子离子质量为：777.32(计算值为：777.36)；理论元素含量(％)C 53H 43N 7：C,81.83；H,5.57；N,12.60；实测元素含量(％)：C,81.85；H,5.57；N,12.58。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 62, the steps were the same, and the compound 2-chloro-4,6-bis(4-isopropylphenyl)-1,3,5-triazine was used instead of the compound 2-chloro-4,6-di (4-Fluorophenyl)-1,3,5-triazine, 0.509 g of a white compound (yield 27.7%) was obtained. The molecular ion mass determined by mass spectrometry analysis is: 777.32 (calculated value: 777.36); theoretical element content (%) C 53 H 43 N 7 : C, 81.83; H, 5.57; N, 12.60; measured element content (%): C, 81.85; H, 5.57; N, 12.58. The above analysis results show that the obtained product is the target product.
实施例124Example 124
Figure PCTCN2020081035-appb-000204
Figure PCTCN2020081035-appb-000204
依照实施例63的合成，步骤相同，用化合物2-氯-4,6-二(4-异丙基苯基)-1,3,5-三嗪代替化合物2-氯-4,6-二(4-氟苯基)-1,3,5-三嗪，得到白色化合物0.529g(产率27.2％)。质谱分析确定的分子离子质量为：779.30(计算值为：779.35)；理论元素含量(％)C 51H 41N 9：C,78.54；H,5.30；N,16.16；实测元素含量(％)：C,78.55；H,5.37；N,16.08。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 63, the steps were the same, and the compound 2-chloro-4,6-bis(4-isopropylphenyl)-1,3,5-triazine was used instead of the compound 2-chloro-4,6-di (4-Fluorophenyl)-1,3,5-triazine, 0.529 g of a white compound (yield 27.2%) was obtained. The molecular ion mass determined by mass spectrometry analysis is: 779.30 (calculated value: 779.35); theoretical element content (%) C 51 H 41 N 9 : C, 78.54; H, 5.30; N, 16.16; measured element content (%): C, 78.55; H, 5.37; N, 16.08. The above analysis results show that the obtained product is the target product.
实施例125Example 125
Figure PCTCN2020081035-appb-000205
Figure PCTCN2020081035-appb-000205
依照实施例64的合成，步骤相同，用化合物2-氯-4,6-二(4-异丙基苯基)-1,3,5-三嗪代替化合物2-氯-4,6-二(4-氟苯基)-1,3,5-三嗪，得到白色化合物0.428g(产率25.6％)。质谱分析确定的分子离子质量为：779.32(计算值为：779.35)；理论元素含量(％)C 51H 41N 9：C,78.54；H,5.30；N,16.16；实测元素含量(％)：C,78.55；H,5.37；N,16.08。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 64, the steps were the same, and the compound 2-chloro-4,6-bis(4-isopropylphenyl)-1,3,5-triazine was used instead of the compound 2-chloro-4,6-di (4-Fluorophenyl)-1,3,5-triazine, 0.428 g of a white compound (yield 25.6%) was obtained. The molecular ion mass determined by mass spectrometry analysis is: 779.32 (calculated value: 779.35); theoretical element content (%) C 51 H 41 N 9 : C, 78.54; H, 5.30; N, 16.16; measured element content (%): C, 78.55; H, 5.37; N, 16.08. The above analysis results show that the obtained product is the target product.
实施例126Example 126
Figure PCTCN2020081035-appb-000206
Figure PCTCN2020081035-appb-000206
依照实施例65的合成，步骤相同，用化合物2-氯-4,6-二(4-异丙基苯基)-1,3,5-三嗪代替化合物2-氯-4,6-二(4-氟苯基)-1,3,5-三嗪，得到白色化合物0.529g(产率27.2％)。质谱分析确定的分子离子质量为：779.30(计算值为：779.35)；理论元素含量(％)C 51H 41N 9：C,78.54；H,5.30；N,16.16；实测元素含量(％)：C,78.55；H,5.37；N,16.08。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 65, the steps were the same, and the compound 2-chloro-4,6-bis(4-isopropylphenyl)-1,3,5-triazine was used instead of the compound 2-chloro-4,6-di (4-Fluorophenyl)-1,3,5-triazine, 0.529 g of a white compound (yield 27.2%) was obtained. The molecular ion mass determined by mass spectrometry analysis is: 779.30 (calculated value: 779.35); theoretical element content (%) C 51 H 41 N 9 : C, 78.54; H, 5.30; N, 16.16; measured element content (%): C, 78.55; H, 5.37; N, 16.08. The above analysis results show that the obtained product is the target product.
实施例127Example 127
Figure PCTCN2020081035-appb-000207
Figure PCTCN2020081035-appb-000207
依照实施例66的合成，步骤相同，用化合物2-氯-4,6-二(4-异丙基苯基)-1,3,5-三嗪代替化合物2-氯-4,6-二(4-氟苯基)-1,3,5-三嗪，得到白色化合物0.427g(产率25.7％)。质谱分析确定的分子离子质量为：779.37(计算值为：779.35)；理论元素含量(％)C 51H 41N 9：C,78.54；H,5.30；N,16.16；实测元素含量(％)：C,78.55；H,5.37；N,16.08。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 66, the steps were the same, and the compound 2-chloro-4,6-bis(4-isopropylphenyl)-1,3,5-triazine was used instead of the compound 2-chloro-4,6-di (4-Fluorophenyl)-1,3,5-triazine, 0.427 g of a white compound (yield 25.7%) was obtained. The molecular ion mass determined by mass spectrometry analysis is: 779.37 (calculated value: 779.35); theoretical element content (%) C 51 H 41 N 9 : C, 78.54; H, 5.30; N, 16.16; measured element content (%): C, 78.55; H, 5.37; N, 16.08. The above analysis results show that the obtained product is the target product.
实施例128Example 128
Figure PCTCN2020081035-appb-000208
Figure PCTCN2020081035-appb-000208
依照实施例67的合成，步骤相同，用化合物2-氯-4,6-二(4-异丙基苯基)-1,3,5-三嗪代替化合物2-氯-4,6-二(4-氟苯基)-1,3,5-三嗪，用化合物N 1-(2-异丙基苯基)苯-1,2-二胺代替化合物N 1-(2-氟苯基)苯-1,2-二胺得到白色化合物0.529g(产率27.2％)。质谱分析确定的分子离子质量为：861.42(计算值为：861.45)；理论元素含量(％)：C 59H 55N 7：C,82.20；H,6.43；N,11.37；实测元素含量(％)：C,82.25；H,6.47；N,11.28。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 67, the steps were the same, and the compound 2-chloro-4,6-bis(4-isopropylphenyl)-1,3,5-triazine was used instead of the compound 2-chloro-4,6-di (4-Fluorophenyl)-1,3,5-triazine, using compound N 1 -(2-isopropylphenyl)benzene-1,2-diamine instead of compound N 1 -(2-fluorophenyl) ) Benzene-1,2-diamine gave 0.529 g of white compound (yield 27.2%). The molecular ion mass determined by mass spectrometry analysis is: 861.42 (calculated value: 861.45); theoretical element content (%): C 59 H 55 N 7 : C, 82.20; H, 6.43; N, 11.37; measured element content (%) : C, 82.25; H, 6.47; N, 11.28. The above analysis results show that the obtained product is the target product.
实施例129Example 129
Figure PCTCN2020081035-appb-000209
Figure PCTCN2020081035-appb-000209
依照实施例68的合成，步骤相同，用化合物2-氯-4,6-二(4-异丙基苯基)-1,3,5-三嗪代替化合物2-氯-4,6-二(4-氟苯基)-1,3,5-三嗪，用化合物N 1-(3-异丙基苯基)苯-1,2-二胺代替化合物N 1-(3-氟苯基)苯-1,2-二胺得到白色化合物0.565g(产率28.2％)。质谱分析确定的分子离子质量为：861.41(计算值为：861.45)；理论元素含量(％)：C 59H 55N 7：C,82.20；H,6.43；N,11.37；实测元素含量(％)：C,82.25；H,6.48；N,11.27。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 68, the steps are the same, and the compound 2-chloro-4,6-bis(4-isopropylphenyl)-1,3,5-triazine is used instead of the compound 2-chloro-4,6-di (4-Fluorophenyl)-1,3,5-triazine, using compound N 1 -(3-isopropylphenyl)benzene-1,2-diamine instead of compound N 1 -(3-fluorophenyl) ) Benzene-1,2-diamine to obtain 0.565 g of a white compound (yield 28.2%). The molecular ion mass determined by mass spectrometry analysis is: 861.41 (calculated value: 861.45); theoretical element content (%): C 59 H 55 N 7 : C, 82.20; H, 6.43; N, 11.37; measured element content (%) : C, 82.25; H, 6.48; N, 11.27. The above analysis results show that the obtained product is the target product.
实施例130Example 130
Figure PCTCN2020081035-appb-000210
Figure PCTCN2020081035-appb-000210
依照实施例69的合成，步骤相同，用化合物2-氯-4,6-二(4-异丙基苯基)-1,3,5-三嗪代替化合物2-氯-4,6-二(4-氟苯基)-1,3,5-三嗪，用化合物N 1-(4-异丙基苯基)苯-1,2-二胺代替化合物N 1-(4-氟苯基)苯-1,2-二胺得到白色化合物0.529g(产率27.2％)。质谱分析确定的分子离子质量为：861.41(计 算值为：861.45)；理论元素含量(％)：C 59H 55N 7：C,82.20；H,6.43；N,11.37；实测元素含量(％)：C,82.25；H,6.47；N,11.28。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 69, the steps were the same, and the compound 2-chloro-4,6-bis(4-isopropylphenyl)-1,3,5-triazine was used instead of the compound 2-chloro-4,6-di (4-Fluorophenyl)-1,3,5-triazine, using compound N 1 -(4-isopropylphenyl)benzene-1,2-diamine instead of compound N 1 -(4-fluorophenyl) ) Benzene-1,2-diamine gave 0.529 g of white compound (yield 27.2%). The molecular ion mass determined by mass spectrometry analysis is: 861.41 (calculated value: 861.45); theoretical element content (%): C 59 H 55 N 7 : C, 82.20; H, 6.43; N, 11.37; measured element content (%) : C, 82.25; H, 6.47; N, 11.28. The above analysis results show that the obtained product is the target product.
实施例131Example 131
Figure PCTCN2020081035-appb-000211
Figure PCTCN2020081035-appb-000211
依照实施例70的合成，步骤相同，用化合物2-氯-4,6-二(4-异丙基苯基)-1,3,5-三嗪代替化合物2-氯-4,6-二(4-氟苯基)-1,3,5-三嗪，用化合物2-异丙基-苯甲醛代替化合物2-氟苯甲醛得到白色化合物0.417g(产率28.2％)。质谱分析确定的分子离子质量为：861.42(计算值为：861.45)；理论元素含量(％)：C 59H 55N 7：C,82.20；H,6.43；N,11.37；实测元素含量(％)：C,82.25；H,6.47；N,11.28。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 70, the steps were the same, and the compound 2-chloro-4,6-bis(4-isopropylphenyl)-1,3,5-triazine was used instead of the compound 2-chloro-4,6-di (4-Fluorophenyl)-1,3,5-triazine, using the compound 2-isopropyl-benzaldehyde instead of the compound 2-fluorobenzaldehyde to obtain 0.417 g of a white compound (yield 28.2%). The molecular ion mass determined by mass spectrometry analysis is: 861.42 (calculated value: 861.45); theoretical element content (%): C 59 H 55 N 7 : C, 82.20; H, 6.43; N, 11.37; measured element content (%) : C, 82.25; H, 6.47; N, 11.28. The above analysis results show that the obtained product is the target product.
实施例132Example 132
Figure PCTCN2020081035-appb-000212
Figure PCTCN2020081035-appb-000212
依照实施例71的合成，步骤相同，用化合物2-氯-4,6-二(4-异丙基苯基)-1,3,5-三嗪代替化合物2-氯-4,6-二(4-氟苯基)-1,3,5-三嗪，用化合物3-异丙基苯甲醛代替化合物3-氟-苯甲醛得到白色化合物0.629g(产率25.8％)。质谱分析确定的分子离子质量为：861.47(计算值为：861.45)；理论元素含量(％)：C 59H 55N 7：C,82.20；H,6.43；N,11.37；实测元素含量(％)：C,82.25；H,6.47；N,11.28。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 71, the steps were the same, and the compound 2-chloro-4,6-bis(4-isopropylphenyl)-1,3,5-triazine was used instead of the compound 2-chloro-4,6-di (4-Fluorophenyl)-1,3,5-triazine, using the compound 3-isopropylbenzaldehyde instead of the compound 3-fluoro-benzaldehyde to obtain 0.629 g of a white compound (yield 25.8%). The molecular ion mass determined by mass spectrometry analysis is: 861.47 (calculated value: 861.45); theoretical element content (%): C 59 H 55 N 7 : C, 82.20; H, 6.43; N, 11.37; measured element content (%) : C, 82.25; H, 6.47; N, 11.28. The above analysis results show that the obtained product is the target product.
实施例133Example 133
Figure PCTCN2020081035-appb-000213
Figure PCTCN2020081035-appb-000213
依照实施例72的合成，步骤相同，用化合物2-氯-4,6-二(4-异丙基苯基)-1,3,5-三嗪代替化合物2-氯-4,6-二(4-氟苯基)-1,3,5-三嗪，用化合物4-异丙基苯甲醛代替化合物4-氟苯甲醛得到白色化合 物0.529g(产率27.2％)。质谱分析确定的分子离子质量为：861.42(计算值为：861.45)；理论元素含量(％)：C 59H 55N 7：C,82.20；H,6.43；N,11.37；实测元素含量(％)：C,82.25；H,6.47；N,11.28。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 72, the steps were the same, and the compound 2-chloro-4,6-bis(4-isopropylphenyl)-1,3,5-triazine was used instead of the compound 2-chloro-4,6-di (4-Fluorophenyl)-1,3,5-triazine, using the compound 4-isopropylbenzaldehyde instead of the compound 4-fluorobenzaldehyde to obtain 0.529 g of a white compound (yield 27.2%). The molecular ion mass determined by mass spectrometry analysis is: 861.42 (calculated value: 861.45); theoretical element content (%): C 59 H 55 N 7 : C, 82.20; H, 6.43; N, 11.37; measured element content (%) : C, 82.25; H, 6.47; N, 11.28. The above analysis results show that the obtained product is the target product.
实施例134Example 134
Figure PCTCN2020081035-appb-000214
Figure PCTCN2020081035-appb-000214
依照实施例73的合成，步骤相同，用化合物2-氯-4,6-二(4-异丙基苯基)-1,3,5-三嗪代替化合物2-氯-4,6-二(4-氟苯基)-1,3,5-三嗪，用化合物N 1-(3,5-二异丙基苯基)苯-1,2-二胺代替化合物N 1-(3,5-二氟苯基)苯-1,2-二胺得到白色化合物0.417g(产率28.3％)。质谱分析确定的分子离子质量为：669.42(计算值为：669.38)；理论元素含量(％)：C 46H 47N 5：C,82.47；H,7.07；N,10.45；实测元素含量(％)：C,82.45；H,7.07；N,10.48。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 73, the steps were the same, and the compound 2-chloro-4,6-bis(4-isopropylphenyl)-1,3,5-triazine was used instead of the compound 2-chloro-4,6-di (4-Fluorophenyl)-1,3,5-triazine, using compound N 1 -(3,5-diisopropylphenyl)benzene-1,2-diamine instead of compound N 1 -(3, 5-difluorophenyl)benzene-1,2-diamine gave 0.417 g of a white compound (yield 28.3%). The molecular ion mass determined by mass spectrometry analysis is: 669.42 (calculated value: 669.38); theoretical element content (%): C 46 H 47 N 5 : C, 82.47; H, 7.07; N, 10.45; measured element content (%) : C, 82.45; H, 7.07; N, 10.48. The above analysis results show that the obtained product is the target product.
实施例135Example 135
Figure PCTCN2020081035-appb-000215
Figure PCTCN2020081035-appb-000215
依照实施例55的合成，步骤相同，用化合物N 1-(2-甲基苯基)苯-1,2-二胺代替化合物N 1-(2-氟苯基)苯-1,2-二胺，得到白色化合物0.509g(产率27.7％)。质谱分析确定的分子离子质量为：721.32(计算值为：721.30)；理论元素含量(％)C 49H 35N 7：C,81.53；H,4.89；N,13.58；实测元素含量(％)：C,81.55；H,4.87；N,13.58。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 55, the steps were the same, and the compound N 1 -(2-methylphenyl)benzene-1,2-diamine was used instead of the compound N 1 -(2-fluorophenyl)benzene-1,2-diamine. Amine, 0.509 g of a white compound was obtained (yield 27.7%). The molecular ion mass determined by mass spectrometry analysis is: 721.32 (calculated value: 721.30); theoretical element content (%) C 49 H 35 N 7 : C, 81.53; H, 4.89; N, 13.58; measured element content (%): C, 81.55; H, 4.87; N, 13.58. The above analysis results show that the obtained product is the target product.
实施例136Example 136
Figure PCTCN2020081035-appb-000216
Figure PCTCN2020081035-appb-000216
依照实施例56的合成，步骤相同，用化合物N 1-(3-甲基苯基)苯-1,2-二胺代替化合物N 1-(3-氟 苯基)苯-1,2-二胺，得到白色化合物0.644g(产率25.9％)。质谱分析确定的分子离子质量为：721.31(计算值为：721.30)；理论元素含量(％)C 49H 35N 7：C,81.53；H,4.89；N,13.58；实测元素含量(％)：C,81.55；H,4.87；N,13.58。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 56, the steps are the same, and the compound N 1 -(3-methylphenyl)benzene-1,2-diamine is used instead of the compound N 1 -(3-fluorophenyl)benzene-1,2-diamine Amine, 0.644 g of a white compound was obtained (yield 25.9%). The molecular ion mass determined by mass spectrometry analysis is: 721.31 (calculated value: 721.30); theoretical element content (%) C 49 H 35 N 7 : C, 81.53; H, 4.89; N, 13.58; measured element content (%): C, 81.55; H, 4.87; N, 13.58. The above analysis results show that the obtained product is the target product.
实施例137Example 137
Figure PCTCN2020081035-appb-000217
Figure PCTCN2020081035-appb-000217
依照实施例57的合成，步骤相同，用化合物N 1-(4-甲基苯基)苯-1,2-二胺代替化合物N 1-(4-氟苯基)苯-1,2-二胺，得到白色化合物0.519g(产率27.7％)。质谱分析确定的分子离子质量为：721.32(计算值为：721.30)；理论元素含量(％)C 49H 35N 7：C,81.53；H,4.89；N,13.58；实测元素含量(％)：C,81.55；H,4.87；N,13.58。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 57, the steps are the same, and the compound N 1 -(4-methylphenyl)benzene-1,2-diamine is used instead of the compound N 1 -(4-fluorophenyl)benzene-1,2-diamine. Amine, 0.519 g of a white compound was obtained (yield 27.7%). The molecular ion mass determined by mass spectrometry analysis is: 721.32 (calculated value: 721.30); theoretical element content (%) C 49 H 35 N 7 : C, 81.53; H, 4.89; N, 13.58; measured element content (%): C, 81.55; H, 4.87; N, 13.58. The above analysis results show that the obtained product is the target product.
实施例138Example 138
Figure PCTCN2020081035-appb-000218
Figure PCTCN2020081035-appb-000218
依照实施例58的合成，步骤相同，用化合物2-甲基苯甲醛代替化合物2-氟苯甲醛，得到白色化合物0.479g(产率25.7％)。质谱分析确定的分子离子质量为：721.37(计算值为：721.30)；理论元素含量(％)C 49H 35N 7：C,81.53；H,4.89；N,13.58；实测元素含量(％)：C,81.55；H,4.87；N,13.58。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 58, the procedure was the same, and the compound 2-methylbenzaldehyde was substituted for the compound 2-fluorobenzaldehyde to obtain 0.479 g of a white compound (yield 25.7%). The molecular ion mass determined by mass spectrometry analysis is: 721.37 (calculated value: 721.30); theoretical element content (%) C 49 H 35 N 7 : C, 81.53; H, 4.89; N, 13.58; measured element content (%): C, 81.55; H, 4.87; N, 13.58. The above analysis results show that the obtained product is the target product.
实施例139Example 139
Figure PCTCN2020081035-appb-000219
Figure PCTCN2020081035-appb-000219
依照实施例59的合成，步骤相同，用化合物3-甲基苯甲醛代替化合物3-氟苯甲醛，得到白色化合物0.509g(产率27.5％)。质谱分析确定的分子离子质量为：721.32(计算值为：721.30)；理论元素含量(％)C 49H 35N 7：C,81.53；H,4.89；N,13.58；实测元素含量(％)：C,81.55；H,4.87；N,13.58。上 述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 59, the procedure was the same, and the compound 3-methylbenzaldehyde was used instead of the compound 3-fluorobenzaldehyde to obtain 0.509 g of a white compound (yield 27.5%). The molecular ion mass determined by mass spectrometry analysis is: 721.32 (calculated value: 721.30); theoretical element content (%) C 49 H 35 N 7 : C, 81.53; H, 4.89; N, 13.58; measured element content (%): C, 81.55; H, 4.87; N, 13.58. The above analysis results show that the obtained product is the target product.
实施例140Example 140
Figure PCTCN2020081035-appb-000220
Figure PCTCN2020081035-appb-000220
依照实施例60的合成，步骤相同，用化合物4-甲基苯甲醛代替化合物4-氟苯甲醛，得到白色化合物0.578g(产率23.8％)。质谱分析确定的分子离子质量为：721.32(计算值为：721.30)；理论元素含量(％)C 49H 35N 7：C,81.53；H,4.89；N,13.58；实测元素含量(％)：C,81.55；H,4.87；N,13.58。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 60, the steps were the same, and the compound 4-methylbenzaldehyde was substituted for the compound 4-fluorobenzaldehyde to obtain 0.578 g of a white compound (yield 23.8%). The molecular ion mass determined by mass spectrometry analysis is: 721.32 (calculated value: 721.30); theoretical element content (%) C 49 H 35 N 7 : C, 81.53; H, 4.89; N, 13.58; measured element content (%): C, 81.55; H, 4.87; N, 13.58. The above analysis results show that the obtained product is the target product.
实施例141Example 141
Figure PCTCN2020081035-appb-000221
Figure PCTCN2020081035-appb-000221
依照实施例61的合成，步骤相同，用化合物2-氯-4,6-二(4-甲基苯基)-1,3,5-三嗪代替化合物2-氯-4,6-二(4-氟苯基)-1,3,5-三嗪得到白色化合物0.529g(产率27.2％)。质谱分析确定的分子离子质量为：721.32(计算值为：721.30)；理论元素含量(％)C 49H 35N 7：C,81.53；H,4.89；N,13.58；实测元素含量(％)：C,81.55；H,4.87；N,13.58。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 61, the steps were the same, and the compound 2-chloro-4,6-bis(4-methylphenyl)-1,3,5-triazine was used instead of the compound 2-chloro-4,6-bis( 4-fluorophenyl)-1,3,5-triazine gave 0.529 g of a white compound (yield 27.2%). The molecular ion mass determined by mass spectrometry analysis is: 721.32 (calculated value: 721.30); theoretical element content (%) C 49 H 35 N 7 : C, 81.53; H, 4.89; N, 13.58; measured element content (%): C, 81.55; H, 4.87; N, 13.58. The above analysis results show that the obtained product is the target product.
实施例142Example 142
Figure PCTCN2020081035-appb-000222
Figure PCTCN2020081035-appb-000222
依照实施例62的合成，步骤相同，用化合物2-氯-4,6-二(4-甲基苯基)-1,3,5-三嗪代替化合物2-氯-4,6-二(4-氟苯基)-1,3,5-三嗪得到白色化合物0.479g(产率25.4％)。质谱分析确定的分子离子质量为：721.30(计算值为：721.30)；理论元素含量(％)C 49H 35N 7：C,81.53；H,4.89；N,13.58；实测元素含量(％)：C,81.55；H,4.87；N,13.58。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 62, the steps were the same, and the compound 2-chloro-4,6-bis(4-methylphenyl)-1,3,5-triazine was used instead of the compound 2-chloro-4,6-bis( 4-fluorophenyl)-1,3,5-triazine gave 0.479 g of a white compound (yield 25.4%). The molecular ion mass determined by mass spectrometry analysis is: 721.30 (calculated value: 721.30); theoretical element content (%) C 49 H 35 N 7 : C, 81.53; H, 4.89; N, 13.58; measured element content (%): C, 81.55; H, 4.87; N, 13.58. The above analysis results show that the obtained product is the target product.
实施例143Example 143
Figure PCTCN2020081035-appb-000223
Figure PCTCN2020081035-appb-000223
依照实施例63的合成，步骤相同，用化合物2-氯-4,6-二(4-甲基苯基)-1,3,5-三嗪代替化合物2-氯-4,6-二(4-氟苯基)-1,3,5-三嗪，得到白色化合物0.529g(产率27.2％)。质谱分析确定的分子离子质量为：723.30(计算值为：723.29)；理论元素含量(％)C 47H 33N 9：C,77.99；H,4.60；N,17.42；实测元素含量(％)：C,77.95；H,4.67；N,17.38。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 63, the steps were the same, and the compound 2-chloro-4,6-bis(4-methylphenyl)-1,3,5-triazine was used instead of the compound 2-chloro-4,6-bis( 4-fluorophenyl)-1,3,5-triazine, 0.529 g of a white compound was obtained (yield 27.2%). The molecular ion mass determined by mass spectrometry analysis is: 723.30 (calculated value: 723.29); theoretical element content (%) C 47 H 33 N 9 : C, 77.99; H, 4.60; N, 17.42; measured element content (%): C, 77.95; H, 4.67; N, 17.38. The above analysis results show that the obtained product is the target product.
实施例144Example 144
Figure PCTCN2020081035-appb-000224
Figure PCTCN2020081035-appb-000224
依照实施例64的合成，步骤相同，用化合物2-氯-4,6-二(4-甲基苯基)-1,3,5-三嗪代替化合物2-氯-4,6-二(4-氟苯基)-1,3,5-三嗪，得到白色化合物0.439g(产率26.2％)。质谱分析确定的分子离子质量为：723.31(计算值为：723.29)；理论元素含量(％)C 47H 33N 9：C,77.99；H,4.60；N,17.42；实测元素含量(％)：C,77.95；H,4.67；N,17.38。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 64, the steps were the same, and the compound 2-chloro-4,6-bis(4-methylphenyl)-1,3,5-triazine was used instead of the compound 2-chloro-4,6-bis( 4-fluorophenyl)-1,3,5-triazine, 0.439 g of a white compound was obtained (yield 26.2%). The molecular ion mass determined by mass spectrometry analysis is: 723.31 (calculated value: 723.29); theoretical element content (%) C 47 H 33 N 9 : C, 77.99; H, 4.60; N, 17.42; measured element content (%): C, 77.95; H, 4.67; N, 17.38. The above analysis results show that the obtained product is the target product.
实施例145Example 145
Figure PCTCN2020081035-appb-000225
Figure PCTCN2020081035-appb-000225
依照实施例65的合成，步骤相同，用化合物2-氯-4,6-二(4-甲基苯基)-1,3,5-三嗪代替化合物2-氯-4,6-二(4-氟苯基)-1,3,5-三嗪，得到白色化合物0.529g(产率27.1％)。质谱分析确定的分子离子质量为：723.30(计算值为：723.29)；理论元素含量(％)C 47H 33N 9：C,77.99；H,4.60；N,17.42；实测元素含量(％)：C,77.95；H,4.67；N,17.38。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 65, the steps were the same, and the compound 2-chloro-4,6-bis(4-methylphenyl)-1,3,5-triazine was used instead of the compound 2-chloro-4,6-bis( 4-fluorophenyl)-1,3,5-triazine to obtain 0.529 g of a white compound (yield 27.1%). The molecular ion mass determined by mass spectrometry analysis is: 723.30 (calculated value: 723.29); theoretical element content (%) C 47 H 33 N 9 : C, 77.99; H, 4.60; N, 17.42; measured element content (%): C, 77.95; H, 4.67; N, 17.38. The above analysis results show that the obtained product is the target product.
实施例146Example 146
Figure PCTCN2020081035-appb-000226
Figure PCTCN2020081035-appb-000226
依照实施例66的合成，步骤相同，用化合物2-氯-4,6-二(4-甲基苯基)-1,3,5-三嗪代替化合物2-氯-4,6-二(4-氟苯基)-1,3,5-三嗪，得到白色化合物0.671g(产率28.3％)。质谱分析确定的分子离子质量为：723.30(计算值为：723.29)；理论元素含量(％)C 47H 33N 9：C,77.99；H,4.60；N,17.42；实测元素含量(％)：C,77.95；H,4.67；N,17.38。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 66, the steps were the same, and the compound 2-chloro-4,6-bis(4-methylphenyl)-1,3,5-triazine was used instead of the compound 2-chloro-4,6-bis( 4-fluorophenyl)-1,3,5-triazine, 0.671 g of a white compound was obtained (yield 28.3%). The molecular ion mass determined by mass spectrometry analysis is: 723.30 (calculated value: 723.29); theoretical element content (%) C 47 H 33 N 9 : C, 77.99; H, 4.60; N, 17.42; measured element content (%): C, 77.95; H, 4.67; N, 17.38. The above analysis results show that the obtained product is the target product.
实施例147Example 147
Figure PCTCN2020081035-appb-000227
Figure PCTCN2020081035-appb-000227
依照实施例67的合成，步骤相同，用化合物2-氯-4,6-二(4-甲基苯基)-1,3,5-三嗪代替化合物2-氯-4,6-二(4-氟苯基)-1,3,5-三嗪，用化合物N 1-(2-甲基苯基)苯-1,2-二胺代替化合物N 1-(2-氟苯基)苯-1,2-二胺得到白色化合物0.529g(产率27.2％)。质谱分析确定的分子离子质量为：749.36(计算值为：749.33)；理论元素含量(％)C 51H 39N 7：C,81.68；H,5.24；N,13.07；实测元素含量(％)：C,81.65；H,5.27；N,13.08。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 67, the steps were the same, and the compound 2-chloro-4,6-bis(4-methylphenyl)-1,3,5-triazine was used instead of the compound 2-chloro-4,6-bis( 4-fluorophenyl)-1,3,5-triazine, using compound N 1 -(2-methylphenyl)benzene-1,2-diamine instead of compound N 1 -(2-fluorophenyl)benzene -1,2-Diamine to obtain 0.529 g of a white compound (yield 27.2%). The molecular ion mass determined by mass spectrometry analysis is: 749.36 (calculated value: 749.33); theoretical element content (%) C 51 H 39 N 7 : C, 81.68; H, 5.24; N, 13.07; measured element content (%): C, 81.65; H, 5.27; N, 13.08. The above analysis results show that the obtained product is the target product.
实施例148Example 148
Figure PCTCN2020081035-appb-000228
Figure PCTCN2020081035-appb-000228
依照实施例68的合成，步骤相同，用化合物2-氯-4,6-二(4-甲基苯基)-1,3,5-三嗪代替化合物2-氯-4,6-二(4-氟苯基)-1,3,5-三嗪，用化合物N 1-(3-甲基苯基)苯-1,2-二胺代替化合物N 1-(3-氟苯基)苯-1,2-二胺得到白色化合物0.679g(产率29.7％)。质谱分析确定的分子离子质量为：749.32(计算值为：749.33)；理论元素含量(％)C 51H 39N 7：C,81.68；H,5.24；N,13.07；实测元素含量(％)：C,81.65；H,5.27；N,13.08。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 68, the steps were the same, and the compound 2-chloro-4,6-bis(4-methylphenyl)-1,3,5-triazine was used instead of the compound 2-chloro-4,6-bis( 4-fluorophenyl)-1,3,5-triazine, using compound N 1 -(3-methylphenyl)benzene-1,2-diamine instead of compound N 1 -(3-fluorophenyl)benzene -1,2-Diamine to obtain 0.679 g of a white compound (yield 29.7%). The molecular ion mass determined by mass spectrometry analysis is: 749.32 (calculated value: 749.33); theoretical element content (%) C 51 H 39 N 7 : C, 81.68; H, 5.24; N, 13.07; measured element content (%): C, 81.65; H, 5.27; N, 13.08. The above analysis results show that the obtained product is the target product.
实施例149Example 149
Figure PCTCN2020081035-appb-000229
Figure PCTCN2020081035-appb-000229
依照实施例69的合成，步骤相同，用化合物2-氯-4,6-二(4-甲基苯基)-1,3,5-三嗪代替化合物2-氯-4,6-二(4-氟苯基)-1,3,5-三嗪，用化合物N 1-(4-甲基苯基)苯-1,2-二胺代替化合物N 1-(4-氟苯基)苯-1,2-二胺得到白色化合物0.508g(产率24.7％)。质谱分析确定的分子离子质量为：749.31(计算值为：749.33)；理论元素含量(％)C 51H 39N 7：C,81.68；H,5.24；N,13.07；实测元素含量(％)：C,81.65；H,5.27；N,13.08。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 69, the steps were the same, and the compound 2-chloro-4,6-bis(4-methylphenyl)-1,3,5-triazine was used instead of the compound 2-chloro-4,6-bis( 4-fluorophenyl)-1,3,5-triazine, using compound N 1 -(4-methylphenyl)benzene-1,2-diamine instead of compound N 1 -(4-fluorophenyl)benzene -1,2-Diamine to obtain 0.508 g of a white compound (yield 24.7%). The molecular ion mass determined by mass spectrometry analysis is: 749.31 (calculated value: 749.33); theoretical element content (%) C 51 H 39 N 7 : C, 81.68; H, 5.24; N, 13.07; measured element content (%): C, 81.65; H, 5.27; N, 13.08. The above analysis results show that the obtained product is the target product.
实施例150Example 150
Figure PCTCN2020081035-appb-000230
Figure PCTCN2020081035-appb-000230
依照实施例70的合成，步骤相同，用化合物2-氯-4,6-二(4-甲基苯基)-1,3,5-三嗪代替化合物2-氯-4,6-二(4-氟苯基)-1,3,5-三嗪，用化合物2-甲基苯甲醛代替化合物2-氟苯甲醛得到白色化合物0.679g(产率29.7％)。质谱分析确定的分子离子质量为：749.31(计算值为：749.33)；理论元素含量(％)C 51H 39N 7：C,81.68；H,5.24；N,13.07；实测元素含量(％)：C,81.65；H,5.27；N,13.08。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 70, the steps were the same, and the compound 2-chloro-4,6-bis(4-methylphenyl)-1,3,5-triazine was used instead of the compound 2-chloro-4,6-bis( 4-fluorophenyl)-1,3,5-triazine, using the compound 2-methylbenzaldehyde instead of the compound 2-fluorobenzaldehyde to obtain 0.679 g of a white compound (yield 29.7%). The molecular ion mass determined by mass spectrometry analysis is: 749.31 (calculated value: 749.33); theoretical element content (%) C 51 H 39 N 7 : C, 81.68; H, 5.24; N, 13.07; measured element content (%): C, 81.65; H, 5.27; N, 13.08. The above analysis results show that the obtained product is the target product.
实施例151Example 151
Figure PCTCN2020081035-appb-000231
Figure PCTCN2020081035-appb-000231
依照实施例71的合成，步骤相同，用化合物2-氯-4,6-二(4-甲基苯基)-1,3,5-三嗪代替化合物2-氯-4,6-二(4-氟苯基)-1,3,5-三嗪，用化合物3-甲基苯甲醛代替化合物3-氟苯甲醛得到白色化合物0.577g(产率26.5％)。质谱分析确定的分子离子质量为：749.37(计算值为：749.33)；理论元素含量(％)C 51H 39N 7：C,81.68；H,5.24；N,13.07；实测元素含量(％)：C,81.65；H,5.27；N,13.08。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 71, the steps were the same, and the compound 2-chloro-4,6-bis(4-methylphenyl)-1,3,5-triazine was used instead of the compound 2-chloro-4,6-bis( 4-fluorophenyl)-1,3,5-triazine, the compound 3-methylbenzaldehyde was substituted for the compound 3-fluorobenzaldehyde to obtain 0.577 g of a white compound (yield 26.5%). The molecular ion mass determined by mass spectrometry analysis is: 749.37 (calculated value: 749.33); theoretical element content (%) C 51 H 39 N 7 : C, 81.68; H, 5.24; N, 13.07; measured element content (%): C, 81.65; H, 5.27; N, 13.08. The above analysis results show that the obtained product is the target product.
实施例152Example 152
Figure PCTCN2020081035-appb-000232
Figure PCTCN2020081035-appb-000232
依照实施例72的合成，步骤相同，用化合物2-氯-4,6-二(4-甲基苯基)-1,3,5-三嗪代替化合物2-氯-4,6-二(4-氟苯基)-1,3,5-三嗪，用化合物4-甲基苯甲醛代替化合物4-氟苯甲醛得到白色化合物0.792g(产率23.7％)。质谱分析确定的分子离子质量为：749.31(计算值为：749.33)；理论元素含量(％)C 51H 39N 7：C,81.68；H,5.24；N,13.07；实测元素含量(％)：C,81.65；H,5.27；N,13.08。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 72, the steps were the same, and the compound 2-chloro-4,6-bis(4-methylphenyl)-1,3,5-triazine was used instead of the compound 2-chloro-4,6-bis( 4-fluorophenyl)-1,3,5-triazine, using the compound 4-methylbenzaldehyde instead of the compound 4-fluorobenzaldehyde to obtain 0.792 g of a white compound (yield 23.7%). The molecular ion mass determined by mass spectrometry analysis is: 749.31 (calculated value: 749.33); theoretical element content (%) C 51 H 39 N 7 : C, 81.68; H, 5.24; N, 13.07; measured element content (%): C, 81.65; H, 5.27; N, 13.08. The above analysis results show that the obtained product is the target product.
实施例153Example 153
Figure PCTCN2020081035-appb-000233
Figure PCTCN2020081035-appb-000233
依照实施例73的合成，步骤相同，用化合物2-氯-4,6-二(4-甲基苯基)-1,3,5-三嗪代替化合物2-氯-4,6-二(4-氟苯基)-1,3,5-三嗪，用化合物N 1-(3，5-二甲基苯基)苯-1,2-二胺代替化合物N 1-(3，5-二氟苯基)苯-1,2-二胺得到白色化合物0.679g(产率29.7％)。质谱分析确定的分子离子质量为：557.29(计算值为：557.26)；理论元素含量(％)C 38H 31N 5：C,81.84；H,5.60；N,12.56；实测元素含量(％)：C,81.85；H,5.67；N,12.48。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 73, the steps were the same, and the compound 2-chloro-4,6-bis(4-methylphenyl)-1,3,5-triazine was used instead of the compound 2-chloro-4,6-bis( 4-fluorophenyl)-1,3,5-triazine, using compound N 1 -(3,5-dimethylphenyl)benzene-1,2-diamine instead of compound N 1 -(3,5- Difluorophenyl)benzene-1,2-diamine gave 0.679 g of a white compound (yield 29.7%). The molecular ion mass determined by mass spectrometry analysis is: 557.29 (calculated value: 557.26); theoretical element content (%) C 38 H 31 N 5 : C, 81.84; H, 5.60; N, 12.56; measured element content (%): C, 81.85; H, 5.67; N, 12.48. The above analysis results show that the obtained product is the target product.
实施例154Example 154
Figure PCTCN2020081035-appb-000234
Figure PCTCN2020081035-appb-000234
依照实施例1的合成，步骤相同，用化合物N 1-([1,1'-联苯]-2-基)苯-1,2-二胺代替化合物邻氨基二苯胺，得到白色化合物0.435g(产率31.3％)。质谱分析确定的分子离子质量为：577.25(计算值为：577.23)；理论元素含量(％)C 40H 27N 5：C,83.17；H,4.71；N,12.12；实测元素含量(％)：C,83.18；H,4.72；N,12.10。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 1, the steps are the same, the compound N 1 -([1,1'-biphenyl]-2-yl)benzene-1,2-diamine is substituted for the compound o-aminodiphenylamine to obtain 0.435g of a white compound (Yield 31.3%). The molecular ion mass determined by mass spectrometry analysis is: 577.25 (calculated value: 577.23); theoretical element content (%) C 40 H 27 N 5 : C, 83.17; H, 4.71; N, 12.12; measured element content (%): C, 83.18; H, 4.72; N, 12.10. The above analysis results show that the obtained product is the target product.
实施例155Example 155
Figure PCTCN2020081035-appb-000235
Figure PCTCN2020081035-appb-000235
依照实施例2的合成，步骤相同，用化合物N 1-([1,1'-联苯]-2-基)苯-1,2-二胺代替化合物邻氨基二苯胺，得到白色化合物0.467g(产率31.6％)。质谱分析确定的分子离子质量为：577.28(计算值为：577.23)；理论元素含量(％)C 40H 27N 5：C,83.17；H,4.71；N,12.12；实测元素含量(％)：C,83.18；H,4.72；N,12.10。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 2, the steps are the same, and the compound N 1 -([1,1'-biphenyl]-2-yl)benzene-1,2-diamine is substituted for the compound o-aminodiphenylamine to obtain 0.467g of a white compound (Yield 31.6%). The molecular ion mass determined by mass spectrometry analysis is: 577.28 (calculated value: 577.23); theoretical element content (%) C 40 H 27 N 5 : C, 83.17; H, 4.71; N, 12.12; measured element content (%): C, 83.18; H, 4.72; N, 12.10. The above analysis results show that the obtained product is the target product.
实施例156Example 156
Figure PCTCN2020081035-appb-000236
Figure PCTCN2020081035-appb-000236
依照实施例3的合成，步骤相同，用化合物N 1-([1,1'-联苯]-2-基)苯-1,2-二胺代替化合物邻氨基二苯胺，得到白色化合物0.438g(产率32.7％)。质谱分析确定的分子离子质量为：577.29(计算值为：577.23)；理论元素含量(％)C 40H 27N 5：C,83.17；H,4.71；N,12.12；实测元素含量(％)：C,83.18；H,4.72；N,12.10。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 3, the steps are the same, the compound N 1 -([1,1'-biphenyl]-2-yl)benzene-1,2-diamine is substituted for the compound o-aminodiphenylamine to obtain 0.438 g of a white compound (Yield 32.7%). The molecular ion mass determined by mass spectrometry analysis is: 577.29 (calculated value: 577.23); theoretical element content (%) C 40 H 27 N 5 : C, 83.17; H, 4.71; N, 12.12; measured element content (%): C, 83.18; H, 4.72; N, 12.10. The above analysis results show that the obtained product is the target product.
实施例157Example 157
Figure PCTCN2020081035-appb-000237
Figure PCTCN2020081035-appb-000237
依照实施例4的合成，步骤相同，用化合物[1,1'-联苯]-2-甲醛代替化合物苯甲醛，得到白色化合物0.503g(产率35.4％)。质谱分析确定的分子离子质量为：577.32(计算值为：577.23)；理论元素含量(％)C 40H 27N 5：C,83.17；H,4.71；N,12.12；实测元素含量(％)：C,83.18；H,4.72；N,12.10。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 4, the steps were the same, and the compound [1,1'-biphenyl]-2-carbaldehyde was used instead of the compound benzaldehyde to obtain 0.503 g of a white compound (yield 35.4%). The molecular ion mass determined by mass spectrometry analysis is: 577.32 (calculated value: 577.23); theoretical element content (%) C 40 H 27 N 5 : C, 83.17; H, 4.71; N, 12.12; measured element content (%): C, 83.18; H, 4.72; N, 12.10. The above analysis results show that the obtained product is the target product.
实施例158Example 158
Figure PCTCN2020081035-appb-000238
Figure PCTCN2020081035-appb-000238
依照实施例5的合成，步骤相同，用化合物[1,1'-联苯]-2-甲醛代替化合物苯甲醛，得到白色化合物0.468g(产率30.3％)。质谱分析确定的分子离子质量为：577.31(计算值为：577.23)；理论元素含量(％)C 40H 27N 5：C,83.17；H,4.71；N,12.12；实测元素含量(％)：C,83.18；H,4.72；N,12.10。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 5, the steps were the same, and the compound [1,1'-biphenyl]-2-carbaldehyde was used instead of the compound benzaldehyde to obtain 0.468 g of a white compound (yield 30.3%). The molecular ion mass determined by mass spectrometry analysis is: 577.31 (calculated value: 577.23); theoretical element content (%) C 40 H 27 N 5 : C, 83.17; H, 4.71; N, 12.12; measured element content (%): C, 83.18; H, 4.72; N, 12.10. The above analysis results show that the obtained product is the target product.
实施例159Example 159
Figure PCTCN2020081035-appb-000239
Figure PCTCN2020081035-appb-000239
依照实施例6的合成，步骤相同，用化合物[1,1'-联苯]-2-甲醛代替化合物苯甲醛，得到白色化合物0.538g(产率38.3％)。质谱分析确定的分子离子质量为：577.30(计算值为：577.23)；理论元素含量(％)C 40H 27N 5：C,83.17；H,4.71；N,12.12；实测元素含量(％)：C,83.18；H,4.72；N,12.10。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 6, the steps were the same, and the compound [1,1'-biphenyl]-2-carbaldehyde was used instead of the compound benzaldehyde to obtain 0.538 g of a white compound (yield 38.3%). The molecular ion mass determined by mass spectrometry analysis is: 577.30 (calculated value: 577.23); theoretical element content (%) C 40 H 27 N 5 : C, 83.17; H, 4.71; N, 12.12; measured element content (%): C, 83.18; H, 4.72; N, 12.10. The above analysis results show that the obtained product is the target product.
实施例160Example 160
Figure PCTCN2020081035-appb-000240
Figure PCTCN2020081035-appb-000240
依照实施例1的合成，步骤相同，用化合物N 1-([1,1'-联苯]-3-基)苯-1,2-二胺代替化合物邻氨基二苯胺，得到白色化合物0.492g(产率34.6％)。质谱分析确定的分子离子质量为：577.28(计算值为：577.23)；理论元素含量(％)C 40H 27N 5：C,83.17；H,4.71；N,12.12；实测元素含量(％)：C,83.18；H,4.72；N,12.10。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 1, the steps are the same, the compound N 1 -([1,1'-biphenyl]-3-yl)benzene-1,2-diamine is substituted for the compound o-aminodiphenylamine to obtain 0.492g of a white compound (Yield 34.6%). The molecular ion mass determined by mass spectrometry analysis is: 577.28 (calculated value: 577.23); theoretical element content (%) C 40 H 27 N 5 : C, 83.17; H, 4.71; N, 12.12; measured element content (%): C, 83.18; H, 4.72; N, 12.10. The above analysis results show that the obtained product is the target product.
实施例161Example 161
Figure PCTCN2020081035-appb-000241
Figure PCTCN2020081035-appb-000241
依照实施例2的合成，步骤相同，用化合物N 1-([1,1'-联苯]-3-基)苯-1,2-二胺代替化合物邻氨基二苯胺，得到白色化合物0.448g(产率32.8％)。质谱分析确定的分子离子质量为：577.28(计算值为：577.23)；理论元素含量(％)C 40H 27N 5：C,83.17；H,4.71；N,12.12；实测元素含量(％)：C,83.18；H,4.72；N,12.10。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 2, the steps are the same, the compound N 1 -([1,1'-biphenyl]-3-yl)benzene-1,2-diamine is substituted for the compound o-aminodiphenylamine to obtain 0.448g of a white compound (Yield 32.8%). The molecular ion mass determined by mass spectrometry analysis is: 577.28 (calculated value: 577.23); theoretical element content (%) C 40 H 27 N 5 : C, 83.17; H, 4.71; N, 12.12; measured element content (%): C, 83.18; H, 4.72; N, 12.10. The above analysis results show that the obtained product is the target product.
实施例162Example 162
Figure PCTCN2020081035-appb-000242
Figure PCTCN2020081035-appb-000242
依照实施例3的合成，步骤相同，用化合物N 1-([1,1'-联苯]-3-基)苯-1,2-二胺代替化合物邻氨基二苯胺，得到白色化合物0.523g(产率31.2％)。质谱分析确定的分子离子质量为：577.21(计算值为：577.23)；理论元素含量(％)C 40H 27N 5：C,83.17；H,4.71；N,12.12；实测元素含量(％)：C,83.18；H,4.72；N,12.10。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 3, the steps are the same, the compound N 1 -([1,1'-biphenyl]-3-yl)benzene-1,2-diamine is substituted for the compound o-aminodiphenylamine to obtain 0.523g of a white compound (Yield 31.2%). The molecular ion mass determined by mass spectrometry analysis is: 577.21 (calculated value: 577.23); theoretical element content (%) C 40 H 27 N 5 : C, 83.17; H, 4.71; N, 12.12; measured element content (%): C, 83.18; H, 4.72; N, 12.10. The above analysis results show that the obtained product is the target product.
实施例163Example 163
Figure PCTCN2020081035-appb-000243
Figure PCTCN2020081035-appb-000243
依照实施例4的合成，步骤相同，用化合物[1,1'-联苯]-3-甲醛代替化合物苯甲醛，得到白色化合物0.495g(产率33.1％)。质谱分析确定的分子离子质量为：577.20(计算值为：577.23)；理论元素含量(％)C 40H 27N 5：C,83.17；H,4.71；N,12.12；实测元素含量(％)：C,83.18；H,4.72；N,12.10。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 4, the steps were the same, and the compound [1,1'-biphenyl]-3-carbaldehyde was substituted for the compound benzaldehyde to obtain 0.495 g of a white compound (yield 33.1%). The molecular ion mass determined by mass spectrometry analysis is: 577.20 (calculated value: 577.23); theoretical element content (%) C 40 H 27 N 5 : C, 83.17; H, 4.71; N, 12.12; measured element content (%): C, 83.18; H, 4.72; N, 12.10. The above analysis results show that the obtained product is the target product.
实施例164Example 164
Figure PCTCN2020081035-appb-000244
Figure PCTCN2020081035-appb-000244
依照实施例5的合成，步骤相同，用化合物[1,1'-联苯]-3-甲醛代替化合物苯甲醛，得到白色化合物0.441g(产率32.1％)。质谱分析确定的分子离子质量为：577.28(计算值为：577.23)；理论元素含量(％)C 40H 27N 5：C,83.17；H,4.71；N,12.12；实测元素含量(％)：C,83.18；H,4.72；N,12.10。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 5, the steps were the same, and the compound [1,1'-biphenyl]-3-carbaldehyde was used instead of the compound benzaldehyde to obtain 0.441 g of a white compound (yield 32.1%). The molecular ion mass determined by mass spectrometry analysis is: 577.28 (calculated value: 577.23); theoretical element content (%) C 40 H 27 N 5 : C, 83.17; H, 4.71; N, 12.12; measured element content (%): C, 83.18; H, 4.72; N, 12.10. The above analysis results show that the obtained product is the target product.
实施例165Example 165
Figure PCTCN2020081035-appb-000245
Figure PCTCN2020081035-appb-000245
依照实施例6的合成，步骤相同，用[1,1'-联苯]-3-甲醛代替化合物苯甲醛，得到白色化合物0.438g(产率32.4％)。质谱分析确定的分子离子质量为：577.25(计算值为：577.23)；理论元素含量(％)C 40H 27N 5：C,83.17；H,4.71；N,12.12；实测元素含量(％)：C,83.18；H,4.72；N,12.10。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 6, the steps are the same, using [1,1'-biphenyl]-3-carbaldehyde instead of the compound benzaldehyde to obtain 0.438 g of a white compound (yield 32.4%). The molecular ion mass determined by mass spectrometry analysis is: 577.25 (calculated value: 577.23); theoretical element content (%) C 40 H 27 N 5 : C, 83.17; H, 4.71; N, 12.12; measured element content (%): C, 83.18; H, 4.72; N, 12.10. The above analysis results show that the obtained product is the target product.
实施例166Example 166
Figure PCTCN2020081035-appb-000246
Figure PCTCN2020081035-appb-000246
依照实施例1的合成，步骤相同，用化合物N 1-([1,1'-联苯]-4-基)苯-1,2-二胺代替化合物邻氨基二苯胺，得到白色化合物0.413g(产率35.6％)。质谱分析确定的分子离子质量为：577.30(计算值为：577.23)；理论元素含量(％)C 40H 27N 5：C,83.17；H,4.71；N,12.12；实测元素含量(％)：C,83.18；H,4.72；N,12.10。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 1, the steps are the same, and the compound N 1 -([1,1'-biphenyl]-4-yl)benzene-1,2-diamine is substituted for the compound o-aminodiphenylamine to obtain 0.413g of a white compound (Yield 35.6%). The molecular ion mass determined by mass spectrometry analysis is: 577.30 (calculated value: 577.23); theoretical element content (%) C 40 H 27 N 5 : C, 83.17; H, 4.71; N, 12.12; measured element content (%): C, 83.18; H, 4.72; N, 12.10. The above analysis results show that the obtained product is the target product.
实施例167Example 167
Figure PCTCN2020081035-appb-000247
Figure PCTCN2020081035-appb-000247
依照实施例2的合成，步骤相同，用化合物N 1-([1,1'-联苯]-4-基)苯-1,2-二胺代替化合物邻氨基二苯胺，得到白色化合物0.448g(产率31.3％)。质谱分析确定的分子离子质量为：577.26(计算值为：577.23)；理论元素含量(％)C 40H 27N 5：C,83.17；H,4.71；N,12.12；实测元素含量(％)：C,83.18；H,4.72；N,12.10。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 2, the steps are the same, and the compound N 1 -([1,1'-biphenyl]-4-yl)benzene-1,2-diamine is substituted for the compound o-aminodiphenylamine to obtain 0.448g of a white compound (Yield 31.3%). The molecular ion mass determined by mass spectrometry analysis is: 577.26 (calculated value: 577.23); theoretical element content (%) C 40 H 27 N 5 : C, 83.17; H, 4.71; N, 12.12; measured element content (%): C, 83.18; H, 4.72; N, 12.10. The above analysis results show that the obtained product is the target product.
实施例168Example 168
Figure PCTCN2020081035-appb-000248
Figure PCTCN2020081035-appb-000248
依照实施例3的合成，步骤相同，用化合物N 1-([1,1'-联苯]-4-基)苯-1,2-二胺代替化合物邻氨基二苯胺，得到白色化合物0.458g(产率33.8％)。质谱分析确定的分子离子质量为：577.28(计算值为：577.23)；理论元素含量(％)C 40H 27N 5：C,83.17；H,4.71；N,12.12；实测元素含量(％)：C,83.18；H,4.72；N,12.10。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 3, the steps are the same, and the compound N 1 -([1,1'-biphenyl]-4-yl)benzene-1,2-diamine is substituted for the compound o-aminodiphenylamine to obtain 0.458g of a white compound (Yield 33.8%). The molecular ion mass determined by mass spectrometry analysis is: 577.28 (calculated value: 577.23); theoretical element content (%) C 40 H 27 N 5 : C, 83.17; H, 4.71; N, 12.12; measured element content (%): C, 83.18; H, 4.72; N, 12.10. The above analysis results show that the obtained product is the target product.
实施例169Example 169
Figure PCTCN2020081035-appb-000249
Figure PCTCN2020081035-appb-000249
依照实施例4的合成，步骤相同，用化合物[1,1'-联苯]-4-甲醛代替化合物苯甲醛，得到白色化合物0.531g(产率36.7％)。质谱分析确定的分子离子质量为：577.29(计算值为：577.23)；理论元素含量(％)C 40H 27N 5：C,83.17；H,4.71；N,12.12；实测元素含量(％)：C,83.18；H,4.72；N,12.10。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 4, the steps were the same, and the compound [1,1'-biphenyl]-4-carbaldehyde was used instead of the compound benzaldehyde to obtain 0.531 g of a white compound (yield 36.7%). The molecular ion mass determined by mass spectrometry analysis is: 577.29 (calculated value: 577.23); theoretical element content (%) C 40 H 27 N 5 : C, 83.17; H, 4.71; N, 12.12; measured element content (%): C, 83.18; H, 4.72; N, 12.10. The above analysis results show that the obtained product is the target product.
实施例170Example 170
Figure PCTCN2020081035-appb-000250
Figure PCTCN2020081035-appb-000250
依照实施例5的合成，步骤相同，用[1,1'-联苯]-4-甲醛代替化合物苯甲醛，得到白色化合物0.538g(产率34.3％)。质谱分析确定的分子离子质量为：577.31(计算值为：577.23)；理论元素含量(％)C 40H 27N 5：C,83.17；H,4.71；N,12.12；实测元素含量(％)：C,83.18；H,4.72；N,12.10。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 5, the steps were the same, and [1,1'-biphenyl]-4-carbaldehyde was used instead of the compound benzaldehyde to obtain 0.538 g of a white compound (yield 34.3%). The molecular ion mass determined by mass spectrometry analysis is: 577.31 (calculated value: 577.23); theoretical element content (%) C 40 H 27 N 5 : C, 83.17; H, 4.71; N, 12.12; measured element content (%): C, 83.18; H, 4.72; N, 12.10. The above analysis results show that the obtained product is the target product.
实施例171Example 171
Figure PCTCN2020081035-appb-000251
Figure PCTCN2020081035-appb-000251
依照实施例6的合成，步骤相同，用[1,1'-联苯]-4-甲醛代替化合物苯甲醛，得到白色化合物0.527g(产率36.7％)。质谱分析确定的分子离子质量为：577.25(计算值为：577.23)；理论元素含量(％)C 40H 27N 5：C,83.17；H,4.71；N,12.12；实测元素含量(％)：C,83.18；H,4.72；N,12.10。上述分析结果表明，获得的产物为目标产品。 According to the synthesis of Example 6, the steps are the same, using [1,1'-biphenyl]-4-carbaldehyde instead of the compound benzaldehyde to obtain 0.527 g of a white compound (yield 36.7%). The molecular ion mass determined by mass spectrometry analysis is: 577.25 (calculated value: 577.23); theoretical element content (%) C 40 H 27 N 5 : C, 83.17; H, 4.71; N, 12.12; measured element content (%): C, 83.18; H, 4.72; N, 12.10. The above analysis results show that the obtained product is the target product.
效果实施例1Effect Example 1
以下利用本发明的材料制备电致发光器件实施例，具体的器件制备工艺如下：透明ITO玻璃作为制备器件的基底材料，后先以5％ITO洗液超声处理30min，之后依次以蒸馏水(2次)、丙酮(2次)、异丙醇(2次)超声洗涤，最后将ITO玻璃保存在异丙醇中。每次使用前，先用丙酮棉球和异丙醇棉球小心擦拭ITO玻璃表面，待异丙醇冲洗后烘干，之后用等离子体处理5min。器件的制备利用真空镀膜设备采用真空蒸镀工艺完成，当真空蒸镀系统的真空度达到5×10 -4Pa以下时开始蒸镀，沉积速率由赛恩斯膜厚仪，利用真空蒸镀工艺在ITO玻璃上依次沉积各种有机层及LiF电子注入层和金属Al电极(具体器件结构见如下效果实施例)。器件的电流、电压、亮度、发光光谱等特性采用PR 650光谱扫描亮度计和Keithley K 2400数字源表系统同步测试。器件的性能测试在无水无氧手套箱中进行。 The following examples of electroluminescent device preparation using the material of the present invention, the specific device preparation process is as follows: transparent ITO glass is used as the base material for the preparation of the device, and then ultrasonically treated with 5% ITO lotion for 30 minutes, followed by distilled water (2 times ), acetone (2 times), isopropanol (2 times) ultrasonic washing, and finally the ITO glass is stored in isopropanol. Before each use, carefully wipe the surface of the ITO glass with an acetone cotton ball and an isopropyl alcohol cotton ball, rinse it with isopropyl alcohol and dry it, and then treat it with plasma for 5 minutes. The device is prepared by vacuum coating equipment using vacuum evaporation process. When the vacuum degree of the vacuum evaporation system reaches 5×10 -4 Pa or less, evaporation starts. The deposition rate is determined by Sainz Film Thickness Meter using vacuum evaporation process. Various organic layers, LiF electron injection layers and metal Al electrodes are sequentially deposited on the ITO glass (see the following effect examples for specific device structures). The current, voltage, brightness, luminescence spectrum and other characteristics of the device are tested simultaneously with PR 650 spectral scanning luminance meter and Keithley K 2400 digital source meter system. The performance test of the device is carried out in anhydrous and oxygen-free glove box.
在效果实施例1-1至171-1的有机电致发光器件中，HATCN被用来作为空穴注入层使用、DBBA被用来作为第1空穴传输层使用、TCTA被作为第2空穴传输层使用、在发光层中TCTA分别与本发明中的化合物1-171混合作为主体材料使用(TCTA与化合物1-171的重量混合比例为1:1)、本发明中的化合物1-171被用作电子传输材料使用。效果实施例有机电致发光器件结构为[ITO/HATCN(5nm)/DBBA(60nm)/TCTA(10nm)/TCTA:n+10wt％IrPPy 3/n(30nm)/LiF(1nm)/Al(100nm)]。n代表化合物序号：1-171，在同一个器件中主体材料里采用的化合物与电子传输层采用的化合物相同，IrPPy 3作为掺杂发光材料使用(重量比掺杂浓度为10WT％)。效果实施例结果见表1-1。 In the organic electroluminescent devices of effect examples 1-1 to 171-1, HATCN is used as the hole injection layer, DBBA is used as the first hole transport layer, and TCTA is used as the second hole The transport layer is used. In the light-emitting layer, TCTA is mixed with the compound 1-171 of the present invention as a host material (the weight mixing ratio of TCTA and compound 1-171 is 1:1), and the compound 1-171 of the present invention is used as a host material. Used as an electronic transmission material. Effect Example The structure of the organic electroluminescent device is [ITO/HATCN(5nm)/DBBA(60nm)/TCTA(10nm)/TCTA:n+10wt%IrPPy 3 /n(30nm)/LiF(1nm)/Al(100nm) )]. n represents the compound number: 1-171. In the same device, the compound used in the host material is the same as that used in the electron transport layer, and IrPPy 3 is used as the doped luminescent material (the weight ratio doping concentration is 10WT%). The results of the effect examples are shown in Table 1-1.
对比实施例1Comparative Example 1
对比实施例1-1至3-1有机电致发光器件中，HATCN被用来作为空穴注入层使用、DBBA被用来作为第1空穴传输层使用、TCTA被作为第2空穴传输层使用；在发光层中TCTA分别与3P-T2T、E1或E2混合作为主体材料，两种材料按照重量比1:1混合，IrPPy 3掺杂发光材料使用(重量比掺杂浓度为10WT％)，3P-T2T、E1或E2分别同时被用作电子传输材料使用。对比实施例1-1至3-1有机电致发光器件结构为[ITO/HATCN(5nm)/DBBA(60nm)/TCTA(10nm)/TCTA:3P-T2T或E1或E2+10wt％IrPPy 3/3P-T2T或E1或E2(30nm)/LiF(1nm)/Al(100nm)]。 In Comparative Examples 1-1 to 3-1 organic electroluminescent devices, HATCN was used as the hole injection layer, DBBA was used as the first hole transport layer, and TCTA was used as the second hole transport layer Use; In the light-emitting layer, TCTA is mixed with 3P-T2T, E1 or E2 as the host material. The two materials are mixed in a weight ratio of 1:1, and IrPPy 3 doped luminescent material is used (the weight ratio doping concentration is 10WT%), 3P-T2T, E1 or E2 are used as electron transport materials at the same time. Comparative Examples 1-1 to 3-1 organic electroluminescent device structure is [ITO/HATCN (5nm)/DBBA (60nm)/TCTA (10nm)/TCTA: 3P-T2T or E1 or E2+10wt% IrPPy 3 / 3P-T2T or E1 or E2(30nm)/LiF(1nm)/Al(100nm)].
对比实施例4-1至15-1器件中，HATCN被用来作为空穴注入层使用、DBBA被用来作为第1空穴传输层使用、TCTA被作为第2空穴传输层使用；对比实施例4-1至15-1器件中TBT-07、TBT-14、ET85、1、3、4、130、135、150、160、165和170分别被用作电子传输层(ETL)材料使用、在发光层中作为主体材料使用。对比实施例4-1至15-1有机电致发光器件结构为[ITO/HATCN(5nm)/DBBA(60nm)/TCTA(10nm)/n+10wt％IrPPy 3/n(30nm)/LiF(1nm)/Al(100nm)]。n代表化合物序号，在同一个器件中主体材料里采用的化合物与电子传输层采用的化合物相同，IrPPy 3作为掺杂发光材料使用(重量比掺杂浓度为10WT％)。对比实施例结果见表2-1。 In the devices of Comparative Examples 4-1 to 15-1, HATCN was used as the hole injection layer, DBBA was used as the first hole transport layer, and TCTA was used as the second hole transport layer; comparative implementation In the devices of Examples 4-1 to 15-1, TBT-07, TBT-14, ET85, 1, 3, 4, 130, 135, 150, 160, 165, and 170 are used as electron transport layer (ETL) materials, respectively. Used as a host material in the light-emitting layer. Comparative Examples 4-1 to 15-1 organic electroluminescent device structure is [ITO/HATCN(5nm)/DBBA(60nm)/TCTA(10nm)/n+10wt%IrPPy 3 /n(30nm)/LiF(1nm) )/Al(100nm)]. n represents the compound number. In the same device, the compound used in the host material is the same as that used in the electron transport layer, and IrPPy 3 is used as the doped luminescent material (the weight ratio doping concentration is 10WT%). The results of the comparative example are shown in Table 2-1.
效果实施例及对比实施例中涉及的化合物结构如下：The structures of the compounds involved in the effect examples and comparative examples are as follows:
Figure PCTCN2020081035-appb-000252
Figure PCTCN2020081035-appb-000252
Figure PCTCN2020081035-appb-000253
Figure PCTCN2020081035-appb-000253
表1-1.实施例器件在驱动电流密度为10mA/cm 2条件下(恒流驱动模式)的测试数据(器件寿命T90表示器件亮度衰减到初始亮度90％所消耗的时间)。 Table 1-1. Test data of the device of the embodiment under the condition of a drive current density of 10 mA/cm 2 (constant current drive mode) (device life T90 represents the time it takes for the device brightness to decay to 90% of the initial brightness).
Figure PCTCN2020081035-appb-000254
Figure PCTCN2020081035-appb-000254
Figure PCTCN2020081035-appb-000255
Figure PCTCN2020081035-appb-000255
Figure PCTCN2020081035-appb-000256
Figure PCTCN2020081035-appb-000256
Figure PCTCN2020081035-appb-000257
Figure PCTCN2020081035-appb-000257
Figure PCTCN2020081035-appb-000258
Figure PCTCN2020081035-appb-000258
Figure PCTCN2020081035-appb-000259
Figure PCTCN2020081035-appb-000259
表2-1.对比实施例器件在驱动电流密度为10mA/cm 2条件下(恒流驱动模式)的测试数据(器件寿命T90表示器件亮度衰减到初始亮度90％所消耗的时间)。 Table 2-1. Test data of the comparative example device under the condition of a drive current density of 10 mA/cm 2 (constant current drive mode) (device life T90 represents the time it takes for the device brightness to decay to 90% of the initial brightness).
Figure PCTCN2020081035-appb-000260
Figure PCTCN2020081035-appb-000260
Figure PCTCN2020081035-appb-000261
Figure PCTCN2020081035-appb-000261
由上述效果实施例1及表1-1可知，采用本发明的1,3,5-三嗪类化合物作为电子传输层，同时作为电子受体材料与电子给体材料构建发光层，制备得到的有机电致发光器件的亮度可达8310cd/m 2-8960cd/m 2；电流效率可达79cd/A-91cd/A；器件寿命可达1023小时-1299小时(T90)。 From the above effect embodiment 1 and Table 1-1, it can be seen that the 1,3,5-triazine compound of the present invention is used as the electron transport layer, and at the same time as the electron acceptor material and the electron donor material to construct the light emitting layer. luminance organic electroluminescent device up to 8310cd / m 2 -8960cd / m 2 ; the current efficiency of up to 79cd / a-91cd / a; device life up to 1023 hours -1299 hours (T90).
由上述对比实施例1及表2-1可知，采用上述化合物作为电子传输层，同时作为电子受体材料构建发光层制备得到的有机电致发光器件的亮度为5082cd/m 2-5810cd/m 2；电流效率为52cd/A-57cd/A；器件寿命为410小时-690小时(T90)。 From the above comparative example 1 and Table 2-1, it can be seen that the brightness of the organic electroluminescent device prepared by using the above compound as the electron transport layer and at the same time as the electron acceptor material to construct the light emitting layer is 5082cd/m 2 -5810cd/m 2 ; Current efficiency is 52cd/A-57cd/A; device lifetime is 410 hours-690 hours (T90).
由此可见，采用本发明的1,3,5-三嗪类化合物作为电子传输层，同时作为电子受体材料与电子给体材料构建发光层制备得到的有机电致发光器件，与上述化合物作为电子传输层，同时作为电子受体材料构建发光层制备得到的有机电致发光器件相比较，亮度提高了43％-76％，电流效率提高了39％-75％；器件寿命提高了48％-216％。It can be seen that the organic electroluminescent device prepared by using the 1,3,5-triazine compound of the present invention as the electron transport layer and at the same time as the electron acceptor material and the electron donor material to construct the light-emitting layer, and the above compound as Compared with the organic electroluminescent device prepared by using the electron transport layer as the electron acceptor material to construct the light-emitting layer, the brightness is increased by 43%-76%, the current efficiency is increased by 39%-75%, and the device life is increased by 48%- 216%.
效果实施例2Effect Example 2
在效果实施例1-2至171-2的有机电致发光器件中，HATCN被用来作为空穴注入层使用、DBBA被用来作为第1空穴传输层使用、TCTA被作为第2空穴传输层使用、在发光层中TCTA分别与本发明中的化合物1-171混合作为主体材料使用(TCTA与化合物1-171的重量混合比例为1:1)、TPBI被用作电子传输材料使用。效果实施例有机电致发光器件结构为[ITO/HATCN(5nm)/DBBA(60nm)/TCTA(10nm)/TCTA:n+10wt％IrPPy 3/TPBI(30nm)/LiF(1nm)/Al(100nm)]。n代表化合物序号：1-171，在同一个器件中主体材料里采用的化合物与电子传输层采用的化合物相同，IrPPy 3作为掺杂发光材料使用(重量比掺杂浓度为10WT％)。效果实施例结果见表1-2。 In the organic electroluminescent devices of effect examples 1-2 to 171-2, HATCN is used as the hole injection layer, DBBA is used as the first hole transport layer, and TCTA is used as the second hole The transport layer is used. In the light-emitting layer, TCTA is mixed with the compound 1-171 of the present invention as a host material (the weight mixing ratio of TCTA and compound 1-171 is 1:1), and TPBI is used as an electron transport material. Effect Example The structure of the organic electroluminescent device is [ITO/HATCN(5nm)/DBBA(60nm)/TCTA(10nm)/TCTA:n+10wt%IrPPy 3 /TPBI(30nm)/LiF(1nm)/Al(100nm) )]. n represents the compound number: 1-171. In the same device, the compound used in the host material is the same as that used in the electron transport layer, and IrPPy 3 is used as the doped luminescent material (the weight ratio doping concentration is 10WT%). The results of the effect examples are shown in Table 1-2.
对比实施例2Comparative Example 2
对比实施例1-2至6-2有机电致发光器件中，HATCN被用来作为空穴注入层使用、DBBA被用来作为第1空穴传输层使用、TCTA被作为第2空穴传输层使用；在发光层中TCTA与3P-T2T、E1、E2、TBT-07、TBT-14和ET85之一混合作为主体材料，两种材料按照重量比1:1混合，IrPPy 3掺杂发光材料使用(重量比掺杂浓度为10WT％)，TPBI被用作电子传输材料使用。对比实施例1-2至6-2有机电致发光器件结构为[ITO/HATCN(5nm)/DBBA(60nm)/TCTA(10nm)/TCTA:3P-T2T、E1、E2、TBT-07、TBT-14或ET85+10wt％IrPPy 3/TPBI(30nm)/LiF(1nm)/Al(100nm)]。 In Comparative Examples 1-2 to 6-2 organic electroluminescent devices, HATCN was used as the hole injection layer, DBBA was used as the first hole transport layer, and TCTA was used as the second hole transport layer Use; TCTA is mixed with one of 3P-T2T, E1, E2, TBT-07, TBT-14 and ET85 as the host material in the light-emitting layer, the two materials are mixed in a weight ratio of 1:1, and IrPPy 3 doped light-emitting material. (Weight ratio doping concentration is 10WT%), TPBI is used as an electron transport material. Comparative Examples 1-2 to 6-2 Organic electroluminescent device structure is [ITO/HATCN (5nm)/DBBA (60nm)/TCTA (10nm)/TCTA: 3P-T2T, E1, E2, TBT-07, TBT -14 or ET85+10wt% IrPPy 3 /TPBI(30nm)/LiF(1nm)/Al(100nm)].
对比实施例7-2至15-2器件中，HATCN被用来作为空穴注入层使用、DBBA被用来作为第1空穴传输层使用、TCTA被作为第2空穴传输层使用、在发光层中化合物1、3、4、130、135、150、160、165和170作为主体材料使用、IrPPy 3被作为掺杂发光材料使用(重量比掺杂浓度为10WT％)；TPBI被用作电子传输材料使用。对比实施例7-2至15-2有机电致发光器件结构为[ITO/HATCN(5nm)/DBBA(60nm)/TCTA(10nm)/n+10wt％IrPPy 3/TPBI(30nm)/LiF(1nm)/Al(100nm)]。对比实施例结果见表2-2。 In the devices of Comparative Examples 7-2 to 15-2, HATCN was used as the hole injection layer, DBBA was used as the first hole transport layer, TCTA was used as the second hole transport layer, Compounds 1, 3 , 4 , 130, 135, 150, 160, 165 and 170 in the layer are used as host materials, IrPPy 3 is used as doped luminescent material (weight ratio doping concentration is 10WT%); TPBI is used as electron Use of transmission materials. Comparative Examples 7-2 to 15-2 organic electroluminescent device structures are [ITO/HATCN(5nm)/DBBA(60nm)/TCTA(10nm)/n+10wt%IrPPy 3 /TPBI(30nm)/LiF(1nm) )/Al(100nm)]. The results of the comparative example are shown in Table 2-2.
表1-2.实施例器件在驱动电流密度为10mA/cm 2条件下(恒流驱动模式)的测试数据(器件寿命T90表示器件亮度衰减到初始亮度90％所消耗的时间)。 Table 1-2. Test data of the device of the embodiment under the condition of a driving current density of 10 mA/cm 2 (constant current driving mode) (device life T90 represents the time it takes for the device brightness to decay to 90% of the initial brightness).
Figure PCTCN2020081035-appb-000262
Figure PCTCN2020081035-appb-000262
Figure PCTCN2020081035-appb-000263
Figure PCTCN2020081035-appb-000263
Figure PCTCN2020081035-appb-000264
Figure PCTCN2020081035-appb-000264
Figure PCTCN2020081035-appb-000265
Figure PCTCN2020081035-appb-000265
Figure PCTCN2020081035-appb-000266
Figure PCTCN2020081035-appb-000266
Figure PCTCN2020081035-appb-000267
Figure PCTCN2020081035-appb-000267
表2-2.对比实施例器件在驱动电流密度为10mA/cm 2条件下(恒流驱动模式)的测试数据(器件寿命T90表示器件亮度衰减到初始亮度90％所消耗的时间)。 Table 2-2. Test data of the comparative example device under the condition of a drive current density of 10 mA/cm 2 (constant current drive mode) (device life T90 represents the time it takes for the device brightness to decay to 90% of the initial brightness).
Figure PCTCN2020081035-appb-000268
Figure PCTCN2020081035-appb-000268
由上述效果实施例2及表1-2可知，采用本发明的1,3,5-三嗪类化合物作为电子受体材料与电子给体材料构建发光层，制备得到的有机电致发光器件的亮度可达7087cd/m 2-7981cd cd/m 2；电流效率可达72cd/A-83cd/A；器件寿命可达827小时-985小时(T90)。 From the above effect example 2 and Table 1-2, it can be seen that the 1,3,5-triazine compound of the present invention is used as the electron acceptor material and the electron donor material to construct the light emitting layer, and the prepared organic electroluminescent device is Brightness can reach 7087cd/m 2 -7981cd cd/m 2 ; current efficiency can reach 72cd/A-83cd/A; device life can reach 827 hours -985 hours (T90).
由上述对比实施例2及表2-2可知，采用上述化合物构建发光层制备得到的有机电致发光器件的 亮度为5082cd/m 2-5781cd/m 2；电流效率为48cd/A-63cd/A；器件寿命为410小时-672小时(T90)。 From the above Comparative Example 2 and Table 2-2, it can be seen that the brightness of the organic electroluminescent device prepared by using the above compound to construct the light-emitting layer is 5082cd/m 2 -5781cd/m 2 ; the current efficiency is 48cd/A-63cd/A ; Device life is 410 hours -672 hours (T90).
由此可见，采用本发明的1,3,5-三嗪类化合物作为电子受体材料与电子给体材料构建发光层制备得到的有机电致发光器件，与上述化合物构建的发光层制备得到的有机电致发光器件相比较，亮度提高了22.6％-57％，电流效率提高了14％-73％；器件寿命提高了23％-140％。It can be seen that the organic electroluminescent device prepared by using the 1,3,5-triazine compound of the present invention as the electron acceptor material and the electron donor material to construct the light emitting layer is prepared by the light emitting layer constructed with the above compound Compared with the organic electroluminescent device, the brightness is increased by 22.6%-57%, the current efficiency is increased by 14%-73%, and the life of the device is increased by 23%-140%.
效果实施例3Effect Example 3
在效果实施例1-3至171-3的有机电致发光器件中，HATCN被用来作为空穴注入层使用、DBBA被用来作为第1空穴传输层使用、TCTA被作为第2空穴传输层使用、在发光层中TCTA作为主体材料使用、化合物1-171分别被用作电子传输材料使用。效果实施例有机电致发光器件结构为[ITO/HATCN(5nm)/DBBA(60nm)/TCTA(10nm)/TCTA+10wt％IrPPy 3/n(30nm)/LiF(1nm)/Al(100nm)]。n代表化合物序号：1-171，在同一个器件中主体材料里采用的化合物与电子传输层采用的化合物相同，IrPPy 3作为掺杂发光材料使用(重量比掺杂浓度为10WT％)。效果实施例结果见表1-3。 In the organic electroluminescent devices of effect examples 1-3 to 171-3, HATCN is used as the hole injection layer, DBBA is used as the first hole transport layer, and TCTA is used as the second hole The transport layer is used, TCTA is used as the host material in the light-emitting layer, and compound 1-171 is used as the electron transport material. Effect Example The structure of the organic electroluminescent device is [ITO/HATCN(5nm)/DBBA(60nm)/TCTA(10nm)/TCTA+10wt%IrPPy 3 /n(30nm)/LiF(1nm)/Al(100nm)] . n represents the compound number: 1-171. In the same device, the compound used in the host material is the same as that used in the electron transport layer, and IrPPy 3 is used as the doped luminescent material (the weight ratio doping concentration is 10WT%). The results of the effect examples are shown in Table 1-3.
对比实施例3Comparative Example 3
对比实施例1-3至6-3有机电致发光器件中，HATCN被用来作为空穴注入层使用、DBBA被用来作为第1空穴传输层使用、TCTA被作为第2空穴传输层使用；在发光层中TCTA作为主体材料，IrPPy 3掺杂发光材料使用(重量比掺杂浓度为10WT％)，3P-T2T、E1、E2、TBT-07、TBT-14和ET85分别被用作电子传输材料使用。对比实施例1-3至6-3有机电致发光器件结构为[ITO/HATCN(5nm)/DBBA(60nm)/TCTA(10nm)/TCTA+10wt％IrPPy 3/3P-T2T、E1、E2、TBT-07、TBT-14或ET85(30nm)/LiF(1nm)/Al(100nm)]。对比实施例结果见表2-3。 In Comparative Examples 1-3 to 6-3 organic electroluminescent devices, HATCN was used as the hole injection layer, DBBA was used as the first hole transport layer, and TCTA was used as the second hole transport layer Use; TCTA as the host material in the light-emitting layer, IrPPy 3 doped light-emitting material (weight ratio doping concentration of 10WT%), 3P-T2T, E1, E2, TBT-07, TBT-14 and ET85 are used as Use of electronic transmission materials. Comparative Examples 1-3 to 6-3 organic electroluminescent device structure is [ITO/HATCN (5nm)/DBBA (60nm)/TCTA (10nm)/TCTA+10wt% IrPPy 3 /3P-T2T, E1, E2, TBT-07, TBT-14 or ET85(30nm)/LiF(1nm)/Al(100nm)]. The results of the comparative example are shown in Table 2-3.
表1-3.实施例器件在驱动电流密度为10mA/cm 2条件下(恒流驱动模式)的测试数据(器件寿命T90表示器件亮度衰减到初始亮度90％所消耗的时间)。 Table 1-3. Test data of the device of the embodiment under the condition of a driving current density of 10 mA/cm 2 (constant current driving mode) (device life T90 represents the time it takes for the device brightness to decay to 90% of the initial brightness).
Figure PCTCN2020081035-appb-000269
Figure PCTCN2020081035-appb-000269
Figure PCTCN2020081035-appb-000270
Figure PCTCN2020081035-appb-000270
Figure PCTCN2020081035-appb-000271
Figure PCTCN2020081035-appb-000271
Figure PCTCN2020081035-appb-000272
Figure PCTCN2020081035-appb-000272
Figure PCTCN2020081035-appb-000273
Figure PCTCN2020081035-appb-000273
Figure PCTCN2020081035-appb-000274
Figure PCTCN2020081035-appb-000274
表2-3.对比实施例器件在驱动电流密度为10mA/cm 2条件下(恒流驱动模式)的测试数据(器件寿命T90表示器件亮度衰减到初始亮度90％所消耗的时间)。 Table 2-3. Test data of the comparative example device under the condition of a driving current density of 10 mA/cm 2 (constant current driving mode) (device life T90 represents the time it takes for the device brightness to decay to 90% of the initial brightness).
Figure PCTCN2020081035-appb-000275
Figure PCTCN2020081035-appb-000275
Figure PCTCN2020081035-appb-000276
Figure PCTCN2020081035-appb-000276
由上述效果实施例3及表1-3可知，采用本发明的1,3,5-三嗪类化合物作为电子传输层制备得到的有机电致发光器件的亮度可达6371cd/m 2-7069cd/m 2；电流效率可达65cd/A-75cd/A；器件寿命可达746小时-877小时(T90)。 From the above effect example 3 and Table 1-3, it can be seen that the brightness of the organic electroluminescent device prepared by using the 1,3,5-triazine compound of the present invention as the electron transport layer can reach 6371cd/m 2 -7069cd/ m 2 ; current efficiency can reach 65cd/A-75cd/A; device lifetime can reach 746 hours-877 hours (T90).
由上述对比实施例3及表2-3可知，采用上述对比实施例中化合物作为电子传输层制备得到的有机电致发光器件的亮度为4862cd/m 2-5196cd/m 2；电流效率为50cd/A-56cd/A；器件寿命为361小时-496小时(T90)。 From the above comparative example 3 and Table 2-3, it can be seen that the organic electroluminescent device prepared by using the compound in the above comparative example as the electron transport layer has a brightness of 4862cd/m 2 -5196cd/m 2 and a current efficiency of 50cd/ A-56cd/A; device life is 361 hours -496 hours (T90).
由此可见，采用本发明的1,3,5-三嗪类化合物与上述现有化合物相比较，作为电子传输层制备得到的有机电致发光器件的亮度提高了22.6％-45.4％，电流效率提高了16％-50％；器件寿命提高了50％-143％。It can be seen that the 1,3,5-triazine compound of the present invention is compared with the above-mentioned existing compounds, and the brightness of the organic electroluminescent device prepared as the electron transport layer is increased by 22.6%-45.4%, and the current efficiency Increased by 16%-50%; device life increased by 50%-143%.
效果实施例4Effect Example 4
在效果实施例1-4至171-4的有机电致发光器件中，HATCN被用来作为空穴注入层使用、DBBA被用来作为第1空穴传输层使用、TCTA被作为第2空穴传输层使用、在发光层中TCTA分别与本发明中的化合物1-171混合作为主体材料使用(TCTA与化合物1-171的重量混合比例为1:1)、本发明中的化合物1-179被用作电子传输材料使用。效果实施例有机电致发光器件结构为[ITO/HATCN(5nm)/DBBA(60nm)/TCTA(10nm)/TCTA:n+1wt％DPh2AAN/n(30nm)/LiF(1nm)/Al(100nm)]。n代表化合物序号：1-171，在同一个器件中主体材料里采用的化合物与电子传输层采用的化合物相同，DPh2AAN作为掺杂发光材料使用(重量比掺杂浓度为1WT％)。效果实施例结果见表1-5。In the organic electroluminescent devices of effect examples 1-4 to 171-4, HATCN is used as the hole injection layer, DBBA is used as the first hole transport layer, and TCTA is used as the second hole The transport layer is used. In the light-emitting layer, TCTA is mixed with the compound 1-171 of the present invention as a host material (the weight mixing ratio of TCTA and compound 1-171 is 1:1), and the compound 1-179 of the present invention is used as a host material. Used as an electronic transmission material. Effect Example The structure of the organic electroluminescent device is [ITO/HATCN(5nm)/DBBA(60nm)/TCTA(10nm)/TCTA:n+1wt%DPh2AAN/n(30nm)/LiF(1nm)/Al(100nm) ]. n represents the compound number: 1-171. In the same device, the compound used in the host material is the same as the compound used in the electron transport layer, and DPh2AAN is used as the doped luminescent material (weight ratio doping concentration is 1WT%). The results of the effect examples are shown in Table 1-5.
对比实施例4Comparative Example 4
对比实施例1-4至3-4有机电致发光器件中，HATCN被用来作为空穴注入层使用、DBBA被用来作为第1空穴传输层使用、TCTA被作为第2空穴传输层使用；在发光层中TCTA分别与3P-T2T、E1或E2混合作为主体材料，两种材料按照重量比1:1混合，DPh2AAN掺杂发光材料使用(重量比掺杂浓度为1WT％)，3P-T2T、E1或E2分别被用作电子传输材料使用。对比实施例1-1至3-1有机电致发光器件结构为[ITO/HATCN(5nm)/DBBA(60nm)/TCTA(10nm)/TCTA:3P-T2T或E1或E2+10wt％DPh2AAN/3P-T2T或E1或E2(30nm)/LiF(1nm)/Al(100nm)]。In Comparative Examples 1-4 to 3-4 organic electroluminescent devices, HATCN was used as the hole injection layer, DBBA was used as the first hole transport layer, and TCTA was used as the second hole transport layer Use; TCTA is mixed with 3P-T2T, E1 or E2 as the host material in the light-emitting layer, the two materials are mixed in a weight ratio of 1:1, DPh2AAN doped luminescent material is used (weight ratio doping concentration is 1WT%), 3P -T2T, E1 or E2 are used as electron transport materials respectively. Comparative Examples 1-1 to 3-1 organic electroluminescent device structure is [ITO/HATCN (5nm)/DBBA (60nm)/TCTA (10nm)/TCTA: 3P-T2T or E1 or E2+10wt%DPh2AAN/3P -T2T or E1 or E2(30nm)/LiF(1nm)/Al(100nm)].
表1-4.实施例器件在驱动电流密度为10mA/cm 2条件下(恒流驱动模式)的测试数据(器件寿命T90表示器件亮度衰减到初始亮度90％所消耗的时间)。 Table 1-4. Test data of the device of the embodiment under the condition of a driving current density of 10 mA/cm 2 (constant current driving mode) (device life T90 represents the time it takes for the brightness of the device to decay to 90% of the initial brightness).
Figure PCTCN2020081035-appb-000277
Figure PCTCN2020081035-appb-000277
Figure PCTCN2020081035-appb-000278
Figure PCTCN2020081035-appb-000278
Figure PCTCN2020081035-appb-000279
Figure PCTCN2020081035-appb-000279
Figure PCTCN2020081035-appb-000280
Figure PCTCN2020081035-appb-000280
Figure PCTCN2020081035-appb-000281
Figure PCTCN2020081035-appb-000281
Figure PCTCN2020081035-appb-000282
Figure PCTCN2020081035-appb-000282
Figure PCTCN2020081035-appb-000283
Figure PCTCN2020081035-appb-000283
表2-4.对比实施例器件在驱动电流密度为10mA/cm 2条件下(恒流驱动模式)的测试数据(器件寿命T90表示器件亮度衰减到初始亮度90％所消耗的时间)。 Table 2-4. Test data of the comparative example device under the condition of a driving current density of 10 mA/cm 2 (constant current driving mode) (device life T90 represents the time it takes for the device brightness to decay to 90% of the initial brightness).
Figure PCTCN2020081035-appb-000284
Figure PCTCN2020081035-appb-000284
由上述效果实施例及表1-4可知，采用本发明的1,3,5-三嗪类化合物作为电子传输层，同时作为电子受体材料与电子给体材料构建发光层，制备得到的有机电致发光器件的亮度可达3501cd/m 2-3900cd/m 2；电流效率可达54cd/A-62cd/A；器件寿命可达910小时-990小时(T90)。 It can be seen from the above effect examples and Tables 1-4 that the 1,3,5-triazine compound of the present invention is used as the electron transport layer, and at the same time as the electron acceptor material and the electron donor material to construct the light emitting layer, the prepared The brightness of the electroluminescent device can reach 3501cd/m 2 -3900cd/m 2 ; the current efficiency can reach 54cd/A-62cd/A; the lifetime of the device can reach 910 hours -990 hours (T90).
由上述对比实施例及表2-4可知，采用上述化合物作为电子传输层，同时作为电子受体材料构建发光层制备得到的有机电致发光器件的亮度为2350cd/m 2-2571cd/m 2；电流效率为39cd/A-41cd/A；器件寿命为402小时-462小时(T90)。 It can be seen from the above comparative examples and Tables 2-4 that the brightness of the organic electroluminescent device prepared by using the above compound as the electron transport layer and at the same time as the electron acceptor material to construct the light-emitting layer is 2350cd/m 2 -2571cd/m 2 ; The current efficiency is 39cd/A-41cd/A; the device life is 402 hours-462 hours (T90).
由此可见，采用本发明的1,3,5-三嗪类化合物作为电子传输层，同时作为电子受体材料与电子给体材料构建发光层制备得到的有机电致发光器件，与上述化合物作为电子传输层，同时作为电子受体材料构建发光层制备得到的有机电致发光器件相比较，亮度提高了36％-66％，电流效率提高了31.7％-59％；器件寿命提高了97％-146％。It can be seen that the organic electroluminescent device prepared by using the 1,3,5-triazine compound of the present invention as the electron transport layer and at the same time as the electron acceptor material and the electron donor material to construct the light-emitting layer, and the above compound as Compared with the organic electroluminescent device prepared by using the electron transport layer as the electron acceptor material to construct the light-emitting layer, the brightness is increased by 36%-66%, the current efficiency is increased by 31.7%-59%, and the life of the device is increased by 97%- 146%.
效果实施例5Effect Example 5
在效果实施例1-5至171-5的有机电致发光器件中，HATCN被用来作为空穴注入层使用、DBBA被用来作为第1空穴传输层使用、TCTA被作为第2空穴传输层使用、在发光层中TCTA分别与本发明中的化合物1-171混合作为主体材料使用(TCTA与化合物1-179的重量混合比例为1:1)、TPBI被用作电子传输材料使用。效果实施例有机电致发光器件结构为[ITO/HATCN(5nm)/DBBA(60nm)/TCTA(10nm)/TCTA:n+1wt％DPh2AAN/TPBI(30nm)/LiF(1nm)/Al(100nm)]。n代表化合物序号：1-179，DPh2AAN作为掺杂发光材料使用(重量比掺杂浓度为1WT％)。效果实施例结果见表1-5。In the organic electroluminescent devices of effect examples 1-5 to 171-5, HATCN is used as the hole injection layer, DBBA is used as the first hole transport layer, and TCTA is used as the second hole The transport layer is used. In the light-emitting layer, TCTA is mixed with the compound 1-171 of the present invention as a host material (the weight mixing ratio of TCTA and compound 1-179 is 1:1), and TPBI is used as an electron transport material. Effect Example The structure of the organic electroluminescent device is [ITO/HATCN(5nm)/DBBA(60nm)/TCTA(10nm)/TCTA:n+1wt%DPh2AAN/TPBI(30nm)/LiF(1nm)/Al(100nm) ]. n represents the compound number: 1-179, DPh2AAN is used as a doped luminescent material (weight ratio doping concentration is 1WT%). The results of the effect examples are shown in Table 1-5.
对比实施例5Comparative Example 5
对比实施例1-5至3-5有机电致发光器件中，HATCN被用来作为空穴注入层使用、DBBA被用来作为第1空穴传输层使用、TCTA被作为第2空穴传输层使用；在发光层中TCTA分别与3P-T2T、E1或E2混合作为主体材料，两种材料按照重量比1:1混合，DPh2AAN掺杂发光材料使用(重量比掺杂浓度为1WT％)，TPBI被用作电子传输材料使用。对比实施例1-5至3-5有机电致发光器件结构为[ITO/HATCN(5nm)/DBBA(60nm)/TCTA(10nm)/TCTA:3P-T2T或E1或E2+10wt％DPh2AAN/TPBI (30nm)/LiF(1nm)/Al(100nm)]。In Comparative Examples 1-5 to 3-5 organic electroluminescent devices, HATCN was used as the hole injection layer, DBBA was used as the first hole transport layer, and TCTA was used as the second hole transport layer Use; TCTA is mixed with 3P-T2T, E1 or E2 as the host material in the light-emitting layer, the two materials are mixed in a weight ratio of 1:1, DPh2AAN doped luminescent material is used (weight ratio doping concentration is 1WT%), TPBI Used as an electronic transmission material. Comparative Examples 1-5 to 3-5 organic electroluminescent device structure is [ITO/HATCN (5nm)/DBBA (60nm)/TCTA (10nm)/TCTA: 3P-T2T or E1 or E2+10wt%DPh2AAN/TPBI (30nm)/LiF(1nm)/Al(100nm)].
表1-5.实施例器件在驱动电流密度为10mA/cm 2条件下(恒流驱动模式)的测试数据(器件寿命T90表示器件亮度衰减到初始亮度90％所消耗的时间)。 Table 1-5. Test data of the device of the embodiment under the condition of a driving current density of 10 mA/cm 2 (constant current driving mode) (device life T90 represents the time it takes for the device brightness to decay to 90% of the initial brightness).
Figure PCTCN2020081035-appb-000285
Figure PCTCN2020081035-appb-000285
Figure PCTCN2020081035-appb-000286
Figure PCTCN2020081035-appb-000286
Figure PCTCN2020081035-appb-000287
Figure PCTCN2020081035-appb-000287
Figure PCTCN2020081035-appb-000288
Figure PCTCN2020081035-appb-000288
Figure PCTCN2020081035-appb-000289
Figure PCTCN2020081035-appb-000289
Figure PCTCN2020081035-appb-000290
Figure PCTCN2020081035-appb-000290
表2-5.对比实施例器件在驱动电流密度为10mA/cm 2条件下(恒流驱动模式)的测试数据(器件寿命T90表示器件亮度衰减到初始亮度90％所消耗的时间)。 Table 2-5. Test data of the comparative example device under the condition of a driving current density of 10 mA/cm 2 (constant current driving mode) (device life T90 represents the time it takes for the device brightness to decay to 90% of the initial brightness).
Figure PCTCN2020081035-appb-000291
Figure PCTCN2020081035-appb-000291
由上述效果实施例及表1-5可知，采用本发明的1,3,5-三嗪类化合物作为电子受体材料与电子给体材料构建发光层，制备得到的有机电致发光器件的亮度可达3205cd/m 2-3600cd/m 2；电流效率可达47cd/A-56cd/A；器件寿命可达650小时-750小时(T90)。 From the above effect examples and Tables 1-5, it can be seen that the 1,3,5-triazine compound of the present invention is used as the electron acceptor material and the electron donor material to construct the light emitting layer, and the brightness of the organic electroluminescent device prepared is It can reach 3205cd/m 2 -3600cd/m 2 ; current efficiency can reach 47cd/A-56cd/A; device life can reach 650 hours -750 hours (T90).
由上述对比实施例及表2-5可知，采用上述化合物作为电子受体材料构建发光层制备得到的有机电致发光器件的亮度为2032cd/m 2-2205cd/m 2；电流效率为34cd/A-38cd/A；器件寿命为342小时-375小时(T90)。 It can be seen from the above comparative examples and Table 2-5 that the organic electroluminescent device prepared by using the above compound as the electron acceptor material to construct the luminescent layer has a brightness of 2032cd/m 2 -2205cd/m 2 and a current efficiency of 34cd/A -38cd/A; device lifetime is 342 hours -375 hours (T90).
由此可见，采用本发明的1,3,5-三嗪类化合物与上述现有化合物相比较，作为电子受体材料构建发光层制备得到的有机电致发光器件，亮度提高了45％-77％，电流效率提高了23.7％-64.7％；器件寿命提高了73％-119％。It can be seen that the 1,3,5-triazine compound of the present invention is used as an electron acceptor material to construct a light-emitting layer, and the brightness of the organic electroluminescent device prepared by using the 1,3,5-triazine compound of the present invention is increased by 45%-77. %, the current efficiency is increased by 23.7% to 64.7%; the device life is increased by 73% to 119%.
由于本发明如式I所示的1,3,5-三嗪类化合物母核为一个苯环通过单键链接一个三嗪和一个或多个苯并咪唑的分子结构较复杂，主要表现在：(1)一个三嗪杂环和一个或多个苯并咪唑杂环构成了一个复杂的复合杂环体系；(2)一个苯环外围通过单键链接一个三嗪衍生物和一个或多个苯并咪唑衍生物，这种分子的分子构象结构非常复杂；(3)三嗪衍生物和苯并咪唑衍生物均属于缺电子基团，而且三嗪衍生物比苯并咪唑衍生物具有更强的缺电子特性，因此会导致这种分子具有一定的分子内电荷转移特性。基于上述三个特点，按照已有的物理化学知识无法对于基于一个三嗪和一个或多个苯并咪唑组成的分子的基本电致发光特性进行预测或判断，因为上述三个特点对于一个材料的电致发光性能 (主要包括效率及稳定性)均具有重要影响。因此，必须通过实际实施例的实验验证方可以对于这些材料的电致发光性质做出判断。另外，在一个三嗪通过一个苯环链接一个或多个苯并咪唑衍生物的基本结构框架下，可以通过引入不同的取代基团在较大范围内调节目标分子的分子量，进而可以在较宽范围内(200-450℃)调节目标分子的升华温度，该特点对于选择与目标产物升华温度相近的匹配材料有利。Since the mother nucleus of the 1,3,5-triazine compound shown in formula I of the present invention is a benzene ring linked by a single bond, the molecular structure of a triazine and one or more benzimidazoles is relatively complicated, and it is mainly manifested in: (1) A triazine heterocycle and one or more benzimidazole heterocycles constitute a complex compound heterocyclic system; (2) A triazine derivative and one or more benzenes are linked by a single bond on the periphery of a benzene ring The molecular conformational structure of this molecule is very complicated; (3) Triazine derivatives and benzimidazole derivatives are both electron-deficient groups, and triazine derivatives are stronger than benzimidazole derivatives Due to the lack of electrons, this molecule will have certain intramolecular charge transfer characteristics. Based on the above three characteristics, it is impossible to predict or judge the basic electroluminescence characteristics of a molecule based on a triazine and one or more benzimidazoles based on the existing physical and chemical knowledge, because the above three characteristics are for a material. The electroluminescence properties (mainly including efficiency and stability) have important effects. Therefore, it is necessary to verify the electroluminescence properties of these materials through experimental verification of actual examples. In addition, under the basic structural framework of a triazine linking one or more benzimidazole derivatives through a benzene ring, the molecular weight of the target molecule can be adjusted in a larger range by introducing different substituent groups, and thus the molecular weight of the target molecule can be adjusted in a wider range. The sublimation temperature of the target molecule is adjusted within the range (200-450°C), which is advantageous for selecting matching materials that are close to the sublimation temperature of the target product.
有机电致发光材料与器件领域内的技术人员公知的是，一个良好的电子传输材料不一定就可能是一个良好的主体材料。作为一个良好的主体材料，通常是应该具有平衡且较好的电子和空穴传输特性。但是，主体材料的性质还取决于与其匹配的掺杂发光材料的载流子传输特性以及掺杂以后掺杂薄膜整体的载流子传输特性。例如一个电子传输主导的主体材料与具有一定空穴传输能力的掺杂材料相匹配就有可能获得较好的效果，与一个一定电子传输能力的掺杂材料相匹配就有可能获得较差的效果。需要指出的是，主体/客体掺杂后获得的复合薄膜的载流子传输性能往往不是两者单独性能的简单叠加，掺杂复合薄膜的载流子传输性能很难准确推测，必须通过具体实验分析验证方可以获得理想的匹配组合。另外，对于由电子给体和电子受体双组份构成的主体材料会更加复杂，其性能也很难凭着经验准确推断。It is well known to those skilled in the field of organic electroluminescent materials and devices that a good electron transport material may not necessarily be a good host material. As a good host material, it should generally have balanced and good electron and hole transport properties. However, the properties of the host material also depend on the carrier transport properties of the matched doped luminescent material and the overall carrier transport properties of the doped film after doping. For example, if a host material dominated by electron transport is matched with a doped material with a certain hole transport ability, it is possible to obtain better results, and if it is matched with a doped material with a certain electron transport ability, it is possible to obtain a poor effect. . It needs to be pointed out that the carrier transport performance of the composite film obtained after the host/guest doping is often not a simple superposition of the two separate properties. The carrier transport performance of the doped composite film is difficult to accurately predict, and specific experiments must be conducted. The analysis and verification party can obtain the ideal matching combination. In addition, the host material composed of the two-component electron donor and electron acceptor will be more complicated, and its performance is also difficult to accurately infer based on experience.
例如，由上述表2-1、2-2及3-2可知，将现有化合物E1、E2或3P-T2T同时作为电子传输材料和发光层主体材料之一，或者仅作为发光层主体材料之一，与其仅作为电子传输材料相比，制备得到的有机电致发光器件的效率及寿命并没有明显的提高。For example, from the above Tables 2-1, 2-2, and 3-2, it can be seen that the existing compounds E1, E2 or 3P-T2T are used as one of the electron transport material and the host material of the light-emitting layer at the same time, or only as one of the host materials of the light-emitting layer. First, compared with only being used as an electron transport material, the efficiency and lifetime of the prepared organic electroluminescent device are not significantly improved.
虽然CN102593374B公开了化合物TPT-07作为电子传输层，或作为电子传输层的同时，单独作为主体材料用于制备电致发光器件。但是，制备得到的发光器件的效率仍偏低。Although CN102593374B discloses the compound TPT-07 as an electron transport layer, or as an electron transport layer, it is used as a host material for the preparation of electroluminescent devices. However, the efficiency of the prepared light-emitting device is still low.
根据上述效果实施例及对比实施例的性能指标对比可知，采用本发明的化合物作为电子受体材料与电子给体材料的组合物，作为发光层主体材料使用时，在同样的驱动电流密度下，制备得到的有机电致发光器件的亮度、效率及寿命明显高于现有技术所公开的材料；进一步地，当采用本发明的化合物作为电子传输层，同时作为电子受体材料与电子给体材料构建发光层，在同样的驱动电流密度下，制备得到的有机电致发光器件，可获得更优的亮度、效率及寿命。特别是在于器件的稳定性具有最明显的技术效果优势。According to the comparison of the performance indicators of the above-mentioned effect examples and comparative examples, it can be seen that when the compound of the present invention is used as a combination of electron acceptor material and electron donor material, when used as the host material of the light-emitting layer, under the same driving current density, The brightness, efficiency and lifetime of the prepared organic electroluminescent device are significantly higher than that of the materials disclosed in the prior art; further, when the compound of the present invention is used as an electron transport layer, it is used as an electron acceptor material and an electron donor material at the same time The light-emitting layer is constructed, and the organic electroluminescent device prepared under the same driving current density can obtain better brightness, efficiency and lifetime. Especially the stability of the device has the most obvious technical effect advantage.

Claims (20)

  1. 一种如式I所示的1,3,5-三嗪类化合物，A 1,3,5-triazine compound as shown in formula I,
    Figure PCTCN2020081035-appb-100001
    Figure PCTCN2020081035-appb-100001
    其中，R 1、R 2、R 3、R 4和R 5中的1个或2个独立地为R；余者独立地为R Y1； Among them, one or two of R 1 , R 2 , R 3 , R 4 and R 5 are independently R; the rest are independently R Y1 ;
    R Y1、R 6、R 7、R 8、R 9、R 10、R 11、R 12、R 13、R 14和R 15独立地为氢、氘、卤素、氰基、C 1～C 10烷基、被一个或多个R a-1取代的C 1～C 10烷基、C 1～C 10烷基-O-、被一个或多个R a-2取代的C 1～C 10烷基-O-、C 6～C 14芳基、被一个或多个R a-3取代的C 6～C 14芳基、5-6元单环杂芳基、被一个或多个R a-4取代的5-6元单环杂芳基或
    Figure PCTCN2020081035-appb-100002
    所述的5-6元单环杂芳基和被一个或多个R a-4取代的5-6元单环杂芳基里的“5-6元单环杂芳基”中杂原子的定义如下：杂原子选自N、O和S中的一种或多种，杂原子数为1～4个；当R a-1、R a-2、R a-3和R a-4独立地为多个时，相同或不同；其中，
    Figure PCTCN2020081035-appb-100003
    为
    Figure PCTCN2020081035-appb-100004
    与
    Figure PCTCN2020081035-appb-100005
    通过单键连接；     R Y1 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 and R 15 are independently hydrogen, deuterium, halogen, cyano, C 1 ～C 10 alkane group, with one or more substituents R a-1 is C 1 ~ C 10 alkyl group, C 1 ~ C 10 alkyl group -O-, with one or more R a-2 substituted C 1 ~ C 10 alkyl group -O-, C 6 ~ C 14 aryl group, substituted with one or more R a-3 substituted C 6 ~ C 14 aryl, 5-6 membered monocyclic heteroaryl, substituted with one or more R a-4 Substituted 5-6 membered monocyclic heteroaryl or
    Figure PCTCN2020081035-appb-100002
    The heteroatoms in the 5-6 membered monocyclic heteroaryl group and the 5-6 membered monocyclic heteroaryl group substituted by one or more Ra -4 The definition is as follows: the heteroatom is selected from one or more of N, O and S, and the number of heteroatoms is 1 to 4; when Ra -1 , Ra -2 , Ra -3 and Ra -4 are independent When there are multiple places, they are the same or different; among them,
    Figure PCTCN2020081035-appb-100003
    for
    Figure PCTCN2020081035-appb-100004
    versus
    Figure PCTCN2020081035-appb-100005
    Connect via a single key;
    R独立地为
    Figure PCTCN2020081035-appb-100006
    R is independently
    Figure PCTCN2020081035-appb-100006
    n1和n2独立地为1、2、3或4；n3为1、2或3；n1 and n2 are independently 1, 2, 3 or 4; n3 is 1, 2 or 3;
    R 1-1、R 2-1、R 1-2、R 2-2、R 1-3、R 1-4、R 2-3独立地为氢、氘、卤素、氰基、C 1～C 10烷基、被一个或多个R b-1取代的C 1～C 10烷基、C 1～C 10烷基-O-、被一个或多个R b-2取代的C 1～C 10烷基-O-、C 6～C 14芳基、被一个或多个R b-3取代的C 6～C 14芳基、5-6元单环杂芳基、被一个或多个R b-4取代的5-6元单环杂芳基或
    Figure PCTCN2020081035-appb-100007
    所述的5-6元单环杂芳基和被一个或多个R b-4取代的5-6元单环杂芳基里的“5-6元单环杂芳基”中杂原子的定义如下：杂原子选自N、O和S中的一种或多种，杂原子数为1～4个；当R b-1、R b-2、R b-3和R b-4独立地为多个时，为相同或不同；其中，
    Figure PCTCN2020081035-appb-100008
    为
    Figure PCTCN2020081035-appb-100009
    与
    Figure PCTCN2020081035-appb-100010
    通过单键连接；     R 1-1 , R 2-1 , R 1-2 , R 2-2 , R 1-3 , R 1-4 , R 2-3 are independently hydrogen, deuterium, halogen, cyano, C 1 ～C 10 alkyl group, C 1 ～C 10 alkyl group substituted by one or more R b-1 , C 1 ～C 10 alkyl group-O-, C 1 ～C 10 substituted by one or more R b-2 alkyl -O-, C 6 ~ C 14 aryl group, substituted with one or more R b-3 is unsubstituted C 6 ~ C 14 aryl, 5-6 membered monocyclic heteroaryl, substituted with one or more R b -4 substituted 5-6 membered monocyclic heteroaryl or
    Figure PCTCN2020081035-appb-100007
    The heteroatoms in the 5-6 membered monocyclic heteroaryl group and the 5-6 membered monocyclic heteroaryl group substituted by one or more R b-4 The definition is as follows: heteroatoms are selected from one or more of N, O and S, and the number of heteroatoms is 1 to 4; when R b-1 , R b-2 , R b-3 and R b-4 are independent When there are multiple places, they are the same or different; among them,
    Figure PCTCN2020081035-appb-100008
    for
    Figure PCTCN2020081035-appb-100009
    versus
    Figure PCTCN2020081035-appb-100010
    Connect via a single key;
    Figure PCTCN2020081035-appb-100011
    独立地为苯基、被一个或多个R c-1取代的苯基、5-6元单环杂芳基、或、被一个或多个R c-2取代的5-6元单环杂芳基；所述的5-6元单环杂芳基和被一个或多个R c-2取代的5-6元单环杂芳基里的“5-6元单环杂芳基”中杂原子的定义如下：杂原子为N，杂原子个数为1～3个；当R c-1和R c-2独立地为多个时，相同或不同；
    Figure PCTCN2020081035-appb-100011
    Independently is phenyl, phenyl substituted with one or more R c-1 , 5-6 membered monocyclic heteroaryl, or, 5-6 membered monocyclic heterocyclic substituted with one or more R c-2 Aryl; the 5-6 membered monocyclic heteroaryl group and the 5-6 membered monocyclic heteroaryl group substituted by one or more R c-2 in the "5-6 membered monocyclic heteroaryl group" The definition of heteroatom is as follows: heteroatom is N, and the number of heteroatoms is 1 to 3; when R c-1 and R c-2 are independently multiple, they are the same or different;
    R a-1、R a-2、R a-3、R a-4、R b-1、R b-2、R b-3、R b-4、R c-1和R c-2独立地为如下取代基：氘、卤素、氰基、三氟甲基、C 1～C 6烷基或C 1～C 6烷基-O-。 R a-1 , R a-2 , R a-3 , R a-4 , R b-1 , R b-2 , R b-3 , R b-4 , R c-1 and R c-2 are independent Ground is the following substituents: deuterium, halogen, cyano, trifluoromethyl, C 1 -C 6 alkyl or C 1 -C 6 alkyl-O-.
  2. 如权利要求1所述的如式I所示的1,3,5-三嗪类化合物，其特征在于，R 1-1、R 2-1、R 1-2、R 2-2、R 1-3、R 1-4、R 2-3、R Y1、R 6、R 7、R 8、R 9、R 10、R 11、R 12、R 13、R 14和R 15独立地为卤素中，所述的卤素独立地为氟、氯、溴或碘； The 1,3,5-triazine compound of formula I according to claim 1, wherein R 1-1 , R 2-1 , R 1-2 , R 2-2 , R 1 -3 , R 1-4 , R 2-3 , R Y1 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 and R 15 are independently in halogen , The halogen is independently fluorine, chlorine, bromine or iodine;
    和/或，R Y1、R 6、R 7、R 8、R 9、R 10、R 11、R 12、R 13、R 14和R 15独立地为C 1～C 10烷基、被一个或多个R a-1取代的C 1～C 10烷基、C 1～C 10烷基-O-或被一个或多个R a-2取代的C 1～C 10烷基-O-中，所述的C 1～C 10烷基独立地为C 1～C 6烷基； And/or, R Y1 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 and R 15 are independently C 1 ～C 10 alkyl groups, which are either one or a plurality of R a-1 is substituted with C 1 ~ C 10 alkyl group, C 1 ~ C 10 alkyl group by one or more -O- R a-2 substituted by C 1 ~ C 10 alkyl group of -O-, The C 1 ～C 10 alkyl group is independently a C 1 ～C 6 alkyl group;
    和/或，R Y1、R 6、R 7、R 8、R 9、R 10、R 11、R 12、R 13、R 14和R 15独立地为C 6～C 14芳基或被一个或多个R a-3取代的C 6～C 14芳基中，所述的C 6～C 14芳基独立地为C 6～C 10芳基； And/or, R Y1 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 and R 15 are independently C 6 ～C 14 aryl groups or are one or Among the C 6 ～C 14 aryl groups substituted by R a-3 , the C 6 ～C 14 aryl groups are independently C 6 ～C 10 aryl groups;
    和/或，R Y1、R 6、R 7、R 8、R 9、R 10、R 11、R 12、R 13、R 14和R 15独立地为5-6元单环杂芳基或被一个或多个R a-4取代的5-6元单环杂芳基中，所述的C 1～C 12杂芳基独立地为杂原子选自N，杂原子数为1～3个； And/or, R Y1 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 and R 15 are independently 5-6 membered monocyclic heteroaryl groups or are In one or more 5-6 membered monocyclic heteroaryl groups substituted by Ra-4 , the C 1 ～C 12 heteroaryl groups are independently heteroatoms selected from N, and the number of heteroatoms is 1 to 3;
    和/或，R 1-1、R 2-1、R 1-2、R 2-2、R 1-3、R 1-4和R 2-3独立地为C 1～C 10烷基、被一个或多个R b-1取代的C 1～C 10烷基、C 1～C 10烷基-O-或被一个或多个R b-2取代的C 1～C 10烷基-O-中，所述的C 1～C 10烷基独立地为C 1～C 6烷基； And/or, R 1-1 , R 2-1 , R 1-2 , R 2-2 , R 1-3 , R 1-4 and R 2-3 are independently C 1 ～C 10 alkyl groups, one or more R b-1 is substituted with C 1 ~ C 10 alkyl group, C 1 ~ C 10 alkyl group by one or more -O- R b-2 is substituted with C 1 ~ C 10 alkyl group -O- Wherein, the C 1 ～C 10 alkyl group is independently a C 1 ～C 6 alkyl group;
    和/或，R 1-1、R 2-1、R 1-2、R 2-2、R 1-3、R 1-4和R 2-3独立地为C 6～C 14芳基或被一个或多个R b-3取代的C 6～C 14芳基中，所述的C 6～C 14芳基独立地为C 6～C 10芳基； And/or, R 1-1 , R 2-1 , R 1-2 , R 2-2 , R 1-3 , R 1-4 and R 2-3 are independently C 6 ～C 14 aryl groups or are In one or more C 6 ～C 14 aryl groups substituted by R b-3 , the C 6 ～C 14 aryl groups are independently C 6 ～C 10 aryl groups;
    和/或，R 1-1、R 2-1、R 1-2、R 2-2、R 1-3、R 1-4和R 2-3独立地为5-6元单环杂芳基或被一个或多个R b-4取代的5-6元单环杂芳基中，所述的C 1～C 12杂芳基独立地为杂原子选自N，杂原子数为1～3个； And/or, R 1-1 , R 2-1 , R 1-2 , R 2-2 , R 1-3 , R 1-4 and R 2-3 are independently 5-6 membered monocyclic heteroaryl groups Or in a 5-6 membered monocyclic heteroaryl group substituted by one or more R b-4 , the C 1 ～C 12 heteroaryl group is independently a heteroatom selected from N, and the number of heteroatoms is 1 to 3. A
    和/或，当
    Figure PCTCN2020081035-appb-100012
    独立地为苯基时，
    Figure PCTCN2020081035-appb-100013
    Figure PCTCN2020081035-appb-100014
    独立地为
    Figure PCTCN2020081035-appb-100015
    And/or when
    Figure PCTCN2020081035-appb-100012
    When independently phenyl,
    Figure PCTCN2020081035-appb-100013
    Figure PCTCN2020081035-appb-100014
    Independently
    Figure PCTCN2020081035-appb-100015
    和/或，
    Figure PCTCN2020081035-appb-100016
    独立地为5-6元单环杂芳基或被一个或多个R c- 2取代的5-6元单环杂芳基中，所述的5-6元单环杂芳基独立地为杂原子选自N，杂原子数为1～2个；     and / or,
    Figure PCTCN2020081035-appb-100016
    Independently is a 5-6 membered monocyclic heteroaryl group or a 5-6 membered monocyclic heteroaryl group substituted with one or more R c- 2 , said 5-6 membered monocyclic heteroaryl group is independently The heteroatom is selected from N, the number of heteroatoms is 1 to 2;
    和/或，R 6和R 11相同，R 7和R 12相同，R 8和R 13相同，R 9和R 14相同，R 10和R 15相同； And/or, R 6 and R 11 are the same, R 7 and R 12 are the same, R 8 and R 13 are the same, R 9 and R 14 are the same, and R 10 and R 15 are the same;
    和/或，R独立地位于所在苯环与
    Figure PCTCN2020081035-appb-100017
    连接位点的邻位、间位或对位；     And/or, R is independently located on the benzene ring and
    Figure PCTCN2020081035-appb-100017
    The ortho, meta or para position of the connection site;
    和/或，R a-1、R a-2、R a-3、R a-4、R b-1、R b-2、R b-3、R b-4、R c-1和R c-2独立地为卤素中，所述的卤素独立地为氟、氯、溴或碘； And/or, R a-1 , R a-2 , R a-3 , R a-4 , R b-1 , R b-2 , R b-3 , R b-4 , R c-1 and R Where c-2 is independently halogen, said halogen is independently fluorine, chlorine, bromine or iodine;
    和/或，R a-1、R a-2、R a-3、R a-4、R b-1、R b-2、R b-3、R b-4、R c-1和R c-2独立地为C 1～C 6烷基或C 1～C 6烷基-O-中，所述的C 1～C 6烷基或C 1～C 6烷基-O-中的C 1～C 6烷基独立地为甲基、乙基、正丙基、异丙基、正丁基、仲丁基、异丁基或叔丁基； And/or, R a-1 , R a-2 , R a-3 , R a-4 , R b-1 , R b-2 , R b-3 , R b-4 , R c-1 and R c-2 is independently C 1 ～C 6 alkyl or C 1 ～C 6 alkyl-O-, in the C 1 ～C 6 alkyl group or C 1 ～C 6 alkyl-O- 1 -C 6 alkyl is independently methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl or tert-butyl;
    和/或，R a-1、R a-2、R a-3、R a-4、R b-1、R b-2、R b-3、R b-4、R c-1和R c-2的个数独立地为1、2或3； And/or, R a-1 , R a-2 , R a-3 , R a-4 , R b-1 , R b-2 , R b-3 , R b-4 , R c-1 and R The number of c-2 is independently 1, 2 or 3;
    和/或，R Y1、R 6、R 7、R 8、R 9、R 10、R 11、R 12、R 13、R 14和R 15独立地为氢、氘、卤素、氰基、C 1～C 10烷基、被一个或多个R a-1取代的C 1～C 10烷基、C 6～C 14芳基或被一个或多个R a-3取代的C 6～C 14芳基； And/or, R Y1 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 and R 15 are independently hydrogen, deuterium, halogen, cyano, C 1 ~ C 10 alkyl group, with one or more substituents R a-1 is C 1 ~ C 10 alkyl group, C 6 ~ C 14 aryl group by one or more R a-3 substituted C 6 ~ C 14 aryl base;
    和/或，R 1-1、R 1-2、R 1-3和R 1-4独立地为氢、氘、C 1～C 10烷基、被一个或多个R b-1取代的C 1～C 10烷基、C 6～C 14芳基、被一个或多个R b-3取代的C 6～C 14芳基、5-6元单环杂芳基、被一个或多个R b-4取代的5-6元单环杂芳基或
    Figure PCTCN2020081035-appb-100018
    R 2-1、R 2-2和R 2-3独立地为氢；     And/or, R 1-1 , R 1-2 , R 1-3 and R 1-4 are independently hydrogen, deuterium, C 1 ～C 10 alkyl, C substituted by one or more R b-1 1 ~ C 10 alkyl group, C 6 ~ C 14 aryl group, substituted with one or more R b-3 is unsubstituted C 6 ~ C 14 aryl, 5-6 membered monocyclic heteroaryl, substituted with one or more R b-4 substituted 5-6 membered monocyclic heteroaryl or
    Figure PCTCN2020081035-appb-100018
    R 2-1 , R 2-2 and R 2-3 are independently hydrogen;
    和/或，R X1、R X2和R X3独立地为
    Figure PCTCN2020081035-appb-100019
    And/or, R X1 , R X2 and R X3 are independently
    Figure PCTCN2020081035-appb-100019
  3. 如权利要求2所述的如式I所示的1,3,5-三嗪类化合物，其特征在于，R 1-1、R 2-1、R 1-2、R 2-2、R 1-3、R 1-4、R 2-3、R Y1、R 6、R 7、R 8、R 9、R 10、R 11、R 12、R 13、R 14和R 15独立地为卤素中，所述的卤素独立地为氟； The 1,3,5-triazine compound of formula I according to claim 2, wherein R 1-1 , R 2-1 , R 1-2 , R 2-2 , R 1 -3 , R 1-4 , R 2-3 , R Y1 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 and R 15 are independently in halogen , The halogen is independently fluorine;
    和/或，R Y1、R 6、R 7、R 8、R 9、R 10、R 11、R 12、R 13、R 14和R 15独立地为C 1～C 10烷基、被一个或多个R a-1取代的C 1～C 10烷基、C 1～C 10烷基-O-或被一个或多个R a-2取代的C 1～C 10烷基-O-中，所述的C 1～C 10烷基独立地为甲基、乙基、正丙基、异丙基、正丁基、仲丁基、异丁基或叔丁基； And/or, R Y1 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 and R 15 are independently C 1 ～C 10 alkyl groups, which are either one or a plurality of R a-1 is substituted with C 1 ~ C 10 alkyl group, C 1 ~ C 10 alkyl group by one or more -O- R a-2 substituted by C 1 ~ C 10 alkyl group of -O-, The C 1 -C 10 alkyl group is independently methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl or tert-butyl;
    和/或，R Y1、R 6、R 7、R 8、R 9、R 10、R 11、R 12、R 13、R 14和R 15独立地为C 6～C 14芳基或被一个或多个R a-3取代的C 6～C 14芳基中，所述的C 6～C 14芳基独立地为苯基或萘基； And/or, R Y1 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 and R 15 are independently C 6 ～C 14 aryl groups or are one or Among the C 6 ～C 14 aryl groups substituted by R a-3 , the C 6 ～C 14 aryl groups are independently phenyl or naphthyl;
    和/或，R Y1、R 6、R 7、R 8、R 9、R 10、R 11、R 12、R 13、R 14和R 15独立地为5-6元单环杂芳基或被一个或多个R a-4取代的5-6元单环杂芳基中，所述的C 1～C 12杂芳基独立地为吡啶基； And/or, R Y1 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 and R 15 are independently 5-6 membered monocyclic heteroaryl groups or are In one or more 5-6 membered monocyclic heteroaryl groups substituted by Ra-4 , the C 1 ～C 12 heteroaryl groups are independently pyridyl;
    和/或，R 1-1、R 2-1、R 1-2、R 2-2、R 1-3、R 1-4和R 2-3独立地为C 1～C 10烷基、被一个或多个R b-1取代的C 1～C 10烷基、C 1～C 10烷基-O-或被一个或多个R b-2取代的C 1～C 10烷基-O-中，所述的C 1～C 10烷基独立地为甲基、乙基、正丙基、异丙基、正丁基、仲丁基、异丁基或叔丁基； And/or, R 1-1 , R 2-1 , R 1-2 , R 2-2 , R 1-3 , R 1-4 and R 2-3 are independently C 1 ～C 10 alkyl groups, one or more R b-1 is substituted with C 1 ~ C 10 alkyl group, C 1 ~ C 10 alkyl group by one or more -O- R b-2 is substituted with C 1 ~ C 10 alkyl group -O- Wherein, the C 1 -C 10 alkyl group is independently methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl or tert-butyl;
    和/或，R 1-1、R 2-1、R 1-2、R 2-2、R 1-3、R 1-4和R 2-3独立地为C 6～C 14芳基或被一个或多个R b-3取代的C 6～C 14芳基中，所述的C 6～C 14芳基独立地为苯基或萘基； And/or, R 1-1 , R 2-1 , R 1-2 , R 2-2 , R 1-3 , R 1-4 and R 2-3 are independently C 6 ～C 14 aryl groups or are In one or more R b-3 substituted C 6 ～C 14 aryl groups, the C 6 ～C 14 aryl groups are independently phenyl or naphthyl;
    和/或，R 1-1、R 2-1、R 1-2、R 2-2、R 1-3、R 1-4和R 2-3独立地为5-6元单环杂芳基或被一个或多个R b-4取代的5-6元单环杂芳基中，所述的C 1～C 12杂芳基独立地为吡啶基； And/or, R 1-1 , R 2-1 , R 1-2 , R 2-2 , R 1-3 , R 1-4 and R 2-3 are independently 5-6 membered monocyclic heteroaryl groups Or in the 5-6 membered monocyclic heteroaryl group substituted by one or more R b-4 , the C 1 ～C 12 heteroaryl group is independently pyridyl;
    和/或，当
    Figure PCTCN2020081035-appb-100020
    独立地为苯基时，
    Figure PCTCN2020081035-appb-100021
    Figure PCTCN2020081035-appb-100022
    独立地为
    Figure PCTCN2020081035-appb-100023
    And/or when
    Figure PCTCN2020081035-appb-100020
    When independently phenyl,
    Figure PCTCN2020081035-appb-100021
    Figure PCTCN2020081035-appb-100022
    Independently
    Figure PCTCN2020081035-appb-100023
    和/或，
    Figure PCTCN2020081035-appb-100024
    独立地为5-6元单环杂芳基或被一个或多个R c- 2取代的5-6元单环杂芳基中，所述的5-6元单环杂芳基独立地为吡啶基；     and / or,
    Figure PCTCN2020081035-appb-100024
    Independently is a 5-6 membered monocyclic heteroaryl group or a 5-6 membered monocyclic heteroaryl group substituted with one or more R c- 2 , said 5-6 membered monocyclic heteroaryl group is independently Pyridyl
    和/或，当R的个数为2个时，R独立地位于所在苯环与
    Figure PCTCN2020081035-appb-100025
    连接位点的间位；     And/or, when the number of R is 2, R is independently located on the benzene ring and
    Figure PCTCN2020081035-appb-100025
    Meta position of connection site;
    和/或，当R Y1、R 6、R 7、R 8、R 9、R 10、R 11、R 12、R 13、R 14和R 15独立地为被一个或多个R a-1取代的C 1～C 10烷基或被一个或多个R a-2取代的C 1～C 10烷基-O-时，所述的取代的C 1～C 10烷基或取代的C 1～C 10烷基-O-中的取代的C 1～C 10烷基独立地为三氟甲基； And/or, when R Y1 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 and R 15 are independently substituted by one or more R a-1 When the C 1 ～C 10 alkyl group or the C 1 ～C 10 alkyl group-O- substituted by one or more Ra -2 , the substituted C 1 ～C 10 alkyl group or the substituted C 1 ～ The substituted C 1 ～C 10 alkyl in C 10 alkyl-O- is independently trifluoromethyl;
    和/或，当R 1-1、R 2-1、R 1-2、R 2-2、R 1-3、R 1-4和R 2-3独立地为被一个或多个R b-1取代的C 1～C 10烷基或被一个或多个R b-2取代的C 1～C 10烷基-O-时，所述的取代的C 1～C 10烷基或取代的C 1～C 10烷基-O-中的取代的C 1～C 10烷基独立地为三氟甲基。 And/or, when R 1-1 , R 2-1 , R 1-2 , R 2-2 , R 1-3 , R 1-4 and R 2-3 are independently controlled by one or more R b- 1 substituted C 1 ～C 10 alkyl group or C 1 ～C 10 alkyl group substituted by one or more R b-2 or C 1 ～C 10 alkyl group-O-, said substituted C 1 ～C 10 alkyl group or substituted C The substituted C 1 to C 10 alkyl group in the 1 to C 10 alkyl group-O- is independently a trifluoromethyl group.
  4. 如权利要求3所述的如式I所示的1,3,5-三嗪类化合物，其特征在于，The 1,3,5-triazine compound of formula I according to claim 3, characterized in that:
    Figure PCTCN2020081035-appb-100026
    独立地为
    Figure PCTCN2020081035-appb-100027
    Figure PCTCN2020081035-appb-100028
    Figure PCTCN2020081035-appb-100026
    Independently
    Figure PCTCN2020081035-appb-100027
    Figure PCTCN2020081035-appb-100028
    和/或，
    Figure PCTCN2020081035-appb-100029
    独立地为
    Figure PCTCN2020081035-appb-100030
    Figure PCTCN2020081035-appb-100031
    and / or,
    Figure PCTCN2020081035-appb-100029
    Independently
    Figure PCTCN2020081035-appb-100030
    Figure PCTCN2020081035-appb-100031
    和/或，
    Figure PCTCN2020081035-appb-100032
    独立地为
    Figure PCTCN2020081035-appb-100033
    and / or,
    Figure PCTCN2020081035-appb-100032
    Independently
    Figure PCTCN2020081035-appb-100033
  5. 如权利要求4所述的如式I所示的1,3,5-三嗪类化合物，其特征在于，R Y1、R 6、R 7、R 8、R 9、R 10、R 11、R 12、R 13、R 14和R 15独立地为氢、氘、卤素、氰基、C 1～C 10烷基或被一个或多个R a-1取代的C 1～C 10烷基； The 1,3,5-triazine compound of formula I according to claim 4, wherein R Y1 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12, R 13, R 14 and R 15 are independently hydrogen, deuterium, halo, cyano, C 1 ~ C 10 alkyl group by one or more substituents R a-1 is C 1 ~ C 10 alkyl group;
    和/或，
    Figure PCTCN2020081035-appb-100034
    独立地为
    Figure PCTCN2020081035-appb-100035
    Figure PCTCN2020081035-appb-100036
    Figure PCTCN2020081035-appb-100037
    and / or,
    Figure PCTCN2020081035-appb-100034
    Independently
    Figure PCTCN2020081035-appb-100035
    Figure PCTCN2020081035-appb-100036
    Figure PCTCN2020081035-appb-100037
    和/或，
    Figure PCTCN2020081035-appb-100038
    独立地为
    Figure PCTCN2020081035-appb-100039
    Figure PCTCN2020081035-appb-100040
    and / or,
    Figure PCTCN2020081035-appb-100038
    Independently
    Figure PCTCN2020081035-appb-100039
    Figure PCTCN2020081035-appb-100040
  6. 如权利要求1所述的如式I所示的1,3,5-三嗪类化合物，其特征在于，R 1、R 2、R 3、R 4和R 5中的1个为R；余者独立地为R Y1；或者，R 2和R 4独立地为R；余者独立地为R Y1； The 1,3,5-triazine compound of formula I according to claim 1, wherein one of R 1 , R 2 , R 3 , R 4 and R 5 is R; R Y1 independently; or R 2 and R 4 independently R; the rest independently R Y1 ;
    和/或，R独立地为
    Figure PCTCN2020081035-appb-100041
    And/or, R is independently
    Figure PCTCN2020081035-appb-100041
    和/或，当R 2和R 2独立地为R时，R 2和R 4相同或不同，例如相同； And/or, when R 2 and R 2 are independently R, R 2 and R 4 are the same or different, such as the same;
    和/或，R Y1独立地为氢； And/or, R Y1 is independently hydrogen;
    和/或，R 6、R 7、R 8、R 9、R 10、R 11、R 12、R 13、R 14和R 15独立地为氢、卤素、C 1～C 10烷基、或被 一个或多个R a-1取代的C 1～C 10烷基；例如，R 8和R 13独立地为氢、卤素、C 1～C 10烷基、或被一个或多个R a-1取代的C 1～C 10烷基；R 6、R 7、R 9、R 10、R 11、R 12、R 14和R 15独立地为氢； And/or, R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 and R 15 are independently hydrogen, halogen, C 1 ～C 10 alkyl, or One or more C 1 ～C 10 alkyl groups substituted by R a-1 ; for example, R 8 and R 13 are independently hydrogen, halogen, C 1 ～C 10 alkyl, or one or more R a-1 Substituted C 1 ～C 10 alkyl; R 6 , R 7 , R 9 , R 10 , R 11 , R 12 , R 14 and R 15 are independently hydrogen;
    和/或，R a-1独立地为卤素； And/or, R a-1 is independently halogen;
    和/或，
    Figure PCTCN2020081035-appb-100042
    与
    Figure PCTCN2020081035-appb-100043
    相同或不同，例如相同；     and / or,
    Figure PCTCN2020081035-appb-100042
    versus
    Figure PCTCN2020081035-appb-100043
    The same or different, such as the same;
    和/或，R 1-1、R 2-1、R 1-2、R 2-2、R 1-3、R 1-4、R 2-3独立地为氢、C 6～C 14芳基、被一个或多个R b-3取代的C 6～C 14芳基、5-6元单环杂芳基、或
    Figure PCTCN2020081035-appb-100044
    例如，R 1-1、R 1-2、R 1-3、R 1-4独立地为氢、C 6～C 14芳基、被一个或多个R b-3取代的C 6～C 14芳基、5-6元单环杂芳基、或
    Figure PCTCN2020081035-appb-100045
    R 2-1、R 2-2、R 2-3独立地为氢。     And/or, R 1-1 , R 2-1 , R 1-2 , R 2-2 , R 1-3 , R 1-4 , R 2-3 are independently hydrogen, C 6 ～C 14 aryl , C 6 ～C 14 aryl substituted by one or more R b-3 , 5-6 membered monocyclic heteroaryl, or
    Figure PCTCN2020081035-appb-100044
    For example, R 1-1, R 1-2, R 1-3, R 1-4 are independently hydrogen, C 6 ~ C 14 aryl group, substituted with one or more R b-3 is unsubstituted C 6 ~ C 14 Aryl, 5-6 membered monocyclic heteroaryl, or
    Figure PCTCN2020081035-appb-100045
    R 2-1 , R 2-2 and R 2-3 are independently hydrogen.
  7. 如权利要求1所述的如式I所示的1,3,5-三嗪类化合物，其特征在于，其为如下方案1或方案2：The 1,3,5-triazine compound represented by formula I according to claim 1, characterized in that it is the following scheme 1 or scheme 2:
    方案1、plan 1,
    R 1、R 2、R 3、R 4和R 5中的1个为R；余者独立地为R Y1；或者，R 2和R 4独立地为R；余者独立地为R Y1，R Y1独立地为氢； One of R 1 , R 2 , R 3 , R 4 and R 5 is R; the others are independently R Y1 ; or, R 2 and R 4 are independently R; the others are independently R Y1 , R Y1 is independently hydrogen;
    R独立地为
    Figure PCTCN2020081035-appb-100046
    R is independently
    Figure PCTCN2020081035-appb-100046
    当R 2和R 4独立地为R时，R 2和R 4相同或不同； When R 2 and R 4 are independently R, R 2 and R 4 are the same or different;
    R 6、R 7、R 8、R 9、R 10、R 11、R 12、R 13、R 14和R 15独立地为氢、卤素、C 1～C 10烷基、或被一个或多个R a-1取代的C 1～C 10烷基； R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 and R 15 are independently hydrogen, halogen, C 1 to C 10 alkyl, or one or more C 1 ～C 10 alkyl substituted by R a-1 ;
    Figure PCTCN2020081035-appb-100047
    与
    Figure PCTCN2020081035-appb-100048
    相同或不同；
    Figure PCTCN2020081035-appb-100047
    versus
    Figure PCTCN2020081035-appb-100048
    The same or different
    R 1-1、R 2-1、R 1-2、R 2-2、R 1-3、R 1-4、R 2-3独立地为氢、C 6～C 14芳基、被一个或多个R b-3取代的C 6～C 14芳基、5-6元单环杂芳基、或
    Figure PCTCN2020081035-appb-100049
    R b-3独立地为卤素、三氟甲基或C 1～C 6烷基；     R 1-1 , R 2-1 , R 1-2 , R 2-2 , R 1-3 , R 1-4 , R 2-3 are independently hydrogen, C 6 ～C 14 aryl, and one or Multiple R b-3 substituted C 6 ～C 14 aryl groups, 5-6 membered monocyclic heteroaryl groups, or
    Figure PCTCN2020081035-appb-100049
    R b-3 is independently halogen, trifluoromethyl or C 1 ～C 6 alkyl;
    方案2、Scenario 2,
    R 1、R 2、R 3、R 4和R 5中的1个为R；余者独立地为R Y1；或者，R 2和R 4独立地为R；余者独立地为R Y1； One of R 1 , R 2 , R 3 , R 4 and R 5 is R; the others are independently R Y1 ; or, R 2 and R 4 are independently R; the others are independently R Y1 ;
    R Y1独立地为氢； R Y1 is independently hydrogen;
    R独立地为
    Figure PCTCN2020081035-appb-100050
    R is independently
    Figure PCTCN2020081035-appb-100050
    当R 2和R 4独立地为R时，R 2和R 4相同； When R 2 and R 4 are independently R, R 2 and R 4 are the same;
    R 8和R 13独立地为氢、卤素、C 1～C 10烷基、或被一个或多个R a-1取代的C 1～C 10烷基； R 8 and R 13 are independently hydrogen, halogen, C 1 ~ C 10 alkyl group, or by one or more substituents R a-1 is C 1 ~ C 10 alkyl group;
    R a-1独立地为卤素； R a-1 is independently halogen;
    R 6、R 7、R 9、R 10、R 11、R 12、R 14和R 15独立地为氢； R 6 , R 7 , R 9 , R 10 , R 11 , R 12 , R 14 and R 15 are independently hydrogen;
    Figure PCTCN2020081035-appb-100051
    与
    Figure PCTCN2020081035-appb-100052
    相同；
    Figure PCTCN2020081035-appb-100051
    versus
    Figure PCTCN2020081035-appb-100052
    the same;
    R 1-1、R 1-2、R 1-3、R 1-4独立地为氢、C 6～C 14芳基、被一个或多个R b-3取代的C 6～C 14芳基、5-6元单环杂芳基、或
    Figure PCTCN2020081035-appb-100053
     R 1-1, R 1-2, R 1-3 , R 1-4 are independently hydrogen, C 6 ~ C 14 aryl group, substituted with one or more R b-3 is unsubstituted C 6 ~ C 14 aryl group , 5-6 membered monocyclic heteroaryl, or
    Figure PCTCN2020081035-appb-100053
    R b-3独立地为卤素、三氟甲基或C 1～C 6烷基； R b-3 is independently halogen, trifluoromethyl or C 1 ～C 6 alkyl;
    R 2-1、R 2-2、R 2-3独立地为氢。 R 2-1 , R 2-2 and R 2-3 are independently hydrogen.
  8. 如权利要求1所述的如式I所示的1,3,5-三嗪类化合物，其特征在于，其为如下任何一个化合物：The 1,3,5-triazine compound of formula I according to claim 1, wherein it is any one of the following compounds:
    Figure PCTCN2020081035-appb-100054
    Figure PCTCN2020081035-appb-100054
    Figure PCTCN2020081035-appb-100055
    Figure PCTCN2020081035-appb-100055
    Figure PCTCN2020081035-appb-100056
    Figure PCTCN2020081035-appb-100056
    Figure PCTCN2020081035-appb-100057
    Figure PCTCN2020081035-appb-100057
    Figure PCTCN2020081035-appb-100058
    Figure PCTCN2020081035-appb-100058
    Figure PCTCN2020081035-appb-100059
    Figure PCTCN2020081035-appb-100059
    Figure PCTCN2020081035-appb-100060
    Figure PCTCN2020081035-appb-100060
    Figure PCTCN2020081035-appb-100061
    Figure PCTCN2020081035-appb-100061
    Figure PCTCN2020081035-appb-100062
    Figure PCTCN2020081035-appb-100062
  9. 一种如权利要求1～8中任一项所述的式I所示的1,3,5-三嗪类化合物作为电子材料、或在有机电致发光器件领域中的应用。An application of the 1,3,5-triazine compound represented by formula I according to any one of claims 1 to 8 as an electronic material or in the field of organic electroluminescent devices.
  10. 如权利要求9所述的应用，所述的电子材料为电子传输材料和/或电子受体材料；The application according to claim 9, wherein the electronic material is an electron transport material and/or an electron acceptor material;
    和/或，所述的式I所示的1,3,5-三嗪类化合物用于制备有机电致发光器件中的电子传输层、空穴阻挡层和发光层中的一种或多种。And/or, the 1,3,5-triazine compound represented by formula I is used to prepare one or more of the electron transport layer, the hole blocking layer and the light emitting layer in an organic electroluminescent device .
  11. 一种有机电致发光组合物，其包括电子给体材料和如权利要求1～8中任一项所述的如式I所示的1,3,5-三嗪类化合物。An organic electroluminescent composition comprising an electron donor material and the 1,3,5-triazine compound represented by formula I according to any one of claims 1-8.
  12. 如权利要求11所述的有机电致发光组合物，其特征在于，所述电子给体材料为苯基或萘基咔唑类电子给体材料；11. The organic electroluminescent composition of claim 11, wherein the electron donor material is a phenyl or naphthylcarbazole type electron donor material;
    和/或，所述的如式I所示的1,3,5-三嗪类化合物与所述的电子给体材料的摩尔比为3:1至1:3；And/or, the molar ratio of the 1,3,5-triazine compound shown in formula I to the electron donor material is 3:1 to 1:3;
    和/或，所述的有机电致发光组合物中还包括掺杂发光材料。And/or, the organic electroluminescent composition further includes a doped luminescent material.
  13. 如权利要求12所述的有机电致发光组合物，其特征在于，所述电子给体材料为苯基或萘基咔唑类电子给体材料中，所述的苯基或萘基咔唑类电子给体材料为含有2-3个苯基咔唑或者萘基咔唑基结构；The organic electroluminescent composition of claim 12, wherein the electron donor material is a phenyl or naphthylcarbazole-based electron donor material, and the phenyl or naphthylcarbazole-based electron donor material The electron donor material contains 2-3 phenylcarbazole or naphthylcarbazolyl structures;
    和/或，所述的如式I所示的1,3,5-三嗪类化合物与所述的电子给体材料的摩尔比为1:1；And/or, the molar ratio of the 1,3,5-triazine compound shown in formula I to the electron donor material is 1:1;
    和/或，所述的有机电致发光组合物中还包括掺杂发光材料时，所述的掺杂发光材料为荧光发光材料和/或磷光发光材料。And/or, when the organic electroluminescent composition further includes a doped luminescent material, the doped luminescent material is a fluorescent luminescent material and/or a phosphorescent luminescent material.
  14. 如权利要求13所述的有机电致发光组合物，其特征在于，所述电子给体材料为如下任一化合物：The organic electroluminescent composition of claim 13, wherein the electron donor material is any of the following compounds:
    Figure PCTCN2020081035-appb-100063
    Figure PCTCN2020081035-appb-100063
    Figure PCTCN2020081035-appb-100064
    Figure PCTCN2020081035-appb-100064
    和/或，所述的有机电致发光组合物中还包括掺杂发光材料、且所述的掺杂发光材料为荧光发光材料时，所述的掺杂发光材料在所述的组合物中的质量百分比为0.5 WT％-2.0 WT％； And/or, when the organic electroluminescent composition further includes a doped luminescent material, and the doped luminescent material is a fluorescent luminescent material, the doped luminescent material is in the composition The mass percentage is 0.5 WT ％-2.0 WT ％;
    和/或，所述的有机电致发光组合物中还包括掺杂发光材料、且所述的掺杂发光材料为磷光发光材料时，所述的掺杂发光材料在所述的组合物中的质量百分比为5.0 WT％-15.0 WT％； And/or, when the organic electroluminescent composition further includes a doped luminescent material, and the doped luminescent material is a phosphorescent luminescent material, the doped luminescent material is in the composition The mass percentage is 5.0 WT %-15.0 WT %;
    和/或，所述的有机电致发光组合物中还包括掺杂发光材料、且所述的掺杂发光材料为磷光发光材料时，所述的掺杂发光材料为如下任一化合物：And/or, when the organic electroluminescent composition further includes a doped luminescent material, and the doped luminescent material is a phosphorescent luminescent material, the doped luminescent material is any of the following compounds:
    Figure PCTCN2020081035-appb-100065
    Figure PCTCN2020081035-appb-100066
    其中，Ra 1、Ra 3、Rb 1、Rb 3、Rd 1、Rd 3、Re 4、Re 5、Re 6、Rf 7、Rf 8、Rf 9、Rb 10-1、Rb 10-2、Re 10-1、Re 10-2、Rf 10-1和Rf 10-2独立地为H或含有1-5个C的直链或支链烷基；Ra 2、Rb 2和Rd 2独立地为H、含有1-5个C的直链或支链烷基、苯基或1-5个C的 直链或支链烷基取代的苯基；
    Figure PCTCN2020081035-appb-100067
    独立地为含有1-2个N的六元芳香杂环；
    Figure PCTCN2020081035-appb-100065
    Figure PCTCN2020081035-appb-100066
    Among them, Ra 1 , Ra 3 , Rb 1 , Rb 3 , Rd 1 , Rd 3 , Re 4 , Re 5 , Re 6 , Rf 7 , Rf 8 , Rf 9 , Rb 10-1 , Rb 10-2 , Re 10 -1 , Re 10-2 , Rf 10-1 and Rf 10-2 are independently H or a linear or branched alkyl group containing 1-5 C; Ra 2 , Rb 2 and Rd 2 are independently H, Containing 1-5 C linear or branched alkyl, phenyl or 1-5 C linear or branched alkyl substituted phenyl;
    Figure PCTCN2020081035-appb-100067
    Independently is a six-membered aromatic heterocycle containing 1-2 N;
    和/或，所述的有机电致发光组合物中还包括掺杂发光材料、且所述的掺杂发光材料为荧光发光材料时，所述的掺杂发光材料为如下任一化合物：And/or, when the organic electroluminescent composition further includes a doped luminescent material, and the doped luminescent material is a fluorescent luminescent material, the doped luminescent material is any of the following compounds:
    Figure PCTCN2020081035-appb-100068
    Figure PCTCN2020081035-appb-100069
    其中，Rg 11-1、Rg 11-2、Rh 11-1、Rh 11-2独立地为含有1-5个C的直链或支链烷基；Rg 12-1、Rg 12-2、Rh 13-1、Rh 13-2、Rh 13-3和Rh 13-4代表含有1-5个C的直链或支链烷基、F或CF 3；Ri 14- 1、Ri 14-2、Ri 15-1、Ri 15-2、Rj 16-1、Rj 16-2、Rj 17-1、Rj 17-2、Rk 18-1、Rk 18-2、Rk 18-3、Rk 18-4、Rk 19-1、Rk 19-2、 Rk 19-3、Rk 19-4、Rl 20-1、Rl 20-2、Rl 20-3、Rl 20-4、Rm 23-1、Rm 24-1、Rn 26-1、Rn 27-1、Ro 29-1、Ro 30-1、Ro 32-1、Rp 34-1、Rp 35-1、Rp 36-1和Rp 37-1独立地为含有1-5个C的直链或支链烷基、环己烷或异丙基苯；Rm 22- 1、Rn 25-1、Ro 28-11和Rp 33-1为含有1-4个C的直链或支链烷基。
    Figure PCTCN2020081035-appb-100068
    Figure PCTCN2020081035-appb-100069
    Among them, Rg 11-1 , Rg 11-2 , Rh 11-1 , and Rh 11-2 are independently linear or branched alkyl groups containing 1-5 C; Rg 12-1 , Rg 12-2 , Rh a straight-chain or branched-chain alkyl group 13-1, Rh 13-2, Rh 13-3 and Rh 13-4 represents an a C 1-5, F, or CF 3; Ri 14- 1, Ri 14-2, Ri 15-1 , Ri 15-2 , Rj 16-1 , Rj 16-2 , Rj 17-1 , Rj 17-2 , Rk 18-1 , Rk 18-2 , Rk 18-3 , Rk 18-4 , Rk 19-1 , Rk 19-2 , Rk 19-3 , Rk 19-4 , Rl 20-1 , Rl 20-2 , Rl 20-3 , Rl 20-4 , Rm 23-1 , Rm 24-1 , Rn 26-1 , Rn 27-1 , Ro 29-1 , Ro 30-1 , Ro 32-1 , Rp 34-1 , Rp 35-1 , Rp 36-1 and Rp 37-1 independently contain 1-5 C is a linear or branched alkyl, cumene or cyclohexane; Rm 22- 1, Rn 25-1, Ro 28-11 and Rp 33-1 containing 1 to 4 straight chain or C Branched alkyl.
  15. 如权利要求14所述的有机电致发光组合物，其特征在于，所述电子给体材料为
    Figure PCTCN2020081035-appb-100070
    The organic electroluminescent composition of claim 14, wherein the electron donor material is
    Figure PCTCN2020081035-appb-100070
    和/或，所述的有机电致发光组合物中还包括掺杂发光材料、且所述的掺杂发光材料为荧光发光材料时，所述的掺杂发光材料在所述的组合物中的质量百分比为1.0 WT％； And/or, when the organic electroluminescent composition further includes a doped luminescent material, and the doped luminescent material is a fluorescent luminescent material, the doped luminescent material is in the composition The mass percentage is 1.0 WT %;
    和/或，所述的有机电致发光组合物中还包括掺杂发光材料、且所述的掺杂发光材料为磷光发光材料时，所述的掺杂发光材料在所述的组合物中的质量百分比为10.0 WT％； And/or, when the organic electroluminescent composition further includes a doped luminescent material, and the doped luminescent material is a phosphorescent luminescent material, the doped luminescent material is in the composition The mass percentage is 10.0 WT %;
    和/或，所述的有机电致发光组合物中还包括掺杂发光材料、且所述的掺杂发光材料为磷光发光材料时，所述的掺杂发光材料为
    Figure PCTCN2020081035-appb-100071
    And/or, when the organic electroluminescent composition further includes a doped luminescent material, and the doped luminescent material is a phosphorescent luminescent material, the doped luminescent material is
    Figure PCTCN2020081035-appb-100071
    和/或，所述的有机电致发光组合物中还包括掺杂发光材料、且所述的掺杂发光材料为荧光发光材料时，所述的掺杂发光材料为
    Figure PCTCN2020081035-appb-100072
    And/or, when the organic electroluminescent composition further includes a doped luminescent material, and the doped luminescent material is a fluorescent luminescent material, the doped luminescent material is
    Figure PCTCN2020081035-appb-100072
  16. 一种如权利要求11～15中任一项所述的有机电致发光组合物作为有机电致发光材料的应用。An application of the organic electroluminescent composition according to any one of claims 11 to 15 as an organic electroluminescent material.
  17. 一种有机电致发光器件，其特征在于，其含如权利要求11～15中任一项所述的有机电致发光组合物。An organic electroluminescence device, characterized in that it contains the organic electroluminescence composition according to any one of claims 11-15.
  18. 如权利要求17所述的有机电致发光器件，其特征在于，所述的有机电致发光组合物为发光层；17. The organic electroluminescent device of claim 17, wherein the organic electroluminescent composition is a light-emitting layer;
    和/或，所述有机电致发光器件中还包括基板，以及依次形成在基板上的阳极层、有机发光功能层和阴极层；所述的有机发光功能层中，包括含如上所述的发光层，还包括空穴注入层、空穴传输层、 电子阻挡层、空穴阻挡层、电子传输层和电子注入层中的任意一种或者多种的组合。And/or, the organic electroluminescence device further includes a substrate, and an anode layer, an organic light-emitting functional layer, and a cathode layer sequentially formed on the substrate; the organic light-emitting functional layer includes the light-emitting The layer also includes any one or a combination of a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer, and an electron injection layer.
  19. 如权利要求18所述的有机电致发光器件，其特征在于，当所述的有机发光功能层中，包括电子传输层时，所述的电子传输层中的电子传输材料与所述的有机电致发光组合物中的1,3,5-三嗪类化合物的结构相同。The organic electroluminescent device according to claim 18, wherein when the organic light-emitting function layer includes an electron transport layer, the electron transport material in the electron transport layer and the organic electroluminescence The 1,3,5-triazine compounds in the electroluminescent composition have the same structure.
  20. 一种如权利要求17～19任一项所述的有机电致发光器件用于制备有机电致发光显示器或有机电致发光照明光源。An organic electroluminescent device according to any one of claims 17-19 for preparing an organic electroluminescent display or an organic electroluminescent lighting source.
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