TW202035377A - Substituted 1,3,5-triazine compounds, compositions and applications thereof - Google Patents

Abstract

The present invention discloses a substituted 1,3,5-triazine compound, composition and use thereof. The present invention provides a 1,3,5-triazine compound as shown in Formula I. The 1,3,5-triazine compound of the present invention can be used not only as an electron transport material but also as an electron acceptor material; it can be used to prepare an electron transport layer or a composition with an electron donor material as a main material of an electroluminescent device, the electroluminescent device prepared therefrom has advantages of higher efficiency, longer lifespan, etc.; the composition composed of the electron acceptor material and the electron donor material can further be used to construct a luminescence layer besides the 1,3,5-triazine compound being used as the electron transport layer, and the electroluminescent device prepared therefrom has advantages of better high efficiency and longer lifespan.

Description

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

The invention relates to a substituted 1,3,5-triazine compound, composition and application thereof.

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.

In the early 1960s, Pope and others 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 and others of Kodak Company in 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 are used as anode and cathode respectively to prepare light-emitting devices. The device has a green light emission 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 worldwide.

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 octaethylporphyrin 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.

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. A large number of materials with excellent performance have made some breakthroughs in organic electroluminescence (see US 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).

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 a high fluorescence quantum yield, but their doped OLED devices are limited to 25% internal quantum efficiency, and the external quantum efficiency is generally lower than 5%, which is comparable to the efficiency of phosphorescent devices. There is still a big gap. For example, the red dye DCM (see CW Tang, SA VanSlyke, and CHChen, J. Appl. Phys., 1989, 65, 3610; US Pat. No. 5, 908, 581), device efficiency <10 cd/A; Green dye quinacridone (see US Pat. No. 5, 227, 252; 5,593,788; CN1482127 A; CN1219778; CN1660844), device efficiency <20 cd/A, etc.

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-triplet annihilation) mechanism (see D. Kondakov, TD Pawlik, 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 rate of singlet exciton generation, 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 heat. 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 and doped into 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).

Since singlet and triplet excitons can be used to emit light at the same time, the performance of the electroluminescent device of TADF material has been 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 two parts: 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 high efficiency The TADF glows. In addition, Exciplex luminescence is a charge transfer excited state luminescence behavior between a donor molecule and an acceptor molecule. Its luminescence originates from the electronic transition between the LUMO orbital of the acceptor molecule and the HOMO orbital of the donor molecule. . 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 thermal activation and 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 emission similar to planar heterojunction (PN) (see: Advanced Materials, 2016, 28, 239-244). Electroluminescent devices prepared with exciplexes 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.

,

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.

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.

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 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, CBP has poor electron transport capability, so the device efficiency is still low.

、

、

。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.

,

,

.

Therefore, compared with single-molecule TADF materials, the current device performance of exciplex still needs to be improved.

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.

其中，R¹ 、R² 、R³ 、R⁴ 和R⁵ 中的1個或2個獨立地為R；餘者（即R¹ 、R² 、R³ 、R⁴ 和R⁵ 中不為R的取代基；例如，當R¹ 、R² 、R³ 、R⁴ 和R⁵ 中的1個獨立地為R、且R³ 獨立地為R時，R¹ 、R² 、R⁴ 和R⁵ 不為R，或者，當R¹ 、R² 、R³ 、R⁴ 和R⁵ 中的2個獨立地為R、且R² 和R⁴ 獨立地為R時，R¹ 、R³ 和R⁵ 不為R）獨立地為R^Y1 ； R^Y1 、R⁶ 、R⁷ 、R⁸ 、R⁹ 、R¹⁰ 、R¹¹ 、R¹² 、R¹³ 、R¹⁴ 和R¹⁵ 獨立地為氫、氘、鹵素、氰基、C₁ ~C₁₀ 烷基、被一個或多個R^a-1 取代的C₁ ~C₁₀ 烷基、C₁ ~C₁₀ 烷基-O-、被一個或多個R^a-2 取代的C₁ ~C₁₀ 烷基-O-、C₆ ~C₁₄ 芳基、被一個或多個R^a-3 取代的C₆ ~C₁₄ 芳基、5-6元單環雜芳基、被一個或多個R^a-4 取代的5-6元單環雜芳基或

；所述的5-6元單環雜芳基和被一個或多個R^a-4 取代的5-6元單環雜芳基裡的“5-6元單環雜芳基”中雜原子的定義如下：雜原子選自N、O和S中的一種或多種，雜原子數為1~4個；當R^a-1 、R^a-2 、R^a-3 和R^a-4 獨立地為多個時，相同或不同；其中，

為

與

通過單鍵連接； R獨立地為

、

或

； n1和n2獨立地為1、2、3或4；n3為1、2或3； R^1-1 、R^2-1 、R^1-2 、R^2-2 、R^1-3 、R^1-4 、R^2-3 獨立地為氫、氘、鹵素、氰基、C₁ ~C₁₀ 烷基、被一個或多個R^b-1 取代的C₁ ~C₁₀ 烷基、C₁ ~C₁₀ 烷基-O-、被一個或多個R^b-2 取代的C₁ ~C₁₀ 烷基-O-、C₆ ~C₁₄ 芳基、被一個或多個R^b-3 取代的C₆ ~C₁₄ 芳基、5-6元單環雜芳基、被一個或多個R^b-4 取代的5-6元單環雜芳基或

；所述的5-6元單環雜芳基和被一個或多個R^b-4 取代的5-6元單環雜芳基裡的“5-6元單環雜芳基”中雜原子的定義如下：雜原子選自N、O和S中的一種或多種，雜原子數為1~4個；當R^b-1 、R^b-2 、R^b-3 和R^b-4 獨立地為多個時，為相同或不同；其中，

為

與

通過單鍵連接；

、

、

和

獨立地為苯基、被一個或多個R^c-1 取代的苯基、5-6元單環雜芳基、或、被一個或多個R^c-2 取代的5-6元單環雜芳基；所述的5-6元單環雜芳基和被一個或多個R^c-2 取代的5-6元單環雜芳基裡的“5-6元單環雜芳基”中雜原子的定義如下：雜原子為N，雜原子個數為1~3個；當R^c-1 和R^c-2 獨立地為多個時，相同或不同； 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 獨立地為如下取代基：氘、鹵素、氰基、三氟甲基、C₁ ~C₆ 烷基或C₁ ~C₆ 烷基-O-。The present invention provides a 1,3,5-triazine compound as shown in formula I,

Among them, one or two of R ¹ , R ² , R ³ , R ⁴ and R ⁵ are independently R; the rest (that is, 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 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 ₁ ~ C ₁₀ alkyl group -O-, with one or more R ^{a- 2} is a 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 , 5-6 membered monocyclic heteroaryl substituted with one or more R ^a-4 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 Is defined as follows: heteroatoms are 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} independently When there are multiple, the same or different; among them,

for

versus

Connected by a single bond; R is independently

,

or

; 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, halo, cyano, C ₁ ~ C ₁₀ alkyl group, with one or more R ^b-1 is substituted with C ₁ ~ C ₁₀ alkyl group, C ₁ ~ C ₁₀ -O- alkyl, substituted with one or more R ^b-2 substituted by C ₁ ~ C ₁₀ alkyl group -O-, C ₆ ~ C ₁₄ aryl group, substituted with one or more R ^b-3 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

; The heteroatom in the 5-6 membered monocyclic heteroaryl group and the 5-6 membered monocyclic heteroaryl group substituted by one or more R ^b-4 Is defined 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} independently When there are multiple, they are the same or different; among them,

for

versus

Connect via a single key;

,

,

with

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 1~3; 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} independently the following substituents: deuterium, Halogen, cyano, trifluoromethyl, C ₁ ~C ₆ alkyl or C ₁ ~C ₆ alkyl-O-.

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 .

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 halogen, and the halogen (for example, fluorine, chlorine, bromine or iodine) is independently fluorine.

In an 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 (such as methyl, ethyl, n-propyl, isopropyl, n-butyl, tertiary butyl , Secondary butyl, isobutyl, pentyl or hexyl), preferably C ₁ ~C ₄ alkyl (such as methyl, ethyl, n-propyl, isopropyl, n-butyl, secondary Butyl, isobutyl or tertiary butyl), more preferably methyl or isopropyl.

In an 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 to C ₁₄ aryl group substituted by one or more Ra ^-3 , the C ₆ to C ₁₄ aryl group is independently a C ₆ to C ₁₀ aryl group; for example, phenyl or naphthyl .

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 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.

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 C ₁ to C ₁₀ alkyl, C ₁ ~C ₁₀ alkyl substituted by one or more R ^b-1 , C ₁ ~C ₁₀ alkyl-O- or C ₁ ~C substituted by one or more R ^b-2 _{In 10} alkyl-O-, the C ₁ ~C ₁₀ alkyl group is independently a C ₁ ~C ₆ alkyl group (such as methyl, ethyl, n-propyl, isopropyl, n-butyl, tertiary butyl, sec-butyl, isobutyl, pentyl or hexyl group), preferably a C ₁ ~ C ₄ alkyl group (e.g. methyl, ethyl, n-propyl, isopropyl, n-butyl, Secondary butyl, isobutyl or tertiary butyl), more preferably methyl or isopropyl.

In an 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 to C ₁₄ aryl group substituted by one or more R ^b-3 , the C ₆ to C ₁₄ aryl group is independently a C ₆ to C ₁₀ aryl group; for example, phenyl or Naphthyl.

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.

、

、

和

獨立地為苯基時，

或

獨立地為

（例如

、

或

）。In an embodiment of the present invention, when

,

,

with

When independently phenyl,

or

Independently

(E.g

,

or

).

、

、

和

獨立地為5-6元單環雜芳基或被一個或多個R^c-2 取代的5-6元單環雜芳基中，所述的5-6元單環雜芳基獨立地為雜原子選自N，雜原子數為1~2個；較佳地為吡啶基。In a certain embodiment of the invention,

,

,

with

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 , the 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.

In a certain embodiment of the 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.

連接位點的鄰位、間位或對位；較佳地，當R的個數為2個時，獨立地位於所在苯環與

連接位點的間位。In an embodiment of the present invention, 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.

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 halogen, and the halogen (for example, fluorine, chlorine, bromine or iodine) is independently fluorine.

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 -O- in the C ₁ ~C ₆ alkyl group (such as methyl, ethyl, n-propyl, isopropyl, n-butyl, tertiary butyl, secondary butyl, isobutyl, pentyl or hexyl ) Are independently C ₁ ~C ₄ alkyl groups (such as methyl, ethyl, n-propyl, isopropyl, n-butyl, secondary butyl, isobutyl or tertiary butyl), more preferably It is methyl or isopropyl.

In a certain embodiment of the present invention, Ra ^-1 , Ra ^-2 , Ra ^-3 , Ra ^-4 , ^Rb-1 , ^Rb-2 , ^Rb-3 , ^Rb-4 , The number of R ^c-1 and R ^c-2 is 1, 2, or 3 independently.

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 R ^a-1 a-substituted C ₁ ~ C ₁₀ alkyl group by one or more R ^a-2 substituted C ₁ ~ C ₁₀ alkyl group -O-, a 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.

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 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^2-1 、R^2-2 和R^2-3 獨立地為氫。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 to 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.

獨立地為

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或

；較佳地為

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或

。In a certain embodiment of the invention,

Independently

,

,

,

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,

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,

or

; Preferably

,

,

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,

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or

.

獨立地為

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或

；較佳地為

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或

。In a certain embodiment of the invention,

Independently

,

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,

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or

; Preferably

,

,

,

,

,

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,

,

,

,

,

or

.

獨立地為

或

。In a certain embodiment of the invention,

Independently

or

.

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 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.

或

。In a certain embodiment of the invention, R is

or

.

或

； R^1-1 、R^1-2 、R^1-3 和R^1-4 獨立地為氫、氘、C_1~ C₁₀ 烷基、被一個或多個R^b-1 取代的C₁ ~C₁₀ 烷基、C₆ ~C₁₄ 芳基、被一個或多個R^b-3 取代的C₆ ~C₁₄ 芳基、5-6元單環雜芳基、被一個或多個R^b-4 取代的5-6元單環雜芳基或

，R^2-1 、R^2-2 和R^2-3 獨立地為氫。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, by 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; and R ⁶ the same as R ^11, R ^{7 is the} same as R ¹² , R ⁸ and R ^{13 are the} same, R ⁹ and R ^{14 are the} same, R ¹⁰ and R ^{15 are the} same; R is independently

or

; R ^1-1 , R ^1-2 , R ^1-3 and R ^{1-4 are} independently hydrogen, deuterium, C _1~ C ₁₀ alkyl, C ₁ to C substituted by one or more R ^b-1 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

, R ^2-1 , R ^2-2 and R ^{2-3 are} independently hydrogen.

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.

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, R ² and/or R ^{4 are} independently R; the rest are independently R ^Y1 .

In a certain embodiment of the invention, R ^{Y1 is} independently hydrogen.

In a certain embodiment of the 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; for example, R ² and/or R ^{4 are} independently R; the rest are independently R ^Y1 .

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; For example, 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 Ra ^-1 is trifluoromethyl.

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.

與

相同或不同，例如相同。In a certain embodiment of the invention,

versus

The same or different, such as the same.

與

相同或不同，例如相同。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 group, or C ₁ ~C ₁₀ alkyl group substituted by one or more Ra ^-1 ; for example, R ⁸ and R ^{13 are} independently hydrogen, halogen, C ₁ ~C ₁₀ alkyl group, or one or A plurality of R ^a-1 substituted C ₁ to C ₁₀ alkyl groups; R ⁶ , R ⁷ , R ⁹ , R ¹⁰ , R ¹¹ , R ¹² , R ¹⁴ and R ^{15 are} independently hydrogen; 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 Ra ^-1 is trifluoromethyl; and/or,

versus

The same or different, such as the same.

； 例如，R^1-1 、R^1-2 、R^1-3 、R^1-4 獨立地為氫、C₆ ~C₁₄ 芳基、被一個或多個R^b-3 取代的C₆ ~C₁₄ 芳基、5-6元單環雜芳基、或

； R^2-1 、R^2-2 、R^2-3 獨立地為氫。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

; ^{E.g., 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.

； 例如，R^b-3 獨立地為鹵素、三氟甲基或C₁ ~C₆ 烷基。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 group, and one or more R ^{b- 3-} substituted C ₆ ~C ₁₄ aryl, 5-6 membered monocyclic heteroaryl, or

; For example, R ^{b-3 is} independently halogen, trifluoromethyl or C ₁ ~C ₆ alkyl.

In a certain embodiment of the invention, R ^2-1 , R ^2-2 and R ^{2-3 are} independently hydrogen.

或

； 當R² 和R⁴ 獨立地為R時，R² 和R⁴ 相同或不同； R⁶ 、R⁷ 、R⁸ 、R⁹ 、R¹⁰ 、R¹¹ 、R¹² 、R¹³ 、R¹⁴ 和R¹⁵ 獨立地為氫、鹵素、C₁ ~C₁₀ 烷基、或被一個或多個R^a-1 取代的C₁ ~C₁₀ 烷基；R^a-1 獨立地為鹵素；

與

相同或不同； R^1-1 、R^2-1 、R^1-2 、R^2-2 、R^1-3 、R^1-4 、R^2-3 獨立地為氫、C₆ ~C₁₄ 芳基、被一個或多個R^b-3 取代的C₆ ~C₁₄ 芳基、5-6元單環雜芳基、或

；R^b-3 獨立地為鹵素、三氟甲基或C₁ ~C₆ 烷基； 例如，當R² 和R⁴ 獨立地為R時，R² 和R⁴ 相同； R⁸ 和R¹³ 獨立地為氫、鹵素、C₁ ~C₁₀ 烷基、或被一個或多個R^a-1 取代的C₁ ~C₁₀ 烷基； R^a-1 獨立地為鹵素； R⁶ 、R⁷ 、R⁹ 、R¹⁰ 、R¹¹ 、R¹² 、R¹⁴ 和R¹⁵ 獨立地為氫；

與

相同； R^1-1 、R^1-2 、R^1-3 、R^1-4 獨立地為氫、C₆ ~C₁₄ 芳基、被一個或多個R^b-3 取代的C₆ ~C₁₄ 芳基、5-6元單環雜芳基、或

； R^b-3 獨立地為鹵素、三氟甲基或C₁ ~C₆ 烷基； R^2-1 、R^2-2 、R^2-3 獨立地為氫。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; for example, R ² and/or R ^{4 are} independently R; the rest are independently R ^Y1 ; R is independently

or

; 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 and R ¹⁵ 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 independently halogen;

versus

Same or different; 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

; R ^{b-3 is} independently halogen, trifluoromethyl or C ₁ ~C ₆ alkyl; for example, when R ² and R ^{4 are} independently R, R ² and R ^{4 are the} same; R ⁸ and R ^{13 are} independent is hydrogen, halo, 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 independently halogen; R ^6, R ^7, R ^9. R ¹⁰ , R ¹¹ , R ¹² , R ¹⁴ and R ^{15 are} independently hydrogen;

versus

^{Same; 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 ^{b-3 is} independently halogen, trifluoromethyl or C ₁ to C ₆ alkyl; R ^2-1 , R ^2-2 , and R ^{2-3 are} independently hydrogen.

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、或

。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:

,

,

,

,

,

,

,

,

,

,

,

,

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,

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,

,

,

,

,

,or

.

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.

； 方案二，合成路線如下所示：

； 方案三，合成路線如下所示：

； 方案四，合成路線如下所示：

； 其中，R^1’ 和R^2’ 的定義同R¹ 、R² 、R³ 、R⁴ 、R⁵ 、R⁶ 、R⁷ 、R⁸ 、R⁹ 和R¹⁰ ，R^1-1 、R^2-1 、R^1-2 、R^2-2 、R¹ 、R² 、R³ 、R⁴ 、R⁵ 、R⁶ 、R⁷ 、R⁸ 、R⁹ 、R¹⁰ 、n1、n2和n3的定義如上所述，m1和m2獨立地為0、1、2、3或4。The present invention provides a method for preparing a 1,3,5-triazine compound as shown in formula I, which may include any of the following schemes: Scheme 1, the synthetic route is as follows:

; Scheme two, the synthetic route is as follows:

; Scheme three, the synthetic route is as follows:

; Scheme 4, the synthetic route is as follows:

; Wherein, 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 definition As described above, m1 and m2 are independently 0, 1, 2, 3, or 4.

The present invention provides an application of a 1,3,5-triazine compound as shown in formula I as an electronic material.

In an embodiment of the present invention, the electronic material is used as an electron transport material and/or electron acceptor material; preferably, it is 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.

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.

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.

、

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、

或

；例如

。In an embodiment of the present invention, the electron donor material in the organic electroluminescent composition can be a conventional phenyl or naphthylcarbazole electron donor material in the art; the benzene The phenyl or naphthylcarbazole-based electron-donor material preferably contains 2-3 phenylcarbazole or naphthylcarbazole-based structures; Any of the following compounds:

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

or

;E.g

.

In the present invention, the molar ratio of the 1,3,5-triazine compound represented by formula I and the electron donor material can be a conventional molar ratio in the art (for example, a conventional molar ratio in the art The molar ratio of the electron acceptor material to the electron donor material in the excimer complex), preferably, the 1,3,5-triazine compound represented by formula I and the electron donor The molar ratio of the bulk material is 3:1 to 1:3; more preferably 1:1.

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 Luminescent materials and/or phosphorescent luminescent materials (also called phosphorescent complex luminescent materials).

In the present invention, the quality percentage of the doped luminescent material in the organic electroluminescent composition can be a conventional quality percentage in the art. When the doped luminescent material is a fluorescent luminescent material, The quality percentage of the doped luminescent material in the composition is preferably 0.5 _WT %-2.0 _WT % (for example, 1 _WT %); when the doped luminescent material is a phosphorescent luminescent material, the The quality percentage of the doped luminescent material in the composition is preferably 5.0 _WT %-15.0 _WT % (for example, 10 _WT %).

、

、

、

、

或

； 其中，Ra¹ 、Ra³ 、Rb¹ 、Rb³ 、Rd¹ 、Rd³ 、Re⁴ 、Re⁵ 、Re⁶ 、Rf⁷ 、Rf⁸ 、Rf⁹ 、Rb^10-1 、Rb^10-2 、Re^10-1 、Re^10-2 、Rf^10-1 和Rf^10-2 獨立地為H或含有1-5個C的直鏈或支鏈烷基； Ra² 、Rb² 和Rd² 獨立地為H、含有1-5個C的直鏈或支鏈烷基、苯基或1-5個C的直鏈或支鏈烷基取代的苯基；

和

獨立地為含有1-2個N的六元芳香雜環。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:

,

,

,

,

or

; 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;

with

It is independently a six-membered aromatic heterocyclic ring containing 1-2 N.

）。In an embodiment of the present invention, in the doped luminescent material, the phosphorescent luminescent material is IrPPy ₃ (

).

、

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、

、

、

或

； 其中，Rg^11-1 、Rg^11-2 、Rh^11-1 、Rh^11-2 獨立地為含有1-5個C的直鏈或支鏈烷基； 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個C的直鏈或支鏈烷基、F或CF₃ ； 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 獨立地為含有1-5個C的直鏈或支鏈烷基、環己烷或異丙基苯； Rm^22-1 、Rn^25-1 、Ro^28-11 和Rp^33-1 為含有1-4個C的直鏈或支鏈烷基。In an embodiment of the present invention, in the doped luminescent material, the fluorescent luminescent material can be a conventional fluorescent luminescent material in the art. In the present invention, it is preferably any of the following compounds:

,

,

,

,

,

,

,

,

or

; 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 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 and Rp ^{37-1 are} independently containing 1- 5 C straight chain or branched alkyl, cyclohexane or cumene; Rm ^22-1 , Rn ^25-1 , Ro ^28-11 and Rp ^33-1 are straight chain containing 1-4 C Or branched alkyl.

。In an embodiment of the present invention, in the doped luminescent material, the fluorescent luminescent material is

.

The present invention provides an application of the above-mentioned organic electroluminescent composition as an organic electroluminescent material.

In an embodiment of the present invention, 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.

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).

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, 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 lighting source.

”是指，相應的基團通過該位點與化合物I中的其它片段、基團進行連接。Those skilled in the art can understand that, according to the conventions used in the art, the "

"Means that the corresponding group is connected to other fragments or groups in compound I through this site.

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.

In the present invention, when the number of the "substitution" is multiple, the "substitution" may be the same or different.

In the present invention, the position of "substitution" can be any position unless otherwise specified.

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%.

In the present invention, the deuterium is D or ² H, which is also called deuterium.

In the present invention, the abundance of deuterium at the deuterium substitution site is greater than 99%.

Term Description

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.

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".

Group definition

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).

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.

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.

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 the carbons that may be present in the substituents of the group.

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.

In addition to the foregoing, when used in the specification of this application and the scope of the patent application, the following terms have the following meanings unless otherwise specified.

In this application, the term "halogen" means fluorine, chlorine, bromine or iodine.

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, secondary butyl, isobutyl or tertiary butyl); pentyl The group 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, tertiary pentyl or neopentyl); hexyl is C ₆ alkyl (including isomers such as n-hexyl or isohexyl).

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.

啉基、喹

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、異喹啉基、

唑基、異

唑基、吲哚基、吡嗪基、噠嗪基、吡啶基、嘧啶基、吡咯基、四氫喹啉。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 this definition include but are not limited to: acridinyl, carbazolyl,

Linyl, quino

Linyl, pyrazolyl, indolyl, benzotriazolyl, furyl, thienyl, benzothienyl, benzofuranyl, quinolinyl, isoquinolinyl,

Azolyl, iso

Azolyl, indolyl, pyrazinyl, pyridazinyl, pyridyl, pyrimidinyl, pyrrolyl, tetrahydroquinoline.

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.

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.

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.

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.

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.

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.

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.

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 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.

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.

2-氯-4,6-二苯基-1,3,5-三嗪4.02g（15mmol），2-甲醯基苯硼酸2.70g（18mmol），碳酸鉀3.73g（27mmol）加入到250mL雙口瓶中，加入THF 100mL，H₂ O 20mL，氮氣條件下加入催化劑四（三苯基膦）鈀，回流12h。用二氯甲烷/水洗滌反應液，有機相旋去溶劑後，柱層析提純，得白色固體中間體（3.58g，產率70.8%）。Example 1

2-Chloro-4,6-diphenyl-1,3,5-triazine 4.02g (15mmol), 2-methanylphenylboronic acid 2.70g (18mmol), potassium carbonate 3.73g (27mmol) added to 250mL In the mouth flask, add 100 mL of THF, 20 mL of H ₂ O, add catalyst tetrakis (triphenylphosphine) palladium under nitrogen conditions, 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%).

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 0.333g (1.81mmol) of o-aminodiphenylamine, add 20mL ethanol, and reflux for 12h under nitrogen protection. After cooling to room temperature, it was filtered to obtain a white crude product. The white solid product 0.630g was obtained by methylene chloride column chromatography (83.5% yield). The molecular ion quality 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.

依照實施例1的合成，步驟相同，用化合物4-甲醯基苯硼酸代替化合物2-甲醯基苯硼酸，得到白色化合物0.523g（產率66.7%），質譜分析確定的分子離子品質為：501.12（計算值為：501.20）；理論元素含量（%）C₃₄ H₂₃ N₅ ：C, 81.42; H, 4.62; N, 13.96；實測元素含量（%）：C, 81.37; H, 4.60; N, 14.28。上述分析結果表明，獲得的產物為目標產品。Example 2

According to the synthesis of Example 1, the steps were the same, and the compound 4-methanylphenylboronic acid was used instead of the compound 2-methanylphenylboronic acid to obtain 0.523g of white compound (yield 66.7%). The molecular ion quality determined by mass spectrometry analysis 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.

依照實施例1的合成，步驟相同，用化合物3-甲醯基苯硼酸代替化合物2-甲醯基苯硼酸，得到白色化合物0.632g（產率80.6%），質譜分析確定的分子離子品質為：501.04（計算值為：501.20）；理論元素含量（%）C₃₄ H₂₃ N₅ ：C, 81.42; H, 4.62; N, 13.96；實測元素含量（%）：C, 81.45; H, 4.65; N, 14.02。上述分析結果表明，獲得的產物為目標產品。Example 3

According to the synthesis of Example 1, the steps are the same, and the compound 3-formylphenylboronic acid is used instead of the compound 2-formylphenylboronic acid to obtain 0.632g of white compound (yield 80.6%). The molecular ion quality determined by mass spectrometry is: 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.

10mL水溶解NaHSO₃ （4.70g，45.0mmol），加入苯甲醛0.350g（3.30mmol），常溫攪拌5h，然後加入N-(4-溴苯基)-1,2-苯二胺0.786g（3.00mmol），加入20mL乙醇，氮氣保護下回流12h。冷卻到室溫後過濾，得到白色固體粗產品1.43g（產率94.7%）。Example 4

Dissolve NaHSO ₃ (4.70g, 45.0mmol) in 10mL of water, add 0.350g (3.30mmol) of benzaldehyde, stir for 5h at room temperature, 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 (94.7% yield).

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 150mg (0.20mmol) of palladium dichloride catalyst [1,1'-bis(diphenylphosphino)ferrocene] dichloride under nitrogen protection, and reflux for 24h. After cooling to room temperature, the potassium acetate was removed by filtration, the filtrate was washed with dichloromethane/water after removing dioxane, and the organic phase was removed from the organic solvent, followed by column chromatography with dichloromethane as a developing solvent to obtain 745 mg of a white solid intermediate (The yield is 93.6%).

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 white solid compound (yield 73.2%). The molecular ion quality 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.

依照實施例4的合成，步驟相同，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（產率85.0%）。質譜分析確定的分子離子品質為：501.08（計算值為：501.20）；理論元素含量（%）C₃₄ H₂₃ N₅ ：C, 81.42; H, 4.62; N, 13.96；實測元素含量（%）：C, 81.35; H, 4.55; N, 14.12。上述分析結果表明，獲得的產物為目標產品。Example 5

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 The white compound is 638 mg (yield 85.0%). The molecular ion quality 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.

依照實施例4的合成，步驟相同，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（產率66.7%），質譜分析確定的分子離子品質為：501.32（計算值為：501.20）；理論元素含量（%）C₃₄ H₂₃ N₅ ：C, 81.42; H, 4.62; N, 13.96；實測元素含量（%）：C, 81.38; H, 4.57; N, 14.02。上述分析結果表明，獲得的產物為目標產品。Example 6

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 White compound 0.523g (yield 66.7%), the molecular ion quality 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.

依照實施例1的合成，步驟相同，用化合物N-（3-吡啶基）-1,2-苯二胺代替化合物鄰氨基二苯胺，得到白色化合物0.553g（產率70.5%），質譜分析確定的分子離子品質為：502.28（計算值為：502.19）；理論元素含量（%）C₃₃ H₂₂ N₆ ：C，78.87；H，4.41；N，16.72，實測元素含量（%）：C，78.95；H，4.33；N，16.85。上述分析結果表明，獲得的產物為目標產品。Example 7

According to the synthesis of Example 1, the steps are the same. The compound N-(3-pyridyl)-1,2-phenylenediamine is used instead of the compound o-aminodiphenylamine to obtain 0.553g of white compound (70.5% yield), which is confirmed by mass spectrometry. The quality of the molecular ion 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.

依照實施例1的合成，步驟相同，用化合物N-（4-吡啶基）-1,2-苯二胺代替化合物鄰氨基二苯胺，得到白色化合物0.356g（產率45.4%），質譜分析確定的分子離子品質為：502.31（計算值為：502.19）；理論元素含量（%）C₃₃ H₂₂ N₆ ：C，78.87；H，4.41；N，16.72，實測元素含量（%）：C，78.95；H，4.61；N，16.63。上述分析結果表明，獲得的產物為目標產品。Example 8

According to the synthesis of Example 1, the steps are the same, the compound N-(4-pyridyl)-1,2-phenylenediamine is used instead of the compound o-aminodiphenylamine to obtain 0.356g of white compound (yield 45.4%), which is confirmed by mass spectrometry The quality of the molecular ion 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.

依照實施例3的合成，步驟相同，用化合物N-（3-吡啶基）-1,2-苯二胺代替化合物鄰氨基二苯胺，得到白色化合物0.435g（產率55.5%），質譜分析確定的分子離子品質為：502.20（計算值為：502.19）；理論元素含量（%）C₃₃ H₂₂ N₆ ：C，78.87；H，4.41；N，16.72，實測元素含量（%）：C，78.85；H，4.41；N，16.83。上述分析結果表明，獲得的產物為目標產品。Example 9

According to the synthesis of Example 3, the steps were the same, 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 quality of the molecular ion 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.

依照實施例3的合成，步驟相同，用化合物N-（4-吡啶基）-1,2-苯二胺代替化合物鄰氨基二苯胺，得到白色化合物0.398g（產率50.8%），質譜分析確定的分子離子品質為：502.18（計算值為：502.19）；理論元素含量（%）C₃₃ H₂₂ N₆ ：C，78.87；H，4.41；N，16.72，實測元素含量（%）：C，78.88；H，4.49；N，16.81。上述分析結果表明，獲得的產物為目標產品。Example 10

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 quality of the molecular ion is: 502.18 (calculated value: 502.19); the 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, 4.49; N, 16.81. The above analysis results show that the obtained product is the target product.

依照實施例2的合成，步驟相同，用化合物N-（3-吡啶基）-1,2-苯二胺代替化合物鄰氨基二苯胺，得到白色化合物0.444g（產率56.6%），質譜分析確定的分子離子品質為：502.08（計算值為：502.19）；理論元素含量（%）C₃₃ H₂₂ N₆ ：C，78.87；H，4.41；N，16.72，實測元素含量（%）：C，78.98；H，4.28；N，16.77。上述分析結果表明，獲得的產物為目標產品。Example 11

According to the synthesis of Example 2, the steps were the same, the compound N-(3-pyridyl)-1,2-phenylenediamine was used instead of the compound o-aminodiphenylamine to obtain 0.444g of white compound (yield 56.6%), which was confirmed by mass spectrometry The quality of the molecular ion 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.

依照實施例2的合成，步驟相同，用化合物N-（4-吡啶基）-1,2-苯二胺代替化合物鄰氨基二苯胺，得到白色化合物0.466g（產率59.4%），質譜分析確定的分子離子品質為：502.18（計算值為：502.19）；理論元素含量（%）C₃₃ H₂₂ N₆ ：C，78.87；H，4.41；N，16.72，實測元素含量（%）：C，78.95；H，4.61；N，16.83。上述分析結果表明，獲得的產物為目標產品。Example 12

According to the synthesis of Example 2, the steps are the same, the compound N-(4-pyridyl)-1,2-phenylenediamine is used instead of the compound o-aminodiphenylamine to obtain 0.466g of white compound (yield 59.4%), which is confirmed by mass spectrometry The quality of the molecular ion 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.

依照實施例6的合成，步驟相同，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（產率54.2%），質譜分析確定的分子離子品質為：502.13（計算值為：502.19）；理論元素含量（%）C₃₃ H₂₂ N₆ ：C，78.87；H，4.41；N，16.72，實測元素含量（%）：C，78.89；H，4.21；N，16.93。上述分析結果表明，獲得的產物為目標產品。Example 13

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 white compound (yield 54.2%). The molecular ion quality 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.

依照實施例6的合成，步驟相同，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（產率36.9%），質譜分析確定的分子離子品質為：502.22（計算值為：502.19）；理論元素含量（%）C₃₃ H₂₂ N₆ ：C，78.87；H，4.41；N，16.72，實測元素含量（%）：C，78.89；H，4.22；N，16.90。上述分析結果表明，獲得的產物為目標產品。Example 14

According to the synthesis of Example 6, the steps were the same, and the compound 4-aldehyde pyridine was substituted for the compound benzaldehyde to obtain 0.289 g of a white compound (yield 36.9%). The molecular ion quality 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.

依照實施例5的合成，步驟相同，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（產率42.5%），質譜分析確定的分子離子品質為：502.22（計算值為：502.19）；理論元素含量（%）C₃₃ H₂₂ N₆ ：C，78.87；H，4.41；N，16.72，實測元素含量（%）：C，78.86；H，4.40；N，16.81。上述分析結果表明，獲得的產物為目標產品。Example 15

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 white compound (yield 42.5%). The molecular ion quality 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.

依照實施例5的合成，步驟相同，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（產率33.0%），質譜分析確定的分子離子品質為：502.23（計算值為：502.19）；理論元素含量（%）C₃₃ H₂₂ N₆ ：C，78.87；H，4.41；N，16.72，實測元素含量（%）：C，78.87；H，4.51；N，16.87。上述分析結果表明，獲得的產物為目標產品。Example 16

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 white compound (yield 33.0%). The molecular ion quality 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.

依照實施例4的合成，步驟相同，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（產率37.7%），質譜分析確定的分子離子品質為：502.15（計算值為：502.19）；理論元素含量（%）C₃₃ H₂₂ N₆ ：C，78.87；H，4.41；N，16.72，實測元素含量（%）：C，78.75；H，4.21；N，16.73。上述分析結果表明，獲得的產物為目標產品。Example 17

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 the white compound (yield 37.7%). The molecular ion quality 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.

依照實施例4的合成，步驟相同，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（產率40.6%），質譜分析確定的分子離子品質為：502.18（計算值為：502.19）；理論元素含量（%）C₃₃ H₂₂ N₆ ：C，78.87；H，4.41；N，16.72，實測元素含量（%）：C，78.88；H，4.42；N，16.84。上述分析結果表明，獲得的產物為目標產品。Example 18

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 the white compound (yield 40.6%). The molecular ion quality determined by mass spectrometry 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.

依照實施例1的合成，步驟相同，用化合物N¹ -(2-氟苯基)-1,2-苯二胺代替化合物鄰氨基二苯胺，得到白色化合物0.523g（產率68.2%），質譜分析確定的分子離子品質為：519.28（計算值為：519.19）；理論元素含量（%）C₃₄ H₂₂ FN₅ ：C, 78.60; H, 4.27; F, 3.66; N, 13.48，實測元素含量（%）：C, 78.55; H, 4.24; F, 3.69; N, 13.41。上述分析結果表明，獲得的產物為目標產品。Example 19

According to the synthesis of Example 1, the steps were the same, and the compound N ¹ -(2-fluorophenyl)-1,2-phenylenediamine was used instead of the compound o-aminodiphenylamine to obtain 0.523 g of a white compound (yield 68.2%). The molecular ion quality 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.

依照實施例1的合成，步驟相同，用化合物N¹ -(3-氟苯基)-1,2-苯二胺代替化合物鄰氨基二苯胺，得到白色化合物0.512g（產率65.6%），質譜分析確定的分子離子品質為：519.33（計算值為：519.19）；理論元素含量（%）C₃₄ H₂₂ FN₅ ：C, 78.60; H, 4.27; F, 3.66; N, 13.48，實測元素含量（%）：C, 78.57; H, 4.26; F, 3.71; N, 13.43。上述分析結果表明，獲得的產物為目標產品。Example 20

According to the synthesis of Example 1, the steps are the same, the compound N ¹ -(3-fluorophenyl)-1,2-phenylenediamine is used instead of the compound o-aminodiphenylamine to obtain 0.512g of white compound (65.6% yield), mass The molecular ion quality 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.

依照實施例1的合成，步驟相同，用化合物N¹ -(4-氟苯基)-1,2-苯二胺代替化合物鄰氨基二苯胺，得到白色化合物0.502g（產率64.4%），質譜分析確定的分子離子品質為：519.09（計算值為：519.19）；理論元素含量（%）C₃₄ H₂₂ FN₅ ：C, 78.60; H, 4.27; F, 3.66; N, 13.48，實測元素含量（%）：C, 78.55; H, 4.24; F, 3.69; N, 13.41。上述分析結果表明，獲得的產物為目標產品。Example 21

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 0.502g of a white compound (yield 64.4%). The molecular ion quality 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.

依照實施例3的合成，步驟相同，用化合物N¹ -(2-氟苯基)-1,2-苯二胺代替化合物鄰氨基二苯胺，得到白色化合物0.488g（產率62.6%），質譜分析確定的分子離子品質為：519.29（計算值為：519.19）；理論元素含量（%）C₃₄ H₂₂ FN₅ ：C, 78.60; H, 4.27; F, 3.66; N, 13.48，實測元素含量（%）：C, 78.57; H, 4.23; F, 3.68; N, 13.40。上述分析結果表明，獲得的產物為目標產品。Example 22

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 compound o-aminodiphenylamine to obtain 0.488g of white compound (yield 62.6%). The molecular ion quality 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.

依照實施例3的合成，步驟相同，用化合物N¹ -(3-氟苯基)-1,2-苯二胺代替化合物鄰氨基二苯胺，得到白色化合物0.532g（產率68.2%），質譜分析確定的分子離子品質為：519.11（計算值為：519.19）；理論元素含量（%）C₃₄ H₂₂ FN₅ ：C, 78.60; H, 4.27; F, 3.66; N, 13.48，實測元素含量（%）：C, 78.66; H, 4.34; F, 3.79; N, 13.51。上述分析結果表明，獲得的產物為目標產品。Example 23

According to the synthesis of Example 3, the steps are the same, and the compound N ¹ -(3-fluorophenyl)-1,2-phenylenediamine is used instead of the o-aminodiphenylamine compound to obtain 0.532 g of a white compound (yield 68.2%), mass spectrum The molecular ion quality 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.

依照實施例3的合成，步驟相同，用化合物N¹ -(4-氟苯基)-1,2-苯二胺代替化合物鄰氨基二苯胺，得到白色化合物0.449g（產率57.6%），質譜分析確定的分子離子品質為：519.05（計算值為：519.19）；理論元素含量（%）C₃₄ H₂₂ FN₅ ：C, 78.60; H, 4.27; F, 3.66; N, 13.48，實測元素含量（%）：C, 78.75; H, 4.34; F, 3.60; N, 13.43。上述分析結果表明，獲得的產物為目標產品。Example 24

According to the synthesis of Example 3, the steps are the same, and the compound N ¹ -(4-fluorophenyl)-1,2-phenylenediamine is used instead of the o-aminodiphenylamine compound to obtain 0.449 g of a white compound (yield 57.6%), mass spectrum The molecular ion quality 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.

依照實施例2的合成，步驟相同，用化合物N¹ -(2-氟苯基)-1,2-苯二胺代替化合物鄰氨基二苯胺，得到白色化合物0.439g（產率56.7%），質譜分析確定的分子離子品質為：519.11（計算值為：519.19）；理論元素含量（%）C₃₄ H₂₂ FN₅ ：C, 78.60; H, 4.27; F, 3.66; N, 13.48，實測元素含量（%）：C, 78.55; H, 4.24; F, 3.69; N, 13.41。上述分析結果表明，獲得的產物為目標產品。Example 25

According to the synthesis of Example 2, the steps were the same, and the compound N ¹ -(2-fluorophenyl)-1,2-phenylenediamine was used instead of the compound o-aminodiphenylamine to obtain 0.439 g of the white compound (yield 56.7%), mass spectrum The molecular ion quality 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.

依照實施例2的合成，步驟相同，用化合物N¹ -(3-氟苯基)-1,2-苯二胺代替化合物鄰氨基二苯胺，得到白色化合物0.429g（產率55.0%），質譜分析確定的分子離子品質為：519.13（計算值為：519.19）；理論元素含量（%）C₃₄ H₂₂ FN₅ ：C, 78.60; H, 4.27; F, 3.66; N, 13.48，實測元素含量（%）：C, 78.66; H, 4.34; F, 3.64; N, 13.45。上述分析結果表明，獲得的產物為目標產品。Example 26

According to the synthesis of Example 2, the steps are the same, and 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 quality determined by analysis is: 519.13 (calculated value: 519.19); the 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, 4.34; F, 3.64; N, 13.45. The above analysis results show that the obtained product is the target product.

依照實施例3的合成，步驟相同，用化合物N¹ -(4-氟苯基)-1,2-苯二胺代替化合物鄰氨基二苯胺，得到白色化合物0.563g（產率72.2%），質譜分析確定的分子離子品質為：519.22（計算值為：519.19）；理論元素含量（%）C₃₄ H₂₂ FN₅ ：C, 78.60; H, 4.27; F, 3.66; N, 13.48，實測元素含量（%）：C, 78.57; H, 4.22; F, 3.67; N, 13.51。上述分析結果表明，獲得的產物為目標產品。Example 27

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 quality 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.

依照實施例1的合成，步驟相同，用化合物N¹ -(3,5-二氟苯基)-1,2-苯二胺代替化合物鄰氨基二苯胺，得到白色化合物0.537g（產率66.7%），質譜分析確定的分子離子品質為：537.28（計算值為：537.18）；理論元素含量（%）C₃₄ H₂₁ F₂ N₅ ：C, 75.97; H, 3.94; F, 7.07; N, 13.03，實測元素含量（%）：C, 76.07; H, 3.99; F, 7.17; N, 13.08。上述分析結果表明，獲得的產物為目標產品。Example 28

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 quality 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.

依照實施例3的合成，步驟相同，用化合物N¹ -(3,5-二氟苯基)-1,2-苯二胺代替化合物鄰氨基二苯胺，得到白色化合物0.454g（產率56.2%），質譜分析確定的分子離子品質為：537.20（計算值為：537.18）；理論元素含量（%）C₃₄ H₂₁ F₂ N₅ ：C, 75.97; H, 3.94; F, 7.07; N, 13.03，實測元素含量（%）：C, 76.00; H, 4.10; F, 7.07; N, 13.18。上述分析結果表明，獲得的產物為目標產品。Example 29

According to the synthesis of Example 3, 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 0.454 g of a white compound (yield 56.2%) ), the molecular ion quality determined by mass spectrometry 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.

依照實施例2的合成，步驟相同，用化合物N¹ -(3,5-二氟苯基)-1,2-苯二胺代替化合物鄰氨基二苯胺，得到白色化合物0.390g（產率48.3%），質譜分析確定的分子離子品質為：537.09（計算值為：537.18）；理論元素含量（%）C₃₄ H₂₁ F₂ N₅ ：C, 75.97; H, 3.94; F, 7.07; N, 13.03，實測元素含量（%）：C, 75.99; H, 3.92; F, 7.09; N, 13.13。上述分析結果表明，獲得的產物為目標產品。Example 30

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 quality 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.

依照實施例6的合成，步驟相同，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（產率50.2%），質譜分析確定的分子離子品質為：519.24（計算值為：519.19）；理論元素含量（%）C₃₄ H₂₂ FN₅ ：C, 78.60; H, 4.27; F, 3.66; N, 13.48，實測元素含量（%）：C, 78.55; H, 4.29; F, 3.69; N, 13.33。上述分析結果表明，獲得的產物為目標產品。Example 31

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 0.392g of white compound (yield 50.2%). The molecular ion quality 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.

依照實施例5的合成，步驟相同，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（產率45.3%），質譜分析確定的分子離子品質為：519.15（計算值為：519.19）；理論元素含量（%）C₃₄ H₂₂ FN₅ ：C, 78.60; H, 4.27; F, 3.66; N, 13.48，實測元素含量（%）：C, 78.66; H, 4.22; F, 3.69; N, 13.59。上述分析結果表明，獲得的產物為目標產品。Example 32

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 quality 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.

依照實施例4的合成，步驟相同，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（產率45.8%），質譜分析確定的分子離子品質為：519.22（計算值為：519.19）；理論元素含量（%）C₃₄ H₂₂ FN₅ ：C, 78.60; H, 4.27; F, 3.66; N, 13.48，實測元素含量（%）：C, 78.59; H, 4.32; F, 3.77; N, 13.61。上述分析結果表明，獲得的產物為目標產品。Example 33

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 molecular ion quality 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.

依照實施例6的合成，步驟相同，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（產率51.9%），質譜分析確定的分子離子品質為：519.15（計算值為：519.19）；理論元素含量（%）C₃₄ H₂₂ FN₅ ：C, 78.60; H, 4.27; F, 3.66; N, 13.48，實測元素含量（%）：C, 78.62; H, 4.28; F, 3.69; N, 13.59。上述分析結果表明，獲得的產物為目標產品。Example 34

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 quality 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, 78.62; H, 4.28; F, 3.69; N, 13.59. The above analysis results show that the obtained product is the target product.

依照實施例5的合成，步驟相同，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（產率53.3%），質譜分析確定的分子離子品質為：519.28（計算值為：519.19）；理論元素含量（%）C₃₄ H₂₂ FN₅ ：C, 78.60; H, 4.27; F, 3.66; N, 13.48，實測元素含量（%）：C, 78.67; H, 4.42; F, 3.47; N, 13.41。上述分析結果表明，獲得的產物為目標產品。Example 35

According to the synthesis of Example 5, the steps were the same, and the compound 3-fluorobenzaldehyde was used instead of the compound benzaldehyde to obtain 0.416 g of a white compound (yield 53.3%). The molecular ion quality 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, the 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.

依照實施例4的合成，步驟相同，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（產率66.7%），質譜分析確定的分子離子品質為：519.22（計算值為：519.19）；理論元素含量（%）C₃₄ H₂₂ FN₅ ：C, 78.60; H, 4.27; F, 3.66; N, 13.48，實測元素含量（%）：C, 78.57; H, 4.22; F, 3.67; N, 13.51。上述分析結果表明，獲得的產物為目標產品。Example 36

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 quality 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.

依照實施例6的合成，步驟相同，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（產率55.8%），質譜分析確定的分子離子品質為：519.25（計算值為：519.19）；理論元素含量（%）C₃₄ H₂₂ FN₅ ：C, 78.60; H, 4.27; F, 3.66; N, 13.48，實測元素含量（%）：C, 78.57; H, 4.22; F, 3.67; N, 13.51。上述分析結果表明，獲得的產物為目標產品。Example 37

According to the synthesis of Example 6, the steps are the same, and the compound 4-fluorobenzaldehyde is substituted for the compound benzaldehyde to obtain 0.435g of white compound (yield 55.8%). The molecular ion quality determined by mass spectrometry is 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.

依照實施例5的合成，步驟相同，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（產率60.5%），質譜分析確定的分子離子品質為：519.10（計算值為：519.19）；理論元素含量（%）C₃₄ H₂₂ FN₅ ：C, 78.60; H, 4.27; F, 3.66; N, 13.48，實測元素含量（%）：C, 78.58; H, 4.22; F, 3.87; N, 13.51。上述分析結果表明，獲得的產物為目標產品。Example 38

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 (60.5% yield). The molecular ion quality 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, the 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.

依照實施例4的合成，步驟相同，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（產率53.4%），質譜分析確定的分子離子品質為：519.14（計算值為：519.19）；理論元素含量（%）C₃₄ H₂₂ FN₅ ：C, 78.60; H, 4.27; F, 3.66; N, 13.48，實測元素含量（%）：C, 78.77; H, 4.12; F, 3.87; N, 13.51。上述分析結果表明，獲得的產物為目標產品。Example 39

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 quality 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.

依照實施例6的合成，步驟相同，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（產率44.9%），質譜分析確定的分子離子品質為：537.33（計算值為：537.18）；理論元素含量（%）C₃₄ H₂₁ F₂ N₅ ：C, 75.97; H, 3.94; F, 7.07; N, 13.03，實測元素含量（%）：C, 76.07; H, 3.99; F, 7.17; N, 13.08。上述分析結果表明，獲得的產物為目標產品。Example 40

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 0.361g of white compound (yield 44.9%). The molecular ion quality 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.

依照實施例5的合成，步驟相同，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（產率47.5%），質譜分析確定的分子離子品質為：537.19（計算值為：537.18）；理論元素含量（%）C₃₄ H₂₁ F₂ N₅ ：C, 75.97; H, 3.94; F, 7.07; N, 13.03，實測元素含量（%）：C, 75.87; H, 4.12; F, 7.07; N, 13.18。上述分析結果表明，獲得的產物為目標產品。Example 41

According to the synthesis of Example 5, the steps are the same, and the compound 3,5-difluorobenzaldehyde is used instead of the compound benzaldehyde to obtain 0.382g of white compound (yield 47.5%). The molecular ion quality determined by mass spectrometry is 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.

依照實施例4的合成，步驟相同，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（產率52.8%），質譜分析確定的分子離子品質為：537.09（計算值為：537.18）；理論元素含量（%）C₃₄ H₂₁ F₂ N₅ ：C, 75.97; H, 3.94; F, 7.07; N, 13.03，實測元素含量（%）：C, 76.11; H, 3.89; F, 7.25; N, 13.18。上述分析結果表明，獲得的產物為目標產品。Example 42

According to the synthesis of Example 4, the steps were the same, and the compound 3,5-difluorobenzaldehyde was used instead of the compound benzaldehyde to obtain 0.425 g of white compound (yield 52.8%). The molecular ion quality determined by mass spectrometry was 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.

依照實施例7的合成，步驟相同，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（產率51.2%），質譜分析確定的分子離子品質為：538.25（計算值為：538.17）；理論元素含量（%）C₃₃ H₂₀ F₂ N₆ ：C, 73.60; H, 3.74; F, 7.06; N, 15.60，實測元素含量（%）：C, 73.58; H, 3.81; F, 7.16; N, 15.77。上述分析結果表明，獲得的產物為目標產品。Example 43

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 quality 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.

依照實施例8的合成，步驟相同，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（產率60.8%），質譜分析確定的分子離子品質為：538.32（計算值為：538.17）；理論元素含量（%）C₃₃ H₂₀ F₂ N₆ ：C, 73.60; H, 3.74; F, 7.06; N, 15.60，實測元素含量（%）：C, 73.49; H, 3.83; F, 7.11; N, 15.53。上述分析結果表明，獲得的產物為目標產品。Example 44

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 quality 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.

依照實施例9的合成，步驟相同，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（產率57.3%），質譜分析確定的分子離子品質為：538.33（計算值為：538.17）；理論元素含量（%）C₃₃ H₂₀ F₂ N₆ ：C, 73.60; H, 3.74; F, 7.06; N, 15.60，實測元素含量（%）：C, 73.59; H, 3.77; F, 7.26; N, 15.58。上述分析結果表明，獲得的產物為目標產品。Example 45

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 quality determined by mass spectrometry 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.

依照實施例10的合成，步驟相同，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（產率47.3%），質譜分析確定的分子離子品質為：538.09（計算值為：538.17）；理論元素含量（%）C₃₃ H₂₀ F₂ N₆ ：C, 73.60; H, 3.74; F, 7.06; N, 15.60，實測元素含量（%）：C, 73.55; H, 3.80; F, 7.14; N, 15.77。上述分析結果表明，獲得的產物為目標產品。Example 46

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 quality 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.

依照實施例11的合成，步驟相同，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（產率55.3%），質譜分析確定的分子離子品質為：538.30（計算值為：538.17）；理論元素含量（%）C₃₃ H₂₀ F₂ N₆ ：C, 73.60; H, 3.74; F, 7.06; N, 15.60，實測元素含量（%）：C, 73.47; H, 3.59; F, 7.21; N, 15.46。上述分析結果表明，獲得的產物為目標產品。Example 47

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, 0.597g of white compound was obtained (yield 55.3%), the molecular ion quality determined by mass spectrometry was 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.

依照實施例12的合成，步驟相同，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（產率47.9%），質譜分析確定的分子離子品質為：538.22（計算值為：538.17）；理論元素含量（%）C₃₃ H₂₀ F₂ N₆ ：C, 73.60; H, 3.74; F, 7.06; N, 15.60，實測元素含量（%）：C, 73.60; H, 3.77; F, 7.16; N, 15.49。上述分析結果表明，獲得的產物為目標產品。Example 48

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 molecular ion quality determined by mass spectrometry analysis 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.

2-氯-4,6-二苯基-1,3,5-三嗪4.02g（15mmol），3,5-二甲醯基苯硼酸3.20g（18mmol），碳酸鉀3.73g（27mmol）加入到250mL雙口瓶中，加入THF 100mL，H₂ O 20mL，氮氣條件下加入催化劑四（三苯基膦）鈀，回流12h。用二氯甲烷/水洗滌反應液，有機相旋去溶劑後，柱層析提純，得白色固體中間體（4.50g，產率82.2%）。Example 49

2-Chloro-4,6-diphenyl-1,3,5-triazine 4.02g (15mmol), 3,5-dimethylphenylboronic acid 3.20g (18mmol), potassium carbonate 3.73g (27mmol) added To a 250mL double-mouth flask, add 100mL THF, 20mL H ₂ O, add catalyst tetrakis (triphenylphosphine) palladium under nitrogen conditions, 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 (4.50 g, yield 82.2%).

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 for 5 hours at room temperature. Then add 0.611g (3.32mmol) of o-aminodiphenylamine, add 20mL ethanol, and reflux for 24h under nitrogen protection. 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 quality 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.

10mL水溶解NaHSO₃ 4.70g（45.0mmol），加入苯甲醛0.398g（3.75mmol），常溫攪拌5h，然後加入N1,N¹ ’-（5-溴-1,3-苯基）雙（1,2-苯二胺）0.552g（1.50mmol），加入20mL乙醇，氮氣保護下回流24h。冷卻到室溫後過濾，得到白色固體粗產品0.700g（產率86.4%）。Example 50

Dissolve 4.70g (45.0mmol) of NaHSO _{3 in} 10mL of water, add 0.398g (3.75mmol) of benzaldehyde, stir at room temperature for 5h, then add N1,N ¹ '-(5-bromo-1,3-phenyl)bis(1, 2-Phenylenediamine) 0.552g (1.50mmol), add 20mL ethanol, and reflux for 24h 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%).

The above crude product 1.08g (2.00mmol), 1.02g (4.00mmol) of pinacol diborate, 1.96g (20.0mmol) of dried potassium acetate, and 120mL of dried 1,4-dioxane in 250mL of dioxane In the mouth flask, add 150mg (0.20mmol) of palladium dichloride catalyst [1,1'-bis(diphenylphosphino)ferrocene] dichloride under nitrogen protection, and reflux for 24h. 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 972 mg of a white solid intermediate. (The yield is 82.6%).

Add 882 mg (1.50 mmol) of the above white intermediate, 1.00 g (1.65 mmol) of 2-chloro-4,6-diphenyl-1,3,5-triazine, and 440 mg (4.5 mmol) of potassium carbonate into 100 mL of 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, 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 quality 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.

依照實施例49的合成，步驟相同，用化合物N-（3-吡啶基）-1,2-苯二胺代替化合物鄰氨基二苯胺，得到白色化合物0.716g（產率68.9%），質譜分析確定的分子離子品質為：695.33（計算值為：695.25）；理論元素含量（%）C₄₅ H₂₉ N₉ ：C, 77.68; H, 4.20; N, 18.12，實測元素含量（%）：C, 77.77; H, 4.15; N, 18.35。上述分析結果表明，獲得的產物為目標產品。Example 51

According to the synthesis of Example 49, the steps are the same, the compound N-(3-pyridyl)-1,2-phenylenediamine is used instead of the compound o-aminodiphenylamine to obtain 0.716g of white compound (yield 68.9%), which is confirmed by mass spectrometry The molecular ion quality 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.

依照實施例49的合成，步驟相同，用化合物N-（4-吡啶基）-1,2-苯二胺代替化合物鄰氨基二苯胺，得到白色化合物0.557g（產率53.6%），質譜分析確定的分子離子品質為：695.33（計算值為：695.25）；理論元素含量（%）C₄₅ H₂₉ N₉ ：C, 77.68; H, 4.20; N, 18.12，實測元素含量（%）：C, 77.73; H, 4.17; N, 18.19。上述分析結果表明，獲得的產物為目標產品。Example 52

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 quality 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.

依照實施例50的合成，步驟相同，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（產率45.6%），質譜分析確定的分子離子品質為：695.46（計算值為：695.25）；理論元素含量（%）C₄₅ H₂₉ N₉ ：C, 77.68; H, 4.20; N, 18.12，實測元素含量（%）：C, 77.70; H, 4.14; N, 18.28。上述分析結果表明，獲得的產物為目標產品。Example 53

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 the white compound (yield 45.6%). The molecular ion quality 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.

依照實施例50的合成，步驟相同，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（產率52.6%），質譜分析確定的分子離子品質為：695.24（計算值為：695.25）；理論元素含量（%）C₄₅ H₂₉ N₉ ：C, 77.68; H, 4.20; N, 18.12，實測元素含量（%）：C, 77.73; H, 4.11; N, 18.20。上述分析結果表明，獲得的產物為目標產品。Example 54

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 of white compound (yield 52.6%). The molecular ion quality 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.

依照實施例49的合成，步驟相同，用化合物N¹ ,N¹ ’-{5-溴-1,3-二（2-氟苯基）}雙（1,2-苯二胺）代替化合物N¹ ,N¹ ’-（5-溴-1,3-二苯基）雙（1,2-苯二胺），得到白色化合物0.504g（產率46.2%），質譜分析確定的分子離子品質為：729.33（計算值為：729.25）；理論元素含量（%）C₄₇ H₂₉ F₂ N₇ ：C, 77.35; H, 4.01; F, 5.21; N, 13.44，實測元素含量（%）：C, 77.42; H, 4.07; F, 5.31; N, 13.52。上述分析結果表明，獲得的產物為目標產品。Example 55

According to the synthesis of Example 49, the steps are the same, and compound N ¹ ,N ¹ '-{5-bromo-1,3-bis(2-fluorophenyl)}bis(1,2-phenylenediamine) is used instead of compound N ¹ ,N ¹ '-(5-bromo-1,3-diphenyl)bis(1,2-phenylenediamine), 0.504g of white compound (yield 46.2%) was obtained, and the molecular ion quality determined by mass spectrometry 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, 4.07; F, 5.31; N, 13.52. The above analysis results show that the obtained product is the target product.

依照實施例49的合成，步驟相同，用化合物N¹ ,N¹ ’-{5-溴-1,3-二（2-氟苯基）}雙（1,2-苯二胺）代替化合物N¹ ,N¹ ’-（5-溴-1,3-二苯基）雙（1,2-苯二胺），得到白色化合物0.560g（產率51.4%），質譜分析確定的分子離子品質為：729.11（計算值為：729.25）；理論元素含量（%）C₄₇ H₂₉ F₂ N₇ ：C, 77.35; H, 4.01; F, 5.21; N, 13.44，實測元素含量（%）：C, 77.33; H, 4.11; F, 5.23; N, 13.56。上述分析結果表明，獲得的產物為目標產品。Example 56

According to the synthesis of Example 49, the steps are the same, and compound N ¹ ,N ¹ '-{5-bromo-1,3-bis(2-fluorophenyl)}bis(1,2-phenylenediamine) is used 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 quality 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.

依照實施例49的合成，步驟相同，用化合物N¹ ,N¹ ’-{5-溴-1,3-二（2-氟苯基）}雙（1,2-苯二胺）代替化合物N¹ ,N¹ ’-（5-溴-1,3-二苯基）雙（1,2-苯二胺），得到白色化合物0.597g（產率54.8%），質譜分析確定的分子離子品質為：729.23（計算值為：729.25）；理論元素含量（%）C₄₇ H₂₉ F₂ N₇ ：C, 77.35; H, 4.01; F, 5.21; N, 13.44，實測元素含量（%）：C, 77.51; H, 4.12; F, 5.16; N, 13.50。上述分析結果表明，獲得的產物為目標產品。Example 57

According to the synthesis of Example 49, the steps are the same, and compound N ¹ ,N ¹ '-{5-bromo-1,3-bis(2-fluorophenyl)}bis(1,2-phenylenediamine) is used instead of compound N ¹ ,N ¹ '-(5-bromo-1,3-diphenyl)bis(1,2-phenylenediamine), 0.597g of white compound (yield 54.8%) is obtained, and the molecular ion quality determined by mass spectrometry is : 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.

依照實施例50的合成，步驟相同，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（產率51.4%），質譜分析確定的分子離子品質為：729.31（計算值為：729.25）；理論元素含量（%）C₄₇ H₂₉ F₂ N₇ ：C, 77.35; H, 4.01; F, 5.21; N, 13.44，實測元素含量（%）：C, 77.46; H, 4.26; F, 5.22; N, 13.47。上述分析結果表明，獲得的產物為目標產品。Example 58

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 quality 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.

依照實施例50的合成，步驟相同，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（產率47.4%），質譜分析確定的分子離子品質為：729.51（計算值為：729.25）；理論元素含量（%）C₄₇ H₂₉ F₂ N₇ ：C, 77.35; H, 4.01; F, 5.21; N, 13.44，實測元素含量（%）：C, 77.55; H, 4.07; F, 5.40; N, 13.24。上述分析結果表明，獲得的產物為目標產品。Example 59

According to the synthesis of Example 50, the steps were the same, and the compound 3-fluorobenzaldehyde was used instead of the compound benzaldehyde to obtain 0.517 g of white compound (yield 47.4%). The molecular ion quality 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.

依照實施例50的合成，步驟相同，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（產率52.8%），質譜分析確定的分子離子品質為：729.25（計算值為：729.25）；理論元素含量（%）C₄₇ H₂₉ F₂ N₇ ：C, 77.35; H, 4.01; F, 5.21; N, 13.44，實測元素含量（%）：C, 77.35; H, 4.01; F, 5.21; N, 13.44。上述分析結果表明，獲得的產物為目標產品。Example 60

According to the synthesis of Example 50, the steps were the same, and the compound 4-fluorobenzaldehyde was used instead of the compound benzaldehyde to obtain 0.577 g of a white compound (yield 52.8%). The molecular ion quality 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, 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.

依照實施例49的合成，步驟相同，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（產率46.6%），質譜分析確定的分子離子品質為：729.50（計算值為：729.25）；理論元素含量（%）C₄₇ H₂₉ F₂ N₇ ：C, 77.35; H, 4.01; F, 5.21; N, 13.44，實測元素含量（%）：C, 77.42; H, 3.99; F, 5.21; N, 13.40。上述分析結果表明，獲得的產物為目標產品。Example 61

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, 0.511g of white compound was obtained (yield 46.6%). The molecular ion quality determined by mass spectrometry was 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.

依照實施例50的合成，步驟相同，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（產率52.3%），質譜分析確定的分子離子品質為：729.33（計算值為：729.25）；理論元素含量（%）C₄₇ H₂₉ F₂ N₇ ：C, 77.35; H, 4.01; F, 5.21; N, 13.44，實測元素含量（%）：C, 77.42; H, 4.12; F, 5.18; N, 13.33。上述分析結果表明，獲得的產物為目標產品。Example 62

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 quality 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.

依照實施例51的合成，步驟相同，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（產率45.8%），質譜分析確定的分子離子品質為：731.17（計算值為：731.24）；理論元素含量（%）C₄₅ H₂₇ F₂ N₉ ：C, 73.86; H, 3.72; F, 5.19; N, 17.23，實測元素含量（%）：C, 73.93; H, 3.88; F, 5.21; N, 17.25。上述分析結果表明，獲得的產物為目標產品。Example 63

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 quality 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.

依照實施例52的合成，步驟相同，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（產率46.1%），質譜分析確定的分子離子品質為：731.11（計算值為：731.24）；理論元素含量（%）C₄₅ H₂₇ F₂ N₉ ：C, 73.86; H, 3.72; F, 5.19; N, 17.23，實測元素含量（%）：C, 73.90; H, 3.88; F, 5.22; N, 17.31。上述分析結果表明，獲得的產物為目標產品。Example 64

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 quality 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.

依照實施例53的合成，步驟相同，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（產率66.7%），質譜分析確定的分子離子品質為：731.24（計算值為：731.24）；理論元素含量（%）C₄₅ H₂₇ F₂ N₉ ：C, 73.86; H, 3.72; F, 5.19; N, 17.23，實測元素含量（%）：C, 73.86; H, 3.72; F, 5.19; N, 17.23。上述分析結果表明，獲得的產物為目標產品。Example 65

According to the synthesis of Example 53, the steps are the same, using the compound 2-chloro-4,6-bis(4-fluorophenyl)-1,3,5-triazine 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 quality 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.

依照實施例54的合成，步驟相同，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（產率52.8%），質譜分析確定的分子離子品質為：731.33（計算值為：731.24）；理論元素含量（%）C₄₅ H₂₇ F₂ N₉ ：C, 73.86; H, 3.72; F, 5.19; N, 17.23，實測元素含量（%）：C, 73.96 H, 3.88; F, 5.21; N, 17.25。上述分析結果表明，獲得的產物為目標產品。Example 66

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, 0.771g white compound (yield 52.8%) was obtained. The molecular ion quality determined by mass spectrometry analysis was 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, 73.96 H, 3.88; F, 5.21; N, 17.25. The above analysis results show that the obtained product is the target product.

依照實施例55的合成，步驟相同，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（產率48.6%），質譜分析確定的分子離子品質為：765.12（計算值為：765.23）；理論元素含量（%）C₄₇ H₂₇ F₄ N₇ ：C, 73.72; H, 3.55; F, 9.92; N, 12.80，實測元素含量（%）：C, 73.68; H, 3.46; F, 9.80; N, 12.79。上述分析結果表明，獲得的產物為目標產品。Example 67

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 of white compound was obtained (yield 48.6%). The molecular ion quality 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.

依照實施例56的合成，步驟相同，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（產率41.5%），質譜分析確定的分子離子品質為：765.23（計算值為：765.23）；理論元素含量（%）C₄₇ H₂₇ F₄ N₇ ：C, 73.72; H, 3.55; F, 9.92; N, 12.80，實測元素含量（%）：C, 73.68; H, 3.66; F, 9.81; N, 12.77。上述分析結果表明，獲得的產物為目標產品。Example 68

According to the synthesis of Example 56, the same steps were used, and the compound 2-chloro-4,6-bis(4-fluorophenyl)-1,3,5-triazine was 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 quality determined by mass spectrometry 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.

依照實施例57的合成，步驟相同，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（產率51.4%），質譜分析確定的分子離子品質為：765.20（計算值為：765.23）；理論元素含量（%）C₄₇ H₂₇ F₄ N₇ ：C, 73.72; H, 3.55; F, 9.92; N, 12.80，實測元素含量（%）：C, 73.68; H, 3.47; F, 9.88; N, 12.76。上述分析結果表明，獲得的產物為目標產品。Example 69

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 quality determined by mass spectrometry 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.

依照實施例58的合成，步驟相同，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（產率50.3%），質譜分析確定的分子離子品質為：765.12（計算值為：765.23）；理論元素含量（%）C₄₇ H₂₇ F₄ N₇ ：C, 73.72; H, 3.55; F, 9.92; N, 12.80，實測元素含量（%）：C, 73.86; H, 3.39; F, 9.79; N, 12.77。上述分析結果表明，獲得的產物為目標產品。Example 70

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 quality 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, 73.86; H, 3.39; F, 9.79; N, 12.77. The above analysis results show that the obtained product is the target product.

依照實施例59的合成，步驟相同，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（產率49.8%），質譜分析確定的分子離子品質為：765.34（計算值為：765.23）；理論元素含量（%）C₄₇ H₂₇ F₄ N₇ ：C, 73.72; H, 3.55; F, 9.92; N, 12.80，實測元素含量（%）：C, 73.62; H, 3.57; F, 9.88; N, 12.93。上述分析結果表明，獲得的產物為目標產品。Example 71

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 white compound was obtained (yield 49.8%), the molecular ion quality 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.

依照實施例60的合成，步驟相同，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（產率52.8%），質譜分析確定的分子離子品質為：765.44（計算值為：765.23）；理論元素含量（%）C₄₇ H₂₇ F₄ N₇ ：C, 73.72; H, 3.55; F, 9.92; N, 12.80，實測元素含量（%）：C, 73.68; H, 3.63; F, 9.94; N, 12.77。上述分析結果表明，獲得的產物為目標產品。Example 72

According to the synthesis of Example 60, the steps are the same, 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 quality 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.

依照實施例29的合成，步驟相同，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（產率52.9%），質譜分析確定的分子離子品質為：573.22（計算值為：573.16）；理論元素含量（%）C₃₄ H₁₉ F₄ N₅ :C, 71.20; H, 3.34; F, 13.25; N, 12.21，實測元素含量（%）：C, 71.24; H, 3.33; F, 13.36 N, 12.31。上述分析結果表明，獲得的產物為目標產品。Example 73

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 quality determined by mass spectrometry 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, 13.36 N, 12.31. The above analysis results show that the obtained product is the target product.

依照實施例1的合成，步驟相同，用化合物N¹ -(3-三氟甲基苯基)-1,2-苯二胺代替化合物鄰氨基二苯胺，得到白色化合物0.498g（產率58.3%），質譜分析確定的分子離子品質為：569.32（計算值為：569.18）；理論元素含量（%）C₃₅ H₂₂ F₃ N₅ ：C, 73.80; H, 3.89; F, 10.01; N, 12.30；實測元素含量（%）：C, 73.77; H, 3.92; F, 10.11; N, 12.35。上述分析結果表明，獲得的產物為目標產品。Example 74

According to the synthesis of Example 1, the steps are the same, the compound N ¹ -(3-trifluoromethylphenyl)-1,2-phenylenediamine is used instead of the compound o-aminodiphenylamine to obtain 0.498g of a white compound (yield 58.3%) ), the molecular ion quality determined by mass spectrometry 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.

依照實施例3的合成，步驟相同，用化合物N¹ -(3-三氟甲基苯基)-1,2-苯二胺代替化合物鄰氨基二苯胺，得到白色化合物0.532g（產率53.2%），質譜分析確定的分子離子品質為：569.12（計算值為：569.18）；理論元素含量（%）C₃₅ H₂₂ F₃ N₅ ：C, 73.80; H, 3.89; F, 10.01; N, 12.30；實測元素含量（%）：C, 73.87; H, 3.91; F, 10.10; N, 12.31。上述分析結果表明，獲得的產物為目標產品。Example 75

According to the synthesis of Example 3, the steps are the same, the compound N ¹ -(3-trifluoromethylphenyl)-1,2-phenylenediamine is used instead of the compound o-aminodiphenylamine to obtain 0.532g of a white compound (yield 53.2%) ), the molecular ion quality determined by mass spectrometry 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.

依照實施例2的合成，步驟相同，用化合物N¹ -(3-三氟甲基苯基)-1,2-苯二胺代替化合物鄰氨基二苯胺，得到白色化合物0.527g（產率61.7%），質譜分析確定的分子離子品質為：569.33（計算值為：569.18）；理論元素含量（%）C₃₅ H₂₂ F₃ N₅ ：C, 73.80; H, 3.89; F, 10.01; N, 12.30；實測元素含量（%）：C, 73.91; H, 3.88; F, 10.06; N, 12.27。上述分析結果表明，獲得的產物為目標產品。Example 76

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 (61.7% yield ), the molecular ion quality determined by mass spectrometry 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.

依照實施例1的合成，步驟相同，用化合物N¹ -(3,5-二（三氟甲基）苯基)-1,2-苯二胺代替化合物鄰氨基二苯胺，得到白色化合物0.524g（產率54.8%），質譜分析確定的分子離子品質為：637.22（計算值為：637.17）；理論元素含量（%）C₃₆ H₂₁ F₆ N₅ ：C, 67.82; H, 3.32; F, 17.88; N, 10.98，實測元素含量（%）：C, 67.77; H, 3.35; F, 17.90; N, 10.87。上述分析結果表明，獲得的產物為目標產品。Example 77

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 quality 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.

依照實施例3的合成，步驟相同，用化合物N¹ -(3,5-二（三氟甲基）苯基)-1,2-苯二胺代替化合物鄰氨基二苯胺，得到白色化合物0.524g（產率54.8%），質譜分析確定的分子離子品質為：637.20（計算值為：637.17）；理論元素含量（%）C₃₆ H₂₁ F₆ N₅ ：C, 67.82; H, 3.32; F, 17.88; N, 10.98，實測元素含量（%）：C, 67.87; H, 3.45; F, 17.82; N, 10. 97。上述分析結果表明，獲得的產物為目標產品。Example 78

According to the synthesis of Example 3, the steps are the same, and the compound N ¹ -(3,5-bis(trifluoromethyl)phenyl)-1,2-phenylenediamine is used instead of the compound o-aminodiphenylamine to obtain 0.524g of a white compound (Yield 54.8%), the molecular ion quality 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.

依照實施例2的合成，步驟相同，用化合物N¹ -(3,5-二（三氟甲基）苯基)-1,2-苯二胺代替化合物鄰氨基二苯胺，得到白色化合物0.585g（產率61.2%），質譜分析確定的分子離子品質為：637.15（計算值為：637.17）；理論元素含量（%）C₃₆ H₂₁ F₆ N₅ ：C, 67.82; H, 3.32; F, 17.88; N, 10.98，實測元素含量（%）：C, 67.87; H, 3.36; F, 17.89; N, 10.94。上述分析結果表明，獲得的產物為目標產品。Example 79

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 quality 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.

依照實施例4的合成，步驟相同，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（產率58.6%），質譜分析確定的分子離子品質為：569.19（計算值為：569.18）；理論元素含量（%）C₃₅ H₂₂ F₃ N₅ ：C, 73.80; H, 3.89; F, 10.01; N, 12.30；實測元素含量（%）：C, 73.88; H, 3.83; F, 10.14; N, 12.34。上述分析結果表明，獲得的產物為目標產品。Example 80

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 0.500g of white compound (yield 58.6%). The molecular ion quality 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.

依照實施例6的合成，步驟相同，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（產率66.7%），質譜分析確定的分子離子品質為：569.33（計算值為：569.18）；理論元素含量（%）C₃₅ H₂₂ F₃ N₅ ：C, 73.80; H, 3.89; F, 10.01; N, 12.30；實測元素含量（%）：C, 73.91; H, 3.88; F, 10.06; N, 12.27。上述分析結果表明，獲得的產物為目標產品。Example 81

According to the synthesis of Example 6, the steps were the same, and the compound 3-trifluoromethylbenzaldehyde was used instead of the compound benzaldehyde to obtain 0.523g of white compound (yield 66.7%). The molecular ion quality determined by mass spectrometry was 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.

依照實施例5的合成，步驟相同，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（產率60.4%），質譜分析確定的分子離子品質為：569.23（計算值為：569.18）；理論元素含量（%）C₃₅ H₂₂ F₃ N₅ ：C, 73.80; H, 3.89; F, 10.01; N, 12.30；實測元素含量（%）：C, 73.82; H, 3.85; F, 10.14; N, 12.33。上述分析結果表明，獲得的產物為目標產品。Example 82

According to the synthesis of Example 5, the steps are the same, and the compound 3-trifluoromethylbenzaldehyde is used instead of the compound benzaldehyde to obtain 0.516g of a white compound (yield 60.4%). The molecular ion quality determined by mass spectrometry is 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.

依照實施例5的合成，步驟相同，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（產率47.5%），質譜分析確定的分子離子品質為：637.21（計算值為：637.17）；理論元素含量（%）C₃₆ H₂₁ F₆ N₅ ：C, 67.82; H, 3.32; F, 17.88; N, 10.98，實測元素含量（%）：C, 67.85; H, 3.30; F, 17.90; N, 10.92。上述分析結果表明，獲得的產物為目標產品。Example 83

According to the synthesis of Example 5, the steps were the same, and the compound 3,5-bis(trifluoromethyl)benzaldehyde was used instead of the compound benzaldehyde to obtain 0.454g of the white compound (yield 47.5%). The molecular ion quality determined by mass spectrometry was : 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.

依照實施例9的合成，步驟相同，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（產率55.6%），質譜分析確定的分子離子品質為：638.18（計算值為：638.17）；理論元素含量（%）C₃₅ H₂₀ F₆ N₆ ：C, 65.83; H, 3.16; F, 17.85; N, 13.16，實測元素含量（%）：C, 65.85; H, 3.10; F, 17.86; N, 13.12。上述分析結果表明，獲得的產物為目標產品。Example 84

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 quality 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.

依照實施例49的合成，步驟相同，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（產率46.6%），質譜分析確定的分子離子品質為：829.24（計算值為：829.24）；理論元素含量（%）C₄₉ H₂₉ F₆ N₇ ：C, 70.92; H, 3.52; F, 13.74; N, 11.82，實測元素含量（%）：C, 70.95; H, 3.54; F, 13.77; N, 11.90。上述分析結果表明，獲得的產物為目標產品。Example 85

According to the synthesis of Example 49, 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, 0.511g of white compound (yield 46.6%) was obtained. The molecular ion quality 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.

依照實施例51的合成，步驟相同，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（產率33.6%），質譜分析確定的分子離子品質為：831.24（計算值為：831.23）；理論元素含量（%）C₄₇ H₂₇ F₆ N₉ ：C, 67.87; H, 3.27; F, 13.70; N, 15.16，實測元素含量（%）：C, 67.86; H, 3.29; F, 13.72; N, 15.14。上述分析結果表明，獲得的產物為目標產品。Example 86

According to the synthesis of Example 51, 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, 0.419g of white compound (yield 33.6%) was obtained, the molecular ion quality 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.

依照實施例53的合成，步驟相同，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（產率35.8%），質譜分析確定的分子離子品質為：831.20（計算值為：831.23）；理論元素含量（%）C₄₇ H₂₇ F₆ N₉ ：C, 67.87; H, 3.27; F, 13.70; N, 15.16，實測元素含量（%）：C, 67.89; H, 3.33; F, 13.74; N, 15.18。上述分析結果表明，獲得的產物為目標產品。Example 87

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 (yield 35.8%) was obtained. The molecular ion quality 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.

依照實施例56的合成，步驟相同，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（產率40.3%），質譜分析確定的分子離子品質為：965.21（計算值為：965.21）；理論元素含量（%）C₅₁ H₂₇ F₁₂ N₇ ：C, 63.42; H, 2.82; F, 23.61; N, 10.15，實測元素含量（%）：C, 63.45; H, 2.90; F, 23.63; N, 10.22。上述分析結果表明，獲得的產物為目標產品。Example 88

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 Group-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 quality determined by mass spectrometry 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.

依照實施例29的合成，步驟相同，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（產率51.2%），質譜分析確定的分子離子品質為：773.18（計算值為：773.14）；理論元素含量（%）C₃₈ H₁₉ F₁₂ N₅ :C, 59.00; H, 2.48; F, 29.47; N, 9.05，實測元素含量（%）：C, 59.08; H, 2.53; F, 29.55; N, 9.12。上述分析結果表明，獲得的產物為目標產品。Example 89

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 was obtained (yield 51.2%), the molecular ion quality 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.

依照實施例49的合成，步驟相同，用化合物N¹ ,N¹ ’-{5-溴-1,3-二（2-三氟甲基苯基）}雙（1,2-苯二胺）代替化合物N¹ ,N¹ ’（5-溴-1,3-二苯基）雙（1,2-苯二胺），得到白色化合物0.599g（產率48.2%），質譜分析確定的分子離子品質為：829.25（計算值為：829.24）；理論元素含量（%）C₄₉ H₂₉ F₆ N₇ ：C, 70.92; H, 3.52; F, 13.74; N, 11.82，實測元素含量（%）：C, 70.93; H, 3.55; F, 13.77; N, 11.80。上述分析結果表明，獲得的產物為目標產品。Example 90

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 Quality: 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.

依照實施例59的合成，步驟相同，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（產率44.2%），質譜分析確定的分子離子品質為：965.23（計算值為：965.21）；理論元素含量（%）C₅₁ H₂₇ F₁₂ N₇ ：C, 63.42; H, 2.82; F, 23.61; N, 10.15，實測元素含量（%）：C, 63.48; H, 2.90; F, 23.66; N, 10.21。上述分析結果表明，獲得的產物為目標產品。Example 91

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, using the compound 3-trifluoromethylbenzaldehyde instead of the compound benzaldehyde to obtain 0.640g of white compound (yield 44.2%). The molecular ion quality determined by mass spectrometry is 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.

依照實施例19的合成，步驟相同，用化合物N¹ -（2-異丙基苯基）苯-1,2-二胺代替化合物N¹ -（2-氟苯基）苯-1,2-二胺，得到白色化合物0.523g（產率37.9%）。質譜分析確定的分子離子品質為：543.26（計算值為：543.24）；理論元素含量（%）C₃₇ H₂₉ N₅ ：C, 81.74; H, 5.38; N, 12.88；實測元素含量（%）：C, 81.75; H, 5.37; N, 12.88。上述分析結果表明，獲得的產物為目標產品。Example 92

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 (yield 37.9%) was obtained. The molecular ion quality 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.

依照實施例20的合成，步驟相同，用化合物N¹ -（3-異丙基苯基）苯-1,2-二胺代替化合物N¹ -（3-氟苯基）苯-1,2-二胺，得到白色化合物0.503g（產率36.9%）。質譜分析確定的分子離子品質為：543.27（計算值為：543.24）；理論元素含量（%）C₃₇ H₂₉ N₅ ：C, 81.74; H, 5.38; N, 12.88；實測元素含量（%）：C, 81.75; H, 5.37; N, 12.88。上述分析結果表明，獲得的產物為目標產品。Example 93

According to the synthesis of Example 20, 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, 0.503 g of white compound was obtained (yield 36.9%). The molecular ion quality 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.

依照實施例21的合成，步驟相同，用化合物N¹ -（4-異丙基苯基）苯-1,2-二胺代替化合物N¹ -（4-氟苯基）苯-1,2-二胺，得到白色化合物0.423g（產率37.0%）。質譜分析確定的分子離子品質為：543.27（計算值為：543.24）；理論元素含量（%）C₃₇ H₂₉ N₅ ：C, 81.74; H, 5.38; N, 12.88；實測元素含量（%）：C, 81.75; H, 5.37; N, 12.88。上述分析結果表明，獲得的產物為目標產品。Example 94

According to the synthesis of Example 21, 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, 0.423 g of a white compound was obtained (yield 37.0%). The molecular ion quality 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.

依照實施例22的合成，步驟相同，用化合物N¹ -（2-異丙基苯基）苯-1,2-二胺代替化合物N¹ -（2-氟苯基）苯-1,2-二胺，得到白色化合物0.523g（產率37.9%）。質譜分析確定的分子離子品質為：543.26（計算值為：543.24）；理論元素含量（%）C₃₇ H₂₉ N₅ ：C, 81.74; H, 5.38; N, 12.88；實測元素含量（%）：C, 81.75; H, 5.37; N, 12.88。上述分析結果表明，獲得的產物為目標產品。Example 95

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 a white compound (yield 37.9%) was obtained. The molecular ion quality 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.

依照實施例23的合成，步驟相同，用化合物N¹ -（3-異丙基苯基）苯-1,2-二胺代替化合物N¹ -（3-氟苯基）苯-1,2-二胺，得到白色化合物0.578g（產率33.9%）。質譜分析確定的分子離子品質為：543.27（計算值為：543.24）；理論元素含量（%）C₃₇ H₂₉ N₅ ：C, 81.74; H, 5.38; N, 12.88；實測元素含量（%）：C, 81.75; H, 5.37; N, 12.88。上述分析結果表明，獲得的產物為目標產品。Example 96

According to the synthesis of Example 23, 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, 0.578 g of a white compound was obtained (yield 33.9%). The molecular ion quality 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.

依照實施例24的合成，步驟相同，用化合物N¹ -（4-異丙基苯基）苯-1,2-二胺代替化合物N¹ -（4-氟苯基）苯-1,2-二胺，得到白色化合物0.513g（產率36.9%）。質譜分析確定的分子離子品質為：543.29（計算值為：543.24）；理論元素含量（%）C₃₇ H₂₉ N₅ ：C, 81.74; H, 5.38; N, 12.88；實測元素含量（%）：C, 81.75; H, 5.37; N, 12.88。上述分析結果表明，獲得的產物為目標產品。Example 97

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 quality 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.

依照實施例25的合成，步驟相同，用化合物N¹ -（2-異丙基苯基）苯-1,2-二胺代替化合物N¹ -（2-氟苯基）苯-1,2-二胺，得到白色化合物0.523g（產率37.9%）。質譜分析確定的分子離子品質為：543.27（計算值為：543.24）；理論元素含量（%）C₃₇ H₂₉ N₅ ：C, 81.74; H, 5.38; N, 12.88；實測元素含量（%）：C, 81.75; H, 5.37; N, 12.88。上述分析結果表明，獲得的產物為目標產品。Example 98

According to the synthesis of Example 25, the procedure is 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 (yield 37.9%) was obtained. The molecular ion quality 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.

依照實施例26的合成，步驟相同，用化合物N¹ -（3-異丙基苯基）苯-1,2-二胺代替化合物N¹ -（3-氟苯基）苯-1,2-二胺，得到白色化合物0.423g（產率37.7%）。質譜分析確定的分子離子品質為：543.29（計算值為：543.24）；理論元素含量（%）C₃₇ H₂₉ N₅ ：C, 81.74; H, 5.38; N, 12.88；實測元素含量（%）：C, 81.75; H, 5.37; N, 12.88。上述分析結果表明，獲得的產物為目標產品。Example 99

According to the synthesis of Example 26, 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, 0.423 g of a white compound was obtained (yield 37.7%). The molecular ion quality 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.

依照實施例27的合成，步驟相同，用化合物N¹ -（4-異丙基苯基）苯-1,2-二胺代替化合物N¹ -（4-氟苯基）苯-1,2-二胺，得到白色化合物0.523g（產率32.9%）。質譜分析確定的分子離子品質為：543.28（計算值為：543.24）；理論元素含量（%）C₃₇ H₂₉ N₅ ：C, 81.74; H, 5.38; N, 12.88；實測元素含量（%）：C, 81.75; H, 5.37; N, 12.88。上述分析結果表明，獲得的產物為目標產品。Example 100

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 quality 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.

依照實施例28的合成，步驟相同，用化合物N¹ -（3,5-二異丙基苯基）苯-1,2-二胺代替化合物N¹ -（3，5-氟苯基）苯-1,2-二胺，得到白色化合物0.523g（產率37.9%）。質譜分析確定的分子離子品質為：585.26（計算值為：585.29）；理論元素含量（%）C₄₀ H₃₅ N₅ ：C, 82.02; H, 6.02; N, 11.96；實測元素含量（%）：C, 82.05; H, 6.07; N, 11.88。上述分析結果表明，獲得的產物為目標產品。Example 101

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, 0.523g of white compound was obtained (yield 37.9%). The molecular ion quality 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.

依照實施例29的合成，步驟相同，用化合物N¹ -（3,5-二異丙基苯基）苯-1,2-二胺代替化合物N¹ -（3，5-氟苯基）苯-1,2-二胺，得到白色化合物0.520g（產率35.9%）。質譜分析確定的分子離子品質為：585.26（計算值為：585.29）；理論元素含量（%）C₄₀ H₃₅ N₅ ：C, 82.02; H, 6.02; N, 11.96；實測元素含量（%）：C, 82.05; H, 6.07; N, 11.88。上述分析結果表明，獲得的產物為目標產品。Example 102

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 quality 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.

依照實施例30的合成，步驟相同，用化合物N¹ -（3,5-二異丙基苯基）苯-1,2-二胺代替化合物N¹ -（3，5-氟苯基）苯-1,2-二胺，得到白色化合物0.527g（產率35.9%）。質譜分析確定的分子離子品質為：585.27（計算值為：585.29）；理論元素含量（%）C₄₀ H₃₅ N₅ ：C, 82.02; H, 6.02; N, 11.96；實測元素含量（%）：C, 82.05; H, 6.07; N, 11.88。上述分析結果表明，獲得的產物為目標產品。Example 103

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 quality 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.

依照實施例31的合成，步驟相同，用化合物2-異丙基苯甲醛代替化合物2-氟苯甲醛，得到白色化合物0.507g（產率37.8%）。質譜分析確定的分子離子品質為：543.27（計算值為：543.24）；理論元素含量（%）C₃₇ H₂₉ N₅ ：C, 81.74; H, 5.38; N, 12.88；實測元素含量（%）：C, 81.75; H, 5.37; N, 12.88。上述分析結果表明，獲得的產物為目標產品。Example 104

According to the synthesis of Example 31, the steps were 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 quality 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.

依照實施例32的合成，步驟相同，用化合物2-異丙基苯甲醛代替化合物2-氟苯甲醛，得到白色化合物0.523g（產率37.6%）。質譜分析確定的分子離子品質為：543.27（計算值為：543.24）；理論元素含量（%）C₃₇ H₂₉ N₅ ：C, 81.74; H, 5.38; N, 12.88；實測元素含量（%）：C, 81.75; H, 5.37; N, 12.88。上述分析結果表明，獲得的產物為目標產品。Example 105

According to the synthesis of Example 32, the steps were 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 37.6%). The molecular ion quality 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.

依照實施例33的合成，步驟相同，用化合物2-異丙基苯甲醛代替化合物2-氟苯甲醛，得到白色化合物0.523g（產率30.9%）。質譜分析確定的分子離子品質為：543.26（計算值為：543.24）；理論元素含量（%）C₃₇ H₂₉ N₅ ：C, 81.74; H, 5.38; N, 12.88；實測元素含量（%）：C, 81.75; H, 5.37; N, 12.88。上述分析結果表明，獲得的產物為目標產品。Example 106

According to the synthesis of Example 33, the steps were 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 quality 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.

依照實施例34的合成，步驟相同，用化合物3-異丙基苯甲醛代替化合物3-氟苯甲醛，得到白色化合物0.523g（產率37.9%）。質譜分析確定的分子離子品質為：543.21（計算值為：543.24）；理論元素含量（%）C₃₇ H₂₉ N₅ ：C, 81.74; H, 5.38; N, 12.88；實測元素含量（%）：C, 81.75; H, 5.37; N, 12.88。上述分析結果表明，獲得的產物為目標產品。Example 107

According to the synthesis of Example 34, the procedure was 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 quality 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.

依照實施例35的合成，步驟相同，用化合物3-異丙基苯甲醛代替化合物3-氟苯甲醛，得到白色化合物0.423g（產率37.2%）。質譜分析確定的分子離子品質為：543.29（計算值為：543.24）；理論元素含量（%）C₃₇ H₂₉ N₅ ：C, 81.74; H, 5.38; N, 12.88；實測元素含量（%）：C, 81.75; H, 5.37; N, 12.88。上述分析結果表明，獲得的產物為目標產品。Example 108

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 quality 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.

依照實施例36的合成，步驟相同，用化合物3-異丙基苯甲醛代替化合物3-氟苯甲醛，得到白色化合物0.479g（產率37.1%）。質譜分析確定的分子離子品質為：543.23（計算值為：543.24）；理論元素含量（%）C₃₇ H₂₉ N₅ ：C, 81.74; H, 5.38; N, 12.88；實測元素含量（%）：C, 81.75; H, 5.37; N, 12.88。上述分析結果表明，獲得的產物為目標產品。Example 109

According to the synthesis of Example 36, the steps were 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 quality 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.

依照實施例37的合成，步驟相同，用化合物4-異丙基苯甲醛代替化合物4-氟苯甲醛，得到白色化合物0.523g（產率37.9%）。質譜分析確定的分子離子品質為：543.28（計算值為：543.24）；理論元素含量（%）C₃₇ H₂₉ N₅ ：C, 81.74; H, 5.38; N, 12.88；實測元素含量（%）：C, 81.75; H, 5.37; N, 12.88。上述分析結果表明，獲得的產物為目標產品。Example 110

According to the synthesis of Example 37, the steps were 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 quality 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.

依照實施例38的合成，步驟相同，用化合物4-異丙基苯甲醛代替化合物4-氟苯甲醛，得到白色化合物0.523g（產率37.9%）。質譜分析確定的分子離子品質為：543.22（計算值為：543.24）；理論元素含量（%）C₃₇ H₂₉ N₅ ：C, 81.74; H, 5.38; N, 12.88；實測元素含量（%）：C, 81.75; H, 5.37; N, 12.88。上述分析結果表明，獲得的產物為目標產品。Example 111

According to the synthesis of Example 38, the steps are the same, and the compound 4-isopropylbenzaldehyde is used instead of the compound 4-fluorobenzaldehyde to obtain 0.523 g of a white compound (yield 37.9%). The molecular ion quality 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.

依照實施例39的合成，步驟相同，用化合物4-異丙基苯甲醛代替化合物4-氟苯甲醛，得到白色化合物0.521g（產率37.4%）。質譜分析確定的分子離子品質為：543.26（計算值為：543.24）；理論元素含量（%）C₃₇ H₂₉ N₅ ：C, 81.74; H, 5.38; N, 12.88；實測元素含量（%）：C, 81.75; H, 5.37; N, 12.88。上述分析結果表明，獲得的產物為目標產品。Example 112

According to the synthesis of Example 39, the steps were the same, and the compound 4-isopropylbenzaldehyde was used instead of the compound 4-fluorobenzaldehyde to obtain 0.521 g of a white compound (yield 37.4%). The molecular ion quality 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.

依照實施例40的合成，步驟相同，用化合物3,5-二異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（產率31.4%）。質譜分析確定的分子離子品質為：585.26（計算值為：585.29）；理論元素含量（%）C₄₀ H₃₅ N₅ ：C, 82.02; H, 6.02; N, 11.96；實測元素含量（%）：C, 82.05; H, 6.07; N, 11.88。上述分析結果表明，獲得的產物為目標產品。Example 113

According to the synthesis of Example 40, the steps were the same, and the compound 3,5-diisopropylbenzaldehyde was used instead of the compound 3,5-difluorobenzaldehyde to obtain 0.514 g of a white compound (yield 31.4%). The molecular ion quality 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.

依照實施例41的合成，步驟相同，用化合物3,5-二異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（產率30.5%）。質譜分析確定的分子離子品質為：585.27（計算值為：585.29）；理論元素含量（%）C₄₀ H₃₅ N₅ ：C, 82.02; H, 6.02; N, 11.96；實測元素含量（%）：C, 82.05; H, 6.07; N, 11.88。上述分析結果表明，獲得的產物為目標產品。Example 114

According to the synthesis of Example 41, the steps were the same, and the compound 3,5-diisopropylbenzaldehyde was substituted for the compound 3,5-difluorobenzaldehyde to obtain 0.520 g of a white compound (yield: 30.5%). The molecular ion quality 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.

依照實施例42的合成，步驟相同，用化合物3,5-二異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（產率37.9%）。質譜分析確定的分子離子品質為：585.27（計算值為：585.29）；理論元素含量（%）C₄₀ H₃₅ N₅ ：C, 82.02; H, 6.02; N, 11.96；實測元素含量（%）：C, 82.05; H, 6.07; N, 11.88。上述分析結果表明，獲得的產物為目標產品。Example 115

According to the synthesis of Example 42, the steps are the same, and the compound 3,5-diisopropylbenzaldehyde is used instead of the compound 3,5-difluorobenzaldehyde to obtain 0.523 g of a white compound (yield 37.9%). The molecular ion quality 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.

依照實施例55的合成，步驟相同，用化合物N¹ -（2-異丙基苯基）苯-1,2-二胺代替化合物N¹ -（2-氟苯基）苯-1,2-二胺，得到白色化合物0.529g（產率27.2%）。質譜分析確定的分子離子質量為：777.30（計算值為：777.36）；理論元素含量（%）C₅₃ H₄₃ N₇ ：C, 81.83; H, 5.57; N, 12.60；實測元素含量（%）：C, 81.85; H, 5.57; N, 12.58。上述分析結果表明，獲得的產物為目標產品。Example 116

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 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.

依照實施例56的合成，步驟相同，用化合物N¹ -（3-異丙基苯基）苯-1,2-二胺代替化合物N¹ -（3-氟苯基）苯-1,2-二胺，得到白色化合物0.579g（產率24.2%）。質譜分析確定的分子離子質量為：777.34（計算值為：777.36）；理論元素含量（%）C₅₃ H₄₃ N₇ ：C, 81.83; H, 5.57; N, 12.60；實測元素含量（%）：C, 81.85; H, 5.57; N, 12.58。上述分析結果表明，獲得的產物為目標產品。Example 117

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 was obtained (yield 24.2%). 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.

依照實施例57的合成，步驟相同，用化合物N¹ -（4-異丙基苯基）苯-1,2-二胺代替化合物N¹ -（4-氟苯基）苯-1,2-二胺，得到白色化合物0.529g（產率27.2%）。質譜分析確定的分子離子質量為：777.30（計算值為：777.36）；理論元素含量（%）C₅₃ H₄₃ N₇ ：C, 81.83; H, 5.57; N, 12.60；實測元素含量（%）：C, 81.85; H, 5.57; N, 12.58。上述分析結果表明，獲得的產物為目標產品。Example 118

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 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.

依照實施例58的合成，步驟相同，用化合物2-異丙基苯甲醛代替化合物2-氟苯甲醛，得到白色化合物0.529g（產率27.2%）。質譜分析確定的分子離子質量為：777.32（計算值為：777.36）；理論元素含量（%）C₅₃ H₄₃ N₇ ：C, 81.83; H, 5.57; N, 12.60；實測元素含量（%）：C, 81.85; H, 5.57; N, 12.58。上述分析結果表明，獲得的產物為目標產品。Example 119

According to the synthesis of Example 58, the steps were 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.

依照實施例59的合成，步驟相同，用化合物3-異丙基苯甲醛代替化合物3-氟苯甲醛，得到白色化合物0.529g（產率27.2%）。質譜分析確定的分子離子質量為：777.30（計算值為：777.36）；理論元素含量（%）C₅₃ H₄₃ N₇ ：C, 81.83; H, 5.57; N, 12.60；實測元素含量（%）：C, 81.85; H, 5.57; N, 12.58。上述分析結果表明，獲得的產物為目標產品。Example 120

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.

依照實施例60的合成，步驟相同，用化合物4-異丙基苯甲醛代替化合物4-氟苯甲醛，得到白色化合物0.629g（產率29.2%）。質譜分析確定的分子離子質量為：777.32（計算值為：777.36）；理論元素含量（%）C₅₃ H₄₃ N₇ ：C, 81.83; H, 5.57; N, 12.60；實測元素含量（%）：C, 81.85; H, 5.57; N, 12.58。上述分析結果表明，獲得的產物為目標產品。Example 121

According to the synthesis of Example 60, the procedure was 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.

依照實施例61的合成，步驟相同，用化合物2-氯-4,6-二（4-異丙基苯基）-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（產率27.2%）。質譜分析確定的分子離子質量為：777.30（計算值為：777.36）；理論元素含量（%）C₅₃ H₄₃ N₇ ：C, 81.83; H, 5.57; N, 12.60；實測元素含量（%）：C, 81.85; H, 5.57; N, 12.58。上述分析結果表明，獲得的產物為目標產品。Example 122

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 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.

依照實施例62的合成，步驟相同，用化合物2-氯-4,6-二（4-異丙基苯基）-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（產率27.7%）。質譜分析確定的分子離子質量為：777.32（計算值為：777.36）；理論元素含量（%）C₅₃ H₄₃ N₇ ：C, 81.83; H, 5.57; N, 12.60；實測元素含量（%）：C, 81.85; H, 5.57; N, 12.58。上述分析結果表明，獲得的產物為目標產品。Example 123

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 white compound was obtained (yield 27.7%). 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.

依照實施例63的合成，步驟相同，用化合物2-氯-4,6-二（4-異丙基苯基）-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（產率27.2%）。質譜分析確定的分子離子質量為：779.30（計算值為：779.35）；理論元素含量（%）C₅₁ H₄₁ N₉ ：C, 78.54; H, 5.30; N, 16.16；實測元素含量（%）：C, 78.55; H, 5.37; N, 16.08。上述分析結果表明，獲得的產物為目標產品。Example 124

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 white compound was obtained (yield 27.2%). 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.

依照實施例64的合成，步驟相同，用化合物2-氯-4,6-二（4-異丙基苯基）-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（產率25.6%）。質譜分析確定的分子離子質量為：779.32（計算值為：779.35）；理論元素含量（%）C₅₁ H₄₁ N₉ ：C, 78.54; H, 5.30; N, 16.16；實測元素含量（%）：C, 78.55; H, 5.37; N, 16.08。上述分析結果表明，獲得的產物為目標產品。Example 125

According to the synthesis of Example 64, 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, 0.428 g of white compound was obtained (yield: 25.6%). 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.

依照實施例65的合成，步驟相同，用化合物2-氯-4,6-二（4-異丙基苯基）-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（產率27.2%）。質譜分析確定的分子離子質量為：779.30（計算值為：779.35）；理論元素含量（%）C₅₁ H₄₁ N₉ ：C, 78.54; H, 5.30; N, 16.16；實測元素含量（%）：C, 78.55; H, 5.37; N, 16.08。上述分析結果表明，獲得的產物為目標產品。Example 126

According to the synthesis of Example 65, 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, 0.529 g of white compound was obtained (yield 27.2%). 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.

依照實施例66的合成，步驟相同，用化合物2-氯-4,6-二（4-異丙基苯基）-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（產率25.7%）。質譜分析確定的分子離子質量為：779.37（計算值為：779.35）；理論元素含量（%）C₅₁ H₄₁ N₉ ：C, 78.54; H, 5.30; N, 16.16；實測元素含量（%）：C, 78.55; H, 5.37; N, 16.08。上述分析結果表明，獲得的產物為目標產品。Example 127

According to the synthesis of Example 66, 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, 0.427 g of a white compound was obtained (yield: 25.7%). 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.

依照實施例67的合成，步驟相同，用化合物2-氯-4,6-二（4-異丙基苯基）-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N¹ -（2-異丙基苯基）苯-1,2-二胺代替化合物N¹ -（2-氟苯基）苯-1,2-二胺得到白色化合物0.529g（產率27.2%）。質譜分析確定的分子離子質量為：861.42（計算值為：861.45）；理論元素含量（%）：C₅₉ H₅₅ N₇ ：C, 82.20; H, 6.43; N, 11.37；實測元素含量（%）：C, 82.25; H, 6.47; N, 11.28。上述分析結果表明，獲得的產物為目標產品。Example 128

According to the synthesis of Example 67, 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 -(2-isopropylphenyl)benzene-1,2-diamine instead of compound N ¹ -(2-fluorophenyl) ) Benzene-1,2-diamine to obtain 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.

依照實施例68的合成，步驟相同，用化合物2-氯-4,6-二（4-異丙基苯基）-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N¹ -（3-異丙基苯基）苯-1,2-二胺代替化合物N¹ -（3-氟苯基）苯-1,2-二胺得到白色化合物0.565g（產率28.2%）。質譜分析確定的分子離子質量為：861.41（計算值為：861.45）；理論元素含量（%）：C₅₉ H₅₅ N₇ ：C, 82.20; H, 6.43; N, 11.37；實測元素含量（%）：C, 82.25; H, 6.48; N, 11.27。上述分析結果表明，獲得的產物為目標產品。Example 129

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 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.

依照實施例69的合成，步驟相同，用化合物2-氯-4,6-二（4-異丙基苯基）-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N¹ -（4-異丙基苯基）苯-1,2-二胺代替化合物N¹ -（4-氟苯基）苯-1,2-二胺得到白色化合物0.529g（產率27.2%）。質譜分析確定的分子離子質量為：861.41（計算值為：861.45）；理論元素含量（%）：C₅₉ H₅₅ N₇ ：C, 82.20; H, 6.43; N, 11.37；實測元素含量（%）：C, 82.25; H, 6.47; N, 11.28。上述分析結果表明，獲得的產物為目標產品。Example 130

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 to obtain 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.

依照實施例70的合成，步驟相同，用化合物2-氯-4,6-二（4-異丙基苯基）-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-異丙基-苯甲醛代替化合物2-氟苯甲醛得到白色化合物0.417g（產率28.2%）。質譜分析確定的分子離子質量為：861.42（計算值為：861.45）；理論元素含量（%）：C₅₉ H₅₅ N₇ ：C, 82.20; H, 6.43; N, 11.37；實測元素含量（%）：C, 82.25; H, 6.47; N, 11.28。上述分析結果表明，獲得的產物為目標產品。Example 131

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.

依照實施例71的合成，步驟相同，用化合物2-氯-4,6-二（4-異丙基苯基）-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-異丙基苯甲醛代替化合物3-氟-苯甲醛得到白色化合物0.629g（產率25.8%）。質譜分析確定的分子離子質量為：861.47（計算值為：861.45）；理論元素含量（%）：C₅₉ H₅₅ N₇ ：C, 82.20; H, 6.43; N, 11.37；實測元素含量（%）：C, 82.25; H, 6.47; N, 11.28。上述分析結果表明，獲得的產物為目標產品。Example 132

According to the synthesis of Example 71, 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 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.

依照實施例72的合成，步驟相同，用化合物2-氯-4,6-二（4-異丙基苯基）-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-異丙基苯甲醛代替化合物4-氟苯甲醛得到白色化合物0.529g（產率27.2%）。質譜分析確定的分子離子質量為：861.42（計算值為：861.45）；理論元素含量（%）：C₅₉ H₅₅ N₇ ：C, 82.20; H, 6.43; N, 11.37；實測元素含量（%）：C, 82.25; H, 6.47; N, 11.28。上述分析結果表明，獲得的產物為目標產品。Example 133

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.

依照實施例73的合成，步驟相同，用化合物2-氯-4,6-二（4-異丙基苯基）-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N¹ -（3,5-二異丙基苯基）苯-1,2-二胺代替化合物N¹ -（3,5-二氟苯基）苯-1,2-二胺得到白色化合物0.417g（產率28.3%）。質譜分析確定的分子離子質量為：669.42（計算值為：669.38）；理論元素含量（%）：C₄₆ H₄₇ N₅ ：C, 82.47; H, 7.07; N, 10.45；實測元素含量（%）：C, 82.45; H, 7.07; N, 10.48。上述分析結果表明，獲得的產物為目標產品。Example 134

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.

依照實施例55的合成，步驟相同，用化合物N¹ -（2-甲基苯基）苯-1,2-二胺代替化合物N¹ -（2-氟苯基）苯-1,2-二胺，得到白色化合物0.509g（產率27.7%）。質譜分析確定的分子離子質量為：721.32（計算值為：721.30）；理論元素含量（%）C₄₉ H₃₅ N₇ ：C, 81.53; H, 4.89; N, 13.58；實測元素含量（%）：C, 81.55; H, 4.87; N, 13.58。上述分析結果表明，獲得的產物為目標產品。Example 135

According to the synthesis of Example 55, the steps are the same, and the compound N ¹ -(2-methylphenyl)benzene-1,2-diamine is used instead of the compound N ¹ -(2-fluorophenyl)benzene-1,2-diamine Amine, 0.509 g of a white compound (27.7% yield) was obtained. 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.

依照實施例56的合成，步驟相同，用化合物N¹ -（3-甲基苯基）苯-1,2-二胺代替化合物N¹ -（3-氟苯基）苯-1,2-二胺，得到白色化合物0.644g（產率25.9%）。質譜分析確定的分子離子質量為：721.31（計算值為：721.30）；理論元素含量（%）C₄₉ H₃₅ N₇ ：C, 81.53; H, 4.89; N, 13.58；實測元素含量（%）：C, 81.55; H, 4.87; N, 13.58。上述分析結果表明，獲得的產物為目標產品。Example 136

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.

依照實施例57的合成，步驟相同，用化合物N¹ -（4-甲基苯基）苯-1,2-二胺代替化合物N¹ -（4-氟苯基）苯-1,2-二胺，得到白色化合物0.519g（產率27.7%）。質譜分析確定的分子離子質量為：721.32（計算值為：721.30）；理論元素含量（%）C₄₉ H₃₅ N₇ ：C, 81.53; H, 4.89; N, 13.58；實測元素含量（%）：C, 81.55; H, 4.87; N, 13.58。上述分析結果表明，獲得的產物為目標產品。Example 137

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.

依照實施例58的合成，步驟相同，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（產率25.7%）。質譜分析確定的分子離子質量為：721.37（計算值為：721.30）；理論元素含量（%）C₄₉ H₃₅ N₇ ：C, 81.53; H, 4.89; N, 13.58；實測元素含量（%）：C, 81.55; H, 4.87; N, 13.58。上述分析結果表明，獲得的產物為目標產品。Example 138

According to the synthesis of Example 58, the procedure was the same, and the compound 2-methylbenzaldehyde was used instead of 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.

依照實施例59的合成，步驟相同，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（產率27.5%）。質譜分析確定的分子離子質量為：721.32（計算值為：721.30）；理論元素含量（%）C₄₉ H₃₅ N₇ ：C, 81.53; H, 4.89; N, 13.58；實測元素含量（%）：C, 81.55; H, 4.87; N, 13.58。上述分析結果表明，獲得的產物為目標產品。Example 139

According to the synthesis of Example 59, the steps were 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.

依照實施例60的合成，步驟相同，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（產率23.8%）。質譜分析確定的分子離子質量為：721.32（計算值為：721.30）；理論元素含量（%）C₄₉ H₃₅ N₇ ：C, 81.53; H, 4.89; N, 13.58；實測元素含量（%）：C, 81.55; H, 4.87; N, 13.58。上述分析結果表明，獲得的產物為目標產品。Example 140

According to the synthesis of Example 60, the steps are the same, and the compound 4-methylbenzaldehyde is 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.

依照實施例61的合成，步驟相同，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（產率27.2%）。質譜分析確定的分子離子質量為：721.32（計算值為：721.30）；理論元素含量（%）C₄₉ H₃₅ N₇ ：C, 81.53; H, 4.89; N, 13.58；實測元素含量（%）：C, 81.55; H, 4.87; N, 13.58。上述分析結果表明，獲得的產物為目標產品。Example 141

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 obtained 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.

依照實施例62的合成，步驟相同，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（產率25.4%）。質譜分析確定的分子離子質量為：721.30（計算值為：721.30）；理論元素含量（%）C₄₉ H₃₅ N₇ ：C, 81.53; H, 4.89; N, 13.58；實測元素含量（%）：C, 81.55; H, 4.87; N, 13.58。上述分析結果表明，獲得的產物為目標產品。Example 142

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.

依照實施例63的合成，步驟相同，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（產率27.2%）。質譜分析確定的分子離子質量為：723.30（計算值為：723.29）；理論元素含量（%）C₄₇ H₃₃ N₉ ：C, 77.99; H, 4.60; N, 17.42；實測元素含量（%）：C, 77.95; H, 4.67; N, 17.38。上述分析結果表明，獲得的產物為目標產品。Example 143

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.

依照實施例64的合成，步驟相同，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（產率26.2%）。質譜分析確定的分子離子質量為：723.31（計算值為：723.29）；理論元素含量（%）C₄₇ H₃₃ N₉ ：C, 77.99; H, 4.60; N, 17.42；實測元素含量（%）：C, 77.95; H, 4.67; N, 17.38。上述分析結果表明，獲得的產物為目標產品。Example 144

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.

依照實施例65的合成，步驟相同，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（產率27.1%）。質譜分析確定的分子離子質量為：723.30（計算值為：723.29）；理論元素含量（%）C₄₇ H₃₃ N₉ ：C, 77.99; H, 4.60; N, 17.42；實測元素含量（%）：C, 77.95; H, 4.67; N, 17.38。上述分析結果表明，獲得的產物為目標產品。Example 145

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, 0.529 g of a white compound was obtained (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.

依照實施例66的合成，步驟相同，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（產率28.3%）。質譜分析確定的分子離子質量為：723.30（計算值為：723.29）；理論元素含量（%）C₄₇ H₃₃ N₉ ：C, 77.99; H, 4.60; N, 17.42；實測元素含量（%）：C, 77.95; H, 4.67; N, 17.38。上述分析結果表明，獲得的產物為目標產品。Example 146

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.

依照實施例67的合成，步驟相同，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N¹ -（2-甲基苯基）苯-1,2-二胺代替化合物N¹ -（2-氟苯基）苯-1,2-二胺得到白色化合物0.529g（產率27.2%）。質譜分析確定的分子離子質量為：749.36（計算值為：749.33）；理論元素含量（%）C₅₁ H₃₉ N₇ ：C, 81.68; H, 5.24; N, 13.07；實測元素含量（%）：C, 81.65; H, 5.27; N, 13.08。上述分析結果表明，獲得的產物為目標產品。Example 147

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.

依照實施例68的合成，步驟相同，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N¹ -（3-甲基苯基）苯-1,2-二胺代替化合物N¹ -（3-氟苯基）苯-1,2-二胺得到白色化合物0.679g（產率29.7%）。質譜分析確定的分子離子質量為：749.32（計算值為：749.33）；理論元素含量（%）C₅₁ H₃₉ N₇ ：C, 81.68; H, 5.24; N, 13.07；實測元素含量（%）：C, 81.65; H, 5.27; N, 13.08。上述分析結果表明，獲得的產物為目標產品。Example 148

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 (29.7% yield). 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.

依照實施例69的合成，步驟相同，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N¹ -（4-甲基苯基）苯-1,2-二胺代替化合物N¹ -（4-氟苯基）苯-1,2-二胺得到白色化合物0.508g（產率24.7%）。質譜分析確定的分子離子質量為：749.31（計算值為：749.33）；理論元素含量（%）C₅₁ H₃₉ N₇ ：C, 81.68; H, 5.24; N, 13.07；實測元素含量（%）：C, 81.65; H, 5.27; N, 13.08。上述分析結果表明，獲得的產物為目標產品。Example 149

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.

依照實施例70的合成，步驟相同，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（產率29.7%）。質譜分析確定的分子離子質量為：749.31（計算值為：749.33）；理論元素含量（%）C₅₁ H₃₉ N₇ ：C, 81.68; H, 5.24; N, 13.07；實測元素含量（%）：C, 81.65; H, 5.27; N, 13.08。上述分析結果表明，獲得的產物為目標產品。Example 150

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.

依照實施例71的合成，步驟相同，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（產率26.5%）。質譜分析確定的分子離子質量為：749.37（計算值為：749.33）；理論元素含量（%）C₅₁ H₃₉ N₇ ：C, 81.68; H, 5.24; N, 13.07；實測元素含量（%）：C, 81.65; H, 5.27; N, 13.08。上述分析結果表明，獲得的產物為目標產品。Example 151

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 used instead of 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.

依照實施例72的合成，步驟相同，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（產率23.7%）。質譜分析確定的分子離子質量為：749.31（計算值為：749.33）；理論元素含量（%）C₅₁ H₃₉ N₇ ：C, 81.68; H, 5.24; N, 13.07；實測元素含量（%）：C, 81.65; H, 5.27; N, 13.08。上述分析結果表明，獲得的產物為目標產品。Example 152

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.

依照實施例73的合成，步驟相同，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N¹ -（3，5-二甲基苯基）苯-1,2-二胺代替化合物N¹ -（3，5-二氟苯基）苯-1,2-二胺得到白色化合物0.679g（產率29.7%）。質譜分析確定的分子離子質量為：557.29（計算值為：557.26）；理論元素含量（%）C₃₈ H₃₁ N₅ ：C, 81.84; H, 5.60; N, 12.56；實測元素含量（%）：C, 81.85; H, 5.67; N, 12.48。上述分析結果表明，獲得的產物為目標產品。Example 153

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 (29.7% yield). 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.

依照實施例1的合成，步驟相同，用化合物N¹ -（[1,1'-聯苯] -2-基）苯-1,2-二胺代替化合物鄰氨基二苯胺，得到白色化合物0.435g（產率31.3%）。質譜分析確定的分子離子質量為：577.25（計算值為：577.23）；理論元素含量（%）C₄₀ H₂₇ N₅ ：C, 83.17; H, 4.71; N, 12.12；實測元素含量（%）：C, 83.18; H, 4.72; N, 12.10。上述分析結果表明，獲得的產物為目標產品。Example 154

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 (The yield is 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.

依照實施例2的合成，步驟相同，用化合物N¹ -（[1,1'-聯苯] -2-基）苯-1,2-二胺代替化合物鄰氨基二苯胺，得到白色化合物0.467g（產率31.6%）。質譜分析確定的分子離子質量為：577.28（計算值為：577.23）；理論元素含量（%）C₄₀ H₂₇ N₅ ：C, 83.17; H, 4.71; N, 12.12；實測元素含量（%）：C, 83.18; H, 4.72; N, 12.10。上述分析結果表明，獲得的產物為目標產品。Example 155

According to the synthesis of Example 2, 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 0.467g of a white compound (The yield is 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.

依照實施例3的合成，步驟相同，用化合物N¹ -（[1,1'-聯苯] -2-基）苯-1,2-二胺代替化合物鄰氨基二苯胺，得到白色化合物0.438g（產率32.7%）。質譜分析確定的分子離子質量為：577.29（計算值為：577.23）；理論元素含量（%）C₄₀ H₂₇ N₅ ：C, 83.17; H, 4.71; N, 12.12；實測元素含量（%）：C, 83.18; H, 4.72; N, 12.10。上述分析結果表明，獲得的產物為目標產品。Example 156

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 (The yield is 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.

依照實施例4的合成，步驟相同，用化合物[1,1'-聯苯] -2-甲醛代替化合物苯甲醛，得到白色化合物0.503g（產率35.4%）。質譜分析確定的分子離子質量為：577.32（計算值為：577.23）；理論元素含量（%）C₄₀ H₂₇ N₅ ：C, 83.17; H, 4.71; N, 12.12；實測元素含量（%）：C, 83.18; H, 4.72; N, 12.10。上述分析結果表明，獲得的產物為目標產品。Example 157

According to the synthesis of Example 4, the steps were the same, and the compound [1,1'-biphenyl]-2-carboxaldehyde 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.

依照實施例5的合成，步驟相同，用化合物[1,1'-聯苯] -2-甲醛代替化合物苯甲醛，得到白色化合物0.468g（產率30.3%）。質譜分析確定的分子離子質量為：577.31（計算值為：577.23）；理論元素含量（%）C₄₀ H₂₇ N₅ ：C, 83.17; H, 4.71; N, 12.12；實測元素含量（%）：C, 83.18; H, 4.72; N, 12.10。上述分析結果表明，獲得的產物為目標產品。Example 158

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.

依照實施例6的合成，步驟相同，用化合物[1,1'-聯苯] -2-甲醛代替化合物苯甲醛，得到白色化合物0.538g（產率38.3%）。質譜分析確定的分子離子質量為：577.30（計算值為：577.23）；理論元素含量（%）C₄₀ H₂₇ N₅ ：C, 83.17; H, 4.71; N, 12.12；實測元素含量（%）：C, 83.18; H, 4.72; N, 12.10。上述分析結果表明，獲得的產物為目標產品。Example 159

According to the synthesis of Example 6, the steps were the same, and the compound [1,1'-biphenyl]-2-carboxaldehyde 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.

依照實施例1的合成，步驟相同，用化合物N¹ -（[1,1'-聯苯] -3-基）苯-1,2-二胺代替化合物鄰氨基二苯胺，得到白色化合物0.492g（產率34.6%）。質譜分析確定的分子離子質量為：577.28（計算值為：577.23）；理論元素含量（%）C₄₀ H₂₇ N₅ ：C, 83.17; H, 4.71; N, 12.12；實測元素含量（%）：C, 83.18; H, 4.72; N, 12.10。上述分析結果表明，獲得的產物為目標產品。Example 160

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 (The yield is 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.

依照實施例2的合成，步驟相同，用化合物N¹ -（[1,1'-聯苯] -3-基）苯-1,2-二胺代替化合物鄰氨基二苯胺，得到白色化合物0.448g（產率32.8%）。質譜分析確定的分子離子質量為：577.28（計算值為：577.23）；理論元素含量（%）C₄₀ H₂₇ N₅ ：C, 83.17; H, 4.71; N, 12.12；實測元素含量（%）：C, 83.18; H, 4.72; N, 12.10。上述分析結果表明，獲得的產物為目標產品。Example 161

According to the synthesis of Example 2, the steps are the same, and the compound N ¹ -([1,1'-biphenyl]-3-yl)benzene-1,2-diamine is substituted for the compound o-aminodiphenylamine to obtain 0.448 g of a white compound (The yield is 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.

依照實施例3的合成，步驟相同，用化合物N¹ -（[1,1'-聯苯] -3-基）苯-1,2-二胺代替化合物鄰氨基二苯胺，得到白色化合物0.523g（產率31.2%）。質譜分析確定的分子離子質量為：577.21（計算值為：577.23）；理論元素含量（%）C₄₀ H₂₇ N₅ ：C, 83.17; H, 4.71; N, 12.12；實測元素含量（%）：C, 83.18; H, 4.72; N, 12.10。上述分析結果表明，獲得的產物為目標產品。Example 162

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 (The yield is 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.

依照實施例4的合成，步驟相同，用化合物[1,1'-聯苯] -3-甲醛代替化合物苯甲醛，得到白色化合物0.495g（產率33.1%）。質譜分析確定的分子離子質量為：577.20（計算值為：577.23）；理論元素含量（%）C₄₀ H₂₇ N₅ ：C, 83.17; H, 4.71; N, 12.12；實測元素含量（%）：C, 83.18; H, 4.72; N, 12.10。上述分析結果表明，獲得的產物為目標產品。Example 163

According to the synthesis of Example 4, the steps were the same, and the compound [1,1'-biphenyl]-3-carbaldehyde was used instead of 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.

依照實施例5的合成，步驟相同，用化合物[1,1'-聯苯] -3-甲醛代替化合物苯甲醛，得到白色化合物0.441g（產率32.1%）。質譜分析確定的分子離子質量為：577.28（計算值為：577.23）；理論元素含量（%）C₄₀ H₂₇ N₅ ：C, 83.17; H, 4.71; N, 12.12；實測元素含量（%）：C, 83.18; H, 4.72; N, 12.10。上述分析結果表明，獲得的產物為目標產品。Example 164

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.

依照實施例6的合成，步驟相同，用[1,1'-聯苯] -3-甲醛代替化合物苯甲醛，得到白色化合物0.438g（產率32.4%）。質譜分析確定的分子離子質量為：577.25（計算值為：577.23）；理論元素含量（%）C₄₀ H₂₇ N₅ ：C, 83.17; H, 4.71; N, 12.12；實測元素含量（%）：C, 83.18; H, 4.72; N, 12.10。上述分析結果表明，獲得的產物為目標產品。Example 165

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.

依照實施例1的合成，步驟相同，用化合物N¹ -（[1,1'-聯苯] -4-基）苯-1,2-二胺代替化合物鄰氨基二苯胺，得到白色化合物0.413g（產率35.6%）。質譜分析確定的分子離子質量為：577.30（計算值為：577.23）；理論元素含量（%）C₄₀ H₂₇ N₅ ：C, 83.17; H, 4.71; N, 12.12；實測元素含量（%）：C, 83.18; H, 4.72; N, 12.10。上述分析結果表明，獲得的產物為目標產品。Example 166

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 (The yield is 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.

依照實施例2的合成，步驟相同，用化合物N¹ -（[1,1'-聯苯] -4-基）苯-1,2-二胺代替化合物鄰氨基二苯胺，得到白色化合物0.448g（產率31.3%）。質譜分析確定的分子離子質量為：577.26（計算值為：577.23）；理論元素含量（%）C₄₀ H₂₇ N₅ ：C, 83.17; H, 4.71; N, 12.12；實測元素含量（%）：C, 83.18; H, 4.72; N, 12.10。上述分析結果表明，獲得的產物為目標產品。Example 167

According to the synthesis of Example 2, the steps are the same, 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 (The yield is 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.

依照實施例3的合成，步驟相同，用化合物N¹ -（[1,1'-聯苯] -4-基）苯-1,2-二胺代替化合物鄰氨基二苯胺，得到白色化合物0.458g（產率33.8%）。質譜分析確定的分子離子質量為：577.28（計算值為：577.23）；理論元素含量（%）C₄₀ H₂₇ N₅ ：C, 83.17; H, 4.71; N, 12.12；實測元素含量（%）：C, 83.18; H, 4.72; N, 12.10。上述分析結果表明，獲得的產物為目標產品。Example 168

According to the synthesis of Example 3, the steps are the same, 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 (The yield is 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.

依照實施例4的合成，步驟相同，用化合物[1,1'-聯苯] -4-甲醛代替化合物苯甲醛，得到白色化合物0.531g（產率36.7%）。質譜分析確定的分子離子質量為：577.29（計算值為：577.23）；理論元素含量（%）C₄₀ H₂₇ N₅ ：C, 83.17; H, 4.71; N, 12.12；實測元素含量（%）：C, 83.18; H, 4.72; N, 12.10。上述分析結果表明，獲得的產物為目標產品。Example 169

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.

依照實施例5的合成，步驟相同，用[1,1'-聯苯] -4-甲醛代替化合物苯甲醛，得到白色化合物0.538g（產率34.3%）。質譜分析確定的分子離子質量為：577.31（計算值為：577.23）；理論元素含量（%）C₄₀ H₂₇ N₅ ：C, 83.17; H, 4.71; N, 12.12；實測元素含量（%）：C, 83.18; H, 4.72; N, 12.10。上述分析結果表明，獲得的產物為目標產品。Example 170

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.

依照實施例6的合成，步驟相同，用[1,1'-聯苯] -4-甲醛代替化合物苯甲醛，得到白色化合物0.527g（產率36.7%）。質譜分析確定的分子離子質量為：577.25（計算值為：577.23）；理論元素含量（%）C₄₀ H₂₇ N₅ ：C, 83.17; H, 4.71; N, 12.12；實測元素含量（%）：C, 83.18; H, 4.72; N, 12.10。上述分析結果表明，獲得的產物為目標產品。Example 171

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.

Effect Example 1

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 min, and then 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 5x10 ^-4 Pa or less, the evaporation starts. The deposition rate is determined by the Sainz Film Thickness Meter and the vacuum evaporation process is used on the ITO. Various organic layers, LiF electron injection layers and metal Al electrodes are sequentially deposited on the 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 an anhydrous and oxygen-free glove box.

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 (5 nm)/DBBA (60 nm)/TCTA (10 nm)/TCTA: n+10 _wt %IrPPy ₃ /n (30 nm)/LiF(1 nm)/Al(100 nm)]. 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 10 _WT %). The results of the effect examples are shown in Table 1-1.

Comparative Example 1

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; 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, and IrPPy ₃ doped luminescent material is used (the weight ratio doping concentration is 10 _WT %) , 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 (5 nm)/DBBA (60 nm)/TCTA (10 nm)/TCTA: 3P-T2T or E1 or E2 +10wt% IrPPy ₃ /3P-T2T or E1 or E2 (30 nm)/LiF(1 nm)/Al(100 nm)].

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 (5 nm)/DBBA (60 nm)/TCTA (10 nm)/n +10wt%IrPPy ₃ /n (30 nm) /LiF(1 nm)/Al(100 nm)]. 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 doping concentration is 10 _WT % by weight). The results of the comparative example are shown in Table 2-1.

、

、

、

、

、

、

、

、

、

、

。The structures of the compounds involved in the effect examples and comparative examples are as follows:

,

,

,

,

,

,

,

,

,

,

.

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). Effect embodiment number Body material (TCTA:n) Electron transmission material (n) Brightness (cd/m ² ) Current efficiency (cd/A) Device life (T90: hour) 1-1 TCTA:1 1 8785 89 1241 2-1 TCTA: 2 2 8960 86 1253 3-1 TCTA: 3 3 8695 87 1187 4-1 TCTA: 4 4 8805 88 1223 5-1 TCTA: 5 5 8423 82 1200 6-1 TCTA: 6 6 8455 84 1204 7-1 TCTA: 7 7 8845 88 1244 8-1 TCTA: 8 8 8376 87 1120 9-1 TCTA: 9 9 8768 87 1230 10-1 TCTA: 10 10 8569 86 1189 11-1 TCTA: 11 11 8755 84 1176 12-1 TCTA: 12 12 8699 83 1263 13-1 TCTA: 13 13 8756 84 1253 14-1 TCTA: 14 14 8459 86 1280 15-1 TCTA: 15 15 8756 85 1253 16-1 TCTA: 16 16 8821 87 1263 17-1 TCTA: 17 17 8754 86 1274 18-1 TCTA: 18 18 8752 87 1237 19-1 TCTA: 19 19 8619 88 1164 20-1 TCTA: 20 20 8665 83 1246 21-1 TCTA: 21 twenty one 8551 82 1268 22-1 TCTA: 22 twenty two 8817 81 1235 23-1 TCTA: 23 twenty three 8663 86 1134 24-1 TCTA: 24 twenty four 8885 84 1249 25-1 TCTA: 25 25 8637 84 1156 26-1 TCTA: 26 26 8889 89 1146 27-1 TCTA: 27 27 8776 82 1187 28-1 TCTA: 28 28 8771 86 1188 29-1 TCTA: 29 29 8634 91 1142 30-1 TCTA: 30 30 8811 90 1119 31-1 TCTA: 31 31 8727 89 1023 32-1 TCTA: 32 32 8810 84 1056 33-1 TCTA: 33 33 8559 86 1205 34-1 TCTA: 34 34 8887 85 1090 35-1 TCTA: 35 35 8608 87 1099 36-1 TCTA: 36 36 8600 88 1138 37-1 TCTA: 37 37 8889 86 1172 38-1 TCTA: 38 38 8442 85 1171 39-1 TCTA: 39 39 8776 88 1181 40-1 TCTA: 40 40 8333 85 1191 41-1 TCTA: 41 41 8770 86 1210 42-1 TCTA: 42 42 8390 84 1246 43-1 TCTA: 43 43 8826 86 1244 44-1 TCTA: 44 44 8455 82 1140 45-1 TCTA: 45 45 8598 82 1023 46-1 TCTA: 46 46 8557 80 1055 47-1 TCTA: 47 47 8450 86 1123 48-1 TCTA: 48 48 8840 83 1050 49-1 TCTA: 49 49 8700 84 1070 50-1 TCTA: 50 50 8549 83 1042 51-1 TCTA: 51 51 8646 87 1130 52-1 TCTA: 52 52 8529 84 1230 53-1 TCTA: 53 53 8434 87 1241 54-1 TCTA: 54 54 8415 85 1287 55-1 TCTA: 55 55 8492 80 1284 56-1 TCTA: 56 56 8706 84 1268 57-1 TCTA: 57 57 8718 87 1249 58-1 TCTA: 58 58 8810 84 1235 59-1 TCTA: 59 59 8637 86 1246 60-1 TCTA: 60 60 8471 87 1235 61-1 TCTA: 61 61 8383 85 1243 62-1 TCTA: 62 62 8821 84 1291 63-1 TCTA: 6 63 8371 81 1218 64-1 TCTA: 64 64 8859 87 1234 65-1 TCTA: 65 65 8767 90 1243 66-1 TCTA: 66 66 8739 83 1235 67-1 TCTA: 67 67 8627 85 1251 68-1 TCTA: 68 68 8721 83 1213 69-1 TCTA: 69 69 8660 86 1238 70-1 TCTA: 70 70 8820 83 1284 71-1 TCTA: 71 71 8501 82 1243 72-1 TCTA: 72 72 8774 87 1143 73-1 TCTA: 73 73 8703 90 1162 74-1 TCTA: 74 74 8651 89 1143 75-1 TCTA: 75 75 8389 87 1136 76-1 TCTA: 76 76 8685 85 1268 77-1 TCTA: 77 77 8462 81 1182 78-1 TCTA: 78 78 8746 87 1246 79-1 TCTA: 79 79 8496 83 1202 80-1 TCTA: 80 80 8753 85 1222 81-1 TCTA: 81 81 8315 87 1123 82-1 TCTA: 82 82 8396 89 1104 83-1 TCTA: 83 83 8886 86 1075 84-1 TCTA: 84 84 8397 79 1260 85-1 TCTA: 85 85 8704 83 1155 86-1 TCTA: 86 86 8373 90 1294 87-1 TCTA: 87 87 8421 84 1143 88-1 TCTA: 88 88 8695 83 1217 89-1 TCTA: 89 89 8446 86 1150 90-1 TCTA: 90 90 8481 81 1167 91-1 TCTA: 91 91 8821 89 1289 92-1 TCTA: 92 92 8786 85 1271 93-1 TCTA: 93 93 8324 89 1286 94-1 TCTA: 94 94 8887 88 1261 95-1 TCTA: 95 95 8515 83 1108 96-1 TCTA: 96 96 8849 84 1183 97-1 TCTA: 97 97 8368 87 1226 98-1 TCTA: 98 98 8520 85 1182 99-1 TCTA: 99 99 8814 86 1225 100-1 TCTA: 100 100 8891 90 1194 101-1 TCTA:101 101 8840 80 1157 102-1 TCTA: 102 102 8311 83 1275 103-1 TCTA:103 103 8727 84 1121 104-1 TCTA: 104 104 8768 85 1252 105-1 TCTA: 105 105 8817 89 1273 106-1 TCTA: 106 106 8763 86 1251 107-1 TCTA:107 107 8753 82 1197 108-1 TCTA: 108 108 8518 81 1119 109-1 TCTA:109 109 8863 83 1216 110-1 TCTA: 110 110 8720 90 1213 111-1 TCTA:111 111 8765 87 1164 112-1 TCTA: 112 112 8868 89 1231 113-1 TCTA: 113 113 8610 88 1186 114-1 TCTA: 114 114 8389 84 1136 115-1 TCTA: 115 115 8576 82 1299 116-1 TCTA: 116 116 8555 82 1260 117-1 TCTA:117 117 8378 84 1268 118-1 TCTA:118 118 8717 83 1207 119-1 TCTA: 119 119 8663 90 1225 120-1 TCTA: 120 120 8772 83 1221 121-1 TCTA: 121 121 8758 85 1232 122-1 TCTA: 122 122 8450 88 1167 123-1 TCTA: 123 123 8513 87 1127 124-1 TCTA:124 124 8321 82 1113 125-1 TCTA: 125 125 8388 80 1276 126-1 TCTA: 126 126 8807 87 1184 127-1 TCTA:127 127 8655 90 1107 128-1 TCTA: 128 128 8653 84 1131 129-1 TCTA: 129 129 8588 82 1114 130-1 TCTA: 130 130 8584 87 1141 131-1 TCTA: 131 131 8485 91 1243 132-1 TCTA: 132 132 8697 83 1138 133-1 TCTA: 133 133 8604 82 1262 134-1 TCTA:134 134 8448 89 1206 135-1 TCTA: 135 135 8335 90 1134 136-1 TCTA:136 136 8665 87 1161 137-1 TCTA:137 137 8512 90 1200 138-1 TCTA:138 138 8666 81 1212 139-1 TCTA: 139 139 8458 89 1287 140-1 TCTA: 140 140 8665 82 1226 141-1 TCTA:141 141 8633 82 1210 142-1 TCTA: 142 142 8814 90 1180 143-1 TCTA: 143 143 8310 84 1206 144-1 TCTA: 144 144 8836 91 1249 145-1 TCTA: 145 145 8845 81 1125 146-1 TCTA: 146 146 8776 82 1186 147-1 TCTA: 147 147 8798 84 1192 148-1 TCTA: 148 148 8347 87 1110 149-1 TCTA:149 149 8421 89 1293 150-1 TCTA: 150 150 8814 88 1155 151-1 TCTA: 151 151 8700 81 1134 152-1 TCTA: 152 152 8396 90 1219 153-1 TCTA: 153 153 8770 83 1241 154-1 TCTA:154 154 8395 83 1176 155-1 TCTA: 155 155 8837 84 1286 156-1 TCTA: 156 156 8522 85 1259 157-1 TCTA: 157 157 8561 87 1124 158-1 TCTA:158 158 8324 84 1136 159-1 TCTA:159 159 8494 83 1229 160-1 TCTA: 160 160 8590 85 1207 161-1 TCTA:161 161 8840 89 1138 162-1 TCTA:162 162 8834 80 1109 163-1 TCTA:163 163 8860 84 1112 164-1 TCTA:164 164 8423 83 1250 165-1 TCTA:165 165 8628 84 1226 166-1 TCTA: 166 166 8746 85 1269 167-1 TCTA:167 167 8642 81 1164 168-1 TCTA:168 168 8491 86 1156 169-1 TCTA:169 169 8743 86 1180 170-1 TCTA: 170 170 8837 83 1197 171-1 TCTA: 171 171 8686 88 1104

Table 2-1. Test data of the comparative example device under the condition of 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). Comparative Example Body material Electron transport material Brightness (cd/m ² ) Current efficiency (cd/A) Device life (T90: hour) 1-1 TCTA: 3P-T2T 3P-T2T 5632 61 443 2-1 TCTA:E1 E1 5180 56 426 3-1 TCTA:E2 E2 5082 52 410 4-1 TBT-07 TBT-07 5539 55 689 5-1 TBT-14 TBT-14 5496 54 663 6-1 ET85 ET85 5337 52 639 7-1 1 1 5770 55 641 8-1 3 3 5764 56 653 9-1 4 4 5691 54 635 10-1 130 130 5593 55 629 11-1 135 135 5766 56 690 12-1 150 150 5810 54 637 13-1 160 160 5749 57 624 14-1 165 165 5576 55 631 15-1 170 170 5731 54 629

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. The brightness of the organic electroluminescent device can reach 8310cd/m ² -8960 cd/m ² ; the current efficiency can reach 79 cd/A -91 cd/A; the lifetime of the device can reach 1023 hours-1299 hours (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 as the electron acceptor material to construct the light emitting layer is 5082 cd/m ² -5810 cd/ m ² ; current efficiency is 52 cd/A -57 cd/A; device lifetime is 410 hours-690 hours (T90).

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%.

Effect Example 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 (5 nm)/DBBA (60 nm)/TCTA (10 nm)/TCTA: n+10 _wt %IrPPy ₃ /TPBI (30 nm)/LiF(1 nm)/Al(100 nm)]. 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 10 _WT %). The results of the effect examples are shown in Table 1-2.

Comparative Example 2

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 10 _WT %), TPBI is used as an electron transport material. Comparative examples 1-2 to 6-2 organic electroluminescent device structure is [ITO/HATCN (5 nm)/DBBA (60 nm)/TCTA (10 nm)/TCTA: 3P-T2T, E1, E2, TBT- 07, TBT-14 or ET85+10wt% IrPPy ₃ /TPBI (30 nm)/LiF(1 nm)/Al(100 nm)].

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 10 _WT %); TPBI is used as Use of electronic transmission materials. Comparative Examples 7-2 to 15-2 organic electroluminescent device structures are [ITO/HATCN (5 nm)/DBBA (60 nm)/TCTA (10 nm)/n+10wt% IrPPy ₃ /TPBI (30 nm) /LiF(1 nm)/Al(100 nm)]. The results of the comparative example are shown in Table 2-2.

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). Effect embodiment number Body material (TCTA:n) Electron transport material Brightness (cd/m ² ) Current efficiency (cd/A) Device life (T90: hour) 1-2 TCTA:1 TPBI 7724 77 963 2-2 TCTA: 2 TPBI 7581 75 957 3-2 TCTA: 3 TPBI 7625 76 900 4-2 TCTA: 4 TPBI 7626 75 905 5-2 TCTA: 5 TPBI 7700 76 970 6-2 TCTA: 6 TPBI 7776 77 985 7-2 TCTA: 7 TPBI 7347 74 956 8-2 TCTA: 8 TPBI 7630 75 867 9-2 TCTA: 9 TPBI 7789 78 895 10-2 TCTA: 10 TPBI 7641 75 963 11-2 TCTA: 11 TPBI 7655 74 921 12-2 TCTA: 12 TPBI 7649 75 917 13-2 TCTA: 13 TPBI 7890 79 935 14-2 TCTA: 14 TPBI 7865 77 901 15-2 TCTA: 15 TPBI 7899 79 908 16-2 TCTA: 16 TPBI 7108 72 964 17-2 TCTA: 17 TPBI 7100 73 971 18-2 TCTA: 18 TPBI 7250 72 962 19-2 TCTA: 19 TPBI 7219 73 946 20-2 TCTA: 20 TPBI 7665 77 956 21-2 TCTA: 21 TPBI 7551 75 864 22-2 TCTA: 22 TPBI 7817 79 854 23-2 TCTA: 23 TPBI 7663 77 847 24-2 TCTA: 24 TPBI 7685 76 865 25-2 TCTA: 25 TPBI 7637 75 869 26-2 TCTA: 26 TPBI 7689 77 971 27-2 TCTA: 27 TPBI 7176 72 952 28-2 TCTA: 28 TPBI 7571 75 964 29-2 TCTA: 29 TPBI 7336 73 856 30-2 TCTA: 30 TPBI 7641 76 883 31-2 TCTA: 31 TPBI 7527 75 867 32-2 TCTA: 32 TPBI 7810 79 879 33-2 TCTA: 33 TPBI 7559 75 836 34-2 TCTA: 34 TPBI 7787 78 908 35-2 TCTA: 35 TPBI 7108 72 907 36-2 TCTA: 36 TPBI 7500 75 946 37-2 TCTA: 37 TPBI 7389 73 972 38-2 TCTA: 38 TPBI 7442 74 869 39-2 TCTA: 39 TPBI 7771 78 914 40-2 TCTA: 40 TPBI 7651 76 918 41-2 TCTA: 41 TPBI 7457 74 933 42-2 TCTA: 42 TPBI 7390 73 941 43-2 TCTA: 43 TPBI 7662 75 899 44-2 TCTA: 44 TPBI 7658 75 897 45-2 TCTA: 45 TPBI 7981 78 977 46-2 TCTA: 46 TPBI 7565 80 973 47-2 TCTA: 47 TPBI 7662 76 911 48-2 TCTA: 48 TPBI 7840 73 940 49-2 TCTA: 49 TPBI 7700 78 970 50-2 TCTA: 50 TPBI 7549 74 942 51-2 TCTA: 51 TPBI 7646 77 940 52-2 TCTA: 52 TPBI 7529 74 930 53-2 TCTA: 53 TPBI 7434 77 841 54-2 TCTA: 54 TPBI 7415 75 887 55-2 TCTA: 55 TPBI 7894 80 984 56-2 TCTA: 56 TPBI 7706 74 868 57-2 TCTA: 57 TPBI 7718 77 949 58-2 TCTA: 58 TPBI 7810 74 935 59-2 TCTA: 59 TPBI 7637 74 846 60-2 TCTA: 60 TPBI 7471 77 935 61-2 TCTA: 61 TPBI 7383 75 943 62-2 TCTA: 62 TPBI 7821 74 891 63-2 TCTA: 6 TPBI 7371 72 918 64-2 TCTA: 64 TPBI 7859 77 934 65-2 TCTA: 65 TPBI 7687 80 943 66-2 TCTA: 66 TPBI 7739 79 935 67-2 TCTA: 67 TPBI 7627 79 851 68-2 TCTA: 68 TPBI 7721 83 913 69-2 TCTA: 69 TPBI 7660 73 938 70-2 TCTA: 70 TPBI 7820 73 984 71-2 TCTA: 71 TPBI 7501 72 943 72-2 TCTA: 72 TPBI 7764 77 943 73-2 TCTA: 73 TPBI 7703 80 862 74-2 TCTA: 74 TPBI 7651 79 943 75-2 TCTA: 75 TPBI 7389 72 936 76-2 TCTA: 76 TPBI 7685 75 868 77-2 TCTA: 77 TPBI 7462 72 882 78-2 TCTA: 78 TPBI 7746 77 946 79-2 TCTA: 79 TPBI 7350 73 856 80-2 TCTA: 80 TPBI 7898 77 890 81-2 TCTA: 81 TPBI 7405 74 876 82-2 TCTA: 82 TPBI 7614 77 973 83-2 TCTA: 83 TPBI 7740 75 870 84-2 TCTA: 84 TPBI 7566 75 957 85-2 TCTA: 85 TPBI 7583 75 943 86-2 TCTA: 86 TPBI 7759 77 928 87-2 TCTA: 87 TPBI 7352 72 835 88-2 TCTA: 88 TPBI 7623 76 944 89-2 TCTA: 89 TPBI 7854 78 857 90-2 TCTA: 90 TPBI 7426 74 973 91-2 TCTA: 91 TPBI 7579 75 899 92-2 TCTA: 92 TPBI 7874 79 965 93-2 TCTA: 93 TPBI 7697 77 832 94-2 TCTA: 94 TPBI 7868 78 886 95-2 TCTA: 95 TPBI 7245 72 964 96-2 TCTA: 96 TPBI 7369 73 923 97-2 TCTA: 97 TPBI 7489 75 872 98-2 TCTA: 98 TPBI 7520 75 905 99-1 TCTA: 99 TPBI 7814 78 882 100-2 TCTA: 100 TPBI 7891 79 894 101-2 TCTA:101 TPBI 7540 76 957 102-2 TCTA: 102 TPBI 7311 73 875 103-2 TCTA:103 TPBI 7727 77 921 104-2 TCTA: 104 TPBI 7468 75 852 105-2 TCTA: 105 TPBI 7817 78 873 106-2 TCTA: 106 TPBI 7463 74 851 107-2 TCTA:107 TPBI 7353 72 897 108-2 TCTA: 108 TPBI 7514 75 919 109-2 TCTA:109 TPBI 7863 79 936 110-2 TCTA: 110 TPBI 7320 73 833 111-2 TCTA:111 TPBI 7658 77 864 112-2 TCTA: 112 TPBI 7862 78 935 113-2 TCTA: 113 TPBI 7296 72 886 114-2 TCTA: 114 TPBI 7389 74 839 115-2 TCTA: 115 TPBI 7576 75 909 116-2 TCTA: 116 TPBI 7565 75 943 117-2 TCTA:117 TPBI 7836 77 898 118-2 TCTA:118 TPBI 7617 76 907 119-2 TCTA: 119 TPBI 7663 78 944 120-2 TCTA: 120 TPBI 7325 73 872 121-2 TCTA: 121 TPBI 7875 79 932 122-2 TCTA: 122 TPBI 7450 74 916 123-2 TCTA: 123 TPBI 7513 75 909 124-2 TCTA:124 TPBI 7421 73 861 125-2 TCTA: 125 TPBI 7839 80 896 126-2 TCTA: 126 TPBI 7087 72 858 127-2 TCTA:127 TPBI 7655 76 917 128-2 TCTA: 128 TPBI 7563 74 931 129-2 TCTA: 129 TPBI 7581 76 841 130-2 TCTA: 130 TPBI 7458 72 925 131-2 TCTA: 131 TPBI 7714 79 912 132-2 TCTA: 132 TPBI 7652 77 965 133-2 TCTA: 133 TPBI 7401 72 971 134-2 TCTA:134 TPBI 7848 80 868 135-2 TCTA: 135 TPBI 7435 73 835 136-2 TCTA:136 TPBI 7665 78 861 137-2 TCTA:137 TPBI 7512 75 920 138-2 TCTA:138 TPBI 7663 74 912 139-2 TCTA: 139 TPBI 7548 76 887 140-2 TCTA: 140 TPBI 7365 72 926 141-2 TCTA:141 TPBI 7633 77 910 142-2 TCTA: 142 TPBI 7814 79 978 143-2 TCTA: 143 TPBI 7507 74 926 144-2 TCTA: 144 TPBI 7836 79 849 145-2 TCTA: 145 TPBI 7845 78 951 146-2 TCTA: 146 TPBI 7276 73 886 147-2 TCTA: 147 TPBI 7798 78 919 148-2 TCTA: 148 TPBI 7347 74 910 149-2 TCTA:149 TPBI 7621 77 932 150-2 TCTA: 150 TPBI 7148 73 955 151-2 TCTA: 151 TPBI 7800 78 934 152-2 TCTA: 152 TPBI 7696 80 928 153-2 TCTA: 153 TPBI 7870 79 914 154-2 TCTA:154 TPBI 7395 74 876 155-2 TCTA: 155 TPBI 7379 74 884 156-2 TCTA: 156 TPBI 7524 76 959 157-2 TCTA: 157 TPBI 7361 72 924 158-2 TCTA:158 TPBI 7424 74 836 159-2 TCTA:159 TPBI 7392 73 892 160-2 TCTA: 160 TPBI 7590 75 907 161-2 TCTA:161 TPBI 7840 79 938 162-2 TCTA:162 TPBI 7383 74 827 163-2 TCTA:163 TPBI 7860 80 830 164-2 TCTA:164 TPBI 7423 75 845 165-2 TCTA:165 TPBI 7628 77 926 166-2 TCTA: 166 TPBI 7746 75 869 167-2 TCTA:167 TPBI 7642 73 964 168-2 TCTA:168 TPBI 7491 76 915 169-2 TCTA:169 TPBI 7743 78 918 170-2 TCTA: 170 TPBI 7837 80 978 171-2 TCTA: 171 TPBI 7686 78 841

Table 2-2. 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). Comparative Example Body material Electron transport material Brightness (cd/m ² ) Current efficiency (cd/A) Device life (T90: hour) 1-2 TCTA: 3P-T2T TPBI 5632 61 443 2-2 TCTA:E1 TPBI 5180 56 426 3-2 TCTA:E2 TPBI 5082 52 410 4-2 TCTA:TBT-07 TPBI 5639 62 672 5-2 TCTA:TBT-14 TPBI 5572 63 657 6-2 TCTA :ET85 TPBI 5715 62 671 7-2 1 TPBI 5564 50 576 8-2 3 TPBI 5781 51 590 9-2 4 TPBI 5623 49 619 10-2 130 TPBI 5543 50 631 11-2 135 TPBI 5706 51 625 12-2 150 TPBI 5649 48 617 13-2 160 TPBI 5607 49 603 14-2 165 TPBI 5590 51 620 15-2 170 TPBI 5631 50 597

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 a brightness of ^{7087 cd / m 2 - 7981cd cd} / m 2; the current efficiency of up to 72 cd / A -83 cd / A ; device life up to 827 hours -985 hours (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 compounds to construct the light-emitting layer is 5082 cd/m ² -5781 cd/m ² ; the current efficiency is 48 cd/A- 63 cd/A; device life is 410 hours -672 hours (T90).

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 organic electroluminescent devices, the brightness is increased by 22.6%-57%, the current efficiency is increased by 14%-73%, and the device life is increased by 23%-140%.

Effect Example 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(5 nm)/DBBA(60 nm)/TCTA(10 nm)/TCTA+10 _wt %IrPPy ₃ /n(30 nm)/LiF(1 nm) /Al(100 nm)]. 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 10 _WT %). The results of the effect examples are shown in Table 1-3.

Comparative Example 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 10 _WT %), 3P-T2T, E1, E2, TBT-07, TBT-14 and ET85 are used Used as an electronic transmission material. Comparative Examples 1-3 to 6-3 organic electroluminescent device structure is [ITO/HATCN (5 nm)/DBBA (60 nm)/TCTA (10 nm)/TCTA +10wt% IrPPy ₃ /3P-T2T, E1 , E2, TBT-07, TBT-14 or ET85 (30 nm)/LiF(1 nm)/Al(100 nm)]. The results of the comparative example are shown in Table 2-3.

Table 1-3. 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). Effect embodiment number Body material Electron transmission material (n) Brightness (cd/m ² ) Current efficiency (cd/A) Device life (T90: hour) 1-3 TCTA 1 6730 73 812 2-3 TCTA 2 6812 72 792 3-3 TCTA 3 6395 68 775 4-3 TCTA 4 6830 74 752 5-3 TCTA 5 6423 68 856 6-3 TCTA 6 6455 68 877 7-3 TCTA twenty one 6845 74 823 8-3 TCTA twenty two 6476 68 846 9-3 TCTA twenty three 6768 73 858 10-3 TCTA twenty four 6569 69 865 11-3 TCTA 25 6755 73 835 12-3 TCTA 26 6687 70 846 13-3 TCTA 27 6756 71 851 14-3 TCTA 28 6459 68 852 15-3 TCTA 29 6756 73 827 16-3 TCTA 30 6821 74 869 17-3 TCTA 31 6754 73 855 18-3 TCTA 32 6752 73 843 19-3 TCTA 61 6619 68 847 20-3 TCTA 62 6765 73 865 21-3 TCTA 63 6551 71 819 22-3 TCTA 64 6715 72 837 23-3 TCTA 65 6763 73 769 24-3 TCTA 66 6885 74 842 25-3 TCTA 67 6637 72 856 26-3 TCTA 68 6489 68 846 27-3 TCTA 69 6576 71 787 28-3 TCTA 70 6771 73 788 29-3 TCTA 71 6634 72 842 30-3 TCTA 72 6811 73 859 31-3 TCTA 73 6727 73 823 32-3 TCTA 74 7010 75 756 33-3 TCTA 75 6559 69 805 34-3 TCTA 76 6887 73 793 35-3 TCTA 77 6708 72 769 36-3 TCTA 78 6620 72 798 37-3 TCTA 79 6789 73 872 38-3 TCTA 80 6442 68 871 39-3 TCTA 81 6476 68 781 40-3 TCTA 82 6653 66 791 41-3 TCTA 83 6770 72 810 42-3 TCTA 84 6390 66 846 43-3 TCTA 141 6826 73 844 44-3 TCTA 142 6465 68 840 45-3 TCTA 143 6598 70 823 46-3 TCTA 144 6547 69 855 47-3 TCTA 145 6450 68 823 48-3 TCTA 146 6846 73 840 49-3 TCTA 164 6705 71 770 50-3 TCTA 165 6549 69 842 51-3 TCTA 166 6646 70 840 52-3 TCTA 167 6529 69 830 53-3 TCTA 168 6434 68 791 54-3 TCTA 169 6415 68 787 55-3 TCTA 170 6894 73 780 56-3 TCTA 171 6706 71 768 57-3 TCTA 172 6718 71 849 58-3 TCTA 173 6810 72 835 59-3 TCTA 174 6637 70 846 60-3 TCTA 175 6471 67 835 61-3 TCTA 176 6383 66 843 62-3 TCTA 177 6826 72 791 63-3 TCTA 178 6371 66 818 64-3 TCTA 179 6859 72 834 65-3 TCTA 180 6778 70 843 66-3 TCTA 181 6739 71 835 67-3 TCTA 182 6627 70 851 68-3 TCTA 183 6721 71 813 69-3 TCTA 184 6570 70 838 70-3 TCTA 185 6820 72 775 71-3 TCTA 186 6501 70 843 72-3 TCTA 187 6774 71 843 73-3 TCTA 189 6703 70 862 74-3 TCTA 196 6651 72 843 75-3 TCTA 197 6389 67 836 76-3 TCTA 198 6685 70 868 77-3 TCTA 199 6462 69 782 78-3 TCTA 200 6746 72 746 79-3 TCTA 201 6591 70 802 80-3 TCTA 202 6583 71 772 81-3 TCTA 203 6415 66 773 82-3 TCTA 204 6396 68 764 83-3 TCTA 205 7035 74 795 84-3 TCTA 219 6439 66 866 85-3 TCTA 226 6904 73 767 86-3 TCTA 227 7033 74 794 87-3 TCTA 228 6621 71 783 88-3 TCTA 229 6395 66 856 89-3 TCTA 230 6446 67 752 90-3 TCTA 231 6881 72 768 91-3 TCTA 232 6821 72 789 92-3 TCTA 233 6386 66 771 93-3 TCTA 234 6568 68 756 94-3 TCTA 235 6463 67 861 95-3 TCTA 236 6615 70 808 96-3 TCTA 237 6849 73 835 97-3 TCTA 238 7069 74 786 98-3 TCTA 239 6420 66 792 99-3 TCTA 240 6514 67 754 100-3 TCTA 241 6691 70 813 101-3 TCTA 242 6840 72 857 102-3 TCTA 243 6483 65 775 103-3 TCTA 244 6727 70 821 104-3 TCTA 245 6688 69 752 105-3 TCTA 246 6381 66 773 106-3 TCTA 247 6563 68 854 107-3 TCTA 248 6453 67 816 108-3 TCTA 249 6716 71 757 109-3 TCTA 250 7023 74 768 110-3 TCTA 251 6908 73 833 111-3 TCTA 252 6654 70 765 112-3 TCTA 253 6568 69 831 113-3 TCTA 254 6862 72 786 114-3 TCTA 255 6389 66 782 115-3 TCTA 256 6576 68 844 116-3 TCTA 313 6575 67 760 117-3 TCTA 314 6973 73 768 118-3 TCTA 315 6717 71 807 119-3 TCTA 316 6863 72 781 120-3 TCTA 317 6972 70 765 121-3 TCTA 318 6854 68 832 122-3 TCTA 319 7050 71 867 123-3 TCTA 320 6513 67 827 124-3 TCTA 321 6821 72 813 125-3 TCTA 322 6983 73 776 126-3 TCTA 323 6807 72 841 127-3 TCTA 324 6715 69 810 128-3 TCTA 325 6753 70 782 129-3 TCTA 326 6982 73 841 130-3 TCTA 327 6584 68 768 131-3 TCTA 328 6485 65 824 132-3 TCTA 329 6797 71 783 133-3 TCTA 330 6604 69 826 134-3 TCTA 331 6948 72 806 135-3 TCTA 332 6835 73 814 136-3 TCTA 333 6545 68 861 137-3 TCTA 334 7012 74 820 138-3 TCTA 335 6701 70 786 139-3 TCTA 336 6580 68 778 140-3 TCTA 337 6715 67 826 141-3 TCTA 338 6433 72 810 142-3 TCTA 339 6814 70 818 143-3 TCTA 340 6907 71 762 144-3 TCTA 341 6736 70 789 145-3 TCTA 342 6945 72 815 146-3 TCTA 343 6776 70 786 147-3 TCTA 344 6598 68 819 148-3 TCTA 345 6847 71 810 149-3 TCTA 346 7021 74 793 150-3 TCTA 347 6814 72 855 151-3 TCTA 348 6970 73 834 152-3 TCTA 349 6896 73 791 153-3 TCTA 350 6470 69 824 154-3 TCTA 381 6395 68 778 155-3 TCTA 382 6837 72 786 156-3 TCTA 383 7022 74 859 157-3 TCTA 384 6561 69 794 158-3 TCTA 385 6824 73 836 159-3 TCTA 386 6494 67 822 160-3 TCTA 387 6890 72 807 161-3 TCTA 388 6371 67 838 162-3 TCTA 389 6834 71 809 163-3 TCTA 390 6960 72 795 164-3 TCTA 391 6423 68 825 165-3 TCTA 392 6628 70 822 166-3 TCTA 393 6646 70 869 167-3 TCTA 394 7050 75 864 168-3 TCTA 395 6991 74 856 169-3 TCTA 396 6743 70 818 170-3 TCTA 397 6837 72 797 171-3 TCTA 398 6686 71 804

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). Comparative Example Body material Electron transport material Brightness (cd/m ² ) Current efficiency (cd/A) Device life (T90: hour) 1-3 TCTA 3P-T2T 5010 54 387 2-3 TCTA E1 4862 51 361 3-3 TCTA E2 4913 50 374 4-3 TCTA TBT-07 5032 53 496 5-3 TCTA TBT-14 5120 56 482 6-3 TCTA: ET85 5196 55 490

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 6371 cd/m ² -7069 cd/m ² ; current efficiency can reach 65 cd/A -75 cd/A; device life can reach 746 hours -877 hours (T90).

Table 2-3 Example 3 and Comparative seen from the above embodiment, the above-described embodiment the compound prepared in Example Comparative electron transport layer as obtained luminance organic electroluminescent device was ^{4862 cd / m 2 -5196 cd /} m 2; the current efficiency was 50 cd/A -56 cd/A; device lifetime is 361 hours -496 hours (T90).

It can be seen that the 1,3,5-triazine compound of the present invention is compared with the above-mentioned existing compounds, the brightness of the organic electroluminescent device prepared as the electron transport layer is increased by 22.6%-45.4%, and the current efficiency is improved. Increased by 16%-50%; device life increased by 50%-143%.

Effect Example 4

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 an electronic transmission material. Effect Example The structure of the organic electroluminescent device is [ITO/HATCN (5 nm)/DBBA (60 nm)/TCTA (10 nm)/TCTA: n+1 _wt %DPh2AAN/n (30 nm)/LiF (1 nm) )/Al(100 nm)]. 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. DPh2AAN is used as the doped luminescent material (doping concentration by weight is 1 _WT %). The results of the effect examples are shown in Table 1-5.

Comparative Example 4

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; In the light-emitting layer, TCTA is mixed with 3P-T2T, E1 or E2 respectively as the host material, the two materials are mixed in a weight ratio of 1:1, and DPh2AAN doped luminescent material is used (weight ratio doping concentration is 1 _WT %) 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 (5 nm)/DBBA (60 nm)/TCTA (10 nm)/TCTA: 3P-T2T or E1 or E2 +10wt% DPh2AAN/3P-T2T or E1 or E2 (30 nm)/LiF(1 nm)/Al(100 nm)].

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 device brightness to decay to 90% of the initial brightness). Effect embodiment number Body material (TCTA:n) Electron transmission material (n) Brightness (cd/m ² ) Current efficiency (cd/A) Device life (T90: hour) 1-4 TCTA:1 1 3842 60 971 2-4 TCTA: 2 2 3791 62 990 3-4 TCTA: 3 3 3832 59 957 4-4 TCTA: 4 4 3810 57 969 5-4 TCTA: 5 5 3850 58 932 6-4 TCTA: 6 6 3677 57 977 7-4 TCTA: 7 7 3875 62 949 8-4 TCTA: 8 8 3856 54 986 9-4 TCTA: 9 9 3593 62 931 10-4 TCTA: 10 10 3618 56 919 11-4 TCTA: 11 11 3733 55 937 12-4 TCTA: 12 12 3744 59 970 13-4 TCTA: 13 13 3710 55 977 14-4 TCTA: 14 14 3728 61 922 15-4 TCTA: 15 15 3717 60 988 16-4 TCTA: 16 16 3518 62 929 17-4 TCTA: 17 17 3519 61 925 18-4 TCTA: 18 18 3871 57 928 19-4 TCTA: 19 19 3711 61 962 20-4 TCTA: 20 20 3879 55 935 21-4 TCTA: 21 twenty one 3823 62 962 22-4 TCTA: 22 twenty two 3661 61 981 23-4 TCTA: 23 twenty three 3634 60 929 24-4 TCTA: 24 twenty four 3852 56 931 25-4 TCTA: 25 25 3568 55 970 26-4 TCTA: 26 26 3811 58 932 27-4 TCTA: 27 27 3789 62 921 28-4 TCTA: 28 28 3730 59 945 29-4 TCTA: 29 29 3539 57 911 30-4 TCTA: 30 30 3526 59 950 31-4 TCTA: 31 31 3712 62 964 32-4 TCTA: 32 32 3646 58 935 33-4 TCTA: 33 33 3698 55 963 34-4 TCTA: 34 34 3821 56 961 35-4 TCTA: 35 35 3571 55 934 36-4 TCTA: 36 36 3679 55 946 37-4 TCTA: 37 37 3650 58 940 38-4 TCTA: 38 38 3763 56 936 39-4 TCTA: 39 39 3697 55 935 40-4 TCTA: 40 40 3787 59 956 41-4 TCTA: 41 41 3550 58 933 42-4 TCTA: 42 42 3900 57 965 43-4 TCTA: 43 43 3545 62 957 44-4 TCTA: 44 44 3628 59 973 45-4 TCTA: 45 45 3607 54 945 46-4 TCTA: 46 46 3553 60 955 47-4 TCTA: 47 47 3868 58 923 48-4 TCTA: 48 48 3802 61 933 49-4 TCTA: 49 49 3652 62 920 50-4 TCTA: 50 50 3710 58 984 51-4 TCTA: 51 51 3501 56 971 52-4 TCTA: 52 52 3853 57 948 53-4 TCTA: 53 53 3859 54 964 54-4 TCTA: 54 54 3701 56 922 55-4 TCTA: 55 55 3625 59 971 56-4 TCTA: 56 56 3775 58 929 57-4 TCTA: 57 57 3708 54 985 58-4 TCTA: 58 58 3617 55 977 59-4 TCTA: 59 59 3609 57 956 60-4 TCTA: 60 60 3810 54 968 61-4 TCTA: 61 61 3694 60 926 62-4 TCTA: 62 62 3675 58 930 63-4 TCTA: 6 63 3750 56 910 64-4 TCTA: 64 64 3844 60 923 65-4 TCTA: 65 65 3687 55 956 66-4 TCTA: 66 66 3772 61 967 67-4 TCTA: 67 67 3725 59 983 68-4 TCTA: 68 68 3504 60 910 69-4 TCTA: 69 69 3893 62 947 70-4 TCTA: 70 70 3545 58 978 71-4 TCTA: 71 71 3873 54 927 72-4 TCTA: 72 72 3785 56 919 73-4 TCTA: 73 73 3754 61 943 74-4 TCTA: 74 74 3869 58 989 75-4 TCTA: 75 75 3592 61 979 76-4 TCTA: 76 76 3767 55 947 77-4 TCTA: 77 77 3856 56 945 78-4 TCTA: 78 78 3705 57 948 79-4 TCTA: 79 79 3772 59 960 80-4 TCTA: 80 80 3548 58 951 81-4 TCTA: 81 81 3846 55 985 82-4 TCTA: 82 82 3621 56 948 83-4 TCTA: 83 83 3728 56 930 84-4 TCTA: 84 84 3634 54 926 85-4 TCTA: 85 85 3610 56 974 86-4 TCTA: 86 86 3675 57 911 87-4 TCTA: 87 87 3618 59 945 88-4 TCTA: 88 88 3599 58 913 89-4 TCTA: 89 89 3743 62 968 90-4 TCTA: 90 90 3607 59 936 91-4 TCTA: 91 91 3685 57 965 92-4 TCTA: 92 92 3862 62 921 93-4 TCTA: 93 93 3625 60 952 94-4 TCTA: 94 94 3550 62 944 95-4 TCTA: 95 95 3554 58 945 96-4 TCTA: 96 96 3587 57 951 97-4 TCTA: 97 97 3548 61 926 98-4 TCTA: 98 98 3683 54 946 99-4 TCTA: 99 99 3608 62 912 100-4 TCTA: 100 100 3789 56 951 101-4 TCTA:101 101 3667 61 967 102-4 TCTA: 102 102 3570 57 930 103-4 TCTA:103 103 3853 60 986 104-4 TCTA: 104 104 3755 58 949 105-4 TCTA: 105 105 3613 59 927 106-4 TCTA: 106 106 3521 54 938 107-4 TCTA:107 107 3859 61 945 108-4 TCTA: 108 108 3663 56 930 109-4 TCTA:109 109 3807 54 931 110-4 TCTA: 110 110 3662 60 984 111-4 TCTA:111 111 3755 54 982 112-4 TCTA: 112 112 3657 58 962 113-4 TCTA: 113 113 3652 57 949 114-4 TCTA: 114 114 3706 62 985 115-4 TCTA: 115 115 3746 56 924 116-4 TCTA: 116 116 3580 60 969 117-4 TCTA:117 117 3846 59 943 118-4 TCTA:118 118 3772 54 981 119-4 TCTA: 119 119 3747 60 961 120-4 TCTA: 120 120 3884 57 953 121-4 TCTA: 121 121 3745 61 954 122-4 TCTA: 122 122 3658 62 954 123-4 TCTA: 123 123 3885 60 973 124-4 TCTA:124 124 3601 54 969 125-4 TCTA: 125 125 3676 57 936 126-4 TCTA: 126 126 3507 55 928 127-4 TCTA:127 127 3809 57 932 128-4 TCTA: 128 128 3675 56 915 129-4 TCTA: 129 129 3655 62 910 130-4 TCTA: 130 130 3556 57 961 131-4 TCTA: 131 131 3660 54 957 132-4 TCTA: 132 132 3813 58 980 133-4 TCTA: 133 133 3750 57 953 134-4 TCTA:134 134 3876 57 959 135-4 TCTA: 135 135 3869 54 922 136-4 TCTA:136 136 3535 55 957 137-4 TCTA:137 137 3723 60 975 138-4 TCTA:138 138 3861 61 950 139-4 TCTA: 139 139 3504 54 953 140-4 TCTA: 140 140 3763 59 917 141-4 TCTA:141 141 3661 57 938 142-4 TCTA: 142 142 3764 55 913 143-4 TCTA: 143 143 3722 58 929 144-4 TCTA: 144 144 3875 62 986 145-4 TCTA: 145 145 3549 59 917 146-4 TCTA: 146 146 3661 54 942 147-4 TCTA: 147 147 3870 56 920 148-4 TCTA: 148 148 3708 57 962 149-4 TCTA:149 149 3686 60 944 150-4 TCTA: 150 150 3605 61 950 151-4 TCTA: 151 151 3723 59 957 152-4 TCTA: 152 152 3850 61 941 153-4 TCTA: 153 153 3729 60 972 154-4 TCTA:154 154 3806 57 961 155-4 TCTA: 155 155 3865 60 947 156-4 TCTA: 156 156 3863 59 946 157-4 TCTA: 157 157 3829 56 939 158-4 TCTA:158 158 3606 55 976 159-4 TCTA:159 159 3892 61 935 160-4 TCTA: 160 160 3610 60 911 161-4 TCTA:161 161 3712 61 985 162-4 TCTA:162 162 3544 60 979 163-4 TCTA:163 163 3582 55 990 164-4 TCTA:164 164 3533 58 962 165-4 TCTA:165 165 3894 57 938 166-4 TCTA: 166 166 3625 55 921 167-4 TCTA:167 167 3516 54 969 168-4 TCTA:168 168 3585 61 973 169-4 TCTA:169 169 3581 54 957 170-4 TCTA: 170 170 3862 61 944 171-4 TCTA: 171 171 3647 59 956

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). Comparative Example Body material Electron transport material Brightness (cd/m ² ) Current efficiency (cd/A) Device life (T90: hour) 1-4 TCTA: 3P-T2T 3P-T2T 2350 41 453 2-4 TCTA:E1 E1 2571 40 462 3-4 TCTA:E2 E2 2427 39 402

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 electroluminescent devices can reach 3501 cd/m ² -3900 cd/m ² ; the current efficiency can reach 54 cd/A -62 cd/A; the lifetime of the device can reach 910 hours to 990 hours (T90).

It can be seen from the above comparative examples and Table 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 2350 cd/m ² -2571 cd/m ² ; Current efficiency is 39 cd/A -41 cd/A; device lifetime is 402 hours -462 hours (T90).

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 device life is increased by 97%- 146%.

Effect Example 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 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(5 nm)/DBBA(60 nm)/TCTA(10 nm)/TCTA: n+1 _wt %DPh2AAN/TPBI(30 nm)/LiF(1 nm) )/Al(100 nm)]. n represents the compound number: 1-179, DPh2AAN is used as a doped luminescent material (weight ratio doping concentration is 1 _WT %). The results of the effect examples are shown in Table 1-5.

Comparative Example 5

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; In the light-emitting layer, TCTA is mixed with 3P-T2T, E1 or E2 respectively as the host material, the two materials are mixed in a weight ratio of 1:1, and DPh2AAN doped luminescent material is used (weight ratio doping concentration is 1 _WT %), TPBI is used as an electronic transmission material. Comparative Examples 1-5 to 3-5 organic electroluminescent device structure is [ITO/HATCN (5 nm)/DBBA (60 nm)/TCTA (10 nm)/TCTA: 3P-T2T or E1 or E2 +10wt% DPh2AAN/TPBI (30 nm)/LiF(1 nm)/Al(100 nm)].

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). Effect embodiment number Body material (TCTA:n) Electron transport material Brightness (cd/m ² ) Current efficiency (cd/A) Device life (T90: hour) 1-5 TCTA:1 TPBI 3517 53 724 2-5 TCTA: 2 TPBI 3362 49 697 3-5 TCTA: 3 TPBI 3496 51 705 4-5 TCTA: 4 TPBI 3565 55 712 5-5 TCTA: 5 TPBI 3286 52 683 6-5 TCTA: 6 TPBI 3600 56 750 7-5 TCTA: 7 TPBI 3465 53 746 8-5 TCTA: 8 TPBI 3426 54 725 9-5 TCTA: 9 TPBI 3268 52 747 10-5 TCTA: 10 TPBI 3275 51 707 11-5 TCTA: 11 TPBI 3346 55 670 12-5 TCTA: 12 TPBI 3245 53 701 13-5 TCTA: 13 TPBI 3547 56 710 14-5 TCTA: 14 TPBI 3540 48 703 15-5 TCTA: 15 TPBI 3527 53 706 16-5 TCTA: 16 TPBI 3524 52 680 17-5 TCTA: 17 TPBI 3472 54 706 18-5 TCTA: 18 TPBI 3205 49 679 19-5 TCTA: 19 TPBI 3263 48 683 20-5 TCTA: 20 TPBI 3328 50 702 21-5 TCTA: 21 TPBI 3373 53 692 22-5 TCTA: 22 TPBI 3527 52 706 23-5 TCTA: 23 TPBI 3442 51 737 24-5 TCTA: 24 TPBI 3351 49 650 25-5 TCTA: 25 TPBI 3371 50 731 26-5 TCTA: 26 TPBI 3590 53 696 27-5 TCTA: 27 TPBI 3387 52 730 28-5 TCTA: 28 TPBI 3506 51 671 29-5 TCTA: 29 TPBI 3243 48 654 30-5 TCTA: 30 TPBI 3564 52 733 31-5 TCTA: 31 TPBI 3290 54 680 32-5 TCTA: 32 TPBI 3582 56 691 33-5 TCTA: 33 TPBI 3364 52 744 34-5 TCTA: 34 TPBI 3450 53 651 35-5 TCTA: 35 TPBI 3543 50 716 36-5 TCTA: 36 TPBI 3452 56 726 37-5 TCTA: 37 TPBI 3376 53 695 38-5 TCTA: 38 TPBI 3246 50 680 39-5 TCTA: 39 TPBI 3491 54 697 40-5 TCTA: 40 TPBI 3274 53 739 41-5 TCTA: 41 TPBI 3437 48 750 42-5 TCTA: 42 TPBI 3360 50 729 43-5 TCTA: 43 TPBI 3266 49 682 44-5 TCTA: 44 TPBI 3420 51 735 45-5 TCTA: 45 TPBI 3452 54 720 46-5 TCTA: 46 TPBI 3437 50 656 47-5 TCTA: 47 TPBI 3532 53 705 48-5 TCTA: 48 TPBI 3473 55 653 49-5 TCTA: 49 TPBI 3341 52 750 50-5 TCTA: 50 TPBI 3415 54 718 51-5 TCTA: 51 TPBI 3573 56 736 52-5 TCTA: 52 TPBI 3350 55 703 53-5 TCTA: 53 TPBI 3424 52 734 54-5 TCTA: 54 TPBI 3552 53 747 55-5 TCTA: 55 TPBI 3379 49 684 56-5 TCTA: 56 TPBI 3398 54 654 57-5 TCTA: 57 TPBI 3424 53 663 58-5 TCTA: 58 TPBI 3279 49 682 59-5 TCTA: 59 TPBI 3324 55 669 60-5 TCTA: 60 TPBI 3276 54 704 61-5 TCTA: 61 TPBI 3435 48 749 62-5 TCTA: 62 TPBI 3264 55 741 63-5 TCTA: 6 TPBI 3405 51 725 64-5 TCTA: 64 TPBI 3395 50 670 65-5 TCTA: 65 TPBI 3316 54 705 66-5 TCTA: 66 TPBI 3243 48 672 67-5 TCTA: 67 TPBI 3586 56 678 68-5 TCTA: 68 TPBI 3567 54 719 69-5 TCTA: 69 TPBI 3413 55 674 70-5 TCTA: 70 TPBI 3572 50 731 71-5 TCTA: 71 TPBI 3306 51 663 72-5 TCTA: 72 TPBI 3419 49 717 73-5 TCTA: 73 TPBI 3521 50 651 74-5 TCTA: 74 TPBI 3289 54 680 75-5 TCTA: 75 TPBI 3527 56 728 76-5 TCTA: 76 TPBI 3482 52 702 77-5 TCTA: 77 TPBI 3396 54 738 78-5 TCTA: 78 TPBI 3289 51 725 79-5 TCTA: 79 TPBI 3469 56 650 80-5 TCTA: 80 TPBI 3319 55 738 81-5 TCTA: 81 TPBI 3219 56 670 82-5 TCTA: 82 TPBI 3502 50 661 83-5 TCTA: 83 TPBI 3454 55 706 84-5 TCTA: 84 TPBI 3238 56 685 85-5 TCTA: 85 TPBI 3450 54 656 86-5 TCTA: 86 TPBI 3527 55 712 87-5 TCTA: 87 TPBI 3517 56 725 88-5 TCTA: 88 TPBI 3469 55 729 89-5 TCTA: 89 TPBI 3524 54 712 90-5 TCTA: 90 TPBI 3345 55 688 91-5 TCTA: 91 TPBI 3406 53 678 92-5 TCTA: 92 TPBI 3313 52 743 93-5 TCTA: 93 TPBI 3492 48 715 94-5 TCTA: 94 TPBI 3268 55 741 95-5 TCTA: 95 TPBI 3361 52 710 96-5 TCTA: 96 TPBI 3412 48 683 97-5 TCTA: 97 TPBI 3371 52 703 98-5 TCTA: 98 TPBI 3356 50 731 99-5 TCTA: 99 TPBI 3550 56 738 100-5 TCTA: 100 TPBI 3231 49 707 101-5 TCTA:101 TPBI 3342 56 680 102-5 TCTA: 102 TPBI 3534 52 672 103-5 TCTA:103 TPBI 3481 53 737 104-5 TCTA: 104 TPBI 3353 50 727 105-5 TCTA: 105 TPBI 3510 53 704 106-5 TCTA: 106 TPBI 3459 54 748 107-5 TCTA:107 TPBI 3525 48 688 108-5 TCTA: 108 TPBI 3371 54 652 109-5 TCTA:109 TPBI 3312 53 721 110-5 TCTA: 110 TPBI 3535 52 693 111-5 TCTA:111 TPBI 3276 53 657 112-5 TCTA: 112 TPBI 3218 50 709 113-5 TCTA: 113 TPBI 3370 49 661 114-5 TCTA: 114 TPBI 3362 56 672 115-5 TCTA: 115 TPBI 3506 50 686 116-5 TCTA: 116 TPBI 3520 51 698 117-5 TCTA:117 TPBI 3416 49 673 118-5 TCTA:118 TPBI 3290 52 655 119-5 TCTA: 119 TPBI 3561 51 701 120-5 TCTA: 120 TPBI 3295 55 716 121-5 TCTA: 121 TPBI 3274 56 704 122-5 TCTA: 122 TPBI 3370 48 699 123-5 TCTA: 123 TPBI 3253 55 662 124-5 TCTA:124 TPBI 3357 52 686 125-5 TCTA: 125 TPBI 3405 49 672 126-5 TCTA: 126 TPBI 3239 51 701 127-5 TCTA:127 TPBI 3380 48 674 128-5 TCTA: 128 TPBI 3543 55 684 129-5 TCTA: 129 TPBI 3245 50 650 130-5 TCTA: 130 TPBI 3403 56 729 131-5 TCTA: 131 TPBI 3301 49 715 132-5 TCTA: 132 TPBI 3589 50 701 133-5 TCTA: 133 TPBI 3469 52 673 134-5 TCTA:134 TPBI 3277 53 654 135-5 TCTA: 135 TPBI 3389 51 743 136-5 TCTA:136 TPBI 3267 54 657 137-5 TCTA:137 TPBI 3509 56 670 138-5 TCTA:138 TPBI 3276 55 713 139-5 TCTA: 139 TPBI 3375 51 724 140-5 TCTA: 140 TPBI 3406 56 650 141-5 TCTA:141 TPBI 3478 54 671 142-5 TCTA: 142 TPBI 3581 52 710 143-5 TCTA: 143 TPBI 3453 53 658 144-5 TCTA: 144 TPBI 3296 51 734 145-5 TCTA: 145 TPBI 3350 53 672 146-5 TCTA: 146 TPBI 3317 55 721 147-5 TCTA: 147 TPBI 3396 49 730 148-5 TCTA: 148 TPBI 3269 56 733 149-5 TCTA:149 TPBI 3360 53 702 150-5 TCTA: 150 TPBI 3287 55 662 151-5 TCTA: 151 TPBI 3554 50 679 152-5 TCTA: 152 TPBI 3597 52 681 153-5 TCTA: 153 TPBI 3550 50 669 154-5 TCTA:154 TPBI 3397 52 652 155-5 TCTA: 155 TPBI 3521 51 705 156-5 TCTA: 156 TPBI 3359 48 711 157-5 TCTA: 157 TPBI 3535 47 708 158-5 TCTA:158 TPBI 3407 49 694 159-5 TCTA:159 TPBI 3265 53 662 160-5 TCTA: 160 TPBI 3582 52 722 161-5 TCTA:161 TPBI 3587 56 739 162-5 TCTA:162 TPBI 3459 50 678 163-5 TCTA:163 TPBI 3514 55 679 164-5 TCTA:164 TPBI 3261 50 668 165-5 TCTA:165 TPBI 3395 49 744 166-5 TCTA: 166 TPBI 3263 48 712 167-5 TCTA:167 TPBI 3356 53 683 168-5 TCTA:168 TPBI 3301 50 686 169-5 TCTA:169 TPBI 3404 49 676 170-5 TCTA: 170 TPBI 3253 54 746 171-5 TCTA: 171 TPBI 3425 53 685

Table 2-5. Test data of the comparative example device under the condition of 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). Comparative Example Body material Electron transport material Brightness (cd/m ² ) Current efficiency (cd/A) Device life (T90: hour) 1-5 TCTA: 3P-T2T TPBI 2032 38 375 2-5 TCTA:E1 TPBI 2171 36 342 3-5 TCTA:E2 TPBI 2205 34 361

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 It can reach 3205 cd/m ² -3600 cd/m ² ; current efficiency can reach 47 cd/A -56 cd/A; device life can reach 650 hours -750 hours (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 light-emitting layer has a brightness of 2032 cd/m ² -2205 cd/m ² and a current efficiency of 34 cd/A -38 cd/A; device life is 342 hours -375 hours (T90).

It can be seen that the 1,3,5-triazine compound of the present invention is compared with the above-mentioned existing compounds as an electron acceptor material to construct the light-emitting layer of the organic electroluminescent device, and the brightness is increased by 45%-77% , The current efficiency is increased by 23.7%-64.7%; the device life is increased by 73%-119%.

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 benzene are linked by a single bond on the periphery of a benzene ring The molecular conformation structure of this molecule is very complex; (3) Triazine derivatives and benzimidazole derivatives are 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. 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 structure 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, which can then be used in a wider range. Adjust the sublimation temperature of the target molecule within the range (200-450℃). This feature is beneficial for selecting matching materials that are close to the sublimation temperature of the target product.

It is well known by 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 characteristics of the matched doped luminescent material and the overall carrier transport characteristics 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 dopant 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 two components of electron donor and electron acceptor will be more complicated, and its performance is difficult to accurately infer based on experience.

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 Compared with only being used as an electron transport material, the efficiency and life span of the prepared organic electroluminescent device are not significantly improved.

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.

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 constructed as an electron acceptor material and an electron donor material. For the light-emitting layer, the organic electroluminescence device prepared under the same driving current density can obtain better brightness, efficiency and life. Especially the stability of the device has the most obvious technical effect advantage.

Although the present invention has been disclosed in the above embodiments, it is not intended to limit the present invention. Those with ordinary knowledge in the technical field to which the present invention pertains can make some changes and modifications without departing from the spirit and scope of the present invention. Therefore, the protection scope of the present invention shall be subject to those defined by the attached patent application scope.

no

no

Claims (20)

A 1,3,5-triazine compound as shown in formula I,

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 and R ^{15 are} independently hydrogen, deuterium, halogen, cyano, C ₁ to C ₁₀ alkyl, C substituted by one or more R ^a-1 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, a Or more C ₆ ~C ₁₄ aryl groups substituted by ^Ra-3 , 5-6 membered monocyclic heteroaryl groups, 5-6 membered monocyclic heteroaryl groups substituted by one or more Ra ^-4 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 Is defined as follows: heteroatoms are 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} independently When there are multiple, the same or different; among them,

for

versus

Connected by a single bond; R is independently

,

or

; 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, halo, cyano, C ₁ ~ C ₁₀ alkyl group, with one or more R ^b-1 is substituted with C ₁ ~ C ₁₀ alkyl group, C ₁ ~ C ₁₀ -O- alkyl, substituted with one or more R ^b-2 substituted by C ₁ ~ C ₁₀ alkyl group -O-, C ₆ ~ C ₁₄ aryl group, substituted with one or more R ^b-3 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

; The heteroatom in the 5-6 membered monocyclic heteroaryl group and the 5-6 membered monocyclic heteroaryl group substituted by one or more R ^b-4 Is defined 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} independently When there are multiple, they are the same or different; among them,

for

versus

Connect via a single key;

,

,

with

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 1~3; 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} independently the following substituents: deuterium, Halogen, cyano, trifluoromethyl, C ₁ ~C ₆ alkyl or C ₁ ~C ₆ alkyl-O-. 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 halogen, so The halogen is independently fluorine, chlorine, bromine or iodine; 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 is independently a C ₁ ~ C ₁₀ alkyl group, 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 In the substituted C ₁ to C ₁₀ alkyl group-O-, the C ₁ to C ₁₀ alkyl group is independently a C ₁ to C ₆ alkyl group; 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 group by one or more R ^a-3 substituted C ₆ ~ C ₁₄ aryl group Wherein, the C ₆ to C ₁₄ aryl group is independently a C ₆ to C ₁₀ aryl group; 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 5-6 membered monocyclic heteroaryl groups substituted by one or more R ^a-4 , said C ₁ ~ C ₁₂ heteroaryl groups are independently heteroatoms selected from N, the number of heteroatoms is 1 to 3; 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 group, with one or more R ^b-1 is substituted with C ₁ ~ C ₁₀ alkyl group, C ₁ ~ C ₁₀ alkyl group -O -Or in the C ₁ ~C ₁₀ alkyl group-O- substituted by one or more R ^b-2 , the C ₁ ~C ₁₀ alkyl group is independently a C ₁ ~C ₆ alkyl group; 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 grouped by one or more In the C ₆ to C ₁₄ aryl group substituted by R ^b-3 , the C ₆ to C ₁₄ aryl group is independently a C ₆ to C ₁₀ aryl group; 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 5- substituted by one or more R ^b-4 In the 6-membered monocyclic heteroaryl group, The C ₁ ~C ₁₂ heteroaryl group is independently a heteroatom selected from N, and the number of heteroatoms is 1 to 3; and/or, when

,

,

with

When independently phenyl,

or

Independently

; And/or,

,

,

with

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 heteroatoms are selected from N, and the number of heteroatoms is 1 to 2; 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 R ^{15 is the} same; and/or, R is independently located on the benzene ring and

The ortho, meta or para position of the connection site; and/or, 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 halogen, and the halogen is independently fluorine, chlorine, bromine or iodine; 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 are} independently C ₁ ~C ₆ alkyl Or in the C ₁ ~C ₆ alkyl group-O-, the C ₁ ~C ₆ alkyl group or the C ₁ ~C ₆ alkyl group in the C ₁ ~C ₆ alkyl group-O- are independently methyl, ethyl Group, n-propyl, isopropyl, n-butyl, secondary butyl, isobutyl or tertiary butyl; and/or, Ra ^-1 , Ra ^-2 , Ra ^-3 , ^{Ra- 4. The number} of R ^b-1 , R ^b-2 , R ^b-3 , R ^b-4 , R ^c-1 and R ^c-2 is independently 1, 2 or 3; 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, 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 group; 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 ₁ ~C ₁₀ alkane substituted by one or more R ^b-1 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 of R ^b-4 5-6 membered monocyclic heteroaryl or

, R ^2-1 , R ^2-2 and R ^{2-3 are} independently hydrogen; and/or, R ^X1 , R ^X2 and R ^{X3 are} independently

or

. The 1,3,5-triazine compound of formula I as described in 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 halogen, so The halogen mentioned above is independently fluorine; 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 to C ₁₀ alkyl, C ₁ ~C ₁₀ alkyl substituted by one or more Ra ^-1 , C ₁ ~C ₁₀ alkyl-O- or C ₁ ~C substituted by one or more Ra ^-2 _{In 10} alkyl-O-, the C ₁ ~C ₁₀ alkyl is independently methyl, ethyl, n-propyl, isopropyl, n-butyl, secondary butyl, isobutyl or tertiary Butyl; 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 or In the C ₆ to C ₁₄ aryl group substituted by one or more R ^a-3 , the C ₆ to C ₁₄ aryl group is independently phenyl or naphthyl; 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 ⁵ substituted by one or more R ^a-4 In the -6 membered monocyclic heteroaryl group, the C ₁ to C ₁₂ heteroaryl group is independently pyridyl; 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 group, with one or more R ^b-1 is substituted with C ₁ ~ C ₁₀ alkyl group, C ₁ ~ C ₁₀ In the alkyl-O- or C ₁ ~C ₁₀ alkyl-O- substituted by one or more R ^b-2 , the C ₁ ~C ₁₀ alkyl is independently methyl, ethyl, n-propyl Butyl, isopropyl, n-butyl, secondary butyl, isobutyl or tertiary butyl; 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 group by one or more R ^b-3 is unsubstituted C ₆ ~ C ₁₄ aryl group, C ₆ ~ C according to ₁₄ Aryl groups are independently phenyl or naphthyl; and/or, R ^1-1 , R ^2-1 , R ^1-2 , R ^2-2 , R ^1-3 , R ^1-4 and R ^2-3 Independently 5-6 membered monocyclic heteroaryl or substituted by one or more R ^b-4 In the 5-6 membered monocyclic heteroaryl group, the C ₁ ~C ₁₂ heteroaryl group is independently pyridyl; and/or, when

,

,

with

When independently phenyl,

or

Independently

,

or

; And/or,

,

,

with

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 Pyridyl; and/or, when the number of R is 2, R is independently located on the benzene ring and

The meta position of the connection site; 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 one or When multiple C ₁ ~C ₁₀ alkyl groups substituted by ^Ra-1 or C ₁ ~C ₁₀ alkyl groups-O- substituted by one or more Ra ^-2 groups, the substituted C ₁ ~C ₁₀ alkane group or a substituted C ₁ ~ C ₁₀ alkyl group substituted with -O- in the C ₁ ~ C ₁₀ alkyl group is independently trifluoromethyl; 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 C ₁ ~C ₁₀ alkyl substituted by one or more R ^b-1 or by one or more R ^{When b-2} substituted C ₁ ~C ₁₀ alkyl-O-, the substituted C ₁ ~C ₁₀ alkyl group or the substituted C ₁ ~C ₁₀ alkyl group-O- substituted C ₁ ~C _{The 10} alkyl group is independently trifluoromethyl. The 1,3,5-triazine compound represented by formula I according to claim 3, wherein:

Independently

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

or

; And/or,

Independently

,

,

,

,

,

,

,

,

,

,

,

,

,

,

or

; And/or,

Independently

or

. 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; and / or ,

Independently

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

or

; And/or,

Independently

,

,

,

,

,

,

,

,

,

,

,

or

. The 1,3,5-triazine compound represented by formula I according to claim 1, wherein one of R ¹ , R ² , R ³ , R ⁴ and R ⁵ is R; the rest are independent The ground is R ^Y1 ; or, R ² and R ^{4 are} independently R; the remainder are independently R ^Y1 ; for example, R ² and/or R ^{4 are} independently R; the remainder are independently R ^Y1 ; and/or, R is independently

or

And/or, when R ² and R ^{4 are} independently R, R ² and R ^{4 are the} same or different, such as the same; and/or, R ^{Y1 is} independently hydrogen; 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 to C ₁₀ alkyl, or substituted by one or more R ^a-1 C ₁ ~ C ₁₀ alkyl group; e.g., 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; and/or, Ra ^{-1 is} independently halogen; and/or,

versus

The same or different, such as the same; 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 group, substituted with one or more R ^b-3 is unsubstituted C ₆ ~ C ₁₄ aryl, 5-6 membered monocyclic heteroaryl, or

; ^{E.g., 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. The 1,3,5-triazine compound represented by formula I according to claim 1, wherein it is the following scheme 1 or scheme 2: Scheme 1, R ¹ , R ² , R ³ , R ⁴ and One of 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 is} independently hydrogen; R is independently

or

; 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 and R ¹⁵ 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;

versus

Same or different; 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

; R ^{b-3 is} independently halogen, trifluoromethyl or C ₁ ~C ₆ alkyl; Scheme 2, One of R ¹ , R ² , R ³ , R ⁴ and R ⁵ is R; the rest are independent The ground is R ^Y1 ; or, R ² and R ^{4 are} independently R; the rest are independently R ^Y1 ; R ^{Y1 is} independently hydrogen; R is independently

or

; When 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, or by one or more R ^a-1 Substituted C ₁ to C ₁₀ alkyl; 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;

versus

^{Same; 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 ^{b-3 is} independently halogen, trifluoromethyl or C ₁ to C ₆ alkyl; R ^2-1 , R ^2-2 , and R ^{2-3 are} independently hydrogen. The 1,3,5-triazine compound of formula I according to claim 1, wherein it is any one of the following compounds:

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

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,

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,

,

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,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,or

. An application of the 1,3,5-triazine compound represented by formula I as described in any one of claims 1 to 8 as an electronic material or in the field of organic electroluminescence devices. The application according to claim 9, wherein the electronic material is an electron transport material and/or an electron acceptor material; 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 the organic electroluminescent device. An organic electroluminescence composition comprising an electron donor material and the 1,3,5-triazine compound represented by formula I according to any one of claims 1 to 8. The organic electroluminescence composition according to claim 11, wherein the electron donor material is a phenyl or naphthylcarbazole type electron donor material; And/or, the molar ratio of the 1,3,5-triazine compound represented by formula I to the electron donor material is 3:1 to 1:3; And/or, the organic electroluminescent composition further includes a doped luminescent material. The organic electroluminescent composition according to claim 12, wherein the electron donor material is a phenyl or naphthylcarbazole type electron donor material, and the phenyl or naphthylcarbazole type electron donor material The body material contains 2-3 phenylcarbazole or naphthylcarbazolyl structures; And/or, the molar ratio of the 1,3,5-triazine compound represented by formula I and the electron donor material is 1:1; 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. The organic electroluminescent composition according to claim 13, wherein the electron donor material is any of the following compounds:

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

or

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 And/or, when the organic electroluminescent composition further includes a doped luminescent material, and the doped luminescent material is a phosphorescent luminescent material, the mass percentage in the organic electroluminescent composition is 0.5 _WT %-2.0 _WT %; The mass percentage of the doped luminescent material in the composition is 5.0 _WT %-15.0 _WT %; and/or, the organic electroluminescent composition further includes a doped luminescent material and the doped luminescent material When the heteroluminescent material is a phosphorescent luminescent material, the doped luminescent material is any of the following compounds:

,

,

,

,

or

; 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 , 1-5 C linear or branched alkyl, phenyl or 1-5 C linear or branched alkyl substituted phenyl;

with

Independently is a six-membered aromatic heterocyclic ring containing 1-2 N; and/or, the organic electroluminescent composition further includes a doped luminescent material, and the doped luminescent material is a fluorescent luminescent material When the doped luminescent material is any of the following compounds:

,

,

,

,

,

,

,

,

or

; Wherein, Rg ^11-1 , Rg ^11-2 , Rh ^11-1 , 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 ; 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 are} independently containing 1- 5 C straight or branched chain alkyl, cyclohexane or cumene; Rm ^22-1 , Rn ^25-1 , Ro ^28-11 and Rp ^33-1 are straight chain containing 1-4 C Or branched alkyl. The organic electroluminescent composition according to claim 14, wherein the electron donor material is

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 mass percentage of 1.0 _WT%; when and / or the organic electroluminescent composition further comprises a light emitting dopant material, and said luminescent material is a phosphorescent dopant material, the dopant emitting The mass percentage of the material in the composition is 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

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

. An application of the organic electroluminescent composition according to any one of claims 11 to 15 as an organic electroluminescent material. An organic electroluminescence device, wherein it contains the organic electroluminescence composition according to any one of claims 11-15. The organic electroluminescent device according to claim 17, wherein the organic electroluminescent composition is a light-emitting layer; And/or, 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 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. The organic electroluminescent device according to claim 18, wherein, when the organic light-emitting functional 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 composition have the same structure. An organic electroluminescent device according to any one of claims 17 to 19 is used to prepare an organic electroluminescent display or an organic electroluminescent lighting source.