Patent Publication Number: US-2023139051-A1

Title: Benzoxazole derivative and electroluminescent application thereof

Description:
CROSS REFERENCE TO RELATED APPLICATIONS 
     This application claims the priority of Chinese Patent Application No. 202210883191.5, filed with the China National Intellectual Property Administration on Jul. 26, 2022, and titled with “BENZOXAZOLE DERIVATIVE AND ELECTROLUMINESCENT APPLICATION THEREOF”, which is hereby incorporated by reference. 
     FIELD 
     The present disclosure relates to the field of organic electroluminescent materials, and in particular to a benzoxazole derivative and an electroluminescent application thereof. 
     BACKGROUND 
     The electron transport material used in traditional electroluminescent devices is Alq3, but the electron mobility of Alq3 is relatively low (about 10 −6  cm 2 /Vs), which makes the electron transport and hole transport of the device unbalanced. With the commercialization and practical application of electroluminescent devices, ETL materials with higher transport efficiency and better performance are expected, in the field of which researchers have done a lot of exploratory work. 
     The glass transition temperature of current materials is low, generally lower than 85° C. When the device is running, the Joule heat generated will lead to molecular degradation and changes in molecular structure, resulting in low efficiency and poor thermal stability of the panel. The materials are easy to be crystallized after a long time, and the intermolecular charge transition mechanism thereof will be different from the mechanism of the amorphous thin film under the normal operation, resulting in a decrease in the performance of electron transport. 
     It is of very important practical application value to design and develop stable and efficient electron transport materials and/or electron injection materials that can have both high electron mobility and high glass transition temperature, and are effectively doped with metal Yb or Liq, to reduce threshold voltage, improving efficiency of device, and prolonging lifetime of device. 
     SUMMARY 
     In view of this, the problem to be solved by the present disclosure is to provide a benzoxazole derivative and an electroluminescent application thereof, which can effectively improve the lifetime and efficiency of the device. 
     The present disclosure provides a benzoxazole derivative having the structure as shown in formula I: 
     
       
         
         
             
             
         
       
     
     R has any of the following structures: 
     
       
         
         
             
             
         
       
     
     A is 
     
       
         
         
             
             
         
       
     
     X 1 , X 2 , X 3  are independently selected from the group consisting of N, O, S or Si; 
     R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10  are independently selected from the group consisting of H, D, halogen, cyano, substituted or unsubstituted aryl or heteroaryl; 
     L 1 , L 2 , L 3  are independently selected from the group consisting of single bonds, substituted or unsubstituted aryl or heteroaryl, and at least two of L 1 , L 2 , and L 3  are not single bonds; 
     Ar 1  and Ar 2  are independently selected from the group consisting of substituted or unsubstituted aryl or heteroaryl; 
     #indicates the linking site. 
     The present disclosure provides an organic light-emitting device, the organic light-emitting device includes an anode, a cathode, and an organic thin film layer located between the anode and the cathode, and the organic thin film layer includes an electron transport layer, and the electron transport layer includes at least one of the above-mentioned benzoxazole derivatives. 
     The present disclosure provides a display panel comprising the above organic light-emitting device. 
    
    
     DETAILED DESCRIPTION 
     The present disclosure provides a benzoxazole derivative having a structure as shown in formula I. 
     
       
         
         
             
             
         
       
     
     R has any of the following structures: 
     
       
         
         
             
             
         
       
       
         
         
             
             
         
       
     
     A is 
     
       
         
         
             
             
         
       
     
     X 1 , X 2 , X 3  are independently selected from the group consisting of N, O, S or Si; 
     R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10  are independently selected from the group consisting of H, D, halogen, cyano, substituted or unsubstituted aryl or heteroaryl; 
     L 1 , L 2 , L 3  are independently selected from the group consisting of single bonds, substituted or unsubstituted aryl or heteroaryl, and at least two of L 1 , L 2 , and L 3  are not single bonds; 
     Ar 1  and Ar 2  are independently selected from the group consisting of substituted or unsubstituted aryl or heteroaryl; 
     #indicates the linking site. 
     In one embodiment, the substituents of the R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , L 1 , L 2 , L 3 , Ar 1  and Ar 2  are independently selected from the group consisting of D, halogen, cyano, aryl or heteroaryl. 
     In one embodiment, the X 2  is O, and the X 3  is N. 
     In one embodiment, the X 1  is O. 
     In one embodiment, the R has any of the following structures: 
     
       
         
         
             
             
         
       
       
         
         
             
             
         
       
     
     R 11  is selected from the group consisting of H, D, halogen, cyano, substituted or unsubstituted aryl or heteroaryl; 
     #is the linking site. 
     In one embodiment, the R 11  is selected from the group consisting of H, D, halogen, cyano, substituted or unsubstituted monocyclic aryl, monocyclic heteroaryl, fused aryl formed by the fusion of 2˜3 aromatic rings, heteroaryl formed by the fusion of 2˜3 aromatic rings and heteroaromatic rings, and heteroaryl formed by the fusion of 2˜3 heteroaromatic rings. 
     In one embodiment, the monocyclic aryl is phenyl. 
     In one embodiment, the monocyclic heteroaryl is a five-membered or six-membered heteroaryl having 1-3 N atoms. 
     In one embodiment, the aromatic ring fused to form the fused aryl is a benzene ring. 
     In one embodiment, the aromatic ring fused to form the heteroaryl is a benzene ring. 
     In one embodiment, the heteroaromatic ring fused to form the heteroaryl is a five-membered or six-membered heteroaryl having 1-3 N atoms. 
     In one embodiment, the R 11  is selected from the group consisting of H, D, halogen, cyano, substituted or unsubstituted phenyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, naphthyl, anthracenyl, phenanthryl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl or 1,5-naphthyridinyl. 
     In one embodiment, the R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10  are independently selected from the group consisting of H, D, halogen, cyano, substituted or unsubstituted monocyclic aryl, monocyclic heteroaryl, fused aryl formed by the fusion of 2˜3 aromatic rings, heteroaryl formed by the fusion of 2˜3 aromatic rings and heteroaromatic rings, and heteroaryl formed by the fusion of 2˜3 heteroaromatic rings. 
     In one embodiment, the monocyclic aryl is phenyl. 
     In one embodiment, the monocyclic heteroaryl is a five-membered or six-membered heteroaryl having 1-3 N atoms. 
     In one embodiment, the aromatic ring fused to form the fused aryl is a benzene ring. 
     In one embodiment, the aromatic ring fused to form the heteroaryl is a benzene ring. 
     In one embodiment, the heteroaromatic ring fused to form the heteroaryl is a five-membered or six-membered heteroaryl having 1-3 N atoms. 
     In one embodiment, the R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10  are independently selected from the group consisting of H, D, halogen, cyano, substituted or unsubstituted phenyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, naphthyl, anthracenyl, phenanthryl, 1,10-phenanthrolinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl or 1,5-naphthyridinyl. 
     In one embodiment, the L 1 , L 2 , L 3  are independently selected from the group consisting of single bonds, substituted or unsubstituted monocyclic aryl, monocyclic heteroaryl, fused aryl formed by the fusion of 2˜3 aromatic rings, heteroaryl formed by the fusion of 2˜3 aromatic rings and heteroaromatic rings, and heteroaryl formed by the fusion of 2˜3 heteroaromatic rings, and at least two of L 1 , L 2 , and L 3  are not single bonds. 
     In one embodiment, the monocyclic aryl is phenyl. 
     In one embodiment, the monocyclic heteroaryl is a five-membered or six-membered heteroaryl having 1-3 N atoms. 
     In one embodiment, the aromatic ring fused to form the fused aryl is a benzene ring. 
     In one embodiment, the aromatic ring fused to form the heteroaryl is a benzene ring. 
     In one embodiment, the heteroaromatic ring fused to form the heteroaryl is a five-membered or six-membered heteroaryl having 1-3 N atoms. 
     In one embodiment, the L 1 , L 2 , L 3  are independently selected from the group consisting of single bonds, substituted or unsubstituted phenyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, naphthyl, anthracenyl, phenanthryl, 1,10-phenanthrolinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl or 1,5-naphthyridinyl, and at least two of L 1 , L 2  and L 3  are not single bonds. 
     In one embodiment, two or three of the L 1 , L 2 , and L 3  are not single bonds. 
     In one embodiment, the Ar 1  and Ar 2  are independently selected from the group consisting of substituted or unsubstituted monocyclic aryl, monocyclic heteroaryl, fused aryl formed by the fusion of 2˜3 aromatic rings, heteroaryl formed by the fusion of 2˜3 aromatic rings and heteroaromatic rings, and heteroaryl formed by the fusion of 2˜3 heteroaromatic rings, and at least two of L 1 , L 2 , and L 3  are not single bonds. 
     In one embodiment, the monocyclic aryl is phenyl. 
     In one embodiment, the monocyclic heteroaryl is a five-membered or six-membered heteroaryl having 1-3 N atoms. 
     In one embodiment, the aromatic ring fused to form the fused aryl is a benzene ring. 
     In one embodiment, the aromatic ring fused to form the heteroaryl is a benzene ring. 
     In one embodiment, the heteroaromatic ring fused to form the heteroaryl is a five-membered or six-membered heteroaryl having 1-3 N atoms. 
     In one embodiment, the Ar 1  and Ar 2  are independently selected from the group consisting of substituted or unsubstituted phenyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, naphthyl, anthracenyl, phenanthryl, 1,10-phenanthrolinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl or 1,5-naphthyridinyl. 
     In one embodiment, the benzoxazole derivative has any of the following structures: 
     
       
         
         
             
             
         
       
       
         
         
             
             
         
       
       
         
         
             
             
         
       
       
         
         
             
             
         
       
       
         
         
             
             
         
       
       
         
         
             
             
         
       
       
         
         
             
             
         
       
       
         
         
             
             
         
       
       
         
         
             
             
         
       
       
         
         
             
             
         
       
       
         
         
             
             
         
       
       
         
         
             
             
         
       
       
         
         
             
             
         
       
       
         
         
             
             
         
       
       
         
         
             
             
         
       
       
         
         
             
             
         
       
       
         
         
             
             
         
       
       
         
         
             
             
         
       
       
         
         
             
             
         
       
       
         
         
             
             
         
       
       
         
         
             
             
         
       
       
         
         
             
             
         
       
       
         
         
             
             
         
       
       
         
         
             
             
         
       
       
         
         
             
             
         
       
       
         
         
             
             
         
       
       
         
         
             
             
         
       
       
         
         
             
             
         
       
       
         
         
             
             
         
       
       
         
         
             
             
         
       
       
         
         
             
             
         
       
       
         
         
             
             
         
       
       
         
         
             
             
         
       
       
         
         
             
             
         
       
     
     
       
         
         
             
             
         
       
       
         
         
             
             
         
       
       
         
         
             
             
         
       
       
         
         
             
             
         
       
       
         
         
             
             
         
       
       
         
         
             
             
         
       
       
         
         
             
             
         
       
       
         
         
             
             
         
       
       
         
         
             
             
         
       
       
         
         
             
             
         
       
       
         
         
             
             
         
       
       
         
         
             
             
         
       
       
         
         
             
             
         
       
       
         
         
             
             
         
       
       
         
         
             
             
         
       
       
         
         
             
             
         
       
       
         
         
             
             
         
       
       
         
         
             
             
         
       
       
         
         
             
             
         
       
       
         
         
             
             
         
       
       
         
         
             
             
         
       
       
         
         
             
             
         
       
       
         
         
             
             
         
       
       
         
         
             
             
         
       
       
         
         
             
             
         
       
     
     The present disclosure provides an organic light-emitting device comprising an anode, a cathode, and an organic thin film layer located between the anode and the cathode, and the organic thin film layer includes an electron transport layer, and the electron transport layer includes at least one of the above-mentioned benzoxazole derivatives. 
     In one embodiment, the electron transport layer includes the benzoxazole derivative and LiQ. 
     The above-mentioned LiQ refers to 8-hydroxyquinolinolato-lithium. 
     The present disclosure provides a display panel comprising the above organic light-emitting device. 
     The organic light-emitting device provided by the present disclosure can be an organic light-emitting device well known to those skilled in the art. In one embodiment of the present disclosure, the organic light-emitting device includes a substrate plate, an ITO anode, a first hole transport layer, a second hole transport layer, an electron blocking layer, a light-emitting layer, a first electron transport layer, a second electron transport layer, a cathode (magnesium-silver electrode, the mass ratio of magnesium-silver is 1:9) and a capping layer (CPL). 
     In one embodiment of the present disclosure, the anode material of the organic light-emitting device can be selected from the group consisting of metals-copper, gold, silver, iron, chromium, nickel, manganese, palladium, platinum, etc. and alloys thereof; such as metal oxides-indium oxide, zinc oxide, indium tin oxide (ITO), indium zinc oxide (IZO); such as conductive polymers—polyaniline, polypyrrole, poly(3-methylthiophene). In addition to the above materials and combinations thereof that contribute to hole injection, materials known to be suitable for use as anodes are also included. 
     In one embodiment of the present disclosure, the cathode material of the organic light-emitting device can be selected from the group consisting of metals-aluminum, magnesium, silver, indium, tin, titanium, etc. and alloys thereof; such as multi-layer metal materials-LiF/Al, LiO 2 /Al, BaF 2 /Al; in addition to the above materials and combinations thereof that contribute to electron injection, materials known to be suitable for use as cathodes are also included. 
     In one embodiment of the present disclosure, the organic thin film layer in the organic photoelectronic device, such as the organic light-emitting device, includes at least one light-emitting layer (EML), and may also include other functional layers, comprising a hole injection layer (HIL), a hole transport layer (HTL), an electron blocking layer (EBL), a hole blocking layer (HBL), an electron transport layer (ETL), and an electron injection layer (EIL). 
     In one embodiment of the present disclosure, the organic light-emitting device is prepared according to the following method: 
     Forming an anode on a transparent or opaque smooth substrate plate, forming an organic thin layer on the anode, and forming a cathode on the organic thin layer. 
     In one embodiment of the present disclosure, known film forming methods such as vapor deposition, sputtering, spin coating, dipping, and ion plating can be used to form the organic thin layer. 
     The present disclosure provides a display device comprising the above-mentioned display panel. 
     In the present disclosure, an organic light-emitting device (OLED device) can be used in a display device, and the organic light-emitting display device can be a mobile phone display, a computer display, a TV display, a smart watch display, a smart car display panel, a VR or AR helmet display, displays of various smart devices, etc. 
     The following will clearly and completely describe the embodiments of the present disclosure. The described examples are only a part of the embodiments of the present disclosure, rather than all the embodiments. Based on the examples of the present disclosure, all other examples may be obtained. 
     Example 1 Preparation of Compounds 
     Preparation of A1 
     
       
         
         
             
             
         
       
     
     2-amino-3-dibenzofuranol (20.0 g, 101 mmol) and triethyl formate (20 mL) were added to a reaction vessel. The obtained mixture was refluxed for 9 hours until the reaction was completed. Triethyl formate was then removed. The residue was separated by column chromatography to obtain M1-1 (18.06 g, 86%). 
     
       
         
         
             
             
         
       
     
     Intermediate 2,4-diphenyl-6-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1,3,5-triazine (8.7 g, 20.00 mmol), 1,4-diiodonaphthalene (7.6 g, 20.05 mmol), Pd(PPh 3 ) 4 (1.13 g, 0.98 mmol), and K 2 CO 3  (8.11 g, 58.66 mmol) were mixed into 100 ml of toluene, 25 ml of H 2 O and 25 ml of EtOH under nitrogen gas stream, and the mixture was stirred at 110° C. for 4 hours. After the reaction was completed, the mixture was extracted with dichloromethane, added with MgSO 4 , and filtered. After the solvent of the filtered organic layer was removed, the residue was subjected to column chromatography to obtain 9.54 g (yield: 85%) of the target compound M1-2. 
     
       
         
         
             
             
         
       
     
     Copper (I) thiophene-2-carboxylate (0.1 g, 0.5 mmol), 2,2′-bipyridine (0.1 g, 0.5 mmol), and lithium were added to tert-butoxide (2.0 g, 25 mmol) and dry N,N-dimethylformamide (50 ml, 0.2 M) with a magnetic stir bar under nitrogen atmosphere. After stirring for 5 minutes, the color of the solvent changed from light green to light yellow, and M1-1 (2.1 g, 10 mmol) and M1-2 (22.4 g, 40 mmol) were added to the mixture. The obtained solution was then irradiated with a blue LED and stirred at room temperature for 16 hours. The obtained suspension was filtered on a pad of silica gel using ethyl acetate as eluent and evaporated in vacuum. The residue was separated by column chromatography to obtain 5.14 g of product A1, (yield: 80%). 
     Preparation of A2 
     
       
         
         
             
             
         
       
     
     M2-1 was prepared in the same way as M1-2, following the same preparation method of M1-2, using the same molar ratio, except that 2,4-diphenyl-6-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1,3,5-triazine was replaced by 2,4-diphenyl-6-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1,3,5-triazine. 
     
       
         
         
             
             
         
       
     
     A2 was prepared in the same way as A1, following the same preparation method of A1, using the same molar ratio, except that M1-2 was replaced by M2-1. 
     Preparation of A5 
     
       
         
         
             
             
         
       
     
     M3-1 was prepared in the same way as M1-2, following the same preparation method of M1-2, using the same molar ratio, except that 1,4-diiodonaphthalene was replaced by 1,4-diiodobenzene, and 2,4-diphenyl-6-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1,3,5-triazine was replaced with 2,4-diphenyl-6-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-naphthyl]-1,3,5-triazine. 
     
       
         
         
             
             
         
       
     
     A5 was prepared in the same way as A1, following the same preparation method of A1, using the same molar ratio, except that M1-2 was replaced by M3-1. 
     Preparation of A12 
     
       
         
         
             
             
         
       
     
     100 ml of ethanol, 2-amino-3-dibenzofuranol (20.0 g, 101 mmol), NBS (2.5 g, 220 mmol) and copper nitrate (1.3 g, 10 mmol) were sequentially added in a reactor, and the mixture was stirred at room temperature for 0.5 h, then heated up to 50° C. and maintained for 3 h until the reaction was completed. Then the reaction solution was cooled to 20° C., and poured into 100 ml of water, and the mixture was stirred for 2 h. The obtained mixture was suction filtered, and the filter cake was stirred with 100 ml of water at room temperature for 1 h. The mixture was suction filtered, and then dried at 50° C. to obtain M4-1 (23.3 g, 84%). 
     
       
         
         
             
             
         
       
     
     M4-2 was prepared in the same way as M1-1, following the same preparation method of M1-1, using the same molar ratio, except that 2-amino-3-dibenzofuranol was replaced by M4-1. 
     
       
         
         
             
             
         
       
     
     M4-3 was prepared in the same way as A1, following the same preparation method of A1, using the same molar ratio, except that M1-2 was replaced with iodobenzene. 
     
       
         
         
             
             
         
       
     
     Intermediate M4-3 (7.2 g, 19.55 mmol), pinacol bisborate (5.96 g, 23.46 mmol), Pd(OAc) 2  (0.13 g, 0.59 mmol), KOAc (3.84 g, 39.11 mmol) and 100 ml of toluene were mixed under nitrogen atmosphere, and the mixture was stirred at 100° C. for 8 hours. After the reaction was completed, the mixture was extracted with dichloromethane, added with MgSO 4 , and the obtained mixture was filtered. After the solvent of the filtered organic layer was removed, the residue was subjected to column chromatography to obtain 7.2 g (yield: 88%) of intermediate M4-4. 
     
       
         
         
             
             
         
       
     
     Intermediates M4-4 (6.7 g, 20.0 mmol), M1-2 (11.2 g, 20.0 mmol), Pd(PPh 3 ) 4 (1.13 g, 0.98 mmol), K 2 CO 3  (8.11 g, 58.66 mmol) were mixed into 100 ml of toluene, 25 ml of H 2 O and 25 ml of EtOH under nitrogen gas stream, and the mixture was stirred at 110° C. for 4 hours. After the reaction was completed, the mixture was extracted with dichloromethane, added with MgSO 4 , and the obtained mixture was filtered. After the solvent of the filtered organic layer was removed, the residue was subjected to column chromatography to obtain 12.9 g (yield: 90%) of the target compound A12. 
     Preparation of A21 
     
       
         
         
             
             
         
       
     
     M5-1 was prepared in the same way as M4-3, following the same preparation method of M4-3, using the same molar ratio, except that M4-2 was replaced with 4-amino-6-chloro-1,3-benzenediol. 
     
       
         
         
             
             
         
       
     
     M5-2 was prepared in the same way as A12, following the same preparation method of A12, using the same molar ratio, except that M4-3 was replaced by M5-1, and M1-2 was replaced by 2-bromo-4-chlorophenol. 
     
       
         
         
             
             
         
       
     
     M5-2 (5.0 g, 20 mmol) and 1,2-dichlorobenzene (250 mL) were added to a reactor. The reaction mixture was heated at 160° C. for 8 hours. After the reaction was completed, the organic substance was dissolved in chloroform (100 mL). After the solvent was removed, the crude compound was separated by column chromatography to obtain M5-3 (4.6 g, 77%). 
     
       
         
         
             
             
         
       
     
     M5-4 was prepared in the same way as M1-1, following the same preparation method of M1-1, using the same molar ratio, except that 2-amino-3-dibenzofuranol was replaced with M5-3. 
     
       
         
         
             
             
         
       
     
     M5-5 was prepared in the same way as A1, following the same preparation method of A1, using the same molar ratio, except that M1-1 was replaced by M5-4, and M1-2 was replaced by 4-iodopyridine. 
     
       
         
         
             
             
         
       
     
     M5-6 was prepared in the same way as M4-3, following the same preparation method of M4-3, using the same molar ratio, except that M4-2 was replaced by M5-5. 
     
       
         
         
             
             
         
       
     
     A21 was prepared in the same way as A12, following the same preparation method of A12, using the same molar ratio, except that M4-4 was replaced by M5-6. 
     Preparation of A24 
     
       
         
         
             
             
         
       
     
     M6-1 was prepared in the same way as A12, following the same preparation method of A12, using the same molar ratio, except that M4-3 was replaced by M6-1, and M1-2 was replaced by 2-bromo-5-chlorophenol. 
     
       
         
         
             
             
         
       
     
     M6-2 was prepared in the same way as M5-3, following the same preparation method of M5-3, using the same molar ratio, except that M5-2 was replaced by M6-1. 
     
       
         
         
             
             
         
       
     
     M6-3 was prepared in the same way as M1-1, following the same preparation method of M1-1, using the same molar ratio, except that 2-amino-3-dibenzofuranol was replaced by M6-2. 
     
       
         
         
             
             
         
       
     
     M6-4 was prepared in the same way as A1, following the same preparation method of A1, using the same molar ratio, except that M1-1 was replaced by M6-3, and M1-2 was replaced by 1-iodonaphthalene. 
     
       
         
         
             
             
         
       
     
     M6-5 was prepared in the same way as M4-3, following the same preparation method of M4-3, using the same molar ratio, except that M4-2 was replaced by M6-4. 
     
       
         
         
             
             
         
       
     
     A24 was prepared in the same way as A12, following the same preparation method of A12, using the same molar ratio, except that M4-4 was replaced by M6-5. 
     Preparation of B1 
     
       
         
         
             
             
         
       
     
     M7-1 was prepared in the same way as M1-1, following the same preparation method of M1-1, using the same molar ratio, except that 2-amino-3-dibenzofuranol was replaced with 3-amino-2-dibenzofuranol. 
     
       
         
         
             
             
         
       
     
     B1 was prepared in the same way as A1, following the same preparation method of A1, using the same molar ratio, except that M1-1 was replaced by M7-1. 
     Preparation of B2 
     
       
         
         
             
             
         
       
     
     B2 was prepared in the same way as A1, following the same preparation method of A1, using the same molar ratio, except that M1-1 was replaced with M7-1, and M1-2 was replaced with M2-1. 
     Preparation of B5 
     
       
         
         
             
             
         
       
     
     B5 was prepared in the same way as A1, following the same preparation method of A1, using the same molar ratio, except that M1-1 was replaced by M7-1, and M1-2 was replaced by M3-1. 
     Preparation of B12 
     
       
         
         
             
             
         
       
     
     M8-1 was prepared in the same way as M4-1, following the same preparation method of M4-1, using the same molar ratio, except that 2-amino-3-dibenzofuranol was replaced with 3-amino-2-dibenzofuranol. 
     
       
         
         
             
             
         
       
     
     M8-2 was prepared in the same way as M1-1, following the same preparation method of M1-1, using the same molar ratio, except that 2-amino-3-dibenzofuranol was replaced with M8-1. 
     
       
         
         
             
             
         
       
     
     M8-3 was prepared in the same way as A1, following the same preparation method of A1, using the same molar ratio, except that M1-1 was replaced by M8-2, and M1-2 was replaced by iodobenzene. 
     
       
         
         
             
             
         
       
     
     M8-4 was the same as that of M4-4, following the same preparation method of M4-4, using the same molar ratio, except that M4-3 was replaced by M8-3. 
     
       
         
         
             
             
         
       
     
     B12 was prepared in the same way as A12, following the same preparation method of A12, using the same molar ratio, except that M4-4 was replaced by M8-4. 
     Preparation of B21 
     
       
         
         
             
             
         
       
     
     M9-1 was prepared in the same way as M4-3, following the same preparation method of M4-3, using the same molar ratio, except that M4-2 was replaced by 2-amino-5-chloro-1,4-benzenediol. 
     
       
         
         
             
             
         
       
     
     M9-2 
     M9-2 was prepared in the same way as A12, following the same preparation method of A12, using the same molar ratio, except that M4-3 was replaced by M9-1, and M1-2 was replaced by 2-bromo-4-chlorophenol. 
     
       
         
         
             
             
         
       
     
     M9-3 was prepared in the same way as M5-3, following the same preparation method of M5-3, using the same molar ratio, except that M5-2 was replaced by M9-2. 
     
       
         
         
             
             
         
       
     
     M9-4 was prepared in the same way as M1-1, following the same preparation method of M1-1, using the same molar ratio, except that 2-amino-3-dibenzofuranol was replaced with M9-3. 
     
       
         
         
             
             
         
       
     
     M9-5 was prepared in the same way as A1, following the same preparation method of A1, using the same molar ratio, except that M1-1 was replaced by M9-4, and M1-2 was replaced by 4-iodopyridine. 
     
       
         
         
             
             
         
       
     
     M9-6 was prepared in the same way as M4-3, following the same preparation method of M4-3, using the same molar ratio, except that M4-2 was replaced by M9-5. 
     
       
         
         
             
             
         
       
     
     B21 was prepared in the same way as A12, following the same preparation method of A12, using the same molar ratio, except that M4-4 was replaced by M9-6. 
     Preparation of B24 
     
       
         
         
             
             
         
       
     
     M10-1 was prepared in the same way as A12, following the same preparation method of A12, using the same molar ratio, except that M4-3 was replaced by M9-1, and M1-2 was replaced by 2-bromo-5-chlorophenol. 
     
       
         
         
             
             
         
       
     
     M10-2 was prepared in the same way as M5-3, following the same preparation method of M5-3, using the same molar ratio, except that M5-2 was replaced by M10-1. 
     
       
         
         
             
             
         
       
     
     M10-3 was prepared in the same way as M1-1, following the same preparation method of M1-1, using the same molar ratio, except that 2-amino-3-dibenzofuranol was replaced with M10-2. 
     
       
         
         
             
             
         
       
     
     M10-4 was prepared in the same way as A1, following the same preparation method of A1, using the same molar ratio, except that M1-1 was replaced by M10-3, and M1-2 was replaced by 1-iodonaphthalene. 
     
       
         
         
             
             
         
       
     
     M10-5 was prepared in the same way as M4-3, following the same preparation method of M4-3, using the same molar ratio, except that M4-2 was replaced by M10-4. 
     
       
         
         
             
             
         
       
     
     B24 was prepared in the same way as A12, following the same preparation method of A12, using the same molar ratio, except that M4-4 was replaced by M10-5. 
     Preparation of C1 
     
       
         
         
             
             
         
       
     
     M11-1 was prepared in the same way as M1-1, following the same preparation method of M1-1, using the same molar ratio, except that 2-amino-3-dibenzofuranol was replaced by 3-amino-4-dibenzofuranol. 
     
       
         
         
             
             
         
       
     
     C1 was prepared in the same way as A1, following the same preparation method of A1, using the same molar ratio, except that M1-1 was replaced by M11-1. 
     Preparation of C2 
     
       
         
         
             
             
         
       
     
     C2 was prepared in the same way as A1, following the same preparation method of A1, using the same molar ratio, except that M1-1 was replaced with M11-1, and M1-2 was replaced with M2-1. 
     Preparation of C5 
     
       
         
         
             
             
         
       
     
     C5 was prepared in the same way as A1, following the same preparation method of A1, using the same molar ratio, except that M1-1 was replaced by M11-1, and M1-2 was replaced by M3-1. 
     Preparation of C11 
     
       
         
         
             
             
         
       
     
     M12-1 was prepared in the same way as M4-1, following the same preparation method of M4-1, using the same molar ratio, except that 2-amino-3-dibenzofuranol was replaced with 3-amino-4-dibenzofuranol. 
     
       
         
         
             
             
         
       
     
     M12-2 was prepared in the same way as M1-1, following the same preparation method of M1-1, using the same molar ratio, except that 2-amino-3-dibenzofuranol was replaced with M12-1. 
     
       
         
         
             
             
         
       
     
     M12-3 was prepared in the same way as A1, following the same preparation method of A1, using the same molar ratio, except that M1-1 was replaced by M12-2, and M1-2 was replaced by iodobenzene. 
     
       
         
         
             
             
         
       
     
     M12-4 was prepared in the same way as M4-4, following the same preparation method of M4-4, using the same molar ratio, except that M4-3 was replaced by M12-3. 
     
       
         
         
             
             
         
       
     
     C11 was prepared in the same way as A12, following the same preparation method of A12, using the same molar ratio, except that M4-4 was replaced by M12-4. 
     Preparation of C21 
     
       
         
         
             
             
         
       
     
     M13-1 was prepared in the same way as M4-3, following the same preparation method of M4-3, using the same molar ratio, except that M4-2 was replaced with 3-amino-6-chloro-1,2-benzenediol. 
     
       
         
         
             
             
         
       
     
     M13-2 was prepared in the same way as A12, following the same preparation method of A12, using the same molar ratio, except that M4-3 was replaced by M13-1, and M1-2 was replaced by 2-bromo-4-chlorophenol. 
     
       
         
         
             
             
         
       
     
     M13-3 was prepared in the same way as M5-3, following the same preparation method of M5-3, using the same molar ratio, except that M5-2 was replaced by M13-2. 
     
       
         
         
             
             
         
       
     
     M13-4 was prepared in the same way as M1-1, following the same preparation method of M1-1, using the same molar ratio, except that 2-amino-3-dibenzofuranol was replaced with M13-3. 
     
       
         
         
             
             
         
       
     
     M13-5 was prepared in the same way as A1, following the same preparation method of A1, using the same molar ratio, except that M1-1 was replaced by M13-4, and M1-2 was replaced by 4-iodopyridine. 
     
       
         
         
             
             
         
       
     
     M13-6 was prepared in the same way as M4-3, following the same preparation method of M4-3, using the same molar ratio, except that M4-2 was replaced by M13-5. 
     
       
         
         
             
             
         
       
     
     C21 was prepared in the same way as A12, following the same preparation method of A12, using the same molar ratio, except that M4-4 was replaced by M13-6. 
     Preparation of C24 
     
       
         
         
             
             
         
       
     
     M14-1 was prepared in the same way as A12, following the same preparation method of A12, using the same molar ratio, except that M4-3 was replaced by M13-1, and M1-2 was replaced by 2-bromo-5-chlorophenol. 
     
       
         
         
             
             
         
       
     
     M14-2 was prepared in the same way as M5-3, following the same preparation method of M5-3, using the same molar ratio, except that M5-2 was replaced by M14-1. 
     
       
         
         
             
             
         
       
     
     M14-3 was prepared in the same way as M1-1, following the same preparation method of M1-1, using the same molar ratio, except that 2-amino-3-dibenzofuranol was replaced by M14-2. 
     
       
         
         
             
             
         
       
     
     M14-4 was prepared in the same way as A1, following the same preparation method of A1, using the same molar ratio, except that M1-1 was replaced by M14-3, and M1-2 was replaced by 1-iodonaphthalene. 
     
       
         
         
             
             
         
       
     
     M14-5 was prepared in the same way as M4-3, following the same preparation method of M4-3, using the same molar ratio, except that M4-2 was replaced by M14-4. 
     
       
         
         
             
             
         
       
     
     C24 was prepared in the same way as A12, following the same preparation method of A12, using the same molar ratio, except that M4-4 was replaced by M14-5. 
     Preparation of D1 
     
       
         
         
             
             
         
       
     
     M15-1 was prepared in the same way as M1-1, following the same preparation method of M1-1, using the same molar ratio, except that 2-amino-3-dibenzofuranol was replaced with 4-amino-3-dibenzofuranol. 
     
       
         
         
             
             
         
       
     
     D1 was prepared in the same way as A1, following the same preparation method of A1, using the same molar ratio, except that M1-1 was replaced by M15-1. 
     Preparation of D2 
     
       
         
         
             
             
         
       
     
     D2 was prepared in the same way as A1, following the same preparation method of A1, using the same molar ratio, except that M1-1 was replaced by M15-1, and M1-2 was replaced by M2-1. 
     Preparation of D5 
     
       
         
         
             
             
         
       
     
     D5 was prepared in the same way as A1, following the same preparation method of A1, using the same molar ratio, except that M1-1 was replaced by M15-1, and M1-2 was replaced by M3-1. 
     Preparation of D11 
     
       
         
         
             
             
         
       
     
     M16-1 was prepared in the same way as M4-1, following the same preparation method of M4-1, using the same molar ratio, except that 2-amino-3-dibenzofuranol was replaced with 4-amino-3-dibenzofuranol. 
     
       
         
         
             
             
         
       
     
     M16-2 was prepared in the same way as M1-1, following the same preparation method of M1-1, using the same molar ratio, except that 2-amino-3-dibenzofuranol was replaced with M16-1. 
     
       
         
         
             
             
         
       
     
     M16-3 was prepared in the same way as A1, following the same preparation method of A1, using the same molar ratio, except that M1-1 was replaced by M16-2, and M1-2 was replaced by iodobenzene. 
     
       
         
         
             
             
         
       
     
     M16-4 was prepared in the same way as M4-4, following the same preparation method of M4-4, using the same molar ratio, except that M4-3 was replaced by M16-3. 
     
       
         
         
             
             
         
       
     
     D11 was prepared in the same way as A12, following the same preparation method of A12, using the same molar ratio, except that M4-4 was replaced by M16-4. 
     Preparation of D21 
     
       
         
         
             
             
         
       
     
     M17-1 was prepared in the same way as M4-3, following the same preparation method of M4-3, using the same molar ratio, except that M4-2 was replaced with 2-amino-4-chloro-1,3-benzenediol. 
     
       
         
         
             
             
         
       
     
     M17-2 was prepared in the same way as A12, following the same preparation method of A12, using the same molar ratio, except that M4-3 was replaced with M17-1, and M1-2 was replaced with 2-bromo-4-chlorophenol. 
     
       
         
         
             
             
         
       
     
     M17-3 was prepared in the same way as M5-3, following the same preparation method of M5-3, using the same molar ratio, except that M5-2 was replaced by M17-2. 
     
       
         
         
             
             
         
       
     
     M17-4 was prepared in the same way as M1-1, following the same preparation method of M1-1, using the same molar ratio, except that 2-amino-3-dibenzofuranol was replaced with M17-3. 
     
       
         
         
             
             
         
       
     
     M17-5 was prepared in the same way as A1, following the same preparation method of A1, using the same molar ratio, except that M1-1 was replaced by M17-4, and M1-2 was replaced by 4-iodopyridine. 
     
       
         
         
             
             
         
       
     
     M17-6 was prepared in the same way as M4-3, following the same preparation method of M4-3, using the same molar ratio, except that M4-2 was replaced by M17-5. 
     
       
         
         
             
             
         
       
     
     D21 was prepared in the same way as A12, following the same preparation method of A12, using the same molar ratio, except that M4-4 was replaced by M17-6. 
     Preparation of D24 
     
       
         
         
             
             
         
       
     
     M18-1 was prepared in the same way as A12, following the same preparation method of A12, using the same molar ratio, except that M4-3 was replaced by M18-1, and M1-2 was replaced by 2-bromo-5-chlorophenol. 
     
       
         
         
             
             
         
       
     
     M18-2 was prepared in the same way as M5-3, following the same preparation method of M5-3, using the same molar ratio, except that M5-2 was replaced by M18-1. 
     
       
         
         
             
             
         
       
     
     M18-3 was prepared in the same way as M1-1, following the same preparation method of M1-1, using the same molar ratio, except that 2-amino-3-dibenzofuranol was replaced with M18-2. 
     
       
         
         
             
             
         
       
     
     M18-4 was prepared in the same way as A1, following the same preparation method of A1, using the same molar ratio, except that M1-1 was replaced by M18-3, and M1-2 was replaced by 1-iodonaphthalene. 
     
       
         
         
             
             
         
       
     
     M18-5 was prepared in the same way as M4-3, following the same preparation method of M4-3, using the same molar ratio, except that M4-2 was replaced by M18-4. 
     
       
         
         
             
             
         
       
     
     D24 was prepared in the same way as A12, following the same preparation method of A12, using the same molar ratio, except that M4-4 was replaced by M18-5. 
     Preparation of E1 
     
       
         
         
             
             
         
       
     
     M19-1 was prepared in the same way as M1-1, following the same preparation method of M1-1, using the same molar ratio, except that 2-amino-3-dibenzofuranol was replaced with 1-amino-2-dibenzofuranol. 
     
       
         
         
             
             
         
       
     
     E1 was prepared in the same way as A1, following the same preparation method of A1, using the same molar ratio, except that M1-1 was replaced by M19-1. 
     Preparation of E2 
     
       
         
         
             
             
         
       
     
     E2 was prepared in the same way as A1, following the same preparation method of A1, using the same molar ratio, except that M1-1 was replaced by M19-1, and M1-2 was replaced by M2-1. 
     Preparation of E5 
     
       
         
         
             
             
         
       
     
     E5 was prepared in the same way as A1, following the same preparation method of A1, using the same molar ratio, except that M1-1 was replaced by M19-1, and M1-2 was replaced by M3-1. 
     Preparation of E12 
     
       
         
         
             
             
         
       
     
     M20-1 was prepared in the same way as M4-1, following the same preparation method of M4-1, using the same molar ratio, except that 2-amino-3-dibenzofuranol was replaced with 1-amino-2-dibenzofuranol. 
     
       
         
         
             
             
         
       
     
     M20-2 was prepared in the same way as M1-1, following the same preparation method of M1-1, using the same molar ratio, except that 2-amino-3-dibenzofuranol was replaced with M20-1. 
     
       
         
         
             
             
         
       
     
     M20-3 was prepared in the same way as A1, following the same preparation method of A1, using the same molar ratio, except that M1-1 was replaced with M20-2, and M1-2 was replaced with iodobenzene. 
     
       
         
         
             
             
         
       
     
     M20-4 was prepared in the same way as M4-4, following the same preparation method of M4-4, using the same molar ratio, except that M4-3 was replaced by M20-3. 
     
       
         
         
             
             
         
       
     
     E12 was prepared in the same way as A12, following the same preparation method of A12, using the same molar ratio, except that M4-4 was replaced by M20-4. 
     Preparation of E21 
     
       
         
         
             
             
         
       
     
     M21-1 was prepared in the same way as M4-3, following the same preparation method of M4-3, using the same molar ratio, except that M4-2 was replaced with 2-amino-3-chloro-1,4-benzenediol. 
     
       
         
         
             
             
         
       
     
     M21-2 was prepared in the same way as A12, following the same preparation method of A12, using the same molar ratio, except that M4-3 was replaced by M21-1, and M1-2 was replaced by 2-bromo-4-chlorophenol. 
     
       
         
         
             
             
         
       
     
     M21-3 was prepared in the same way as M5-3, following the same preparation method of M5-3, using the same molar ratio, except that M5-2 was replaced by M21-2. 
     
       
         
         
             
             
         
       
     
     M21-4 was prepared in the same way as M1-1, following the same preparation method of M1-1, using the same molar ratio, except that 2-amino-3-dibenzofuranol was replaced with M21-3. 
     
       
         
         
             
             
         
       
     
     M21-5 was prepared in the same way as A1, following the same preparation method of A1, using the same molar ratio, except that M1-1 was replaced by M21-4, and M1-2 was replaced by 4-iodopyridine. 
     
       
         
         
             
             
         
       
     
     M21-6 was prepared in the same way as M4-3, following the same preparation method of M4-3, using the same molar ratio, except that M4-2 was replaced by M21-5. 
     
       
         
         
             
             
         
       
     
     E21 was prepared in the same way as A12, following the same preparation method of A12, using the same molar ratio, except that M4-4 was replaced by M21-6. 
     Preparation of E24 
     
       
         
         
             
             
         
       
     
     M22-1 was prepared in the same way as A12, following the same preparation method of A12, using the same molar ratio, except that M4-3 was replaced by M21-1, and M1-2 was replaced by 2-bromo-5-chlorophenol. 
     
       
         
         
             
             
         
       
     
     M22-2 was prepared in the same way as A M5-3, following the same preparation method of M5-3, using the same molar ratio, except that M5-2 was replaced by M22-1. 
     
       
         
         
             
             
         
       
     
     M22-3 was prepared in the same way as M1-1, following the same preparation method of M1-1, using the same molar ratio, except that 2-amino-3-dibenzofuranol was replaced with M22-2. 
     
       
         
         
             
             
         
       
     
     M22-4 was prepared in the same way as A1, following the same preparation method of A1, using the same molar ratio, except that M1-1 was replaced by M22-3, and M1-2 was replaced by 1-iodonaphthalene. 
     
       
         
         
             
             
         
       
     
     M22-5 was prepared in the same way as M4-3, following the same preparation method of M4-3, using the same molar ratio, except that M4-2 was replaced by M22-4. 
     
       
         
         
             
             
         
       
     
     E24 was prepared in the same way as A12, following the same preparation method of A12, using the same molar ratio, except that M4-4 was replaced by M22-5 
     Preparation of F1 
     
       
         
         
             
             
         
       
     
     M23-1 was prepared in the same way as M1-1, following the same preparation method of M1-1, using the same molar ratio, except that 2-amino-3-dibenzofuranol was replaced by 2-amino-1-dibenzofuranol. 
     
       
         
         
             
             
         
       
     
     F1 was prepared in the same way as A1, following the same preparation method of A1, using the same molar ratio, except that M1-1 was replaced by M23-1. 
     Preparation of F2 
     
       
         
         
             
             
         
       
     
     F2 was prepared in the same way as A1, following the same preparation method of A1, using the same molar ratio, except that M1-1 was replaced by M23-1, and M1-2 was replaced by M2-1. 
     Preparation of F5 
     
       
         
         
             
             
         
       
     
     F5 was prepared in the same way as A1, following the same preparation method of A1, using the same molar ratio, except that M1-1 was replaced by M23-1, and M1-2 was replaced by M3-1. 
     Preparation of F12 
     
       
         
         
             
             
         
       
     
     M24-1 was prepared in the same way as M4-1, following the same preparation method of M4-1, using the same molar ratio, except that 2-amino-3-dibenzofuranol was replaced by 2-amino-1-dibenzofuranol. 
     
       
         
         
             
             
         
       
     
     M24-2 was prepared in the same way as M1-1, following the same preparation method of M1-1, using the same molar ratio, except that 2-amino-3-dibenzofuranol was replaced with M24-1. 
     
       
         
         
             
             
         
       
     
     M24-3 was prepared in the same way as A1, following the same preparation method of A1, using the same molar ratio, except that M1-1 was replaced with M24-2, and M1-2 was replaced with iodobenzene. 
     
       
         
         
             
             
         
       
     
     M24-4 was prepared in the same way as M4-4, following the same preparation method of M4-4, using the same molar ratio, except that M4-3 was replaced by M24-3. 
     
       
         
         
             
             
         
       
     
     F12 was prepared in the same way as A12, following the same preparation method of A12, using the same molar ratio, except that M4-4 was replaced by M24-4. 
     Preparation of F21 
     
       
         
         
             
             
         
       
     
     M25-1 was prepared in the same way as M4-3, following the same preparation method of M4-3, using the same molar ratio, except that M4-2 was replaced by 4-amino-2-chloro-1,3-benzenediol. 
     
       
         
         
             
             
         
       
     
     M25-2 was prepared in the same way as A12, following the same preparation method of A12, using the same molar ratio, except that M4-3 was replaced by M25-1, and M1-2 was replaced by 2-bromo-4-chlorophenol. 
     
       
         
         
             
             
         
       
     
     M25-3 was prepared in the same way as M5-3, following the same preparation method of M5-3, using the same molar ratio, except that M5-2 was replaced by M25-2. 
     
       
         
         
             
             
         
       
     
     M25-4 was prepared in the same way as M1-1, following the same preparation method of M1-1, using the same molar ratio, except that 2-amino-3-dibenzofuranol was replaced with M25-3. 
     
       
         
         
             
             
         
       
     
     M25-5 was prepared in the same way as A1, following the same preparation method of A1, using the same molar ratio, except that M1-1 was replaced by M25-4, and M1-2 was replaced by 4-iodopyridine. 
     
       
         
         
             
             
         
       
     
     M25-6 was prepared in the same way as M4-3, following the same preparation method of M4-3, using the same molar ratio, except that M4-2 was replaced by M25-5. 
     
       
         
         
             
             
         
       
     
     F21 was prepared in the same way as A12, following the same preparation method of A12, using the same molar ratio, except that M4-4 was replaced by M25-6. 
     Preparation of F24 
     
       
         
         
             
             
         
       
     
     M26-1 was prepared in the same way as A12, following the same preparation method of A12, using the same molar ratio, except that M4-3 was replaced by M25-1, and M1-2 was replaced by 2-bromo-5-chlorophenol. 
     
       
         
         
             
             
         
       
     
     M26-2 was prepared in the same way as M5-3, following the same preparation method of M5-3, using the same molar ratio, except that M5-2 was replaced by M26-1. 
     
       
         
         
             
             
         
       
     
     M26-3 was prepared in the same way as M1-1, following the same preparation method of M1-1, using the same molar ratio, except that 2-amino-3-dibenzofuranol was replaced with M26-2. 
     
       
         
         
             
             
         
       
     
     M26-4 was prepared in the same way as A1, following the same preparation method of A1, using the same molar ratio, except that M1-1 was replaced by M26-3, and M1-2 was replaced by 1-iodonaphthalene. 
     
       
         
         
             
             
         
       
     
     M26-5 was prepared in the same way as M4-3, following the same preparation method of M4-3, using the same molar ratio, except that M4-2 was replaced by M26-4. 
     
       
         
         
             
             
         
       
     
     F24 was prepared in the same way as A12, following the same preparation method of A12, using the same molar ratio, except that M4-4 was replaced by M26-5. 
     The compounds synthesized in the above examples were identified by matrix-assisted laser desorption ionization time-of-flight mass spectrometry and elemental analysis, and the results thereof are shown in Table 1 below. 
     
       
         
           
               
               
               
               
               
               
             
               
                 TABLE 1 
               
               
                   
               
               
                   
                 MALDI-TOF MS 
                 MALDI-TOF MS 
                 UV 
                   
                   
               
               
                   
                 theoretical 
                 measured 
                 absorption 
                 Elemental analysis 
                 Elemental analysis 
               
               
                 Compound 
                 value (m/z) 
                 value (m/z) 
                 (nm) 
                 theoretical value 
                 measured value 
               
               
                   
               
             
            
               
                   
               
            
           
           
               
               
               
               
               
               
            
               
                 A1 
                 642.21 
                 641.54 
                 387 
                 C: 82.23; H: 4.08; 
                 C: 82.20; H: 4.12; 
               
               
                   
                   
                   
                   
                 N: 8.72; 
                 N: 8.70; 
               
               
                 A2 
                 642.21 
                 641.88 
                 354 
                 C: 82.23; H: 4.08; 
                 C: 82.21; H: 4.08; 
               
               
                   
                   
                   
                   
                 N: 8.72; 
                 N: 8.73; 
               
               
                 A5 
                 642.21 
                 642.20 
                 367 
                 C: 82.23; H: 4.08; 
                 C: 82.24; H: 4.09; 
               
               
                   
                   
                   
                   
                 N: 8.72; 
                 N: 8.72; 
               
               
                 A12 
                 718.24 
                 718.33 
                 381 
                 C: 83.55; H: 4.21; 
                 C: 83.52; H: 4.23; 
               
               
                   
                   
                   
                   
                 N: 7.79; 
                 N: 7.78; 
               
               
                 A21 
                 719.23 
                 719.08 
                 400 
                 C: 81.76; H: 4.06; 
                 C: 81.76; H: 4.06; 
               
               
                   
                   
                   
                   
                 N: 9.73; 
                 N: 9.73; 
               
               
                 A24 
                 768.25 
                 768.09 
                 412 
                 C: 84.36; H: 4.20; 
                 C: 84.37; H: 4.18; 
               
               
                   
                   
                   
                   
                 N: 7.29; 
                 N: 7.28; 
               
               
                 B1 
                 642.21 
                 641.74 
                 377 
                 C: 82.23; H: 4.08; 
                 C: 82.23; H: 4.08; 
               
               
                   
                   
                   
                   
                 N: 8.72; 
                 N: 8.72; 
               
               
                 B2 
                 642.21 
                 641.86 
                 349 
                 C: 82.23; H: 4.08; 
                 C: 82.23; H: 4.10; 
               
               
                   
                   
                   
                   
                 N: 8.72; 
                 N: 8.69; 
               
               
                 B5 
                 642.21 
                 642.08 
                 361 
                 C: 82.23; H: 4.08; 
                 C: 82.22; H: 4.09; 
               
               
                   
                   
                   
                   
                 N: 8.72; 
                 N: 8.70; 
               
               
                 B12 
                 718.24 
                 718.18 
                 371 
                 C: 83.55; H: 4.21; 
                 C: 83.56; H: 4.23; 
               
               
                   
                   
                   
                   
                 N: 7.79; 
                 N: 7.78; 
               
               
                 B21 
                 719.23 
                 719.05 
                 392 
                 C: 81.76; H: 4.06; 
                 C: 81.76; H: 4.06; 
               
               
                   
                   
                   
                   
                 N: 9.73; 
                 N: 9.73; 
               
               
                 B24 
                 768.25 
                 768.11 
                 401 
                 C: 84.36; H: 4.20; 
                 C: 84.36; H: 4.22; 
               
               
                   
                   
                   
                   
                 N: 7.29; 
                 N: 7.25; 
               
               
                 C1 
                 642.21 
                 642.19 
                 397 
                 C: 82.23; H: 4.08; 
                 C: 82.22; H: 4.09; 
               
               
                   
                   
                   
                   
                 N: 8.72; 
                 N: 8.71; 
               
               
                 C2 
                 642.21 
                 642.11 
                 364 
                 C: 82.23; H: 4.08; 
                 C: 82.23; H: 4.08; 
               
               
                   
                   
                   
                   
                 N: 8.72; 
                 N: 8.72; 
               
               
                 C5 
                 642.21 
                 641.94 
                 377 
                 C: 82.23; H: 4.08; 
                 C: 82.23; H: 4.08; 
               
               
                   
                   
                   
                   
                 N: 8.72; 
                 N: 8.72; 
               
               
                 C11 
                 718.24 
                 718.16 
                 391 
                 C: 83.55; H: 4.21; 
                 C: 83.56; H: 4.19; 
               
               
                   
                   
                   
                   
                 N: 7.79; 
                 N: 7.78; 
               
               
                 C21 
                 719.23 
                 719.15 
                 410 
                 C: 81.76; H: 4.06; 
                 C: 81.76; H: 4.06; 
               
               
                   
                   
                   
                   
                 N: 9.73; 
                 N: 9.73; 
               
               
                 C24 
                 768.25 
                 768.28 
                 421 
                 C: 84.36; H: 4.20; 
                 C: 84.35; H: 4.22; 
               
               
                   
                   
                   
                   
                 N: 7.29; 
                 N: 7.26; 
               
               
                 D1 
                 642.21 
                 642.06 
                 380 
                 C: 82.23; H: 4.08; 
                 C: 82.23; H: 4.08; 
               
               
                   
                   
                   
                   
                 N: 8.72; 
                 N: 8.72; 
               
               
                 D2 
                 642.21 
                 642.13 
                 349 
                 C: 82.23; H: 4.08; 
                 C: 82.23; H: 4.08; 
               
               
                   
                   
                   
                   
                 N: 8.72; 
                 N: 8.72; 
               
               
                 D5 
                 642.21 
                 642.17 
                 362 
                 C: 82.23; H: 4.08; 
                 C: 82.23; H: 4.08; 
               
               
                   
                   
                   
                   
                 N: 8.72; 
                 N: 8.72; 
               
               
                 D11 
                 718.24 
                 718.27 
                 376 
                 C: 83.55; H: 4.21; 
                 C: 83.55; H: 4.21; 
               
               
                   
                   
                   
                   
                 N: 7.79; 
                 N: 7.79; 
               
               
                 D21 
                 719.23 
                 719.06 
                 394 
                 C: 81.76; H: 4.06; 
                 C: 81.77; H: 4.07; 
               
               
                   
                   
                   
                   
                 N: 9.73; 
                 N: 9.69; 
               
               
                 D24 
                 768.25 
                 768.33 
                 407 
                 C: 84.36; H: 4.20; 
                 C: 84.36; H: 4.20; 
               
               
                   
                   
                   
                   
                 N: 7.29; 
                 N: 7.29; 
               
               
                 E1 
                 642.21 
                 642.28 
                 392 
                 C: 82.23; H: 4.08; 
                 C: 82.23; H: 4.08; 
               
               
                   
                   
                   
                   
                 N: 8.72; 
                 N: 8.72; 
               
               
                 E2 
                 642.21 
                 642.41 
                 359 
                 C: 82.23; H: 4.08; 
                 C: 82.23; H: 4.08; 
               
               
                   
                   
                   
                   
                 N: 8.72; 
                 N: 8.72; 
               
               
                 E5 
                 642.21 
                 641.95 
                 374 
                 C: 82.23; H: 4.08; 
                 C: 82.23; H: 4.08; 
               
               
                   
                   
                   
                   
                 N: 8.72; 
                 N: 8.72; 
               
               
                 E12 
                 718.24 
                 718.39 
                 386 
                 C: 83.55; H: 4.21; 
                 C: 83.55; H: 4.22; 
               
               
                   
                   
                   
                   
                 N: 7.79; 
                 N: 7.82; 
               
               
                 E21 
                 719.23 
                 719.37 
                 405 
                 C: 81.76; H: 4.06; 
                 C: 81.75; H: 4.08; 
               
               
                   
                   
                   
                   
                 N: 9.73; 
                 N: 9.69; 
               
               
                 E24 
                 768.25 
                 768.43 
                 417 
                 C: 84.36; H: 4.20; 
                 C: 84.36; H: 4.20; 
               
               
                   
                   
                   
                   
                 N: 7.29; 
                 N: 7.29; 
               
               
                 F1 
                 642.21 
                 642..32 
                 370 
                 C: 82.23; H: 4.08; 
                 C: 82.24; H: 4.10; 
               
               
                   
                   
                   
                   
                 N: 8.72; 
                 N: 8.67; 
               
               
                 F2 
                 642.21 
                 642.47 
                 344 
                 C: 82.23; H: 4.08; 
                 C: 82.24; H: 4.06; 
               
               
                   
                   
                   
                   
                 N: 8.72; 
                 N: 8.73; 
               
               
                 F5 
                 642.21 
                 642.38 
                 351 
                 C: 82.23; H: 4.08; 
                 C: 82.23; H: 4.08; 
               
               
                   
                   
                   
                   
                 N: 8.72; 
                 N: 8.72; 
               
               
                 F12 
                 718.24 
                 718.01 
                 364 
                 C: 83.55; H: 4.21; 
                 C: 83.56; H: 4.23; 
               
               
                   
                   
                   
                   
                 N: 7.79; 
                 N: 7.74; 
               
               
                 F21 
                 719.23 
                 719.41 
                 386 
                 C: 81.76; H: 4.06; 
                 C: 81.77; H: 4.05; 
               
               
                   
                   
                   
                   
                 N: 9.73; 
                 N: 9.71; 
               
               
                 F24 
                 768.25 
                 768.35 
                 398 
                 C: 84.36; H: 4.20; 
                 C: 84.35; H: 4.23; 
               
               
                   
                   
                   
                   
                 N: 7.29; 
                 N: 7.24; 
               
               
                   
               
            
           
         
       
     
     For the organic compounds provided by the present disclosure, the distribution of the molecular frontier orbitals HOMO and LUMO was optimized and calculated through the Gaussian 09 program package (Gaussian Inc.) at the B3LYP/6-31G(d) calculation level using density functional theory (DFT). In one embodiment, the singlet energy level E S  and triplet energy level E T  of compound molecules were simulated and calculated based on time-dependent density functional theory (TDDFT). The results are shown in Table 2. 
     
       
         
           
               
               
               
               
               
               
             
               
                   
                 TABLE 2 
               
               
                   
                   
               
               
                   
                 Organic 
                 HOMO 
                 LUMO 
                 E S   
                 E T   
               
               
                   
                 compound number 
                 (eV) 
                 (eV) 
                 (eV) 
                 (eV) 
               
               
                   
                   
               
             
            
               
                   
               
            
           
           
               
               
               
               
               
               
            
               
                   
                 A1 
                 −5.67 
                 −1.86 
                 3.20 
                 2.77 
               
               
                   
                 A2 
                 −5.71 
                 −1.91 
                 3.51 
                 2.86 
               
               
                   
                 A5 
                 −5.65 
                 1.89 
                 3.38 
                 2.71 
               
               
                   
                 A12 
                 −5.75 
                 −1.95 
                 3.25 
                 2.66 
               
               
                   
                 A21 
                 −5.60 
                 −1.97 
                 3.10 
                 2.80 
               
               
                   
                 A24 
                 −5.64 
                 −1.83 
                 3.01 
                 2.81 
               
               
                   
                 B1 
                 −5.68 
                 −1.85 
                 3.29 
                 2.72 
               
               
                   
                 B2 
                 −5.72 
                 −1.90 
                 3.55 
                 2.81 
               
               
                   
                 B5 
                 −5.66 
                 1.88 
                 3.43 
                 2.66 
               
               
                   
                 B12 
                 −5.76 
                 −1.94 
                 3.34 
                 2.61 
               
               
                   
                 B21 
                 −5.61 
                 −1.96 
                 3.16 
                 2.75 
               
               
                   
                 B24 
                 −5.65 
                 −1.82 
                 3.09 
                 2.76 
               
               
                   
                 C1 
                 −5.71 
                 −1.82 
                 3.12 
                 2.82 
               
               
                   
                 C2 
                 −5.75 
                 −1.87 
                 3.41 
                 2.91 
               
               
                   
                 C5 
                 −5.69 
                 1.85 
                 3.29 
                 2.76 
               
               
                   
                 C11 
                 −5.79 
                 −1.91 
                 3.17 
                 2.71 
               
               
                   
                 C21 
                 −5.64 
                 −1.93 
                 3.02 
                 2.85 
               
               
                   
                 C24 
                 −5.68 
                 −1.79 
                 2.94 
                 2.86 
               
               
                   
                 D1 
                 −5.73 
                 −1.80 
                 3.26 
                 2.80 
               
               
                   
                 D2 
                 −5.77 
                 −1.85 
                 3.55 
                 2.89 
               
               
                   
                 D5 
                 −5.71 
                 1.83 
                 3.43 
                 2.74 
               
               
                   
                 D11 
                 −5.81 
                 −1.89 
                 3.30 
                 2.69 
               
               
                   
                 D21 
                 −5.66 
                 −1.91 
                 3.15 
                 2.83 
               
               
                   
                 D24 
                 −5.70 
                 −1.77 
                 3.05 
                 2.84 
               
               
                   
                 E1 
                 −5.70 
                 −1.84 
                 3.16 
                 2.84 
               
               
                   
                 E2 
                 −5.74 
                 −1.89 
                 3.45 
                 2.93 
               
               
                   
                 E5 
                 −5.68 
                 1.87 
                 3.32 
                 2.78 
               
               
                   
                 E12 
                 −5.78 
                 −1.93 
                 3.21 
                 2.73 
               
               
                   
                 E21 
                 −5.63 
                 −1.95 
                 3.06 
                 2.87 
               
               
                   
                 E24 
                 −5.67 
                 −1.81 
                 2.97 
                 2.88 
               
               
                   
                 F1 
                 −5.69 
                 −1.83 
                 3.35 
                 2.86 
               
               
                   
                 F2 
                 −5.73 
                 −1.88 
                 3.60 
                 2.95 
               
               
                   
                 F5 
                 −5.67 
                 1.86 
                 3.33 
                 2.80 
               
               
                   
                 F12 
                 −5.77 
                 −1.92 
                 3.41 
                 2.75 
               
               
                   
                 F21 
                 −5.62 
                 −1.94 
                 3.21 
                 2.89 
               
               
                   
                 F24 
                 −5.66 
                 −1.80 
                 3.12 
                 2.90 
               
               
                   
                   
               
            
           
         
       
     
     Comparative Example 
     A glass substrate plate coated with ITO (indium tin oxide) in a thin film at a thickness of 1000 Å was put into distilled water in which a detergent was dissolved, and washed with ultrasonic waves. The ITO was washed for 30 minutes, ultrasonic washed for 10 minutes with distilled water twice. After the ITO was washed with distilled water, it was ultrasonic washed with a solvent of isopropanol, acetone, and methanol, dried, and then transported to a plasma cleaning machine. In one embodiment, after the above substrate plate was washed for 5 minutes by oxygen plasma, it was transported to a vacuum deposition machine. 
     On the ITO transparent electrode prepared above, the following compound [HI] was thermally vacuum-deposited to a thickness of 600 Å to form a hole injection layer. On the above hole injection layer, hexacyano hexaazatriphenylene (HAT) of the following chemical formula and the following compound [HT] were sequentially vacuum-deposited to 50 Å and 600 Å respectively to form a hole transport layer. 
     Next, on the above hole transport layer, the following compounds [BH] and [BD] were vacuum deposited at a weight ratio of 25:1 to a film thickness of 200 Å to form a light-emitting layer. 
     On the above light-emitting layer, the following compounds [ET] and [LiQ] (8-hydroxyquinolinolato-lithium) were vacuum-deposited at a weight ratio of 1:1 to form an electron injection and transport layer in a thickness of 150 Å. On the above electron injection and transport layer, lithium fluoride (LiF) and aluminum were sequentially vapor deposited to a thickness of 10 Å and 1000 Å respectively to form a cathode. 
     In the above process, the vapor deposition rate of organic substance was maintained at 0.4 to 0.9 Å/sec, the vapor deposition rate of lithium fluoride of the cathode was maintained at 0.3 Å/sec, and the vapor deposition rate of aluminum was maintained at 2 Å/sec, during vapor deposition, the vacuum degree was maintained at 1×10 −7  to 5×10 −8  Torr, to produce an organic light-emitting device. 
     
       
         
         
             
             
         
       
       
         
         
             
             
         
       
     
     Experimental Example 1-36 
     Organic light-emitting devices were produced by the same method as in the Comparative Example, according to the above Comparative Example, except that the compound [ET] was replaced with the compounds synthesized in Example 1. 
     The driving voltage and luminous efficiency were measured at a current density of 10 mA/cm 2  for the organic light-emitting devices fabricated using the respective compounds as electron transport layers in the above-mentioned Experimental Examples and Comparative Example, and the time required to reach 95% of the initial brightness (LT95) was measured at a current density of 20 mA/cm 2 . The results are shown in Table 3 below. 
     
       
         
           
               
               
               
               
               
               
             
               
                   
                 TABLE 3 
               
               
                   
                   
               
               
                   
                   
                 Electron 
                   
                 Current 
                   
               
               
                   
                   
                 transport 
                 Voltage 
                 efficiency 
               
               
                   
                 Name 
                 layer 
                 (V) 
                 (cd/A) 
                 LT95(h) 
               
               
                   
                   
               
             
            
               
                   
               
            
           
           
               
               
               
               
               
               
            
               
                   
                 Comparative 
                 ET 
                 5.14 
                 4.11 
                 95 
               
               
                   
                 Example 
               
               
                   
                 Experimental 
                 A1 
                 5.09 
                 4.17 
                 116 
               
               
                   
                 Example 1 
               
               
                   
                 Experimental 
                 A2 
                 5.09 
                 4.23 
                 121 
               
               
                   
                 Example 2 
               
               
                   
                 Experimental 
                 A5 
                 5.05 
                 4.15 
                 131 
               
               
                   
                 Example 3 
               
               
                   
                 Experimental 
                 A12 
                 5.08 
                 4.27 
                 116 
               
               
                   
                 Example 4 
               
               
                   
                 Experimental 
                 A21 
                 5.10 
                 4.19 
                 117 
               
               
                   
                 Example 5 
               
               
                   
                 Experimental 
                 A24 
                 5.08 
                 4.15 
                 117 
               
               
                   
                 Example 6 
               
               
                   
                 Experimental 
                 B1 
                 5.07 
                 4.20 
                 117 
               
               
                   
                 Example 7 
               
               
                   
                 Experimental 
                 B2 
                 5.07 
                 4.25 
                 120 
               
               
                   
                 Example 8 
               
               
                   
                 Experimental 
                 B5 
                 5.09 
                 4.12 
                 127 
               
               
                   
                 Example 9 
               
               
                   
                 Experimental 
                 B12 
                 5.09 
                 4.31 
                 127 
               
               
                   
                 Example 10 
               
               
                   
                 Experimental 
                 B21 
                 5.06 
                 4.21 
                 118 
               
               
                   
                 Example 11 
               
               
                   
                 Experimental 
                 B24 
                 5.08 
                 4.12 
                 118 
               
               
                   
                 Example 12 
               
               
                   
                 Experimental 
                 C1 
                 5.05 
                 4.16 
                 120 
               
               
                   
                 Example 13 
               
               
                   
                 Experimental 
                 C2 
                 5.05 
                 4.24 
                 125 
               
               
                   
                 Example 14 
               
               
                   
                 Experimental 
                 C5 
                 5.07 
                 4.17 
                 119 
               
               
                   
                 Example 15 
               
               
                   
                 Experimental 
                 C11 
                 5.08 
                 4.28 
                 119 
               
               
                   
                 Example 16 
               
               
                   
                 Experimental 
                 C21 
                 5.07 
                 4.18 
                 121 
               
               
                   
                 Example 17 
               
               
                   
                 Experimental 
                 C24 
                 5.06 
                 4.17 
                 120 
               
               
                   
                 Example 18 
               
               
                   
                 Experimental 
                 D1 
                 5.06 
                 4.19 
                 121 
               
               
                   
                 Example 19 
               
               
                   
                 Experimental 
                 D2 
                 5.05 
                 4.27 
                 124 
               
               
                   
                 Example 20 
               
               
                   
                 Experimental 
                 D5 
                 5.07 
                 4.14 
                 116 
               
               
                   
                 Example 21 
               
               
                   
                 Experimental 
                 D11 
                 5.08 
                 4.31 
                 120 
               
               
                   
                 Example 22 
               
               
                   
                 Experimental 
                 D21 
                 5.06 
                 4.21 
                 122 
               
               
                   
                 Example 23 
               
               
                   
                 Experimental 
                 D24 
                 5.07 
                 4.14 
                 119 
               
               
                   
                 Example 24 
               
               
                   
                 Experimental 
                 E1 
                 5.07 
                 4.16 
                 119 
               
               
                   
                 Example 25 
               
               
                   
                 Experimental 
                 E2 
                 5.06 
                 4.22 
                 119 
               
               
                   
                 Example 26 
               
               
                   
                 Experimental 
                 E5 
                 5.09 
                 4.14 
                 130 
               
               
                   
                 Example 27 
               
               
                   
                 Experimental 
                 E12 
                 5.09 
                 4.30 
                 126 
               
               
                   
                 Example 28 
               
               
                   
                 Experimental 
                 E21 
                 5.06 
                 4.21 
                 116 
               
               
                   
                 Example 29 
               
               
                   
                 Experimental 
                 E24 
                 5.05 
                 4.15 
                 129 
               
               
                   
                 Example 30 
               
               
                   
                 Experimental 
                 F1 
                 5.08 
                 4.20 
                 117 
               
               
                   
                 Example 31 
               
               
                   
                 Experimental 
                 F2 
                 5.07 
                 4.26 
                 119 
               
               
                   
                 Example 32 
               
               
                   
                 Experimental 
                 F5 
                 5.05 
                 4.13 
                 118 
               
               
                   
                 Example 33 
               
               
                   
                 Experimental 
                 F12 
                 5.08 
                 4.34 
                 116 
               
               
                   
                 Example 34 
               
               
                   
                 Experimental 
                 F21 
                 5.06 
                 4.25 
                 116 
               
               
                   
                 Example 35 
               
               
                   
                 Experimental 
                 F24 
                 5.07 
                 4.15 
                 116 
               
               
                   
                 Example 36 
               
               
                   
                   
               
            
           
         
       
     
     As shown in Table 3, the organic light-emitting devices of Experimental Examples using the compounds provided by the present disclosure as electron transport layer materials exhibited superior device characteristics compared to the organic light-emitting device prepared in Comparative Example using the compound that was not included in formula 1. 
     In general, considering that the luminous efficiency and lifetime characteristics of organic light-emitting devices have a trade-off relationship with each other, it can be seen that compared with the device of the Comparative Example, when the substituents in formula 1 are changed, the electron transport rate can be adjusted, and the balance of current carrier of the device can be adjusted, which shows a marked improvement. 
     The descriptions of the above examples are only used to help understand the method and the embodiments of the present disclosure. It should be noted that several improvements and modifications can be made to the present disclosure, and these improvements and modifications also fall within the claims and the embodiments of the present disclosure.