An organic compound and its application

Abstract

The present invention provides an organic compound and an application thereof. The organic compound of the present invention belongs to a material with a specific large conjugated fused ring structure, has suitable HOMO and LUMO values, and effectively improves the ability of electron transmission; has high electron mobility, excellent thermal stability and film stability, is conducive to improving luminous efficiency, reducing injection barriers, and reducing device operating voltage; and can improve electron transmission rate, balance electron and hole injection, and improve device luminous efficiency and life; an organic electroluminescent device using the organic compound of the present invention has a lower driving voltage, a higher current efficiency and a longer life.

Description

Technical Field

[0001] The invention belongs to the field of electroluminescent materials and relates to an organic compound and application thereof. Background Art

[0002] The electron transport material used in traditional electroluminescent devices is Alq3, but the electron mobility of Alq3 is relatively low (about 10-6cm 2 / Vs), which makes the electron and hole transmission of the device unbalanced. With the commercialization and practical application of electroluminescent devices, people hope to obtain ETL materials with higher transmission efficiency and better performance. In this field, researchers have done a lot of exploratory work.

[0003] Designing and developing stable and efficient electron transport materials and / or electron injection materials that have both high electron mobility and high glass transition temperature and are effectively doped with metal Yb or Liq can reduce threshold voltage, improve device efficiency, and extend device life, which has very important practical application value.

[0004] The glass transition temperature of existing electron transport materials is low, generally less than 85°C. When the device is running, the Joule heat generated will cause the degradation of molecules and changes in molecular structure, resulting in low panel efficiency and poor thermal stability. After a long time, it is easy to crystallize, and the charge transition mechanism between molecules will be different from the normal operation of the amorphous film mechanism, resulting in reduced electron transport performance.

[0005] Therefore, in this field, further developing materials that can make the device have stable performance, reduce its driving voltage and improve its device luminous efficiency and lifespan remains a research focus. Summary of the invention

[0006] In view of the deficiencies in the prior art, the present invention aims to provide an organic compound and application thereof.

[0007] To achieve this object, the present invention adopts the following technical solutions:

[0008] One of the purposes of the present invention is to provide an organic compound having a structure as shown in Formula I:

[0009]

[0010] wherein X is selected from O, S or NR; R is selected from H, deuterium, halogen, cyano, substituted or unsubstituted C5-C30 aryl, substituted or unsubstituted C4-C30 heteroaryl;

[0011] Z1 to Z 11 is selected from N or C, and at least one of Z1 to Z3 is N;

[0012] L is selected from a single bond or a substituted or unsubstituted C5-C30 arylene group, or a substituted or unsubstituted C4-C30 heteroarylene group;

[0013] Ar1 to Ar3 are each independently selected from a substituted or unsubstituted C5-C30 arylene group, or a substituted or unsubstituted C4-C30 heteroarylene group;

[0014] The substituent in the substituted C5-C30 arylene group or the substituted C4-C30 heteroarylene group is selected from C5-C20 arylene group or C4-C20 heteroarylene group.

[0015] In the present invention, C5-C30 can each independently be C6, C7, C8, C9, C10, C12, C13, C14, C15, C16, C18, C20, C22, C24, C26, C28, C29, etc.

[0016] The C4-C30 can each independently be C4, C5, C6, C7, C8, C9, C10, C12, C13, C14, C15, C16, C18, C20, C22, C24, C26, C28, C29, etc.

[0017] The C5-C20 can each independently be C6, C7, C8, C9, C10, C12, C13, C14, C15, C16, C18, C20, etc.

[0018] The C4-C20 can each independently be C5, C7, C8, C9, C10, C12, C13, C14, C15, C16, C18, C20, etc.

[0019] In the present invention, the organic compound has electrochemical reducibility and reversibility, has a sufficiently high reduction potential, is conducive to electron transmission, has a suitable HOMO energy level and LUMO energy level, minimizes the electron injection barrier, so that the device can have a lower turn-on and operating voltage, and has a certain hole blocking ability, high electron mobility, ensures that the electrons in the device can recombine in the light-emitting layer, so that the generation rate of excitons is increased, the glass transition temperature Tg and thermal decomposition stability are high, and thus the influence of the Joule heat generated by the device during operation on the device life and efficiency is avoided; the organic compound has good film-forming property, good film-forming uniformity, no pinholes, and presents an amorphous film morphology, avoiding degradation or attenuation caused by light scattering or crystallization.

[0020] The organic compound of the invention belongs to a material with a specific large conjugated condensed ring structure, and can make an organic electroluminescent device using the organic compound have a lower driving voltage, a higher current efficiency and a longer lifespan.

[0021] A second object of the present invention is to provide an electron blocking material, wherein the electron blocking material comprises the organic compound as described in the first object.

[0022] A third object of the present invention is to provide an electron transport material, wherein the electron transport material comprises the organic compound as described in one of the objects.

[0023] A fourth object of the present invention is to provide an OLED device, comprising an anode, a cathode and an organic thin film layer disposed between the anode and the cathode, wherein the material of the organic thin film layer comprises the organic compound as described in one of the objects.

[0024] The fifth object of the present invention is to provide a display panel, which includes the OLED device as described in the fourth object.

[0025] A sixth object of the present invention is to provide an organic light-emitting display device, wherein the organic light-emitting display device includes the display panel as described in the fifth object.

[0026] Compared with the prior art, the present invention has the following beneficial effects:

[0027] The organic compound of the present invention belongs to a material with a specific large conjugated fused ring structure, has suitable HOMO and LUMO values, and effectively improves the ability of electron transmission; has high electron mobility, excellent thermal stability and film stability, is conducive to improving luminous efficiency, reducing injection barriers, and reducing device operating voltage; and can improve electron transmission rate, balance electron and hole injection, and improve device luminous efficiency and life; an organic electroluminescent device using the organic compound of the present invention has a lower driving voltage, a higher current efficiency and a longer life. DETAILED DESCRIPTION

[0028] The technical solution of the present invention is further described below by specific implementation methods. It should be understood by those skilled in the art that the embodiments are only to help understand the present invention and should not be regarded as specific limitations of the present invention.

[0029] One of the purposes of the present invention is to provide an organic compound having a structure as shown in Formula I:

[0030]

[0031] wherein X is selected from O, S or NR; R is selected from H, deuterium, halogen, cyano, substituted or unsubstituted C5-C30 aryl, substituted or unsubstituted C4-C30 heteroaryl;

[0032] Z1 to Z 11 is selected from N or C, and at least one of Z1 to Z3 is N;

[0033] L is selected from a single bond or a substituted or unsubstituted C5-C30 arylene group, or a substituted or unsubstituted C4-C30 heteroarylene group;

[0034] Ar1 to Ar3 are each independently selected from a substituted or unsubstituted C5-C30 arylene group, or a substituted or unsubstituted C4-C30 heteroarylene group;

[0035] The substituent in the substituted C5-C30 arylene group or the substituted C4-C30 heteroarylene group is selected from C5-C20 arylene group or C4-C20 heteroarylene group.

[0036] In the present invention, C5-C30 can each independently be C6, C7, C8, C9, C10, C12, C13, C14, C15, C16, C18, C20, C22, C24, C26, C28, C29, etc.

[0037] The C4-C30 can each independently be C4, C5, C6, C7, C8, C9, C10, C12, C13, C14, C15, C16, C18, C20, C22, C24, C26, C28, C29, etc.

[0038] The C5-C20 can each independently be C6, C7, C8, C9, C10, C12, C13, C14, C15, C16, C18, C20, etc.

[0039] The C4-C20 can each independently be C5, C7, C8, C9, C10, C12, C13, C14, C15, C16, C18, C20, etc.

[0040] In the present invention, the organic compound has electrochemical reducibility and reversibility, has a sufficiently high reduction potential, is conducive to electron transmission, has a suitable HOMO energy level and LUMO energy level, minimizes the electron injection barrier, so that the device can have a lower turn-on and operating voltage, and has a certain hole blocking ability, high electron mobility, ensures that the electrons in the device can recombine in the light-emitting layer, so that the generation rate of excitons is increased, the glass transition temperature Tg and thermal decomposition stability are high, and thus the influence of the Joule heat generated by the device during operation on the device life and efficiency is avoided; the organic compound has good film-forming property, good film-forming uniformity, no pinholes, and presents an amorphous film morphology, avoiding degradation or attenuation caused by light scattering or crystallization.

[0041] The organic compound of the invention belongs to a material with a specific large conjugated condensed ring structure, and can make an organic electroluminescent device using the organic compound have a lower driving voltage, a higher current efficiency and a longer lifespan.

[0042] In some embodiments, the organic compound has a structure as shown in Formula II:

[0043]

[0044] wherein X is selected from O, S or NR; R is selected from H, deuterium, halogen, cyano, substituted or unsubstituted C5-C30 aryl, substituted or unsubstituted C4-C30 heteroaryl;

[0045] Z1 to Z 14 is selected from N or C, and at least one of Z1 to Z3 is N, Z 12 To Z 16 At least one of them is N;

[0046] L is selected from a single bond or a substituted or unsubstituted C5-C30 arylene group, or a substituted or unsubstituted C4-C30 heteroarylene group;

[0047] Ar2 and Ar3 are each independently selected from substituted or unsubstituted C5-C30 arylene, substituted or unsubstituted C4-C30 heteroarylene;

[0048] The substituent in the substituted C5-C30 arylene group or the substituted C4-C30 heteroarylene group is selected from C5-C20 arylene group or C4-C20 heteroarylene group.

[0049] The use of the organic compound having the structure of Formula II in the present invention can expand the LUMO distribution, facilitate the transmission of electrons, and improve the efficiency of the device.

[0050] In some embodiments, in the structure shown in Formula I or the structure shown in Formula II, R is selected from H, deuterium, halogen, cyano, or substituted or unsubstituted groups: phenyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, naphthyl, anthracenyl, phenanthrenyl, quinolyl, isoquinolyl, quinoxalinyl or quinazolinyl, and the substituted substituent is halogen or C1-C5 alkyl.

[0051] In some embodiments, in the structure shown in Formula I or the structure shown in Formula II, X is preferably O or NR.

[0052] In some embodiments, in the structure shown in Formula I or the structure shown in Formula II, Z1 to Z3 are all N.

[0053] In some embodiments, in the structure shown in Formula I or the structure shown in Formula II, L is selected from a single bond, Z is independently selected from C or N, and the wavy line represents the attachment site of the group.

[0054] In some embodiments, in the structure shown in Formula I, Ar1 to Ar3 are selected from any one of the following substituted or unsubstituted groups: phenyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, naphthyl, anthracenyl, phenanthryl, quinolyl, isoquinolyl, quinoxalinyl or quinazolinyl phenyl, carbazolyl, dibenzothiophenyl, dibenzofuranyl, 1-phenylbenzimidazolyl, 2-phenylbenzimidazolyl, benzoxazolyl, benzothiazolyl, and the substituted substituent is halogen or C1-C5 alkyl.

[0055] In some embodiments, the organic compound is any one of the following compounds:

[0056]

[0057]

[0058]

[0059]

[0060]

[0061]

[0062]

[0063]

[0064]

[0065] A second object of the present invention is to provide an electron blocking material, wherein the electron blocking material comprises the organic compound as described in the first object.

[0066] A third object of the present invention is to provide an electron transport material, wherein the electron transport material comprises the organic compound as described in one of the objects.

[0067] A fourth object of the present invention is to provide an OLED device, comprising an anode, a cathode and an organic thin film layer disposed between the anode and the cathode, wherein the material of the organic thin film layer comprises the organic compound as described in one of the objects.

[0068] In the OLED device provided by the present invention, the anode material can be a metal, a metal oxide or a conductive polymer; wherein the metal includes copper, gold, silver, iron, chromium, nickel, manganese, palladium, platinum, etc. and their alloys, the metal oxide includes indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide, indium gallium zinc oxide (IGZO), etc., and the conductive polymer includes polyaniline, polypyrrole, poly (3-methylthiophene), etc. In addition to the above materials and combinations thereof that facilitate hole injection, known materials suitable for anodes are also included.

[0069] In the OLED device, the cathode material may be a metal or a multilayer metal material; wherein the metal includes aluminum, magnesium, silver, indium, tin, titanium, etc. and their alloys, and the multilayer metal material includes LiF / Al, LiO2 / Al, BaF2 / Al, etc. In addition to the above materials and combinations thereof that facilitate electron injection, known materials suitable for the cathode are also included.

[0070] In the OLED device, the organic thin film layer includes at least one light-emitting layer (EML) and any one or a combination of at least two of 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) or an electron injection layer (EIL) disposed on both sides of the light-emitting layer. A cap layer (CPL) may also be optionally disposed on the cathode (the side away from the anode) of the OLED device.

[0071] In some embodiments, the organic thin film layer includes an electron blocking layer, and a material of the electron blocking layer includes at least one of the organic compounds described above.

[0072] In some embodiments, the organic thin film layer includes an electron transport layer, and a material of the electron transport layer includes at least one of the organic compounds described above.

[0073] The OLED device of the present invention can be prepared by the following method: forming an anode on a transparent or opaque smooth substrate, forming an organic thin layer on the anode, and forming a cathode on the organic thin layer. The organic thin layer can be formed by known film forming methods such as evaporation, sputtering, spin coating, dipping, ion plating, etc.

[0074] The fifth object of the present invention is to provide a display panel, which includes the OLED device as described in the fourth object.

[0075] A sixth object of the present invention is to provide an organic light-emitting display device, wherein the organic light-emitting display device includes the display panel as described in the fifth object.

[0076] The following are several examples of preparing the organic compounds of the present invention:

[0077] Preparation Example

[0078] Preparation of Compound A1

[0079]

[0080] In the reactor, add 100 ml of ethanol, 10-amino-9-phenanthranol (21.0 g, 100 mmol), NBS (2.5 g, 220 mmol) and copper nitrate (1.3 g, 10 mmol) in sequence, stir at room temperature for 0.5 h, then heat to 50 ° C and keep for 3 h until the reaction is complete. Cool to 20 ° C, pour the reaction solution into 100 ml of water and stir for 2 h. Filter by suction, stir the filter cake with 100 ml of water at room temperature for 1 h, filter by suction, and dry at 50 ° C to obtain M1-1 (24.1 g, 84%).

[0081]

[0082] M1-1 (29.0 g, 101 mmol) and triethyl formate (20 mL) were added to the reaction vessel. The resulting mixture was refluxed for 9 hours until the reaction was complete. The triethyl formate was then removed. The residue was separated by column chromatography to obtain M1-2 (25.8 g, 86%).

[0083]

[0084] Copper (I) thiophene-2-carboxylate (0.1 g, 0.5 mmol), 2,2'-bipyridine (0.1 g, 0.5 mmol), lithium were added to tert-butoxide (2.0 g, 25 mmol) and anhydrous N,N-dimethylformamide (50 ml, 0.2 M) under nitrogen atmosphere with a magnetic stirring bar. After stirring for 5 minutes, the color of the solvent changed from light green to light yellow, and M1-2 (3.0 g, 10 mmol) and 4-iodopyridine (8.2 g, 40 mmol) were added to the mixture. The resulting solution was then irradiated with a blue LED and stirred at room temperature for 16 hours. Using ethyl acetate as the eluent, the resulting suspension was filtered on a silica gel pad and evaporated in vacuo. The residue was separated by column chromatography to obtain 2.99 g of the product M1-3. (Yield: 80%).

[0085]

[0086] Under nitrogen atmosphere, intermediate M1-3 (7.3 g, 19.55 mmol), bis(boronic acid) pinacol ester (5.96 g, 23.46 mmol), Pd(OAc)2 (0.13 g, 0.59 mmol), KOAc (3.84 g, 39.11 mmol) were mixed with 100 ml of toluene and stirred at 100 ° C for 8 hours. After the reaction was completed, the mixture was extracted with dichloromethane, MgSO4 was added, and the mixture was filtered. After removing the solvent of the filtered organic layer, 7.3 g (yield: 88%) of intermediate M1-4 was obtained by column chromatography.

[0087]

[0088] Intermediate M1-4 (8.4 g, 20.0 mmol), 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine (7.7 g, 20.0 mmol), Pd(PPh3)4 (1.13 g, 0.98 mmol), K2CO3 (8.11 g, 58.66 mmol) were mixed with 100 ml of toluene, 25 ml of H2O and 25 ml of EtOH under nitrogen flow and stirred at 110°C for 4 hours. After the reaction was completed, the mixture was extracted with dichloromethane, MgSO4 was added, and the mixture was filtered. After removing the solvent of the filtered organic layer, 10.9 g (yield: 90%) of the target compound A1 was obtained by column chromatography.

[0089] Preparation of Compound A7

[0090]

[0091] The preparation method of M2-1 is consistent with that of M1-3. According to the preparation method of M1-3, the same molar ratio is used and 4-iodopyridine is replaced with 5-iodopyrimidine.

[0092]

[0093] The preparation method of M2-2 is consistent with that of M1-4. According to the preparation method of M1-4, use the same molar ratio and replace M1-3 with M2-1.

[0094]

[0095] The preparation method of A7 is consistent with that of A1. According to the preparation method of A1, using the same molar ratio, M1-4 is replaced by M2-2.

[0096] Preparation of compound A14

[0097]

[0098] The preparation method of A14 is consistent with that of A1. According to the preparation method of A1, using the same molar ratio, 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine is replaced by 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine.

[0099] Preparation of Compound A17

[0100]

[0101] The preparation method of M3-1 is consistent with that of M1-1. According to the preparation method of M1-1, the same molar ratio is used to replace 10-amino-9-phenanthranol with phenanthro[9,10-d]oxazole.

[0102]

[0103] The preparation method of M3-2 is consistent with that of M1-3. According to the preparation method of M1-3, use the same molar ratio and replace M1-2 with M3-1.

[0104]

[0105] The preparation method of M3-3 is consistent with that of M1-4. According to the preparation method of M1-4, use the same molar ratio and replace M1-3 with M3-2.

[0106]

[0107] The preparation method of A17 is consistent with that of A1. According to the preparation method of A1, using the same molar ratio, M1-4 is replaced by M3-3.

[0108] Preparation of Compound A23

[0109]

[0110] Carbazole (20.5 g, 122.7 mmol), 2-chloro-4-(3-chlorophenyl)-6-phenyl-1,3,5-triazine (37.0 g, 122.9 mmol), tris(dibenzylideneacetone)dipalladium (1.1 g, 1.2 mmol), 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (1.02 g, 2.5 mmol) and sodium tert-butoxide (17.9 g, 186 mmol) were added to toluene (240 mL), heated to 108 ° C under nitrogen protection, stirred for 3 h, and then cooled to room temperature. The reaction solution was washed with water and dried with magnesium sulfate. After filtering, the filtrate was decompressed to remove the solvent, and the crude product was recrystallized and purified using a toluene system to obtain intermediate M4-3 (42.4 g, yield 80%).

[0111]

[0112] The preparation method of A23 is consistent with that of A1. According to the preparation method of A1, using the same molar ratio, 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine is replaced by M4-1.

[0113] Preparation of Compound A42

[0114]

[0115] The intermediate 2,4-dibromo-6-(3-chlorophenyl)-1,3,5-triazine (10.0 g, 28.82 mmol), 1-phenyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxybenzaldehyde-2-yl)-1H benzimidazole (18.5 g, 57.81 mmol), Pd(PPh3)4 (2.26 g, 1.96 mmol), K2CO3 (16.22 g, 117.32 mmol) were mixed with 250 mL of toluene, 50 mL of H2O and 50 mL of EtOH under nitrogen flow and stirred at 110° C. for 4 h. After the reaction was completed, the mixture was extracted with dichloromethane, MgSO4 was added, and the mixture was filtered.

[0116] After removing the solvent of the filtered organic layer, 14.58 g (yield: 88%) of the target compound M5-1 was obtained by column chromatography.

[0117]

[0118] The preparation method of A42 is consistent with that of A1. According to the preparation method of A1, using the same molar ratio, 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine is replaced by M5-1.

[0119] Preparation of compound A50

[0120]

[0121] The preparation method of A50 is consistent with that of A1. According to the preparation method of A1, the same molar ratio is used to replace 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine with 2-(4-bromo-1-naphthyl)-4,6-diphenyl-1,3,5-triazine.

[0122] Preparation of compound A51

[0123]

[0124] The intermediate 2-chloro-6-(4,4,5,5-tetramethyl-1,3,2-dioxybenzaldehyde-2-yl)pyridine (4.8 g, 20.1 mmol), 2-bromo-4,6-diphenyl-1,3,5-triazine (9.3 g, 29.9 mmol), Pd(PPh3)4 (1.13 g, 0.98 mmol), K2CO3 (8.11 g, 58.66 mmol) under nitrogen flow was mixed with 100 ml of toluene, 25 ml of H2O and 25 ml of EtOH and stirred at 110°C for 4 hours. After the reaction was completed, the mixture was extracted with dichloromethane, MgSO4 was added, and the mixture was filtered. After removing the solvent of the filtered organic layer, 6.2 g (yield: 90%) of the target compound M6-1 was obtained by column chromatography.

[0125]

[0126] The preparation method of A51 is consistent with that of A1. According to the preparation method of A1, the same molar ratio is used and 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine is replaced by M6-1.

[0127] Preparation of compound B14

[0128]

[0129] The preparation method of B14 is consistent with that of A1. B14 can be obtained by following the preparation method of A1 and using the same molar ratio.

[0130] Preparation of compound C1

[0131]

[0132] Compound 9,10-phenanthrenedione (11.6 g, 55.8 mmol), 250 ml of dichloromethane and 3 ml of concentrated sulfuric acid were added to the reactor. After the addition was completed, 12 ml of N-bromosuccinimide was added in several portions under stirring at room temperature. After the addition was completed, the reaction was stirred at room temperature for 12 hours. After the reaction was completed by HPLC monitoring, the reaction was stopped, 500 ml of ethanol was added to the reaction solution, and a solid was precipitated. The solid was filtered to obtain a filter cake. The filter cake was boiled in toluene for 3 hours, cooled to room temperature and filtered to obtain 8.8 g (yield: 55%) of the target compound M7-1.

[0133]

[0134] A mixture of M7-1 (41 g, 143.4 mmol), 23 ml of formaldehyde, 560 ml of glacial acetic acid and ammonium acetate (230.7 g, 2.99 mol) was refluxed for 4 hours. After cooling, the reaction mixture was diluted with 600 ml of water and neutralized to neutrality with concentrated ammonia. A precipitate was obtained. Filtered, washed with water, acetone, dichloromethane and ether, and then dried to obtain 40.3 g (95% yield) of M7-2.

[0135]

[0136] The reactor containing K3PO4 (67.0 g, 300 mmol) was dried in vacuo with a hot air gun for 3 minutes, and then filled with argon after cooling to room temperature. Ni(OTf)2 (3.6 g, 10 mmol), M7-2 (29.6 g, 100 mmol), 4-pyridyl N, N-dimethylcarbamate (24.9 g, 150 mmol) and 3,4-bis(dicyclohexylphosphino)thiophene (5.7 g, 12 mmol) were placed in a reactor under an argon atmosphere. Dry and degassed tert-amyl alcohol (400 mL) was then added thereto under an argon stream. The reaction mixture was stirred at 120°C for 36 hours. After the reaction mixture was cooled to room temperature, the mixture was diluted with EtOAc, the organic layer was washed with water and brine, dried over Na2SO4, and filtered. The filtrate was concentrated in vacuo, and the residue was purified by flash silica gel column chromatography to obtain 29.8 g (80% yield) of M7-3.

[0137]

[0138] The preparation method of M7-4 is consistent with that of M1-4. According to the preparation method of M1-4, use the same molar ratio and replace M1-3 with M7-3.

[0139]

[0140] The preparation method of C1 is consistent with that of A1. According to the preparation method of A1, the same molar ratio is used and M1-4 is replaced by M7-4.

[0141] Preparation of compound C14

[0142]

[0143] The preparation method of C14 is consistent with that of A1. According to the preparation method of A1, using the same molar ratio, M1-4 is replaced by M7-4, and 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine is replaced by 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine.

[0144] Preparation of compound D1

[0145]

[0146] The preparation method of D1 is consistent with that of A1. According to the preparation method of A1, the same molar ratio is used to replace 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine with 4-bromo-5'-phenyl-1,1':3',1"-terphenyl.

[0147] Preparation of compound D2

[0148]

[0149] The preparation method of D1 is consistent with that of A1. According to the preparation method of A1, using the same molar ratio, 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine is replaced by M1-2, and M1-4 is replaced by 2,4-diphenyl-6-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1,3,5-triazine.

[0150] 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 are shown in Table 1 below.

[0151] Table 1

[0152]

[0153]

[0154] Device Embodiment

[0155] Comparative Example 1-1

[0156] ITO (indium tin oxide) is used The glass substrate coated with a film of thickness of 1000 nm was placed in distilled water dissolved with detergent and washed with ultrasound. After washing the ITO for 30 minutes, ultrasonic washing was repeated twice with distilled water for 10 minutes. After the distilled water washing was completed, ultrasonic washing was performed with a solvent of isopropanol, acetone, and methanol, and after drying, it was transported to a plasma cleaning machine. In addition, the above substrate was cleaned for 5 minutes using oxygen plasma, and then the substrate was transported to a vacuum evaporation machine.

[0157] On the ITO transparent electrode prepared above, the following compounds were thermally vacuum deposited in sequence: and On the hole injection layer, the following chemical formula is vacuum-deposited Then vacuum evaporation is performed to form a hole transport layer. As an electron blocking layer.

[0158] Next, on the electron blocking layer, the following compounds [BH] and [BD] were coated at a weight ratio of 96:4 and a film thickness of The light emitting layer is formed by vacuum deposition.

[0159] On the above-mentioned light-emitting layer, a hole blocking layer is vacuum deposited Then, ET and Liq were vacuum-deposited at a weight ratio of 1:1. The Liq compound was then vacuum deposited onto On the electron injection layer, magnesium and silver are sequentially deposited in a weight ratio of 10:1 to a thickness of The thickness of aluminum is A cathode is formed, thereby manufacturing an organic light emitting diode.

[0160]

[0161]

[0162] Examples 1-1 to 1-11 and Comparative Examples 1-2 to 1-4 were prepared using the same method as Comparative Example 1-1, except that the compounds shown in Table 2 were used as hole blocking layer materials, to manufacture corresponding light-emitting devices.

[0163] The structure of the material D1 used in Comparative Examples 1-3 is as follows:

[0164] The structure of the material D2 used in Comparative Examples 1-4 is as follows:

[0165] For the above organic light emitting device, at 10 mA / cm 2 The driving voltage and luminous efficiency were measured at a current density of 20 mA / cm 2 The time required for the luminance to reach 95% of the initial luminance (LT95) was measured at a current density of . The results are shown in Table 2 below.

[0166] Table 2

[0167] name Electron blocking layer Voltage (V) Current efficiency (cd / A) LT95(h) Example 1-1 A1 3.51 6.01 182 Example 1-2 A7 3.54 5.84 169 Examples 1-3 A14 3.50 6.14 190 Examples 1-4 A17 3.55 5.52 171 Examples 1-5 A23 3.67 5.34 174 Examples 1-6 A42 3.60 5.30 165 Examples 1-7 A50 3.56 5.77 180 Examples 1-8 A51 3.59 5.54 176 Examples 1-9 B14 3.72 5.61 179 Examples 1-10 C1 3.66 5.60 175 Embodiment 1-11 C14 3.64 5.80 186 Comparative Example 1-1 HB 4.34 4.87 108 Comparative Example 1-2 LG-03 3.85 5.26 161 Comparative Examples 1-3 D1 4.92 3.15 113 Comparative Examples 1-4 D2 4.41 4.11 64

[0168] It can be seen from Table 2 that using the organic compound of the present invention as the electron blocking layer material of the organic electroluminescent device, the device has a lower driving voltage (below 3.72V), a higher current efficiency (above 5.30cd / A) and a longer life (above 165h).

[0169] Comparative Example 2-1

[0170] ITO (indium tin oxide) is used The glass substrate coated with a film of thickness of 1000 nm was placed in distilled water dissolved with detergent and washed with ultrasound. After washing the ITO for 30 minutes, ultrasonic washing was repeated twice with distilled water for 10 minutes. After the distilled water washing was completed, ultrasonic washing was performed with a solvent of isopropanol, acetone, and methanol, and after drying, it was transported to a plasma cleaning machine. In addition, the above substrate was cleaned for 5 minutes using oxygen plasma, and then the substrate was transported to a vacuum evaporation machine.

[0171] On the ITO transparent electrode prepared above, the following compounds were thermally vacuum deposited in sequence: and On the hole injection layer, the following chemical formula is vacuum-deposited Then vacuum evaporation is performed to form a hole transport layer. As an electron blocking layer.

[0172] Next, on the electron blocking layer, the following compounds [BH] and [BD] were coated at a weight ratio of 96:4 and a film thickness of The light emitting layer is formed by vacuum deposition.

[0173] On the above-mentioned light-emitting layer, a hole blocking layer is vacuum deposited Then, LG-03 and Liq were vacuum-deposited at a weight ratio of 1:1. The Liq compound was then vacuum deposited onto On the electron injection layer, magnesium and silver are sequentially deposited in a weight ratio of 10:1 to a thickness of The thickness of aluminum is A cathode is formed, thereby manufacturing an organic light emitting diode.

[0174] Examples 2-1 to 2-11 were prepared by the same method as Comparative Examples 2-1 to 2-3, except that the compounds shown in Table 3 were used as electron transport layer materials, and corresponding light-emitting devices were manufactured.

[0175] For the above organic light emitting device, at 10 mA / cm 2 The driving voltage and luminous efficiency were measured at a current density of 20 mA / cm 2 The time required for the luminance to reach 95% of the initial luminance (LT95) was measured at a current density of . The results are shown in Table 3 below.

[0176] Table 3

[0177] name Electron transport layer Voltage (V) Current efficiency (cd / A) LT95(h) Example 2-1 A1 3.43 6.71 201 Example 2-2 A7 3.46 6.21 187 Example 2-3 A14 3.42 6.69 210 Embodiment 2-4 A17 3.47 6.04 194 Embodiment 2-5 A23 3.59 5.85 191 Embodiment 2-6 A42 3.52 5.72 182 Embodiment 2-7 A50 3.48 6.27 199 Embodiment 2-8 A51 3.51 5.96 193 Embodiment 2-9 B14 3.64 6.04 197 Embodiment 2-10 C1 3.58 6.13 190 Example 2-11 C14 3.56 6.23 204 Comparative Example 2-1 LG-03 3.75 5.20 158 Comparative Example 2-2 D1 6.65 3.34 106 Comparative Example 2-3 D2 4.02 4.74 59

[0178] It can be seen from Table 3 that using the organic compound of the present invention as the electron transport layer material of the organic electroluminescent device, the device has a lower driving voltage (below 3.64V), a higher current efficiency (above 5.72cd / A) and a longer life (above 182h).

[0179] It can be seen that the organic light-emitting device of the comparative example using the compound not included in Chemical Formula 1, the organic light-emitting device of the embodiment using the compound of the present invention as an electron blocking layer material or an electron transport layer material exhibits excellent device characteristics.

[0180] Generally, considering that the luminous efficiency and lifespan characteristics of an organic light-emitting device have a trade-off relationship with each other, it can be seen that compared with the device of the comparative example, it can be confirmed that when the type of substituent or atom in Chemical Formula 1 is changed, the electron transfer rate can be adjusted, and then the balance of the device carriers can be adjusted, showing a significant improvement.

[0181] The applicant declares that the present invention illustrates the compounds and applications of the present invention through the above-mentioned embodiments, but the present invention is not limited to the above-mentioned embodiments, that is, it does not mean that the present invention must rely on the above-mentioned embodiments to be implemented. Those skilled in the art should understand that any improvement of the present invention, equivalent replacement of various raw materials of the product of the present invention, addition of auxiliary components, selection of specific methods, etc., all fall within the protection scope and disclosure scope of the present invention.

Claims

1. An organic compound, characterized in that The organic compound has a structure as shown in Formula II: wherein X is selected from O, S or NR; R is selected from phenyl; Among them, Z1 to Z3 are all N, Z4 to Z 11 Selected from C, Z 12 To Z 16 is selected from C or N, and Z 12 To Z 16 At least one of them is N; L is selected from Z is independently selected from C or N, and the wavy line represents the attachment site of the group; Ar2 and Ar3 are selected from any one of the following groups: phenyl, carbazolyl or 1-phenylbenzimidazolyl.

2. The organic compound according to claim 1, characterized in that The organic compound is any one of the following compounds:

3. An electron blocking material, characterized in that: The electron blocking material includes the organic compound as claimed in claim 1 or 2.

4. An electron transport material, characterized in that The electron transport material includes the organic compound according to claim 1 or 2.

5. An OLED device, characterized in that: The OLED device comprises an anode, a cathode and an organic thin film layer located between the anode and the cathode, wherein the material of the organic thin film layer comprises at least one of the organic compounds as claimed in claim 1 or 2.

6. The OLED device according to claim 5, characterized in that: The organic thin film layer includes an electron transport layer, and a material of the electron transport layer includes at least one of the organic compounds according to claim 1 or 2.

7. A display panel, characterized in that: The display panel comprises the OLED device according to claim 5 or 6.

8. An electronic device, characterized in that: The electronic device comprises the display panel according to claim 7.

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