A compound containing a nitrogen heterocyclic structure and an organic electroluminescent device

Abstract

The present application relates to a kind of compound containing nitrogen heterocyclic structure and organic electroluminescent device.The active site of compound deuterium or aryl substitution improves the chemical stability, photoelectric stability and thermal stability of compound, improves the stability of device, and further improves the life.Can form good Premix material with the P-type compound of the present application, has good P / N stability and mass production stability in the process of evaporation, and the Premix material formed has more balanced carrier mobility, and then the efficiency and life of device are greatly improved.The material of the present application all has excellent solubility, can effectively solve the problem of hole blocking of production line and the problem of Mask cleaning difficulty, while the preparation and recovery cost of material can be greatly reduced.

Description

TECHNICAL FIELD

[0001] The present application relates to the technical field of organic electroluminescence, in particular, the present application relates to a kind of compound and organic electroluminescent device. BACKGROUND

[0002] Organic electroluminescence, generally refers to organic light emitting diode (OLED) by current drive organic semiconductor thin film to achieve luminescence, and then display purposes.

[0003] The composition structure of organic electroluminescent device includes cathode, anode and organic layer arranged between the two. The organic layer structure of OLED device currently applied in industry is usually multilayer structure, for example, it includes hole injection layer, hole transport layer, electron blocking layer, light emitting layer, hole blocking layer, electron transport layer, electron injection layer and other film layers. For the OLED device containing the above film layers, voltage is applied between the two electrodes, then the hole is injected from the anode to the organic layer, and the electron is injected from the cathode to the organic layer, when the hole and the electron meet, the exciton is formed, when the exciton transfers energy to the dopant material, light is emitted through the radiation transition of the dopant material.

[0004] In the existing OLED device, due to the poor compatibility between the green light host, the energy cannot be efficiently transferred to the dopant material, and the efficiency of the conductor OLED device is reduced. At the same time, since it is not deuterated at the active point of the material molecule and the point with high electron density, the chemical stability, thermal stability and photoelectric stability are poor, which further affects the service life of the device, and the P / N ratio of the current green light host will change greatly with the extension of evaporation time, which leads to large fluctuation of device performance, poor stability and low yield.

[0005] The premix material formed by the N-type compound and the P-type compound of the present application is deuterated at the active site of each structure, so it has good thermal stability, chemical stability and photoelectric stability. At the same time, the premix material formed by the compound of the present application has balanced carrier mobility, further expands the exciton recombination region, and further improves the service life and efficiency of the device. SUMMARY

[0006] The purpose of the present application is to provide a compound containing nitrogen heterocyclic structure and organic electroluminescent device on the basis of prior art.

[0007] The purpose of the present application can be achieved by the following measures:

[0008] A compound containing nitrogen heterocyclic structure, its structural formula is shown in the following formula 1:

[0009]

[0010] X is O, S or Se;

[0011] Ar1and Ar2are each independently selected from the group consisting of substituted or unsubstituted phenyl, biphenyl, terphenyl, naphthyl, anthryl, pyridyl, pyrimidyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, spirobifluorenyl, 9,9-dimethylfluorenyl, the substituents of said Ar1and Ar2being selected from one or more of deuterium, fluorine, cyano, C1-C10 alkyl, C1-C10 deuterated alkyl, C1-C10 cycloalkyl, C1-C10 deuterated cycloalkyl, C6-C30 aryl, C6-C30 deuterated aryl, C5-C30 heteroaryl;

[0012] L1-L3are each independently selected from the group consisting of a single bond, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, the substituents of said L1-L3being selected from one or more of deuterium, fluorine, cyano, C1-C10 alkyl, C6-C18 aryl, C5-C20 heteroaryl;

[0013] A1-A 10 are each independently selected from the group consisting of deuterium, fluorine, cyano, substituted or unsubstituted phenyl, biphenyl, naphthyl, pyridyl, the substituents of said A1-A 10 being selected from one or more of deuterium, fluorine, cyano, phenyl, biphenyl, methyl, ethyl, t-butyl, cyclopentyl, cyclohexyl, and at least one of A1-A 10 is substituted or unsubstituted phenyl, biphenyl, naphthyl, pyridyl.

[0014] Preferably, it has the structural formula as shown in the following Formula 2-Formula 4:

[0015]

[0016] X is O, S or Se;

[0017] Ar1and Ar2are selected from the group consisting of substituted or unsubstituted phenyl, biphenyl, terphenyl, naphthyl, anthryl, pyridyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, spirobifluorenyl, 9,9-dimethylfluorenyl, the substituents of said Ar1and Ar2being deuterium, fluorine, cyano, one or more of the following groups which are deuterated or not deuterated: phenyl, biphenyl, methyl, ethyl, t-butyl, cyclopentyl, cyclohexyl;

[0018] L1and L2are each independently selected from the group consisting of a single bond, phenyl, deuterated phenyl, biphenyl, deuterated biphenyl, pyridyl;

[0019] A1-A 10each independently selected from deuterium, fluorine, cyano, one or more of the following groups which are substituted or unsubstituted: phenyl, biphenyl, naphthyl, pyridyl, and A1-A 10 the substituents of A1-A 10 are selected from deuterium, fluorine, cyano, one or more of the following groups: phenyl, biphenyl, methyl, ethyl, t-butyl, cyclopentyl, cyclohexyl, and at least one of A1-A

[0020] each R1is independently selected from hydrogen, deuterium, fluorine, cyano, one or more of the following groups which are deuterated or undeuterated: phenyl, methyl, t-butyl, and

[0021] n is an integer from 0 to 4.

[0022] Preferably, X is O or S.

[0023] Ar1and Ar2are selected from the following groups which are substituted or unsubstituted: phenyl, biphenyl, carbazolyl, diphenylfuryl, dibenzothiophenyl, and the substituents of Ar1and Ar2are selected from deuterium, fluorine, cyano, one or more of the following groups which are deuterated or undeuterated: phenyl, biphenyl, methyl, t-butyl, cyclopentyl, cyclohexyl, and

[0024] each of L1and L2is independently selected from a single bond, phenyl, deuterated phenyl, biphenyl, deuterated biphenyl.

[0025] A1-A 10 each independently selected from deuterium, fluorine, cyano, one or more of the following groups which are substituted or unsubstituted: phenyl, biphenyl, naphthyl, and A1-A 10 the substituents of A1-A 10 are selected from deuterium, fluorine, cyano, one or more of the following groups: phenyl, biphenyl, methyl, t-butyl, and at least one of A1-A

[0026] each R1is independently selected from hydrogen, deuterium, fluorine, cyano, one or more of the following groups which are deuterated or undeuterated: phenyl, methyl, t-butyl, and

[0027] n is an integer from 0 to 4.

[0028] Preferably, X is O or S.

[0029] Ar1and Ar2are selected from the following groups which are substituted or unsubstituted: phenyl, biphenyl, carbazolyl, diphenylfuryl, dibenzothiophenyl, and the substituents of Ar1and Ar2are selected from deuterium, deuterated or undeuterated phenyl, biphenyl, methyl, t-butyl.

[0030] L1and L2are each independently selected from the group consisting of a single bond, phenyl, deutero-phenyl, biphenyl, deutero-biphenyl;

[0031] A1-A 10 are each independently selected from the group consisting of deuterium, substituted or unsubstituted phenyl, biphenyl, naphthyl, and wherein at least one of A1-A 10 is substituted with one or more of deuterium, phenyl, deutero-phenyl, biphenyl, deutero-biphenyl, and wherein at least one of A1-A 10 is substituted or unsubstituted phenyl, biphenyl, naphthyl;

[0032] R1is each independently selected from the group consisting of hydrogen, deuterium, deutero- or non-deutero- substituted phenyl, methyl, t-butyl;

[0033] n is an integer from 0 to 4.

[0034] Further preferably, X is O or S;

[0035] Ar1and Ar2are each independently selected from the group consisting of substituted or unsubstituted phenyl, biphenyl, and wherein the substituents of Ar1and Ar2are one or more of deuterium, phenyl, deutero-phenyl, methyl, t-butyl;

[0036] L1and L2are each independently selected from the group consisting of a single bond, phenyl, deutero-phenyl, biphenyl, deutero-biphenyl;

[0037] A1-A 10 are each independently selected from the group consisting of deuterium, substituted or unsubstituted phenyl, biphenyl, naphthyl, and wherein at least one of A1-A 10 is substituted with one or more of deuterium, phenyl, deutero-phenyl, and wherein at least one of A1-A 10 is substituted or unsubstituted phenyl, biphenyl, naphthyl;

[0038] R1is each independently selected from the group consisting of hydrogen or deuterium;

[0039] n is an integer from 0 to 4.

[0040] In one preferred embodiment, the compound of the present application is any one of the following compounds:

[0041] .

[0042] An organic electroluminescence device comprising a first electrode, a second electrode and an organic layer formed between the first electrode and the second electrode; wherein the organic layer contains a compound of the present application.

[0043] Further, the organic layer comprises a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer; wherein the light-emitting layer contains a compound of the present application.

[0044] Further, the light-emitting layer further contains at least one of the following Formula 5 or Formula 6:

[0045] wherein,

[0046] Ar4and Ar5are each independently selected from the group consisting of substituted or unsubstituted C6-C30aryl, C5-C30heteroaryl, the substituents of said Ar4and Ar5are selected from one or more of deuterium, fluorine, cyano, C1-C10alkyl, C1-C10deuterated alkyl, C1-C10cycloalkyl, C1-C10deuterated cycloalkyl, C6-C30aryl, C6-C30deuterated aryl, C5-C30heteroaryl;

[0047] L4and L5are each independently selected from the group consisting of a single bond, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, the substituents of said L4and L5are selected from one or more of deuterium, fluorine, cyano, C1-C10alkyl, C6-C18aryl, C5-C20heteroaryl;

[0048] R2-R5are each independently selected from the group consisting of hydrogen, deuterium, fluorine, cyano, one or more of the following groups which are deuterated or not deuterated: phenyl, biphenyl, methyl, ethyl, t-butyl;

[0049] m and p are each independently an integer from 0 to 7;

[0050] k is an integer from 0 to 6;

[0051] g is an integer from 0 to 4.

[0052] Further, the light-emitting layer contains a light-emitting host material, and the light-emitting host material is formed by mixing any one or more of the compound in the present application and compounds P-1 to P-88, which are shown below:

[0053] .

[0054] An electronic display device containing the organic electroluminescent device of the present application.

[0055] An OLED lighting device containing the organic electroluminescent device of the present application.

[0056] The room temperature of the present application is 25±5℃.

[0057] The beneficial effects of the present application are:

[0058] The present application designs a new class of organic electroluminescent materials, and has the following excellent properties:

[0059] 1. The deuterium substitution or aryl substitution of the active site improves the chemical stability, photoelectric stability and thermal stability of the compound, improves the stability of the device, and further improves the service life.

[0060] 2. It can form a good Premix material with the P-type compound of the present application, has good P / N stability and mass production stability in the evaporation process, and the formed Premix material has more balanced carrier mobility, thereby greatly improving the efficiency and service life of the device.

[0061] 3. The materials of the present application all have excellent solubility, which can effectively solve the problems of hole blockage and mask cleaning difficulty in the production line, and can greatly reduce the preparation and recovery cost of the materials. BRIEF DESCRIPTION OF DRAWINGS

[0062] Figure 1 The structure diagram of the organic electroluminescent device provided by the present application is shown in the figure;

[0063] The labels in the figure respectively represent: 1-anode, 2-hole injection layer, 3-hole transport layer, 4-electron blocking layer, 5-emitting layer, 6-hole blocking layer, 7-electron transport layer, 8-electron injection layer, 9-cathode;

[0064] Figure 2 The HPLC chart of compound 16 prepared in Example 1 of the present application is shown in the figure;

[0065] Figure 3 The DSC spectrum of compound 16 prepared in Example 1 of the present application is shown in the figure, Figure 3 It can be seen that the glass transition temperature Tg value of compound 16 is 135.26℃;

[0066] Figure 4 The TGA spectrum of compound 16 prepared in Example 1 of the present application is shown in the figure, Figure 4 It can be seen that the thermal weight loss temperature Td value is 457.22℃. DETAILED DESCRIPTION

[0067] Embodiments of various aspects are further illustrated and described below. It is to be understood that the description herein is not intended to limit the claims to the particular aspects described. Rather, the intention is to cover any alternatives, modifications, and equivalents that can be included within the spirit and scope of the disclosure defined by the claims.

[0068] As used herein, in “substituted” or “unsubstituted”, the term “substituted” means that at least one hydrogen in the group is re-coordinated with deuterium, hydrocarbyl, hydrocarbyl derivative group, halogen, or cyano (-CN). The term “unsubstituted” means that at least one hydrogen in the group is not re-coordinated with deuterium, hydrocarbyl, hydrocarbyl derivative group, halogen, or cyano (-CN). Examples of hydrocarbyl or hydrocarbyl derivative groups can include C1 to C30 alkyl, C2 to C30 alkenyl, C2 to C30 alkynyl, C6 to C30 aryl, C5 to C30 heteroaryl, C1 to C30 alkylamino, C6 to C30 arylamino, C6 to C30 heteroarylamino, C6 to C30 arylheteroarylamino, and the like, but are not limited thereto.

[0069] Deuterium in the present invention refers to a stable form of isotope of hydrogen, also known as heavy hydrogen, with the element symbol D.

[0070] As used herein, in “deuterated” or “un-deuterated”, the term “deuterated” means that at least one hydrogen in the group is re-coordinated with deuterium. The term “un-deuterated” means that all hydrogens in the group are not re-coordinated with deuterium.

[0071] n is an integer from 0 to 4, meaning that n can be 0, 1, 2, 3, 4. Similarly, m and p are each independently an integer from 0 to 7, meaning that m and p can each independently be 0, 1, 2, 3, 4, 5, 6, 7; k is an integer from 0 to 6, meaning that k can be 0, 1, 2, 3, 4, 5, 6; g is an integer from 0 to 4, meaning that g can be 0, 1, 2, 3, 4.

[0072] Aryl in the present invention refers to a fully carbon monocyclic or fused polycyclic group of 6 to 30 carbon atoms with a fully conjugated pi-electron system. Non-limiting examples of aryl groups are phenyl, naphthyl, anthryl, biphenyl, o-terphenyl, m-terphenyl, p-terphenyl, triphenylenyl, triphenyl[1,12-bcd]furyl, phenanthryl, and the like.

[0073] “Heteroaryl” herein refers to a heteroaryl group resulting from the substitution of one or more C in the structure of “aryl” with one or more heteroatoms (such as N, O, or S).

[0074] Unless otherwise indicated, conventional conditions or manufacturer’s recommendations were followed in the examples. Reagents or instruments used were conventional products available commercially unless otherwise indicated.

[0075] Example 1:

[0076]

[0077] The synthesis method of compound 16 is as follows:

[0078]

[0079] A 1L three-necked flask was charged with 1-a (80 g, 0.227 mol, 1 eq) and deuterated benzene (382 g, 4.54 mol, 20 eq), and trifluoromethanesulfonic acid (238.5 g, 1.589 mol, 7 eq) was slowly added dropwise. After the dropwise addition was completed, the reaction was stirred at 50°C for 18-24 h. The reaction was stopped, and the reaction liquid was slowly poured into 2000 ml of ice water and stirred for crystallization for 2 h. Filtration was performed, the filter cake was washed with water and toluene, and the filter cake was dried. Then, 100 g of 100-200 mesh silica gel was added to prepare sand, 800 g of 100-200 mesh silica gel was packed into a column, PE / DCM=100 / 1-50 / 1-20 / 1 was used for collection of the product point, and vacuum concentration was performed until dryness to obtain 68.9 g of white solid 1-b with a yield of 84%.

[0080]

[0081] A 2L three-necked flask was charged with 1-b (68 g, 0.1883 mol, 1 eq), 1-c (24.1 g, 0.1977 mol, 1.05 eq), potassium carbonate (52 g, 0.3766 mol, 2 eq), and toluene / ethanol / water (700 ml+350 ml+210 ml). Under the protection of N2, tetra-triphenylphosphine palladium (4.35 g, 3.766 mmol, 0.02 eq) was added, the reaction was stirred at reflux, and HPLC monitoring was performed until 1-b≤1%. The reaction was stopped, 200 ml of water was added, and the mixture was stirred and separated into two phases. The aqueous phase was extracted with DCM, the combined organic phases were filtered through silica gel, the filtrate was concentrated to dryness under reduced pressure, 150 ml of ethanol was added and heated to stir and pulp for 2 h, and the mixture was cooled to room temperature for crystallization. Filtration was performed, and the filter cake was dried at 85°C with air blowing to obtain 51 g of white solid 1-d with a yield of 75.6%.

[0082]

[0083] 1L three-necked flask was charged with 1-d (50 g, 0.14 mol, 1 eq), 1-e (54.2 g, 0.14 mol, 1 eq), sodium tert-butoxide (20.2 g, 0.21 mol, 1.5 eq) and toluene (500 ml), under N2protection, Xphos Pd G4 (2.41 g, 2.8 mmol, 0.02 eq) was added, the reaction was stirred at 100 °C, HPLC monitoring 1-d ≤ 1%. The reaction was stopped, hot silica gel was used to extract the filtrate, the filtrate was concentrated to dryness under reduced pressure, 200 ml of toluene was added to hot solution, 200 ml of ethanol was added, the mixture was stirred to crystallize at room temperature, extracted by filtration, the filter cake was recrystallized with toluene / ethanol for 4 times, and then recrystallized with pure toluene for 2 times, extracted by filtration, the filter cake was dried at 85 °C with air blowing, 45.6 g of white solid compound 16 was obtained, with a yield of 48.9%.

[0084] The following compounds 1, 2, 6, 7, 13, 17, 20, 24, 26, 28, 29, 30, 35, 37, 48, 49, 50, 61, 62, 64, 65, 68, 69, 73, 74, 77, 78, 85, 97, 98, 101, 102, 109, 110, 113, 114, 120, 121, 122, 125, 126, 133, 134, 138, 139, 145, 146, 149, 150, 157, 169, 170, 173, 174, 181, 182, 183, 187, 188, 189, 197, 198, 201, 205, 210, 221, 222, 230 were obtained in a similar manner:

[0085] Table 1-1

[0086]

[0087] Table 1-2

[0088]

[0089] Table 1-3

[0090]

[0091] Table 1-4

[0092]

[0093] Table 1-5

[0094]

[0095] Table 1-6

[0096]

[0097] Table 1-7

[0098]

[0099] Table 1-8

[0100]

[0101] Table 1-9

[0102]

[0103] Table 1-10

[0104]

[0105] Table 1-11

[0106]

[0107] Table 1-12

[0108]

[0109] Table 1-13

[0110]

[0111] Table 1-14

[0112]

[0113] Table 1-15

[0114]

[0115] Table 1-16

[0116]

[0117] Table 1-17

[0118]

[0119] Table 1-18

[0120]

[0121] Table 1-19

[0122]

[0123] Table 1-20

[0124]

[0125] Table 1-21

[0126]

[0127] Table 1-22

[0128]

[0129] The synthetic identification results of the compounds prepared above are shown in Table 2 below:

[0130] Table 2

[0131] Compound FD-mass Compound FD-mass 1 m / z = 665.21 (C45H19D9N4S = 665.26) 113 m / z = 725.27 (C51H23D9N4O = 725.31) 2 m / z = 665.22 (C45H19D9N4S = 665.26) 114 m / z = 725.25 (C51H23D9N4O = 725.31) 6 m / z = 665.21 (C45H19D9N4S = 665.26) 120 m / z = 725.28 (C51H23D9N4O = 725.31) 7 m / z = 665.24 (C45H19D9N4S = 665.26) 121 m / z = 725.27 (C51H23D9N4O = 725.31) 13 m / z = 715.25 (C49H21D9N4S = 715.28) 122 m / z = 725.28 (C51H23D9N4O = 725.31) 16 m / z = 665.22 (C45H19D9N4S = 665.26) 125 m / z = 725.28 (C51H23D9N4O = 725.31) 17 m / z = 665.24 (C45H19D9N4S = 665.26) 126 m / z = 725.27 (C51H23D9N4O = 725.31) 20 m / z = 665.21 (C45H19D9N4S = 665.26) 133 m / z = 725.28 (C51H23D9N4O = 725.31) 24 m / z = 670.25 (C45H14D14N4S = 670.29) 134 m / z = 725.25 (C51H23D9N4O = 725.31) 26 m / z = 665.23 (C45H19D9N4S = 665.26) 137 m / z = 725.26 (C51H23D9N4O = 725.31) 28 m / z = 715.27 (C49H21D9N4S = 715.28) 138 m / z = 725.26 (C51H23D9N4O = 725.31) 29 m / z = 665.24 (C45H19D9N4S = 665.26) 139 m / z = 725.28 (C51H23D9N4O = 725.31) 30 m / z = 665.23 (C45H19D9N4S = 665.26) 145 m / z = 725.27 (C51H23D9N4O = 725.31) 35 m / z = 670.26 (C45H14D14N4S = 670.29) 146 m / z = 725.29 (C51H23D9N4O = 725.31) 37 m / z = 741.24 (C51H23D9N4S = 741.29) 149 m / z = 725.27 (C51H23D9N4O = 725.31) 48 m / z = 741.25 (C51H23D9N4S = 741.29) 150 m / z = 725.28 (C51H23D9N4O = 725.31) 49 m / z = 741.23 (C51H23D9N4S = 741.29) 157 m / z = 725.28 (C51H23D9N4O = 725.31) 50 m / z = 741.25 (C51H23D9N4S = 741.29) 169 m / z = 725.24 (C51H23D9N4O = 725.31) 61 m / z = 741.26 (C51H23D9N4S = 741.29) 170 m / z = 725.26 (C51H23D9N4O = 725.31) 62 m / z = 741.26 (C51H23D9N4S = 741.29) 173 m / z = 725.25 (C51H23D9N4O = 725.31) 64 m / z = 746.29 (C51H18D14N4S = 746.32) 174 m / z = 725.24 (C51H23D9N4O = 725.31) 65 m / z = 741.27 (C51H23D9N4S = 741.29) 181 m / z = 649.25 (C45H19D9N4O = 649.28) 68 m / z = 741.25 (C51H23D9N4S = 741.29) 182 m / z = 649.23 (C45H19D9N4O = 649.28) 69 m / z = 746.25 (C51H18D14N4S = 746.32) 183 m / z = 654.25 (C45H14D14N4O = 654.31) 73 m / z = 741.27 (C51H23D9N4S = 741.29) 187 m / z = 649.24 (C45H19D9N4O = 649.28) 74 m / z = 741.24 (C51H23D9N4S = 741.29) 188 m / z = 699.27 (C49H21D9N4O = 699.30) 77 m / z = 741.24 (C51H23D9N4S = 741.29) 189 m / z = 649.21 (C45H19D9N4O = 649.28) 78 m / z = 741.25 (C51H23D9N4S = 741.29) 197 m / z = 649.25 (C45H19D9N4O = 649.28) 85 m / z = 741.26 (C51H23D9N4S = 741.29) 198 m / z = 649.24 (C45H19D9N4O = 649.28) 97 m / z = 741.24 (C51H23D9N4S = 741.29) 201 m / z = 699.25 (C49H21D9N4O = 699.30) 98 m / z = 741.24 (C51H23D9N4S = 741.29) 205 m / z = 699.24 (C49H21D9N4O = 699.30) 101 m / z = 741.26 (C51H23D9N4S = 741.29) 210 m / z = 649.22 (C45H19D9N4O = 649.28) 102 m / z = 741.25 (C51H23D9N4S = 741.29) 221 m / z = 649.24 (C45H19D9N4O = 649.28) 109 m / z = 725.24 (C51H23D9N4O = 725.31) 222 m / z = 649.23 (C45H19D9N4O = 649.28) 110 m / z = 725.26 (C51H23D9N4O = 725.31) 230 m / z = 654.28 (C45H14D14N4O = 654.31)

[0132] Device performance test:

[0133] The thermal weight loss temperature Td and the glass transition temperature Tg of the compounds 1, 2, 6, 7, 13, 16, 17, 20, 24, 26, 28, 29, 30, 35, 37, 48, 49, 50, 61, 62, 64, 65, 68, 69, 73, 74, 77, 78, 85, 97, 98, 101, 102, 109, 110, 113, 114, 120, 121, 122, 125, 126, 133, 134, 138, 139, 145, 146, 149, 150, 157, 169, 170, 173, 174, 181, 182, 183, 187, 188, 189, 197, 198, 201, 205, 210, 221, 222, 230 in Examples 1-70 of the application were tested, and the results are shown in Table 3:

[0134] Note: The thermal weight loss temperature Td is the temperature at which 5% weight loss occurs in a nitrogen atmosphere, and is measured on a TGA N-1000 thermal gravimetric analyzer with a nitrogen flow rate of 10 mL / min. The glass transition temperature Tg is measured by differential scanning calorimetry (DSC, Shinco DSC N-650) at a heating rate of 10℃ / min.

[0135] Table 3:

[0136] Test material (compound) Td (°C) Tg (°C) Test material (compound) Td (°C) Tg (°C) 1 466.51 148.36 113 440.91 147.29 2 458.69 137.45 114 446.28 136.25 6 445.23 138.20 120 451.39 148.98 7 469.21 140.57 121 470.41 126.34 13 472.55 135.67 122 465.32 130.58 16 457.22 135.26 125 445.68 126.81 17 429.74 145.31 126 462.50 132.74 20 444.39 153.20 133 453.98 143.11 24 437.26 143.54 134 455.35 141.62 26 438.37 137.48 137 462.64 139.48 28 449.30 146.32 138 438.58 128.79 29 462.71 148.08 139 439.71 137.56 30 452.36 136.89 145 459.67 135.25 35 468.17 141.59 146 460.64 139.87 37 462.85 151.48 149 449.42 142.60 48 458.86 134.61 150 453.88 134.72 49 443.92 127.85 157 472.30 127.45 50 438.08 133.87 169 463.97 130.65 61 448.69 136.54 170 466.83 142.38 62 459.10 141.86 173 457.09 137.50 64 463.28 139.47 174 448.34 135.18 65 452.84 136.79 181 458.40 142.67 68 459.33 140.87 182 450.92 126.15 69 468.12 128.45 183 466.20 135.67 73 452.57 130.70 187 459.24 148.78 74 463.82 134.55 188 471.31 145.62 77 446.16 141.46 189 466.82 139.50 78 438.94 143.92 197 468.29 134.22 85 459.25 138.73 198 459.41 145.15 97 451.14 137.63 201 462.87 135.87 98 442.65 129.88 205 448.05 137.28 101 448.16 132.81 210 452.94 140.85 102 452.97 145.97 221 469.86 139.01 109 437.68 136.42 222 475.62 147.49 110 432.56 144.25 230 453.62 138.27

[0137] As can be seen from Table 3 above, the compounds of the application have high Td values and Tg values, indicating that they have excellent thermal stability. When they are applied to organic electroluminescent devices, the service life of the organic electroluminescent devices can be effectively prolonged, and better use effects can be obtained.

[0138] Device performance test:

[0139] Application Example 1:

[0140] ITO is used as the reflective layer anode substrate material, and the surface is treated with water, acetone, N2 plasma in sequence;

[0141] On the ITO anode substrate, 10 nm of HT-1 doped with 5% NDP-9 is deposited to form a hole injection layer (HIL);

[0142] On the hole injection layer (HIL), 100 nm of HT-1 is evaporated to form a hole transport layer (HTL);

[0143] On the hole transport layer (HTL), GP is vacuum evaporated to form a second hole transport layer (GPL) with a thickness of 10 nm;

[0144] The compound 16 prepared in Example 1 of the present application and the compound P-1 are co-evaporated in a ratio of 5:5 as the light-emitting host material, and GD-1 is evaporated on the second hole transport layer (GPL) as the dopant material (the amount of GD-1 is 8% of the total weight of compound 16 and P-1) to form a light-emitting layer with a thickness of 20 nm;

[0145] HB-1 is evaporated on the light-emitting layer to obtain a hole blocking layer (HBL) with a thickness of 20 nm;

[0146] ET-1 and LiQ are co-evaporated on the hole blocking layer (HBL) in a ratio of 5:5 to obtain an electron transport layer (ETL) with a thickness of 30 nm;

[0147] Magnesium (Mg) and silver (Ag) are mixed and evaporated on the electron transport layer (ETL) in a ratio of 9:1 to form an electron injection layer (EIL) with a thickness of 50 nm;

[0148] Thereafter, silver (Ag) is evaporated on the electron injection layer to form a cathode with a thickness of 100 nm, and DNTPD is deposited on the above cathode sealing layer with a thickness of 50 nm. In addition, the cathode surface is sealed with a UV-hardened adhesive and a seal cap containing a desiccant to protect the organic electroluminescent device from the influence of oxygen or moisture in the atmosphere. Thus, the organic electroluminescent device is prepared.

[0149]

[0150] Application Example 2-70

[0151] The organic electroluminescent devices of application examples 2-70 were prepared in the same manner as in application example 1 except that the compound 16 in application example 1 was replaced by the compound 1, 2, 6, 7, 13, 17, 20, 24, 26, 28, 29, 30, 35, 37, 48, 49, 56, 61, 62, 64, 65, 68, 69, 73, 74, 77, 78, 85, 97, 98, 101, 102, 109, 110, 113, 114, 120, 121, 122, 125, 126, 133, 134, 138, 139, 145, 146, 149, 150, 157, 169, 170, 173, 174, 181, 182, 183, 187, 188, 189, 197, 198, 201, 205, 210, 221, 222, 230 in the compounds of the present application examples 2-70, respectively, and the other parts were the same as in application example 1.

[0152] Comparative examples 1-3

[0153] The comparative examples 1-3 and application example 1 differ in that the compound D1 and D2 in CN117751111A, the compound D3 in CN106661041A were used instead of the compound 16 in application example 1, and the rest was the same as in application example 1.

[0154] The organic electroluminescent devices prepared in application examples 1-70 and comparative examples 1-3 were tested, and the test results are shown in Table 4.

[0155] Table 4

[0156] Experimental group Host material for luminescence Current density (mA / cm 2 ) Voltage (V) Luminescence efficiency (Cd / A) Color of luminescence Comparative example 1 D1+P-1 10 3.59 166.3 Green Comparative example 2 D2+P-1 10 3.56 159.7 Green Comparative example 3 D3+P-1 10 3.70 161.5 Green Application example 1 16+P-1 10 3.30 217.3 Green Application example 2 1+P-1 10 3.36 208.5 Green Application example 3 2+P-1 10 3.35 197.3 Green Application example 4 6+P-1 10 3.38 195.7 Green Application example 5 7+P-1 10 3.36 192.1 Green Application example 6 13+P-1 10 3.43 202.6 Green Application example 7 17+P-1 10 3.38 192.4 Green Application example 8 20+P-1 10 3.42 205.0 Green Application example 9 24+P-1 10 3.36 197.4 Green Application example 10 26+P-1 10 3.31 185.4 Green Application example 11 28+P-1 10 3.42 208.1 Green Application example 12 29+P-1 10 3.37 198.0 Green Application example 13 30+P-1 10 3.31 193.7 Green Application example 14 35+P-1 10 3.37 196.5 Green Application example 15 37+P-1 10 3.31 193.4 Green Application example 16 48+P-1 10 3.40 203.8 Green Application example 17 49+P-1 10 3.39 207.5 Green Application example 18 50+P-1 10 3.32 196.3 Green Application example 19 61+P-1 10 3.37 198.0 Green Application example 20 62+P-1 10 3.35 195.9 Green Application example 21 61+P-1 10 3.34 194.6 Green Application example 22 65+P-1 10 3.32 196.8 Green Application example 23 68+P-1 10 3.39 201.3 Green Application example 24 69+P-1 10 3.38 196.7 Green Application example 25 73+P-1 10 3.41 210.5 Green Application example 26 74+P-1 10 3.38 196.5 Green Application example 27 77+P-1 10 3.39 204.6 Green Application example 28 78+P-1 10 3.36 193.2 Green Application example 29 85+P-1 10 3.42 198.3 Green Application example 30 97+P-1 10 3.40 208.6 Green Application example 31 98+P-1 10 3.37 196.2 Green Application example 32 101+P-1 10 3.42 198.3 Green Application example 33 102+P-1 10 3.32 192.6 Green Application example 34 109+P-1 10 3.35 199.3 Green Application example 35 110+P-1 10 3.38 190.5 Green Application example 36 113+P-1 10 3.35 188.3 Green Application example 37 114+P-1 10 3.40 196.3 Green Application example 38 120+P-1 10 3.43 197.2 Green Application example 39 121+P-1 10 3.35 192.7 Green Application example 40 122+P-1 10 3.39 201.8 Green Application example 41 125+P-1 10 3.45 203.6 Green Application example 42 126+P-1 10 3.37 186.3 Green Application example 43 133+P-1 10 3.37 194.3 Green Application example 44 134+P-1 10 3.41 198.5 Green Application example 45 137+P-1 10 3.46 203.8 Green Application example 46 138+P-1 10 3.34 187.3 Green Application example 47 139+P-1 10 3.38 196.7 Green Application example 48 145+P-1 10 3.37 192.5 Green Application example 49 146+P-1 10 3.43 203.6 Green Application example 50 149+P-1 10 3.41 199.6 Green Application example 51 150+P-1 10 3.38 195.3 Green Application example 52 157+P-1 10 3.35 186.7 Green Application example 53 169+P-1 10 3.36 185.5 Green Application example 54 170+P-1 10 3.34 183.0 Green Application example 55 173+P-1 10 3.38 192.6 Green Application example 56 174+P-1 10 3.41 198.3 Green Application example 57 181+P-1 10 3.36 197.6 Green Application example 58 182+P-1 10 3.41 201.0 Green Application example 59 183+P-1 10 3.35 192.4 Green Application example 60 187+P-1 10 3.36 197.3 Green Application example 61 188+P-1 10 3.41 197.2 Green Application example 62 189+P-1 10 3.44 203.4 Green Application example 63 197+P-1 10 3.37 196.0 Green Application example 64 198+P-1 10 3.40 194.3 Green Application example 65 201+P-1 10 3.39 196.7 Green Application example 66 205+P-1 10 3.46 199.4 Green Application example 67 210+P-1 10 3.38 190.8 Green Application example 68 221+P-1 10 3.41 197.6 Green Application example 69 222+P-1 10 3.44 198.9 Green Application example 70 230+P-1 10 3.38 192.4 Green

[0157] From the above Table 4, it can be seen that the compound of the present application applied to the organic electroluminescent device as the host material of the light-emitting layer can improve the luminous efficiency of the organic electroluminescent device to a certain extent, and the starting voltage is reduced and the power consumption is relatively reduced.

[0158] The organic electroluminescent devices prepared in comparative examples 1-6 and application examples 1-15, 36-40 were tested for luminous life, and the T97% data (time for the luminous intensity to decrease to 97% of the initial luminous intensity) was obtained. The test equipment was a TEO luminescent device life test system. The results are shown in Table 5.

[0159] Table 5

[0160] Experimental group Current density (mA / cm 2 )]]> T97% Comparative example 1 10 98% Comparative example 2 10 100% Comparative example 3 10 90% Application example 1 10 159% Application example 2 10 146% Application example 3 10 147% Application example 4 10 132% Application example 5 10 142% Application example 6 10 153% Application example 7 10 140% Application example 8 10 147% Application example 9 10 142% Application example 10 10 138% Application example 11 10 141% Application example 12 10 152% Application example 13 10 147% Application example 14 10 146% Application example 15 10 142% Application example 36 10 138% Application example 37 10 146% Application example 38 10 149% Application example 39 10 144% Application example 40 10 146%

[0161] From the above Table 5, it can be seen that the compound of the present application applied to the organic electroluminescent device as the host material of the light-emitting layer can greatly improve the service life of the prepared organic electroluminescent device, so it has a very broad application prospect.

Claims

1. A compound containing a nitrogen heterocyclic structure, characterized in that, The compound is any one of the following compounds: 。 2. An organic electroluminescent device, characterized in that, It includes a first electrode, a second electrode, and an organic layer formed between the first electrode and the second electrode; the organic layer contains a compound as described in any one of claims 1.

3. The organic electroluminescent device as described in claim 2, characterized in that, The organic layer comprises a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer; the light-emitting layer contains a compound as described in any one of claims 1.

4. The organic electroluminescent device as described in claim 3, characterized in that, The light-emitting layer also contains at least one of the following formulas 5 or 6: ； in, Ar4 and Ar5 are each independently selected from substituted or unsubstituted groups of the following: C6-C30 aryl, C5-C30 heteroaryl, wherein the substituents of Ar4 and Ar5 are selected from one or more of deuterium, fluorine, cyano, C1-C10 alkyl, C1-C10 deuterated alkyl, C1-C10 cycloalkyl, C1-C10 deuterated cycloalkyl, C6-C30 aryl, C6-C30 deuterated aryl, and C5-C30 heteroaryl. L4 and L5 are each independently selected from single bonds, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, and the substituents of L4 and L5 are selected from one or more of deuterium, fluorine, cyano, C1-C10 alkyl, C6-C18 aryl, and C5-C20 heteroaryl. R2-R5 are each independently selected from one or more of the following groups: hydrogen, deuterium, fluorine, cyano, deuterated or undeuterated: phenyl, biphenyl, methyl, ethyl, tert-butyl; m and p are each independent integers from 0 to 7; k is an integer between 0 and 6; g is an integer between 0 and 4.

5. The organic electroluminescent device as described in claim 2 or 3, characterized in that, The light-emitting layer contains a light-emitting host material, which is a mixture of the compound according to any one of claims 1 and any one or more of compounds P-1 to P-88, as shown below: 。 6. An electronic display device, characterized in that, It contains the organic electroluminescent device as described in claim 2.

Images