A compound containing a carbazolophenoxazine group, intermediates for its preparation and use thereof

Abstract

The present application provides a kind of carbazole and phenazine group-containing compound, the intermediate for preparing it and its application.The carbazole and phenazine group-containing compound has the structure shown in formula I as follows.The present application is designed by the structure formula of carbazole and phenazine group-containing compound, and the organic electroluminescent device prepared by the carbazole and phenazine group-containing compound with specific structure has lower driving voltage, higher current efficiency and longer life.

Description

TECHNICAL FIELD

[0001] The present application belongs to the technical field of organic electroluminescent materials, and particularly relates to a compound containing a carbazolophenazine group, an intermediate for preparing the compound, and application of the compound and the intermediate, and more particularly to a compound containing a carbazolophenazine group, an intermediate, an organic electroluminescent device, and a display device. BACKGROUND

[0002] An organic light-emitting device (OLED) has attracted the attention of many display panel manufacturers due to its advantages such as self-luminous, ultra-light and thin, wide viewing angle, fast response speed, high luminous efficiency, wide temperature adaptation range, flexible display device, low driving voltage, and low energy consumption, and is regarded as the next generation of mainstream display technology.

[0003] An organic electroluminescent device generally comprises an anode, a hole transport layer, an organic light-emitting layer, an interface modification layer, and a cathode. Electrons and holes are injected from the corresponding electrodes into the light-emitting layer to form excitons, and radiative recombination light is emitted.

[0004] Overall, the future direction of OLED is to develop devices with high efficiency, high brightness, long service life, and low cost, so it is particularly important to continuously research and innovate organic electroluminescent devices with high performance. SUMMARY

[0005] In view of the deficiencies of the prior art, the purpose of the present application is to provide a compound containing a carbazolophenazine group, an intermediate for preparing the compound, and application, and more particularly to provide a compound containing a carbazolophenazine group, an intermediate, an organic electroluminescent device, and a display device. The organic electroluminescent device prepared from the compound containing a carbazolophenazine group with a specific structure and having a carbazole group and a phenazine group has a lower driving voltage, a higher current efficiency, and a longer service life.

[0006] To achieve this purpose, the present application adopts the following technical solutions:

[0007] In a first aspect, the present application provides a compound containing a carbazolophenazine group, which has the following structure shown in formula I:

[0008]

[0009] wherein L is selected from any one of a substituted or unsubstituted C6-C40 arylene group and a substituted or unsubstituted C3-C20 heteroarylene group;

[0010] n is selected from 0 or 1;

[0011] Ar has the following structure shown in formula II:

[0012]

[0013] Ar passes through formula II sp 2 The hybrid carbon atom or any one of R1 or R2 is bonded to the L group or N atom in Formula I by a single bond;

[0014] R1 or R2 is independently selected from any one of substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C6-C40 aryl, or substituted or unsubstituted C3-C30 heteroaryl;

[0015] R3 is selected from H, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C6-C20 aryl;

[0016] The substituents described in L, R1-R3 are each independently selected from at least one of C1-C4 straight-chain or branched alkyl groups and C6-C20 aryl groups;

[0017] The hydrogen atom in the compound of formula I may be replaced by at least one of -F, -CN, -D, C1-C6 alkyl, C1-C6 alkoxy, phenyl, biphenyl, naphthyl, phenanthryl, anthracene, fluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, terphenyl, triphenylene, fluoranyl, pyrene, peryl, spirofluorenyl, indo[a]fluorenyl, or hydrogenated benzo[a]anthryl.

[0018] This invention designs the structural formula of compounds containing carbazole and phenazine groups, and the organic electroluminescent devices prepared by these compounds with specific structures have lower driving voltage, higher current efficiency, and longer lifespan.

[0019] In this invention, C6 to C40 can be C6, C10, C12, C15, C18, C24, C30, C36 or C40, etc.

[0020] C3 to C20 can be C3, C4, C5, C7, C8, C9, C12, C15, C18, or C20, etc.

[0021] C1 to C6 can be C1, C2, C3, C4, C5, or C6.

[0022] C3 to C20 can be C3, C4, C5, C7, C8, C12, C15, C18, C20, C24, C27, or C30, etc.

[0023] C6 to C20 can be C6, C10, C12, C15, C18, or C20, etc.

[0024] C1 to C6 can be C1, C2, C3, or C4.

[0025] It is noted that Ar is bonded to the nitrogen atom in the phenoxazine group of the compound of formula I through a single bond via sp 2 Hybridized carbon atom or either R1 or R2 is single-bonded to the L group or the N atom in the compound of formula I means that when n is 0 in the compound of formula I, Ar is single-bonded to the nitrogen atom in the phenoxazine group of the compound of formula I, specifically Ar is single-bonded to the nitrogen atom in the phenoxazine group of the compound of formula I through sp 2 Hybridized carbon atom (i.e. the carbon atom on the benzene ring in Ar) or either R1 or R2 is single-bonded to the L group in the compound of formula I; when n is 1 in the compound of formula I, Ar is single-bonded to the L group in the compound of formula I, specifically Ar is single-bonded to the L group in the compound of formula I through sp 2 Hybridized carbon atom (i.e. the carbon atom on the benzene ring in Ar) or either R1 or R2 is single-bonded to the L group in the compound of formula I.

[0026] The following are preferred technical solutions of the present application, but not as a restriction on the technical solutions provided by the present application, through the following preferred technical solutions, the purpose and beneficial effects of the present application can be better achieved and realized.

[0027] As a preferred technical solution of the present application, the L is selected from any one of the following substituted or unsubstituted compounds: benzene, biphenyl, naphthalene, phenanthrene, anthracene, fluorene, benzofluorene, dibenzofluorene, dibenzofuran, dibenzothiophene, triphenylene, fluoranthene, pyrene, perylene, spirofluorene, pyridine, pyrazine, pyrimidine, triazine, quinoline, isoquinoline, quinoxaline, quinazoline, imidazole, benzimidazole, indenofluorene or hydrogenated benzanthracene;

[0028] The substituent is selected from at least one of the following: methyl, ethyl, propyl, butyl, phenyl.

[0029] Preferably, the L is selected from any one of the following groups:

[0030]

[0031] Wherein, the short line represents the connection site of the group.

[0032] As a preferred technical solution of the present application, the R1 is selected from any one of the following substituted or unsubstituted compounds: methane, ethane, propane, butane, pentane, hexane, benzene, biphenyl, naphthalene, phenanthrene, anthracene, fluorene, benzofluorene, dibenzofluorene, triphenylene, fluoranthene, pyrene, perylene, spirofluorene, dibenzofuran, dibenzothiophene, indenofluorene or hydrogenated benzanthracene;

[0033] The substituent is selected from at least one of the following: methyl, ethyl, propyl, butyl, phenyl.

[0034] Preferably, R1 is selected from any one of the following groups:

[0035] ethyl, butyl,

[0036] wherein the short line indicates the connection site of the group.

[0037] Preferably, R2 is selected from any one of the following groups:

[0038] The substituent is selected from at least one of the following groups: methyl, ethyl, propyl, butyl, phenyl.

[0039] Preferably, R2 is selected from any one of the following groups:

[0040] ethyl,

[0041] wherein the short line indicates the connection site of the group.

[0042] Preferably, R1 and R2 are not simultaneously substituted or unsubstituted C1-C6 alkyl.

[0043] Preferably, R3 is selected from any one of the following groups:

[0044] Preferably, R3 is selected from any one of the following groups:

[0045] wherein the short line indicates the connection site of the group.

[0046] Preferably, the hydrogen atom in the compound of formula I can be replaced by at least one of the following groups: -F, -CN, -D, C1-C3 alkyl, C1-C3 alkoxy, phenyl, biphenyl, naphthyl, fluorenyl, terphenyl, triphenylenyl, fluoranthene.

[0047] Preferably, the compound of formula I is selected from any one of the following compounds:

[0048]

[0049]

[0050]

[0051]

[0052]

[0053]

[0054]

[0055] In a second aspect, the present application provides an intermediate, which has a structure as shown in any one of M-C-X, M-C-B, M-C-B1:

[0056]

[0057] wherein each L in M-C-X, M-C-B, M-C-B1 is independently selected from any one of a single bond, a substituted or unsubstituted C6-C40 arylene group, and a substituted or unsubstituted C3-C20 heteroarylene group;

[0058] the substituents in the substituted substituents in L are selected from at least one of a C1-C4 (e.g., C1, C2, C3, or C4) straight chain or branched alkyl group, and a C6-C20 (e.g., C6, C10, C12, C15, C18, or C20, etc.) aryl group;

[0059] X is selected from any one of F, Cl, Br, and I;

[0060] R 101 and R 102 are each independently selected from a C1-C6 (e.g., C1, C2, C3, C4, C5, or C6) alkyl group, R 101 and R 102 may be connected by a single bond to form a ring;

[0061] The intermediate is used for preparing the carbazolophenazinyl-containing compound as described in the first aspect.

[0062] Preferably, L is selected from any one of a single bond, a phenylene group, a biphenylene group, a dibenzofuranyl group, a dithiophenyl group, and a 9,9-dimethylfluorenyl group.

[0063] Preferably, the intermediate is selected from any one of the following compounds:

[0064]

[0065] It should be noted that the present application does not have any special limitation on the preparation method of the above-mentioned intermediate, and the intermediate can be prepared by a method commonly used in the art.

[0066] The preparation method of the compound containing carbazolophenazine group is not particularly limited in the present application, and can be prepared by a method commonly used in the art.

[0067] In a third aspect, the present application provides an organic electroluminescent device comprising the compound containing carbazolophenazine group according to the first aspect.

[0068] Preferably, the organic electroluminescent device comprises a hole transport layer and a light-emitting layer.

[0069] Preferably, the material of the hole transport layer comprises the compound containing carbazolophenazine group according to the first aspect.

[0070] In a fourth aspect, the present application provides a display device comprising the organic electroluminescent device according to the third aspect.

[0071] Compared with the prior art, the present application has the following beneficial effects:

[0072] The organic electroluminescent device prepared by the compound containing carbazolophenazine group with a specific structure has a lower driving voltage, a higher current efficiency and a longer service life. DETAILED DESCRIPTION

[0073] For the purpose of facilitating the understanding of the present application, the present application is illustrated by the following examples. It should be understood by those skilled in the art that the examples are only for the purpose of understanding the present application, and should not be regarded as a specific limitation of the present application.

[0074] Synthesis Example 1

[0075] The present synthesis example provides a compound A containing carbazolophenazine group, and the synthesis method is as follows:

[0076]

[0077] (1) Synthesis of intermediate I

[0078] Into a 250 mL three-necked flask, 60 mL of toluene, 20 mL of ethanol, 10 mL of water, 2.56 g (0.01 mol) of 5H-indolo[3,2,1-de]phenazin, 1.57 g (0.01 mol) of 1-chloro-2-nitrobenzene, 2.12 g (0.02 mol) of sodium carbonate and 0.115 g (0.0001 mol) of tetrakis-triphenylphosphine palladium were added, and the mixture was slowly warmed to reflux for 6 h. After cooling, the mixture was partitioned between water and toluene. The organic layer was washed with water and dried over magnesium sulfate. After removing the magnesium sulfate by filtration, the solvent was removed under reduced pressure. The obtained solid was separated by column chromatography using petroleum ether: ethyl acetate: dichloromethane = 8:1:1 (volume ratio) as eluent to obtain 2.58 g of the intermediate I at a yield of 68.4%.

[0079] The intermediate I was subjected to mass spectrometry, and m / z was 377.

[0080] (2) Synthesis of the intermediate II

[0081] Into a 250 mL three-necked flask, 60 mL of toluene, 20 mL of ethanol, 10 mL of water, 2.56 g (0.01 mol) of 5H-indolo[3,2,1-de]phenazin, 1.57 g (0.01 mol) of 1-chloro-2-nitrobenzene, 2.12 g (0.02 mol) of sodium carbonate and 0.115 g (0.0001 mol) of tetrakis-triphenylphosphine palladium were added, and the mixture was slowly warmed to reflux for 6 h. After cooling, the mixture was partitioned between water and toluene. The organic layer was washed with water and dried over magnesium sulfate. After removing the magnesium sulfate by filtration, the solvent was removed under reduced pressure. The obtained solid was separated by column chromatography using petroleum ether: ethyl acetate: dichloromethane = 8:1:1 (volume ratio) as eluent to obtain 2.58 g of the intermediate I at a yield of 68.4%.

[0082] The intermediate II was subjected to mass spectrometry, and m / z was 345.

[0083] The intermediate II was subjected to nuclear magnetic resonance, and the data were as follows: 1H-NMR (Switzerland Bruker Company, Avance Ⅱ 400 MHz nuclear magnetic resonance spectrometer, CDCl3), δ 9.11 (s, 1H), δ 8.56 (m, 1H), δ 7.88 (m, 1H), δ 7.50 (m, 1H), δ 7.30 (m, 2H), δ 7.17-7.05 (m, 7H), δ 6.88 (m, 2H).

[0084] (3) Synthesis of the intermediate III

[0085] In a 500 mL flask, under nitrogen protection, 120 mL of toluene, 50 mL of DMF, 2.73 g (0.01 mol) of 5-bromo-3-phenyl-1H-indazole and 2.04 g (0.01 mol) of iodobenzene, 2.12 g (0.02 mol) of potassium carbonate, 0.3 g of cuprous iodide were added, and the temperature was raised to 110°C under stirring, and the reaction was carried out for 15 h. After the reaction was completed, the temperature was cooled to room temperature, water was added for liquid separation, and the organic phase was evaporated to obtain a solid, which was separated by column chromatography, and eluted with petroleum ether: dichloromethane = 8: 1 (volume ratio) to obtain 2.58 g of intermediate III, with a yield of 75%.

[0086] The intermediate of formula III was detected by mass spectrometry, and m / z was 348.

[0087] (4) Synthesis of compound A

[0088] In a 500 mL flask, under nitrogen protection, 180 mL of toluene, 60 mL of DMF, 3.45 g (0.01 mol) of intermediate II and 3.48 g (0.01 mol) of intermediate III, 2.12 g (0.02 mol) of potassium carbonate, 0.3 g of cuprous iodide were added, and the temperature was raised to 100°C under stirring, and the reaction was carried out for 15 h. After the reaction was completed, the temperature was cooled to room temperature, water was added for liquid separation, and the organic phase was evaporated to obtain a solid, which was separated by column chromatography, and eluted with petroleum ether: ethyl acetate: dichloromethane = 8: 1: 1 (volume ratio) to obtain 5.03 g of compound A, with a yield of 82%.

[0089] Compound A was detected by mass spectrometry, and m / z was 613.

[0090] Synthesis Example 2

[0091] The present synthesis example provides a carbazolophenazine group-containing compound B, and the synthesis method is as follows:

[0092]

[0093] (1) Synthesis of intermediate I

[0094] Intermediate I was prepared according to the synthesis method of intermediate I in synthesis example 1.

[0095] (2) Synthesis of intermediate II

[0096] Intermediate II was prepared according to the synthesis method of intermediate II in synthesis example 1.

[0097] (3) Synthesis of intermediate IV

[0098] The synthesis method of the intermediate III in the synthesis example 1 was referred to, and only different from the preparation method of the intermediate III was that the 5-bromo-3-phenyl-1 H-indazole was replaced by the 5-bromo-3-ethyl-1 H-indazole with equal amount of substance to obtain 2.556 g of the intermediate IV with a yield of 67%.

[0099] The intermediate of the formula IV was detected by mass spectrometry with m / z of 300.

[0100] (4) Synthesis of compound B

[0101] The synthesis method of the compound A in the synthesis example 1 was referred to, and only different from the preparation method of the compound A was that the intermediate III was replaced by the intermediate IV with equal amount of substance to obtain 5.52 g of the compound B.

[0102] The compound B was detected by mass spectrometry with m / z of 565.

[0103] Synthesis example 3

[0104] The synthesis example provides a compound C containing a carbazole and phenoxazine group, and the synthesis method is as follows:

[0105]

[0106] (1) Synthesis of intermediate I

[0107] The intermediate I was prepared according to the synthesis method of the intermediate I in the synthesis example 1.

[0108] (2) Synthesis of intermediate II

[0109] The intermediate II was prepared according to the synthesis method of the intermediate II in the synthesis example 1.

[0110] (3) Synthesis of intermediate V

[0111] The synthesis method of the intermediate III in the synthesis example 1 was referred to, and only different from the preparation method of the intermediate III was that the 5-bromo-3-phenyl-1 H-indazole was replaced by the 6-bromo-3-phenyl-1 H-indazole with equal amount of substance to obtain 2.35 g of the intermediate V.

[0112] The intermediate of the formula V was detected by mass spectrometry with m / z of 300.

[0113] (4) Synthesis of compound C

[0114] The synthesis method of the compound A in the synthesis example 1 was referred to, and only different from the preparation method of the compound A was that the intermediate III was replaced by the intermediate V with equal amount of substance to obtain 5.5 g of the compound C.

[0115] The compound C was subjected to mass spectrometry, and the m / z was 565.

[0116] Synthesis Example 4

[0117] The present synthesis example provides a compound D containing a carbazolophenazine group, and the synthesis method is as follows:

[0118]

[0119] (1) Synthesis of intermediate I

[0120] Referring to the synthesis method of intermediate I in Synthesis Example 1, intermediate I was prepared.

[0121] (2) Synthesis of intermediate II

[0122] Referring to the synthesis method of intermediate II in Synthesis Example 1, intermediate II was prepared.

[0123] (3) Synthesis of intermediate III

[0124] Referring to the synthesis method of intermediate III in Synthesis Example 1, intermediate III was prepared.

[0125] (4) Synthesis of intermediate VI

[0126] Under nitrogen protection, 2.67 g (0.01 mol) of the intermediate shown in formula II, 2.83 g (0.01 mol) of 4-bromoiodobenzene, 1.06 g of sodium carbonate, 100 mL of DMF, 1.0 g of cuprous iodide and 0.4 g of 1,10-phenanthroline were added into a 250 mL three-necked flask, and the reaction was heated to reflux for 24 h, and then cooled to room temperature. Water was added, and the obtained solid was filtered. The solid was dried and then dissolved by heating with toluene. The insoluble matter was filtered, and the mother liquor was concentrated to dryness. The obtained solid was separated by column chromatography, and eluted with petroleum ether: dichloromethane = 8:1 (volume ratio) to obtain 3.14 g of intermediate VI.

[0127] Mass spectrometry was performed on the intermediate shown in VI: the two peaks with the largest mass-to-charge ratio (m / z) were 499.07 and 501.07, and the molecular formula of the intermediate VI was determined as: C 30 H 18 BrN3.

[0128] (5) Synthesis of intermediate VII

[0129] Into a 250 mL three-necked flask, 80 mL of tetrahydrofuran and 4.99 g (0.01 mol) of intermediate VI were added under nitrogen protection, and the mixture was cooled to -78 °C. Then 7.5 mL (0.012 mol) of 1.6 M n-butyllithium solution in n-hexane was slowly added dropwise. After the addition was completed, the mixture was kept at -78 °C for 30 min, and then 1.56 g (0.015 mol) of trimethyl borate was added. The mixture was slowly warmed to room temperature and reacted for 2 h. Water and ethyl acetate were added for liquid separation. The organic phase was washed with brine, dried over magnesium sulfate, filtered to remove magnesium sulfate, and concentrated to dryness to obtain the intermediate VII, which was used directly in the next step without further purification.

[0130] (6) Synthesis of compound D

[0131] Into a 500 mL three-necked flask, the intermediate VII and intermediate III (4.02 g, 0.012 mol) prepared in the previous step were added to 220 mL of toluene solution. After complete dissolution at 80 °C, 2 M potassium carbonate aqueous solution (110 mL) was added. After the addition of tetrakis(triphenylphosphine)palladium (0.061 g, 0.05 mmol), the mixture was heated and stirred for 12 h. The temperature was lowered to room temperature, and the mixture was liquid separated, washed with water, extracted with 100 mL*2 toluene twice, and the combined organic phase was dried over silica gel column (50 g, 200-300 mesh). The column eluate was concentrated to dryness, 100 mL of ethanol and 20 mL of toluene were added, and the mixture was warmed to 80 °C to dissolve, then 20 mL of water was slowly added dropwise, and then the mixture was cooled to room temperature. The mixture was filtered under suction to obtain compound D, which was dried to obtain 4.32 g.

[0132] Mass spectrometry was performed on compound D, and the m / z was 689.

[0133] The remaining compounds for which the specific synthesis method is not specified can be synthesized by referring to the above examples and using the existing synthesis methods in the art.

[0134] The specific structures of the compounds used in the following device examples and device comparative examples are shown below:

[0135]

[0136]

[0137] Device Example 1

[0138] The device example provides an organic electroluminescent device, and the compound provided in the above part synthesis example is used as a hole transport material in the organic electroluminescent device (see Table 1 for details, which are respectively denoted as device examples 1-1 to 1-5);

[0139] The organic electroluminescent device provided by the device embodiment has the structure of ITO / hole transport material (40 nm) / EB01 (15 nm) / EM1 (30 nm) / Alq3 (30 nm) / LiF (0.5 nm) / Al (150 nm).

[0140] The organic electroluminescent device is prepared as follows:

[0141] (1) The glass substrate coated with the ITO transparent conductive layer (as an anode) is subjected to ultrasonic treatment in a cleaning agent, then washed in deionized water, then subjected to ultrasonic oil removal in a mixed solvent of acetone and ethanol, then baked in a clean environment until completely dehydrated, washed with ultraviolet light and ozone, and the surface is bombarded with a low-energy positive ion beam to improve the surface properties;

[0142] (2) The above glass substrate is placed in a vacuum chamber, vacuumed to 1×10 -5 ~ 1×10 -6 Pa, compound A is vacuum evaporated on the anode as a hole transport layer, the evaporation rate is 0.1 nm / s, and the total evaporation film thickness is 40 nm;

[0143] (3) EB01 is vacuum evaporated on the hole transport layer as an electron blocking layer of the device, the evaporation rate is 0.1 nm / s, and the total evaporation film thickness is 15 nm;

[0144] (4) EM1 is vacuum evaporated on the electron blocking layer as an organic light-emitting layer of the device, the evaporation rate is 0.1 nm / s, and the total evaporation film thickness is 30 nm;

[0145] (5) Alq3 is vacuum evaporated on the organic light-emitting layer as an electron transport layer of the organic electroluminescent device; the evaporation rate is 0.1 nm / s, and the total evaporation film thickness is 30 nm;

[0146] (6) 0.5 nm of LiF and 150 nm of Al are vacuum evaporated on the electron transport layer as an electron injection layer and a cathode.

[0147] Device Comparative Example 1-1

[0148] The device comparative example provides an organic electroluminescent device, which is different from the device embodiment 1 only in that HT1 is selected as the hole transport material in the organic electroluminescent device, and other conditions are the same as those in the device embodiment 1.

[0149] Device Comparative Example 1-2

[0150] The device comparative example provides an organic electroluminescent device, which is different from the device embodiment 1 only in that HT2 is selected as the hole transport material in the organic electroluminescent device, and other conditions are the same as those in the device embodiment 1.

[0151] Performance test:

[0152] The brightness, driving voltage, current efficiency and lifetime test LT90 of the organic electroluminescent device provided above are tested by using OLED-1000 multi-channel accelerated aging lifetime and light color performance analysis system produced by Hangzhou Yuanfang, wherein the lifetime test LT90 refers to the time required for the brightness to reduce to 90% of the initial brightness at room temperature (25-27℃) while keeping the current density at the initial brightness unchanged (1000cd / m 2 2 in the present application), and the unit is hour; LT90 high temperature refers to the time required for the brightness to reduce to 90% of the initial brightness at 90-95℃ while keeping the current density at the initial brightness unchanged (1000cd / m 2 2 in the present application), and the unit is hour.

[0153] The specific test results are shown in Table 1:

[0154] Table 1

[0155]

[0156] As can be seen from the content of Table 1, by using the compound provided by the present application as a hole transport material, the organic electroluminescent device prepared has a lower driving voltage, higher current efficiency and longer lifetime.

[0157] After using the compound A, the compound C and the compound J provided by the present application as a hole transport material, the LT90 lifetime of the organic electroluminescent device is significantly improved, and the LT90 high temperature lifetime is also longer.

[0158] After using the compound B, the compound I provided by the present application as a hole transport material, the driving voltage of the organic electroluminescent device is significantly reduced, and the current efficiency of the organic electroluminescent device is improved.

[0159] In summary, by designing the structural formula of the compound containing carbazole and phenoxazine, the organic electroluminescent device prepared by using the compound containing carbazole and phenoxazine with a specific structure has a lower driving voltage, higher current efficiency and longer lifetime.

[0160] The applicant declares that the detailed process flow of the present application is illustrated by the above examples, but the present application is not limited to the above detailed process flow, that is, it does not mean that the present application must rely on the above detailed process flow to be implemented. It should be understood by those skilled in the art that any improvement of the present application, equivalent replacement of each raw material of the product of the present application, addition of auxiliary ingredients, selection of specific mode, etc. fall within the protection scope and disclosure scope of the present application.

Claims

1. A compound containing a carbazolophenazine group, characterized by, The carbazolophenazine group-containing compound has a structure shown in Formula I below: ； wherein L is selected from any one of the following groups: ; a dash represents the point of attachment of the group; n is selected from 0 or 1; Ar has a structure shown in Formula II below: ； Ar is bonded to the sp 2 any one of the hybridized carbon atoms or R1in Formula I is single-bonded to the L group or N atom in Formula I; R1is selected from any one of the following groups: ethyl, butyl, , , , , ; a dash represents the point of attachment of the groups; R2is selected from any one of the following groups: , , ; a dash represents the point of attachment of the group; R3is selected from H; The hydrogen atom in the compound of Formula I can be replaced by at least one of -F, -CN, -D, C1-C6 alkyl, C1-C6 alkoxy; The carbazolophenazine group-containing compound further includes Compound J: 。 2. The compound according to claim 1, wherein The hydrogen atom in the compound of Formula I can be replaced by at least one of -F, -CN, -D, C1-C3 alkyl, C1-C3 alkoxy.

3. The compound according to claim 1, wherein The compound of Formula I is selected from any one of the following compounds: 。 4. An intermediate characterized by, The intermediate has a structure shown in any one of M-C-X, M-C-B, M-C-B1: ； wherein each L in M-C-X, M-C-B, M-C-B1is independently selected from a single bond, any one of the following groups: ; a dash represents the point of attachment of the groups; X is selected from any one of H, F, Cl, Br, I; R 101 and R 102 each independently is selected from the group consisting of C1-C6alkyl; The intermediate is used for preparing the carbazolophenazine group-containing compound as claimed in any one of claims 1-3.

5. The intermediate of claim 4, wherein, The intermediate is selected from any one of the following compounds: .

6. An organic electroluminescent device, characterized by The organic electroluminescent device includes the carbazolophenazine group-containing compound as claimed in any one of claims 1-3.

7. The organic electroluminescent device according to claim 6, characterized in that The organic electroluminescent device includes a hole transport layer and a light-emitting layer.

8. The organic electroluminescent device according to claim 7, characterized in that, The material of the hole transport layer includes the carbazolophenazine group-containing compound as claimed in any one of claims 1-3.

9. A display device, characterized by comprising: The display device includes the organic electroluminescent device as claimed in any one of claims 6-8.

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