Aromatic amine compounds containing aliphatic bridge rings and their applications

Abstract

The present invention relates to the field of H01L51 / 50, specifically to aromatic amine compounds containing aliphatic bridged rings and applications thereof. The introduction of bridged ring alkyl groups in the compounds of the present invention is beneficial to improving the thermal stability and chemical stability of the materials. Simultaneously, the introduction of side aromatic groups R in the compounds is beneficial to increasing the glass transition temperature of the molecules and making the energy levels of the molecules easier to adjust, thus meeting the requirements of R, G, and B hole transport materials. When used as hole transport materials in organic photoluminescent devices, the compounds are beneficial to the photoelectric conversion efficiency of the devices and extend their service life.

Description

Technical Field

[0001] The present invention relates to the field of H01L51 / 50, in particular to aromatic amine compounds containing aliphatic bridge rings and applications thereof. Background Art

[0002] Organic electroluminescent devices (OLEDs) are attracting widespread attention from both academia and industry due to their advantages, including high brightness, low power consumption, light weight, thinness, fast response speed, high contrast, and wide viewing angle. Currently, common OLEDs consist primarily of three components: an electrode, a carrier transport layer, and a light-emitting layer. The hole transport layer plays a crucial role in transferring holes from the anode to the light-emitting layer.

[0003] At present, the hole transport layer material mainly adopts aromatic amine compounds. This type of molecule has good hole transport properties, and the frontier orbital energy level is easy to adjust. Chinese patent CN101510592B discloses an organic white light device based on TAPC as the light-emitting layer and its preparation method. 1,1-bis[(di-4-methylphenylamino)phenyl]cyclohexane (TAPC) has a moderate highest occupied orbital energy level and good hole mobility. It is widely used in organic electroluminescent devices of various colors. However, the glass transition temperature of this molecule is low, and the device is prone to phase change under the action of accumulated Joule heat when working for a long time, which has a greater impact on the life of the device. Therefore, it is very necessary to design a hole transport material with both high mobility and glass transition temperature.

[0004] Therefore, in order to solve the above problems, the present invention provides an aromatic amine compound containing an aliphatic bridge ring with good heat resistance and chemical stability, which can be used as a hole injection layer, hole transport layer or electron blocking layer material in organic electroluminescent devices, so that they have a lower driving voltage, higher luminous efficiency and longer service life, which has high market application and promotion value. Summary of the Invention

[0005] In one aspect, the present invention provides an aromatic amine compound containing an aliphatic bridge ring, which has the following structural formula:

[0006] Wherein, Cy is a polycyclic alkylene group having 7 to 30 carbon atoms, and the polycyclic alkylene group is formed by any two aliphatic rings sharing two carbon atoms that are not directly connected; any position and any number of hydrogen atoms in the polycyclic alkylene group can be substituted by deuterium, a C1 to C6 alkyl group, or a C1 to C6 cycloalkyl group; in the polycyclic alkylene group, the carbon atoms connected to the two substituent groups are the same carbon atom or any different carbon atoms.

[0007] As a preferred technical solution, the structural formulas of the Z1 and Z2 groups in the structural formula of the aromatic amine compound containing an aliphatic bridge ring are as follows:

[0008] Wherein, the structural formulas of the Z1 and Z2 groups contain the same or different Ar1, Ar2, L1, R, R0, A1, and A2.

[0009] As a preferred technical solution, in the structural formula of the Z1 and Z2 groups, Ar1 is selected from substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C3-C30 heteroaryl groups, and Ar2 is selected from phenylene groups in which any number of hydrogen atoms are replaced by deuterium or are not replaced by deuterium. Further preferably, Ar1 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzoselenophene, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzoselenophene, substituted or unsubstituted fluorenyl, substituted or unsubstituted silanyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted benzonaphthothiophenyl, substituted or unsubstituted benzonaphthofuranyl, substituted or unsubstituted benzonaphthoselenophene, substituted or unsubstituted benzofluorenyl, substituted or unsubstituted benzocarbazolyl.

[0010] As a preferred technical solution, in the structural formula of the Z1 and Z2 groups, L1 is selected from a single bond, a substituted or unsubstituted C6-C30 arylene group, or a substituted or unsubstituted C3-C30 heteroarylene group; further preferably, L1 is selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted dibenzothiophenylene group, or a substituted or unsubstituted dibenzofuranyl group.

[0011] As a preferred technical solution, in the structural formula of the Z1 and Z2 groups, R is selected from substituted or unsubstituted C3-C30 cycloalkyl, C3-C30 heterocycloalkyl, C6-C30 aryl, and C3-C30 heteroaryl; further preferably, in the structural formula of the Z1 and Z2 groups, R is selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzoselenophene, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzoselenophene, substituted or unsubstituted fluorenyl, substituted or unsubstituted silyfluorenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted cyclopentyl, and substituted or unsubstituted cyclohexyl.

[0012] As a preferred technical solution, the substituted group is substituted by one or more substituents selected from the group consisting of deuterium, a halogen group, a cyano group, a nitro group, a C1-C12 alkyl group, a C1-C12 cycloalkyl group, a C1-C10 alkoxy group, a C1-C10 alkylthio group, a C6-C18 aryl group, or a C3-C18 heteroaryl group. Further preferably, the substituted group is substituted by one or more substituents selected from the group consisting of deuterium, a fluorine group, a cyano group, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a tert-butyl group, a methoxy group, an ethoxy group, a methylthio group, an ethylthio group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a phenyl group, a naphthyl group, a biphenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a carbazolyl group, or a fluorenyl group.

[0013] As a preferred technical solution, in the structural formula of the Z1 and Z2 groups (-R0) n The Z1 and Z2 groups are substituted with n R0 groups, wherein n is a positive integer between 1 and 5, and wherein the n R0 groups are the same or different; in the structural formula of the Z1 and Z2 groups, R0 is selected from hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a C1-C20 alkyl group, a C1-C20 cycloalkyl group, a C1-C20 alkoxy group, a C1-C20 alkylthio group, a C6-C30 aryl group, and a C3-C30 heteroaryl group. Further preferably, in the structural formula of the Z1 and Z2 groups, R0 is selected from hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a tert-butyl group, a methoxy group, an ethoxy group, a methylthio group, an ethylthio group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted carbazolyl group, or a substituted or unsubstituted fluorenyl group.

[0014] As a preferred technical solution, in the structural formulas of the Z1 and Z2 groups, A1 and A2 are each independently selected from the R0 group, and are a ring formed by at least one C, N, O, or S atom.

[0015] Preferably, in the structural formula of the Z1 and Z2 groups, A1 and A2 are selected from any one of the following groups or a combination of multiple groups:

[0016] -R0, -S-, -CR1R2-, -CH=CH-, -CR1R2-O-, -O-CR1R2-.

[0017] Further preferably, in the structural formula of the Z1 and Z2 groups, A1 and A2 are selected from the combination represented by any one of the following structural formulas:

[0018] Wherein * represents the connection site of the nitrogen atom in the structural formula of the Z1 and Z2 groups, R1 and R2 exist independently or R1 and R2 are connected to form a C5-C10 cycloalkylene group, and R1 and R2 are each independently selected from C1-C6 alkyl, phenyl, and tolyl.

[0019] As a preferred technical solution, the aromatic amine compound containing an aliphatic bridge ring is the following A series compound (A X ), B series compounds (B X ) in any of the following ways:

[0020]

[0021]

[0022]

[0023] Another aspect of the present invention provides an application of an aromatic amine compound containing an aliphatic bridge ring, which is applied to the preparation of an organic electroluminescent device.

[0024] Beneficial effects

[0025] 1. The present invention provides an aromatic amine compound containing an aliphatic bridge ring with good heat resistance and chemical stability, which can be used as a hole injection layer, hole transport layer or electron blocking layer material in organic electroluminescent devices, enabling them to have a lower driving voltage, higher luminous efficiency and longer service life, which has high market application and promotion value.

[0026] 2. The introduction of a bridged cycloalkyl group into the compound of the present invention improves the thermal and chemical stability of the material. Simultaneously, the introduction of a pendant aromatic group (R) into the compound increases the glass transition temperature of the molecule and makes the energy level of the molecule more easily adjustable, thus meeting the requirements of R, G, and B hole transport materials. Application of such hole transport materials in organic photoluminescent devices improves the photoelectric conversion efficiency of the devices and prolongs their service life. DETAILED DESCRIPTION

[0027] Example 1

[0028] Example 1 of the present invention provides an aromatic amine compound containing an aliphatic bridge ring, and its general synthetic formula is as follows:

[0029]

[0030] Among them, the synthesis method of intermediate compound ii-A1 is:

[0031] Under a nitrogen atmosphere, 2-adamantanone (compound i-A1, 24.0 g, 160 mmol, 1 eq), aniline (45.0 g, 480 mmol, 3 eq), and aniline hydrochloride (41.5 g, 320 mmol, 2 eq) were added sequentially to a three-necked flask. The mixture was thoroughly stirred and then heated to reflux for 20 hours. After the reaction system cooled to room temperature, aqueous NaOH was added to make the solution alkaline (pH = 10). The organic phase was then separated and unreacted aniline was removed by vacuum distillation to obtain a crude product. The crude product was then treated with activated carbon to remove the dark color and recrystallized from ethyl acetate to obtain compound ii-A1 (18.0 g, 35.3% yield).

[0032] The synthesis method of intermediate compound iii-A1 is:

[0033] 2,2-Bis(4-aminophenyl)adamantane (Compound ii-A1, 5.2 g, 16.3 mmol, 1 eq), deionized water (20 mL), and aqueous HBr (48% w / w, 24 mL, 13 eq) were added sequentially to a three-necked flask. The mixture was stirred overnight at room temperature in the dark. An ice-water bath was then used to cool the mixture to 0-3°C. A solution of sodium nitrite (2.4 g, 34.2 mmol, 1 eq) in water (10 mL) was slowly added dropwise over 30 minutes to yield a gray suspension. The ice-water bath was removed, and the reaction system was allowed to warm to room temperature before stirring for an additional 2 hours. Under a nitrogen atmosphere, the resulting mixture in a three-necked flask was slowly added to a solution of cuprous bromide (4.7 g, 32.6 mmol, 2 eq) in aqueous hydrogen bromide (48% w / w, 18 mL). The flask was rinsed with aqueous hydrogen bromide (48% w / w, 2 x 10 mL) and the same solution was added to the cuprous bromide solution and stirred thoroughly. The mixture was heated to 90°C for 1 hour, then cooled to room temperature. Deionized water (400 mL) and dichloromethane (200 mL) were added sequentially. The mixture was separated using a separatory funnel, and the organic phase was collected. The aqueous phase was extracted with dichloromethane (3 x 50 mL). The combined organic phases were dried over anhydrous sodium sulfate, filtered, and the solvent was removed by rotary evaporation to obtain a crude product. The crude product was purified by flash silica gel column chromatography (mobile phase: n-hexane) to obtain compound iii-A1 (3.8 g, yield 51.4%).

[0034] The synthesis method of intermediate compound vi-A1 is:

[0035] Under a nitrogen atmosphere, 3-bromo-4-chloro-1,1'-biphenyl (compound iv-A1, 8.0 g, 30.0 mmol, 1 eq), phenylboronic acid (compound v-A1, 3.7 g, 30.0 mmol, 1 eq), and degassed toluene (240 mL) were added sequentially to a three-necked flask. After thorough mixing, potassium carbonate (10.4 g, 75.0 mmol, 2.5 eq), tetrakis(triphenylphosphine)palladium (173.3 mg, 0.15 mmol, 0.5% eq), degassed ethanol (120 mL), and deionized water (80 mL) were added sequentially. Stirring was initiated and the system was thoroughly mixed. The mixture was then heated to reflux under a nitrogen atmosphere and allowed to react for 15 hours. Thin-layer chromatography analysis revealed virtually no residual starting material, and heating was discontinued. After the reaction solution was cooled to room temperature, it was poured into 200 mL of toluene. After standing and stratification, the organic phase was collected using a separatory funnel. The aqueous phase was extracted with toluene (3 × 80 mL). The resulting organic phases were combined and dried over anhydrous magnesium sulfate, filtered, and the solvent was removed by distillation under reduced pressure to obtain a crude product. The crude product was purified by silica gel column chromatography (mobile phase: n-hexane / dichloromethane mixed solvent) to obtain compound vi-A1 (6.0 g, yield 75.6%).

[0036] The synthesis method of intermediate compound viii-A1 is:

[0037] Under a nitrogen atmosphere, compound vi-A1 (4.4 g, 20.0 mmol, 1 eq), aniline (compound vii-A1, 1.9 g, 20.0 mmol, 1 eq), and anhydrous toluene (160 mL) were added sequentially to a three-necked flask. The mixture was thoroughly stirred. Sodium tert-butoxide (2.9 g, 30.0 mmol, 1.5 eq), bisdibenzylideneacetone palladium (80.5 mg, 0.14 mmol, 0.7% eq), and tri-tert-butylphosphine (10% solution in n-hexane, 0.71 mL, 0.3 mmol, 1.5% eq) were then added. Stirring was initiated and the mixture was thoroughly mixed. The mixture was then heated to reflux under a nitrogen atmosphere. After heating for 11 hours, thin-layer chromatography analysis revealed virtually no starting material remaining, and heating was discontinued. When the reaction solution was cooled to below 45°C, a mixed solution of 5 mL of concentrated hydrochloric acid (37% aqueous solution) and 100 mL of deionized water was added to the reaction system, stirred and allowed to stand, and separated using a separatory funnel. The organic phase was retained, and the aqueous phase was extracted with toluene (3×50 mL), combined with the retained organic phase, dried over anhydrous magnesium sulfate, filtered, and the solvent was removed by distillation under reduced pressure to obtain a crude product. The crude product was purified by silica gel column chromatography (mobile phase: a mixed solvent of n-hexane / ethyl acetate) and recrystallized from a mixed solvent of ethanol / n-hexane to obtain compound viii-A1 (4.5 g, yield 70.0%).

[0038] The synthesis method of compound A1 is:

[0039] Under a nitrogen atmosphere, compound iii-A1 (2.2 g, 5.0 mmol, 1 eq), compound viii-A1 (3.5 g, 11.0 mmol, 2.2 eq), and anhydrous toluene (60 mL) were added sequentially to a three-necked flask. The mixture was thoroughly stirred. Sodium tert-butoxide (720.8 mg, 7.5 mmol, 1.5 eq), tris(dibenzylideneacetone)palladium (22.9 mg, 0.025 mmol, 0.5% eq), and tri-tert-butylphosphine (10% solution in n-hexane, 0.18 mL, 0.075 mmol, 1.5% eq) were then added. Stirring was initiated and the mixture was thoroughly mixed. The mixture was then heated to reflux under a nitrogen atmosphere. After heating for 10 hours, thin-layer chromatography analysis revealed virtually no residual starting compound iii-A1. Heating was then discontinued. When the reaction solution cooled to room temperature, a mixed solution of 5 mL of concentrated hydrochloric acid (37% aqueous solution) and 100 mL of deionized water was added to the reaction system, stirred, and allowed to stand. The mixture was separated using a separatory funnel, and the organic phase was retained. The aqueous phase was extracted with toluene (3×50 mL), combined with the retained organic phase, dried over anhydrous magnesium sulfate, filtered, and the solvent was removed by distillation under reduced pressure. The crude product was purified by silica gel column chromatography (mobile phase: a mixed solvent of n-hexane / dichloromethane) and recrystallized from a mixed solvent of ethanol / n-hexane to obtain Compound A1 (3.4 g, yield 73.3%). Mass spectrum (m / z) = 927.46 [M+H] + The total yield of the three-step reaction from compound iv-A1 to target product A1 was 38.8%.

[0040] The synthesis methods for other aliphatic bridged aromatic amines A2-A104 are identical to those for A1, differing only in the starting materials used. In Examples 2-14, compounds iv-Ax, v-Ax, and vii-Ax were used in equivalent amounts to replace compounds iv-A1, v-A1, and vii-A1, respectively. Specific implementations, yields, and mass spectrometric characterization data are shown in Table 1.

[0041] Table 1

[0042]

[0043]

[0044] Example 14

[0045] Example 14 of the present invention provides an aromatic amine compound containing an aliphatic bridge ring, and its general synthetic formula is as follows:

[0046]

[0047] Wherein: The synthesis method of intermediate compound ii-B5 is:

[0048] Under a nitrogen atmosphere, 1,3-dibromoadamantane (5.9 g, 20.0 mmol), anhydrous ferric chloride (129.6 mg, 0.8 mmol), and bromobenzene (50.2 g, 320 mmol) were added sequentially to a three-necked flask. Stirring was initiated, the system was thoroughly mixed, and the temperature was slowly raised to reflux for 18 hours. After the reaction system cooled to room temperature, the reaction solution was slowly poured into 100 mL of hydrochloric acid (0.1 mol / L aqueous HCl solution) and 100 mL of chloroform was added. The layers were separated using a separatory funnel. The organic phase was retained and washed with saturated sodium bicarbonate solution, dried over anhydrous magnesium sulfate, filtered, and the solvent was distilled off. The crude product was purified by flash silica gel column chromatography (mobile phase: n-hexane) to obtain compound ii-B5 (4.6 g, 51.7% yield).

[0049] The synthesis method for the intermediate compound viii-B5 in this step is specifically the same as the synthesis method for the intermediate compound viii-A5. The starting materials iv-B5 and iv-A1 are the same, except that the starting materials v-B5 (p-methylphenylboronic acid) are used in an equivalent amount to replace the compound v-A1 (phenylboronic acid), and the starting material vii-B5 (4-aminobiphenyl) is used in an equivalent amount to replace the compound vii-A1 (aniline). Next, the target compound B5 is obtained by referring to the synthesis method of compound A1, except that the compounds ii-B5 and viii-B5 are used in an equivalent amount to replace the compounds iii-A1 and viii-A1, respectively. The total yield of the three-step reaction from v-B5 to the target product B5 is 42.5%.

[0050] The synthesis methods for other aliphatic bridged aromatic amine compounds B1-B105 are identical to those for B5, except for slightly different starting materials. In Examples 15-26, compounds iv-Bx, v-Bx, and vii-Bx were used in equivalent amounts to replace compounds iv-B5, v-B5, and vii-B5, respectively. Specific implementations, yields, and mass spectrometric characterization data are shown in Table 2.

[0051] Table 2

[0052]

[0053]

[0054]

[0055] Application Example 1

[0056] Application Example 1 of the present invention provides an aromatic amine compound containing an aliphatic bridge ring for use in the preparation of a blue organic electroluminescent device. The specific preparation process is as follows:

[0057] On a glass substrate 101, a transparent anode ITO film layer with a thickness of 150 nm was formed to obtain a first electrode 102 as an anode, and then a mixed material of compound 1 and compound A1 of the present invention was evaporated as a hole injection layer 103 with a mixing ratio of 3:97 (mass ratio) and a thickness of 10 nm. Then, a 100 nm thick compound HT-2 was evaporated to obtain a first hole transport layer 104, and then a 20 nm thick compound 1-2 was evaporated to obtain a second hole transport layer 105. Then, compounds 1-3 and 1-4 (thickness 30 nm) were evaporated at a deposition rate of 95:5 to prepare a blue light emitting unit 106, and then a 10 nm thick compound 5 was evaporated in sequence to form a hole blocking layer 107, and a compound 6 and LiQ with a mixing ratio of 4:6 (mass ratio) were formed to form an electron transport layer 108 (thickness 30 nm). Then, ytterbium (Yb) with a thickness of 3 nm, magnesium (Mg) with a thickness of 10 nm, and silver (Ag) with a thickness of 1:9 were vacuum evaporated on the electron injection layer to serve as the second electrode 109. Subsequently, 70 nm of compound 7 was evaporated as the covering layer material to complete the device fabrication. The structures of the various compounds are shown in Table 3.

[0058] Table 3

[0059]

[0060]

[0061] Application Examples 2-14 provide the preparation of aromatic amine compounds containing aliphatic bridge rings for use in blue organic electroluminescent devices. The specific preparation process is the same as that of Application Example 1, except that Compounds A10, A29, A44, A70, A75, A84, A98, B19, B42, B69, B75, B87, and B98 are used instead of Compound A1 in Application Example 1 for preparation.

[0062] Application Example 15

[0063] Application Example 15 of the present invention provides an aromatic amine compound containing an aliphatic bridge ring for use in the preparation of a red organic electroluminescent device. The specific preparation process is as follows:

[0064] On a glass substrate 101, a transparent anode ITO film (thickness 150nm) is formed to obtain a first electrode 102 as an anode. Subsequently, by a vacuum evaporation method, a mixed material of compound 1 in Table 3 and compound 2-2 in Table 4 is evaporated on the anode surface as a hole injection layer 103, and a mixing ratio of 3:97 (mass ratio) is used, and a thickness of 10nm is obtained. Subsequently, compound 2-2 with a thickness of 100nm is evaporated on the hole injection layer to obtain a first layer of hole transport layer 104. Subsequently, compound B5 of the present invention with a thickness of 10nm is evaporated on the first hole transport layer to obtain a second layer of hole transport layer 105. On the second hole transport layer, compound 2-3 and compound 2-4 are co-evaporated with a mass ratio of 95:5 to form an organic light-emitting layer 106 with a thickness of 40nm. Next, compound 5 was sequentially evaporated onto the organic light-emitting layer to form a hole-blocking layer 107 (10 nm thick). Compound 6 and LiQ, mixed at a 4:6 mass ratio, formed an electron-transporting layer 108 (30 nm thick). Finally, magnesium (Mg) and silver (Ag) were mixed at a 1:9 deposition rate and vacuum-evaporated onto the electron-injection layer to form the second electrode 109, completing the fabrication of the organic electroluminescent device. The structures of the compounds are shown in Table 4.

[0065] Table 4

[0066]

[0067]

[0068] Application Examples 15-27 provide the preparation of aromatic amine compounds containing aliphatic bridge rings for use in red organic electroluminescent devices. The specific preparation process is the same as that of Application Example 15, except that the compounds B10, B19, B40, B44, B61, B92, B105, A5, A17, A51, A64, and A100 of the present invention are used instead of compound B5 in Application Example 15 for the preparation.

[0069] Comparative Example 1

[0070] The specific implementation of Comparative Example 1 of the present invention is the same as that of Application Example 1, except that the compound TAPC is used instead of the compound A1 in Application Example 1 for preparation. The structure of the compound TAPC is shown in Table 3.

[0071] Comparative Example 2

[0072] The specific implementation of Comparative Example 2 of the present invention is the same as that of Application Example 2, except that Compound HT-A is used instead of Compound B5 in Application Example 2 for preparation, wherein the structure of Compound HT-A is shown in Table 4.

[0073] Performance testing methods

[0074] Performance tests were performed on Application Examples 1-27 and Comparative Examples 1-2 of the present invention, and their operating voltage and efficiency were calculated using a computer-controlled Keithley 2400 test system. The device lifespan under dark conditions was measured using a Polaronix (McScience Co.) lifespan measurement system equipped with a power supply and a photodiode as a detection unit. The devices obtained from Application Examples 1-14 were produced and tested in the same batch as the device from Comparative Example 1. The operating voltage, efficiency, and lifespan of the device from Comparative Example 1 were each recorded as 1, and the ratios of the corresponding indices of the devices from Application Examples 1-14 were calculated. The results are shown in Table 5. The devices from Application Examples 15-27 were produced and tested in the same batch as the device from Comparative Example 2. The operating voltage, efficiency, and lifespan of the device from Comparative Example 1 were each recorded as 1, and the ratios of the corresponding indices of the devices from Application Examples 15-27 were calculated. The results are shown in Table 6.

[0075] Table 5

[0076]

[0077]

[0078] Table 6

[0079] Second hole transport layer Relative working voltage Relative efficiency Relative lifespan Comparative Example 2 HT-A 1 1 1 Application Example 15 B5 0.930 1.169 1.440 Application Example 16 B10 0.922 1.083 1.325 Application Example 17 B19 0.902 1.104 1.395 Application Example 18 B40 0.946 1.078 1.505 Application Example 19 B44 0.935 1.126 1.311 Application Example 20 B61 0.918 1.177 1.482 Application Example 21 B92 0.937 1.096 1.365 Application Example 22 B105 0.908 1.146 1.337 Application Example 23 A5 0.931 1.115 1.454 Application Example 24 A17 0.912 1.180 1.378 Application Example 25 A51 0.928 1.151 1.410 Application Example 26 A63 0.941 1.173 1.358 Application Example 27 A100 0.960 1.101 1.254

Claims

1. An aromatic amine compound containing an aliphatic bridge ring, characterized in that: It has the following structural formula: Wherein, Cy is a polycyclic alkylene group having 7 to 30 carbon atoms, wherein the polycyclic alkylene group is formed by any two aliphatic rings sharing two carbon atoms that are not directly connected; The Z1 and Z2 are the same, and the structural formulas of the Z1 and Z2 groups are as follows: , wherein the structural formulas of the Z1 and Z2 groups have the same Ar1, Ar2, L1, R, R0, A1, A2; The L1 is a single bond; The Ar1 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, unsubstituted naphthyl, unsubstituted dibenzothiophenyl, unsubstituted dibenzoselenophene, and substituted fluorenyl; Said Ar2 is a phenylene group; In the structural formula of the Z1 and Z2 groups, R is selected from substituted or unsubstituted phenyl, unsubstituted dibenzothienyl, unsubstituted dibenzofuranyl, and substituted fluorenyl; The structural formula of the Z1 and Z2 groups is shown as a fragment A combination selected from any one of the following structural formulas: 、 、 、 、 、 、 、 、 、 、 、 、 、 , wherein * represents the connection site of the nitrogen atom in the structural formula of the Z1 and Z2 groups, and R1 and R2 are methyl groups; In the structural formula of the Z1 and Z2 groups (-R0) n is substituted with n R0 groups, wherein n is 1 or 2, and wherein n R0 groups are the same; in the structural formula of the Z1 and Z2 groups, R0 is hydrogen, methyl, or substituted or unsubstituted phenyl; The substituted groups are one or more of deuterium, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclobutyl, cyclopentyl, cyclohexyl, and phenyl.

2. An application of the aromatic amine compound containing an aliphatic bridge ring according to claim 1, characterized in that: It is used in the preparation of hole injection layers and hole transport layers of organic electroluminescent devices.

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