CN115385800A - Aromatic amine compound containing aliphatic bridged ring and application thereof - Google Patents

Aromatic amine compound containing aliphatic bridged ring and application thereof Download PDF

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CN115385800A
CN115385800A CN202210569707.9A CN202210569707A CN115385800A CN 115385800 A CN115385800 A CN 115385800A CN 202210569707 A CN202210569707 A CN 202210569707A CN 115385800 A CN115385800 A CN 115385800A
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aromatic amine
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何睦
王湘成
王鹏
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Shanghai Yaoyi Electronic Technology Co ltd
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Abstract

The invention relates to the field of H01L51/50, in particular to an aromatic amine compound containing an aliphatic bridged ring and application thereof, wherein the introduction of a bridged cycloalkyl group in the compound is beneficial to the improvement of the thermal stability and the chemical stability of materials; meanwhile, the introduction of side aryl R in the compound is beneficial to improving the glass transition temperature of molecules, the energy level of the molecules is easier to adjust, the requirements of R, G and B hole transport materials are met, and the side aryl R serving as the hole transport material is applied to an organic photoluminescence device and is beneficial to photoelectric conversion efficiency and service life extension of the device.

Description

Aromatic amine compound containing aliphatic bridged ring and application thereof
Technical Field
The invention relates to the field of H01L51/50, in particular to an aromatic amine compound containing an aliphatic bridged ring and application thereof.
Background
Organic electroluminescent devices (OLEDs) have advantages of high brightness, low power consumption, light weight, thin thickness, fast response speed, high contrast, wide viewing angle, and the like, and are receiving wide attention from both academic and industrial fields. At present, a common organic electroluminescent device mainly comprises an electrode, a carrier transport layer and a light-emitting layer, wherein a hole transport layer material is responsible for transferring holes at an anode to the light-emitting layer and occupies a very important position.
At present, the hole transport layer material mainly adopts aromatic amine compounds, and the molecules have good hole transport characteristics, and the front line rail energy level is easy to adjust. Chinese patent CN101510592B discloses an organic white light device based on TAPC as a light emitting layer and a method for preparing the same, 1-bis [ (di-4-toluidino) phenyl ] cyclohexane (TAPC) is widely used in organic electroluminescent devices of various colors due to its moderate highest occupied orbital level and good hole mobility. However, the glass transition temperature of the molecule is low, and the device is easy to change phase under the action of accumulated joule heat during long-time operation, so that the service life of the device is greatly influenced. Therefore, it is necessary to design a hole transport material having both higher mobility and glass transition temperature.
Therefore, in order to solve the above problems, the present invention provides an aromatic amine compound containing an aliphatic bridged ring, which has good heat resistance and chemical stability, and can be used as a hole injection layer, a hole transport layer or an electron blocking layer material for an organic electroluminescent device, so that the aromatic amine compound has a low driving voltage, a high light emitting efficiency and a long service life, and thus has high market application and popularization values.
Disclosure of Invention
The invention provides an aromatic amine compound containing an aliphatic bridged ring, which has the following structural formula:
Figure BDA0003658662340000011
wherein Cy is a polycyclic alkylene group having 7 to 30 carbon atoms, the polycyclic alkylene group being optionally substituted with a group consisting ofTwo aliphatic rings share two carbon atoms which are not directly connected; any number of hydrogen atoms at any position in the polycyclic alkylene group can be replaced by deuterium, C1-C6 alkyl, C1-C6 cycloalkyl; in the polycyclic alkylene group, the carbon atoms connected to the two substituent groups are the same carbon atom or different arbitrary carbon atoms.
As a preferable technical scheme, Z in the structural formula of the aromatic amine compound containing the aliphatic bridged ring 1 、Z 2 The structural formula of the group is as follows:
Figure BDA0003658662340000021
wherein, Z 1 、Z 2 Ar in the radical structural formula is the same or different 1 ，Ar 2 ，L 1 ，R，R 0 ，A 1 ，A 2 。
As a preferred embodiment, Z is 1 、Z 2 Ar in the radical structural formula 1 Selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, ar 2 Selected from phenylene in which any number of hydrogens are replaced with deuterium, or are not replaced with deuterium. Further preferably, ar1 is selected from the group consisting of a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzoselenophenyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzoselenophenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted silafluorenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted benzonaphthothiophenyl group, a substituted or unsubstituted benzonaphthofuranyl group, a substituted or unsubstituted benzonaphthoselenophenyl group, a substituted or unsubstituted benzofluorenyl group, and a substituted or unsubstituted benzocarbazolyl group.
As a preferred embodiment, Z is 1 、Z 2 In the radical structural formula L 1 Selected from the group consisting of a single bond, a substituted or unsubstituted C6-C30 arylene group,A substituted or unsubstituted C3-C30 heteroarylene group; further preferably, L1 is selected from the group consisting of 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, and a substituted or unsubstituted dibenzofuranylene group.
As a preferred embodiment, Z is 1 、Z 2 In the group structural formula, R is selected from substituted or unsubstituted C3-C30 cycloalkyl, C3-C30 heterocycloalkyl, C6-C30 aryl and C3-C30 heteroaryl; further preferably, Z is 1 、Z 2 In the group structural formula, R is selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzoselenophenyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzoselenophenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted silafluorenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted cyclopentyl and substituted or unsubstituted cyclohexyl.
As a preferred embodiment, the substituted group is substituted by one or more substituents selected from deuterium, a halogen group, cyano, nitro, C1-C12 alkyl, C1-C12 cycloalkyl, C1-C10 alkoxy, C1-C10 alkylthio, C6-C18 aryl and C3-C18 heteroaryl. Further preferably, the substituted group is substituted by one or more substituents selected from deuterium, fluorine, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, methoxy, ethoxy, methylthio, ethylthio, cyclobutyl, cyclopentyl, cyclohexyl, phenyl, naphthyl, biphenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl and fluorenyl.
As a preferred embodiment, Z is 1 、Z 2 In the radical structural formula (-R) 0 ) n Is n R 0 The group is substituted, wherein n is a positive integer between 1 and 5, wherein n R 0 The groups are the same or different; the described Z 1 、Z 2 In the radical structural formula R 0 Selected from the group consisting of hydrogen, deuterium, a halogen group, cyano, nitro, C1-C20 alkyl, C1-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylthio, C6-C30 aryl, C3-C30 heteroaryl. Further preferably, Z is 1 、Z 2 In the radical structural formula R 0 Selected from the group consisting of hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a 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, and a substituted or unsubstituted fluorenyl group.
As a preferred embodiment, Z is 1 、Z 2 In the radical structural formula A 1 、A 2 Each independently selected from R 0 Group, ring comprising at least one C, N, O, S atom.
Preferably, Z is 1 、Z 2 In the radical structural formula A 1 、A 2 Selected from any one or a combination of more of the following groups:
-R 0 、-S-、-CR 1 R 2 -、-CH＝CH-、-CR 1 R 2 -O-、-O-CR 1 R 2 -。
further preferably, Z is 1 、Z 2 In the radical structural formula A 1 、A 2 Selected from the group consisting of combinations represented by any of the following structural formulae:
Figure BDA0003658662340000031
Figure BDA0003658662340000041
Figure BDA0003658662340000042
wherein represents Z 1 、Z 2 Group knotThe attachment site of the nitrogen atom in the formula, R 1 、R 2 Independently exist or R 1 、R 2 To form C5-C10 cycloalkylene, said R 1 、R 2 Each independently selected from C1-C6 alkyl, phenyl, tolyl.
As a preferable technical scheme, the aromatic amine compound containing aliphatic bridged ring is the following A series compound (A) X ) B series compound (B) X ) Any one of:
Figure BDA0003658662340000043
Figure BDA0003658662340000051
Figure BDA0003658662340000061
the invention also provides application of the aromatic amine compound containing the aliphatic bridged ring, which is applied to the preparation of organic electroluminescent devices.
Advantageous effects
1. The aromatic amine compound containing aliphatic bridged ring, which has good heat resistance and chemical stability, can be used as a material of a hole injection layer, a hole transport layer or an electron blocking layer to be applied to an organic electroluminescent device, so that the aromatic amine compound has lower driving voltage, higher luminous efficiency and longer service life, and has high market application and popularization values.
2. The introduction of the bridged cycloalkyl group in the compound is beneficial to the improvement of the thermal stability and the chemical stability of materials; meanwhile, the introduction of side aryl R in the compound is beneficial to improving the glass transition temperature of molecules, the energy level of the molecules is easier to adjust, the requirements of R, G and B hole transport materials are met, and the side aryl R serving as the hole transport material is applied to an organic photoluminescence device and is beneficial to photoelectric conversion efficiency and service life extension of the device.
Detailed Description
Example 1
The embodiment 1 of the present invention provides an aromatic amine compound containing an aliphatic bridged ring, which has the following synthetic general formula:
Figure BDA0003658662340000062
the synthesis method of the intermediate compound ii-A1 comprises the following steps:
2-adamantanone (compound i-A1,24.0g, 160mmol, 1eq), aniline (45.0 g,480mmol, 3eq), and aniline hydrochloride (41.5g, 320mmol, 2eq) were added in this order to a three-necked flask in a nitrogen atmosphere, and the mixture was sufficiently stirred and then heated to reflux reaction for 20 hours. After the reaction system was cooled to room temperature, an aqueous NaOH solution was added to make the solution alkaline (pH = 10). Subsequently, the organic phase was separated, unreacted aniline was removed by distillation under the reduced pressure to obtain a crude product, which was subjected to activated carbon treatment to remove a dark color and ethyl acetate recrystallization in this order to obtain compound ii-A1 (18.0 g, yield 35.3%).
The synthesis method of the intermediate compound iii-A1 comprises the following steps:
2, 2-bis (4-aminophenyl) adamantane (compound ii-A1,5.2g,16.3mmol, 1eq), deionized water (20 mL) and aqueous HBr (48% w/w,24mL, 13eq) were added in this order to a three-necked flask, and the mixture was stirred overnight at room temperature in the dark. The mixture was then cooled to 0-3 ℃ using an ice-water bath, and a solution of sodium nitrite (2.4 g,34.2mmol, 1eq) in water (10 mL) was slowly added dropwise over a period of 30 minutes to complete the dropwise addition, yielding a gray suspension. The ice water bath was removed and the reaction was allowed to warm to room temperature and stirred for an additional 2 hours. The resulting mixed system in the three-necked flask was slowly added to an aqueous hydrogen bromide solution (48% w/w,18 mL) containing cuprous bromide (4.7 g, 32.6mmol, 2eq) under a nitrogen atmosphere, and the three-necked flask was washed with the aqueous hydrogen bromide solution (48% w/w,2 × 10 mL), and the same was added to the above cuprous bromide-containing solution, and sufficiently stirred. After warming to 90 ℃ for 1 hour, followed by cooling to room temperature, deionized water (400 mL) and dichloromethane (200 mL) were sequentially added, the separation was performed using a separatory funnel, the organic phase was collected, the aqueous phase was extracted with dichloromethane (3 × 50 mL), the combined organic phases were dried over anhydrous sodium sulfate, filtered, and the solvent was removed by rotary evaporation to give a crude product, which was purified by flash silica gel column chromatography (mobile phase was n-hexane) to give compound iii-A1 (3.8 g, yield 51.4%).
The synthesis method of the intermediate compound vi-A1 comprises the following steps:
to a three-necked flask were added 3-bromo-4-chloro-1, 1' -biphenyl (compound iv-A1, 8.0g,30.0mmol, 1eq), phenylboronic acid (compound v-A1,3.7g,30.0mmol, 1eq), and degassed toluene (240 mL) in this order under a nitrogen atmosphere, followed by addition of potassium carbonate (10.4 g,75.0mmol, 2.5eq), tetrakis (triphenylphosphine) palladium (173.3mg, 0.15mmol,0.5 eq), degassed ethanol (120 mL), and deionized water (80 mL) in this order, after thorough mixing. Stirring is started, the system is fully mixed, the temperature is increased to reflux under the nitrogen atmosphere, the reaction is carried out for 15 hours, basically no raw materials are left through analysis of thin layer chromatography, and heating is stopped. After the reaction solution was cooled to room temperature, it was poured into 200mL of toluene, and after standing and layering, the organic phase was collected with a separatory funnel, and the aqueous phase was extracted with toluene (3 × 80 mL), and the resulting organic phases were combined and dried over anhydrous magnesium sulfate, filtered, and the solvent was distilled off under reduced pressure to obtain a crude product. The crude product thus obtained 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%).
The synthesis method of the intermediate compound viii-A1 comprises the following steps:
under a nitrogen atmosphere, compounds vi-A1 (4.4g, 20.0mmol, 1eq), aniline (compounds vii-A1,1.9g,20.0mmol, 1eq), and anhydrous toluene (160 mL) were added in this order to a three-necked flask, and the mixture was sufficiently stirred, and sodium tert-butoxide (2.9g, 30.0mmol, 1.5eq), palladium bis-dibenzylideneacetone (80.5 mg, 0.14mmol,0.7 eq), and tri-tert-butylphosphine (10% n-hexane solution, 0.71mL,0.3mmol,1.5 eq), respectively, were added. Stirring is started, the system is fully mixed, the temperature is raised to reflux in the nitrogen atmosphere, after the heating is carried out for 11 hours, the thin layer chromatography is used for analyzing that no raw material is left basically, and the heating is stopped. When the reaction solution was cooled to 45 ℃ or lower, a mixed solution of 5mL of concentrated hydrochloric acid (37% aqueous solution) and 100mL of deionized water was added to the reaction system, the mixture was stirred and left to stand, the organic phase was separated by a separatory funnel, the aqueous phase was extracted with toluene (3 × 50 mL), the mixture was combined with the remaining organic phase, dried over anhydrous magnesium sulfate, filtered, and the solvent was removed by distillation under reduced pressure to obtain a crude product, which was purified by silica gel column chromatography (mobile phase was n-hexane/ethyl acetate mixed solvent) and recrystallized from a mixed solvent of ethanol/n-hexane in this order to obtain compound viii-A1 (4.5 g, yield 70.0%).
The synthesis method of the compound A1 comprises the following steps:
under a nitrogen atmosphere, the compound iii-A1 (2.2g, 5.0mmol, 1eq), the compound viii-A1 (3.5g, 11.0mmol, 2.2eq), and anhydrous toluene (60 mL) were sequentially added to a three-necked flask, and the mixture was sufficiently stirred, and further, sodium tert-butoxide (720.8mg, 7.5mmol, 1.5eq), tris (dibenzylideneacetone) palladium (22.9 mg, 0.025mmol,0.5 eq), and tri-tert-butylphosphine (10% n-hexane solution, 0.18mL,0.075mmol, 1.5 eq) were added, respectively. Stirring is started, the system is fully mixed, the temperature is increased to reflux under the nitrogen atmosphere, after heating is carried out for 10 hours, the residual of the compound iii-A1 which is basically not generated in the raw material is analyzed through thin layer chromatography, and heating is stopped. When the reaction solution was cooled to room temperature, a mixed solution of 5mL of concentrated hydrochloric acid (37% aqueous solution) and 100mL of deionized water was added to the reaction system, the mixture was stirred and allowed to stand, a separating funnel was used for separating liquid, an organic phase was retained, an aqueous phase was extracted with toluene (3 × 50 mL), the organic phase and the aqueous phase were combined with the retained organic phase, dried over anhydrous magnesium sulfate, filtered, and distilled under reduced pressure to remove the solvent, and the crude product was purified by silica gel column chromatography in this order (mobile phase was n-hexane/dichloromethane mixed solvent), and recrystallized from an ethanol/n-hexane mixed solvent to obtain compound A1 (3.4 g, yield 73.3%). Mass spectrum (m/z) =927.46[ M + H ]] + . The overall yield of the three-step reaction from compound iv-A1 to the target product A1 was 38.8%.
The synthesis method of other aromatic amine compounds A2-A104 containing aliphatic bridged ring is completely the same as A1, except that the added raw materials are slightly different. In examples 2 to 14, compounds iv-Ax, v-Ax and vii-Ax were used in place of compounds iv-A1, v-A1 and vii-A1, respectively, in equivalent amounts. See table 1 for specific embodiments, yields, and mass spectral characterization data.
TABLE 1,
Figure BDA0003658662340000091
Figure BDA0003658662340000101
Example 14
Example 14 of the present invention provides an aromatic amine compound containing an aliphatic bridged ring, having the general formula:
Figure BDA0003658662340000102
wherein: the synthesis method of the intermediate compounds ii-B5 comprises the following steps:
1, 3-dibromodiamantane (5.9g, 20.0mmol), anhydrous ferric trichloride (129.6mg, 0.8mmol) and bromobenzene (50.2g, 320mmol) are added into a three-neck flask in sequence under a nitrogen atmosphere, stirring is started, the system is fully mixed, the temperature is slowly increased to reflux, and the reaction is carried out for 18 hours. After the reaction system was cooled to room temperature, the reaction solution was slowly poured into 100mL of hydrochloric acid (0.1 mol/L aqueous HCl solution), and 100mL of chloroform was added, followed by separation with a separatory funnel after separation, the organic phase was retained, and washed with saturated aqueous sodium bicarbonate solution, dried over anhydrous magnesium sulfate, filtered, and the solvent was distilled off. The crude product was purified by flash column chromatography on silica gel (n-hexane as mobile phase) to obtain compound ii-B5 (4.6 g, yield 51.7%).
The method for synthesizing the intermediate compound viii-B5 in the above-mentioned step is specifically the same as the method for synthesizing the intermediate compound viii-A5, and the starting material iv-B5 is the same as iv-A1 except that the starting material compound v-B5 (p-tolylboronic acid) is used in an equivalent amount in place of the compound v-A1 (phenylboronic acid), and the starting material compound vii-B5 (4-aminobiphenyl) is used in an equivalent amount in place of the compound vii-A1 (aniline). Next, the objective compound B5 was obtained by referring to the synthesis method of the compound A1, except that the compounds ii to B5 and viii to B5 were used in equivalent amounts instead of the compounds iii to A1 and viii to A1, respectively. From v-B5 to the target product B5, the total yield of the three-step reaction was 42.5%.
The synthesis method of other aromatic amine compounds B1-B105 containing aliphatic bridged ring is completely the same as B5, except that the added raw materials are slightly different. In examples 15 to 26, compounds iv-Bx, v-Bx and vii-Bx were used in equivalent amounts instead of compounds iv-B5, v-B5 and vii-B5, respectively. See table 2 for specific embodiments, yields, and mass spectral characterization data.
TABLE 2,
Figure BDA0003658662340000111
Figure BDA0003658662340000121
Figure BDA0003658662340000131
Application example 1
An application embodiment 1 of the present invention provides a preparation method of an aromatic amine compound containing an aliphatic bridged ring applied to a blue organic electroluminescent device, and the specific preparation process comprises:
a transparent anode ITO film layer is formed on a glass substrate 101, and the film thickness is 150nm, so that a first electrode 102 is obtained as an anode, then a mixed material of a compound 1 and a compound A1 of the present invention is evaporated as a hole injection layer 103, the mixing ratio is 3. Then sequentially carrying out vacuum evaporation on ytterbium (Yb) with the thickness of 3nm and magnesium (Mg) and silver (Ag) with the thickness of 10nm on the electron injection layer at the evaporation rate of 1: 9 to obtain a second electrode 109, and then carrying out evaporation on a compound 7 with the thickness of 70nm to obtain a covering layer material to obtain a device; wherein the structure of each compound is shown in table 3.
TABLE 3,
Figure BDA0003658662340000132
Figure BDA0003658662340000141
Application examples 2 to 14 provide the preparation of aromatic amine based compounds containing an aliphatic bridged ring for use in the preparation of blue organic electroluminescent devices, specifically by the same process as in application example 1 except that the compounds a10, a29, a44, a70, a75, a84, a98, B19, B42, B69, B75, B87, B98 in application example 1 were used in place of the compound A1.
Application example 15
An application example 15 of the present invention provides a process for preparing an aromatic amine compound containing an aliphatic bridged ring for use in a red organic electroluminescent device, which comprises:
a transparent anode ITO film (thickness 150 nm) was formed on a glass substrate 101 to obtain a first electrode 102 as an anode. Subsequently, a mixed material of compound 1 in table 3 and compound 2-2 in table 4 was evaporated as a hole injection layer 103 on the surface of the anode by a vacuum evaporation method at a mixing ratio of 3 (mass ratio) to 97 (thickness of 10 nm). Subsequently, compound 2-2 was vapor-deposited on the hole injection layer to a thickness of 100nm to obtain a first hole transport layer 104. Followed by vapor deposition of the compound B5 of the present invention on the first hole transporting layer to a thickness of 10nm to obtain a second hole transporting layer 105. On the second hole transport layer, the compound 2-3 and the compound 2-4 were co-evaporated at a mass ratio of 95. Then, on the organic light-emitting layer, a compound 5 was sequentially vapor-deposited to form a hole blocking layer 107 (thickness 10 nm), and a compound 6 and LiQ at a mixing ratio of 4. Finally, magnesium (Mg) and silver (Ag) are mixed at the evaporation rate of 1: 9, and are evaporated on the electron injection layer in vacuum to be used as a second electrode 109, so that the manufacturing of the organic electroluminescent device is completed; the structures of the compounds are shown in Table 4.
TABLE 4,
Figure BDA0003658662340000142
Figure BDA0003658662340000151
Application examples 15 to 27 provide aromatic amine-based compounds having aliphatic bridged rings for the production of red organic electroluminescent elements by the same process as in application example 15 except that the compounds B10, B19, B40, B44, B61, B92, B105, A5, A17, A51, A64 and A100 of the present invention were used in place of the compound B5 in application example 15.
Comparative example 1
Comparative example 1 of the present invention was prepared in the same manner as in application example 1 except that compound TAPC, the structure of which is shown in table 3, was used instead of compound A1 in application example 1.
Comparative example 2
Comparative example 2 of the present invention was prepared in the same manner as in application example 2 except that compound HT-A, the structure of which is shown in Table 4, was used instead of compound B5 in application example 2.
Performance test method
The performance of the invention using examples 1-27 and comparative examples 1-2 was tested and the operating voltage and efficiency calculated using a computer controlled Keithley 2400 test system. The lifetime of the device under dark conditions was obtained using a Polaronix (mccience co.) lifetime measurement system equipped with a power supply and a photodiode as a detection unit. Wherein the devices obtained in application examples 1 to 14 and the device of comparative example 1 were produced and tested in the same batch, the operating voltage, efficiency and lifetime of the device of comparative example 1 were each respectively noted as 1, and the ratio of the corresponding indices of the devices of application examples 1 to 14 was respectively calculated, and the results are shown in table 5. The devices of application examples 15 to 27 and comparative example 2 were produced and tested in the same batch, the operating voltage, efficiency and life of the device of comparative example 1 were each designated as 1, and the ratio of the respective indices of the devices of application examples 15 to 27 was calculated, respectively, and the results are shown in table 6.
TABLE 5,
Figure BDA0003658662340000152
Figure BDA0003658662340000161
TABLE 6,
A second hole transport layer Relative operating voltage Relative efficiency Relative life time
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 (10)

1. An aromatic amine compound containing an aliphatic bridged ring, which is characterized by having the following structural formula:
Figure FDA0003658662330000011
wherein Cy is a polycyclic alkylene group having 7 to 30 carbon atoms, the polycyclic alkylene group being formed by any two aliphatic rings sharing two carbon atoms which are not directly connected; any position and any number of hydrogen atoms in the polycyclic alkylene can be replaced by deuterium, C1-C6 alkyl and C1-C6 cycloalkyl; in the polycyclic alkylene, the carbon atoms connected with the two substituent groups are the same carbon atom or different arbitrary carbon atoms; z 1 、Z 2 The groups are the same or different aromatic amine groups.
2. The aromatic amine compound containing aliphatic bridged ring according to claim 1, wherein Z in the structural formula of the aromatic amine compound containing aliphatic bridged ring 1 、Z 2 The structural formula of the group is shown as follows:
Figure FDA0003658662330000012
wherein Z is 1 、Z 2 Radical structureIn which Ar are the same or different 1 ，Ar 2 ，L 1 ，R，R 0 ，A 1 ，A 2 。
3. The aromatic amine compound containing an aliphatic bridged ring according to claim 2, wherein Z is 1 、Z 2 Ar in the radical structural formula 1 Selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, ar 2 Selected from phenylene in which any number of hydrogens are substituted or unsubstituted with deuterium.
4. The aromatic amine compound containing an aliphatic bridged ring according to claim 2, wherein Z is 1 、Z 2 In the radical structural formula L 1 Selected from the group consisting of a single bond, a substituted or unsubstituted C6-C30 arylene, and a substituted or unsubstituted C3-C30 heteroarylene.
5. The aromatic amine compound containing an aliphatic bridged ring according to claim 2, wherein Z is 1 、Z 2 In the group structural formula, R is selected from substituted or unsubstituted C3-C30 cycloalkyl, C3-C30 heterocycloalkyl, C6-C30 aryl and C3-C30 heteroaryl.
6. The aromatic amine compound containing an aliphatic bridged ring according to any one of claims 3 to 5, wherein said substituted group is substituted by one or more substituents selected from deuterium, a halogen group, cyano, nitro, C1-C12 alkyl, C1-C12 cycloalkyl, C1-C10 alkoxy, C1-C10 alkylthio, C6-C18 aryl, and C3-C18 heteroaryl.
7. The aromatic amine compound containing an aliphatic bridged ring according to claim 6, wherein Z is 1 、Z 2 In the radical structural formula R 0 Selected from hydrogen, deuterium, halogen groups, cyano, nitro, C1-C20 alkyl, C1-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylthio, C6-C30 aryl, C3-C30 heteroaryl.
8. The process according to claim 2, wherein Z is a linear or branched aliphatic bridged aromatic amine 1 、Z 2 In the radical structural formula A 1 、A 2 Each independently selected from R 0 Group, ring comprising at least one C, N, O, S atom.
9. The aromatic amine compound containing an aliphatic bridged ring according to claim 8, wherein Z is 1 、Z 2 In the radical structural formula A 1 、A 2 Selected from any one or a combination of more of the following groups: -R 0 、-S-、-CR 1 R 2 -、-CH＝CH-、-CR 1 R 2 -O-、-O-CR 1 R 2 -。
10. Use of an aromatic amine compound containing an aliphatic bridged ring according to any one of claims 1 to 9 in the preparation of an organic electroluminescent device.
CN202210569707.9A 2022-05-24 2022-05-24 Aromatic amine compound containing aliphatic bridged ring and application thereof Pending CN115385800A (en)

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