Amino compound and organic electroluminescent device

Abstract

The invention discloses a compound and an organic electroluminescent device, and relates to the technical field of organic electroluminescence, the compound at least contains more than one deuterium at a specific position of a benzene ring substituent group, and the introduction of deuterium, aryl or deuterated aryl groups at the position greatly improves the thermal stability and chemical stability of a material. And the service life of the device is prolonged. Meanwhile, larger steric hindrance and torque, better stability, better solubility, higher efficiency and longer service life are achieved.

Description

Technical Field

[0001] The invention relates to the technical field of organic electroluminescence, and in particular to an amine compound and an organic electroluminescence device. Background Art

[0002] OLED is a current-type organic light-emitting device. It emits light through the injection and recombination of carriers. The luminous intensity is proportional to the injected current. Under the action of the electric field, the holes generated by the anode and the electrons generated by the cathode will move, inject into the hole transport layer and the electron transport layer respectively, and migrate to the light-emitting layer. When the two meet in the light-emitting layer, energy excitons are generated, which excite the light-emitting molecules and finally produce visible light.

[0003] OLED does not require the backlight system used in LCD. When LCD is working, it selectively blocks certain backlight areas to allow the image to appear, while OLED relies on its own light. Because OLED does not require a backlight system, its power consumption is less than LCD (most of the power consumed by LCD is used for the backlight system). This is especially important for battery-powered devices.

[0004] As far as the actual needs of the current organic electroluminescent industry are concerned, the current development of organic electroluminescent materials is far from enough and lags far behind the requirements of panel manufacturers. In addition, the research pace of domestic companies is also far behind that of American, Japanese and Korean companies. Therefore, developing and providing more selectable organic electroluminescent materials is the top priority for domestic panel companies. Summary of the invention

[0005] The purpose of the present invention is to provide an amino compound and an organic electroluminescent device in view of the above technical problems.

[0006] The purpose of the present invention can be achieved by the following measures:

[0007] An amino compound having a structure as shown in Formula 1:

[0008]

[0009] in,

[0010] Ar1 is a substituted or unsubstituted group: a C6-C30 aromatic group or a C5-C30 heteroaromatic group, wherein the substituent is selected from one or more of deuterium, cyano, C1-C4 alkyl, C1-C4 deuterated alkyl, C6-C20 aryl, C6-C20 deuterated aryl, and C3-C20 heteroaromatic group;

[0011] R1-R8 are independently selected from hydrogen, deuterium, or the following groups which may or may not be deuterated: one or more of a C1-C10 alkyl group, a C3-C10 cycloalkyl group, a C6-C30 aromatic group, or a C5-C30 heteroaryl group;

[0012] A1-A5 are independently hydrogen, deuterium, C6-C20 aryl or deuterated C6-C20 aryl, and at least one of A1-A5 is deuterium;

[0013] m, n, o, p or q is a positive integer from 0 to 4;

[0014] r is a positive integer from 0 to 3.

[0015] Further preferably, the structural formula of the compound of the present invention is shown in Formula 2-Formula 5 below:

[0016]

[0017] In Formula 2 to Formula 5, the meanings of R1-R8, A1-A5, Ar1, m, n, o, p, q, and r are the same as in the above description.

[0018] Preferably, Ar1 is a substituted or unsubstituted group as follows: phenyl, biphenyl, carbazolyl, N-phenylcarbazolyl, dibenzofuranyl, dibenzothiophenyl; and its substituent is selected from one or more of deuterium, cyano, C1-C4 alkyl, C1-C4 deuterated alkyl, C6-C20 aryl, C6-C20 deuterated aryl, and C3-C20 heteroaryl.

[0019] More preferably, Ar1 is a substituted or unsubstituted group: phenyl, biphenyl, N-phenylcarbazolyl, dibenzofuranyl or dibenzothiophenyl; and its substituent is selected from one or more of deuterium, methyl, deuterated methyl, tert-butyl, phenyl and deuterated phenyl.

[0020] Preferably, A1-A5 are independently hydrogen, deuterium, phenyl or deuterated phenyl, and at least one of A1-A5 is deuterium.

[0021] Preferably, R1-R8 are independently hydrogen, deuterium, methyl, deuterated methyl, ethyl, deuterated ethyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, cyclopentyl, deuterated cyclopentyl, cyclohexyl, deuterated cyclohexyl, phenyl, deuterated phenyl.

[0022] Further preferably, Ar1 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted N-phenylcarbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothienyl group; wherein the phenyl group, the biphenyl group, the N-phenylcarbazolyl group, the dibenzofuranyl group, or the dibenzothienyl group are unsubstituted or at least one hydrogen therein is replaced by deuterium, methyl, deuterated methyl, tert-butyl or phenyl.

[0023] More preferably, R1 is hydrogen, deuterium, phenyl or deuterated phenyl.

[0024] More preferably, R6 and R7 are each independently hydrogen or methyl.

[0025] Preferably, m, n, o, p, and q are integers of 0-4, such as 0, 1, 2, 3, and 4.

[0026] Furthermore, the compound of the present invention may be any one of the following compounds:

[0027]

[0028]

[0029]

[0030]

[0031]

[0032]

[0033]

[0034]

[0035]

[0036] The compound having the structure shown in Formula 1 of the present invention has a synthesis reaction route as follows:

[0037]

[0038] An organic electroluminescent device comprises a first electrode, a second electrode and an organic layer formed between the first electrode and the second electrode, wherein the organic layer contains the above compound.

[0039] Furthermore, the organic layer comprises a hole injection layer, a first hole transport layer, a second hole transport layer, a light-emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer; and at least one of the hole injection layer, the first hole transport layer, the second hole transport layer, the light-emitting layer, the hole blocking layer, the electron transport layer, and the electron injection layer contains the above-mentioned compound.

[0040] Furthermore, the hole transport layer contains the above-mentioned compound.

[0041] An electronic display device containing the organic electroluminescent device.

[0042] An OLED lighting device containing the organic electroluminescent device.

[0043] The room temperature described in the present invention is 25±5°C.

[0044] Beneficial effects of the present invention:

[0045] The present invention designs a new type of organic electroluminescent material. The significant feature is that at least one of the benzene ring substituents A1-A5 of the compound of the present invention is deuterium, and the introduction of deuterium, aryl or deuterated aryl groups at this position has the following two advantages:

[0046] 1. The introduction of deuterium greatly improves the thermal and chemical stability of the material, thereby increasing the life of the device.

[0047] 2. Greater steric hindrance and torque, better stability, better solubility, higher efficiency and longer life. BRIEF DESCRIPTION OF THE DRAWINGS

[0048] Figure 1 It is a schematic structural diagram of an organic electroluminescent device of the present invention;

[0049] The numbers in the figure represent: 1-anode, 2-hole injection layer, 3-first hole transport layer, 4-second hole transport layer, 5-light-emitting layer, 6-hole blocking layer, 7-electron transport layer, 8-electron injection layer, 9-cathode.

[0050] Figure 2 This is the HPLC chart of compound 20 prepared in Example 12 of the present invention.

[0051] Figure 3 is the DSC spectrum of compound 20 prepared in Example 12 of the present invention, Figure 3 It can be seen that the Tg value of compound 20 is 128.40°C.

[0052] Figure 4 is the TGA spectrum of compound 20 prepared in Example 12 of the present invention, Figure 4It can be seen that the thermal weight loss temperature Td value is 408.44℃.

[0053] Figure 5 is a life graph of the organic electroluminescent device in Application Example 1 and Comparative Example 1 of the present invention; Figure 5 It can be seen that the T97% lifespans of the organic electroluminescent devices prepared in Application Example 1 and Comparative Example 1 of the present invention are 837 h and 570 h, respectively.

[0054] Figure 6 This is the NMR chart of compound 20 prepared in Example 12 of the present invention. DETAILED DESCRIPTION

[0055] The following further illustrates and describes embodiments of various aspects. It should be understood that the description herein is not intended to limit the claims to the specific aspects described. On the contrary, it is intended to cover substitutions, modifications and equivalents that may be included in the spirit and scope of the present disclosure defined by the appended claims.

[0056] As used herein, in "deuterated" or "undeuterated", the term "deuterated" means that at least one hydrogen in the group is re-coordinated with deuterium. The term "undeuterated" means that all hydrogens in the group are not re-coordinated with deuterium.

[0057] The "aromatic group", "aryl" or "aromatic group" herein refers to a group containing one or more aromatic rings, and the aromatic rings here include but are not limited to benzene, naphthalene, phenanthrene, fluorene, acenaphthene, pyridine, pyrimidine, pyrrole, furan, thiophene, etc. C6-C30 in the C6-C30 aromatic group means that the group contains 6-30 carbon atoms. In the C6-C20 aromatic group substituted with C1-C10 alkyl, C1-C10 refers to the number of carbon atoms of the substituent, and C6-C20 refers to the number of carbon atoms of the aromatic group without substituents. Aromatic groups can be divided into monocyclic aromatic groups and polycyclic aromatic groups. Specific aromatic groups in the present invention include but are not limited to phenyl, biphenyl, terphenyl, anthracene, naphthyl, phenanthryl, fluorenyl, dibenzofuranyl, dibenzothiophenyl, 9,9-spirobifluorenyl, 9,9-dimethylfluorenyl or 9,9-diphenylfluorenyl, etc. Aromatic groups can be substituted or unsubstituted.

[0058] "Cycloalkyl" herein refers to a monocyclic or fused ring ("fused" ring means that each ring in the system shares a pair of adjacent carbon atoms with other rings in the system) group that is all carbon, wherein one or more rings are saturated alicyclic rings, which generally have 3-20 carbon atoms, preferably 3-12 carbon atoms, and more preferably 3-10 carbon atoms. Cycloalkyl can be divided into monocyclic alkyls having only one ring and fused cyclic alkyls having multiple rings. Examples of monocyclic alkyls include, but are not limited to, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane. Cycloalkyl can be substituted and unsubstituted.

[0059] "Cycloalkenyl" herein refers to a monocyclic or fused ring ("fused" ring means that each ring in the system shares a pair of adjacent carbon atoms with other rings in the system) group that is all carbon, wherein one or more rings do not have a completely connected π electron system and contain at least one alkenyl group, which generally has 3-20 carbon atoms, preferably 3-12 carbon atoms, more preferably 3-10 carbon atoms, and the examples of cycloalkenyl groups include but are not limited to cyclopentene, cyclohexene, cyclohexadiene, cycloheptatriene. Cycloalkenyl groups may be substituted and unsubstituted.

[0060] The "deuterated aromatic group" herein refers to a group in which one or more hydrogen atoms in an aromatic group are substituted with deuterium.

[0061] The "deuterated phenyl group" herein refers to a group in which one or more hydrogen atoms in a phenyl group are replaced by deuterium.

[0062] Herein, “m, n, o, p, q are integers of 0-4” means that m, n, o, p, q can be 0, 1, 2, 3, 4 independently.

[0063] Herein, “r is an integer of 0-3” means that r can be 0, 1, 2, or 3 independently.

[0064] "At least one of A1-A5 is deuterium" herein means that at least one of A1, A2, A3, A4 and A5 is deuterium, and the others are hydrogen; or at least two of A1, A2, A3, A4 and A5 are deuterium, and the others are hydrogen; or at least three of A1, A2, A3, A4 and A5 are deuterium, and the others are hydrogen; or at least four of A1, A2, A3, A4 and A5 are deuterium, and the others are hydrogen; or A1, A2, A3, A4 and A5 are all deuterium.

[0065] The "heteroaryl" herein refers to a heteroaryl group obtained by replacing one or more C atoms in the structure of the "aryl" with one or more heteroatoms (such as N, O or S).

[0066] If the specific conditions are not specified in the examples, the experiments were carried out under conventional conditions or conditions recommended by the manufacturer. If the manufacturers of the reagents or instruments are not specified, they are all conventional products that can be purchased commercially.

[0067] Embodiment 1:

[0068] The synthesis method of compound 3 is as follows:

[0069]

[0070]

[0071] S0: Under nitrogen protection, add halide 1-a (15.8g, 0.1mol, 1eq) to the reaction bottle, dry THF 200ml, cool to -78°C, add 2.5M n-butyl lithium (44ml, 0.11mol, 1.1eq), keep stirring at -78°C for 1h after the addition is complete, add triisopropyl borate (18.8g, 0.1mol, 1eq) after the addition is complete, naturally warm to room temperature and stir for 2h. Post-treatment, add saturated ammonium chloride aqueous solution to the reaction solution, separate the liquids, and concentrate the organic phase to dryness to obtain about 9.8g of product 1-b with a yield of 79.7%.

[0072] S1: Under nitrogen protection, 3-chlorobenzoyl chloride 1-c (62.5 g, 0.357 mol, 1 eq), deuterated phenylboronic acid 1-b (50 g, 0.3937 mol, 1.1 eq), 600 ml of toluene, cesium carbonate (582 g, 1.786 mol, 5 eq), and Pd(PPh3)4 (15 g, 0.013 mol, 3.64% eq) were added to the reaction flask. After the addition was completed, the reaction solution was heated and refluxed for 15 h. After post-treatment, the reaction solution was cooled and washed with water, separated and filtered through silica gel, concentrated to dryness, and column chromatography was performed to obtain about 24 g of intermediate 1-d, with a yield of about 30%.

[0073] S2: Under nitrogen protection, add 2-bromobiphenyl 1-e (27.2 g, 0.1167 mol, 1 eq) and 300 ml of ultra-dry tetrahydrofuran to the reaction flask, cool to -78 °C, add n-butyl lithium (55 ml, 0.1375 mol, 1.18 eq) dropwise, keep at -78 °C for 1 h after the addition is complete, dissolve the intermediate 1-d (24 g, 0.1108 mol, 0.95 eq) in 200 ml of tetrahydrofuran and add dropwise to the reaction flask. The mixture was stirred for 2 h at room temperature, and the reaction mixture was quenched with 1 M hydrochloric acid solution. The aqueous phase was extracted with ethyl acetate, and the organic phases were combined, dried over anhydrous sodium sulfate, and concentrated to dryness. 300 ml of dichloromethane was added, and methanesulfonic acid (67 g, 0.68 ml, 6 eq) was added dropwise at 0 ° C. After the addition was completed, the mixture was stirred for 2 h at room temperature. The reaction mixture was washed with water and separated. The organic phase was dried and concentrated, and column chromatography was performed to obtain about 29 g of the intermediate 1-f product with a yield of about 73%.

[0074] S3: Under nitrogen protection, the intermediate 1-f (29 g, 0.081 mol, 1.05 eq), amine compound 1-g (29 g, 0.077 mol, 1.1 q), 500 ml of toluene, sodium tert-butoxide (9 g, 0.093 mol, 1.2 eq), palladium acetate (0.2 g, 0.0009 mol, 1.2% eq), and X-phos (0.8 g, 0.00168 mol, 2.2% eq) were added to the reaction bottle. After the addition was completed, the reaction solution was heated and refluxed for 2 h. The raw material reaction was detected by HPLC.

[0075] After post-treatment, the reaction solution was cooled and washed with water, separated, the organic phase was concentrated to dryness after passing through silica gel, and recrystallized using a toluene / ethanol system. Finally, compound 3 (about 26 g, yield 43.5%) was obtained, HPLC purity 99.92%, ESI-MS (m / z) (M+): theoretical value 678.90, measured value 678.83, elemental analysis results (molecular formula C52H38DN): theoretical value C, 92.00; H, 5.94; N, 2.06; measured value C, 92.03; H, 5.92; N, 2.05.

[0076] The following product compounds were obtained in a similar manner:

[0077] Table 1

[0078]

[0079]

[0080]

[0081] Embodiment 11:

[0082]

[0083] The synthesis method of compound 17 is as follows:

[0084]

[0085] S1: Under nitrogen protection, 3-chlorobenzoyl chloride 11-a (62.5 g, 0.357 mol, 1 eq), deuterated phenylboronic acid 11-b (50 g, 0.3937 mol, 1.1 eq), 600 ml of toluene, cesium carbonate (582 g, 1.786 mol, 5 eq), and Pd(PPh3)4 (15 g, 0.013 mol, 3.64% eq) were added to the reaction flask. After the addition was completed, the reaction solution was heated and refluxed for 15 h. After post-treatment, the reaction solution was cooled and washed with water, separated and filtered through silica gel, concentrated to dryness, and column chromatography was performed to obtain about 24 g of intermediate 11-c with a yield of about 30%.

[0086] S2: Under nitrogen protection, 2-bromobiphenyl 11-d (27.2 g, 0.1167 mol, 1 eq) and 300 ml of ultra-dry tetrahydrofuran were added to the reaction flask, the temperature was lowered to -78 °C, n-butyl lithium (55 ml, 0.1375 mol, 1.18 eq) was added dropwise, and after the addition was completed, the temperature was maintained at -78 °C for 1 h. The intermediate 11-c (24 g, 0.1108 mol, 0.95 eq) was dissolved in 200 ml of tetrahydrofuran and then added dropwise to the reaction flask. The reaction mixture was naturally warmed to room temperature and stirred for 2 hours. The reaction solution was quenched with 1M hydrochloric acid solution, separated, the aqueous phase was extracted with ethyl acetate, the organic phases were combined, dried over anhydrous sodium sulfate, and concentrated to dryness. 300 ml of dichloromethane was added, and methanesulfonic acid (67 g, 0.68 ml, 6 eq) was added dropwise at 0°C. After the addition was complete, the reaction mixture was stirred for 2 hours at room temperature. The reaction solution was washed with water and separated. The organic phase was dried and concentrated, and column chromatography was performed to obtain about 29 g of the intermediate 11-f product with a yield of about 73%.

[0087] S3: Under nitrogen protection, the intermediate 11-f (29 g, 0.081 mol, 1.05 eq), amine compound 11-g (29 g, 0.077 mol, 1.1 q), 500 ml of toluene, sodium tert-butoxide (9 g, 0.093 mol, 1.2 eq), palladium acetate (0.2 g, 0.0009 mol, 1.2% eq), and X-phos (0.8 g, 0.00168 mol, 2.2% eq) were added to the reaction bottle. After the addition was completed, the reaction solution was heated and refluxed for 2 hours. The sample was taken and HPLC was used to detect whether the raw material reaction was complete.

[0088] After post-treatment, the reaction solution was cooled and washed with water, separated, the organic phase was concentrated to dryness after passing through silica gel, and recrystallized using a toluene / ethanol system. Finally, compound 17 (about 26 g, yield 48.4%) was obtained, HPLC purity 99.92%, ESI-MS (m / z) (M+): theoretical value 682.92, measured value 683.05, elemental analysis results (molecular formula C52H34D5N): theoretical value C, 91.46; H, 6.49; N, 2.05; measured value C, 91.54; H, 6.40; N, 2.06.

[0089] The following product compounds were obtained in a similar manner:

[0090] Table 2

[0091]

[0092]

[0093]

[0094]

[0095]

[0096]

[0097] The synthetic identification results of the compounds prepared in Tables 1 and 2 above are shown in Table 3 below:

[0098] Table 3

[0099]

[0100] Material property test:

[0101] The thermal weight loss temperature Td and the glass transition temperature Tg of compounds 3, 10, 12, 14, 17, 20, 26, 29, 30, 31, 38, 46, 50, 53, 57, 65, 66, 70, 71, 73, 80, 84, 86, 92, 93, 94, 95, 97, 98, 99, 100, 101, 102, 103, 104, 105, 107, 109, 110, and 111 of the present invention were tested, and the test results are shown in Table 4 below.

[0102] Note: The thermal weight loss temperature Td is the temperature at which the weight loss ratio is 5% in a nitrogen atmosphere, and is measured on a TGA N-1000 thermogravimetric analyzer with a nitrogen flow rate of 10 mL / min. The glass transition temperature Tg is measured by differential scanning calorimetry (DSC, Shinco DSC N-650) with a heating rate of 10°C / min.

[0103] Table 4:

[0104]

[0105]

[0106] It can be seen from the above data that the compounds synthesized in the present invention have excellent thermal stability, which means that the compounds conforming to the general structural formula of the present invention all have excellent thermal stability and can meet the requirements for the use of organic electroluminescent materials.

[0107] Device performance test:

[0108] Application Example 1:

[0109] ITO was used as the reflective layer anode substrate material, and its surface was treated with water, acetone, and N2 plasma in sequence;

[0110] On top of the ITO anode substrate, 10 nm of HT-1 doped with 2% by mass of NDP-9 was deposited to form a hole injection layer (HIL);

[0111] 100 nm of HT-1 was evaporated on the hole injection layer (HIL) to form the first hole transport layer (HTL);

[0112] Vacuum evaporation of the compound 3 designed by the present invention on the first hole transport layer (HTL) to form a second hole transport layer (GPL) with a thickness of 30 nm;

[0113] Compounds G1 and G2 were co-evaporated at a mass ratio of 5:5 as green light host materials, and GD-1 was evaporated as a doping material (the amount of GD-1 was 8% of the total mass of G1 and G2) on the second hole transport layer (GPL) to form a light-emitting layer with a thickness of 30 nm;

[0114] HB-1 was evaporated onto the light-emitting layer to obtain a hole blocking layer (HBL) with a thickness of 20 nm;

[0115] ET-1 and LiQ were co-evaporated onto the hole blocking layer (HBL) in a mass ratio of 5:5 to obtain an electron transport layer (ETL) with a thickness of 30 nm;

[0116] Magnesium (Mg) and silver (Ag) were mixed and evaporated on the electron transport layer (ETL) in a mass ratio of 9:1 to form an electron injection layer (EIL) with a thickness of 50 nm;

[0117] Thereafter, silver (Ag) is evaporated onto the electron injection layer to form a cathode with a thickness of 100 nm, and a DNTPD with a thickness of 50 nm is deposited on the cathode sealing layer. In addition, the cathode surface is sealed with a UV curable adhesive and a sealing film (seal cap) containing a dehumidifier to protect the organic electroluminescent device from being affected by oxygen or moisture in the atmosphere. Thus, an organic electroluminescent device is prepared.

[0118]

[0119] Application Example 2-40

[0120] Compounds 10, 12, 14, 17, 20, 26, 29, 30, 31, 38, 46, 50, 53, 57, 65, 66, 70, 71, 73, 80, 84, 86, 92, 93, 94, 95, 97, 98, 99, 100, 101, 102, 103, 104, 105, 107, 109, 110, and 111 in Examples 2-40 of the present invention are respectively used as the second hole transport material, and the other parts are consistent with those in Application Example 1, and the organic electroluminescent devices of Application Examples 2-40 are prepared accordingly.

[0121] Comparative Example 1-9:

[0122] The difference from Application Example 1 is that compounds 202, 226, 306, 337, 340 in CN202010376812.1 and compounds 2-72, 2-89, 2-111, 2-112 in WO2019151682A1 are used instead of compound 3 in this application as the second hole transport material, and the rest is the same as Application Example 1.

[0123] The characteristics of the organic electroluminescent device manufactured in the above application example and the organic electroluminescent device manufactured in the control example are that at a current density of 10 mA / cm 2 The results were shown in Table 5.

[0124] Table 5:

[0125]

[0126]

[0127]

[0128] As shown in Table 5 above, when the compounds of the present invention are applied to organic electroluminescent devices, at the same current density, the luminous efficiency is greatly improved, the starting voltage of the device is reduced, the power consumption of the device is relatively reduced, and the life of the device is correspondingly improved.

[0129] The organic electroluminescent devices prepared in the control examples 1-9 and the application examples 1-15 were respectively subjected to luminescence life tests to obtain the luminescence life T97% data (the time when the luminescence brightness decreases to 97% of the initial brightness). The test equipment was a TEO luminescent device life test system. The results are shown in Table 6:

[0130] Table 6:

[0131]

[0132] It can be seen from Table 6 above that when the compound of the present invention is applied to an organic electroluminescent device, the service life is greatly improved at the same current density, and the compound has broad application prospects.

Claims

1. An amino compound having a structure as shown in Formula 1, characterized in that: in, Ar1 is a substituted or unsubstituted group: a C6-C30 aromatic group or a C5-C30 heteroaromatic group, wherein the substituent is selected from one or more of deuterium, cyano, C1-C4 alkyl, C1-C4 deuterated alkyl, C6-C20 aryl, C6-C20 deuterated aryl, and C3-C20 heteroaromatic group; R1-R8 are independently selected from hydrogen, deuterium, or the following groups which may or may not be deuterated: one or more of a C1-C10 alkyl group, a C3-C10 cycloalkyl group, a C6-C30 aromatic group, or a C5-C30 heteroaryl group; A1-A5 are independently hydrogen, deuterium, C6-C20 aryl or deuterated C6-C20 aryl, and at least one of A1-A5 is deuterium; m, n, o, p or q is a positive integer from 0 to 4; r is a positive integer from 0 to 3.

2. The compound according to claim 1, characterized in that Its structural formula is shown in Formula 2-5 below:

3. The amino compound according to claim 1, characterized in that Ar1 is a substituted or unsubstituted group: phenyl, biphenyl, carbazolyl, N-phenylcarbazolyl, dibenzofuranyl, dibenzothiophenyl; the substituent is selected from one or more of deuterium, cyano, C1-C4 alkyl, C1-C4 deuterated alkyl, C6-C20 aryl, C6-C20 deuterated aryl, C3-C20 heteroaryl; A1-A5 are independently hydrogen, deuterium, phenyl or deuterated phenyl, and at least one of A1-A5 is deuterium; R1-R8 are independently hydrogen, deuterium, methyl, deuterated methyl, ethyl, deuterated ethyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, cyclopentyl, deuterated cyclopentyl, cyclohexyl, deuterated cyclohexyl, phenyl or deuterated phenyl.

4. The amino compound according to claim 3, characterized in that Ar1 is a substituted or unsubstituted group: phenyl, biphenyl, N-phenylcarbazolyl, dibenzofuranyl or dibenzothiophenyl; and its substituent is selected from one or more of deuterium, methyl, deuterated methyl, tert-butyl, phenyl and deuterated phenyl.

5. The amino compound according to claim 3, characterized in that R1 is hydrogen, deuterium, phenyl or deuterated phenyl, and R6 and R7 are each independently hydrogen or methyl.

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

7. An organic electroluminescent device, characterized in that: The invention comprises a first electrode, a second electrode and an organic layer formed between the first electrode and the second electrode, wherein the organic layer contains the compound according to any one of claims 1 to 6.

8. The organic electroluminescent device according to claim 7, characterized in that: The organic layer comprises a hole injection layer, a first hole transport layer, a second hole transport layer, a light-emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer; at least one of the hole injection layer, the first hole transport layer, the second hole transport layer, the light-emitting layer, the hole blocking layer, the electron transport layer, and the electron injection layer contains the compound described in any one of claims 1 to 6, especially the hole transport layer contains the compound described in any one of claims 1 to 6.

9. An electronic display device, characterized in that: Contains the organic electroluminescent device as claimed in claim 7.

10. An OLED lighting device, characterized in that: Contains the organic electroluminescent device as claimed in claim 7.

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