CN110903258A - Aromatic amine compound and application thereof - Google Patents

Aromatic amine compound and application thereof Download PDF

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CN110903258A
CN110903258A CN201811087033.9A CN201811087033A CN110903258A CN 110903258 A CN110903258 A CN 110903258A CN 201811087033 A CN201811087033 A CN 201811087033A CN 110903258 A CN110903258 A CN 110903258A
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aromatic amine
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李崇
谢丹丹
王芳
赵四杰
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Jiangsu Sunera Technology Co Ltd
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Abstract

The invention discloses an aromatic amine compound and application thereof, belonging to the technical field of semiconductors. The structure of the aromatic amine compound provided by the invention is shown as a general formula (1):
Figure DDA0001803402760000011
the invention also discloses application of the compound. The compound is an aromatic amine compound, has strong hole transmission capacity and high hole mobility, can be used as a hole transmission material, and can improve the efficiency of an organic electroluminescent device at high hole transmission rate; under a proper LUMO energy level, the organic electroluminescent device can play a role in blocking electrons, so that the recombination efficiency of excitons in a light-emitting layer is improved, the efficiency roll-off under high current density is reduced, the voltage of the device is reduced, the current efficiency of the device is improved, and the service life of the device is prolonged.

Description

Aromatic amine compound and application thereof
Technical Field
The invention relates to an aromatic amine compound and application thereof, belonging to the technical field of semiconductors.
Background
The photoelectric functional materials of the OLED can be divided into two categories, namely, charge injection transport materials and light-emitting materials, and further, the charge injection transport materials can be divided into electron injection transport materials, electron blocking materials, hole injection transport materials and hole blocking materials. In order to manufacture a high-performance OLED light-emitting device, various organic functional materials are required to have good photoelectric properties, for example, as a charge transport material, it is required to have good carrier mobility, high glass transition temperature, and the like.
The OLED photoelectric functional material film layer for forming the OLED device at least comprises more than two layers of structures, the OLED device structure applied in industry comprises a hole injection layer, a hole transmission layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transmission layer, an electron injection layer and other various film layers, namely the photoelectric functional material applied to the OLED device at least comprises a hole injection material, a hole transmission material, a light emitting material, an electron transmission material and the like, and the material type and the matching form have the characteristics of richness and diversity. In addition, for the collocation of OLED devices with different structures, the used photoelectric functional material has stronger selectivity, and the performance of the same material in the devices with different structures can be completely different.
Therefore, aiming at the industrial application requirements of the current OLED device and the requirements of different functional film layers and photoelectric characteristics of the OLED device, a more suitable OLED functional material or material combination with higher performance needs to be selected to realize the comprehensive characteristics of high efficiency, long service life and low voltage of the device.
Disclosure of Invention
An object of the present invention is to provide an aromatic amine compound. The compound takes triarylamine as a core, has higher hole mobility and proper HOMO and LUMO energy levels, and can effectively improve the photoelectric property and the service life of an OLED device through device structure optimization.
The technical scheme for solving the technical problems is as follows: an aromatic amine compound having a structure represented by general formula (1):
Figure BDA0001803402740000021
in the general formula (1), L1Is represented by one of the structures shown in a general formula (2), a general formula (3), a general formula (4), a general formula (5), a general formula (6), a general formula (7), a general formula (8), a general formula (9), a general formula (10) or a general formula (11);
Figure BDA0001803402740000022
said X1And X3Each independently represents N or C-R8Said X is2Represented by-O-, -S-or-CH2In the general formula (2), the general formula (3), the general formula (4), the general formula (5), the general formula (6), the general formula (7), the general formula (8), the general formula (9), the general formula (10) or the general formula (11), a dotted line represents a nitrogen atom, and L1Or L2The attachment site of (a);
said L2Represents one of structures shown by a single bond, substituted or unsubstituted phenylene, substituted or substituted biphenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted naphthyridine, substituted or unsubstituted pyridylene, a general formula (2), a general formula (3), a general formula (4), a general formula (5), a general formula (6), a general formula (7), a general formula (8), a general formula (9), a general formula (10) or a general formula (11);
ar is1、Ar2、Ar3、Ar4Each independently represents one of a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted terphenylene, a substituted or unsubstituted naphthyridine and a substituted or unsubstituted pyridylene;
the R is1、R2、R3、R4Each independently represents one of substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted pyrenyl, substituted or unsubstituted anthryl, and a structure shown in a general formula (18) or a general formula (19);
Figure BDA0001803402740000031
in the general formula (18) and the general formula (19), Z represents N or C-R9；
Ar1、Ar2、Ar3、Ar4Z at the site of attachment to the general formula (18) represents a carbon atom;
said X3、X4、X5Independently represent-O-, -S-, -C(R10)(R11) -or-N (R)12) -one of the above; said X3、X5May also be each a single bond;
the R is5、R6、R7Are each independently represented by C1-C20Alkyl, substituted or unsubstituted C6-C40One of a substituted or unsubstituted 5-to 40-membered heteroaryl group containing one or more heteroatoms;
the R is8、R9Each independently represents a hydrogen atom, a halogen, a cyano group, or C1-C20Alkyl of (C)2-C20Alkenyl of (a), substituted or unsubstituted C6-C40One of a substituted or unsubstituted 5-to 40-membered heteroaryl group containing one or more heteroatoms; two or more adjacent R9Can be bonded to each other to form a ring;
the R is10To R12Are each independently represented by C1-C20Alkyl, substituted or unsubstituted C6-C40One of a substituted or unsubstituted 5-to 40-membered heteroaryl group containing one or more heteroatoms; r10And R11May be bonded to each other to form a ring;
the substituent for substituting each of the above-mentioned substitutable groups is optionally selected from halogen, cyano, C1-C10Alkyl radical, C6-C40One or more of aryl, 5-to 40-membered heteroaryl containing one or more heteroatoms;
the heteroatom in the heteroaryl group is optionally selected from one or more of N, O or S.
As a further improvement of the present invention, in the general formula (1), L1Is represented by one of the structures shown in a general formula (2), a general formula (3), a general formula (4), a general formula (5), a general formula (6), a general formula (7), a general formula (8), a general formula (9), a general formula (10), a general formula (11), a general formula (12), a general formula (13), a general formula (14), a general formula (15), a general formula (16) or a general formula (17);
Figure BDA0001803402740000032
Figure BDA0001803402740000041
as a further improvement of the present invention, the general formula (1) is represented by one of the structures represented by general formula (1-1) -general formula (1-18):
Figure BDA0001803402740000042
Figure BDA0001803402740000051
the ring A is represented by
Figure BDA0001803402740000052
Any one of the above, wherein the ring a is connected through adjacent sites marked with asterisks to a phenylene fused ring in the general formula (1-15) or the general formula (1-16), and the ring a and two carbons marked with asterisks after the phenylene fused ring in the general formula (1-15) or the general formula (1-16) become common ring-forming carbons;
wherein the symbols and indices used have the meanings given in claim 1.
As a further improvement of the invention, R is1、R2、R3、R4Each independently represented by one of the following structures:
Figure BDA0001803402740000061
as a further improvement of the invention, L is2Represented as one of the following structures:
Figure BDA0001803402740000062
as a further improvement of the invention, R is5、R6、R7Each independently represents a methyl group, an ethyl group, a,Propyl, isopropyl, tert-butyl, pentyl, phenyl, biphenyl, naphthyl, naphthyridinyl, benzopyrolyl, pyridyl or furanyl;
the R is8、R9Each independently represents a hydrogen atom, a fluorine atom, a cyano group, a methyl group, an ethyl group, a propyl group, an isopropyl group, a tert-butyl group, a pentyl group, a phenyl group, a biphenyl group, a naphthyl group, a naphthyridinyl group, a pyridyl group or a furyl group;
the R is10To R12Each independently represents methyl, ethyl, propyl, isopropyl, tert-butyl, pentyl, phenyl, biphenyl, naphthyl, naphthyridinyl or pyridyl;
the substituent for substituting each of the above substitutable groups is optionally selected from halogen, cyanomethyl, ethyl, propyl, isopropyl, tert-butyl, pentyl, phenyl, biphenyl, naphthyl, naphthyridinyl, pyridyl or furyl.
As a further improvement of the present invention, the aromatic amine compound has a specific structural formula:
Figure BDA0001803402740000063
Figure BDA0001803402740000071
Figure BDA0001803402740000081
Figure BDA0001803402740000091
Figure BDA0001803402740000101
Figure BDA0001803402740000111
Figure BDA0001803402740000121
Figure BDA0001803402740000131
Figure BDA0001803402740000141
Figure BDA0001803402740000151
Figure BDA0001803402740000161
Figure BDA0001803402740000171
Figure BDA0001803402740000181
Figure BDA0001803402740000191
Figure BDA0001803402740000201
Figure BDA0001803402740000202
any one of them.
The second object of the present invention is to provide the use of the aromatic amine compound in the preparation of organic electroluminescent devices. When the compound is applied to an OLED device, the structure of the device is optimized, so that high film stability can be kept, the photoelectric property of the OLED device can be effectively improved, and the service life of the OLED device can be effectively prolonged.
The technical scheme for solving the technical problems is as follows: use of the above aromatic amine compound for the preparation of an organic electroluminescent device.
It is a further object of the present invention to provide an organic electroluminescent device. The compound has good application effect in OLED luminescent devices and good industrialization prospect.
The technical scheme for solving the technical problems is as follows: an organic electroluminescent device having a plurality of organic thin film layers between an anode and a cathode, at least one of the organic thin film layers containing the aromatic amine compound.
On the basis of the technical scheme, the invention can be further improved as follows.
Further, the organic thin film layer includes a hole transport layer, and the material of the hole transport layer is the aromatic amine compound.
Further, the organic thin film layer comprises an electron blocking layer, and the electron blocking layer is made of the aromatic amine compound.
The fourth object of the present invention is to provide a display device. The organic electroluminescent device can be applied to display elements, so that the current efficiency, the power efficiency and the external quantum efficiency of the device are greatly improved; meanwhile, the service life of the device is obviously prolonged, and the OLED luminescent device has a good application effect and a good industrialization prospect.
The technical scheme for solving the technical problems is as follows: a display element comprising the above organic electroluminescent device.
The invention has the beneficial effects that:
1. the compound is an aromatic amine compound, has strong hole transmission capacity and high hole mobility, can be used as a hole transmission material, and can improve the efficiency of an organic electroluminescent device at high hole transmission rate; under a proper LUMO energy level, the organic electroluminescent device can play a role in blocking electrons, so that the recombination efficiency of excitons in a light-emitting layer is improved, the efficiency roll-off under high current density is reduced, the voltage of the device is reduced, the current efficiency of the device is improved, and the service life of the device is prolonged.
2. The compound of the invention contains a benzidine structure, the connected branched chains are radial, and after the material is formed into a film, the branched chains can be mutually crossed to form a film layer with high compactness, thereby prolonging the service life of devices.
3. The compound provided by the invention has higher glass transition temperature and proper decomposition temperature, and the evaporation temperature can be regulated and controlled by carrying out different collocation on the connecting branched chains, so that the compound has a wider industrial processing window.
4. When the compound is applied to an OLED device, high film stability can be kept through device structure optimization, and the service life of the OLED device can be effectively prolonged. The compound has good application effect and industrialization prospect in OLED luminescent devices.
Drawings
Fig. 1 is a schematic structural diagram of the application of the materials enumerated in the present invention to an OLED device, wherein the components represented by the respective reference numerals are as follows:
the organic electroluminescent device comprises a substrate layer 1, a substrate layer 2, an ITO anode layer 3, a hole injection layer 4, a hole transport layer 5, an electron blocking layer 6, a light emitting layer 7, a hole blocking/electron transport layer 8, an electron injection layer 9 and a cathode reflection electrode layer;
FIG. 2 is a graph showing the current efficiency variation trend of the devices obtained in examples 1, 14 and 28 of the device of the present invention and the device obtained in comparative example 1 at a temperature range of-10 to 80 ℃.
Detailed Description
The principles and features of this invention are described below in conjunction with the following drawings, which are set forth by way of illustration only and are not intended to limit the scope of the invention.
Example 1: preparation of Compound 69
Figure BDA0001803402740000221
A250 mL three-necked flask was prepared, and 0.01mol of the raw material A-1, 0.012mol of the raw material B-1, 0.03mol of sodium tert-butoxide, and 1X 10 mol thereof were added under a nitrogen atmosphere-4molPd2(dba)3，1×10-4Heating and refluxing tri-tert-butylphosphine and 150mL of toluene for 12 hours, sampling a sample, completely reacting, naturally cooling, filtering, rotatably evaporating filtrate, and passing through a silica gel column to obtain an intermediate C-1; HPLC purity 98.64%, yield 77.8%; elemental analysis Structure (molecular formula C)22H17N2OBr): theoretical value C, 65.20; h, 4.23; n, 6.91; o, 3.95; br, 19.72; test values are: c, 65.10; h, 4.25; n, 6.90; o, 3.93; br, 19.73.
ESI-MS (M/z) (M +): theoretical value is 404.05, found 404.03.
Figure BDA0001803402740000222
A250 mL three-necked flask was prepared, and 0.01mol of intermediate C-1, 0.012mol of raw material D-2, 0.03mol of sodium tert-butoxide, 1X 10 mol were added under a nitrogen atmosphere-4molPd2(dba)3，1×10-4Heating and refluxing tri-tert-butylphosphine and 150mL of toluene for 12 hours, sampling a sample, completely reacting, naturally cooling, filtering, rotatably evaporating filtrate, and passing through a silica gel column to obtain an intermediate E-1; HPLC purity 98.67%, yield 78.8%; elemental analysis Structure (molecular formula C)34H25N2OBr): theoretical value C, 73.25; h, 4.52; n, 5.03; o, 2.87; br, 14.33; test value C, 73.22; h, 4.51; n, 5.02; o, 2.86; br, 14.33.
ESI-MS (M/z) (M +): theoretical value is 556.12, found 556.10.
Figure BDA0001803402740000231
A250 mL three-necked flask was prepared, and 0.01mol of the starting material F-1, 0.012mol of the intermediate E-1, 0.03mol of sodium tert-butoxide, and 1X 10 mol were added under a nitrogen atmosphere-4molPd2(dba)3，1×10-4Heating and refluxing tri-tert-butylphosphine and 150mL of toluene for 12 hours, sampling a sample, completely reacting, naturally cooling, filtering, rotatably evaporating filtrate, and passing through a silica gel column by using petroleum ether as an eluent to obtain a compound 69; the HPLC purity is 99.66 percent,the yield is 76.8%; elemental analysis Structure (molecular formula C)58H43N3O): theoretical value C, 87.30; h, 5.43; n, 5.27; o, 2.00; test values are: c, 87.31; h, 5.41; n, 5.25; and O, 2.01. ESI-MS (M/z) (M +): theoretical value is 797.34, found 797.31.
The starting materials and intermediates involved in compounds 137, 101, 185, 204, 217, 235, 251, 265, 281, 297, 305, 315 are shown in table 1, and the preparation of the starting materials and intermediates involved is referred to the above methods.
TABLE 1
Figure BDA0001803402740000232
Figure BDA0001803402740000241
For ease of presentation and understanding, the same species above appears in different reactions using different reference numbers.
Example 2: preparation of Compound 137
Figure BDA0001803402740000251
The preparation was carried out according to the synthesis method of compound 69, except that starting material F-1 was replaced with starting material F-2 and intermediate E-1 was replaced with intermediate E-2, and the purity of the obtained objective product was 98.3% and the yield was 76.5%. Elemental analysis Structure (molecular formula C)58H43N3O): theoretical value: c, 87.30; h, 5.43; n, 5.27; o,2.00 test value: c, 87.29; h, 5.42; n, 5.25; o, 2.01; ESI-MS (M/z) (M +): theoretical value is 797.34, found 797.31.
Example 3: preparation of Compound 102
Figure BDA0001803402740000252
Prepared according to the synthetic method of the compound 69, except that the raw material F-3 is used for replacing the raw material F-1, and the intermediate E-3 is used for replacing the intermediateThe purity of the obtained target product was 99.1% and the yield was 84.3% for the form E-1. Elemental analysis Structure (molecular formula C)49H39N3O): theoretical value: c, 85.81; h, 5.73; n, 6.13; o, 2.33; test values are: c, 85.82; h, 5.71; n, 6.12; o, 2.31; ESI-MS (M/z) (M +): theoretical value is 685.31, found 685.30.
Example 4: preparation of Compound 185
Figure BDA0001803402740000253
Prepared according to the synthetic method of compound 69, except that intermediate E-4 was used instead of intermediate E-1, the purity of the obtained objective product was 99.4%, and the yield was 81.5%. Elemental analysis Structure (molecular formula C)60H40N2S2): theoretical value: c, 84.47; h, 4.73; n, 3.28; s, 7.52; test values are: c, 84.45; h, 4.72; n, 3.27; s, 7.51; ESI-MS (M/z) (M +): theoretical value is 852.26, found 852.25.
Example 5: preparation of Compound 204
Figure BDA0001803402740000261
Prepared according to the synthetic method of compound 69, except that intermediate E-5 was used instead of intermediate E-1, the purity of the obtained target product was 98.9%, and the yield was 83.4%. Elemental analysis Structure (molecular formula C)64H42N2O2): theoretical value: c, 88.25; h, 4.86; n, 3.22; o, 3.67; test values are: c, 88.23; h, 4.85; n, 3.21; o, 3.66; ESI-MS (M/z) (M +): theoretical value is 870.32, found 870.30.
Example 6: preparation of Compound 217
Figure BDA0001803402740000262
Prepared according to the synthetic method of the compound 69, except that the raw material F-4 is used for replacing the raw material F-1, the intermediate E-6 is used for replacing the intermediate E-1, and the pure target product is obtainedThe degree was 99.1%, and the yield was 85.3%. Elemental analysis Structure (molecular formula C)66H48N2O): theoretical value: c, 89.56; h, 5.47; n, 3.16; o, 1.81; test values are: c, 89.54; h, 5.45; n, 3.15; o, 1.82; ESI-MS (M/z) (M +): theoretical value is 884.38, found 884.35.
Example 7: preparation of Compound 235
Figure BDA0001803402740000271
Prepared according to the synthetic method of compound 69, except that intermediate E-7 was used instead of intermediate E-1, the purity of the obtained target product was 98.5%, and the yield was 81.5%. Elemental analysis Structure (molecular formula C)62H43N3O2): theoretical value: c, 86.39; h, 5.03; n, 4.87; o, 3.71; test values are: c, 86.37; h, 5.01; n, 4.86; o, 3.72; ESI-MS (M/z) (M +): theoretical value is 861.34, found 861.30.
Example 8: preparation of Compound 251
Figure BDA0001803402740000272
The preparation was carried out according to the synthesis method of compound 69, except that starting material F-5 was used instead of starting material F-1 and intermediate E-8 was used instead of intermediate E-1, and that the purity of the obtained objective product was 99.7% and the yield was 73.9%. Elemental analysis Structure (molecular formula C)54H39N3O2): theoretical value: c, 85.13; h, 5.16; n, 5.52; o, 4.20; test values are: c, 85.11; h, 5.15; n, 5.50; o, 4.23; ESI-MS (M/z) (M +): theoretical value is 761.30, found 761.33.
Example 9: preparation of Compound 265
Figure BDA0001803402740000273
Is prepared according to the synthesis method of the compound 69, except that the intermediate E-9 is used for replacing the intermediate E-1, the purity of the obtained target product is 99.2 percent, and the yield is 82.5 percent. Elemental analysis Structure (molecular formula C)55H39N3O): theoretical value: c, 87.16; h, 5.19; n, 5.54; o, 2.11; test values are: c, 87.15; h, 5.18; n, 5.52; o, 2.13; ESI-MS (M/z) (M +): theoretical value is 757.31, found 757.33.
Example 10: preparation of Compound 281
Figure BDA0001803402740000281
The preparation was carried out according to the synthesis method of compound 69, except that starting material F-6 was used instead of starting material F-1 and intermediate E-10 was used instead of intermediate E-1, and that the purity of the obtained objective product was 99.4% and the yield was 80.6%. Elemental analysis Structure (molecular formula C)59H42N4): theoretical value: c, 87.81; h, 5.25; n, 6.94; test values are: c, 87.82; h, 5.23; n, 6.95; ESI-MS (M/z) (M +): theoretical value is 806.34, found 806.36.
Example 11: preparation of Compound 69
Figure BDA0001803402740000282
The preparation was carried out according to the synthesis method of compound 69, except that starting material F-6 was used instead of starting material F-1 and intermediate E-11 was used instead of intermediate E-1, and that the purity of the obtained objective product was 99.5% and the yield was 80.1%.
Elemental analysis Structure (molecular formula C)60H42N2O): theoretical value: c, 89.30; h, 5.25; n, 3.47; o, 1.98; test values are: c, 89.31; h, 5.23; n, 3.45; o, 1.97; ESI-MS (M/z) (M +): theoretical value is 806.33, found 806.30.
Example 12: preparation of Compound 305
Figure BDA0001803402740000291
Prepared according to the synthetic method of the compound 69, except that the raw material F-6 is used for replacing the raw material F-1, the intermediate E-12 is used for replacing the intermediate E-1, and the purity of the obtained target product is99.2%, yield 82.7%. Elemental analysis Structure (molecular formula C)60H42N2S): theoretical value: c, 87.56; h, 5.14; n, 3.40; s, 3.90; test values are: c, 87.55; h, 5.13; n, 3.42; s, 3.91; ESI-MS (M/z) (M +): theoretical value is 822.31, found 822.33.
Example 13: preparation of Compound 315
Figure BDA0001803402740000292
Prepared according to the synthetic method of compound 69, except that intermediate E-13 was used instead of intermediate E-1, the purity of the obtained target product was 98.8%, and the yield was 86.3%. Elemental analysis Structure (molecular formula C)55H39N3S): theoretical value: c, 85.35; h, 5.08; n, 5.43; s, 4.14; test values are: c, 85.33; h, 5.06; n, 5.42; s, 4.15; ESI-MS (M/z) (M +): theoretical value is 773.29, found 773.27.
Example 14: preparation of Compound 1
Figure BDA0001803402740000293
Dissolving 26.3mmol of reactant 1 in 45mL of DMF, adding 26.3mmol of N-bromosuccinimide, reacting for 5h, pouring the mixed solution after the reaction into 150mL of ice water, filtering, washing the obtained solid with distilled water, dissolving the washed solid in dichloromethane, drying with anhydrous magnesium sulfate, filtering, performing rotary evaporation, passing through a silica gel column, using a mixed solvent of diethyl ether and dichloromethane 1:4 as an eluent, and obtaining the intermediate product 1 with the purity of 99.6% and the yield of 87.3%.
Elemental analysis Structure (molecular formula C)7H5N2BrO): theoretical value: c, 39.47; h, 2.37; n, 13.15; o, 7.51; br, 37.51; test values are: c, 39.45; h, 2.35; n, 13.13; o, 7.52; br, 37.52;
ESI-MS (M/z) (M +): theoretical value is 211.96, found 211.95.
Figure BDA0001803402740000301
A250 mL three-necked flask was prepared, and 0.01mol of raw material G, 0.012mol of raw material H, 0.03mol of sodium tert-butoxide, and 1X 10 in a nitrogen atmosphere were added-4mol Pd2(dba)3，1×10-4Heating and refluxing tri-tert-butylphosphine and 150mL of toluene for 12 hours, sampling a sample, completely reacting, naturally cooling, filtering, rotatably evaporating filtrate, and passing through a silica gel column to obtain an intermediate I; HPLC purity 99.7%, yield 81.9%; elemental analysis Structure (molecular formula C)19H13N2OBr): theoretical value: c, 62.48; h, 3.59; n, 7.67; o, 4.38; br, 21.88; test values are: c, 62.46; h, 3.58; n, 7.66; o, 4.39; br, 21.89; ESI-MS (M/z) (M +): theoretical value is 364.02, found 364.03.
Figure BDA0001803402740000302
A250 mL three-necked flask was prepared, and 0.01mol of intermediate I, 0.012mol of raw material J, 0.03mol of sodium tert-butoxide, and 1X 10 in a nitrogen atmosphere were added-4molPd2(dba)3，1×10-4Heating and refluxing tri-tert-butylphosphine and 150mL of toluene for 12 hours, sampling a sample, completely reacting, naturally cooling, filtering, rotatably evaporating filtrate, and passing through a silica gel column to obtain an intermediate K; HPLC purity 97.9%, yield 82.4%; elemental analysis Structure (molecular formula C)31H21N2OBr): theoretical value: c, 71.96; h, 4.09; n, 5.41; o, 3.09; br, 15.44; test values are: c, 71.95; h, 4.08; n, 5.42; o, 3.08; br, 15.45; ESI-MS (M/z) (M +): theoretical value is 516.08, found 516.06.
Figure BDA0001803402740000311
A250 mL three-necked flask was prepared, and 0.01mol of the raw material L, 0.012mol of the raw material M, 0.03mol of sodium tert-butoxide, and 1X 10 in a nitrogen atmosphere were added-4molPd2(dba)3，1×10-4mol tri-tert-butylphosphine, 150mL toluene, heating reflux for 12 hours, sampling the sample, and finishing the reactionNaturally cooling, filtering, rotatably steaming the filtrate, and passing through a silica gel column to obtain an intermediate N; HPLC purity 99.4%, yield 87.3%; elemental analysis Structure (molecular formula C)12H10NBr): theoretical value: c, 58.09; h, 4.06; n, 5.65; br, 32.2; test values are: c, 58.07; h, 4.05; n, 5.65; br, 32.3; ESI-MS (M/z) (M +): theoretical value is 247.00, found 247.03.
Figure BDA0001803402740000312
A250 mL three-necked flask was prepared, and 0.01mol of intermediate N, 0.012mol of starting material O, 0.03mol of sodium tert-butoxide, and 1X 10 in a nitrogen atmosphere were added-4molPd2(dba)3，1×10-4Heating and refluxing tri-tert-butylphosphine and 150mL of toluene for 12 hours, sampling a sample, completely reacting, naturally cooling, filtering, rotatably evaporating filtrate, and passing through a silica gel column to obtain an intermediate S; HPLC purity 99.5%, yield 85.4%; elemental analysis Structure (molecular formula C)27H22NBr): theoretical value: c, 73.64; h, 5.04; n, 3.18; br, 18.14; test values are: c, 73.65; h, 5.03; n, 3.17; br, 18.15; ESI-MS (M/z) (M +): theoretical value is 439.09, found 439.07.
Figure BDA0001803402740000313
Weighing 0.01mol of intermediate S under the nitrogen atmosphere, dissolving the intermediate S in 45mL of tetrahydrofuran, cooling to-78 ℃, slowly dripping a cyclohexane solution containing 0.02mol of n-butyllithium, and keeping the temperature and stirring for 30 minutes after dripping is finished; slowly dripping tetrahydrofuran solution containing 0.035mol trimethyl borate, after dripping, slowly heating to room temperature, and reacting for 10 hours under the condition of heat preservation; after the reaction is finished, cooling to 0 ℃, slowly dripping distilled water, stirring for 1 hour after no gas is generated, and then heating to room temperature; the reaction mixture was extracted with 150mL of ethyl acetate, the extract was washed with 150mL of saturated brine three times, finally dried over anhydrous magnesium sulfate, the solution was distilled under reduced pressure, and the obtained solid was purified by distillation with 400mL of toluene: recrystallizing the mixed solution of 3:1 ethanol to obtain an intermediate P; pureThe degree was 94.7%, and the yield was 76.8%. Elemental analysis Structure (molecular formula C)27H24BNO2): theoretical value: c, 80.01; h, 5.97; b, 2.67; n, 3.46; o, 7.89; test values are: c, 80.02; h, 5.96; b, 2.66; n, 3.45; o, 7.89; ESI-MS (M/z) (M +): theoretical value is 405.19, found 405.16.
Figure BDA0001803402740000321
To a 200mL three-necked flask, 0.01mol of intermediate K, 0.011mol of intermediate P, 0.03mol of potassium carbonate, and 1X 10 mol of potassium carbonate were placed under a nitrogen atmosphere-4mol Pd(PPh3)Cl2And 1X 10-4mol of triphenylphosphine, then 120mL of toluene: ethanol: the mixture of water and water in a ratio of 1:1:1 was heated under reflux for 24 hours, and the reaction was observed by TLC until the reaction was complete. Naturally cooling to room temperature, filtering, and rotatably evaporating the filtrate until no fraction is obtained. The resulting material was purified by silica gel column (dichloromethane: mixed solvent of petroleum ether ═ 1:5 as eluent) to obtain the target product compound 1 with purity of 99.4% and yield of 76.7%.
Elemental analysis Structure (molecular formula C)58H43N3O): theoretical value: c, 87.30; h, 5.43; n, 5.27; o, 2.00; test values are: c, 87.32; h, 5.41; n, 5.25; o, 2.00; ESI-MS (M/z) (M +): theoretical value is 797.34, found 797.35.
The starting materials for compounds 65, 9, 14, 30, 22, 53, 215, 193, 232, 248, 259, 275, 298, 303, 319, 81, 122 are shown in table 2, and reference is made to the above methods for the preparation of the starting materials and intermediates involved.
TABLE 2
Figure BDA0001803402740000322
Figure BDA0001803402740000331
Figure BDA0001803402740000341
For convenience of presentation and understanding, the same materials above appear in different reactions using different reference numbers;
example 15: preparation of Compound 65
Figure BDA0001803402740000342
The compound was prepared according to the synthesis method of compound 1 except that intermediate K-2 was used instead of intermediate K-1 and intermediate P-2 was used instead of intermediate P-1, and the purity of the obtained objective product was 98.1% and the yield was 79.5%. Elemental analysis Structure (molecular formula C)61H43N3O): theoretical value: c, 87.85; h, 5.20; n, 5.04; o, 1.92; test values are: c, 87.83; h, 5.21; n, 5.03; o, 1.93; ESI-MS (M/z) (M +): theoretical value is 833.34, found 833.35.
Example 16: preparation of Compound 9
Figure BDA0001803402740000351
Prepared according to the synthetic method of the compound 1, except that the intermediate P-3 is used to replace the intermediate P-1, the purity of the obtained target product is 98.6%, and the yield is 74.5%. Elemental analysis Structure (molecular formula C)57H39N3O): theoretical value: c, 87.55; h, 5.03; n, 5.37; o, 2.05; test values are: c, 87.53; h, 5.02; n, 5.35; o, 2.03; ESI-MS (M/z) (M +): theoretical value is 781.31, found 781.30.
Example 17: preparation of Compound 14
Figure BDA0001803402740000352
The compound was prepared according to the synthesis method of compound 1 except that intermediate K-3 was used instead of intermediate K-1 and intermediate P-4 was used instead of intermediate P-1, and the purity of the obtained objective product was 99.2% and the yield was 83.5%. Elemental analysis Structure (molecular formula C)51H35N3O2): theoretical value: c, 84.86; h, 4.89; n, 5.82; o, 4.43; test values are: c, 84.85; h, 4.88; n, 5.83; o, 4.42; ESI-MS (M/z) (M +): theoretical value is 721.27, found 721.25.
Example 18: preparation of Compound 69
Figure BDA0001803402740000353
The compound was prepared according to the synthesis method of compound 1 except that intermediate K-4 was used instead of intermediate K-1 and intermediate P-5 was used instead of intermediate P-1, and the purity of the obtained objective product was 99.5% and the yield was 82.3%. Elemental analysis Structure (molecular formula C)55H38N4O): theoretical value: c, 85.69; h, 4.97; n, 7.27; o, 2.08; test values are: c, 85.67; h, 4.95; n, 7.25; o, 2.07; ESI-MS (M/z) (M +): theoretical value is 770.30, found 770.28.
Example 19: preparation of Compound 22
Figure BDA0001803402740000361
The compound was prepared according to the synthetic method of compound 1 except that intermediate K-5 was used instead of intermediate K-1 and intermediate P-6 was used instead of intermediate P-1, and the purity of the obtained objective product was 99.4% and the yield was 78.3%. Elemental analysis Structure (molecular formula C)69H45N3O): theoretical value: c, 88.91; h, 4.87; n, 4.51; o, 1.72; test values are: c, 88.90; h, 4.85; n, 4.52; o, 1.73; ESI-MS (M/z) (M +): theoretical value is 931.36, found 931.35.
Example 20: preparation of Compound 53
Figure BDA0001803402740000362
Prepared according to the synthetic method of the compound 1, except that the intermediate K-6 is used to replace the intermediate K-1, and the intermediate P-7 is used to replace the intermediate P-1, the purity of the target product is 98.6%, and the yield is 74.5%. Elemental analysis Structure (molecular formula C)51H33N3O3): theoretical value: c, 83.25; h, 4.52; n, 5.71; o, 6.52; test values are: c, 83.25; h, 4.50; n, 5.73; o, 6.53; ESI-MS (M/z) (M +): theoretical value is 735.25, found 735.28.
Example 21: preparation of Compound 215
Figure BDA0001803402740000371
The compound was prepared according to the synthetic method of compound 1 except that intermediate K-7 was used instead of intermediate K-1 and intermediate P-8 was used instead of intermediate P-1, and the purity of the obtained objective product was 99.0% and the yield was 83.5%. Elemental analysis Structure (molecular formula C)57H37N3O2): theoretical value: c, 86.01; h, 4.69; n, 5.28; o, 4.02; test values are: c, 86.02; h, 4.67; n, 5.25; o, 4.03; ESI-MS (M/z) (M +): theoretical value is 795.29, found 795.30.
Example 22: preparation of Compound 193
Figure BDA0001803402740000372
Prepared according to the synthetic method of the compound 1, except that the intermediate K-8 is used for replacing the intermediate K-1, and the intermediate P-9 is used for replacing the intermediate P-1, the purity of the obtained target product is 98.6%, and the yield is 74.5%. Elemental analysis Structure (molecular formula C)54H36N2S2): theoretical value: c, 83.47; h, 4.67; n, 3.61; s, 8.25; test values are: c, 83.45; h, 4.65; n, 3.62; s, 8.23; ESI-MS (M/z) (M +): theoretical value is 776.23, found 776.21.
Example 23: preparation of Compound 232
Figure BDA0001803402740000373
Prepared according to the synthesis method of the compound 1, except that an intermediate K-9 is used for replacing the intermediate K-1, an intermediate P-10 is used for replacing the intermediate P-1, the purity of the obtained target product is 99.1 percent,the yield thereof was found to be 84.2%. Elemental analysis Structure (molecular formula C)66H48N2O): theoretical value: c, 89.56; h, 5.47; n, 3.16; o, 1.81; test values are: c, 89.55; h, 5.45; n, 3.17; o, 1.82; ESI-MS (M/z) (M +): theoretical value is 884.38, found 884.36.
Example 24: preparation of Compound 248
Figure BDA0001803402740000381
The compound was prepared according to the synthetic method of compound 1 except that intermediate K-10 was used instead of intermediate K-1 and intermediate P-11 was used instead of intermediate P-1, and the purity of the obtained objective product was 99.3% and the yield was 82.5%. Elemental analysis Structure (molecular formula C)74H51N3O): theoretical value: c, 89.04; h, 5.15; n, 4.21; o, 1.60; test values are: c, 89.03; h, 5.15; n, 4.22; o, 1.63; ESI-MS (M/z) (M +): theoretical value is 997.40, found 997.43.
Example 25: preparation of Compound 259
Figure BDA0001803402740000382
The compound was prepared according to the synthetic method of compound 1 except that intermediate K-11 was used instead of intermediate K-1 and intermediate P-12 was used instead of intermediate P-1, and the purity of the obtained objective product was 98.7% and the yield was 82.2%. Elemental analysis Structure (molecular formula C)65H46N2O2): theoretical value: c, 88.01; h, 5.23; n, 3.16; o, 3.61; test values are: c, 88.00; h, 5.22; n, 3.15; o, 3.63; ESI-MS (M/z) (M +): theoretical value is 886.36, found 886.35.
Example 26: preparation of Compound 275
Figure BDA0001803402740000383
Prepared according to the synthetic method of the compound 1, except that the intermediate K-12 is used for replacing the intermediate K-1, the intermediate P-13 is used for replacing the intermediate P-1,the purity of the obtained target product was 98.9%, and the yield was 78.3%. Elemental analysis Structure (molecular formula C)48H34N4O): theoretical value: c, 84.43; h, 5.02; n, 8.21; o, 2.34; test values are: c, 84.41; h, 5.00; n, 8.25; o, 2.38; ESI-MS (M/z) (M +): theoretical value is 682.27, found 682.25.
Example 27: preparation of Compound 289
Figure BDA0001803402740000391
Prepared according to the synthetic method of the compound 1, except that the intermediate K-13 is used to replace the intermediate K-1, and the intermediate P-14 is used to replace the intermediate P-1, the purity of the obtained target product is 99.3%, and the yield is 79.5%. Elemental analysis Structure (molecular formula C)64H45N5): theoretical value: c, 86.95; h, 5.13; n, 7.92; test values are: c, 86.96; h, 5.15; n, 7.93; ESI-MS (M/z) (M +): theoretical value is 883.37, found 883.35.
Example 28: preparation of Compound 303
Figure BDA0001803402740000392
Prepared according to the synthetic method of the compound 1, except that the intermediate K-14 is used to replace the intermediate K-1, and the intermediate P-15 is used to replace the intermediate P-1, the purity of the obtained target product is 99.2%, and the yield is 79.7%. Elemental analysis Structure (molecular formula C)71H53N3O): theoretical value: c, 88.44; h, 5.54; n, 4.36; o, 1.66; test values are: c, 88.42; h, 5.55; n, 4.37; o, 1.65; ESI-MS (M/z) (M +): theoretical value is 963.42, found 963.43.
Example 29: preparation of Compound 319
Figure BDA0001803402740000401
Prepared according to the synthetic method of the compound 1, except that the intermediate K-15 is used for replacing the intermediate K-1, and the intermediate P-16 is used for replacing the intermediateThe purity of the target product obtained by the method for preparing the P-1 derivative is 98.7%, and the yield is 83.4%. Elemental analysis Structure (molecular formula C)61H43N3S): theoretical value: c, 86.19; h, 5.10; n, 4.94; s, 3.77; test values are: c, 86.20; h, 5.11; n, 4.95; s, 3.75; ESI-MS (M/z) (M +): theoretical value is 849.32, found 849.34.
Example 30: preparation of Compound 81
Figure BDA0001803402740000402
The compound was prepared according to the synthesis method of compound 1 except that intermediate K-16 was used instead of intermediate K-1 and intermediate P-17 was used instead of intermediate P-1, and the purity of the obtained objective product was 99.3% and the yield was 75.5%. Elemental analysis Structure (molecular formula C)62H47N3O): theoretical value: c, 87.60; h, 5.57; n, 4.94; o, 1.88; test values are: c, 87.59; h, 5.56; n, 4.95; o, 1.87; ESI-MS (M/z) (M +): theoretical value is 849.37, found 849.35.
Example 31: preparation of Compound 122
Figure BDA0001803402740000403
The compound was prepared according to the synthesis method of compound 1 except that intermediate K-17 was used instead of intermediate K-1 and intermediate P-18 was used instead of intermediate P-1, and the purity of the obtained objective product was 99.4% and the yield was 76.1%. Elemental analysis Structure (molecular formula C)47H33N3O): theoretical value: c, 86.08; h, 5.07; n, 6.41; o, 2.44; test values are: c, 86.06; h, 5.05; n, 6.44; o, 2.44; ESI-MS (M/z) (M +): theoretical value is 655.26, found 655.28.
The organic compound of the present invention is used in a light emitting device, and can be used as a hole transport layer material or an electron blocking layer material, and the compounds of the present invention are respectively tested for T1 energy level, thermal property and HOMO energy level, and the test results are shown in table 3.
TABLE 3
Figure BDA0001803402740000411
Figure BDA0001803402740000421
Note: the triplet energy level T1 was measured by Hitachi F4600 fluorescence spectrometer under the conditions of 2X 10- 5A toluene solution of mol/L; the glass transition temperature Tg is determined by differential scanning calorimetry (DSC, DSC204F1 DSC, Germany Chi corporation), the heating rate is 10 ℃/min; the thermogravimetric temperature Td is a temperature at which 1% of the weight loss is observed in a nitrogen atmosphere, and is measured on a TGA-50H thermogravimetric analyzer of Shimadzu corporation, Japan, and the nitrogen flow rate is 20 mL/min; the highest occupied molecular orbital HOMO energy level was tested by the ionization energy test system (IPS-3), which is an atmospheric environment.
As can be seen from the data in table 3, the organic compound of the present invention has a suitable HOMO energy level, can be applied to a hole transport layer, has a higher triplet energy level and a higher thermal stability, and can improve the efficiency and the lifetime of the manufactured OLED device containing the organic compound of the present invention.
The effect of the compounds of the present invention as hole transport layer materials or electron blocking layer materials in devices is detailed below by device examples 1-31 and device comparative example 1. Device examples 2 to 31 and device comparative example 1 compared with device example 1, the manufacturing processes of the devices were completely the same, and the same substrate material and electrode material were used, and the film thicknesses of the electrode materials were also kept the same, except that the hole transport layer material or the electron blocking layer material in the devices were changed. The device stack structure is shown in table 4, and the performance test results of each device are shown in tables 5 and 6.
Device example 1
The preparation method of the device comprises the following steps:
a) cleaning the ITO anode layer 2 on the transparent substrate layer 1, respectively ultrasonically cleaning the ITO anode layer 2 with deionized water, acetone and ethanol for 15 minutes, and then treating the ITO anode layer 2 in a plasma cleaner for 2 minutes;
b) evaporating a hole injection layer material HAT-CN on the ITO anode layer 2 in a vacuum evaporation mode, wherein the thickness of the hole injection layer material HAT-CN is 10nm, and the hole injection layer material HAT-CN is used as a hole injection layer 3;
c) evaporating a compound 1 on the hole injection layer 3 in a vacuum evaporation mode, wherein the thickness of the compound is 60nm, and the layer is a hole transport layer 4;
d) evaporating an electron blocking material EB-1 on the hole transmission layer 4 in a vacuum evaporation mode, wherein the thickness of the electron blocking material EB-1 is 20nm, and the electron blocking layer 5 is formed on the hole transmission layer;
e) evaporating a light-emitting layer 6 on the electron blocking layer 5, wherein GH-1 and GH-2 are used as host materials of the light-emitting layer, GD-1 is used as a doping material, and the mass ratio of GH-1 to GH-2 to GD-1 is 45:45: 10;
f) evaporating electron transport materials ET-1 and Liq on the light emitting layer 6 in a vacuum evaporation mode according to the mass ratio of 1:1, wherein the thickness is 35nm, and the organic material of the layer is used as a hole blocking/electron transport layer 7;
g) vacuum evaporating an electron injection layer LiF with the thickness of 1nm on the hole blocking/electron transport layer 7, wherein the layer is an electron injection layer 8;
h) on the electron injection layer 8, cathode Al (100nm) was vacuum-evaporated, and this layer was a cathode reflective electrode layer 9.
Figure BDA0001803402740000431
After the electroluminescent device is manufactured according to the steps, the driving voltage and the current efficiency of the device are measured.
TABLE 4
Figure BDA0001803402740000432
Figure BDA0001803402740000441
Figure BDA0001803402740000451
The efficiency and lifetime data for each device example and device comparative example 1 are shown in table 5.
TABLE 5
Figure BDA0001803402740000452
Figure BDA0001803402740000461
As can be seen from the device data results of table 5, the organic light emitting device of the present invention achieves a greater improvement in both efficiency and lifetime over OLED devices of known materials.
In order to compare the efficiency attenuation of different devices under high current density, the efficiency attenuation coefficient phi is defined and expressed, and the efficiency attenuation coefficient phi represents that the driving current is 100mA/cm2The larger the phi value is, the more serious the efficiency roll-off of the device is, and otherwise, the problem of rapid attenuation of the device under high current density is controlled. The efficiency attenuation coefficient φ was measured for each of the device examples 1-31 and the device comparative example 1, and the results are shown in Table 6:
TABLE 6
Device code Coefficient of attenuation of efficiency phi Device code Coefficient of attenuation of efficiency phi
Device example 1 0.22 Device example 17 0.20
Device example 2 0.23 Device example 18 0.22
Device example 3 0.24 Device example 19 0.21
Device example 4 0.24 Device example 20 0.23
Device example 5 0.26 Device example 21 0.23
Device example 6 0.21 Device example 22 0.24
Device example 7 0.25 Device example 23 0.20
Device example 8 0.23 Device example 24 0.22
Device example 9 0.24 Device example 25 0.20
Device example 10 0.26 Device example 26 0.21
Device example 11 0.27 Device example 27 0.23
Device example 12 0.22 Device example 28 0.21
Device example 13 0.23 Device example 29 0.20
Device example 14 0.24 Device example 30 0.20
Device example 15 0.26 Device example 31 0.22
Device example 16 0.26 Device comparative example 1 0.40
From the data in table 6, it can be seen that the organic light emitting device of the present invention can effectively reduce the efficiency roll-off by comparing the efficiency roll-off coefficients of the examples and the comparative examples.
Further, the efficiency of the OLED device prepared by the material is stable when the OLED device works at low temperature, the efficiency test is carried out on the device examples 1, 14 and 28 and the device comparative example 1 at the temperature of-10-80 ℃, and the obtained results are shown in the table 7 and the figure 2.
TABLE 7
Figure BDA0001803402740000471
As can be seen from the data in table 7, device examples 1, 14, and 28 are device structures in which the material of the present invention and the known material are combined, and compared with device comparative example 1, the efficiency is high at low temperature, and the efficiency is steadily increased during the temperature increase process.
The above description is only for the purpose of illustrating the preferred embodiments of the present invention and is not to be construed as limiting the invention, and any modifications, equivalents, improvements and the like that fall within the spirit and principle of the present invention are intended to be included therein.

Claims (10)

1. An aromatic amine compound characterized by having a structure represented by general formula (1):
Figure FDA0001803402730000011
in the general formula (1), L1Is represented by one of the structures shown in a general formula (2), a general formula (3), a general formula (4), a general formula (5), a general formula (6), a general formula (7), a general formula (8), a general formula (9), a general formula (10) or a general formula (11);
Figure FDA0001803402730000012
said X1And X3Each independently represents N or C-R8Said X is2Represented by-O-, -S-or-CH2In the general formula (2), the general formula (3), the general formula (4), the general formula (5), the general formula (6), the general formula (7), the general formula (8), the general formula (9), the general formula (10) or the general formula (11), a dotted line represents a nitrogen atom, and L1Or L2The attachment site of (a);
said L2Represents one of structures shown by a single bond, substituted or unsubstituted phenylene, substituted or substituted biphenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted naphthyridine, substituted or unsubstituted pyridylene, a general formula (2), a general formula (3), a general formula (4), a general formula (5), a general formula (6), a general formula (7), a general formula (8), a general formula (9), a general formula (10) or a general formula (11);
ar is1、Ar2、Ar3、Ar4Each independently represents one of a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted terphenylene, a substituted or unsubstituted naphthyridine and a substituted or unsubstituted pyridylene;
the R is1、R2、R3、R4Each independently represents one of substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted pyrenyl, substituted or unsubstituted anthryl, and a structure shown in a general formula (18) or a general formula (19);
Figure FDA0001803402730000021
in the general formula (18) and the general formula (19), Z represents N or C-R9；
Ar1、Ar2、Ar3、Ar4Z at the site of attachment to the general formula (18) represents a carbon atom;
said X3、X4、X5Independently represent-O-, -S-, -C (R)10)(R11) -or-N (R)12) -one of the above; said X3、X5May also be each a single bond;
the R is5、R6、R7Each independently represents a hydrogen atom, C1-C20Alkyl, substituted or unsubstituted C6-C40One of a substituted or unsubstituted 5-to 40-membered heteroaryl group containing one or more heteroatoms;
the R is8、R9Each independently represents a hydrogen atom, a halogen, a cyano group, or C1-C20Alkyl of (C)2-C20Alkenyl of (a), substituted or unsubstituted C6-C40One of a substituted or unsubstituted 5-to 40-membered heteroaryl group containing one or more heteroatoms; two or more adjacent R9Can be bonded to each other to form a ring;
the R is10To R12Are each independently represented by C1-C20Alkyl, substituted or unsubstituted C6-C40One of a substituted or unsubstituted 5-to 40-membered heteroaryl group containing one or more heteroatoms; r10And R11May be bonded to each other to form a ring;
the substituent for substituting each of the above-mentioned substitutable groups is optionally selected from halogen, cyano, C1-C10Alkyl radical, C6-C40One or more of aryl, 5-to 40-membered heteroaryl containing one or more heteroatoms;
the heteroatom in the heteroaryl group is optionally selected from one or more of N, O or S.
2. The aromatic amine compound according to claim 1, wherein L in the general formula (1)1Is represented by one of the structures shown in a general formula (2), a general formula (3), a general formula (4), a general formula (5), a general formula (6), a general formula (7), a general formula (8), a general formula (9), a general formula (10), a general formula (11), a general formula (12), a general formula (13), a general formula (14), a general formula (15), a general formula (16) or a general formula (17);
Figure FDA0001803402730000031
3. the aromatic amine compound according to claim 1, wherein the general formula (1) is represented by one of structures represented by general formulae (1-1) to (1-18):
Figure FDA0001803402730000032
Figure FDA0001803402730000041
the ring a is represented as:
Figure FDA0001803402730000042
any one of (a) said ring(s) a are connected to a phenylene fused ring through adjacent sites marked with asterisks;
wherein the symbols and signs used have the meanings given in claim 1.
4. The aromatic amine compound of claim 1, wherein R is1、R2、R3、R4Each independently represented by one of the following structures:
Figure FDA0001803402730000051
5. the aromatic amine compound according to claim 1, wherein L is2Represented as one of the following structures:
Figure FDA0001803402730000052
6. the aromatic amine compound of claim 1, wherein R is5、R6、R7Each independently represents methyl, ethyl, propyl, isopropyl, tert-butyl, pentyl, phenyl, biphenyl, naphthyl, naphthyridinyl, benzopyrrole, pyridyl or furyl;
the R is8、R9Each independently represents a hydrogen atom, a fluorine atom, a cyano group, a methyl group, an ethyl group, a propyl group, an isopropyl group, a tert-butyl group, a pentyl group, a phenyl group, a biphenyl group, a naphthyl group, a naphthyridinyl group, a pyridyl group or a furyl group;
the R is10To R12Each independently represents methyl, ethyl, propyl, isopropyl, tert-butyl, pentyl, phenyl, biphenyl, naphthyl, naphthyridinyl or pyridyl;
the substituent for substituting each of the above substitutable groups is optionally selected from halogen, cyanomethyl, ethyl, propyl, isopropyl, tert-butyl, pentyl, phenyl, biphenyl, naphthyl, naphthyridinyl, pyridyl or furyl.
7. The aromatic amine compound according to any one of claims 1 to 6, wherein the aromatic amine compound has a specific structural formula:
Figure FDA0001803402730000061
Figure FDA0001803402730000071
Figure FDA0001803402730000081
Figure FDA0001803402730000091
Figure FDA0001803402730000101
Figure FDA0001803402730000111
Figure FDA0001803402730000121
Figure FDA0001803402730000131
Figure FDA0001803402730000141
Figure FDA0001803402730000151
Figure FDA0001803402730000161
Figure FDA0001803402730000171
Figure FDA0001803402730000181
any one of them.
8. Use of the aromatic amine compound according to any one of claims 1 to 7 for the preparation of an organic electroluminescent device.
9. An organic electroluminescent device comprising a plurality of organic thin film layers between an anode and a cathode, wherein at least one of the organic thin film layers comprises the aromatic amine compound according to any one of claims 1 to 6.
10. The organic electroluminescent device according to claim 9, wherein the organic thin film layer comprises a hole transport layer or an electron blocking layer, and the material of the hole transport layer or the electron blocking layer is the aromatic amine compound according to any one of claims 1 to 6.
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CN113461593B (en) * 2020-03-31 2024-04-23 江苏三月科技股份有限公司 Biphenyl amine derivative and application thereof
CN111675687A (en) * 2020-07-09 2020-09-18 吉林奥来德光电材料股份有限公司 Organic electroluminescent compound and preparation method and application thereof
CN112250679A (en) * 2020-11-10 2021-01-22 长春海谱润斯科技股份有限公司 Phenylenediamine organic compound and organic light-emitting device thereof
CN112250679B (en) * 2020-11-10 2021-12-21 长春海谱润斯科技股份有限公司 Phenylenediamine organic compound and organic light-emitting device thereof
CN114478265A (en) * 2020-11-13 2022-05-13 江苏三月科技股份有限公司 Arylamine compound and application thereof in organic electroluminescent device
CN112358455A (en) * 2020-11-16 2021-02-12 吉林奥来德光电材料股份有限公司 Dibenzo seven-membered heterocyclic compound and preparation method and application thereof
CN114685284A (en) * 2020-12-29 2022-07-01 江苏三月科技股份有限公司 Triarylamine organic compound and application thereof
CN113402525A (en) * 2021-05-21 2021-09-17 吉林奥来德光电材料股份有限公司 Compound containing cyano aromatic group, synthetic method thereof, organic material, functional layer and organic electroluminescent device
WO2022268176A1 (en) 2021-06-24 2022-12-29 江苏先声药业有限公司 Steroid compound, and pharmaceutical composition thereof and use thereof

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