AROMATIC AMINE COMPOUND, COVERING LAYER MATERIAL, AND LIGHT-EMITTING ELEMENT

Abstract

The present invention provides an aromatic amine compound as represented by formula (1) for improving the light extraction efficiency and color purity of an organic light-emitting element, an organic light-emitting element material containing the aromatic amine compound, a covering layer material of organic light-emitting element, and an organic light-emitting element.

##STR00001##

The organic light-emitting element provided by the present invention can achieve high luminous efficiency and color reproducibility. The organic light-emitting element of the present invention can be used for an organic EL display, a backlight source of a liquid crystal display, illumination, light sources for gauges, a sign board, a marker light, etc. The present invention provides an organic light-emitting element having greatly improved light extraction efficiency and excellent color purity.

Claims

1. An aromatic amine compound comprising a structure represented by formula (1): ##STR00024## wherein, X.sup.1 and X.sup.2 are selected from a sulfur atom, an oxygen atom or NR, wherein R is independently selected from one or more of the group consisting of hydrogen, deuterium, optionally substituted alkyl group, optionally substituted cycloalkyl group, optionally substituted heterocyclic group, optionally substituted alkenyl group, optionally substituted cycloalkenyl group, optionally substituted alkynyl group, optionally substituted alkoxyl group, optionally substituted alkyl sulphanyl group, optionally substituted aryl ether group, optionally substituted aryl thioether group, optionally substituted aryl group, optionally substituted heteroaryl group, optionally substituted carbonyl group, optionally substituted carboxyl group, optionally substituted oxycarbonyl group, optionally substituted carbamoyl group, optionally substituted alkylamino group, or optionally substituted silanyl group; L.sup.1 and L.sup.2 may be identical or different, and independently selected from one of arylene group, heteroarylene group or direct bonding; Ar.sup.1 is selected from arylene group; Ar.sup.2 and Ar.sup.3 may be identical or different heteroaryl groups; wherein, R.sup.1 and R.sup.2 may be identical or different, and are independently selected from one or more of the group consisting of hydrogen, deuterium, halogen, optionally substituted alkyl group, optionally substituted cycloalkyl group, optionally substituted heterocyclic group, optionally substituted alkenyl group, optionally substituted cycloalkenyl group, optionally substituted alkynyl group, optionally substituted alkoxyl group, optionally substituted alkyl sulphanyl group, optionally substituted aryl ether group, optionally substituted aryl thioether group, optionally substituted aryl group, optionally substituted heteroaryl group, optionally substituted cyano group, optionally substituted carbonyl group, optionally substituted carboxyl group, optionally substituted oxycarbonyl group, optionally substituted carbamoyl group, optionally substituted alkylamino group, or optionally substituted silanyl group; or may also be bonded with adjacent substituents to form a ring.

2. The aromatic amine compound according to claim 1, wherein, in formula (1), R.sup.1, R.sup.2 are one or more of aryl group or heteroaryl group.

3. The aromatic amine compound according to claim 1, wherein the X.sup.1 and X.sup.2 are selected from sulfur atoms; L.sup.1 and L.sup.2 are selected from arylene group; R.sup.1 and R.sup.2 are aryl group.

4. The aromatic amine compound according to claim 1, wherein the Ar.sup.1 is non-condensed-ring aryl group.

5. The aromatic amine compound according to claim 1, wherein the Ar.sup.2 and Ar.sup.3 are heteroaryl group directly connected to nitrogen.

6. The aromatic amine compound according to claim 1, wherein in formula (1), alkyl group is a C1-C20 alkyl group, cycloalkyl group is C3-C20 cycloalkyl group, heterocyclic group is C2-C20 heterocyclic group; alkenyl group is C2-C20 alkenyl group; cycloalkenyl group is C3-C20 cycloalkenyl group; alkynyl group is C2-C20 alkynyl group; alkoxyl group is C1-C20 alkoxyl group; alkyl sulphanyl group is C1-C20 alkyl sulphanyl group; aryl ether group is C6-C40 aryl ether group; the aryl thioether group is C6-C60 aryl thioether group; aryl group is C6-C60 aryl group; and heteroaryl group is C4-C60 aromatic heterocyclic group.

7. An organic light-emitting element material, wherein the material contains the aromatic amine compound according to claim 1.

8. An organic light-emitting element, comprising a substrate, a first electrode, a light-emitting layer containing one or more organic layer film, a second electrode, and a covering layer, wherein the organic light-emitting element contains the organic light-emitting element material according to claim 7.

9. A covering layer material of organic light-emitting element, wherein the material contains the aromatic amine compound according to claim 1.

10. An organic light-emitting element, comprising: a substrate, a first electrode, one or more organic layer film including a light-emitting layer, a second electrode, and a covering layer, wherein the covering layer contains the covering layer material of organic light-emitting element according to claim 9.

Description

DETAILED DESCRIPTION OF EMBODIMENTS OF THE INVENTION

[0084] The aromatic amine compound of the present invention is exemplified by the following embodiments, but the present invention is not limited to the aromatic amine compounds and synthetic methods exemplified by these embodiments.

[0085] Toluene, xylene, methanol, 3-aminopyridine, and the like are commercially purchased from Sinopharm; 4,4-dibromobiphenyl, 2-(4-bromophenyl)-5-phenylthiophene, and the like are commercially purchased from Zhengzhou Haikuo Optoelectronics Co., Ltd. Various palladium catalysts are commercially purchased from Aldrich Company.

[0086] .sup.1H-NMR spectrum is measured using a JEOL (400 MHz) nuclear magnetic resonance instrument; a HPLC spectrum is measured using a Shimadzu LC-20AD high-performance liquid chromatography.

[0087] The following substances are used in the preparation examples, examples and comparative examples:

[0088] Compound [1]: 4,4-bis(N-(3-pyridyl)-(4-(2-(5-phenylthienyl))phenyl)amine)yl-straight-chain terphenyl

[0089] Compound [4]: 4,4-bis(N-(3-pyridyl)-2-(5-phenylthienyl)amine)yl-straight-chain terphenyl

[0090] Compound [8]: 4,4-bis(N-(3-pyridyl)-(4-(2-(5-phenylthienyl))phenyl)amine)yl-biphenyl

[0091] Compound [23]: 4,4-bis(N-(3-pyridyl)-(4-(2-(5-benzofuran))phenyl)amine)yl-biphenyl

[0092] Compound [38]: 4,4-bis(N-(3-pyridyl)-(4-(2-(5-phenyl N-phenylpyrrole))phenyl)amine)yl-biphenyl

[0093] Compound [43]: 4,4-bis(N-(3-pyridyl)-(4-(2-(5-phenyl N-phenylpyrrole))N-phenylpyrrole)amine)yl-biphenyl

[0094] Com-2: N,N,N,N-tetra(4-biphenyl)diamino biphenylene

[0095] NPD: N,N-diphenyl-N,N-bis(1-naphthyl)-1,1-biphenyl-4,4-diamine (the structure is as follows)

##STR00012##

[0096] F4-TCNQ: 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanodimethyl p-benzoquinone) (the structure is as follows)

##STR00013##

[0097] BH: (9-(2-naphthyl)-10-(4-(1-naphthyl)phenyl)anthracene (the structure is as follows)

##STR00014##

[0098] BD: (E-7-(4-(diphenyl amino)styryl)-N,N-diphenyl-9,9-dimethylfluorenyl-2-amine) (the structure is as follows)

##STR00015##

[0099] Alq.sub.3: tris(8-hydroxyquinoline)aluminum (the structure is as follows)

##STR00016##

[0100] SPA: 2,5-bis(4-(N-(-3-biphenyl)-(N-3-pyridyl)aminophenyl)thiophene (the structure is as follows)

##STR00017##

Preparation Example 1

[0101] Synthesis of Compound [1]

##STR00018##

[0102] In the presence of nitrogen, 2.07 g of 3-aminopyridine (22 mmol), 6.305 g of 2-(4-bromophenyl)-5-phenylthiophene (20 mmol), 4.61 g of sodium tert-butoxide (48 mmol), 0.23 g of bis(dibenzylidene)acetone)palladium (4.0 mmol), 0.38 g of 2-dicyclohexyl phosphonium-2,4,6-triisopropyl biphenyl (8 mmol), 50 ml of toluene and 50 ml of xylene are added to a reactor, and stirred and refluxed for 6 hours. The reactant is filtered after being cooled to room temperature. A filter cake is rinsed with 100 ml of xylene, washed twice with 200 ml of water and filtered, washed while stirring twice with 200 ml of methanol and filtered, and vacuum-dried to obtain 5.6 g of [4-(5-phenyl-thiophen-2-phenyl]-3-pyridylamine.

[0103] .sup.1HNMR (DMSO): 8.52 (s, 1H), 8.22 (s, 1H), 8.12 (s, 1H), 7.88 (s, 2H), 7.48 to 7.41 (m, 3H), 7.32 to 7.22 (m, 6H), 6.54 to 6.51 (m, 2H)

##STR00019##

[0104] In the presence of nitrogen, 5.25 g of [4-(5-phenyl-thiophen-2-phenyl]-3-pyridylamine (16 mmol), 3.10 g of 4,4-dibromoterphenyl (8 mmol), 0.18 mg of bis(dibenzylidene)acetone)palladium (0.32 mmol), 0.30 mg of 2-dicyclohexyl phosphonium-2,4,6-triisopropyl biphenyl (0.64 mmol), 1.85 g of sodium tert-butoxide (19.2 mmol), 60 ml of toluene and 60 ml of xylene are added to a reactor, heated, refluxed and stirred for 4 hours. The reactant is filtered after being cooled to room temperature. A filter cake is rinsed with 200 ml of xylene, washed with a mixture of 100 ml of water and 100 ml of methanol, then washed with 200 ml of water, filtered and dried to obtain 4.7 g of crude product. The crude product is sublimed at a pressure of 310.sup.3 Pa and a temperature of 330 C. to obtain 2.4 g of the compound [1] (light yellow solid).

[0105] .sup.1HNMR (CDCl.sub.3): 8.55 to 8.51 (s, 2H), 8.25 to 8.21 (m, 2H), 7.66 to 7.63 (s, 4H), 7.56 to 7.52 (m, 4H), 7.50 to 7.46 (m, 4H), 7.42 to 7.38 (m, 2H), 7.34 to 7.30 (m, 4H), 7.27 to 7.21 (m, 12H), 6.54 to 6.50 (m, 8H).

[0106] HPLC (purity=98.1%)

Preparation Example 2

[0107] Synthesis of Compound [8]

##STR00020##

[0108] In the presence of nitrogen, 2.07 g of 3-aminopyridine (22 mmol), 6.305 g of 2-(4-bromophenyl)-5-phenylthiophene (20 mmol), 4.61 g of sodium tert-butoxide (48 mmol), 0.23 g of bis(dibenzylidene)acetone)palladium (4.0 mmol), 0.38 g of 2-dicyclohexyl phosphonium-2,4,6-triisopropyl biphenyl (8 mmol), 50 ml of toluene and 50 ml of xylene are added to a reactor, and stirred and refluxed for 6 hours. The reactant is filtered after being cooled to room temperature. A filter cake is rinsed with 100 ml of xylene, washed twice with 200 ml of water and filtered, washed while stirring twice with 200 ml of methanol and filtered, and vacuum-dried to obtain 5.6 g of [4-(5-phenyl-thiophen-2-phenyl]-3-pyridylamine.

[0109] .sup.1HNMR (DMSO): 8.52 (s, 1H), 8.22 (s, 1H), 8.12 (s, 1H), 7.88 (s, 2H), 7.48 to 7.41 (m, 3H), 7.32 to 7.22 (m, 6H), 6.54 to 6.51 (m, 2H)

##STR00021##

[0110] In the presence of nitrogen, 5.25 g of [4-(5-phenyl-thiophen-2-phenyl]-3-pyridylamine (16 mmol), 2.5 g of 4,4-dibromoterphenyl (8 mmol), 0.18 mg of bis(dibenzylidene)acetone)palladium (0.32 mmol), 0.30 mg of 2-dicyclohexyl phosphonium-2,4,6-triisopropyl biphenyl (0.64 mmol), 1.85 g of sodium tert-butoxide (19.2 mmol), 60 ml of toluene and 60 ml of xylene are added to a reactor, and heated, refluxed and stirred for 4 hours. The reactant is filtered after being cooled to room temperature. A filter cake is rinsed with 200 ml of xylene, washed with a mixture of 100 ml of water and 100 ml of methanol, washed with 200 ml of water, filtered and dried to obtain 4.5 g of crude product. The crude product is sublimed at a pressure of 310.sup.3 Pa and a temperature of 310 C. to obtain 2.2 g of the compound [12] (light yellow solid).

[0111] .sup.1HNMR (CDCl.sub.3): 8.55 to 8.51 (s, 2H), 8.25 to 8.21 (m, 2H), 7.66 to 7.63 (s, 4H), 7.56 to 7.52 (m, 4H), 7.50 to 7.46 (m, 4H), 7.42 to 7.38 (m, 2H), 7.34 to 7.30 (m, 4H), 7.27 to 7.21 (m, 8H), 6.54 to 6.50 (m, 8H).

[0112] HPLC (purity=98.6%)

Preparation Example 3

[0113] Synthesis of Compound [4]

##STR00022##

[0114] In the presence of nitrogen, 2.07 g of 3-aminopyridine (22 mmol), 4.78 g of 2-bromo-5-phenylthiophene (20 mmol), 4.61 g of sodium tert-butoxide (48 mmol), 0.23 g of bis(dibenzylidene acetone)palladium (4.0 mmol), 0.38 g of 2-dicyclohexyl phosphonium-2,4,6-triisopropyl biphenyl (8 mmol), 50 ml of toluene and 50 ml of xylene are added to a reactor, and stirred and refluxed for 6 hours. The reactant is filtered after being cooled to room temperature. A filter cake is rinsed with 100 ml of xylene, washed twice with 200 ml of water and filtered, washed while stirring twice with 200 ml of methanol and filtered, and vacuum-dried to obtain 4.3 g of [(5-phenyl-thiophen)]-3-pyridylamine.

[0115] .sup.1HNMR (DMSO): 8.52 (s, 1H), 8.22 (s, 1H), 8.12 (s, 1H), 7.48 to 7.41 (m, 3H), 7.32 to 7.22 (m, 4H), 6.54 to 6.51 (m, 2H)

[0116] HPLC (purity=98.1%)

##STR00023##

[0117] In the presence of nitrogen, 4.03 g of [(5-phenyl-thiophen]-3-pyridylamine (16 mmol), 3.10 g of 4,4-dibromoterphenyl (8 mmol), 0.18 mg of bis(dibenzylidene acetone)palladium (0.32 mmol), 0.30 mg of 2-dicyclohexyl phosphonium-2,4,6-triisopropyl biphenyl (0.64 mmol), 1.85 g of sodium tert-butoxide (19.2 mmol), 60 ml of toluene and 60 ml of xylene are added to a reactor, heated, stirred and refluxed for 4 hours. The reactant is filtered after being cooled to room temperature. A filter cake is rinsed with 200 ml of xylene, washed with a mixture of 100 ml of water and 100 ml of methanol, washed with 200 ml of water, and filtered and dried to obtain 3.6 g of crude product. The crude product is sublimed at a pressure of 310.sup.3 Pa and a temperature of 300 C. to obtain 1.8 g of compound [4] (light yellow solid).

[0118] .sup.1HNMR (CDCl.sub.3): 8.55 to 8.51 (s, 2H), 8.25 to 8.21 (m, 2H), 7.66 to 7.63 (s, 4H), 7.56 to 7.52 (m, 4H), 7.50 to 7.46 (m, 4H), 7.42 to 7.38 (m, 2H), 7.34 to 7.30 (m, 4H), 7.27 to 7.21 (m, 8H), 6.54 to 6.50 (m, 4H).

Preparation Example 4

[0119] Synthesis of Compound [23]

[0120] Besides that 2-(4-bromophenyl)-5-phenylthiophene is replaced with 2-(4-bromophenyl)-5-phenylfuran, the rest is the same as that in Preparation Example 1. 2.3 g of compound [23] (white solid) is obtained.

[0121] .sup.1HNMR (CDCl.sub.3): 8.54 to 8.51 (s, 2H), 8.25 to 8.21 (m, 2H), 7.67 to 7.63 (s, 4H), 7.56 to 7.52 (m, 4H), 7.50 to 7.46 (m, 4H), 7.43 to 7.38 (m, 2H), 7.34 to 7.30 (m, 4H), 7.27 to 7.21 (m, 12H), 6.55 to 6.51 (m, 8H).

[0122] HPLC (purity=98.5%)

Preparation Example 5

[0123] Synthesis of Compound [38]

[0124] Besides that 2-(4-bromophenyl)-5-phenylthiophene is replaced with 2-(4-bromophenyl)-1,5-diphenyl-pyrrole, the rest is the same as that in Preparation Example 1. 2.6 g of compound [38] (white solid) is obtained.

[0125] .sup.1HNMR (CDCl.sub.3): 8.55 to 8.52 (s, 2H), 8.25 to 8.21 (m, 2H), 7.67 to 7.63 (s, 4H), 7.56 to 7.52 (m, 4H), 7.50 to 7.46 (m, 4H), 7.43 to 7.38 (m, 2H), 7.35 to 7.29 (m, 12H), 7.25 to 7.21 (m, 12H), 6.53 to 6.50 (m, 8H).

[0126] HPLC (purity=98.7%)

Preparation Example 6

[0127] Synthesis of Compound [43]

[0128] Besides that 2-(4-bromophenyl)-5-phenylthiophene is replaced with 4-[5-(4-bromobenzene)-2-thienyl]-pyridine, the rest is the same as that in Preparation Example 1. 2.0 g of compound [43] (white solid) is obtained.

[0129] .sup.1HNMR (CDCl.sub.3): 8.55 to 8.51 (s, 2H), 8.25 to 8.21 (m, 2H), 7.66 to 7.63 (s, 4H), 7.56 to 7.52 (m, 4H), 7.50 to 7.46 (m, 4H), 7.42 to 7.38 (m, 2H), 7.34 to 7.30 (m, 4H), 7.27 to 7.21 (m, 10H), 6.54 to 6.50 (m, 8H).

[0130] HPLC (purity=98.3%)

Example 1

[0131] Production Method of Thin Film Sample

[0132] An alkali-free glass substrate (Asahi Glass Co., Ltd., AN100) is subjected to UV ozone cleaning treatment for 20 minutes, further arranged in a vacuum evaporation apparatus and exhausted until the compound [12] is evaporated by a resistance heating evaporation method in the case that the vacuum degree in the apparatus is higher than 110.sup.3 Pa, so as to prepare a thin film of about 50 nm. The evaporation rate is 0.1 nm/s.

[0133] The measurement of the refractive index and attenuation coefficient of the thin film sample prepared above is performed at Toray Research Center, Inc., and the adopted instrument is ellipsometric spectroscopy (J.A. Woollam Corporation M-2000).

TABLE-US-00001 TABLE 1 Refractive index (n) Compound = 430 nm = 460 nm = 500 nm [8] 2.52 2.33 2.13

[0134] Examples 2 to 6 and Comparative Examples 1, 2

Example 2

[0135] Besides that the compound [8] is replaced with the compound [1], the rest is the same as that in Example 1.

[0136] The organic light-emitting element is evaluated. The evaluation results are shown in Table 2.

Example 3

[0137] Besides that the compound [8] is replaced with the compound [4], the rest is the same as that in Example 1.

[0138] The organic light-emitting element is evaluated. The evaluation results are shown in Table 2.

Example 4

[0139] Besides that the compound [8] is replaced with the compound [23], the rest is the same as that in Example 1.

[0140] The organic light-emitting element is evaluated. The evaluation results are shown in Table 2.

Example 5

[0141] Besides that the compound [8] is replaced with the compound [38], the rest is the same as that in Example 1.

[0142] The organic light-emitting element is evaluated. The evaluation results are shown in Table 2.

Example 6

[0143] Besides that the compound [8] is replaced with the compound [43], the rest is the same as that in Example 1.

[0144] The organic light-emitting element is evaluated. The evaluation results are shown in Table 2.

Comparative Example 1

[0145] Besides that the compound [8] is replaced with NPD, the rest is the same as that in Example 1.

Comparative Example 2

[0146] Besides that the compound [8] is replaced with SPA, the rest is the same as that in Example 1.

[0147] The organic light-emitting element is evaluated. The evaluation results are shown in Table 2.

TABLE-US-00002 TABLE 2 Refractive index (n) Compound = 430 nm = 460 nm = 500 nm Example 2 [1] 2.50 2.31 2.12 Example 3 [4] 2.48 2.30 2.12 Example 4 [23] 2.48 2.32 2.12 Example 5 [38] 2.50 2.30 2.09 Example 6 [43] 2.51 2.32 2.13 Comparative NPD 1.99 1.92 1.87 example 1 Comparative SPA 2.45 2.29 2.10 example 2

[0148] As shown in Table 2, the refractive indexes of Examples 2 to 6 are significantly higher than those of Comparative Example 1. Further, the performances of the light-emitting element are tested.

[0149] Evaluation Method of Light-emitting Element

Example 7

[0150] The alkali-free glass is ultrasonically washed in isopropyl alcohol for 15 minutes, and then subjected to UV ozone washing treatment in the atmosphere for 30 minutes. A vacuum evaporation method is used for evaporating 100 nm of aluminum as an anode and then sequentially laminate a hole injection layer (NPD and F4-TCNQ (weight ratio 97:3), 50 nm), a hole transport layer (NPD, 80 nm), a blue light-emitting layer (BH and BD (weight ratio 97:3, 20 nm), an electron transport layer (Alq.sub.3, 30 nm), and an electron injection layer (LiF, 1 nm) by evaporation on the anode, and Mg and Ag (weight ratio 10:1, 15 nm) are then co-evaporated to obtain a translucent cathode.

[0151] Subsequently, the compound [8] (60 nm) is evaporated as a covering layer.

[0152] Finally, in a glove box with a dry nitrogen atmosphere, a sealing board made of alkali-free glass is sealed with an epoxy resin adhesive to produce a light-emitting element.

[0153] The above-mentioned light-emitting element is tested for brightness and color purity at room temperature and in the atmosphere by applying a direct current of 10 mA/cm.sup.2 by means of a spectroradiometer (CS1000, Konica Minolta Co., Ltd.) for light emission from the sealing board. As measured according to the above-mentioned measured values, the photometric efficiency is 7.3 cd/A, and the color purity is CIE (x, y)=(0.139, 0.051). When the compound [8] is used as the covering layer, a high-performance light-emitting element with high light-emitting efficiency and high color purity is obtained.

[0154] The organic light-emitting element is evaluated. The evaluation results are shown in Table 3.

Example 8

[0155] Besides that the covering layer material is the compound [1], the rest is the same as that in Example 7.

[0156] The organic light-emitting element is evaluated. The evaluation results are shown in Table 3.

Example 9

[0157] Besides that the covering layer material is the compound [4], the rest is the same as that in Example 7.

[0158] The organic light-emitting element is evaluated. The evaluation results are shown in Table 3.

Example 10

[0159] Besides that the covering layer material is the compound [23], the rest is the same as that in Example 7.

[0160] The organic light-emitting element is evaluated. The evaluation results are shown in Table 3.

Example 11

[0161] Besides that the covering layer material is the compound [38], the rest is the same as that in Example 7.

[0162] The organic light-emitting element is evaluated. The evaluation results are shown in Table 3.

Example 12

[0163] Besides that the covering layer material is the compound [43], the rest is the same as that in Example 7.

[0164] The organic light-emitting element is evaluated. The evaluation results are shown in Table 3.

Comparative Example 3

[0165] Besides that the covering layer material is NPD, the rest is the same as that in Example 7.

[0166] The organic light-emitting element is evaluated. The evaluation results are shown in Table 3.

Comparative Example 4

[0167] Besides that the covering layer material is SPA, the rest is the same as that in Example 7.

[0168] The organic light-emitting element is evaluated. The evaluation results are shown in Table 3.

TABLE-US-00003 TABLE 3 Luminous Color purity Compound efficiency (cd/A) CIE (x, y) Example 7 [8] 7.3 0.139, 0.051 Example 8 [1] 6.9 0.139, 0.051 Example 9 [4] 6.6 0.138, 0.049 Example 10 [23] 7.1 0.139, 0.050 Example 11 [38] 7.0 0.139, 0.051 Example 12 [43] 7.2 0.139, 0.051 Comparative NPD 4.5 0.139, 0.048 example 3 Comparative SPA 6.5 0.137, 0.051 example 4

[0169] As shown in Table 3, the light-emitting elements of Examples 7 to 12 satisfy both high light-emitting efficiency and high color purity. On the other hand, the light-emitting elements of Comparative Examples 3 to 4 have the same color purity as that in the examples, but have lower luminous efficiency than that in the examples. The light-emitting element in each example has higher luminous efficiency than that in Comparative Examples 3 and 4.

[0170] From the above results, it is derived that the aromatic amine compound according to embodiments of the present invention is suitable for organic light-emitting element materials to obtain the light-emitting element that satisfies high luminous efficiency and high color purity simultaneously, and is thus a more excellent covering layer material.