Light-emitting device and amine compound for light-emitting device

Abstract

The present application provides a light-emitting device and an amine compound for the light-emitting device, wherein the light-emitting device includes a first electrode, a hole transport region on the first electrode, an emission layer on the hole transport region, an electron transport region on the emission layer, and a second electrode on the electron transport region. The hole transport region may include an amine compound represented by Formula 1, thereby exhibiting high luminous efficiency: Formula 1

Description

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS

[0002] This application claims priority to and the benefit of Korean Patent Application No. 10-2020-0136728, filed on October 21, 2020, which is hereby incorporated by reference in its entirety. Technical Field

[0003] One or more aspects of the embodiments of the present disclosure relate to light-emitting devices and amine compounds for use in light-emitting devices. Background Art

[0004] Recently, organic electroluminescent displays (ELDs) have been actively developed as image displays. Unlike liquid crystal displays (LCDs), ELDs are self-luminescent displays in which holes and electrons injected from a first electrode and a second electrode recombine in an emissive layer, causing the luminescent material (including organic compounds) in the emissive layer to emit light, thereby displaying an image.

[0005] When light-emitting devices are applied to display devices, light-emitting devices having low driving voltage, high luminous efficiency and long service life (lifespan) are needed or desired, and development of materials for light-emitting devices that can stably (or appropriately) obtain these characteristics is ongoing. Summary of the Invention

[0006] One or more aspects of embodiments of the present disclosure relate to a light-emitting device and an amine compound for a light-emitting device, and more particularly, to a light-emitting device having high efficiency and an amine compound included in a hole transport region of the light-emitting device.

[0007] One or more embodiments of the present disclosure provide an amine compound represented by the following Formula 1:

[0008] Formula 1

[0009]

[0010] In the above formula 1, R1 to R 10 R1 to R2 may each independently be a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms. 10 At least one of them is represented by the following Formula 2, and Ring A and Ring B may each independently be represented by the following Formula 3 or Formula 4, but are represented by different formulas.

[0011] Formula 2

[0012]

[0013] In the above formula 2, L may be a directly connected (e.g., a chemical bond such as a single bond), a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms; n may be an integer selected from 0 to 3, and Ar1 and Ar2 may each independently be a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms.

[0014] Formula 3

[0015]

[0016] Formula 4

[0017]

[0018] In the above formula 3 and formula 4, R 11 and R 12 Each of them may independently be a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring-forming carbon atoms; a may be an integer selected from 0 to 4; and b may be an integer selected from 0 to 6.

[0019] In one or more embodiments, the above formula 1 can be represented by the following formula 5 or formula 6:

[0020] Formula 5

[0021]

[0022] Formula 6

[0023]

[0024] Among them, in the above formula 5 and formula 6,

[0025] R1 to R 12 , a and b are the same as those defined in Formula 1, Formula 3 and Formula 4.

[0026] In one or more embodiments, the amine compound may be a monoamine compound.

[0027] In one or more embodiments, the above formula 5 can be represented by the following formula 7-1:

[0028] Formula 7-1

[0029]

[0030] In the above formula 7-1, R x and R5 to R 10 each independently may be a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring carbon atoms; c may be an integer selected from 0 to 3; L may be a directly linked, substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms; n may be an integer selected from 0 to 3; Ar1 ​​and Ar2 may each independently be a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms; and R 11 、R 12 , a and b are the same as those defined in Formula 5.

[0031] In one or more embodiments, the above formula 5 can be represented by the following formula 7-2 or formula 7-3:

[0032] Formula 7-2

[0033]

[0034] Formula 7-3

[0035]

[0036] In the above formulas 7-2 and 7-3, R y and R1 to R4 may each independently be a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring carbon atoms; d may be an integer selected from 0 to 3; L may be a directly linked, substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms; n may be an integer selected from 0 to 3; Ar1 ​​and Ar2 may each independently be a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms; and R 11 、R 12 , a and b are the same as those defined in Formula 5.

[0037] In one or more embodiments, the above formula 6 can be represented by the following formula 8-1:

[0038] Formula 8-1

[0039]

[0040] In the above formula 8-1, R x , R5 to R 12 , L, Ar1, Ar2, a to c and n are the same as defined in Formula 6.

[0041] In one or more embodiments, the above formula 6 can be represented by the following formula 8-2:

[0042] Formula 8-2

[0043]

[0044] In the above formula 8-2, R y , R1 to R 12 , L, Ar1, Ar2, a, b, d and n are the same as defined in Formula 6.

[0045] In one or more embodiments, the above formula 6 can be represented by the following formula 9-1:

[0046] Formula 9-1

[0047]

[0048] In the above formula 9-1, R x and R5 to R 10 each independently may be a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring carbon atoms; c may be an integer selected from 0 to 3; L may be a directly linked, substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms; n may be an integer selected from 0 to 3; Ar1 ​​and Ar2 may each independently be a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms; and R 11 、R 12 , a and b are the same as those defined in Formula 6.

[0049] In one or more embodiments, the above formula 6 can be represented by the following formula 9-2 or formula 9-3:

[0050] Formula 9-2

[0051]

[0052] Formula 9-3

[0053]

[0054] In the above formulas 9-2 and 9-3, R y and R1 to R4 may each independently be a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring carbon atoms; d may be an integer selected from 0 to 5; L may be a directly linked, substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms; n may be an integer selected from 0 to 3; Ar1 ​​and Ar2 may each independently be a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms; and R 11 、R 12 , a and b are the same as those defined in Formula 6.

[0055] In one or more embodiments, the above formula 9-1 can be represented by the following formula 10-1:

[0056] Formula 10-1

[0057]

[0058] In the above formula 10-1, R x , R5 to R 12 , L, Ar1, Ar2, a to c and n are the same as defined in Formula 9-1.

[0059] In one or more embodiments, the above formula 9-2 can be represented by the following formula 10-2:

[0060] Formula 10-2

[0061]

[0062] In the above formula 10-2, R y , R1 to R4, R 11 、R 12 , L, Ar1, Ar2, a, b, d and n are the same as defined in Formula 9-2.

[0063] In the amine compound of one or more embodiments, n may be 1, and L may be directly linked.

[0064] In one or more embodiments, the amine compound represented by Formula 1 may be at least one selected from the group consisting of compounds shown in the following Compound Group 1.

[0065] In one or more embodiments of the present disclosure, the light-emitting device includes a first electrode, a hole transport region disposed (e.g., placed) on the first electrode, an emission layer disposed on the hole transport region, an electron transport region disposed on the emission layer, and a second electrode disposed on the electron transport region, wherein the hole transport region includes an amine compound according to one or more embodiments.

[0066] In one or more embodiments, the hole transport region may include a hole injection layer disposed on the first electrode and a hole transport layer disposed on the hole injection layer, and the hole transport layer or the hole injection layer may include the amine compound according to one or more embodiments.

[0067] In one or more embodiments, the hole transport region may include an electron blocking layer disposed on the hole transport layer. BRIEF DESCRIPTION OF THE DRAWINGS

[0068] The accompanying drawings are included to provide a further understanding of the present disclosure and are incorporated in and constitute a part of this specification. The accompanying drawings illustrate embodiments of the present disclosure and, together with the description, serve to explain the principles of the present disclosure. In the drawings:

[0069] Figure 1 is a plan view of a display device according to one or more embodiments of the present disclosure;

[0070] Figure 2 is a cross-sectional view of a display device according to one or more embodiments of the present disclosure;

[0071] Figure 3 A cross-sectional view schematically illustrating a light emitting device according to one or more embodiments of the present disclosure;

[0072] Figure 4 A cross-sectional view schematically illustrating a light emitting device according to one or more embodiments of the present disclosure;

[0073] Figure 5 A cross-sectional view schematically illustrating a light emitting device according to one or more embodiments of the present disclosure;

[0074] Figure 6 A cross-sectional view schematically illustrating a light emitting device according to one or more embodiments of the present disclosure;

[0075] Figure 7 is a cross-sectional view of a display device according to one or more embodiments of the present disclosure; and

[0076] Figure 8 is a cross-sectional view of a display device according to one or more embodiments of the present disclosure. DETAILED DESCRIPTION

[0077] The present disclosure can be modified in many alternative forms, and therefore specific embodiments will be provided as examples in the drawings and described in more detail. However, it should be understood that this description is not intended to limit the present disclosure to the particular forms disclosed, but is intended to cover all modifications, equivalents, and alternatives falling within the spirit and scope of the present disclosure.

[0078] When explaining each accompanying drawing, the same reference numerals are used to refer to the same elements. In the accompanying drawings, for the clarity of this disclosure, the size of each structure is exaggerated. It should be understood that although the terms "first", "second", etc. can be used to describe various elements, these elements should not be limited by these terms. These terms are only used to distinguish one element from another element. For example, without departing from the scope of this disclosure, the first element can be referred to as the second element, and similarly, the second element can be referred to as the first element. Terms in the singular form can include plural forms unless the context clearly indicates otherwise.

[0079] In this application, it should be understood that the term "including" or "having" specifies the presence of a feature, fixed number, step, process, element, component or a combination thereof disclosed in the specification, but does not exclude the possibility of the presence or addition of one or more other features, fixed numbers, steps, processes, elements, components or a combination thereof.

[0080] In this application, when a layer, film, region or plate is referred to as being "above" or "upper" another layer, film, region or plate, it can be not only directly on the layer, film, region or plate (without any intervening elements), but also one or more intervening layers, films, regions or plates may be present. Similarly, when a layer, film, region or plate is referred to as being "below" or "lower" another layer, film, region or plate, it can be not only directly below the layer, film, region or plate (without any intervening elements), but also one or more intervening layers, films, regions or plates may be present. Furthermore, it should be understood that when a layer, film, region or plate is referred to as being "on" another layer, film, region or plate, it can be not only disposed (e.g., placed) on the layer, film, region or plate, but also disposed below the layer, film, region or plate.

[0081] As used herein, the terms "use," "using," and "used" may be considered synonymous with the terms "utilize," "utilizing," and "utilized," respectively.

[0082] As used herein, expressions such as “at least one of,” “one of,” and “selected from,” when preceding a list of elements, modify the entire list of elements and do not modify the individual elements of the list.

[0083] As used herein, the term "and / or" includes any and all combinations of one or more of the associated listed items. Further, when describing embodiments of the present disclosure, the use of "may" refers to "one or more embodiments of the present disclosure."

[0084] As used herein, the terms "substantially," "about," and similar terms are used as terms of approximation, not as terms of degree, and are intended to account for the inherent deviations in measured or calculated values ​​that one of ordinary skill in the art would recognize. As used herein, "about" or "approximately" is inclusive of the recited value and means within the range of acceptable deviations from the particular value as determined by one of ordinary skill in the art, taking into account the measurement in question and the errors associated with the measurement of the particular quantity (i.e., the limitations of the measurement system). For example, "about" can mean within one or more standard deviations, or within ±30%, ±20%, ±10%, or ±5% of the recited value.

[0085] Any numerical range described herein is intended to include all subranges of the same numerical precision contained within the range. For example, the range of "1.0 to 10.0" is intended to include all subranges between (and including) the minimum value of 1.0 and the maximum value of 10.0, i.e., a minimum value equal to or greater than 1.0 and a maximum value equal to or less than 10.0, such as 2.4 to 7.6. Any maximum numerical limit described herein is intended to include all lower numerical limits contained therein, and any minimum numerical limit described in this specification is intended to include all higher numerical limits contained therein. Therefore, the applicant reserves the right to amend this specification (including the claims) to explicitly list any subranges contained within the ranges explicitly listed herein.

[0086] Hereinafter, embodiments of the present disclosure will be described with reference to the accompanying drawings.

[0087] Figure 1 A plan view of a display device DD for explaining one or more embodiments. Figure 2 is a cross-sectional view of a display device DD according to an embodiment. Figure 2 To explain the Figure 1 A cross-sectional view of a portion taken along line II'.

[0088] The display device DD may include a display panel DP and an optical layer PP disposed on the display panel DP. The display panel DP includes light-emitting devices ED-1, ED-2, and ED-3. The display device DD may include a plurality of light-emitting devices ED-1, ED-2, and ED-3. The optical layer PP may be disposed on the display panel DP and control light reflected from the display panel DP by external light. The optical layer PP may include, for example, a polarizing layer or a color filter layer. In one or more embodiments, the optical layer PP may be omitted from the display device DD of one or more embodiments.

[0089] The display panel DP may include a base layer BS, a circuit layer DP-CL provided on the base layer BS, and a display device layer DP-ED. The display device layer DP-ED may include a pixel defining film PDL, light-emitting devices ED-1, ED-2, and ED-3 disposed between portions of the pixel defining film PDL, and an encapsulation layer TFE disposed on the light-emitting devices ED-1, ED-2, and ED-3.

[0090] The base layer BS may be a member that provides a base surface on which the display device layer DP-ED is disposed. The base layer BS may be a glass substrate, a metal substrate, and / or a plastic substrate, etc. However, the embodiments of the present disclosure are not limited thereto, and the base layer BS may be an inorganic layer, an organic layer, or a composite material layer (e.g., including an inorganic material and an organic material).

[0091] In one or more embodiments, the circuit layer DP-CL is disposed on the base layer BS and may include a plurality of transistors. Each transistor may include a control electrode, an input electrode, and an output electrode. For example, the circuit layer DP-CL may include a switching transistor and a driving transistor to drive the light-emitting devices ED-1, ED-2, and ED-3 of the display device layer DP-ED.

[0092] Each of the light emitting devices ED-1, ED-2 and ED-3 may have a Figures 3 to 6 The structure of the light-emitting device ED according to one or more embodiments will be described below. Each of the light-emitting devices ED-1, ED-2, and ED-3 may include a first electrode EL1, a hole transport region HTR, emission layers EML-R, EML-G, and EML-B, an electron transport region ETR, and a second electrode EL2.

[0093] Figure 2 One or more embodiments are described in which the emission layers EML-R, EML-G, and EML-B of the light-emitting devices ED-1, ED-2, and ED-3 are arranged in corresponding openings OH defined in the pixel-defining film PDL, and the hole transport region HTR, the electron transport region ETR, and the second electrode EL2 are provided as common layers in all the light-emitting devices ED-1, ED-2, and ED-3. However, the embodiments of the present disclosure are not limited thereto, and in one or more embodiments, the hole transport region HTR and the electron transport region ETR may be provided by patterning in the opening OH defined in the pixel-defining film PDL. For example, the hole transport region HTR, the emission layers EML-R, EML-G, and EML-B, and the electron transport region ETR in one or more embodiments may be provided by patterning in an inkjet printing method.

[0094] The encapsulation layer TFE may cover the light-emitting devices ED-1, ED-2, and ED-3. The encapsulation layer TFE may seal the elements (e.g., the light-emitting devices ED-1, ED-2, and ED-3) of the display device layer DP-ED (e.g., may have a sealing function in the display device layer DP-ED). The encapsulation layer TFE may be a thin film encapsulation layer. The encapsulation layer TFE may be formed by laminating one or more layers. The encapsulation layer TFE includes at least one insulating layer. The encapsulation layer TFE according to one or more embodiments may include at least one inorganic film (hereinafter, encapsulation-inorganic film). The encapsulation layer TFE according to one or more embodiments may include at least one organic film (hereinafter, encapsulation-organic film) and at least one encapsulation-inorganic film.

[0095] The encapsulation-inorganic film protects the display device layer DP-ED from moisture / oxygen, and the encapsulation-organic film protects the display device layer DP-ED from foreign matter such as dust particles. The encapsulation-inorganic film may include silicon nitride, silicon oxynitride, silicon oxide, titanium oxide, and / or aluminum oxide, etc., but the embodiments of the present disclosure are not particularly limited thereto. The encapsulation-organic film may include acrylic compounds and / or epoxy compounds, etc. The encapsulation-organic film may include a photopolymerizable organic material, but the embodiments of the present disclosure are not particularly limited thereto.

[0096] The encapsulation layer TFE may be disposed on the second electrode EL2 and may be disposed to fill the opening OH.

[0097] refer to Figure 1 and Figure 2 , the display device DD may include a non-emission area NPXA and emission areas PXA-R, PXA-G, and PXA-B. The emission areas PXA-R, PXA-G, and PXA-B may each be an area that emits (or will emit) light generated by the light-emitting devices ED-1, ED-2, and ED-3, respectively. The emission areas PXA-R, PXA-G, and PXA-B may be spaced apart from each other on a plane (e.g., in a plan view).

[0098] Each of the light-emitting areas PXA-R, PXA-G, and PXA-B may be an area separated by a pixel-defining film PDL. The non-light-emitting area NPXA may be an area between adjacent light-emitting areas PXA-R, PXA-G, and PXA-B, which corresponds to a portion of the pixel-defining film PDL. In one or more embodiments, each of the light-emitting areas PXA-R, PXA-G, and PXA-B may correspond to a pixel. The pixel-defining film PDL may separate the light-emitting devices ED-1, ED-2, and ED-3. The emission layers EML-R, EML-G, and EML-B of the light-emitting devices ED-1, ED-2, and ED-3 may be disposed in an opening OH defined by the pixel-defining film PDL and separated from each other.

[0099] The light emitting areas PXA-R, PXA-G, and PXA-B may be divided into a plurality of groups according to the colors of light generated (or to be generated) from the plurality of light emitting devices ED-1, ED-2, and ED-3. Figure 1 and Figure 2 In the display device DD of one or more embodiments shown in FIG, three light-emitting regions PXA-R, PXA-G, and PXA-B that emit (or will emit) red light, green light, and blue light, respectively, are exemplarily illustrated. For example, the display device DD of one or more embodiments may include different red light-emitting regions PXA-R, green light-emitting regions PXA-G, and blue light-emitting regions PXA-B.

[0100] In a display device DD according to one or more embodiments, a plurality of light-emitting devices ED-1, ED-2, and ED-3 may emit light in different wavelength regions. For example, in one or more embodiments, the display device DD may include a first light-emitting device ED-1 that emits (or will emit) red light, a second light-emitting device ED-2 that emits (or will emit) green light, and a third light-emitting device ED-3 that emits (or will emit) blue light. For example, the red light-emitting region PXA-R, the green light-emitting region PXA-G, and the blue light-emitting region PXA-B of the display device DD may correspond to the first light-emitting device ED-1, the second light-emitting device ED-2, and the third light-emitting device ED-3, respectively.

[0101] However, the embodiments of the present disclosure are not limited thereto, and the first to third light-emitting devices ED-1, ED-2, and ED-3 may emit light within the same wavelength range, or at least one light-emitting device may emit light within different wavelength ranges. For example, the first to third light-emitting devices ED-1, ED-2, and ED-3 may all emit blue light.

[0102] The light emitting regions PXA-R, PXA-G, and PXA-B in the display device DD according to one or more embodiments may be arranged in a stripe form. Figure 1 , a plurality of red light-emitting areas PXA-R may be arranged along the second direction axis DR2, a plurality of green light-emitting areas PXA-G may be arranged along the second direction axis DR2, and a plurality of blue light-emitting areas PXA-B may be arranged along the second direction axis DR2. In addition, the red light-emitting areas PXA-R, the green light-emitting areas PXA-G, and the blue light-emitting areas PXA-B may be alternately arranged in this order along the first direction axis DR1.

[0103] Figure 1 and Figure 2Although all the light-emitting regions PXA-R, PXA-G, and PXA-B have the same area, the embodiments of the present disclosure are not limited thereto, and the light-emitting regions PXA-R, PXA-G, and PXA-B may have different areas from each other according to the wavelength range of the emitted light. In this case, the areas of the light-emitting regions PXA-R, PXA-G, and PXA-B may refer to their areas when viewed on a plane defined by the first direction axis DR1 and the second direction axis DR2 (e.g., in a plan view).

[0104] The arrangement of the light emitting areas PXA-R, PXA-G and PXA-B is not limited to Figure 1 The features explained in the above description are provided, and the order in which the red light emitting area PXA-R, the green light emitting area PXA-G and the blue light emitting area PXA-B are arranged can be variously appropriately combined and provided according to the characteristics of the display quality required in the display device DD. For example, the arrangement of the light emitting areas PXA-R, PXA-G and PXA-B can be as follows: Layout form ( is a registered trademark owned by Samsung Display Co., Ltd.) or in a diamond-shaped arrangement.

[0105] In one or more embodiments, the areas of the light-emitting regions PXA-R, PXA-G, and PXA-B may be different from each other. For example, in one or more embodiments, the area of ​​the green light-emitting region PXA-G may be smaller than the area of ​​the blue light-emitting region PXA-B, but the embodiments of the present disclosure are not limited thereto.

[0106] Below, Figures 3 to 6 Each of the light emitting devices ED according to the embodiment may include a first electrode EL1, a hole transport region HTR, an emission layer EML, an electron transport region ETR, and a second electrode EL2 sequentially stacked.

[0107] The light-emitting device ED of one or more embodiments may include the monoamine compound of one or more embodiments in the hole transport region HTR provided between the first electrode EL1 and the second electrode EL2, which will be described below. However, the embodiment is not limited thereto, and the light-emitting device ED may include the monoamine compound not only in the hole transport region HTR but also in the emission layer EML and / or the electron transport region ETR (which are among the plurality of functional layers provided between the first electrode EL1 and the second electrode EL2), or in the capping layer CPL provided on the second electrode EL2.

[0108] and Figure 3 Compare, Figure 4A cross-sectional view of a light emitting device ED according to one or more embodiments is illustrated, wherein the hole transport region HTR includes a hole injection layer HIL and a hole transport layer HTL, and the electron transport region ETR includes an electron injection layer EIL and an electron transport layer ETL. Figure 3 Compare, Figure 5 A cross-sectional view illustrating a light emitting device ED according to one or more embodiments, wherein the hole transport region HTR includes a hole injection layer HIL, a hole transport layer HTL, and an electron blocking layer EBL, and the electron transport region ETR includes an electron injection layer EIL, an electron transport layer ETL, and a hole blocking layer HBL. Figure 4 Compare, Figure 6 A cross-sectional view of a light emitting device ED according to one or more embodiments including a capping layer CPL disposed on the second electrode EL2 is illustrated.

[0109] The first electrode EL1 is conductive. The first electrode EL1 may be formed of a metal alloy or any suitable conductive compound. The first electrode EL1 may be an anode or a cathode. However, embodiments of the present disclosure are not limited thereto. In one or more embodiments, the first electrode EL1 may be a pixel electrode. The first electrode EL1 may be a transmissive electrode, a transflective electrode, or a reflective electrode. If the first electrode EL1 is a transmissive electrode, the first electrode EL1 may be formed using a transparent metal oxide such as indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), and / or indium tin zinc oxide (ITZO). If the first electrode EL1 is a transflective electrode or a reflective electrode, the first electrode EL1 may include Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF, Mo, Ti, compounds thereof, or mixtures thereof (e.g., a mixture of Ag and Mg), or a material including a multilayer structure such as LiF / Ca or LiF / Al. In one or more embodiments, the first electrode EL1 may have a multilayer structure including a reflective layer or a transflective layer formed of any of the above materials, and a transparent conductive layer formed of ITO, IZO, ZnO, ITZO, etc. For example, the first electrode EL1 may have a three-layer structure of ITO / Ag / ITO, but the embodiments of the present disclosure are not limited thereto. The thickness of the first electrode EL1 may be about 100 nm. to about For example, the thickness of the first electrode EL1 may be about to about

[0110] The hole transport region HTR is provided on the first electrode EL1. The hole transport region HTR may include at least one selected from the group consisting of a hole injection layer HIL, a hole transport layer HTL, a hole buffer layer, and an electron blocking layer EBL. The thickness of the hole transport region HTR may be, for example, about 100 Å. to about

[0111] The hole transport region HTR may have a single layer formed of a single material, a single layer formed of a plurality of different materials, or a multi-layered structure including a plurality of layers formed of a plurality of different materials.

[0112] For example, the hole transport region HTR may have a single layer structure of a hole injection layer HIL or a hole transport layer HTL, or may have a single layer structure formed of a hole injection material and a hole transport material. In one or more embodiments, the hole transport region HTR may have a single layer structure formed of a plurality of different materials, or a structure in which hole injection layer HIL / hole transport layer HTL, hole injection layer HIL / hole transport layer HTL / hole buffer layer, hole injection layer HIL / hole buffer layer, hole transport layer HTL / hole buffer layer, or hole injection layer HIL / hole transport layer HTL / electron blocking layer EBL are stacked in the order described from the first electrode EL1, but embodiments of the present disclosure are not limited thereto.

[0113] The hole transport region HTR in the light emitting device ED of one or more embodiments includes the monoamine compound according to one or more embodiments of the present disclosure.

[0114] As used herein, the term "substituted or unsubstituted" may refer to a functional group or substituent that is unsubstituted or substituted with at least one substituent selected from the group consisting of: a deuterium atom, a halogen atom, a cyano group, a nitro group, an amine group, a silyl group, an oxy group, a sulfenyl group, a sulfinyl group, a sulfonyl group, a carbonyl group, a boron group, a phosphine oxide group, a phosphine sulfide group, an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, a hydrocarbon ring group, an aryl group, and a heterocyclic group. In one or more embodiments, each of the substituents exemplified above may itself be substituted or unsubstituted. For example, a biphenyl group may be interpreted as an aryl group or a phenyl group substituted with a phenyl group.

[0115] In the description, the term "bonded to an adjacent group to form a ring" may indicate that it (e.g., a functional group or substituent) is bonded to an adjacent group to form a substituted or unsubstituted hydrocarbon ring, or a substituted or unsubstituted heterocycle. Hydrocarbon rings include aliphatic hydrocarbon rings and aromatic hydrocarbon rings. Heterocycles include aliphatic heterocycles and aromatic heterocycles. The ring formed by bonding to an adjacent group may be monocyclic or polycyclic. In one or more embodiments, the ring formed by bonding to each other may be connected to another ring to form a spiro structure.

[0116] In the description, the term "adjacent groups" may refer to a pair of substituents in which the first substituent is attached to an atom that is directly attached to another atom substituted by the second substituent; a pair of substituents attached to the same atom; or a pair of substituents in which the first substituent is located closest to the second substituent in space. For example, the two methyl groups in 1,2-dimethylbenzene can be interpreted as "adjacent groups" to each other, and the two ethyl groups in 1,1-diethylcyclopentane can be interpreted as "adjacent groups" to each other.

[0117] In the specification, examples of the halogen atom may include a fluorine atom, a chlorine atom, a bromine atom and / or an iodine atom.

[0118] In the specification, the alkyl group may be a linear, branched, or cyclic alkyl group. The number of carbon atoms in the alkyl group may be 1 to 50, 1 to 30, 1 to 20, 1 to 10, or 1 to 6. Examples of the alkyl group may include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, isobutyl, 2-ethylbutyl, 3,3-dimethylbutyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, cyclopentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 2-butylhexyl, cyclohexyl, 4-methylcyclohexyl, 4-tert-butylcyclohexyl, n-heptyl, 1-methylheptyl, 2,2-dimethylheptyl, 2-ethylheptyl, 2-butylheptyl, n-octyl, tert-octyl, 2-ethyloctyl, 2-butyloctyl, 2-hexyloctyl, 3,7-dimethyloctyl, cyclooctyl, n-nonyl, n-decyl, adamantyl, 2-ethyldecyl, 2-butyldecyl, 2-hexyldecyl The present invention also includes 2-decyl, 2-octyldecyl, 2-undecyl, 2-dodecyl, 2-ethyldodecyl, 2-butyldodecyl, 2-hexyldodecyl, 2-octyldodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, 2-ethylhexadecyl, 2-butylhexadecyl, 2-hexylhexadecyl, 2-octylhexadecyl, n-heptadecyl, n-octadecyl, n-nonadecyl, n-eicosyl, 2-ethyleicosyl, 2-butyleicosyl, 2-hexyleicosyl, 2-octyleicosyl, n-heneicosyl, n-docosyl, n-tricosyl, n-tetracosyl, n-pentacosyl, n-hexacosyl, n-heptacosyl, n-octacosyl, n-nonacosyl, n-triacontyl and the like, but the embodiments of the present disclosure are not limited thereto.

[0119] In the specification, an alkenyl group may refer to a hydrocarbon group having at least one carbon-carbon double bond in the middle and / or at the end of an alkyl group having 2 or more carbon atoms in its main hydrocarbon chain. The alkenyl group may be straight chain or branched. The carbon number is not specifically limited, but may be 2 to 30, 2 to 20, or 2 to 10. Examples of alkenyl groups include, but are not limited to, vinyl, 1-butenyl, 1-pentenyl, 1,3-butadienyl, styryl, styrylvinyl, and the like.

[0120] In the specification, an alkynyl group may refer to a hydrocarbon group having at least one carbon-carbon triple bond in the middle and / or at the end of an alkyl group having 2 or more carbon atoms in its main hydrocarbon chain. An alkynyl group may be straight or branched. The carbon number is not particularly limited, but may be 2 to 30, 2 to 20, or 2 to 10. Examples of alkynyl groups include, but are not limited to, ethynyl, propynyl, and the like.

[0121] In the specification, the hydrocarbon ring group may be any functional group or substituent derived from an aliphatic hydrocarbon ring, or any functional group or substituent derived from an aromatic hydrocarbon ring. The number of ring carbon atoms in the hydrocarbon ring group may be 5 to 60, 5 to 30, or 5 to 20.

[0122] As used herein, aryl refers to any functional group or substituent derived from an aromatic hydrocarbon ring. The aryl may be a monocyclic aryl or a polycyclic aryl. The number of ring carbon atoms in the aryl may be 6 to 30, 6 to 20, or 6 to 15. Examples of aryl may include phenyl, naphthyl, fluorenyl, anthracenyl, phenanthrenyl, biphenyl, terphenyl, quaterphenyl, pentyl, hexyl, triphenylene, pyrenyl, benzofluoranthenyl, 1,2-triphenylenyl, etc., but embodiments of the present disclosure are not limited thereto.

[0123] In the specification, the fluorenyl group may be substituted, and two substituents may be combined with each other to form a spiro structure. Examples of the case where the fluorenyl group is substituted are as follows. However, the embodiments of the present disclosure are not limited thereto:

[0124]

[0125] In the specification, a heterocyclic group may refer to any functional group or substituent derived from a ring containing at least one heteroatom selected from the group consisting of B, O, N, P, Si and S. Heterocyclic groups include aliphatic heterocyclic groups and aromatic heterocyclic groups. Aromatic heterocyclic groups may be heteroaryl groups. Aliphatic heterocyclic rings (e.g., aliphatic heterocyclic groups) and aromatic heterocyclic rings (e.g., aromatic heterocyclic groups) may each independently be monocyclic or polycyclic.

[0126] In the specification, the heterocyclic group may include at least one selected from the group consisting of B, O, N, P, Si and S as a heteroatom. If the heterocyclic group includes two or more heteroatoms, the two or more heteroatoms may be the same or different. The heterocyclic group may be a monocyclic heterocyclic group or a polycyclic heterocyclic group and has the concept of including a heteroaryl group. The ring carbon number (e.g., the number of ring carbon atoms) of the heterocyclic group may be 2 to 30, 2 to 20 or 2 to 10.

[0127] In the specification, the aliphatic heterocyclic group may include at least one heteroatom selected from the group consisting of B, O, N, P, Si, and S. The number of ring-forming carbon atoms in the aliphatic heterocyclic group may be 2 to 30, 2 to 20, or 2 to 10. Examples of the aliphatic heterocyclic group include an oxiranyl group, a pyranyl group, a pyrrolidinyl group, a piperidinyl group, a tetrahydrofuranyl group, a tetrahydrothienyl group, a thianyl group, a tetrahydropyranyl group, a 1,4-dioxanyl group, and the like, but embodiments of the present disclosure are not limited thereto.

[0128] In the specification, the heteroaryl group may include at least one selected from the group consisting of B, O, N, P, Si and S as a heteroatom. When the heteroaryl group contains two or more heteroatoms, the two or more heteroatoms may be the same or different from each other. The heteroaryl group may be a monocyclic heteroaryl group or a polycyclic heteroaryl group. The number of ring carbon atoms in the heteroaryl group may be 2 to 30, 2 to 20 or 2 to 10. Examples of heteroaryl groups may include thienyl, furyl, pyrrolyl, imidazolyl, triazolyl, pyridyl, bipyridyl, pyrimidyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, quinazolinyl, quinoxalinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolyl, indolyl, carbazolyl, N-arylcarbazolyl, N-heteroaryl Carbazolyl, N-alkylcarbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothiophenyl, dibenzothiophenyl, thienothiphenyl, benzofuranyl, phenanthrolinyl, thiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, thiadiazolyl, phenothiazinyl, dibenzosilyl, dibenzofuranyl, and the like, but the embodiments of the present disclosure are not limited thereto.

[0129] In the specification, the number of carbon atoms in the amino group is not particularly limited, but may be 1 to 30. The amino group may include an alkylamino group, an arylamino group, and / or a heteroarylamino group. Examples of the amino group include a methylamino group, a dimethylamino group, a phenylamino group, a diphenylamino group, a naphthylamino group, a 9-methyl-anthrylamino group, and the like, but embodiments of the present disclosure are not limited thereto.

[0130] In the specification, the above description about the arylene group applies to the arylene group except that the arylene group is a divalent group.

[0131] In the specification, the above description about the heteroarylene group applies to the heteroarylene group, except that the heteroarylene group is a divalent group.

[0132] In the specification, "-*" herein means a position to be linked (eg, a bonding site).

[0133] In the specification, the silyl group may be an alkylsilyl group or an arylsilyl group. Examples of the silyl group may include trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, ethyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, etc., but the embodiments of the present disclosure are not limited thereto.

[0134] In the specification, an oxy group may be an oxygen atom combined with an alkyl group or an aryl group as defined above. The oxy group may include an alkoxy group or an aryloxy group. The alkoxy group may be a straight chain, a branched chain, or a cyclic chain. The number of carbon atoms in the alkoxy group is not particularly limited, but may be, for example, 1 to 20 or 1 to 10. Examples of the oxy group may include a methoxy group, an ethoxy group, a n-propoxy group, an isopropoxy group, a butoxy group, a pentyloxy group, a hexyloxy group, an octyloxy group, a nonyloxy group, a decyloxy group, a benzyloxy group, etc., but embodiments of the present disclosure are not limited thereto.

[0135] In the specification, the thio group may include an alkylthio group or an arylthio group. The thio group may be a sulfur atom combined with an alkyl group or an aryl group as defined above. Examples of the thio group may include a methylthio group, an ethylthio group, a propylthio group, a pentylthio group, a hexylthio group, an octylthio group, a dodecylthio group, a cyclopentylthio group, a cyclohexylthio group, a phenylthio group, a naphthylthio group, etc., but embodiments of the present disclosure are not limited thereto.

[0136] In the specification, the boryl group may include an alkyl boryl group and an aryl boryl group. The boryl group may be a boron atom combined with an alkyl group or an aryl group as defined above. Examples of the boryl group may include dimethyl boryl, diethyl boryl, di-tert-butyl boryl, diphenyl boryl, etc., but the embodiments of the present disclosure are not limited thereto.

[0137] In the specification, the sulfinyl group may include an alkylsulfinyl group and an arylsulfinyl group. The sulfonyl group may include an alkylsulfonyl group and an arylsulfonyl group. The number of carbon atoms in the sulfinyl group and the sulfonyl group is not particularly limited, but may be, for example, 1 to 30.

[0138] In the specification, the number of carbon atoms in the carbonyl group is not particularly limited, but the carbon number may be, for example, 1 to 40, 1 to 30, or 1 to 20. For example, the carbonyl group may include the following structure, but is not limited thereto.

[0139]

[0140] The amine compound according to one or more embodiments of the present disclosure is represented by the following Formula 1:

[0141] Formula 1

[0142]

[0143] In Formula 1, R1 to R 10may each independently be a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, provided that R1 to R 10 At least one of them is represented by the following formula 2.

[0144] In Formula 1, Ring A and Ring B may each independently be represented by Formula 3 or Formula 4 below, provided that Ring A and Ring B are represented by different formulas (e.g., have different chemical structures). For example, when Ring A is represented by Formula 3 below, Ring B may be represented by Formula 4 below. When Ring A is represented by Formula 4 below, Ring B may be represented by Formula 3 below.

[0145] Formula 2

[0146]

[0147] In Formula 2, L may be a directly linked, substituted or unsubstituted arylene group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring-forming carbon atoms.

[0148] In Formula 2, n may be an integer selected from 0 to 3. When n is 2 or greater, a plurality of Ls may be the same as or different from each other.

[0149] In Formula 2, Ar1 and Ar2 may each independently be a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms.

[0150] Formula 3

[0151]

[0152] Formula 4

[0153]

[0154] In Equations 3 and 4, R 11 and R 12 Each may independently be a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms.

[0155] In Formula 3 and Formula 4, a may be an integer selected from 0 to 4, and b may be an integer selected from 0 to 6. When a is 2 or greater, a plurality of R 11 may be the same as or different from each other, and when b is 2 or greater, multiple R12 They may be the same as or different from each other.

[0156] In one or more embodiments, R1 to R 10 Only one of may be represented by Formula 2. In one or more other embodiments, the amine compound represented by Formula 1 may not include an amine group other than the amine group represented by Formula 2 (e.g., may include the amine group represented by Formula 2 as the only amine group). For example, the amine compound represented by Formula 1 may be a monoamine compound.

[0157] In one or more embodiments, Formula 1 may be represented by Formula 5 or Formula 6 below:

[0158] Formula 5

[0159]

[0160] Formula 6

[0161]

[0162] In Equations 5 and 6, R1 to R 12 , a and b are the same as those defined in Formula 1, Formula 3 and Formula 4.

[0163] In one or more embodiments, Formula 5 can be represented by the following Formula 7-1:

[0164] Formula 7-1

[0165]

[0166] In formula 7-1, R x and R5 to R 10 Each may independently be a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms.

[0167] In Formula 7-1, c may be an integer selected from 0 to 3, and when c is 2 or greater, a plurality of R x the same as or different from each other.

[0168] In Formula 7-1, L may be a directly linked, substituted or unsubstituted arylene group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring-forming carbon atoms.

[0169] In Formula 7-1, n may be an integer selected from 0 to 2, and when n is 2 or greater, a plurality of Ls are the same as or different from each other.

[0170] In Formula 7-1, Ar1 and Ar2 may each independently be a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms.

[0171] In formula 7-1, R 11 、R 12 , a and b are the same as those defined in Formula 5.

[0172] In one or more embodiments, Formula 5 may be represented by the following Formula 7-2 or Formula 7-3:

[0173] Formula 7-2

[0174]

[0175] Formula 7-3

[0176]

[0177] In Equations 7-2 and 7-3, R y and R1 to R4 may each independently be a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms.

[0178] In Formula 7-2 and Formula 7-3, d may be an integer selected from 0 to 5, and when d is 2 or greater, a plurality of R y the same as or different from each other.

[0179] In Formula 7-2 and Formula 7-3, L may be a directly linked, substituted or unsubstituted arylene group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring-forming carbon atoms.

[0180] In Formula 7-2 and Formula 7-3, n may be an integer selected from 0 to 3, and when n is 2 or greater, a plurality of Ls are the same as or different from each other.

[0181] In Formula 7-2 and Formula 7-3, Ar1 and Ar2 may each independently be a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms.

[0182] In Equations 7-2 and 7-3, R 11 、R 12 , a and b are the same as those defined in Formula 5.

[0183] In one or more embodiments, Formula 6 may be represented by the following Formula 8-1:

[0184] Formula 8-1

[0185]

[0186] In formula 8-1, R x , R5 to R 12 , L, Ar1, Ar2, a to c and n are the same as defined in Formula 6.

[0187] In one or more embodiments, Formula 6 may be represented by the following Formula 8-2:

[0188] Formula 8-2

[0189]

[0190] In formula 8-2, R y , R1 to R4, R 11 、R 12 , L, Ar1, Ar2, a, b, d and n are the same as defined in Formula 6.

[0191] In one or more embodiments, Formula 6 can be represented by the following Formula 9-1:

[0192] Formula 9-1

[0193]

[0194] In formula 9-1, R x and R5 to R 10 Each may independently be a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms.

[0195] In Formula 9-1, c may be an integer selected from 0 to 3, and when c is 2 or greater, a plurality of R x the same as or different from each other.

[0196] In Formula 9-1, L may be a directly linked, substituted or unsubstituted arylene group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring-forming carbon atoms.

[0197] In Formula 9-1, n may be an integer selected from 0 to 2, and when n is 2 or greater, a plurality of Ls are the same as or different from each other.

[0198] In Formula 9-1, Ar1 and Ar2 may each independently be a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms.

[0199] In formula 9-1, R 11 、R 12 , a and b are the same as those defined in Formula 6.

[0200] In one or more embodiments, Formula 6 may be represented by the following Formula 9-2 or Formula 9-3:

[0201] Formula 9-2

[0202]

[0203] Formula 9-3

[0204]

[0205] In Equations 9-2 and 9-3, R y and R1 to R4 may each independently be a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms.

[0206] In Formula 9-2 and Formula 9-3, d may be an integer selected from 0 to 5, and when d is 2 or greater, a plurality of R y the same as or different from each other.

[0207] In Formula 9-2 and Formula 9-3, L may be a directly linked, substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms.

[0208] In Formula 9-2 and Formula 9-3, n may be an integer selected from 0 to 3, and when n is 2 or greater, a plurality of Ls are the same as or different from each other.

[0209] In Formula 9-2 and Formula 9-3, Ar1 and Ar2 may each independently be a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms.

[0210] In Equations 9-2 and 9-3, R 11 、R 12 , a and b are the same as those defined in Formula 6.

[0211] In one or more embodiments, Formula 9-1 can be represented by the following Formula 10-1:

[0212] Formula 10-1

[0213]

[0214] In formula 10-1, R x , R5 to R 12 , L, Ar1, Ar2, a to c and n are the same as defined in Formula 9-1.

[0215] In one or more embodiments, Formula 9-2 may be represented by the following Formula 10-2:

[0216] Formula 10-2

[0217]

[0218] In formula 10-2, R y , R1 to R4, R 11 、R 12 , L, Ar1, Ar2, a, b, d and n are the same as defined in Formula 9-2.

[0219] In one or more embodiments, in any one of Formula 1 to Formula 10-2, n may be 1, and L may be directly connected.

[0220] The amine compound represented by Formula 1 according to one or more embodiments of the present disclosure may be any one selected from the compounds represented by the following compound group 1. However, the embodiments of the present disclosure are not limited thereto:

[0221] Compound Group 1

[0222]

[0223]

[0224]

[0225]

[0226] Will refer to Figures 3 to 6 A light emitting device ED according to one or more embodiments of the present disclosure is described.

[0227] As described above, the hole transport region HTR includes the amine compound according to one or more embodiments of the present disclosure as described above. For example, the hole transport region HTR includes the amine compound represented by Formula 1.

[0228] When the hole transport region HTR has a multilayer structure having a plurality of layers, any one of the plurality of layers may include the amine compound represented by Formula 1. For example, the hole transport region HTR may include a hole injection layer HIL disposed on the first electrode EL1 and a hole transport layer HTL disposed on the hole injection layer HIL, and the hole transport layer HTL or the hole injection layer HIL may include the amine compound represented by Formula 1. However, embodiments of the present disclosure are not limited thereto, and for example, the hole transport region HTR may include an electron blocking layer EBL disposed on the hole transport layer HTL, and the electron blocking layer EBL may include the amine compound represented by Formula 1.

[0229] The hole transport region HTR may include one or two or more amine compounds represented by Formula 1. For example, the hole transport region HTR may include at least one selected from the compounds represented by Compound Group 1 as described above.

[0230] The hole transport region HTR may be formed using one or more appropriate methods such as vacuum deposition, spin coating, casting, Langmuir-Brockett (LB) method, inkjet printing, laser printing, and / or laser induced thermal imaging (LITI).

[0231] The hole transport region HTR may further include a compound represented by the following formula H-1:

[0232] Formula H-1

[0233]

[0234] In the above formula H-1, L1 and L2 may each independently be a directly connected, substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms. In formula H-1, Ar1 and Ar2 may each independently be a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms. In one or more embodiments, in formula H-1, Ar3 may be a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms.

[0235] The compound represented by the above formula H-1 may be a monoamine compound. In one or more embodiments, the compound represented by the above formula H-1 may be a diamine compound, wherein at least one of Ar1 to Ar3 includes an amino group as a substituent. In one or more embodiments, the compound represented by the above formula H-1 may be a carbazole compound including a substituted or unsubstituted carbazole group in at least one of Ar1 or Ar2, or a fluorene compound including a substituted or unsubstituted fluorene group in at least one of Ar1 or Ar2.

[0236] The compound represented by formula H-1 may be represented by any one of the compounds of the following compound group H. However, the compounds listed in the following compound group H are examples, and the compound represented by formula H-1 is not limited to the compounds represented by the following compound group H:

[0237] Compound Group H

[0238]

[0239] The hole transport region HTR may further include a phthalocyanine compound (such as copper phthalocyanine), N 1 ,N 1 '-([1,1'-biphenyl]-4,4'-diyl)bis(N 1 -phenyl-N 4 ,N 4 -di-m-tolylphenyl-1,4-diamine)(DNTPD), 4,4',4"-[tris(3-methylphenyl)phenylamino]triphenylamine (m-MTDATA), 4,4',4"-tris(N,N-diphenylamino)triphenylamine (TDATA), 4,4',4"-tris[N-(1-naphthyl)-N-phenylamino]-triphenylamine (1-TNATA), 4,4',4"-tris[N-(2-naphthyl)-N-phenylamino]-triphenylamine (2-TNATA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDO T / PSS), polyaniline / dodecylbenzenesulfonic acid (PANI / DBSA), polyaniline / camphorsulfonic acid (PANI / CSA), polyaniline / poly(4-styrenesulfonate) (PANI / PSS), N,N'-di(naphthalene-l-yl)-N,N'-diphenyl-benzidine (NPB), triphenylamine-containing polyetherketone (TPAPEK), 4-isopropyl-4'-methyldiphenyliodonium [tetrakis(pentafluorophenyl)borate], dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile (HAT-CN), etc.

[0240] The hole transport region HTR may further include, for example, carbazole derivatives (such as N-phenylcarbazole and / or polyvinylcarbazole), fluorene derivatives, N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (TPD), triphenylamine derivatives (such as 4,4',4"-tris(N-carbazolyl)triphenylamine (TCTA)), N,N'-di(naphthalene-l-yl)-N,N'-diphenyl-benzidine (NPB), 4,4'-cyclohexylenebis[N,N-bis(4-methylphenyl)aniline] (TAPC), 4,4'-bis[N,N'-(3-tolyl)amino]-3,3'-dimethylbiphenyl (HMTPD), 1,3-bis(N-carbazolyl)benzene (mCP), etc.

[0241] The hole transport region HTR may further include 9-(4-tert-butylphenyl)-3,6-bis(triphenylsilyl)-9H-carbazole (CzSi), 9-phenyl-9H-3,9'-bicarbazole (CCP), 1,3-bis(1,8-dimethyl-9H-carbazole-9-yl)benzene (mDCP), and the like.

[0242] The hole transport region HTR may include the above-mentioned compound of the hole transport region HTR in at least one of the hole injection layer HIL, the hole transport layer HTL, and the electron blocking layer EBL. The thickness of the hole transport region HTR may be about to about For example, about to about When the hole transport region HTR includes the hole injection layer HIL, the hole injection layer HIL may have, for example, about to about When the hole transport region HTR includes the hole transport layer HTL, the hole transport layer HTL may have a thickness of about to about When the hole transport region HTR includes the electron blocking layer EBL, the electron blocking layer EBL may have a thickness of about to about If the thicknesses of the hole transport region HTR, the hole injection layer HIL, the hole transport layer HTL, and the electron blocking layer EBL satisfy the above respective ranges, satisfactory or appropriate hole transport characteristics can be achieved without a significant increase in driving voltage.

[0243] As described above, in addition to the hole injection layer HIL and the hole transport layer HTL, the hole transport region HTR may further include at least one selected from the group consisting of a hole buffer layer and an electron blocking layer EBL. The hole buffer layer can compensate for the resonance distance according to the wavelength of light emitted from the emission layer EML, thereby increasing the light emission efficiency. Any material that can be included in the hole transport region HTR can be used as the material included in the hole buffer layer. The electron blocking layer EBL is a layer used to prevent or reduce electron injection from the electron transport region ETR into the hole transport region HTR.

[0244] The emission layer EML is provided on the hole transport region HTR. The emission layer EML may have, for example, about to about or about to about The emission layer EML may have a single layer formed of a single material, a single layer formed of a plurality of different materials, or a multilayer structure having a plurality of layers formed of a plurality of different materials.

[0245] In the light emitting device ED of one or more embodiments, the emission layer EML may include a material selected from the group consisting of anthracene derivatives, pyrene derivatives, fluoranthene derivatives, 1,2-triphenylene derivatives, dehydrobenzanthracene derivatives, and triphenylene derivatives. For example, the emission layer EML may include anthracene derivatives and / or pyrene derivatives.

[0246] exist Figures 3 to 6 In each light emitting device ED of the illustrated embodiment, the emission layer EML may include a host and a dopant, and the emission layer EML may include a compound represented by the following formula E-1. The compound represented by the following formula E-1 may be used as a fluorescent host material.

[0247] Formula E-1

[0248]

[0249] In formula E-1, R 31 to R 40 Each may independently be a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, or may be bonded to an adjacent group to form a ring. 31 to R 40 Any one of may be bonded to an adjacent group to form a saturated hydrocarbon ring or an unsaturated hydrocarbon ring.

[0250] In Formula E-1, c and d may each independently be an integer selected from 0 to 5.

[0251] Formula E-1 can be represented by any one of the following compounds E1 to E19:

[0252]

[0253]

[0254] In one or more embodiments, the emission layer EML may include a compound represented by Formula E-2a or Formula E-2b below. The compound represented by Formula E-2a or Formula E-2b below may be used as a phosphorescent host material.

[0255] Formula E-2a

[0256]

[0257] In formula E-2a, L a It may be directly connected, or a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms. In one or more embodiments, in Formula E-2a, A1 to A5 may each independently be N or CR i . R a to R i Each of the R groups may independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted amino group, a substituted or unsubstituted thiol group, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, or may be bonded to an adjacent group to form a ring. a to R i Any of may be bonded to an adjacent group to form a hydrocarbon ring or heterocyclic ring containing N, O, S, etc. as a ring-constituting atom.

[0258] In formula E-2a, two or three selected from A1 to A5 may be N, and the rest may be CR i .

[0259] Formula E-2b

[0260]

[0261] In Formula E-2b, Cbz1 and Cbz2 may each independently be an unsubstituted carbazolyl group or a carbazolyl group substituted with an aryl group having 6 to 30 ring carbon atoms. b It may be a directly linked or substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms.

[0262] The compound represented by Formula E-2a or Formula E-2b may be represented by any one of the compounds of Compound Group E-2 described below. However, the compounds listed in Compound Group E-2 described below are examples, and the compound represented by Formula E-2a or Formula E-2b is not limited to the compounds represented by Compound Group E-2 described below.

[0263] Compound Group E-2

[0264]

[0265]

[0266] The emission layer EML may further include any appropriate material as a host material. For example, the emission layer EML may include at least one selected from the group consisting of bis[2-(diphenylphosphino)phenyl]ether oxide (DPEPO), 4,4'-bis(N-carbazol-9-yl)-1,1'-biphenyl (CBP), 1,3-bis(carbazol-9-yl)benzene (mCP), 2,8-bis(diphenylphosphino)dibenzo[b,d]furan (PPF), 4,4',4"-tris(carbazol-9-yl)-triphenylamine (TCTA), and 1,3,5-tris(1-phenyl-1H-benzo[d]imidazol-2-yl)benzene (TPBi) as a host material. However, embodiments of the present disclosure are not limited thereto, and for example, tris(8- Hydroxyquinolyl) aluminum (Alq3), poly (N-vinylcarbazole) (PVK), 9,10-di(naphthalene-2-yl)anthracene (ADN), 2-tert-butyl-9,10-di(naphthalene-2-yl)anthracene (TBADN), distyryl aromatic hydrocarbon (DSA), 4,4'-bis(9-carbazolyl)-2,2'-dimethyl-biphenyl (CDBP), 2-methyl-9,10-bis(naphthalene-2-yl)anthracene (MADN), hexaphenylcyclotriphosphazene (CP1), 1,4-bis(triphenylsilyl)benzene (UGH2), hexaphenylcyclotrisiloxane (DPSiO3), octaphenylcyclotetrasiloxane (DPSiO4), etc. can be used as the main materials.

[0267] The emission layer EML may include a compound represented by the following Formula Ma or Formula Mb. The compound represented by the following Formula Ma or Formula Mb may be used as a phosphorescent dopant material.

[0268] Formula Ma

[0269]

[0270] In the above formula Ma, Y1 to Y4 and Z1 to Z4 may each independently be CR1 or N; R1 to R4 may each independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted amine group, a substituted or unsubstituted thiol group, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, or may be bonded to an adjacent group to form a ring. In formula Ma, m is 0 or 1, and n is 2 or 3. In formula Ma, when m is 0, n is 3, and when m is 1, n is 2.

[0271] The compound represented by the formula Ma may be used as a red phosphorescent dopant or a green phosphorescent dopant.

[0272] The compound represented by formula Ma may be represented by any one of compounds M-a1 to M-a19 described below. However, compounds M-a1 to M-a19 described below are examples, and the compound represented by formula Ma is not limited to the compounds represented by compounds M-a1 to M-a19 described below.

[0273]

[0274] Compound M-a1 and Compound M-a2 may be used as red dopant materials, and Compound M-a3 and Compound M-a4 may be used as green dopant materials.

[0275] Formula Mb

[0276]

[0277] In formula Mb, Q1 to Q4 may each independently be C or N; and C1 to C4 may each independently be a substituted or unsubstituted hydrocarbon ring having 5 to 30 ring carbon atoms, or a substituted or unsubstituted heterocycle having 2 to 30 ring carbon atoms. 21 To L 24 Can be directly connected, *-o-**-s-* a substituted or unsubstituted divalent alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms; and e1 to e4 may each independently be 0 or 1. R 31 to R 39Each of them may be independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, or may be bonded to an adjacent group to form a ring; and d1 to d4 may each independently be an integer selected from 0 to 4.

[0278] The compound represented by Formula Mb may be used as a blue phosphorescent dopant or a green phosphorescent dopant.

[0279] The compound represented by Formula Mb may be represented by any one of the following compounds. However, the following compounds are examples, and the compound represented by Formula Mb is not limited to the compounds represented by the following compounds.

[0280]

[0281] In the compound included in the emission layer EML, the R-substituent, R 38 and R 39 Each of them may independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms.

[0282] The emission layer EML may include a compound represented by any one of Formulas Fa to Fc below. The compound represented by any one of Formulas Fa to Fc below may be used as a fluorescent dopant material.

[0283] Style

[0284]

[0285] In the formula Fa, R a to R j Two of them can be independently replaced by *--NAr1Ar2. a to R jThe other groups not substituted by *-NAr1Ar2 can each independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms. In *-NAr1Ar2, Ar1 and Ar2 can each independently be a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms. For example, at least one of Ar1 or Ar2 can be a heteroaryl group containing O or S as a ring atom.

[0286] Formula Fb

[0287]

[0288] In formula Fb, R a and R b Each of Ar1 to Ar4 may be independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, or may be bonded to an adjacent group to form a ring. Ar1 to Ar4 may each independently be a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms.

[0289] In formula Fb, U and V may each independently be a substituted or unsubstituted hydrocarbon ring having 5 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic ring having 2 to 30 ring carbon atoms.

[0290] In formula Fb, the number of rings represented by U and V can be 0 or 1 independently of each other. For example, in formula Fb, when the number of U or V is 1, one ring forms a condensed ring in the portion described as U or V, and when the number of U or V is 0, the ring described as U or V does not exist. For example, when the number of U is 0 and the number of V is 1, or when the number of U is 1 and the number of V is 0, the condensed ring with the fluorene core of formula Fb can be a four-membered ring cyclic compound (e.g., a benzofluorene moiety). In one or more embodiments, when each number of U and V is 0, the condensed ring with the fluorene core of formula Fb can be a three-membered ring cyclic compound (e.g., a fluorene moiety). In one or more embodiments, when each number of U and V is 1, the condensed ring with the fluorene core of formula Fb can be a five-membered ring cyclic compound (e.g., a dibenzofluorene moiety).

[0291] Formula Fc

[0292]

[0293] In formula Fc, A1 and A2 can each independently be O, S, Se or NR m , and R m It may be a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms. 11 Each may independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted amino group, a substituted or unsubstituted boron group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thiol group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, or may be bonded to an adjacent group to form a ring.

[0294] In Formula Fc, A1 and A2 may each independently bond to a substituent of an adjacent ring to form a fused ring. For example, when A1 and A2 are each independently NR m When A1 is bonded to R4 or R5 to form a ring. In one or more embodiments, A2 is bonded to R7 or R8 to form a ring.

[0295] In one or more embodiments, the emission layer EML may include styryl derivatives (e.g., 1,4-bis[2-(3-N-ethylcarbazolyl)vinyl]benzene (BCzVB), 4-(di-p-tolylamino)-4'-[(di-p-tolylamino)styryl]stilbene (DPAVB) and / or N-(4-((E)-2-(6-((E)-4-(diphenylamino)styryl)naphthalene-2-yl)vinyl)phenyl)-N-phenylaniline (N-BDAVBi)), perylene and / or its derivatives (e.g., 2,5,8,11-tetra-tert-butylperylene (TBP)), pyrene and / or its derivatives (e.g., 1,1'-dipyrene, 1,4-dipyrenylbenzene and / or 1,4-bis(N,N-diphenylamino)pyrene), etc. as dopant materials.

[0296] The emission layer EML may include a suitable phosphorescent dopant material. For example, a metal complex including iridium (Ir), platinum (Pt), osmium (Os), gold (Au), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), and / or thulium (Tm) may be used as a phosphorescent dopant. For example, bis(4,6-difluorophenylpyridine-N,C2') pyridinecarboxylate iridium (III) (FIrpic), bis(2,4-difluorophenylpyridine)-tetrakis(1-pyrazolyl) borate iridium (III) (FIr6), and / or octaethylporphyrin platinum (PtOEP) may be used as a phosphorescent dopant. However, embodiments of the present disclosure are not limited thereto.

[0297] The emission layer EML may include a quantum dot material. The core of the quantum dot may be selected from Group II-VI compounds, Group III-VI compounds, Group I-III-VI compounds, Group III-V compounds, Group III-II-V compounds, Group IV-VI compounds, Group IV elements, Group IV compounds, and combinations thereof.

[0298] The II-VI compound may be selected from the group consisting of: a binary compound selected from the group consisting of CdSe, CdTe, CdS, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, MgSe, MgS, and mixtures thereof; a ternary compound selected from the group consisting of CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, CdZnSe , CdZnTe, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, MgZnSe, MgZnS and mixtures thereof; and a quaternary compound selected from the group consisting of HgZnTeS, CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe, HgZnSTe and mixtures thereof.

[0299] The Group III-VI compounds may include binary compounds such as In2S3 and / or In2Se3; ternary compounds such as InGaS3 and / or InGaSe3; or any combination thereof.

[0300] The Group I-III-VI compounds may be selected from the group consisting of: ternary compounds selected from the group consisting of AgInS, AgInS2, CuInS, CuInS2, AgGaS2, CuGaS2, CuGaO2, AgGaO2, AgAlO2 and mixtures thereof; and quaternary compounds such as AgInGaS2 and / or CuInGaS2.

[0301] The III-V compound may be selected from the group consisting of a binary compound selected from the group consisting of GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, InSb, and mixtures thereof; a ternary compound selected from the group consisting of GaNPs, GaNAs, GaNSb, GaPAs, GaPSb, AlNPs, AlNAs, AlNSb, AlPAs, AlPSb, InGaP, InAlP, InNP, InNAs, InNSb, InPAs, InPSb, and mixtures thereof; and a quaternary compound selected from the group consisting of GaAlNPs, GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNPs, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNPs, InAlNAs, InAlNSb, InAlPAs, InAlPSb, and mixtures thereof. The III-V compound may further include a Group II metal. For example, InZnP or the like may be selected as the Group III-II-V compound.

[0302] The Group IV-VI compound may be selected from the group consisting of a binary compound selected from the group consisting of SnS, SnSe, SnTe, PbS, PbSe, PbTe, and mixtures thereof; a ternary compound selected from the group consisting of SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, SnPbTe, and mixtures thereof; and a quaternary compound selected from the group consisting of SnPbSSe, SnPbSeTe, SnPbSTe, and mixtures thereof. The Group IV element may be selected from the group consisting of Si, Ge, and mixtures thereof. The Group IV compound may be a binary compound selected from the group consisting of SiC, SiGe, and mixtures thereof.

[0303] The binary, ternary, and / or quaternary compounds may be present in a uniform concentration distribution within the particle, or may be present in the same particle with partially different concentration distributions. In one or more embodiments, the quantum dots may have a core / shell structure, wherein one quantum dot surrounds another quantum dot. The interface between the core and the shell may have a concentration gradient, wherein the concentration of the element present in the shell decreases toward the core.

[0304] In some embodiments, quantum dots may have the above-described core / shell structure including a core having nanocrystals and a shell surrounding the core (e.g., around the core). The shell of the quantum dot can be used as a protective layer to prevent or reduce chemical modification of the core to maintain semiconductor properties, and / or as a charging layer to impart electrophoretic properties to the quantum dot. The shell can be a single layer or multiple layers. The interface between the core and the shell can have a concentration gradient, wherein the concentration of the element present in the shell decreases toward the core. Examples of the shell of the quantum dot can include metal or non-metal oxides, semiconductor compounds, or combinations thereof.

[0305] For example, the metal or non-metal oxide may be a binary compound such as SiO2, Al2O3, TiO2, ZnO, MnO, Mn2O3, Mn3O4, CuO, FeO, Fe2O3, Fe3O4, CoO, Co3O4 and / or NiO; and / or a ternary compound such as MgAl2O4, CoFe2O4, NiFe2O4 and / or CoMn2O4, but the embodiments of the present disclosure are not limited thereto.

[0306] In one or more embodiments, the semiconductor compound may be, for example, CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnSeS, ZnTeS, GaAs, GaP, GaSb, HgS, HgSe, HgTe, InAs, InP, InGaP, InSb, AlAs, AlP, AlSb, etc., but the embodiments of the present disclosure are not limited thereto.

[0307] The quantum dots may have a full width at half maximum (FWHM) of a light emission wavelength spectrum of about 45 nm or less, for example, about 40 nm or less, or about 30 nm or less, and may improve color purity or color reproducibility within any of the above ranges. In one or more embodiments, light emitted by the quantum dots is emitted in all directions, thereby improving a wide viewing angle.

[0308] In one or more embodiments, although the form of quantum dots is not particularly limited as long as it is in a suitable form, for example, quantum dots in the form of spherical, pyramidal, multi-arm and / or cubic nanoparticles, nanotubes, nanowires, nanofibers, nanoplates, etc. can be used.

[0309] Quantum dots can control the color of emitted light depending on their particle size. Therefore, quantum dots can have various light emission colors such as blue, red and / or green.

[0310] exist Figures 3 to 6In each light emitting device ED of the embodiment illustrated in FIG, an electron transport region ETR is provided on the emission layer EML. The electron transport region ETR may include at least one selected from the group consisting of a hole blocking layer HBL, an electron transport layer ETL, and an electron injection layer EIL, but the embodiments of the present disclosure are not limited thereto.

[0311] The electron transport region ETR may have a single layer formed of a single material, a single layer formed of a plurality of different materials, or a multilayer structure including a plurality of layers formed of a plurality of different materials.

[0312] For example, the electron transport region ETR may have a single layer structure of an electron injection layer EIL or an electron transport layer ETL, or may have a single layer structure formed of an electron injection material and an electron transport material. In one or more embodiments, the electron transport region ETR may have a single layer structure formed of a plurality of different materials, or may have a structure in which an electron transport layer ETL / electron injection layer EIL, or a hole blocking layer HBL / electron transport layer ETL / electron injection layer EIL is stacked in the order described from the emission layer EML, but the embodiments of the present disclosure are not limited thereto. The electron transport region ETR may have, for example, about to about thickness.

[0313] The electron transport region ETR can be formed by using one or more appropriate methods such as vacuum deposition, spin coating, casting, Langmuir-Brockett (LB) method, inkjet printing, laser printing, laser induced thermal imaging (LITI), etc.

[0314] The electron transport layer ETL may include a compound represented by the following formula ET-1:

[0315] Formula ET-1

[0316]

[0317] In formula ET-1, at least one of X1 to X3 is N, and the others are CR a . R a It may be a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms. Ar1 to Ar3 may each independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms.

[0318] In Formula ET-1, a to c may each independently be an integer selected from 0 to 10. In Formula ET-1, L1 to L3 may each independently be a directly linked, substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms. When a to c are each independently an integer of 2 or greater, each L1 to L3 may each independently be a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms.

[0319] The electron transport region ETR may include an anthracene compound. However, the embodiments of the present disclosure are not limited thereto, and the electron transport region ETR may include, for example, tris(8-hydroxyquinoline)aluminum (Alq3), 1,3,5-tris[(3-pyridyl)-phenyl-3-yl]benzene, 2,4,6-tris(3'-(pyridin-3-yl)biphenyl-3-yl)-1,3,5-triazine, 2-(4-(N-phenylbenzimidazol-1-yl)phenyl)-9,10-dinaphthylanthracene, 1,3,5-tris(1-phenyl-1H-benzo[d]imidazole-2- 1,2,4-triazole (NTAZ), 2-(4-biphenyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole ( t Bu-PBD), bis(2-methyl-8-quinolinolhydroxy-N1,O8)-(1,1'-biphenyl-4-hydroxy)aluminum (BAlq), bis(benzoquinolinol-10-hydroxy)beryllium (Bebq2), 9,10-di(naphthalene-2-yl)anthracene (ADN), 1,3-bis[3,5-di(pyridin-3-yl)phenyl]benzene (BmPyPhB) or a mixture thereof.

[0320] In one or more embodiments, the electron transport region ETR may include a metal halide (such as LiF, NaCl, CsF, RbCl, RbI, CuI and / or KI), a lanthanide metal (such as Yb) and / or a co-deposited material of a metal halide and a lanthanide metal. For example, the electron transport region ETR may include KI:Yb, RbI:Yb, etc. as a co-deposited material. In one or more embodiments, the electron transport region ETR may be formed using metal oxides such as Li2O and / or BaO, or 8-hydroxy-quinoline lithium (Liq), etc., but the embodiments of the present disclosure are not limited thereto. The electron transport region ETR may also be formed by a mixed material of an electron transport material and an insulating organic metal salt. The insulating organic metal salt may be a material with an energy band gap of about 4 eV or greater. For example, the insulating organic metal salt may include a metal acetate, a metal benzoate, a metal acetoacetate, a metal acetylacetonate and / or a metal stearate, but the embodiments of the present disclosure are not limited thereto.

[0321] The electron transport region ETR may include any of the above-mentioned compounds of the electron transport region ETR in at least one selected from the group consisting of the electron injection layer EIL, the electron transport layer ETL, and the hole blocking layer HBL.

[0322] When the electron transport region ETR includes the electron transport layer ETL, the electron transport layer ETL may have a thickness of about to about For example, about to about If the thickness of the electron transport layer ETL satisfies any of the above ranges, satisfactory or appropriate electron transport characteristics can be obtained without a significant increase in driving voltage. When the electron transport region ETR includes the electron injection layer EIL, the electron injection layer EIL may have a thickness of about to about For example, about to about If the thickness of the electron injection layer EIL satisfies any of the above ranges, satisfactory or appropriate electron injection characteristics can be obtained without a significant increase in driving voltage.

[0323] The second electrode EL2 is provided on the electron transport region ETR. The second electrode EL2 may be a common electrode. The second electrode EL2 may be a cathode or an anode, but the embodiments of the present disclosure are not limited thereto. For example, when the first electrode EL1 is an anode, the second electrode EL2 may be a cathode, and when the first electrode EL1 is a cathode, the second electrode EL2 may be an anode.

[0324] The second electrode EL2 may be a transmissive electrode, a transflective electrode, or a reflective electrode. When the second electrode EL2 is a transmissive electrode, the second electrode EL2 may be formed of a transparent metal oxide, such as indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), indium tin zinc oxide (ITZO), etc.

[0325] When the second electrode EL2 is a transflective electrode or a reflective electrode, the second electrode EL2 may include Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF, Mo, Ti, Yb, or a compound or mixture thereof (e.g., AgMg, AgYb and / or MgYb), or a material including a multilayer structure such as LiF / Ca or LiF / Al. In one or more embodiments, the second electrode EL2 may have a multilayer structure including a reflective layer or a transflective layer formed of any of the above materials, and a transparent conductive layer formed of ITO, IZO, ZnO, ITZO, or the like. For example, the second electrode EL2 may include any of the above metal materials, a combination of at least two of the above metal materials, an oxide of the above metal materials, or the like.

[0326] In one or more embodiments, the second electrode EL2 may be connected to the auxiliary electrode. If the second electrode EL2 is connected to the auxiliary electrode, the resistance of the second electrode EL2 may be reduced.

[0327] In one or more embodiments, a capping layer CPL may be further provided on the second electrode EL2 of the light emitting device ED of one or more embodiments. The capping layer CPL may include a plurality of layers or a single layer.

[0328] In one or more embodiments, the capping layer CPL may be an organic layer or an inorganic layer. For example, when the capping layer CPL includes an inorganic material, the inorganic material may include an alkali metal compound such as LiF, an alkaline earth metal compound such as MgF2, SiON, SiN x and / or SiO y wait.

[0329] For example, when the capping layer CPL includes an organic material, the organic material may include 2,2'-dimethyl-N,N'-di-[(1-naphthyl)-N,N'-diphenyl]-1,1'-biphenyl-4,4'-diamine (α-NPD), NPB, TPD, m-MTDATA, Alq3, CuPc, N4,N4,N4',N4'-tetrakis(biphenyl-4-yl)biphenyl-4,4'-diamine (TPD15), 4,4',4"-tris(carbazol-9-yl)triphenylamine (TCTA), etc.; epoxy resin; and / or acrylate such as methacrylate. However, embodiments of the present disclosure are not limited thereto, and the organic material may also include any one of the following compounds P1 to P5:

[0330]

[0331]

[0332] The refractive index of the capping layer CPL may be about 1.6 or greater. For example, for light with a wavelength ranging from about 550 nm to about 660 nm, the refractive index of the capping layer CPL may be about 1.6 or greater.

[0333] Figure 7 and Figure 8 Each is a cross-sectional view of a display device according to one or more embodiments. Figure 7 and Figure 8 In describing the display device of one or more embodiments, the display device already described will not be described again. Figures 1 to 6 The features described in , but the differences will be mainly described.

[0334] refer to Figure 7 , a display device DD according to one or more embodiments may include a display panel DP including a display device layer DP-ED, a light control layer CCL disposed on the display panel DP, and a color filter layer CFL.

[0335] exist Figure 7 In one or more embodiments explained in , the display panel DP may include a base layer BS, a circuit layer DP-CL provided on the base layer BS, and a display device layer DP-ED, and the display device layer DP-ED may include a light emitting device ED.

[0336] The light emitting device ED may include a first electrode EL1, a hole transport region HTR disposed on the first electrode EL1, an emission layer EML disposed on the hole transport region HTR, an electron transport region ETR disposed on the emission layer EML, and a second electrode EL2 disposed on the electron transport region ETR. In one or more embodiments, as described above Figures 4 to 6 The structure of the light emitting device ED can be similarly applied to Figure 7 The structure of the light emitting device ED shown in FIG.

[0337] refer to Figure 7 , the emission layer EML may be provided in the opening OH defined in the pixel defining film PDL. For example, the emission layer EML provided corresponding to each of the light-emitting regions PXA-R, PXA-G, and PXA-B, separated by the pixel defining film PDL, may emit light within the same wavelength range. In the display device DD of one or more embodiments, the emission layer EML may emit blue light. In one or more embodiments, the emission layer EML may be provided as a common layer in (e.g., passing through) the entire light-emitting regions PXA-R, PXA-G, and PXA-B.

[0338] The light control layer (CCL) may be disposed on the display panel DP. The light control layer (CCL) may include a light converter. The light converter may be quantum dots and / or phosphors. The light converter may convert the wavelength of light provided by the light converter to emit the light. For example, the light control layer (CCL) may be a layer containing quantum dots or a layer containing phosphors.

[0339] The light control layer CCL may include a plurality of light control units CCP1, CCP2, and CCP3. The light control units CCP1, CCP2, and CCP3 may be spaced apart from each other (in a plan view).

[0340] refer to Figure 7 , the partition patterns BMP may be disposed between the light control units CCP1 , CCP2 , and CCP3 that are spaced apart from each other, but embodiments of the present disclosure are not limited thereto. Figure 7 It is explained that the partition pattern BMP does not overlap with the light control units CCP1 , CCP2 , and CCP3 , but at least a portion of the edges of the light control units CCP1 , CCP2 , and CCP3 may be defined as (eg, overlap) the partition pattern BMP.

[0341] The light control layer CCL may include a first light control unit CCP1 containing a first quantum dot QD1 that converts (or will convert) the first color light provided by the light-emitting device ED into a second color light, a second light control unit CCP2 containing a second quantum dot QD2 that converts (or will convert) the first color light into a third color light, and a third light control unit CCP3 that transmits (or will transmit) the first color light.

[0342] In one or more embodiments, the first light control unit CCP1 may provide red light as the second color light, and the second light control unit CCP2 may provide green light as the third color light. The third light control unit CCP3 may transmit blue light, which is the first color light provided in the light-emitting device ED. For example, the first quantum dot QD1 may be a red quantum dot, and the second quantum dot QD2 may be a green quantum dot. The same description provided above applies to quantum dots QD1 and QD2.

[0343] In one or more embodiments, the light control layer CCL may further include a scatterer SP. The first light control unit CCP1 may include a first quantum dot QD1 and a scatterer SP, the second light control unit CCP2 may include a second quantum dot QD2 and a scatterer SP, and the third light control unit CCP3 may not include any quantum dots but may include a scatterer SP.

[0344] The scatterers SP may be inorganic particles. For example, the scatterers SP may include at least one selected from the group consisting of TiO2, ZnO, Al2O3, SiO2, and hollow silicon oxide. The scatterers SP may include any one of TiO2, ZnO, Al2O3, SiO2, and hollow silicon oxide, or may be a mixture of at least two materials selected from TiO2, ZnO, Al2O3, SiO2, and hollow silicon oxide.

[0345] The first light control unit CCP1, the second light control unit CCP2, and the third light control unit CCP3 may respectively include base resins BR1, BR2, and BR3 of dispersed quantum dots QD1 and QD2 and scatterers SP. In an embodiment, the first light control unit CCP1 may include first quantum dots QD1 and scatterers SP dispersed in a first base resin BR1, the second light control unit CCP2 may include second quantum dots QD2 and scatterers SP dispersed in a second base resin BR2, and the third light control unit CCP3 may include scatterers SP dispersed in a third base resin BR3. Base resins BR1, BR2, and BR3 are media in which quantum dots QD1 and QD2 and scatterers SP are dispersed, and may be formed from various resin compositions (which may be generally referred to as adhesives). For example, base resins BR1, BR2, and BR3 may be acrylic resins, urethane resins, silicone resins, epoxy resins, and the like. Base resins BR1, BR2, and BR3 may be transparent resins. In an embodiment, the first base resin BR1, the second base resin BR2, and the third base resin BR3 may be the same as or different from each other.

[0346] The light control layer CCL may include an isolation layer BFL1. The isolation layer BFL1 may be used to prevent or reduce the penetration of moisture and / or oxygen (hereinafter, referred to as "moisture / oxygen"). The isolation layer BFL1 may be provided on the light control units CCP1, CCP2, and CCP3 to block or reduce exposure of the light control units CCP1, CCP2, and CCP3 to moisture / oxygen. The isolation layer BFL1 may cover the light control units CCP1, CCP2, and CCP3. In one or more embodiments, the isolation layer BFL2 may be provided between the light control units CCP1, CCP2, and CCP3 and the optical filters CF1, CF2, and CF3.

[0347] Isolation layers BFL1 and BFL2 may include at least one inorganic layer. For example, isolation layers BFL1 and BFL2 may each independently include an inorganic material. For example, isolation layers BFL1 and BFL2 may include silicon nitride, aluminum nitride, zirconium nitride, titanium nitride, hafnium nitride, tantalum nitride, silicon oxide, aluminum oxide, titanium oxide, tin oxide, cerium oxide, silicon oxynitride, or any suitable metal film that ensures light transmittance. In one or more embodiments, isolation layers BFL1 and BFL2 may each independently further include an organic film. Isolation layers BFL1 and BFL2 may each independently be formed of a single layer or multiple layers.

[0348] In the display device DD of one or more embodiments, the color filter layer CFL may be disposed on the light control layer CCL. For example, the color filter layer CFL may be directly disposed on the light control layer CCL. In this case, the isolation layer BFL2 may be omitted.

[0349] The color filter layer CFL may include a light shielding unit BM and filters CF1, CF2, and CF3. The color filter layer CFL may include a first filter CF1 configured to transmit second color light, a second filter CF2 configured to transmit third color light, and a third filter CF3 configured to transmit first color light. For example, the first filter CF1 may be a red filter, the second filter CF2 may be a green filter, and the third filter CF3 may be a blue filter. Each of the filters CF1, CF2, and CF3 may include a polymerized photosensitive resin and a pigment and / or dye. The first filter CF1 may include a red pigment and / or dye, the second filter CF2 may include a green pigment and / or dye, and the third filter CF3 may include a blue pigment and / or dye. However, embodiments of the present disclosure are not limited thereto, and the third filter CF3 may not include a pigment or dye. The third filter CF3 may include a polymerized photosensitive resin and may not include a pigment or dye. The third filter CF3 may be transparent. The third filter CF3 may be formed of a transparent photosensitive resin.

[0350] In addition, in one or more embodiments, the first filter CF1 and the second filter CF2 may be yellow filters. The first filter CF1 and the second filter CF2 may not be separated but may be provided as one filter.

[0351] The light shielding unit BM may be a black matrix. The light shielding unit BM may include an organic light shielding material or an inorganic light shielding material containing a black pigment and / or dye. The light shielding unit BM may prevent or reduce light leakage and may separate the boundaries between adjacent filters CF1, CF2, and CF3. In one or more embodiments, the light shielding unit BM may be formed of a blue filter.

[0352] The first to third filters CF1, CF2, and CF3 may be disposed to correspond to the red light emitting area PXA-R, the green light emitting area PXA-G, and the blue light emitting area PXA-B, respectively.

[0353] The base substrate BL may be disposed on the color filter layer CFL. The base substrate BL may be a member providing a base surface, and the color filter layer CFL and / or the light control layer CCL, etc., are disposed on the base surface. The base substrate BL may be a glass substrate, a metal substrate, a plastic substrate, etc. However, embodiments of the present disclosure are not limited thereto, and the base substrate BL may be an inorganic layer, an organic layer, or a composite material layer (e.g., including inorganic and organic materials). In one or more embodiments, the base substrate BL may be omitted.

[0354] Figure 8 A cross-sectional view illustrating a portion of a display device according to one or more embodiments. Figure 8 The interpretation corresponds to Figure 7 sectional view of a portion of the display panel DP. In the display device DD-TD of one or more embodiments, the light emitting device ED-BT may include a plurality of light emitting structures OL-B1, OL-B2, and OL-B3. The light emitting device ED-BT may include a first electrode EL1 and a second electrode EL2 facing each other, and the plurality of light emitting structures OL-B1, OL-B2, and OL-B3 may be sequentially stacked between the first electrode EL1 and the second electrode EL2 in a thickness direction. Each of the light emitting structures OL-B1, OL-B2, and OL-B3 may include an emission layer EML ( Figure 7 ) and a hole transport region HTR and an electron transport region ETR ( Figure 7 ).

[0355] For example, the light-emitting device ED-BT included in the display apparatus DD-TD of one or more embodiments may be a light-emitting device having a tandem structure and including a plurality of emission layers EML.

[0356] exist Figure 8 In one or more embodiments described in

[0026] , each light emitted from each of the light-emitting structures OL-B1, OL-B2, and OL-B3 may be blue light. However, the embodiments of the present disclosure are not limited thereto, and the light emitted from each of the light-emitting structures OL-B1, OL-B2, and OL-B3 may be within a different wavelength range from one another. For example, a light-emitting device ED-BT (including a plurality of light-emitting structures OL-B1, OL-B2, and OL-B3, each of which emits light within a different wavelength range from one another) may emit white light.

[0357] The charge generation layers CGL1 and CGL2 may be disposed between adjacent light emitting structures OL-B1, OL-B2, and OL-B3. The charge generation layers CGL1 and CGL2 may include a p-type charge generation layer and / or an n-type charge generation layer.

[0358] Hereinafter, the present embodiment will be described in detail with reference to specific examples and comparative examples. The following examples are merely illustrations to help understand the present disclosure, and the scope of the present disclosure is not limited thereto.

[0359] Synthesis example

[0360] The amine compound according to one or more embodiments of the present disclosure may be synthesized, for example, as follows: However, the synthesis method of the amine compound according to one or more embodiments of the present disclosure is not limited thereto.

[0361] 1. Synthesis of compound 1

[0362]

[0363] 1-1. (Synthesis of Intermediate 1a)

[0364] 1,8-Dibromonaphthalene (1.0 eq.), phenylboronic acid (1.0 eq.), tetrakis(triphenylphosphine)palladium (0.05 eq.) and potassium carbonate (2.0 eq.) were dissolved in THF:H2O at a volume ratio of about 4:1, and the mixture was stirred at about 90°C for about 12 hours under a nitrogen atmosphere. After cooling, the resulting product was washed three times with ethyl acetate and water, and then an organic layer was obtained. The resulting organic layer was dried over MgSO4 and then dried under reduced pressure. The dried organic layer was purified by column chromatography to obtain Intermediate 1a. (Yield: 62%)

[0365] 1-2. (Synthesis of Intermediate 1c)

[0366] 1-Bronaphthalene (1.0 eq.), bis(pinacolato)diboron (2.0 eq.), potassium acetate (4.0 eq.), and palladium acetate (0.05 eq.) were dissolved in 1,4-dioxane, and the mixture was stirred at about 80°C for about 3 hours under a nitrogen atmosphere. After cooling, the resulting product was washed three times with ethyl acetate and water, and an organic layer was obtained. The resulting organic layer was dried over MgSO4 and then dried under reduced pressure. The dried organic layer was purified by column chromatography to obtain Intermediate 1c. (Yield: 85%)

[0367] 1-3. (Synthesis of Intermediate 1d)

[0368] Intermediate 1c (1.0 eq.), 3-bromobenzoyl chloride (1.5 eq.), tetrakis(triphenylphosphine)palladium (0.05 eq.), and potassium carbonate (2.0 eq.) were dissolved in THF:H2O at a volume ratio of about 4:1, and the mixture was stirred at about 80°C under a nitrogen atmosphere for about 12 hours. After cooling, the resulting product was washed three times with ethyl acetate and water, and an organic layer was obtained. The resulting organic layer was dried over MgSO4 and then dried under reduced pressure. The dried organic layer was purified by column chromatography to obtain Intermediate 1d. (Yield: 66%)

[0369] 1-4, (Synthetic intermediate 1e)

[0370] Intermediate 1d (1.0 eq.), palladium acetate (0.01 eq.), and silver (I) oxide (1.5 eq.) were dissolved in trifluoroacetic acid, and the mixture was stirred at approximately 130° C. under a nitrogen atmosphere for approximately 36 hours. After cooling, the resulting product was washed three times with ethyl acetate and water, and an organic layer was obtained. The resulting organic layer was dried over MgSO 4 and then dried under reduced pressure. The dried organic layer was purified by column chromatography to obtain Intermediate 1e. (Yield: 70%)

[0371] 1-5. (Synthesis of Intermediate 1b and Intermediate 1f)

[0372] Anhydrous diethyl ether was added dropwise to intermediate 1a (1.0 eq.), magnesium (5.0 eq.) and dichloroethane (0.01 eq.), and the mixture was stirred at about 40° C. for about 1 hour under a nitrogen atmosphere to produce a solution of intermediate 1b. After the solution of intermediate 1b was cooled to about 0° C., the cooled solution was slowly added dropwise to a solution of intermediate 1e dissolved in THF, and the mixture was stirred at about 40° C. for about 1 hour. After cooling, ammonium chloride solution was slowly added dropwise thereto, and the resulting product was washed three times with ethyl acetate and water to obtain an organic layer. The resulting organic layer was dried over MgSO4 and then dried under reduced pressure. The dried organic layer was purified by column chromatography to obtain intermediate 1f.

[0373] (Yield: 75%)

[0374] 1-6, (Synthetic intermediate C1)

[0375] Intermediate 1f (1.0 eq.) was dissolved in acetic acid:hydrochloric acid at a volume ratio of approximately 9:1, and the mixture was stirred at approximately 80°C for approximately 2 hours under a nitrogen atmosphere. After cooling, the resulting product was washed three times with ethyl acetate and water, and an organic layer was obtained. The resulting organic layer was dried over MgSO4 and then dried under reduced pressure. The dried organic layer was purified by column chromatography to obtain Intermediate C1. (Yield: 69%)

[0376] 1-7, (synthetic intermediate 1g)

[0377] 2-Bromo-9,9-dimethyl-9H-fluorene (1 eq.), aniline (1.1 eq.), tris(dibenzylideneacetone)dipalladium(0) (0.03 eq.), tri-tert-butylphosphine (0.06 eq.) and sodium tert-butoxide (2.0 eq.) were dissolved in toluene, and the mixture was stirred at about 80° C. for about 2 hours in a nitrogen atmosphere. After cooling, the resulting product was washed three times with ethyl acetate and water, and then an organic layer was obtained. The resulting organic layer was dried over MgSO 4 and then dried under reduced pressure. The dried organic layer was purified by column chromatography to obtain 1 g of the intermediate. (Yield: 85%)

[0378] 1-8. Synthesis of Compound 1

[0379] Intermediate C1 (1.0 eq.), Intermediate 1g (1.1 eq.), tris(dibenzylideneacetone)dipalladium(0) (0.05 eq.), tri-tert-butylphosphine (0.10 eq.) and sodium tert-butoxide (2.0 eq.) were dissolved in toluene, and the mixture was stirred at about 90° C. for about 2 hours under a nitrogen atmosphere. After cooling, the resulting product was washed three times with ethyl acetate and water, and an organic layer was obtained. The obtained organic layer was dried over MgSO 4 and then dried under reduced pressure. The dried organic layer was purified by column chromatography to obtain Compound 1. (Yield: 82%)

[0380] 2. Synthesis of compound 2

[0381]

[0382] 2-1. (Synthesis of Intermediate 2a)

[0383] 2,3-Dihydroxynaphthalene (1.0 eq.) and triethylamine (6.0 eq.) were dissolved in dichloromethane and cooled to approximately 0°C under a nitrogen atmosphere. Trifluoromethanesulfonic anhydride (3.0 eq.) was then slowly added dropwise. The mixture was stirred at room temperature under a nitrogen atmosphere for approximately 3 hours. The resulting product was washed three times with ethyl acetate and water to obtain an organic layer. The resulting organic layer was dried over MgSO4 and then dried under reduced pressure. The dried organic layer was purified by column chromatography to obtain Intermediate 2a.

[0384] (Yield: 85%)

[0385] 2-2. (Synthesis of Intermediate 2b)

[0386] Intermediate 2a (1.0 eq.), phenylboronic acid (1.0 eq.), tetrakis(triphenylphosphine)palladium (0.05 eq.), and potassium carbonate (2.0 eq.) were dissolved in THF:H2O at a volume ratio of about 4:1, and the mixture was stirred at about 80°C for about 12 hours under a nitrogen atmosphere. After cooling, the resulting product was washed three times with ethyl acetate and water to obtain an organic layer. The resulting organic layer was dried over MgSO4 and then dried under reduced pressure. The dried organic layer was purified by column chromatography to obtain Intermediate 2b. (Yield: 85%)

[0387] 2-3. (Synthesis of Intermediate 2c)

[0388] Intermediate 2b (1.0 eq.), aniline (1.1 eq.), tris(dibenzylideneacetone)dipalladium(0) (0.05 eq.), tri-tert-butylphosphine (0.10 eq.) and sodium tert-butoxide (2.0 eq.) were dissolved in toluene, and the mixture was stirred at about 80° C. for about 2 hours under a nitrogen atmosphere. After cooling, the resulting product was washed three times with ethyl acetate and water, and an organic layer was obtained. The resulting organic layer was dried over MgSO 4 and then dried under reduced pressure. The dried organic layer was purified by column chromatography to obtain Intermediate 2c. (Yield: 75%)

[0389] 2-4. Synthesis of Compound 2

[0390] Intermediate C1 (1.0 eq.), Intermediate 2c (1.1 eq.), tris(dibenzylideneacetone)dipalladium(0) (0.05 eq.), tri-tert-butylphosphine (0.10 eq.) and sodium tert-butoxide (2.0 eq.) were dissolved in toluene, and the mixture was stirred at about 100° C. for about 2 hours under a nitrogen atmosphere. After cooling, the resulting product was washed three times with ethyl acetate and water, and an organic layer was obtained. The resulting organic layer was dried over MgSO 4 and then dried under reduced pressure. The dried organic layer was purified by column chromatography to obtain Compound 2. (Yield: 80%)

[0391] 3. Synthesis of compound 4

[0392]

[0393] 3-1. (Synthesis of Intermediate 4a)

[0394] 1,8-Dibromonaphthalene (1.0 eq.), [1,1'-biphenyl]-4-ylboronic acid (1.0 eq.), tetrakis(triphenylphosphine)palladium (0.05 eq.) and potassium carbonate (2.0 eq.) were dissolved in THF:H2O at a volume ratio of about 4:1, and the mixture was stirred at about 80°C for about 12 hours under a nitrogen atmosphere. After cooling, the resulting product was washed three times with ethyl acetate and water, and then an organic layer was obtained. The resulting organic layer was dried over MgSO4 and then dried under reduced pressure. The dried organic layer was purified by column chromatography to obtain Intermediate 4a. (Yield: 65%)

[0395] 3-2. (Synthesis of Intermediates 4b and 4c)

[0396] Anhydrous diethyl ether was added dropwise to intermediate 4a (1.0 eq.), magnesium (5.0 eq.) and dichloroethane (0.01 eq.), and the mixture was stirred at about 40° C. for about 1 hour in a nitrogen atmosphere to produce a solution of intermediate 4b. After the solution of intermediate 4b was cooled to about 0° C., the cooled solution was slowly added dropwise to a solution of intermediate 1e dissolved in THF, and the mixture was stirred at about 40° C. for about 1 hour. After cooling, an ammonium chloride solution was slowly added dropwise thereto, and the resulting product was rinsed three times with ethyl acetate and water to obtain an organic layer. The resulting organic layer was dried over MgSO 4 and then dried under reduced pressure. The dried organic layer was purified by column chromatography to obtain intermediate 4c.

[0397] (Yield: 75%)

[0398] 3-3. (Synthesis of Intermediate C2)

[0399] Intermediate 4c (1.0 eq.) was dissolved in acetic acid:hydrochloric acid at a volume ratio of approximately 9:1, and the mixture was stirred at approximately 80°C for approximately 2 hours under a nitrogen atmosphere. After cooling, the resulting product was washed three times with ethyl acetate and water, and an organic layer was obtained. The resulting organic layer was dried over MgSO4 and then dried under reduced pressure. The dried organic layer was purified by column chromatography to obtain Intermediate C2. (Yield: 69%)

[0400] 3-4. Synthesis of Compound 4

[0401] Intermediate C2 (1.0 eq.), Intermediate 1a (1.1 eq.), tris(dibenzylideneacetone)dipalladium(0) (0.05 eq.), tri-tert-butylphosphine (0.10 eq.) and sodium tert-butoxide (2.0 eq.) were dissolved in toluene, and the mixture was stirred at about 90° C. for about 2 hours under a nitrogen atmosphere. After cooling, the resulting product was washed three times with ethyl acetate and water, and an organic layer was obtained. The obtained organic layer was dried over MgSO 4 and then dried under reduced pressure. The dried organic layer was purified by column chromatography to obtain Compound 4. (Yield: 79%)

[0402] 4. Synthesis of compound 5

[0403]

[0404] Intermediate C2 (1.0 eq.), Intermediate 2c (1.1 eq.), tris(dibenzylideneacetone)dipalladium(0) (0.05 eq.), tri-tert-butylphosphine (0.10 eq.) and sodium tert-butoxide (2.0 eq.) were dissolved in toluene, and the mixture was stirred at about 90° C. for about 2 hours under a nitrogen atmosphere. After cooling, the resulting product was washed three times with ethyl acetate and water, and an organic layer was obtained. The resulting organic layer was dried over MgSO 4 and then dried under reduced pressure. The dried organic layer was purified by column chromatography to obtain Compound 5. (Yield: 75%)

[0405] 5. Synthesis of compound 10

[0406]

[0407] 5-1. (Synthesis of Intermediate 10a)

[0408] 1,8-Dibromonaphthalene (1.0 eq.), 4-chlorophenylboronic acid (1.0 eq.), tetrakis(triphenylphosphine)palladium (0.05 eq.), and potassium carbonate (2.0 eq.) were dissolved in THF:H2O at a volume ratio of about 4:1, and the mixture was stirred at about 90°C for about 12 hours under a nitrogen atmosphere. After cooling, the resulting product was washed three times with ethyl acetate and water, and an organic layer was obtained. The resulting organic layer was dried over MgSO4 and then dried under reduced pressure. The dried organic layer was purified by column chromatography to obtain Intermediate 10a. (Yield: 62%)

[0409] 5-2. (Synthesis of Intermediate 10c)

[0410] 1,5-Dibromonaphthalene (1.0 eq.), phenylboronic acid (1.0 eq.), tetrakis(triphenylphosphine)palladium (0.05 eq.), and potassium carbonate (2.0 eq.) were dissolved in toluene / EtOH:H2O at a volume ratio of about 4:1:1, and the mixture was stirred at about 100°C for about 12 hours under a nitrogen atmosphere. After cooling, the resulting product was washed three times with ethyl acetate and water, and an organic layer was obtained. The resulting organic layer was dried over MgSO4 and then dried under reduced pressure. The dried organic layer was purified by column chromatography to obtain Intermediate 10c. (Yield: 68%)

[0411] 5-3. (Synthesis of Intermediate 10d)

[0412] Intermediate 10c (1.0 eq.), bis(pinacolato)diboron (2.5 eq.), potassium acetate (5.0 eq.), and palladium acetate (0.05 eq.) were dissolved in 1,4-dioxane, and the mixture was stirred at approximately 80°C for approximately 3 hours under a nitrogen atmosphere. After cooling, the resulting product was washed three times with ethyl acetate and water, and an organic layer was obtained. The resulting organic layer was dried over MgSO4 and then dried under reduced pressure. The dried organic layer was purified by column chromatography to obtain Intermediate 10d. (Yield: 81%)

[0413] 5-4. (Synthesis of Intermediate 10e)

[0414] Intermediate 10d (1.0 eq.), benzoyl chloride (1.5 eq.), tetrakis(triphenylphosphine)palladium (0.05 eq.), and potassium carbonate (2.0 eq.) were dissolved in THF:H2O at a volume ratio of approximately 4:1, and the mixture was stirred at approximately 80°C under a nitrogen atmosphere for approximately 12 hours. After cooling, the resulting product was washed three times with ethyl acetate and water, and an organic layer was obtained. The resulting organic layer was dried over MgSO4 and then dried under reduced pressure. The dried organic layer was purified by column chromatography to obtain Intermediate 10e. (Yield: 60%)

[0415] 5-5. (Synthesis of Intermediate 10f)

[0416] Intermediate 10e (1.0 eq.), palladium acetate (0.01 eq.), and silver (I) oxide (1.5 eq.) were dissolved in trifluoroacetic acid, and the mixture was stirred at about 130° C. for about 36 hours under a nitrogen atmosphere. After cooling, the resulting product was washed three times with ethyl acetate and water, and an organic layer was obtained. The resulting organic layer was dried over MgSO4 and then dried under reduced pressure. The dried organic layer was purified by column chromatography to obtain Intermediate 10f. (Yield: 70%)

[0417] 5-6. (Synthesis of Intermediate 10b and Intermediate 10g)

[0418] Anhydrous diethyl ether is added dropwise to intermediate 10a (1.0 eq.), magnesium (5.0 eq.) and dichloroethane (0.01 eq.), and the mixture is then stirred at about 40 ° C for about 1 hour in a nitrogen atmosphere to produce a solution of intermediate 10b. After the solution of intermediate 10b is cooled to about 0 ° C, the cooled solution is slowly added dropwise to a solution of intermediate 10f dissolved in THF, and the mixture is then stirred at about 40 ° C for about 1 hour. After cooling, ammonium chloride solution is slowly added dropwise thereto, and the resulting product is rinsed three times with ethyl acetate and water to obtain an organic layer. The resulting organic layer is dried over MgSO4 and then dried under reduced pressure. The dried organic layer is purified by column chromatography to obtain intermediate 10g.

[0419] (Yield: 65%)

[0420] 5-7, (Synthesis of Intermediate C3)

[0421] 10 g (1.0 eq.) of the intermediate was dissolved in acetic acid:hydrochloric acid at a volume ratio of approximately 9:1, and the mixture was stirred at approximately 80°C for approximately 2 hours under a nitrogen atmosphere. After cooling, the resulting product was washed three times with ethyl acetate and water, and an organic layer was obtained. The resulting organic layer was dried over MgSO4 and then dried under reduced pressure. The dried organic layer was purified by column chromatography to obtain Intermediate C3. (Yield: 68%)

[0422] 5-8. Synthesis of Compound 10

[0423] Intermediate C3 (1.0 eq.), Intermediate 1g (1.1 eq.), tris(dibenzylideneacetone)dipalladium(0) (0.05 eq.), tri-tert-butylphosphine (0.10 eq.) and sodium tert-butoxide (2.0 eq.) were dissolved in toluene, and the mixture was stirred at about 90° C. for about 2 hours under a nitrogen atmosphere. After cooling, the resulting product was washed three times with ethyl acetate and water, and an organic layer was obtained. The resulting organic layer was dried over MgSO 4 and then dried under reduced pressure. The dried organic layer was purified by column chromatography to obtain Compound 10. (Yield: 78%)

[0424] 6. Synthesis of compound 11

[0425]

[0426] Intermediate C3 (1.0 eq.), Intermediate 2c (1.1 eq.), tris(dibenzylideneacetone)dipalladium(0) (0.05 eq.), tri-tert-butylphosphine (0.10 eq.) and sodium tert-butoxide (2.0 eq.) were dissolved in toluene, and the mixture was stirred at about 90° C. for about 2 hours under a nitrogen atmosphere. After cooling, the resulting product was washed three times with ethyl acetate and water, and an organic layer was obtained. The resulting organic layer was dried over MgSO 4 and then dried under reduced pressure. The dried organic layer was purified by column chromatography to obtain Compound 11. (Yield: 75%)

[0427] 7. Synthesis of compound 73

[0428]

[0429] 7-1. (Synthesis of Intermediate 73a)

[0430] Aniline (1.0 eq.), 2-bromo-9-phenyl-9H-carbazole (1.1 eq.), tris(dibenzylideneacetone)dipalladium(0) (0.05 eq.), tri-tert-butylphosphine (0.10 eq.), and sodium tert-butoxide (2.0 eq.) were dissolved in toluene, and the mixture was stirred at about 90° C. for about 2 hours under a nitrogen atmosphere. After cooling, the resulting product was washed three times with ethyl acetate and water, and then an organic layer was obtained.

[0431] The resulting organic layer was dried over MgSO4 and then dried under reduced pressure. The dried organic layer was purified by column chromatography to obtain Intermediate 73a. (Yield: 78%)

[0432] 7-2. Synthesis of Compound 73

[0433] Intermediate C1 (1.0 eq.), Intermediate 73a (1.1 eq.), tris(dibenzylideneacetone)dipalladium(0) (0.05 eq.), tri-tert-butylphosphine (0.10 eq.) and sodium tert-butoxide (2.0 eq.) were dissolved in toluene, and the mixture was stirred at about 90° C. for about 2 hours under a nitrogen atmosphere. After cooling, the resulting product was washed three times with ethyl acetate and water to obtain an organic layer. The obtained organic layer was dried over MgSO 4 and then dried under reduced pressure. The dried organic layer was purified by column chromatography to obtain Compound 73. (Yield: 75%)

[0434] 8. Synthesis of compound 76

[0435]

[0436] Intermediate C2 (1.0 eq.), Intermediate 73a (1.1 eq.), tris(dibenzylideneacetone)dipalladium(0) (0.05 eq.), tri-tert-butylphosphine (0.10 eq.) and sodium tert-butoxide (2.0 eq.) were dissolved in toluene, and the mixture was stirred at about 90° C. for about 2 hours under a nitrogen atmosphere. After cooling, the resulting product was washed three times with ethyl acetate and water to obtain an organic layer. The obtained organic layer was dried over MgSO 4 and then dried under reduced pressure. The dried organic layer was purified by column chromatography to obtain Compound 76. (Yield: 72%)

[0437] 9. Synthesis of compound 82

[0438]

[0439] Intermediate C3 (1.0 eq.), Intermediate 73a (1.1 eq.), tris(dibenzylideneacetone)dipalladium(0) (0.05 eq.), tri-tert-butylphosphine (0.10 eq.) and sodium tert-butoxide (2.0 eq.) were dissolved in toluene, and the mixture was stirred at about 90° C. for about 2 hours under a nitrogen atmosphere. After cooling, the resulting product was washed three times with ethyl acetate and water to obtain an organic layer. The obtained organic layer was dried over MgSO 4 and then dried under reduced pressure. The dried organic layer was purified by column chromatography to obtain Compound 82. (Yield: 70%)

[0440] 10. Synthesis of compound 94

[0441]

[0442] 10-1. (Synthesis of Intermediate 94a)

[0443] Intermediate 10d (1.0 eq.), 3-bromobenzoyl chloride (1.5 eq.), tetrakis(triphenylphosphine)palladium (0.05 eq.), and potassium carbonate (2.0 eq.) were dissolved in THF:H2O at a volume ratio of about 4:1, and the mixture was stirred at about 80°C under a nitrogen atmosphere for about 12 hours. After cooling, the resulting product was washed three times with ethyl acetate and water to obtain an organic layer. The resulting organic layer was dried over MgSO4 and then dried under reduced pressure. The dried organic layer was purified by column chromatography to obtain Intermediate 94a. (Yield: 60%)

[0444] 10-2. (Synthesis of Intermediate 94b)

[0445] Intermediate 94a (1.0 eq.), palladium acetate (0.01 eq.), and silver (I) oxide (1.5 eq.) were dissolved in trifluoroacetic acid, and the mixture was stirred at about 130° C. under a nitrogen atmosphere for about 36 hours. After cooling, the resulting product was washed three times with ethyl acetate and water to obtain an organic layer. The resulting organic layer was dried over MgSO 4 and then dried under reduced pressure. The dried organic layer was purified by column chromatography to obtain Intermediate 94b. (Yield: 70%)

[0446] 10-3. (Synthesis of Intermediate 1b and Intermediate 94c)

[0447] Anhydrous diethyl ether was added dropwise to intermediate 1a (1.0 eq.), magnesium (5.0 eq.) and dichloroethane (0.01 eq.), and the mixture was stirred at about 40° C. for about 1 hour under a nitrogen atmosphere to produce a solution of intermediate 1b. After the solution of intermediate 1b was cooled to about 0° C., the cooled solution was slowly added dropwise to a solution of intermediate 94b dissolved in THF, and the mixture was stirred at about 40° C. for about 1 hour. After cooling, an ammonium chloride solution was slowly added dropwise thereto, and the resulting product was washed three times with ethyl acetate and water to obtain an organic layer. The resulting organic layer was dried over MgSO 4 and then dried under reduced pressure. The dried organic layer was purified by column chromatography to obtain intermediate 94c.

[0448] (Yield: 65%)

[0449] 10-4, (Synthetic intermediate C4)

[0450] Intermediate 94c (1.0 eq.) was dissolved in acetic acid:hydrochloric acid at a volume ratio of approximately 9:1, and the mixture was stirred at approximately 80°C under a nitrogen atmosphere for approximately 2 hours. After cooling, the resulting product was washed three times with ethyl acetate and water, and an organic layer was obtained. The resulting organic layer was dried over MgSO4 and then dried under reduced pressure. The dried organic layer was purified by column chromatography to obtain Intermediate C4. (Yield: 68%)

[0451] 10-5. Synthesis of Compound 94

[0452] Intermediate C4 (1.0 eq.), Intermediate 73a (1.1 eq.), tris(dibenzylideneacetone)dipalladium(0) (0.05 eq.), tri-tert-butylphosphine (0.10 eq.) and sodium tert-butoxide (2.0 eq.) were dissolved in toluene, and the mixture was stirred at about 90° C. for about 2 hours under a nitrogen atmosphere. After cooling, the resulting product was washed three times with ethyl acetate and water to obtain an organic layer. The obtained organic layer was dried over MgSO 4 and then dried under reduced pressure. The dried organic layer was purified by column chromatography to obtain Compound 94. (Yield: 75%)

[0453] Device Manufacturing Example

[0454] A light-emitting device was manufactured using (for example, utilizing) the following example compounds and comparative example compounds as hole transport layer materials:

[0455] Example compounds

[0456]

[0457] Comparative Example Compounds

[0458]

[0459] The light-emitting devices of the embodiments and comparative examples are manufactured by the following method. A 120nm-thick ITO is patterned on a glass substrate, which is then rinsed with ultrapure water and treated with UV and ozone to form a first electrode. 2-TNATA is then deposited thereon to a thickness of about 60nm, and the embodiment compound or the comparative example compound is used to form a 30nm-thick hole transport layer, respectively. DPAVBi is then doped into 9,10-di(naphthalene-2-yl)anthracene (DNA) at 2% to form a 30nm-thick emission layer, a 30nm-thick layer is formed on the emission layer with Alq3, and a 1nm-thick layer is formed with LiF to form an electron transport region. A 300nm-thick second electrode is then formed with aluminum (Al). Each layer is formed by a vacuum deposition method.

[0460] The measured values ​​according to Examples 1 to 10 and Comparative Examples 1 to 4 are shown in Table 1 below. 2 The luminous efficiency and half-life were measured.

[0461] Table 1

[0462]

[0463]

[0464] Referring to Table 1 above, it can be confirmed that each of Examples 1 to 10 achieves high brightness and long service life compared to Comparative Examples 1 to 4. It can be confirmed that Comparative Examples 2 to 4 and Examples 1 to 10 achieve high efficiency compared to Comparative Example 1. It can be confirmed that Comparative Examples 2 to 4 and Examples 1 to 10 achieve low voltage compared to Comparative Example 1.

[0465] The amine compound according to the embodiment of the present disclosure is used in the hole transport region to achieve (for example, to contribute to) low driving voltage, high efficiency and long service life of the light-emitting device. The amine compound according to the embodiment of the present disclosure is bonded to the 7,7'-spirodi[benz[de]anthracene] structure. Without being bound by any particular theory, it is believed that the amine compound according to the embodiment of the present disclosure can have a broadband value and a high glass transition temperature. Therefore, the hole transport properties can be improved, thereby increasing the exciton generation efficiency, thereby achieving high luminous efficiency.

[0466] The amine compound according to an embodiment of the present disclosure is used in a hole transport region to achieve low driving voltage, high efficiency, and long lifetime of a light emitting device.

[0467] The light emitting device according to one or more embodiments of the present disclosure has excellent efficiency.

[0468] The amine compound according to one or more embodiments of the present disclosure may be used as a material of a hole transport region of a light-emitting device, so that the light-emitting device may have improved efficiency.

[0469] Although the embodiments of the present disclosure are described herein, those skilled in the art will appreciate that the present disclosure can be implemented in other specific forms without changing the technical concept or basic features. Therefore, the above embodiments should be understood in all aspects as illustrative rather than restrictive.

Claims

1. An amine compound represented by Formula 1: Formula 1 in, In formula 1, R1 to R 10 are each independently a hydrogen atom, a deuterium atom, or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, R1 to R 10 One of them is represented by Equation 2, and Ring A and Ring B are each independently represented by Formula 3 or Formula 4, and are represented by different formulas: Formula 2 In formula 2, L is a direct connection, n is 1, and Ar1 and Ar2 are each independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms: Formula 3 Formula 4 and Among them, in formula 3 and formula 4, R 11 and R 12 are each independently a hydrogen atom, a deuterium atom, or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a is an integer selected from 0 to 4, and b is an integer selected from 0 to 6, The substituent used for the substitution is at least one substituent selected from the group consisting of a deuterium atom, a halogen atom, a cyano group, a nitro group, an amino group, an alkyl group having 1 to 20 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, and an aryl group having 6 to 20 ring-forming carbon atoms.

2. The amine compound according to claim 1, wherein Formula 1 is represented by Formula 5 or Formula 6: Formula 5 Formula 6 as well as in, In Equation 5 and Equation 6, R1 to R 12 , a and b are the same as those defined in Formula 1, Formula 3 and Formula 4.

3. The amine compound according to claim 2, wherein Formula 5 is represented by Formula 7-1: Formula 7-1 as well as in, In formula 7-1, R x and R5 to R 10 are each independently a hydrogen atom, a deuterium atom, or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, c is an integer selected from 0 to 3, L is a direct connection, n is 1, Ar1 and Ar2 are each independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, R 11 、R 12 , a and b are the same as those defined in Formula 5, and The substituents used for the substitution are the same as defined in Formula 1.

4. The amine compound according to claim 2, wherein Formula 5 is represented by Formula 7-2 or Formula 7-3: Formula 7-2 Formula 7-3 in, In Equation 7-2 and Equation 7-3, R y and R1 to R4 are each independently a hydrogen atom, a deuterium atom, or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, d is an integer selected from 0 to 5, L is a direct connection, n is 1, Ar1 and Ar2 are each independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, R 11 、R 12 , a and b are the same as those defined in Formula 5, and The substituents used for the substitution are the same as defined in Formula 1.

5. The amine compound according to claim 2, wherein Formula 6 is represented by Formula 8-1: Formula 8-1 And among them, In formula 8-1, R x , R5 to R 12 , L, Ar1, Ar2, a to c and n are the same as defined in Formula 6.

6. The amine compound according to claim 2, wherein Formula 6 is represented by Formula 8-2: Formula 8-2 And among them, In formula 8-2, R y , R1 to R4, R 11 、R 12 , L, Ar1, Ar2, a, b, d and n are the same as defined in Formula 6.

7. The amine compound according to claim 2, wherein Formula 6 is represented by Formula 9-1: Formula 9-1 as well as in, In formula 9-1, R x and R5 to R 10 are each independently a hydrogen atom, a deuterium atom, or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, c is an integer selected from 0 to 3, L is a direct connection, n is 1, Ar1 and Ar2 are each independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, R 11 、R 12 , a and b are the same as those defined in Formula 6, and The substituents used for the substitution are the same as defined in Formula 1.

8. The amine compound according to claim 2, wherein Formula 6 is represented by Formula 9-2 or Formula 9-3: Formula 9-2 Formula 9-3 as well as in, In formula 9-2 and formula 9-3, R y and R1 to R4 are each independently a hydrogen atom, a deuterium atom, or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, d is an integer selected from 0 to 5, L is a direct connection, n is 1, Ar1 and Ar2 are each independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, R 11 、R 12 , a and b are the same as those defined in Formula 6, and The substituents used for the substitution are the same as defined in Formula 1.

9. The amine compound according to claim 7, wherein Formula 9-1 is represented by Formula 10-1: Formula 10-1 as well as in, In formula 10-1, R x , R5 to R 12 , L, Ar1, Ar2, a to c and n are the same as defined in Formula 9-1.

10. The amine compound according to claim 8, wherein Formula 9-2 is represented by Formula 10-2: Formula 10-2 as well as in, In formula 10-2, R y , R1 to R4, R 11 、R 12 , L, Ar1, Ar2, a, b, d and n are the same as defined in Formula 9-2.

11. The amine compound according to claim 1, wherein the amine compound represented by Formula 1 is at least one selected from the group consisting of compounds represented by Compound Group 1: Compound Group 1 12. A light-emitting device comprising: a first electrode; a hole transport region on the first electrode; an emissive layer on the hole transport region; an electron transport region on the emissive layer; and a second electrode on the electron transport region, wherein the hole transport region comprises the amine compound according to any one of claims 1 to 11.

13. The light-emitting device according to claim 12, wherein the hole transport region comprises: a hole injection layer on the first electrode; and a hole transport layer on the hole injection layer, and The hole transport layer or the hole injection layer includes the amine compound represented by Formula 1. The light-emitting device of claim 13 , wherein the hole transport region further comprises an electron blocking layer on the hole transport layer.

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