Light-emitting device and polycyclic compound for a light-emitting device

Abstract

The present application relates to a light emitting device including a first electrode, a hole transport zone disposed on the first electrode, an emission layer disposed on the hole transport zone, an electron transport zone disposed on the emission layer, and a second electrode disposed on the electron transport zone, wherein the hole transport zone can contain a polycyclic compound represented by Formula 1, thereby showing long service life and high efficiency.

Description

[0001] Cross-references to related applications

[0002] This application claims priority and benefit to Korean Patent Application No. 10-2021-0005555, filed with the Korean Intellectual Property Office on January 14, 2021, the entire contents of which are incorporated herein by reference. Technical Field

[0003] This disclosure relates to light-emitting devices and polycyclic compounds for use in said light-emitting devices. Background Technology

[0004] Active development of light-emitting devices as image display equipment continues. Compared with liquid crystal display devices, light-emitting devices are so-called self-emissive displays, in which holes and electrons injected from the first electrode and the second electrode recombine in the emitting layer, causing the light-emitting material in the emitting layer, which includes organic compounds, to emit light to achieve display.

[0005] In applications ranging from light-emitting devices to image display devices, there is a demand for light-emitting devices with low driving voltage, high luminous efficiency, and long lifespan, and there is a need for continuous development of materials for light-emitting devices that can reliably achieve such characteristics.

[0006] It should be understood that this background section is intended to provide some useful context for understanding the art. However, this background section may also include ideas, concepts, or knowledge that were not known or understood by a person skilled in the art prior to the relevant valid application date of the subject matter disclosed herein. Summary of the Invention

[0007] This disclosure provides a highly efficient light-emitting device and a polycyclic compound contained in the hole transport region of the light-emitting device.

[0008] The implementation scheme provides a polycyclic compound that can be represented by the following formula 1:

[0009] [Formula 1]

[0010]

[0011] In Formula 1 above, X1 can be O or S, Ar1 can be a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, but Ar1 is not a heteroaryl group containing two or more nitrogen (N) atoms, R1 can be a hydrogen atom, a deuterium atom, a halogen atom, or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, and R2 can be a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted alkyl group having 6 to 30 cyclic carbon atoms. An aryl group with 0 cyclic carbon atoms, or a heteroaryl group with 2 to 30 cyclic carbon atoms, substituted or unsubstituted, or which may be bonded to an adjacent group to form a ring, where a can be an integer from 0 to 4, b can be an integer from 0 to 3, L can be a direct bond, a substituted or unsubstituted aryl group with 6 to 30 cyclic carbon atoms, or a heteroaryl group with 2 to 30 cyclic carbon atoms, but L does not include a carbazole group, and A can be a group represented by formula 2-1 or formula 2-2, but when A is a group represented by formula 2-2, L is not a direct bond:

[0012] [Equation 2-1]

[0013]

[0014] [Equation 2-2]

[0015]

[0016] In Equations 2-1 and 2-2 above, Y can be N (Ar3), O, or S, X2 can be O or S, Ar2 and Ar3 can each be independently substituted or unsubstituted aryl groups having 6 to 30 cyclic carbon atoms or substituted or unsubstituted heteroaryl groups having 2 to 30 cyclic carbon atoms, but Ar2 and Ar3 are not heteroaryl groups containing two or more nitrogen (N) atoms, and R3 to R5 can each be independently hydrogen atoms, deuterium atoms, halogen atoms, substituted or unsubstituted atoms. The substituted alkyl group having 1 to 20 carbon atoms, the substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or the substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, or may be bonded to an adjacent group to form a ring, R6 may be a hydrogen atom, a deuterium atom, a halogen atom, or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, c and e may each be independently an integer from 0 to 3, and d and f may each be independently an integer from 0 to 4. In Formulas 2-1 and 2-2, —* indicates a bonding site with an adjacent atom.

[0017] In the implementation scheme, the polycyclic compound represented by Formula 1 above can be represented by any one of Formulas 3-1 to 3-3:

[0018] [Equation 3-1]

[0019]

[0020] [Equation 3-2]

[0021]

[0022] [Equation 3-3]

[0023]

[0024] In Equations 3-1 to 3-3 above, R1 to R4, L, Ar1, Ar3 and a to d can be the same as those defined with respect to Equations 1 and 2-1.

[0025] In the implementation scheme, the polycyclic compound represented by Formula 1 above can be represented by any one of Formulas 4-1 to 4-3:

[0026] [Equation 4-1]

[0027]

[0028] [Equation 4-2]

[0029]

[0030] [Equation 4-3]

[0031]

[0032] In Equations 4-1 to 4-3 above, R1 to R4, L, Ar1, Ar3 and a to d can be the same as those defined with respect to Equations 1 and 2-1.

[0033] In the implementation scheme, the polycyclic compound represented by Formula 1 above can be represented by any one of Formulas 5-1 to 5-3:

[0034] [Equation 5-1]

[0035]

[0036] [Equation 5-2]

[0037]

[0038] [Equation 5-3]

[0039]

[0040] In Equations 5-1 to 5-3 above, R1, R2, R5, R6, L, Ar1, Ar2, a, b, e, and f can be the same as those defined with respect to Equations 1 and 2-2.

[0041] In the implementation scheme, the polycyclic compound represented by Formula 1 above can be represented by Formula 6:

[0042] [Formula 6]

[0043]

[0044] In Formula 6 above, R7 can 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 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, g can be an integer from 0 to 5, and R1 to R3, L, Ar1, Y, X1 and a to c can be the same as defined with respect to Formula 1 and Formula 2-1.

[0045] In the implementation scheme, the polycyclic compound represented by Formula 1 above can be represented by any one of Formulas 7-1 to 7-3:

[0046] [Equation 7-1]

[0047]

[0048] [Equation 7-2]

[0049]

[0050] [Equation 7-3]

[0051]

[0052] In Equations 7-1 to 7-3 above, R1 to R3, L, Ar1, Y, X1 and a to c can be the same as those defined with respect to Equations 1 and 2-1.

[0053] In the implementation scheme, R1 can be a hydrogen atom or a deuterium atom.

[0054] In the implementation scheme, Ar1, Ar2 and Ar3 can each be independently a substituted or unsubstituted phenyl group.

[0055] In the implementation scheme, L can be a direct link, a substituted or unsubstituted aryl group having 6 to 18 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 6 to 12 cyclic carbon atoms, but L may not include a carbazole group.

[0056] In the implementation scheme, L can be a direct link, or it can be a group represented by any of the following L-1 to L-4:

[0057]

[0058] In L-1 to L-4 above, X3 can be O or S, R8 can 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 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, p can be an integer from 0 to 4, and —* indicates a binding site with an adjacent atom.

[0059] In the implementation scheme, the polycyclic compound represented by Formula 1 above may be at least one selected from Group 1 of compounds.

[0060] In an embodiment, the light-emitting device may include a first electrode, a hole transport region disposed 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 may contain a polycyclic compound represented by Formula 1 above.

[0061] In an implementation, 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, wherein the hole transport layer may contain the polycyclic compound represented by Formula 1 above.

[0062] In an implementation, the hole transport region may include a hole transport layer disposed on the first electrode and an electron blocking layer disposed on the hole transport layer, wherein the electron blocking layer may contain the polycyclic compound represented by Formula 1 above. Attached Figure Description

[0063] The accompanying drawings are included to provide a further understanding of the embodiments, and are incorporated in and form part of this specification. The drawings illustrate embodiments of the present disclosure and their principles. The above and other aspects and features of the present disclosure will become more apparent from the detailed description of the embodiments of the present disclosure with reference to the accompanying drawings, in which:

[0064] Figure 1 This is a plan view illustrating a display device according to an embodiment;

[0065] Figure 2 This is a schematic cross-sectional view illustrating a display device according to an embodiment;

[0066] Figure 3This is a schematic cross-sectional view illustrating a light-emitting device according to an embodiment;

[0067] Figure 4 This is a schematic cross-sectional view illustrating a light-emitting device according to an embodiment;

[0068] Figure 5 This is a schematic cross-sectional view illustrating a light-emitting device according to an embodiment;

[0069] Figure 6 This is a schematic cross-sectional view illustrating a light-emitting device according to an embodiment;

[0070] Figure 7 This is a schematic cross-sectional view illustrating a display device according to an embodiment; and

[0071] Figure 8 This is a schematic cross-sectional view illustrating a display device according to an embodiment. Detailed Implementation

[0072] This disclosure will now be described more fully below with reference to the accompanying drawings, in which embodiments are illustrated. However, this disclosure may be implemented in various forms and should not be construed as being limited to the embodiments set forth herein. Rather, these embodiments are provided so that this disclosure will be thorough and complete, and will fully communicate the scope of this disclosure to those skilled in the art.

[0073] In the accompanying drawings, the size, thickness, scale, and dimensions of the components may be enlarged for ease of description and clarity. The same numbers throughout refer to the same components.

[0074] In the description, it should be understood that when an element (or area, layer, component, etc.) is described as being "on," "connected to," or "attached to" another element, it can be directly on, directly connected to, or directly attached to the other element, or one or more intermediate elements may exist therein. In a similar sense, when an element (or area, layer, component, etc.) is described as "covering" another element, it can directly cover the other element, or one or more intermediate elements may exist therein.

[0075] In the description, when an element is "directly on" another element, "directly connected to" another element, or "directly linked to" another element, there is no intermediate element. For example, "directly on" can mean setting two layers or two elements without any additional elements in between, such as adhesive elements.

[0076] As used herein, expressions such as “a”, “an” and “the” used for the singular are intended to also include the plural form, unless the context clearly indicates otherwise.

[0077] As used herein, the term “and / or” includes any and all combinations of one or more of the related listed items. For example, “A and / or B” can be understood to mean “A, B, or A and B”. The terms “and” and “or” can be used in the sense of conjunctions or antonymous conjunctions and can be understood as equivalent to “and / or”.

[0078] For purposes of meaning and interpretation, the term "at least one of..." is intended to include the meaning of "selected from at least one of...". For example, "at least one of A and B" can be understood to mean "A, B, or A and B". When following a column of elements, the term "at least one of..." modifies the elements of the entire column but not any individual element in the column.

[0079] It should be understood that although the terms first, second, etc., may be used herein to describe various elements, these elements should not be limited by these terms. These terms are used only to distinguish one element from another. Therefore, without departing from the teachings of this disclosure, a first element may be referred to as a second element. Similarly, without departing from the scope of this disclosure, a second element may be referred to as a first element.

[0080] For ease of description, the spatial relative terms “below,” “under,” “down,” “above,” “up,” etc., may be used herein to describe the relationship between one element or component and another, as illustrated in the accompanying drawings. It should be understood that the spatial relative terms are intended to cover different orientations of the device during use or operation, other than those depicted in the drawings. For example, where the device illustrated in the drawings is flipped, a device located “below” or “under” another device may be placed “above” another device. Thus, the exemplary term “below” can include both a lower position and an upper position. The device may also be oriented in other directions, and therefore the spatial relative terms may be interpreted differently depending on the orientation.

[0081] As used herein, the terms “about” or “approximately” include a specified value and mean within an acceptable range of deviation from the value as determined by a person skilled in the art taking into account the relevant measurements and errors associated with the measurement of the quantity (i.e., limitations of the measurement system). For example, “about” may mean within one or more standard deviations, or within ±20%, ±10%, or ±5% of the specified value.

[0082] It should be understood that the terms “comprises,” “comprising,” “includes,” “including,” “have,” “having,” “contains,” “containing,” etc., are intended to indicate the presence of the features, integers, steps, operations, elements, components, or combinations thereof specified in this disclosure, but do not exclude the presence or addition of one or more other features, integers, steps, operations, elements, components, or combinations thereof.

[0083] Unless otherwise defined or implied herein, all terms used (including technical and scientific terms) have the same meaning as commonly understood by one of ordinary skill in the art to which this disclosure pertains. It should be further understood that terms (e.g., those defined in common dictionaries) should be interpreted as having a meaning consistent with their meaning in the context of the relevant field and should not be interpreted in an idealized or overly formal sense unless expressly defined in the specification.

[0084] In the following description, embodiments of the present disclosure will be described with reference to the accompanying drawings.

[0085] Figure 1 This is a plan view illustrating an implementation of a display device DD. Figure 2 This is a schematic cross-sectional view of the display device DD according to the implementation scheme. Figure 2 This is an example along Figure 1 A schematic cross-sectional view of the portion cut off by line I-I'.

[0086] 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 may include light-emitting devices ED-1, ED-2, and ED-3. The display device DD may include multiple of each of the light-emitting devices ED-1, ED-2, and ED-3. The optical layer PP may be disposed on the display panel DP and can control the 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. Although not shown in the figures, in embodiments, the optical layer PP may be omitted from the display device DD.

[0087] The display panel DP may include a substrate layer BS, a circuit layer DP-CL provided on the substrate 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 in the pixel defining film PDL, and an encapsulation layer TFE disposed on the light-emitting devices ED-1, ED-2, and ED-3.

[0088] The substrate layer BS can provide a substrate surface on which the display device layer DP-ED is disposed. The substrate layer BS can be a glass substrate, a metal substrate, a plastic substrate, etc. However, the embodiments are not limited to these, and the substrate layer BS can include an inorganic layer, an organic layer, or a composite material layer.

[0089] In this embodiment, the circuit layer DP-CL may be disposed on the substrate layer BS, and the circuit layer DP-CL may include transistors (not shown). Each of the transistors (not shown) may include a control electrode, an input electrode, and an output electrode. For example, the circuit layer DP-CL may include switching transistors and driving transistors to drive the light-emitting devices ED-1, ED-2, and ED-3 of the display device layer DP-ED.

[0090] Each of the light-emitting devices ED-1, ED-2, and ED-3 may have the following characteristics as described later. Figures 3 to 6 The structure of the light-emitting device ED according to the implementation scheme. Each of the light-emitting devices ED-1, ED-2 and ED-3 may include a first electrode EL1, a hole transport region HTR, an emitter layer EML-R, EML-G and EML-B, an electron transport region ETR and a second electrode EL2.

[0091] Figure 2 An example is shown in which the emitting layers EML-R, EML-G, and EML-B of light-emitting devices ED-1, ED-2, and ED-3 are disposed in openings OH defined in a pixel-defining film PDL, and the hole transport region HTR, electron transport region ETR, and second electrode EL2 are each provided as a common layer for the entire light-emitting devices ED-1, ED-2, and ED-3. However, the embodiments are not limited to this. Although Figure 2 Not shown, but in embodiments, the hole transport region HTR and electron transport region ETR can each be patterned and provided within an opening OH defined in the pixel-defining film PDL. For example, in embodiments, the hole transport region HTR, emitting layers EML-R, EML-G, and EML-B, and electron transport region ETR of light-emitting devices ED-1, ED-2, and ED-3 can each be patterned and provided by inkjet printing.

[0092] The encapsulation layer TFE can cover the light-emitting devices ED-1, ED-2, and ED-3. The encapsulation layer TFE can seal the display device layer DP-ED. The encapsulation layer TFE can be a thin-film encapsulation layer. The encapsulation layer TFE can be a single layer or a stack of multiple layers. The encapsulation layer TFE can include at least one insulating layer. According to an embodiment, the encapsulation layer TFE can include at least one inorganic film (hereinafter, encapsulating inorganic film). According to an embodiment, the encapsulation layer TFE can also include at least one organic film (hereinafter, encapsulating organic film) and at least one encapsulating inorganic film.

[0093] Encapsulating inorganic films can protect the display device layer DP-ED from moisture and / or oxygen, while encapsulating organic films can protect the display device layer DP-ED from foreign substances such as dust particles. Encapsulating inorganic films may contain silicon nitrides, silicon oxide nitrides, silicon oxides, titanium oxides, aluminum oxides, etc., but the embodiments are not limited to these. Encapsulating organic films may contain acrylic-based compounds, epoxy-based compounds, etc. Encapsulating organic films may contain photopolymerizable organic materials, but the embodiments are not limited to these.

[0094] The encapsulation layer TFE can be placed on the second electrode EL2 and can be configured to fill the opening OH.

[0095] refer to Figure 1 and Figure 2 The display device DD may include a non-emitting area NPXA and emitting areas PXA-R, PXA-G, and PXA-B. The emitting areas PXA-R, PXA-G, and PXA-B may each be an area that emits light generated by light-emitting devices ED-1, ED-2, and ED-3, respectively. The emitting areas PXA-R, PXA-G, and PXA-B may be spaced apart from each other in a plane.

[0096] Each of the light-emitting areas PXA-R, PXA-G, and PXA-B can be a region separated by a pixel-defining film PDL. The non-light-emitting area NPXA can be the region between adjacent light-emitting areas PXA-R, PXA-G, and PXA-B, and can correspond to a portion of the pixel-defining film PDL. In the specification, each of the light-emitting areas PXA-R, PXA-G, and PXA-B can correspond to a pixel. The pixel-defining film PDL can separate the light-emitting devices ED-1, ED-2, and ED-3. The emitting layers EML-R, EML-G, and EML-B of the light-emitting devices ED-1, ED-2, and ED-3 can be disposed within the opening OH defined by the pixel-defining film PDL and separated from each other.

[0097] Based on the color of the light produced by each of the light-emitting devices ED-1, ED-2, and ED-3, the light-emitting areas PXA-R, PXA-G, and PXA-B can be grouped. Figure 1 and Figure 2 In the display device DD of the embodiment shown, three light-emitting areas PXA-R, PXA-G, and PXA-B are illustrated, emitting red light, green light, and blue light respectively. For example, the display device DD of the embodiment may include a red light-emitting area PXA-R, a green light-emitting area PXA-G, and a blue light-emitting area PXA-B that are separated from each other.

[0098] In the display device DD according to the embodiment, light-emitting devices ED-1, ED-2, and ED-3 can each emit light with different wavelengths from each other. For example, in the embodiment, the display device DD may include a first light-emitting device ED-1 that emits red light, a second light-emitting device ED-2 that emits green light, and a third light-emitting device ED-3 that emits blue light. For example, the red light-emitting area PXA-R, the green light-emitting area PXA-G, and the blue light-emitting area PXA-B of the display device DD can 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.

[0099] However, the implementation is not limited to this, and the first to third light-emitting devices ED-1, ED-2, and ED-3 can emit light within the same wavelength range, or at least one light-emitting device can emit light within a different wavelength range. For example, the first to third light-emitting devices ED-1, ED-2, and ED-3 can all emit blue light.

[0100] According to the implementation scheme, the light-emitting areas PXA-R, PXA-G, and PXA-B in the display device DD can be arranged in a stripe pattern. (Reference) Figure 1 The red luminous area PXA-R, the green luminous area PXA-G, and the blue luminous area PXA-B can each be arranged along the second directional axis DR2. The red luminous area PXA-R, the green luminous area PXA-G, and the blue luminous area PXA-B can be arranged alternately along the first directional axis DR1 in this order.

[0101] Figure 1 and Figure 2 The illustration shows that all emitting regions PXA-R, PXA-G, and PXA-B have similar areas, but the implementation is not limited to this, and the emitting regions PXA-R, PXA-G, and PXA-B may have different areas depending on the wavelength range of the emitted light. The areas of the emitting regions PXA-R, PXA-G, and PXA-B can be the areas in a plan view defined by the first directional axis DR1 and the second directional axis DR2.

[0102] The arrangement of the luminescent regions PXA-R, PXA-G, and PXA-B is not limited to... Figure 1 The features illustrated herein, and the order in which the red emitting areas PXA-R, green emitting areas PXA-G, and blue emitting areas PXA-B are arranged, can be combined and provided differently depending on the display quality characteristics required in the display device DD. For example, the arrangement of the emitting areas PXA-R, PXA-G, and PXA-B can be... Arrangement pattern or diamond arrangement pattern.

[0103] In the implementation, the areas of the luminescent regions PXA-R, PXA-G, and PXA-B can differ in size from each other. For example, in the implementation, the area of ​​the green luminescent region PXA-G can be smaller than the area of ​​the blue luminescent region PXA-B, but the implementation is not limited to this.

[0104] In the following text, Figures 3 to 6 Each of the above is a schematic cross-sectional view illustrating a light-emitting device according to an embodiment. Each of the light-emitting devices ED according to the embodiment may include a first electrode EL1, a hole transport region HTR, an emitter layer EML, an electron transport region ETR, and a second electrode EL2 stacked in sequence.

[0105] The light-emitting device ED of the embodiment includes a polycyclic compound, which will be described later, in the hole transport region HTR disposed between the first electrode EL1 and the second electrode EL2. However, the embodiment is not limited to this, and the light-emitting device ED of the embodiment may include the compound, which will be described later, not only in the hole transport region HTR, but also in the emission layer EML or electron transport region ETR in the functional layer disposed between the first electrode EL1 and the second electrode EL2, or in the capping layer CPL disposed on the second electrode EL2.

[0106] and Figure 3 compared to, Figure 4 A schematic cross-sectional view of a light-emitting device ED according to an embodiment is shown, 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 compared to, Figure 5 A schematic cross-sectional view of a light-emitting device ED according to an embodiment is shown, 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 compared to, Figure 6 A schematic cross-sectional view of an embodiment of a light-emitting device ED including a cover layer CPL disposed on a second electrode EL2 is shown.

[0107] The first electrode EL1 is conductive. The first electrode EL1 can be formed of a metal alloy or a conductive compound. The first electrode EL1 can be an anode or a cathode. However, the embodiments are not limited to this. In some embodiments, the first electrode EL1 can be a pixel electrode. The first electrode EL1 can be a transmissive electrode, a semi-transmissive reflective electrode, or a reflective electrode. If the first electrode EL1 is a transmissive electrode, it can be formed using a transparent metal oxide (e.g., indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), and indium tin zinc oxide (ITZO)). If the first electrode EL1 is a semi-transmissive reflective electrode or a reflective electrode, it can contain Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF, Mo, Ti, their compounds, or mixtures thereof (e.g., a mixture of Ag and Mg). In some embodiments, the first electrode EL1 can have a multilayer structure, comprising a reflective layer or a semi-transmissive reflective layer formed of the materials described above, and a transparent conductive layer formed of ITO, IZO, ZnO, ITZO, etc. For example, the first electrode EL1 can have a three-layer structure of ITO / Ag / ITO, but the implementation is not limited to this. The thickness of the first electrode EL1 can be approximately to approximately For example, the thickness of the first electrode EL1 can be approximately to approximately

[0108] A hole transport region HTR is provided on the first electrode EL1. The hole transport region HTR may include at least one of a hole injection layer HIL, a hole transport layer HTL, a hole buffer layer (not shown), and an electron blocking layer EBL. The thickness of the hole transport region HTR may be, for example, approximately to approximately

[0109] The hole transport region (HTR) can have a layer formed of a single material, a layer formed of different materials, or a multilayer structure including layers formed of different materials.

[0110] For example, the hole transport region HTR can have a single-layer structure of a hole injection layer HIL or a hole transport layer HTL, or it can have a single-layer structure formed of a hole injection material and a hole transport material. In an embodiment, the hole transport region HTR can have a single-layer structure formed 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 (not shown), hole injection layer HIL / hole buffer layer (not shown), hole transport layer HTL / hole buffer layer or hole injection layer HIL / hole transport layer HTL / electron blocking layer EBL are stacked sequentially from the first electrode EL1, but the embodiment is not limited to this.

[0111] The hole transport region HTR in the light-emitting device ED of the embodiment contains a polycyclic compound according to the embodiment.

[0112] In this specification, the term "substituted or unsubstituted" as used herein may mean a group substituted or unsubstituted by 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, a silyl group, an oxy group, a thio 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 alkoxy group, an aliphatic hydrocarbon cyclic group, an aryl group, and a heterocyclic group. Each of the substituents listed above may be substituted or unsubstituted on its own. For example, a biphenyl group may be interpreted as an aryl group or as a phenyl group substituted by a phenyl group.

[0113] In this specification, the term "bonded to an adjacent group to form a ring" can refer to a group bonded to an adjacent group to form a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocyclic ring. Hydrocarbon rings can include aliphatic and aromatic hydrocarbon rings. Heterocyclic rings can include aliphatic and aromatic heterocyclic rings. Hydrocarbon rings and heterocyclic rings can each be monocyclic or polycyclic. A ring formed by the bonding of groups to each other can be attached to another ring to form a spirostructure.

[0114] In this specification, the term "adjacent group" can mean a substituent that replaces an atom directly bonded to the atom substituted by the corresponding substituent, another substituent that replaces the atom substituted by the corresponding substituent, or a substituent spatially located at the position closest to the corresponding substituent. 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. For example, the two methyl groups in 4,5-dimethylphenanthrene can be interpreted as "adjacent groups" to each other.

[0115] In the specification, examples of halogen atoms may include fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms.

[0116] In the specification, the alkyl group can be straight-chain, branched, or cyclic. The number of carbon atoms in the alkyl group can be 1 to 50, 1 to 30, 1 to 20, 1 to 10, or 1 to 6. Examples of alkyl groups include methyl groups, ethyl groups, n-propyl groups, isopropyl groups, n-butyl groups, sec-butyl groups, tert-butyl groups, isobutyl groups, 2-ethylbutyl groups, 3,3-dimethylbutyl groups, n-pentyl groups, isopentyl groups, neopentyl groups, tert-pentyl groups, cyclopentyl groups, 1-methylpentyl groups, 3-methylpentyl groups, 2-ethylpentyl groups, 4-methyl-2-pentyl groups, n-hexyl groups, 1-methylhexyl groups, and 2-ethylhexyl groups. Groups, 2-butylhexyl group, cyclohexyl group, 4-methylcyclohexyl group, 4-tert-butylcyclohexyl group, n-heptyl group, 1-methylheptyl group, 2,2-dimethylheptyl group, 2-ethylheptyl group, 2-butylheptyl group, n-octyl group, tert-octyl group, 2-ethyloctyl group, 2-butyloctyl group, 2-hexyloctyl group, 3,7-dimethyloctyl group, cyclooctyl group, n-nonyl group, n-decyl group, adamantyl group, 2-ethyldecyl group 2-Butyldecyl group, 2-hexyldecyl group, 2-octyldecyl group, n-undecyl group, n-dodecyl group, 2-ethyldodecyl group, 2-butyldodecyl group, 2-hexyldodecyl group, 2-octyldodecyl group, n-tridecyl group, n-tetradecyl group, n-pentadecanyl group, n-hexadecyl group, 2-ethylhexadecyl group, 2-butylhexadecyl group, 2-hexylhexadecyl group, 2-octylhexadecyl group, n-heptadecyl group, n-octa ...

[0117] In the specification, an alkenyl group can be a hydrocarbon group containing at least one carbon double bond at the middle or end of an alkyl group having two or more carbon atoms. The alkenyl group can be straight-chain or branched. The number of carbon atoms is not particularly limited, but can be 2 to 30, 2 to 20, or 2 to 10. Examples of alkenyl groups include, but are not limited to, vinyl groups, 1-butenyl groups, 1-pentenyl groups, 1,3-butadienylaryl groups, styryl groups, styrylvinyl groups, etc.

[0118] In the specification, the alkynyl group can be a hydrocarbon group containing at least one carbon triple bond at the middle or end of an alkyl group having two or more carbon atoms. The alkynyl group can be straight-chain or branched. The number of carbon atoms is not particularly limited, but can be 2 to 30, 2 to 20, or 2 to 10. Examples of alkynyl groups can include, but are not limited to, ethynyl groups, propynyl groups, etc.

[0119] In the specification, the hydrocarbon ring group can 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 cyclic carbon atoms in the hydrocarbon ring group can be 5 to 60, 5 to 30, or 5 to 20.

[0120] In the specification, the aryl group can be any functional group or substituent derived from an aromatic hydrocarbon ring. The aryl group can be a monocyclic aryl group or a polycyclic aryl group. The number of cyclic carbon atoms in the aryl group can be 6 to 30, 6 to 20, or 6 to 15. Examples of aryl groups can include phenyl groups, naphthyl groups, fluorenyl groups, anthraceneyl groups, phenanthrene groups, biphenyl groups, triphenyl groups, tetraphenyl groups, pentaphenyl groups, hexaphenyl groups, benzo[a]phenanthrene groups, pyrene groups, benzo[a]fluorantheneyl groups, etc. The implementation scheme may include basic groups, etc., but is not limited to these.

[0121] In the specification, the fluorenyl group may be substituted, and two substituents may combine with each other to form a spirostructure. Examples of substituted fluorenyl groups are as follows. However, the embodiments are not limited to these.

[0122]

[0123] In the specification, the heterocyclic group can be any functional group or substituent derived from a ring containing at least one of B, O, N, P, Si, and S as a heteroatom. The heterocyclic group can be an aliphatic heterocyclic group or an aromatic heterocyclic group. The aromatic heterocyclic group can be a heteroaryl group. Both aliphatic and aromatic heterocyclic groups can be monocyclic or polycyclic.

[0124] In the specification, the heterocyclic group may contain at least one of B, O, N, P, Si, and S as a heteroatom. If the heterocyclic group contains two or more heteroatoms, the two or more heteroatoms may be the same or different from each other. The heterocyclic group may be a monocyclic heterocyclic group or a polycyclic heterocyclic group, and the heterocyclic group may be a heteroaryl group. The number of cyclic carbon atoms in the heterocyclic group may be 2 to 30, 2 to 20, or 2 to 10.

[0125] In the specification, the aliphatic heterocyclic group may contain at least one of B, O, N, P, Si, and S as a heteroatom. The number of cyclic carbon atoms in the aliphatic heterocyclic group may be 2 to 30, 2 to 20, or 2 to 10. Examples of aliphatic heterocyclic groups may include oxetane groups, thiohexane groups, pyrrolidinyl groups, piperidinyl groups, tetrahydrofuran groups, tetrahydrothiophene groups, thiohexane groups, tetrahydropyran groups, 1,4-dioxetane groups, etc., but the embodiments are not limited thereto.

[0126] In the specification, the heteroaryl group may contain at least one 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 cyclic carbon atoms in the heteroaryl group may be 2 to 30, 2 to 20, or 2 to 10. Examples of heteroaryl groups may include groups derived from: thiophene group, furan group, pyrrole group, imidazole group, triazole group, pyridine group, bipyridine group, pyrimidine group, triazine group, acridine group, pyridazine group, pyrazine group, quinoline group, quinazoline group, quinoxaline group, phenoxazine group, phthalazine group, pyridopyrimidine group, pyridopyrazine group, pyrazinopyrazine group, isoquinoline group, indole group, carbazole group, N- Arylcarbazole group, N-heteroarylcarbazole group, N-alkylcarbazole group, benzoxazole group, benzimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, thiophene-thiophene group, benzofuran group, phenanthroline group, thiazole group, isoxazole group, oxazole group, oxadiazole group, thiadiazole group, phenothiazine group, dibenzothiophene group, dibenzofuran group, etc., but the implementation scheme is not limited to these.

[0127] In the specification, the number of carbon atoms in the amine group is not particularly limited, but can be from 1 to 30. The amine group can include alkylamine groups, arylamine groups, or heteroarylamine groups. Examples of amine groups can include methylamine groups, dimethylamine groups, phenylamine groups, diphenylamine groups, naphthylamine groups, 9-methyl-anthraylamine groups, etc., but the embodiments are not limited to these.

[0128] The above description of aryl groups in the specification applies to arylene groups, but arylene groups are divalent groups.

[0129] The above description of heteroaryl groups in the specification applies to heteroaryl groups, but heteroaryl groups are divalent groups.

[0130] In the specification, as used herein, —* and —* each represent the binding site with adjacent atoms.

[0131] According to the implementation scheme, the polycyclic compound can be represented by the following formula 1:

[0132] [Formula 1]

[0133]

[0134] In Equation 1, X1 can be O or S.

[0135] In Formula 1, Ar1 can be a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, but Ar1 is not a heteroaryl group containing two or more nitrogen (N) atoms.

[0136] In Formula 1, R1 can be a hydrogen atom, a deuterium atom, a halogen atom, or a substituted or unsubstituted alkyl group having one to 20 carbon atoms.

[0137] In Formula 1, R2 can 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 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, or can be bonded to an adjacent group to form a ring.

[0138] In Equation 1, a can be an integer from 0 to 4, and b can be an integer from 0 to 3. When a is 2 or greater than 2, multiple R1 groups can be the same or different from each other, and when b is 2 or greater than 2, multiple R2 groups can be the same or different from each other.

[0139] In Formula 1, L can be a straight bond, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, but L does not include a carbazole group.

[0140] In Formula 1, A can be a group represented by Formula 2-1 or Formula 2-2. However, when A is a group represented by Formula 2-2, L in Formula 1 may not be a direct bond.

[0141] [Equation 2-1]

[0142]

[0143] [Equation 2-2]

[0144]

[0145] In Equations 2-1 and 2-2, Y can be N(Ar3), O, or S, and X2 can be O or S.

[0146] In Formulas 2-1 and 2-2, Ar2 and Ar3 may each be independently a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, but neither Ar2 nor Ar3 is a heteroaryl group containing two or more nitrogen (N) atoms.

[0147] In Formulas 2-1 and 2-2, R3 to R5 may each be independently 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 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, or may be bonded to adjacent groups to form a ring.

[0148] In Formula 2-2, R6 can be a hydrogen atom, a deuterium atom, a halogen atom, or a substituted or unsubstituted alkyl group having one to 20 carbon atoms.

[0149] In Equations 2-1 and 2-2, c and e can each be an integer from 0 to 3 independently. When c is 2 or greater than 2, multiple R3 groups can be the same or different from each other, and when e is 2 or greater than 2, multiple R5 groups can be the same or different from each other.

[0150] In Equations 2-1 and 2-2, d and f can each be an integer from 0 to 4 independently. When d is 2 or greater than 2, multiple R4 groups can be the same or different from each other, and when f is 2 or greater than 2, multiple R6 groups can be the same or different from each other.

[0151] In the implementation scheme, R1 in Formula 1 can be a hydrogen atom or a deuterium atom.

[0152] In the implementation scheme, Ar1, Ar2 and Ar3 in Formula 1 can each be independently a substituted or unsubstituted phenyl group.

[0153] In the embodiments, L in Formula 1 can be a direct link, a substituted or unsubstituted aryl group having 6 to 18 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 6 to 12 cyclic carbon atoms. However, L may not include a carbazole group.

[0154] In the embodiments, X1 in Formula 1 can be O, and A in Formula 1 can be a group represented by Formula 2-1. In the embodiments, the polycyclic compound represented by Formula 1 can be represented by any one of the following Formulas 3-1 to 3-3:

[0155] [Equation 3-1]

[0156]

[0157] [Equation 3-2]

[0158]

[0159] [Equation 3-3]

[0160]

[0161] In Equations 3-1 to 3-3, R1 to R4, L, Ar1, Ar3 and a to d can be the same as those defined with respect to Equations 1 and 2-1.

[0162] In the embodiments, X1 in Formula 1 can be S, and A in Formula 1 can be a group represented by Formula 2-1. In the embodiments, the polycyclic compound represented by Formula 1 can be represented by any one of the following Formulas 4-1 to 4-3:

[0163] [Equation 4-1]

[0164]

[0165] [Equation 4-2]

[0166]

[0167] [Equation 4-3]

[0168]

[0169] In Equations 4-1 to 4-3, R1 to R4, L, Ar1, Ar3, and a to d can be the same as those defined with respect to Equations 1 and 2-1.

[0170] In the implementation scheme, in any of formulas 3-1 to 3-3 and 4-1 to 4-3, L can be a direct bond, or L can be a group represented by any of the following L-1 to L-4:

[0171]

[0172] In L-1 to L-3, R8 can 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 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms.

[0173] In L-1 to L-3, p can be an integer from 0 to 4. When p is 2 or greater than 2, multiple R8 groups can be the same or different from each other.

[0174] In L-4, X3 can be O or S.

[0175] In the embodiments, A in Formula 1 can be a group represented by Formula 2-2. In the embodiments, the polycyclic compound represented by Formula 1 can be represented by any one of the following Formulas 5-1 to 5-3:

[0176] [Equation 5-1]

[0177]

[0178] [Equation 5-2]

[0179]

[0180] [Equation 5-3]

[0181]

[0182] In Formulas 5-1 to 5-3, in embodiments, L may be a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, but L may not include a carbazole group.

[0183] In Equations 5-1 to 5-3, R1, R2, R5, R6, L, Ar1, Ar2, a, b, e, and f can be the same as those defined with respect to Equations 1 and 2-2.

[0184] In the implementation scheme, in any of formulas 5-1 to 5-3, L can be a group represented by any of the following L-1 to L-4:

[0185]

[0186] In L-1 to L-3, R8 can 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 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms.

[0187] In L-1 to L-3, p can be an integer from 0 to 4. When p is 2 or greater than 2, multiple R8 groups can be the same or different from each other.

[0188] In L-4, X3 can be O or S.

[0189] In the implementation scheme, the polycyclic compound represented by Formula 1 can be represented by the following Formula 6:

[0190] [Formula 6]

[0191]

[0192] In Formula 6, R7 can 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 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms.

[0193] In Equation 6, g can be an integer from 0 to 5. When g is 2 or greater, multiple R7 groups can be the same or different from each other.

[0194] In Equation 6, R1 to R3, L, Ar1, Y, X1 and a to c can be the same as those defined with respect to Equations 1 and 2-1.

[0195] In the implementation scheme, the polycyclic compound represented by Formula 1 can be represented by any one of the following Formulas 7-1 to 7-3:

[0196] [Equation 7-1]

[0197]

[0198] [Equation 7-2]

[0199]

[0200] [Equation 7-3]

[0201]

[0202] In Equations 7-1 to 7-3, R1 to R3, L, Ar1, Y, X1, and a to c can be the same as those defined with respect to Equations 1 and 2-1.

[0203] The polycyclic compound represented by Formula 1 according to the embodiments can be any one selected from Group 1 of compounds below. However, the embodiments are not limited to this.

[0204] [Compound Group 1]

[0205]

[0206]

[0207]

[0208]

[0209]

[0210]

[0211]

[0212]

[0213]

[0214]

[0215]

[0216]

[0217]

[0218]

[0219]

[0220]

[0221]

[0222]

[0223]

[0224]

[0225]

[0226]

[0227]

[0228]

[0229]

[0230]

[0231]

[0232]

[0233]

[0234]

[0235]

[0236]

[0237]

[0238]

[0239]

[0240]

[0241]

[0242]

[0243]

[0244]

[0245]

[0246]

[0247]

[0248]

[0249]

[0250]

[0251]

[0252]

[0253]

[0254]

[0255]

[0256]

[0257]

[0258]

[0259]

[0260]

[0261]

[0262]

[0263] Reference Figures 3 to 6Further description of the light-emitting device ED according to the implementation scheme.

[0264] As described above, the hole transport region (HTR) comprises a polycyclic compound as described above according to the embodiments. For example, the hole transport region (HTR) may comprise a polycyclic compound represented by Formula 1.

[0265] When the hole transport region HTR comprises multiple layers, any one of the layers may contain a polycyclic compound represented by Formula 1. For example, in one embodiment, 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, wherein the hole transport layer HTL may contain a polycyclic compound represented by Formula 1. However, the embodiments are not limited thereto, and for example, the hole injection layer HIL may contain a polycyclic compound represented by Formula 1. For example, in another embodiment, the hole transport region HTR may include a hole transport layer HTL disposed on the first electrode EL1 and an electron blocking layer EBL disposed on the hole transport layer HTL, wherein the electron blocking layer EBL may contain a polycyclic compound represented by Formula 1.

[0266] The hole transport region (HTR) may contain one or more polycyclic compounds represented by Formula 1. For example, the hole transport region (HTR) may contain at least one compound selected from group 1 as described above.

[0267] Hole transport regions (HTRs) can be formed using various methods, such as vacuum deposition, spin coating, tape casting, Langmuir-Blodgett (LB) method, inkjet printing, laser printing, and laser-induced thermal imaging (LITI).

[0268] The hole transport region (HTR) may further comprise a compound represented by the following formula H-1:

[0269] [Formula H-1]

[0270]

[0271] In the above equation H-1, L a1 and L a2 Each of the L groups can be an independent, directly bonded, substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms. In formula H-1, a-1 and b-1 can each be an independent integer from 0 to 10. In formula H-1, when a-1 or b-1 is 2 or greater than 2, multiple L groups... a1 Group or multiple L a2The groups can be independently substituted or unsubstituted aryl groups having 6 to 30 cyclic carbon atoms, or substituted or unsubstituted heteroaryl groups having 2 to 30 cyclic carbon atoms.

[0272] In equation H-1, Ar a1 To Ar a3 Each can be an aryl group having 6 to 30 cyclic carbon atoms, substituted or unsubstituted, or a heteroaryl group having 2 to 30 cyclic carbon atoms, either independently.

[0273] The compound represented by formula H-1 above can be a monoamine compound. In another embodiment, the compound represented by formula H-1 above can be a diamine compound, wherein Ar a1 To Ar a3 At least one of them contains an amine group as a substituent. For example, the compound represented by the above formula H-1 can be in Ar a1 and Ar a2 At least one of the carbazole-based compounds includes a substituted or unsubstituted carbazole group, or in Ar a1 and Ar a2 At least one of the fluorene-based compounds includes a substituted or unsubstituted fluorene group.

[0274] The compound represented by formula H-1 can be any of the compounds selected from the following group of compounds H. However, the compounds listed in the following group of compounds H are examples, and the compound represented by formula H-1 is not limited to those listed in the following group of compounds H.

[0275] [Compound Group H]

[0276]

[0277] Hole transport region (HTR) may contain phthalocyanine compounds (e.g., 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) (PED) OT / PSS), polyaniline / dodecylbenzenesulfonic acid (PANI / DBSA), polyaniline / camphor sulfonic acid (PANI / CSA), polyaniline / poly(4-styrene sulfonate) (PANI / PSS), N,N'-di(naphthyl-1-yl)-N,N'-diphenyl-benzidine (NPB), triphenylamine-containing polyether ketone (TPAPEK), 4-isopropyl-4'-methyldiphenyliodonium [tetra(pentafluorophenyl)borate], dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarboxynitrile (HATCN), etc.

[0278] Hole transport regions (HTRs) can contain carbazole derivatives (e.g., N-phenylcarbazole and polyvinylcarbazole), fluorene derivatives, N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (TPD), triphenylamine derivatives (e.g., 4,4',4”-tris(N-carbazolyl)triphenylamine (TCTA)), N,N'-bis(naphthyl-1-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.

[0279] 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), etc.

[0280] The hole transport region HTR may contain a compound with the hole transport region described above in at least one of the hole injection layer HIL, the hole transport layer HTL, and the electron blocking layer EBL.

[0281] The thickness of the hole transport region (HTR) can be approximately to approximately For example, the thickness of the hole transport region (HTR) can be approximately to approximately The thickness of the hole injection layer (HIL) can be, for example, approximately to approximately Furthermore, the thickness of the hole transport layer (HTL) can be approximately... to approximately For example, the thickness of the electron blocking layer EBL can be approximately to approximately If the thicknesses of the hole transport region (HTR), hole injection layer (HIL), hole transport layer (HTL), and electron blocking layer (EBL) meet the ranges described above, satisfactory hole transport characteristics can be achieved without a significant increase in driving voltage.

[0282] In addition to the materials described above, the hole transport region (HTR) may further include a charge-generating material to increase conductivity. The charge-generating material may be uniformly or non-uniformly dispersed in the hole transport region (HTR). The charge-generating material may be, for example, a p-doper. The p-doper may include at least one of quinone derivatives, metal oxides, and compounds containing cyano groups, but the embodiments are not limited thereto. For example, non-limiting examples of p-dopers may include quinone derivatives (e.g., tetracyanoquinone dimethyl ether (TCNQ) and 2,3,5,6-tetrafluoro-7,7'8,8'-tetracyanoquinone dimethyl ether (F4-TCNQ)), metal oxides (e.g., tungsten oxide and molybdenum oxide), etc., but the embodiments are not limited thereto.

[0283] 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 of a hole buffer layer (not shown) and an electron blocking layer EBL. The hole buffer layer (not shown) can compensate for the resonant distance according to the wavelength of light emitted from the emitter layer EML, and can therefore increase luminous efficiency. Materials that can be included in the hole transport region HTR can be used as materials included in the hole buffer layer (not shown). The electron blocking layer EBL can prevent electron injection from the electron transport region ETR to the hole transport region HTR.

[0284] An emitter layer EML is provided on the hole transport region (HTR). The emitter layer EML can have, for example, approximately to approximately The thickness. For example, the emitter layer EML can have approximately... to approximately The thickness of the emitter layer (EML) is as follows. The EML can have a layer formed of a single material, a layer formed of different materials, or a multilayer structure with layers formed of different materials.

[0285] In the light-emitting device ED of the implementation scheme, the emitting layer EML may include anthracene derivatives, pyrene derivatives, fluoranthene derivatives, etc. Derivatives, dihydrobenzanthracene derivatives, or benzo[a]phenanthrene derivatives. For example, in an embodiment, the emitter layer EML may contain anthracene derivatives or pyrene derivatives.

[0286] exist Figures 3 to 6 In each embodiment of the light-emitting device ED illustrated herein, the emitting layer EML may comprise a host and a dopant, and the emitting layer EML may comprise 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.

[0287] [Equation E-1]

[0288]

[0289] In equation E-1, R 31 To R 40 Each group can be independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted silyl group, a substituted or unsubstituted thio group, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted alkenyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, or can be bonded to adjacent groups to form a ring. In formula E-1, R 31 To R 40 It can bond to adjacent groups to form saturated or unsaturated hydrocarbon rings, saturated or unsaturated heterocycles.

[0290] In E-1, c and d can each be an integer from 0 to 5 independently.

[0291] The compound represented by formula E-1 can be any one of the following compounds E1 to E19:

[0292]

[0293]

[0294] In an embodiment, the emitting layer EML may contain a compound represented by formula E-2a or E-2b. The compound represented by formula E-2a or E-2b may be used as a phosphorescent host material.

[0295] [Equation E-2a]

[0296]

[0297] In equation E-2a, a can be an integer from 0 to 10, L aIt can be a directly linked, substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms. When a is 2 or greater than 2, multiple L a The groups can be independently substituted or unsubstituted aryl groups having 6 to 30 cyclic carbon atoms, or substituted or unsubstituted heteroaryl groups having 2 to 30 cyclic carbon atoms.

[0298] In equation E-2a, A1 to A5 can each be N or C(R) independently. i R a To R i Each group can be independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted amine group, a substituted or unsubstituted thio 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 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, or can be bonded to an adjacent group to form a ring. R a To R i It can bond to adjacent groups to form hydrocarbon rings or heterocycles containing N, O, S, etc. as cyclic atoms.

[0299] In equation E-2a, two or three of A1 to A5 can be N, and the remainder of A1 to A5 can be C(R). i ).

[0300] [Equation E-2b]

[0301]

[0302] In formula E-2b, Cbz1 and Cbz2 can each be an unsubstituted carbazole group or a carbazole group substituted with an aryl group having 6 to 30 cyclic carbon atoms. b It can be a directly linked, substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms. In formula E-2b, b can be an integer from 0 to 10. When b is 2 or greater than 2, multiple L b The groups can be independently substituted or unsubstituted aryl groups having 6 to 30 cyclic carbon atoms, or substituted or unsubstituted heteroaryl groups having 2 to 30 cyclic carbon atoms.

[0303] The compound represented by formula E-2a or E-2b may be selected from any of the compounds in group E-2 below. However, the compounds listed in group E-2 below are merely examples, and the compounds represented by formula E-2a or E-2b are not limited to those listed in group E-2 below.

[0304] [Compound Group E-2]

[0305]

[0306]

[0307]

[0308] The emitter layer EML may further comprise materials commonly used in the art as the host material. For example, the emitter layer EML may comprise at least one of bis[2-(diphenylphosphino)phenyl]ether oxide (DPEPO), 4,4'-bis(N-carbazolyl)-1,1'-biphenyl (CBP), 1,3-bis(carbazol-9-yl)benzene (mCP), 2,8-bis(diphenylphospho)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 the host material. However, the embodiments are not limited thereto, and for example, tris(8-hydroxy) Alq3, 9,10-bis(naphthyl-2-yl)anthracene (ADN), 2-tert-butyl-9,10-bis(naphthyl-2-yl)anthracene (TBADN), stilbeneyl arylene (DSA), 4,4'-bis(9-carbazolyl)-2,2'-dimethyl-biphenyl (CDBP), 2-methyl-9,10-bis(naphthyl-2-yl)anthracene (MADN), hexaphenylcyclotriphosphazene (CP1), 1,4-bis(triphenylsilyl)benzene (UGH2), hexaphenylcyclotrisiloxane (DPSiO3), and octaphenylcyclotetrasiloxane (DPSiO4) can be used as host materials.

[0309] The emitter layer (EML) may contain compounds represented by the formula Ma or Mb. Compounds represented by the formula Ma or Mb can be used as phosphorescent dopant materials.

[0310] [Formula]

[0311]

[0312] In the above formula Ma, Y1 to Y4 and Z1 to Z4 can each be independently C(R1) or N, and R1 to R4 can each be independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted amine group, a substituted or unsubstituted thio 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 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, or can be bonded to adjacent groups to form a ring. In formula Ma, m can be 0 or 1, and n can be 2 or 3. In formula Ma, when m is 0, n can be 3, and when m is 1, n can be 2.

[0313] Compounds represented by the formula Ma can be used as phosphorescent dopants.

[0314] The compound represented by formula Ma can be any one selected from the following compounds M-a1 to M-a25. However, the following compounds M-a1 to M-a25 are examples, and the compound represented by formula Ma is not limited to the following compounds M-a1 to M-a25.

[0315]

[0316]

[0317] Compounds M-a1 and M-a2 can be used as red dopant materials, and compounds M-a3 and M-a4 can be used as green dopant materials.

[0318] [Formula Mb]

[0319]

[0320] In formula Mb, Q1 to Q4 can each be independently C or N, and C1 to C4 can each be independently a substituted or unsubstituted hydrocarbon ring having 5 to 30 cyclic carbon atoms or a substituted or unsubstituted heterocycle having 2 to 30 cyclic carbon atoms. In formula Mb, L 21 To L 24 Each can be a direct key, *-O-*, *-S-*, or any other key that can be used independently. The formula Mb contains a substituted or unsubstituted divalent alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, wherein e1 to e4 can each be 0 or 1 independently. In the formula Mb, R 31 To R 39Each of the following can be an independent 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 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, or can be bonded to an adjacent group to form a ring, and d1 to d4 can each be an independent integer from 0 to 4.

[0321] Compounds represented by the formula Mb can be used as blue or green phosphorescent dopants.

[0322] The compound represented by the formula Mb can be selected from any of the following compounds. However, the following compounds are examples, and the compound represented by the formula Mb is not limited to the following compounds.

[0323]

[0324] In compounds, R, R 38 and R 39 Each of the following can be independently 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 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms.

[0325] The emitter layer (EML) may contain compounds represented by any one of the following formulas: Fa to Fc. Compounds represented by the following formulas: Fa to Fc can be used as fluorescent dopant materials.

[0326] [Form Fa]

[0327]

[0328] In the formula Fa, the formula is selected from R. a To R j The two values ​​in R can be replaced independently by *-NAr1Ar2. a To R jThe unsubstituted elements of *-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 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms. In the group *-NAr1Ar2, Ar1 and Ar2 can each independently be a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms. For example, at least one of Ar1 and Ar2 can be a heteroaryl group containing O or S as a cyclic atom.

[0329] [Formula Fb]

[0330]

[0331] In equation Fb, R a and R b Each of the Ar1 to Ar4 can 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 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, or can be bonded to adjacent groups to form a ring. Each of the Ar1 to Ar4 can be independently a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms.

[0332] In formula Fb, U and V can each be 0 or 1 independently. In formula Fb, U represents the number of rings bonded at position U, and V represents the number of rings bonded at position V. For example, when U or V is 1, the rings represented by U or V can form fused rings, and when U or V is 0, the rings represented by U or V may not exist. When U is 0 and V is 1, or when U is 1 and V is 0, the fused ring with a fluorene core in formula Fb can be a tetracyclic compound. When both U and V are 0, the fused ring in formula Fb can be a tricyclic compound. When both U and V are 1, the fused ring with a fluorene core in formula Fb can be a pentacyclic compound.

[0333] In formula Fb, when U or V is 1, U and V can each be independently a substituted or unsubstituted hydrocarbon ring having 5 to 30 cyclic carbon atoms or a substituted or unsubstituted heterocycle having 2 to 30 cyclic carbon atoms.

[0334] [Formula Fc]

[0335]

[0336] In equation Fc, A1 and A2 can each be independently O, S, Se, or N(R). m ), and R m It can 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 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms. R1 to R 11 Each group may be independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted amine group, a substituted or unsubstituted boron group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thio group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, or may be bonded to an adjacent group to form a ring.

[0337] In formula Fc, A1 and A2 can each independently bond to substituents of adjacent rings to form fused rings. For example, when A1 and A2 are each independently N(R m When A1 is bonded to R4 or R5 to form a ring, A2 can be bonded to R7 or R8 to form a ring.

[0338] In the implementation, the emitter layer EML may contain styrene derivatives (e.g., 1,4-bis[2-(3-N-ethylcarbazolyl)vinyl]benzene (BCzVB), 4-(di-p-tolylamino)-4'-[(di-p-tolylamino)styrene]stilbene (DPAVB) and N-(4-((E)-2-(6-((E)-4-(diphenylamino)styrene)naphth-2-yl)vinyl)phenyl)-N-phenylaniline (N-BDAVBi)), perylene and its derivatives (e.g., 2,5,8,11-tetratert-butylperylene (TBP)), pyrene and its derivatives (e.g., 1,1'-dipyrene, 1,4-dipyrenebenzene, 1,4-bis(N,N-diphenylamino)pyrene) as dopant materials.

[0339] The emitter layer (EML) can contain phosphorescent dopant materials. For example, metal complexes containing iridium (Ir), platinum (Pt), osmium (Os), gold (Au), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), or thulium (Tm) can be used as phosphorescent dopant. For instance, iridium(III) bis(4,6-difluorophenylpyridyl-N,C2')pyridinecarboxylate (FIrpic), iridium(III) bis(2,4-difluorophenylpyridyl)tetra(1-pyrazolyl)borate (Fir6), or octaethylporphyrin platinum (PtOEP) can be used as phosphorescent dopant. However, the embodiments are not limited to these.

[0340] The emitter layer (EML) may contain quantum dot materials. Quantum dots 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.

[0341] Group II-VI compounds may be selected from the group consisting of: binary compounds selected from CdSe, CdTe, CdS, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, MgSe, MgS, and mixtures thereof; and ternary compounds selected from CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, CdZnS, and CdZnO. The group consisting of nSe, CdZnTe, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, MgZnSe, MgZnS and mixtures thereof; and quaternary compounds selected from the group consisting of HgZnTeS, CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe, HgZnSTe and mixtures thereof.

[0342] Group III-VI compounds may include: binary compounds, such as In2S3 and In2Se3; ternary compounds, such as InGaS3 and InGaSe3; or any combination thereof.

[0343] Group I-III-VI compounds may be selected from: ternary compounds, which are selected from the group consisting of AgInS, AgInS2, CuInS, CuInS2, AgGaS2, CuGaS2, CuGaO2, AgGaO2, AgAlO2 and mixtures thereof; or quaternary compounds, such as AgInGaS2 and CuInGaS2.

[0344] Group III-V compounds may be selected from the group consisting of: binary compounds selected from GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, InSb, and mixtures thereof; ternary compounds selected from GaNP, GaNAs, GaNSb, GaPAs, GaPSb, AlNP, AlNAs, AlNSb, AlPAs, AlPSb, InGaP, InAlP, InNP, InNAs, InNSb, InPAs, InPSb, and mixtures thereof; and quaternary compounds selected from GaAlNP, GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNP, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs, InAlPSb, and mixtures thereof. Group III-V compounds may further include Group II metals. For example, InZnP and other compounds can be selected as III-II-V group compounds.

[0345] Group IV-VI compounds may be selected from the group consisting of: binary compounds selected from SnS, SnSe, SnTe, PbS, PbSe, PbTe, and mixtures thereof; ternary compounds selected from SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, SnPbTe, and mixtures thereof; and quaternary compounds selected from SnPbSSe, SnPbSeTe, SnPbSTe, and mixtures thereof. Group IV elements may be selected from the group consisting of Si, Ge, and mixtures thereof. Group IV compounds may be binary compounds selected from the group consisting of SiC, SiGe, and mixtures thereof.

[0346] Binary, ternary, or quaternary compounds can exist in the particles at a uniform concentration distribution, or they can exist in the same particle at partially different concentration distributions. In an embodiment, the quantum dots can have a core / shell structure, with one quantum dot surrounding another. The interface between the core and shell can have a concentration gradient, wherein the concentration of the element present in the shell decreases towards the core.

[0347] In implementations, quantum dots may have the core-shell structure described above, comprising a core containing nanocrystals and a shell surrounding the core. The shell of the quantum dot may be a protective layer to prevent chemical deformation of the core in order to maintain semiconductor properties and / or a charging layer to impart electrophoretic properties to the quantum dot. The shell may be single-layered or multi-layered. Examples of shells for quantum dots may include oxides of metals or non-metals, semiconductor compounds, or combinations thereof.

[0348] For example, the oxides of metals or nonmetals can be binary compounds, such as SiO2, Al2O3, TiO2, ZnO, MnO, Mn2O3, Mn3O4, CuO, FeO, Fe2O3, Fe3O4, CoO, Co3O4, and NiO; or ternary compounds, such as MgAl2O4, CoFe2O4, NiFe2O4, and CoMn2O4, but the embodiments are not limited thereto.

[0349] The semiconductor compound can 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 implementation is not limited to these.

[0350] Quantum dots can have a full width at half maximum (FWHM) of a light emission wavelength spectrum equal to or less than about 45 nm. For example, quantum dots can have an FWHM of a light emission wavelength spectrum equal to or less than about 40 nm. For example, quantum dots can have an FWHM of a light emission wavelength spectrum equal to or less than about 30 nm. Within these ranges, color purity and / or color reproducibility can be improved. Light emitted by such quantum dots can be emitted in all directions, and therefore a wide viewing angle can be improved.

[0351] The form of quantum dots is not particularly limited and can be any form commonly used in the field. For example, quantum dots can be spherical, pyramidal, multi-armed, or cubic in shape, or they can take the form of nanotubes, nanowires, nanofibers, nanoparticles, etc.

[0352] Quantum dots can be used to control the color of emitted light based on their particle size. Therefore, quantum dots can have a variety of light emission colors, such as blue, red, and green.

[0353] exist Figures 3 to 6 In each of the illustrated embodiments of the light-emitting device ED, an electron transport region (ETR) is provided on the emitter layer (EML). The electron transport region (ETR) may include at least one of a hole blocking layer (HBL), an electron transport layer (ETL), and an electron injection layer (EIL), but the embodiments are not limited thereto.

[0354] The electron transport region (ETR) can have a layer formed of a single material, a layer formed of different materials, or a multi-layer structure including layers formed of different materials.

[0355] For example, the electron transport region (ETR) can have a single-layer structure of an electron injection layer (EIL) or an electron transport layer (ETL), or it can have a single-layer structure formed of an electron injection material and an electron transport material. In embodiments, the ETR can have a single-layer structure formed of different materials, or it can 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) are stacked sequentially from the emitter layer (EML), but embodiments are not limited thereto. The ETR can have, for example, approximately to approximately The thickness.

[0356] Electron transport regions (ETRs) can be formed using various methods, such as vacuum deposition, spin coating, tape casting, Langmuir-Blodgett (LB) method, inkjet printing, laser printing, laser-induced thermal imaging (LITI), etc.

[0357] The electron transport region (ETR) may contain a compound represented by the following formula: ET-1

[0358] [Formula ET-1]

[0359]

[0360] In equation ET-1, at least one of X1 to X3 can be N, and the remainder of X1 to X3 can be C(R). a R a It can 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 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms. In formula ET-1, Ar1 to Ar3 can 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 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms.

[0361] In Formula ET-1, a to c can each be an integer from 0 to 10 independently. In Formula ET-1, L1 to L3 can each be a directly linked, substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms. In Formula ET-1, when a to c are 2 or greater than 2, L1 to L3 can each be a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms.

[0362] When the electron transport region (ETR) includes an electron transport layer (ETL), the ETR may contain an anthracene-based compound. However, embodiments are not limited to this, and the ETR may contain, for example, tris(8-hydroxyquinoline)aluminum (Alq3), 1,3,5-tris[(3-pyridyl)-benzyl-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-benzimidazol-2-yl)benzene (TPBi), 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), 3- (4-Biphenyl)-4-phenyl-5-tert-butylphenyl-1,2,4-triazole (TAZ), 4-(naphth-1-yl)-3,5-diphenyl-4H-1,2,4-triazole (NTAZ), 2-(4-biphenyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (tBu-PBD), bis(2-methyl-8-quinoline-N1,O8)-(1,1'-biphenyl-4-oline)aluminum (BAlq), bis(benzoquinoline-10-oline)beryllium (Bebq2), 9,10-bis(naphth-2-yl)anthracene (ADN), 1,3-bis[3,5-bis(pyridin-3-yl)phenyl]benzene (BmPyPhB), or mixtures thereof.

[0363] The electron transport region (ETR) may contain at least one compound selected from compounds ET1 to ET36:

[0364]

[0365]

[0366]

[0367]

[0368] The electron transport region (ETR) can comprise a metal halide (e.g., LiF, NaCl, CsF, RbCl, RbI, CuI, or KI), a lanthanide (e.g., Yb), or a co-deposited material of a metal halide and a lanthanide. For example, the ETR can comprise KI:Yb, RbI:Yb, etc., as co-deposited materials. The ETR can comprise metal oxides such as Li₂O or BaO, or lithium 8-hydroxyquinoline (Liq), but embodiments are not limited thereto. The ETR can also be formed from a mixture of an electron transport material and an insulating organometallic salt. The insulating organometallic salt can be a material having a band gap equal to or greater than about 4 eV. For example, the insulating organometallic salt can comprise metal acetates, metal benzoates, metal acetoacetates, metal acetylacetonates, or metal stearates, but embodiments are not limited thereto.

[0369] The electron transport region (ETR) may contain a compound of the electron transport region described above in at least one of the electron injection layer (EIL), the electron transport layer (ETL), and the hole blocking layer (HBL).

[0370] When the electron transport region (ETR) includes the electron transport layer (ETL), the ETL can have approximately to approximately The thickness. For example, the electron transport layer (ETL) can have approximately [a certain thickness]. to approximately The thickness of the electron transport layer (ETL) is within the aforementioned range. If the thickness of the ETL meets these requirements, satisfactory electron transport characteristics can be obtained without a significant increase in the driving voltage. When the ETL includes an electron injection layer (EIL), the EIL can have approximately [missing information - likely a specific thickness]. to approximately The thickness. For example, the electron-injected layer (EIL) can have approximately [a certain thickness]. to approximately The thickness of the electron injection layer (EIL) is crucial. If the thickness of the EIL meets the range described above, satisfactory electron injection characteristics can be obtained without a significant increase in driving voltage.

[0371] The second electrode EL2 is provided on the electron transport region ETR. The second electrode EL2 can be a common electrode. The second electrode EL2 can be a cathode or an anode, but the embodiments are not limited thereto. For example, when the first electrode EL1 is an anode, the second electrode EL2 can be a cathode, and when the first electrode EL1 is a cathode, the second electrode EL2 can be an anode.

[0372] The second electrode EL2 can be a transmission electrode, a semi-transmissive reflection electrode, or a reflection electrode. When the second electrode EL2 is a transmission electrode, it can be formed from a transparent metal oxide (e.g., indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), indium tin zinc oxide (ITZO), etc.).

[0373] When the second electrode EL2 is a semi-transparent reflective electrode or a reflective electrode, the second electrode EL2 may contain Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF, Mo, Ti, Yb, W, their compounds, or mixtures thereof (e.g., AgMg, AgYb, or MgAg). In embodiments, the second electrode EL2 may have a multilayer structure, including a reflective or semi-transparent reflective film formed from the materials described above, and a transparent conductive film formed from ITO, IZO, ZnO, ITZO, etc. For example, the second electrode EL2 may contain the metallic materials described above, a combination of at least two of the metallic materials described above, oxides of the metallic materials described above, etc.

[0374] Although not shown in the accompanying drawings, the second electrode EL2 can be electrically connected to the auxiliary electrode. If the second electrode EL2 is electrically connected to the auxiliary electrode, the resistance of the second electrode EL2 can be reduced.

[0375] In an embodiment, the light-emitting device ED may further include a cover layer CPL disposed on the second electrode EL2. The cover layer CPL may include multiple layers or a single layer.

[0376] In the implementation scheme, the capping layer CPL may include an organic layer or an inorganic layer. For example, when the capping layer CPL contains inorganic materials, the inorganic materials may include alkali metal compounds, such as LiF; or alkaline earth metal compounds, such as MgF2, SiON, and SiN. x SiO y wait.

[0377] For example, when the capping layer CPL contains organic materials, the organic materials may include α-NPD, NPB, TPD, m-MTDATA, Alq3, CuPc, N4,N4,N4',N4'-tetra(biphenyl-4-yl)biphenyl-4,4'-diamine (TPD15), 4,4',4”-tris(carbazole-9-yl)triphenylamine (TCTA), or epoxy resin, or (meth)acrylate (e.g., methacrylate). However, the embodiments are not limited to this, and the organic materials may also include compounds P1 to P5.

[0378]

[0379] The refractive index of the capping layer CPL can be equal to or greater than about 1.6. For example, the refractive index of the capping layer CPL can be equal to or greater than about 1.6 relative to light in the wavelength range of about 550 nm to about 660 nm.

[0380] Figure 7 and Figure 8 Each is a schematic cross-sectional view of a display device according to an embodiment. In the following, in reference... Figure 7 and Figure 8 When describing the display device of the implementation scheme, the description previously used will no longer be included. Figures 1 to 6 The features already described will be explained, but the differences between them will be described.

[0381] refer to Figure 7 According to the implementation scheme, the display device DD may include a display panel DP including a display device layer DP-ED, a light control layer CCL and a color filter layer CFL disposed on the display panel DP.

[0382] exist Figure 7 In the illustrated embodiments, the display panel DP may include a substrate layer BS, a circuit layer DP-CL provided on the substrate layer BS, and a display device layer DP-ED, and the display device layer DP-ED may include a light-emitting device ED.

[0383] The light-emitting device ED may include a first electrode EL1, a hole transport region HTR disposed on the first electrode EL1, an emitter layer EML disposed on the hole transport region HTR, an electron transport region ETR disposed on the emitter layer EML, and a second electrode EL2 disposed on the electron transport region ETR. As described above Figures 3 to 6 The structure of the light-emitting device can be applied in the same way. Figure 7 The structure of the light-emitting device ED is shown in the figure.

[0384] refer to Figure 7 The emitting layer EML can be disposed in the opening OH defined in the pixel defining film PDL. For example, the emitting layer EML provided by the pixel defining film PDL and corresponding to each of the light-emitting areas PXA-R, PXA-G, and PXA-B can emit light within the same wavelength range. In the display device DD of the embodiment, the emitting layer EML can emit blue light. Although not shown in the figures, in an embodiment, the emitting layer EML can be provided as a common layer for all light-emitting areas PXA-R, PXA-G, and PXA-B.

[0385] A light control layer (CCL) can be disposed on a display panel (DP). The CCL may include a light converter. The light converter may include quantum dots, phosphors, etc. The light converter can convert the wavelength of the supplied light and emit the converted light. For example, the CCL may be a layer containing quantum dots or a layer containing phosphors.

[0386] The optical control layer (CCL) may include optical control components CCP1, CCP2, and CCP3. The optical control components CCP1, CCP2, and CCP3 may be spaced apart from each other.

[0387] refer to Figure 7 The separated pattern BMP can be set between the light control components CCP1, CCP2 and CCP3 that are spaced apart from each other, but the implementation is not limited to this. Figure 7 The example shows that the separated pattern BMP does not overlap with the light control components CCP1, CCP2 and CCP3, but at least a portion of the edges of the light control components CCP1, CCP2 and CCP3 may overlap with the separated pattern BMP.

[0388] The light control layer CCL may include: a first light control component CCP1 containing a first quantum dot QD1 that converts a first color light provided by the light-emitting device ED into a second color light, a second light control component CCP2 containing a second quantum dot QD2 that converts the first color light into a third color light, and a third light control component CCP3 that transmits the first color light.

[0389] In this implementation, the first light control component CCP1 can provide red light as a second color light, and the second light control component CCP2 can provide green light as a third color light. The third light control component CCP3 can provide blue light by transmitting blue light, which is the first color light provided by the light-emitting device ED. For example, the first quantum dot QD1 can be a red quantum dot, and the second quantum dot QD2 can be a green quantum dot. The same description as above regarding quantum dots can be applied to quantum dots QD1 and QD2.

[0390] The optical control layer CCL may further include a scatterer SP. The first optical control component CCP1 may include a first quantum dot QD1 and a scatterer SP, the second optical control component CCP2 may include a second quantum dot QD2 and a scatterer SP, and the third optical control component CCP3 may not contain any quantum dots but may contain a scatterer SP.

[0391] The scatterer SP can be inorganic particles. For example, the scatterer SP can include at least one selected from TiO2, ZnO, Al2O3, SiO2, and hollow silica. The scatterer SP can contain any one of TiO2, ZnO, Al2O3, SiO2, or hollow silica, or can be a mixture of at least two materials selected from TiO2, ZnO, Al2O3, SiO2, and hollow silica. The first light control component CCP1, the second light control component CCP2, and the third light control component CCP3 can each include matrix resins BR1, BR2, and BR3, wherein quantum dots QD1 and QD2 are dispersed and the scatterer SP is dispersed. In an embodiment, the first light control component CCP1 can include the first quantum dot QD1 dispersed in the first matrix resin BR1 and the scatterer SP, the second light control component CCP2 can include the second quantum dot QD2 dispersed in the second matrix resin BR2 and the scatterer SP, and the third light control component CCP3 can include the scatterer SP dispersed in the third matrix resin BR3. Matrix resins BR1, BR2, and BR3 are the media in which quantum dots QD1 and QD2 and scatterers SP are dispersed, and can be formed from various suitable resin compositions, each of which can generally be referred to as a binder. For example, matrix resins BR1, BR2, and BR3 can each independently be acrylic-based resins, urethane-based resins, silicone-based resins, epoxy-based resins, etc. Matrix resins BR1, BR2, and BR3 can be transparent resins. In embodiments, the first matrix resin BR1, the second matrix resin BR2, and the third matrix resin BR3 can each be the same as or different from each other.

[0392] The light control layer CCL may include a barrier layer BFL1. The barrier layer BFL1 prevents the penetration of moisture and / or oxygen (hereinafter referred to as "moisture / oxygen"). The barrier layer BFL1 may be disposed on the light control components CCP1, CCP2, and CCP3 to prevent the light control components CCP1, CCP2, and CCP3 from being exposed to moisture / oxygen. The barrier layer BFL1 may cover the light control components CCP1, CCP2, and CCP3. In an embodiment, the barrier layer BFL2 may be provided between the light control components CCP1, CCP2, and CCP3 and the color filter layer CFL.

[0393] Barrier layers BFL1 and BFL2 may include at least one inorganic layer. For example, barrier layers BFL1 and BFL2 may contain inorganic materials. For instance, barrier layers BFL1 and BFL2 may contain 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 a thin metal film ensuring transmittance. Barrier layers BFL1 and BFL2 may further include an organic film. Barrier layers BFL1 and BFL2 may be formed from a single layer or from multiple layers.

[0394] In the display device DD of the implementation scheme, the color filter layer CFL can be disposed on the light control layer CCL. For example, the color filter layer CFL can be directly disposed on the light control layer CCL. In the implementation scheme, the blocking layer BFL2 can be omitted.

[0395] 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 that transmits a second color of light, a second filter CF2 that transmits a third color of light, and a third filter CF3 that transmits a first color of 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. Filters CF1, CF2, and CF3 may each contain a polymer photosensitive resin and a pigment or dye. The first filter CF1 may contain a red pigment or dye, the second filter CF2 may contain a green pigment or dye, and the third filter CF3 may contain a blue pigment or dye. However, the embodiments are not limited to this, and the third filter CF3 may not contain any pigment or dye. The third filter CF3 may contain a polymer photosensitive resin and may not contain any pigment or dye. The third filter CF3 may be transparent. The third filter CF3 may be formed of a transparent photosensitive resin.

[0396] In the implementation scheme, the first filter CF1 and the second filter CF2 can each be a yellow filter. The first filter CF1 and the second filter CF2 can also be provided as a single filter, rather than being separate.

[0397] The light-shielding unit BM can be a black matrix. The light-shielding unit BM can contain organic or inorganic light-shielding materials including black pigments or dyes. The light-shielding unit BM prevents light leakage and separates the boundaries between adjacent filters CF1, CF2, and CF3. In an embodiment, the light-shielding unit BM can be formed from a blue filter.

[0398] The first to the third filters CF1, CF2 and CF3 can be set 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.

[0399] The substrate BL can be disposed on the color filter layer CFL. The substrate BL can provide a substrate surface on which the color filter layer CFL, light control layer CCL, etc., are disposed. The substrate BL can be a glass substrate, a metal substrate, a plastic substrate, etc. However, the embodiments are not limited to these, and the substrate BL can include inorganic layers, organic layers, or composite material layers. Although not shown in the figures, the substrate BL may be omitted in embodiments.

[0400] Figure 8 This is a schematic cross-sectional view illustrating a portion of a display device according to an embodiment. Figure 8 Examples are shown corresponding to Figure 7 A schematic cross-sectional view of a portion of a display panel DP. In the display device DD-TD of the embodiment, the light-emitting device ED-BT may include 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 light-emitting structures OL-B1, OL-B2, and OL-B3 stacked sequentially in the thickness direction between the first electrode EL1 and the second electrode EL2. The light-emitting structures OL-B1, OL-B2, and OL-B3 may each include an emissive layer EML (Emitting Layer). Figure 7 ), and the hole transport region HTR and electron transport region ETR located within the emitter layer EML. Figure 7 ).

[0401] For example, the light-emitting device ED-BT included in the display device DD-TD in the implementation scheme can be a light-emitting device having a series structure and including multiple emission layers.

[0402] exist Figure 8 In the illustrated embodiment, all light emitted by the light-emitting structures OL-B1, OL-B2, and OL-B3 can be blue light. However, the embodiment is not limited to this, and the light emitted by the light-emitting structures OL-B1, OL-B2, and OL-B3 can have different wavelength ranges from each other. For example, the light-emitting device ED-BT, which includes light-emitting structures OL-B1, OL-B2, and OL-B3 emitting light with different wavelength ranges from each other, can emit white light.

[0403] Charge generation layers CGL1 and CGL2 can be disposed between adjacent light-emitting structures OL-B1, OL-B2, and OL-B3. Charge generation layers CGL1 and CGL2 can each independently include a p-type charge generation layer and / or an n-type charge generation layer.

[0404] The embodiments will be described below through examples and comparative examples. The following examples are merely illustrative to aid in understanding the present disclosure, and the scope of the present disclosure is not limited thereto.

[0405] (synthesis example)

[0406] The polycyclic compounds according to embodiments of the present invention can be synthesized, for example, as follows. However, the methods for synthesizing polycyclic compounds according to embodiments of the present invention are not limited thereto.

[0407] 1. Synthesis of intermediate A-4 and intermediate B-4

[0408]

[0409] (1) Synthesis of intermediate B-1

[0410] Under an Ar atmosphere, in a 500 mL three-necked flask, B1 (12.37 g, 50 mmol) and diethyl ether (250 mL) were added and cooled to approximately -78 °C. n-BuLi (74.07 g, 120 mmol) was then added dropwise and the mixture was stirred for approximately 1 hour. B(OMe)3 (15.59 g, 150 mmol) was added dropwise, and the reaction mixture was brought to room temperature and stirred for approximately 3 hours. After the reaction, the product was neutralized with 1 M HCl, extracted with CH2Cl2, dried over MgSO4, and concentrated. The crude product was purified by silica gel column chromatography to obtain intermediate B-1 (7.65 g, 72% yield) as a white solid.

[0411] By measuring with FAB-MS, the mass number of m / z = 212 was observed through the molecular ion peak, thus confirming intermediate B-1.

[0412] (2) Synthesis of intermediate B-2

[0413] Under an Ar atmosphere, 2-nitrobromobenzene (7.0 g, 34.6 mmol), intermediate B-1 (7.36 g, 41.6 mmol), K3PO4 (14.7 g, 69.3 mmol), toluene (138.6 mL), ethanol (69.3 mL), and H2O (34.6 mL) were added sequentially to a 500 mL three-necked flask and bubbled thoroughly. Finally, Pd(PPh3)4 (1.2 g, 1.04 mmol) was added, and the mixture was heated and stirred at approximately 80 °C for about 4 hours. After cooling the mixture to room temperature, the reaction solvent was removed by distillation to obtain the crude product. The crude product was purified by silica gel column chromatography to obtain intermediate B-2 (7.8 g, 78% yield) as a white solid.

[0414] By measuring with FAB-MS, the mass number of m / z = 289 was observed through the molecular ion peak, thus confirming intermediate B-2.

[0415] (3) Synthesis of intermediate B-3

[0416] Under an Ar atmosphere, B-2 (7.5 g, 25.9 mmol), PPh3 (6.8 g, 25.9 mmol), and o-dichlorobenzene (o-DCB, 105 mL) were added to a 500 mL three-necked flask and refluxed with stirring for approximately 24 hours. The mixture was air-cooled to room temperature and filtered. The filtrate was concentrated and purified by silica gel column chromatography to obtain intermediate B-3 (5.3 g, 79% yield).

[0417] By measuring with FAB-MS, the mass number of m / z = 257 was observed through the molecular ion peak, thus confirming intermediate B-3.

[0418] (4) Synthesis of intermediate B-4

[0419] Under an Ar atmosphere, intermediate B-3 (5.0 g, 19.4 mmol), Pd(dba)2 (0.56 g, 0.05 equivalent, 0.97 mmol), NaOtBu (1.86 g, 1 equivalent, 19.40 mmol), toluene (194 mL), bromobenzene (3.05 g, 1.1 equivalent, 21.34 mmol), and tBu3P (0.79 g, 0.2 equivalent, 3.88 mmol) were added sequentially to a 500 mL three-necked flask, and the mixture was heated and stirred under reflux for approximately 6 hours. After the mixture was cooled to room temperature, the organic layer was fractionated by adding water to the reaction solvent. The organic layer was further extracted by adding toluene to the aqueous layer, and the combined organic layers were washed with brine and dried over MgSO4. The MgSO4 and the concentrated organic layer were filtered, and the resulting crude product was purified by silica gel column chromatography to obtain intermediate B-4 (5.6 g, 87% yield) as a white solid.

[0420] By measuring with FAB-MS, the mass number of m / z = 333 was observed through the molecular ion peak, thus confirming intermediate B-4.

[0421] (5) Synthesis of intermediate A-4

[0422] Intermediate A-4 was synthesized using the same method as intermediate B-4, but with A1 used instead of B1.

[0423] By measuring with FAB-MS, the mass number of m / z = 371 was observed through the molecular ion peak, thus confirming intermediate A-4.

[0424] 2. Synthesis of Compound 1

[0425]

[0426] Under an Ar atmosphere, A-4 (5.0 g, 14.98 mmol), C-1 (3.6 g, 14.98 mmol), Pd(dba)2 (0.43 g, 0.05 equivalent, 0.75 mmol), Cs2CO3 (14.64 g, 3 equivalent, 14.98 mmol), and DMF (100 mL) were added sequentially to a 200 mL three-necked flask, and the mixture was heated and stirred under reflux at approximately 130 °C for about 6 hours. After the mixture was cooled to room temperature, the organic layer was fractionated by adding water to the reaction solvent. The organic layer was further extracted by adding toluene to the aqueous layer, and the combined organic layers were washed with brine and dried over MgSO4. The MgSO4 and the concentrated organic layer were filtered, and the resulting crude product was purified by silica gel column chromatography to obtain compound 1 (5.9 g, 75% yield) as a white solid.

[0427] Compound 1 was confirmed by observing the mass number of m / z = 524 through the molecular ion peak using FAB-MS.

[0428] 3. Synthesis of Compound 481

[0429]

[0430] Compound 481 was synthesized using the same synthetic method as compound 1, but with DBT-1BPin used instead of C-1.

[0431] Compound 481 was confirmed by observing the mass number at m / z = 465 through the molecular ion peak using FAB-MS.

[0432] 4. Synthesis of Compound 241

[0433]

[0434] Compound 241 was synthesized using the same synthetic method as compound 1, but with 6-Ph-DBF-4BPin used instead of C-1.

[0435] Compound 241 was confirmed by observing the mass number of m / z = 541 through the molecular ion peak using FAB-MS.

[0436] 5. Synthesis of Compound 249

[0437]

[0438] Compound 249 was synthesized using the same synthetic method as compound 1, but with NaP-DBF-4BPin used instead of C-1.

[0439] Compound 249 was confirmed by observing the mass number at m / z = 515 through the molecular ion peak using FAB-MS.

[0440] 6. Synthesis of Compound 561

[0441]

[0442] Compound 561 was synthesized using the same synthetic method as compound 1, but with 4-Ph-DBT-3'BPin used instead of C-1.

[0443] Compound 561 was confirmed by observing the mass number at m / z = 557 through the molecular ion peak using FAB-MS.

[0444] 7. Synthesis of Compound 865

[0445]

[0446] Compound 865 was synthesized using the same synthetic method as compound 1, but with benzene-1,2-BPin used instead of C-1.

[0447] Compound 865 was confirmed by observing the mass number at m / z = 640 through the molecular ion peak using FAB-MS.

[0448] 8. Synthesis of Compound 883

[0449]

[0450] Compound 883 was synthesized using the same synthetic method as compound 1, but with DBT-4,4'-BPin used instead of C-1.

[0451] Compound 883 was confirmed by observing the mass number of m / z = 746 through the molecular ion peak using FAB-MS.

[0452] 9. Synthesis of Compound 906

[0453]

[0454] Compound 906 was synthesized using the same synthetic method as compound 1, but with A4 instead of A-4 and 6-Ph-DBF-4-BPin instead of C-1.

[0455] Compound 906 was confirmed by observing the mass number at m / z = 535 through the molecular ion peak using FAB-MS.

[0456] (Example of device manufacturing)

[0457] The following compounds from the examples and comparative examples were used as emitting layer materials to fabricate light-emitting devices:

[0458] [Example Compounds]

[0459]

[0460] [Comparative Compounds]

[0461]

[0462] The light-emitting devices of the embodiments and comparative examples were manufactured using the following method. A 150 nm thick layer of ITO was patterned on a glass substrate, and the glass substrate was washed with ultrapure water and treated with UV and ozone for approximately 10 minutes to form a first electrode. 2-TNATA was deposited on it to a thickness of approximately 60 nm, and a 30 nm thick hole transport layer was formed using either the embodiment compound or the comparative example compound. TBP was doped into ADN at 3% to form a 25 nm thick emitter layer, a 25 nm thick layer was formed on the emitter layer using Alq3, and a 1 nm thick layer was formed using LiF to form an electron transport region. A 100 nm thick second electrode was formed using aluminum (Al). Each layer was formed by vacuum deposition.

[0463] Table 1 below shows the measurement values ​​according to Examples 1 to 8 and Comparative Examples 1 to 6. At 10 mA / cm 2 The current efficiency is measured, and the half-life is expressed relative to 1,000 cd / m². 2 The time it takes to reduce the initial brightness to about 50%.

[0464] [Table 1]

[0465]

[0466]

[0467] Referring to Table 1 above, it can be confirmed that, compared with Comparative Examples 1 to 6, Examples 1 to 8 all achieved low voltage, long service life and high efficiency.

[0468] The polycyclic compound according to the embodiments is used in the hole transport region to contribute to low driving voltage, high efficiency, and long lifespan of organic electroluminescent devices. The polycyclic compound according to the embodiments is a nonamine compound having a linear benzoheterole-fused tetracyclic heteroacene skeleton containing multiple heteroatoms. The polycyclic compound contains structural bonds of indole and benzoheterole. Typically, the indole side is relatively stable, while the benzoheterole side lacks stability. The polycyclic compound according to the embodiments can be made into a more stable structure by adding substituents that increase stability to the unstable benzoheterole. Therefore, the polycyclic compound according to the embodiments can exhibit excellent properties in terms of heat resistance and charge resistance, and achieve a long lifespan of the light-emitting device. It is believed that the N, S, or O atoms contained in the polycyclic compound of the embodiments can improve the hole transport capability of the entire molecule, and thus improve the recombination probability of holes and electrons in the emitter layer, thereby improving the luminous efficiency of the light-emitting device.

[0469] As can be seen, Example 5 achieved high device efficiency. In Example 5, it is believed that the introduction of an asymmetric m-phenyl (4-dibenzothiophene) group into the benzo5-membered heterocyclic-fused tetracyclic heterocyclic benzene ring disrupted the symmetry of the entire molecule, thereby suppressing crystallinity and improving hole transport properties, and thus improving the recombination probability of holes and electrons in the emitter layer.

[0470] In Comparative Examples 1 and 2, the planarity increased due to the further fusion of the benzene ring adjacent to N, and a large spatial volume structure could not be used. Therefore, compared with the examples, the efficiency and lifespan of the light-emitting device were reduced.

[0471] In Comparative Examples 5 and 6, the formation of a film in the device was suppressed due to the increased symmetry of the molecules and the resulting good crystallinity. This, in turn, reduced the efficiency and lifespan of the light-emitting device.

[0472] The light-emitting device according to the implementation plan has excellent efficiency.

[0473] According to the implementation scheme, the polycyclic compound can be used as a material for the hole transport region of the light-emitting device, and thus the light-emitting device can have improved efficiency.

[0474] This document discloses embodiments, and although terminology is used, it is used and interpreted in a general and descriptive sense only, and not for limiting purposes. In some instances, as will be apparent to those skilled in the art, features, characteristics, and / or elements described with respect to embodiments may be used alone or in combination with features, characteristics, and / or elements described with respect to other embodiments, unless specifically indicated otherwise. Therefore, those skilled in the art will understand that various changes in form and detail may be made without departing from the spirit and scope of this disclosure as set forth in the claims.

Claims

1. Polycyclic compounds represented by Formula 1: [Formula 1] In Equation 1, X1 is O or S. Ar1 is an aryl group, substituted or unsubstituted, having 6 to 30 cyclic carbon atoms, or a heteroaryl group, substituted or unsubstituted, having 2 to 30 cyclic carbon atoms, but Ar1 is not a heteroaryl group containing two or more nitrogen atoms. R1 is a hydrogen atom, a deuterium atom, a halogen atom, or a substituted or unsubstituted alkyl group having one to 20 carbon atoms. R2 is 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 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, or is bonded to an adjacent group to form a ring. a is an integer from 0 to 4. b is an integer between 0 and 3. L is a direct bond or a group represented by one of L-1 to L-4: Among them, in L-1 to L-4, X3 is O or S. R8 is 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 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms. p is an integer from 0 to 4, and Indicates the binding site with adjacent atoms, and A is a group represented by formula 2-1 or formula 2-2, but when A is a group represented by formula 2-2, L is not a direct bond: [Equation 2-1] [Equation 2-2] In equations 2-1 and 2-2, Y is N(Ar3), O, or S. X2 is O or S. Ar2 and Ar3 are each independently a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, but neither Ar2 nor Ar3 is a heteroaryl group containing two or more nitrogen atoms. R3 to R5 are each independently 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 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, or are bonded to adjacent groups to form a ring. R6 is a hydrogen atom, a deuterium atom, a halogen atom, or a substituted or unsubstituted alkyl group having one to 20 carbon atoms. c and e are each an independent integer from 0 to 3. d and f are each an independent integer from 0 to 4, and Indicates the binding site with adjacent atoms. The term "substituted or unsubstituted" means substituted or unsubstituted by at least one substituent selected from the group consisting of deuterium atom, halogen atom, cyano group, nitro group and alkyl group having 1 to 20 carbon atoms.

2. The polycyclic compound of claim 1, wherein the polycyclic compound represented by formula 1 is represented by one of formulas 3-1 to 3-3: [Equation 3-1] [Equation 3-2] [Equation 3-3] Among them, in equations 3-1 to 3-3, R1 to R4, L, Ar1, Ar3, and a to d are the same as those defined with respect to Equations 1 and 2-1.

3. The polycyclic compound of claim 1, wherein the polycyclic compound represented by formula 1 is represented by one of formulas 4-1 to 4-3: [Equation 4-1] [Equation 4-2] [Equation 4-3] Among them, in equations 4-1 to 4-3, R1 to R4, L, Ar1, Ar3, and a to d are the same as those defined with respect to Equations 1 and 2-1.

4. The polycyclic compound of claim 1, wherein the polycyclic compound represented by formula 1 is represented by one of formulas 5-1 to 5-3: [Equation 5-1] [Equation 5-2] [Equation 5-3] Among them, in equations 5-1 to 5-3, R1, R2, R5, R6, L, Ar1, Ar2, a, b, e, and f are the same as those defined with respect to Equations 1 and 2-2.

5. The polycyclic compound of claim 1, wherein the polycyclic compound represented by formula 1 is represented by formula 6: [Formula 6] In Equation 6, R7 is 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 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, wherein "substituted or unsubstituted" is the same as defined in claim 1, and g is an integer from 0 to 5, and R1 to R3, L, Ar1, Y, X1 and a to c are the same as those defined with respect to Equations 1 and 2-1.

6. The polycyclic compound of claim 1, wherein the polycyclic compound represented by formula 1 is represented by one of formulas 7-1 to 7-3: [Equation 7-1] [Equation 7-2] [Equation 7-3] Among them, in equations 7-1 to 7-3, R1 to R3, L, Ar1, Y, X1 and a to c are the same as those defined with respect to Equations 1 and 2-1.

7. A polycyclic compound, wherein the polycyclic compound is selected from at least one of the compounds in group 1: [Compound Group 1] 。 8. A light-emitting device, comprising: First electrode; A hole transport region disposed on the first electrode; An emission layer disposed on the hole transmission region; An electron transmission area is disposed on the emission layer; as well as The second electrode is disposed on the electron transport region, wherein The hole transport region comprises a polycyclic compound according to any one of claims 1 to 7.

9. The light-emitting device of claim 8, wherein the hole transport region comprises: A hole injection layer disposed on the first electrode; as well as A hole transport layer is disposed on the hole injection layer, wherein The hole transport layer comprises a polycyclic compound according to any one of claims 1 to 7.

10. The light-emitting device of claim 8, wherein the hole transport region comprises: A hole transport layer disposed on the first electrode; as well as An electron blocking layer disposed on the hole transport layer, wherein The electron blocking layer comprises a polycyclic compound according to any one of claims 1 to 7.

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