Light emitting element and amine compound for light emitting element

Abstract

A light emitting element and an amine compound for a light emitting element are disclosed. A light emitting element of one embodiment can include a first electrode, a second electrode arranged over the first electrode, and at least one functional layer arranged between the first electrode and the second electrode. The at least one functional layer can include an amine compound represented by the following Chemical Formula 1. Thus, a light emitting element of one embodiment can exhibit improved emission efficiency and element lifetime.[Chemical Formula 1]

Description

Technical Field

[0001] The present invention relates to a light-emitting element and an amine compound for the light-emitting element, and more specifically, to an amine compound used as a hole transport material and a light-emitting element comprising the amine compound. Background Technology

[0002] Recently, as an image display device, there has been a great deal of development on organic electroluminescence display devices and the like. Organic electroluminescence display devices are display devices that include so-called self-emissive light-emitting elements that achieve display by causing the light-emitting material of the light-emitting layer to emit light through the recombination of holes and electrons injected from the first electrode and the second electrode in the light-emitting layer.

[0003] When applying light-emitting elements to display devices, there is a need for low driving voltage, high luminous efficiency, and long lifespan, and there is a continuous need to develop materials for light-emitting elements that can reliably achieve these goals. Summary of the Invention

[0004] The purpose of this invention is to provide a light-emitting element that exhibits excellent luminous efficiency and long lifespan.

[0005] Another object of the present invention is to provide an amine compound as a material for light-emitting elements having high efficiency and long lifespan characteristics.

[0006] One embodiment provides a light-emitting element, comprising: a first electrode; a second electrode disposed on the first electrode; and at least one functional layer disposed between the first electrode and the second electrode, and comprising an amine compound represented by the following chemical formula 1.

[0007] [Chemical Formula 1]

[0008]

[0009] In the aforementioned chemical formula 1, n1 and n2 are independently 0 or 1, a1 and a2 are independently integers of 0 to 5, a3 to a6 are independently integers of 0 to 4, R1 to R6 are independently hydrogen atoms, deuterium atoms, halogen atoms, alkyl groups with 1 to 15 substituted or unsubstituted carbon atoms, or heteroaryl groups with 2 to 20 substituted or unsubstituted cyclic carbon atoms, and Q1 is represented by the following chemical formula 2.

[0010] [Chemical Formula 2]

[0011]

[0012] In the aforementioned chemical formula 2, X is O or S. When X is O, N in chemical formula 1 combines with any one of C1, C2, and C4. a11 is an integer between 0 and 7. R 11 An aryl group consisting of 6 to 12 cyclic carbon atoms, which are hydrogen atoms, deuterium atoms, or substituted or unsubstituted carbon atoms.

[0013] The chemical formula 1 can be represented by the following chemical formula 1-1 or the following chemical formula 1-2.

[0014] [Chemical Formula 1-1]

[0015]

[0016] [Chemical Formula 1-2]

[0017]

[0018] In chemical formulas 1-1 and 1-2, a1 to a6, R1 to R6, n1, and n2 are defined as in chemical formula 1, and a11 and R... 11 Same as the definition in Chemical Formula 2.

[0019] Chemical formula 2 can be represented by any one of the following chemical formulas 2-1 to 2-4.

[0020]

[0021]

[0022] In the chemical formulas 2-1 to 2-4, a11, R 11 And X is defined in the same way as in the chemical formula 2.

[0023] The chemical formula 1 can be represented by any one of the following chemical formulas 1-A to 1-C.

[0024] [Chemical Formula 1-A]

[0025]

[0026] [Chemical Formula 1-B]

[0027]

[0028] [Chemical Formula 1-C]

[0029]

[0030] In chemical formulas 1-A to 1-C, a1 to a6, R1 to R6, n1, n2, and Q1 are defined as in chemical formula 1.

[0031] The chemical formula 1-A can be represented by any one of the following chemical formulas 1-A1 to 1-A3.

[0032] [Chemical Formula 1-A1]

[0033]

[0034] [Chemical Formula 1-A2]

[0035]

[0036] [Chemical Formula 1-A3]

[0037]

[0038] In the chemical formulas 1-A1 to 1-A3, a1 to a6, R1 to R6, n1, n2, and Q1 are defined in the same way as in the chemical formula 1-A.

[0039] R1 and R5 can be either fluorine atoms or methyl groups, respectively.

[0040] a11 is either 0 or 1. When a11 is 1, R 11 It can be a substituted or unsubstituted phenyl group.

[0041] At least one of R1 to R3 can be a deuterium atom.

[0042] The at least one functional layer may include: a light-emitting layer; a hole transport region disposed between the first electrode and the light-emitting layer; and an electron transport region disposed between the light-emitting layer and the second electrode, wherein the hole transport region may include the amine compound.

[0043] The hole transport region may include: a hole injection layer disposed on the first electrode; a hole transport layer disposed on the hole injection layer; and an electron blocking layer disposed on the hole transport layer, wherein at least one of the hole injection layer, the hole transport layer, and the electron blocking layer may include the amine compound.

[0044] One embodiment provides an amine compound represented by the chemical formula 1.

[0045] One embodiment of the light-emitting element can exhibit high efficiency and long lifetime characteristics by including an amine compound of one embodiment in the hole transport region.

[0046] One embodiment of the amine compound can improve the luminous efficiency and lifespan of the light-emitting element. Attached Figure Description

[0047] Figure 1 This is a plan view showing a display device according to an embodiment.

[0048] Figure 2 This is a cross-sectional view showing a display device according to an embodiment.

[0049] Figure 3 This is a schematic cross-sectional view of a light-emitting element according to one embodiment.

[0050] Figure 4 This is a schematic cross-sectional view of a light-emitting element according to one embodiment.

[0051] Figure 5 This is a schematic cross-sectional view of a light-emitting element according to one embodiment.

[0052] Figure 6 This is a schematic cross-sectional view of a light-emitting element according to one embodiment.

[0053] Figure 7 This is a cross-sectional view showing a display device according to an embodiment.

[0054] Figure 8 This is a cross-sectional view showing a display device according to an embodiment.

[0055] [Explanation of Labels in the Attached Image]

[0056] DD, DD-TD: Display device; ED: Light-emitting element

[0057] EL1: First electrode; EL2: Second electrode

[0058] HTR: Hole Transport Region; EML: Emitting Layer

[0059] ETR: Electron Transmission Region; CPL: Capping Layer Detailed Implementation

[0060] This invention can be modified in many ways and can have many forms. Specific embodiments are illustrated in the accompanying drawings and described in detail herein. However, it is not intended to limit the invention to the specific disclosed forms, and should be understood to include all modifications, equivalents, and substitutions encompassed by the spirit and scope of the invention.

[0061] In this specification, when a component (or region, layer, part, etc.) is referred to as being "above", "connected" to, or "combined" with another component, it means that it can be directly arranged / connected / combined with the other component, or that a third component may be arranged between them.

[0062] The same reference numerals refer to the same constituent elements. Furthermore, for the purpose of effective explanation of the technical content, the thickness, scale, and dimensions of the constituent elements are exaggerated in the drawings.

[0063] "And / or" includes all combinations of related components that can be defined.

[0064] The terms "first," "second," etc., can be used to describe multiple constituent elements, but the constituent elements should not be limited by the terms. The terms are used only to distinguish one constituent element from another. For example, without departing from the scope of the invention, a first constituent element can be named a second constituent element, and similarly, a second constituent element can be named a first constituent element. Singular expressions include plural expressions unless the context explicitly indicates a different meaning.

[0065] Furthermore, terms such as "below," "lower side," "above," and "upper side" are used to describe the relationships between the components shown in the accompanying drawings. These terms are relative concepts and are explained based on the directions indicated in the accompanying drawings.

[0066] Unless otherwise defined, all terms (including technical and scientific terms) used in this specification shall have the same meaning as commonly understood by one of ordinary skill in the art to which this invention pertains. Furthermore, terms such as those defined in commonly used dictionaries shall be interpreted as having the same meaning as in the context of the relevant art, and are hereby explicitly defined unless interpreted as having an ideal or overly formal meaning.

[0067] Terms such as “including” or “having” should be understood as being intended to specify the presence of features, figures, steps, operations, constituent elements, components or combinations thereof described in the specification, rather than precluding the presence or possibility of one or more other features or figures, steps, operations, constituent elements, components or combinations thereof.

[0068] Hereinafter, an embodiment of the present invention will be described with reference to the accompanying drawings.

[0069] Figure 1 This is a plan view showing an embodiment of the display device DD. Figure 2 This is a cross-sectional view of a display device DD according to an embodiment. Figure 2 It is shown that... Figure 1 A cross-sectional view of the portion corresponding to the I-I' line.

[0070] The display device DD may include: a display panel DP; and an optical layer PP disposed on the display panel DP. The display panel DP includes light-emitting elements ED-1, ED-2, and ED-3. The display device DD may include multiple light-emitting elements ED-1, ED-2, and ED-3. The optical layer PP may be disposed on the display panel DP to control reflected light at the display panel DP caused by external light. The optical layer PP may, for example, include a polarizing layer or a color filter layer. Furthermore, unlike the case shown in the figures, in one embodiment of the display device DD, the optical layer PP may be omitted.

[0071] A base substrate BL can be disposed on the optical layer PP. The base substrate BL can be a component that provides a base surface for disposing the optical layer PP. The base substrate BL can be a glass substrate, a metal substrate, a plastic substrate, etc. However, the embodiments are not limited to this; the base substrate BL can be an inorganic layer, an organic layer, or a composite material layer. Furthermore, unlike the illustrated case, in one embodiment, the base substrate BL can be omitted.

[0072] The display device DD according to one embodiment may further include a filler layer (not shown). The filler layer (not shown) may be disposed between the display element layer DP-ED and the base substrate BL. The filler layer (not shown) may be an organic layer. The filler layer (not shown) may include at least one of acrylic resin, silicone resin and epoxy resin.

[0073] The display panel DP may include a base layer BS, a circuit layer DP-CL disposed on the base layer BS, and a display element layer DP-ED. The display element layer DP-ED may include: a pixel defining film PDL; light-emitting elements ED-1, ED-2, and ED-3 disposed between the pixel defining films PDL; and an encapsulation layer TFE disposed on the light-emitting elements ED-1, ED-2, and ED-3.

[0074] The base layer BS can be a component that provides a base surface for arranging the display element layer DP-ED. The base layer BS can be a glass substrate, a metal substrate, a plastic substrate, etc. However, the embodiments are not limited to this; the base layer BS can be an inorganic layer, an organic layer, or a composite material layer.

[0075] In one embodiment, a circuit layer DP-CL is disposed on a base layer BS, and the circuit layer DP-CL may include a plurality of transistors (not shown). Each transistor (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 for driving the light-emitting elements ED-1, ED-2, and ED-3 of the display element layer DP-ED.

[0076] Each of the light-emitting elements ED-1, ED-2, and ED-3 may have the following characteristics. Figures 3 to 6 The structure of a light-emitting element ED according to one embodiment. Each of the light-emitting elements ED-1, ED-2, and ED-3 may include a first electrode EL1, a hole transport region HTR, light-emitting layers EML-R, EML-G, EML-B, an electron transport region ETR, and a second electrode EL2.

[0077] exist Figure 2 An embodiment is shown below: the light-emitting layers EML-R, EML-G, and EML-B of light-emitting elements ED-1, ED-2, and ED-3 are arranged within the opening OH defined by the pixel-defining film PDL. The hole transport region HTR, the electron transport region ETR, and the second electrode EL2 are provided as a common layer throughout the light-emitting elements ED-1, ED-2, and ED-3. However, the embodiment is not limited to this, and... Figure 2 In a different embodiment, the hole transport region HTR and electron transport region ETR can be patterned and provided within the opening OH defined by the pixel defining film PDL. For example, in one embodiment, the hole transport region HTR, the light-emitting layers EML-R, EML-G, EML-B, and the electron transport region ETR of the light-emitting elements ED-1, ED-2, and ED-3 can be patterned using an inkjet printing method.

[0078] The encapsulation layer TFE can cover the light-emitting elements ED-1, ED-2, and ED-3. The encapsulation layer TFE can seal the display element layer DP-ED. The encapsulation layer TFE can be a thin-film encapsulation layer. The encapsulation layer TFE can be a single layer or composed of multiple stacked layers. The encapsulation layer TFE includes at least one insulating layer. According to one embodiment, the encapsulation layer TFE can include at least one inorganic film (hereinafter referred to as the encapsulation inorganic film). Furthermore, according to one embodiment, the encapsulation layer TFE can include at least one organic film (hereinafter referred to as the encapsulation organic film) and at least one encapsulation inorganic film.

[0079] An inorganic encapsulation film protects the DP-ED display element layer from moisture and oxygen, while an organic encapsulation film protects the DP-ED display element layer from foreign matter such as dust particles. The inorganic encapsulation film may include, but is not specifically limited to, silicon nitride, silicon oxynitride, silicon oxide, titanium dioxide, or aluminum oxide. The organic encapsulation film may include, but is not specifically limited to, acrylic compounds, epoxy compounds, etc. The organic encapsulation film may include photopolymerizable organic materials.

[0080] The encapsulation layer TFE can be disposed on the second electrode EL2. Furthermore, the encapsulation layer TFE can be disposed to fill the opening OH.

[0081] Reference Figure 1 and Figure 2 The display device DD may include a non-light-emitting area NPXA and light-emitting areas PXA-R, PXA-G, and PXA-B. Each light-emitting area PXA-R, PXA-G, and PXA-B may be an area that emits light generated from each light-emitting element ED-1, ED-2, and ED-3. The light-emitting areas PXA-R, PXA-G, and PXA-B may be spaced apart from each other on a plane.

[0082] Each of the light-emitting regions PXA-R, PXA-G, and PXA-B can be a region defined by a pixel-defining film (PDL). The non-light-emitting region NPXA is the region between adjacent light-emitting regions PXA-R, PXA-G, and PXA-B, and can be a region corresponding to the pixel-defining film (PDL). Furthermore, in this specification, each of the light-emitting regions PXA-R, PXA-G, and PXA-B can correspond to a pixel. The pixel-defining film (PDL) can divide the light-emitting elements ED-1, ED-2, and ED-3. The light-emitting layers EML-R, EML-G, and EML-B of the light-emitting elements ED-1, ED-2, and ED-3 can be divided by being arranged at the opening OH defined by the pixel-defining film (PDL).

[0083] The luminescent regions PXA-R, PXA-G, and PXA-B can be divided into multiple groups based on the color of the light generated by the luminescent elements ED-1, ED-2, and ED-3. Figure 1 and Figure 2 In one embodiment of the display device DD, three light-emitting regions PXA-R, PXA-G, and PXA-B emitting red, green, and blue light are exemplarily shown. For example, one embodiment of the display device DD may include red light-emitting regions PXA-R, green light-emitting regions PXA-G, and blue light-emitting regions PXA-B that are divided from each other.

[0084] In a display device DD according to one embodiment, a plurality of light-emitting elements ED-1, ED-2, and ED-3 can emit light in different wavelengths. For example, in one embodiment, the display device DD may include a first light-emitting element ED-1 that emits red light, a second light-emitting element ED-2 that emits green light, and a third light-emitting element ED-3 that emits blue light. That is, 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 element ED-1, the second light-emitting element ED-2, and the third light-emitting element ED-3, respectively.

[0085] However, the embodiments are not limited thereto. The first to third light-emitting elements ED-1, ED-2, and ED-3 may emit light of the same wavelength, or at least one of them may emit light of different wavelengths. For example, the first to third light-emitting elements ED-1, ED-2, and ED-3 may all emit blue light.

[0086] According to one embodiment, the light-emitting regions PXA-R, PXA-G, and PXA-B in the display device DD can be arranged in a stripe pattern. (See reference...) Figure 1 Multiple red emitting regions PXA-R, multiple green emitting regions PXA-G, and multiple blue emitting regions PXA-B can be arranged along the second directional axis DR2. Furthermore, they can be arranged alternately along the first directional axis DR1 in the order of red emitting regions PXA-R, green emitting regions PXA-G, and blue emitting regions PXA-B.

[0087] exist Figure 1 and Figure 2 The illustration shows a scenario where the areas of the luminescent regions PXA-R, PXA-G, and PXA-B are all similar, but the embodiment is not limited to this. The areas of the luminescent regions PXA-R, PXA-G, and PXA-B can differ from each other depending on the wavelength of the emitted light. Furthermore, the areas of the luminescent regions PXA-R, PXA-G, and PXA-B can represent the areas when viewed from a plane defined by the first direction axis DR1 and the second direction axis DR2.

[0088] Furthermore, the arrangement of the luminescent regions PXA-R, PXA-G, and PXA-B is not limited to... Figure 1 As shown, the arrangement order of the red emitting areas PXA-R, green emitting areas PXA-G, and blue emitting areas PXA-B can be varied and provided according to the display quality characteristics required by the display device DD. For example, the arrangement of the emitting areas PXA-R, PXA-G, and PXA-B can be a pentile arrangement or a diamond arrangement.

[0089] Furthermore, the areas of the light-emitting regions PXA-R, PXA-G, and PXA-B can be different from each other. For example, in one embodiment, the area of ​​the green light-emitting region PXA-G can be smaller than the area of ​​the blue light-emitting region PXA-B, but the embodiment is not limited to this.

[0090] the following, Figures 3 to 6 This is a schematic cross-sectional view of a light-emitting element according to one embodiment. The light-emitting element ED according to one embodiment may include a first electrode EL1, a hole transport region HTR, a light-emitting layer EML, an electron transport region ETR, and a second electrode EL2, stacked sequentially.

[0091] compared to Figure 3 , Figure 4 A cross-sectional view of a light-emitting element (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). Furthermore, compared to... Figure 3 , Figure 5 A cross-sectional view of a light-emitting element (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). Compared to... Figure 4 , Figure 6 A cross-sectional view of a light-emitting element ED, including a capping layer CPL disposed on a second electrode EL2, is shown.

[0092] The first electrode EL1 is conductive. The first electrode EL1 can be formed of a metallic material, 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. Furthermore, the first electrode EL1 can be a pixel electrode. The first electrode EL1 can be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode. In the case where the first electrode EL1 is a transmissive electrode, the first electrode EL1 can include a transparent metal oxide, such as indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), indium tin zinc oxide (ITZO), etc. When the first electrode EL1 is a semi-transparent or reflective electrode, the first electrode EL1 may include Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF, Mo, Ti, W, their compounds or mixtures (e.g., a mixture of Ag and Mg), or a material having a multilayer structure such as LiF / Ca or LiF / Al. Alternatively, the first electrode EL1 may be a multilayer structure including a reflective or semi-transparent film formed from the aforementioned materials and a transparent conductive film formed from indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), indium tin zinc oxide (ITZO), etc. For example, the first electrode EL1 may have a three-layer structure of ITO / Ag / ITO, but is not limited thereto. Furthermore, the embodiments are not limited thereto; the first electrode EL1 may include the aforementioned metallic materials, a combination of two or more metallic materials selected from the aforementioned metallic materials, or oxides of the aforementioned metallic materials, etc. The thickness of the first electrode EL1 can be approximately up to approximately For example, the thickness of the first electrode EL1 can be approximately up to approximately

[0093] The hole transport region HTR is provided on the first electrode EL1. In one embodiment of the light-emitting element ED, the hole transport region HTR may include an amine compound.

[0094] In this specification, "substituted or unsubstituted" can mean that the substance is substituted or unsubstituted by one or more substituents selected from the group consisting of deuterium, halogen, cyano, nitro, amino, silyl, oxy, thio, sulfinyl, sulfonyl, carbonyl, boron, phosphonyl oxide, phosphonyl sulfide, alkyl, alkenyl, alkynyl, alkylcycloyl, aryl, and heterocyclic groups. Furthermore, each of the substituents exemplified above can be either substituted or unsubstituted. For example, biphenyl can be interpreted as aryl or as a phenyl group substituted with a phenyl group.

[0095] Examples of halogen atoms in this specification include fluorine, chlorine, bromine, or iodine atoms.

[0096] In this specification, alkyl groups can be straight-chain, branched, or cyclic. The number of carbon atoms in an alkyl group is 1 to 50, 1 to 30, 1 to 20, 1 to 10, or 1 to 6. Examples of alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, isobutyl, 2-ethylbutyl, 3,3-dimethylbutyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, cyclopentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 2-butylhexyl, cyclohexyl, 4-methylcyclohexyl, 4-tert-butylcyclohexyl, n-heptyl, 1-methylheptyl, 2,2-dimethylheptyl, 2-ethylheptyl, 2-butylheptyl, n-octyl, tert-octyl, 2-ethyloctyl, 2-butyloctyl, 2-hexyloctyl, 3,7-dimethyloctyl, cyclooctyl, n-nonyl, n-decyl, adamantyl, 2-ethyldecyl, 2-butyldecyl, 2 - Hexyldecyl, 2-octyldecyl, undecyl, dodecyl, 2-ethyldodecyl, 2-butyldodecyl, 2-hexyldodecyl, 2-octyldodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, 2-ethylhexadecyl, 2-butylhexadecyl, 2-hexylhexadecyl, 2-octylhexadecyl, heptadecanyl, octadecyl, nonadecanyl, eicosyl, 2-ethyleicosyl, 2-butyleicosyl, 2-hexyleicosyl, 2-octyleicosyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecanyl, hexadecyl, octadecyl, nonadecanyl, and triadecyl, etc., but not limited to these.

[0097] In this specification, aryl represents any functional group or substituent derived from an aromatic hydrocarbon ring. Aryl groups can be monocyclic or polycyclic. The number of carbon atoms in the cyclic aryl group can be 6 to 30, 6 to 20, or 6 to 15. Examples of aryl groups include phenyl, naphthyl, fluorenyl, anthraceneyl, phenanthryl, biphenyl, terphenyl, tetraphenyl, quinquephenyl, hexaphenyl, benzo[9,10]phenanthryl, pyrene, benzofluoranthracene, etc. It includes, but is not limited to, basic, and advanced technologies.

[0098] In this specification, a heteroaryl group may include one or more of B, O, N, P, Si, and S as a heteroatom. When a heteroaryl group includes two or more heteroatoms, these heteroatoms may be identical or different from each other. A heteroaryl group may be a monocyclic heterocyclic group or a polycyclic heteroaryl group. The number of carbon atoms in the ring-forming structure of the heteroaryl group may be 2 to 30, 2 to 20, or 2 to 10. Examples of heteroaryl groups include thiophene, furanyl, pyrrole, imidazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinel, pyridazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazole, N-arylcarbazole, and N-heteroarylcarbazole. N-alkylcarbazolyl, benzoxazolyl, benzoimidazolyl, benzothiazolyl, benzocarbazolyl, benzothiophene, dibenzothiophene, thiophene-thiophene, benzofuranyl, phenanthrolinel, thiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, thiadiazolyl, phenothiazinyl, dibenzosilole, and dibenzofuranyl, etc., but not limited to these.

[0099]

[0100] In one embodiment of the light-emitting element ED, the hole transport region HTR may include an amine compound represented by the following chemical formula 1.

[0101] [Chemical Formula 1]

[0102]

[0103] In chemical formula 1, n1 and n2 can be 0 or 1 independently, respectively. For example, when n1 is 1, the benzene ring including R1 can include a phenyl group as a substituent. When n2 is 1, the benzene ring including R2 can include a phenyl group as a substituent.

[0104] In chemical formula 1, a1 and a2 can each be an integer greater than or equal to 0 and less than or equal to 5. a3 to a6 can each be an integer greater than or equal to 0 and less than or equal to 4. When a1 is an integer greater than or equal to 2, all R1s can be the same, or at least one of the R1s can be different. When a2 is an integer greater than or equal to 2, all R2s can be the same, or at least one of the R2s can be different. When a3 is an integer greater than or equal to 2, all R3s can be the same, or at least one of the R3s can be different. When a4 is an integer greater than or equal to 2, all R4s can be the same, or at least one of the R4s can be different. When a5 is an integer greater than or equal to 2, all R5s can be the same, or at least one of the R5s can be different. When a6 is an integer greater than or equal to 2, all R6s can be the same, or at least one of the R6s can be different.

[0105] R1 to R6 can each be independently a hydrogen atom, a deuterium atom, a halogen atom, an alkyl group with 1 to 15 substituted or unsubstituted carbon atoms, or a heteroaryl group with 2 to 20 substituted or unsubstituted cyclic carbon atoms. R1 and R5 can each be independently a fluorine atom or a methyl atom. For example, a1 can be 0 or 1. When a1 is 1, R1 can be methyl. a5 can be 0 or 1. When a5 is 1, R5 can be methyl or a fluorine atom.

[0106] According to one embodiment, at least one of R1 to R3 can be a deuterium atom. When a1 is 5, multiple R1s can be deuterium atoms. When a1 and a2 are 5, multiple R1s and multiple R2s can be deuterium atoms. When a1 and a3 are 5, multiple R1s and multiple R3s can be deuterium atoms.

[0107] In chemical formula 1, Q1 can be represented by chemical formula 2. In chemical formula 2, C1 to C4 represent the positions of carbon atoms, which can combine with N in chemical formula 1.

[0108] [Chemical Formula 2]

[0109]

[0110] In chemical formula 2, X can be O or S. When X is O, N and C3 in chemical formula 1 may not be combined. When X is O, N in chemical formula 1 can combine with any one of C1, C2, and C4.

[0111] Q1 can be a substituted or unsubstituted dibenzofuranyl or a substituted or unsubstituted dibenzothiophenylyl. In the case where Q1 is a substituted or unsubstituted dibenzofuranyl, the N in Formula 1 and the C3 of the 3rd carbon in the cyclizing atom of the substituted or unsubstituted dibenzofuranyl may not be bonded.

[0112] In chemical formula 2, a11 can be an integer greater than 0 and less than 7. When a11 is an integer greater than 2, multiple R... 11 They can all be the same, or multiple Rs. 11 At least one of them can be different. R 11 It can be a hydrogen atom, a deuterium atom, or an aryl group with 6 to 12 cyclic carbon atoms, either substituted or unsubstituted. For example, a11 can be 0 or 1. In the case where a11 is 1, R... 11 It can be a substituted or unsubstituted phenyl group. R 11 It can be an unsubstituted phenyl group. Furthermore, R 11 It can be a phenyl group that has been substituted with a phenyl group.

[0113] For example, when a11 is 1, R 11 The N in Formula 1 can be independently bonded to the C4 or C1 position of Formula 2. However, this is merely exemplary, and the embodiments are not limited thereto.

[0114] According to one embodiment, chemical formula 2 can be represented by any one of chemical formulas 2-1 to 2-4. Chemical formula 2-1 shows the case where the carbon bonded to N in chemical formula 1 is C1. Chemical formula 2-2 shows the case where the carbon bonded to N in chemical formula 1 is C2. Chemical formula 2-3 shows the case where X is S and the carbon bonded to N in chemical formula 1 is C3. Chemical formula 2-4 shows the case where the carbon bonded to N in chemical formula 1 is C4.

[0115]

[0116] Chemical formulas 2-1, 2-2, and 2-4 can each be independently a substituted or unsubstituted dibenzofuranyl or a substituted or unsubstituted dibenzothiopheneyl. In chemical formulas 2-1 to 2-4, a11, R... 11 And X can be applied to the same content as described in Chemical Formula 1.

[0117] In one embodiment, Formula 1 can be represented by either Formula 1-1 or Formula 1-2. Formula 1-1 shows the case where Q1 is represented by Formula 2, where X in Formula 2 is O. Formula 1-2 shows the case where Q1 is represented by Formula 2, where X in Formula 2 is S. Formula 1-1 shows the case where Q1 is a substituted or unsubstituted dibenzofuranyl group, and Formula 1-2 shows the case where Q1 is a substituted or unsubstituted dibenzothiophenyl group.

[0118] [Chemical Formula 1-1]

[0119]

[0120] [Chemical Formula 1-2]

[0121]

[0122] In Chemical Formulas 1-1 and 1-2, a1 to a6, R1 to R6, n1, and n2 can be used with the same content as described in Chemical Formula 1, a11, and R... 11 The same content as that described in Chemical Formula 2 can be applied.

[0123] According to one embodiment, Formula 1 can be represented by any one of Formulas 1-A to 1-C. Formula 1-A shows the case where N and a benzene ring including R4 are bonded to the para position of a benzene ring including R6. Formula 1-B shows the case where N and a benzene ring including R4 are bonded to the meta position of a benzene ring including R6. Formula 1-C shows the case where N and a benzene ring including R4 are bonded to the ortho position of a benzene ring including R6.

[0124] [Chemical Formula 1-A]

[0125]

[0126] [Chemical Formula 1-B]

[0127]

[0128] [Chemical Formula 1-C]

[0129]

[0130] In Formulas 1-A to 1-C, a1 to a6, R1 to R6, n1, n2, and Q1 may be the same as those described in Formula 1. For example, in Formula 1-B, a benzene ring including R3 and N may be attached to the meta position of a benzene ring including R5. In Formula 1-C, a benzene ring including R3 and N may be attached to the ortho position of a benzene ring including R5. In Formulas 1-B and 1-C, n1 and n2 may be 0.

[0131] Furthermore, Formula 1-A can be represented by any one of Formulas 1-A1 to 1-A3. Formula 1-A1 shows the case in Formula 1-A where the benzene ring including R3 and N are bonded at the para position to the benzene ring including R5. Formula 1-A2 shows the case in Formula 1-A where the benzene ring including R3 and N are bonded at the meta position to the benzene ring including R5. Formula 1-A3 shows the case in Formula 1-A where the benzene ring including R3 and N are bonded at the ortho position to the benzene ring including R5.

[0132] [Chemical Formula 1-A1]

[0133]

[0134] [Chemical Formula 1-A2]

[0135]

[0136] [Chemical Formula 1-A3]

[0137]

[0138] In chemical formulas 1-A1 to 1-A3, a1 to a6, R1 to R6, n1, n2, and Q1 may be the same as those described in chemical formula 1.

[0139] An amine compound represented by Chemical Formula 1 in one embodiment can be represented by any one of the compounds in Compound Group 1 below. The hole transport region (HTR) of a light-emitting element (ED) in one embodiment can include at least one of the amine compounds disclosed in Compound Group 1 below.

[0140] [Compound Group 1]

[0141]

[0142]

[0143]

[0144]

[0145] In compounds 74 to 77 of compound group 1, D is a deuterium atom.

[0146] An amine compound of one embodiment, represented by Chemical Formula 1, may include two terphenyl groups bonded to a nitrogen atom and a heteroaryl group. The heteroaryl group may be a substituted or unsubstituted dibenzofuranyl group or a substituted or unsubstituted dibenzothiophenyl group. An amine compound of one embodiment may include a molecular structure represented by the following Chemical Formula Z, in which an ortho-terphenyl group is directly bonded to a nitrogen atom.

[0147] [Chemical Formula Z]

[0148]

[0149] Due to the stereochemical properties of the terphenyl group bonded to the nitrogen atom, the amine compound of one embodiment exhibits improved material stability and hole transport properties. When the amine compound of one embodiment is included in the hole transport region of the light-emitting element, hole transport is enhanced, thereby increasing the probability of recombination of holes and electrons within the light-emitting layer. Therefore, the luminous efficiency and lifetime of the light-emitting element can be improved.

[0150] The hole transport region (HTR) may include at least one of a hole injection layer (HIL), a hole transport layer (HTL), a buffer layer or a light-emitting auxiliary layer (not shown), and an electron blocking layer (EBL). At least one of the hole injection layer (HIL), the hole transport layer (HTL), and the electron blocking layer (EBL) may include an amine compound according to one embodiment. For example, the hole transport region (HTR) may include a hole injection layer (HIL), a hole transport layer (HTL), and an electron blocking layer (EBL), and the hole transport layer (HTL) may include an amine compound according to one embodiment.

[0151] The thickness of the hole transport region (HTR) can be, for example, approximately up to approximately The hole transport region (HTR) can have a single-layer structure composed of a single substance, a single-layer structure composed of multiple different substances, or a multi-layer structure composed of multiple different substances.

[0152] For example, the hole transport region HTR can have a single-layer structure of hole transport layer HTL, or it can have a single-layer structure composed of hole injection material and hole transport material. Furthermore, the hole transport region HTR can have a single-layer structure composed of multiple different materials, or it can have a structure consisting of hole injection layer HIL / hole transport layer HTL, hole injection layer HIL / hole transport layer HTL / buffer layer (not shown), hole injection layer HIL / buffer layer (not shown), hole transport layer HTL / buffer layer (not shown), or hole injection layer HIL / hole transport layer HTL / electron blocking layer EBL, stacked sequentially from the first electrode EL1. However, the embodiments are not limited to these.

[0153] Hole transport regions (HTRs) can be formed using various methods, including vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) method, inkjet printing, laser printing, and laser-induced thermal imaging (LITI).

[0154] In addition to the amine compound of the above embodiment, the light-emitting element ED of one embodiment may also include the hole transport material described below. The hole transport region HTR may include a compound represented by the following chemical formula H-1.

[0155] [Chemical formula H-1]

[0156]

[0157] In the chemical formula H-1, L1 and L2 can each be independently a directly linked aryl group with 6 to 30 cyclic carbon atoms (substituted or unsubstituted) or a heteroaryl group with 2 to 30 cyclic carbon atoms (substituted or unsubstituted). a and b can each be independently an integer from 0 to 10. Furthermore, when a or b is an integer of 2 or more, multiple L1 and L2 can each be independently an aryl group with 6 to 30 cyclic carbon atoms (substituted or unsubstituted) or a heteroaryl group with 2 to 30 cyclic carbon atoms (substituted or unsubstituted).

[0158] In the chemical formula H-1, Ar1 and Ar2 can each be independently an aryl group with 6 to 30 cyclic carbon atoms (substituted or unsubstituted) or a heteroaryl group with 2 to 30 cyclic carbon atoms (substituted or unsubstituted). Furthermore, in the chemical formula H-1, Ar3 can be an aryl group with 6 to 30 cyclic carbon atoms (substituted or unsubstituted).

[0159] The compound represented by the chemical formula H-1 can be a monoamine compound. Alternatively, the compound represented by the chemical formula H-1 can be a diamine compound comprising at least one of Ar1 to Ar3, with an amino group as a substituent. Furthermore, the compound represented by the chemical formula H-1 can be a carbazole compound comprising at least one of Ar1 and Ar2, with a substituted or unsubstituted carbazole group, or a fluorene compound comprising at least one of Ar1 and Ar2, with a substituted or unsubstituted fluorene group.

[0160] A compound represented by the chemical formula H-1 can be represented by any one of the compounds in the following compound group H. However, the compounds listed in the following compound group H are exemplary, and compounds represented by the chemical formula H-1 are not limited to those shown in the following compound group H.

[0161] [Compound Group H]

[0162]

[0163] The hole transport region (HTR) may also include phthalocyanine compounds such as copper phthalocyanine, N... 1 N 1 '-([1,1'-biphenyl]-4,4'-diyl)bis(N 1 -Phenyl-N 4 N 4 -di-m-tolylphenyl-1,4-diamine)(DNTPD:N 1 N 1 '-([1,1'-biphenyl]-4,4'-diyl)bis(N 1 -phenyl-N 4 N 4-di-m-tolylbenzene-1,4-diamine), 4,4',4"-[tris(3-methylphenyl)phenylamino]triphenylamine (m-MTDATA: 4,4',4"-[tris(3-methylphenyl)phenylamino]triphenylamine), 4,4',4"-tris(N,N-diphenylamino)triphenylamine (TDATA: 4,4',4"-Tris(N,N-diphenylamino)triphenylamine), 4,4',4"-tris[N-(2-naphthyl)-N-phenylamine]triphenylamine 4,4',4"-tris[N-(2-naphthyl)-N-phenylamino]-triphenylamine, poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / dodecylbenzenesulfonic acid (PANI / DBSA), polyaniline / camphor sulfonic acid (PANI / CSA) sulfonicacid), polyaniline / poly(4-styrenesulfonate) (PANI / PSS: Polyaniline / Poly(4-styrenesulfonate)), N,N'-di(naphthalene-1-yl)-N,N'-diphenyl-benzidine (NPB: N,N'-di(naphthalene-l-yl)-N,N'-diphenyl-benzidine), triphenylamine-containing polyetherketone (TPAPEK), 4-isopropyl-4'-methyldiphenyliodonium [tetra(pentafluoro) [4-Isopropyl-4'-methyldiphenyliodonium[Tetrakis(pentafluorophenyl)borate]], dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile, etc.

[0164] Furthermore, the hole transport region (HTR) can also include carbazole derivatives such as N-phenylcarbazole and polyvinylcarbazole, fluorene derivatives, N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (TPD: N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine), and 4,4',4"-tris(N-carbazolyl)triphenylamine (TCTA: 4,4 Triphenylamine derivatives such as ',4'-tris(N-carbazolyl)triphenylamine, N,N'-di(naphthalene-1-yl)-N,N'-diphenyl-benzidine (NPB: N,N'-di(naphthalene-l-yl)-N,N'-diphenyl-benzidine), and 4,4'-cyclohexylbis[N,N-bis(4-methylphenyl)aniline] (TAPC: 4,4′-Cyclohexylidenebis[N,N-bis(4-me 4,4'-bis[N,N'-(3-tolyl)amino]-3,3'-dimethylbiphenyl (HMTPD: 4,4'-Bis[N,N'-(3-tolyl)amino]-3,3'-dimethylbiphenyl), 9-(4-tert-butylphenyl)-3,6-bis(triphenylsilyl)-9H-carbazole (CzSi: 9-(4-tert-Butylphenyl)-3,6-bis(triphenylsilyl) Examples of carbazoles include 9-phenyl-9H-3,9'-bicarbazole (CCP: 9-phenyl-9H-3,9'-bicarbazole), 1,3-bis(N-carbazolyl)benzene (mCP: 1,3-Bis(N-carbazolyl)benzene), and 1,3-bis(1,8-dimethyl-9H-carbazol-9-yl)benzene (mDCP: 1,3-bis(1,8-dimethyl-9H-carbazol-9-yl)benzene).

[0165] The hole transport region HTR can be a compound comprising at least one of the hole injection layer HIL, the hole transport layer HTL, and the electron blocking layer EBL.

[0166] The thickness of the hole transport region (HTR) can be approximately up to approximately For example, it can be approximately up to approximately In the case where the hole transport region (HTR) includes a hole injection layer (HIL), the thickness of the hole injection layer (HIL) can be, for example, approximately... up to approximately In the case where the hole transport region (HTR) includes the hole transport layer (HTL), the thickness of the hole transport layer (HTL) can be approximately... up to approximately For example, in the case where the hole transport region HTR includes an electron blocking layer EBL, the thickness of the electron blocking layer EBL can be approximately up to approximately When 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 obtained without substantially increasing the driving voltage.

[0167] In addition to the substances mentioned above, the hole transport region (HTR) may also include a charge-generating substance to improve conductivity. The charge-generating substance may be uniformly or non-uniformly dispersed within the hole transport region (HTR). The charge-generating substance may, for example, be a p-dopant. The p-dopant may include, but is not limited to, at least one of metal halide compounds, quinone derivatives, metal oxides, and cyano-containing compounds. For example, p-dopers can include: metal halide compounds, such as CuI and RbI; quinone derivatives, such as tetracyanoquinone dimethylethane (TCNQ) and 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinone dimethylethane (F4-TCNQ); metal oxides, such as tungsten oxide and molybdenum oxide; and cyano-containing compounds, such as dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexanitrile (HAT-CN: dipyrazino[2, Examples of quinoxaline-2,3,6,7,10,11-hexacarbonitrile include 3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile and 4-[[2,3-bis[cyano-(4-cyano-2,3,5,6-tetrafluorophenyl)methylidene]cyclopropylidene]-cyanomethyl]-2,3,5,6-tetrafluorobenzonitrile, but the examples are not limited thereto.

[0168] As previously mentioned, in addition to the hole injection layer (HIL) and the hole transport layer (HTL), the hole transport region (HTR) may also include at least one of a buffer layer (not shown) and an electron blocking layer (EBL). The buffer layer (not shown) can improve light emission efficiency by compensating for the resonant distance based on the wavelength of light emitted from the light-emitting layer (EML). The material included in the buffer layer (not shown) can be any material capable of being included in the hole transport region (HTR). The electron blocking layer (EBL) is a layer that prevents electrons from being injected from the electron transport region (ETR) into the hole transport region (HTR).

[0169] An emissive layer (EML) is provided on the hole transport region (HTR). In one embodiment of the light-emitting element (ED), the EML may include the amine compound described in the above embodiment. The amine compound may be used as a dopant material or a host material in the EML.

[0170] Furthermore, in one embodiment of the light-emitting element ED, the light-emitting layer EML may include anthracene derivatives, pyrene derivatives, fluoranthene derivatives, etc. Derivatives, dihydrobenzanthracene derivatives, or benzo[9,10]phenanthrene derivatives. Specifically, the luminescent layer EML may include anthracene derivatives or pyrene derivatives.

[0171] exist Figures 3 to 6 In one embodiment of the light-emitting element (ED) shown, the light-emitting layer (EML) may include a host and a dopant. The EML may include a compound represented by the following chemical formula E-1. The compound represented by the following chemical formula E-1 can be used as a fluorescent host material.

[0172] [Chemical Formula E-1]

[0173]

[0174] In chemical formula E-1, R 31 To R 40 It can be independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted silyl group, an alkyl group with 1 to 10 carbon atoms (substituted or unsubstituted), an aryl group with 6 to 30 carbon atoms (substituted or unsubstituted), or a heteroaryl group with 2 to 30 carbon atoms (substituted or unsubstituted), or it can be combined with adjacent groups to form a ring. Furthermore, R 31 To R 40 It can combine with adjacent groups to form saturated or unsaturated hydrocarbon rings.

[0175] In chemical formula E-1, c and d can each be an independent integer greater than 0 and less than 5. Chemical formula E-1 can be represented by any one of the following compounds E1 to E19.

[0176]

[0177]

[0178]

[0179] In one embodiment, the luminescent layer (EML) may include a compound represented by the following chemical formula E-2a or E-2b. The compound represented by the following chemical formula E-2a or E-2b may be used as a phosphorescent host material.

[0180] [Chemical formula E-2a]

[0181]

[0182] In the chemical formula E-2a, 'a' can be an integer from 0 to 10, and 'La' can be a directly bonded, substituted or unsubstituted cyclic aryl group with 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted cyclic aryl group with 2 to 30 cyclic carbon atoms. Furthermore, when 'a' is an integer of 2 or more, multiple 'La's can each independently be a substituted or unsubstituted cyclic aryl group with 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted cyclic aryl group with 2 to 30 cyclic carbon atoms.

[0183] Furthermore, in chemical formula E-2a, A1 to A5 can each be independently N or CR. i R a To R i It can be independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted amino group, a substituted or unsubstituted thio group, a substituted or unsubstituted oxy group, an alkyl group with 1 to 20 carbon atoms, an alkenyl group with 2 to 20 carbon atoms, an aryl group with 6 to 30 carbon atoms, or a heteroaryl group with 2 to 30 carbon atoms, or it can be combined with adjacent groups to form a ring. R a To R i It can combine with adjacent groups to form hydrocarbon rings or heterocycles that include N, O, S, etc. as cyclic atoms.

[0184] Furthermore, in chemical formula E-2a, two or three selected from A1 to A5 can be N, and the rest can be CR. i .

[0185] [Chemical formula E-2b]

[0186]

[0187] In chemical formula E-2b, Cbz1 and Cbz2 can be independently either 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 bonded, substituted or unsubstituted cyclic aryl group with 6 to 30 carbon atoms, or a substituted or unsubstituted cyclic aryl group with 2 to 30 carbon atoms. b can be an integer from 0 to 10. When b is an integer of 2 or more, multiple L... bIt can be independently a cyclic aryl group with 6 to 30 substituted or unsubstituted carbon atoms, or a heteroaryl group with 2 to 30 substituted or unsubstituted carbon atoms.

[0188] A compound represented by chemical formula E-2a or E-2b may be represented by any one of the compounds in the following compound group E-2. However, the compounds listed in the following compound group E-2 are exemplary, and compounds represented by chemical formula E-2a or E-2b are not limited to those shown in the following compound group E-2.

[0189] [Compound Group E-2]

[0190]

[0191]

[0192] The luminescent layer EML can also include common materials known in the art as the host material. For example, the luminescent layer EML may include bis[2-(diphenylphosphino)phenyl]ether oxide (DPEPO: Bis[2-(diphenylphosphino)phenyl]ether oxide), 4,4'-bis(carbazol-9-yl)biphenyl (CBP: 4,4'-Bis(carbazol-9-yl)biphenyl), 1,3-bis(carbazol-9-yl)benzene (mCP: 1,3-Bis(carbazol-9-yl)benzene), 2,8-bis(diphenylphosphoryl)dibenzo[b,d]furan (PPF: 2,8-Bis(diphenylphosphoryl)dibenzo[b,d]furan). The main substance is at least one of uran), 4,4',4”-tris(carbazol-9-yl)-triphenylamine (TCTA: 4,4',4”-Tris(carbazol-9-yl)-triphenylamine) and 1,3,5-tris(1-phenyl-1H-benzo[d]imidazol-2-yl)benzene (TPBi: 1,3,5-tris(1-phenyl-1H-benzo[d]imidazol-2-yl)benzene).However, it is not limited to this; for example, tris(8-hydroxyquinolino)aluminum (Alq3: tris(8-hydroxyquinolino)aluminum), 4,4'-bis(N-carbazolyl)-1,1'-biphenyl (CBP: 4,4'-bis(N-carbazolyl)-1,1'-biphenyl), poly(N-vinylcabazole) (PVK: poly(N-vinylcabazole)), 9,10-di(naphthalene-2-yl)anthracene (ADN: 9,10-di(naphthalene-2-yl)anthracene), and 4,4',4"-tris(carbazol-9-yl)-triphenylamine (TCTA: 4,4',4"-Tris(carbazol-9-yl)-triph Enylamine, 2-tert-butyl-9,10-di(naphth-2-yl)anthracene (TBADN: 2-tert-butyl-9,10-di(naphth-2-yl)anthracene), distyrylarylene (DSA: distyrylarylene), 4,4'-bis(9-carbazolyl)-2,2'-dimethylbiphenyl (CDBP: 4,4′-bis(9-carbazolyl)-2,2′-dimethyl-biphenyl), 2-methyl-9,10-bis(naphth-2-yl)anthracene (MADN: 2-Methyl-9,10-bis(naphthalen-2-yl)anthracene), hexaphenylcyclotriphosphazene (CP1: Hexaphenyl) Cyclotriphosphazene, 1,4-bis(triphenylsilyl)benzene (UGH2: 1,4-Bis(triphenylsilyl)benzene), hexaphenylcyclotrisiloxane (DPSiO3: Hexaphenylcyclotrisiloxane), octaphenylcyclotetrasiloxane (DPSiO4: Octaphenylcyclotetrasiloxane), 2,8-bis(diphenylphosphoryl)dibenzofuran (PPF: 2,8-Bis(diphenylphosphoryl)dibenzofuran) and other similar compounds are used as the main materials.

[0193] The luminescent layer (EML) may include compounds represented by the chemical formulas Ma or Mb. These compounds can be used as phosphorescent dopant materials.

[0194] [Chemical formula Ma]

[0195]

[0196] In the chemical formula Ma, Y1 to Y4 and Z1 to Z4 are each independently CR1 or N, and R1 to R4 can each be independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted amino group, a substituted or unsubstituted thio group, a substituted or unsubstituted oxygen group, an alkyl group with 1 to 20 carbon atoms, an alkenyl group with 2 to 20 carbon atoms, an aryl group with 6 to 30 carbon atoms, or a heteroaryl group with 2 to 30 carbon atoms, or can be combined with adjacent groups to form a ring. In the chemical formula Ma, m is 0 or 1, and n is 2 or 3. In the chemical formula Ma, when m is 0, n is 3; when m is 1, n is 2.

[0197] Compounds represented by the chemical formula Ma can be used as red or green phosphorescent dopants.

[0198] Compounds represented by the chemical formula Ma can be represented by any one of the following compounds M-a1 to M-a19. However, compounds M-a1 to M-a19 are exemplary, and compounds represented by the chemical formula Ma are not limited to those represented by compounds M-a1 to M-a19.

[0199]

[0200]

[0201] Compounds M-a1 and M-a2 can be used as red dopant materials, while compounds M-a3 to M-a5 can be used as green dopant materials.

[0202] [Chemical formula Mb]

[0203]

[0204] In the chemical formula Mb, Q1 to Q4 are independently C or N, and C1 to C4 are independently hydrocarbon rings with 5 to 30 substituted or unsubstituted carbon atoms, or heterocycles with 2 to 30 substituted or unsubstituted carbon atoms. 21 To L 24 Each can be independently represented as direct binding, *-O-*, *-S-*, etc. The substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, the substituted or unsubstituted cyclic aryl group having 6 to 30 carbon atoms, or the substituted or unsubstituted cyclic aryl group having 2 to 30 carbon atoms, wherein e1 to e4 are independently 0 or 1. R31 To R 39 Each of the following groups is independently composed of a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted amino group, an alkyl group with 1 to 20 substituted or unsubstituted carbon atoms, an aryl group with 6 to 30 substituted or unsubstituted cyclic carbon atoms, or a heteroaryl group with 2 to 30 substituted or unsubstituted cyclic carbon atoms, or a ring formed by combining with adjacent groups, wherein d1 to d4 are independently integers of 0 to 4.

[0205] Compounds represented by the chemical formula Mb can be used as blue or green phosphorescent dopants.

[0206] Compounds represented by the chemical formula Mb can be represented by any of the compounds listed below. However, the compounds listed below are exemplary, and compounds represented by the chemical formula Mb are not limited to those represented by the compounds listed below.

[0207]

[0208] In the compound, R, R 38 and R 39 It can be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted amino group, an alkyl group with 1 to 20 carbon atoms, a substituted or unsubstituted cyclic carbon group with 6 to 30 carbon atoms, or a heteroaryl group with 2 to 30 carbon atoms.

[0209] The luminescent layer (EML) may include a compound represented by any one of the following chemical formulas: Fa to Fc. Compounds represented by the following chemical formulas: Fa to Fc can be used as fluorescent dopant materials.

[0210] [Chemical formula Fa]

[0211]

[0212] In the chemical formula Fa, the components are selected from R. a To R j The two values ​​can be replaced independently by *-NAr1Ar2. In R a To R jIn *-NAr1Ar2, the remaining groups not substituted by * can be independently hydrogen atoms, deuterium atoms, halogen atoms, cyano groups, substituted or unsubstituted amino groups, alkyl groups with 1 to 20 carbon atoms (substituted or unsubstituted), aryl groups with 6 to 30 cyclic carbon atoms (substituted or unsubstituted), or heteroaryl groups with 2 to 30 cyclic carbon atoms (substituted or unsubstituted). In *-NAr1Ar2, Ar1 and Ar2 can be independently independently aryl groups with 6 to 30 cyclic carbon atoms (substituted or unsubstituted) or heteroaryl groups with 2 to 30 cyclic carbon atoms (substituted or unsubstituted). For example, at least one of Ar1 and Ar2 can be a heteroaryl group including O or S as a cyclic atom.

[0213] [Chemical formula Fb]

[0214]

[0215] In the chemical formula Fb, R a and R b Each group can be independently composed of a hydrogen atom, a deuterium atom, an alkyl group with 1 to 20 substituted or unsubstituted carbon atoms, an alkenyl group with 2 to 20 substituted or unsubstituted carbon atoms, an aryl group with 6 to 30 substituted or unsubstituted cyclic carbon atoms, or a heteroaryl group with 2 to 30 substituted or unsubstituted cyclic carbon atoms, or can be combined with adjacent groups to form a ring. Ar1 to Ar4 can each be independently composed of an aryl group with 6 to 30 substituted or unsubstituted cyclic carbon atoms, or a heteroaryl group with 2 to 30 substituted or unsubstituted cyclic carbon atoms.

[0216] In the chemical formula Fb, U and V can be, independently, either substituted or unsubstituted cyclic hydrocarbon rings with 5 to 30 carbon atoms, or substituted or unsubstituted cyclic heterocycles with 2 to 30 carbon atoms.

[0217] In the chemical formula Fb, the number of rings represented by U and V can be independently 0 or 1. For example, in the chemical formula Fb, when the number of U or V is 1, it means that in the part described as U or V, one ring forms a condensed ring; when the number of U or V is 0, it means that there are no rings described as U or V. Specifically, when the number of U is 0 and the number of V is 1, or when the number of U is 1 and the number of V is 0, the condensed ring of the fluorene core having the chemical formula Fb can be a tetracyclic cyclic compound. Furthermore, when the number of both U and V is 0, the condensed ring of the chemical formula Fb can be a tricyclic cyclic compound. And, when the number of both U and V is 1, the condensed ring of the fluorene core having the chemical formula Fb can be a pentacyclic cyclic compound.

[0218] [Chemical formula Fc]

[0219]

[0220] In the chemical formula Fc, A1 and A2 are independently O, S, Se, or NR, respectively. m R m It can be a hydrogen atom, a deuterium atom, an alkyl group with 1 to 20 substituted or unsubstituted carbon atoms, an aryl group with 6 to 30 substituted or unsubstituted cyclic carbon atoms, or a heteroaryl group with 2 to 30 substituted or unsubstituted cyclic carbon atoms. R1 to R 11 It is independently composed of a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted amino group, a substituted or unsubstituted boron group, a substituted or unsubstituted oxygen group, a substituted or unsubstituted thio group, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, or a heteroaryl group having 2 to 30 carbon atoms, or a cyclic group formed by combining with adjacent groups to form a ring.

[0221] In the chemical formula Fc, A1 and A2 can independently combine with substituents of adjacent rings to form condensed rings. For example, when A1 and A2 are independently NR... m In this case, A1 can combine with R4 or R5 to form a ring. Furthermore, A2 can combine with R7 or R8 to form a ring.

[0222] In one embodiment, the light-emitting layer (EML) may include styrene derivatives as known dopant materials (e.g., 1,4-bis[2-(3-N-ethylcarbazolyl)vinyl]benzene (BCzVB: 1,4-bis[2-(3-N-ethylcarbazolyl)vinyl]benzene), 4-(di-p-tolylamino)-4'-[(di-p-tolylamino)styryl]stilbene (DPAVB: 4-(di-p-tolylamino)-4'-[(di-p-tolylamino)styryl]stilbene), N-(4-((E)-2-(6-((E)-4-(diphenylamino)styryl)naphthyl-2-yl)vinyl)phenyl)-N-phenylaniline (N-BDAVBi: N-(4-((E)-2-(6-((E)-4-(diphenylamino)styryl)naphthyl ... Phthalen-2-yl)vinyl)phenyl)-N-phenylbenzenamine), 4,4'-bis[2-(4-(N,N-diphenylamino)phenyl)vinyl]biphenyl (DPAVBi: 4,4'-bis[2-(4-(N,N-diphenylamino)phenyl)vinyl]biphenyl), perylene and its derivatives (e.g., 2,5,8,11-tetra-t-butylperylene (TBP: 2,5,8,11-Tetra-t-butylperylene)), pyrene and its derivatives (e.g., 1,1'-dipyrene, 1,4-dipyrenylbenzene, 1,4-bis(N,N-diphenylamino)pyrene, etc.).

[0223] The light-emitting layer (EML) can include known phosphorescent dopant materials. For example, phosphorescent dopant can be a metal complex including iridium (Ir), platinum (Pt), osmium (Os), gold (Au), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), or thulium (Tm). Specifically, iridium(III)bis(4,6-difluorophenylpyridinato-N,C2')picolinate (FIrpic: iridium(III)bis(4,6-difluorophenylpyridinato-N,C2′)picolinate), iridium(III)bis(2,4-difluorophenylpyridinato)-tetrakis(1-pyrazolyl)borate iridium(III) (FIr6: Bis(2,4-difluorophenylpyridinato)-tetrakis(1-pyrazolyl)borate iridium(III)), or platinumoctaethyl porphyrin (PtOEP: platinumoctaethyl porphyrin) can be used as phosphorescent dopants. However, the examples are not limited to these.

[0224] The luminescent layer (EML) can include quantum dot materials. The core of the quantum dots can 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.

[0225] Group II-VI compounds can be selected from the group consisting of the following compounds: binary compounds, selected from the group consisting of CdSe, CdTe, CdS, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, MgSe, MgS, and mixtures thereof; ternary compounds, selected from the group consisting of CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, and CdZnSe. The group consisting of 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.

[0226] III-VI group compounds may include: binary compounds, such as In2S3, In2Se3, etc.; ternary compounds, such as InGaS3, InGaSe3, etc.; or any combination thereof.

[0227] Group I-III-VI compounds may be selected from: ternary compounds, selected from the group consisting of AgInS, AgInS2, CuInS, CuInS2, AgGaS2, CuGaS2, CuGaO2, AgGaO2, AgAlO2 and mixtures thereof; or quaternary compounds, selected from AgInGaS2, CuInGaS2, etc.

[0228] 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. Furthermore, Group III-V compounds may also include Group II metals. For example, InZnP, etc., can be selected as a group III-II-V compound.

[0229] Group IV-VI compounds can 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 can be selected from the group consisting of Si, Ge, and mixtures thereof. Group IV compounds can be binary compounds selected from the group consisting of SiC, SiGe, and mixtures thereof.

[0230] At this point, binary, ternary, or quaternary compounds can exist within the particle at a uniform concentration, or they can exist dispersedly within the same particle with locally different concentration distributions. Furthermore, they can possess a core / shell structure with one quantum dot surrounding other quantum dots. The core-shell interface can exhibit a concentration gradient where the concentration of the element present in the shell decreases towards the center.

[0231] In some embodiments, the quantum dot may have a core-shell structure comprising a core containing the aforementioned nanocrystals and a shell surrounding the core. The shell of the quantum dot may function as a protective layer to prevent chemical degradation of the core and maintain semiconductor properties, and / or as a charging layer to impart electrophoretic properties to the quantum dot. The shell may be a single layer or multiple layers. The interface between the core and the shell may have a concentration gradient in which the concentration of the element present in the shell decreases towards the center. Examples of the shell of the quantum dot may be metal or non-metal oxides, semiconductor compounds, or combinations thereof.

[0232] For example, the oxides of the metal or nonmetal can be exemplified as: binary compounds, such as SiO2, Al2O3, TiO2, ZnO, MnO, Mn2O3, Mn3O4, CuO, FeO, Fe2O3, Fe3O4, CoO, Co3O4, NiO, etc.; or ternary compounds, such as MgAl2O4, CoFe2O4, NiFe2O4, CoMn2O4, etc., but the present invention is not limited thereto.

[0233] Quantum dots can have a full width at half maximum (FWHM) of an emission wavelength spectrum of approximately 45 nm or less, preferably approximately 40 nm or less, and more preferably approximately 30 nm or less. Within this range, color purity or color reproducibility can be improved. Furthermore, light emitted by such quantum dots is emitted in all directions, thereby improving the viewing angle.

[0234] Furthermore, the morphology of quantum dots is not particularly restricted, as long as it is a morphology commonly used in the field. More specifically, spherical, pyramidal, multi-arm, or cubic nanoparticles, nanotubes, nanowires, nanofibers, nanoplate particles, and other morphologies can be used.

[0235] Quantum dots can adjust the color of the emitted light according to their particle size, thus they can have a variety of emitting colors such as blue, red, and green.

[0236] exist Figures 3 to 6In one embodiment of the light-emitting element ED, an electron transport region (ETR) is provided on the light-emitting 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 embodiment is not limited thereto.

[0237] The electron transport region (ETR) can have a single-layer structure composed of a single substance, a single-layer structure composed of multiple different substances, or a multi-layer structure composed of multiple different substances.

[0238] For example, the electron transport region (ETR) can have a single-layer structure of either the electron injection layer (EIL) or the electron transport layer (ETL), or it can have a single-layer structure composed of an electron injection material and an electron transport material. Furthermore, the ETR can have a single-layer structure composed of multiple different materials, or it can have a structure of electron transport layer (ETL) / electron injection layer (EIL), hole blocking layer (HBL) / electron transport layer (ETL) / electron injection layer (EIL) stacked sequentially from the emitting layer (EML), but it is not limited to these. The thickness of the ETR can, for example, be approximately... up to approximately

[0239] Electron transport regions (ETRs) can be formed using various methods, including vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) method, inkjet printing, laser printing, and laser-induced thermal imaging (LITI).

[0240] The electron transport region (ETR) may include compounds represented by the following chemical formula ET-1.

[0241] [Chemical formula ET-1]

[0242]

[0243] In the chemical formula ET-1, at least one of X1 to X3 is N, and the rest are CR. a R a Ar1 to Ar3 can be hydrogen atoms, deuterium atoms, alkyl groups with 1 to 20 substituted or unsubstituted carbon atoms, aryl groups with 6 to 30 substituted or unsubstituted cyclic carbon atoms, or heteroaryl groups with 2 to 30 substituted or unsubstituted cyclic carbon atoms.

[0244] In chemical formula ET-1, a to c can each be an integer from 0 to 10 or less. In chemical formula ET-1, L1 to L3 can each be an arylene group with 6 to 30 substituted or unsubstituted cyclic carbon atoms, or a heteroarylene group with 2 to 30 substituted or unsubstituted cyclic carbon atoms, respectively, through direct linkage. Furthermore, when a to c are integers of 2 or more, L1 to L3 can each be an arylene group with 6 to 30 substituted or unsubstituted cyclic carbon atoms, or a heteroarylene group with 2 to 30 substituted or unsubstituted cyclic carbon atoms, respectively.

[0245] Electron transport region (ETR) compounds may include anthracene compounds. However, they are not limited to this; for example, ETRs may include tris(8-hydroxyquinolino)aluminum, 1,3,5-tris[(3-pyridyl)-phen-3-yl]benzene, and 2,4,6-tris(3'-(pyridin-3-yl)biphenyl-3-yl)-1,3,5-triazine. ine), 2-(4-(N-phenylbenzimidazol-1-yl)phenyl)-9,10-dinaphthylanthracene, 1,3,5-tri(1-phenyl-1H-benzo[d]imidazol-2-yl)benzene (TPBi: 1,3,5-tri(1-phenyl-1H-benzo[d]imidazol-2-yl)benzene), 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP: 2,9-Dim ethyl-4,7-diphenyl-1,10-phenanthroline), 4,7-diphenyl-1,10-phenanthroline (Bphen: 4,7-Diphenyl-1,10-phenanthroline), 3-(4-biphenyl)-4-phenyl-5-tert-butylphenyl-1,2,4-triazole (TAZ: 3-(4-Biphenylyl)-4-phenyl-5-tert-butylphenyl-1,2,4-triazole), 4-(naphthyl-1-yl)-3,5-diphenyl-4H-1,2,4-triazole (NTAZ: 4-(Naphthalen-1-yl)-3,5-diphenyl-4H-1,2,4-triazole), 2-(4-biphenyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (tBu-PBD: 2-(4-Biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole), bis(2-methyl-8-quinolino-N1,O8)-(1,1'-biphenyl-4-hydroxy)aluminum (BAlq: Bis(2-methyl-8-quinolinolato-N1,O8)-(1,1'-Biphenyl-4-olato)aluminum), bis(benzoquinolin-10-olate)beryllium (Bebq2: berylliumbis(benzoquinolin-10-olate)), 9,10-di(naphthalene-2-yl)anthracene (ADN: 9,10-di(naphthalene-2-yl)anthracene), 1,3-bis[3,5-di(pyridin-3-yl)phenyl]benzene (BmPyPhB: (1,3-Bis[3,5-di(pyridin-3-yl)phenyl]benzene), and mixtures thereof.

[0246] Furthermore, the electron transport region (ETR) can include: metal halides, such as LiF, NaCl, CsF, RbCl, RbI, CuI, KI, etc.; lanthanide group metals, such as Yb, etc., and can include co-deposited materials of said metal halides and lanthanide group metals. For example, the ETR can include KI:Yb, RbI:Yb, etc., as co-deposited materials. In addition, the ETR can use metal oxides such as Li₂O, BaO, or lithium 8-hydroxyl-Lithiumquinolate (Liq), but the embodiments are not limited to these. The ETR can also be composed of a mixture of electron transport material and insulating organometallic salt. The organometallic salt can be a material with an energy band gap of approximately 4 eV or higher. Specifically, for example, organometallic salts may include metal acetate, metal benzoate, metal acetoacetate, metal acetylacetonate, or metal stearate.

[0247] In addition to the materials mentioned above, the electron transport region (ETR) may also include at least one of 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP: 2,9-Dimethyl-4,7-diphenyl-1,10-phenanthroline) and 4,7-diphenyl-1,10-phenanthroline (Bphen: 4,7-Diphenyl-1,10-phenanthroline), but the embodiments are not limited thereto.

[0248] The electron transport region (ETR) can be a compound comprising at least one of the electron injection layer (EIL), the electron transport layer (ETL), and the hole blocking layer (HBL).

[0249] In the case where the electron transport region ETR includes the electron transport layer ETL, the thickness of the electron transport layer ETL can be approximately up to approximately For example, it can be approximately up to approximately When the thickness of the electron transport layer (ETL) meets the range described above, satisfactory electron transport characteristics can be obtained without a substantial increase in the driving voltage. When the electron transport region (ETL) includes an electron injection layer (EIL), the thickness of the EIL can be approximately... up to approximately About up to approximately When the thickness of the electron injection layer (EIL) meets the range described above, satisfactory electron injection characteristics can be obtained without a substantial increase in the driving voltage.

[0250] 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, if the first electrode EL1 is an anode, the second electrode EL2 can be a cathode, and if the first electrode EL1 is a cathode, the second electrode EL2 can be an anode.

[0251] The second electrode EL2 can be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode. In the case where the second electrode EL2 is a transmissive electrode, it can be composed of a transparent metal oxide, such as indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), or indium tin zinc oxide (ITZO).

[0252] When the second electrode EL2 is a semi-transparent or reflective electrode, it may include Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF, Mo, Ti, Yb, W, compounds or mixtures thereof (e.g., AgMg, AgYb, or MgYb), or materials having a multilayer structure such as LiF / Ca or LiF / Al. Alternatively, the second electrode EL2 may be a multilayer structure comprising a reflective or semi-transparent film formed from the aforementioned materials, and a transparent conductive film formed from indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), indium tin zinc oxide (ITZO), etc. For example, the second electrode EL2 may include the aforementioned metallic materials, a combination of two or more metallic materials selected from the aforementioned metallic materials, or oxides of the aforementioned metallic materials.

[0253] Although not shown, the second electrode EL2 can be connected to the auxiliary electrode. If the second electrode EL2 is connected to the auxiliary electrode, the resistance of the second electrode EL2 can be reduced.

[0254] Furthermore, in one embodiment, a capping layer CPL may be disposed on the second electrode EL2 of the light-emitting element ED. The capping layer CPL may be a single layer or multiple layers.

[0255] In one embodiment, the capping layer CPL can be an organic layer or an inorganic layer. For example, when the capping layer CPL includes inorganic materials, the inorganic materials may include: alkali metal compounds, such as LiF; alkaline earth metal compounds, such as MgF2; and SiON, SiN. X SiO y wait.

[0256] For example, when the capping layer CPL includes an organic compound, the organic compound may include α-NPD, NPB, TPD, m-MTDATA, Alq3, CuPc, N4,N4,N4',N4'-tetra(biphenyl-4-yl)biphenyl-4,4'-diamine (TPD15: N4,N4,N4',N4'-tetra(biphenyl-4-yl)biphenyl-4,4'-diamine), 4,4',4"-tris(carbazol-9-yl)triphenylamine (TCTA: 4,4',4"-Tris(carbazol-9-yl)triphenylamine), etc., or may include epoxy resin or acrylate such as methacrylate. However, the embodiments are not limited thereto, and the capping layer CPL may include at least one of compounds P1 to P5 as described below.

[0257]

[0258]

[0259] Furthermore, the refractive index of the capping layer CPL can be 1.6 or higher. Specifically, for light in the wavelength range of 550 nm to 660 nm, the refractive index of the capping layer CPL can be 1.6 or higher.

[0260] Figure 7 as well as Figure 8 These are cross-sectional views of a display device according to one embodiment. Hereinafter, in conjunction with the reference... Figure 7 and Figure 8 When describing a display device according to one embodiment, the description will not repeat the descriptions of the above-described display device. Figures 1 to 6 The content repeated in the explanation should be explained mainly based on the differences.

[0261] Reference Figure 7 According to one embodiment, the display device DD may include a display panel DP including a display element layer DP-ED, a light control layer CCL and a color filter layer CFL disposed on the display panel DP.

[0262] exist Figure 7 In one embodiment shown, the display panel DP may include a base layer BS, a circuit layer DP-CL disposed on the base layer BS, and a display element layer DP-ED, wherein the display element layer DP-ED may include a light-emitting element ED.

[0263] The light-emitting element (ED) may include: a first electrode EL1; a hole transport region HTR disposed on the first electrode EL1; a light-emitting layer EML disposed on the hole transport region HTR; an electron transport region ETR disposed on the light-emitting layer EML; and a second electrode EL2 disposed on the electron transport region ETR. Furthermore, Figure 7 The structure of the light-emitting element ED shown can be applied in the same way as described above. Figures 4 to 6 The structure of the light-emitting element.

[0264] Reference Figure 7 The emissive layer EML can be disposed within the opening OH defined by the pixel defining film PDL. For example, the emissive layers EML provided corresponding to each emissive region PXA-R, PXA-G, and PXA-B, divided by the pixel defining film PDL, can emit light of the same wavelength. In a display device DD according to one embodiment, the emissive layer EML can emit blue light. Furthermore, unlike the illustrated case, in one embodiment, the emissive layer EML can be provided as a common layer throughout the entire emissive region PXA-R, PXA-G, and PXA-B.

[0265] The light control layer (CCL) can be disposed on the display panel (DP). The light control layer (CCL) may include a light converter. The light converter may be a quantum dot or a phosphor, etc. The light converter can convert the wavelength of the received light and emit it. That is, the light control layer (CCL) may be a layer including quantum dots or a layer including phosphors.

[0266] The optical control layer (CCL) may include multiple optical control units CCP1, CCP2, and CCP3. The optical control units CCP1, CCP2, and CCP3 may be spaced apart from each other.

[0267] Reference Figure 7 A segmented pattern BMP can be arranged between the light control units CCP1, CCP2, and CCP3 that are separated from each other, but the embodiment is not limited to this. Although in Figure 7 The diagram shows a case where the segmentation pattern BMP does not overlap with the light control units CCP1, CCP2, and CCP3, but the edges of the light control units CCP1, CCP2, and CCP3 may overlap with at least a portion of the segmentation pattern BMP.

[0268] The light control layer CCL may include: a first light control unit CCP1, including a first quantum dot QD1 that converts first-color light provided by the light-emitting element ED into second-color light; a second light control unit CCP2, including a second quantum dot QD2 that converts first-color light into third-color light; and a third light control unit CCP3 that transmits first-color light.

[0269] In one embodiment, the first light control unit CCP1 can provide red light as a second color light, and the second light control unit CCP2 can provide green light as a third color light. The third light control unit CCP3 can transmit blue light, which is the first color light provided from the light-emitting element ED, to provide blue light. 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 content as described above can be applied to quantum dots QD1 and QD2.

[0270] Furthermore, the optical control layer CCL may also include a scatterer SP. The first optical control unit CCP1 may include a first quantum dot QD1 and a scatterer SP, the second optical control unit CCP2 may include a second quantum dot QD2 and a scatterer SP, and the third optical control unit CCP3 may not include a quantum dot but may include a scatterer SP.

[0271] The scatterer SP can be inorganic particles. For example, the scatterer SP can include at least one of TiO2, ZnO, Al2O3, SiO2, and hollow silica. The scatterer SP can include any one of TiO2, ZnO, Al2O3, SiO2, and hollow silica, or it can be a mixture of two or more substances selected from TiO2, ZnO, Al2O3, SiO2, and hollow silica.

[0272] Each of the first light control unit CCP1, the second light control unit CCP2, and the third light control unit CCP3 may include base resins BR1, BR2, and BR3 for dispersing quantum dots QD1, QD2, and scatterers SP. In one embodiment, the first light control unit CCP1 may include the first quantum dots QD1 and scatterers SP dispersed in the first base resin BR1, the second light control unit CCP2 may include the second quantum dots QD2 and scatterers SP dispersed in the second base resin BR2, and the third light control unit CCP3 may include scatterers SP dispersed in the third base resin BR3. The base resins BR1, BR2, and BR3, as media for dispersing quantum dots QD1, QD2, and scatterers SP, may be composed of various resin compositions commonly referred to as binders. For example, the base resins BR1, BR2, and BR3 may be acrylic resins, polyurethane resins, silicone resins, epoxy resins, etc. The base resins BR1, BR2, and BR3 may be transparent resins. In one embodiment, the first base resin BR1, the second base resin BR2, and the third base resin BR3 may be the same as or different from each other.

[0273] The light control layer CCL may include a barrier layer BFL1. The barrier layer BFL1 serves to prevent the penetration of moisture and / or oxygen (hereinafter referred to as "moisture / oxygen"). The barrier layer BFL1 may be disposed on the light control units CCP1, CCP2, and CCP3 to prevent them from being exposed to moisture / oxygen. Furthermore, the barrier layer BFL1 may cover the light control units CCP1, CCP2, and CCP3. Additionally, a barrier layer BFL2 may also be provided between the light control units CCP1, CCP2, and CCP3 and the filters CF1, CF2, and CF3 (described later).

[0274] Barrier layers BFL1 and BFL2 may include at least one inorganic layer. That is, barrier layers BFL1 and BFL2 may be formed from inorganic materials. For example, barrier layers BFL1 and BFL2 may be formed from silicon nitride, aluminum nitride, zirconium nitride, titanium nitride, hafnium nitride, tantalum nitride, silicon oxide, aluminum oxide, titanium oxide, tin oxide, cerium oxide, and silicon nitride, or a metal thin film that ensures light transmittance. Furthermore, barrier layers BFL1 and BFL2 may also include an organic film. Barrier layers BFL1 and BFL2 may consist of a single layer or multiple layers.

[0275] In one embodiment of the display device DD, the color filter layer CFL can be disposed on the light control layer CCL. For example, the color filter layer CFL can be disposed directly on the light control layer CCL. In this case, the blocking layer BFL2 can be omitted.

[0276] The color filter layer CFL may include a light-shielding portion BM and filters CF1, CF2, and CF3. Furthermore, the color filter layer CFL may also include a blocking layer BFL2. The color filter layer CFL may include: a first filter CF1 that allows the transmission of a second color light; a second filter CF2 that allows the transmission of a third color light; and a third filter CF3 that allows the transmission of a first color light. For example, the first filter CF1 may be a red filter, the second filter CF2 may be a green filter, and the third filter CF3 may be a blue filter. Each of the filters CF1, CF2, and CF3 may include a photosensitive polymer and a pigment or dye. The first filter CF1 may include a red pigment or dye, the second filter CF2 may include a green pigment or dye, and the third filter CF3 may include a blue pigment or dye. However, the embodiments are not limited thereto; the third filter CF3 may not include any pigment or dye. The third filter CF3 may include a photosensitive polymer and may not include any pigment or dye. The third filter CF3 may be transparent. The third filter CF3 can be formed from a transparent photosensitive resin.

[0277] Furthermore, in one embodiment, the first filter CF1 and the second filter CF2 can be yellow filters. The first filter CF1 and the second filter CF2 can be provided integrally without distinguishing them from each other.

[0278] The light-shielding portion BM can be a black matrix. The light-shielding portion BM can be formed from organic or inorganic light-shielding materials containing black pigments or dyes. The light-shielding portion BM can prevent light leakage and define the boundaries between adjacent filters CF1, CF2, and CF3. Furthermore, in one embodiment, the light-shielding portion BM can be formed from a blue filter.

[0279] The first to the third filters CF1, CF2, and CF3 can be arranged to correspond to the red emitting area PXA-R, the green emitting area PXA-G, and the blue emitting area PXA-B, respectively.

[0280] A base substrate BL can be disposed on the color filter layer CFL. The base substrate BL can be a component that provides a base surface for disposing the color filter layer CFL and the light control layer CCL, etc. The base substrate BL can be a glass substrate, a metal substrate, a plastic substrate, etc. However, the embodiments are not limited to this, and the base substrate BL can be an inorganic layer, an organic layer, or a composite material layer. Furthermore, unlike the illustrated case, in one embodiment, the base substrate BL can be omitted.

[0281] Figure 8 This is a cross-sectional view showing a portion of a display device according to one embodiment. Figure 8 It shows the relationship with Figure 7 A cross-sectional view of a portion of the display panel DP. In a display device DD-TD of one embodiment, the light-emitting element ED-BT may include a plurality of light-emitting structures OL-B1, OL-B2, and OL-B3. The light-emitting element ED-BT may include: a first electrode EL1 and a second electrode EL2 facing each other; and a plurality of light-emitting structures OL-B1, OL-B2, and OL-B3, which are provided by being stacked sequentially in the thickness direction between the first electrode EL1 and the second electrode EL2. Each of the light-emitting structures OL-B1, OL-B2, and OL-B3 may include a light-emitting layer EML (Emitting Material Layer). Figure 7 ), with an EML light-emitting layer sandwiched in the middle ( Figure 7 The hole transmission region (HTR) and electron transmission region (ETR) are arranged accordingly.

[0282] That is, the light-emitting element ED-BT of the display device DD-TD included in one embodiment can be a light-emitting element with a tandem structure including multiple light-emitting layers.

[0283] exist Figure 8In one embodiment shown, the light emitted from each of the light-emitting structures OL-B1, OL-B2, and OL-B3 can all be blue light. However, the embodiment is not limited to this, and the wavelengths of the light emitted from each of the light-emitting structures OL-B1, OL-B2, and OL-B3 can be different from each other. For example, a light-emitting element ED-BT comprising multiple light-emitting structures OL-B1, OL-B2, and OL-B3 that emit light in different wavelengths can emit white light.

[0284] Charge generation layers CGL1 and CGL2 can be arranged between adjacent light-emitting structures OL-B1, OL-B2, and OL-B3. Charge generation layers CGL1 and CGL2 may include p-type charge generation layers and / or n-type charge generation layers.

[0285] Hereinafter, a compound according to an embodiment of the present invention and a light-emitting element according to an embodiment will be specifically described with reference to examples and comparative examples. Furthermore, the examples shown below are merely illustrative to aid in understanding the present invention, and the scope of the present invention is not limited thereto.

[0286] [Example]

[0287] 1. Synthesis of an amine compound according to an example

[0288] First, the synthesis methods of compounds 1, 2, 3, 8, 22, 51, and 82 according to the embodiments of this invention will be specifically described by way of example. Furthermore, the synthesis method of the amine compounds described below is one embodiment, and the synthesis methods of the compounds according to the embodiments of this invention are not limited to the following embodiments.

[0289] (1) Synthesis of Compound 1

[0290] According to one embodiment, amine compound 1 can be synthesized, for example, by the steps described in reaction formulas 1-1 to 1-4 below.

[0291] <Synthesis of Intermediate A>

[0292] Intermediate A was synthesized using the following reaction formula 1-1.

[0293] [Reaction 1-1]

[0294]

[0295] Under an argon atmosphere, 2-bromobiphenyl (35.0 g), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (49.3 g), tetrakis(triphenylphosphine)palladium(0) (Pd(PPh3)4:Tetrakis(triphenylphosphine)palladium(0)) (8.7 g), and potassium carbonate (K2CO3:Potassium carbonate) (41.5 g) were added to a 2 L three-necked flask and dissolved in a mixed solvent of toluene, water, and ethanol (10:2:1 (volume ratio), 600 mL). The mixture was heated and stirred at 80 °C for 18 hours. Water was added and the mixture was extracted with dichloromethane (CH2Cl2). The organic layers were combined, dried over magnesium sulfate (MgSO4), and the solvent was removed under reduced pressure. The crude product was purified by silica gel column chromatography to obtain 24.8 g of intermediate A (yield 67%). The molecular weight of intermediate A was determined to be 245 by FAB-MS.

[0296] <Synthesis of Intermediate C>

[0297] Intermediate C was synthesized using the following reaction formulas 1-2.

[0298] [Reaction 1-2]

[0299]

[0300] Under an argon atmosphere, 2-bromobiphenyl (20.0 g), 4-chlorophenylboronic acid (13.4 g), tetrakis(triphenylphosphine)palladium(O)(Pd(PPh3)4) (9.9 g), and potassium carbonate (K2CO3) (23.7 g) were added to a 1 L three-necked flask and dissolved in a mixed solvent of toluene, water, and ethanol (10:2:1 (v / v), 400 mL). The mixture was heated and stirred at 80 °C for 12 hours. Water was added and the mixture was extracted with dichloromethane. The organic layers were combined, dried over magnesium sulfate, and the solvent was removed under reduced pressure. The crude product was purified by silica gel column chromatography to obtain 13.6 g of intermediate C (60% yield). The molecular weight of intermediate C was determined to be 264 by FAB-MS.

[0301] Synthesis of intermediate G

[0302] Intermediate G was synthesized via the following reaction formulas 1-3.

[0303] [Reaction Formula 1-3]

[0304]

[0305] Under an argon atmosphere, intermediates A (15.0 g), C (16.2 g), bis(dibenzylideneacetone)palladium(0) (Pd(dba)2:Bis(dibenzylideneacetone)palladium(0)) (3.5 g), and sodium tert-butoxide (NaOtBu:Sodium tert-butoxide) (5.9 g) were added to a 1 L three-necked flask and dissolved in toluene (300 mL). Then, tri-tert-butylphosphine (P(tBu)3:Tri-tert-butylphosphine) (2.0 M, 6.0 mL in toluene) was added, and the mixture was heated to reflux for 6 hours. Water was added, and the mixture was extracted with dichloromethane. The organic layers were combined, dried over magnesium sulfate, and the solvent was removed under reduced pressure. The crude product was purified by silica gel column chromatography to obtain 17.9 g of intermediate G (62% yield). The molecular weight of intermediate G was determined to be 473 by FAB-MS.

[0306] <Synthesis of Compound 1>

[0307] Amine compound 1 was synthesized via the following reactions 1-4.

[0308] [Reaction Equations 1-4]

[0309]

[0310] Under an argon atmosphere, intermediate G (5.0 g), 4-bromodibenzofuran (2.6 g), bis(dibenzylacetone)palladium(O)(Pd(dba)2) (0.6 g), and sodium tert-butoxide (NaOtBu) (1.1 g) were added to a 500 mL three-necked flask and dissolved in toluene (50 mL). Tri-tert-butylphosphine (P(tBu)3) (2.0 M in toluene, 1.0 mL) was added, and the mixture was heated to reflux for 6 hours. Water was added, and the mixture was extracted with dichloromethane. The organic layers were combined, dried over magnesium sulfate, and the solvent was removed under reduced pressure. The crude product was purified by silica gel column chromatography to give 5.81 g of compound 1 (yield 86%). The molecular weight of compound 1 was determined to be 639 by FAB-MS.

[0311] (2) Synthesis of Compound 2

[0312] According to one embodiment, amine compound 2 can be synthesized, for example, by the steps of reaction formula 2 below.

[0313] [Reaction 2]

[0314]

[0315] Compound 2 was synthesized using the same method as compound 1, but with 4-bromodibenzothiophene (2.8 g) substituted for 4-bromodibenzofuran (2.6 g) to obtain 5.7 g of compound 2 (yield 83%). The molecular weight of compound 2 was determined to be 655 by FAB-MS.

[0316] (3) Synthesis of compound 3

[0317] According to one embodiment, amine compound 3 can be synthesized, for example, by the steps of reaction formula 3 below.

[0318] [Reaction 3]

[0319]

[0320] Compound 3 was synthesized using the same method as compound 1, but with 1-bromodibenzofuran (2.6 g) substituted for 4-bromodibenzofuran (2.6 g) to obtain 5.5 g of compound 3 (yield 82%). The molecular weight of compound 3 was determined to be 639 by FAB-MS.

[0321] (4) Synthesis of compound 8

[0322] According to one embodiment, amine compound 8 can be synthesized, for example, by the steps of reaction formulas 4-1 to 4-4 described below.

[0323] <Synthesis of Intermediate E>

[0324] Intermediate E was synthesized via the following reaction formula 4-1.

[0325] [Reaction 4-1]

[0326]

[0327] Under an argon atmosphere, 25.0 g of 1-bromo-2-iodobenzene, 13.8 g of 4-chlorophenylboronic acid, 5.1 g of tetrakis(triphenylphosphine)palladium(O)(Pd(PPh3)4) (K2CO3 ...) (K2CO3) (K2CO3) (K2CO3) (K2CO3) (K2CO3)) (K2CO3) (K2CO3) (K2CO3) (K2CO3) (K2CO3) (K2CO3)) (K2CO3) (K2CO3) (K2CO3) (K2CO3) (K2CO3) (K2CO3)) (K2CO3) (K2CO3) (K2CO3) (K2CO3) (K2CO3) (K2CO3) (K2CO3) (K2CO3) (K2CO3) (K2CO3) (K2CO3) (K2CO3) (K2CO3) (K2CO3) (K2CO3) (K2CO3) (K2CO3) (K2CO3) (K2CO3) (K2CO3

[0328] <Synthesis of Intermediate F>

[0329] Intermediate F was synthesized via the following reaction formula 4-2.

[0330] [Reaction 4-2]

[0331]

[0332] Under an argon atmosphere, intermediate E (15.0 g), 2-biphenylboronic acid (11.1 g), tetrakis(triphenylphosphine)palladium(O)(Pd(PPh3)4) (6.5 g), and potassium carbonate (K2CO3) (15.5 g) were added to a 1 L three-necked flask and dissolved in a mixed solvent of toluene, water, and ethanol (10:2:1 (v / v), 280 mL). The mixture was heated and stirred at 80 °C for 10 hours. Water was added and the mixture was extracted with dichloromethane. The organic layers were combined, dried over magnesium sulfate, and the solvent was removed under reduced pressure. The crude product was purified by silica gel column chromatography to obtain 12.4 g of intermediate F (65% yield). The molecular weight of intermediate F was determined to be 340 by FAB-MS.

[0333] <Synthesis of intermediate H>

[0334] Intermediate H was synthesized via the following reaction formula 4-3.

[0335] [Reaction 4-3]

[0336]

[0337] Intermediate H (yield 59%) was obtained by replacing intermediate A (15.0 g) with intermediate A (5.0 g) and intermediate C (16.2 g) with intermediate F (6.9 g) using the same method as the synthesis of intermediate G. The molecular weight of intermediate H was determined to be 549 by FAB-MS.

[0338] <Synthesis of Compound 8>

[0339] Amine compound 8 was synthesized via the following reaction formula 4-4.

[0340] [Reaction 4-4]

[0341]

[0342] Using the same method as the synthesis of compound 1, intermediate G (5.0 g) was replaced with intermediate H (5.0 g), and 4-bromodibenzofuran (2.3 g) was replaced with 4-bromodibenzofuran (2.6 g) to obtain 5.3 g of compound 8 (yield 82%). The molecular weight of compound 8 was determined to be 715 by FAB-MS.

[0343] (5) Synthesis of compound 22

[0344] According to one embodiment, amine compound 22 can be synthesized, for example, by the steps described in reaction formulas 5-1 to 5-3 below.

[0345] <Synthesis of Intermediate D>

[0346] Intermediate D was synthesized via the following reaction formula 5-1.

[0347] [Reaction 5-1]

[0348]

[0349] Intermediate D (yield 58%) was obtained in 13.2 g using the same method as intermediate C, with the aid of 2-bromobiphenyl (20.0 g) and 3-chlorophenylboronic acid (13.4 g). The molecular weight of intermediate D was determined to be 264 by FAB-MS.

[0350] <Synthesis of Intermediate J>

[0351] Intermediate J was synthesized via the following reaction formula 5-2.

[0352] [Reaction 5-2]

[0353]

[0354] Intermediate J (5.8 g, 60% yield) was obtained by replacing intermediate A (15.0 g) with intermediate A (5.0 g) and intermediate C (16.2 g) with intermediate D (5.4 g). The molecular weight of intermediate J was determined to be 473 by FAB-MS.

[0355] <Synthesis of Compound 22>

[0356] Amine compound 22 was synthesized via the following reaction formula 5-3.

[0357] [Reaction 5-3]

[0358]

[0359] Compound 22 was synthesized using the same method as compound 1, but with intermediate J (5.0 g) substituted for intermediate G (5.0 g) to obtain 5.4 g of compound 22 (yield 80%). The molecular weight of compound 22 was determined to be 639 by FAB-MS.

[0360] (6) Synthesis of compound 51

[0361] According to one embodiment, amine compound 51 can be synthesized, for example, by the steps of reaction formulas 6-1 to 6-3 described below.

[0362] <Synthesis of Intermediate B>

[0363] Intermediate B was synthesized using the following reaction formula 6-1.

[0364] [Reaction 6-1]

[0365]

[0366] Intermediate B (65% yield) was obtained by using the same method as the synthesis of intermediate A, by replacing 2-bromobiphenyl (20.0 g) (35.0 g) with 2-bromobiphenyl (35.0 g) and replacing 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (49.3 g) with 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (49.3 g) with 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (49.3 g) with 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline) (49.3 g) (49.3 g). The molecular weight of intermediate B was determined to be 245 by FAB-MS.

[0367] Synthesis of intermediate K

[0368] Intermediate K was synthesized via the following reaction formula 6-2.

[0369] [Reaction 6-2]

[0370]

[0371] Intermediate K (5.8 g, 60% yield) was obtained by replacing intermediate A (15.0 g) with intermediate B (5.0 g) and intermediate C (16.2 g) with intermediate D (5.4 g). The molecular weight of intermediate K was determined to be 473 by FAB-MS.

[0372] <Synthesis of Compound 51>

[0373] Amine compound 51 was synthesized via the following reaction formula 6-3.

[0374] [Reaction 6-3]

[0375]

[0376] Using the same method as in the synthesis of compound 1, intermediate G (5.0 g) was replaced with intermediate K (5.0 g), and 4-bromodibenzothiophene (2.8 g) was replaced with 4-bromodibenzofuran (2.6 g) to obtain 5.3 g of compound 51 (77% yield). The molecular weight of compound 51 was determined to be 655 by FAB-MS.

[0377] (7) Synthesis of compound 82

[0378] According to one embodiment, amine compound 82 can be synthesized, for example, by the steps of reaction formula 7 below.

[0379] [Reaction Formula 7]

[0380]

[0381] Using the same method as in the synthesis of compound 1, 5.6 g of compound 82 (75% yield) was obtained by replacing 4-bromo-6-phenyldibenzofuran (3.4 g) with 4-bromo-6-phenyldibenzofuran (2.6 g). The molecular weight of compound 82 was determined to be 715 by FAB-MS.

[0382] 2. Energy level evaluation of compounds

[0383] Table 2 below shows the lowest singlet excitation level (S1 level) and lowest triplet excitation level (T1 level) of compounds 1, 2, 3, 8, 22, 51, 82, and the following comparative examples X-1 to X-6.

[0384] Comparative compound X-1 to comparative compound X-6 are shown in Table 1.

[0385] Table 1

[0386]

[0387]

[0388]

[0389] The energy level values ​​in Table 2 were calculated using a non-empirical molecular orbital method. Specifically, calculations were performed using Gaussian 09 from Gaussian Corporation, with the energy level B3LYP / 6-31G(d).

[0390] Table 2

[0391] Compound types S1 energy level (eV) T1 energy level (eV) Compound 1 3.35 2.82 Compound 2 3.37 2.87 Compound 3 3.35 2.85 Compound 8 3.36 2.82 Compound 22 3.40 2.85 Compound 51 3.47 2.92 Compound 82 3.21 2.88 Comparative compound X-1 3.37 2.72 Comparative compound X-2 3.42 2.73 Comparative compound X-3 3.38 2.75 Comparative compound X-4 3.29 2.83 Comparative compound X-5 3.37 2.87 Comparative compound X-6 3.40 2.72

[0392] Referring to Table 2, it can be seen that compounds 1, 2, 3, 8, 22, 51, and 82, as amine compounds in one embodiment, exhibit higher lowest triplet excitation energy levels compared to comparative examples X-1 to X-3 and X-6. Furthermore, it can be seen that comparative examples X-4 and X-5 exhibit higher lowest triplet excitation energy levels compared to comparative examples X-1 to X-3 and X-6. Since compounds 1, 2, 3, 8, 22, 51, and 82 exhibit lowest triplet excitation energy levels of 2.8 eV or higher, they can be used as hole transport materials for blue phosphorescent elements. Furthermore, since comparative examples X-4 and X-5 exhibit lowest triplet excitation energy levels of 2.8 eV or higher, they can be used as hole transport materials for blue phosphorescent elements.

[0393] 3. Manufacturing and evaluation of light-emitting elements

[0394] (1) Manufacturing of light-emitting elements

[0395] Light-emitting elements comprising an amine compound of one embodiment or a comparative compound in a hole transport layer were manufactured using the following method. Compounds 1, 2, 3, 8, 22, 51, and 82, which are amine compounds of one embodiment, were used as hole transport layer materials to manufacture light-emitting elements of Examples 1 to 7. Light-emitting elements of Comparative Examples 1 to 6 were manufactured by using comparative example compounds X-1 to X-6 in the hole transport layer, respectively.

[0396] On a glass substrate, a thickness of After patterning the ITO, it was washed with ultrapure water, ultrasonically cleaned, irradiated with UV for 30 minutes, and then treated with ozone. Then, with... Thickness of HAT-CN deposition, to The thickness of TAPC deposition, and the compound of the example or the comparative example compound with The thickness of the deposition forms the hole transport region.

[0397] Then, FIRPIC and mCBP were co-deposited at a ratio of 5:95 (by weight) to form a thickness of [thickness value missing]. The light-emitting layer is then formed on the light-emitting layer using TmPyPB, with a thickness of [missing information]. A layer was formed using LiF with a thickness of [missing information]. The electron transport region was formed by a layer of aluminum (Al). Then, a layer with a thickness of [missing information] was formed. The second electrode. A layer with a thickness of [thickness missing] was formed on the second electrode using the following compound P4. The capping layer. In this embodiment, a hole transport region, a light-emitting layer, an electron transport region, and a second electrode are formed using a vacuum deposition apparatus.

[0398] Furthermore, the HAT-CN, TAPC, mCBP, FIrpic, and TmPyPB used in the manufacture of light-emitting elements are known substances, and commercially available products were sublimated and purified before being used.

[0399]

[0400]

[0401] (2) Evaluation of light-emitting elements

[0402] Table 3 below shows the luminous efficiency and device lifetime of the light-emitting elements of the embodiments and comparative examples. In Table 3, the luminous efficiency and device lifetime are relative values, showing the values ​​compared when the luminous efficiency and device lifetime of the light-emitting element of Comparative Example 1 are set to 100%. For luminous efficiency, a current density of 10 mA / cm² is used. 2 The luminous efficiency values ​​are shown by comparison. The Hamamatsu Photonics C9920-11 luminance orientation characteristic measurement device was used to measure the luminous efficiency. Component lifetime (LT) 50 The time taken to reduce the brightness of the light-emitting element to half is compared and shown.

[0403] Table 3

[0404]

[0405]

[0406] Referring to Table 3, it can be seen that the light-emitting elements of Examples 1 to 7 have superior luminous efficiency and lifetime compared to the light-emitting elements of Comparative Examples 1 to 6. The light-emitting elements of Examples 1 to 7 include the amine compounds of the above-described embodiments, specifically Compound 1, Compound 2, Compound 3, Compound 8, Compound 22, Compound 51, and Compound 82. The light-emitting elements of Examples 1 to 7 include Compound 1, Compound 2, Compound 3, Compound 8, Compound 22, Compound 51, and Compound 82 in the hole transport layer, which have higher lowest triplet excitation energy levels than Comparative Examples X-1 to X-3 and X-6. The relatively high lowest triplet excitation energy levels of Compound 1, Compound 2, Compound 3, Compound 8, Compound 22, Compound 51, and Compound 82 can prevent excitons from migrating from the light-emitting layer to functional layers such as the hole transport layer, thereby preventing the excitons from disappearing due to lack of light emission. Furthermore, as mentioned above, the light-emitting elements of Examples 1 to 7 exhibit improved device lifetime due to the use of an amine compound from one embodiment, which improves the stability of the material by including o-terphenyl. The o-terphenyl included in the amine compound of one embodiment does not reduce the stability of the amine compound and can contribute to maintaining a higher energy level at the lowest triplet excitation level of the amine compound. Therefore, it is determined that the light-emitting element including the amine compound of one embodiment will exhibit improved luminous efficiency and device lifetime.

[0407] In a light-emitting element (ED), as voltages are applied to the first electrode EL1 and the second electrode EL2, holes injected from the first electrode EL1 move through the hole transport region (HTR) to the light-emitting layer (EML), while electrons injected from the second electrode EL2 move through the electron transport region (ETR) to the EML. Electrons and holes recombine in the EML to generate excitons, which emit light as they transition from the excited state to the ground state.

[0408] Furthermore, Comparative Example compounds X-4 and X-5, like 3',6'-diphenyl-1,1':2',1”-terphenyl (3',6'-diphenyl-1,1':2',1”-terphenyl) or 3'-phenyl-1,1':2',1”-terphenyl (3'-phenyl-1,1':2',1”-terphenyl), contain sterically hindered substituents. In Table 2, Comparative Example compounds X-4 and X-5 exhibited higher lowest triplet excitation energy levels compared to Comparative Example compounds X-1 to X-3. However, due to the sterically hindered substituents, the light-emitting elements of Comparative Examples 4 and 5, including Comparative Example compounds X-4 and X-5, were judged to have decreased luminous efficiency and lifetime.

[0409] One embodiment of the amine compound comprises two o-terphenyl groups bonded to a nitrogen atom, thereby exhibiting improved material stability and hole transport properties. Therefore, when the amine compound of one embodiment is used in a light-emitting element, luminous efficiency and element lifetime can be improved.

[0410] One embodiment of the light-emitting element may include a first electrode, a second electrode, and at least one functional layer disposed between the first electrode and the second electrode. In one embodiment of the light-emitting element, the at least one functional layer may exhibit improved element lifetime and luminous efficiency by including an amine compound of one embodiment.

[0411] Although the above description has been made with reference to preferred embodiments of the present invention, it will be understood by those skilled in the art or those with ordinary knowledge of the art that various modifications and alterations can be made to the present invention without departing from the spirit and technical scope of the invention as set forth in the claims.

[0412] Therefore, the technical scope of this invention should not be limited to the contents described in the detailed specification, but should be determined by the claims.

Claims

1. An amine compound represented by the following Chemical Formula 1: [Chemical Formula 1] ， In the Chemical Formula 1, n1 and n2 are each independently 0 or 1, a1 and a2 are each independently an integer of 0 or more and 5 or less, a3 to a6 are each independently an integer of 0 or more and 4 or less, R1 to R6 are each independently a hydrogen atom, a deuterium atom, a halogen atom, or a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms, Q1 is represented by the following Chemical Formula 2: [Chemical Formula 2] ， In the Chemical Formula 2, X is O or S, and in the case where X is O, N of the Chemical Formula 1 is bonded to any one of C1, C2, and C4, a11 is an integer of 0 or more and 7 or less, R 11 is a hydrogen atom, a deuterium atom, or a substituted or unsubstituted aryl group having 6 to 12 ring-forming carbon atoms.

2. The amine compound according to claim 1, wherein the Chemical Formula 1 is represented by the following Chemical Formula 1-1: [Chemical Formula 1-1] ， In the Chemical Formula 1-1, a1 to a6, R1 to R6, n1 and n2 are the same as defined in the Chemical Formula 1, a11 and R 11 the same as defined in the Chemical Formula 2.

3. The amine compound according to claim 1, wherein the Chemical Formula 2 is represented by any one of the following Chemical Formula 2-1, the following Chemical Formula 2-2, and the following Chemical Formula 2-4: [Chemical Formula 2-1] [Chemical Formula 2-2] [Chemical Formula 2-4] ， In the Chemical Formula 2-1, the Chemical Formula 2-2, and the Chemical Formula 2-4, a11, R 11 and X is the same as defined in the chemical formula 2.

4. The amine compound according to claim 1, wherein the Chemical Formula 1 is represented by the following Chemical Formula 1-A or the following Chemical Formula 1-B: [Chemical Formula 1-A] [Chemical Formula 1-B] ， In the Chemical Formula 1-A and the Chemical Formula 1-B, a1 to a6, R1 to R6, n1, n2, and Q1 are the same as defined in the Chemical Formula 1.

5. The amine compound according to claim 4, wherein the Chemical Formula 1-A is represented by any one of the following Chemical Formula 1-A1 to Chemical Formula 1-A3: [Chemical Formula 1-A1] [Chemical Formula 1-A2] [Chemical Formula 1-A3] ， In the Chemical Formula 1-A1 to Chemical Formula 1-A3, a1 to a6, R1 to R6, n1, n2, and Q1 are the same as defined in the Chemical Formula 1-A.

6. The amine compound according to claim 1, wherein a11 is 0 or 1, In the case where said a11 is 1, R 11 is a substituted or unsubstituted phenyl group.

7. The amine compound according to claim 1, wherein at least one of R1 to R3 is a deuterium atom.

8. The amine compound according to claim 1, wherein the Chemical Formula 1 is represented by any one of the following Compound Group 1: [Compound Group 1] ， In the Compound Group 1, D is a deuterium atom.

9. A light-emitting element comprising: a first electrode; a second electrode disposed over the first electrode; and at least one functional layer disposed between the first electrode and the second electrode, and including the amine compound according to any one of claims 1 to 8.

10. The light-emitting element according to claim 9, wherein the at least one functional layer includes a light-emitting layer, a hole-transport region disposed between the first electrode and the light-emitting layer, and an electron-transport region disposed between the light-emitting layer and the second electrode, wherein the hole-transport region includes the amine compound. ​

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