Light-emitting element, condensed polycyclic compound for light-emitting element, and electronic device containing the light-emitting element.

Abstract

To provide a light-emitting element with improved luminous efficiency and element lifespan. [Solution] One embodiment of the light-emitting device includes a first electrode, a second electrode placed on the first electrode, and a light-emitting layer placed between the first electrode and the second electrode and containing a first compound represented by a specific chemical formula.

Description

[Technical Field]

[0001] The present invention relates to a light-emitting element, a condensed polycyclic compound used in a light-emitting element, and an electronic device including a light-emitting element. [Background technology]

[0002] Recently, there has been a great deal of development activity in organic electroluminescence displays as image display devices. Unlike liquid crystal displays and the like, organic electroluminescence displays are so-called self-emissive display devices that achieve display by recombining holes and electrons injected from the first and second electrodes in the light-emitting layer, causing a light-emitting material containing an organic compound in the light-emitting layer to emit light.

[0003] When applying organic electroluminescent devices to display devices, there is a demand for lower driving voltage, higher luminous efficiency, and longer lifespan for these devices. Therefore, there is a continuous need for the development of organic electroluminescent device materials that can stably achieve these requirements.

[0004] In particular, recently, technologies have been developed for phosphorescence emission that utilizes the energy of the triplet state and fluorescence emission that utilizes the phenomenon of triplet exciton collisions generating singlet excitons (Triplet-triplet annihilation, TTA) in order to realize highly efficient organic electroluminescent devices. Development is also underway for thermally activated delayed fluorescence (TADF) materials that utilize delayed fluorescence phenomena. [Overview of the project] [Problems that the invention aims to solve]

[0005] The objective of the present invention is to provide a light-emitting element with improved luminous efficiency and element lifespan.

[0006] Another object of the present invention is to provide a condensed polycyclic compound that can improve the luminescence efficiency and device lifetime of a light-emitting element.

[0007] Another object of the present invention is to provide a display device that includes a light-emitting element with improved luminous efficiency and lifespan, and has excellent display quality. [Means for solving the problem]

[0008] A light-emitting element according to one embodiment of the present invention includes a first electrode, a second electrode disposed on the first electrode, and at least one light-emitting layer disposed between the first electrode and the second electrode and containing a first compound represented by the following chemical formula 1.

[0009] <Chemical formula 1> JPEG2026076767000002.jpg166155

[0010] In the above chemical formula 1, X 1 ~X 3 These are O, S, or NAr, respectively, independently. 1 Ar1 is a substituted or unsubstituted aryl group with 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group with 2 to 30 ring-forming carbon atoms, and R 1 ~R 15 Each of these is independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, and R 13 When R is a diphenylamine group or a carbazole group, 10 If the atom is a hydrogen atom or contains a diphenylamine group, it is excluded, and the first compound represented by chemical formula 1 includes a structure in which at least one hydrogen atom is replaced by a deuterium atom.

[0011] The light-emitting layer comprises a host and a dopant, and the dopant may comprise a first compound represented by the chemical formula 1.

[0012] The first compound represented by the chemical formula 1 can be represented by any one of the following chemical formulas 2-1 to 2-4.

[0013] <Chemical formula 2-1> JPEG2026076767000003.jpg108154

[0014] <Chemical formula 2-2> JPEG2026076767000004.jpg108137

[0015] <Chemical formula 2-3> JPEG2026076767000005.jpg107120

[0016] <Chemical formula 2-4> JPEG2026076767000006.jpg161158

[0017] In the chemical formulas 2-1 to 2-4, X 2a to X 3a are each independently O or S, and R 21 to R 24 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, and n1 to n4 are each independently an integer of 0 or more and 5 or less.

[0018] In the chemical formulas 2-1 to 2-4, X 1 , and R 1 to R<关于“ 15 ”的翻译,由于原内容中此处为特定标签,未明确具体含义,所以保留原文 15 can be applied the same explanation as defined in the chemical formula 1.

[0019] The first compound represented by the chemical formula 1 can be represented by any one of the following chemical formulas 3-1 to 3-4. <关于“ ”的翻译,由于原内容中此处为特定标签,未明确具体含义,所以保留原文

[0020] <Chemical formula 3-1> JPEG2026076767000007.jpg104154

[0021] <Chemical formula 3-2> JPEG2026076767000008.jpg108137

[0022] <Chemical formula 3-3> JPEG2026076767000009.jpg105122

[0023] <Chemical formula 3-4> JPEG2026076767000010.jpg156154

[0024] In the above chemical formulas 3-1 and 3-4, R 21 ~R 24 Each of these is independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, and each of n1 to n4 is independently an integer between 0 and 5, and in the above chemical formula 3-2, R 13 If R is a diphenylamine group or a carbazole group, 10 This can be an unsubstituted alkyl group having 1 to 20 carbon atoms, or an unsubstituted aryl group having 6 to 20 ring-forming carbon atoms.

[0025] In the above chemical formulas 3-1 to 3-4, X 1 , and R 1 ~R 15 The same explanation as that defined in chemical formula 1 above may apply to it.

[0026] The first compound represented by chemical formula 1 can be represented by any one of the following chemical formulas 4-1 to 4-4.

[0027] <Chemical formula 4-1> JPEG2026076767000011.jpg106141

[0028] <Chemical formula 4-2> JPEG2026076767000012.jpg106141

[0029] <Chemical formula 4-3> JPEG2026076767000013.jpg105124

[0030] <Chemical formula 4-4> JPEG2026076767000014.jpg156150

[0031] In the above chemical formulas 4-1 to 4-4, X 1a ~X 2a Each is independently O or S, and R 31 ~R 34 Each of these is independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, and each of n11 to n14 can independently be an integer between 0 and 5.

[0032] In the aforementioned chemical formulas 4-1 to 4-4, X 3 , and R 1 ~R 15 The same explanation as that defined in chemical formula 1 above can be applied to it.

[0033] The first compound represented by the aforementioned chemical formula 1 can also be represented by the following chemical formula 5.

[0034] <Chemical formula 5> JPEG2026076767000015.jpg160146

[0035] In the aforementioned chemical formula 5, X 1b , X2b , and X 3b Of these, at least one is represented by chemical formula 6-1 or chemical formula 6-2 below, and the remaining ones are independently O, S, or NAr. 2 And Ar 2 This can be a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms.

[0036] In the above chemical formula 5, R 1 ~R 15 The same explanation as that defined in chemical formula 1 above may apply to it.

[0037] <Chemical formula 6-1> JPEG2026076767000016.jpg78111

[0038] <Chemical formula 6-2> JPEG2026076767000017.jpg64117

[0039] In the above chemical formulas 6-1 to 6-2, R 41 and R 45 Each of these is independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, and n21, n23, and n25 are each independently integers between 0 and 5, n22 is an integer between 0 and 4, and n24 is an integer between 0 and 3. JPEG2026076767000018.jpg2145 This is the position where it is connected to the chemical formula 5.

[0040] The aforementioned X 1 ~X 3 Each is independently O or NAr 3 And Ar 3 This can be a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms.

[0041] In the above chemical formula 1, R 13 If R is a diphenylamine group or a carbazole group, 10 R is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms. 10 If substitution occurs, the substituent may be a deuterium atom, a cyano group, an unsubstituted alkyl group having 1 to 10 carbon atoms, an unsubstituted aryl group having 6 to 15 carbon atoms, or an unsubstituted heteroaryl group having 2 to 15 carbon atoms.

[0042] The light-emitting layer may further contain at least one of the following: a second compound represented by the chemical formula HT-1, a third compound represented by the chemical formula ET-1, and a fourth compound represented by the chemical formula D-1.

[0043] <Chemical formula HT-1> JPEG2026076767000019.jpg106131

[0044] In the aforementioned chemical formula HT-1, M1 to M8 are each independently N or CR. 51 L1 is a direct linkage, a substituted or unsubstituted ring-forming arylene group with 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heteroarylene group with 2 to 30 carbon atoms, and Y a Direct coupling, CR 52 R 53 , or SiR 54 R 55 And Ar a R is a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 6 to 30 ring-forming carbon atoms, 51 ~R 55Each of these groups is independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted thio group, a substituted or unsubstituted oxy group, a substituted or unsubstituted amine group, a substituted or unsubstituted boron group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted ring-forming aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted ring-forming heteroaryl group having 2 to 60 carbon atoms, or can bond with adjacent groups to form a ring.

[0045] <Chemical formula ET-1> JPEG2026076767000020.jpg107132

[0046] In the aforementioned chemical formula ET-1, Z a ~Z c At least one of them is N and the rest are CR 56 And R 56 b1 to b3 are each an integer between 0 and 10. b ~Ar d Each of these is independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, and each of L2 to L4 is independently a directly bonded, substituted or unsubstituted arylene group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring-forming carbon atoms.

[0047] <Chemical formula D-1> JPEG2026076767000021.jpg167164

[0048] In the chemical formula D-1, Q1 to Q4 are each independently C or N, and C1 to C4 are each independently a substituted or unsubstituted hydrocarbon ring having 5 to 30 ring-forming carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heterocycle having 2 to 30 ring-forming carbon atoms, X 11 ~X 14 Each can be directly connected or JPEG2026076767000022.jpg1450, L 11 ~L 13 Each is independent, directly connected, JPEG2026076767000023.jpg29156 A substituted or unsubstituted divalent alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted ring-forming arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heteroarylene group having 2 to 30 carbon atoms, where b11 to b13 are each independently 0 or 1, R 61 ~R 66 Each of these is independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted thio group, a substituted or unsubstituted oxy group, a substituted or unsubstituted amine group, a substituted or unsubstituted boron group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 ring-forming carbon atoms, and each of d1 to d4 is independently an integer between 0 and 4.

[0049] An electronic device according to one embodiment of the present invention includes a base layer, a circuit layer disposed on the base layer, and a display element layer disposed on the circuit layer and including a light-emitting element, wherein the light-emitting element includes a first electrode, a second electrode disposed on the first electrode, and a light-emitting layer disposed between the first electrode and the second electrode and containing a first compound represented by chemical formula 1.

[0050] The light-emitting element further includes a capping layer disposed on the second electrode, the refractive index of the capping layer may be 1.6 or more for light in the wavelength range of 550 nm to 660 nm.

[0051] The light-emitting element is disposed on the display element layer and further includes a color control unit including a quantum dot, the light-emitting element emits a first color light, and the light control layer may include a first color control unit including a first quantum dot that converts the first color light into a second color light in a longer wavelength region than the first color light, a second light control unit including a second quantum dot that converts the first color light into a third color light in a longer wavelength region than the first color light and the second color light, and a third color control unit that transmits the first color light.

[0052] The system further includes a color filter layer disposed on top of the color control unit, the color filter layer may include a first filter that transmits the second color light, a second filter that transmits the third color light, and a third filter that transmits the first color light.

[0053] The aforementioned electronic device can be selected from among large display devices such as televisions, monitors, and external billboards, as well as medium- and small-sized display devices such as personal computers, laptop computers, personal digital assistants, vehicle display devices, game consoles, portable electronic devices, and cameras.

[0054] A condensed polycyclic compound according to one embodiment of the present invention is represented by the above chemical formula 1. [Effects of the Invention]

[0055] The light-emitting element of one embodiment may exhibit improved element characteristics, including high efficiency and long lifespan.

[0056] The condensed polycyclic compound of one embodiment can be included in the light-emitting layer of a light-emitting device and contribute to the high efficiency and long lifespan of the light-emitting device.

[0057] The display device of one embodiment may exhibit excellent display quality. [Brief explanation of the drawing]

[0058] [Figure 1] This is a plan view of a display device according to one embodiment of the present invention. [Figure 2] This is a cross-sectional view of a display device according to one embodiment of the present invention. [Figure 3] This is a schematic cross-sectional view showing a light-emitting element according to one embodiment of the present invention. [Figure 4] This is a schematic cross-sectional view showing a light-emitting element according to one embodiment of the present invention. [Figure 5] This is a schematic cross-sectional view showing a light-emitting element according to one embodiment of the present invention. [Figure 6] This is a schematic cross-sectional view showing a light-emitting element according to one embodiment of the present invention. [Figure 7] This is a cross-sectional view of a display device according to one embodiment of the present invention. [Figure 8] This is a cross-sectional view of a display device according to one embodiment of the present invention. [Figure 9] This is a cross-sectional view showing a display device according to one embodiment of the present invention. [Figure 10] This is a cross-sectional view showing a display device according to one embodiment of the present invention. [Figure 11] This figure shows a vehicle equipped with a display device according to one embodiment. [Modes for carrying out the invention]

[0059] Because the present invention can be modified in various ways and take on various forms, specific embodiments are illustrated in the drawings and described in detail in the text. However, this should be understood not as an attempt to limit the present invention to any particular disclosure, but rather as including all modifications, equivalents, or substitutes that fall within the spirit and technical scope of the present invention.

[0060] In describing each drawing, similar reference numerals are used for similar components. In the attached drawings, the dimensions of structures are shown enlarged for clarity of the invention. Terms such as "first," "second," etc., are used to describe a variety of components, but the components are not limited to those described by these terms. These terms are used solely for the purpose of distinguishing one component from another. For example, without departing from the scope of the invention, the first component may be named the second component, and similarly, the second component may also be named the first component. Singular expressions include plural expressions unless the context clearly indicates otherwise.

[0061] In this application, terms such as “includes” or “having” should be understood to indicate the presence of features, figures, steps, actions, components, parts, or combinations thereof described in the specification, without prejudice to the presence or possibility of adding one or more other features, figures, steps, actions, components, parts, or combinations thereof.

[0062] In this application, when a part such as a layer, film, region, or plate is said to be "above" or "above" another part, this includes not only when it is "directly above" another part, but also when there is another part in between. Conversely, when a part such as a layer, film, region, or plate is said to be "below" or "below" another part, this includes not only when it is "directly below" another part, but also when there is another part in between. Furthermore, in this application, "positioned above" may include not only when it is above, but also when it is positioned below.

[0063] In this specification, "substituted or unsubstituted" may mean that a molecule is substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium atoms, halogen atoms, cyano groups, nitro groups, amino groups, silyl groups, oxy groups, thio groups, sulfinyl groups, sulfonyl groups, carbonyl groups, boron groups, phosphine oxide groups, phosphine sulfide groups, alkyl groups, alkenyl groups, alkynyl groups, hydrocarbon ring groups, aryl groups, and heterocyclic groups. Furthermore, each of the substituents exemplified above may be substituted or unsubstituted. For example, a biphenyl group may be interpreted as an aryl group, or as a phenyl group substituted with a phenyl group.

[0064] In this specification, "bonding with adjacent groups to form a ring" may mean bonding with adjacent groups to form a substituted or unsubstituted hydrocarbon ring, or a substituted or unsubstituted heterocycle. Hydrocarbon rings include aliphatic hydrocarbon rings and aromatic hydrocarbon rings. Heterocycles include aliphatic heterocycles and aromatic heterocycles. Hydrocarbon rings and heterocycles may be monocyclic or polycyclic. Furthermore, rings formed by bonding with each other may be linked to other rings to form a spirostructure.

[0065] In this specification, "adjacent group" may mean a substituent substituted on an atom directly linked to the atom on which the substituent is substituted, another substituent substituted on the atom on which the substituent is substituted, or the substituent that is most stereostructically adjacent to the substituent in question. For example, the two methyl groups in 1,2-dimethylbenzene may be interpreted as "adjacent groups," and the two ethyl groups in 1,1-diethylcyclopentene may be interpreted as "adjacent groups." Similarly, the two methyl groups in 4,5-dimethylphenanthrene may be interpreted as "adjacent groups."

[0066] In this specification, examples of halogen atoms include fluorine, chlorine, bromine, or iodine atoms.

[0067] In this specification, alkyl groups may be linear, branched, or cyclic. The number of carbon atoms in an alkyl group may be 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, s-butyl, t-butyl, i-butyl, 2-ethylbutyl, 3,3-dimethylbutyl, n-pentyl, i-pentyl, neopentyl, t-pentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 2-butylhexyl, n-heptyl, and 1-methyl Peptyl group, 2,2-dimethylheptyl group, 2-ethylheptyl group, 2-butylheptyl group, n-octyl group, t-octyl group, 2-ethyloctyl group, 2-butyloctyl group, 2-hexyloctyl group, 3,7-dimethyloctyl group, n-nonyl group, n-decyl group, adamantyl group, 2-ethyldecyl group, 2-butyldecyl group, 2-hexyldecyl group, 2-octyldecyl group, n-undecyl group, n-dodecyl group, 2-ethyldodecyl group, 2-butyldodecyl group, 2-hexyldodecyl group, 2 - Octyldecyl group, n-tridecyl group, n-tetradecyl group, n-pentadecyl group, n-hexadecyl group, 2-ethylhexadecyl group, 2-butylhexadecyl group, 2-hexylhexadecyl group, 2-octylhexadecyl group, n-heptadecyl group, n-octadecyl group, n-nonadecyl group, n-icosyl group, 2-ethylicosyl group, 2-butylicosyl group, 2-hexylicosyl group, 2-octylicosyl group, n-henicosyl group, n-docosyl group, n-tricosyl group, n-tetracosyl group Examples include, but are not limited to, n-pentacosyl group, n-hexacosyl group, n-heptacosyl group, n-octacosyl group, n-nonacosyl group, n-triacontyl group, cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, 4-methylcyclohexyl group, 4-t-butylcyclohexyl group, cycloheptyl group, cyclooctyl group, cyclononyl group, cyclodecyl group, norbornyl group, 1-adamantyl group, 2-adamantyl group, isobornyl group, and bicycloheptyl group.

[0068] In this specification, an alkenyl group means a hydrocarbon group containing one or more carbon double bonds in the middle or terminal of an alkyl group having two or more carbon atoms. An alkenyl group may be linear or branched. The number of carbon atoms is not particularly limited, but is 2 to 30, 2 to 20, or 2 to 10. Examples of alkenyl groups include, but are not limited to, vinyl, 1-butenyl, 1-pentenyl, 1,3-butadienylaryl, styrenyl, and styrylvinyl groups.

[0069] In this specification, an alkynyl group means a hydrocarbon group containing one or more carbon triple bonds in the middle or terminal of an alkyl group having two or more carbon atoms. An alkynyl group may be linear or branched. The number of carbon atoms is not particularly limited, but is typically 2 to 30, 2 to 20, or 2 to 10. Specific examples of alkynyl groups include, but are not limited to, ethynyl and propynyl groups.

[0070] In this specification, a hydrocarbon ring group means any active group or substituent derived from an aliphatic hydrocarbon ring. A hydrocarbon ring group may be a saturated hydrocarbon ring group having 5 to 20 carbon atoms.

[0071] In this specification, an aryl group means any active group or substituent derived from an aromatic hydrocarbon ring. An aryl group may be a monocyclic aryl group or a polycyclic aryl group. The number of ring-forming carbon atoms in an aryl group is 6 to 30, 6 to 20, or 6 to 15. Examples of aryl groups include, but are not limited to, phenyl, naphthyl, fluorenyl, anthracenyl, phenantrenyl, biphenylyl, terphenylyl, quarterphenylyl, quincphenylyl, sexiphenylyl, triphenylenyl, pyrenyl, benzofluorantene, and chrysene.

[0072] In this specification, the fluorenyl group may be substituted, or two substituents may be bonded to each other to form a spiro structure. Examples of substitutions of the fluorenyl group are, but are not limited to, the following.

[0073] JPEG2026076767000024.jpg38153

[0074] In this specification, a heterocyclic group means any active group or substituent derived from a ring containing one or more heteroatoms from B, O, N, P, Si, and S. Heterocyclic groups include aliphatic heterocyclic groups and aromatic heterocyclic groups. Aromatic heterocyclic groups may be heteroaryl groups. Aliphatic heterocycles and aromatic heterocycles may be monocyclic and polycyclic.

[0075] In this specification, a heterocyclic group may contain one or more heteroatoms from B, O, N, P, Si, and S. If a heterocyclic group contains two or more heteroatoms, the two or more heteroatoms may be the same or different. A heterocyclic group may be a monocyclic heterocyclic group or a polycyclic heterocyclic group, and is a concept that includes a heteroaryl group. The number of ring-forming carbon atoms in a heterocyclic group may be 2 to 30, 2 to 20, or 2 to 10.

[0076] In this specification, an aliphatic heterocyclic group may contain one or more heteroatoms from B, O, N, P, Si, and S. The number of ring-forming carbon atoms in an aliphatic heterocyclic group may be 2 to 30, 2 to 20, or 2 to 10. Examples of aliphatic heterocyclic groups include, but are not limited to, oxirane groups, thiirane groups, pyrrolidine groups, piperidine groups, tetrahydrofuran groups, tetrahydrothiophene groups, thian groups, tetrahydropyran groups, and 1,4-dioxane groups.

[0077] In this specification, a heteroaryl group may contain one or more heteroatoms from B, O, N, P, Si, and S. If a heteroaryl group contains two or more heteroatoms, the two or more heteroatoms may be the same or different. A heteroaryl group may be a monocyclic heterocyclic group or a polycyclic heterocyclic group. The number of ring-forming carbon atoms in a heteroaryl group is 2 to 30, 2 to 20, or 2 to 10. Examples of heteroaryl groups include thienyl group, furyl group, pyrrolyl group, imidazolyl group, pyridyl group, bipyridinyl group, triazolyl group, acridinyl group, pyridadinyl group, pyrazinyl group, quinolyl group, quinazolyl group, quinoxalinyl group, phenoxazinyl group, phthalazinyl group, pyridopyrimidinyl group, pyridopyradinyl group, pyrazinopyradinyl group, isoquinolinyl group, indolyl group, carbazolyl group, N-arylcarbazolyl group, and N-heteroaryl group. Examples include, but are not limited to, rubazolyl, N-alkylcarbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothiophenyl, dibenzothiophenyl, thienothiophenyl, benzofuranyl, phenanthrolinyl, thiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, thiadiazolyl, phenothiazinyl, dibenzosilolyl, and dibenzofuranyl groups.

[0078] In this specification, the above description of aryl groups may apply, except that arylene groups are divalent. The above description of heteroaryl groups may apply, except that heteroarylene groups are divalent.

[0079] In this specification, the silyl group includes alkylsilyl groups and arylsilyl groups. Examples of silyl groups include, but are not limited to, trimethylsilyl, triethylsilyl, t-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, and phenylsilyl groups.

[0080] In this specification, the number of carbon atoms in the carbonyl group is not particularly limited, but may be 1 to 40, 1 to 30, or 1 to 20. For example, it may have, but is not limited to, the following structure.

[0081] JPEG2026076767000025.jpg38170

[0082] In this specification, the number of carbon atoms in the sulfinyl group and the sulfonyl group is not particularly limited, but may be between 1 and 30. The sulfinyl group may include an alkyl sulfinyl group and an aryl sulfinyl group. The sulfonyl group may include an alkyl sulfonyl group and an aryl sulfonyl group.

[0083] In this specification, the thio group may include alkylthio groups and arylthio groups. The thio group may mean a group to which a sulfur atom is bonded to the alkyl or aryl group as defined above. Examples of thio groups include, but are not limited to, methylthio, ethylthio, propylthio, pentylthio, hexylthio, octylthio, dodecylthio, cyclopentylthio, cyclohexylthio, phenylthio, and naphthylthio groups.

[0084] In this specification, an oxy group may mean a group in which an oxygen atom is bonded to an alkyl group or aryl group as defined above. Oxy groups may include alkoxy groups and aryloxy groups. Alkoxy groups may be linear, branched, or cyclic. The number of carbon atoms in an alkoxy group is not particularly limited, but may be, for example, 1 to 20 or 1 to 10. Examples of oxy groups include, but are not limited to, ethoxy, methoxy, n-propoxy, isopropoxy, butoxy, pentyloxy, hexyloxy, octyloxy, nonyloxy, decyloxy, and benzyloxy.

[0085] In this specification, a boron group means a group in which a boron atom is bonded to an alkyl or aryl group as defined above. A boron group includes alkylboron groups and arylboron groups. Examples of boron groups include, but are not limited to, dimethylboron groups, diethylboron groups, t-butylmethylboron groups, diphenylboron groups, and phenylboron groups.

[0086] In this specification, the number of carbon atoms in the amine group is not particularly limited, but may be between 1 and 30. The amine group may include alkylamines and arylamines. Examples of amine groups include, but are not limited to, methylamines, dimethylamines, phenylamines, diphenylamines, naphthylamines, and 9-methyl-anthracenylamines.

[0087] In this specification, among alkylthio groups, alkylsulfoxy groups, alkylaryl groups, alkylamino groups, alkylboron groups, alkylsilyl groups, and alkylamine groups, alkyl groups are as exemplified by the alkyl groups described above.

[0088] In this specification, among the aryloxy group, arylthio group, arylsulfoxy group, arylamino group, arylboron group, arylsilyl group, and arylamine group, the aryl group is as exemplified by the aryl group described above.

[0089] In this specification, direct bonding may mean a single bond.

[0090] On the other hand, in this specification, JPEG2026076767000026.jpg27162 indicates the position where the images are concatenated.

[0091] Hereinafter, an embodiment of the present invention will be described with reference to the drawings.

[0092] Figure 1 is a plan view showing one embodiment of the display device DD. Figure 2 is a cross-sectional view of the display device DD according to one embodiment. Figure 2 is a cross-sectional view showing the portion corresponding to the line I-I' in Figure 1.

[0093] The display device DD may include a display panel DP and an optical layer PP disposed on the display panel DP. The display panel PP 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 is disposed on the display panel DP and can control the reflected light on the display panel DP due to external light. The optical layer PP may include, for example, a polarizing layer or a color filter layer. On the other hand, contrary to the figures, the optical layer PP may be omitted from the display device DD of one embodiment.

[0094] A base substrate BL may be placed on top of the optical layer PP. The base substrate BL may be a component that provides a base surface on which the optical layer PP is placed. The base substrate BL may be a glass substrate, a metal substrate, a plastic substrate, etc. However, the embodiment is not limited to these, and the base substrate BL may be an inorganic layer, an organic layer, or a composite material layer. Also, contrary to the figures, the base substrate BL may be omitted in one embodiment.

[0095] The display device DD according to one embodiment may further include a charging layer (not shown). A packing layer (not shown) may be disposed between the display element layer DP-ED and the base substrate BL. The packing layer (not shown) may be an organic layer. The packing layer (not shown) may contain at least one of acrylic resin, silicone resin, and epoxy resin.

[0096] The display panel DP may include a base layer BS, a circuit layer DP-CL provided on the base layer BS, and a display element layer DP-ED. The display element layer DP-ED may include a pixel definition film PDL, light-emitting elements ED-1, ED-2, and ED-3 positioned between the pixel definition film PDL, and a sealing layer TFE positioned on the light-emitting elements ED-1, ED-2, and ED-3.

[0097] The base layer BS may be a component that provides the base surface on which the display element layer EP-ED is arranged. The base layer BS may be a glass substrate, a metal substrate, a plastic substrate, etc. However, the examples are not limited to these, and the base layer BS may be an inorganic layer, an organic layer, or a composite material layer.

[0098] In one embodiment, the circuit layer DP-CL is placed on the base layer BS, but 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-ED may include a switching transistor and a drive transistor for driving the organic electroluminescent elements ED-1, ED-2, and ED-3.

[0099] Each of the light-emitting elements ED-1, ED-2, and ED-3 may have the structure of one embodiment of the light-emitting element ED shown in Figures 3 to 6, which will be described later. 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.

[0100] Figure 2 shows an embodiment in which 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 an opening OH defined in the pixel delimiting (defining) film PDL, and the hole transport region HTR, electron transport region ETR, and second electrode EL2 are provided as a common layer for all light-emitting elements ED-1, ED-2, and ED-3. However, the embodiments are not limited to this, and in one embodiment, contrary to the illustration in Figure 2, the hole transport region HTR and electron transport region ETR may be patterned and provided inside the opening OH defined in the pixel delimiting (defining) film PDL. For example, in one embodiment, the hole transport region HTR, light-emitting layers EML-R, EML-G, EML-B, and electron transport region ETR of light-emitting elements ED-1, ED-2, and ED-3 may be patterned and provided by an inkjet printing method.

[0101] The sealing layer TFE may cover the organic electroluminescent elements ED-1, ED-2, and ED-3. The sealing layer TFE may seal the display element layer DP-ED. The sealing layer TFE may be a thin film sealing layer. The sealing layer TFE may consist of one or more layers stacked together. The sealing layer TFE includes at least one insulating layer. The sealing layer TFE according to one embodiment may include at least one inorganic film (hereinafter referred to as the sealing inorganic film). Furthermore, the sealing layer TFE according to one embodiment may include at least one organic film (hereinafter referred to as the sealing organic film) and at least one sealing inorganic film.

[0102] The encapsulating inorganic film protects the display element layer DP-ED from moisture / oxygen, and the encapsulating organic film protects the display element layer DP-ED from foreign matter such as dust particles. The encapsulating inorganic film may contain, but is not limited to, silicon nitride, silicon oxynitride, silicon oxide, titanium oxide, or aluminum oxide. The encapsulating organic film may contain, but is not limited to, acrylic compounds or epoxy compounds. The encapsulating organic film may contain, but is not limited to, photopolymerizable organic substances.

[0103] The sealing layer TFE may be placed on top of the second electrode EL2 and fill the opening OH.

[0104] Referring to Figures 1 and 2, the display device DD may include a non-emitting region NPXA and emitting regions PXA-R, PXA-G, and PXA-B. Each of the emitting regions PXA-R, PXA-G, and PXA-B may be a region from which light generated from each of the light-emitting elements ED-1, ED-2, and ED-3 is emitted. The emitting regions PXA-R, PXA-G, and PXA-B may be spaced apart from each other on a plane.

[0105] Each of the light-emitting regions PXA-R, PXA-G, and PXA-B may be a region separated by a pixel delimiting (defining) film PPL. The non-light-emitting region NPXA is a region between adjacent light-emitting regions PXA-R, PXA-G, and PXA-B, and may correspond to a pixel delimiting (defining) film PDL. On the other hand, in this specification, each of the light-emitting regions PXA-R, PXA-G, and PXA-B may correspond to a pixel. The pixel delimiting (defining) film PDL may separate light-emitting elements ED-1, ED-2, and ED-3. The light-emitting layers EML-R, EML-G, and EML-B of light-emitting elements ED-1, ED-2, and ED-3 may be located in and separated by an opening OH that is partitioned (defined) by the pixel delimiting (defining) film PDL.

[0106] The light-emitting regions PXA-R, PXA-G, and PXA-B can be divided into multiple groups according to the color of the light generated from the light-emitting elements ED-1, ED-2, and ED-3. The display device DD of one embodiment shown in Figures 1 and 2 exemplifies three light-emitting regions PXA-R, PXA-G, and PXA-B that emit red, green, and blue light, respectively. For example, the display device DD of one embodiment may include a red light-emitting region PXA-R, a green light-emitting region PXA-G, and a blue light-emitting region PXA-B that are separated from each other.

[0107] In one embodiment of the display device DD, the multiple light-emitting elements ED-1, ED-2, and ED-3 may emit light of different wavelengths. For example, in one embodiment, the display device DD may include a light-emitting element ED-1 that emits red light, a second light-emitting element ED-3 that emits green light, and a third light-emitting element ED-3 that emits blue light. In other words, the red light-emitting region PXA-R, the green light-emitting region PXA-G, and the blue light-emitting region PXA-B of the display device DD may correspond to the first light-emitting element ED-1, the second light-emitting element ED-2, and the third light-emitting element ED-3, respectively.

[0108] However, the examples are not limited to these, and the first to third light-emitting elements ED-1, ED-2, and ED-3 may emit light in the same wavelength range, or at least one of them may emit light in a different wavelength range. Furthermore, all of the first to third light-emitting elements ED-1, ED-2, and ED-3 may emit blue light.

[0109] In one embodiment of the display device DD, the light-emitting regions PXA-R, PXA-G, and PXA-B may be arranged in a striped pattern. Referring to Figure 1, multiple red light-emitting regions PXA-R, multiple green light-emitting regions PXA-G, and multiple blue light-emitting regions PXA-B may be aligned along the second directional axis DR2. Alternatively, the red light-emitting regions PXA-R, green light-emitting regions PXA-G, and blue light-emitting regions PXA-B may be arranged alternately along the first directional axis DR1.

[0110] In Figures 1 and 2, the areas of the light-emitting regions PXA-R, PXA-G, and PXA-B are shown to be similar, but the examples are not limited to these, and the areas of the light-emitting regions PXA-R, PXA-G, and PXA-B may differ from each other depending on the wavelength range of the emitted light. On the other hand, the areas of the light-emitting regions PXA-R, PXA-G, and PXA-B may represent the area as viewed from the plane defined by the first directional axis DR1 and the second directional axis DR2.

[0111] On the other hand, the arrangement of the light-emitting regions PXA-R, PXA-G, and PXA-B is not limited to that shown in Figure 1. The order in which the red light-emitting region PXA-R, the green light-emitting region PXA-G, and the blue light-emitting region PXA-B are arranged can be provided in various combinations depending on the display quality characteristics required by the display device DD. For example, the arrangement of the light-emitting regions PXA-R, PXA-G, and PXA-B can be Pentile. TM ) Arrangement form, or diamond (Diamond Pixel) TM ) It may have the form of an array.

[0112] Furthermore, the areas of the light-emitting regions PXA-R, PXA-G, and PXA-B may differ from each other. For example, in one embodiment, the area of ​​the green light-emitting region PXA-G may be smaller than the area of ​​the blue light-emitting region PXA-B, but the embodiment is not limited to this.

[0113] Figures 3 to 6 below are schematic cross-sectional views showing a light-emitting element according to one embodiment. The light-emitting element ED according to one embodiment may include a first electrode EL1, a second electrode EL2 facing the first electrode EL1, and at least one functional layer disposed between the first electrode EL1 and the second electrode EL2. The light-emitting element ED according to one embodiment may include a condensed polycyclic compound according to one embodiment, described later, in at least one functional layer.

[0114] The light-emitting element ED may include a hole transport region HTR, an emissive layer EML, and an electron transport region ETR, which are sequentially stacked as at least one functional layer. In other words, one embodiment of the light-emitting element ED may include a first electrode EL1, a hole transport region HTR, an emissive layer EML, an electron transport region ETR, and a second electrode EL2, which are sequentially stacked.

[0115] Figure 4 shows a cross-sectional view of an embodiment of a light-emitting element ED, compared to Figure 3, in which the hole transport region HTR includes a hole injection layer HIL and a hole transport layer HTL, and the electron transport region ETR includes an electron injection layer EIL and an electron transport layer ETL. Figure 5 also shows a cross-sectional view of an embodiment of a light-emitting element ED, compared to Figure 3, in which the hole transport region HTR includes a hole injection layer HIL, a hole transport layer HTL and an electron blocking layer EBL, and the electron transport region ETR includes an electron injection layer EIL, an electron transport layer ETL and a hole blocking layer HBL. Figure 6 shows a cross-sectional view of an embodiment of a light-emitting element ED, compared to Figure 4, in which a capping layer CPL is placed on the second electrode EL2.

[0116] In one embodiment, the light-emitting element ED may contain the condensed polycyclic compound of the embodiment described later in at least one functional layer included in the light-emitting element ED. In the light-emitting element ED of the embodiment, the condensed polycyclic compound of the embodiment may be included in at least one of the hole transport region HTR, the light-emitting layer EML, and the electron transport region ETR. For example, in the light-emitting element ED of the embodiment, the light-emitting layer EML may contain the condensed polycyclic compound of the embodiment.

[0117] The first electrode EL1 is conductive. The first electrode EL1 may consist of a metallic material, a metallic alloy, or a conductive compound. The first electrode EL1 may be an anode or a cathode, however, the examples are not limited to these. The first electrode EL1 may also be a pixel electrode. The first electrode EL1 may be a transmissive electrode, a semitransmissive electrode, or a reflective electrode. The first electrode EL1 may contain at least one selected from Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF, Mo, Ti, W, In, Sn, and Zn, two or more compounds selected from these, a mixture of two or more selected from these, or oxides thereof.

[0118] If the first electrode EL1 is a transmissive electrode, it may contain transparent metal oxides, such as ITO (indium tin oxide), IZO (indium zinc oxide), ZnO (zinc oxide), ITZO (indium tin zinc oxide), etc. If the first electrode EL1 is a semi-transmissive or reflective electrode, it may contain Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF / Ca (a layered structure of LiF and Ca), LiF / Al (a layered structure of LiF and Al), Mo, Ti, W, or compounds or mixtures thereof (for example, a mixture of Ag and Mg). Alternatively, the first electrode EL1 may have a multi-layer structure including a reflective or semi-transmissive film made of the aforementioned materials, and a transparent conductive film made of ITO, IZO, ZnO, ITZO, etc. For example, the first electrode EL1 may have a three-layer structure of ITO / Ag / ITO, but is not limited to this. Furthermore, the examples are not limited to this, and the first electrode EL1 may include the above-mentioned metal material, a combination of two or more metal materials selected from the above-mentioned metal materials, or an oxide of the above-mentioned metal material. The thickness of the first electrode EL1 may be about 700 Å to about 10000 Å. For example, the thickness of the first electrode EL1 may be about 1000 Å to about 3000 Å.

[0119] A hole transport region (HTR) may be provided on the first electrode EL1. The hole transport region (HTR) may include at least one of a hole injection layer (HIL), a hole transport layer (HTL), a hole buffer layer or luminescence auxiliary layer (not shown), and an electron blocking layer (EBL). The thickness of the hole transport region (HTR) may be, for example, about 50 Å to about 15,000 Å.

[0120] The hole transport region (HTR) may have a single layer made of a single material, a single layer made of multiple different materials, or a multilayer structure having multiple layers made of multiple different materials.

[0121] For example, the hole transport region HTR may have a single-layer structure of a hole injection layer HIL or a hole transport layer HTL, or it may have a single-layer structure consisting of a hole injection material and a hole transport material. Furthermore, the hole transport region HTR may have a single-layer structure consisting of multiple different materials, or it may have a structure of a hole injection layer HIL / hole transport layer HTL, a hole injection layer HIL / hole transport layer HTL / buffer layer (not shown), a hole injection layer HIL / buffer layer (not shown), a hole transport layer HTL / buffer layer (not shown), or a hole injection layer HIL / hole transport layer HTL / hole blocking layer EBL stacked in order from the first electrode EL1, but the examples are not limited to these.

[0122] Hole transport regions (HTRs) can be formed using a variety of methods, including vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) method, inkjet printing, laser printing, and laser-induced thermal imaging (LITI).

[0123] The hole transport region (HTR) may contain a compound represented by the following chemical formula H-1.

[0124] <Chemical formula H-1> JPEG2026076767000027.jpg83129

[0125] In chemical formula H-1, L1 and L2 can each independently be directly bonded, substituted, or unsubstituted arylene groups with 6 to 30 ring-forming carbon atoms, or substituted or unsubstituted heteroarylene groups with 2 to 30 ring-forming carbon atoms. a and b can each independently be integers between 0 and 10. On the other hand, if a or b is an integer of 2 or more, then multiple L1 and L2 can each independently be substituted or unsubstituted arylene groups with 6 to 30 ring-forming carbon atoms, or substituted or unsubstituted heteroarylene groups with 2 to 30 ring-forming carbon atoms.

[0126] In chemical formula H-1, Ar1 to Ar2 can each independently be a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms. Furthermore, in chemical formula H-1, Ar3 can be a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms.

[0127] The compound represented by the chemical formula H-1 may be a monoamine compound. Alternatively, the compound represented by the chemical formula H-1 may be a diamine compound in which at least one of Ar1 to Ar3 contains an amine group as a substituent. Alternatively, the compound represented by the chemical formula H-1 may be a carbazole compound in which at least one of Ar1 to Ar2 contains a substituted or unsubstituted carbazole group, or a cafluorene compound in which at least one of Ar1 to Ar2 contains a substituted or unsubstituted fluorene group.

[0128] A compound represented by the chemical formula H-1 can be represented by any one of the compounds in compound group H below. However, the compounds listed in compound group H below are illustrative examples, and the compound represented by the chemical formula H-1 is not limited to those shown in compound group H below.

[0129] <Compound group H> JPEG2026076767000028.jpg90170

[0130] JPEG2026076767000029.jpg47170

[0131] JPEG2026076767000030.jpg47140

[0132] JPEG2026076767000031.jpg103157

[0133] The hole transport region (HTR) is used for phthalocyanine compounds such as copper phthalocyanine, and 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), m-MTDATA(4,4',4”-[tris(3-methylphenyl)phenylamino)triphenylamino], TDATA(4,4',4”-tris(N,N-diphenylamino)triphenylamine), 2-TNATA(4,4',4”-tris[N(2-naphthyl)-N-phenylamino]-triphenylamine), PEDOT / PSS(poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate), PANI / DBSA(polyaniline / dodecylbenzenesulfonic acid), PANI / CSA(polyaniline / camphorsulfonic acid), PANI / PSS((polyaniline) / poly(4-styrenesulfonate)), NPB It may contain (N,N'-di(naphthalene-1-yl)-N,N'-diphenyl-benzidine), polyether ketone containing triphenylamine (TPAPEK), 4-isopropyl-4'-methyldiphenyliodonium tetrakis(pentafluorophenyl) borate, HATCN (dipyradino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonnitrile), etc.

[0134] The hole transport region HTR may include, for example, carbazole derivatives such as N-phenylcarbazole and polyvinylcarbazole, fluorene derivatives, triphenylamine derivatives such as TPD (N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1-biphenyl]-4,4'-diamine) and TCTA (4,4',4"-tris(N-carbazolyl)triphenylamine), NPB (N,N'-di(naphthalene-1-yl)-N,N'-diphenyl-benzidine), TAPC (4,4'-cyclohexylidenebis[N,N-bis(4-methylphenyl)benzeneamine]), HMTPD (4,4'-bis[N,N'-(3-tolyl)amino]-3,3'-dimethylbiphenyl)), and mCP (1,3-bis(N-carbazolyl)benzene).

[0135] Furthermore, the hole transport region HTR may include CzSi(9-(4-tert-butylphenyl)-3,6-bis(triphenylsilyl)-9H-(carbazole), CCP(9-phenyl-9H-3,9'-bicarbazole), or mDCP(1,3-bis(1,8-dimethyl-9H-carbazole-9-yl)benzene).

[0136] In one embodiment, the hole transport region (HTR) may include any one of the compounds in the second group of compounds described below.

[0137] The hole transport region (HTR) may include at least one of the hole injection layer (HIL), hole transport layer (HTL), and electron blocking layer (EBL) as the hole transport region compound described above.

[0138] The thickness of the hole transport region (HTR) can be approximately 100 Å to approximately 10,000 Å, for example, approximately 100 Å to approximately 5,000 Å. If the hole transport region (HTR) includes a hole injection layer (HIL), the thickness of the hole injection layer (HIL) can be, for example, approximately 30 Å to approximately 1,000 Å. If the hole transport region (HTR) includes a hole transport layer (HTL), the thickness of the hole transport layer (HTL) can be approximately 30 Å to approximately 1,000 Å. For example, if the hole transport region (HTR) includes a hole blocking layer (EBL), the thickness of the hole blocking layer (EBL) can be, for example, approximately 10 Å to approximately 1,000 Å. If the thicknesses of the hole transport region (HTR), hole injection layer (HIL), hole transport layer (HTL), and electron blocking layer (EBL) satisfy the above-described ranges, satisfactory hole transport characteristics can be obtained without a substantial increase in the driving voltage.

[0139] The hole transport region (HTR) may further contain charge-generating materials in addition to the materials described above to improve conductivity. The charge-generating material may be uniformly or non-uniformly dispersed within the hole transport region (HTR). The charge-generating material may be, for example, a p-dopant. The p-dopant may contain, but is not limited to, at least one of metal halide compounds, quinone derivatives, metal oxides, and cyano group-containing compounds. For example, p-dopants include metal halide compounds such as CuI and RBI, quinone derivatives such as TCNQ (tetracyanoquinodimethane) and F4-TCNQ (2,3,5,6-tetrafluoro-7,7',8,8-tetracyanoquinodimethane), metal oxides such as tungsten oxide and molybdenum oxide, and cyano group-containing compounds such as HATCN (dipyradino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonnitrile) and NDP9 (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 to these.

[0140] As described above, the hole transport region (HTR) may further include at least one of a buffer layer (not shown) and an electron blocking layer (EBL) in addition to the hole transport layer (HTL) and the hole injection layer (HIL). The buffer layer (not shown) can increase the light emission efficiency by compensating for the resonance distance due to the wavelength of light emitted from the light emission layer (EML). The material included in the buffer layer (not shown) may be a material that can be included in the hole transport region (HTR). The electron blocking layer (EBL) may be a layer that prevents the injection of electrons from the electron transport region (ETR) into the hole transport region (HTR).

[0141] The luminescent layer (EML) may be provided on top of the hole transport region (HTR). The luminescent layer (EML) may have a thickness of, for example, about 100 Å to about 1000 Å, or about 100 Å to about 300 Å. The luminescent layer (EML) may have a multilayer structure consisting of a single layer made of a single material, a single layer made of multiple different materials, or multiple layers made of multiple different materials.

[0142] In one embodiment, the light-emitting element ED may contain a condensed polycyclic compound represented by the following chemical formula 1 in at least one functional layer disposed between the first electrode EL1 and the second electrode EL2. In the light-emitting element ED of one embodiment, the light-emitting layer EML may contain the condensed polycyclic compound of one embodiment. In one embodiment, the light-emitting layer EML may contain the condensed polycyclic compound of one embodiment as a dopant. The condensed polycyclic compound of one embodiment may be a dopant material for the light-emitting layer EML. On the other hand, in this specification, the condensed polycyclic compound of one embodiment may be referred to as the first compound.

[0143] The condensed polycyclic compound of one embodiment comprises first and second condensed cores, each containing a boron-centered condensed skeleton. In the condensed polycyclic compound of one embodiment, the first and second condensed cores may be linked to each other by sharing one benzene ring and one nitrogen atom. The condensed polycyclic compound of the present invention, having a structure in which the first and second condensed cores are linked by a specified linking structure, can exhibit a small full width at half maximum and Stokes-shift characteristics, and can exhibit high luminescence quantum efficiency.

[0144] In one embodiment, the first condensed core may have a structure in which six rings are condensed around a first boron atom, a first nitrogen atom, a first heteroatom, and a second heteroatom. The first condensed core may form six condensed rings by linking three substituted or unsubstituted benzene rings with the first boron atom, the first nitrogen atom, the first heteroatom, and the second heteroatom. More specifically, in the three benzene rings included in the first condensed core, the three benzene rings may be linked around the first boron atom, the first and second benzene rings may be linked via the first nitrogen atom, the first and third benzene rings may be linked via the first heteroatom, and the second and third benzene rings may be linked via the second heteroatom. In the first condensed core, the first benzene ring and the first nitrogen atom may be shared with the second condensed core described above. The first condensed core and the second condensed core may be linked to each other by sharing the first benzene ring and the first nitrogen atom.

[0145] In one embodiment, the second condensed core may have a structure in which five rings are condensed around a second boron atom, a first nitrogen atom, and a third heteroatom. The second condensed core may form five condensed rings by linking substituted or unsubstituted benzene rings with a second boron atom, a first nitrogen atom, and a third heteroatom. More specifically, in the three benzene rings included in the second condensed core, the three benzene rings are linked around a second boron atom, the first and fourth benzene rings are linked via a first nitrogen atom, and the first and fifth benzene rings are linked via a third heteroatom. Between the fourth and fifth benzene rings, there may be no heteroatoms other than the boron atom. In the second condensed core, the first benzene ring and the first nitrogen atom may be shared with the first condensed core described above.

[0146] In one example of a condensed polycyclic compound, the first condensation core may be represented by the following structure S1, and the second condensation core may be represented by the following structure S2. On the other hand, for the sake of explanation, substituents linked to the benzene ring are omitted in each of the following structures S1 and S2.

[0147] JPEG2026076767000032.jpg72142

[0148] In structure S1, A may correspond to the first nitrogen atom described above, and B1 may correspond to the first benzene ring described above. In structure S2, A is It could be JPEG2026076767000033.jpg3540, X 2 and X 3 Each is independent It could be JPEG2026076767000034.jpg27121.

[0149] In structure S2, A corresponds to the first nitrogen atom described above, and B1 can correspond to the first benzene ring described above. In structure S2, A is It could be JPEG2026076767000035.jpg4243, X 1 teeth It could be JPEG2026076767000036.jpg28123.

[0150] In structures S1 and S2, Ar 1 This can be a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms.

[0151] In structures S1 and S2, JPEG2026076767000037.jpg1640 represents the part connected to the aforementioned structure S1, JPEG2026076767000038.jpg3244 represents the portion connected to structure S2.

[0152] In the polycyclic condensed compound of one embodiment, the first condensed core represented by structure S1 and the second condensed core represented by structure S2 can be linked to each other by sharing the first benzene ring B1 and the first nitrogen atom N. In the polycyclic condensed compound of one embodiment, the first condensed core and the second condensed core can be linked to each other by sharing the first benzene ring B1 and the first nitrogen atom N to form a 10-ring condensed ring as shown in structure S3 below.

[0153] JPEG2026076767000039.jpg145112

[0154] In structure S3, the B1 ring corresponds to the first benzene ring described above, and the nitrogen atom N can correspond to the first nitrogen atom described above.

[0155] In structure S3, X 1 ~X 3 The same provisions described above can be applied to structures S1 and S2.

[0156] Thermally activated delayed fluorescence materials with a boron-centered condensed ring skeleton are attracting attention as organic light-emitting devices due to their narrow full width at half maximum (FMAX) and high emission quantum yield. Diboron-based thermally activated delayed fluorescence materials are expected to improve device lifetime and efficiency due to their high absorbance and fast reverse intersystem crossing. However, condensed skeletons based on two boron atoms generally have larger FMAX and Stokes shifts compared to single-boron-based condensed skeletons due to the effects of structural relaxation in the excited and ground states, making them still insufficient for use as materials in high-performance displays.

[0157] The condensed polycyclic compound of the present invention has a structure in which a first condensed core and a second condensed core are linked by a specified linkage structure, thereby exhibiting a small full width at half maximum and Stokes shift characteristics, and can exhibit high luminescence quantum efficiency.

[0158] In one embodiment of the condensed polycyclic compound, the first condensed core has a structure in which three benzene rings are linked around a boron atom, and in particular, in the three benzene rings, the ortho carbons relative to the boron atom are all linked via heteroatoms such as N, O, and S to form a condensed ring. As a result, structural relaxation of the excited and ground states of the molecule is suppressed, and it can exhibit a smaller full width at half maximum and Stokes shift characteristics compared to conventional condensed skeletons.

[0159] Furthermore, the condensed polycyclic compound of one embodiment can weaken molecular symmetry by including a structure in which a second condensed core is bonded to a first condensed core, thereby exhibiting improved photoluminescence quantum yield (PLQY) characteristics. Generally, thermally activated delayed fluorescence materials containing a condensed ring skeleton centered on boron have the problem of a significant decrease in photoluminescence quantum yield due to molecular symmetry issues. For example, when the ortho carbon atoms of the boron atoms, as in the first condensed core, both form a condensed ring skeleton, the molecular symmetry increases and the emission quantum efficiency may decrease. However, the condensed polycyclic compound of the present invention has a structure in which a second condensed core is bonded to a first condensed core by a specific linkage structure, thereby suppressing molecular symmetry while maintaining excellent characteristics of full width at half maximum and Stokes shift derived from the first condensed core, and exhibiting improved photoluminescence quantum yield characteristics.

[0160] The condensed polycyclic compound of one embodiment can be represented by the following chemical formula 1.

[0161] <Chemical formula 1> JPEG2026076767000040.jpg166155

[0162] The polycyclic condensed compound of one embodiment, represented by chemical formula 1, comprises a first and a second condensed core, each containing a condensed skeleton centered on a boron atom. In the polycyclic condensed compound of one embodiment, the first and second condensed cores may be linked to each other by sharing one benzene ring and one nitrogen atom.

[0163] On the one hand, in the present specification, in Chemical Formula 1, R 15 The benzene ring substituted with the substituent represented by corresponds to the first benzene ring, and R 9 to R 11 The benzene ring substituted with the substituent represented by corresponds to the second benzene ring, and R 12 to R 14 The benzene ring substituted with the substituent represented by corresponds to the third benzene ring, and R 5 to R 8 The benzene ring substituted with the substituent represented by corresponds to the fourth benzene ring, and R 1 to R 4 The benzene ring substituted with the substituent represented by may correspond to the fifth benzene ring. In Chemical Formula 1, the nitrogen atom N may correspond to the first nitrogen atom described above. <0OO0845>

[0164] In Chemical Formula 1, X 1 to X 3 are each independently O, S, or NAr 1 For example, X 1 to X 3 may each independently be O or NAr 1 In Chemical Formula 1, Ar1 is a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms. In one embodiment, Ar1 may be a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms. For example, Ar1 may be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted quater-phenyl group, or a substituted or unsubstituted quinkphenyl group.

[0166] In Chemical Formula 1, R 1 to R 15 ​​​​is, independently of each other, a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms. For example, R 1 to R 15 are each independently a hydrogen atom, a deuterium atom, a cyano group, a substituted or unsubstituted diphenylamine group, a substituted or unsubstituted methyl group, a substituted or unsubstituted isopropyl group, a substituted or unsubstituted t-butyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted quarterphenyl group, a substituted or unsubstituted quinquephenyl group, or a substituted or unsubstituted carbazole group.

[0167] On the other hand, in the condensed polycyclic compound of one embodiment, when R 13 is a diphenylamine group or a carbazole group, R 10 is a hydrogen atom or is excluded when it contains a diphenylamine group. That is, in the condensed polycyclic compound of one embodiment, when R 13 is a diphenylamine group or a carbazole group, when R 10 is a hydrogen atom, and when R 10 contains a diphenylamine group as a substituent, both cases can be excluded.

[0168] The condensed polycyclic compound represented by Chemical Formula 1 according to one embodiment includes a structure in which at least one hydrogen atom is substituted with a deuterium atom.

[0169] In one embodiment, the first compound represented by Chemical Formula 1 can be represented by any one of the following Chemical Formulas 2-1 to 2-4.

[0170] <Chemical Formula 2-1> JPEG2026076767000041.jpg108154

[0171] <Chemical Formula 2-2> JPEG2026076767000042.jpg108137

[0172] <Chemical formula 2-3> JPEG2026076767000043.jpg107120

[0173] <Chemical formula 2-4> JPEG2026076767000044.jpg161158

[0174] X 2a ~X 3a Each of these can independently be either O or S.

[0175] In chemical formulas 2-1 to 2-3, R 21 ~R 24 Each of these can independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms. For example, R 21 ~R 24 Each of these can independently be a hydrogen atom, a substituted or unsubstituted methyl group, a substituted or unsubstituted t-butyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, or a substituted or unsubstituted carbazole group.

[0176] In chemical formulas 2-1 to 2-3, n1 to n4 are each independent integers between 0 and 5. If each of n1 to n4 in chemical formulas 2-1 to 2-3 is 0, then the condensed polycyclic compound of one example is R 21 ~R 24 It is possible that none of them are substituted. In chemical formulas 2-1 to 2-3, n1 to n4 are each 5, and R 21 ~R 24If each of them is a hydrogen atom, it may be the same as the case where n1 to n4 are each 0 in Chemical Formulas 2-1 to 2-3. If each of n1 to n4 is an integer of 2 or more, a plurality of R 21 to R 24 are each the same, or at least one of the plurality of R 21 to R 24 can be different.

[0177] In Chemical Formulas 2-1 to 2-4, X 1 , and R 1 to R 15 may be applied the same content as described in the above Chemical Formula 1.

[0178] In one embodiment, the first compound represented by Chemical Formula 1 may be represented by any one of the following Chemical Formulas 3-1 to 3-4.

[0179] <Chemical Formula 3-1> JPEG2026076767000045.jpg104154

[0180] <Chemical Formula 3-2> JPEG2026076767000046.jpg108137

[0181] <Chemical Formula 3-3> JPEG2026076767000047.jpg105122

[0182] <Chemical Formula 3-4> JPEG​​​​​​​​​​​​If R is a diphenylamine group or a carbazole group, 10 R can be an unsubstituted alkyl group having 1 to 20 carbon atoms, or an unsubstituted aryl group having 6 to 20 ring-forming carbon atoms. For example, in chemical formula 3-2, 13 If R is a diphenylamine group or a carbazole group, 10 This can be an unsubstituted t-butyl group, an unsubstituted phenyl group, or an unsubstituted biphenyl group.

[0185] In chemical formulas 3-1 to 3-4, X 1 , and R 1 ~R 15 The same principles described for chemical formula 1 above may apply to this.

[0186] The first compound represented by chemical formula 1 can be represented by any one of the following chemical formulas 4-1 to 4-4.

[0187] <Chemical formula 4-1> JPEG2026076767000049.jpg106141

[0188] <Chemical formula 4-2> JPEG2026076767000050.jpg106141

[0189] <Chemical formula 4-3> JPEG2026076767000051.jpg105124

[0190] <Chemical formula 4-4> JPEG2026076767000052.jpg156150

[0191] In chemical formulas 4-2 to 4-4, X 1a ~X 2a Each of these can independently be either O or S.

[0192] In chemical formulas 4-1 to 4-3, R 31 ~R 34Each of these can independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms. For example, R 31 ~R 34 Each of these can independently be a hydrogen atom, a substituted or unsubstituted methyl group, a substituted or unsubstituted t-butyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, or a substituted or unsubstituted carbazole group.

[0193] In chemical formulas 4-1 to 4-4, n11 to n14 are each independent integers between 0 and 5. If each of n11 to n14 in chemical formulas 4-1 to 4-4 is 0, then the condensed polycyclic compound of one example is R 31 ~R 34 Each of them may be unsubstituted. In chemical formulas 4-1 to 4-4, n11 to n14 are each 5, and R 31 ~R 34 If each of them is a hydrogen atom, it may be the same as when each of n11 to n14 is 0 in chemical formulas 4-1 to 4-4. If each of n11 to n14 is an integer of 2 or more, multiple R values ​​are provided. 31 ~R 34 Each of them is the same, or multiple R 31 ~R 34 At least one of them may be different.

[0194] In chemical formulas 4-1 to 4-4, X 3 , and R 1 ~R 15 The same principles described for chemical formula 1 above may apply to this.

[0195] In one embodiment of the condensed polycyclic compound, at least one of the first to third heteroatoms may be a second nitrogen atom substituted with a first substituent. In one embodiment, the first substituent may include a first benzene substructure and a first subsubstituent substituted with carbon at a specific position of the first benzene substructure. For example, the first substituent may include a first benzene substructure (moiety) linked to the second nitrogen atom, and a structure in which the first subsubstituent is linked to one ortho position relative to the second nitrogen atom. Alternatively, the first substituent may include a first benzene substructure linked to the second nitrogen atom, and a structure in which the first subsubstituent is linked to two ortho positions relative to the second nitrogen atom. The first subsubstituent may be a substituted or unsubstituted phenyl group. On the other hand, in this specification, the second nitrogen atom substituted with a first substituent may be represented by the following chemical formula 6-1 or chemical formula 6-2.

[0196] In one embodiment, the condensed polycyclic compound can effectively maintain the trigonal planar structure of the boron atom due to the steric hindrance effect of the first substituent. In the case of the boron atom, the empty p orbital gives it electron-deficient properties, which can lead to bonding with other nucleiogens and a change to a tetrahedral structure, which can cause device degradation. According to the present invention, the condensed polycyclic compound in one embodiment contains a first substituent with a steric hindrance structure, which effectively protects the empty p orbital of the boron atom, thus preventing degradation due to structural deformation.

[0197] In addition, in one embodiment, the condensed polycyclic compound can control the formation of excimers or exciplexes by suppressing intermolecular interactions through the introduction of the first substituent, thereby increasing the luminescence efficiency. Further, the condensed polycyclic compound of one embodiment represented by Chemical Formula 1 has the effect of increasing the intermolecular distance and reducing Dexter energy transfer by including the first substituent. Dexter energy transfer is a phenomenon in which triplet excitons between molecules move. If the intermolecular distance is short, it increases, which is a factor increasing the quenching phenomenon due to an increase in the triplet concentration. According to the present invention, in one embodiment, the condensed polycyclic compound has a structure with a large steric hindrance, increasing the distance between adjacent molecules and suppressing Dexter energy transfer, thereby suppressing the deterioration of the lifetime caused by an increase in the triplet concentration. Therefore, if the condensed polycyclic compound of one embodiment is applied to the emission layer EML of the light-emitting device ED, it is possible not only to increase the luminescence efficiency but also to improve the device lifetime.

[0198] In one embodiment, the first compound represented by Chemical Formula 1 may be represented by the following Chemical Formula 5.

[0199] <Chemical Formula 5> JPEG2026076767000053.jpg160146

[0200] In Chemical Formula 5, X 1b , X 2b and X 3b At least one of them is represented by the following Chemical Formula 6-1 or Chemical Formula 6-2, and the rest may each independently be O, S, or NAr 2 respectively.

[0201] In Chemical Formula 5, Ar 2 may be a substituted or unsubstituted aryl group having 6 or more and 30 or less ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 or more and 30 or less ring-forming carbon atoms. In one embodiment, Ar 2This can be a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms. For example, it can be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted terphenyl group.

[0202] In chemical formula 5, R 1 ~R 15 The same principles described in Chemical Formula 1 above may apply to this.

[0203] <Chemical formula 6-1> JPEG2026076767000054.jpg78111

[0204] <Chemical formula 6-2> JPEG2026076767000055.jpg64117

[0205] In chemical formulas 6-1 to 6-2, R 41 ~R 45 Each of these can independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms. For example, R 41 ~R 45 Each of these can independently be a hydrogen atom, a substituted or unsubstituted t-butyl group, or a substituted or unsubstituted phenyl group.

[0206] In chemical formulas 6-1 to 6-2, n21, n23, and n25 are each independent integers between 0 and 5. If n21, n23, and n25 are each 0 in chemical formulas 6-1 to 6-2, then the condensed polycyclic compound of one example is R 41 , R 43 , and R 45 It is possible that none of them are substituted. In chemical formulas 6-1 to 6-2, n21, n23, and n25 are each 0, and R 41 , R 43 , and R45 If each of them is a hydrogen atom, then in chemical formulas 6-1 and 6-2, n21, n23, and n25 may be the same as when each is 0. If each of n21, n23, and n25 is an integer of 2 or more, then multiple R values ​​are provided. 41 , R 43 , and R 45 Each of them is either the same or multiple Rs. 41 , R 43 , and R 45 At least one of them may be different.

[0207] In chemical formula 6-1, n22 is an integer between 0 and 4. In chemical formula 6-1, if n22 is 0, then the condensed polycyclic compound of one example is R 42 It may not be substituted. In chemical formula 6-1, n22 is 4, R 42 If all of them are hydrogen atoms, it can be the same as when n22 is 0 in chemical formula 6-1. If n22 is an integer of 2 or more, multiple R values ​​are provided. 42 They are all the same, or multiple R 42 At least one of them may be different.

[0208] In chemical formula 6-2, n24 is an integer between 0 and 3. In chemical formula 6-2, if n24 is 0, the condensed polycyclic compound of one example is R 44 It may not be substituted. In chemical formula 6-2, n24 is 3, R 44 If all of them are hydrogen atoms, it can be the same as when n24 is 0 in chemical formula 6-2. If n24 is an integer of 2 or more, multiple R values ​​are provided. 44 They are all the same, or multiple R 44 At least one of them may be different.

[0209] In chemical formulas 6-1 and 6-2, JPEG2026076767000056.jpg2145 This is the position where it is connected to the chemical formula 5.

[0210] In one example, the condensed polycyclic compound of the example represented by chemical formula 1 may contain at least one deuterium atom as a substituent. The condensed polycyclic compound of the example represented by chemical formula 1 may include a structure in which at least one hydrogen atom is substituted with a deuterium atom.

[0211] The condensed polycyclic compound in one embodiment may be any one of the compounds shown in the first compound group below. At least one functional layer included in the light-emitting element ED of one embodiment may contain at least one condensed polycyclic compound from the compounds shown in the first compound group. The light-emitting element ED of one embodiment may contain at least one condensed polycyclic compound from the compounds shown in the first compound group in the light-emitting layer EML.

[0212] <First compound group> JPEG2026076767000057.jpg115158

[0213] JPEG2026076767000058.jpg131161

[0214] JPEG2026076767000059.jpg127151

[0215] JPEG2026076767000060.jpg124152

[0216] JPEG2026076767000061.jpg128149

[0217] JPEG2026076767000062.jpg117158

[0218] JPEG2026076767000063.jpg128160

[0219] JPEG2026076767000064.jpg124166

[0220] JPEG2026076767000065.jpg120146

[0221] JPEG2026076767000066.jpg127145

[0222] JPEG2026076767000067.jpg127156

[0223] JPEG2026076767000068.jpg123161

[0224] JPEG2026076767000069.jpg125143

[0225] JPEG2026076767000070.jpg126152

[0226] JPEG2026076767000071.jpg130134

[0227] JPEG2026076767000072.jpg123143

[0228] JPEG2026076767000073.jpg116148

[0229] JPEG2026076767000074.jpg124154

[0230] JPEG2026076767000075.jpg126154

[0231] JPEG2026076767000076.jpg124153

[0232] JPEG2026076767000077.jpg121134

[0233] JPEG2026076767000078.jpg120135

[0234] JPEG2026076767000079.jpg130139

[0235] JPEG2026076767000080.jpg118132

[0236] JPEG2026076767000081.jpg128144

[0237] JPEG2026076767000082.jpg123137

[0238] JPEG2026076767000083.jpg56145

[0239] The emission spectrum of the condensed polycyclic compound of one embodiment represented by chemical formula 1 has a full width at half maximum (FMAX) of 10 nm to 50 nm, preferably 20 nm to 40 nm. Having the emission spectrum of the first dopant of one embodiment represented by chemical formula 1 within this FMAX range can improve luminous efficiency when applied to a device. Furthermore, when used as a material for a blue light-emitting element, it can improve the device lifespan.

[0240] In one embodiment, the condensed polycyclic compound represented by chemical formula 1 can be a thermally activated delayed fluorescence material. Furthermore, the condensed polycyclic compound represented by chemical formula 1 has a difference (ΔE) between the lowest triplet excitation energy level (T1 level) and the lowest singlet excitation energy level (S1 level). ST ) may be a thermally activated delayed fluorescent dopant having a ΔE of 0.6 eV or less. The condensed polycyclic compound of one example represented by chemical formula 1 has a difference (ΔE) between the lowest triplet excitation energy level (T1 level) and the lowest singlet excitation energy level (S1 level). ST ) may be a thermally activated delayed fluorescent dopant with a voltage of 0.2 eV or less. However, the examples are not limited to this.

[0241] The condensed polycyclic compound of one embodiment of the present invention, represented by chemical formula 1, has a structure in which a second condensed core is bonded to a first condensed core by a specific linking structure. This structure suppresses molecular symmetry while maintaining excellent properties of full width at half maximum and Stokes shift, and can exhibit improved photoluminescence quantum yield characteristics. As a result, the condensed polycyclic compound of one embodiment of the present invention can exhibit improved thermally activated delayed fluorescence characteristics.

[0242] The condensed polycyclic compound of one embodiment, represented by chemical formula 1, may be a light-emitting material having a emission center wavelength in the wavelength range of 430 nm to 490 nm. For example, the condensed polycyclic compound of one embodiment, represented by chemical formula 1, may be a blue thermally activated delayed fluorescence (TADF) dopant. However, the examples are not limited to this, and when the condensed polycyclic compound of one embodiment is used as a light-emitting material, the first dopant may be used as a dopant substance that emits light in various wavelength ranges, such as a red light-emitting dopant or a green light-emitting dopant.

[0243] In one embodiment of the light-emitting element ED, the light-emitting layer EML may emit delayed fluorescence. For example, the light-emitting layer EML may emit thermally activated delayed fluorescence (TADF).

[0244] Furthermore, the light-emitting layer (EML) of the light-emitting element (ED) may emit blue light. For example, the light-emitting layer (EML) of the organic electroluminescent element (ED) in one embodiment may emit blue light in the wavelength range of 490 nm or less. However, the embodiment is not limited to this, and the light-emitting layer (EML) may emit green light or red light.

[0245] On the other hand, the condensed polycyclic compound of one embodiment may be included in the light-emitting layer EML. The condensed polycyclic compound of one embodiment may be included in the light-emitting layer EML as a dopant material. The condensed polycyclic compound of one embodiment may be a thermally activated delayed fluorescence light-emitting material. The condensed polycyclic compound of one embodiment may be used as a thermally activated delayed fluorescence dopant. For example, in the light-emitting element ED of one embodiment, the light-emitting layer EML may contain at least one of the condensed polycyclic compounds shown in the first compound group described above as a thermally activated delayed fluorescence dopant. However, the uses of the condensed polycyclic compound of one embodiment are not limited to this.

[0246] In one embodiment, the light-emitting layer EML may contain multiple compounds. The light-emitting layer EML of one embodiment may contain a condensed polycyclic compound represented by chemical formula 1, i.e., a first compound, and in addition, may contain at least one of the following: a second compound represented by chemical formula HT-1, a third compound represented by chemical formula ET-1, and a fourth compound represented by chemical formula D-1.

[0247] In one embodiment, the light-emitting layer EML contains a first compound represented by chemical formula 1, and may also contain at least one of a second compound represented by the following chemical formula HT-1, and a third compound represented by the following chemical formula ET-1.

[0248] In one embodiment, the light-emitting layer EML may contain a second compound represented by the following chemical formula HT-1. In one embodiment, the second compound may be used as a hole-transporting host material for the light-emitting layer EML. <Chemical formula HT-1> JPEG2026076767000084.jpg106131

[0249] In the chemical formula HT-1, M1 to M8 are each independently either N or CR. 51 It is possible. For example, M1 through M8 are all CR 51 It is possible. Alternatively, one of M1 through M8 is N, and the rest are CR. 51 It is possible.

[0250] L1 can be a direct linkage, a substituted or unsubstituted arylene group with 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroarylene group with 2 to 30 ring-forming carbon atoms. For example, L a These may be directly bonded, substituted or unsubstituted phenylene groups, substituted or unsubstituted divalent biphenyl groups, substituted or unsubstituted divalent carbazole groups, etc., but the examples are not limited to these.

[0251] In the chemical formula HT-1, Y a This is direct bonding, CR 52 R 53 , or SiR 54 R 55 It is possible. In other words, the two benzene rings linked to the nitrogen atom of chemical formula HT-1 are directly bonded. This could mean that they are concatenated via JPEG2026076767000085.jpg40127. In the chemical formula HT-1, Y a If the bond is direct, the substituent represented by the chemical formula HT-1 may include a carbazole substructure.

[0252] In the chemical formula HT-1, Ar a This can be a substituted or unsubstituted aryl group with 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group with 2 to 30 ring-forming carbon atoms. For example, Ar a The group may be a substituted or unsubstituted carbazole group, a substituted or unsubstituted dibenzofuran group, a substituted or unsubstituted dibenzothiophene group, or a substituted or unsubstituted biphenyl group, but the examples are not limited to these.

[0253] In the chemical formula HT-1, R 51 ~R 55Each of these can independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted thio group, a substituted or unsubstituted oxy group, a substituted or unsubstituted amine group, a substituted or unsubstituted boron group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 ring-forming carbon atoms. 51 ~R 55 Each of these can bond with an adjacent group to form a ring. For example, R 51 ~R 55 Each of these can independently be a hydrogen atom or a deuterium atom. 51 ~R 55 These can each be independently an unsubstituted methyl group or an unsubstituted phenyl group.

[0254] In one embodiment, the second compound represented by the chemical formula HT-1 may be any one of the compounds shown in the second compound group below. The light-emitting layer EML may contain at least one of the compounds shown in the second compound group below as a hole-transporting host material.

[0255] <Second compound group> JPEG2026076767000086.jpg47170

[0256] JPEG2026076767000087.jpg35170

[0257] JPEG2026076767000088.jpg42170

[0258] JPEG2026076767000089.jpg39170

[0259] JPEG2026076767000090.jpg37170

[0260] JPEG2026076767000091.jpg31170

[0261] JPEG2026076767000092.jpg32170

[0262] JPEG2026076767000093.jpg32170

[0263] JPEG2026076767000094.jpg32170

[0264] JPEG2026076767000095.jpg32170

[0265] JPEG2026076767000096.jpg33170

[0266] JPEG2026076767000097.jpg33170

[0267] JPEG2026076767000098.jpg38170

[0268] JPEG2026076767000099.jpg35170

[0269] JPEG2026076767000100.jpg38170

[0270] JPEG2026076767000101.jpg40170

[0271] In the specific compounds presented in the second group of compounds, "D" represents a deuterium atom, and "Ph" can be an unsubstituted phenyl group.

[0272] In one embodiment, the luminescent layer EML may contain a third compound represented by the following chemical formula ET-1. For example, the third compound can be used as an electron-transporting host material for the luminescent layer EML.

[0273] <Chemical formula ET-1> JPEG2026076767000102.jpg48170

[0274] In the chemical formula ET-1, Z a ~Z c At least one of them is N, and the rest are CR 56 For example, Z a ~Z c One of them is N, and the remaining two are CR independently. 56 This is possible. In this case, the third compound represented by chemical formula ET-1 may include a pyridine substructure. Or, Z a ~Z c Two of them are N, and the remaining one is CR 56 This is possible. In this case, the third compound represented by the chemical formula ET-1 may include a pyrimidine substructure. For example, Z a ~Z c All of these can be N. In this case, the third compound represented by the chemical formula ET-1 may contain a triazine substructure.

[0275] In chemical formula ET-1, R 56 This can be a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 ring-forming carbon atoms.

[0276] In chemical formula ET-1, b1 to b3 can each be an independent integer between 0 and 10.

[0277] In chemical formula ET-1, Ar b ~Ar d Each of these can independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms. For example, Ar b ~Ar d This can be a substituted or unsubstituted phenyl group, or a substituted or unsubstituted carbazole group.

[0278] In the chemical formula ET-1, L b ~L d Each of these can independently be a directly bonded, substituted, or unsubstituted arylene group with 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroarylene group with 2 to 30 ring-forming carbon atoms. On the other hand, if b1 to b3 are integers of 2 or more, L b ~L d Each of these can independently be a substituted or unsubstituted arylene group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring-forming carbon atoms.

[0279] In one embodiment, the third compound may be represented by any one of the compounds in the third compound group described below. The light-emitting element ED of one embodiment may contain any one of the compounds in the third compound group described below.

[0280] <3rd compound group> JPEG2026076767000103.jpg136170

[0281] JPEG2026076767000104.jpg142170

[0282] JPEG2026076767000105.jpg140170

[0283] JPEG2026076767000106.jpg137170

[0284] JPEG2026076767000107.jpg160170

[0285] JPEG2026076767000108.jpg156170

[0286] JPEG2026076767000109.jpg135170

[0287] JPEG2026076767000110.jpg40170

[0288] JPEG2026076767000111.jpg107170

[0289] In the specific compounds presented in the third group of compounds, "D" represents a deuterium atom, and "Ph" represents an unsubstituted phenyl group.

[0290] The EML luminescent layer contains a second compound and a third compound, and the second and third compounds can form an exciplex. In the EML luminescent layer, an exciplex can be formed by a hole-transporting host and an electron-transporting host. In this case, the triplet energy of the exciplex formed by the hole-transporting host and the electron-transporting host may correspond to the difference between the LUMO (Lowest Unoccupied Molecular Orbital) energy level of the electron-transporting host and the HOMO (Highest Occupied Molecular Orbital) energy level of the hole-transporting host.

[0291] For example, the absolute value of the triplet energy (T1) of an exciplex formed by a hole-transporting host and an electron-transporting host may be between 2.4 eV and 3.0 eV. Furthermore, the triplet energy of the exciplex may be smaller than the energy gap of each host material. An exciplex may have a triplet energy of 3.0 eV or less, which is the energy gap between the hole-transporting host and the electron-transporting host.

[0292] In one embodiment, the light-emitting layer (EML) may contain a fourth compound in addition to the first to third compounds described above. The fourth compound may be used as a phosphorescent sensitizer for the light-emitting layer (EML). Energy can be transferred from the fourth compound to the first compound, causing light emission.

[0293] For example, the light-emitting layer EML may contain Pt (platinum) as the central metal atom and an organometallic complex containing a ligand bound to the central metal atom as the fourth compound. In one embodiment of the light-emitting element ED, the light-emitting layer EML may contain a compound represented by the following chemical formula D-1 as the fourth compound.

[0294] <Chemical formula D-1> JPEG2026076767000112.jpg87170

[0295] In chemical formula D-1, Q1 to Q4 can each be independently either C or N.

[0296] In chemical formula D-1, Cy1 to Cy4 are each independently a substituted or unsubstituted hydrocarbon ring with 5 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heterocycle with 2 to 30 ring-forming carbon atoms.

[0297] X 11 ~X 14 Each can be directly connected or JPEG2026076767000113.jpg1450 It is possible. For example, X 11 ~X 14 One of the following is JPEG2026076767000114.jpg1450 The remaining ones can be direct bonds.

[0298] In chemical formula D-1, L 11 ~L 13 Each is independently and directly connected. JPEG2026076767000115.jpg29156 It may be a substituted or unsubstituted divalent alkyl group having 1 to 20 ring-forming carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring-forming carbon atoms. L 11 ~L 13 In, JPEG2026076767000116.jpg1640 represents the region connected to Cy1 through Cy4.

[0299] In chemical formula D-1, b11 to b13 can each be independently 0 or 1. If b11 is 0, Cy1 and Cy2 may not be linked to each other. If b12 is 0, Cy2 and Cy3 may not be linked to each other. If b13 is 0, Cy3 and Cy4 may not be linked to each other.

[0300] In chemical formula D-1, R 61 ~R 66 Each of these can independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted thio group, a substituted or unsubstituted oxy group, a substituted or unsubstituted amine group, a substituted or unsubstituted boron group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 ring-forming carbon atoms. 61 ~R 66 Each can bond with an adjacent group to form a ring. 61 ~R 66 Each of these can independently be a substituted or unsubstituted methyl group, or a substituted or unsubstituted t-butyl group.

[0301] In chemical formula D-1, d1 to d4 are each independent integers between 0 and 4. If each of d1 to d4 in chemical formula D-1 is 0, then the fourth compound is R 61 ~R 66 It is possible that they are not each substituted. Each of d1 through d4 is 4, R 61 ~R 66 If each of them is a hydrogen atom, it can be the same as when each of d1 to d4 is 0. If each of d1 to d4 is an integer of 2 or more, multiple R values ​​are provided. 61 ~R64 Each of them is either the same or multiple Rs. 61 ~R 64 At least one of them may be different.

[0302] In chemical formula D-1, Cy1 to Cy4 can each independently be a substituted or unsubstituted hydrocarbon ring, or a substituted or unsubstituted heterocycle, represented by any one of the following C-1 to C-5.

[0303] JPEG2026076767000117.jpg110170

[0304] In C-1 to C-4, P1 is JPEG2026076767000118.jpg6170 or CR 74 Therefore, P2 is JPEG2026076767000119.jpg6170 or NR 81 Therefore, P3 is JPEG2026076767000120.jpg6170 or NR 82 Therefore, P4 is JPEG2026076767000121.jpg6170 or CR 88 Therefore, P6 is JPEG2026076767000122.jpg6170 or CR 90 It is possible. R 71 and R 90 Each of these groups may independently be a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms forming a ring, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms forming a ring by bonding with adjacent groups.

[0305] Furthermore, in C-1 to C-4, JPEG2026076767000123.jpg3244 is the part connected to the central metal atom, Pt. JPEG2026076767000124.jpg2145 is a combination of adjacent ring groups (Cy1 to Cy4) or linkers (L 11 ~L 13 This could be the part that is connected to ).

[0306] In one embodiment, the luminescent layer EML comprises a first compound, which is a condensed polycyclic compound, and at least one of the second to fourth compounds. For example, the luminescent layer EML may include the first compound, the second compound, and the third compound. In the luminescent layer EML, the second and third compounds form an exciplex, and energy can be transferred from the exciplex to the first compound, causing luminescence.

[0307] Furthermore, the light-emitting layer EML may contain a first compound, a second compound, a third compound, and a fourth compound. In the light-emitting layer EML, the second and third compounds form an exciplex, and energy can be transferred from the exciplex to the fourth and first compounds, causing light emission. In one embodiment, the fourth chemical formula may be a sensitizer. In the light-emitting element ED of one embodiment, the fourth compound contained in the light-emitting layer EML may function as a sensitizer and play a role in transferring energy from the host to the first compound, which is a light-emitting dopant. In other words, the fourth compound, which acts as an auxiliary dopant, can accelerate the transfer of energy to the first compound, which is a light-emitting dopant, and increase the light emission ratio of the first compound. Therefore, the light-emitting layer EML of one embodiment may have improved luminescence efficiency. Also, if the transfer of energy to the first compound is increased, the excitons formed in the light-emitting layer EML will emit light quickly without accumulating inside the light-emitting layer EML, thus reducing the degradation of the element. Therefore, the lifespan of the light-emitting element ED of one embodiment is increased.

[0308] In one embodiment, the light-emitting element (ED) may contain all of the first, second, third, and fourth compounds, and the light-emitting layer (EML) may contain a combination of two host materials and two dopant materials. In the light-emitting element (ED) of one embodiment, the light-emitting layer (EML) can achieve excellent luminescence efficiency by simultaneously containing two different host compounds, the second and third compounds, the first compound which emits delayed fluorescence, and the fourth compound which contains an organometallic complex.

[0309] In one embodiment, the fourth compound represented by chemical formula D-1 may be represented by at least one of the compounds shown in the fourth compound group below. The luminescent layer EML may contain at least one of the compounds shown in the fourth compound group below as a sensitizer substance.

[0310] <4th compound group> JPEG2026076767000125.jpg186170

[0311] JPEG2026076767000126.jpg159170

[0312] JPEG2026076767000127.jpg171170

[0313] JPEG2026076767000128.jpg171170

[0314] In the specific compounds presented in the fourth group of compounds, "D" represents a deuterium atom.

[0315] On the other hand, the light-emitting element ED of one embodiment may include multiple light-emitting layers. The multiple light-emitting layers are provided by sequentially stacking them, and for example, the light-emitting element ED including multiple light-emitting layers may emit white light. The light-emitting element including multiple light-emitting layers may be a tandem structure light-emitting element. If the light-emitting element ED includes multiple light-emitting layers, at least one light-emitting layer EML may contain the first compound represented by the chemical formula of one embodiment. Furthermore, if the light-emitting element ED includes multiple light-emitting layers, at least one light-emitting layer EML may contain any of the first compound, second compound, third compound, and fourth compound as described above.

[0316] In one embodiment of the light-emitting element ED, if the light-emitting layer EML contains all three compounds as described above, the content of the first compound may be 0.1 wt% or more and 5 wt% or less based on the total weight of the first, second, and third compounds. However, it is not limited to this. If the content of the first compound satisfies the above-mentioned ratio, the energy transfer from the second and third compounds to the first compound will increase, thereby increasing the luminous efficiency and the device lifetime.

[0317] In the luminescent layer EML, the content of the second and third compounds may be the remainder after excluding the weight of the first compound as described above. For example, in the luminescent layer EML, the content of the second and third compounds may be 65 wt% to 95 wt% based on the total weight of the first, second, and third compounds.

[0318] In terms of the total weight of the second and third compounds, the weight ratio of the second compound to the third compound may be approximately 3:7 to 7:3.

[0319] If the content of the second and third compounds satisfies the above-mentioned ratio, the charge balance characteristics within the EML (electroluminescent layer) will be improved, which may increase the luminous efficiency and device lifetime. If the content of the second and third compounds deviates from the above-mentioned ratio, the charge balance within the EML will be disrupted, the luminous efficiency will decrease, and the device may easily deteriorate.

[0320] When the luminescent layer EML contains the fourth compound, the content of the fourth compound in the luminescent layer EML may be approximately 4 wt% to 30 wt%, based on the total weight of the first, second, third, and fourth compounds. However, it is not limited to this. If the content of the fourth compound satisfies the above-mentioned content, the energy transfer from the host to the first compound, which is a luminescent dopant, increases, improving the effective ratio, and thereby improving the luminescence efficiency of the luminescent layer EML. If the first, second, third, and fourth compounds contained in the luminescent layer EML satisfy the above-mentioned content ratio range, excellent luminescence efficiency and long lifetime can be achieved.

[0321] In one embodiment of the light-emitting element ED, the light-emitting layer EML may contain an anthracene derivative, a pyrene derivative, a fluorantene derivative, a chrysene derivative, a dihydrobenzanthracene derivative, or a triphenylene derivative. More specifically, the light-emitting layer EML may contain an anthracene derivative or a pyrene derivative.

[0322] In the light-emitting element ED of one embodiment shown in Figures 3 to 6, the light-emitting layer EML further includes known hosts and dopants in addition to the hosts and dopants described above. For example, the light-emitting layer 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.

[0323] <Chemical formula E-1> JPEG2026076767000129.jpg53170

[0324] In chemical formula E-1, R 31 ~R 40Each of these groups may independently be a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted silyl group, a substituted or unsubstituted thio group, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms, a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heteroaryl group having 2 to 30 carbon atoms, or a group that forms a ring by bonding with adjacent groups. On the other hand, R 31 ~R 40 These groups can bond with adjacent groups to form saturated hydrocarbon rings, unsaturated hydrocarbon rings, saturated heterocycles, or unsaturated heterocycles.

[0325] In chemical formula E-1, c and d can each be independent integers between 0 and 5, inclusive.

[0326] Chemical formula E-1 may be represented by any one of the following compounds E1 through E19.

[0327] JPEG2026076767000130.jpg36170

[0328] JPEG2026076767000131.jpg43170

[0329] JPEG2026076767000132.jpg36170

[0330] JPEG2026076767000133.jpg38170

[0331] JPEG2026076767000134.jpg54170

[0332] JPEG2026076767000135.jpg61170

[0333] JPEG2026076767000136.jpg61170

[0334] In one embodiment, the light-emitting layer EML may contain a compound represented by the following chemical formula E-2a or chemical formula E-2b. The compound represented by the following chemical formula E-2a or chemical formula E-2b can be used as a phosphorescent host material.

[0335] <Chemical formula E-2a> JPEG2026076767000137.jpg48170

[0336] In chemical formula E-2a, a is an integer between 0 and 10, and L a This can be a directly bonded, substituted, or unsubstituted arylene group with 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroarylene group with 2 to 30 ring-forming carbon atoms. On the other hand, if a is an integer of 2 or more, L a Each of these can independently be a substituted or unsubstituted arylene group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring-forming carbon atoms.

[0337] In chemical formula E-2a, A1 to A5 are each independently N or CR. i It is possible. R a ~R i Each of these groups may independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted amine group, a substituted or unsubstituted thio group, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heteroaryl group having 2 to 30 carbon atoms, or may bond with adjacent groups to form a ring. Ra to Ri may bond with adjacent groups to form a hydrocarbon ring or a heterocycle containing N, O, S, etc. as ring-forming atoms.

[0338] On the other hand, in chemical formula E-2a, two or three selected from A1 to A5 are N and the rest are CR. i It is possible.

[0339] <Chemical formula E-2b> JPEG2026076767000138.jpg17170

[0340] In the chemical formula E-2b, Cbz1 and Cbz2 can each be independently a carbazole group or a carbazole group substituted with an aryl group having 6 to 30 ring-forming carbon atoms. b This can be a directly bonded, substituted, or unsubstituted arylene group with 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroarylene group with 2 to 30 ring-forming carbon atoms. On the other hand, b is an integer between 0 and 10, and if b is an integer of 2 or more, multiple L b Each of these can independently be a substituted or unsubstituted arylene group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring-forming carbon atoms.

[0341] The compound represented by chemical formula E-2a or E-2b may be represented by any one of the compounds in compound group E-2 below. However, the compounds listed in compound group E-2 below are illustrative examples, and the compound represented by chemical formula E-2a or E-2b is not limited to those shown in compound group E-2 below.

[0342] <Compound group E-2> JPEG2026076767000139.jpg84170

[0343] JPEG2026076767000140.jpg104170

[0344] JPEG2026076767000141.jpg90170

[0345] JPEG2026076767000142.jpg96170

[0346] The luminescent layer (EML) may further include common materials known in the relevant art as host materials. For example, the luminescent layer EML uses BCPDS (bis(4-(9H-carbazole-9-yl)phenyl)diphenylsilane), POPCPA ((4-(1-(4-(diphenylamino)phenyl)cyclohexyl)phenyl)diphenylphosphine oxide), DPEPO (bis[2-(diphenylphosphino)phenyl]ether oxide), CBP (4,4'-bis(N-carbazolyl)-1,1'-biphenyl), mCP (1,3-bis(carbazole-9-yl)benzene), PPF (2,8-bis(diphenylphosphoryl)dibenzo[b,d]furan), TCTA (4,4',4”-tris(carbazole-9-yl)-triphenylamine), and TPBi (1,3,5-tris(1-phenyl-1H-benzo[d]imidazole-2-yl)ben It may contain at least one of the following: However, it is not limited to these, and for example, Alq3 (tris(8-hydroxyquinolino)aluminum), ADN (9,10-di(naphthalene-2-yl)anthracene), TBADN (3-tert-butyl-9,10-di(naphtho-2-yl)anthracene), DSA (distylyl arylene), CDBP (4,4'-bis(9-carbazolyl)-2,2'-dimethyl-biphenyl), MADN (2-methyl-9,10-bis(naphthalene-2-yl)anthracene), CP1 (hexaphenylcyclotriphosphazene), UGH2 (1,4-bis(triphenylsilyl)benzene), DPSiO3 (hexaphenylcyclotrisiloxane), DPSiO4 (octaphenylcyclotetrasiloxane), etc. can be used as host materials.

[0347] The luminescent layer EML may contain a compound represented by the following chemical formula Ma. This compound represented by the following chemical formula Ma can be used as a phosphorescent dopant material.

[0348] <Chemical formula Ma> JPEG2026076767000143.jpg50170

[0349] In the chemical formula Ma, Y1 to Y4 and Z1 to Z4 are each independently CR1 or N, and R1 to R4 are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted amine group, a substituted or unsubstituted thio group, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heteroaryl group having 2 to 30 carbon atoms, or a group that forms a ring by bonding with an adjacent group. In the chemical formula Ma, m is 0 or 1, and n is 2 or 3. In the chemical formula Ma, if m is 0, then n is 3, and if m is 1, then n is 2.

[0350] Compounds represented by the chemical formula Ma can be used as phosphorescent dopants.

[0351] A compound represented by the chemical formula Ma may be any one of the compounds in the following group of compounds M-a1 to M-a25. However, the following compounds M-a1 to M-a25 are illustrative examples, and the compound represented by the chemical formula Ma is not limited to those represented by the following compounds M-a1 to M-a25.

[0352] JPEG2026076767000144.jpg56170

[0353] JPEG2026076767000145.jpg45170

[0354] JPEG2026076767000146.jpg49170

[0355] JPEG2026076767000147.jpg136170

[0356] JPEG2026076767000148.jpg72170

[0357] The luminescent layer EML may contain a compound represented by any one of the following chemical formulas: Fa to Fc. These compounds can be used as fluorescent dopant materials.

[0358] <Chemical formula Fa> JPEG2026076767000149.jpg45170

[0359] In the aforementioned chemical formula Fa, R a ~R j The two selected from among them are independent of each other. This may be replaced by JPEG2026076767000150.jpg7170. a ~R j Of these, The remaining unsubstituted elements in JPEG2026076767000151.jpg7170 can each independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms. In JPEG2026076767000152.jpg7170, Ar1 and Ar2 can each be independently a substituted or unsubstituted aryl group with 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group with 2 to 30 ring-forming carbon atoms. For example, at least one of Ar1 and Ar2 may be a heteroaryl group containing O or S as a ring-forming atom.

[0360] <Chemical formula Fb> JPEG2026076767000153.jpg35170

[0361] In the chemical formula Fb, R a and R bEach of these groups may independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted ring-forming alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heteroaryl group having 2 to 30 carbon atoms, or a group that forms a ring by bonding with an adjacent group. Ar1 and Ar4 may independently be a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heteroaryl group having 2 to 30 carbon atoms.

[0362] In chemical formula Fb, U and V can each independently be a substituted or unsubstituted hydrocarbon ring having 5 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heterocycle having 2 to 30 ring-forming carbon atoms. At least one of Ar1 to Ar4 may be a heteroaryl group containing O or S as a ring-forming atom.

[0363] In the chemical formula Fb, the number of rings represented by U and V can be 0 or 1 independently. For example, in the chemical formula Fb, if the number of U or V is 1, the part represented by U or V constitutes a single-ring condensed ring, and if the number of U or V is 0, it means that the ring represented by U or V does not exist. More specifically, if the number of U is 0 and the number of V is 1, or if the number of U is 1 and the number of V is 0, the condensed ring with a fluorene core in the chemical formula Fb can be a four-ring cyclic compound. Also, if the number of both U and V is 0, the condensed ring with a fluorene core in the chemical formula Fb can be a three-ring cyclic compound. Furthermore, if the number of U and V is 1, the condensed ring with a fluorene core in the chemical formula Fb can be a five-ring cyclic compound.

[0364] <Chemical formula Fc> JPEG2026076767000154.jpg53170

[0365] In the chemical formula Fc, A1 and A2 are independently O, S, Se, or NR, respectively. m And Rm R1 to R 11 Each of these groups is independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted amine group, a substituted or unsubstituted boryl group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thio group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, or is bonded to an adjacent group to form a ring.

[0366] In the chemical formula Fc, A1 and A2 can independently bond to substituents on adjacent rings to form fused rings. For example, A1 and A2 can independently form NR m Therefore, A1 may bond with R4 or R5 to form a ring. Also, A2 may bond with R7 or R8 to form a ring.

[0367] In one embodiment, the luminescent layer EML is a known dopant material, and is a styryl derivative (e.g., 1,4-bis[2-(3-N-ethylcarbazol)vinyl]benzene (BCzVB), 4-(di-p-tolylamino)-4'-[(di-p-tolylamino)styryl]stilbene (DPAVB), N-(4-((E)-2-(6-((E)-4-(diphenylamino)styryl)naphthalen-2-yl)vinyl)phenyl)- The following may further be included: N-phenylbenzeneamine (N-BDAVBi), 4,4'-bis[2-(4-(N,N-diphenylamino)phenyl)vinyl]biphenyl (DPAVBi), perylene and its derivatives (e.g., 2,5,8,11-tetra-t-butylperylene (TBP)), pyrene and its derivatives (e.g., 1,1-dipylene, 1,4-dipyrenylbenzene, 1,4-bis(N,N-diphenylamino)pyrene).

[0368] The luminescent layer EML may further contain known phosphorescent dopant materials. For example, metal complexes containing iridium (Ir), platinum (Pt), osmium (Os), gold (Au), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), or thulium (Tm) may be used as phosphorescent dopants. Specifically, Flrpic (iridium(III)bis(4,6-difluorophenylpyridinate-N,C2')picolinate), Fir6 (bis(2,4-difluorophenylpyridinate)-tetrakis(1-pyrazolyl)borate-iridium(III)) or PtOEP (platinum-octaethylporphyrin) can be used as phosphorescent dopants. However, the examples are not limited to these.

[0369] The light-emitting layer may include quantum dots.

[0370] In this specification, "quantum dot" refers to a crystal of a semiconductor compound. Quantum dots can emit light of various emission wavelengths depending on the size of the crystal. Quantum dots may also emit light of various emission wavelengths by adjusting the elemental ratio within the quantum dot compound.

[0371] The diameter of the quantum dot may be, for example, about 1 nm to 10 nm.

[0372] The quantum dots can be synthesized by wet chemical processes, organometallic chemical vapor deposition processes, molecular beam epitaxy processes, or similar processes.

[0373] The aforementioned wet chemical process involves mixing an organic solvent with a precursor material and then growing quantum dot particle crystals. During crystal growth, the organic solvent acts as a dispersant naturally coordinated to the surface of the quantum dot crystals, thereby regulating the crystal growth. Therefore, the wet chemical process is simpler and less expensive than vapor deposition methods such as metal-organic chemical vapor deposition (MOCVD) or molecular arrow beam epitaxy (MBE), allowing for control of quantum dot particle growth.

[0374] The light-emitting layer of the present invention may include a quantum dot material. The core of the quantum dot may be selected from group II-VI compounds, group III-V compounds, group III-VI compounds, group I-III-V compounds, group IV-VI compounds, group IV elements, group IV compounds, and combinations thereof.

[0375] Group II-VI compounds are binary compounds selected from the group consisting of CdSe, CdTe, CdS, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, MgSe, MgS, and mixtures thereof, including CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, CdZnSe, CdZnTe, CdHgS, CdHgSe, CdHgT The group may be selected from the group consisting of e, HgZnS, HeZnSe, HeZnTe, MgZnSe, MgZnS, and mixtures thereof, and from the group consisting of quaternary compounds selected from the group consisting of HgZnTeS, CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe, HgZnSTe, and mixtures thereof. On the other hand, the group II-VI semiconductor compounds may further contain group I metals and / or group IV elements. The group I-II-VI compounds may be selected from CuSnS or CuZnS, and the group II-IV-VI compounds may be selected from ZnSnS, etc. The group I-II-IV-VI compounds may be selected from the group consisting of Cu2ZnSnS2, Cu2ZnSnS4, Cu2ZnSnSe4, Ag2ZnSnS2, and mixtures thereof.

[0376] Group III-VI compounds may include dielemental compounds such as In2S3 and In2Se3, trielemental compounds such as InGaS3 and InGaSe3, or any combination thereof.

[0377] Group I-III-VI compounds may be selected from the group consisting of AgInS, AgInS2, CuInS, CuInS2, AgGaS2, CuGaS2, CuGaO2, AgGaO2, AgAlO2, and mixtures thereof, or from quaternary compounds such as AgInGaS2 and CuInGaS2.

[0378] Group III-V compounds can be selected from the group consisting of binary compounds selected from the group consisting of GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, InSb, and mixtures thereof; ternary compounds selected from the group consisting of 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 the group consisting of GaAlNP, GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNP, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs, InAlPSb, and mixtures thereof. On the other hand, Group III-V compounds may further contain Group II metals. For example, InZnP could be selected as a III-II-V group compound.

[0379] Group IV-VI compounds may be selected from the group consisting of binary compounds selected from the group consisting of SnS, SnSe, SnTe, PbS, PbSe, PbTe, and mixtures thereof; ternary compounds selected from the group consisting of SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, SnPbTe, and mixtures thereof; and quaternary compounds selected from the group consisting of SnPbSSe, SnPbSeTe, SnPbSTe, and mixtures thereof.

[0380] Examples of the aforementioned II-IV-V semiconductor compounds may be ternary compounds selected from the group consisting of ZnSnP, ZnSnP2, ZnSnAs2, ZnGeP2, ZnGeAs2, CdSnP2, and CdGeP2, and mixtures thereof.

[0381] Group IV elements may be selected from the group consisting of Si, Ge, and mixtures thereof. Group IV compounds may be binary compounds selected from the group consisting of SiC, SiGe, and mixtures thereof.

[0382] Each element in a multi-element compound, such as the binary, ternary, and quaternary compounds, can exist within the particles at uniform or non-uniform concentrations. In other words, the chemical formula represents the types of elements contained in the compound, and the elemental ratios within the compound can vary. For example, AgInGaS2 is AgIn x Ga 1-x This could mean S² (where X is a real number between 0 and 1).

[0383] In this case, binary, ternary, or quaternary compounds may exist within the particle at a uniform concentration, or they may be separated into states with partially different concentration distributions and exist within the same particle. Furthermore, a core / shell structure may exist in which one quantum dot surrounds another. In a core / shell structure, there may be a concentration gradient where the concentration of elements present in the shell decreases as you move towards the core.

[0384] In some embodiments, quantum dots may have a core-shell structure comprising a core containing the nanocrystals described above, and a shell surrounding the core. The shell of the quantum dot may act 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. Examples of the shell of the quantum dot include metallic or nonmetallic oxides, semiconductor compounds, or combinations thereof.

[0385] For example, the metal or nonmetal oxides include binary compounds such as SiO2, Al2O3, TiO2, ZnO, MnO, Mn2O3, Mn3O4, CuO, FeO, Fe2O3, Fe3O4, CoO, Co3O4, and NiO, or ternary compounds such as MgAl2O4, CoFe2O4, NiFe2O4, and CoMn2O4, but the present invention is not limited to these.

[0386] Furthermore, examples of the semiconductor compound include CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnSeS, ZnTeS, GaAs, GaP, GaSb, HgS, HgSe, HgTe, InAs, InP, InGaP, InSb, AlAs, AlP, AlSb, and the like, but the present invention is not limited to these.

[0387] Quantum dots have an emission wavelength spectrum with a full width at half maximum (FWHM) of approximately 45 nm or less, preferably approximately 40 nm or less, and more preferably approximately 30 nm or less, and can improve color purity and color reproducibility within this range. Furthermore, since the light emitted through such quantum dots is emitted in all directions, the optical viewing angle can be improved.

[0388] Furthermore, the form of the quantum dots is not limited to those commonly used in this field, but more specifically, spherical, pyramidal, multi-arm, or cubic nanoparticles, nanotubes, nanowires, nanofibers, or nanoplate-like particles may be used.

[0389] The energy band gap can be adjusted by controlling the size of the quantum dots or the elemental ratio within the quantum dot compound, thereby enabling the emission of light across a wide range of wavelengths in the quantum dot light-emitting layer. Therefore, by using quantum dots of different sizes or with different elemental ratios within the quantum dot compound, a light-emitting device emitting light of various wavelengths can be realized. Specifically, the size of the quantum dots and the elemental ratio within the quantum dot compound can be selected to emit red, green, and / or blue light. Furthermore, the quantum dots can be configured to emit white light by combining light of various colors.

[0390] In one embodiment of the light-emitting element ED shown in Figures 3 to 6, the electron transport region ETR is provided on the light-emitting layer EML. The electron transport region ETR includes, but is not limited to, at least one of the hole blocking layer HBL, electron transport layer ETL, and electron injection layer EIL.

[0391] The electron transport region (ETR) may have a single layer made of a single material, a single layer made of multiple different materials, or a multilayer structure having multiple layers made of multiple different materials.

[0392] For example, the electron transport region (ETR) may have a single-layer structure of an electron injection layer (EIL) or electron transport layer (ETL), or a single-layer structure consisting of an electron injection material and an electron transport material. Furthermore, the electron transport region (ETR) may have a single-layer structure consisting of multiple different materials, or it may have an electron transport layer (ETL) / electron injection layer (EIL) or hole blocking layer (HBL) / electron transport layer (ETL) / electron injection layer (EIL) structure stacked sequentially from the light-emitting layer (EML), but is not limited to these. The thickness of the electron transport region (ETR) may be, for example, about 1000 Å to about 1500 Å.

[0393] Electron transport regions (ETRs) can be formed using a variety of methods, such as vacuum deposition, spin coating, casting, LB, inkjet printing, laser printing, and laser thermal transfer (LITI).

[0394] The electron transport region (ETR) may contain compounds represented by the following chemical formula ET-2.

[0395] <Chemical formula ET-2> JPEG2026076767000155.jpg51169

[0396] In the chemical formula ET-2, at least one of X1 to X3 is N, and the rest are CR. a That is. R aAr1 to Ar3 are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms.

[0397] In chemical formula ET-2, a to c can each be an integer between 0 and 10, independently of each other. In chemical formula ET-2, L1 and L3 can each be an arylene group with 6 to 30 directly bonded, substituted, or unsubstituted ring-forming carbon atoms, or a heteroarylene group with 2 to 30 substituted ring-forming carbon atoms, independently of each other. On the other hand, if a to c are integers of 2 or more, then multiple L1 and L3 can each be an arylene group with 6 to 30 substituted ring-forming carbon atoms, independently of each other, or a heteroarylene group with 2 to 30 substituted ring-forming carbon atoms, independently of each other.

[0398] The electron transport region (ETR) may include anthracene compounds. However, it is not limited to these; examples of electron transport region ETRs include Alq3(tris(8-hydroxyquinolinato)aluminum), 1,3,5-tri[(3-pyridyl)phen-3-yl]benzene, 2,4,6-tris(3'-pyridine-3-yl)biphenyl-3-yl)-1,3,5-triazine, and 2-(4-(N-phenylbenzimidazole-1-yl)phenyl)-9,10-dinaphthylant Spiral, TPBi (1,3,5-tri(1-phenyl-1H-benzo[d]imidazole-2-yl)benzene), BCP (2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline), Bphen (4,7-diphenyl-1,10-phenanthroline), TAZ (3-(4-biphenylyl)-4-phenyl-5-terto-butylphenyl-1,2,4-triazole), NTAZ (4 -(naphthalene-1-yl)-3,5-diphenyl-4H-1,2,4-triazole), tBu-PBD(2-(4-biphenylyl)-5-(4-tertobutylphenyl)-1,3,4-oxadiazole), BAlq(bis(2-methyl-8-quinolinolato-N1,O8)-(1,1'-biphenyl-4-olato)aluminum), Bebq2(beryllium bis(benzoquinoline-10-ol) It may contain, ADN (9,10-di(naphthalene-2-yl)anthracene), BmPyPhB (1,3-bis[3,5-di(pyridine-3-yl)phenyl]benzene), CNNPTRZ (4'-(4-(4-(4,6-diphenyl-1,3,5-triazine-2-yl)phenyl)naphthalene-1-yl)-[1,1'-biphenyl]-4-carbonitrile), and mixtures thereof.

[0399] In one embodiment, the electron injection region (ETR) may contain any one of the compounds from the third group of compounds listed below.

[0400] The electron transport region (ETR) may contain at least one of the following compounds ET1 to ET36.

[0401] JPEG2026076767000156.jpg100170

[0402] JPEG2026076767000157.jpg55170

[0403] JPEG2026076767000158.jpg114170

[0404] JPEG2026076767000159.jpg125170

[0405] JPEG2026076767000160.jpg96170

[0406] JPEG2026076767000161.jpg105170

[0407] JPEG2026076767000162.jpg50170

[0408] Furthermore, the electron transport region (ETR) may include metal halides such as LiF, NaCl, CsF, RbCl, RbI, CuI, and KI, lanthanum group metals such as Yb, or co-deposited materials of the aforementioned metal halides and lanthanum group metals. For example, the electron transport region (ETR) may include KI:Yb, RbI:Yb, LiF:Yb, etc., as co-deposited materials. On the other hand, the electron transport region (ETR) may also be metal oxides such as Li2O and BaO, or Liq (8-hydroxylithium quinolate), but the examples are not limited to these. The electron transport region (ETR) may also consist of a mixture of an electron transport material and an insulating organometallic salt. The organometallic salt may be a material with an energy band gap of about 4 eV or more. For more details, organometallic salts may include metal acetate, metal benzoate, metal acetoacetate, metal acetylacetonate, or metal stearate.

[0409] The electron transport region (ETR) may, but is not limited to, further contain at least one of the following materials: BCP (2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline), TSPO1 (diphenyl(4-(triphenylsilyl)phenyl)phosphine oxide), and Bphen (4,7-diphenyl-1,10-phenanthroline).

[0410] The electron transport region ETR may contain the aforementioned electron transport region compound in at least one of the electron injection layer EIL, electron transport layer ETL, and hole blocking layer HBL.

[0411] If the electron transport region (ETR) includes an electron transport layer (ETL), the thickness of the electron transport layer (ETL) may be approximately 100 Å to approximately 1000 Å, for example, approximately 150 Å to approximately 500 Å. If the thickness of the electron transport layer (HTL) satisfies the above-mentioned range, satisfactory electron transport characteristics can be obtained without a substantial increase in the driving voltage. If the electron transport region (ETR) includes an electron injection layer (EIL), the thickness of the electron injection layer (EIL) may be approximately 1 Å to approximately 100 Å, or approximately 3 Å to approximately 90 Å. If the thickness of the electron injection layer (EIL) satisfies the above-mentioned range, satisfactory electron injection characteristics can be obtained without a substantial increase in the driving voltage.

[0412] The second electrode EL2 is provided on the electron transport region ETR. The second electrode EL2 may be a common electrode. The second electrode EL2 may be a cathode or an anor rond, but the examples are not limited to these. For example, if the first electrode EL1 is an anode, the second electrode may be a cathode, and if the first electrode EL1 is a cathode, the second electrode EL2 may be an anode.

[0413] The second electrode EL2 can be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode. If the second electrode EL2 is a transmissive electrode, it can be made of a transparent metal oxide, such as ITO (indium tin oxide), IZO (indium zinc oxide), ZnO (zinc oxide), or ITZO (indium tin zinc oxide).

[0414] If the second electrode EL2 is a semi-transparent or reflective electrode, the second electrode EL2 may contain Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF / Ca, LiF / Al, Mo, Ti, Yb, W, or compounds or mixtures containing these (e.g., AgMg, AgYb, or MgYb). Alternatively, the second electrode EL2 may have a multi-layer structure including a reflective or semi-transparent film made of the above-mentioned material, and a transparent conductive film made of ITO, IZO, ZnO, ITZO, etc. For example, the second electrode EL2 may contain the above-mentioned metallic material, a combination of two or more metallic materials selected from the above-mentioned metallic materials, or an oxide of the above-mentioned metallic material.

[0415] Although not shown in the diagram, the second electrode EL2 can be connected to an auxiliary electrode. Connecting the second electrode EL2 to an auxiliary electrode reduces the resistance of the second electrode EL2.

[0416] On the other hand, a capping layer CPL may be further disposed on the second electrode EL2 of the light-emitting element ED in one embodiment. The capping layer CPL may include a multilayer or monolayer.

[0417] In one embodiment, the capping layer CPL may be an organic or inorganic layer. For example, if the capping layer CPL contains an inorganic substance, the inorganic substance may include alkali metal compounds such as LiF, alkaline earth compounds such as MgF2, SiON, SiNx, SiOy, etc.

[0418] For example, if the capping layer CPL contains organic matter, it may include α-NPD, NPB, TPD, m-MTDATA, Alq3, CuPc, TPD15 (N4,N4,N4',N4'-tetra(biphenyl-4-yl)biphenyl-4,4'-diamine), TCTA (4,4',4”-tris(carbazole-9-yl)triphenylamine), or epoxy resin, or acrylates such as methacrylate. However, the examples are not limited to these, and the capping layer CPL may contain at least one of the compounds P1 to P5 described below.

[0419] JPEG2026076767000163.jpg128170

[0420] JPEG2026076767000164.jpg81170

[0421] On the other hand, the refractive index of the capping layer CPL may be 1.6 or higher. More specifically, for light in the wavelength range of 550 nm to 660 nm, the refractive index of the capping layer CPL may be 1.6 or higher.

[0422] Figures 7 and 10 are cross-sectional views of a display device according to one embodiment. In the following description of the display device according to one embodiment, with reference to Figures 7 and 10, any content that overlaps with the content described in Figures 1 to 6 above will not be explained again, and the focus will be on the differences.

[0423] Referring to Figure 7, one embodiment of the display device DD-a may include a display panel DP including a display element layer DP-ED, an optical control layer CCL disposed on the display panel DP, and a color filter layer CFL. In the embodiment shown in Figure 7, the display panel DP includes a base layer BS, a circuit layer DP-CL provided on the base layer BS, and a display element layer DP-ED, and the display element layer DP-ED may include a light-emitting element ED.

[0424] The light-emitting element ED may include a first electrode EL1, a hole transport region HTR placed on the first electrode EL1, an emissive layer EML placed on the hole transport region HTR, an electron transport region ETR placed on the emissive layer EML, and a second electrode EL2 placed on the electron transport region ETR. On the other hand, the structure of the light-emitting element ED shown in Figure 7 can also be to which the structures of the light-emitting elements shown in Figures 3 to 6 described above are applied.

[0425] In the display device DD-a according to one embodiment, the light-emitting layer EML of the light-emitting element ED includes the condensed polycyclic compound of the embodiment described above.

[0426] Referring to Figure 7, the light-emitting layer EML may be located within an opening OH that is partitioned (defined) in the pixel delimiting (defining) film DPL. For example, the light-emitting layer EML provided to correspond to each light-emitting region PXA-R, PXA-G, and PXA-B, separated by the pixel delimiting (defining) film PDL, may emit light in the same wavelength range. In one embodiment of the display device DD-a, the light-emitting layer EML may emit blue light. On the other hand, contrary to the illustration, in one embodiment, the light-emitting layer EML may be provided as a common layer for the entire light-emitting regions PXA-R, PXA-G, and PXA-B.

[0427] The optical control layer (CCL) may be placed on top of the display panel (DP). The optical control layer (CCL) may contain photoconverters. These photoconverters may be quantum dots or phosphors, etc. The photoconverters may wavelength-convert the provided light and emit it. In other words, the optical control layer (CCL) may contain quantum dots or may be a layer containing phosphors.

[0428] 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 separated from each other.

[0429] Referring to Figure 7, a segmentation pattern BMP is provided between the optical control units CCP1, CCP2, and CCP3, which are separated from each other, but the embodiment is not limited to this. In Figure 7, it is shown that the segmentation pattern BMP does not overlap with the optical control units CCP1, CCP2, and CCP3, but the edges of the optical control units CCP1, CCP2, and CCP3 may overlap with the segmentation pattern BMP in at least part.

[0430] The optical control layer CCL may include a first optical control unit CCP1 containing a first quantum dot QD1 that converts the first color light provided by the light-emitting element ED into second color light, a second optical control unit CCP2 containing a second quantum dot QD2 that converts the first color light into third color light, and a third optical control unit CCP3 that transmits the first color light. In one embodiment, the first optical control unit CCP1 may provide red light, which is the second color light, and the second optical control unit CCP2 may provide green light, which is the third color light. The third optical control unit CCP3 may transmit and provide blue light, which is the first color light provided by the light-emitting element ED. For example, the first quantum dot QD1 may be a red quantum dot, and the second quantum dot QD2 may be a green quantum dot. The same provisions as described above may apply to quantum dots QD1 and QD2.

[0431] Furthermore, the optical control layer CCL may further include a scatterer SP. The first optical control unit CCP1 includes a first quantum dot QD1 and a scatterer SP, the second optical control unit CCP2 includes a second quantum dot QD2 and a scatterer SP, and the third optical control unit CCP3 may include a scatterer SP without a quantum dot.

[0432] The scatterer SP may be inorganic particles. For example, the scatterer SP may contain at least one of TiO2, ZnO, Al2O3, SiO2, and hollow silica. The scatterer SP may contain at least one of TiO2, ZnO, Al2O3, SiO2, and hollow silica, or it may be a mixture of two or more substances selected from TiO2, ZnO, Al2O3, SiO2, and hollow silica.

[0433] Each of the first optical control unit CCP1, the second optical control unit CCP2, and the third optical control unit CCP3 may include base resins BR1, BR2, and BR3 for dispersing quantum dots QD1 and QD2 and scatterers SP. In one embodiment, the first optical control unit CCP1 may include first quantum dots QD1 and scatterers SP dispersed in the first base resin BR1, the second optical control unit CCP2 may include second quantum dots QD2 and scatterers SP dispersed in the second base resin BR2, and the third optical control unit CCP1 may include scatterers SP dispersed in the third base resin BR3.

[0434] The base resins BR1, BR2, and BR3 are the medium in which the quantum points QD1, QD2 and the scatterer SP are dispersed, and can consist of various resin compositions generally referred to as binders. For example, the base resins BR1, BR2, and BR3 may be acrylic resins, urethane 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.

[0435] The light control layer CCL may include a barrier layer BFL1. The barrier layer BFL1 may serve to prevent the penetration of moisture and / or oxygen (hereinafter referred to as "moisture / oxygen"). The barrier layer BFL1 may block the light control units CCP1, CCP2, and CCP3 from being exposed to moisture / oxygen. On the other hand, the barrier layer BFL1 may cover the light control units CCP1, CCP2, and CCP3. Furthermore, a barrier layer BLF2 may be provided between the light control units CCP1, CCP2, and CCP3 and the color filter layer CFL.

[0436] The barrier layers BFL1 and BFL2 may include at least one inorganic layer. In other words, the barrier layers BFL1 and BFL2 may be formed by including inorganic materials. For example, the barrier layers BFL1 and BFL2 may be formed by including silicon nitride, aluminum nitride, zirconium nitride, titanium nitride, hafnium nitride, tantalum nitride, silicon oxide, aluminum oxide, titanium oxide, tin oxide, cerium oxide, and silicon oxynitride, or a thin metal film with sufficient light transmittance. On the other hand, the barrier layers BFL1 and BFL2 may further include an organic film. The barrier layers BFL1 and BFL2 may consist of a single layer or multiple layers.

[0437] In one embodiment of the display device DD-a, the color filter layer CFL may be placed on top of the light control layer CCL. For example, the color filter layer CFL may be placed directly on top of the color control layer CCL. In this case, the barrier layer BFL2 may be omitted.

[0438] The color filter layer CFL may include filters CF1, CF2, and CF3. Each of the first to third filters CF1, CF2, and CF3 may be positioned corresponding to the red emission region PXA-R, the green emission region PXA-G, and the blue emission region PXA-B, respectively.

[0439] A color filter CFL may include a first filter CF1 that transmits a second color of light, a second filter CF2 that transmits a third color of light, and a third filter CF3 that transmits a first color of light. For example, the first filter CF1 may be a red filter, the second filter CF2 a green filter, and the third filter CF3 a blue filter. Each of filters CF1, CF2, and CF3 may contain a polymer photosensitive resin and a pigment or dye. The first filter CF1 may contain a red pigment or dye, the second filter CF2 may contain a green pigment or dye, and the third filter CF3 may contain a blue pigment or dye.

[0440] On the other hand, the examples are not limited to these, and the third filter CF3 may not contain pigments or dyes. The third filter CF3 may contain a polymer photosensitive resin and may not contain pigments or dyes. The third filter CF3 may be transparent. The third filter CF3 may be made of a transparent photosensitive resin.

[0441] In one embodiment, the first filter CF1 and the second filter CF2 may be yellow filters. The first filter CF1 and the second filter CF2 may be provided as a single unit without being separated from each other.

[0442] Although not shown, the color filter layer CFL may further include a light-shielding section (not shown). The light-shielding section may be a black matrix. The light-shielding section may be formed by comprising an organic or inorganic light-shielding material containing a black pigment or black dye. The light-shielding section may prevent light leakage and demarcate the boundaries between adjacent filters CF1, CF2, and CF3.

[0443] A base substrate BL may be placed on top of the color filter layer CFL. The base substrate BL may be a component that provides a base surface on which the color filter layer CFL and the light control layer CCL are placed. The base substrate BL may be a glass substrate, a metal substrate, a plastic substrate, etc. However, the embodiment is not limited to these, and the base substrate BL may be an inorganic layer, an organic layer, or a composite material layer. Also, contrary to the figures, the base substrate BL may be omitted in one embodiment.

[0444] Figure 8 is a cross-sectional view showing a part of a display device according to one embodiment. In the 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 that are sequentially stacked 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 (Figure 7) and a hole transport region HTR and an electron transport region ETR arranged between the light-emitting layer EML (Figure 7).

[0445] In other words, the light-emitting element ED-BT included in the display device DD-TD of one embodiment may be a light-emitting element with a tandem structure including multiple light-emitting layers.

[0446] In one embodiment shown in Figure 8, 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 wavelength ranges 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, an ED-BT light-emitting element containing multiple light-emitting structures OL-B1, OL-B2, and OL-B3 that emit light in different wavelength ranges from each other can emit white light.

[0447] Charge generation layers CGL1 and CGL2 may be arranged between adjacent light-emitting structures OL-B1, OL-B2, and OL-B3. Charge generation layers CGL1 and CGL2 include a p-type charge generation layer and / or an n-type charge generation layer.

[0448] In one embodiment, at least one of the light-emitting structures OL-B1, OL-B2, and OL-B3 contained in the display device DD-TD contains the condensed polycyclic compound of the embodiment described above. In other words, at least one of the multiple light-emitting layers contained in the light-emitting device ED-BT contains the condensed polycyclic compound of the embodiment.

[0449] Figure 9 is a cross-sectional view showing a display device according to one embodiment of the present invention. Figure 10 is a cross-sectional view showing a display device according to one embodiment of the present invention.

[0450] Referring to Figure 9, the display device DD-b according to one embodiment may include light-emitting elements ED-1, ED-2, and ED-3, each having two stacked light-emitting layers. Compared to the display device DD of one embodiment shown in Figure 2, the difference in the embodiment shown in Figure 9 is that the first to third light-emitting elements ED-1, ED-2, and ED-3 each include two light-emitting layers stacked in the thickness direction. In each of the first to third light-emitting elements ED-1, ED-2, and ED-3, the two light-emitting layers may emit light in the same wavelength range.

[0451] The first light-emitting element ED-1 may include a first red light-emitting layer EML-R1 and a second red light-emitting layer EML-R2. The second light-emitting element ED-2 may include a first green light-emitting layer EML-G1 and a second green light-emitting layer EML-G2. The third light-emitting element ED-3 may include a first blue light-emitting layer EML-B1 and a second blue light-emitting layer EML-B2. Light-emitting auxiliary units OG may be arranged between the first red light-emitting layer EML-R1 and the second red light-emitting layer EML-R2, between the first green light-emitting layer EML-G1 and the second green light-emitting layer EML-G2, and between the first blue light-emitting layer EML-B1 and the second blue light-emitting layer EML-B2.

[0452] The light-emitting auxiliary section OG may include a single layer or a multilayer. The light-emitting auxiliary section OG may include a charge generation layer. More specifically, the light-emitting auxiliary section OG may include sequentially stacked electron transport regions, a charge generation layer, and hole transport regions. The light-emitting auxiliary section OG may be provided in common across the first to third light-emitting elements ED-1, ED-2, and ED-3. However, the examples are not limited thereto, and the light-emitting auxiliary section OG may be provided patterned within an aperture OH defined in the pixel-defining film PDL.

[0453] The first red light-emitting layer EML-R1, the first green light-emitting layer EML-G1, and the first blue light-emitting layer EML-B1 may be arranged between the light-emitting auxiliary region OG and the electron transport region ETR. The second red light-emitting layer EML-R2, the second green light-emitting layer EML-G2, and the second blue light-emitting layer EML-B2 may be arranged between the hole transport region HTR and the light-emitting auxiliary region OG.

[0454] In other words, the first light-emitting element ED-1 may include a first electrode EL1 stacked sequentially, a hole transport region HTR, a second red light-emitting layer EML-R2, a light-emitting auxiliary section OG, a first red light-emitting layer EML-R1, an electron transport region ETR, and a second electrode EL2. The second light-emitting element ED-2 may include a first electrode EL1 stacked sequentially, a hole transport region HTR, a second green light-emitting layer EML-G2, a light-emitting auxiliary section OG, a first green light-emitting layer EML-G1, an electron transport region ETR, and a second electrode EL2. The third light-emitting element ED-3 may include a first electrode EL1 stacked sequentially, a hole transport region HTR, a second blue light-emitting layer EML-B2, a light-emitting auxiliary section OG, a first blue light-emitting layer EML-B1, an electron transport region ETR, and a second electrode EL2.

[0455] On the other hand, an optical auxiliary layer PL may be placed on the display element layer DP-ED. The optical auxiliary layer PL may include a polarizing layer. The optical auxiliary layer PL is placed on the display panel DP and can control the reflected light on the display panel DP due to external light. In one embodiment of the display device, the optical auxiliary layer PL may be omitted, contrary to the illustration.

[0456] At least one light-emitting layer included in the display device DD-b of one embodiment shown in Figure 9 contains the condensed polycyclic compound of the embodiment described above. For example, in one embodiment, at least one of the first blue light-emitting layer EML-B1 and the second blue light-emitting layer EML-B2 may contain the condensed polycyclic compound of the embodiment.

[0457] Unlike Figures 8 and 9, the display device DD-c in Figure 10 is shown to include four light-emitting structures OL-B1, OL-B2, OL-B3, and OL-C1. The light-emitting element ED-CT may include a first electrode EL1 and a second electrode EL2 facing each other, and first to fourth light-emitting structures OL-B1, OL-B2, OL-B3, and OL-C1 sequentially stacked in the thickness direction between the first electrode EL1 and the second electrode EL2. Charge generation layers CGL1, CGL2, and CGL3 may be arranged between the first to fourth light-emitting structures OL-B1, OL-B2, OL-B3, and OL-C1. Of the four light-emitting structures, the first to third light-emitting structures OL-B1, OL-B2, and OL-B3 may emit blue light, and the fourth light-emitting structure OL-C1 may emit green light. However, the examples are not limited to these, and the first to fourth light-emitting structures OL-B1, OL-B2, OL-B3, and OL-C1 can emit light in different wavelength regions.

[0458] The charge generation layers GCL1, CGL2, and CGL3, positioned between adjacent light-emitting structures OL-B1, OL-B2, OL-B3, and OL-C1, may include p-type charge generation layers and / or n-type charge generation layers.

[0459] In the first embodiment, at least one of the light-emitting structures OL-B1, OL-B2, OL-B3, and OL-C1 contained in the display device DD-c contains the condensed polycyclic compound of the first embodiment described above. For example, in the first embodiment, at least one of the first to third light-emitting structures OL-B1, OL-B2, and OL-B3 may contain the condensed polycyclic compound of the first embodiment described above.

[0460] A light-emitting element (ED) according to one embodiment of the present invention exhibits excellent luminous efficiency and improved lifetime characteristics by including the polycyclic compound of the embodiment represented by chemical formula 1 described above in at least one functional layer disposed between the first electrode EL1 and the second electrode EL2. For example, the polycyclic compound of the embodiment may be included in the light-emitting layer EML of the light-emitting element (ED) according to the embodiment, and the light-emitting element of the embodiment exhibits long lifetime characteristics.

[0461] In one embodiment, the electronic device may include a display device containing a plurality of light-emitting elements and a control unit that controls the display device. The electronic device in one embodiment may be a device that is activated by an electrical signal. The electronic device may include electronic devices of various embodiments. For example, the display device may include large electronic devices such as televisions, monitors, or external billboards, as well as small and medium-sized display devices such as personal computers, laptop computers, PDAs, vehicle display devices, game consoles, portable electronic devices, and cameras.

[0462] Figure 11 shows a vehicle AM ​​in which the first to fourth display devices DD-1, DD-2, DD-3, and DD-4 are arranged. At least one of the first to fourth display devices DD-1, DD-2, DD-3, and DD-4 may also include the same configuration as the display devices DD, DD-TD, DD-a, DD-b, and DD-c of one embodiment described with reference to Figures 1, 2, and 7 to 10.

[0463] Although Figure 11 shows an automobile as the vehicle AM, this is illustrative, and the first to fourth display devices DD-1, DD-2, DD-3, and DD-4 may be installed in other means of transport such as bicycles, motorcycles, trains, ships, and airplanes. Furthermore, at least one of the first to fourth display devices DD-1, DD-2, DD-3, and DD-4, which also include the configuration of the display devices DD, DD-TD, DD-a, DD-b, and DD-c of one embodiment, may be used in personal computers, laptop computers, PDAs, game consoles, portable electronic devices, televisions, monitors, external advertising boards, etc. Moreover, these are merely presented as embodiments, and may be display devices used in other electronic devices as long as they do not deviate from the concept of the present invention.

[0464] At least one of the first to fourth display devices DD-1, DD-2, DD-3, and DD-4 includes a light-emitting element ED of one embodiment described with reference to Figures 3 to 6. The light-emitting element ED of one embodiment includes a heterocyclic compound of one embodiment. The display life is improved by including a light-emitting element ED containing the heterocyclic compound of one embodiment in at least one of the first to fourth display devices DD-1, DD-2, DD-3, and DD-4.

[0465] Referring to Figure 11, the vehicle AM ​​includes a steering wheel HA and a gear GR for operating the vehicle AM. The vehicle AM ​​also includes a forward window GL positioned to face the driver.

[0466] The first display device DD-1 may be positioned in a first area that overlaps with the steering wheel HA. For example, the first display device DD-1 may be a digital cluster that displays first information of the vehicle AM. The first information may include a first scale representing the vehicle AM's speed, a second scale indicating the engine speed (i.e., RPM (revolutions per minute)), and an image indicating the fuel status. The first and second scales may be displayed as digital images.

[0467] The second display device DD-2 may be positioned in a second area facing the driver's seat and overlapping with the front window GL. The driver's seat may be the seat on which the steering wheel HA is located. For example, the second display device DD-2 may be a head-up display (HUD) that displays second information of the vehicle AM. The second display device DD-2 may be optically transparent. The second information may include digital figures indicating the vehicle AM's speed and may further include information such as the current time. Contrary to the illustration, the second information of the second display device DD-2 may be projected onto the front window GL.

[0468] The third display device DD-3 may be located in a third area adjacent to the gear GR. For example, the third display device DD-3 may be located between the driver's seat and the passenger seat and may be a Center Information Display (CID) for displaying third information. The passenger seat may be a seat separated from the driver's seat with the gear GR in between. The third information may include information about road conditions (e.g., navigation information), music or radio playback, dynamic video (or image) playback, and the temperature inside the vehicle AM.

[0469] The fourth display device DD-4 may be located in a fourth area adjacent to the side of the vehicle AM, separated from the steering wheel HA and gear GR. For example, the fourth display device DD-4 may be a digital side mirror that displays fourth information. The fourth display device DD-4 may display images of the outside of the vehicle AM ​​captured by a camera module CM located outside the vehicle AM. The fourth information may include images of the outside of the vehicle AM.

[0470] The first to fourth pieces of information described above are illustrative, and the first to fourth display devices DD-1, DD-2, DD-3, and DD-4 may further display information relating to the interior and exterior of the vehicle AM. The first to fourth pieces of information may contain different information from each other. However, the embodiments are not limited thereto, and some of the first to fourth pieces of information may contain the same information from each other.

[0471] The following describes in detail a condensed polycyclic compound and a light-emitting element according to one embodiment of the present invention, with reference to examples and comparative examples. Furthermore, the following examples are illustrative to aid in understanding the present invention, and the scope of the present invention is not limited thereto.

[0472] [Examples] 1. Synthesis of condensed polycyclic compounds First, the synthesis method of condensed polycyclic compounds according to this embodiment will be explained in detail, with examples of the synthesis methods for compounds B-11, G-7, C-21, C-16, C-19, and I-3. Furthermore, the synthesis method of condensed polycyclic compounds described below is just one example, and the synthesis method of condensed polycyclic compounds according to the embodiments of the present invention is not limited to the following examples.

[0473] (1) Synthesis of compound B-11 The condensed polycyclic compound B-11 according to one example can be synthesized, for example, by the following reaction.

[0474] (Synthesis of intermediate B-11-6) JPEG2026076767000165.jpg105162

[0475] Intermediate B-11-6-1 (200 mmol), B-11-6-2 (220 mmol), and K2CO3 (350 mmol) were added to a three-necked flask and substituted with Ar. Then, 200 mL of N-methyl-2-pyrrolidone (NMP) was added and the mixture was stirred at 150°C for 6 hours. Water was added to the reaction system, and the organic layer was extracted using toluene. The mixture was then dried over magnesium sulfate, and the solvent was removed by evaporation. The resulting crude product was purified by silica gel column chromatography (hexane / toluene mixed solvent) and recrystallization (ethanol / toluene mixed solvent) to obtain 154 mmol of a white solid (yield 77%). The molecular weight of the purified product was confirmed to be 541 by FAB-MS, confirming that intermediate B-11-6 had been obtained.

[0476] (Synthesis of intermediate B-11-3) JPEG2026076767000166.jpg91154

[0477] Intermediate B-11-1 (150 mmol), intermediate B-11-2 (300 mmol), tBuONa (600 mmol), Pd(dba)2 (15 mmol), and [(tBu)3PH]BF4 (30 mmol) were added to a three-necked flask and substituted with Ar. Then 1000 mL of toluene was added and the mixture was stirred at 100°C for 3 hours. Water was added to the reaction system, and the organic layer was extracted using toluene. The mixture was then dried over magnesium sulfate, and the solvent was evaporated to remove it. The resulting crude product was purified by silica gel column chromatography (hexane / toluene mixed solvent) and recrystallization (ethanol / toluene mixed solvent) to obtain 145 mmol of a white solid (97% yield). FAB-MS measurement of the purified product confirmed that the molecular weight was 773, confirming that intermediate B-11-3 had been obtained.

[0478] (Synthesis of intermediate B-11-5) JPEG2026076767000167.jpg48148

[0479] Next, intermediates B-11-3 (145 mmol), B-11-4 (435 mmol), K2CO3 (1015 mmol), and CuI (145 mmol) were added to a three-necked flask, and after ar substitution, the mixture was stirred at 210°C for 24 hours. Water was added to the reaction system, and the organic layer was extracted using toluene. The mixture was then dried over magnesium sulfate, and the solvent was removed by evaporation. The resulting crude product was purified by silica gel column chromatography (hexane / toluene mixed solvent) and recrystallization (ethanol / toluene mixed solvent) to obtain 80 mmol of a white solid (yield 55%). FAB-MS analysis of the purified product confirmed that the molecular weight was 883, confirming that intermediate B-11-5 had been obtained.

[0480] (Synthesis of intermediate B-11-7) JPEG2026076767000168.jpg68138

[0481] Intermediate B-11-5 (80 mmol), intermediate B-11-6 (154 mmol), K2CO3 (240 mmol), and CuI (80 mmol) were added to a three-necked flask, and after ar substitution, the mixture was stirred at 210°C for 50 hours. Water was added to the reaction system, and the organic layer was extracted using toluene. The mixture was then dried over magnesium sulfate, and the solvent was removed by evaporation. The resulting crude product was purified by silica gel column chromatography (hexane / toluene mixed solvent) and recrystallization (ethanol / toluene mixed solvent) to obtain 61 mmol of a white solid (yield 76%). FAB-MS analysis of the purified product confirmed that the molecular weight was 1207, confirming that intermediate B-11-7 had been obtained.

[0482] (Synthesis of intermediate B-11-9) JPEG2026076767000169.jpg62149

[0483] Intermediate B-11-7 (61 mmol), intermediate B-11-8 (65 mmol), tBuONa (65 mmol), Pd(dba)2 (6 mmol), and [(tBu)3PH]BF4 (12 mmol) were added to a three-necked flask and substituted with Ar. Then 200 mL of toluene was added and the mixture was stirred at 100°C for 6 hours. Water was added to the reaction system, and the organic layer was extracted using toluene. The mixture was then dried over magnesium sulfate, and the solvent was removed by evaporation. The resulting crude product was purified by silica gel column chromatography (hexane / toluene mixed solvent) and recrystallization (ethanol / toluene mixed solvent) to obtain 58 mmol of a white solid (yield 95%). FAB-MS measurement of the purified product confirmed that the molecular weight was 1295, confirming that intermediate B-11-9 had been obtained.

[0484] (Synthesis of intermediate B-11-10) JPEG2026076767000170.jpg61149

[0485] tBuONa (87 mmol), Pd(dba)2 (8 mmol), and SPhos (16 mmol) were added to a three-necked flask and substituted with Ar. Then, 1000 mL of toluene was added and the mixture was stirred at 100°C. To the stirred solution, a solution of intermediate B-11-9 (58 mmol) dissolved in 200 mL of toluene was added to the reaction system by dropwise addition, and the mixture was stirred for 4 hours. Water was added to the reaction system, and the organic layer was extracted using toluene. The mixture was then dried over magnesium sulfate, and the solvent was evaporated to remove it. The resulting crude product was purified by silica gel column chromatography (hexane / toluene mixed solvent) and recrystallization (ethanol / toluene mixed solvent) to obtain 22 mmol of a white solid (yield 38%). FAB-MS analysis of the purified product confirmed that the molecular weight was 1259, confirming that intermediate B-11-10 had been obtained.

[0486] (Synthesis of compound B-11) JPEG2026076767000171.jpg61150

[0487] Intermediate B-11-10 (22 mmol) was added to a three-necked flask and substituted with Ar. Then, 20 mL of 1,2-dichlorobenzene (ODCB) was added and dissolved further. Finally, BI3 (88 mmol) was added and the mixture was stirred at 140°C for 2 hours. The reaction mixture was dispersed and washed with a large amount of acetonitrile, and the solid was collected by filtration. The obtained crude product was purified by silica gel column chromatography (hexane / dichloromethane mixed solvent) and recrystallization (ethanol / toluene mixed solvent) to obtain 15 mmol of yellow solid (yield 68%). FAB-MS measurement of the obtained purified product confirmed that the molecular weight was 1274, confirming that intermediate B-11 had been obtained.

[0488] (2) Synthesis of compound G-7 The condensed polycyclic compound G-7 according to one example can be synthesized, for example, by the following reaction.

[0489] (Synthesis of intermediate a) JPEG2026076767000172.jpg52153

[0490] Intermediate a-1 (300 mmol), intermediate a-3 (330 mmol), and K2CO3 (600 mmol) were added to a three-necked flask and substituted with Ar. Then 200 mL of NMP was added and the mixture was stirred at 150°C for 24 hours. Water was added to the reaction system, and the organic layer was extracted using toluene. The mixture was then dried over magnesium sulfate, and the solvent was evaporated to remove it. The resulting crude product was purified by silica gel column chromatography (hexane / toluene mixed solvent) and recrystallization (ethanol / toluene mixed solvent) to obtain 243 mmol of a white solid (yield 81%). FAB-MS analysis of the purified product confirmed that the molecular weight was 404, confirming that intermediate a-3 had been obtained.

[0491] Next, intermediate a-3 (243 mmol), intermediate a-4 (243 mmol), tBuONa (365 mmol), Pd(dba)2 (20 mmol), and [(tBu)3PH]BF4 (40 mmol) were added to a three-necked flask and substituted with Ar. Then, 1000 mL of toluene was added and the mixture was stirred at 100°C for 1 hour. Water was added to the reaction system, and the organic layer was extracted using toluene. The mixture was then dried over magnesium sulfate, and the solvent was removed by evaporation. The resulting crude product was purified by silica gel column chromatography (hexane / toluene mixed solvent) and recrystallization (ethanol / toluene mixed solvent) to obtain 146 mmol of a white solid (yield 60%). FAB-MS analysis of the purified product confirmed that the molecular weight was 492, confirming that intermediate a had been obtained.

[0492] (Synthesis of intermediate G-7-3) JPEG2026076767000173.jpg82132

[0493] Intermediate G-7-1 (400 mmol), intermediate G-7-2 (200 mmol), tBuONa (220 mmol), Pd(dba)2 (30 mmol), and [(tBu)3PH]BF4 (60 mmol) were added to a three-necked flask and substituted with Ar. Then 1000 mL of toluene was added and the mixture was stirred at 100°C for 8 hours. Water was added to the reaction system, and the organic layer was extracted using toluene. The mixture was then dried over magnesium sulfate, and the solvent was evaporated to remove it. The resulting crude product was purified by silica gel column chromatography (hexane / toluene mixed solvent) and recrystallization (ethanol / toluene mixed solvent) to obtain 157 mmol of a white solid (yield 79%). FAB-MS analysis of the purified product confirmed that the molecular weight was 430, confirming that intermediate G-7-3 had been obtained.

[0494] (Synthesis of intermediate G-7-5) JPEG2026076767000174.jpg72167

[0495] Intermediate G-7-3 (157 mmol), intermediate G-7-4 (200 mmol), K3PO4 (220 mmol), Pd(dba)2 (30 mmol), and [(tBu)3PH]BF4 (60 mmol) were added to a three-necked flask and substituted with Ar. Then, 1000 mL of toluene, 20 mL of EtOH, and 20 mL of H2O were added and the mixture was stirred at 100°C for 3 hours. Water was added to the reaction system, and the organic layer was extracted using toluene. The mixture was then dried over magnesium sulfate, and the solvent was evaporated to remove it. The resulting crude product was purified by silica gel column chromatography (hexane / toluene mixed solvent) and recrystallization (ethanol / toluene mixed solvent) to obtain 145 mmol of a white solid (92% yield). FAB-MS analysis of the purified product confirmed that the molecular weight was 428, confirming that intermediate G-7-5 had been obtained.

[0496] (Synthesis of intermediate G-7-6) JPEG2026076767000175.jpg66166

[0497] Intermediate G-7-5 (145 mmol) was added to 200 mL of dichloromethane (DCM) in a three-necked flask, and the flask was placed in an ice bath to bring the internal temperature to 0°C. Then, BBr3 (290 mmol) was added dropwise to a solution of DCM dissolved in 100 mL, and the mixture was allowed to return to room temperature and stirred for 12 hours. Water was added to the reaction system, and the organic layer was extracted using DCM. The mixture was then dried over magnesium sulfate, and the solvent was removed by evaporation. The resulting crude product was purified by silica gel column chromatography (hexane / toluene mixed solvent) and recrystallization (ethanol / toluene mixed solvent) to obtain 120 mmol of white solid (yield 83%). FAB-MS analysis of the purified product confirmed that the molecular weight was 414, confirming that intermediate G-7-6 had been obtained.

[0498] (Synthesis of intermediate G-7-8) JPEG2026076767000176.jpg70160

[0499] Intermediate G-7-6 (120 mmol), intermediate G-7-7 (1200 mmol), Cs2CO3 (240 mmol), CuI (20 mmol), and dipivaloylmethane (20 mmol) were added to a three-necked flask and substituted with Ar. The mixture was then stirred at 120°C for 3 hours. Water was added to the reaction system, and the organic layer was extracted using toluene. The mixture was then dried over magnesium sulfate, and the solvent was removed by evaporation. The resulting crude product was purified by silica gel column chromatography (hexane / toluene mixed solvent) and recrystallization (ethanol / toluene mixed solvent) to obtain 86 mmol of a white solid (72% yield). FAB-MS analysis of the purified product confirmed that the molecular weight was 741, confirming that intermediate G-7-8 had been obtained.

[0500] (Synthesis of intermediate G-7-9) JPEG2026076767000177.jpg65141

[0501] Intermediate G-7-8 (86 mmol), intermediate G-7-4 (86 mmol), K3PO4 (240 mmol), Pd(dba)2 (10 mmol), and [(tBu)3PH]BF4 (20 mmol) were added to a three-necked flask and substituted with Ar. Then, 1000 mL of toluene, 20 mL of EtOH, and 20 mL of H2O were added and the mixture was stirred at 100°C for 5 hours. Water was added to the reaction system, and the organic layer was extracted using toluene. The mixture was then dried over magnesium sulfate, and the solvent was removed by evaporation. The resulting crude product was purified by silica gel column chromatography (hexane / toluene mixed solvent) and recrystallization (ethanol / toluene mixed solvent) to obtain 56 mmol of a white solid (yield 65%). FAB-MS analysis of the purified product confirmed that the molecular weight was 692, confirming that intermediate G-7-9 had been obtained.

[0502] (Synthesis of intermediate G-7-10) JPEG2026076767000178.jpg71170

[0503] Intermediate G-7-9 (400 mmol), intermediate a (56 mmol), tBuONa (112 mmol), Pd(dba)2 (10 mmol), and [(tBu)2PH]BF4 (20 mmol) were added to a three-necked flask and substituted with Ar. Then 500 mL of toluene was added and the mixture was stirred at 100°C for 3 hours. Water was added to the reaction system, and the organic layer was extracted using toluene. The mixture was then dried over magnesium sulfate, and the solvent was evaporated to remove it. The resulting crude product was purified by silica gel column chromatography (hexane / toluene mixed solvent) and recrystallization (ethanol / toluene mixed solvent) to obtain 49 mmol of a white solid (yield 88%). FAB-MS analysis of the purified product confirmed that the molecular weight was 1056, confirming that intermediate G-7-10 had been obtained.

[0504] (Synthesis of intermediate G-7-11) JPEG2026076767000179.jpg90166

[0505] Intermediate G-7-10 (49 mmol), K2CO3 (490 mmol), CuI (49 mmol), and 100 mL of xylene were added to a three-necked flask, substituted with Ar, and stirred at 210°C for 24 hours. Water was added to the reaction system, and the organic layer was extracted using toluene. The mixture was then dried over magnesium sulfate, and the solvent was removed by evaporation. The resulting crude product was purified by silica gel column chromatography (hexane / toluene mixed solvent) and recrystallization (ethanol / toluene mixed solvent) to obtain 34 mmol of a white solid (yield 69%). FAB-MS measurement of the purified product confirmed a molecular weight of 975, confirming that intermediate G-7-11 had been obtained.

[0506] (Synthesis of compound G-7) JPEG2026076767000180.jpg70141

[0507] Intermediate G-7-11 (34 mmol) was added to a three-necked flask and substituted with Ar. 50 mL of ODCB was then added to further dissolve the mixture. BI3 (132 mmol) was added, and the mixture was stirred at 140°C for 6 hours. The reaction mixture was dispersed and washed with a large amount of acetonitrile, and the solid was collected by filtration. The resulting crude product was purified by silica gel column chromatography (hexane / dichloromethane mixed solvent) and recrystallization (ethanol / toluene mixed solvent) to obtain 14 mmol of yellow solid (41% yield). FAB-MS analysis of the purified product confirmed a molecular weight of 991, confirming that intermediate G-7 had been obtained.

[0508] (3) Synthesis of compound C-21 The condensed polycyclic compound C-21 according to one example can be synthesized, for example, by the following reaction.

[0509] (Synthesis of intermediate b) JPEG2026076767000181.jpg91131

[0510] Intermediate b-1 (400 mmol), intermediate b-2 (20 mmol), tBuONa (220 mmol), Pd(dba)2 (30 mmol), and [(tBu)3PH]BF4 (60 mmol) were added to a three-necked flask and substituted with Ar. Then 1000 mL of toluene was added and the mixture was stirred at 100°C for 3 hours. Water was added to the reaction system, and the organic layer was extracted using toluene. The mixture was then dried over magnesium sulfate, and the solvent was evaporated to remove it. The resulting crude product was purified by silica gel column chromatography (hexane / toluene mixed solvent) and recrystallization (ethanol / toluene mixed solvent) to obtain 177 mmol of a white solid (yield 89%). FAB-MS analysis of the purified product confirmed that the molecular weight was 456, confirming that intermediate b had been obtained.

[0511] (Synthesis of intermediate C-21-3) JPEG2026076767000182.jpg99137

[0512] Intermediate C-21-1 (400 mmol), intermediate C-21-2 (20 mmol), tBuONa (220 mmol), Pd(dba)2 (30 mmol), and [(tBu)3PH]BF4 (60 mmol) were added to a three-necked flask and substituted with Ar. Then 1000 mL of toluene was added and the mixture was stirred at 100°C for 4 hours. Water was added to the reaction system, and the organic layer was extracted using toluene. The mixture was then dried over magnesium sulfate, and the solvent was removed by evaporation. The resulting crude product was purified by silica gel column chromatography (hexane / toluene mixed solvent) and recrystallization (ethanol / toluene mixed solvent) to obtain 168 mmol of a white solid (yield 84%). FAB-MS analysis of the purified product confirmed that the molecular weight was 430, confirming that intermediate C-21-3 had been obtained.

[0513] (Synthesis of intermediate C-21-5) JPEG2026076767000183.jpg62170

[0514] Intermediate C-21-3 (168 mmol), K2CO3 (1176 mmol), CuI (168 mmol), and 200 mL of xylene were added to a three-necked flask, and after ar substitution, the mixture was stirred at 210°C for 49 hours. Water was added to the reaction system, and the organic layer was extracted using toluene. The mixture was then dried over magnesium sulfate, and the solvent was removed by evaporation. The resulting crude product was purified by silica gel column chromatography (hexane / toluene mixed solvent) and recrystallization (ethanol / toluene mixed solvent) to obtain 126 mmol of a white solid (yield 75%). FAB-MS analysis of the purified product confirmed that the molecular weight was 583, confirming that intermediate C-21-5 had been obtained.

[0515] (Synthesis of intermediate C-21-7) JPEG2026076767000184.jpg73170

[0516] Intermediate C-21-5 (126 mmol), intermediate C-21-6 (189 mmol), tBuONa (378 mmol), Pd(dba)2 (20 mmol), and [(tBu)3PH]BF4 (40 mmol) were added to a three-necked flask and substituted with Ar. Then 500 mL of toluene was added and the mixture was stirred at 100°C for 2 hours. Water was added to the reaction system, and the organic layer was extracted using toluene. The mixture was then dried over magnesium sulfate, and the solvent was removed by evaporation. The resulting crude product was purified by silica gel column chromatography (hexane / toluene mixed solvent) and recrystallization (ethanol / toluene mixed solvent) to obtain 101 mmol of a white solid (80% yield). FAB-MS analysis of the purified product confirmed that the molecular weight was 629, confirming that intermediate C-21-7 had been obtained.

[0517] (Synthesis of intermediate C-21-9) JPEG2026076767000185.jpg63170

[0518] Intermediate C-21-7 (101 mmol), intermediate C-21-8 (152 mmol), K3PO4 (303 mmol), Pd(dba)2 (10 mmol), and SPhos (20 mmol) were added to a three-necked flask and substituted with Ar. Then, 200 mL of toluene, 20 mL of EtOH, and 20 mL of H2O were added and the mixture was stirred at 110°C for 12 hours. Water was added to the reaction system, and the organic layer was extracted using toluene. The mixture was then dried over magnesium sulfate, and the solvent was removed by evaporation. The resulting crude product was purified by silica gel column chromatography (hexane / toluene mixed solvent) and recrystallization (ethanol / toluene mixed solvent) to obtain 88 mmol of white solid (yield 87%). FAB-MS analysis of the purified product confirmed that the molecular weight was 671, confirming that intermediate C-21-9 had been obtained.

[0519] (Synthesis of intermediate C-21-10) JPEG2026076767000186.jpg54170

[0520] Intermediate C-21-9 (88 mmol) and 200 mL of DCM were added to a three-necked flask, and the flask was placed in an ice bath to bring the internal temperature to 0°C. Then, 3166 mmol of BBr was dissolved in 100 mL of DCM and added, and the mixture was stirred for 24 hours at room temperature. Water was added to the reaction system, and the organic layer was extracted using DCM. The mixture was then dried over magnesium sulfate, and the solvent was removed by evaporation. The resulting crude product was purified by silica gel column chromatography (hexane / toluene mixed solvent) and recrystallization (ethanol / toluene mixed solvent) to obtain 60 mmol of white solid (yield 68%). FAB-MS analysis of the purified product confirmed that the molecular weight was 657, confirming that intermediate C-21-10 had been obtained.

[0521] (Synthesis of intermediate C-21-11) JPEG2026076767000187.jpg62170

[0522] Intermediate C-21-10 (120 mmol), intermediate b (60 mmol), Cs2CO3 (240 mmol), CuI (20 mmol), and dipivaloylmethane (20 mmol) were added to a three-necked flask and substituted with Ar. The mixture was then stirred at 140°C for 6 hours. Water was added to the reaction system, and the organic layer was extracted using toluene. The mixture was then dried over magnesium sulfate, and the solvent was removed by evaporation. The resulting crude product was purified by silica gel column chromatography (hexane / toluene mixed solvent) and recrystallization (ethanol / toluene mixed solvent) to obtain 47 mmol of a white solid (78% yield). FAB-MS analysis of the purified product confirmed that the molecular weight was 1032, confirming that intermediate C-21-11 had been obtained.

[0523] (Synthesis of intermediate C-21-13) JPEG2026076767000188.jpg61170

[0524] Intermediate C-21-11 (47 mmol), K2CO3 (329 mmol), CuI (47 mmol), and 400 mL of xylene were added to a three-necked flask, substituted with Ar, and stirred at 210°C for 56 hours. Water was added to the reaction system, and the organic layer was extracted using toluene. The mixture was then dried over magnesium sulfate, and the solvent was removed by evaporation. The resulting crude product was purified by silica gel column chromatography (hexane / toluene mixed solvent) and recrystallization (ethanol / toluene mixed solvent) to obtain 21 mmol of a white solid (yield 45%). FAB-MS analysis of the purified product confirmed a molecular weight of 1183, confirming that intermediate C-21-13 had been obtained.

[0525] (Synthesis of compound C-21) JPEG2026076767000189.jpg59170

[0526] Intermediate C-21-13 (21 mmol) was added to a three-necked flask and substituted with Ar. Then, 20 mL of ODCB was added to further dissolve the mixture, followed by the addition of BI3 (84 mmol) and stirring at 140°C for 6 hours. The reaction mixture was dispersed and washed with a large amount of acetonitrile, and the solid was collected by filtration. The resulting crude product was purified by silica gel column chromatography (hexane / dichloromethane mixed solvent) and recrystallization (ethanol / toluene mixed solvent) to obtain 7 mmol of yellow solid (yield 33%). FAB-MS analysis of the purified product confirmed a molecular weight of 1198, confirming the acquisition of intermediate C-21.

[0527] (4) Synthesis of compound C-16 (Synthesis of intermediate C-16-3) JPEG2026076767000190.jpg61170

[0528] Intermediate C-16-1 (400 mmol), intermediate C-16-2 (400 mmol), tBuONa (450 mmol), Pd(dba)2 (40 mmol), and [(tBu)3PH]BF4 (80 mmol) were added to a three-necked flask and substituted with Ar. Then 1000 mL of toluene was added and the mixture was stirred at 100°C for 8 hours. Water was added to the reaction system, and the organic layer was extracted using toluene. The mixture was then dried over magnesium sulfate, and the solvent was removed by evaporation. The resulting crude product was purified by silica gel column chromatography (hexane / toluene mixed solvent) and recrystallization (ethanol / toluene mixed solvent) to obtain 356 mmol of a white solid (yield 89%). FABMS analysis of the purified product confirmed that the molecular weight was 301, confirming that intermediate C-16-3 had been obtained.

[0529] (Synthesis of intermediate C-16-5) JPEG2026076767000191.jpg56170

[0530] Intermediate C-16-3 (356 mmol), intermediate C-16-4 (356 mmol), tBuONa (400 mmol), Pd(dba)2 (36 mmol), and [(tBu)3PH]BF4 (72 mmol) were added to a three-necked flask and substituted with Ar. Then 1000 mL of toluene was added and the mixture was stirred at 80°C for 5 hours. Water was added to the reaction system, and the organic layer was extracted using toluene. The mixture was then dried over magnesium sulfate, and the solvent was removed by evaporation. The resulting crude product was purified by silica gel column chromatography (hexane / toluene mixed solvent) and recrystallization (ethanol / toluene mixed solvent) to obtain 299 mmol of a white solid (yield 84%). FABMS analysis of the purified product confirmed that the molecular weight was 486, confirming that intermediate C-16-5 had been obtained.

[0531] (Synthesis of intermediate C-16-7) JPEG2026076767000192.jpg53170

[0532] Intermediate C-16-5 (299 mmol), intermediate C-16-6 (299 mmol), tBuONa (450 mmol), Pd(dba)2 (29 mmol), and [(tBu)3PH]BF4 (58 mmol) were added to a three-necked flask and substituted with Ar. Then 1000 mL of toluene was added and the mixture was stirred at 100°C for 1 hour. Water was added to the reaction system, and the organic layer was extracted using toluene. The mixture was then dried over magnesium sulfate, and the solvent was removed by evaporation. The resulting crude product was purified by silica gel column chromatography (hexane / toluene mixed solvent) and recrystallization (ethanol / toluene mixed solvent) to obtain 280 mmol of white solid (yield 94%). FABMS analysis of the purified product confirmed that the molecular weight was 630, confirming that intermediate C-16-7 had been obtained.

[0533] (Synthesis of intermediate C-16-8) JPEG2026076767000193.jpg56170

[0534] Intermediate C-16-7 (280 mmol) and 500 mL of DCM were added to a three-necked flask, and the flask was placed in an ice bath to bring the internal temperature to 0°C. Then, 3420 mmol of BBr was dissolved in 200 mL of DCM and added, and the mixture was stirred for 24 hours at room temperature. Water was added to the reaction system, and the organic layer was extracted using DCM. The mixture was then dried over magnesium sulfate, and the solvent was removed by evaporation. The resulting crude product was purified by silica gel column chromatography (hexane / toluene mixed solvent) and recrystallization (ethanol / toluene mixed solvent) to obtain 255 mmol of white solid (91% yield). FABMS analysis of the purified product confirmed that the molecular weight was 617, confirming that intermediate C-16-8 had been obtained.

[0535] (Synthesis of intermediate C-16-10) JPEG2026076767000194.jpg67170

[0536] Intermediate C-16-8 (255 mmol), K2CO3 (765 mmol), and 200 mL of NMP were added to a three-necked flask, and after ar substitution, the mixture was stirred at 150°C for 30 hours. Water was added to the reaction system, and the organic layer was extracted using toluene. The mixture was then dried over magnesium sulfate, and the solvent was removed by evaporation. The resulting crude product was purified by silica gel column chromatography (hexane / toluene mixed solvent) and recrystallization (ethanol / toluene mixed solvent) to obtain 124 mmol of a white solid (49% yield). FABMS analysis of the purified product confirmed that the molecular weight was 936, confirming that intermediate C-16-10 had been obtained.

[0537] (Synthesis of intermediate C-16-12) JPEG2026076767000195.jpg54170

[0538] Intermediate C-16-10 (124 mmol), intermediate C-16-11 (124 mmol), K2CO3 (868 mmol), and CuI (248 mmol) were added to a three-necked flask, and after ar substitution, the mixture was stirred at 210°C for 80 hours. Water was added to the reaction system, and the organic layer was extracted using toluene. The mixture was then dried over magnesium sulfate, and the solvent was removed by evaporation. The resulting crude product was purified by silica gel column chromatography (hexane / toluene mixed solvent) and recrystallization (ethanol / toluene mixed solvent) to obtain a white solid of 56 mmol (yield 45%). FABMS analysis of the purified product confirmed that the molecular weight was 1086, confirming that intermediate C-16-12 had been obtained.

[0539] (Synthesis of compound C-16) JPEG2026076767000196.jpg57170

[0540] Intermediate C-16-12 (56 mmol) was added to a three-necked flask and substituted with Ar. Then, 20 mL of ODCB was added to further dissolve the mixture, followed by the addition of BI3 (224 mmol) and stirring at 140°C for 3 hours. The reaction mixture was dispersed and washed using a large amount of acetonitrile, and the solid was collected by filtration. The resulting crude product was purified by silica gel column chromatography (hexane / dichloromethane mixed solvent) and recrystallization (ethanol / toluene mixed solvent) to obtain 14 mmol of yellow solid (25% yield). FABMS analysis of the purified product confirmed a molecular weight of 1102, confirming the acquisition of intermediate C-16.

[0541] (5) Synthesis of compound C-19 (Synthesis of intermediate C-19-3) JPEG2026076767000197.jpg56170

[0542] Intermediate C-19-1 (600 mmol), intermediate C-19-2 (600 mmol), tBuONa (800 mmol), Pd(dba)2 (60 mmol), and [(tBu)3PH]BF4 (120 mmol) were added to a three-necked flask and substituted with Ar. Then 2000 mL of toluene was added and the mixture was stirred at 100°C for 12 hours. Water was added to the reaction system, and the organic layer was extracted using toluene. The mixture was then dried over magnesium sulfate, and the solvent was removed by evaporation. The resulting crude product was purified by silica gel column chromatography (hexane / toluene mixed solvent) and recrystallization (ethanol / toluene mixed solvent) to obtain a white solid of 354 mmol (yield 59%). FABMS analysis of the purified product confirmed that the molecular weight was 354, confirming that intermediate C-19-3 had been obtained.

[0543] (Synthesis of intermediate C-19-5) JPEG2026076767000198.jpg55170

[0544] Intermediate C-16-3 (354 mmol), intermediate C-16-4 (354 mmol), tBuONa (531 mmol), Pd(dba)2 (36 mmol), and [(tBu)3PH]BF4 (72 mmol) were added to a three-necked flask and substituted with Ar. Then 1000 mL of toluene was added and the mixture was stirred at 80°C for 22 hours. Water was added to the reaction system, and the organic layer was extracted using toluene. The mixture was then dried over magnesium sulfate, and the solvent was removed by evaporation. The resulting crude product was purified by silica gel column chromatography (hexane / toluene mixed solvent) and recrystallization (ethanol / toluene mixed solvent) to obtain 320 mmol of white solid (90% yield). FABMS analysis of the purified product confirmed that the molecular weight was 366, confirming that intermediate C-19-5 had been obtained.

[0545] (Synthesis of intermediate C-19-6) JPEG2026076767000199.jpg43170

[0546] Intermediate C-19-5 (320 mmol) and 600 mL of DCM were added to a three-necked flask, and the flask was placed in an ice bath to bring the internal temperature to 0°C. Then, 3480 mmol of BBr was dissolved in 200 mL of DCM and added, and the mixture was stirred for 24 hours at room temperature. Water was added to the reaction system, and the organic layer was extracted using DCM. The mixture was then dried over magnesium sulfate, and the solvent was removed by evaporation. The resulting crude product was purified by silica gel column chromatography (hexane / toluene mixed solvent) and recrystallization (ethanol / toluene mixed solvent) to obtain 290 mmol of white solid (yield 91%). FABMS analysis of the purified product confirmed that the molecular weight was 352, confirming that intermediate C-19-6 had been obtained.

[0547] (Synthesis of intermediate C-19-9) JPEG2026076767000200.jpg48170

[0548] Intermediate C-19-7 (299 mmol), intermediate C-19-8 (299 mmol), tBuONa (450 mmol), Pd(dba)2 (30 mmol), and [(tBu)3PH]BF4 (60 mmol) were added to a three-necked flask and substituted with Ar. Then 1000 mL of toluene was added and the mixture was stirred at 100°C for 2 hours. Water was added to the reaction system, and the organic layer was extracted using toluene. The mixture was then dried over magnesium sulfate, and the solvent was removed by evaporation. The resulting crude product was purified by silica gel column chromatography (hexane / toluene mixed solvent) and recrystallization (ethanol / toluene mixed solvent) to obtain 249 mmol of a white solid (yield 83%). FABMS analysis of the purified product confirmed that the molecular weight was 298, confirming that intermediate C-19-9 had been obtained.

[0549] (Synthesis of intermediate C-19-10) JPEG2026076767000201.jpg59170

[0550] Intermediate C-19-6 (249 mmol), intermediate C-19-9 (249 mmol), and 300 mL of K2CO3 (747 mmol)NMP were added to a three-necked flask, and after argon substitution, the mixture was stirred at 150°C for 22 hours. Water was added to the reaction system, and the organic layer was extracted using toluene. The mixture was then dried over magnesium sulfate, and the solvent was removed by evaporation. The resulting crude product was purified by silica gel column chromatography (hexane / toluene mixed solvent) and recrystallization (ethanol / toluene mixed solvent) to obtain 211 mmol of a white solid (yield 85%). FABMS analysis of the purified product confirmed that the molecular weight was 630, confirming that intermediate C-19-10 had been obtained.

[0551] (Intermediate C-19-12) JPEG2026076767000202.jpg62170

[0552] Intermediate C-19-10 (211 mmol), intermediate C-19-11 (211 mmol), K2CO3 (1477 mmol), and CuI (422 mmol) were added to a three-necked flask, and after ar substitution, the mixture was stirred at 210°C for 85 hours. Water was added to the reaction system, and the organic layer was extracted using toluene. The mixture was then dried over magnesium sulfate, and the solvent was removed by evaporation. The resulting crude product was purified by silica gel column chromatography (hexane / toluene mixed solvent) and recrystallization (ethanol / toluene mixed solvent) to obtain a white solid of 43 mmol (yield 20%). FABMS analysis of the purified product confirmed that the molecular weight was 856, confirming that intermediate C-19-12 had been obtained.

[0553] (Intermediate C-19-13) JPEG2026076767000203.jpg51170

[0554] Intermediate C-19-12 (43 mmol) was added to a three-necked flask and substituted with Ar. After further dissolution with 15 mL of ODCB, BI3 (172 mmol) was added and the mixture was stirred at 140°C for 2 hours. The reaction mixture was dispersed and washed using a large amount of acetonitrile, and the solid was collected by filtration. The resulting crude product was purified by silica gel column chromatography (hexane / dichloromethane mixed solvent) and recrystallization (ethanol / toluene mixed solvent) to obtain 20 mmol of yellow solid (47% yield). FABMS analysis of the purified product confirmed a molecular weight of 872, confirming the acquisition of intermediate C-19-13.

[0555] (Synthesis of compound C-19) JPEG2026076767000204.jpg54170

[0556] Intermediate C-19-13 (20 mmol), intermediate C-19-14 (30 mmol), tBuONa (45 mmol), Pd(dba)2 (5 mmol), and [(tBu)3PH]BF4 (10 mmol) were added to a three-necked flask and substituted with Ar. Then 100 mL of toluene was added and the mixture was stirred at 100°C for 6 hours. Water was added to the reaction system, and the organic layer was extracted using toluene. The mixture was then dried over magnesium sulfate, and the solvent was removed by evaporation. The resulting crude product was purified by silica gel column chromatography (hexane / toluene mixed solvent) and recrystallization (ethanol / toluene mixed solvent) to obtain 12 mmol of yellow solid (yield 60%). FABMS analysis of the purified product confirmed that the molecular weight was 1003, confirming that intermediate C-19 had been obtained.

[0557] (6) Synthesis of Compound I-3 (Synthesis of intermediate I-3-3) JPEG2026076767000205.jpg56170

[0558] Intermediate I-3-1 (600 mmol), intermediate I-3-2 (600 mmol), tBuONa (800 mmol), Pd(dba)2 (60 mmol), and [(tBu)3PH]BF4 (120 mmol) were added to a three-necked flask and substituted with Ar. Then 2000 mL of toluene was added and the mixture was stirred at 100°C for 8 hours. Water was added to the reaction system, and the organic layer was extracted using toluene. The mixture was then dried over magnesium sulfate, and the solvent was removed by evaporation. The resulting crude product was purified by silica gel column chromatography (hexane / toluene mixed solvent) and recrystallization (ethanol / toluene mixed solvent) to obtain 390 mmol of white solid (yield 65%). FABMS analysis of the purified product confirmed that the molecular weight was 359, confirming that intermediate I-3-3 had been obtained.

[0559] (Synthesis of intermediates I-3-5) JPEG2026076767000206.jpg52170

[0560] Intermediate I-3-3 (359 mmol), intermediate I-3-4 (394 mmol), tBuONa (539 mmol), Pd(dba)2 (36 mmol), and [(tBu)3PH]BF4 (72 mmol) were added to a three-necked flask and substituted with Ar. Then 1000 mL of toluene was added and the mixture was stirred at 80°C for 18 hours. Water was added to the reaction system, and the organic layer was extracted using toluene. The mixture was then dried over magnesium sulfate, and the solvent was removed by evaporation. The resulting crude product was purified by silica gel column chromatography (hexane / toluene mixed solvent) and recrystallization (ethanol / toluene mixed solvent) to obtain 309 mmol of a white solid (yield 86%). FABMS analysis of the purified product confirmed that the molecular weight was 371, confirming that intermediate I-3-5 had been obtained.

[0561] (Synthesis of intermediate I-3-8) JPEG2026076767000207.jpg56170

[0562] Intermediate I-3-6 (1000 mmol), intermediate I-3-4 (1000 mmol), tBuONa (1200 mmol), Pd(dba)2 (100 mmol), and [(tBu)3PH]BF4 (200 mmol) were added to a three-necked flask and substituted with Ar. Then 2000 mL of toluene was added and the mixture was stirred at 100°C for 6 hours. Water was added to the reaction system, and the organic layer was extracted using toluene. The mixture was then dried over magnesium sulfate, and the solvent was removed by evaporation. The resulting crude product was purified by silica gel column chromatography (hexane / toluene mixed solvent) and recrystallization (ethanol / toluene mixed solvent) to obtain 800 mmol of white solid (80% yield). FABMS analysis of the purified product confirmed that the molecular weight was 291, confirming that intermediate I-3-7 had been obtained.

[0563] (Synthesis of intermediate I-3-9) JPEG2026076767000208.jpg44170

[0564] Intermediate I-3-8 (800 mmol) was added to a three-necked flask and substituted with Ar. Then, 1000 mL of DCM was added and the mixture was cooled to 0°C using ice water. Next, 1 M BBr3 solution was added to the reaction mixture using a dropping funnel over 1 hour, and the mixture was stirred at room temperature for 24 hours. Water was added to the reaction system, and the organic layer was extracted using DCM. The mixture was then dried over magnesium sulfate, and the solvent was removed by evaporation. The resulting crude product was purified by silica gel column chromatography (hexane / DCM mixed solvent) to obtain 655 mmol of a white solid (yield 81%). FABMS analysis of the purified product confirmed that the molecular weight was 277, confirming that intermediate I-3-9 had been obtained.

[0565] (Synthesis of intermediate I-3-10) JPEG2026076767000209.jpg61170

[0566] Intermediate I-3-5 (309 mmol), intermediate I-3-9 (309 mmol), K2CO3 (464 mmol), and 500 mL of NMP were added to a three-necked flask, and after ar substitution, the mixture was stirred at 150°C for 24 hours. Water was added to the reaction system, and the organic layer was extracted using toluene. The mixture was then dried over magnesium sulfate, and the solvent was removed by evaporation. The resulting crude product was purified by silica gel column chromatography (hexane / toluene mixed solvent) and recrystallization (ethanol / toluene mixed solvent) to obtain 244 mmol of a white solid (yield 79%). FABMS analysis of the purified product confirmed that the molecular weight was 629, confirming that intermediate I-3-10 had been obtained.

[0567] (Synthesis of intermediate I-3-12) JPEG2026076767000210.jpg56170

[0568] Intermediate I-3-10 (244 mmol), intermediate I-3-11 (244 mmol), K2CO3 (1708 mmol), and CuI (488 mmol) were added to a three-necked flask, and after ar substitution, the mixture was stirred at 210°C for 60 hours. Water was added to the reaction system, and the organic layer was extracted using toluene. The mixture was then dried over magnesium sulfate, and the solvent was removed by evaporation. The resulting crude product was purified by silica gel column chromatography (hexane / toluene mixed solvent) and recrystallization (ethanol / toluene mixed solvent) to obtain a white solid of 52 mmol (yield 21%). FABMS analysis of the purified product confirmed that the molecular weight was 703, confirming that intermediate I-3-12 had been obtained.

[0569] (Synthesis of Compound I-3) JPEG2026076767000211.jpg52170

[0570] Intermediate I-3-12 (52 mmol) was added to a three-necked flask and substituted with Ar. Then, 20 mL of ODCB was added to further dissolve the compound, followed by the addition of BI3 (206 mmol) and stirring at 140°C for 6 hours. The reaction mixture was dispersed and washed using a large amount of acetonitrile, and the solid was collected by filtration. The resulting crude product was purified by silica gel column chromatography (hexane / dichloromethane mixed solvent) and recrystallization (ethanol / toluene mixed solvent) to obtain 15 mmol of yellow solid (29% yield). FABMS analysis of the purified product confirmed a molecular weight of 719, confirming the acquisition of compound I-3.

[0571] 2. Fabrication and evaluation of light-emitting devices A light-emitting element of one embodiment, containing the condensed polycyclic compound of one embodiment in the light-emitting layer, was manufactured by the following method. The above-mentioned compounds B-11, G-7, C-21, C-16, C-19, and the I-3 condensed polycyclic compound were used as dopant materials for the light-emitting layer to manufacture the light-emitting elements of Examples 1 to 6. Comparative Examples 1 to 5 correspond to light-emitting elements manufactured using comparative compound X-1 to comparative compound X-5 as dopant materials for the light-emitting layer.

[0572] [Example Compounds] JPEG2026076767000212.jpg94156

[0573] JPEG2026076767000213.jpg69129

[0574] JPEG2026076767000214.jpg88153

[0575] [Comparative Compounds] JPEG2026076767000215.jpg75136

[0576] JPEG2026076767000216.jpg81153

[0577] JPEG2026076767000217.jpg159116

[0578] (Fabrication of light-emitting elements) A 150 nm thick first electrode is formed with ITO, a 10 nm thick hole injection layer is formed on the first electrode with HATCN (dipyradino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonnitrile), a 40 nm thick hole transport layer is formed on the hole injection layer with NPD (N,N'-di(1-naphthyl)-N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine), a 5 nm thick luminescence auxiliary layer is formed on the hole transport layer with mCP (1,3-bis(N-carbazolyl)benzene), and mC A 20 nm thick luminescent layer was formed by doping BP(3,3'-di(9H-carbazole-9-yl)-1,1'-biphenyl) with 1% of the example compound or comparative example compound. A 30 nm thick electron transport layer was formed on the luminescent layer using TPBi(2,2',2"-(1,3,5-Benzinetriyl)-tris(1-phenyl-1-H-benzimidazole)). An electron injection layer with a thickness of 0.5 nm was formed on the electron transport layer using LiF, and a 300 nm thick second electrode was formed on the electron injection layer using Al. Each layer was formed by vapor deposition under a vacuum atmosphere.

[0579] The compounds used in the fabrication of the light-emitting devices in the examples and comparative examples are disclosed below. The substances listed below are known substances, and commercially available products were manufactured and used in the fabrication of the devices.

[0580] JPEG2026076767000218.jpg100165

[0581] (Evaluation of physical properties of the compounds in the examples and comparative examples) Table 1 below shows the evaluated physical properties of the example compounds B-11, G-7, C-21, C-16, C-19, and I-3, and the comparative compounds X-1 to X-5. Table 1 below shows the emission wavelength (λ) of the vapor-deposited films of the example compounds and comparative compounds. film ), and fluorescence quantum yield were measured.

[0582] To evaluate the luminescence properties, a JASCO V-670 spcetrometer was used. A 20 wt% Dope film was deposited using PPF as a matrix and purified to a quArtz glass phase, and the fluorescence emission spectrum was measured. The fluorescence quantum yield was measured using the JASCOILF-835 integrating sphere system.

[0583] JPEG2026076767000219.jpg6896

[0584] [Table 1]

[0585] Referring to Table 1, it can be confirmed that the example compound has a higher fluorescence quantum yield compared to the comparative example compound. Therefore, it can be expected that the example compound will exhibit higher luminescence efficiency in the blue light wavelength region when applied to a light-emitting device compared to the comparative example compound.

[0586] (Evaluation of light-emitting element characteristics) Table 2 shows the evaluation results of the light-emitting elements for Examples 1 to 6 and Comparative Examples 1 to 5. Table 2 shows the maximum emission wavelength (λ) of the fabricated light-emitting elements. max ), the maximum value of the external quantum efficiency (EQE) max The luminance and relative lifetime (LT50) are shown for comparison. The voltage and current density of the light-emitting element were measured using a source meter (Keithley Instruments, 2400 series), and the luminance and external quantum efficiency were measured using an external quantum efficiency measuring device C9920-12 manufactured by Hamamatsu Photonics. The relative lifetime is calculated with an initial luminance of 100 cd / m². 2 The brightness half-life was evaluated and shown. The relative lifetime was shown relative to the results of Comparative Example 1.

[0587] [Table 2]

[0588] Referring to the results in Table 2, it can be seen that in the case of an example of a light-emitting device using a condensed polycyclic compound according to one embodiment of the present invention as a light-emitting material, the luminous efficiency and lifetime characteristics are improved compared to the comparative example.

[0589] In the case of the example compounds, each contains a first and second condensed core, each containing a condensed skeleton centered on a boron atom. The first condensed core may contain a structure in which six rings are condensed around a first boron atom, and the second condensed core may contain a structure in which five rings are condensed around a second boron atom. The example compounds may contain a 10-ring post-condensed ring formed by linking the first and second condensed cores together such that they share one benzene ring and one nitrogen atom. The example compounds, having a structure in which the first and second condensed cores are linked by a specified linking structure, can exhibit small full width at half maximum and Stokes shift characteristics, and can exhibit high emission quantum efficiency. As a result, the example compounds can exhibit improved thermally activated delayed fluorescence characteristics, and when the example compounds are applied to light-emitting devices, high luminescence efficiency and extended lifetime can be realized. The light-emitting device of one example can achieve high device efficiency, particularly in the blue light wavelength region, by including the condensed polycyclic compound of one example as an effective dopant for a thermally activated delayed fluorescence (TADF) light-emitting device.

[0590] Although all of the comparative compounds have a structure containing two boron atoms within a condensed polycyclic compound, it can be confirmed that, compared to the example compounds, both the luminous efficiency and lifetime characteristics of the light-emitting device were reduced when applied to the device.

[0591] Looking at Comparative Example 1, the comparative compound X-1 included in Comparative Example 1 has a different condensation structure compared to the example compound. As mentioned above, the example compound contains a first condensation core in which the ortho carbon atoms around the central boron atom are all linked via heteroatoms, but comparative compound X-1 does not contain such a skeleton. As a result, in comparative compound X-1, the LUMO orbital in the acceptor site is biased towards the upper skeleton centered on oxygen-boron-oxygen (OBO). Therefore, comparative compound X-1 undergoes greater structural relaxation in the excited state, reducing molecular stability, and if applied to a light-emitting device, the luminous efficiency and device lifetime of the light-emitting device will decrease. In contrast, the example compound can suppress structural relaxation in the excited state more than conventional compounds, and therefore has high stability when applied to a device.

[0592] In Comparative Examples 2, 4, and 5, comparative compounds X-2, X-4, and X-5, included in Comparative Examples 2, 4, and 5, have a condensation structure similar to the example compounds, but when applied to light-emitting devices, they showed a decrease in device lifetime and efficiency characteristics compared to the examples. In comparative compounds X-2, X-4, and X-5, R 13 Although it has a structure of a diphenylamine group or a carbazole group, in this case, R 10 If it contains a hydrogen atom or a diphenylamine group, the HOMO level becomes shallow, and the stability is relatively reduced when applied to the device. In this invention, a condensed polycyclic compound R 13 When R is a diphenylamine group or a carbazole group, 10 Stabilization of the compound can be achieved by excluding cases where the compound contains a hydrogen atom or a diphenylamine group.

[0593] Looking at Comparative Example 3, the comparative compound X-3 included in Comparative Example 3 has a different condensation structure compared to the example compound. As mentioned above, the example compound contains a first condensation core in which the ortho carbon atoms around the central boron atom are all linked via heteroatoms, but comparative compound X-3 does not contain such a skeleton. In the case of comparative compound X-3, the ortho carbon position is linked to the boron atom via a direct bond. In the case of a direct bond, it is significantly different from oxygen (O), nitrogen (N), and sulfur (S) atoms, so the twisting of the molecule increases, leading to a decrease in material stability. In the case of the condensed polycyclic compound of the present invention, the heteroatoms linking the ortho carbon atoms around the boron atom consist only of oxygen (O), nitrogen (N), and sulfur (S) atoms, so the twisting of the molecule is suppressed and the material stability is improved.

[0594] Although preferred embodiments of the present invention have been described so far with reference, a person skilled in the art or with ordinary knowledge in the art will understand that the present invention can be modified and altered in various ways without departing from the spirit and art domain of the invention as described in the claims below.

[0595] Therefore, the technical scope of the present invention is not limited to what is described in the detailed description of the specification, but should be determined by the claims. [Explanation of Symbols]

[0596] DD, DD-TD: Display device; ED: Light-emitting element; EL1: First electrode EL2: Second electrode HTR: Hole transport region EML: Emitting layer ETR: Electron transport region

Claims

1. First electrode and A second electrode is placed on the first electrode, A light-emitting element comprising a light-emitting layer disposed between the first electrode and the second electrode and containing a first compound represented by the following chemical formula 1: <Chemical formula 1> In the aforementioned chemical formula 1, X １ ~X ３ These are O, S, or NAr, respectively, independently. １ And, Ar １ This is a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms. R １ ~R １５ Each of these is independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms. R １３ When R is a diphenylamine group or a carbazole group, １０ If it is a hydrogen atom or contains a diphenylamine group, it is excluded. The first compound represented by the chemical formula 1 includes a structure in which at least one hydrogen atom is replaced by a deuterium atom.

2. The light-emitting layer includes a host and a dopant. The light-emitting element according to claim 1, wherein the dopant comprises the first compound represented by the chemical formula 1.

3. The first compound represented by chemical formula 1 is the light-emitting element according to claim 1, which is represented by any one of the following chemical formulas 2-1 to 2-4: <Chemical formula 2-1> <Chemical formula 2-2> <Chemical formula 2-3> <Chemical formula 2-4> In the aforementioned chemical formulas 2-1 to 2-4, X ２ａ to X ３ａ is each independently O or S, R ２１ ~R ２４ Each of these is independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms. n1 through n4 are each independent integers between 0 and 5, X １ , and R １ ~R １５ This is as defined in Chemical Formula 1 above.

4. The first compound represented by the chemical formula 1 is the light-emitting element according to claim 1, which is represented by any one of the following chemical formulas 3-1 to 3-4: <Chemical formula 3-1> <Chemical formula 3-2> <Chemical formula 3-3> <Chemical formula 3-4> In the aforementioned chemical formulas 3-1 to 3-4, R ２１ ~R ２４ Each of these is independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms. n1 through n4 are each independent integers between 0 and 5, In the aforementioned chemical formula 3-2, R １３ If R is a diphenylamine group or a carbazole group, １０ This is an unsubstituted alkyl group having 1 to 20 carbon atoms, or an unsubstituted aryl group having 6 to 20 carbon atoms forming a ring. X １ , and R １ ~R １５ This is as defined in Chemical Formula 1 above.

5. The first compound represented by the chemical formula 1 is a light-emitting element according to claim 1, represented by any one of the following chemical formulas 4-1 to 4-4: <Chemical formula 4-1> <Chemical formula 4-2> <Chemical formula 4-3> <Chemical formula 4-4> In the aforementioned chemical formulas 4-1 to 4-4, X １ａ ~X ２ａ Each is independently either O or S, R ３１ ~R ３４ Each of these is independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms. n11 through n14 are each independent integers between 0 and 5, X ３ , and R １ ~R １５ This is as defined in Chemical Formula 1 above.

6. The first compound represented by the chemical formula 1 is the light-emitting element according to claim 1, represented by the following chemical formula 5: <Chemical formula 5> In the aforementioned chemical formula 5, X １ｂ , X ２ｂ , and X ３ｂ Of these, at least one is represented by chemical formula 6-1 or chemical formula 6-2 below, and the remaining ones are independently O, S, or NAr. ２ And, Ar ２ This is a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms. R １ ~R １５ This is defined in the above chemical formula 1: <Chemical formula 6-1> <Chemical formula 6-2> In the aforementioned chemical formulas 6-1 and 6-2, R ４１ and R ４５ Each of these is independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms. n21, n23, and n25 are each independent integers between 0 and 5, n22 is an integer between 0 and 4, n24 is an integer between 0 and 3, This is the position where it is connected to the chemical formula 5.

7. X １ ~X ３ Each is independently O or NAr ３ And, Ar ３ The light-emitting element according to claim 1, wherein is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms in a ring.

8. In the aforementioned chemical formula 1, R １３ If R is a diphenylamine group or a carbazole group, １０ These are substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 ring-forming carbon atoms, or substituted or unsubstituted heteroaryl groups having 2 to 30 ring-forming carbon atoms. R １０ The light-emitting element according to claim 3, wherein, if substituted, the substituent is a deuterium atom, a cyano group, an unsubstituted alkyl group having 1 to 10 carbon atoms, an unsubstituted aryl group having 6 to 15 carbon atoms, or an unsubstituted heteroaryl group having 2 to 15 carbon atoms.

9. The light-emitting layer further comprises at least one of the following: a second compound represented by the chemical formula HT-1, a third compound represented by the chemical formula ET-1, and a fourth compound represented by the chemical formula D-1, according to claim 1: <Chemical formula HT-1> In the aforementioned chemical formula HT-1, M １ ~M ８ Each is independently N or CR ５１ And, L １ This is a directly linked, substituted or unsubstituted ring-forming arylene group with 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heteroarylene group with 2 to 30 carbon atoms. Y ａ Direct bonding, CR ５２ R ５３ , or SiR ５４ R ５５ And, Ar ａ This is a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms. R ５１ ~R ５５ Each of these groups is independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted thio group, a substituted or unsubstituted oxy group, a substituted or unsubstituted amine group, a substituted or unsubstituted boron group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted ring-forming aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted ring-forming heteroaryl group having 2 to 60 carbon atoms, or is bonded to an adjacent group to form a ring: <Chemical formula ET-1> In the aforementioned chemical formula ET-1, Z ａ ~Z ｃ Of these, at least one is N, and the rest are CR ５６ And, R ５６ This is a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 ring-forming carbon atoms. b1 to b3 are each independent integers between 0 and 10, Ar ｂ ~Ar ｄ Each of these is independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms. L ２ ~L ４ These are, independently, directly bonded, substituted, or unsubstituted arylene groups having 6 to 30 ring-forming carbon atoms, or substituted or unsubstituted heteroarylene groups having 2 to 30 ring-forming carbon atoms: <Chemical formula D-1> In the aforementioned chemical formula D-1, Q １ ~Q ４ Each is independently either C or N, C1 to C4 are each independently a substituted or unsubstituted hydrocarbon ring having 5 to 30 ring-forming carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 30 ring-forming carbon atoms. X １１ ~X １４ Each can be directly connected or And, L １１ ~L １３ Each is independent, directly connected, A substituted or unsubstituted divalent alkyl group having 1 to 20 ring-forming carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring-forming carbon atoms. b11 to b13 are each independently either 0 or 1. R ６１ ~R ６６ Each of these is independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted thio group, a substituted or unsubstituted oxy group, a substituted or unsubstituted amine group, a substituted or unsubstituted boron group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, an alkenyl group having 2 to 20 substituted or unsubstituted carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 ring-forming carbon atoms. d1 through d4 are each independent integers between 0 and 4, inclusive.

10. The first compound represented by the chemical formula 1 comprises at least one compound from the following first group of compounds, according to claim 1: <First compound group> 。

11. Base layer and A circuit layer placed on the base layer, The circuit layer includes a display element layer which includes a light-emitting element, The light-emitting element is an electronic device comprising a first electrode, a second electrode placed on the first electrode, and a light-emitting layer placed between the first electrode and the second electrode and containing a first compound represented by the following chemical formula 1: <Chemical formula 1> In the aforementioned chemical formula 1, X １ ~X ３ These are O, S, or NAr, respectively, independently. １ And, Ar １ This is a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms. R １ and R １５ Each of these is independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms. R １３ When R is a diphenylamine group or a carbazole group, １０ If it is a hydrogen atom or contains a diphenylamine group, it is excluded. The first compound represented by the chemical formula 1 includes a structure in which at least one hydrogen atom is replaced by a deuterium atom.

12. The light-emitting element further includes a capping layer disposed on the second electrode, The electronic device according to claim 11, wherein the refractive index of the capping layer is 1.6 or more for light in the wavelength range of 550 nm to 660 nm.

13. Displaced on the aforementioned display element layer, further includes a color control unit containing quantum dots, The light-emitting element emits a first color of light, The aforementioned optical control layer is A first color control unit including a first quantum dot that converts a first color light into a second color light in a longer wavelength region than the first color light, A second optical control unit including a second quantum dot that converts the first color light into a third color light in a longer wavelength region than the first color light and the second color light, The electronic device according to claim 11, further comprising a third color control unit that transmits the first color light.

14. The optical control layer further includes a color filter layer disposed on top of the optical control layer, The aforementioned color filter layer is A first filter that transmits the second color light, A second filter that transmits the aforementioned third color light, The electronic device according to claim 13, further comprising a third filter that transmits the first color light.

15. The electronic device according to claim 11, wherein the electronic device is selected from among large display devices such as televisions, monitors, and external billboards, personal computers, laptop computers, personal information terminals, vehicle display devices, game consoles, portable electronic devices, and small to medium-sized display devices such as cameras.

16. The condensed polycyclic compound represented by the following chemical formula 1: <Chemical formula 1> In the aforementioned chemical formula 1, X １ ~X ３ These are O, S, or NAr, respectively, independently. １ And, Ar １ This is a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms. R １ and R １５ Each of these is independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms. R １３ When R is a diphenylamine group or a carbazole group, １０ If it is a hydrogen atom or contains a diphenylamine group, it is excluded. The condensed polycyclic compound represented by the chemical formula 1 includes a structure in which at least one hydrogen atom is replaced by a deuterium atom.

17. The condensed polycyclic compound represented by chemical formula 1 is the condensed polycyclic compound according to claim 16, which is represented by any one of the following chemical formulas 2-1 to 2-4: <Chemical formula 2-1> <Chemical formula 2-2> <Chemical formula 2-3> <Chemical formula 2-4> In the aforementioned chemical formulas 2-1 to 2-4, X ２ａ to X ３ａ are each independently O or S, R ２１ and R ２４ Each of these is independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms. n1 through n4 are each independent integers between 0 and 5, X １ , and R １ ~R １５ This is as defined in Chemical Formula 1 above.

18. The condensed polycyclic compound represented by chemical formula 1 is the condensed polycyclic compound according to claim 16, which is represented by any one of the following chemical formulas 3-1 to 3-4: <Chemical formula 3-1> <Chemical formula 3-2> <Chemical formula 3-3> <Chemical formula 3-4> In the aforementioned chemical formulas 3-1 to 3-4, R ２１ and R ２４ are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, n1 through n4 are each independent integers between 0 and 5, In the aforementioned chemical formula 3-2, R １３ If R is a diphenylamine group or a carbazole group, １０ This is an unsubstituted alkyl group having 1 to 20 carbon atoms, or an unsubstituted aryl group having 6 to 20 carbon atoms forming a ring. X １ , and R １ ~R １５ This is as defined in Chemical Formula 1 above.

19. The condensed polycyclic compound represented by chemical formula 1 is the condensed polycyclic compound according to claim 16, which is represented by any one of the following chemical formulas 4-1 to 4-4: <Chemical formula 4-1> <Chemical formula 4-2> <Chemical formula 4-3> <Chemical formula 4-4> In the aforementioned chemical formulas 4-1 to 4-4, X １ａ ~X ２ａ Each is independently either O or S, R ３１ and R ３４ Each of these is independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms. n11 through n14 are each independent integers between 0 and 5, X ３ , and R １ ~R １５ This is as defined in Chemical Formula 1 above.

20. The condensed polycyclic compound represented by the chemical formula 1 is the condensed polycyclic compound according to claim 16, comprising at least one compound from the following first group of compounds: <First compound group> 。

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