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

Abstract

To provide a light-emitting element with improved element lifespan. [Solution] The 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, which contains a first compound represented by the following formula. JPEG2026139258000304.jpg72170

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] Organic electroluminescent display devices, which include organic electroluminescent elements, are used as display devices within electronic equipment. Organic electroluminescent displays are display devices that include so-called self-emissive light-emitting elements, which inject holes and electrons injected from the first and second electrodes into the light-emitting layer, causing the light-emitting material of the light-emitting layer to emit light and realize a display.

[0003] When applying light-emitting elements to display devices, improvements in efficiency and lifespan are required, and there is a continuous need for the development of light-emitting element materials that can stably achieve these improvements. [Overview of the project] [Problems that the invention aims to solve]

[0004] The objective of the present invention is to provide a light-emitting element with improved element lifespan.

[0005] Another object of the present invention is to provide a condensed polycyclic compound that can improve the device lifetime of a light-emitting element.

[0006] Another object of the present invention is to provide an electronic device that includes a light-emitting element with improved element lifetime and has excellent display quality. [Means for solving the problem]

[0007] 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.

[0008] [Chemical formula 1] JPEG2026139258000002.jpg72170

[0009] In Chemical Formula 1, R 1 to R 11 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano 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 are bonded to each other with adjacent groups to form a ring; two or three consecutive groups selected from R 1 to R 4 and R 8 to R 11 are each a position to be linked to the following Chemical Formula 2, and X 1 and X 2 are each independently O, S, or Se, or are represented by any one of the following Chemical Formulas 3 to 5.

[0010] [Chemical Formula 2] JPEG2026139258000003.jpg53170

[0011] In Chemical Formula 2, R 12 to R 19 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano 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 are bonded to each other with adjacent groups to form a ring, X 3 and X 4 are each independently O, S, or Se, or are represented by any one of the following Chemical Formulas 3 to 5, JPEG2026139258000004.jpg5170 is a position to be linked to Chemical Formula 1, JPEG2026139258000005.jpg3170 is a position to be linked to Chemical Formula 1, or to be linked to R 12 in said Chemical Formula 2.

[0012] [Chemical formula 3] JPEG2026139258000006.jpg51170[Chemical formula 4] JPEG2026139258000007.jpg28170[Chemical formula 5] JPEG2026139258000008.jpg23170

[0013] In the aforementioned chemical formulas 3 to 5, JPEG2026139258000009.jpg5170 is the position linked to chemical formula 1 or chemical formula 2, and R 20 ~R 26 Each of these is independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano 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 20 ~R 24 At least one of them is a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, Ar is a substituted or unsubstituted aryl group having 10 to 30 ring-forming carbon atoms, Z is a carbon atom or a silicon atom, and if Z is a silicon atom, then R 25 and R 26 It is not a hydrogen atom, but X 1 ~X 4 At least one of them is represented by the above chemical formula 3, and in the above chemical formula 1, X 1 and X 2 When represented by the above chemical formula 4, cases in the above chemical formula 4 where Ar is a fluorenyl group or a heteroaryl group are excluded, and in the above chemical formula 1, X 1 and X 2 When any one of them is represented by the chemical formula 3, in the chemical formula 3, R 20 and R 24 If any one of them is not a substituted or unsubstituted aryl group with 6 to 30 carbon atoms forming a ring, it is excluded.

[0014] The light-emitting layer comprises a host and a dopant, and the dopant may comprise a first compound represented by the chemical formula 1.

[0015] The aforementioned X 1 ~X 4 At least two of these can be represented by the chemical formula 3.

[0016] The aforementioned chemical formula 3 can also be represented by the following chemical formula 3-1 or chemical formula 3-2.

[0017] [Chemical formula 3-1] JPEG2026139258000010.jpg54170[Chemical formula 3-2] JPEG2026139258000011.jpg57170

[0018] In chemical formulas 3-1 and 3-2, JPEG2026139258000012.jpg5170 is the position linked to chemical formula 2 or chemical formula 3, and R 31 ~R 35 , and R 41 ~R 50 Each of these can independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano 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.

[0019] In the above chemical formulas 3-1 and 3-2, R 21 ~R 24 The same explanation as the definition of chemical formula 3 above can be applied to this.

[0020] The first compound represented by the aforementioned chemical formula 1 can also be represented by the following chemical formulas 1-1-1 or 1-1-2.

[0021] [Chemical formula 1-1-1] JPEG2026139258000013.jpg93170[Chemical formula 1-1-2] JPEG2026139258000014.jpg93170

[0022] In the aforementioned chemical formulas 1-1-1 and 1-1-2, X 2a is O, S, or Se, or represented by the aforementioned chemical formula 4 or chemical formula 5, R 24a R is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms in a ring, 51 ~R 55 , R 61 ~R 70 , R 21b ~R 24b , and R 21c ~R 24c Each of these can independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano 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.

[0023] In the above chemical formulas 1-1-1 and 1-1-2, R 1 ~R 11 The same explanation as the definition of chemical formula 1 above can be applied to this.

[0024] The first compound represented by the aforementioned chemical formula 1 can also be represented by the following chemical formulas 1-2.

[0025] [Chemical formula 1-2] JPEG2026139258000015.jpg93170

[0026] In chemical formula 1-2, R 71 ~R 90 , R 21d ~R 23d , and R 21e ~R 23e Each of these can independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano 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.

[0027] In the above chemical formula 1-2, R 1 ~R 11 The same explanation as the definition of chemical formula 1 above can be applied to this.

[0028] The first compound represented by chemical formula 1 can be represented by any one of the following chemical formulas 1-3-1 to 1-3-3.

[0029] [Chemical formula 1-3-1] JPEG2026139258000016.jpg93170[Chemical formula 1-3-2] JPEG2026139258000017.jpg93170[Chemical formula 1-3-3] JPEG2026139258000018.jpg93170

[0030] In chemical formulas 1-3-1 to 1-3-3, X 3a , X 3b , X 4a , and X 4b Each of these is independently O, S, or Se, or is represented by one of the chemical formulas 3 to 5, and R 12a ~R 19a , and R 12b ~R 19b Each of these can independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano 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.

[0031] In the aforementioned chemical formulas 1-3-1 to 1-3-3, X 1 , X 2 , and R 5 ~R 7 The same explanation as the definition of chemical formula 1 above applies to this.

[0032] The first compound represented by chemical formula 1 can be represented by any one of the following chemical formulas 1-4-1 to 1-4-3.

[0033] [Chemical formula 1-4-1] JPEG2026139258000019.jpg93170[Chemical formula 1-4-2] JPEG2026139258000020.jpg93170[Chemical formula 1-4-3] JPEG2026139258000021.jpg93170

[0034] In chemical formulas 1-4-1 to 1-4-3, X 3a , X 3b , X 4a , and X 4b Each of these is independently O, S, or Se, or is represented by one of the chemical formulas 3 to 5, and R 12a ~R 19a , and R 12b ~R 19b Each of these can independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano 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.

[0035] In the above chemical formulas 1-4-1 to 1-4-3, X 1 , X 2 , and R 5 ~R 7 The same explanation as the definition of chemical formula 1 above applies to this.

[0036] 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.

[0037] [Chemical formula HT-1] JPEG2026139258000022.jpg54170

[0038] In the aforementioned chemical formula HT-1, M1 to M8 are each independently N or CR.a1 , wherein L1 is a direct linkage, 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, and Y a is a direct bond, CR a2 R a3 , or SiR a4 R a5 , and Ar a 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, and R a1 to R a5 are each 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 30 ring-forming carbon atoms, or may be bonded to each other with an adjacent group to form a ring.

[0039] [Chemical formula ET-1] JPEG2026139258000023.jpg56170

[0040] In the above chemical formula ET-1, at least one of Z a to Z c is N, and the remainder are CR a6 , R a6 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 independently an integer of 0 to 10. Ar b to Ar deach independently represents 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 L2 to L4 each independently may be a direct bond, 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.

[0041] [Chemical Formula D-1] JPEG2026139258000024.jpg76170

[0042] In the above Chemical Formula D-1, Q1 to Q4 each independently are C or N, C1 to C4 each independently are 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, and X 11 to X 14 each independently are a direct bond or JPEG2026139258000025.jpg6170, and L 11 to L 13 each independently are a direct bond, JPEG2026139258000026.jpg23170a substituted or unsubstituted divalent alkyl group having 1 to 20 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 each independently are 0 or 1, and R b1 to R b6Each 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.

[0043] 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 may include 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 the chemical formula 1.

[0044] 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.

[0045] 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.

[0046] 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.

[0047] The aforementioned electronic device may 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 information terminals, vehicle display devices, game consoles, portable electronic devices, and cameras.

[0048] A condensed polycyclic compound according to one embodiment of the present invention is represented by the above chemical formula 1. [Effects of the Invention]

[0049] The light-emitting element of one embodiment may exhibit improved element characteristics with a longer lifespan.

[0050] The condensed polycyclic compound of one embodiment can be included in the light-emitting layer of a light-emitting device and contribute to extending the lifespan of the device.

[0051] The electronic device of one embodiment may exhibit excellent display quality and improved reliability characteristics. [Brief explanation of the drawing]

[0052] [Figure 1] This is a block diagram of an electronic device according to one embodiment. [Figure 2] This is a schematic diagram of an electronic device according to one embodiment. [Figure 3] This is a plan view of a display device according to one embodiment of the present invention. [Figure 4] This is a cross-sectional view of a display device 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 schematic cross-sectional view showing a light-emitting element according to one embodiment of the present invention. [Figure 8] This is a schematic cross-sectional view showing a light-emitting element according to one embodiment of the present invention. [Figure 9] This is a cross-sectional view of a display module according to one embodiment of the present invention. [Figure 10]This is a cross-sectional view of a display module according to one embodiment of the present invention. [Figure 11] This is a cross-sectional view showing a display module according to one embodiment of the present invention. [Figure 12] This is a cross-sectional view showing a display module according to one embodiment of the present invention. [Figure 13] This is a perspective view of an electronic device according to one embodiment. [Figure 14] This is a perspective view of an electronic device according to one embodiment. [Figure 15] This figure shows a vehicle on which a display device according to one embodiment is installed. [Figure 16] This figure shows the three-dimensional molecular model of the comparative example compound. [Figure 17a] This figure shows a three-dimensional molecular model of the example compound. [Figure 17b] This figure shows a three-dimensional molecular model of the example compound. [Figure 18a] This figure shows a three-dimensional molecular model of the example compound. [Figure 18b] This figure shows a three-dimensional molecular model of the example compound. [Modes for carrying out the invention]

[0053] 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.

[0054] 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 they are clearly meant to be different in context.

[0055] 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.

[0056] 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.

[0057] In this specification, "substituted or unsubstituted" may mean 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.

[0058] 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.

[0059] 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."

[0060] Examples of halogen atoms in this specification include fluorine, chlorine, Brom, or iodine atoms.

[0061] 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, n Examples of nonacosyl groups include, but are not limited to, pentacosyl, n-hexacosyl, n-heptacosyl, n-octacosyl, n-nonacosyl, and n-triacontyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4-t-butylcyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, norbornyl, 1-adamantyl, 2-adamantyl, isobornyl, and bicycloheptyl groups.

[0062] 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 groups, 1-butenyl groups, 1-pentenyl groups, 1,3-butadienylaryl groups, styrenyl groups, and styrylvinyl groups.

[0063] 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.

[0064] 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.

[0065] 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.

[0066] In this specification, the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure. Examples of substitutions of the fluorenyl group are as follows, but are not limited to these. JPEG2026139258000027.jpg28170

[0067] 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.

[0068] 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.

[0069] 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.

[0070] 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, pyradadinyl group, pyrazinyl group, quinolyl group, quinazolyl group, quinoxalinyl group, phenoxadinyl 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 group, N-alkylcarbazolyl group, benzoxazolyl group, benzimidazolyl group, benzothiazolyl group, benzocarbazolyl group, benzothiophenyl group, dibenzothiophenyl group, thienothiophenyl group, benzofuranyl group, phenanthrolinyl group, thiazolyl group, isoxazolyl group, oxazolyl group, oxadiazolyl group, thiadiazolyl group, phenothiazinyl group, dibenzosilolyl group, and dibenzofuranyl group.

[0071] 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.

[0072] 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.

[0073] 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. JPEG2026139258000028.jpg34170

[0074] 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.

[0075] 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.

[0076] 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, methoxy, ethoxy, n-propoxy, isopropoxy, butoxy, pentyloxy, hexyloxy, octyloxy, nonyloxy, decyloxy, and benzyloxy.

[0077] 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.

[0078] 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 alkylamine groups and arylamine groups. Examples of amine groups include, but are not limited to, methylamine groups, dimethylamine groups, phenylamine groups, diphenylamine groups, naphthylamine groups, and 9-methyl-anthracenylamine groups.

[0079] In this specification, among alkylthio groups, alkylsulfoxy groups, alkylaryl groups, alkylamino groups, alkylboron groups, alkylsilyl groups, and alkylamine groups, alkyl groups are as exemplified above.

[0080] 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 above.

[0081] In this specification, direct bonding may mean a single bond.

[0082] On the other hand, in this specification, JPEG2026139258000029.jpg14170 indicates the position where the images are concatenated.

[0083] Hereinafter, an embodiment of the present invention will be described with reference to the drawings.

[0084] Figure 1 is a block diagram of an electronic device according to one embodiment. Referring to Figure 1, the electronic device EA according to one embodiment may include a display module DM, a processor PR, a memory MR, and a power supply module PM.

[0085] A processor PR may include at least one of the following: a central processing unit (CPU), an application processor (AP), a graphics processing unit (GPU), a communication processor (CP), an image signal processor (ISP), or a controller.

[0086] Memory MR may store data information necessary for the operation of the processor PR and the display module DM. When the processor PR executes an application stored in memory MR, video data signals and / or input control signals are transmitted to the display module DM, which can process the provided signals and output video information via a display screen. The display module DM may include a display panel for displaying video.

[0087] The power module PM may include a power supply module such as a power adapter or battery device, and a power conversion module that converts the power supplied by the power supply module to generate the power necessary for the operation of the electronic device EA.

[0088] At least one of the components of the electronic device EA described above may be included in a display module according to one embodiment described later, and in a display device according to one embodiment including the same. Furthermore, some of the individual modules functionally contained within a single module may be included in the display device, while others may be provided separately from the display device. For example, the display device may include a display module DM, while the processor PR, memory MR, and power supply module PM may be provided in the form of other devices within the electronic device EA rather than in the display device.

[0089] Figure 2 is a schematic diagram of one example of various electronic devices.

[0090] Referring to Figure 2, the various electronic devices including the display module according to one embodiment may include not only electronic devices for displaying images such as smartphones EA_1a, tablet PCs EA_1b, laptops EA_1c, televisions EA_1d, and desk monitors EA_1e, but also wearable electronic devices such as smart glasses EA_2a, head-mounted displays EA_2b, and smartwatches EA_2c, as well as automotive electronic devices EA_3 such as CIDs (Center Information Displays) and rearview mirror displays located on the instrument panel, center fascia, and dashboard of an automobile.

[0091] Figure 3 is a plan view showing one embodiment of the display module DM. Figure 4 is a cross-sectional view of the display module DM according to one embodiment. Figure 4 is a cross-sectional view showing the portion corresponding to the line I-I' in Figure 3.

[0092] The display module DM may include a plurality of light-emitting elements ED-1, ED-2, and ED-3. In one embodiment, the display module DM may include a display panel DP containing a plurality of light-emitting elements ED-1, ED-2, and ED-3, and a light-emitting layer PP disposed on the display panel DP.

[0093] 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 films PDL, and a sealing layer TFE positioned on top of the light-emitting elements ED-1, ED-2, and ED-3.

[0094] 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.

[0095] In one embodiment, the circuit layer DP-CL is located 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. 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 5 to 9, 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.

[0096] The optical layer PP is positioned on the display panel DP and can control the reflected light from the display panel DP due to external light. The optical layer PP may include, for example, a polarizing layer or a color filter layer. Contrary to the illustration, the optical layer PP may be omitted from the display module DM in one embodiment.

[0097] 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.

[0098] A display module DM 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.

[0099] Figure 4 shows an embodiment in which the light-emitting layers EML-R, EML-G, and EML-B of the light-emitting elements ED-1, ED-2, and ED-3 are arranged within the opening OH defined in the pixel-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 4, the hole transport region HTR and electron transport region ETR may be patterned and provided inside the opening OH defined in the pixel-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 the light-emitting elements ED-1, ED-2, and ED-3 may be patterned and provided by an inkjet printing method.

[0100] 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.

[0101] 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 include, but is not limited to, silicon nitride, silicon oxynitride, silicon oxide, titanium oxide, or aluminum oxide. The encapsulating organic film may include acrylic compounds, epoxy compounds, etc. The encapsulating organic film may include, but is not limited to, photopolymerizable organic materials.

[0102] The sealing layer TFE may be placed on top of the second electrode EL2 and fill the opening OH.

[0103] Referring to Figures 3 and 4, the display module DM 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 by the light-emitting elements ED-1, ED-2, and ED-3, respectively, is emitted. The display module DM may include a first emitting region PXA-R, a second emitting region PXA-G, and a third emitting region PXA-B that are spaced apart from each other on a plane.

[0104] The first to third light-emitting regions PXA-R, PXA-G, and PXA-B may each be regions separated by a pixel-defining film PPL. The non-light-emitting region NPXA is the region between adjacent light-emitting regions PXA-R, PXA-G, and PXA-B, and may correspond to a pixel-defining film PDL. In this specification, each of the light-emitting regions PXA-R, PXA-G, and PXA-B may correspond to a pixel. The pixel-defining film PDL may separate the light-emitting elements ED-1, ED-2, and ED-3. The light-emitting layers EML-R, EML-G, and EML-B of the light-emitting elements ED-1, ED-2, and ED-3 may be located in and separated by an aperture OH defined in the pixel-defining film PDL.

[0105] 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 module DM of one embodiment shown in Figures 3 and 4 exemplifies three light-emitting regions PXA-R, PXA-G, and PXA-B that emit red, green, and blue light, respectively. For example, the first light-emitting region PXA-R may be called the red light-emitting region, the second light-emitting region PXA-G the green light-emitting region, and the third light-emitting region PXA-B the blue light-emitting region.

[0106] In one embodiment of the display module DM, 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 module DM 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. That is, the red light-emitting region PXA-R, the green light-emitting region PXA-G, and the blue light-emitting region PXA-B 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.

[0107] 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.

[0108] In one embodiment, the light-emitting regions PXA-R, PXA-G, and PXA-B in the display module DM may be arranged in a striped pattern. Referring to Figure 3, multiple first light-emitting regions PXA-R, multiple second light-emitting regions PXA-G, and multiple third light-emitting regions PXA-B may be aligned along the second directional axis DR2. Alternatively, the first light-emitting region PXA-R, the second light-emitting region PXA-G, and the third light-emitting region PXA-B may be arranged alternately along the first directional axis DR1.

[0109] Although Figures 3 and 4 show that the areas of the light-emitting regions PXA-R, PXA-G, and PXA-B are all similar, the embodiments 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. 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.

[0110] The arrangement of the light-emitting regions PXA-R, PXA-G, and PXA-B is not limited to that shown in Figure 3. The order in which the first light-emitting region PXA-R, the second light-emitting region PXA-G, and the third light-emitting region PXA-B are arranged is provided in various combinations depending on the display quality characteristics required from the display module DM. For example, the arrangement of the light-emitting regions PXA-R, PXA-G, and PXA-B is Pentile. TM ) Arrangement form, or diamond (Diamond Pixel) TM ) It may have the form of an array.

[0111] 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 second light-emitting region PXA-G, which is a green light-emitting region, may be smaller than the area of ​​the third light-emitting region PXA-B, which is a blue light-emitting region, but the embodiment is not limited to this.

[0112] Figures 5 to 8 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.

[0113] 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.

[0114] Figure 6 shows a cross-sectional view of an embodiment of a light-emitting element ED, compared to Figure 5, 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 7 also shows a cross-sectional view of an embodiment of a light-emitting element ED, compared to Figure 5, 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 8 shows a cross-sectional view of an embodiment of a light-emitting element ED, compared to Figure 6, in which a capping layer CPL is placed on the second electrode EL2.

[0115] One embodiment of 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 one embodiment of the light-emitting element ED, 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 one embodiment of the light-emitting element ED, the light-emitting layer EML may contain the condensed polycyclic compound of the embodiment.

[0116] 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.

[0117] 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 above-mentioned material, 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 those described above, 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 approximately 700 Å to approximately 10000 Å. For example, the thickness of the first electrode EL1 may be approximately 1000 Å to approximately 3000 Å.

[0118] The hole transport region (HTR) is provided on the first electrode EL1. The hole transport region (HTR) may include at least one of a hole injection layer (HIL), a hole transport layer (HTL), a hole buffer layer 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.

[0119] 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.

[0120] 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.

[0121] 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).

[0122] The hole transport region (HTR) may contain a compound represented by the following chemical formula H-1.

[0123] [Chemical formula H-1] JPEG2026139258000030.jpg33170

[0124] In Chemical Formula H-1, L1 and L2 may each independently be a direct bond, 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. a and b may each independently be an integer of 0 or more and 10 or less. Meanwhile, when a or b is an integer of 2 or more, a plurality of L1 and L2 may each 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.

[0125] In Chemical Formula H-1, Ar1 to Ar2 may each independently be a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms. Also, in Chemical Formula H-1, Ar3 may be a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms.

[0126] The compound represented by Chemical Formula H-1 may be a monoamine compound. Alternatively, the compound represented by Chemical Formula H-2 may be a diamine compound in which at least one of Ar1 to Ar3 comprises an amine group as a substituent. Alternatively, the compound represented by Chemical Formula H-1 may be a carbazole-based compound in which at least one of Ar1 to Ar2 comprises a substituted or unsubstituted carbazole group, or a fluorene-based compound in which at least one of Ar1 to Ar2 comprises a substituted or unsubstituted fluorene group.

[0127] The compound represented by Chemical Formula H-1 may be represented by any one of the compounds in the following compound group H. However, the compounds listed in the following compound group H are exemplary, and the compound represented by Chemical Formula H-1 is not limited to those shown in the following compound group H.

[0128] [Compound Group H] JPEG2026139258000031.jpg255165

[0129] 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.

[0130] 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]), and HMTPD (4,4'-bis[N,N'-(3-tolyl)amino]-3,3'-dimethylbiphenyl).

[0131] 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).

[0132] In one embodiment, the hole transport region (HTR) may include any one of the compounds in the second group of compounds described below.

[0133] The hole transport region HTR comprises the hole transport region compound described above, and at least one of the hole injection layer HIL, hole transport layer HTL, and electron blocking layer EBL.

[0134] 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.

[0135] 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.

[0136] 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 electron injection from the electron transport region (ETR) to the hole transport region (HTR).

[0137] 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.

[0138] In one embodiment, the light-emitting element ED contains 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 contains the condensed polycyclic compound of one embodiment. In one embodiment, the light-emitting layer EMLML contains the condensed polycyclic compound of one embodiment as a dopant. The condensed polycyclic compound of one embodiment is the dopant material of 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.

[0139] The condensed polycyclic compound of one embodiment includes first to third condensed cores, each containing a boron-centered condensed skeleton. In the condensed polycyclic compound of one embodiment, the second and third condensed cores may each be linked to the first condensed core by sharing one benzene ring. The second condensed core may be linked to the first condensed core by sharing one benzene ring, while the third condensed core may be linked to the first condensed core by sharing one different benzene ring. The condensed polycyclic compound of the present invention, having a structure in which the first to third 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.

[0140] In one embodiment, the first condensed core may have a structure in which five rings are condensed around a first boron atom, a first atom, and a second atom. In one embodiment, the first atom and the second atom may each independently be a nitrogen atom, a carbon atom, or a silicon atom. The first condensed core may form five condensed rings by linking three substituted or unsubstituted benzene rings via a first boron atom, a first atom, and a second atom. More specifically, in the three benzene rings included in the first condensed core, the three benzene rings may be linked around a first boron atom, the first and second benzene rings may be linked via a first atom, and the second and third benzene rings may be linked via a second atom. In the first condensed core, the first benzene ring may be shared with the second condensed core described above, and the third benzene ring may be shared with the third condensed core described above. In other words, the first condensed core and the second condensed core can be linked to each other by sharing a first benzene ring, and the first condensed core and the third condensed core can be linked to each other by sharing a third benzene ring.

[0141] In one embodiment, the second condensed core may have a structure in which five rings are condensed around a second boron atom, a third atom, and a fourth atom. In one embodiment, the third and fourth atoms may each independently be an oxygen atom, a sulfur atom, a selenium atom, a nitrogen atom, a carbon atom, or a silicon atom. The second condensed core may form five condensed rings by linking three substituted or unsubstituted benzene rings via a second boron atom, a third atom, and a fourth atom. In the three benzene rings included in the second condensed core, the three benzene rings are linked around the second boron atom, and the first and fourth benzene rings may be linked via the third atom. The remaining fifth benzene ring may be linked to the first or fourth benzene ring via the fourth atom. In the second condensed core, the first benzene ring may be shared with the first condensed core described above.

[0142] In one embodiment, the third condensed core may have a structure in which five rings are condensed around a third boron atom, a fifth atom, and a sixth atom. In one embodiment, the fifth and sixth atoms may each be independently an oxygen atom, a sulfur atom, a selenium atom, a nitrogen atom, a carbon atom, or a silicon atom. The third condensed core may form five condensed rings by linking three substituted or unsubstituted benzene rings via the third boron atom, the fifth atom, and the sixth atom. In the three benzene rings included in the third condensed core, the three benzene rings are linked around the third boron atom, and the third and sixth benzene rings may be linked via the fifth atom. The remaining seventh benzene ring may be linked to the third or sixth benzene ring via the sixth atom. In the third condensed core, the third benzene ring may be shared with the first condensed core described above.

[0143] In one example of a condensed polycyclic compound, the first condensation core is represented by the following structure S1, the second condensation core by the following structure S2a or structure S2b, and the third condensation core by the following structure S3a or S3b. For the sake of clarity, substituents linked to the benzene ring are omitted in the following structures S1, S2a, S2b, S3a, and S3b. JPEG2026139258000032.jpg86170

[0144] In structure S1, the B1 ring corresponds to the first benzene ring described above, the B2 ring corresponds to the second benzene ring described above, and the B3 ring can correspond to the third benzene ring described above. Also, X 1 and X 2 Each of these atoms may independently be an oxygen atom, a sulfur atom, or a selenium atom, or a substituted nitrogen atom represented by chemical formula 3 or chemical formula 4 described later, or a substituted carbon atom or a substituted silicon atom represented by chemical formula 5 described later.

[0145] Structure S2a shows the case where the fifth benzene ring is linked to the first benzene ring via the fourth atom in the second condensation core, and structure S2b shows the case where the fifth benzene ring is linked to the fourth benzene ring via the fourth atom in the second condensation core. Structure S3a shows the case where the seventh benzene ring is linked to the third benzene ring via the sixth atom in the third condensation core, and structure S3b shows the case where the seventh benzene ring is linked to the sixth benzene ring via the sixth atom in the second condensation core.

[0146] In structures S2a and S2b, the B1 ring may correspond to the first benzene ring described above, the B4 ring may correspond to the fourth benzene ring described above, and the B5 ring may correspond to the fifth benzene ring described above. In structures S3a and S3b, the B3 ring may correspond to the third benzene ring described above, the B6 ring may correspond to the sixth benzene ring described above, and the B7 ring may correspond to the seventh benzene ring described above.

[0147] In structures S2a, S2b, S3a, and S3b, X 3 and X 4each independently represents an oxygen atom, a sulfur atom, or a selenium atom, or is a substituted nitrogen atom represented by chemical formula 3 or chemical formula 4 described later, or may be a substituted carbon atom represented by chemical formula 5 described later or a substituted silicon atom. X contained in structure S2a and structure S2b 3 contained in structure S3a and structure S3b 3 may be the same as or different from X. X contained in structure S2a and structure S2b 4 contained in structure S3a and structure S3b 4 may be the same as or different from X.

[0148] In a fused polycyclic compound according to one embodiment, a first fused core represented by structure S1 and a second fused core represented by structure S2a or structure S2b may be linked to each other by sharing a first benzene ring B1. Further, the first fused core represented by structure S1 and a third fused core represented by structure S3a or structure S3b may be linked to each other by sharing a third benzene ring B3. In one embodiment, the first fused ring is linked to each of the second and third fused rings so as to share one benzene ring B1 and B3, respectively, and may form a 13-ring fused ring such as structure S-F1 to structure S-F3 below. JPEG2026139258000033.jpg62170JPEG2026139258000034.jpg62170JPEG2026139258000035.jpg61170

[0149] In structure S-F1 to structure S-F3, X 3a , X 3b , X 4a , and X 4b each independently represent an oxygen atom, a sulfur atom, or a selenium atom, or are a substituted nitrogen atom represented by chemical formula 3 or chemical formula 4 described later, or may be a substituted carbon atom represented by chemical formula 5 described later or a substituted silicon atom.

[0150] In structure S-F1 to structure S-F3, the B1 ring corresponds to the first benzene ring described above, and the B3 ring may correspond to the third benzene ring described above.

[0151] In structures S-F1 to S-F3, X 1 and X 2 The same provisions described above for structure S1 can also be applied to this matter.

[0152] Thermally activated delayed fluorescence materials having a boron-centered condensed ring skeleton are attracting attention as organic light-emitting element materials because they exhibit a narrow full width at half maximum (FMAX) and high emission quantum yield. Triboron-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 three boron atoms generally have larger FMAX and Stokes shifts compared to single-boron-based condensed skeletons due to the influence of structural relaxation in the excited and ground states, and are therefore still insufficient for use as materials for high-performance displays. The condensed polycyclic compound of the present invention has a structure in which the first to third condensed cores are linked by a specified linkage structure, thereby exhibiting small FMAX and Stokes shift characteristics and high emission quantum efficiency.

[0153] In one embodiment of the condensed polycyclic compound, at least one of the first to sixth atoms may be a nitrogen atom substituted with a first substituent. In one embodiment, the first substituent may include a first benzene substructure and a first subsubstituted bonded to a carbon at a specific position of the first benzene substructure. More specifically, the first substituent may include a first benzene substructure bonded to the nitrogen atom and a first subsubstituted bonded to at least one of two ortho positions relative to the nitrogen atom. For example, the first substituent may include a structure in which the first benzene substructure bonded to the nitrogen atom is bonded to one ortho position relative to the nitrogen atom, and the first subsubstituted is bonded to one ortho position relative to the nitrogen atom. Alternatively, the first substituent may include a structure in which the first benzene substructure bonded to the nitrogen atom is bonded to each of two ortho positions relative to the nitrogen atom, and the first subsubstituted is bonded to each of the two ortho positions relative to the nitrogen atom. The first subsubstituted may be a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms. For example, the first subsubstituted may be a substituted or unsubstituted phenyl group. On the other hand, in this specification, a nitrogen atom substituted with the first substituent may be represented by chemical formula 3, which will be described later.

[0154] In one embodiment, the condensed polycyclic compound can effectively maintain the trigonal palanar 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 nucleophiles and a change to a tetrahedral structure, which can cause device degradation. According to the present invention, the condensed polycyclic compound in one embodiment can effectively protect the empty p orbital of the boron atom by including the first substituent with a steric hindrance structure, thereby preventing degradation due to structural deformation.

[0155] Furthermore, by introducing a first substituent into the condensed polycyclic compound of one embodiment, intermolecular interactions can be suppressed, thereby controlling the formation of excimers or exciplexes, and thus increasing the luminescence efficiency. In addition, the condensed polycyclic compound of one embodiment, represented by chemical formula 1, by including the first substituent has the effect of increasing the branching distance and reducing Dexter energy transfer. Dexter energy transfer is a phenomenon in which triplet excitons move between molecules, and it increases if the branching distance is short, which can be a factor in increasing the quenching phenomenon due to the increase in triplet concentration. According to the present invention, the condensed polycyclic compound of one embodiment can suppress Dexter energy transfer by increasing the distance between adjacent molecules due to the structure with high steric hindrance, and thus can suppress the deterioration of lifetime that occurs when the triplet concentration increases. Therefore, if the condensed polycyclic compound of one embodiment is applied to the EML of the light-emitting layer of a light-emitting element ED, not only can the luminescence efficiency be increased, but the lifetime of the element can also be improved.

[0156] One example of a condensed polycyclic compound can be represented by the following chemical formula 1.

[0157] [Chemical formula 1] JPEG2026139258000036.jpg72170

[0158] The polycyclic condensed compound of one embodiment, represented by chemical formula 1, comprises first and third condensed cores, each containing a condensed skeleton centered on a boron atom. In the polycyclic condensed compound of one embodiment, the first condensed core may be linked to the second and third condensed cores by sharing one benzene ring with each.

[0159] On the other hand, in this specification, R in chemical formula 1 1 ~R 4 The benzene ring substituted with the substituent represented by corresponds to the first benzene ring described above, R 5 ~R 7 The benzene ring substituted with the substituent represented by corresponds to the second benzene ring described above, R 8 ~R11 A benzene ring substituted with the substituent represented by can correspond to the third benzene ring described above. Also, in chemical formula 2 described below, R 12 ~R 15 A benzene ring substituted with the substituent represented by corresponds to the fourth or sixth benzene ring described above, R 16 ~R 19 A benzene ring substituted with the substituent represented by can correspond to the fifth or seventh benzene ring described above.

[0160] In chemical formula 1, R 1 ~R 11 Each of these is independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano 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. Also, R 1 ~R 11 It can bond with adjacent groups to form a ring. For example, R 1 ~R 11 Each of these can independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted t-butyl group, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted biphenyl group.

[0161] In chemical formula 1, R 1 ~R 4 , and R 8 ~R 11 The two or three consecutive elements selected from each are the positions that are linked to the chemical formula 2 below. For example, in chemical formula 1, R 1 ~R 4 R 1 ~R 3 And, R 8 ~R 11 R 9 ~R 11 This can be a position linked to the following chemical formula 2. Or, R 1 ~R 4 R 1 ~R 3 And, R 8 ~R 11R 9 and R 10 This can be a position linked to the following chemical formula 2. Or, R 1 ~R 4 R 2 and R 3 And, R 8 ~R 11 R 9 and R 10 This can be a position where it is linked to the following chemical formula 2.

[0162] In chemical formula 1, X 1 and X 2 Each of these elements is either independently O, S, or Se, or can be represented by any one of the following chemical formulas 3 through 5.

[0163] [Chemical formula 2] JPEG2026139258000037.jpg54170

[0164] In chemical formula 2, R 12 ~R 19 Each of these is independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano 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, R 12 ~R 19 Each can bond with an adjacent group to form a ring. For example, R 12 ~R 19 Each of these can independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted t-butyl group, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted biphenyl group.

[0165] In chemical formula 2, X 3 and X 4 Each of these elements is either independently O, S, or Se, or can be represented by any one of the following chemical formulas 3 through 5.

[0166] In chemical formula 2, JPEG2026139258000038.jpg5170 is the position linked to chemical formula 1.

[0167] In chemical formula 2, JPEG2026139258000039.jpg3170 is linked to the aforementioned chemical formula 1, or R in the aforementioned chemical formula 2. 12 This is the position where it is connected.

[0168] [Chemical formula 3] JPEG2026139258000040.jpg45170[Chemical formula 4] JPEG2026139258000041.jpg28170[Chemical formula 5] JPEG2026139258000042.jpg23170

[0169] In chemical formulas 3 to 5, JPEG2026139258000043.jpg5170 is the position linked to chemical formula 1 or chemical formula 2.

[0170] In chemical formulas and chemical formula 5, R 20 ~R 26 Each of these is independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano 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 20 ~R 26 Each of these can independently be a hydrogen atom, a deuterium atom, or a substituted or unsubstituted phenyl group.

[0171] In chemical formula 3, R 20 and R 24 At least one of them is a substituted or unsubstituted ring-forming aryl group with 6 to 30 carbon atoms. In one example, in chemical formula 3, R 20 and R 24 At least one of them may be a substituted or unsubstituted phenyl group. For example, in chemical formula 3, R20 and R 24 Either one of them is a substituted or unsubstituted phenyl group, or R 20 and R 24 Each of these can independently be a substituted or unsubstituted phenyl group.

[0172] In chemical formula 4, Ar is a substituted or unsubstituted aryl group having 10 to 30 carbon atoms in a ring.

[0173] In chemical formula 5, Z is either a carbon atom or a silicon atom. However, if Z is a silicon atom, then R 25 and R 26 It is not a hydrogen atom.

[0174] In chemical formulas 1 and 2, X 1 ~X 4 At least one of them is represented by chemical formula 3. In one example, X 1 ~X 4 At least two of these can be represented by chemical formula 3. In one embodiment, X 1 and X 2 Each of these can be independently represented by chemical formula 3.

[0175] In chemical formula 1, X 1 and X 2 When represented by chemical formula 4, cases where Ar in chemical formula 4 is a fluorenyl group or a heteroaryl group are excluded.

[0176] In chemical formula 1, X 1 and X 2 When any one of them is represented by chemical formula 3, in chemical formula 3, R 20 and R 24 If any one of them is not a substituted or unsubstituted aryl group with 6 to 30 ring-forming carbon atoms, it is excluded. In other words, X 1 and X 2 When any one of them is represented by chemical formula 3, in chemical formula 3, R 20 and R 24 Each of these can be a substituted or unsubstituted aryl group with 6 to 30 ring-forming carbon atoms.

[0177] Figure 16 shows the three-dimensional molecular model of the comparative condensed polycyclic compound C-S1. Figure 17a shows the three-dimensional molecular model of the condensed polycyclic compound E-S1 of one example. Figure 17b shows the three-dimensional molecular model of the condensed polycyclic compound E-S2 of one example. Figures 16, 17a, and 17b show the three-dimensional molecular models of the comparative and example compounds viewed from the side. The structures of comparative compound C-S1, and example compounds E-S1 and E-S2 are shown below. The explanations below, referring to Figures 16, 17a, and 17b, are not limited to structure S-F1, but can also be applied to structures S-F2 and S-F3. JPEG2026139258000044.jpg70170JPEG2026139258000045.jpg70170JPEG2026139258000046.jpg87170

[0178] In multiple resonance molecules centered around a boron atom, luminescence transitions occur in a plate-like core, necessitating protection of the core from external nucleophiles, radicals, and decomposition products within the device. Therefore, a method of introducing sterically elongated substituents to physically obscure the boron atom's p-orbital may be employed. Figures 16, 17a, and 17b show the differences in molecular structure depending on the type of substituent introduced for steric hindrance in condensed polycyclic compounds.

[0179] Comparative compound C-S1 has X in chemical formula 1. 1 and X 2 One of these is represented by chemical formula 3, and in chemical formula 3, R 20 and R 24 This applies when at least one of the groups is not a substituted or unsubstituted ring-forming aryl group with 6 to 30 carbon atoms. In other words, comparative compound C-S1 is X in chemical formula 1. 1 and X 2 One of these is represented by chemical formula 3, and in chemical formula 3, R 20 and R 24 This corresponds to the case where only one of them is a phenyl group.

[0180] Example compound E-S1 is X in chemical formula 1. 1 and X 2 These all correspond to cases where the compound is represented by chemical formula 3. Example compound E-S2 is represented by X in chemical formula 1. 1 and X 2 When any one of them is represented by chemical formula 3, in chemical formula 3, R 20 and R 24 This corresponds to the case where each of them is a phenyl group.

[0181] Referring to Figures 16, 17a, and 17b, the condensed polycyclic compounds E-S1 and E-S2 of one example may have an increased steric shielding effect on the condensed skeleton compared to the comparative compound C-S1.

[0182] Comparative compound C-S1 is X 1 and X 2 One of these structures is represented by chemical formula 3, but the presence of only one phenyl group P1 at the ortho position of the nitrogen atom reduces the steric shielding effect on the condensed skeleton. Comparative example compound C-S1 contains a structure in which only one phenyl group P1 is introduced at the ortho position of the nitrogen atom, and has stericity in only one direction relative to the plate-like structure of the condensed skeleton. As a result, the opposite side of the plate-like structure is not protected, and there is a problem that the boron atom cannot be effectively protected from external nucleophiles, radicals, and decomposition products within the device that approach the opposite side.

[0183] In contrast, the example compound E-S1 is X 1 and X 2 Both are represented by chemical formula 3, and the presence of two or more substituted phenyl groups P1 and P2 in the ortho position increases the shielding effect on the condensed skeleton compared to comparative example compound C-S1. In addition, example compound E-S2 is X 1 and X 2Even if only one of them is represented by chemical formula 3, the presence of phenyl groups P1 and P1' at each of the two ortho positions increases the shielding effect on the condensed skeleton compared to comparative example compound C-S1. Since example compounds E-S1 and E-S2 can have stericity in both directions relative to the plate-like structure of the condensed skeleton, the boron atom can be effectively protected sterically, and the lifetime and efficiency can be further improved compared to comparative example compound C-S1. The condensed polycyclic compound according to one embodiment of the present invention is X 1 and X 2 When both are represented by chemical formula 3, a sufficient steric shielding effect on the condensed skeleton can be achieved by introducing at least two phenyl groups substituted in the ortho position.

[0184] In one embodiment, chemical formula 3 may be represented by chemical formula 3-1 or chemical formula 3-2.

[0185] [Chemical formula 3-1] JPEG2026139258000047.jpg54170[Chemical formula 3-2] JPEG2026139258000048.jpg57170

[0186] Chemical formulas 3-1 and 3-2 are R in chemical formula 3. 20 ~R 24 This applies when the type is specified. Chemical formula 3-1 is R in chemical formula 3. 20 When is a substituted or unsubstituted phenyl group, chemical formula 3-2 is R in chemical formula 3. 20 and R 24 These correspond to the cases of substituted or unsubstituted phenyl groups, respectively.

[0187] In chemical formulas 3-1 and 3-2, JPEG2026139258000049.jpg5170 may be a position linked to chemical formula 2 or chemical formula 3.

[0188] In chemical formulas 3-1 and 3-2, R 31 ~R 35 , and R 41 ~R 50Each of these can independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano 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 35 , and R 41 ~R 50 Each of these can independently be a hydrogen atom or a substituted or unsubstituted phenyl group.

[0189] In chemical formulas 3-1 and 3-2, R 21 ~R 24 The same principles described for chemical formula 3 above may apply to this.

[0190] In one embodiment, the first compound represented by chemical formula 1 may be represented by the following chemical formulas 1-1-1 or 1-1-2.

[0191] [Chemical formula 1-1-1] JPEG2026139258000050.jpg93170[Chemical formula 1-1-2] JPEG2026139258000051.jpg97170

[0192] Chemical formulas 1-1-1 and 1-1-2 are X in chemical formula 1. 1 and X 2 This indicates a case where the type is specified. Chemical formula 1-1-1 is where X is in chemical formula 1. 1 This indicates that the compound is represented by chemical formula 3, where S2 is O, S, or Se, or represented by chemical formula 4 or chemical formula 5. Chemical formula 1-1-2 is where X is in the chemical formula. 1 and X 2 This shows the case where it is represented by chemical formula 3. In chemical formulas 1-1-1 and 1-1-2, X of chemical formula 1 1 and X 2 The chemical formulas corresponding to each are R 20 This applies when the group is a substituted or unsubstituted phenyl group.

[0193] In chemical formula 1-1-1, X2a is O, S, or Se, or can be represented by the aforementioned chemical formula 4 or chemical formula 5.

[0194] In chemical formula 1-1-1, R 24a R can be a substituted or unsubstituted aryl group with 6 to 30 ring-forming carbon atoms. For example, R 24a This can be a substituted or unsubstituted phenyl group.

[0195] In chemical formulas 1-1-1 and 1-1-2, R 51 ~R 55 , R 61 ~R 70 , R 21b ~R 24b , and R 21c ~R 24c Each of these can independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano 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 51 ~R 55 , R 61 ~R 70 , R 21b ~R 24b , and R 21c ~R 24c Each of these can independently be a hydrogen atom or a substituted or unsubstituted phenyl group.

[0196] In chemical formulas 1-1-1 to 1-1-2, R 1 ~R 11 The same explanation as described above for chemical formula 1 can be applied to this.

[0197] In the condensed polycyclic compound of one example, at least one of the first and second atoms contained in the first condensed ring may be a nitrogen atom substituted with the first substituent described above. In the condensed polycyclic compound of one example, X in chemical formula 1 1 and X 2 At least one of them can be represented by chemical formula 3. For example, in chemical formula 1, X 1and X 2 Each of these can be independently represented by chemical formula 3. The condensed polycyclic compound of one example may increase the steric shielding effect on the condensed skeleton by including a structure in which a nitrogen atom represented by chemical formula 3 is introduced at the position of the first condensed ring.

[0198] Figures 18a and 18b are diagrams showing three-dimensional molecular models of a condensed polycyclic compound of one embodiment. Figures 18a and 18b exemplify the three-dimensional molecular models of a condensed polycyclic compound of one embodiment having the structure S-F1 described above. Figure 18a shows the three-dimensional molecular model of the condensed polycyclic compound of one embodiment viewed from direction "a", and Figure 18b shows the three-dimensional molecular model of the condensed polycyclic compound of one embodiment viewed from direction "b". The content described herein with reference to Figures 18a and 18b is not limited to structure S-F1, but can also be applied to structures S-F2 and S-F3. JPEG2026139258000052.jpg81170

[0199] The condensed polycyclic compound according to one embodiment may contain a condensed polycyclic ring containing three boron atoms. In order to impart sufficient durability to the condensed skeleton containing boron atoms, the condensed skeleton should be adequately shielded and protected sterically. The condensed polycyclic compound according to one embodiment, represented by chemical formula 1, may have a structure to which substituents that sterically protect the condensed skeleton are linked. The condensed polycyclic compound according to one embodiment has the effect of adequately shielding the condensed skeleton sterically by containing at least one substituent represented by chemical formula 3.

[0200] In a condensed polycyclic compound according to one embodiment of the present invention, the relative positional relationship of the condensed rings is also important in order to achieve a sufficient shielding effect of the condensed skeleton. The skeleton of the condensed polycyclic compound according to one embodiment, represented by structure S-F1, is composed of a first condensed ring B, a second condensed ring A, and a third condensed ring C, as shown in structure S-F1. Referring to Figures 18a and 18b, the second condensed ring A and the second condensed ring C are in an overlapping configuration. Therefore, the shielding effect required by the first condensed ring B must be greater than the shielding effect required by the second condensed ring A or the third condensed ring C in order to achieve a sufficient effect. The condensed polycyclic compound of the present invention contains X in the first condensed ring B. 1 and X 2 If at least one of these contains the structure represented by chemical formula 3, the steric shielding effect on the condensed skeleton can be increased.

[0201] In one embodiment, the first compound represented by chemical formula 1 may be represented by the following chemical formulas 1-2.

[0202] [Chemical formula 1-2] JPEG2026139258000053.jpg93170

[0203] In chemical formula 1-2, R 71 ~R 90 , R 21d ~R 23d , and R 21e ~R 23e Each of these can independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano 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 71 ~R 90 , R 21d ~R 23d , and R 21e ~R 23e Each of these can independently be a hydrogen atom or a substituted or unsubstituted phenyl group.

[0204] In chemical formula 1-2, R 1 ~R11 The same principles described above for chemical formula 1 may apply to this.

[0205] In one embodiment, the first compound represented by chemical formula 1 may be represented by any one of the following chemical formulas 1-3-1 to 1-3-3.

[0206] [Chemical formula 1-3-1] JPEG2026139258000054.jpg93170[Chemical formula 1-3-2] JPEG2026139258000055.jpg93170[Chemical formula 1-3-3] JPEG2026139258000056.jpg93170

[0207] In chemical formulas 1-3-1 to 1-3-3, X 3a , X 3b , X 4a , and X 4b Each of these elements can be independently O, S, or Se, or can be represented by any one of the chemical formulas 3 to 5.

[0208] In chemical formulas 1-3-1 to 1-3-3, R 12a ~R 19a , and R 12b ~R 19b Each of these can independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano 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 12a ~R 19a , and R 12b ~R 19b Each of these can independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted t-butyl group, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted biphenyl group.

[0209] In chemical formulas 1-3-1 to 1-3-3, X 1 , X 2 , and R5 ~R 7 The same principles as those described in Chemical Formula 1 apply to this.

[0210] In one embodiment, the first compound represented by chemical formula 1 may be represented by any one of the following chemical formulas 1-4-1 to 1-4-3.

[0211] [Chemical formula 1-4-1] JPEG2026139258000057.jpg93170[Chemical formula 1-4-2] JPEG2026139258000058.jpg93170[Chemical formula 1-4-3] JPEG2026139258000059.jpg93170

[0212] In chemical formulas 1-4-1 to 1-4-3, X 3a , X 3b , X 4a , and X 4b Each of these elements can be independently O, S, or Se, or can be represented by any one of the chemical formulas 3 to 5.

[0213] In chemical formulas 1-4-1 to 1-4-3, R 12a ~R 19a , and R 12b ~R 19b Each of these can independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano 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 12a ~R 19a , and R 12b ~R 19b Each of these can independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted t-butyl group, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted biphenyl group.

[0214] In chemical formulas 1-4-1 to 1-4-3, X 1 , X2 , and R 5 ~R 7 The same principles as those described in Chemical Formula 1 apply to this.

[0215] 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.

[0216] 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.

[0217] [First compound group] JPEG2026139258000060.jpg111170JPEG2026139258000061.jpg111170JPEG2026139258 000062.jpg49170JPEG2026139258000063.jpg43170JPEG2026139258000064.jpg111170 JPEG2026139258000065.jpg111170JPEG2026139258000066.jpg50170JPEG20261392580 00067.jpg43170JPEG2026139258000068.jpg111170JPEG2026139258000069.jpg111170 JPEG2026139258000070.jpg111170JPEG2026139258000071.jpg111170

[0218] 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.

[0219] 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 in one embodiment 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.

[0220] The condensed polycyclic compound of one embodiment, represented by chemical formula 1, may be a light-emitting material having a center emission 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 condensed polycyclic compound may consist of dopant substances that emit light in various wavelength ranges, such as red light-emitting dopants and green light-emitting dopants.

[0221] 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).

[0222] 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.

[0223] 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.

[0224] 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.

[0225] 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 the following: a second compound represented by chemical formula HT-1, and a third compound represented by chemical formula ET-1.

[0226] 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.

[0227] [Chemical formula HT-1] JPEG2026139258000072.jpg50170

[0228] In the chemical formula HT-1, M1 to M8 are each independently either N or CR. a1 It is possible. For example, M1 through M8 are all CR a1 It is possible. Alternatively, one of M1 through M8 is N, and the rest are CR. a1 It is possible.

[0229] In the chemical formula HT-1, L1 is 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. For example, L1 may be a directly bonded, substituted, or unsubstituted phenylene group, a substituted or unsubstituted divalent biphenyl group, or a substituted or unsubstituted divalent carbazole group, but the examples are not limited to these.

[0230] In the chemical formula HT-1, Y a Direct coupling, CR a2 R a3 , or SiR a4 R a5 It is possible. In other words, the two benzene rings linked to the nitrogen atom of chemical formula HT-1 are directly bonded. JPEG2026139258000073.jpg22170, or This could mean that they are concatenated via JPEG2026139258000074.jpg22170. 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.

[0231] 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.

[0232] In the chemical formula HT-1, Ra1 ~R a5 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. a1 ~R a5 Each can bond with an adjacent group to form a ring. For example, R a1 ~R a5 Each of these can independently be a hydrogen atom or a deuterium atom. a1 ~R a5 Each of these can independently be an unsubstituted methyl group or an unsubstituted phenyl group.

[0233] 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.

[0234] [Second compound group] JPEG2026139258000075.jpg45170JPEG2026139258000076.jpg33170JPEG2026139258000077.jpg40170JPEG2026139258000078.jpg38170 JPEG2026139258000079.jpg35170JPEG2026139258000080.jpg28170JPEG2026139258000081.jpg30170JPEG2026139258000082.jpg30170 JPEG2026139258000083.jpg30170JPEG2026139258000084.jpg30170JPEG2026139258000085.jpg30170JPEG2026139258000086.jpg30170 JPEG2026139258000087.jpg35170JPEG2026139258000088.jpg33170JPEG2026139258000089.jpg35170JPEG2026139258000090.jpg38170

[0235] In the specific compounds presented in the second group of compounds, "D" represents a deuterium atom, and "Ph" can be an unsubstituted phenyl group.

[0236] 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.

[0237] [Chemical formula ET-1] JPEG2026139258000091.jpg50170

[0238] In the chemical formula ET-1, Z a ~Z c At least one of them is N, and the rest are CR. a6 For example, Z a ~Z c One of them is N, and the remaining two are CR independently. a6This 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 a6 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.

[0239] In chemical formula ET-1, R a6 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.

[0240] In chemical formula ET-1, b1 to b3 can each be an independent integer between 0 and 10.

[0241] 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.

[0242] In chemical formula ET-1, L2 to L4 are each independently 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, then L2 to L4 are each independently 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.

[0243] 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 in one embodiment may contain any one of the compounds in the third compound group described below.

[0244] [Third compound group] JPEG2026139258000092.jpg135170JPEG2026139258000093.jpg140170JPEG202 6139258000094.jpg137170JPEG2026139258000095.jpg135170JPEG2026139258 000096.jpg157170JPEG2026139258000097.jpg155170JPEG2026139258000098. jpg132170JPEG2026139258000099.jpg38170JPEG2026139258000100.jpg103170

[0245] In the specific compounds presented in the third group of compounds, "D" represents a deuterium atom, and "Ph" represents an unsubstituted phenyl group.

[0246] The luminescent layer EML contains a second compound and a third compound, and the second and third compounds can form an exciplex. In the luminescent layer EML, 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.

[0247] 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.

[0248] 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 can 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.

[0249] 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.

[0250] [Chemical formula D-1] JPEG2026139258000101.jpg77170

[0251] In chemical formula D-1, Q1 to Q4 can each be independently either C or N.

[0252] In chemical formula D-1, C1 to C4 are each independently substituted or unsubstituted hydrocarbon rings with 5 to 30 ring-forming carbon atoms, or substituted or unsubstituted heterocycles with 2 to 30 ring-forming carbon atoms.

[0253] X 11 ~X 14 Each can be directly connected or It could be JPEG2026139258000102.jpg6170. For example, X 11 ~X 14 One of the following is The file is JPEG2026139258000103.jpg6170, and the rest can be directly combined.

[0254] In chemical formula D-1, L 11 ~L 13 Each is independently and directly connected. JPEG2026139258000104.jpg24170 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, JPEG2026139258000105.jpg8170 represents the portion connected to C1 through C4.

[0255] In chemical formula D-1, b11 to b13 can each be independently 0 or 1. If b11 is 0, C1 and C2 do not need to be linked to each other. If b12 is 0, C2 and C3 do not need to be linked to each other. If b13 is 0, C3 and C4 do not need to be linked to each other.

[0256] In chemical formula D-1, R b1 ~R b6Each 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. b1 ~R b6 Each can bond with an adjacent group to form a ring. b1 ~R b6 Each of these can independently be a substituted or unsubstituted methyl group, or a substituted or unsubstituted t-butyl group.

[0257] In chemical formula D-1, d1 to d4 are each independent integers between 0 and 4. If d1 to d4 are all 0 in chemical formula D-1, then the fourth compound is R b1 ~R b6 It does not have to be replaced. Each of d1 to d4 is 4, R b1 ~R b6 If each of them is a hydrogen atom, it is the same as when d1 to d4 are all 0. If each of d1 to d4 is an integer of 2 or more, multiple R values ​​are provided. b1 ~R b6 Each of them is either the same or multiple Rs. b1 ~R b6 At least one of them is different.

[0258] In chemical formula D-1, C1 to C4 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. JPEG2026139258000106.jpg57170JPEG2026139258000107.jpg45170

[0259] In C-1 to C-4, P1 is JPEG2026139258000108.jpg6170 or CR c4 Therefore, P2 is JPEG2026139258000109.jpg6170 or NR c11 Therefore, P3 is JPEG2026139258000110.jpg6170 or NR c12 Therefore, P4 is JPEG2026139258000111.jpg6170 or CR c18 Therefore, P6 is JPEG2026139258000112.jpg6170 or CR c20 It is possible. R c1 and R c20 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.

[0260] Furthermore, in C-1 to C-4, JPEG2026139258000113.jpg12170 is the part connected to the central metal atom, Pt. JPEG2026139258000114.jpg7170 is a combination of adjacent ring groups (C1 to C4) or linkers (L 11 ~L 13 This could be the part that is connected to ).

[0261] 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 contain 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.

[0262] 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 not accumulate inside the light-emitting layer EML and will emit light quickly, thus reducing the degradation of the element. Therefore, the lifespan of the light-emitting element ED of one embodiment is increased.

[0263] 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.

[0264] 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.

[0265] [Fourth compound group] JPEG2026139258000115.jpg184170JPEG2026139258000116.jpg156170JPEG2026139258000117.jpg169170JPEG2026139258000118.jpg169170

[0266] In the specific compounds presented in the fourth group of compounds, "D" represents a deuterium atom.

[0267] 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, a light-emitting element ED including multiple light-emitting layers may emit white light. A 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.

[0268] 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.

[0269] 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.

[0270] In terms of the total weight of the second and third compounds, the weight ratio of the second and third compounds may be approximately 3:7 to 7:3.

[0271] If the content of the second and third compounds satisfies the above-mentioned ratio, the charge balance characteristics within the EML (electroluminescent layer) will improve, potentially increasing 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, reducing luminous efficiency and potentially degrading the device.

[0272] 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.

[0273] 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.

[0274] In the light-emitting element ED of one embodiment shown in Figures 5 to 8, the light-emitting layer EML further contains known hosts and dopants in addition to the hosts and dopants described above. For example, the light-emitting layer EML may contain 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.

[0275] [Chemical formula E-1] JPEG2026139258000119.jpg60170

[0276] In chemical formula E-1, R 31 ~R 40Each of these can 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.

[0277] In chemical formula E-1, c and d can each be independent integers between 0 and 5, inclusive.

[0278] Chemical formula E-1 may be represented by any one of the following compounds E1 through E19.

[0279] JPEG2026139258000120.jpg81170JPEG2026139258000121.jpg76170JPEG2026139258000122.jpg118170JPEG2026139258000123.jpg60170

[0280] 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.

[0281] [Chemical formula E-2a] JPEG2026139258000124.jpg55170

[0282] In chemical formula E-2a, a is an integer between 0 and 10, and L ais a directly bonded, 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. 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.

[0283] 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 aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, or may 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.

[0284] 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.

[0285] [Chemical formula E-2b] JPEG2026139258000125.jpg14170

[0286] 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. bcan be a directly bonded, 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. 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.

[0287] The compound represented by chemical formula E-2a and the compound represented by 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 compounds represented by chemical formula E-2a or chemical formula E-2b are not limited to those shown in compound group E-2 below.

[0288] [Compound group E-2] JPEG2026139258000126.jpg82170JPEG2026139258000127.jpg102170JPEG2026139258000128.jpg92170JPEG2026139258000129.jpg94170

[0289] 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)benzene) as host materials. 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.

[0290] 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.

[0291] [Chemical formula Ma] JPEG2026139258000130.jpg53170

[0292] 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.

[0293] The compound represented by the chemical formula Ma can be used as a phosphorescent dopant.

[0294] 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.

[0295] JPEG2026139258000131.jpg59170JPEG2026139258000132.jpg96170JPEG2026139258000133.jpg139170JPEG2026139258000134.jpg71170

[0296] 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.

[0297] [Chemical formula Fa] JPEG2026139258000135.jpg52170

[0298] 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 JPEG2026139258000136.jpg5170. a ~R j among The remaining unsubstituted atoms in JPEG2026139258000137.jpg5170 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 JPEG2026139258000138.jpg5170, 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.

[0299] [Chemical formula Fb] JPEG2026139258000139.jpg33170

[0300] In the chemical formula Fb, R a and R b Each 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.

[0301] In chemical formula Fb, U and V can each be independently 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.

[0302] 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.

[0303] [Chemical formula Fc] JPEG2026139258000140.jpg62170

[0304] In the chemical formula Fc, A1 and A2 are independently O, S, Se, or NR, respectively. m And R m R1 to R 11Each 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.

[0305] In the chemical formula Fc, A1 and A2 can each independently bond with substituents on adjacent rings to form fused rings. For example, A1 and A2 can each 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.

[0306] 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).

[0307] 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.

[0308] The light-emitting layer may include quantum dots.

[0309] 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.

[0310] The diameter of the quantum dot may be, for example, about 1 nm to 10 nm.

[0311] The quantum dots can be synthesized by wet chemical processes, organometallic chemical vapor deposition processes, molecular beam epitaxy processes, or similar processes.

[0312] 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 naturally acts as a dispersant coordinated to the surface of the quantum dot crystals, thereby regulating the crystal growth. Therefore, the wet chemical process is simpler than vapor deposition methods such as metal-organic chemical vapor deposition (MOCVD) or molecular beam epitaxy (MBE), and allows for control of quantum dot particle growth through a low-cost process.

[0313] The light-emitting layer of the present invention may include a quantum dot material. The core of the quantum dot can 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.

[0314] 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 A ternary compound selected from the group consisting of e, HgZnS, HeZnSe, HeZnTe, MgZnSe, MgZnS, and mixtures thereof, and a quaternary compound selected from the group consisting of HgZnTeS, CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe, HgZnSTe, and mixtures thereof. On the other hand, group II-VI semiconductor compounds may further contain group I metals and / or group IV elements. Group I-II-VI compounds are selected from CuSnS or CuZnS, and group II-IV-VI compounds may be selected from ZnSnS, etc. Group I-II-IV-VI compounds may be selected from the group consisting of Cu2ZnSnS2, Cu2ZnSnS4, Cu2ZnSnSe4, Ag2ZnSnS2, and mixtures thereof.

[0315] Group III-VI compounds may include dielemental compounds such as In2S3 and In2Se3, trielemental compounds such as InGaS3 and InGaSe3, or any combination thereof.

[0316] 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.

[0317] 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.

[0318] 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.

[0319] 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.

[0320] 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.

[0321] 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).

[0322] 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, one quantum dot may have a core / shell structure surrounding other quantum dots. 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.

[0323] In some embodiments, the quantum dot 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 its 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.

[0324] 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.

[0325] 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.

[0326] 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.

[0327] 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.

[0328] 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, it is possible to realize light-emitting devices that emit light at various wavelengths. 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.

[0329] In one embodiment of the light-emitting element ED shown in Figures 5 to 8, 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.

[0330] 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.

[0331] 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 a structure of electron transport layer (ETL) / electron injection layer (EIL) or hole blocking layer (HBL) / electron transport layer (ETL) / electron injection layer (EIL) 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.

[0332] 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).

[0333] The electron transport region (ETR) may contain compounds represented by the following chemical formula ET-2.

[0334] [Chemical formula ET-2] JPEG2026139258000141.jpg53170

[0335] 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.

[0336] 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.

[0337] 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, 2-(4-(N-phenylbenzimidazole-1-yl)phenyl)-9,10-dinaphthylanthracene, 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-terto-butylphenyl)-1,3,4-oxadiazole), BAlq(bis(2-methyl-8-quinolinolato-N1,O8)-(1,1'-biphenyl-4-orato)aluminum), Bebq2(beryllium bis(benzoquinoline-10-orato), ADN(9,10-di(naphthalene-2-yl)anthracene), BmPyPhB(1,3-bis[3,5-di(pyridine-3-yl)phenyl]benzene), CNNPTRZ may contain 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.

[0338] In one embodiment, the electron injection region (ETR) may contain any one of the compounds from the third group of compounds listed below.

[0339] The electron transport region (ETR) may contain at least one of the following compounds ET1 to ET36.

[0340] JPEG2026139258000142.jpg161170JPEG2026139258000143.jpg240170JPEG2026139258000144.jpg253170

[0341] 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 a metal oxide such as Li2O, 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.

[0342] 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).

[0343] 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.

[0344] 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.

[0345] 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.

[0346] 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).

[0347] 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.

[0348] 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.

[0349] 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.

[0350] In one embodiment, the capping layer CPL may be an organic or inorganic layer. For example, if the capping layer CPL contains inorganic material, the inorganic material may include alkali metal compounds such as LiF, alkaline earth compounds such as MgF2, SiON, SiNx, SiOy, etc.

[0351] 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), 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 listed below.

[0352] JPEG2026139258000145.jpg125170JPEG2026139258000146.jpg78170

[0353] 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.

[0354] Figures 9 and 12 are cross-sectional views of a display module according to one embodiment. In the following description of the display module according to one embodiment, with reference to Figures 9 and 12, we will not repeat the content described in Figures 3 to 8 above, but will focus on the differences.

[0355] Referring to Figure 9, a display module DM-a according to one embodiment 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 9, 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.

[0356] 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 9 can also be to which the structures of the light-emitting elements shown in Figures 5 to 8 described above are also applicable.

[0357] In the display module DM-a according to one embodiment, the light-emitting layer EML of the light-emitting element ED contains the condensed polycyclic compound of the embodiment described above.

[0358] Referring to Figure 9, the light-emitting layer EML may be located within the aperture OH defined in the pixel definition film DPL. For example, the light-emitting layers EML provided corresponding to each light-emitting region PXA-R, PXA-G, and PXA-B, separated by the pixel definition film PDL, may emit light in the same wavelength range. In one embodiment of the display module DM-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.

[0359] 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.

[0360] 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.

[0361] Referring to Figure 9, a segmented pattern BMP is provided between the optical control units CCP1, CCP2, and CCP3, which are spaced apart from each other, but the embodiment is not limited to this. In Figure 9, it is shown that the segmented 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 segmented pattern BMP in at least part.

[0362] 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.

[0363] 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.

[0364] 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.

[0365] The first optical control unit CCP1, the second optical control unit CCP2, and the third optical control unit CCP3 may each 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.

[0366] 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.

[0367] 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.

[0368] 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.

[0369] In one embodiment of the display module DM-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.

[0370] The color filter layer CFL may include filters CF1, CF2, and CF3. The first to third filters CF1, CF2, and CF3 may be arranged to correspond to the red emission region PXA-R, the green emission region PXA-G, and the blue emission region PXA-B, respectively.

[0371] 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 the 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.

[0372] 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.

[0373] 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.

[0374] 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.

[0375] 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.

[0376] Figure 10 is a cross-sectional view showing a part of a display module according to one embodiment. In the display module DM-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. At least one of the plurality of light-emitting structures OL-B1, OL-B2, and OL-B3 may include the polycyclic compound of one embodiment. As a result, the light-emitting element ED-BT can exhibit high efficiency and long lifespan characteristics. Furthermore, the light-emitting element ED-BT of one embodiment can exhibit high light efficiency and long lifespan characteristics in the blue light emission region.

[0377] The light-emitting element ED-BT may include a plurality of light-emitting structures OL-B1, OL-B2, and OL-B3, which are sequentially stacked in the thickness direction between a first electrode EL1 and a second electrode EL2 facing each other. Each of the light-emitting structures OL-B1, OL-B2, and OL-B3 may include a light-emitting layer EML (Figure 5) and a hole transport region HTR and an electron transport region ETR arranged between the light-emitting layer EML (Figure 5). In other words, the light-emitting element ED-BT included in the display module DM-TD according to one embodiment may be a light-emitting element with a tandem structure including a plurality of light-emitting layers.

[0378] In one embodiment shown in Figure 10, the light emitted from each of the light-emitting structures OL-B1, OL-B2, and OL-B3 can be blue light. However, the embodiment is not limited to this, and the 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, a light-emitting element ED-BT 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.

[0379] Charge generation layers CGL1 and CGL2 may be arranged between adjacent light-emitting structures OL-B1, OL-B2, and OL-B3. In one embodiment shown in Figure 10, the charge generation layers CGL1 and CGL2 may include a first charge generation layer CGL1 arranged between the first light-emitting structure OL-B1 and the second light-emitting structure OL-B2, and a second charge generation layer CGL2 arranged between the second light-emitting structure OL-B2 and the third light-emitting structure OL-B3. The first and second charge generation layers CGL1 and CGL2 may each independently include a p-type charge generation layer and / or an n-type charge generation layer.

[0380] In one embodiment, at least one of the light-emitting structures OL-B1, OL-B2, and OL-B3 included in the display module DM-TD may contain the condensed polycyclic compound of the embodiment described above. In other words, at least one of the multiple light-emitting layers included in the light-emitting element ED-BT contains the condensed polycyclic compound of the embodiment.

[0381] Figure 11 is a cross-sectional view showing a display device according to one embodiment of the present invention. Figure 12 is a cross-sectional view showing a display device according to one embodiment of the invention.

[0382] Referring to Figure 11, the display module 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 module DD of one embodiment shown in Figure 4, the difference in the embodiment shown in Figure 11 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.

[0383] 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.

[0384] 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.

[0385] 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 positioned 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 positioned between the hole transport region HTR and the light-emitting auxiliary region OG.

[0386] 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.

[0387] 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.

[0388] At least one light-emitting layer included in the display module DD-b of one embodiment shown in Figure 11 may contain 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.

[0389] Unlike Figures 10 and 11, the display module DD-c in Figure 12 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.

[0390] 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.

[0391] In one embodiment, at least one of the luminescent structures OL-B1, OL-B2, OL-B3, and OL-C1 included in the display module DD-c contains the condensed polycyclic compound of the embodiment described above. For example, in one embodiment, at least one of the first to third luminescent structures OL-B1, OL-B2, and OL-B3 may contain the condensed polycyclic compound of the embodiment described above.

[0392] A light-emitting element (ED) according to one embodiment of the present invention can exhibit excellent luminescence 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 condensed polycyclic compound of the embodiment can be included in the light-emitting layer EML of the light-emitting element (ED) of the embodiment, and the light-emitting element of the embodiment can exhibit long lifetime characteristics.

[0393] In one embodiment, the electronic device may include a display device containing a plurality of light-emitting elements and a control unit for controlling the display device. In the electronic device of one embodiment, at least one of the plurality of light-emitting elements may contain the condensed polycyclic compound of the embodiment described above in its light-emitting layer.

[0394] The electronic device of one embodiment may be a device that is activated by an electrical signal. The electronic device of one embodiment may include a display device that includes a display module according to one embodiment described with reference to Figures 3 and 9 to 12, etc. For example, the display device may include large electronic devices such as televisions, monitors, or external billboards, as well as medium and small display devices such as personal computers, laptop computers, personal information terminals, vehicle display devices, game consoles, portable electronic devices, and cameras.

[0395] The display device of one embodiment includes a display module containing the condensed polycyclic compound of one embodiment and can exhibit high efficiency and long life characteristics. The electronic device of one embodiment has improved display efficiency and display life and can exhibit excellent display quality.

[0396] Figure 13 shows a tablet terminal as an example of an electronic device EA. The display device EA of one embodiment may include a display module DM according to one embodiment. For example, an electronic module, camera module, or power supply module, which are mounted on the main board together with the display module DM, can be arranged in a bracket / enclosure HAU to constitute a tablet terminal.

[0397] The electronic device EA of one embodiment shown in Figure 14 may include a display module of one embodiment described with reference to Figures 3 and 9 to 12, etc.

[0398] In one embodiment, an electronic device EA is shown that includes a display module DM having a planar display surface, but it is not limited to this. The electronic device EA may include a curved display surface or a three-dimensional display surface. For example, a three-dimensional display surface may include multiple display areas that indicate different directions from each other, and may include a folded display surface. The electronic device EA according to this embodiment may be a flexible electronic device. A flexible electronic device may be a foldable electronic device that can be folded.

[0399] As shown in Figure 13, the display surface EA-IS includes an active area AA where the image is displayed, and a bezel area NAA adjacent to the active area AA. The bezel area NAA is an area where the image is not displayed. Figure 13 shows an icon image as an example of an image. The active area AA may be referred to as the display area of ​​the display module DM, and the bezel area NAA may be referred to as the non-display area of ​​the display module DM.

[0400] Figure 14 shows a portable terminal as an example of the electronic device EA-M of one embodiment. Referring to Figure 14, the electronic device EA-M of one embodiment may include multiple display surfaces. The electronic device EA-M of one embodiment may include display surfaces IS-M, IS-S1, IS-S2, IS-S3, and IS-S4, each having a different primary display direction.

[0401] In one embodiment, the electronic device EA-M may be a stereoscopic display device including an upper display surface IS-M and a plurality of side display surfaces IS-S1, IS-S2, IS-S3, IS-S4. Each of the plurality of side display surfaces IS-S1, IS-S2, IS-S3, IS-S4 may be a display surface extending from one side of the upper display surface IS-M. In one embodiment, the electronic device EA-M may include a main display surface that primarily provides an image in one direction and a plurality of sub-display surfaces that provide images in a direction different from that of the main display surface. In the embodiment of the electronic device EA-M shown in Figure 14, the main display surface is the upper display surface IS-M, and the sub-display surfaces may be the side display surfaces IS-S1, IS-S2, IS-S3, IS-S4.

[0402] The side display surfaces IS-S1, IS-S2, IS-S3, and IS-S4 may have display surfaces that are not parallel to the upper display surface IS-M. On the other hand, the multiple side display surfaces IS-S1, IS-S2, IS-S3, and IS-S4 are display areas that are folded and extended from one side of the upper display surface IS-M, and for example, the multiple side display surfaces IS-S1, IS-S2, IS-S3, and IS-S4 may be folded display areas.

[0403] The electronic device EA-M of one embodiment shown in Figure 14 may include a display module according to one embodiment described with reference to Figures 3 and 9 to 12, etc.

[0404] Figure 15 shows a vehicle AM ​​in which the first to fourth electronic devices EA-1, EA-2, EA-3, and EA-4 are installed. At least one of the first to fourth electronic devices EA-1, EA-2, EA-3, and EA-4 may include a display module of one embodiment described with reference to the figure and Figures 9 to 12.

[0405] Although Figure 15 shows an automobile as the vehicle AM, this is illustrative, and the first to fourth electronic devices EA-1, EA-2, EA-3, and EA-4 may be installed in other means of transport such as bicycles, motorcycles, trains, ships, and airplanes.

[0406] At least one of the first to fourth electronic devices EA-1, EA-2, EA-3, and EA-4 may include a light-emitting element ED of one embodiment described with reference to Figures 5 to 8. At least one of the first to fourth electronic devices EA-1, EA-2, EA-3, and EA-4 may include a polycyclic compound of one embodiment. As a result, the first to fourth electronic devices EA-1, EA-2, EA-3, and EA-4 containing the condensed polycyclic compound of one embodiment may have improved display efficiency and display life. Furthermore, the first to fourth electronic devices EA-1, EA-2, EA-3, and EA-4 containing the condensed polycyclic compound of one embodiment may exhibit excellent display quality.

[0407] Referring to Figure 15, the vehicle AM ​​may include a steering wheel HA and a gear GR for controlling its operation, and may include a forward window GL located in front of the driver.

[0408] The first electronic device EA-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 driving speed, a second scale indicating the engine speed (RPM (revolutions per minute)), and an image indicating the fuel status. The first and second scales may be displayed as digital images. In one embodiment shown in Figure 15, the first electronic device EA-1 may be positioned in a first area that overlaps with the steering wheel HA. However, the embodiment is not limited to this, and the first electronic device EA-1 may be positioned across the entire dashboard, or separated and positioned in the portion facing the driver's seat and the portion facing the passenger seat, respectively.

[0409] The second electronic device EA-2 may be positioned in a second area between the driver's seat and the front window GL. For example, the second electronic device EA-2 may be a head-up display (HUD) that displays second information about the vehicle AM. The second electronic device EA-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 electronic device EA-2 may be projected onto the front window GL. The display surface of the second electronic device EA-2 may face the driver's seat. Alternatively, the second electronic device EA-2 may provide an image in the direction of the front window GL.

[0410] The third electronic device EA-3 may be located in a third area adjacent to the gear GR. For example, the third electronic device EA-3 may be located between the driver's seat and the passenger seat and may be a Center Information Display (CID) that displays 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 playback, and the temperature inside the vehicle AM.

[0411] The fourth electronic device EA-4 may be located in a fourth area adjacent to the sides of both AMs, separated from the steering wheel HA and gear GR. For example, the fourth electronic device EA-4 may be a digital side mirror that displays fourth information. The fourth electronic device EA-4 may display images of the outside of the vehicle AM ​​captured by a camera module CM located on the outside of the vehicle AM. The fourth information may include images of the outside of the vehicle AM.

[0412] The first to fourth pieces of information described above are illustrative, and the first to fourth electronic devices EA-1, EA-2, EA-3, and EA-4 may further display information relating to the interior and exterior of the vehicle. 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.

[0413] Figures 13 to 15 illustrate an example of an electronic device or an example including an electronic device, and a display module including a light-emitting element containing a condensed polycyclic compound of one embodiment can be used in other electronic devices without departing from the concept of the semi-inventive.

[0414] 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.

[0415] [Examples] 1. Synthesis of condensed polycyclic compounds First, the method for synthesizing condensed polycyclic compounds according to this embodiment will be specifically explained by illustrating the synthesis methods for compounds 1 to 12 and 14 to 16. Furthermore, the synthesis method for condensed polycyclic compounds described below is just one example, and the synthesis method for condensed polycyclic compounds according to the embodiments of the present invention is not limited to the following examples.

[0416] (1) Synthesis of compound 1

[0417] (Synthesis of intermediate 1C) JPEG2026139258000147.jpg49170

[0418] Under an Ar atmosphere, intermediate 1A (1,3-difluoro-5-iodobenzene, 50 g), intermediate 1B (phenol, 50 g), K2CO3 (87 g), and 1-methyl-2-pyrrolidone (400 mL) were added to a 1000 mL three-necked flask and heated and stirred at 160 °C for 16 hours. After returning to room temperature, water was added and extracted with CH2Cl2. The organic layer was dried in one step over MgSO4, and the solvent was removed by distillation under reduced pressure. Purification by silica gel column chromatography yielded 67 g of intermediate 1C (80% yield). The mass number of intermediate 1C, as measured by FAB-MS, was 404.

[0419] (Synthesis of intermediate 1F) JPEG2026139258000148.jpg48170

[0420] Under an Ar atmosphere, intermediate 1D (1,3-dibromo-5-tert-butylbenzene, 30 g), intermediate 1E (51 g), bis(dibenzylideneacetone)palladium(0) (Pd(dba)2, 0.6 g), tri-tert-butylphosphine tetrafluoroborate (0.6 g), sodium tert-butoxide (NaOtBu, 25 g), and toluene (800 mL) were added to a 2000 mL three-necked flask and heated and stirred at 80°C for 24 hours. After returning to room temperature, water was added and the mixture was extracted with toluene. The organic layer was dried in one step over MgSO4, and the solvent was removed by distillation under reduced pressure. The mixture was purified by silica gel column chromatography to obtain 58 g of intermediate 1F (yield 91%). The mass number of intermediate 1F, as measured by FAB-MS, was 621.

[0421] (Synthesis of intermediate 1G) JPEG2026139258000149.jpg48170

[0422] Under an Ar atmosphere, intermediate 1F (12 g), intermediate 1C (31 g), CuI (7.5 g), and K2CO3 (20 g) were added to a 200 mL three-necked flask and heated and stirred at 230 °C for 48 hours. After returning to room temperature, water was added and extracted with CH2Cl2. The organic layer was dried in one step over MgSO4, and the solvent was removed by distillation under reduced pressure. Purification by silica gel column chromatography yielded 7.1 g of intermediate 1G (yield 32%). The mass number of intermediate 1G, as measured by FAB-MS, was 1141.

[0423] (Synthesis of Compound 1) JPEG2026139258000150.jpg50170

[0424] Under an Ar atmosphere, 1 g (7.1 g) of the intermediate was placed in a 500 mL three-necked flask and dissolved in o-dichlorobenzene (ODCB, 150 mL). The mixture was cooled to 0°C in an ice bath, boron triiodide (BI3, 14.7 g) was added, and the mixture was heated and stirred at 140°C for 6 hours. After cooling to 0°C in an ice bath, N,N-diisopropylethylamine (DIPEA, 30 mL) was added. After returning to room temperature, the reaction solution was filtered through silica gel, and the filtrate solvent was removed by distillation under reduced pressure. The resulting crude product was purified by silica gel column chromatography to obtain 3 g of compound 1 (yield 42%). The molecular weight of compound 1, as measured by FAB-MS, was 1165.

[0425] (2) Synthesis of compound 2

[0426] (Synthesis of intermediate 2B) JPEG2026139258000151.jpg34170

[0427] Under an Ar atmosphere, intermediate 2A (1,3-dibromo-5-butylbenzene, 20 g), intermediate 1E (37 g), bis(dibenzylideneacetone)palladium(0) (Pd(dba)2, 0.4 g), tri-tert-butylphosphine tetrafluoroborate (0.4 g), sodium tert-butoxide (NaOtBu, 18 g), and toluene (500 mL) were added to a 1000 mL three-necked flask and heated and stirred at 60°C for 24 hours. After returning to room temperature, water was added and extracted with toluene. The organic layer was dried in one step over MgSO4, and the solvent was removed by distillation under reduced pressure. Purification by silica gel column chromatography yielded 35.3 g of intermediate 2B (80% yield). The mass number of intermediate 2B, as measured by FAB-MS, was 599.

[0428] (Synthesis of intermediate 2C) JPEG2026139258000152.jpg50170

[0429] Under an Ar atmosphere, intermediate 2B (12 g), intermediate 1C (32 g), CuI (7.6 g), and K2CO3 (20 g) were added to a 200 mL three-necked flask and heated and stirred at 230 °C for 48 hours. After returning to room temperature, water was added and extracted with CH2Cl2. The organic layer was dried in one step over MgSO4, and the solvent was removed by distillation under reduced pressure. Purification by silica gel column chromatography yielded 7.6 g of intermediate 2C (yield 34%). The mass number of intermediate 2C, as measured by FAB-MS, was 1120.

[0430] (Synthesis of 2D intermediates) JPEG2026139258000153.jpg55170

[0431] Under an Ar atmosphere, 7.6 g of intermediate 2C was placed in a 500 mL three-necked flask and dissolved in o-dichlorobenzene (ODCB, 150 mL). The mixture was cooled to 0°C in an ice bath, and after adding boron triiodide (BI3, 16 g), the mixture was heated and stirred at 140°C for 6 hours. The mixture was then cooled to 0°C in an ice bath, and N,N-diisopropylethylamine (DIPEA, 30 mL) was added. After returning to room temperature, the reaction solution was filtered through silica gel, and the filtrate solvent was removed by distillation under reduced pressure. The resulting crude product was purified by silica gel column chromatography to obtain 1.1 g of intermediate 2D (yield 14%). The molecular weight of intermediate 2D, as measured by FAB-MS, was 1143.

[0432] (Synthesis of Compound 2) JPEG2026139258000154.jpg55170

[0433] Under an Ar atmosphere, intermediate 2D (1.1 g), bis[di-tert-butyl(4-dimethylaminophenyl)phosphine]dichloropalladium(II) (PdCl2(Amphos)2, 0.07 g), potassium ferrocyanide (K4Fe(CN)6, 0.6 g), NA2CO3 (0.4 g), and DMA (N,N-dimethylacetamine, 10 mL) were added to a 200 mL three-necked flask and heated and stirred at 140 °C for 24 hours. After returning to room temperature, water was added and the mixture was extracted with toluene. The organic layer was dried in one step over MgSO4, and the solvent was removed by distillation under reduced pressure. The mixture was purified by silica gel column chromatography to obtain 0.93 g of compound 2 (yield 85%). The mass number of compound 2, as measured by FAB-MS, was 1137.

[0434] (3) Synthesis of compound 3

[0435] (Synthesis of intermediate 3B) JPEG2026139258000155.jpg48170

[0436] Under an Ar atmosphere, intermediate 1A (50g), intermediate 3A (90g), K2CO3 (87g), and 1-methyl-2-pyrrolidone (400mL) were added to a 1000mL three-necked flask and heated and stirred at 160°C for 16 hours. After returning to room temperature, water was added and extracted with CH2Cl2. The organic layer was dried in one go over MgSO4, and the solvent was removed by distillation under reduced pressure. Purification by silica gel column chromatography yielded 79g of intermediate 3B (70% yield). The mass number of intermediate 3B, as measured by FAB-MS, was 540.

[0437] (Synthesis of intermediate 3C) JPEG2026139258000156.jpg24170

[0438] Under an Ar atmosphere, intermediate 1D (25 g), intermediate 1B (8 g), CuI (3.2 g), dipivaloylmethane (6.3 g), Cs2CO3 (42 g), and 1-methyl-2-pyrrolidone (200 mL) were added to a 500 mL three-necked flask and heated and stirred at 80 °C for 16 hours. After returning to room temperature, water was added and extracted with CH2Cl2. The organic layer was dried in one step over MgSO4, and the solvent was removed by distillation under reduced pressure. Purification by silica gel column chromatography yielded 10 g of intermediate 3C (yield 39%). The mass number of intermediate 3C, as measured by FAB-MS, was 309.

[0439] (Synthesis of intermediate 3E) JPEG2026139258000157.jpg43170

[0440] Under an Ar atmosphere, intermediate 1F (24 g), intermediate 3D (36 g), CuI (7.3 g), and K2CO3 (32 g) were added to a 300 mL three-necked flask and heated and stirred at 210 °C for 48 hours. After returning to room temperature, water was added and extracted with CH2Cl2. The organic layer was dried in one step over MgSO4, and the solvent was removed by distillation under reduced pressure. Purification by silica gel column chromatography yielded 7 g of intermediate 3E (yield 25%). The mass number of intermediate 3E, as measured by FAB-MS, was 727.

[0441] (Synthesis of intermediate 3F) JPEG2026139258000158.jpg54170

[0442] Under an Ar atmosphere, intermediate 3E (7g), intermediate 3B (21g), CuI (1.8g), and K2CO3 (6g) were added to a 200mL three-necked flask and heated and stirred at 230°C for 48 hours. After returning to room temperature, water was added and extracted with CH2Cl2. The organic layer was dried in one go over MgSO4, and the solvent was removed by distillation under reduced pressure. Purification by silica gel column chromatography yielded 4.6g of intermediate 3F (42% yield). The mass number of intermediate 3F, as measured by FAB-MS, was 1139.

[0443] (Synthesis of intermediate 3G) JPEG2026139258000159.jpg54170

[0444] Under an Ar atmosphere, 4.6 g of intermediate 3F was placed in a 200 mL three-necked flask and dissolved in 100 mL of dichloromethane. The mixture was cooled to 0°C in an ice bath, and 2.9 g of boron tribromide (BBr3) was added. The mixture was then heated and stirred at room temperature for 24 hours. Ice water was added to the reaction solution, and the mixture was extracted with CH2Cl2. The solvent was removed by distillation under reduced pressure. The resulting crude product was purified by silica gel column chromatography to obtain 3.8 g of intermediate 3G (84% yield). The molecular weight of intermediate 3G, as measured by FAB-MS, was 1125.

[0445] (Synthesis of intermediate 3H) JPEG2026139258000160.jpg49170

[0446] Under an Ar atmosphere, intermediate 3G (3.8g), intermediate 3C (2g), CuI (0.6g), K2CO3 (1.2g), and o-dichlorobenzene (ODCB, 30mL) were added to a 200mL three-necked flask and heated and stirred at 180°C for 16 hours. After returning to room temperature, water was added and extracted with CH2Cl2. The organic layer was dried in one step over MgSO4, and the solvent was removed by distillation under reduced pressure. Purification by silica gel column chromatography yielded 4g of intermediate 3H (yield 88%). The mass number of intermediate 3H measured by FAB-MS was 1350.

[0447] (Synthesis of Compound 3) Under an Ar atmosphere, 4 g of intermediate 3H was placed in a 300 mL three-necked flask and dissolved in o-dichlorobenzene (ODCB, 100 mL). The mixture was cooled to 0°C in an ice bath, and boron triiodide (BI3, 7 g) was added. The mixture was then heated and stirred at 140°C for 6 hours, cooled to 0°C in an ice bath, and N,N-diisopropylethylamine (DIPEA, 15 mL) was added. After returning to room temperature, the reaction solution was filtered through silica gel, and the filtrate solvent was removed by distillation under reduced pressure. The resulting crude product was purified by silica gel column chromatography to obtain 1.5 g of compound 3 (yield 37%). The molecular weight of compound 3, as measured by FAB-MS, was 1373.

[0448] (4) Synthesis of compound 4

[0449] (Synthesis of intermediate 4A) JPEG2026139258000161.jpg48170

[0450] Under an Ar atmosphere, intermediate 1F (40 g), intermediate 3D (62 g), CuI (13 g), and K2CO3 (56 g) were added to a 300 mL three-necked flask and heated and stirred at 210 °C for 48 hours. After returning to room temperature, water was added and extracted with CH2Cl2. The organic layer was dried in one go over MgSO4, and the solvent was removed by distillation under reduced pressure. Purification by silica gel column chromatography yielded 19.8 g of intermediate 4A (yield 38%). The mass number of intermediate 4A, as measured by FAB-MS, was 705.

[0451] (Synthesis of intermediate 4B) JPEG2026139258000162.jpg45170

[0452] Under an Ar atmosphere, intermediate 4A (19.8 g), intermediate 1C (40 g), CuI (4.8 g), and K2CO3 (14 g) were added to a 200 mL three-necked flask and heated and stirred at 230 °C for 48 hours. After returning to room temperature, water was added and extracted with CH2Cl2. The organic layer was dried in one step over MgSO4, and the solvent was removed by distillation under reduced pressure. Purification by silica gel column chromatography yielded 12.6 g of intermediate 4B (52% yield). The mass number of intermediate 4B, as measured by FAB-MS, was 966.

[0453] (Synthesis of intermediate 4C) Under an Ar atmosphere, 12.6 g of intermediate 4B was placed in a 300 mL three-necked flask and dissolved in 150 mL of dichloromethane. The mixture was cooled to 0°C in an ice bath, and 6.4 g of boron tribromide (BBr3) was added. The mixture was then heated and stirred at room temperature for 24 hours. Ice water was added to the reaction solution, and the mixture was extracted with CH2Cl2. The solvent was removed by distillation under reduced pressure. The resulting crude product was purified by silica gel column chromatography to obtain 10.8 g of intermediate 4C (87% yield). The molecular weight of intermediate 4C, as measured by FAB-MS, was 952.

[0454] (Synthesis of intermediate 4D) JPEG2026139258000163.jpg49170

[0455] Under an Ar atmosphere, intermediate 4C (10.8 g), intermediate 3C (6.4 g), CuI (2 g), K2CO3 (3 g), and o-dichlorobenzene (ODCB, 60 mL) were added to a 200 mL three-necked flask and heated and stirred at 180 °C for 16 hours. After returning to room temperature, water was added and extracted with CH2Cl2. The organic layer was dried in one step over MgSO4, and the solvent was removed by distillation under reduced pressure. Purification by silica gel column chromatography yielded 12.4 g of intermediate 4D (93% yield). The mass number of intermediate 4D, as measured by FAB-MS, was 1179.

[0456] (Synthesis of intermediate 4E) JPEG2026139258000164.jpg49170

[0457] Under an Ar atmosphere, 12.4 g of intermediate 4D was placed in a 500 mL three-necked flask and dissolved in o-dichlorobenzene (ODCB, 200 mL). The mixture was cooled to 0°C in an ice bath, 25 g of boron triiodide (BI3) was added, and the mixture was heated and stirred at 140°C for 6 hours. The mixture was then cooled to 0°C in an ice bath, and 50 mL of N,N-diisopropylethylamine (DIPEA) was added. After returning to room temperature, the reaction solution was filtered through silica gel, and the filtrate solvent was removed by distillation under reduced pressure. The resulting crude product was purified by silica gel column chromatography to obtain 2 g of intermediate 4E (yield 16%). The molecular weight of intermediate 4E, as measured by FAB-MS, was 1199.

[0458] (Synthesis of Compound 4) JPEG2026139258000165.jpg52170

[0459] Under an Ar atmosphere, 2 g of intermediate 4E, 1 g of 2-biphenylboronic acid, 75 mg of palladium(II) acetate (Pd(OAc)2), 0.27 g of 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (SPhos), 1 g of K3PO4, and 30 mL of toluene were added to a 100 mL three-necked flask and heated and stirred at 110 °C for 24 hours. After returning to room temperature, water was added and the mixture was extracted with CH2Cl2. The organic layer was dried in one step over MgSO4, and the solvent was removed by distillation under reduced pressure. The mixture was purified by silica gel column chromatography to obtain 0.83 g of compound 4 (43% yield). The mass number of compound 4, as measured by FAB-MS, was 1165.

[0460] (5) Synthesis of compound 5

[0461] (Synthesis of intermediate 5A) JPEG2026139258000166.jpg55170

[0462] Under an Ar atmosphere, intermediate 3E (12 g), intermediate 1C (26 g), CuI (3.1 g), and K2CO3 (14 g) were added to a 200 mL three-necked flask and heated and stirred at 230 °C for 48 hours. After returning to room temperature, water was added and extracted with CH2Cl2. The organic layer was dried in one step over MgSO4, and the solvent was removed by distillation under reduced pressure. Purification by silica gel column chromatography yielded 8.6 g of intermediate 5A (yield 53%). The mass number of intermediate 5A, as measured by FAB-MS, was 987.

[0463] (Synthesis of intermediate 5B) JPEG2026139258000167.jpg51170

[0464] Under an Ar atmosphere, 8.6 g of intermediate 5A was placed in a 300 mL three-necked flask and dissolved in 100 mL of dichloromethane. The mixture was cooled to 0°C in an ice bath, and 4.3 g of boron tribromide (BBr3) was added. The mixture was then heated and stirred at room temperature for 24 hours. Ice water was added to the reaction solution, and the mixture was extracted with CH2Cl2. The solvent was removed by distillation under reduced pressure. The resulting crude product was purified by silica gel column chromatography to obtain 7.8 g of intermediate 5B (92% yield). The molecular weight of intermediate 5B, as measured by FAB-MS, was 973.

[0465] (Synthesis of intermediate 5C) JPEG2026139258000168.jpg50170

[0466] Under an Ar atmosphere, intermediate 5B (7.8g), intermediate 1C (4.9g), CuI (1.5g), K2CO3 (3g), and o-dichlorobenzene (ODCB, 50mL) were added to a 200mL three-necked flask and heated and stirred at 180°C for 16 hours. After returning to room temperature, water was added and extracted with CH2Cl2. The organic layer was dried in one step over MgSO4, and the solvent was removed by distillation under reduced pressure. Purification by silica gel column chromatography yielded 8.6g of intermediate 5C (90% yield). The mass number of intermediate 5C, as measured by FAB-MS, was 1198.

[0467] (Synthesis of Compound 5) JPEG2026139258000169.jpg49170

[0468] Under an Ar atmosphere, 8.6 g of intermediate 5C was placed in a 500 mL three-necked flask and dissolved in o-dichlorobenzene (ODCB, 200 mL). The mixture was cooled to 0°C in an ice bath, 17 g of boron triiodide (BI3) was added, and the mixture was heated and stirred at 140°C for 6 hours. The mixture was then cooled to 0°C in an ice bath, and 30 mL of N,N-diisopropylethylamine (DIPEA) was added. After returning to room temperature, the reaction solution was filtered through silica gel, and the filtrate solvent was removed by distillation under reduced pressure. The resulting crude product was purified by silica gel column chromatography to obtain 2.2 g of compound 5 (yield 22%). The molecular weight of compound 5, as measured by FAB-MS, was 1220.

[0469] (6) Synthesis of compound 6

[0470] (Synthesis of intermediate 6B) JPEG2026139258000170.jpg20170

[0471] Under an Ar atmosphere, intermediate 6A (50 g), intermediate 1B (15 g), CuI (6 g), dipivaloylmethane (11.6 g), Cs2CO3 (77 g), and 1-methyl-2-pyrrolidone (400 mL) were added to a 1000 mL three-necked flask and heated and stirred at 50 °C for 16 hours. After returning to room temperature, water was added and extracted with CH2Cl2. The organic layer was dried in one step over MgSO4, and the solvent was removed by distillation under reduced pressure. Purification by silica gel column chromatography yielded 22 g of intermediate 6B (49% yield). The mass number of intermediate 6B, as measured by FAB-MS, was 284.

[0472] (Synthesis of intermediate 6C) JPEG2026139258000171.jpg55170

[0473] Under an Ar atmosphere, intermediate 4C (30g), intermediate 6B (18g), CuI (6g), K2CO3 (16g), and o-dichlorobenzene (ODCB, 200mL) were added to a 500mL three-necked flask and heated and stirred at 180°C for 16 hours. After returning to room temperature, water was added and extracted with CH2Cl2. The organic layer was dried in one step over MgSO4, and the solvent was removed by distillation under reduced pressure. Purification by silica gel column chromatography yielded 33g of intermediate 6C (92% yield). The mass number of intermediate 6C, as measured by FAB-MS, was 1154.

[0474] (Synthesis of intermediate 6D) JPEG2026139258000172.jpg49170

[0475] Under an Ar atmosphere, 33 g of intermediate 6C was placed in a 1000 mL three-necked flask and dissolved in o-dichlorobenzene (ODCB, 400 mL). The mixture was cooled to 0°C in an ice bath, 67 g of boron triiodide (BI3) was added, and the mixture was heated and stirred at 140°C for 6 hours. The mixture was then cooled to 0°C in an ice bath, and 100 mL of N,N-diisopropylethylamine (DIPEA) was added. After returning to room temperature, the reaction solution was filtered through silica gel, and the filtrate solvent was removed by distillation under reduced pressure. The resulting crude product was purified by silica gel column chromatography to obtain 4 g of intermediate 6D (yield 12%). The molecular weight of intermediate 6D, as measured by FAB-MS, was 1178.

[0476] (Synthesis of Compound 6) JPEG2026139258000173.jpg54170

[0477] Under an Ar atmosphere, intermediate 6D (4 g), 2-biphenylboronic acid (4 g), palladium(II) acetate (Pd(OAc)2, 0.15 g), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (SPhos, 0.56 g), K3PO4 (4.3 g), and toluene (80 mL) were added to a 200 mL three-necked flask and heated and stirred at 110 °C for 24 hours. After returning to room temperature, water was added and extracted with CH2Cl2. The organic layer was dried in one step over MgSO4, and the solvent was removed by distillation under reduced pressure. The compound was purified by silica gel column chromatography to obtain 0.79 g of compound 6 (yield 21%). The mass number of compound 6, as measured by FAB-MS, was 1109.

[0478] (7) Synthesis of compound 7

[0479] (Synthesis of intermediate 7A) JPEG2026139258000174.jpg57170

[0480] Under an Ar atmosphere, intermediate 5B (30g), intermediate 6B (18g), CuI (3g), K2CO3 (6g), and o-dichlorobenzene (ODCB, 120mL) were added to a 300mL three-necked flask and heated and stirred at 180°C for 16 hours. After returning to room temperature, water was added and extracted with CH2Cl2. The organic layer was dried in one step over MgSO4, and the solvent was removed by distillation under reduced pressure. Purification by silica gel column chromatography yielded 16g of intermediate 7A (yield 88%). The mass number of intermediate 7A, as measured by FAB-MS, was 1176.

[0481] (Synthesis of intermediate 7B) JPEG2026139258000175.jpg53170

[0482] Under an Ar atmosphere, 16 g of intermediate 7A was placed in a 500 mL three-necked flask and dissolved in o-dichlorobenzene (ODCB, 200 mL). The mixture was cooled to 0°C in an ice bath, 32 g of boron triiodide (BI3) was added, and the mixture was heated and stirred at 140°C for 6 hours. The mixture was then cooled to 0°C in an ice bath, and 50 mL of N,N-diisopropylethylamine (DIPEA) was added. After returning to room temperature, the reaction solution was filtered through silica gel, and the filtrate solvent was removed by distillation under reduced pressure. The resulting crude product was purified by silica gel column chromatography to obtain 2.9 g of intermediate 7B (yield 19%). The molecular weight of intermediate 7B, as measured by FAB-MS, was 1200.

[0483] (Synthesis of Compound 7) JPEG2026139258000176.jpg53170

[0484] Under an Ar atmosphere, intermediate 7B (2.9 g), 2-biphenylboronic acid (1.4 g), palladium(II) acetate (Pd(OAc)2, 0.11 g), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (SPhos, 0.39 g), K3PO4 (1.5 g), and toluene (40 mL) were added to a 100 mL three-necked flask and heated and stirred at 110 °C for 24 hours. After returning to room temperature, water was added and extracted with CH2Cl2. The organic layer was dried in one step over MgSO4, and the solvent was removed by distillation under reduced pressure. The compound was purified by silica gel column chromatography to obtain 0.85 g of compound 7 (yield 30%). The mass number of compound 7, as measured by FAB-MS, was 1165.

[0485] (8) Synthesis of compound 8

[0486] (Synthesis of intermediate 8B) JPEG2026139258000177.jpg48170

[0487] Under an Ar atmosphere, intermediate 1C (33g), intermediate 8A (18g), CuI (11g), and K2CO3 (23g) were added to a 300mL three-necked flask and heated and stirred at 230°C for 48 hours. After returning to room temperature, water was added and extracted with CH2Cl2. The organic layer was dried in one go over MgSO4, and the solvent was removed by distillation under reduced pressure. Purification by silica gel column chromatography yielded 9.8g of intermediate 8B (yield 33%). The mass number of intermediate 8B, as measured by FAB-MS, was 533.

[0488] (Synthesis of intermediate 8C) JPEG2026139258000178.jpg58170

[0489] Under an Ar atmosphere, intermediate 5B (10 g), intermediate 8B (9.8 g), CuI (1.9 g), K2CO3 (3.9 g), and o-dichlorobenzene (ODCB, 100 mL) were added to a 300 mL three-necked flask and heated and stirred at 180 °C for 16 hours. After returning to room temperature, water was added and extracted with CH2Cl2. The organic layer was dried in one step over MgSO4, and the solvent was removed by distillation under reduced pressure. Purification by silica gel column chromatography yielded 12.4 g of intermediate 8C (88% yield). The mass number of intermediate 8C, as measured by FAB-MS, was 1425.

[0490] (Synthesis of Compound 8) JPEG2026139258000179.jpg56170

[0491] Under an Ar atmosphere, 12.4 g of intermediate 8C was placed in a 500 mL three-necked flask and dissolved in o-dichlorobenzene (ODCB, 150 mL). The mixture was cooled to 0°C in an ice bath, 20 g of boron triiodide (BI3) was added, and the mixture was heated and stirred at 140°C for 6 hours. After cooling to 0°C in an ice bath, 35 mL of N,N-diisopropylethylamine (DIPEA) was added. After returning to room temperature, the reaction solution was filtered through silica gel, and the filtrate solvent was removed by distillation under reduced pressure. The resulting crude product was purified by silica gel column chromatography to obtain 3.0 g of compound 8 (yield 24%). The molecular weight of compound 8, as measured by FAB-MS, was 1448.

[0492] (9) Synthesis of compound 9

[0493] (Synthesis of intermediate 9B) JPEG2026139258000180.jpg39170

[0494] Under an Ar atmosphere, intermediate 3C (15g), intermediate 9A (11g), bis(dibenzylideneacetone)palladium(0)(Pd(dba)2, 0.56g), (±)-BINAP (1.2g), sodium tert-butoxide (NaOtBu, 7g), and toluene (200mL) were added to a 500mL three-necked flask and heated and stirred at 60°C for 12 hours. After returning to room temperature, water was added and extracted with toluene. The organic layer was dried in one go over MgSO4, and the solvent was removed by distillation under reduced pressure. Purification by silica gel column chromatography yielded 17g of intermediate 9B (yield 88%). The mass number of intermediate 9B, as measured by FAB-MS, was 394.

[0495] (Synthesis of intermediate 9C) JPEG2026139258000181.jpg50170

[0496] Under an Ar atmosphere, intermediate 1F (30 g), intermediate 1C (56 g), CuI (9.2 g), and K2CO3 (27 g) were added to a 300 mL three-necked flask and heated and stirred at 230 °C for 48 hours. After returning to room temperature, water was added and extracted with CH2Cl2. The organic layer was dried in one step over MgSO4, and the solvent was removed by distillation under reduced pressure. Purification by silica gel column chromatography yielded 13.6 g of intermediate 9C (yield 32%). The mass number of intermediate 9C, as measured by FAB-MS, was 881.

[0497] (Synthesis of intermediate 9E) JPEG2026139258000182.jpg48170

[0498] Under an Ar atmosphere, intermediate 9C (13.6 g), intermediate 9D (22 g), CuI (2.9 g), and K2CO3 (8.5 g) were added to a 200 mL three-necked flask and heated and stirred at 230 °C for 48 hours. After returning to room temperature, water was added and extracted with CH2Cl2. The organic layer was dried in one step over MgSO4, and the solvent was removed by distillation under reduced pressure. Purification by silica gel column chromatography yielded 8.1 g of intermediate 9E (yield 53%). The mass number of intermediate 9E, as measured by FAB-MS, was 992.

[0499] (Synthesis of intermediate 9F) JPEG2026139258000183.jpg49170

[0500] Under an Ar atmosphere, intermediate 9E (8.1 g), intermediate 9B (4.8 g), bis(dibenzylideneacetone)palladium(0) (Pd(dba)2, 0.14 g), tri-tert-butylphosphine tetrafluoroborate (0.14 g), sodium tert-butoxide (NaOtBu, 1.6 g), and toluene (80 mL) were added to a 200 mL three-necked flask and heated and stirred at 110 °C for 24 hours. After returning to room temperature, water was added and the mixture was extracted with toluene. The organic layer was dried in one step over MgSO4, and the solvent was removed by distillation under reduced pressure. The mixture was purified by silica gel column chromatography to obtain 7.9 g of intermediate 9F (yield 72%). The mass number of intermediate 9F, as measured by FAB-MS, was 1349.

[0501] (Synthesis of Compound 9) JPEG2026139258000184.jpg45170

[0502] Under an Ar atmosphere, 12.4 g of intermediate 9F was placed in a 300 mL three-necked flask and dissolved in o-dichlorobenzene (ODCB, 100 mL). The mixture was cooled to 0°C in an ice bath, and after adding boron triiodide (BI3, 14 g), it was heated and stirred at 140°C for 6 hours. The mixture was then cooled to 0°C in an ice bath, and N,N-diisopropylethylamine (DIPEA, 20 mL) was added. After returning to room temperature, the reaction solution was filtered through silica gel, and the filtrate solvent was removed by distillation under reduced pressure. The resulting crude product was purified by silica gel column chromatography to obtain 2.9 g of compound 9 (yield 36%). The molecular weight of compound 9, as measured by FAB-MS, was 1372.

[0503] (10) Synthesis of compound 10

[0504] (Synthesis of intermediate 10B) JPEG2026139258000185.jpg39170

[0505] Under an Ar atmosphere, intermediate 10A (50g), intermediate 1B (34g), K2CO3 (60g), and 1-methyl-2-pyrrolidone (400mL) were added to a 1000mL three-necked flask and heated and stirred at 140°C for 16 hours. After returning to room temperature, water was added and extracted with CH2Cl2. The organic layer was dried in one go over MgSO4, and the solvent was removed by distillation under reduced pressure. Purification by silica gel column chromatography yielded 51g of intermediate 10B (84% yield). The mass number of intermediate 10B, as measured by FAB-MS, was 422.

[0506] (Synthesis of intermediate 10D) JPEG2026139258000186.jpg53170

[0507] Under an Ar atmosphere, intermediate 10B (51 g), intermediate 10C (39 g), bis(dibenzylideneacetone)palladium(0) (Pd(dba)2, 0.69 g), (±)-BINAP (1.5 g), sodium tert-butoxide (NaOtBu, 17.4 g), and toluene (400 mL) were added to a 1000 mL three-necked flask and heated and stirred at 100 °C for 12 hours. After returning to room temperature, water was added and extracted with toluene. The organic layer was dried in one go over MgSO4, and the solvent was removed by distillation under reduced pressure. Purification by silica gel column chromatography yielded 23 g of intermediate 10D (yield 31%). The mass number of intermediate 10D measured by FAB-MS was 616.

[0508] (Synthesis of intermediate 10E) JPEG2026139258000187.jpg54170

[0509] Under an Ar atmosphere, intermediate 10D (23 g), intermediate 3E (13 g), CuI (3.4 g), and K2CO3 (7.4 g) were added to a 200 mL three-necked flask and heated and stirred at 230 °C for 48 hours. After returning to room temperature, water was added and extracted with CH2Cl2. The organic layer was dried in one step over MgSO4, and the solvent was removed by distillation under reduced pressure. Purification by silica gel column chromatography yielded 6.5 g of intermediate 10E (30% yield). The mass number of intermediate 10E, as measured by FAB-MS, was 1215.

[0510] (Synthesis of intermediate 10F) JPEG2026139258000188.jpg51170

[0511] Under an Ar atmosphere, 6.5 g of intermediate 10E was placed in a 300 mL three-necked flask and dissolved in 100 mL of dichloromethane. The mixture was cooled to 0°C in an ice bath, and 2.7 g of boron tribromide (BBr3) was added. The mixture was then heated and stirred at room temperature for 24 hours. Ice water was added to the reaction solution, and the mixture was extracted with CH2Cl2. The solvent was removed by distillation under reduced pressure. The resulting crude product was purified by silica gel column chromatography to obtain 5.5 g of intermediate 10F (86% yield). The molecular weight of intermediate 10F, as measured by FAB-MS, was 1201.

[0512] (Synthesis of intermediate 10G) JPEG2026139258000189.jpg50170

[0513] Under an Ar atmosphere, intermediate 10F (5.5g), intermediate 3C (2.8g), CuI (0.8g), K2CO3 (2g), and o-dichlorobenzene (ODCB, 60mL) were added to a 200mL three-necked flask and heated and stirred at 180°C for 16 hours. After returning to room temperature, water was added and extracted with CH2Cl2. The organic layer was dried in one step over MgSO4, and the solvent was removed by distillation under reduced pressure. Purification by silica gel column chromatography yielded 5.7g of intermediate 10G (yield 88%). The mass number of intermediate 10G, as measured by FAB-MS, was 1425.

[0514] (Synthesis of compound 10) JPEG2026139258000190.jpg54170

[0515] Under an Ar atmosphere, 10 g (5.7 g) of the intermediate was placed in a 300 mL three-necked flask and dissolved in o-dichlorobenzene (ODCB, 100 mL). The mixture was cooled to 0°C in an ice bath, and after adding boron triiodide (BI3, 9.4 g), the mixture was heated and stirred at 140°C for 6 hours. The mixture was then cooled to 0°C in an ice bath, and N,N-diisopropylethylamine (DIPEA, 15 mL) was added. After returning to room temperature, the reaction solution was filtered through silica gel, and the filtrate solvent was removed by distillation under reduced pressure. The resulting crude product was purified by silica gel column chromatography to obtain 1.8 g of compound 10 (yield 31%). The molecular weight of compound 10, as measured by FAB-MS, was 1448.

[0516] (11) Synthesis of compound 11

[0517] (Synthesis of intermediate 11B) JPEG2026139258000191.jpg43170

[0518] Under an Ar atmosphere, intermediate 10B (30g), intermediate 111A (23g), bis(dibenzylideneacetone)palladium(0) (Pd(dba)2, 0.41g), (±)-BINAP (0.88g), sodium tert-butoxide (NaOtBu, 10g), and toluene (400mL) were added to a 1000mL three-necked flask and heated and stirred at 100°C for 12 hours. After returning to room temperature, water was added and extracted with toluene. The organic layer was dried in one go over MgSO4, and the solvent was removed by distillation under reduced pressure. Purification by silica gel column chromatography yielded 14.9g of intermediate 11B (yield 34%). The mass number of intermediate 11B, as measured by FAB-MS, was 616.

[0519] (Synthesis of intermediate 11C) JPEG2026139258000192.jpg39170

[0520] Under an Ar atmosphere, intermediate 2A (10 g), intermediate 9A (12.5 g), bis(dibenzylideneacetone)palladium(0) (Pd(dba)2, 0.43 g), (±)-BINAP (0.92 g), sodium tert-butoxide (NaOtBu, 9 g), and toluene (250 mL) were added to a 500 mL three-necked flask and heated and stirred at 100 °C for 12 hours. After returning to room temperature, water was added and extracted with toluene. The organic layer was dried in one go over MgSO4, and the solvent was removed by distillation under reduced pressure. Purification by silica gel column chromatography yielded 13.2 g of intermediate 11C (80% yield). The mass number of intermediate 11C, as measured by FAB-MS, was 447.

[0521] (Synthesis of intermediate 11D) JPEG2026139258000193.jpg54170

[0522] Under an Ar atmosphere, intermediate 11C (10 g), intermediate 11B (13.8 g), bis(dibenzylideneacetone)palladium(0) (Pd(dba)2, 0.13 g), tri-tert-butylphosphine tetrafluoroborate (0.13 g), sodium tert-butoxide (NaOtBu, 3.2 g), and toluene (100 mL) were added to a 300 mL three-necked flask and heated and stirred at 110 °C for 24 hours. After returning to room temperature, water was added and extracted with toluene. The organic layer was dried in one step over MgSO4, and the solvent was removed by distillation under reduced pressure. Purification by silica gel column chromatography yielded 6.7 g of intermediate 11D (yield 32%). The mass number of intermediate 11D, as measured by FAB-MS, was 935.

[0523] (Synthesis of intermediate 11E) JPEG2026139258000194.jpg52170

[0524] Under an Ar atmosphere, intermediate 11D (6.7g), intermediate 3B (3.9g), bis(dibenzylideneacetone)palladium(0) (Pd(dba)2, 0.04g), tri-tert-butylphosphinetetrafluoroborate (0.04g), sodium tert-butoxide (NaOtBu, 1g), and toluene (60mL) were added to a 200mL three-necked flask and heated and stirred at 60°C for 24 hours. After returning to room temperature, water was added and extracted with toluene. The organic layer was dried in one go over MgSO4, and the solvent was removed by distillation under reduced pressure. Purification by silica gel column chromatography yielded 8.3g of intermediate 11E (yield 86%). The mass number of intermediate 11E, as measured by FAB-MS, was 1347.

[0525] (Synthesis of intermediate 11G) JPEG2026139258000195.jpg55170

[0526] Under an Ar atmosphere, intermediate 11E (8.3g), intermediate 11F (2.3g), palladium(II) acetate (Pd(OAc)2, 0.069g), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (SPhos, 0.25g), K3PO4 (3.9g), and toluene (80mL) were added to a 200mL three-necked flask and heated and stirred at 100°C for 24 hours. After returning to room temperature, water was added and extracted with CH2Cl2. The organic layer was dried in one step over MgSO4, and the solvent was removed by distillation under reduced pressure. Purification by silica gel column chromatography yielded 5.6g of intermediate 11G (yield 65%). The mass number of intermediate 11G, as measured by FAB-MS, was 1389.

[0527] (Synthesis of Compound 11) JPEG2026139258000196.jpg54170

[0528] Under an Ar atmosphere, 11g (5.6g) of the intermediate was placed in a 300mL three-necked flask and dissolved in o-dichlorobenzene (ODCB, 100mL). The mixture was cooled to 0°C in an ice bath, and after adding boron triiodide (BI3, 9.5g), it was heated and stirred at 140°C for 6 hours. The mixture was then cooled to 0°C in an ice bath, and N,N-diisopropylethylamine (DIPEA, 15mL) was added. After returning to room temperature, the reaction solution was filtered through silica gel, and the filtrate solvent was removed by distillation under reduced pressure. The resulting crude product was purified by silica gel column chromatography to obtain 2.4g (42% yield) of compound 11. The molecular weight of compound 11, as measured by FAB-MS, was 1412.

[0529] (12) Synthesis of compound 12

[0530] (Synthesis of intermediate 12A) JPEG2026139258000197.jpg43170

[0531] Under an Ar atmosphere, intermediate 1F (15g), intermediate 3D (45g), CuI (9.2g), and K2CO3 (27g) were added to a 300mL three-necked flask and heated and stirred at 210°C for 48 hours. After returning to room temperature, water was added and extracted with CH2Cl2. The organic layer was dried in one go over MgSO4, and the solvent was removed by distillation under reduced pressure. Purification by silica gel column chromatography yielded 9.3g of intermediate 12A (46% yield). The mass number of intermediate 12A, as measured by FAB-MS, was 833.

[0532] (Synthesis of intermediate 12B) JPEG2026139258000198.jpg40170

[0533] Under an Ar atmosphere, 9.3 g of intermediate 12A was placed in a 500 mL three-necked flask and dissolved in 200 mL of dichloromethane. The mixture was cooled to 0°C in an ice bath, and 11 g of boron tribromide (BBr3) was added. The mixture was then heated and stirred at room temperature for 24 hours. Ice water was added to the reaction solution, and the mixture was extracted with CH2Cl2. The solvent was removed by distillation under reduced pressure. The resulting crude product was purified by silica gel column chromatography to obtain 4.6 g of intermediate 12B (yield 52%). The molecular weight of intermediate 12B, as measured by FAB-MS, was 805.

[0534] (Synthesis of intermediate 12C) JPEG2026139258000199.jpg45170

[0535] Under an Ar atmosphere, intermediate 12B (4.6g), intermediate 3C (7g), CuI (2.2g), K2CO3 (5g), and o-dichlorobenzene (ODCB, 80mL) were added to a 200mL three-necked flask and heated and stirred at 180°C for 16 hours. After returning to room temperature, water was added and extracted with CH2Cl2. The organic layer was dried in one step over MgSO4, and the solvent was removed by distillation under reduced pressure. Purification by silica gel column chromatography yielded 5.6g of intermediate 12C (yield 78%). The mass number of intermediate 12C, as measured by FAB-MS, was 1254.

[0536] (Synthesis of Compound 12) JPEG2026139258000200.jpg52170

[0537] Under an Ar atmosphere, 5.6 g of intermediate 12C was placed in a 300 mL three-necked flask and dissolved in o-dichlorobenzene (ODCB, 100 mL). The mixture was cooled to 0°C in an ice bath, and boron triiodide (BI3, 10.5 g) was added. The mixture was then heated and stirred at 140°C for 6 hours, cooled to 0°C in an ice bath, and N,N-diisopropylethylamine (DIPEA, 20 mL) was added. After returning to room temperature, the reaction solution was filtered through silica gel, and the filtrate solvent was removed by distillation under reduced pressure. The resulting crude product was purified by silica gel column chromatography to obtain 2.2 g of compound 12 (yield 39%). The molecular weight of compound 12, as measured by FAB-MS, was 1277.

[0538] (13) Synthesis of compound 14

[0539] (Synthesis of intermediate 14B) JPEG2026139258000201.jpg39170

[0540] Under an Ar atmosphere, intermediate 1A (20 g), intermediate 14A (27 g), K2CO3 (35 g), and 1-methyl-2-pyrrolidone (200 mL) were added to a 500 mL three-necked flask and heated and stirred at 140 °C for 16 hours. After returning to room temperature, water was added and extracted with CH2Cl2. The organic layer was dried in one step over MgSO4, and the solvent was removed by distillation under reduced pressure. Purification by silica gel column chromatography yielded 23 g of intermediate 14B (yield 61%). The mass number of intermediate 14B, as measured by FAB-MS, was 457.

[0541] (Synthesis of intermediate 14D) JPEG2026139258000202.jpg40170

[0542] Under an Ar atmosphere, intermediate 14B (23g), intermediate 14C (17g), tetrakis(triphenylphosphine)palladium(0)(Pd(PPh3)4, 1.1g), K2CO3 (14g), and toluene / ethanol / H2O (150 / 60 / 30mL) were heated and stirred in a 500mL three-necked flask at 80°C for 24 hours. After returning to room temperature, water was added and extracted with toluene. The organic layer was dried in one step over MgSO4, and the solvent was removed by distillation under reduced pressure. Purification by silica gel column chromatography yielded 9.5g of intermediate 14D (42% yield). The mass number of intermediate 14D, as measured by FAB-MS, was 449.

[0543] (Synthesis of intermediate 14F) JPEG2026139258000203.jpg29170

[0544] Under an Ar atmosphere, intermediate 14E (20 g), intermediate 14C (12.3 g), tetrakis(triphenylphosphine)palladium(0)(Pd(PPh3)4, 0.9 g), K2CO3 (21 g), and toluene / ethanol / H2O (150 / 60 / 30 mL) were heated and stirred in a 500 mL three-necked flask at 80°C for 24 hours. After returning to room temperature, water was added and extracted with toluene. The organic layer was dried in one step over MgSO4, and the solvent was removed by distillation under reduced pressure. Purification by silica gel column chromatography yielded 6.9 g of intermediate 14F (30% yield). The mass number of intermediate 14F, as measured by FAB-MS, was 305.

[0545] (Synthesis of intermediate 14H) JPEG2026139258000204.jpg38170

[0546] Under an Ar atmosphere, intermediate 14F (6.9 g), intermediate 14G (6.1 g), bis(dibenzylideneacetone)palladium(0) (Pd(dba)2, 0.13 g), (±)-BINAP (0.28 g), sodium tert-butoxide (NaOtBu, 3.3 g), and toluene (80 mL) were added to a 300 mL three-necked flask and heated and stirred at 100 °C for 12 hours. After returning to room temperature, water was added and extracted with toluene. The organic layer was dried in one go over MgSO4, and the solvent was removed by distillation under reduced pressure. Purification by silica gel column chromatography yielded 8.4 g of intermediate 14H (80% yield). The mass number of intermediate 14H measured by FAB-MS was 470.

[0547] (Synthesis of intermediate 14I) JPEG2026139258000205.jpg49170

[0548] Under an Ar atmosphere, intermediate 14H (8.4 g), intermediate 14D (4 g), bis(dibenzylideneacetone)palladium(0) (Pd(dba)2, 0.15 g), tri-tert-butylphosphine tetrafluoroborate (0.15 g), sodium tert-butoxide (NaOtBu, 3.4 g), and toluene (100 mL) were added to a 300 mL three-necked flask and heated and stirred at 110 °C for 24 hours. After returning to room temperature, water was added and extracted with toluene. The organic layer was dried in one step over MgSO4, and the solvent was removed by distillation under reduced pressure. Purification by silica gel column chromatography yielded 8.2 g of intermediate 14I (70% yield). The mass number of intermediate 14I, as measured by FAB-MS, was 1316.

[0549] (Synthesis of intermediate 14J) JPEG2026139258000206.jpg49170

[0550] Under an Ar atmosphere, 8.2 g of intermediate 14I was placed in a 500 mL three-necked flask and dissolved in 200 mL of dichloromethane. The mixture was cooled to 0°C in an ice bath, and 6.2 g of boron tribromide (BBr3) was added. The mixture was then heated and stirred at room temperature for 24 hours. Ice water was added to the reaction solution, and the mixture was extracted with CH2Cl2. The solvent was removed by distillation under reduced pressure. The resulting crude product was purified by silica gel column chromatography to obtain 4.4 g of intermediate 14J (yield 55%). The molecular weight of intermediate 14J, as measured by FAB-MS, was 1288.

[0551] (Synthesis of intermediate 14L) JPEG2026139258000207.jpg49170

[0552] Under an Ar atmosphere, 14J (4.4g) of intermediate, 14K (2.1g) of intermediate, 1.3g of CuI, 3g of K2CO3, and 80mL of o-dichlorobenzene (ODCB) were added to a 200mL three-necked flask and heated and stirred at 180°C for 16 hours. After returning to room temperature, water was added and extracted with CH2Cl2. The organic layer was dried in one step over MgSO4, and the solvent was removed by distillation under reduced pressure. Purification by silica gel column chromatography yielded 4.5g of 14L of intermediate (91% yield). The mass number of 14L of intermediate, as measured by FAB-MS, was 1440.

[0553] (Synthesis of Compound 14) JPEG2026139258000208.jpg49170

[0554] Under an Ar atmosphere, 14 L (4.2 g) of the intermediate was placed in a 300 mL three-necked flask, dissolved in o-dichlorobenzene (ODCB, 100 mL), cooled to 0°C in an ice bath, and after adding boron triiodide (BI3, 6.8 g), the mixture was heated and stirred at 140°C for 6 hours, cooled to 0°C in an ice bath, and N,N-diisopropylethylamine (DIPEA, 15 mL) was added. After returning to room temperature, the reaction solution was filtered through silica gel, and the filtrate solvent was removed by distillation under reduced pressure. The resulting crude product was purified by silica gel column chromatography to obtain 1.5 g of compound 14 (yield 35%). The molecular weight of compound 14, as measured by FAB-MS, was 1463.

[0555] (14) Synthesis of compound 15

[0556] (Synthesis of intermediate 15C) JPEG2026139258000209.jpg43170

[0557] Under an Ar atmosphere, intermediate 15A (10 g), intermediate 15B (7.3 g), CuI (10.5 g), K2CO3 (15 g), and o-dichlorobenzene (ODCB, 150 mL) were added to a 500 mL three-necked flask and heated and stirred at 120 °C for 16 hours. After returning to room temperature, water was added and extracted with CH2Cl2. The organic layer was dried in one step over MgSO4, and the solvent was removed by distillation under reduced pressure. Purification by silica gel column chromatography yielded 7.1 g of intermediate 15C (yield 78%). The mass number of intermediate 15C, as measured by FAB-MS, was 329.

[0558] (Synthesis of intermediate 15F) JPEG2026139258000210.jpg43170

[0559] Under an Ar atmosphere, intermediate 15D (15 g), intermediate 15E (8 g), palladium(II) acetate (Pd(OAc)2, 0.27 g), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (Xantphos, 0.73 g), sodium tert-butoxide (NaOtBu, 6.8 g), and toluene (200 mL) were added to a 500 mL three-necked flask and heated and stirred at 80°C for 24 hours. After returning to room temperature, water was added and the mixture was extracted with toluene. The organic layer was dried in one step over MgSO4, and the solvent was removed by distillation under reduced pressure. The mixture was purified by silica gel column chromatography to obtain 14.9 g of intermediate 15F (yield 78%). The mass number of intermediate 15F, as measured by FAB-MS, was 403.

[0560] (Synthesis of intermediate 15H) JPEG2026139258000211.jpg40170

[0561] Under an Ar atmosphere, intermediate 15F (9 g), intermediate 15G (11 g), bis(dibenzylideneacetone)palladium(0) (Pd(dba)2, 0.26 g), (±)-BINAP (0.56 g), sodium tert-butoxide (NaOtBu, 5.4 g), and toluene (150 mL) were added to a 500 mL three-necked flask and heated and stirred at 100 °C for 12 hours. After returning to room temperature, water was added and extracted with toluene. The organic layer was dried in one step over MgSO4, and the solvent was removed by distillation under reduced pressure. Purification by silica gel column chromatography yielded 13.4 g of intermediate 15H (82% yield). The mass number of intermediate 15H, as measured by FAB-MS, was 732.

[0562] (Synthesis of intermediate 15I) JPEG2026139258000212.jpg51170

[0563] Under an Ar atmosphere, intermediate 15I (13.4 g), intermediate 15C (6 g), bis(dibenzylideneacetone)palladium(0) (Pd(dba)2, 0.21 g), tri-tert-butylphosphine tetrafluoroborate (0.21 g), sodium tert-butoxide (NaOtBu, 2.6 g), and toluene (100 mL) were added to a 300 mL three-necked flask and heated and stirred at 110 °C for 24 hours. After returning to room temperature, water was added and the mixture was extracted with toluene. The organic layer was dried in one step over MgSO4, and the solvent was removed by distillation under reduced pressure. The mixture was purified by silica gel column chromatography to obtain 7.5 g of intermediate 15I (40% yield). The mass number of intermediate 15I, as measured by FAB-MS, was 1024.

[0564] (Synthesis of intermediate 15J) JPEG2026139258000213.jpg51170

[0565] Under an Ar atmosphere, intermediate 15I (7.5g), intermediate 1C (2.8g), bis(dibenzylideneacetone)palladium(0)(Pd(dba)2, 0.04g), tri-tert-butylphosphinetetrafluoroborate (0.04g), sodium tert-butoxide (NaOtBu, 1g), and toluene (80mL) were added to a 200mL three-necked flask and heated and stirred at 100°C for 24 hours. After returning to room temperature, water was added and extracted with toluene. The organic layer was dried in one step over MgSO4, and the solvent was removed by distillation under reduced pressure. Purification by silica gel column chromatography yielded 7.9g of intermediate 15J (yield 84%). The mass number of intermediate 15J, as measured by FAB-MS, was 1284.

[0566] (Synthesis of Compound 15) JPEG2026139258000214.jpg52170

[0567] Under an Ar atmosphere, 15 J (7.9 g) of the intermediate was placed in a 500 mL three-necked flask and dissolved in o-dichlorobenzene (ODCB, 150 mL). The mixture was cooled to 0°C in an ice bath, and after adding boron triiodide (BI3, 14.6 g), the mixture was heated and stirred at 140°C for 6 hours. The mixture was then cooled to 0°C in an ice bath, and N,N-diisopropylethylamine (DIPEA, 25 mL) was added. After returning to room temperature, the reaction solution was filtered through silica gel, and the filtrate solvent was removed by distillation under reduced pressure. The resulting crude product was purified by silica gel column chromatography to obtain 3.9 g of compound 15 (yield 48%). The molecular weight of compound 15, as measured by FAB-MS, was 1308.

[0568] (15) Synthesis of compound 16

[0569] (Synthesis of intermediate 16A) JPEG2026139258000215.jpg37170

[0570] Under an Ar atmosphere, intermediate 6A (19.4g), intermediate 1E (15g), bis(dibenzylideneacetone)palladium(0) (Pd(dba)2, 0.35g), (±)-BINAP (0.76g), sodium tert-butoxide (NaOtBu, 8.8g), and toluene (300mL) were added to a 1000mL three-necked flask and heated and stirred at 60°C for 12 hours. After returning to room temperature, water was added and extracted with toluene. The organic layer was dried in one go over MgSO4, and the solvent was removed by distillation under reduced pressure. Purification by silica gel column chromatography yielded 13.6g of intermediate 16A (yield 51%). The mass number of intermediate 16A, as measured by FAB-MS, was 434.

[0571] (Synthesis of intermediate 16B) JPEG2026139258000216.jpg33170

[0572] Under an Ar atmosphere, intermediate 16A (13.6g), intermediate 15G (24.1g), bis(dibenzylideneacetone)palladium(0) (Pd(dba)2, 0.32g), (±)-BINAP (0.69g), sodium tert-butoxide (NaOtBu, 8g), and toluene (300mL) were added to a 1000mL three-necked flask and heated and stirred at 60°C for 12 hours. After returning to room temperature, water was added and extracted with toluene. The organic layer was dried in one go over MgSO4, and the solvent was removed by distillation under reduced pressure. Purification by silica gel column chromatography yielded 30.6g of intermediate 16B (92% yield). The mass number of intermediate 16B, as measured by FAB-MS, was 599.

[0573] (Synthesis of intermediate 16C) JPEG2026139258000217.jpg47170

[0574] Under an Ar atmosphere, intermediate 16B (20 g), intermediate 1C (78 g), CuI (12.7 g), and K2CO3 (37 g) were added to a 500 mL three-necked flask and heated and stirred at 230 °C for 48 hours. After returning to room temperature, water was added and extracted with CH2Cl2. The organic layer was dried in one step over MgSO4, and the solvent was removed by distillation under reduced pressure. Purification by silica gel column chromatography yielded 17.2 g of intermediate 16C (46% yield). The mass number of intermediate 16C, as measured by FAB-MS, was 1120.

[0575] (Synthesis of intermediate 16D) JPEG2026139258000218.jpg45170

[0576] Under an Ar atmosphere, 17.2 g of intermediate 16C was placed in a 1000 mL three-necked flask and dissolved in o-dichlorobenzene (ODCB, 300 mL). The mixture was cooled to 0°C in an ice bath, and boron triiodide (BI3, 36 g) was added. The mixture was then heated and stirred at 140°C for 6 hours, cooled to 0°C in an ice bath, and N,N-diisopropylethylamine (DIPEA, 60 mL) was added. After returning to room temperature, the reaction solution was filtered through silica gel, and the filtrate solvent was removed by distillation under reduced pressure. The resulting crude product was purified by silica gel column chromatography to obtain 4 g of intermediate 16D (yield 23%). The molecular weight of intermediate 16D, as measured by FAB-MS, was 1143.

[0577] (Synthesis of Compound 16) JPEG2026139258000219.jpg49170

[0578] Under an Ar atmosphere, intermediate 16D (4 g), 2-biphenylboronic acid (2.1 g), palladium(II) acetate (Pd(OAc)2, 0.16 g), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (SPhos, 0.57 g), K3PO4 (2.2 g), and toluene (60 mL) were added to a 200 mL three-necked flask and heated and stirred at 110 °C for 24 hours. After returning to room temperature, water was added and extracted with CH2Cl2. The organic layer was dried in one step over MgSO4, and the solvent was removed by distillation under reduced pressure. The compound was purified by silica gel column chromatography to obtain 0.7 g of compound 16 (yield 18%). The mass number of compound 16 measured by FAB-MS was 1109.

[0579] 2. Fabrication and evaluation of light-emitting devices An example of a light-emitting device containing the condensed polycyclic compound of one example in the light-emitting layer was manufactured by the following method. The condensed polycyclic compounds 1 to 12 and 14 to 16, which are the example compounds described above, were used as dopant materials for the light-emitting layer to manufacture the light-emitting devices of Examples 1 to 15. Comparative Examples 1 to 9 are light-emitting devices manufactured using comparative compound X-1 to comparative compound X-9 as dopant materials for the light-emitting layer.

[0580] [Example Compounds] JPEG2026139258000220.jpg50170JPEG2026139258000221.jpg50170JPEG2026139258000222.jpg45170JPEG2026139258 000223.jpg55170JPEG2026139258000224.jpg48170JPEG2026139258000225.jpg54170JPEG2026139258000226.jpg94170

[0581] [Comparative Compounds] JPEG2026139258000227.jpg49170 JPEG2026139258000228.jpg54170JPEG2026139258000229.jpg50170JPEG2026139258000230.jpg104170

[0582] In the comparative example compound, "Mes" refers to an unsubstituted mesityl group (2,4,6-trimethylphenyl group), and "Me" refers to an unsubstituted methyl group.

[0583] (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), an 80 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 on the luminescence auxiliary layer A 20 nm thick luminescent layer was formed by doping mCBP (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.

[0584] 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.

[0585] JPEG2026139258000231.jpg88170

[0586] (Evaluation of light-emitting element characteristics) Table 1 shows the evaluation results of the light-emitting elements for Examples 1 to 15 and Comparative Examples 1 to 9. Table 1 shows the relative lifetime (LT) of the fabricated light-emitting elements. 50 The relative lifetime was shown by comparing the two. The relative lifetime was 900 cd / m² of initial brightness. 2 The half-life of the brightness was evaluated and shown. The relative lifetime was shown relative to the results of Comparative Example 9.

[0587] [Table 1]

[0588] Referring to the results in Table 1, it can be seen that in the 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 lifetime characteristics are improved compared to the comparative examples. In contrast, although all of the comparative examples contain a condensed skeleton with three or more boron atoms in the molecule, it can be seen that the lifetime characteristics of the devices are all worse when applied to light-emitting devices compared to the example compounds.

[0589] Looking at Comparative Examples 1, 5, and 7, we can see that the comparative compounds X-1, X-5, and X-7 included in Comparative Examples 1, 5, and 7 differ from the condensed polycyclic compounds of the present invention in the crosslinking positions of the condensed rings, and it can be confirmed that their lifetime characteristics are significantly reduced compared to the examples. In particular, comparative compounds X-1 and X-7 have a form in which additional crosslinking is formed between adjacent condensed rings, which broadens the HOMO orbital and promotes hole trapping, making it difficult to achieve a long lifetime. In contrast, it can be confirmed that the condensed polycyclic compounds of the examples can achieve a longer lifetime compared to comparative compounds X-1, X-5, and X-7 because the first to third condensed rings take on a specific condensed ring form.

[0590] In Comparative Examples 2 and 3, comparative compounds X-2 and X-3, which are included in Comparative Examples 2 and 3, have a structure in which a methyl group is substituted at the ortho position relative to the nitrogen atom. As a result, the steric shielding effect is insufficient, and when applied to the device, the lifetime characteristics are reduced compared to the examples.

[0591] Comparing Comparative Example 2 and Example 13, Comparative Example Compound X-2 is X 3 The only difference is that a methyl group, rather than a phenyl group, is linked to the ortho position of the nitrogen atom. Since the methyl group is significantly smaller than an aryl group like the phenyl group, it is difficult to achieve a sufficient shielding effect, and as a result, comparative compound X-2 has lower molecular stability compared to example compound 14, and it can be confirmed that its lifetime is significantly reduced when applied to a light-emitting device.

[0592] Comparing Comparative Example 3 and Example 14, Comparative Compound X-3 is X 1 and X 2 The only difference is that a methyl group, rather than a phenyl group, is linked to the ortho position of the nitrogen atom at that position. Since the methyl group is significantly smaller than an aryl group like the phenyl group, it is difficult to achieve a sufficient shielding effect, and as a result, comparative compound X-3 has lower molecular stability compared to example compound 15, and it can be confirmed that its lifetime is significantly reduced when applied to a light-emitting element.

[0593] Looking at Comparative Example 4, Comparative Example Compound X-4 is X 1 and X 2 One of these is represented by chemical formula 3, and in chemical formula 3, R 20 and R 24 This applies when at least one of the groups is not an aryl group. Comparative example compound X-4 is X 1 and X 2 One of these is represented by chemical formula 3, and in chemical formula 3, R 20 and R 24 This corresponds to the case where only one of the groups is a phenyl group. In comparative example compound X-4, the presence of only one phenyl group at the ortho position of the nitrogen atom reduced the steric shielding effect on the condensed skeleton, resulting in a shorter lifespan compared to the example when applied to a light-emitting element.

[0594] Looking at Comparative Examples 6 and 8, Comparative Compounds X-6 and X-8 included in Comparative Examples 6 and 8 have X in Chemical Formula 1. 1 and X 2 This corresponds to the case where the compound is represented by chemical formula 4, and in chemical formula 4, Ar is a fluorenyl group or a heteroaryl group. When the substituent corresponding to Ar is a fluorenyl group or a heteroaryl group, as in comparative examples X-6 and X-8, hole trapping is promoted and device degradation can be induced. As a result, it can be confirmed that comparative examples 6 and 8, including comparative examples X-6 and X-8, have lower luminous efficiency and device lifetime compared to the examples. In the present invention, in condensed polycyclic compounds, X 1 and X 2When the compound is represented by chemical formula 4, the stabilization of the compound can be achieved by excluding the cases in chemical formula 4 where Ar is a fluorenyl group or a heteroaryl group.

[0595] Looking at Comparative Example 9, it can be seen that Comparative Example Compound X-9, included in Comparative Example 9, does not contain the substituent represented by Chemical Formula 3 compared to the Example Compound, and its lifetime characteristics are significantly reduced compared to the Example. Comparative Example Compound X-9 has a phenyl group substituted at the para position of the nitrogen atom, and its steric shielding effect on the condensed skeleton is reduced compared to the Example Compound. As a result, the molecular stability of Comparative Example Compound X-9 is reduced, and when applied to a light-emitting device, the lifetime of the light-emitting device is reduced. In contrast, the Example Compound, by containing at least one of Chemical Formula 3, can exhibit an excellent shielding effect and high stability when applied to a device.

[0596] 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.

[0597] 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]

[0598] 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, R １ ~R １１ Each of these is independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms that form a ring, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms that form a ring by bonding with adjacent groups. R １ ~R ４ and R ８ ~R １１ The two or three consecutive elements selected from each are the positions that are linked to the following chemical formula 2. X １ and X ２ Each of these is either O, S, or Se, or is represented by one of the following chemical formulas 3 through 5: [Chemical formula 2] In the aforementioned chemical formula 2, R １２ to R １９ each independently represent a hydrogen atom, a deuterium atom, a halogen atom, a cyano 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 are bonded to each other with an adjacent group to form a ring, X ３ and X ４ Each of these is either O, S, or Se independently, or can be represented by any one of the following chemical formulas 3 to 5: This is the position that is connected to the chemical formula 1, is linked to the chemical formula 1, or R in the chemical formula 2. １２ It is a position connected to: [Chemical formula 3] [Chemical formula 4] [Chemical formula 5] In the aforementioned chemical formulas 3 to 5, This is a position that is connected to chemical formula 1 or chemical formula 2, R ２０ ~R ２６ Each of these is independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano 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 ２０ ~R ２４ At least one of these is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms in a ring, Ar is a substituted or unsubstituted aryl group having 10 to 30 carbon atoms in a ring. Z is a carbon or silicon atom. If Z is a silicon atom, then R ２５ and R ２６ It is not a hydrogen atom, X １ ~X ４ At least one of them is represented by the above chemical formula 3, In the aforementioned chemical formula 1, X １ and X ２ When represented by the above chemical formula 4, cases in the above chemical formula 4 where Ar is a fluorenyl group or a heteroaryl group are excluded. In the aforementioned chemical formula 1, X １ and X ２ When any one of them is represented by the chemical formula 3, in the chemical formula 3, R ２０ and R ２４ If any one of them is not a substituted or unsubstituted aryl group with 6 to 30 carbon atoms forming a ring, it is excluded.

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 aforementioned X １ ~X ４ The light-emitting element according to claim 1, wherein at least two of the elements are represented by the chemical formula 3.

4. The aforementioned chemical formula 3 is represented by the following chemical formula 3-1 or chemical formula 3-2, and is the light-emitting element according to claim 1: [Chemical formula 3-1] [Chemical formula 3-2] In the aforementioned chemical formulas 3-1 and 3-2, This is a position that is connected to chemical formula 2 or chemical formula 3, R ３１ ~R ３５ , and R ４１ ~R ５０ Each of these is independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano 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 ２１ ~R ２４ This is as defined in chemical formula 3 above.

5. The first compound represented by the chemical formula 1 is the light-emitting element according to claim 1, represented by the following chemical formula 1-1-1 or chemical formula 1-1-2: [Chemical formula 1-1-1] [Chemical formula 1-1-2] In the aforementioned chemical formulas 1-1-1 and 1-1-2, X ２ａ is O, S, or Se, or is represented by the aforementioned chemical formula 4 or chemical formula 5. R ２４ａ This is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms in a ring, R ５１ ~R ５５ , R ６１ ~R ７０ , R ２１ｂ ~R ２４ｂ , and R ２１ｃ ~R ２４ｃ Each of these is independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano 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 １ ~R １１ 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 formulas 1-2: [Chemical formula 1-2] In the aforementioned chemical formula 1-2, R ７１ ~R ９０ , R ２１ｄ ~R ２３ｄ , and R ２１ｅ ~R ２３ｅ Each of these is independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano 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 １ ~R １１ This is as defined in Chemical Formula 1 above.

7. The first compound represented by the chemical formula 1 is a light-emitting element according to item 1, which is represented by any one of the following chemical formulas 1-3-1 to 1-3-3: [Chemical formula 1-3-1] [Chemical formula 1-3-2] [Chemical formula 1-3-3] In the above chemical formulas 1-3-1 to 1-3-3, X ３ａ , X ３ｂ , X ４ａ , and X ４ｂ Each of these is independently O, S, or Se, or is represented by one of the chemical formulas 3 to 5 above. R １２ａ ~R １９ａ , and R １２ｂ ~R １９ｂ Each of these is independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano 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. X １ , X ２ , and R ５ ~R ７ This is as defined in Chemical Formula 1 above.

8. The first compound represented by the chemical formula 1 is a light-emitting element according to item 1, which is represented by any one of the following chemical formulas 1-4-1 to 1-4-3: [Chemical formula 1-4-1] [Chemical formula 1-4-2] [Chemical formula 1-4-3] In the aforementioned chemical formulas 1-4-1 to 1-4-3, X ３ａ , X ３ｂ , X ４ａ , and X ４ｂ Each of these is independently O, S, or Se, or is represented by one of the chemical formulas 3 to 5 above. R １２ａ ~R １９ａ , and R １２ｂ ~R １９ｂ Each of these is independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano 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. X １ , X ２ , and R ５ ~R ７ This is as defined in Chemical Formula 1 above.

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 ａ１ 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 ａ２ R ａ３ , or SiR ａ４ R ａ５ 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 ａ１ to R ａ５ each independently represent 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, or adjacent groups may be bonded to each other to form a ring: [Chemical formula ET-1] In the aforementioned chemical formula ET-1, Z ａ ~Z ｃ At least one of them is N and the rest are CR ａ６ And, R ａ６ 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 to Ar ｄ each independently represent 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 Each of these 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: [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 heteroaryl 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 independently and 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 ｂ１ ~R ｂ６ 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. 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 positioned on the first electrode, and a light-emitting layer positioned 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, R １ ~R １１ Each of these is independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms that form a ring, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms that form a ring by bonding with adjacent groups. R １ ~R ４ and R ８ ~R １１ The two or three consecutive elements selected from each are the positions that are linked to the following chemical formula 2. X １ and X ２ Each of these is either O, S, or Se, or is represented by one of the following chemical formulas 3 through 5: [Chemical formula 2] In the aforementioned chemical formula 2, R １２ ~R １９ Each of these is independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms that form a ring, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms that form a ring by bonding with adjacent groups. X ３ and X ４ Each of these is either O, S, or Se independently, or can be represented by any one of the following chemical formulas 3 to 5: This is the position that is connected to the chemical formula 1, is linked to the chemical formula 1, or R in the chemical formula 2. １２ It is a position connected to: [Chemical formula 3] [Chemical formula 4] [Chemical formula 5] In the aforementioned chemical formulas 3 to 5, This is a position that is connected to chemical formula 2 or chemical formula 3, R ２０ ~R ２６ Each of these is independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano 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 ２０ ~R ２４ At least one of these is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms in a ring, Ar is a substituted or unsubstituted aryl group having 10 to 30 carbon atoms in a ring. Z is a carbon or silicon atom. If Z is a silicon atom, then R ２５ and R ２６ It is not a hydrogen atom, X １ ~X ４ At least one of them is represented by the above chemical formula 3, In the aforementioned chemical formula 1, X １ and X ２ When represented by the above chemical formula 4, cases in the above chemical formula 4 where Ar is a fluorenyl group or a heteroaryl group are excluded. In the aforementioned chemical formula 1, X １ and X ２ When any one of them is represented by the chemical formula 3, in the chemical formula 3, R ２０ and R ２４ If any one of them is not a substituted or unsubstituted aryl group with 6 to 30 carbon atoms forming a ring, it is excluded.

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, R １ ~R １１ Each of these is independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms that form a ring, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms that form a ring by bonding with adjacent groups. R １ ~R ４ and R ８ ~R １１ The two or three consecutive elements selected from each are the positions that are linked to the following chemical formula 2. X １ and X ２ Each of these is either O, S, or Se, or is represented by one of the following chemical formulas 3 through 5: [Chemical formula 2] In the aforementioned chemical formula 2, R １２ ~R １９ Each of these is independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms that form a ring, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms that form a ring by bonding with adjacent groups. X ３ and X ４ Each of these is either O, S, or Se independently, or can be represented by any one of the following chemical formulas 3 to 5: This is the position that is connected to the chemical formula 1, is linked to the chemical formula 1, or R in the chemical formula 2. １２ It is a position connected to: [Chemical formula 3] [Chemical formula 4] [Chemical formula 5] In the aforementioned chemical formulas 3 to 5, This is a position that is connected to chemical formula 2 or chemical formula 3, R ２０ ~R ２６ Each of these is independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano 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 ２０ ~R ２４ At least one of these is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms in a ring, Ar is a substituted or unsubstituted aryl group having 10 to 30 carbon atoms in a ring. Z is a carbon or silicon atom. If Z is a silicon atom, then R ２５ and R ２６ It is not a hydrogen atom, X １ ~X ４ At least one of them is represented by the above chemical formula 3, In the aforementioned chemical formula 1, X １ and X ２ When represented by the above chemical formula 4, cases in the above chemical formula 4 where Ar is a fluorenyl group or a heteroaryl group are excluded. In the aforementioned chemical formula 1, X １ and X ２ When any one of them is represented by the chemical formula 3, in the chemical formula 3, R ２０ and R ２４ If any one of them is not a substituted or unsubstituted aryl group with 6 to 30 carbon atoms forming a ring, it is excluded.

17. The condensed polycyclic compound represented by chemical formula 1 is the condensed polycyclic compound according to claim 16, represented by the following chemical formula 1-1-1 or chemical formula 1-1-2: [Chemical formula 1-1-1] [Chemical formula 1-1-2] In the aforementioned chemical formulas 1-1-1 and 1-1-2, X ２ａ is O, S, or Se, or is represented by the aforementioned chemical formula 4 or chemical formula 5. R ２４ａ This is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms in a ring, R ５１ ~R ５５ , R ６１ ~R ７０ , R ２１ｂ ~R ２４ｂ , and R ２１ｃ ~R ２４ｃ Each of these is independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano 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 １ ~R １１ 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, represented by the following chemical formulas 1-2: [Chemical formula 1-2] In the aforementioned chemical formula 1-2, R ７１ ~R ９０ , R ２１ｄ ~R ２３ｄ , and R ２１ｅ ~R ２３ｅ Each of these is independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano 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 １ ~R １１ 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 1-4-1 to 1-4-3: [Chemical formula 1-4-1] [Chemical formula 1-4-2] [Chemical formula 1-4-3] In the aforementioned chemical formulas 1-4-1 to 1-4-3, X ３ａ , X ３ｂ , X ４ａ , and X ４ｂ Each of these is independently O, S, or Se, or is represented by one of the chemical formulas 3 to 5 above. R １２ａ ~R １９ａ , and R １２ｂ ~R １９ｂ Each of these is independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano 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. X １ , X ２ , and R ５ ~R ７ 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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