Fused polycyclic compound, and light-emitting element and electronic device including the same

Abstract

Provided are a fused polycyclic compound represented by Formula 1; a light-emitting element including a first electrode, a second electrode provided over the first electrode, a light-emitting layer provided between the first electrode and the second electrode and containing the fused polycyclic compound, and an electronic device including the light-emitting element.[Formula 1]

Description

[0001] Cross-reference to related applications

[0002] This application claims priority and benefit to Japanese Patent Application No. 2025-027220, filed on February 21, 2025, the entire contents of which are hereby incorporated by reference. Technical Field

[0003] This disclosure relates to light-emitting elements, fused polycyclic compounds for light-emitting elements, and electronic devices including light-emitting elements. Background Technology

[0004] Recently, the development of organic electroluminescent display devices (and / or the like) as image display devices has been actively underway. Organic electroluminescent display devices (or the like) may include so-called self-emissive light-emitting elements, which generate a display (or image) by recombinating holes and electrons injected from a first electrode and a second electrode, respectively, in an emitting layer to cause the light-emitting material in the emitting layer to emit light.

[0005] For the application of light-emitting elements in display devices, improvements in aspects such as lifespan have been explored, and there is an increasing need to develop materials for light-emitting elements that can reliably meet or exceed industrial requirements. Summary of the Invention

[0006] This disclosure provides light-emitting elements with improved emission efficiency and lifespan, as well as electronic devices including said light-emitting elements.

[0007] This disclosure also provides fused polycyclic compounds, which are materials for use in light-emitting elements, improving emission efficiency and lifespan.

[0008] At least one exemplary embodiment of the present invention provides a light-emitting element comprising a first electrode, a second electrode on the first electrode, and an emitting layer between the first electrode and the second electrode, the emitting layer comprising a first compound represented by Formula 1.

[0009] [Formula 1]

[0010] In Equation 1 above, X 1 To X 4 Each is independently O, S, or NR. y1 R y1 It is a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 cyclic carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, or represented by the following formula 2, R1 To R 6 and R b1 To R b4 Each of the following is independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted amine group, a substituted or unsubstituted oxygen 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 60 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, wherein R 1 To R 6 and R b1 To R b4 Optionally bonded to adjacent groups to form a ring, R 7 To R 10 R a1 and R a2 Each of the following is independently a hydrogen atom, a deuterium atom, a cyano group, a halogen atom, 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 60 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, R a1 and R a2 At least one of them is the substituted or unsubstituted aryl group having 6 to 60 cyclic carbon atoms, R b1 To R b4 At least one of them is the substituted or unsubstituted alkyl group having 1 to 20 carbon atoms or an electron-donating group, and the electron-donating group is a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted alkylamine group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted arylamine group, or a substituted or unsubstituted carbazole group.

[0011] [Equation 2]

[0012] In Equation 2 above, n1 is an integer from 0 to 5, and R y2 It is a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms. Indicates the connection position, when R b2 and R b3 When they bond together, R b2 and R b3 Form the part represented by the formula RB, and R a1 and Ra2 The at least one of them is the unsubstituted aryl group having 6 to 60 cyclic carbon atoms.

[0013] [RB style]

[0014] In the above equation RB, b2 corresponds to R b2 The position, and b3 corresponds to R. b3 The position of, and / or the first compound includes a chemical structure in which hydrogen atoms are optionally replaced by deuterium atoms.

[0015] In at least one exemplary embodiment, the emitter layer may further comprise at least one of a second compound represented by the formula HT-1, a third compound represented by the formula ET-1, and a fourth compound represented by the formula D-1.

[0016] [Formula HT-1]

[0017] In the above formula HT-1, A1 to A8 can each be N or CR independently. 51 L1 can be a straight-linked, substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms. a It can be a direct-connect key, CR 52 R 53 or SiR 54 R 55 Ar1 can be a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, R 51 To R 55 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 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 cyclic carbon atoms, wherein R 51 To R 55 Optionally bonded to adjacent groups to form a ring.

[0018] [Formula ET-1]

[0019] In the above equation ET-1, X 1 To X 3 At least one of them can be N, and X 1 To X 3 The remainder can be CR 56 R 56 It can be a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 cyclic carbon atoms. b1 to b3 can each be an integer from 0 to 10. Ar2 to Ar4 can each be a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms. L2 to L4 can each be a straight bond, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms.

[0020] [Formula D-1]

[0021] In formula D-1 above, Q1 to Q4 can each be independently C or N, and C1 to C4 can each be independently a substituted or unsubstituted hydrocarbon ring having 5 to 30 cyclic carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heterocycle having 2 to 30 cyclic carbon atoms. 11 To L 13 Each can be a direct-connect key independently. , , , The following are possible interpretations: substituted or unsubstituted divalent alkyl groups having 1 to 20 carbon atoms; substituted or unsubstituted aryl groups having 6 to 30 cyclic carbon atoms; or substituted or unsubstituted heteroaryl groups having 2 to 30 cyclic carbon atoms and in the L... 11 To L 13 middle, This refers to the portion connected to C1 to C4, where b11 to b13 can each be 0 or 1 independently, and R 61 To R 66Each of the following can be 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 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 cyclic carbon atoms, and d1 to d4 can each be independently an integer from 0 to 4.

[0022] In at least one exemplary embodiment, Formula 1 above can be represented by at least one of Formula 1-A1 to Formula 1-A6.

[0023] [Equation 1-A1]

[0024] [Equation 1-A2]

[0025] [Equation 1-A3]

[0026] [Equation 1-A4]

[0027] [Formula 1-A5]

[0028] [Equation 1-A6]

[0029] In equations 1-A1 to 1-A6 above, X 11 To X 14 Each can be independently O or S, and n2 to n5 can each be an integer from 0 to 5, R y11 To R y14 Each of these can be independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms. R 1 To R 6 R b1 To R b4 R 7 To R 10 R a1 and R a2 Same as defined in Equation 1 above.

[0030] In at least one exemplary embodiment, in Equation 1 above, R b1 To R b4 At least one of them may be a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted isopropyl group, a substituted or unsubstituted n-butyl group, a substituted or unsubstituted tert-butyl group, a substituted or unsubstituted cyclopentyl group, a substituted or unsubstituted cyclohexyl group, a substituted or unsubstituted methoxy group, a substituted or unsubstituted propoxy group, a substituted or unsubstituted isopropoxy group, a substituted or unsubstituted tert-butoxy group, a substituted or unsubstituted cyclohexoxy group, a substituted or unsubstituted phenoxy group, a substituted or unsubstituted dimethylamine group, a substituted or unsubstituted ethylamine group, a substituted or unsubstituted N-methylphenylamine group, a substituted or unsubstituted N-propylphenylamine group, a substituted or unsubstituted diphenylamine group, a substituted or unsubstituted methylthio group, a substituted or unsubstituted isopropylthio group, a substituted or unsubstituted propylthio group, a substituted or unsubstituted tert-butylthio group, a substituted or unsubstituted phenylthio group, or a substituted or unsubstituted carbazole group.

[0031] In at least one exemplary embodiment, in Equation 1 above, R b1 To R b4 At least one of them can be represented by at least one of the following Rb-1 to Rb-45.

[0032]

[0033] Among Rb-1 to Rb-45 above, Indicates the connection location. In Rb-28 to Rb-45 above, two... It corresponds to R b1 To R b4 The positions of two adjacent groups in the middle.

[0034] In at least one exemplary embodiment, in Equation 1 above, the above R a1 and R a2 At least one of them can be represented by at least one of the following Ra-1 to Ra-5:

[0035] Among Ra-1 to Ra-5 above, This indicates the connection position. In Ra-2 above, D is a deuterium atom.

[0036] In at least one exemplary embodiment, in Equation 1 above, Ra1 and R a2 The remainder can be a hydrogen atom, a deuterium atom, a cyano group, a substituted or unsubstituted diphenylamine group, or a substituted or unsubstituted carbazole group.

[0037] In at least one exemplary embodiment, R in Equation 1 above... y1 It can be represented by at least one of the following Y1-1 to Y1-18:

[0038] In Y1-1 to Y1-18 above, Indicates the connection location.

[0039] In at least one exemplary embodiment of the present invention, a fused polycyclic compound represented by the following Formula 1 is provided.

[0040] [Formula 1]

[0041] In Equation 1 above, X 1 To X 4 Each is independently O, S, or NR. y1 R y1 It is a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 cyclic carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, or represented by the following formula 2, R 1 To R 6 and R b1 To R b4 Each of the following is independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted amine group, a substituted or unsubstituted oxygen 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 60 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, wherein R 1 To R 6 and R b1 To R b4 Optionally bonded to adjacent groups to form a ring, R 7 To R 10 R a1 and R a2Each of the following is independently a hydrogen atom, a deuterium atom, a cyano group, a halogen atom, 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 60 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, R a1 and R a2 At least one of them is an aryl group, either substituted or unsubstituted, having 6 to 60 cyclic carbon atoms, R b1 To R b4 At least one of them is the substituted or unsubstituted alkyl group having 1 to 20 carbon atoms or an electron-donating group, and / or the electron-donating group is a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted alkylamine group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted arylamine group, or a substituted or unsubstituted carbazole group.

[0042] [Equation 2]

[0043] In Equation 2 above, n1 can be an integer from 0 to 5, and R y2 It can be a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms. Indicates the connection position, and when R b2 and R b3 When they bond together to form a part represented by the following formula RB, R a1 and R a2 At least one of them can be an unsubstituted aryl group having 6 to 60 cyclic carbon atoms.

[0044] [RB style]

[0045] In the above equation RB, b2 corresponds to R b2 The position, and b3 corresponds to R. b3 The position of the fused polycyclic compound, and the chemical structure in which hydrogen atoms are optionally replaced by deuterium atoms.

[0046] In at least one exemplary embodiment of the present invention, an electronic device is provided that includes a display device for providing an image, the display device including a substrate layer, a circuit layer disposed on the substrate layer, and a display element layer disposed on the circuit layer and including a light-emitting element, wherein the light-emitting element includes a first electrode, a second electrode disposed on the first electrode, and an emitting layer disposed between the first electrode and the second electrode and comprising the fused polycyclic compound represented by Formula 1 above.

[0047] In at least one exemplary embodiment, the electronic device may further include at least one of a light control layer and a color filter layer, wherein the light control layer may contain quantum dots and the color filter layer may contain at least one of pigments and dyes.

[0048] In at least one exemplary embodiment, the electronic device may further include at least one of a processor, a memory, and a power module. Attached Figure Description

[0049] The accompanying drawings are included to provide a further understanding of the inventive concept and / or are incorporated in and constitute a part of this specification. The drawings illustrate embodiments of the inventive concept and, together with the description, serve to explain the principles of the inventive concept. In the drawings: Figure 1 This is a plan view illustrating a display device according to at least one exemplary embodiment; Figure 2 It shows along Figure 1 A cross-sectional view of a portion cut off by line I-I' in the image; Figure 3 This is a schematic cross-sectional view of a light-emitting element according to at least one exemplary embodiment; Figure 4 This is a schematic cross-sectional view of a light-emitting element according to at least one exemplary embodiment; Figure 5 This is a schematic cross-sectional view of a light-emitting element according to at least one exemplary embodiment; Figure 6 This is a schematic cross-sectional view of a light-emitting element according to at least one exemplary embodiment; Figure 7A This is a graph illustrating the highest occupied molecular orbital (HOMO) distribution of a fused polycyclic compound according to at least one exemplary embodiment; Figure 7B This is a graph illustrating the distribution of the lowest unoccupied molecular orbitals (LUMOs) of a fused polycyclic compound according to at least one exemplary embodiment; Figure 8This is a cross-sectional view showing a display device according to at least one exemplary embodiment; Figure 9 This is a cross-sectional view showing a display device according to at least one exemplary embodiment; Figure 10 This is a cross-sectional view showing a display device according to at least one exemplary embodiment; Figure 11 This is a cross-sectional view showing a display device according to at least one exemplary embodiment; Figure 12 This is a view showing the interior of a vehicle in which a display device according to at least one exemplary embodiment is provided; Figure 13 This is a perspective view illustrating an electronic device according to at least one exemplary embodiment; Figure 14 This is an exploded perspective view illustrating an electronic device according to at least one exemplary embodiment; Figure 15 It is a block diagram of an electronic device according to at least one exemplary embodiment; and Figure 16 Schematic diagrams of electronic devices according to various implementation schemes are shown. Detailed Implementation

[0050] This disclosure may be modified in many alternative forms, and / or therefore specific exemplary embodiments will be shown and described in detail in the accompanying drawings. However, it should be understood that this disclosure is not intended to be limited to the particular forms disclosed, but rather to cover all modifications, equivalents, and / or substitutions falling within the spirit and scope of this disclosure.

[0051] In this specification, it should be understood that when an element (or area, layer, section, etc.) is referred to as being "on" another element, "connected" to another element, or "attached to" another element, it may be directly disposed on another element, directly connected to another element, and / or directly attached to another element, and / or other elements may be disposed between them, unless otherwise expressly indicated.

[0052] The same reference numerals or symbols refer to the same elements throughout. In the accompanying drawings, the thickness, ratios, and / or dimensions of the elements are enlarged for effective description of the technical content. The term "and / or" includes any and all combinations of one or more of the related listed elements.

[0053] It should be understood that although the terms “first,” “second,” etc., may be used herein to describe various elements, the elements are not limited to these terms. These terms are used only to distinguish one element from another. For example, a first element may be referred to as a second element without departing from the scope of the inventive concept. Similarly, a second element may be referred to as a first element. The singular forms “a,” “an,” and “the” are intended to also include the plural forms unless the context clearly indicates otherwise.

[0054] Furthermore, the terms “below,” “under,” “below the lower side,” “above,” “above,” “on the upper side,” etc., may be used to describe the relationships between the elements shown in the accompanying drawings. These terms are relative concepts and are described based on the directions indicated in the drawings. For example, it should be understood that such spatially relative terms are intended to also include different orientations of the device in use or operation in addition to the orientations depicted in the drawings, and / or therefore the device may be oriented in other ways (rotated 90 degrees or in other orientations), and the spatially relative terms used herein are interpreted accordingly.

[0055] Additionally, when terms such as “about,” “approximately,” or “substantially” are used in relation to numerical values, the relevant numerical value may be interpreted as including manufacturing or operational deviations (e.g., ±10%). Furthermore, regardless of whether a numerical value of a shape is limited by the use of “about,” “approximately,” or “substantially,” such a numerical value or shape should be understood to include manufacturing or operational deviations (e.g., ±10%).

[0056] It should also be understood that the terms “comprises,” “includes,” “has,” and / or “comprising,” “including,” “having,” when used in this specification, indicate the presence of specified features, numbers, steps, operations, elements, components, and / or combinations thereof, but do not preclude the possibility of the presence or addition of one or more other features, numbers, steps, operations, elements, components, and / or combinations thereof.

[0057] Unless otherwise defined, all terms used herein (including technical and scientific terms) shall have the same meaning as commonly understood by one of ordinary skill in the art to which this invention pertains. It should also be understood that terms defined, for example, in common dictionaries, shall be interpreted as having meanings consistent with their meanings in the context of the relevant field and shall not be interpreted in an idealized or overly formal sense, unless expressly defined herein.

[0058] Furthermore, as used in this specification, terms such as “unit” and “module” refer to a functional unit that processes at least one function or operation, and / or can be implemented as processing circuitry, such as hardware, software, and / or a combination of hardware and software. For example, processing circuitry may more specifically include, but is not limited to, a central processing unit (CPU), an arithmetic logic unit (ALU), a digital signal processor, a microcomputer, a field-programmable gate array (FPGA), an architecture-on-a-chip (SoC), a programmable logic unit, a microprocessor, an application-specific integrated circuit (ASIC), etc. Processing circuitry may include electrical components (e.g., at least one of transistors, resistors, capacitors, etc.) and / or electronic circuitry including said components.

[0059] In this document, the term "substituted or unsubstituted" can mean that a group is substituted by at least one substituent or is unsubstituted, wherein the substituent is selected from the group consisting of deuterium, halogen, cyano, nitro, amine, amino, silyl, oxy, thio, sulfinyl, sulfonyl, acyl, boron, hydroxyl, phosphine oxide, phosphine sulfide, alkyl, alkenyl, alkynyl, cyclic, aryl, and heterocyclic groups. Furthermore, each of the substituents presented as examples above can be substituted or unsubstituted. For example, a biphenyl group can be interpreted as an aryl group or a phenyl group substituted by a phenyl group.

[0060] In this document, the term "bonded to an adjacent group to form a ring" can refer to a group bonding to an adjacent group to form a substituted or unsubstituted hydrocarbon ring, or a substituted or unsubstituted heterocycle. Hydrocarbon rings include aliphatic and aromatic hydrocarbon rings. Heterocycles include aliphatic and aromatic heterocycles. Hydrocarbon rings and heterocycles can be monocyclic or polycyclic. Furthermore, rings formed by bonding to each other can be attached to another ring to form a spirocyclic structure.

[0061] In this document, the term "adjacent group" can refer to a substituent that replaces an atom directly attached to the atom substituted by the corresponding substituent, another substituent that replaces the atom substituted by the corresponding substituent, or the substituent that is spatially closest to the corresponding substituent. For example, the two methyl groups in 1,2-dimethylbenzene can be interpreted as "adjacent groups," and the two ethyl groups in 1,1-diethylcyclopentane can be interpreted as "adjacent groups." Furthermore, the two methyl groups in 4,5-dimethylphenanthrene can be interpreted as "adjacent groups."

[0062] In this document, examples of halogen atoms may include fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms.

[0063] In this document, alkyl groups can be straight-chain, branched, or cyclic groups. Alkyl groups can include cycloalkyl groups. The number of carbon atoms in an alkyl group is 1 to 60, 1 to 50, 1 to 30, 1 to 20, 1 to 10, or 1 to 6. Examples of alkyl groups include methyl groups, ethyl groups, n-propyl groups, isopropyl groups, n-butyl groups, sec-butyl groups, tert-butyl groups, isobutyl groups, 2-ethylbutyl groups, 3,3-dimethylbutyl groups, n-pentyl groups, isopentyl groups, neopentyl groups, tert-pentyl groups, 1-methylpentyl groups, 3-methylpentyl groups, 2-ethylpentyl groups, 4-methyl-2-pentyl groups, n-hexyl groups, 1-methylhexyl groups, 2-Ethylhexyl group, 2-Butylhexyl group, n-Heptyl group, 1-Methylheptyl group, 2,2-Dimethylheptyl group, 2-Ethylheptyl group, 2-Butylheptyl group, n-Octyl group, tert-Octyl group, 2-Ethyloctyl group, 2-Butyloctyl group, 2-Hexyloctyl group, 3,7-Dimethyloctyl group, n-Nonyl group, n-Decyl group, 2-Ethyldecyl group, 2-Butyldecyl group, 2-Hexyldecyl group, 2-Octyl Decyl group, n-undecyl group, n-dodecyl group, 2-ethyldodecyl group, 2-butyldodecyl group, 2-hexyldodecyl group, 2-octyldodecyl group, n-tridecyl group, n-tetradecyl group, n-pentadecanyl group, n-hexadecyl group, 2-ethylhexadecyl group, 2-butylhexadecyl group, 2-hexylhexadecyl group, 2-octylhexadecyl group, n-heptadecyl group, n-octadecyl group, n-nonadecanyl group, n-eicosyl group, 2-ethyleicosyl group, 2-butyleicosyl group, 2-hexyleicosyl group, 2-octyleicosyl group, n-eicosyl group, n-eicosyl group, n-eicosyl group, n-eicosyl group, n-eicosyl group, n-eicosyl group, n-eicosyl group, n-eicosyl group, n-eicosyl group, n-eicosyl group, n-eicosyl group, etc., but not limited to these.

[0064] In this document, cycloalkyl groups may refer to cyclic alkyl groups. The number of carbon atoms in a cycloalkyl group is 3 to 60, 3 to 50, 3 to 30, 3 to 20, or 3 to 10. Examples of cycloalkyl groups include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, norbornyl, 1-adamantyl, 2-adamantyl, isobornyl, and bicycloheptyl groups.

[0065] In this document, an alkenyl group refers to a hydrocarbon group containing at least one carbon-carbon double bond at the middle or end of an alkyl group having two or more carbon atoms. The alkenyl group can be straight-chain or branched. The number of carbon atoms is not particularly limited, but is 2 to 60, 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-butadienyl groups, styryl groups, styrylvinyl groups, etc.

[0066] In this document, an alkynyl group refers to a hydrocarbon group containing at least one triple bond in the middle or at the end of an alkyl group having two or more carbon atoms. The alkynyl group can be straight-chain or branched. The number of carbon atoms is not particularly limited, but is 2 to 30, 2 to 20, or 2 to 10. Specific examples of alkynyl groups may include, but are not limited to, ethynyl groups, propynyl groups, etc.

[0067] In this document, cyclic hydrocarbon groups refer to any functional group or substituent derived from an aliphatic hydrocarbon ring. Cyclic hydrocarbon groups can be saturated cyclic hydrocarbon groups having 5 to 60, 5 to 30, 5 to 20, 5 to 15, or 5 to 10 cyclic carbon atoms.

[0068] In this document, aryl group refers to any functional group or substituent derived from an aromatic hydrocarbon ring. Aryl group can be a monocyclic or polycyclic aryl group. The number of cyclic carbon atoms in the aryl group can be 6 to 60, 6 to 30, 6 to 20, 6 to 15, or 6 to 10. Examples of aryl groups may include, but are not limited to, phenyl, naphthyl, fluorenyl, anthraceneyl, phenanthrene, biphenyl, triphenyl, tetraphenyl, pentaphenyl, hexaphenyl, benzo[a]phenanthrene, pyrene, benzo[a]fluorene-anthrayl, alkyl, etc.

[0069] In this document, the fluorene group may be substituted, and / or two substituents may be bonded to each other to form a spirocyclic structure. Some examples of substituted fluorene groups are given below. However, the exemplary embodiments are not limited thereto.

[0070]

[0071] In this document, a heterocyclic group refers to any functional group or substituent derived from a ring containing at least one of B, O, N, P, Si, and S as a heteroatom. Heterocyclic groups include aliphatic heterocyclic groups and aromatic heterocyclic groups. Aromatic heterocyclic groups may be heteroaryl groups. Aliphatic and aromatic heterocyclic groups may be monocyclic or polycyclic.

[0072] In this document, the heterocyclic group may contain at least one of B, O, N, P, Si, and S as a heteroatom. The number of heteroatoms in the heterocyclic group may be 1 to 10, for example, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10. When the heterocyclic group contains two or more heteroatoms, the two or more heteroatoms may be the same or different from each other. The heterocyclic group may be a monocyclic heterocyclic group or a polycyclic heterocyclic group, and / or include a heteroaryl group. The number of cyclic carbon atoms in the heterocyclic group may be 2 to 60, 2 to 30, 2 to 20, or 2 to 10.

[0073] In this document, aliphatic heterocyclic groups may contain at least one of B, O, N, P, Si, and S as heteroatoms. The number of cyclic carbon atoms in an aliphatic heterocyclic group may be 2 to 60, 2 to 30, 2 to 20, or 2 to 10. Examples of aliphatic heterocyclic groups include, but are not limited to, oxetane propane groups, thiohexane propane groups, pyrrolithyl groups, piperidine groups, tetrahydrofuran groups, tetrahydrothiophene groups, thiohexane groups, tetrahydropyran groups, and 1,4-dioxane groups.

[0074] In this document, a heteroaryl group may contain at least one of B, O, N, P, Si, and S as a heteroatom. When a heteroaryl group contains two or more heteroatoms, the two or more heteroatoms may be the same or different from each other. The heteroaryl group may be a monocyclic heteroaryl group or a polycyclic heteroaryl group. The number of cyclic carbon atoms in the heteroaryl group may be 2 to 60, 2 to 30, 2 to 20, or 2 to 10. Examples of heteroaryl groups include, but are not limited to, thiophene groups, furan groups, pyrrole groups, imidazole groups, pyridine groups, bipyridine groups, pyrimidine groups, triazine groups, triazole groups, acridine groups, pyridazine groups, pyrazinyl groups, quinoline groups, quinazoline groups, quinoxaline groups, phenoxazine groups, phthalazine groups, pyridopyrimidine groups, pyridopyrazine groups, pyrazinopyrazine groups, isoquinoline groups, indole groups, carbazole groups, N-arylcarbazole groups, N-heteroarylcarbazole groups, N-alkylcarbazole groups, benzoxazole groups, benzimidazole groups, benzothiazole groups, benzocarbazole groups, benzothiophene groups, dibenzothiophene groups, thienothiophene groups, benzofuran groups, phenanthroline groups, thiazole groups, isoxazole groups, oxazole groups, oxadiazole groups, thiadiazole groups, phenothiazine groups, dibenzothiophene groups, dibenzofuran groups, etc.

[0075] In this paper, the above description of aryl groups can also be applied to arylene groups, but arylene groups are divalent groups. Similarly, the above description of heteroaryl groups can also be applied to heteroarylene groups, but heteroarylene groups are divalent groups.

[0076] In this document, silyl groups include alkylsilyl groups and arylsilyl groups. The alkyl group and its carbon number in alkylsilyl groups are defined as described above for alkyl groups. The aryl group and its carbon number in arylsilyl groups are defined as described above for aryl groups. Examples of silyl groups include, but are not limited to, trimethylsilyl groups, triethylsilyl groups, tert-butyldimethylsilyl groups, dimethylsilyl groups, propyldimethylsilyl groups, triphenylsilyl groups, diphenylsilyl groups, and phenylsilyl groups.

[0077] In this document, the acyl group is represented by R-CO-, where R can be hydrogen, an alkyl group, or an aryl group, wherein the alkyl and aryl groups are as defined above. There is no particular limitation on the number of carbon atoms in the acyl group, but it can be 1 to 40, 1 to 30, 1 to 20, 1 to 15, or 1 to 10. For example, the acyl group can have the following structures, but is not limited thereto.

[0078]

[0079] In this document, the number of carbon atoms in sulfinyl groups and sulfonyl groups is not particularly limited, but can be 1 to 30, 1 to 20, 1 to 15, or 1 to 10. Sulfinyl groups can include alkyl sulfinyl groups and aryl sulfinyl groups. The definition of the alkyl group in an alkyl sulfinyl group can be as defined in the above definition of alkyl groups. The definition of the aryl group in an aryl sulfinyl group can be as defined in the above definition of aryl groups. Sulfinyl groups can include alkyl sulfonyl groups and aryl sulfonyl groups.

[0080] In this document, a thio group may include alkylthio groups and arylthio groups. A thio group may represent a group in which a sulfur atom is bonded to an alkyl group or an 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 naphthio groups.

[0081] In this document, an oxy group can refer to a group in which an oxygen atom is bonded to an alkyl or aryl group as defined above. Oxy groups can include alkoxy groups and aryloxy groups. Alkoxy groups can be linear, branched, or cyclic. The number of carbon atoms in an alkoxy group is not particularly limited, but can be, for example, 1 to 20, 1 to 15, or 1 to 10. Examples of oxy groups include, but are not limited to, methoxy, ethoxy, n-propoxy, isopropoxy, butoxy, pentoxy, hexoxy, octoxy, nonoxy, decoxy, benzyloxy, etc.

[0082] In this document, a boron group can refer to a group in which a boron atom is bonded to an alkyl group or an aryl group as defined above. Boron groups include alkylboron groups and arylboron groups. Examples of boron groups include, but are not limited to, dimethylboron groups, diethylboron groups, tert-butylmethylboron groups, diphenylboron groups, phenylboron groups, etc.

[0083] In this document, the number of carbon atoms in the amine group is not particularly limited, but can be 1 to 50, 1 to 30, 1 to 20, 1 to 15, or 1 to 10. The amine group can 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, 9-methyl-anthraylamine groups, etc.

[0084] In this document, the examples of alkyl groups described above also apply to alkyl groups in the categories of alkylthio groups, alkylsulfonyloxy groups, alkylaryl groups, alkylamino groups, alkylboron groups, alkylsilylalkyl groups, and alkylamine groups.

[0085] In this document, the examples of aryl groups described above also apply to aryl groups in the categories of aryloxy groups, arylthio groups, arylsulfonoxy groups, arylamino groups, arylboronic groups, arylsilyl groups, and arylamine groups.

[0086] In this article, a direct-connected key can represent a single key. In this article, " "and" "Indicates the connection position.

[0087] In the following description, some exemplary embodiments of the inventive concept will be described with reference to the accompanying drawings.

[0088] Figure 1 This is a plan view of a display device DD illustrating at least one exemplary embodiment. Figure 2 This is a cross-sectional view of a display device DD illustrating at least one exemplary embodiment. Figure 2 It shows the corresponding Figure 1 A cross-sectional view of a portion of line I-I'.

[0089] The display device DD may include a display panel DP and an optical layer PP disposed on the display panel DP. The display panel DP includes light-emitting elements ED-1, ED-2, and / or ED-3. The display device DD may include multiple light-emitting elements ED-1, ED-2, and / or ED-3. The optical layer PP may be disposed on the display panel DP to control reflected light in the display panel DP caused by external light. The optical layer PP may include, for example, a polarizing layer or a color filter layer. Unlike that shown in the figures, the optical layer PP may not be provided in the display device DD of at least one exemplary embodiment.

[0090] The substrate BL can be disposed on the optical layer PP. The substrate BL can be a component providing a substrate surface on which the optical layer PP is disposed. The substrate BL can be a glass substrate, a metal substrate, a plastic substrate, etc. However, exemplary embodiments are not limited thereto, and / or the substrate BL can be an inorganic layer, an organic layer, or a composite material layer. Furthermore, unlike those shown, in at least one exemplary embodiment, the substrate BL may not be provided.

[0091] The display device DD according to at least one exemplary embodiment may further include a filler layer (not shown). The filler layer (not shown) may be disposed between the display element layer DP-ED and the substrate BL. The filler layer (not shown) may be an organic material layer. The filler layer (not shown) may contain at least one of an acrylic-based resin, a silicone-based resin, and an epoxy-based resin.

[0092] The display panel DP may include a substrate layer BS, a circuit layer DP-CL provided on the substrate layer BS, and / or a display element layer DP-ED. The display element layer DP-ED may include a pixel defining film PDL, a plurality of light-emitting elements ED-1, ED-2 and / or ED-3 disposed between the pixel defining films PDL, and / or an encapsulation layer TFE disposed on the plurality of light-emitting elements ED-1, ED-2 and / or ED-3.

[0093] The substrate layer BS can be a component providing a substrate surface on which the display element layer DP-ED is disposed. The substrate layer BS can be a glass substrate, a metal substrate, a plastic substrate, etc. However, exemplary embodiments are not limited thereto, and / or the substrate layer BS can be an inorganic layer, an organic layer, or a composite material layer.

[0094] In at least one exemplary embodiment, the circuit layer DP-CL may be disposed on the substrate layer BS, and / or 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 / or an output electrode. For example, the circuit layer DP-CL may include a switching transistor for driving the light-emitting elements ED-1, ED-2, and ED-3 of the display element layer DP-ED.

[0095] The light-emitting elements ED-1, ED-2 and / or ED-3 may each have, as described later, the following: Figures 3 to 6 The structure of a light-emitting element ED according to at least one exemplary embodiment. The light-emitting elements ED-1, ED-2 and / or ED-3 may each include a first electrode EL1, a hole transport region HTR, an emitter layer EML-R, EML-G and / or EML-B, an electron transport region ETR, and / or a second electrode EL2.

[0096] Figure 2 At least one exemplary embodiment is shown, wherein the emitting layers EML-R, EML-G, and / or EML-B of the light-emitting elements ED-1, ED-2, and / or ED-3 are disposed in openings OH defined in the pixel-defining film PDL, and / or the hole transport region HTR, the electron transport region ETR, and / or the second electrode EL2 are provided as a common layer throughout the light-emitting elements ED-1, ED-2, and / or ED-3. However, the exemplary embodiment is not limited thereto, and / or may be related to... Figure 2 As shown in the diagram, in at least one exemplary embodiment, the hole transport region HTR and the electron transport region ETR can be provided as patterned within an opening OH defined in the pixel-defined film PDL. For example, in at least one exemplary embodiment, the hole transport region HTR, the emitting layer EML-R, EML-G and / or EML-B, and / or the electron transport region ETR of the light-emitting elements ED-1, ED-2, and / or ED-3 can be patterned and provided by inkjet printing.

[0097] The encapsulation layer TFE can cover the light-emitting elements ED-1, ED-2, and ED-3. The encapsulation layer TFE can seal the display element layer DP-ED. The encapsulation layer TFE can be a thin-film encapsulation layer. The encapsulation layer TFE can be a single layer or a stack of multiple layers. The encapsulation layer TFE can include at least one insulating layer. The encapsulation layer TFE according to at least one exemplary embodiment can include at least one inorganic film (hereinafter, encapsulating inorganic film). Furthermore, the encapsulation layer TFE according to at least one exemplary embodiment can include at least one organic film (hereinafter, encapsulating organic film) and / or at least one encapsulating inorganic film.

[0098] The encapsulating inorganic film is configured to protect the display element layer DP-ED from moisture / oxygen, and / or 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 particularly limited to, silicon nitrides, silicon oxides, silicon oxides, titanium oxides, aluminum oxides, etc. The encapsulating organic film may include acrylic-based compounds, epoxy-based compounds, etc. The encapsulating organic film may include photopolymerizable organic materials, and is not particularly limited thereto.

[0099] The encapsulation layer TFE can be disposed on the second electrode EL2, and / or can be disposed to fill the opening OH.

[0100] refer to Figure 1 and Figure 2The display device DD may include a non-emitting area NPXA and emitting areas PXA-R, PXA-G, and / or PXA-B. The emitting areas PXA-R, PXA-G, and / or PXA-B may each be an area that emits light generated from each of the light-emitting elements ED-1, ED-2, and / or ED-3. When viewed on a plane, the emitting areas PXA-R, PXA-G, and / or PXA-B may be spaced apart from each other.

[0101] The emitting regions PXA-R, PXA-G, and / or PXA-B can each be a region separated by a pixel-defining film (PDL). The non-emitting region NPXA can be the region between adjacent emitting regions PXA-R, PXA-G, and / or PXA-B, and / or can correspond to the pixel-defining film (PDL). In this document, the emitting regions PXA-R, PXA-G, and / or PXA-B can each correspond to a pixel. The pixel-defining film (PDL) can separate the light-emitting elements ED-1, ED-2, and ED-3. The emitting layers EML-R, EML-G, and / or EML-B of the light-emitting elements ED-1, ED-2, and ED-3 can be disposed in the opening OH defined by the pixel-defining film (PDL) and are therefore separated.

[0102] Based on the color of the light emitted from the light-emitting elements ED-1, ED-2, and / or ED-3, the light-emitting areas PXA-R, PXA-G, and / or PXA-B can be divided into multiple groups. Figure 1 and Figure 2 In the display device DD of at least one exemplary embodiment shown, three light-emitting areas PXA-R, PXA-G, and / or PXA-B emitting red, green, and / or blue light are shown as examples. For example, the display device DD of at least one exemplary embodiment may include red light-emitting areas PXA-R, green light-emitting areas PXA-G, and / or blue light-emitting areas PXA-B that are different from each other.

[0103] In a display device DD according to at least one exemplary embodiment, a plurality of light-emitting elements ED-1, ED-2, and / or ED-3 can emit light with different wavelength ranges. For example, in at least one exemplary embodiment, the display device DD may include a first light-emitting element ED-1 emitting red light, a second light-emitting element ED-2 emitting green light, and / or a third light-emitting element ED-3 emitting blue light. That is, the red light-emitting areas PXA-R, green light-emitting areas PXA-G, and / or blue light-emitting areas PXA-B of the display device DD can correspond to the first light-emitting element ED-1, the second light-emitting element ED-2, and / or the third light-emitting element ED-3, respectively.

[0104] However, the exemplary embodiments are not limited thereto, and / or the first to third light-emitting elements ED-1, ED-2 and ED-3 may emit light within the same wavelength range or emit light within at least one different wavelength range. For example, the first to third light-emitting elements ED-1, ED-2 and / or ED-3 may all emit blue light.

[0105] According to at least one exemplary embodiment, the light-emitting areas PXA-R, PXA-G, and / or PXA-B in the display device DD can be arranged in the form of stripes. (Reference) Figure 1 Multiple red emitting areas PXA-R, multiple green emitting areas PXA-G, and / or multiple blue emitting areas PXA-B can each be arranged along the second directional axis DR2. Alternatively, the red emitting areas PXA-R, green emitting areas PXA-G, and / or blue emitting areas PXA-B can be arranged alternately along the first directional axis DR1 in this order.

[0106] Figure 1 and Figure 2 The emitting regions PXA-R, PXA-G, and / or PXA-B are shown to be similar in size, but the exemplary embodiments are not limited thereto, and / or the emitting regions PXA-R, PXA-G, and / or PXA-B may differ in size from each other depending on the wavelength range of the emitted light. The area of ​​the emitting regions PXA-R, PXA-G, and / or PXA-B can be represented as the area when viewed in a plane defined by the first directional axis DR1 and the second directional axis DR2.

[0107] The arrangement of the luminescent regions PXA-R, PXA-G, and / or PXA-B is not limited to... Figure 1 The arrangement shown, and / or the order in which the red emitting areas PXA-R, green emitting areas PXA-G, and / or blue emitting areas PXA-B are arranged, can be varied in combination according to the display quality characteristics required by the display device DD. For example, the emitting areas PXA-R, PXA-G, and / or PXA-B can be arranged in a corrugated (PENTILE) shape. ® ) or diamond (Diamond Pixel) ® Arranged in the form of ).

[0108] Furthermore, the area of ​​each of the emitting regions PXA-R, PXA-G, and / or PXA-B may differ from each other in size. For example, in at least one exemplary embodiment, the green emitting region PXA-G may be smaller in size than the blue emitting region PXA-B, but the exemplary embodiments are not limited thereto.

[0109] In the following text, Figures 3 to 6 This is a schematic cross-sectional view of a light-emitting element according to at least one exemplary embodiment. Figure 3A light-emitting element ED according to at least one exemplary embodiment is shown, comprising a first electrode EL1, a hole transport region HTR, an emitter layer EML, an electron transport region ETR, and / or a second electrode EL2 stacked in sequence.

[0110] and Figure 3 compared to, Figure 4 A cross-sectional view of a light-emitting element (ED) according to at least one exemplary embodiment is shown, wherein the hole transport region (HTR) includes a hole injection layer (HIL) and a hole transport layer (HTL), and / or the electron transport region (ETR) includes an electron injection layer (EIL) and an electron transport layer (ETL). Furthermore, with Figure 3 and Figure 4 compared to, Figure 5 A cross-sectional view of a light-emitting element (ED) according to at least one exemplary embodiment is shown, wherein the hole transport region (HTR) includes a hole injection layer (HIL), a hole transport layer (HTL), and / or an electron blocking layer (EBL), and / or the electron transport region (ETR) includes an electron injection layer (EIL), an electron transport layer (ETL), and / or a hole blocking layer (HBL). Figure 4 compared to, Figure 6 A cross-sectional view of a light-emitting element ED according to at least one exemplary embodiment is shown, wherein a cover layer CPL is provided on a second electrode EL2.

[0111] The first electrode EL1 is configured to be conductive. For example, electrode EL1 may include a conductive material (or a conductive material). The first electrode EL1 may be formed of a metallic material, a metal alloy, a conductive compound, etc. The first electrode EL1 may be an anode or a cathode. However, exemplary embodiments are not limited thereto. Furthermore, the first electrode EL1 may be a pixel electrode. The first electrode EL1 may be a transmission electrode, a semi-transparent reflection electrode, a reflection electrode, etc. 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, at least two compounds selected from these compounds, mixtures selected from two or more of these compounds, oxides thereof, etc.

[0112] When the first electrode EL1 is a transmission electrode, it may comprise a transparent metal oxide, such as indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), and / or indium tin zinc oxide (ITZO). When the first electrode EL1 is a semi-transparent or reflective electrode, it may comprise Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, Mo, Ti, W, their compounds, or mixtures thereof (e.g., a mixture of Ag and Mg); or LiF / Ca (a stacked structure of LiF and Ca), or LiF / Al (a stacked structure of LiF and Al). Alternatively, the first electrode EL1 may have a multilayer structure comprising a reflective or semi-transparent reflective film formed from the materials described above, and / or a transparent conductive film formed from indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), indium tin zinc oxide (ITZO), etc. For example, the first electrode EL1 may have a three-layer structure of ITO / Ag / ITO, but the exemplary embodiments are not limited thereto. Furthermore, the exemplary embodiments are not limited thereto, and / or the first electrode EL1 may comprise the metallic materials described above, a combination of two or more metallic materials selected from the metallic materials described above, and / or oxides of the metallic materials described above. The first electrode EL1 may have a thickness of about 700 Å to about 10000 Å. For example, the first electrode EL1 may have a thickness of about 1000 Å to about 3000 Å.

[0113] A hole transport region (HTR) is provided on the first electrode EL1. The hole transport region (HTR) may include at least one of a hole injection layer (HIL), a hole transport layer (HTL), a buffer layer or emission assist layer (not shown), and an electron blocking layer (EBL). The thickness of the hole transport region (HTR) may be, for example, from about 50 Å to about 15,000 Å.

[0114] The hole transport region (HTR) can have a single layer formed of a single material, a single layer formed of multiple different materials, or a multilayer structure including multiple layers formed of multiple different materials.

[0115] For example, the hole transport region HTR can have a single-layer structure of a hole injection layer HIL or a hole transport layer HTL, or it can have a single-layer structure formed of a hole injection material and a hole transport material. Furthermore, the hole transport region HTR can have a single-layer structure formed of various different materials, or a structure in which hole injection layer HIL / hole transport layer HTL, hole injection layer HIL / hole transport layer HTL / buffer layer (not shown), hole injection layer HIL / buffer layer (not shown), hole transport layer HTL / buffer layer (not shown), and / or hole injection layer HIL / hole transport layer HTL / electron blocking layer EBL are stacked sequentially from the first electrode EL1, but the embodiments of the present invention are not limited thereto.

[0116] Hole transport regions (HTRs) can be formed using various methods, such as vacuum deposition, spin coating, tape casting, Langmuir-Blodgett (LB) method, inkjet printing, laser printing and / or laser-induced thermal imaging (LITI).

[0117] The hole transport region (HTR) may contain a compound represented by the following formula H-1: [Formula H-1]

[0118] In formula H-1, L1 and L2 can each be independently a straight-linked, substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms. a and b can each be independently an integer from 0 to 10. When a or b is an integer of 2 or greater than 2, multiple L1 or L2 can each be independently a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms.

[0119] In formula H-1, Ar1 and Ar2 can each independently be a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms. Furthermore, in formula H-1, Ar3 can be a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms.

[0120] The compounds represented by formula H-1 above can be monoamine compounds. Alternatively, the compounds represented by formula H-1 above can be diamine compounds, wherein at least one of Ar1 to Ar3 includes an amine group as a substituent. Furthermore, the compounds represented by formula H-1 above can be carbazole-based compounds comprising a substituted or unsubstituted carbazole group in at least one of Ar1 and Ar2, and / or fluorene-based compounds comprising a substituted or unsubstituted fluorene group in at least one of Ar1 and Ar2.

[0121] A compound represented by formula H-1 may be represented by at least one of the compounds in the following group of compounds H. However, the compounds listed in the following group of compounds H are examples, and / or the compounds represented by formula H-1 are not limited to those represented by the following group of compounds H.

[0122] [Compound Group H]

[0123] Hole transport region (HTR) can contain phthalocyanine compounds, such as copper phthalocyanine; N 1 N 1 '-([1,1'-biphenyl]-4,4'-diyl)bis(N 1 -Phenyl-N 4 N 4 4,4',4''-[tris(3-methylphenyl)phenylamino]triphenylamine (m-MTDATA), 4,4',4''-tris(N,N-diphenylamino)triphenylamine (TDATA), 4,4',4''-tris(N(2-naphthyl)-N-phenylamino]triphenylamine (2-TNATA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS) Polyaniline / dodecylbenzenesulfonic acid (PANI / DBSA), polyaniline / camphor sulfonic acid (PANI / CSA), polyaniline / poly(4-styrene sulfonate) (PANI / PSS), N,N'-di(naphthyl-1-yl)-N,N'-diphenyl-benzidine (NPB), triphenylamine-containing polyether ketone (TPAPEK), 4-isopropyl-4'-methyldiphenyliodonium [tetra(pentafluorophenyl)borate], dipyrazino[2,3-f: 2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarboxylonitrile (HAT-CN), etc.

[0124] Hole transport regions (HTRs) can contain carbazole-based derivatives (e.g., N-phenylcarbazole or polyvinylcarbazole), fluorene-based derivatives, triphenylamine-based derivatives (e.g., N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1-biphenyl]-4,4'-diamine (TPD) or 4,4',4''-tris(N-carbazolyl)triphenylamine (TCTA)), N,N'-bis(naphthyl-1-yl)-N,N'-diphenyl-benzidine (NPB), 4,4'-cyclohexylenebis[N,N-bis(4-methylphenyl)aniline] (TAPC), 4,4'-bis[N,N'-(3-tolyl)amino]-3,3'-dimethylbiphenyl (HMTPD), 1,3-bis(N-carbazolyl)benzene (mCP), etc.

[0125] In addition, the hole transport region (HTR) can contain 9-(4-tert-butylphenyl)-3,6-bis(triphenylsilyl)-9H-carbazole (CzSi), 9-phenyl-9H-3,9'-bicarbazole (CCP), 1,3-bis(1,8-dimethyl-9H-carbazole-9-yl)benzene (mDCP), etc.

[0126] The hole transport region HTR can contain the compounds described above for hole transport regions in at least one of the hole injection layer HIL, the hole transport layer HTL, and the electron blocking layer EBL.

[0127] The thickness of the hole transport region HTR can be from about 100 Å to about 10,000 Å, for example, from about 100 Å to about 5,000 Å. When the hole transport region HTR includes a hole injection layer HIL, the hole injection layer HIL can have a thickness of, for example, from about 30 Å to about 1,000 Å. When the hole transport region HTR includes a hole transport layer HTL, the hole transport layer HTL can have a thickness of about 30 Å to about 1,000 Å. For example, when the hole transport region HTR includes an electron blocking layer EBL, the electron blocking layer EBL can have a thickness of about 10 Å to about 1,000 Å. If the thicknesses of the hole transport region HTR, the hole injection layer HIL, the hole transport layer HTL, and the electron blocking layer EBL satisfy the ranges described above, satisfactory hole transport properties can be achieved without a significant increase in driving voltage.

[0128] In addition to the materials described above, the hole transport region (HTR) may further include a charge-generating material to increase conductivity. The charge-generating material may be uniformly or non-uniformly dispersed in the hole transport region (HTR). The charge-generating material may be, for example, a p-dopant. The p-dopant may include at least one of metal halide compounds, quinone derivatives, metal oxides, and compounds containing cyano groups, but exemplary embodiments are not limited thereto. For example, p-dopers may include metal halide compounds (e.g., CuI or RbI), quinone derivatives (e.g., tetracyanoquinone dimethyl ether (TCNQ) or 2,3,5,6-tetrafluoro-7,7',8,8'-tetracyanoquinone dimethyl ether (F4-TCNQ)), metal oxides (e.g., tungsten oxide or molybdenum oxide), cyano-containing compounds (e.g., dipyrazino[2,3-f: 2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarboxynitrile (HAT-CN) or 4-[[2,3-bis[cyano-(4-cyano-2,3,5,6-tetrafluorophenyl)methylene]cyclopropyl]-cyanomethyl]-2,3,5,6-tetrafluorobenzyl nitrile (NDP9)), etc., but exemplary embodiments are not limited thereto.

[0129] As described above, in addition to the hole injection layer HIL and the hole transport layer HTL, the hole transport region HTR may further include at least one of a buffer layer (not shown) and an electron blocking layer EBL. The buffer layer (not shown) can compensate for the resonant distance according to the wavelength of light emitted from the emission layer EML, and thus can improve emission efficiency. Materials that can be included in the hole transport region HTR can be used as materials included in the buffer layer (not shown). The electron blocking layer EBL is a layer used to suppress electron injection from the electron transport region ETR to the hole transport region HTR (e.g., to prevent electron injection from the electron transport region ETR to the hole transport region HTR and / or reduce the likelihood of electron injection from the electron transport region ETR to the hole transport region HTR).

[0130] In at least one exemplary embodiment, the emitter layer EML may comprise a first compound according to at least one exemplary embodiment. The emitter layer EML according to at least one exemplary embodiment may further comprise at least one of a second to a fourth compound. The second compound may comprise a tricyclic fused ring system containing a nitrogen atom as a cyclizing atom. The third compound may comprise a six-membered cyclic group containing at least one nitrogen atom as a cyclizing atom. The fourth compound may comprise an organometallic complex. The second to fourth compounds will be described in more detail later.

[0131] In this specification, a first compound may be referred to as a fused polycyclic compound according to at least one exemplary embodiment. A fused polycyclic compound according to at least one exemplary embodiment may include a core structure, a first substituent bonded to the core structure, and / or a second substituent bonded to the core structure. A fused polycyclic compound according to at least one exemplary embodiment may include a nine-ring fused ring system comprising four heteroatoms and two boron atoms as cyclic atoms. The four heteroatoms may each be N, O, or S. The first substituent is a substituted or unsubstituted aryl group having 6 to 60 cyclic carbon atoms and may be bonded at the para position relative to the boron atom of the core structure. The second substituent is a substituted or unsubstituted alkyl group or electron-donating group having 1 to 20 carbon atoms and may be bonded to another cyclic group different from the cyclic group bonded to the first substituent. Therefore, a fused polycyclic compound according to at least one exemplary embodiment may have dimensional and high charge transfer (CT) properties in space, and / or may therefore further accelerate reverse intersystem crossing (RISC). Fused polycyclic compounds according to at least one exemplary embodiment can contribute to the improvement of emission efficiency and lifespan of light-emitting elements (EDs).

[0132] A light-emitting element ED according to at least one exemplary embodiment may comprise a fused polycyclic compound according to at least one exemplary embodiment. The fused polycyclic compound according to at least one exemplary embodiment may be represented by the following formula 1.

[0133] [Formula 1]

[0134] In Equation 1, B represents boron.

[0135] In Equation 1, X 1 To X 4 It can correspond to at least one of the four heteroatoms described above. R a1 and R a2 It can correspond to at least one of the first substituents described above. R b1 To R b4 At least one of them can correspond to at least one of the second substituents described above.

[0136] For example, in Equation 1, X 1 To X 4 They can be O, S, or NR independently. y1 For example, X 1 To X 4 At least one of them can be NR y1 .

[0137] R y1It can be a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, or represented by the following formula 2. For example, R y1 It can be a substituted or unsubstituted aryl group having 6 to 60 cyclic carbon atoms, or represented by the following formula 2.

[0138] [Equation 2]

[0139] In Equation 2, n1 can be an integer from 0 to 5. y2 It can be a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms. Indicates the connection location.

[0140] If n1 is an integer of 2 or greater than 2, then multiple R y2 They can all be the same, or multiple Rs. y2 At least one of them can be different from the others. The case where n1 is 0 can be different from the case where n1 is 5 and there are 5 R's. y2 The same applies when the atom is hydrogen.

[0141] R y1 Equation 2 can be represented by at least one of Y1-1 to Y1-18 below. In Y1-1 to Y1-18, Indicates the connection location.

[0142]

[0143] In Equation 1, R 1 To R 6 and R b1 To R b4 Each group can be independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted amine group, a substituted or unsubstituted oxygen 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 60 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, or can be bonded to an adjacent group to form a ring, etc. For example, R 1 To R 6Each of these can be independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted isopropyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted dimethylfluorenyl group.

[0144] In at least one exemplary implementation, R b1 To R b4 At least one of them can be a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or an electron-donating group. The electron-donating group can be a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted alkylamine group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted arylamine group, or a substituted or unsubstituted carbazole group. In the following text, for ease of explanation, R... b1 To R b4 At least one of them is called a "second substituent".

[0145] For example, the second substituent can be a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted isopropyl group, a substituted or unsubstituted n-butyl group, a substituted or unsubstituted tert-butyl group, a substituted or unsubstituted cyclopentyl group, a substituted or unsubstituted cyclohexyl group, a substituted or unsubstituted methoxy group, a substituted or unsubstituted propoxy group, a substituted or unsubstituted isopropoxy group, a substituted or unsubstituted tert-butoxy group, a substituted or unsubstituted cyclohexoxy group, a substituted or unsubstituted phenoxy group, a substituted or unsubstituted dimethylamine group, a substituted or unsubstituted ethylamine group, a substituted or unsubstituted N-methylphenylamine group, a substituted or unsubstituted N-propylphenylamine group, a substituted or unsubstituted diphenylamine group, a substituted or unsubstituted methylthio group, a substituted or unsubstituted isopropylthio group, a substituted or unsubstituted propylthio group, a substituted or unsubstituted tert-butylthio group, a substituted or unsubstituted phenylthio group, or a substituted or unsubstituted carbazole group. The second substituent may be represented by at least one of the following Rb-1 to Rb-45.

[0146]

[0147] Between Rb-28 and Rb-45, two It can correspond to R b1 To R b4 The positions of two adjacent groups in the R group. b1 and R b2 It can be two adjacent groups. R b2 and R b3It can be two adjacent groups. R b3 and R b4 These can be two adjacent groups. For example, in Rb-30, two... These can be respectively corresponding to R b3 and R b4 The location. In Rb-31, two These can be respectively corresponding to R b2 and R b3 The location.

[0148] For example, R b1 To R b4 The remainder, which is not a second substituent, may each independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted dibenzofuran group. However, this is an example, and exemplary embodiments are not limited thereto.

[0149] In Equation 1, R 7 To R 10 R a1 and R a2 Each of these can independently be a hydrogen atom, a deuterium atom, a cyano group, a halogen atom, 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 60 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms. For example, R 7 To R 10 Each of these can be a hydrogen atom, a deuterium atom, a substituted or unsubstituted tert-butyl group, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted terphenyl group.

[0150] In at least one exemplary implementation, R a1 and R a2 At least one of them can be a substituted or unsubstituted aryl group having 6 to 60 cyclic carbon atoms. In the following text, for ease of explanation, R... a1 and R a2 The at least one of the following is referred to as a "first substituent". The first substituent can be represented by at least one of the following Ra-1 to Ra-5. In the following Ra-2, D is a deuterium atom. R a1 and R a2 The other substituent that is not the first substituent can be a hydrogen atom, a deuterium atom, a cyano group, a substituted or unsubstituted diphenylamine group, or a substituted or unsubstituted carbazole group.

[0151]

[0152] In Equation 1, when R b2 and R b3When the groups bond together to form a moiety represented by the following formula RB, the first substituent may be an unsubstituted aryl group having 6 to 60 cyclic carbon atoms. In the following formula RB, b2 may be a group corresponding to R. b2 The position, and / or b3 can be corresponding to R b3 The location.

[0153] [RB style]

[0154] Formula RB can be a portion included in the previously described Rb-41. For example, in Rb-41, when two The carbon atom adjacent to Located in R b2 At, and / or adjacent to oxygen atoms Located in R b3 In this case, the first substituent can be an unsubstituted aryl group having 6 to 60 cyclic carbon atoms.

[0155] A fused polycyclic compound according to at least one exemplary embodiment may include a chemical structure in which any hydrogen atom in the molecule is replaced by a deuterium atom. For example, at least one hydrogen atom may optionally be replaced by a deuterium atom. In at least one exemplary embodiment, at least one hydrogen atom is replaced by a deuterium atom. A fused polycyclic compound according to at least one exemplary embodiment may include a deuterium atom directly bonded to the core structure or may include a substituent directly bonded to the core structure and replaced by a deuterium atom. In Formula 1, R 1 To R 10 R a1 R a2 R b1 To R b4 and R y1 At least one of them can be a deuterium atom, or it can include a substituent substituted by a deuterium atom. For example, in Formula 1, R 1 To R 6 R a1 and R a2 At least one of them can be a phenyl group substituted with a deuterium atom. However, this is an example, and exemplary embodiments are not limited thereto.

[0156] In at least one exemplary embodiment, Formula 1 may be represented by at least one of the following Formulas 1-A1 to 1-A6. Formulas 1-A1 to 1-A6 represent where X in Formula 1 is specified. 1 To X 4 The situation is as follows. Equation 1-A1 can represent the case where X in Equation 1... 1 To X 4 Each independently as NR y1The situation is as follows. Equation 1-A2 can represent the case where X in Equation 1... 1 X 3 and X 4 Each is an independent NR y1 , and / or X 2 This is the case of O or S. Equation 1-A3 can represent where X in Equation 1... 3 and X 4 Each is an independent NR y1 , and / or X 1 and X 2 Each is an independent case of O or S. Equation 1-A4 can represent where X in Equation 1 1 It is NR y1 , and / or X 2 To X 4 Each is an independent case of O or S. Equation 1-A5 can represent the case where X in Equation 1... 4 It is NR y1 , and / or X 1 To X 3 Each case is either O or S independently. Equation 1-A6 can represent the case where X in Equation 1... 3 It is NR y1 , and / or X 1 X 2 and X 4 Each case is either O or S, independent of the others.

[0157] [Equation 1-A1]

[0158] [Equation 1-A2]

[0159] [Equation 1-A3]

[0160] [Equation 1-A4]

[0161] [Formula 1-A5]

[0162] [Equation 1-A6]

[0163] The details described in Equation 1 above can be applied to R in Equations 1-A1 to 1-A6. 1 To R 6 R b1 To R b4 R 7 To R10 R a1 and R a2 X 11 To X 14 Each can be O or S independently. For example, in Equation 1-A6, X 11 X 12 and X 14 It can be O.

[0164] In equations 1-A1 to 1-A6, n2 to n5 can each be an integer from 0 to 5 independently. R y11 To R y14 Each of these can independently be a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms. In Formulas 1-A1 to 1-A6, R is included. y11 cyclic groups, including R y12 cyclic groups, including R y13 cyclic groups and including R y14 The cyclic groups can each be independently represented by at least one of the previously described Y1-1 to Y1-18.

[0165] If n² is an integer of 2 or greater than 2, then multiple R y11 They can all be the same, or multiple Rs. y11 At least one of them can be different from the others. The case where n2 is 0 can be the same as the case where n2 is 5 and there are 5 R's. y11 The same applies if n3 is a hydrogen atom. If n3 is an integer of 2 or greater than 2, then multiple R... y12 They can all be the same, or multiple Rs. y12 At least one of them can be different from the rest. The case where n3 is 0 can be different from the case where n3 is 5 and there are 5 R's. y12 The same applies when the atom is hydrogen.

[0166] If n4 is an integer of 2 or greater than 2, then multiple R y13 They can all be the same, or multiple Rs. y13 At least one of them can be different from the others. The case where n4 is 0 can be different from the case where n4 is 5 and there are 5 R's. y13 The same applies if n5 is a hydrogen atom. If n5 is an integer of 2 or greater than 2, then multiple R... y14 They can all be the same, or multiple Rs. y14 At least one of them can be different from the others. The case where n5 is 0 can be the same as the case where n5 is 5 and there are 5 R's. y14 The same applies when the atom is hydrogen.

[0167] Formula 1 can be represented by at least one of the compounds in Group 1. A fused polycyclic compound according to at least one exemplary embodiment can be represented by at least one of the compounds in Group 1. A light-emitting element ED according to at least one exemplary embodiment can contain at least one of the compounds in Group 1. An emitting layer EML can contain at least one of the compounds in Group 1. In Group 1, D is a deuterium atom. In Group 1, OMe is a methoxy group, and SMe is a methylthio group.

[0168] [Compound Group 1]

[0169] A light-emitting element ED comprising a fused polycyclic compound according to at least one exemplary embodiment may have a peak emission wavelength in the wavelength region of about 430 nm to about 470 nm. The peak emission wavelength may refer to the wavelength at which the emission intensity is maximum in the emission spectrum. A light-emitting element ED comprising a fused polycyclic compound according to at least one exemplary embodiment may emit blue light. A third light-emitting element ED-3 emitting blue light (… Figure 2 It may contain a fused polycyclic compound according to at least one exemplary embodiment.

[0170] The emitter layer (EML) may contain a fused polycyclic compound according to at least one exemplary embodiment as a dopant. The fused polycyclic compound according to at least one exemplary embodiment may be a delayed fluorescence material. The fused polycyclic compound according to at least one exemplary embodiment may be a thermally activated delayed fluorescence (TADF) material. In the fused polycyclic compound according to at least one exemplary embodiment, a triplet exciton may be converted into a singlet exciton due to a reverse intersystem crossing (RISC) mechanism, thereby emitting light.

[0171] The fused polycyclic compound according to at least one exemplary embodiment may include a nine-ring fused ring system as the core structure, comprising four heteroatoms and two boron atoms as cyclic atoms. Furthermore, the fused polycyclic compound according to at least one exemplary embodiment may include a first substituent and a second substituent, each bonded to the core structure. The first substituent is a substituted or unsubstituted aryl group having 6 to 60 cyclic carbon atoms, and is the previously described R... a1 and R a2 At least one group in the core may be bonded to the para position of a boron atom relative to the core structure. The second substituent may be a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or an electron-donating group, and may be the R group previously described. b1 To R b4 At least one group in the group. The second substituent may be a group with high electron-donating properties.

[0172] Fused polycyclic compounds according to at least one exemplary embodiment, including the nine-ring fused ring system comprising four heteroatoms and two boron atoms as cyclic atoms, can contribute to the improvement of emission efficiency and lifetime of light-emitting elements (EDs) due to their high absorbance, narrow full width at half maximum (FWHM), and rapid reverse intersystem crossing.

[0173] Typical compounds including nine-ring fused-ring systems exhibit high planarity, leading to unwanted (e.g., undesirable) intermolecular energy transfer and potentially degrading lifetime at high concentrations. Fused-ring polycyclic compounds according to at least one exemplary embodiment possess increased spatial volume while maintaining the nine-ring fused-ring system, and utilize substituents with high electron-donating properties, thus suppressing Dexter energy transfer (DET) and potentially increasing charge transfer (CT) properties. Dexter energy transfer (DET) can be an unwanted intermolecular energy transfer. Furthermore, an aryl group (i.e., the first substituent) is introduced at the para position relative to a boron atom, which is a cyclizing atom in the nine-ring fused-ring system of the fused-ring polycyclic compound according to at least one exemplary embodiment, and / or thus potentially improves molecular resonance stability. Therefore, in the fused-ring polycyclic compound according to at least one exemplary embodiment, the reduction in lifetime at high concentrations can be suppressed, improved lifetime can be exhibited at low concentrations, and RISC can be accelerated. Therefore, the fused-ring polycyclic compound according to at least one exemplary embodiment can contribute to the improvement of luminous efficiency and lifetime of light-emitting elements (EDs).

[0174] Figure 7A This is a diagram showing the distribution of the highest occupied molecular orbitals (HOMO) of compound C-18. Figure 7B This is a graph showing the distribution of the lowest unoccupied molecular orbitals (LUMOs) of compound C-18. Compound C-18 is a fused polycyclic compound according to at least one exemplary embodiment. For ease of explanation, compound C-18 and... Figure 7B The "P1" and "P2" in the compound, and P1 and P2 in compound C-18 correspond to respectively Figure 7B P1 and P2 in the example.

[0175]

[0176] In compound C-18, R in formula 1 b3 It is an unsubstituted tert-butyl group, and the unsubstituted tert-butyl group is an electron-donating substituent (i.e., a second substituent). Reference Figure 7A Compound C-18 exhibits a relatively large HOMO due to the introduction of a tert-butyl group. Compound C-18, exhibiting a relatively large HOMO, possesses significantly enhanced charge transfer properties. The tert-butyl group is a spatially large substituent and can suppress the dexter energy transfer of the compound by preventing intermolecular interactions. Therefore, it can be seen that fused polycyclic compounds containing electron-donating substituents such as tert-butyl groups according to at least one exemplary embodiment have suppressed dexter energy transfer and will exhibit excellent charge transfer properties.

[0177] In compound C-18, R in formula 1 a1 and R a2 Each is an unsubstituted phenyl group, and the unsubstituted phenyl group corresponds to a cyclic group designated P1 or P2. The unsubstituted phenyl group may correspond to the first substituent described above. (See reference) Figure 7B As can be seen, LUMO extends to cyclic groups referred to as P1 or P2, due to the introduction of phenyl groups at the para position relative to the boron atom.

[0178] With the ΔE of compound C-18, in which the first and second substituents are introduced, ST The emission efficiency becomes lower, RISC is further accelerated, and therefore compound C-18 can contribute to high emission efficiency and roll-off suppression in light-emitting elements (EDs). Roll-off refers to the phenomenon of a sharp decrease in emission efficiency at high current densities. If RISC is promoted, triplet excitons with long lifetimes can rapidly convert to singlet excitons. ΔE ST It refers to the absolute value between the energy levels of the triplet and singlet states.

[0179] In compound C-18, the first and second substituents effectively protect the boron atoms in the core structure, and thus prevent material degradation due to reactions with water and oxygen molecules during the synthesis and / or deposition of the compound. Therefore, the fused polycyclic compound containing the first and second substituents according to at least one exemplary embodiment can exhibit excellent material stability. The fused polycyclic compound with improved material stability according to at least one exemplary embodiment can contribute to the improvement of the emission efficiency and lifespan of light-emitting elements (EDs).

[0180] In at least one exemplary embodiment, the emitter layer EML may comprise a fused polycyclic compound according to at least one exemplary embodiment, and further comprise at least one of a second to a fourth compound. In at least one exemplary embodiment, the emitter layer EML may comprise a second compound represented by the formula HT-1. For example, the second compound may be used as a hole transport host material in the emitter layer EML.

[0181] [Formula HT-1]

[0182] In formula HT-1, A1 to A8 can each be N or CR independently. 51 For example, A1 to A8 can all be CR. 51 Alternatively, at least one of A1 to A8 can be N, and the remainder can be CR. 51 .

[0183] In formula HT-1, L1 can be a linear bond, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms. For example, L1 can be a linear bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted divalent biphenyl group, a substituted or unsubstituted divalent carbazole group, etc., but the embodiments of the present invention are not limited thereto.

[0184] In equation HT-1, Y a It can be a direct-connect key, CR 52 R 53 or SiR 54 R 55 In other words, it can refer to the two benzene rings in formula HT-1 connected to the nitrogen atom via direct bonding, or Connection, where Indicates the connection position. In equation HT-1, when Y... a When the bond is a direct linker, the second compound represented by formula HT-1 may contain a carbazole moiety.

[0185] In formula HT-1, Ar1 can be a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms. For example, Ar1 can be a substituted or unsubstituted carbazole group, a substituted or unsubstituted dibenzofuran group, a substituted or unsubstituted dibenzothiophene group, a substituted or unsubstituted biphenyl group, etc., but the embodiments of the present invention are not limited thereto.

[0186] In equation HT-1, R 51 To R 55 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 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 cyclic carbon atoms. Alternatively, R 51 To R 55 Each of these groups can bond to an adjacent group to form a ring. For example, R 51 To R 55 Each can be an independent hydrogen atom or a deuterium atom. R 51 To R 55 Each can be an unsubstituted methyl group or an unsubstituted phenyl group, which can be independent of each other.

[0187] In at least one exemplary embodiment, the second compound represented by formula HT-1 may be represented by at least one of the compounds represented by compound group 2. The emitter layer EML may contain at least one of the compounds represented by compound group 2 as a hole transport host material.

[0188] [Compound Group 2]

[0189] In the compounds presented in Compound Group 2, "D" may refer to a deuterium atom, and "Ph" may refer to a substituted or unsubstituted phenyl group. For example, in the embodiment compounds presented in Compound Group 2, "Ph" may refer to an unsubstituted phenyl group.

[0190] In at least one exemplary embodiment, the emitter layer EML may contain a third compound represented by the formula ET-1. For example, the third compound may be used as an electron transport host material for the emitter layer EML.

[0191] [Formula ET-1]

[0192] In Equation ET-1, at least one of X1 to X3 is N, and the rest are CR. 56 For example, at least one of X1 to X3 can be N, and the others can each be CR independently. 56 In this case, the third compound represented by formula ET-1 may include a pyridine moiety. Alternatively, two of X1 to X3 may be N, and the remainder may be CR. 56 In this case, the third compound represented by formula ET-1 may include a pyrimidine moiety. Alternatively, X1 to X3 may all be N. In this case, the third compound represented by formula ET-1 may include a triazine moiety.

[0193] In equation ET-1, R 56 It can be a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 cyclic carbon atoms.

[0194] In Equation ET-1, b1 to b3 can each be an integer from 0 to 10 independently.

[0195] In formula ET-1, Ar2 to Ar4 can each independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms. For example, Ar2 to Ar4 can each independently be a substituted or unsubstituted phenyl group or a substituted or unsubstituted carbazole group.

[0196] In formula ET-1, L2 to L4 can each be independently a straight-linked, substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms. When b1 to b3 are 2 or greater than 2, L2 to L4 can each be independently a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms.

[0197] In at least one exemplary embodiment, the third compound may be represented by at least one compound from the following group 3. The light-emitting element ED of at least one exemplary embodiment may contain at least one compound from the following group 3.

[0198] [Compound Group 3]

[0199] In the examples presented in compound group 3, “D” refers to a deuterium atom and “Ph” refers to an unsubstituted phenyl group.

[0200] The emitter layer EML can contain a second compound and a third compound, and the second and third compounds can form an excitocomplex. In the emitter layer EML, an excitocomplex can be formed by a hole transport host and an electron transport host. In this case, the triplet energy of the excitocomplex formed by the hole transport host and the electron transport host can correspond to the difference between the lowest unoccupied molecular orbital (LUMO) energy level of the electron transport host and the highest occupied molecular orbital (HOMO) energy level of the hole transport host.

[0201] For example, the absolute value of the triplet energy (T1) of the excimer complex formed by the hole transport host and the electron transport host can be from about 2.4 eV to about 3.0 eV. Furthermore, the triplet energy of the excimer complex can be less than the energy gap between each host material. The excimer complex can have a triplet energy of about 3.0 eV or less (e.g., as an energy gap between the hole transport host and the electron transport host).

[0202] In at least one exemplary embodiment, in addition to the first to third compounds as described above, the emission layer EML may also contain a fourth compound. The fourth compound may serve as a phosphorescent sensitizer for the emission layer EML. Energy can be transferred from the fourth compound to the first compound, thereby emitting light.

[0203] For example, the emitting layer EML may contain an organometallic complex containing platinum (Pt) as a central metal atom and ligands attached to the central metal atom as a fourth compound. The emitting layer EML in at least one exemplary embodiment of the light-emitting element ED may contain a compound represented by the following formula D-1 as the fourth compound.

[0204] [Formula D-1]

[0205] In equation D-1, Q1 to Q4 can each be C or N independently.

[0206] In formula D-1, C1 to C4 can each be independently a substituted or unsubstituted hydrocarbon ring having 5 to 30 cyclic carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heterocycle having 2 to 30 cyclic carbon atoms.

[0207] In equation D-1, L 11 To L 13 Each can be a direct-connect key independently. , , , Substituted or unsubstituted divalent alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 cyclic carbon atoms, or substituted or unsubstituted heteroaryl groups having 2 to 30 cyclic carbon atoms. In L 11 To L 13 middle," "" refers to the part connected to C1 to C4.

[0208] In equation D-1, b11 to b13 can each be 0 or 1 independently. If b11 is 0, C1 and C2 can be unconnected to each other. If b12 is 0, C2 and C3 can be unconnected to each other. If b13 is 0, C3 and C4 can be unconnected to each other.

[0209] In equation D-1, R 61 To R 66 Each of these can independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted thio group, a substituted or unsubstituted oxy group, a substituted or unsubstituted amine group, a substituted or unsubstituted boron group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 cyclic carbon atoms. Alternatively, R 61 To R 66 Each of the groups can bond to an adjacent group to form a ring. R 61 To R 66 Each can be a substituted or unsubstituted methyl group or a substituted or unsubstituted tert-butyl group, which can be independent of each other.

[0210] In equation D-1, d1 to d4 are each an independent integer from 0 to 4. In equation D-1, if each of d1 to d4 is 0, the fourth compound can be unaffected by R. 61 To R 64 Each of d1 to d4 is replaced. Where each of d1 to d4 is 4 and R 61 To R 64 The case where each of the individual atoms is a hydrogen atom is the same as the case where each of d1 to d4 is 0. When each of d1 to d4 is an integer of 2 or greater, multiple R... 61 To R 64 They can be the same, or multiple Rs. 61 To R 64 At least one of them may be different from the others.

[0211] In formula D-1, C1 to C4 can each be independently a substituted or unsubstituted hydrocarbon ring, or a substituted or unsubstituted heterocycle represented by at least one of the following C-1 to C-4:

[0212] In C-1 to C-4, P1 can be... or CR 74 P2 can be or NR 81 P3 can be or NR 82 , and / or P4 can be or CR 88 R 71 To R 88 Each group may be independently a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, or may be bonded to an adjacent group to form a ring.

[0213] Furthermore, in C-1 to C-4, " "Corresponds to the portion attached to Pt as the central metal atom, and" "Corresponds to the linkage to an adjacent cyclic group (C1 to C4) or a linker group (L)" 11 To L 13 () part.

[0214] At least one exemplary embodiment of the emitter layer EML may contain a first compound as a fused polycyclic compound and at least one of a second to a fourth compound. For example, the emitter layer EML may contain a first compound, a second compound, and / or a third compound. In the emitter layer EML, the second and third compounds may form an excimer complex, and energy may be transferred from the excimer complex to the first compound, thereby emitting light.

[0215] Furthermore, the emitter layer EML may contain a first compound, a second compound, a third compound, and / or a fourth compound. In the emitter layer EML, the second and third compounds can form an exciton complex, and energy can be transferred from the exciton complex to the fourth and first compounds, thereby emitting light. In at least one exemplary embodiment, the fourth compound may be a sensitizer. The fourth compound contained in the emitter layer EML of the light-emitting element ED in at least one exemplary embodiment can act as a sensitizer to transfer energy from the host to the first compound, which is a light-emitting dopant. That is, the fourth compound, acting as an auxiliary dopant, accelerates the energy transfer to the first compound, which is a light-emitting dopant, thereby increasing the emission ratio of the first compound. Therefore, the emitter layer EML of at least one exemplary embodiment can improve emission efficiency. Furthermore, when the energy transfer to the first compound is increased, excitons formed in the emitter layer EML do not accumulate inside the emitter layer EML and emit light rapidly, thus reducing device degradation. Therefore, the lifetime of the light-emitting element ED of at least one exemplary embodiment can be increased.

[0216] At least one exemplary embodiment of the light-emitting element (ED) may comprise all of the first compound, the second compound, the third compound, and / or the fourth compound, and / or the emission layer (EML) may comprise a combination of two host materials and two dopant materials. In at least one exemplary embodiment of the light-emitting element (ED), the emission layer (EML) may simultaneously comprise the second and third compounds as two different hosts, the first compound emitting delayed fluorescence, and / or the fourth compound including an organometallic complex, thereby exhibiting excellent emission efficiency characteristics.

[0217] In at least one exemplary embodiment, the fourth compound represented by formula D-1 may represent at least one of the compounds represented by group 4 of compounds below. The emitter layer EML may contain at least one of the compounds represented by group 4 of compounds as a sensitizer material.

[0218] [Compound Group 4]

[0219] In the exemplary compounds presented in compound group 4, "D" refers to a deuterium atom.

[0220] When the emitting layer EML in the light-emitting device ED of at least one exemplary embodiment contains all of the first compound, the second compound, and the third compound, the content of the first compound may be from about 0.1 wt% to about 5 wt% relative to the total weight of the first compound, the second compound, and the third compound. However, embodiments of the present invention are not limited thereto. When the content of the first compound meets the ratio described above, the energy transfer from the second and third compounds to the first compound may be increased, and therefore the emission efficiency and device lifespan may be increased.

[0221] The content of the second and third compounds in the emitter layer EML can be a margin excluding the weight of the first compound. For example, the content of the second and third compounds in the emitter layer EML can be from about 65 wt% to about 95 wt% relative to the total weight of the first, second and third compounds.

[0222] In the total weight of the second and third compounds, the weight ratio of the second and third compounds can be from about 3:7 to about 7:3.

[0223] When the contents of the second and third compounds meet the ratios described above, the charge balance characteristics in the emitter layer EML are improved, and thus the emission efficiency and device lifespan can be increased. When the contents of the second and third compounds deviate from the ratio ranges described above, the charge balance in the emitter layer EML is disrupted, and therefore the emission efficiency may decrease and the device may be prone to degradation.

[0224] When the emitter layer EML contains a fourth compound, the content of the fourth compound in the emitter layer EML can be from about 10 wt% to about 30 wt% relative to the total weight of the first, second, third, and fourth compounds. However, exemplary embodiments are not limited to this. When the content of the fourth compound meets the content described above, the energy transfer from the host to the first compound, which acts as a light-emitting dopant, can be increased, thereby improving the luminescence ratio and / or thus improving the emission efficiency of the emitter layer EML. When the first, second, third, and fourth compounds contained in the emitter layer EML meet the content ratio range described above, excellent emission efficiency and long lifetime can be achieved.

[0225] An emitter layer (EML) is provided on the hole transport region (HTR). The emitter layer (EML) may have a thickness of, for example, from about 100 Å to about 1,000 Å or from about 100 Å to about 300 Å. The emitter layer (EML) may have a single layer formed of a single material, a single layer formed of multiple different materials, and / or a multilayer structure having multiple layers formed of multiple different materials.

[0226] In addition to the fused polycyclic compound of at least one exemplary embodiment, the emitter layer EML may further comprise the compounds described below.

[0227] In at least one exemplary embodiment of the light-emitting element (ED), the emitting layer (EML) may comprise anthracene derivatives, pyrene derivatives, fluoranthene derivatives, β-derived derivatives, dehydrobenzoxanthracene derivatives, and / or benzophenanthrene derivatives. Specifically, the emitting layer (EML) may comprise anthracene derivatives or pyrene derivatives.

[0228] exist Figures 3 to 6 In each light-emitting element (ED) shown, the emission layer (EML) may further comprise a host and dopant in addition to the host and dopant described above, and / or, for example, the emission layer (EML) may comprise a compound represented by the following formula E-1. The compound represented by the following formula E-1 can be used as a fluorescent host material.

[0229] [Equation E-1]

[0230] In equation E-1, R 31 To R 40 Each group can be independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted silyl group, a substituted or unsubstituted thio group, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, or can be bonded to adjacent groups to form a ring. R 31 To R 40 It can bond to adjacent groups to form saturated or unsaturated hydrocarbon rings, saturated heterocycles, or unsaturated heterocycles.

[0231] In E-1, c and d can each be an integer from 0 to 5 independently.

[0232] Formula E-1 can be represented by at least one of the following compounds E1 to E21.

[0233]

[0234] In at least one exemplary embodiment, the emitting layer EML may comprise a compound represented by formula E-2a or E-2b. The compound represented by formula E-2a or E-2b may be used as the host material of the phosphorescent emitting layer.

[0235] [Equation E-2a]

[0236] In equation E-2a, a can be an integer from 0 to 10, and L a It can be a directly linked, substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms. When a is 2 or an integer greater than 2, multiple L a Each can be independently a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms.

[0237] Furthermore, in E-2a, A1 to A5 can each be N or CR independently. i R a To R i Each group can be independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted amine group, a substituted or unsubstituted thio group, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, or can be bonded to an adjacent group to form a ring. R a To R i It can bond to adjacent groups to form hydrocarbon rings or heterocycles containing N, O, S, etc. as cyclic atoms.

[0238] In equation E-2a, two or three selected from A1 to A5 can be N, and the remainder can be CR. i .

[0239] [Equation E-2b]

[0240] In formula E-2b, Cbz1 and Cbz2 can each be an unsubstituted carbazole group or a carbazole group substituted with an aryl group having 6 to 30 cyclic carbon atoms. b It is a directly linked, substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms. b is an integer from 0 to 10, and when b is an integer of 2 or greater than 2, multiple L... b Each can be independently a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms.

[0241] In at least some exemplary embodiments, the compound represented by formula E-2a or E-2b may be represented by at least one of the compounds in the following group of compounds E-2.

[0242] [Compound Group E-2]

[0243] The emitter layer EML may further comprise materials commonly used in the art as host materials. For example, the emitter layer EML may comprise at least one of bis(4-(9H-carbazole-9-yl)phenyl)diphenylsilane (BCPDS), (4-(1-(4-(diphenylamino)phenyl)cyclohexyl)phenyl)diphenylphosphine oxide (POPCPA), bis[2-(diphenylphosphino)phenyl]ether oxide (DPEPO), 4,4'-bis(N-carbazole)-1,1'-biphenyl (CBP), 1,3-bis(N-carbazole)benzene (mCP), 2,8-bis(diphenylphosphino)dibenzo[b,d]furan (PPF), 4,4',4''-tris(carbazole-9-yl)-triphenylamine (TCTA), and 1,3,5-tris(1-phenyl-1H-benzo[d]imidazol-2-yl)benzene (TPBi) as host materials. However, the embodiments of the present invention are not limited thereto. For example, tris(8-hydroxyquinoline)aluminum (Alq3), 9,10-bis(naphthyl-2-yl)anthracene (ADN), 2-tert-butyl-9,10-bis(naphthyl-2-yl)anthracene (TBADN), stilbene arylene (DSA), 4,4'-bis(9-carbazolyl)-2,2'-dimethylbiphenyl (CDBP), 2-methyl-9,10-bis(naphthyl-2-yl)anthracene (MADN), hexaphenylcyclotriphosphazene (CP1), 1,4-bis(triphenylsilyl)benzene (UGH2), hexaphenylcyclotrisiloxane (DPSiO3), octaphenylcyclotetrasiloxane (DPSiO4), etc., can be used as main materials.

[0244] The emitter layer (EML) may contain compounds represented by the formula Ma. Compounds represented by the formula Ma can be used as phosphorescent dopant materials.

[0245] [Formula]

[0246] In the above formula Ma, Y1 to Y4 and Z1 to Z4 can each be independently CR1 or N, and R1 to R4 can each be independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted amine group, a substituted or unsubstituted thio group, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, or can be bonded to adjacent groups to form a ring. In formula Ma, m is 0 or 1, and n is 2 or 3. In formula Ma, when m is 0, n is 3, and when m is 1, n is 2.

[0247] Compounds represented by the formula Ma can be used as phosphorescent dopants.

[0248] In at least some exemplary embodiments, the compound represented by formula Ma can be represented by at least one of the following compounds M-a1 to M-a25.

[0249]

[0250] The emitter layer (EML) may contain a compound represented by at least one of the following formulas: Fa to Fc. A compound represented by at least one of the following formulas: Fa to Fc may be used as a fluorescent dopant material.

[0251] [Form Fa]

[0252] In the above formula Fa, the value is selected from R. a To R j The two in can be independently... Replace. R a To R j The un-included The remaining substituted groups can each independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms.

[0253] exist In this context, Ar1 and Ar2 can each be independently a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms. For example, at least one of Ar1 and Ar2 can be a heteroaryl group containing O or S as a cyclic atom.

[0254] [Formula Fb]

[0255] In the above formula Fb, R a and R b Each of Ar1 to Ar4 can be independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, or can be bonded to adjacent groups to form a ring. Each of Ar1 to Ar4 can be independently a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms.

[0256] In formula Fb, U and V can each be independently a substituted or unsubstituted hydrocarbon ring having 5 to 30 cyclic carbon atoms, or a substituted or unsubstituted heterocycle having 2 to 30 cyclic carbon atoms. At least one of Ar1 to Ar4 can be a heteroaryl group containing O or S as a cyclic atom.

[0257] In formula Fb, the number of rings represented by U and V can each be 0 or 1 independently. For example, in formula Fb, it means that when the number of U or V is 1, a ring forms a fused ring at the portion indicated by U or V, and when the number of U or V is 0, there is no ring indicated by U or V. Specifically, when the number of U is 0 and the number of V is 1, or when the number of U is 1 and the number of V is 0, the fused ring with a fluorene core in formula Fb can be a cyclic compound with four rings. Furthermore, when the number of each of U and V is 0, the fused ring with a fluorene core in formula Fb can be a cyclic compound with three rings. In some embodiments, when the number of each of U and V is 1, the fused ring with a fluorene core in formula Fb can be a cyclic compound with five rings.

[0258] [Formula Fc]

[0259] In equation Fc, A1 and A2 can each be independently O, S, Se, or NR. m And R mIt can be a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms. R1 to R 11 Each of the following is independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted amine group, a substituted or unsubstituted boron group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thio group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, or is bonded to an adjacent group to form a ring.

[0260] In formula Fc, A1 and A2 can each independently bond to substituents of adjacent rings to form fused rings. For example, when A1 and A2 are each independently NR m In this case, A1 can be bonded to R4 or R5 to form a ring. Additionally, A2 can be bonded to R7 or R8 to form a ring.

[0261] In at least one exemplary embodiment, the emitter layer EML may further comprise styrene derivatives (e.g., 1,4-bis[2-(3-N-ethylcarbazolyl)vinyl]benzene (BCzVB), 4-(di-p-tolylamino)-4'-[(di-p-tolylamino)styrene]stilbene (DPAVB) and / or N-(4-((E)-2-(6-(((E)-4-(diphenylamino)styrene)naphth-2-yl)vinyl)phenyl)-N-phenylaniline (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-tert-butylperylene (TBP)), pyrene and its derivatives (e.g., 1,1-dipyrene, 1,4-dipyrenebenzene, 1,4-bis(N,N-diphenylamino)pyrene) as dopant materials).

[0262] The emitter layer (EML) may further comprise phosphorescent dopant materials. For example, metal complexes comprising iridium (Ir), platinum (Pt), osmium (Os), gold (Au), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), and / or thulium (Tm) can be used as phosphorescent dopant. Specifically, iridium(III) bis(4,6-difluorophenylpyridyl-N,C2')pyridinecarboxylic acid (FIrpic), iridium(III) tetra(1-pyrazolyl)borate (FIr6), and / or octaethylporphyrin platinum (PtOEP) can be used as phosphorescent dopant. However, embodiments of the present invention are not limited thereto.

[0263] The emitter layer (EML) may contain quantum dot materials. The core of the quantum dots may be selected from group II-VI compounds, group I-II-VI compounds, group II-IV-VI compounds, group I-II-IV-VI compounds, group II-IV-V compounds, group III-VI compounds, group I-III-VI compounds, group III-V compounds, group III-II-V compounds, group IV-VI compounds, group IV elements, group IV compounds, and combinations thereof.

[0264] Group II-VI compounds can be at least one of the following: binary compounds (e.g., at least one of CdSe, CdTe, CdS, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, MgSe, MgS, and mixtures thereof); ternary compounds (e.g., CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, CdZn). At least one of Se, CdZnTe, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, MgZnSe, MgZnS and mixtures thereof; and quaternary compounds (e.g., at least one of HgZnTeS, CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe and mixtures thereof).

[0265] Group II-VI compounds may further include Group I metals and / or Group IV elements. Group I-II-VI compounds may be CuZnS, and / or ZnSnS, etc., may be selected as Group II-IV-VI compounds. Group I-II-IV-VI compounds may be selected from quaternary compounds, said quaternary compounds including at least one of Cu₂ZnSnS₂, Cu₂ZnSnS₄, Cu₂ZnSnSe₄, Ag₂ZnSnS₂ and mixtures thereof.

[0266] II-IV-V group compounds may be at least one of ternary compounds selected from ZnSnP, ZnSnP2, ZnSnAs2, ZnGeP2, ZnGeAs2, CdSnP2, CdGeP2 and mixtures thereof.

[0267] III-VI group compounds may include: binary compounds, such as GaS, Ga2S3, GaSe, Ga2Se3, GaTe, InTe, InS, InSe, In2S3 and / or In2Se3; ternary compounds, such as InGaS3 and / or InGaSe3; and / or any combination thereof.

[0268] Group I-III-VI compounds may be selected from: ternary compounds, including at least one of AgInS, AgInS2, CuInS, CuInS2, AgGaS2, CuGaS2, CuGaO2, AgGaO2, AgAlO2 and mixtures thereof; and quaternary compounds, such as AgInGaS2 and / or CuInGaS2.

[0269] Group III-V compounds may include at least one of the following: binary compounds (including, for example, at least one of GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, InSb, and mixtures thereof); ternary compounds (including, for example, at least one of GaNP, GaNAs, GaNSb, GaPAs, GaPSb, AlNP, AlNAs, AlNSb, AlPAs, AlPSb, InGaP, InAlP, InNP, InNAs, InNSb, InPAs, InPSb, and mixtures thereof); and quaternary compounds (including, for example, at least one of GaAlNP, GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNP, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs, InAlPSb, and mixtures thereof). Group III-V compounds may further include Group II metals. For example, InZnP and other compounds can be selected as III-II-V group compounds.

[0270] Group IV-VI compounds may include at least one of the following: binary compounds (including, for example, at least one of SnS, SnSe, SnTe, PbS, PbSe, PbTe, and mixtures thereof); ternary compounds (including, for example, at least one of SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, SnPbTe, and mixtures thereof); and quaternary compounds (including, for example, at least one of SnPbSSe, SnPbSeTe, SnPbSTe, and mixtures thereof). Group IV elements may be, for example, Si, Ge, or mixtures thereof. Group IV compounds may be binary compounds, such as SiC, SiGe, or mixtures thereof.

[0271] Each element contained in a multi-component compound (e.g., binary, ternary, and / or quaternary compounds) can exist in the particles at a homogeneous or non-homogeneous concentration. That is, the above formula can show the types of elements contained in the compound, and the element ratios in the compound can vary. For example, AgInGaS2 can represent AgInx Ga 1-x S2 (where x is a real number between 0 and 1).

[0272] Quantum dots can have a core-shell dual structure or a single structure, in which the concentration of each element contained in the respective quantum dot is uniform. For example, the material contained in the core can be different from the material contained in the shell.

[0273] The shell of a quantum dot can serve as a protective layer to prevent the core from being chemically modified to maintain its semiconductor properties, and / or as a charged layer to impart electrophoretic properties to the quantum dot. The shell can have a single layer or multiple layers. The interface between the core and the shell can have a concentration gradient, where the concentration of elements present in the shell decreases towards the core.

[0274] In some exemplary embodiments, the quantum dot may have a core-shell structure comprising a core containing the core material described above and a shell surrounding the core. Examples of the shell of the quantum dot may include oxides of metals or nonmetals, semiconductor compounds, or combinations thereof.

[0275] For example, oxides of metals or nonmetals may include binary compounds such as SiO2, Al2O3, TiO2, ZnO, MnO, Mn2O3, Mn3O4, CuO, FeO, Fe2O3, Fe3O4, CoO, Co3O4 and / or NiO; and / or ternary compounds such as MgAl2O4, CoFe2O4, NiFe2O4 and / or CoMn2O4, but the inventive concept is not limited thereto.

[0276] In addition, examples of semiconductor compounds may include CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnSeS, ZnTeS, GaAs, GaP, GaSb, HgS, HgSe, HgTe, InAs, InP, InGaP, InSb, AlAs, AlP, AlSb, etc., but the inventive concept is not limited thereto.

[0277] Each element contained in a multi-component compound (e.g., binary and ternary compounds) may exist in the particles at a uniform or non-uniform concentration. That is, the above formula may refer to the types of elements contained in the compound, and the ratio of elements in the compound may vary.

[0278] Quantum dots can have a full width at half maximum (FWHM) of about 45 nm or less, specifically about 40 nm or less, or more specifically about 30 nm or less in the emission wavelength spectrum, and can improve color purity and color reproducibility within this range. Furthermore, light emitted through quantum dots is emitted in all directions, and thus the optical viewing angle can be improved.

[0279] Furthermore, there are no particular restrictions on the type (e.g., shape) of quantum dots. For example, quantum dots can be spherical nanoparticles, pyramidal nanoparticles, multi-armed nanoparticles, cubic nanoparticles, nanotubes, nanowires, nanofibers, nanosheets, etc.

[0280] The band gap can be controlled by manipulating the size of the quantum dots or by controlling the element ratios in the quantum dot compound, and thus light with various wavelength bands can be emitted from the quantum dot emitting layer. Therefore, light-emitting elements emitting light with various wavelengths can be realized by using such quantum dots (where quantum dots of different sizes are used or the element ratios in the quantum dot compound are varied). Specifically, the size of the quantum dots and the element ratios in 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 various colors of light.

[0281] exist Figures 3 to 6 In each of the light-emitting elements (EDs) illustrated in the embodiments, an electron transport region (ETR) is provided on the emitting layer (EML). The electron transport region (ETR) may include at least one of a hole blocking layer (HBL), an electron transport layer (ETL), and an electron injection layer (EIL), but embodiments of the present invention are not limited thereto.

[0282] The electron transport region (ETR) can have a single layer made of a single material, a single layer made of multiple different materials, or a multilayer structure with multiple layers made of multiple different materials.

[0283] For example, the electron transport region (ETR) can have a single-layer structure of an electron injection layer (EIL) or an electron transport layer (ETL), or it can have a single-layer structure formed of an electron injection material and an electron transport material. Furthermore, the ETR can have a single-layer structure formed of multiple different materials, or it can have a structure in which the electron transport layer (ETL) / electron injection layer (EIL), hole blocking layer (HBL) / electron transport layer (ETL) / electron injection layer (EIL) are stacked sequentially from the emitter layer (EML), but the embodiments of the present invention are not limited thereto. The ETR can have a thickness of, for example, from about 1,000 Å to about 1,500 Å.

[0284] Various methods can be used to form the electron transport region (ETR) such as vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) method, inkjet printing, laser printing and / or laser-induced thermal imaging (LITI).

[0285] The electron transport region (ETR) may contain a compound represented by the following formula: ET-2 [Formula ET-2]

[0286] In Equation ET-2, at least one of X1 to X3 is N, and the remainder is CR. a R a It can be a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms. Ar1 to Ar3 can each independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms.

[0287] In Formula ET-2, a to c can each be an integer from 0 to 10 independently. In Formula ET-2, L1 to L3 can each be a directly linked, substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms. When a to c are each an integer of 2 or greater, L1 to L3 can each be an substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms.

[0288] The electron transport region (ETR) may comprise anthracene-based compounds. However, embodiments of the present invention are not limited thereto, and / or the ETR may comprise, for example, tris(8-hydroxyquinoline)aluminum (Alq3), 1,3,5-tris[(3-pyridyl)-benzene-3-yl]benzene, 2,4,6-tris(3'-(pyridin-3-yl)biphenyl-3-yl)-1,3,5-triazine, 2-(4-(N-phenylbenzimidazol-1-yl)phenyl)-9,10-dinaphthylanthracene, 1,3,5-tris(1-phenyl-1H-benzimidazol-2-yl)benzene (TPBi), 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), and 4,7-diphenyl-1,10-phenanthroline (Bphen). 3-(4-biphenyl)-4-phenyl-5-tert-butylphenyl-1,2,4-triazole (TAZ), 4-(naphth-1-yl)-3,5-diphenyl-4H-1,2,4-triazole (NTAZ), 2-(4-biphenyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (tBu-PBD), bis(2-methyl-8-quinoline-N1,O8)-(1,1'-biphenyl-4-oline)aluminum (BAlq), bis(benzoquinoline-10-oline)beryllium (Bebq2), 9,10-bis(naphth-2-yl)anthracene (ADN), 1,3-bis[3,5-bis(pyridin-3-yl)phenyl]benzene (BmPyPhB), or mixtures thereof.

[0289] The electron transport region (ETR) may contain at least one of the following compounds: ET1 to ET36.

[0290]

[0291] Furthermore, the electron transport region (ETR) can comprise metal halides (e.g., LiF, NaCl, CsF, RbCl, RbI, CuI, and / or KI), lanthanides (e.g., Yb), and / or co-deposition materials of metal halides and lanthanides. For example, the ETR can comprise KI:Yb, RbI:Yb, LiF:Yb, etc., as co-deposition materials. The ETR can be formed using metal oxides such as Li₂O or BaO and / or lithium 8-hydroxyquinoline (Liq), but embodiments of the present invention are not limited thereto. The ETR can also be formed from a mixture of an electron transport material and an insulating organometallic salt. The organometallic salt can be a material having a band gap of about 4 eV or greater than 4 eV. Specifically, the organometallic salt can include, for example, metal acetates, metal benzoates, metal acetoacetates, metal acetylacetonates, and / or metal stearates.

[0292] In addition to the materials described above, the electron transport region (ETR) may further comprise at least one of 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), diphenyl(4-(triphenylsilyl)phenyl)phosphine oxide (TSPO1), and 4,7-diphenyl-1,10-phenanthroline (Bphen), but embodiments of the present invention are not limited thereto.

[0293] The electron transport region (ETR) may contain a compound of the hole transport region described above in at least one of the electron injection layer (EIL), the electron transport layer (ETL), and the hole blocking layer (HBL).

[0294] When the electron transport region (ETR) includes an electron transport layer (ETL), the ETL can have a thickness of about 100 Å to about 1,000 Å, for example, about 150 Å to about 500 Å. If the thickness of the ETL meets the above range, satisfactory electron transport characteristics can be obtained without a significant increase in driving voltage. When the ETR includes an electron injection layer (EIL), the EIL can have a thickness of about 1 Å to about 100 Å, for example, about 3 Å to about 90 Å. If the thickness of the EIL meets the range described above, satisfactory electron injection characteristics can be obtained without a significant increase in driving voltage.

[0295] The second electrode EL2 is provided on the electron transport region ETR. The second electrode EL2 can be a common electrode. The second electrode EL2 can be a cathode or an anode, but the embodiments of the present invention are not limited thereto. For example, when the first electrode EL1 is an anode, the second electrode EL2 can be a cathode, and / or when the first electrode EL1 is a cathode, the second electrode EL2 can be an anode.

[0296] The second electrode EL2 can be a transmission electrode, a semi-transparent reflection electrode, and / or a reflection electrode. When the second electrode EL2 is a transmission electrode, it can be formed of a transparent metal oxide (e.g., indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), indium tin zinc oxide (ITZO), etc.).

[0297] When the second electrode EL2 is a semi-transparent reflective electrode or a reflective electrode, the second electrode EL2 may contain Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, Mo, Ti, Yb, W, Na, or compounds or mixtures thereof (e.g., AgMg, AgYb, MgYb, AgLi, and / or AgNa); or LiF / Ca, or LiF / Al. Alternatively, the second electrode EL2 may have a multilayer structure, which includes a reflective or semi-transparent reflective film formed from the materials described above, and / or a transparent conductive film formed from ITO, IZO, ZnO, ITZO, etc. For example, the second electrode EL2 may contain the metallic materials described above, a combination of at least two of the metallic materials described above, oxides of the metallic materials described above, etc.

[0298] Although not shown, the second electrode EL2 can be connected to the auxiliary electrode. If the second electrode EL2 is connected to the auxiliary electrode, the resistance of the second electrode EL2 can be reduced.

[0299] The cover layer CPL may be further disposed on the second electrode EL2 of the light-emitting element ED in at least one exemplary embodiment. The cover layer CPL may comprise multiple layers or a single layer.

[0300] In at least one exemplary embodiment, the capping layer CPL may be or include an organic layer and / or an inorganic layer. For example, when the capping layer CPL contains inorganic materials, the inorganic materials may include alkali metal compounds (e.g., LiF), alkaline earth metal compounds (e.g., MgF2), SiON, SiN. x SiO y wait.

[0301] For example, when the capping layer CPL contains organic materials, the organic materials may include 2,2'-dimethyl-N,N'-bis[(1-naphthyl)-N,N'-diphenyl]-1,1'-biphenyl-4,4'-diamine (α-NPD), NPB, TPD, m-MTDATA, Alq3, CuPc, N4,N4,N4',N4'-tetra(biphenyl-4-yl)biphenyl-4,4'-diamine (TPD15), 4,4',4''-tris(carbazole-9-yl)triphenylamine (TCTA), and / or epoxy resins, and / or acrylates (e.g., methacrylates). However, exemplary embodiments are not limited thereto, and / or the capping layer CPL may contain at least one of the following compounds P1 to P5.

[0302]

[0303] The refractive index of the capping layer CPL can be about 1.6 or greater than 1.6. Specifically, the refractive index of the capping layer CPL can be about 1.6 or greater than 1.6 relative to light in the wavelength range of about 550 nm to about 660 nm.

[0304] Figures 8 to 11 This is a cross-sectional view of the display device according to the embodiment. In the following, in reference... Figures 8 to 11 In the explanation of the display device according to the implementation scheme, the related concepts will no longer be explained. Figures 1 to 7B The overlapping content explained in the text will be explained, and / or the differences will be explained primarily.

[0305] refer to Figure 8 A display device DD-a according to at least one exemplary embodiment may include a display panel DP comprising a display element layer DP-ED, a light control layer CCL disposed on the display panel DP, and a color filter layer CFL. Figure 8 In at least one exemplary embodiment shown, the display panel DP may include a substrate layer BS, a circuit layer DP-CL provided on the substrate layer BS, and a display element layer DP-ED, wherein the display element layer DP-ED may include a light-emitting element ED.

[0306] A light-emitting element (ED) may include a first electrode EL1, a hole transport region HTR disposed on the first electrode EL1, an emitter layer EML disposed on the hole transport region HTR, an electron transport region ETR disposed on the emitter layer EML, and / or a second electrode EL2 disposed on the electron transport region ETR. Figures 3 to 6 The same structure as the light-emitting element ED can be applied to Figure 8 The structure of the light-emitting element ED is shown in the figure. Figure 8The light-emitting element (ED) shown may include at least one fused polycyclic compound of an exemplary embodiment. The light-emitting element (ED) comprising at least one fused polycyclic compound of an exemplary embodiment can exhibit high emission efficiency and long lifetime.

[0307] refer to Figure 8 The emitting layer EML can be disposed in the opening OH defined in the pixel-defining film PDL. For example, the emitting layer EML separated by the pixel-defining film PDL and provided corresponding to each light-emitting area PXA-R, PXA-G, and / or PXA-B can emit light within the same wavelength range. In the display device DD-a of at least one exemplary embodiment, the emitting layer EML can emit blue light. Unlike the illustrated configuration, in at least one exemplary embodiment, the emitting layer EML can be provided as a common layer in all light-emitting areas PXA-R, PXA-G, and / or PXA-B.

[0308] The light control layer (CCL) can be disposed on the display panel (DP). The CCL may include a light converter. The light converter emits the supplied light by converting the wavelength of the supplied light. The light converter can be quantum dots, phosphors, etc. In other words, the CCL can be a layer containing quantum dots and / or a layer containing phosphors.

[0309] The optical control layer (CCL) may include multiple optical control components CCP1, CCP2, and CCP3. The optical control components CCP1, CCP2, and / or CCP3 may be spaced apart from each other.

[0310] refer to Figure 8 The partition pattern BMP can be disposed between the light control components CCP1, CCP2 and CCP3 that are spaced apart from each other, but the embodiments of the present invention are not limited thereto. Figure 8 The example shows that the partition pattern BMP does not overlap with the light control components CCP1, CCP2 and CCP3, but at least a portion of the edges of the light control components CCP1, CCP2 and CCP3 may overlap with the partition pattern BMP.

[0311] The light-emitting element (ED) can emit light of a first color. The light control layer (CCL) may include: a first light control component CCP1 containing a first quantum dot QD1 that converts the first color light provided by the light-emitting element (ED) into a second color light; a second light control component CCP2 containing a second quantum dot QD2 that converts the first color light into a third color light; and / or a third light control component CCP3 that transmits the first color light.

[0312] In at least one exemplary embodiment, the first light control component CCP1 can provide red light as a second color light, and / or the second light control component CCP2 can provide green light as a third color light. The third light control component CCP3 can provide blue light by transmitting blue light as the first color light provided by the light-emitting element ED. For example, the first quantum dot QD1 can be a red quantum dot, and / or the second quantum dot QD2 can be a green quantum dot. The same as described above can be applied to quantum dots QD1 and QD2.

[0313] Furthermore, the light control layer CCL may further include a scatterer SP. The first light control component CCP1 may include a first quantum dot QD1 and the scatterer SP, the second light control component CCP2 may include a second quantum dot QD2 and the scatterer SP, and / or the third light control component CCP3 may not contain any quantum dots but may include the scatterer SP. The scatterer SP can be configured to scatter light generated in the light-emitting element ED.

[0314] The scatterer SP can be inorganic particles. For example, the scatterer SP can include at least one selected from TiO2, ZnO, Al2O3, SiO2, and hollow spherical silica. The scatterer SP can include at least one selected from TiO2, ZnO, Al2O3, SiO2, and hollow spherical silica, and / or can be a mixture of at least two materials selected from TiO2, ZnO, Al2O3, SiO2, and hollow spherical silica.

[0315] The first light control component CCP1, the second light control component CCP2, and / or the third light control component CCP3 may each comprise a matrix resin BR1, BR2, and / or BR3 in which quantum dots QD1 and QD2 and a scatterer SP are dispersed. In at least one exemplary embodiment, the first light control component CCP1 may comprise a first quantum dot QD1 and a scatterer SP dispersed in a first matrix resin BR1, the second light control component CCP2 may comprise a second quantum dot QD2 and a scatterer SP dispersed in a second matrix resin BR2, and / or the third light control component CCP3 may comprise a scatterer SP dispersed in a third matrix resin BR3.

[0316] The matrix resins BR1, BR2, and / or BR3 are media in which quantum dots QD1 and QD2 and scatterers SP are dispersed, and / or can be formed from various resin compositions (which may generally be referred to as binders). For example, the matrix resins BR1, BR2, and / or BR3 can be acrylic-based resins, urethane-based resins, silicone-based resins, epoxy-based resins, etc. The matrix resins BR1, BR2, and / or BR3 can be transparent resins. In at least one exemplary embodiment, the first matrix resin BR1, the second matrix resin BR2, and / or the third matrix resin BR3 can be the same as or different from each other.

[0317] The light control layer CCL may include a barrier layer BFL1. Barrier layer BFL1 serves to prevent the penetration of moisture and / or oxygen (hereinafter referred to as "moisture / oxygen"). Barrier layer BFL1 prevents light control components CCP1, CCP2, and CCP3 from being exposed to moisture / oxygen. Barrier layer BFL1 may cover light control components CCP1, CCP2, and / or CCP3. Furthermore, barrier layer BFL2 may be provided between light control components CCP1, CCP2, and / or CCP3 and the color filter layer CFL.

[0318] Barrier layers BFL1 and BFL2 may include at least one inorganic layer. That is, barrier layers BFL1 and BFL2 may contain inorganic materials. For example, barrier layers BFL1 and BFL2 may contain silicon nitrides, aluminum nitrides, zirconium nitrides, titanium nitrides, hafnium nitrides, tantalum nitrides, silicon oxides, aluminum oxides, titanium oxides, tin oxides, cerium oxides, silicon nitrides, or metal thin films that ensure transmittance. Barrier layers BFL1 and BFL2 may further include organic films. Barrier layers BFL1 and BFL2 may be formed from a single layer or multiple layers.

[0319] In at least one exemplary embodiment of the display device DD-a, the color filter layer CFL can be disposed on the light control layer CCL. For example, the color filter layer CFL can be disposed directly on the light control layer CCL. In this case, the barrier layer BFL2 can be omitted.

[0320] A color filter layer (CFL) may include filters CF1, CF2, and / or CF3. The CFL may include a first filter CF1 configured to transmit a second color of light, a second filter CF2 configured to transmit a third color of light, and / or a third filter CF3 configured to transmit a first color of light. For example, the first filter CF1 may be a red filter, the second filter CF2 may be a green filter, and / or the third filter CF3 may be a blue filter. Filters CF1, CF2, and / or CF3 may each contain a polymeric 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 / or the third filter CF3 may contain a blue pigment or dye.

[0321] The embodiments of the present invention are not limited thereto, and / or 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 formed of a transparent photosensitive resin.

[0322] Furthermore, in at least one exemplary embodiment, the first filter CF1 and the second filter CF2 may be yellow filters. The first filter CF1 and the second filter CF2 may not be separate but provided as a single filter.

[0323] Although not illustrated, the color filter layer CFL may further include a light-shielding component (not shown). The light-shielding component may be a black matrix. The light-shielding component may comprise an organic or inorganic light-shielding material containing black pigment or dye. The light-shielding component may prevent light leakage and / or may separate the boundaries between adjacent filters CF1, CF2, and / or CF3. In at least one exemplary embodiment, the light-shielding component may be formed from a blue filter.

[0324] The first to the third filters CF1, CF2 and / or CF3 can be set to correspond to the red light-emitting area PXA-R, the green light-emitting area PXA-G and / or the blue light-emitting area PXA-B, respectively.

[0325] The substrate BL can be disposed on the color filter layer CFL. The substrate BL can be a component providing the color filter layer CFL, light control layer CCL, etc., disposed therein on the surface of a substrate. The substrate BL can be a glass substrate, a metal substrate, a plastic substrate, etc. However, exemplary embodiments are not limited thereto, and / or the substrate BL can be an inorganic layer, an organic layer, and / or a composite material layer. Furthermore, unlike the illustrated configuration, in at least one exemplary embodiment, the substrate BL can be omitted.

[0326] Figure 9This is a cross-sectional view illustrating a portion of a display device according to at least one exemplary embodiment. In the display device DD-TD of at least one exemplary embodiment, the light-emitting element ED-BT may include a plurality of light-emitting structures OL-B1, OL-B2, and OL-B3. The light-emitting element ED-BT may include a first electrode EL1 and a second electrode EL2 disposed opposite to each other, and / or a plurality of light-emitting structures OL-B1, OL-B2, and OL-B3, which are stacked sequentially in the thickness direction and provided between the first electrode EL1 and the second electrode EL2. Each of the light-emitting structures OL-B1, OL-B2, and OL-B3 may include an emissive layer EML (Emitting Layer). Figure 8 ), and / or hole transport region HTR and electron transport region ETR, emitter layer EML ( Figure 8 It is disposed between the hole transport region (HTR) and the electron transport region (ETR). That is, the light-emitting element (ED-BT) included in the display device DD-TD of at least one exemplary embodiment can be a light-emitting element with a series structure, including multiple emitting layers.

[0327] At least one of the light-emitting structures OL-B1, OL-B2, and OL-B3 may contain at least one fused polycyclic compound of an exemplary embodiment. Light-emitting elements (ED-BTs) containing at least one fused polycyclic compound of an exemplary embodiment can exhibit high emission efficiency and long lifetime.

[0328] exist Figure 9 In at least one exemplary embodiment shown, all light beams emitted from the light-emitting structures OL-B1, OL-B2, and / or OL-B3 may be blue light. However, the exemplary embodiments are not limited thereto, and / or the light beams emitted from the light-emitting structures OL-B1, OL-B2, and / or OL-B3 may have different wavelength ranges from each other. For example, a light-emitting element ED-BT comprising multiple light-emitting structures OL-B1, OL-B2, and / or OL-B3 emitting light beams with different wavelength ranges from each other may emit white light.

[0329] The charge generation layers CGL1 and CGL2 can be disposed between two adjacent light-emitting structures OL-B1, OL-B2 and / or OL-B3, respectively. The charge generation layers CGL1 and CGL2 can include p-type charge generation layers and / or n-type charge generation layers.

[0330] refer to Figure 10 The display device DD-b according to at least one exemplary embodiment may include light-emitting elements ED-1, ED-2, and ED-3 in which two emitting layers are stacked. This is similar to the display device DD (e.g., according to at least one exemplary embodiment) Figure 2 Compared to (as shown in the image), Figure 10The difference in the example shown is that each of the first to third light-emitting elements ED-1, ED-2, and ED-3 includes two emitting layers stacked in the thickness direction. The two emitting layers in each of the first to third light-emitting elements ED-1, ED-2, and ED-3 can emit light with the same wavelength range.

[0331] At least one of the light-emitting elements ED-1, ED-2, and ED-3 may contain at least one fused polycyclic compound of an exemplary embodiment. At least one of the light-emitting elements ED-1, ED-2, and ED-3 containing at least one fused polycyclic compound of an exemplary embodiment may exhibit high emission efficiency and long lifespan.

[0332] The first light-emitting element ED-1 may include a first red emitting layer EML-R1 and a second red emitting layer EML-R2. The second light-emitting element ED-2 may include a first green emitting layer EML-G1 and a second green emitting layer EML-G2. Furthermore, the third light-emitting element ED-3 may include a first blue emitting layer EML-B1 and a second blue emitting layer EML-B2. An emission assist component OG may be disposed between the first red emitting layer EML-R1 and the second red emitting layer EML-R2, between the first green emitting layer EML-G1 and the second green emitting layer EML-G2, and / or between the first blue emitting layer EML-B1 and the second blue emitting layer EML-B2.

[0333] The emission assist component OG may comprise a single layer or multiple layers. The emission assist component OG may include a charge generation layer. More specifically, the emission assist component OG may include sequentially stacked electron transport regions, charge generation layers, and / or hole transport regions. The emission assist component OG may be provided as a common layer for all the first to third light-emitting elements ED-1, ED-2, and / or ED-3. However, embodiments of the inventive concept are not limited thereto, and / or the emission assist component OG may be provided by patterning in openings OH defined in the pixel defining film PDL.

[0334] The first red emission layer EML-R1, the first green emission layer EML-G1, and / or the first blue emission layer EML-B1 can be disposed between the emission auxiliary component OG and the electron transport region ETR. The second red emission layer EML-R2, the second green emission layer EML-G2, and / or the second blue emission layer EML-B2 can be disposed between the hole transport region HTR and the emission auxiliary component OG.

[0335] In other words, the first light-emitting element ED-1 may include a first electrode EL1, a hole transport region HTR, a second red emitting layer EML-R2, an emission auxiliary component OG, an electron transport region ETR, and / or a second electrode EL2, stacked sequentially. The second light-emitting element ED-2 may include a first electrode EL1, a hole transport region HTR, a second green emitting layer EML-G2, an emission auxiliary component OG, a first green emitting layer EML-G1, an electron transport region ETR, and / or a second electrode EL2, stacked sequentially. The third light-emitting element ED-3 may include a first electrode EL1, a hole transport region HTR, a second blue emitting layer EML-B2, an emission auxiliary component OG, a first blue emitting layer EML-B1, an electron transport region ETR, and / or a second electrode EL2, stacked sequentially.

[0336] An optical auxiliary layer PL may be disposed on the display element layer DP-ED. The optical auxiliary layer PL may include a polarizing layer. The optical auxiliary layer PL may be disposed on the display panel DP and control the reflected light generated in the display panel DP due to external light. Unlike the illustrated configuration, the optical auxiliary layer PL in the display device according to at least one exemplary embodiment may be omitted.

[0337] Unlike Figure 9 and Figure 10 , Figure 11 The display device DD-c shown includes 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 disposed opposite each other, and / or first to fourth light-emitting structures OL-B1, OL-B2, OL-B3, and OL-C1 stacked sequentially in the thickness direction between the first electrode EL1 and the second electrode EL2. At least one of the first to fourth light-emitting structures OL-B1, OL-B2, OL-B3, and OL-C1 may contain at least one fused polycyclic compound according to an exemplary embodiment. The light-emitting element ED-CT containing at least one fused polycyclic compound according to an exemplary embodiment can exhibit high emission efficiency and long lifespan.

[0338] Charge generation layers CGL1, CGL2, and / or CGL3 can be disposed between the first to fourth light-emitting structures OL-B1, OL-B2, OL-B3, and / or OL-C1. Of the four light-emitting structures, the first to third light-emitting structures OL-B1, OL-B2, and / or OL-B3 can emit blue light, and / or the fourth light-emitting structure OL-C1 can emit green light. However, embodiments of the present invention are not limited thereto, and / or the first to fourth light-emitting structures OL-B1, OL-B2, OL-B3, and / or OL-C1 can emit light beams in different wavelength regions.

[0339] The charge generation layers CGL1, CGL2 and / or CGL3 disposed between adjacent light-emitting structures OL-B1, OL-B2, OL-B3 and / or OL-C1 may include p-type charge generation layers and / or n-type charge generation layers.

[0340] In at least one exemplary embodiment, the electronic device may include: a display device comprising a plurality of light-emitting elements and a control component for controlling the display device. The electronic device of at least one exemplary embodiment may be a device activated by an electrical signal. The electronic device may include display devices of various embodiments. For example, the electronic device may include large-size display devices, such as televisions, monitors, and / or billboards, and / or small-to-medium-size display devices, such as personal computers, laptops, personal digital terminals, display devices for automobiles, game consoles, portable electronic devices, and / or cameras.

[0341] Figure 12 This diagram illustrates an automotive AM (Automotive Access Module) in which first to fourth display devices DD-1, DD-2, DD-3, and DD-4 are provided. At least one of the first to fourth display devices DD-1, DD-2, DD-3, and DD-4 may include components compatible with reference to... Figure 1 , Figure 2 and Figures 8 to 11 The display devices DD, DD-TD, DD-a, DD-b, and DD-c of the explained implementation scheme have the same configuration.

[0342] exist Figure 12 In this design, the vehicle is shown as an automobile AM, but this is merely an example, and the first to fourth display devices DD-1, DD-2, DD-3, and DD-4 can be arranged on other modes of transportation, such as bicycles, motorcycles, trains, ships, and airplanes. Furthermore, at least one of the first to fourth display devices DD-1, DD-2, DD-3, and DD-4, including configurations identical to those of display devices DD, DD-TD, DD-a, DD-b, and DD-c, can be incorporated into personal computers, laptops, personal digital terminals, game consoles, portable electronic devices, televisions, monitors, external billboards, etc. Moreover, these are shown as examples, and / or the display devices can be incorporated into other electronic devices without departing from the inventive concept.

[0343] At least one of the first to fourth display devices DD-1, DD-2, DD-3, and DD-4 may include a reference. Figures 3 to 6The light-emitting element ED is explained. At least one of the first to fourth display devices DD-1, DD-2, DD-3, and DD-4 may contain at least one fused polycyclic compound of an exemplary embodiment. Display devices (at least one of the first to fourth display devices DD-1, DD-2, DD-3, and DD-4) containing at least one fused polycyclic compound of an exemplary embodiment can exhibit excellent display quality.

[0344] refer to Figure 12 The vehicle AM ​​may include a steering wheel HA and a gearshift knob GR for driving the vehicle AM. Additionally, the vehicle AM ​​may include a windshield GL configured to face the driver.

[0345] The first display device DD-1 may be located in a first zone overlapping with the steering wheel HA. For example, the first display device DD-1 may be a digital cluster component displaying first information about the vehicle AM. The first information may include a first scale indicating the vehicle AM's speed, a second scale indicating engine speed (i.e., revolutions per minute (RPM)), an image indicating fuel status, etc. The first and second scales may be displayed as digital images.

[0346] The second display device DD-2 can be disposed in a second zone facing the driver's seat and overlapping with the windshield GL. The driver's seat can be a seat in which the steering wheel HA is located. For example, the second display device DD-2 can be a head-up display (HUD) displaying second information about the vehicle AM. The second display device DD-2 can be optically transparent. The second information can include a number indicating the vehicle's speed and may further include information such as the current time. Unlike the illustrated configuration, the second information of the second display device DD-2 can be projected onto the windshield GL for display.

[0347] The third display device DD-3 can be located in a third zone adjacent to the gear shifter GR. For example, the third display device DD-3 can be located between the driver's seat and the passenger seat, and can be a central information display (CID) of the vehicle for displaying third information. The passenger seat can be a seat spaced apart from the driver's seat, and the gear shifter GR is located between the passenger seat and the driver's seat. The third information may include information about traffic (e.g., navigation information), playing music or radio or video (or images), the temperature inside the vehicle's AM, etc.

[0348] The fourth display device DD-4 may be spaced apart from the steering wheel HA and gear shift GR, and / or may be located in a fourth zone adjacent to the side of the vehicle AM. For example, the fourth display device DD-4 may be a digital side mirror displaying fourth information. The fourth display device DD-4 may display images of the exterior of the vehicle AM ​​captured by a camera module CM located on the exterior of the vehicle AM.

[0349] The first to fourth information described above may be examples, and / or the first to fourth display devices DD-1, DD-2, DD-3, and DD-4 may further display information about the interior and exterior of the vehicle AM. The first to fourth information may include different information. However, embodiments of the inventive concept are not limited thereto, and / or a portion of the first to fourth information may include the same information as each other.

[0350] Figure 13 This is a perspective view illustrating an electronic device according to at least one exemplary embodiment. Figure 14 This is an exploded perspective view showing an electronic device according to at least one exemplary embodiment.

[0351] Figure 13 A portable electronic device is shown as an example of an electronic device EA. The electronic device EA can display an image IM via a display surface EA-IS. The image IM can include still images and moving images. The display surface EA-IS can be parallel to the plane defined by a first directional axis DR1 and a second directional axis DR2. Figure 13 An electronic device EA including a flat display surface EA-IS is shown, but exemplary embodiments are not limited thereto. For example, the electronic device EA may also include a curved display surface or a three-dimensional display surface. A three-dimensional display surface may also include multiple display areas indicating different orientations from each other.

[0352] The display surface EA-IS can include a display area EA-DA and a non-display area EA-NDA. The electronic device EA can display an image IM through the display area EA-DA.

[0353] The non-display area EA-NDA may not be optically transparent and may be colored. The non-display area EA-NDA may be adjacent to the display area EA-DA. The non-display area EA-NDA may surround the display area EA-DA. Therefore, the shape of the display area EA-DA can be substantially defined by the non-display area EA-NDA. However, Figure 13 The example shown is an instance, and the non-display area EA-NDA can be set to be adjacent only to one side of the display area EA-DA, and / or can be omitted.

[0354] refer to Figure 14The electronic device EA may include a display device DD. Furthermore, the electronic device EA may further include a window component WM and a housing HAU.

[0355] A window member WM can cover the entire exterior of an electronic device EA. The window member WM can include a transmissive area TA and a border area BZA. The front surface of the window member WM, including the transmissive area TA and the border area BZA, can correspond to the front surface of the electronic device EA. The transmissive area TA can correspond to... Figure 13 The display area EA-DA and / or border area BZA of the electronic device EA shown in the figure can correspond to Figure 13 The non-display area EA-NDA of the electronic device EA shown in the figure.

[0356] The transmissive region TA can be an optically transparent region. The border region BZA can be a region with a relatively lower transmittance than the transmissive region TA. The border region BZA may not be optically transparent and may be colored. The border region BZA may be adjacent to the transmissive region TA and may surround the transmissive region TA. The border region BZA may define the shape of the transmissive region TA. However, at least one exemplary embodiment is not limited to what is illustrated, and / or the border region BZA may be configured to be adjacent only to one side of the transmissive region TA, and / or a portion thereof may be omitted.

[0357] The housing HAU may comprise a material with relatively high rigidity. For example, the housing HAU may comprise a frame and / or panel made of glass, plastic, and / or metal. Multiple frames and / or panels may be provided. The housing HAU provides a receiving space. The display device DD can be housed within this receiving space and protected from external impacts.

[0358] According to the reference Figure 1 , Figure 2 and Figures 8 to 11 The described embodiment indicates that the display device DD may include the same structure as at least one of the display devices DD, DD-TD, DD-a, DD-b, and DD-c. The display device DD may include reference... Figures 3 to 6 The light-emitting element ED is described. Therefore, the electronic device EA, including the display device DD according to at least one exemplary embodiment, can exhibit excellent reliability.

[0359] The display device DD can respond to the activation of an electrical signal and provide an image IM (). Figure 13 The display device DD can be activated to display the electronic device EA in the display area EA-DA ( ). Figure 13 The image IM( is displayed in ) Figure 13 The active area DM-AA and the surrounding area DM-NAA can be defined in the display device DD. The active area DM-AA can be... Figure 13The illustrated display area EA-DA overlaps, and the surrounding area DM-NAA can be aligned with it. Figure 13 The non-display area EA-NDA overlaps as shown in the example.

[0360] The active region DM-AA can be a region activated in response to an electrical signal. The surrounding region DM-NAA can be a region located adjacent to at least one side of the active region DM-AA. The active region DM-AA can include a non-emitting region NPXA and emitting regions PXA-R, PXA-G, and / or PXA-B. The surrounding region DM-NAA can be configured to cover the active region DM-AA. However, exemplary embodiments are not limited thereto, and / or, unlike the example, a portion of the surrounding region DM-NAA may be omitted. In the surrounding region DM-NAA, drive circuitry, drive lines, etc., for driving the active region DM-AA can be provided.

[0361] According to at least one example implementation scheme ( Figure 1 , Figure 2 and / or Figures 8 to 11 The display devices DD, DD-TD, DD-a, DD-b, and / or DD-c described above can be applied to various electronic devices. An electronic device EA according to at least one exemplary embodiment may include the display devices DD-TD, DD-a, DD-b, and / or DD-c described above. Figure 1 , Figure 2 and / or Figures 8 to 11 ), and / or may further include, in addition to display devices DD-TD, DD-a, DD-b and / or DD-c ( Figure 1 , Figure 2 and / or Figures 8 to 11 A module or device with an additional function besides ( ).

[0362] Figure 15 This is a block diagram of an electronic device according to at least one exemplary embodiment. (Reference) Figure 15 The electronic device EA may include a display module 11, a processor 12, a memory 13 and / or a power module 14.

[0363] The processor 12 may include at least one of a central processing unit (CPU), an application processor (AP), a graphics processing unit (GPU), a communication processor (CP), an image signal processor (ISP), and a controller.

[0364] The memory 13 can store the data information required for the operation of the processor 12 or the display module 11. When the processor 12 executes the application stored in the memory 13, image data signals and / or input control signals are transmitted to the display module 11, and / or the display module 11 can process the received signals and output image information through the display screen.

[0365] The power module 14 may include a power supply module, such as a power adapter or battery device, and / or a power conversion module that converts the power supplied by the power supply module to generate the power required for the operation of the electronic device EA.

[0366] At least one of the components of an electronic device EA may be included in a display device according to some exemplary embodiments. Furthermore, some individual modules that are functionally included in one module of the components of the electronic device EA may be included in the display device, and / or some other modules may be provided separately from the display device. For example, the display device may include display module 11 and / or processor 12, while memory 13 and power module 14 may be provided as other devices within the electronic device EA, rather than the display device.

[0367] Figure 16 Schematic diagrams of electronic devices according to various embodiments are shown. (Reference) Figure 16 The various electronic devices used in the display device according to the implementation scheme may include not only image display electronic devices, such as smartphones EA_1a, tablet computers EA_1b, laptop computers EA_1c, TVs EA_1d and / or desktop monitors EA_1e, but also wearable electronic devices, such as smart glasses EA_2a, head-mounted displays EA_2b and / or smartwatches EA_2c, and / or vehicle electronic devices EA_3 that include display modules, such as car dashboards, center panels, central information displays (CID) set in the dashboard, and / or rearview mirror displays, etc.

[0368] In the following, fused polycyclic compounds according to at least one exemplary embodiment of the present invention and light-emitting elements according to at least one exemplary embodiment will be described in detail with reference to embodiments and comparative examples. Furthermore, the embodiments shown below are merely illustrative to aid in understanding the inventive concept, and / or the scope of the inventive concept is not limited thereto.

[0369] [Example]

[0370] 1. Synthesis of a fused polycyclic compound according to one embodiment

[0371] The method for synthesizing fused polycyclic compounds according to this embodiment will be explained by illustrating the synthesis methods of fused polycyclic compounds B-2, B-14, B-17, B-24, B-25, C-2, C-16, C-18, C-20, C-30, D-15, and E-1. Furthermore, the methods for synthesizing fused polycyclic compounds explained below are examples, and therefore the method for synthesizing compounds according to this embodiment is not limited to the following examples.

[0372] (1) Synthesis of fused polycyclic compound B-2

[0373] According to one embodiment, the fused polycyclic compound B-2 can be synthesized by, for example, the following steps.

[0374] [Synthesis of compound B-2-10]

[0375] Compound B-2-8 (300 mmol), compound B-2-9 (300 mmol), tBuONa (450 mmol), bis(dibenzylacetone)palladium(0) (“Pd(dba)2”) (15 mmol) and (9,9-dimethyl-9 H Xanthos(-4,5-diyl)bis(diphenylphosphine) (“XantPhos”) (30 mmol) was added to a three-necked flask, which was purged with argon (Ar), followed by the addition of 1000 mL of toluene. The resulting mixture was stirred at approximately 80 °C for approximately 8 hours. Water was added to the reaction mixture, and the organic layer was extracted with toluene. The extracted organic layer was dried over magnesium sulfate, and the solvent was removed by distillation. The crude product was purified by silica gel column chromatography (using a mixed solvent of hexane and toluene) to give 285 mmol of compound B-2-10 (approximately 95% yield). The purified product was identified as having a molecular weight of approximately 245 by rapid atomic impact mass spectrometry (FABMS).

[0376] [Synthesis of compound B-2-6]

[0377] Compounds B-2-11 (300 mmol), B-2-12 (300 mmol), and K₂CO₃ (600 mmol) were added to a three-necked flask, which was then purged with Ar. 200 mL of N-methyl-2-pyrrolidone (NMP) was added, and the mixture was stirred at approximately 150 °C for approximately 24 hours. Water was added to the reaction mixture, and the organic layer was extracted with toluene. The obtained organic layer was dried over magnesium sulfate, and the solvent was removed by distillation. The crude product was purified by silica gel column chromatography (using a mixed solvent of hexane and toluene) to give 258 mmol of compound B-2-13 (yield approximately 86%). The purified product was identified as having a molecular weight of approximately 344 by FABMS.

[0378] Compounds B-2-13 (258 mmol), B-2-10 (258 mmol), tBuONa (387 mmol), Pd(dba)2 (13 mmol), and XantPhos (26 mmol) were added to a three-necked flask, which was then purged with Ar. 800 mL of toluene was added, and the mixture was stirred at approximately 80 °C for approximately 8 hours. Water was added to the reaction mixture, and the organic layer was extracted with toluene. The obtained organic layer was dried over magnesium sulfate, and the solvent was removed by distillation. The crude product was purified by silica gel column chromatography (using a mixed solvent of hexane and toluene) to obtain approximately 227 mmol of compound B-2-6 (yield approximately 88%). The purified product was identified as having a molecular weight of approximately 508 by FABMS.

[0379] [Synthesis of compound B-2]

[0380] Compound B-2-1 (200 mmol), compound B-2-2 (410 mmol), tBuONa (600 mmol), Pd(dba)2 (10 mmol), and tri-tert-butylphosphine tetrafluoroborate (“[(tBu)3PH]BF4”) (20 mmol) were added to a three-necked flask, which was purged with Ar, followed by the addition of 1000 mL of toluene. The resulting mixture was stirred at approximately 90 °C for approximately 7 hours. Water was added to the reaction mixture, and the organic layer was extracted with toluene. The extracted organic layer was dried over magnesium sulfate, and the solvent was removed by distillation. The crude extract was purified by silica gel column chromatography (using a mixed solvent of hexane and toluene) and recrystallization (using a mixed solvent of ethanol and toluene) to give approximately 170 mmol of compound B-2-3 (yield approximately 85%). The purified product was identified as having a molecular weight of approximately 620 by FABMS.

[0381] Compounds B-2-3 (150 mmol), B-2-4 (750 mmol), K₂CO₃ (900 mmol), and CuI (165 mmol) were added to a three-necked flask, the flask was purged with Ar, and the resulting mixture was stirred at approximately 210 °C for approximately 72 hours. Water was added to the reaction mixture, and the organic layer was extracted with toluene. The extracted organic layer was dried over magnesium sulfate, and the solvent was removed by distillation. The crude product was purified by silica gel column chromatography (using a mixed solvent of hexane and toluene) and recrystallization (using a mixed solvent of ethanol and toluene) to give approximately 62 mmol of compound B-2-5 (yield approximately 41%). The purified product was identified as having a molecular weight of approximately 740 by FABMS.

[0382] Compounds B-2-5 (62 mmol), B-2-6 (310 mmol), K₂CO₃ (372 mmol), and CuI (68 mmol) were added to a three-necked flask, the flask was purged with Ar, and the resulting mixture was stirred at approximately 210 °C for approximately 72 hours. Water was added to the reaction mixture, and the organic layer was extracted with toluene. The extracted organic layer was dried over magnesium sulfate, and the solvent was removed by distillation. The crude product was purified by silica gel column chromatography (using a mixed solvent of hexane and toluene) and recrystallization (using a mixed solvent of ethanol and toluene) to give approximately 41 mmol of compound B-2-7 (yield approximately 66%). The purified product was identified as having a molecular weight of approximately 1167 by FABMS.

[0383] Compound B-2-7 (41 mmol) was added to a three-necked flask, which was then purged with Ar. 21 mL of 1,2-dichlorobenzene (“ODCB”) was added and dissolved, followed by the addition of BI3 (164 mmol). The mixture was stirred at approximately 140 °C for approximately 3 hours. The reaction mixture was dispersed and washed with a large amount of acetonitrile, and then filtered to collect the solid. The crude product was purified by silica gel column chromatography (using a mixed solvent of hexane / toluene) and recrystallization (using a mixed solvent of ethanol / toluene) to give approximately 20 mmol of compound B-2 (yield approximately 49%). The purified product was identified as having a molecular weight of approximately 1183 as determined by FABMS.

[0384] (2) Synthesis of compound B-14

[0385] The fused polycyclic compound B-14 according to at least one exemplary embodiment can be synthesized by, for example, the following steps.

[0386] [Synthesis of compound B-14-11]

[0387] Compounds B-14-12 (300 mmol), B-14-13 (300 mmol), tBuONa (450 mmol), Pd(dba)2 (15 mmol), and XantPhos (30 mmol) were added to a three-necked flask, which was then purged with Ar. 1000 mL of toluene was added, and the mixture was stirred at approximately 80 °C for approximately 8 hours. Water was added to the reaction mixture, and the organic layer was extracted with toluene. The extracted organic layer was dried over magnesium sulfate, and the solvent was removed by distillation. The crude product was purified by silica gel column chromatography (using a mixed solvent of hexane and toluene) to give 264 mmol of compound B-14-11 (yield approximately 88%). The purified product was identified as having a molecular weight of approximately 287 by FABMS.

[0388] [Synthesis of compound B-14-6]

[0389] Compounds B-14-8 (300 mmol), B-14-9 (300 mmol), and K₂CO₃ (600 mmol) were added to a three-necked flask, which was then purged with Ar. 200 mL of NMP was added, and the mixture was stirred at approximately 150 °C for approximately 24 hours. Water was added to the reaction mixture, and the organic layer was extracted with toluene. The extracted organic layer was dried over magnesium sulfate, and the solvent was removed by distillation. The crude product was purified by silica gel column chromatography (using a mixed solvent of hexane and toluene) to give approximately 240 mmol of compound B-14-10 (yield approximately 80%). The purified product was identified as having a molecular weight of approximately 467 by FABMS.

[0390] Compounds B-14-10 (240 mmol), B-14-11 (240 mmol), tBuONa (360 mmol), Pd(dba)2 (12 mmol), and XantPhos (24 mmol) were added to a three-necked flask, and the flask was purged with Ar. Then, 800 mL of toluene was added, and the mixture was stirred at approximately 80 °C for approximately 8 hours. Water was added to the reaction mixture, and the organic layer was extracted with toluene. The extracted organic layer was dried over magnesium sulfate, and the solvent was removed by distillation. The crude product was purified by silica gel column chromatography (using a mixed solvent of hexane and toluene) to give approximately 228 mmol of compound B-14-6 (yield approximately 95%). The purified product was identified as having a molecular weight of approximately 626 by FABMS.

[0391] [Synthesis of compound B-14]

[0392] Compounds B-14-1 (200 mmol), B-14-2 (410 mmol), tBuONa (600 mmol), Pd(dba)2 (10 mmol), and [(tBu)3PH]BF4 (20 mmol) were added to a three-necked flask, which was then purged with Ar. 1000 mL of toluene was added, and the mixture was stirred at approximately 90 °C for approximately 5 hours. Water was added to the reaction mixture, and the organic layer was extracted with toluene. The extracted organic layer was dried over magnesium sulfate, and the solvent was removed by distillation. The crude product was purified by silica gel column chromatography (using a mixed solvent of hexane and toluene) and recrystallization (using a mixed solvent of ethanol and toluene) to give approximately 162 mmol of compound B-14-3 (yield approximately 81%). The purified product was identified as having a molecular weight of approximately 620 by FABMS.

[0393] Compounds B-14-3 (162 mmol), B-14-4 (810 mmol), K₂CO₃ (972 mmol), and CuI (178 mmol) were added to a three-necked flask, purged with Ar, and the resulting mixture was stirred at approximately 210 °C for approximately 72 hours. Water was added to the reaction mixture, and the organic layer was extracted with toluene. The extracted organic layer was dried over magnesium sulfate, and the solvent was removed by distillation. The crude product was purified by silica gel column chromatography (using a mixed solvent of hexane and toluene) and recrystallization (using a mixed solvent of ethanol and toluene) to give approximately 87 mmol of compound B-14-5 (yield approximately 54%). The purified product was identified as having a molecular weight of approximately 813 by FABMS.

[0394] Compounds B-14-5 (87 mmol), B-14-6 (228 mmol), K₂CO₃ (522 mmol), and CuI (96 mmol) were added to a three-necked flask, the flask was purged with Ar, and the resulting mixture was stirred at approximately 210 °C for approximately 72 hours. Water was added to the reaction mixture, and the organic layer was extracted with toluene. The extracted organic layer was dried over magnesium sulfate, and the solvent was removed by distillation. The crude product was purified by silica gel column chromatography (using a mixed solvent of hexane and toluene) and recrystallization (using a mixed solvent of ethanol and toluene) to give approximately 44 mmol of compound B-14-7 (yield approximately 51%). The purified product was identified as having a molecular weight of approximately 1358 by FABMS.

[0395] Compound B-14-7 (44 mmol) was added to a three-necked flask, which was then purged with Ar. 22 mL of ODCB was added and dissolved, followed by the addition of BI3 (176 mmol). The resulting mixture was stirred at approximately 140 °C for approximately 3 hours. The reaction mixture was dispersed and washed with a large amount of acetonitrile, and then filtered to collect the solid. The crude product was purified by silica gel column chromatography (using a mixed solvent of hexane / dichloromethane) and recrystallization (using a mixed solvent of ethanol / toluene) to give approximately 10 mmol of compound B-14 (yield approximately 23%). The purified product was identified as having a molecular weight of approximately 1374 by FABMS.

[0396] (3) Synthesis of compound B-17

[0397] The fused polycyclic compound B-17 according to at least one exemplary embodiment can be synthesized by, for example, the following steps.

[0398] [Synthesis of compound B-17-9]

[0399] Compounds B-17-10 (300 mmol), B-17-11 (300 mmol), tBuONa (450 mmol), Pd(dba)2 (15 mmol), and XantPhos (30 mmol) were added to a three-necked flask, which was then purged with Ar. 1000 mL of toluene was added, and the mixture was stirred at approximately 80 °C for approximately 8 hours. Water was added to the reaction mixture, and the organic layer was extracted with toluene. The extracted organic layer was dried over magnesium sulfate, and the solvent was removed by distillation. The crude product was purified by silica gel column chromatography (using a mixed solvent of hexane and toluene) to obtain 276 mmol of compound B-17-9 (yield approximately 92%). The purified product was identified as having a molecular weight of approximately 321 by FABMS.

[0400] [Synthesis of compound B-17-3]

[0401] Compounds B-14-8 (300 mmol), B-17-7 (300 mmol), and K₂CO₃ (600 mmol) were added to a three-necked flask, which was then purged with Ar. 200 mL of NMP was added, and the mixture was stirred at approximately 150 °C for approximately 24 hours. Water was added to the reaction mixture, and the organic layer was extracted with toluene. The extracted organic layer was dried over magnesium sulfate, and the solvent was removed by distillation. The crude product was purified by silica gel column chromatography (using a mixed solvent of hexane and toluene) to give approximately 249 mmol of compound B-17-8 (yield approximately 83%). The purified product was identified as having a molecular weight of approximately 451 by FABMS.

[0402] Compounds B-17-8 (249 mmol), B-17-9 (249 mmol), tBuONa (373 mmol), Pd(dba)2 (12 mmol), and XantPhos (24 mmol) were added to a three-necked flask, which was then purged with Ar. 800 mL of toluene was added, and the mixture was stirred at approximately 80 °C for approximately 8 hours. Water was added to the reaction mixture, and the organic layer was extracted with toluene. The extracted organic layer was dried over magnesium sulfate, and the solvent was removed by distillation. The crude product was purified by silica gel column chromatography (using a mixed solvent of hexane and toluene) to give approximately 224 mmol of compound B-17-3 (yield approximately 90%). The purified product was identified as having a molecular weight of approximately 644 by FABMS.

[0403] [Synthesis of Compound B-17]

[0404] Compounds B-14-3 (150 mmol), B-17-1 (750 mmol), K₂CO₃ (900 mmol), and CuI (165 mmol) were added to a three-necked flask, purged with Ar, and the resulting mixture was stirred at approximately 210 °C for approximately 72 hours. Water was added to the reaction mixture, and the organic layer was extracted with toluene. The extracted organic layer was dried over magnesium sulfate, and the solvent was removed by distillation. The crude product was purified by silica gel column chromatography (using a mixed solvent of hexane and toluene) and recrystallization (using a mixed solvent of ethanol and toluene) to give approximately 68 mmol of compound B-17-2 (yield approximately 45%). The purified product was identified as having a molecular weight of approximately 731 by FABMS.

[0405] Compounds B-17-2 (68 mmol), B-17-3 (224 mmol), K₂CO₃ (408 mmol), and CuI (75 mmol) were added to a three-necked flask, purged with Ar, and the resulting mixture was stirred at approximately 210 °C for approximately 72 hours. Water was added to the reaction mixture, and the organic layer was extracted with toluene. The extracted organic layer was dried over magnesium sulfate, and the solvent was removed by distillation. The crude product was purified by silica gel column chromatography (using a mixed solvent of hexane and toluene) and recrystallization (using a mixed solvent of ethanol and toluene) to give approximately 41 mmol of compound B-17-4 (yield approximately 61%). The purified product was identified as having a molecular weight of approximately 1295 by FABMS.

[0406] Compound B-17-4 (41 mmol) was added to a three-necked flask, which was then purged with Ar. 21 mL of ODCB was added and dissolved, followed by the addition of BI3 (164 mmol). The resulting mixture was stirred at approximately 140 °C for approximately 3 hours. The reaction mixture was dispersed and washed with a large amount of acetonitrile, and then filtered to collect the solid. The crude product was purified by silica gel column chromatography (using a mixed solvent of hexane / dichloromethane) and recrystallization (using a mixed solvent of ethanol / toluene) to give approximately 22 mmol of compound B-17-5 (yield approximately 53%). The purified product was identified as having a molecular weight of approximately 1310 as determined by FABMS.

[0407] Compounds B-17-5 (22 mmol), B-17-6 (44 mmol), Pd(dba)2 (2 mmol), 2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl (SPhos) (4 mmol), and tBuONa (66 mmol) were added to a three-necked flask, which was purged with Ar, followed by the addition of 22 mL of toluene. The mixture was stirred at approximately 110 °C for approximately 8 hours. Water was added to the reaction mixture, and the organic layer was extracted with toluene. The extracted organic layer was dried over magnesium sulfate, and the solvent was removed by distillation. The crude product was purified by silica gel column chromatography (using a mixed solvent of hexane and toluene) and recrystallization (using a mixed solvent of ethanol and toluene) to give approximately 15 mmol of compound B-17 (yield approximately 70%). The purified product was identified as having a molecular weight of approximately 1441 by FABMS.

[0408] (4) Synthesis of compound B-24

[0409] The fused polycyclic compound B-24 according to at least one exemplary embodiment can be synthesized by, for example, the following steps.

[0410] [Synthesis of compound B-24-3]

[0411] Compounds B-14-12 (300 mmol), B-24-6 (300 mmol), tBuONa (450 mmol), Pd(dba)2 (15 mmol), and XantPhos (30 mmol) were added to a three-necked flask, which was then purged with Ar. 1000 mL of toluene was added, and the mixture was stirred at approximately 80 °C for approximately 8 hours. Water was added to the reaction mixture, and the organic layer was extracted with toluene. The extracted organic layer was dried over magnesium sulfate, and the solvent was removed by distillation. The crude product was purified by silica gel column chromatography (using a mixed solvent of hexane and toluene) to give approximately 273 mmol of compound B-24-7 (yield approximately 91%). The purified product was identified as having a molecular weight of approximately 279 by FABMS.

[0412] Compounds B-24-7 (273 mmol), B-17-8 (273 mmol), tBuONa (410 mmol), Pd(dba)2 (14 mmol), and XantPhos (28 mmol) were added to a three-necked flask, which was then purged with Ar. 910 mL of toluene was added, and the mixture was stirred at approximately 80 °C for approximately 8 hours. Water was added to the reaction mixture, and the organic layer was extracted with toluene. The extracted organic layer was dried over magnesium sulfate, and the solvent was removed by distillation. The crude product was purified by silica gel column chromatography (using a mixed solvent of hexane and toluene) to obtain approximately 246 mmol of compound B-24-3 (yield approximately 90%). The purified product was identified as having a molecular weight of approximately 602 by FABMS.

[0413] [Synthesis of compound B-24]

[0414] Compounds B-14-3 (150 mmol), B-24-1 (750 mmol), K₂CO₃ (900 mmol), and CuI (165 mmol) were added to a three-necked flask, purged with Ar, and the resulting mixture was stirred at approximately 210 °C for approximately 72 hours. Water was added to the reaction mixture, and the organic layer was extracted with toluene. The extracted organic layer was dried over magnesium sulfate, and the solvent was removed by distillation. The crude product was purified by silica gel column chromatography (using a mixed solvent of hexane and toluene) and recrystallization (using a mixed solvent of ethanol and toluene) to give approximately 78 mmol of compound B-24-2 (yield approximately 52%). The purified product was identified as having a molecular weight of approximately 803 by FABMS.

[0415] Compounds B-24-2 (78 mmol), B-24-3 (246 mmol), K₂CO₃ (468 mmol), and CuI (86 mmol) were added to a three-necked flask, the flask was purged with Ar, and the resulting mixture was stirred at approximately 210 °C for approximately 72 hours. Water was added to the reaction mixture, and the organic layer was extracted with toluene. The extracted organic layer was dried over magnesium sulfate and the solvent was removed by distillation. The crude product was purified by silica gel column chromatography (using a mixed solvent of hexane and toluene) and recrystallization (using a mixed solvent of ethanol and toluene) to give approximately 43 mmol of compound B-24-4 (yield approximately 55%). The purified product was identified as having a molecular weight of approximately 1325 by FABMS.

[0416] Compound B-24-4 (43 mmol) was added to a three-necked flask, which was then purged with Ar. 22 ml of ODCB was added and dissolved, followed by the addition of BI3 (172 mmol). The resulting mixture was stirred at approximately 140 °C for approximately 3 hours. The reaction mixture was dispersed and washed with a large amount of acetonitrile, and then filtered and the solid was collected. The crude product was purified by silica gel column chromatography (using a mixed solvent of hexane / dichloromethane) and recrystallization (using a mixed solvent of ethanol / toluene) to give approximately 11 mmol of compound B-24-5 (yield approximately 25%). The purified product was identified as having a molecular weight of approximately 1340 by FABMS.

[0417] Compounds B-24-5 (11 mmol), B-17-6 (22 mmol), Pd(dba)2 (1 mmol), SPhos (2 mmol), and tBuONa (33 mmol) were added to a three-necked flask, which was then purged with Ar. 11 mL of toluene was added, and the mixture was stirred at approximately 110 °C for approximately 8 hours. Water was added to the reaction mixture, and the organic layer was extracted with toluene. The extracted organic layer was dried over magnesium sulfate, and the solvent was removed by distillation. The crude product was purified by silica gel column chromatography (using a mixed solvent of hexane and toluene) and recrystallization (using a mixed solvent of ethanol and toluene) to give approximately 8 mmol of compound B-24 (yield approximately 72%). The purified product was identified as having a molecular weight of approximately 1471 by FABMS.

[0418] (5) Synthesis of compound B-25

[0419] The fused polycyclic compound B-25 according to at least one exemplary embodiment can be synthesized by, for example, the following steps.

[0420] [Synthesis of compound B-25-7]

[0421] Compounds B-14-12 (300 mmol), B-25-6 (300 mmol), tBuONa (450 mmol), Pd(dba)2 (15 mmol), and XantPhos (30 mmol) were added to a three-necked flask, which was then purged with Ar. 1000 mL of toluene was added, and the mixture was stirred at approximately 80 °C for approximately 8 hours. Water was added to the reaction mixture, and the organic layer was extracted with toluene. The extracted organic layer was dried over magnesium sulfate, and the solvent was removed by distillation. The crude product was purified by silica gel column chromatography (using a mixed solvent of hexane and toluene) to give approximately 282 mmol of compound B-25-7 (yield approximately 94%). The purified product was identified as having a molecular weight of approximately 321 by FABMS.

[0422] [Synthesis of compound B-25-3]

[0423] Compounds B-14-8 (300 mmol), B-25-8 (300 mmol), and K₂CO₃ (600 mmol) were added to a three-necked flask, which was then purged with Ar. 200 mL of NMP was added, and the mixture was stirred at approximately 150 °C for approximately 24 hours. Water was added to the reaction mixture, and the organic layer was extracted with toluene. The extracted organic layer was dried over magnesium sulfate, and the solvent was removed by distillation. The crude product was purified by silica gel column chromatography (using a mixed solvent of hexane and toluene) to give approximately 243 mmol of compound B-25-9 (yield approximately 81%). The purified product was identified as having a molecular weight of approximately 409 by FABMS.

[0424] Compounds B-25-9 (243 mmol), B-25-7 (243 mmol), tBuONa (364 mmol), Pd(dba)2 (12 mmol), and XantPhos (24 mmol) were added to a three-necked flask, purged with Ar, and then 800 mL of toluene was added. The resulting mixture was stirred at approximately 80 °C for approximately 8 hours. Water was added to the reaction mixture, and the organic layer was extracted with toluene. The extracted organic layer was dried over magnesium sulfate, and the solvent was removed by distillation. The crude product was purified by silica gel column chromatography (using a mixed solvent of hexane and toluene) to give approximately 221 mmol of compound B-25-3 (yield approximately 91%). The purified product was identified as having a molecular weight of approximately 602 by FABMS.

[0425] [Synthesis of Compound B-25]

[0426] Compounds B-14-3 (150 mmol), B-25-1 (750 mmol), K₂CO₃ (900 mmol), and CuI (165 mmol) were added to a three-necked flask, purged with Ar, and the resulting mixture was stirred at approximately 210 °C for approximately 72 hours. Water was added to the reaction mixture, and the organic layer was extracted with toluene. The extracted organic layer was dried over magnesium sulfate, and the solvent was removed by distillation. The crude product was purified by silica gel column chromatography (using a mixed solvent of hexane and toluene) and recrystallization (using a mixed solvent of ethanol and toluene) to give approximately 69 mmol of compound B-25-2 (yield approximately 46%). The purified product was identified as having a molecular weight of approximately 771 by FABMS.

[0427] Compounds B-25-2 (69 mmol), B-25-3 (221 mmol), K₂CO₃ (414 mmol), and CuI (76 mmol) were added to a three-necked flask, the flask was purged with Ar, and the mixture was stirred at approximately 210 °C for approximately 72 hours. Water was added to the reaction mixture, and the organic layer was extracted with toluene. The extracted organic layer was dried over magnesium sulfate and the solvent was removed by distillation. The crude product was purified by silica gel column chromatography (using a mixed solvent of hexane and toluene) and recrystallization (using a mixed solvent of ethanol and toluene) to give approximately 41 mmol of compound B-25-4 (yield approximately 59%). The purified product was identified as having a molecular weight of approximately 1293 by FABMS.

[0428] Compound B-25-4 (41 mmol) was added to a three-necked flask, which was then purged with Ar. 21 mL of ODCB was added and dissolved, followed by the addition of BI3 (164 mmol). The resulting mixture was stirred at approximately 140 °C for approximately 3 hours. The reaction mixture was dispersed and washed with a large amount of acetonitrile, and then filtered and the solid was collected. The crude product was purified by silica gel column chromatography (using a mixed solvent of hexane / dichloromethane) and recrystallization (using a mixed solvent of ethanol / toluene) to obtain approximately 21 mmol of compound B-25-5 (yield approximately 50%). The purified product was identified as having a molecular weight of approximately 1308 as determined by FABMS.

[0429] Compounds B-25-5 (21 mmol), B-17-6 (42 mmol), Pd(dba)2 (2 mmol), SPhos (4 mmol), and tBuONa (63 mmol) were added to a three-necked flask, which was then purged with Ar. 21 mL of toluene was added, and the mixture was stirred at approximately 110 °C for approximately 8 hours. Water was added to the reaction mixture, and the organic layer was extracted with toluene. The extracted organic layer was dried over magnesium sulfate, and the solvent was removed by distillation. The crude product was purified by silica gel column chromatography (using a mixed solvent of hexane and toluene) and recrystallization (using a mixed solvent of ethanol and toluene) to give approximately 16 mmol of compound B-25 (yield approximately 77%). The purified product was identified as having a molecular weight of approximately 1439 by FABMS.

[0430] (6) Synthesis of compound C-2

[0431] The fused polycyclic compound C-2 according to at least one exemplary embodiment can be synthesized by, for example, the following steps.

[0432] [Synthesis of compound C-2-4]

[0433] Compounds B-14-10 (600 mmol), B-17-7 (300 mmol), K₂CO₃ (1800 mmol), CuI (330 mmol), and 40 mL of ODCB were added to a three-necked flask, which was purged with Ar, and the resulting mixture was stirred at approximately 170 °C for approximately 8 hours. Water was added to the reaction mixture, and the organic layer was extracted with toluene. The extracted organic layer was dried over magnesium sulfate, and the solvent was removed by distillation. The crude product was purified by silica gel column chromatography (using a mixed solvent of hexane and toluene) and recrystallization (using a mixed solvent of ethanol and toluene) to give approximately 240 mmol of compound C-2-4 (yield approximately 80%). The purified product was identified as having a molecular weight of approximately 509 by FABMS.

[0434] [Synthesis of compound C-2]

[0435] Compounds B-14-1 (200 mmol), B-14-12 (410 mmol), tBuONa (600 mmol), Pd(dba)2 (10 mmol), and [(tBu)3PH]BF4 (20 mmol) were added to a three-necked flask, which was then purged with Ar. 1000 mL of toluene was added, and the mixture was stirred at approximately 90 °C for approximately 5 hours. Water was added to the reaction mixture, and the organic layer was extracted with toluene. The extracted organic layer was dried over magnesium sulfate, and the solvent was removed by distillation. The crude product was purified by silica gel column chromatography (using a mixed solvent of hexane and toluene) to give approximately 186 mmol of compound C-2-1 (yield approximately 93%). The purified product was identified as having a molecular weight of approximately 468 by FABMS.

[0436] Compounds C-2-1 (186 mmol), C-2-2 (169 mmol), tBuONa (186 mmol), Pd(dba)2 (8 mmol), and [(tBu)3PH]BF4 (16 mmol) were added to a three-necked flask, which was then purged with Ar. 845 mL of toluene was added, and the mixture was stirred at approximately 90 °C for approximately 5 hours. Water was added to the reaction mixture, and the organic layer was extracted with toluene. The extracted organic layer was dried over magnesium sulfate, and the solvent was removed by distillation. The crude product was purified by silica gel column chromatography (using a mixed solvent of hexane and toluene) to give approximately 130 mmol of compound C-2-3 (yield approximately 77%). The purified product was identified as having a molecular weight of approximately 600 by FABMS.

[0437] Compounds C-2-3 (130 mmol), C-2-4 (143 mmol), tBuONa (260 mmol), Pd(dba)2 (6 mmol), and [(tBu)3PH]BF4 (12 mmol) were added to a three-necked flask, which was then purged with Ar. 650 mL of toluene was added, and the mixture was stirred at approximately 90 °C for approximately 7 hours. Water was added to the reaction mixture, and the organic layer was extracted with toluene. The extracted organic layer was dried over magnesium sulfate, and the solvent was removed by distillation. The crude product was purified by silica gel column chromatography (using a mixed solvent of hexane and toluene) to give approximately 104 mmol of compound C-2-5 (yield approximately 80%). The purified product was identified as having a molecular weight of approximately 1029 by FABMS.

[0438] Compound C-2-5 (104 mmol) was added to a three-necked flask, which was then purged with Ar. 52 mL of ODCB was added and dissolved, followed by the addition of BI3 (416 mmol). The resulting mixture was stirred at approximately 140 °C for approximately 3 hours. The reaction mixture was dispersed and washed with a large amount of acetonitrile, and then filtered and the solid was collected. The crude product was purified by silica gel column chromatography (using a mixed solvent of hexane / dichloromethane) and recrystallization (using a mixed solvent of ethanol / toluene) to give approximately 8 mmol of compound C-2 (yield approximately 8%). The purified product was identified as having a molecular weight of approximately 1044 as determined by FABMS.

[0439] (7) Synthesis of compound C-16

[0440] The fused polycyclic compound C-16 according to at least one exemplary embodiment can be synthesized by, for example, the following steps.

[0441] [Synthesis of compound C-16-1]

[0442] Compounds C-16-5 (300 mmol), B-17-7 (630 mmol), and Cs₂CO₃ (900 mmol) were added to a three-necked flask, which was then purged with Ar. 500 mL of NMP was added, and the mixture was stirred at approximately 165 °C for about 3 hours. Water was added to the reaction mixture, and the organic layer was extracted with toluene. The extracted organic layer was dried over magnesium sulfate, and the solvent was removed by distillation. The crude product was purified by silica gel column chromatography (using a mixed solvent of hexane and toluene) to give approximately 240 mmol of compound C-16-1 (yield approximately 80%). The purified product was identified as having a molecular weight of approximately 540 by FABMS.

[0443] [Synthesis of compound C-16]

[0444] Compound B-14-3 (50 mmol), compound C-16-1 (240 mmol), K₂CO₃ (300 mmol), and CuI (55 mmol) were added to a three-necked flask, the flask was purged with Ar, and the mixture was stirred at approximately 210 °C for approximately 72 hours. Water was added to the reaction mixture, and the organic layer was extracted with toluene. The extracted organic layer was dried over magnesium sulfate and the solvent was removed by distillation. The crude product was purified by silica gel column chromatography (using a mixed solvent of hexane and toluene) and recrystallization (using a mixed solvent of ethanol and toluene) to give approximately 28 mmol of compound C-16-2 (yield approximately 55%). The purified product was identified as having a molecular weight of approximately 1033 by FABMS.

[0445] Compounds C-16-2 (8 mmol), C-16-3 (40 mmol), K₂CO₃ (48 mmol), and CuI (9 mmol) were added to a three-necked flask, the flask was purged with Ar, and the resulting mixture was stirred at approximately 210 °C for approximately 48 hours. Water was added to the reaction mixture, and the organic layer was extracted with toluene. The extracted organic layer was dried over magnesium sulfate, and the solvent was removed by distillation. The crude product was purified by silica gel column chromatography (using a mixed solvent of hexane and toluene) and recrystallization (using a mixed solvent of ethanol and toluene) to give approximately 6 mmol of compound C-16-4 (yield approximately 80%). The purified product was identified as having a molecular weight of approximately 1139 by FABMS.

[0446] Compound C-16-4 (6 mmol) was added to a three-necked flask, which was then purged with Ar. 57 mL of ODCB was added and dissolved, followed by the addition of BI3 (27 mmol). The resulting mixture was stirred at approximately 140 °C for approximately 3 hours. The reaction mixture was dispersed and washed with a large amount of acetonitrile, and then filtered and the solid was collected. The crude product was purified by silica gel column chromatography (using a mixed solvent of hexane / dichloromethane) and recrystallization (using a mixed solvent of ethanol / toluene) to give approximately 3 mmol of compound C-16 (yield approximately 43%). The purified product was identified as having a molecular weight of approximately 1155 as determined by FABMS.

[0447] (8) Synthesis of compound C-18

[0448] The fused polycyclic compound C-18 according to at least one exemplary embodiment can be synthesized by, for example, the following steps.

[0449]

[0450] Compound C-16-2 (8 mmol), compound C-18-1 (54 mmol), K₂CO₃ (46 mmol), and CuI (8 mmol) were added to a three-necked flask, the flask was purged with Ar, and the resulting mixture was stirred at approximately 210 °C for approximately 38 hours. Water was added to the reaction mixture, and the organic layer was extracted with toluene. The extracted organic layer was dried over magnesium sulfate, and the solvent was removed by distillation. The crude product was purified by silica gel column chromatography (using a mixed solvent of hexane and toluene) and recrystallization (using a mixed solvent of ethanol and toluene) to give approximately 7 mmol of compound C-18-2 (yield approximately 88%). The purified product was identified as having a molecular weight of approximately 1165 as determined by FABMS.

[0451] Compound C-18-2 (7 mmol) was added to a three-necked flask, which was then purged with Ar. 57 mL of ODCB was added and dissolved, followed by the addition of BI3 (27 mmol). The resulting mixture was stirred at approximately 140 °C for approximately 3 hours. The reaction mixture was dispersed and washed with a large amount of acetonitrile, and then filtered and the solid was collected. The crude product was purified by silica gel column chromatography (using a mixed solvent of hexane / dichloromethane) and recrystallization (using a mixed solvent of ethanol / toluene) to give approximately 3 mmol of compound C-18 (yield approximately 47%). The purified product was identified as having a molecular weight of approximately 1181 as determined by FABMS.

[0452] (9) Synthesis of compound C-20

[0453] The fused polycyclic compound C-20 according to at least one exemplary embodiment can be synthesized by, for example, the following steps.

[0454]

[0455] Compound C-16-2 (8 mmol), compound C-20-1 (40 mmol), K₂CO₃ (48 mmol), and CuI (9 mmol) were added to a three-necked flask, the flask was purged with Ar, and the resulting mixture was stirred at approximately 210 °C for approximately 48 hours. Water was added to the reaction mixture, and the organic layer was extracted with toluene. The extracted organic layer was dried over magnesium sulfate, and the solvent was removed by distillation. The crude product was purified by silica gel column chromatography (using a mixed solvent of hexane and toluene) and recrystallization (using a mixed solvent of ethanol and toluene) to give approximately 7 mmol of compound C-20-2 (yield approximately 89%). The purified product was identified as having a molecular weight of approximately 1276 by FABMS.

[0456] Compound C-20-2 (7 mmol) was added to a three-necked flask, which was then purged with Ar. 56 mL of ODCB was added and dissolved, followed by the addition of BI3 (21 mmol). The resulting mixture was stirred at approximately 140 °C for approximately 3 hours. The reaction mixture was dispersed and washed with a large amount of acetonitrile, and then filtered and the solid was collected. The crude product was purified by silica gel column chromatography (using a mixed solvent of hexane / dichloromethane) and recrystallization (using a mixed solvent of ethanol / toluene) to give approximately 3 mmol of compound C-20 (yield approximately 42%). The purified product was identified as having a molecular weight of approximately 1292 as determined by FABMS.

[0457] (10) Synthesis of compound C-30

[0458] The fused polycyclic compound C-30 according to at least one exemplary embodiment can be synthesized by, for example, the following steps.

[0459]

[0460] Compound C-16-2 (8 mmol), compound C-30-1 (40 mmol), K₂CO₃ (48 mmol), and CuI (9 mmol) were added to a three-necked flask, the flask was purged with Ar, and the resulting mixture was stirred at approximately 210 °C for approximately 38 hours. Water was added to the reaction mixture, and the organic layer was extracted with toluene. The extracted organic layer was dried over magnesium sulfate, and the solvent was removed by distillation. The crude product was purified by silica gel column chromatography (using a mixed solvent of hexane and toluene) and recrystallization (using a mixed solvent of ethanol and toluene) to give approximately 7 mmol of compound C-30-2 (yield approximately 87%). The purified product was identified as having a molecular weight of approximately 1201 by FABMS.

[0461] Compound C-30-2 (7 mmol) was added to a three-necked flask, which was then purged with Ar. 56 mL of ODCB was added and dissolved, followed by the addition of BI3 (21 mmol). The resulting mixture was stirred at approximately 140 °C for approximately 3 hours. The reaction mixture was dispersed and washed with a large amount of acetonitrile, and then filtered and the solid was collected. The crude product was purified by silica gel column chromatography (using a mixed solvent of hexane / dichloromethane) and recrystallization (using a mixed solvent of ethanol / toluene) to give approximately 3 mmol of compound C-30 (yield approximately 46%). The purified product was identified as having a molecular weight of approximately 1217 as determined by FABMS.

[0462] (11) Synthesis of compound D-15

[0463] The fused polycyclic compound D-15 according to at least one exemplary embodiment can be synthesized by, for example, the following steps.

[0464]

[0465] Compound C-16-1 (281 mmol), KOH (843 mmol), Pd(dba)2 (2 mmol), and tBuXPhos (8 mmol) were added to a three-necked flask, which was then purged with Ar. 60 mL of dioxane and 60 mL of H2O were added, and the mixture was stirred at approximately 100 °C for approximately 6 hours. 10 vol% hydrochloric acid was added to the reaction mixture, and the organic layer was extracted with toluene and dried over magnesium sulfate. The solvent was removed by distillation. The crude product was purified by silica gel column chromatography (using a mixed solvent of hexane and toluene) to give approximately 132 mmol of compound D-15-1 (yield approximately 47%). The purified product was identified as having a molecular weight of approximately 430 by FABMS.

[0466] Compounds D-15-1 (132 mmol), D-15-2 (132 mmol), and K₂CO₃ (396 mmol) were added to a three-necked flask, which was then purged with Ar. 400 mL of NMP was added, and the mixture was stirred at approximately 165 °C for about 5 hours. Water was added to the reaction mixture, and the organic layer was extracted with toluene. The extracted organic layer was dried over magnesium sulfate, and the solvent was removed by distillation. The crude product was purified by silica gel column chromatography (using a mixed solvent of hexane and toluene) to give approximately 119 mmol of compound D-15-3 (yield approximately 90%). The purified product was identified as having a molecular weight of approximately 641 by FABMS.

[0467] Compounds D-15-3 (119 mmol), B-14-2 (131 mmol), tBuONa (179 mmol), Pd(dba)2 (6 mmol), and XantPhos (12 mmol) were added to a three-necked flask, which was then purged with Ar. 1000 mL of toluene was added, and the mixture was stirred at approximately 90 °C for approximately 6 hours. Water was added to the reaction mixture, and the organic layer was extracted with toluene. The extracted organic layer was dried over magnesium sulfate, and the solvent was removed by distillation. The crude product was purified by silica gel column chromatography (using a mixed solvent of hexane and toluene) to give approximately 108 mmol of compound D-15-4 (yield approximately 91%). The purified product was identified as having a molecular weight of approximately 806 by FABMS.

[0468] Compounds D-15-4 (108 mmol), D-15-5 (540 mmol), K₂CO₃ (648 mmol), and CuI (119 mmol) were added to a three-necked flask, purged with Ar, and the resulting mixture was stirred at approximately 210 °C for approximately 72 hours. Water was added to the reaction mixture, and the organic layer was extracted with toluene. The extracted organic layer was dried over magnesium sulfate, and the solvent was removed by distillation. The crude product was purified by silica gel column chromatography (using a mixed solvent of hexane and toluene) and recrystallization (using a mixed solvent of ethanol and toluene) to give approximately 66 mmol of compound D-15-6 (yield approximately 61%). The purified product was identified as having a molecular weight of approximately 964 by FABMS.

[0469] Compound D-15-6 (66 mmol) was added to a three-necked flask, which was then purged with Ar. 198 mL of ODCB was added and dissolved, followed by the addition of BI3 (198 mmol). The resulting mixture was stirred at approximately 140 °C for approximately 3 hours. The reaction mixture was dispersed and washed with a large amount of acetonitrile, and then filtered and the solid was collected. The crude product was purified by silica gel column chromatography (using a mixed solvent of hexane / dichloromethane) and recrystallization (using a mixed solvent of ethanol / toluene) to give approximately 9 mmol of compound D-15 (yield approximately 14%). The purified product was identified as having a molecular weight of approximately 979 as determined by FABMS.

[0470] (12) Synthesis of compound E-1

[0471] The fused polycyclic compound E-1 according to at least one exemplary embodiment can be synthesized by, for example, the following steps.

[0472]

[0473] Compounds D-15-2 (300 mmol), E-1-1 (300 mmol), and K₂CO₃ (600 mmol) were added to a three-necked flask, which was then purged with Ar. 200 mL of NMP was added, and the mixture was stirred at approximately 150 °C for about 8 hours. Water was added to the reaction mixture, and the organic layer was extracted with toluene. The extracted organic layer was dried over magnesium sulfate, and the solvent was removed by distillation. The crude product was purified by silica gel column chromatography (using a mixed solvent of hexane and toluene) to give approximately 234 mmol of compound E-1-2 (yield approximately 78%). The purified product was identified as having a molecular weight of approximately 361 by FABMS.

[0474] Compound E-1-2 (234 mmol), KOH (702 mmol), Pd(dba)2 (2 mmol), and 2,2-di-tert-butylphosphino-2',4',6'-triisopropylbiphenyl (“tBuXPhos”) (8 mmol) were added to a three-necked flask, which was then purged with Ar. 60 mL of dioxane and 60 mL of H2O were added, and the mixture was stirred at approximately 100 °C for approximately 6 hours. 10 vol% hydrochloric acid was added to the reaction mixture, and the organic layer was extracted with toluene. The extracted organic layer was dried over magnesium sulfate, and the solvent was removed by distillation. The crude product was purified by silica gel column chromatography (using a mixed solvent of hexane and toluene) to give approximately 105 mmol of compound E-1-3 (yield approximately 45%). The purified product was identified as having a molecular weight of approximately 298 by FABMS.

[0475] Compound E-1-3 (105 mmol), compound B-17-3 (315 mmol), K₂CO₃ (630 mmol), CuI (116 mmol), and 14 mL of ODCB were added to a three-necked flask, which was purged with Ar, and the resulting mixture was stirred at approximately 170 °C for approximately 8 hours. Water was added to the reaction mixture, and the organic layer was extracted with toluene. The extracted organic layer was dried over magnesium sulfate, and the solvent was removed by distillation. The crude product was purified by silica gel column chromatography (using a mixed solvent of hexane and toluene) to give approximately 51 mmol of compound E-1-4 (yield approximately 49%). The purified product was identified as having a molecular weight of approximately 862 by FABMS.

[0476] Compound E-1-4 (51 mmol) was added to a three-necked flask, which was then purged with Ar. 26 mL of ODCB was added and dissolved, followed by the addition of BI3 (204 mmol). The resulting mixture was stirred at approximately 140 °C for approximately 3 hours. The reaction mixture was dispersed and washed with a large amount of acetonitrile, and then filtered and the solid was collected. The crude product was purified by silica gel column chromatography (using a mixed solvent of hexane / dichloromethane) and recrystallization (using a mixed solvent of ethanol / toluene) to give approximately 3 mmol of compound E-1 (yield approximately 6%). The purified product was identified as having a molecular weight of approximately 877 by FABMS.

[0477] 2. Evaluation of compounds

[0478] The compounds of the Examples and the Comparative Examples were evaluated, and the evaluation results are listed in Table 1 below. Compounds B-2, B-14, B-17, B-24, B-25, C-2, C-16, C-18, C-20, C-30, D-15, and E-1 (which are fused polycyclic compounds according to the Examples) were evaluated as Examples. Comparative Examples X1 to X11 were evaluated as Comparative Examples.

[0479] <Example Compounds>

[0480] <Comparative Compounds>

[0481] Table 1 shows the evaluation results of the luminescence properties. A 20 wt% doped film was deposited using PPF as a matrix on a quartz glass substrate. Its fluorescence emission spectrum was observed using a JASCO V-670 spectrometer, and the λ was confirmed from the spectrum. max Fluorescence quantum efficiency was measured using a JASCOILF-835 integrating sphere system.

[0482]

[0483] [Table 1]

[0484] Referring to Table 1, it can be seen that the compounds in the examples and the comparative examples each have a λ of about 450 nm to about 470 nm. max It can be seen that the example compounds exhibit higher fluorescence quantum efficiencies than comparative example compounds X1, X2, and X4 to X11. Example compounds B-2, B-14, B-17, B-24, B-25, C-2, C-16, C-18, C-20, C-30, D-15, and E-1 are fused polycyclic compounds according to the examples and contain a first substituent and a second substituent bonded to a nine-ring fused ring system (i.e., a core structure). The first substituent corresponds to R in Formula 1 as previously described. a1 and R a2 At least one of the following, and is a substituted or unsubstituted aryl group having 6 to 60 cyclic carbon atoms. The second substituent corresponds to R in Formula 1 as previously described.b1 To R b4 At least one of the following, and is an electron-donating substituent. Therefore, it can be seen that fused polycyclic compounds comprising a first substituent and a second substituent bonded to a nine-ring fused ring system according to at least one exemplary embodiment exhibit excellent fluorescence quantum efficiency.

[0485] Comparative compounds X1 to X3 each comprise a nine-ring fused ring system but do not contain a first substituent or a second substituent. Comparative compound X4 comprises a nine-ring fused ring system and a first substituent but does not contain a second substituent. Comparative compounds X5 to X9 and comparative compound X11 each comprise a nine-ring fused ring system and a second substituent but do not contain a first substituent. Comparative compound X10 corresponds to R in Formula 1 as previously described. b2 and R b3 They are bonded together to form a moiety represented by formula RB, but the first substituent is a phenyl group substituted with a methyl group. In the fused polycyclic compound represented by formula 1 according to at least one exemplary embodiment, when R b2 and R b3 When the compounds bond together to form a moiety represented by the formula RB, the first substituent is an unsubstituted aryl group. Therefore, comparative example compounds X1, X2, and X4 to X11 each exhibit relatively low fluorescence quantum efficiencies.

[0486] 3. Manufacturing and evaluation of light-emitting elements

[0487] (1) Manufacturing of light-emitting elements

[0488] Light-emitting elements comprising fused polycyclic compounds according to the embodiments or comparative examples in their emitting layers were manufactured using the following methods. Light-emitting elements according to Examples 1 to 12 were manufactured using compounds B-2, B-14, B-17, B-24, B-25, C-2, C-16, C-18, C-20, C-30, D-15, and E-1 (which are fused polycyclic compounds according to the embodiments) as dopant materials for the emitting layer. Light-emitting elements according to Comparative Examples 1 to 11 were manufactured using comparative example compounds X1 to X11 as dopant materials for the emitting layer.

[0489] An ITO layer with a thickness of approximately 1500 Å was patterned on a glass substrate as the first electrode, and the glass substrate was then cleaned with ultrapure water and subjected to UV ozone treatment for approximately 10 minutes. Subsequently, a hole injection layer with a thickness of approximately 100 Å was formed by HAT-CN, and a hole transport layer with a thickness of approximately 400 Å was formed by α-NPD.

[0490] Then, an electron blocking layer with a thickness of about 50 Å is formed from 3,3'-bis(9H-carbazole-9-yl)-1,1'-biphenyl (mCBP), and an emission layer is formed from the example compound or comparative example compound and mCBP in a weight ratio of about 1:99. An emission layer with a thickness of about 200 Å is formed. An electron transport layer with a thickness of about 300 Å is formed on the emission layer from TPBi, and an electron injection layer with a thickness of about 5 Å is formed from LiF. Subsequently, a second electrode with a thickness of about 1000 Å is formed from aluminum (Al). The hole injection layer, hole transport layer, electron blocking layer, emission layer, electron transport layer, electron injection layer, and second electrode are formed using a vacuum deposition system.

[0491] (2) Evaluation of light-emitting elements

[0492] The light-emitting elements according to the embodiments and comparative examples were evaluated, and the evaluation results are listed in Table 2 below. The voltage and current density of the light-emitting elements were measured using a source meter (manufactured by Keithley Instruments, 2400 series), and the luminance and external quantum efficiency (EQE) were measured using an external quantum efficiency measurement system C9920-12 manufactured by Hamamatsu Photonics. The time taken for the luminance to decrease from 100% to 50% of its initial luminance was measured, and the relative value of the measurement time to 100% for the light-emitting element according to Comparative Example 1 is listed as lifetime (LT). 50 ).

[0493] [Table 2]

[0494] Referring to Table 2, it can be seen that the light-emitting elements according to Examples 1 to 12 each emit light with a wavelength of approximately 460 nm. It can also be seen that the light-emitting elements according to Examples 1 to 12 each have a longer lifespan than the light-emitting elements according to Comparative Examples 1 to 11. Furthermore, it can be seen that the light-emitting elements according to Examples 1 to 12 each exhibit higher external quantum efficiency and a longer lifespan than the light-emitting elements according to Comparative Examples 1, 2, and 4 to 11. The light-emitting elements according to Examples 1 to 12 respectively comprise compounds B-2, B-14, B-17, B-24, B-25, C-2, C-16, C-18, C-20, C-30, D-15, and E-1, and compounds B-2, B-14, B-17, B-24, B-25, C-2, C-16, C-18, C-20, C-30, D-15, and E-1 are fused polycyclic compounds according to the examples. Compounds B-2, B-14, B-17, B-24, B-25, C-2, C-16, C-18, C-20, C-30, D-15, and E-1 each contain a first substituent and a second substituent bonded to a nine-ring fused ring system. Therefore, it can be seen that the light-emitting element comprising a fused polycyclic compound according to at least one exemplary embodiment exhibits high emission efficiency and long lifetime.

[0495] Gaussian calculations of the molecular orbitals of Examples B-14, B-17, B-24, C-2, C-18, and E-1 demonstrated that each of these compounds possesses a charge transfer type in which the HOMO and LUMO distributions are separated. In Comparative Examples X1 and X2, the HOMO and LUMO distributions are separated, but neither the first nor the second substituent is present, and therefore the charge transfer (“CT”) characteristic is weak. In Comparative Example X3, the HOMO and LUMO distributions are not completely separated, and therefore Comparative Example X3 has an incomplete CT. Therefore, even when electron-donating substituents are bonded to Comparative Example X3, the HOMO and LUMO slightly overlap, ΔEST The efficiency and roll-off suppression are not expected to improve as a result. The light-emitting elements according to Comparative Examples 1 to 3 respectively comprise comparative example compounds X1 to X3. Comparative example compounds X1 to X3 each do not contain a first substituent and a second substituent at a predetermined position, and are therefore different from the fused polycyclic compounds according to at least one exemplary embodiment. Therefore, the light-emitting elements according to Comparative Examples 1 to 3 each exhibit relatively low external quantum efficiency and short lifetime.

[0496] Comparative compound X4 does not contain a second substituent at a predetermined position, and therefore exhibits weaker CT characteristics than the compounds of the examples, and is not expected to have DET suppression and boron atom protection as steric effects. The light-emitting element according to Comparative Example 4 contains comparative compound X4. Therefore, the light-emitting element according to Comparative Example 4 exhibits relatively low external quantum efficiency and short lifetime.

[0497] The light-emitting elements according to Comparative Examples 5 to 8 each comprise comparative example compounds X5 to X8. Comparative example compounds X5 to X8 do not contain a first substituent at the para position relative to the boron atom, and are therefore different from the fused polycyclic compounds according to the examples. In comparative example compound X6, the aryl group is bonded at the meta position relative to the boron atom, LUMO is not extended, and therefore comparative example compound X6 has weaker CT characteristics than the compounds of the examples. Therefore, the light-emitting elements according to Comparative Examples 5 to 8 each exhibit relatively low external quantum efficiency and short lifetime.

[0498] The light-emitting elements according to Comparative Examples 9 and 11 respectively comprise comparative example compound X9 and comparative example compound X11. Comparative example compound X9 and comparative example compound X11 each comprise a nine-ring fused ring system and a second substituent, but do not contain a first substituent. Therefore, the light-emitting elements according to Comparative Examples 9 and 11 exhibit relatively low external quantum efficiency and short lifetime.

[0499] The light-emitting element according to Comparative Example 10 comprises Comparative Example Compound X10. Comparative Example Compound X10 corresponds to R in Formula 1 described above. b2 and R b3 They bond to each other to form a part represented by formula RB, but the first substituent is a phenyl group replaced by a methyl group. Therefore, the light-emitting element according to Comparative Example 10 exhibits relatively low external quantum efficiency and short lifetime.

[0500] According to some exemplary embodiments, an electronic device may include a light-emitting element, and the light-emitting element may comprise a fused polycyclic compound. The fused polycyclic compound according to at least one exemplary embodiment may comprise a nine-ring fused ring system, a first substituent, and a second substituent. The nine-ring fused ring system may be a core structure and may contain four heteroatoms and two boron atoms as cyclic atoms. The first substituent is bonded at the para position relative to the boron atom (which is a cyclic atom) and may be a substituted or unsubstituted aryl group. In the nine-ring fused ring system, the second substituent is bonded to another cyclic group not bonded to the first substituent and may be an electron-donating substituent. Therefore, in the fused polycyclic compound according to at least one exemplary embodiment, RISC is accelerated, and the fused polycyclic compound according to at least one exemplary embodiment may contribute to improved emission efficiency and lifetime.

[0501] The light-emitting element according to at least one exemplary embodiment and the electronic device including the light-emitting element contain a fused polycyclic compound according to at least one exemplary embodiment, and thus can exhibit high emission efficiency and long lifespan characteristics.

[0502] Fused polycyclic compounds according to at least one exemplary embodiment can contribute to the improvement of emission efficiency and long service life of light-emitting elements.

[0503] Thus far, although some exemplary embodiments of the inventive concept have been described with reference to preferred embodiments, those skilled in the art or those with ordinary knowledge in the art will understand that various modifications and changes can be made without departing from the technical idea or features of the inventive concept described in the claims.

[0504] Therefore, the technical scope of this invention is not limited to the content set forth in the detailed description of this specification, but should be defined by the claims.

Claims

1. Fused polycyclic compounds represented by Formula 1: [Formula 1] in, In Equation 1, X 1 To X 4 Each is independently O, S, or NR. y1 , R y1 It is a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, or represented by Formula 2. R 1 To R 6 and R b1 To R b4 Each of the following is independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted amine group, a substituted or unsubstituted oxygen 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 60 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, wherein R 1 To R 6 and R b1 To R b4 Optionally bonded to adjacent groups to form a ring, R 7 To R 10 R a1 and R a2 Each of the following is independently a hydrogen atom, a deuterium atom, a cyano group, a halogen atom, 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 60 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms. R a1 and R a2 At least one of them is a substituted or unsubstituted aryl group having 6 to 60 cyclic carbon atoms. R b1 To R b4 At least one of them is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms or an electron-donating group. The electron-donating group is a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted alkylamine group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted arylamine group, or a substituted or unsubstituted carbazole group. [Equation 2] In Equation 2, n1 is an integer between 0 and 5. R y2 It is a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms. Indicates the connection position. When R b2 and R b3 When they bond together, R b2 and R b3 Form the part represented by the formula RB, and R a1 and R a2 At least one of the components is the unsubstituted aryl group having 6 to 60 cyclic carbon atoms. [RB style] In equation RB, b2 corresponds to R b2 The position, and b3 corresponds to R. b3 Location, and The fused polycyclic compound includes a chemical structure in which hydrogen atoms are optionally replaced by deuterium atoms.

2. The fused polycyclic compound of claim 1, wherein the fused polycyclic compound is represented by at least one of formulas 1-A1 to 1-A6: [Equation 1-A1] [Equation 1-A2] [Equation 1-A3] [Equation 1-A4] [Formula 1-A5] [Formula 1-A6] in, In equations 1-A1 to 1-A6, X 11 To X 14 Each is either O or S independently. n2 to n5 are each an independent integer from 0 to 5. R y11 To R y14 Each of the following is independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, and R 1 To R 6 R b1 To R b4 R 7 To R 10 R a1 and R a2 Same as defined in Equation 1.

3. The fused polycyclic compound of claim 1, wherein, R b1 To R b4 At least one of them includes a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted isopropyl group, a substituted or unsubstituted n-butyl group, a substituted or unsubstituted tert-butyl group, a substituted or unsubstituted cyclopentyl group, a substituted or unsubstituted cyclohexyl group, a substituted or unsubstituted methoxy group, a substituted or unsubstituted propoxy group, a substituted or unsubstituted isopropoxy group, a substituted or unsubstituted tert-butoxy group, a substituted or unsubstituted cyclohexoxy group, a substituted or unsubstituted phenoxy group, a substituted or unsubstituted dimethylamine group, a substituted or unsubstituted ethylamine group, a substituted or unsubstituted N-methylphenylamine group, a substituted or unsubstituted N-propylphenylamine group, a substituted or unsubstituted diphenylamine group, a substituted or unsubstituted methylthio group, a substituted or unsubstituted isopropylthio group, a substituted or unsubstituted propylthio group, a substituted or unsubstituted tert-butylthio group, a substituted or unsubstituted phenylthio group, or a substituted or unsubstituted carbazole group.

4. The fused polycyclic compound of claim 1, wherein, In Equation 1, R b1 To R b4 At least one of Rb-1 to Rb-45 is represented by: , in, Indicates the connection location.

5. The fused polycyclic compound of claim 1, wherein in formula 1, R a1 and R a2 The at least one mentioned in the text is represented by at least one of Ra-1 to Ra-5: in, This indicates the connection position, and in Ra-2, D is a deuterium atom.

6. The fused polycyclic compound of claim 1, wherein, In Equation 1, R a1 and R a2 The remainder are hydrogen atoms, deuterium atoms, cyano groups, substituted or unsubstituted diphenylamine groups, or substituted or unsubstituted carbazole groups.

7. The fused polycyclic compound of claim 1, wherein R y1 At least one of the following representations: Y1-1 to Y1-18 ， in, Indicates the connection location.

8. The fused polycyclic compound of claim 1, wherein the fused polycyclic compound is represented by at least one of the compounds in group 1: [Compound Group 1] in, In compound group 1, D is a deuterium atom.

9. Light-emitting elements, including: First electrode; The second electrode on the first electrode; as well as An emission layer is provided between the first electrode and the second electrode, the emission layer comprising a first compound, and The first compound is a fused polycyclic compound according to any one of claims 1 to 8.

10. The light-emitting element of claim 9, wherein the emitting layer further comprises at least one of a second compound represented by formula HT-1, a third compound represented by formula ET-1, and a fourth compound represented by formula D-1: [Formula HT-1] in, In formula HT-1, A1 through A8 are each independently either N or CR. 51 , L1 is a linearly bonded, substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms. Y a It is a direct-connect key, CR 52 R 53 or SiR 54 R 55 , Ar1 is a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms. R 51 To R 55 Each of the following 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 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 cyclic carbon atoms, wherein R 51 To R 55 Optionally bonded to adjacent groups to form a ring, [Formula ET-1] In Equation ET-1, At least one of X1 to X3 is N, and the remainder of X1 to X3 is CR. 56 , R 56 It 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 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 cyclic carbon atoms. b1 to b3 are each an independent integer from 0 to 10. Ar2 to Ar4 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 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms. L2 to L4 are each independently a straight-linked, substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms. [Formula D-1] In equation D-1, Q1 through Q4 are each independently either C or N. C1 through C4 are each independently a substituted or unsubstituted hydrocarbon ring having 5 to 30 cyclic carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heterocycle having 2 to 30 cyclic carbon atoms. L 11 To L 13 Each is an independent direct-connect key. , , , The following are considered as separate categories: substituted or unsubstituted divalent alkyl groups having 1 to 20 carbon atoms; substituted or unsubstituted aryl groups having 6 to 30 cyclic carbon atoms; or substituted or unsubstituted heteroaryl groups having 2 to 30 cyclic carbon atoms, and in L... 11 To L 13 middle, This refers to the portion connected to C1 through C4. b11 to b13 are each independently 0 or 1. R 61 To R 66 Each of the following 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 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 cyclic carbon atoms. d1 to d4 are each an independent integer from 0 to 4.

11. Electronic devices, including display devices configured to provide images, in, The display device includes a substrate layer, a circuit layer disposed on the substrate layer, and a display element layer disposed on the circuit layer and including light-emitting elements. The light-emitting element includes a first electrode, a second electrode on the first electrode, and an emitting layer between the first electrode and the second electrode. The emitter layer comprises a fused polycyclic compound according to any one of claims 1 to 8.

12. The electronic device of claim 11, further comprising: At least one of the light control layer and the color filter layer, The light control layer comprises quantum dots, and The color filter layer contains at least one of pigments and dyes.

13. The electronic device of claim 11, further comprising: At least one of a processor, memory, and power module.

Images