Light emitting device, fused polycyclic compound for the same, and electronic device including the same

Abstract

A light-emitting element of one embodiment comprises a first electrode, a second electrode disposed on the first electrode, and at least one functional layer disposed between the first electrode and the second electrode and comprising a first compound represented by the following chemical formula 1. [Chemical Formula 1]

Description

Technology Field

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

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

[0003] In applying organic light-emitting diodes to display devices, there is a demand for lower driving voltage, higher luminous efficiency, and longer lifespan of the devices, and there is a continuous demand for the development of materials for organic light-emitting diodes that can stably realize these requirements.

[0004] In particular, recently, to realize high-efficiency organic electroluminescent devices, technologies for phosphorescent emission using the energy of the triplet state or fluorescence emission using the phenomenon of triplet-triplet annihilation (TTA), in which a singlet exciton is generated by the collision of a triplet exciton, are being developed, and the development of thermally activated delayed fluorescence (TADF) materials using the delayed fluorescence phenomenon is underway. The problem to be solved

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

[0006] Another objective of the present invention is to provide a condensed polycyclic compound capable of improving the device lifespan of a light-emitting device.

[0007] Another objective of the present invention is to provide an electronic device having excellent display quality, including a light-emitting element with an improved lifespan. means of solving the problem

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

[0009] [Chemical Formula 1]

[0010]

[0011] In the above Chemical Formula 1, X is O, S, or NR 12 and, R1 to R 11 Each is independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a hydroxyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cyclic aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted cyclic heteroaryl group having 2 to 30 carbon atoms, and R 12 Is A substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heteroaryl group having 2 to 30 carbon atoms. , However, R 12 If is a substituted or unsubstituted ring-forming heteroaryl group having 2 to 30 carbon atoms, R 12 It does not contain two or more of any one of dibenzofuran moiety, dibenzothiophen moiety, and carbazole moiety, and Ar is a substituent represented by the following chemical formula 2, and

[0012] [Chemical Formula 2]

[0013]

[0014] In the above chemical formula 2, R x1to R x4 Each is independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a hydroxyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cyclic aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted cyclic heteroaryl group having 2 to 30 carbon atoms, and R x1 to R x3 At least one of them is a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heteroaryl group having 2 to 30 carbon atoms, and R y1 to R y4, and R z1 to R z5 Each is independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a hydroxyl group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thio group, a substituted or unsubstituted boron group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heteroaryl group having 2 to 30 carbon atoms, or forms a ring by bonding to an adjacent group, and is the position connected to the above chemical formula 1.

[0015] The above at least one functional layer comprises a light-emitting layer, a hole transport region disposed between the first electrode and the light-emitting layer, and an electron transport region disposed between the light-emitting layer and the second electrode, and the light-emitting layer may comprise the first compound.

[0016] The above-mentioned light-emitting layer can emit delayed fluorescence with a light-emitting center wavelength of 430 nm or more and 490 nm or less.

[0017] R x1 to Rx4 Each is independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cyclic aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted cyclic heteroaryl group having 2 to 30 carbon atoms, and R x1 to R x3 At least one of them may be a substituent represented by any one of the following chemical formulas 3-1 to 3-4.

[0018] [Chemical Formula 3-1]

[0019]

[0020] [Chemical Formula 3-2]

[0021]

[0022] [Chemical Formula 3-3]

[0023]

[0024] [Chemical Formula 3-4]

[0025]

[0026] In the above chemical formulas 3-1 to 3-4, Y1 to Y7 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cyclic aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted cyclic heteroaryl group having 2 to 30 carbon atoms; n1 and n3 are each independently integers from 0 to 5; n2, n5, and n7 are each independently integers from 0 to 4; and n4 and n6 are each independently integers from 0 to 3. may be a position connected to the above chemical formula 2.

[0027] R x1 to R x3Any one of them is a substituent represented by any one of the above chemical formulas 3-1 to 3-4, and R x1 to R x3 The remainder of the group may be hydrogen atoms, deuterium atoms, or unsubstituted t-butyl groups.

[0028] The substituent represented by the above chemical formula 2 may be represented by any one of the following chemical formulas 2-1 to 2-3.

[0029] [Chemical Formula 2-1]

[0030]

[0031] [Chemical Formula 2-2]

[0032]

[0033] [Chemical Formula 2-3]

[0034]

[0035] In the above chemical formulas 2-1 to 2-3, Z1 to Z6 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; m1, m4, and m6 are each independently an integer from 0 to 4; m2 is an integer from 0 to 5; m3 and m5 are each independently an integer from 0 to 3; and R x1 to R x4 It may be the same as defined in Chemical Formula 2 above.

[0036] The first compound represented by the above chemical formula 1 may include at least one of the compounds of the following compound group 1.

[0037] A condensed polycyclic compound according to one embodiment of the present invention is represented by the above chemical formula 1.

[0038] A display device according to one embodiment of the present invention comprises a base layer, a circuit layer disposed on the base layer, and a display element layer disposed on the circuit layer and including a light-emitting element, wherein the light-emitting element comprises a first electrode, a second electrode disposed on the first electrode, and a light-emitting layer disposed between the first electrode and the second electrode and including a first compound represented by the chemical formula 1. Effects of the invention

[0039] The light-emitting device of one embodiment can exhibit improved device characteristics with a long lifespan.

[0040] A condensed polycyclic compound of one embodiment can be included in the light-emitting layer of a light-emitting device to contribute to extending the lifespan of the light-emitting device.

[0041] The electronic device of one embodiment can exhibit excellent display quality. Brief explanation of the drawing

[0042] FIG. 1 is a plan view of a display device according to one embodiment of the present invention. FIG. 2 is a cross-sectional view of a display device according to one embodiment of the present invention. FIG. 3 is a cross-sectional view schematically showing a light-emitting element according to one embodiment of the present invention. FIG. 4 is a cross-sectional view schematically showing a light-emitting element according to one embodiment of the present invention. FIG. 5 is a cross-sectional view schematically showing a light-emitting element according to one embodiment of the present invention. FIG. 6 is a cross-sectional view schematically showing a light-emitting element according to one embodiment of the present invention. FIGS. 7 and FIGS. 8 are cross-sectional views of a display device according to one embodiment of the present invention. FIG. 9 is a cross-sectional view showing a display device according to one embodiment of the present invention. FIG. 10 is a cross-sectional view showing a display device according to one embodiment of the present invention. FIG. 11 is a drawing showing a vehicle with a display device installed according to one embodiment. FIG. 12 is a graph showing the lowest singlet excitation energy level and the lowest triplet excitation energy level for each of the light-emitting devices containing the example compounds and comparative example compounds as dopant materials. Specific details for implementing the invention

[0043] The present invention is capable of various modifications and may take various forms, and specific embodiments are illustrated in the drawings and described in detail in the text. However, this is not intended to limit the invention to the specific disclosed forms, and it should be understood that the invention includes all modifications, equivalents, and substitutions that fall within the spirit and scope of the invention.

[0044] In describing each drawing, similar reference numerals have been used for similar components. In the attached drawings, the dimensions of the structures are depicted enlarged from their actual size for clarity of the invention. Terms such as "first," "second," etc., may be used to describe various components, but said components should not be limited by said terms. These terms are used solely for the purpose of distinguishing one component from another. For example, without departing from the scope of the invention, the first component may be named the second component, and similarly, the second component may be named the first component. A singular expression includes a plural expression unless the context clearly indicates otherwise.

[0045] In this application, terms such as "comprising" or "having" are intended to specify the existence of the features, numbers, steps, actions, components, parts, or combinations thereof described in the specification, and should be understood as not precluding the existence or addition of one or more other features, numbers, steps, actions, components, parts, or combinations thereof.

[0046] In this application, when a part such as a layer, film, region, or plate is described as being "on" or "upper" to another part, this includes not only cases where it is "immediately above" the other part, but also cases where there is another part in between. Conversely, when a part such as a layer, film, region, or plate is described as being "under" or "lower" to another part, this includes not only cases where it is "immediately below" the other part, but also cases where there is another part in between. Furthermore, in this application, being "placed on" may include cases where it is placed not only on the upper part but also on the lower part.

[0047] In this specification, "substituted or unsubstituted" may mean substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium atoms, halogen atoms, cyano groups, nitro groups, amino groups, silyl groups, oxy groups, thio groups, sulfinyl groups, sulfonyl groups, carbonyl groups, boron groups, phosphine oxide groups, phosphine sulfide groups, alkyl groups, alkenyl groups, alkynyl groups, hydrocarbon ring groups, aryl groups, and heterocyclic groups. Additionally, each of the substituents exemplified above may be substituted or unsubstituted. For example, a biphenyl group may be interpreted as an aryl group or as a phenyl group substituted with a phenyl group.

[0048] In this specification, "forming a ring by combining with adjacent groups" may mean forming a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted hetero ring by combining with adjacent groups. The hydrocarbon ring includes an aliphatic hydrocarbon ring and an aromatic hydrocarbon ring. The hetero ring includes an aliphatic hetero ring and an aromatic hetero ring. The hydrocarbon ring and the hetero ring may be monocyclic or polycyclic. Additionally, the ring formed by combining with each other may be connected to another ring to form a spiro structure.

[0049] In this specification, "adjacent group" may mean a substituent substituted on an atom directly connected to the atom on which the substituent is substituted, another substituent substituted on the atom on which the substituent is substituted, or a substituent that is stereostructively closest to the substituent. For example, in 1,2-dimethylbenzene, two methyl groups may be interpreted as "adjacent groups," and in 1,1-diethylcyclopentane, two ethyl groups may be interpreted as "adjacent groups." Additionally, in 4,5-dimethylphenanthrene, two methyl groups may be interpreted as "adjacent groups."

[0050] In this specification, examples of halogen atoms include fluorine atoms, chlorine atoms, bromine atoms, or iodine atoms.

[0051] In this specification, the alkyl group may be of the straight chain or branched chain type. The number of carbon atoms in the alkyl group is 1 or more and 50 or less, 1 or more and 30 or less, 1 or more and 20 or less, 1 or more and 10 or less, or 1 or more and 6 or less. Examples of alkyl groups include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, s-butyl group, t-butyl group, i-butyl group, 2-ethylbutyl group, 3,3-dimethylbutyl group, n-pentyl group, i-pentyl group, neopentyl group, t-pentyl group, 1-methylpentyl group, 3-methylpentyl group, 2-ethylpentyl group, 4-methyl-2-pentyl group, n-hexyl group, 1-methylhexyl group, 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, t-octyl group, 2-ethyloctyl group, 2-butyloctyl group, 2-hexyloctyl group. 3,7-dimethyloctyl group, n-nonyl group, n-decyl group, adamantyl group, 2-ethyldecyl group, 2-butyldecyl group, 2-hexyldecyl group, 2-octyldecyl group, n-undecyl group, n-dodecyl group, 2-ethyldodecyl group, 2-butyldodecyl group, 2-hexyldodecyl group, 2-octyldodecyl group, n-tridecyl group, n-tetradecyl group, n-pentadecyl group, n-hexadecyl group, 2-ethylhexadecyl group, 2-butylhexadecyl group, 2-hexylhexadecyl group, 2-octylhexadecyl group, n-heptadecyl group, n-octadecyl group, n-nonadecyl group, n-icosyl group, 2-ethylicosyl group, 2-butylicosyl group, Examples include, but are not limited to, 2-hexylicosyl groups, 2-octylicosyl groups, n-henicosyl groups, n-docosyl groups, n-tricosyl groups, n-tetracosyl groups, n-pentacosyl groups, n-hexacosyl groups, n-heptacosyl groups, n-octacosyl groups, n-nonacosyl groups, and n-triacontyl groups.

[0052] In this specification, a cycloalkyl group may refer to a cyclic alkyl group. The number of carbon atoms in a cycloalkyl group is 3 or more and 50 or less, 3 or more and 30 or less, or 3 or more and 20 or less, or 3 or more and 10. Examples of cycloalkyl groups include, but are not limited to, cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, 4-methylcyclohexyl group, 4-t-butylcyclohexyl group, cycloheptyl group, cyclooctyl group, cyclononyl group, cyclodecyl group, norbornyl group, 1-adamantyl group, 2-adamantyl group, isobornyl group, bicycloheptyl group, etc.

[0053] In this specification, an alkenyl group refers to a hydrocarbon group comprising one or more carbon double bonds at the middle or terminal of an alkyl group having two or more carbon atoms. The alkenyl group may be straight or branched. The number of carbon atoms is not particularly limited, but is 2 or more and 30 or less, 2 or more and 20 or less, or 2 or more and 10 or less. Examples of alkenyl groups include, but are not limited to, vinyl groups, 1-butenyl groups, 1-pentenyl groups, 1,3-butadienyl aryl groups, styrenyl groups, styrylvinyl groups, etc.

[0054] In this specification, an alkynyl group refers to a hydrocarbon group comprising one or more carbon triple bonds at the middle or terminal of an alkyl group having two or more carbon atoms. The alkynyl group may be straight 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, ethinyl groups, propynyl groups, etc.

[0055] In this specification, a hydrocarbon ring group refers to any functional group or substituent derived from an aliphatic hydrocarbon ring. The hydrocarbon ring group may be a saturated hydrocarbon ring group having 5 to 20 carbon atoms forming the ring.

[0056] In this specification, an aryl group refers to any functional group or substituent derived from an aromatic hydrocarbon ring. The aryl group may be a monocyclic aryl group or a polycyclic aryl group. The number of ring-forming carbon atoms in the aryl group may be 6 or more and 30 or less, 6 or more and 20 or less, or 6 or more and 15 or less. Examples of aryl groups may include, but are not limited to, phenyl groups, naphthyl groups, fluorenyl groups, anthracenyl groups, phenanthryl groups, biphenyl groups, terphenyl groups, quarterphenyl groups, quinquephenyl groups, sexphenyl groups, triphenylenyl groups, pyrenyl groups, benzofluranthenyl groups, crisenyl groups, etc.

[0057] In this specification, the fluorenyl group may be substituted, and two substituents may be combined to form a spiro structure. Examples of cases where the fluorenyl group is substituted are as follows. However, it is not limited thereto.

[0058]

[0059] In this specification, a heterocyclic group refers to any functional group or substituent derived from a ring comprising one or more of B, O, N, P, Si, and S as heteroatoms. Heterocyclic groups include aliphatic heterocyclic groups and aromatic heterocyclic groups. Aromatic heterocyclic groups may be heteroaryl groups. Aliphatic heterocyclic groups and aromatic heterocyclic groups may be monocyclic or polycyclic.

[0060] In this specification, a heterocyclic group may include one or more of B, O, N, P, Si, and S as heteroatoms. If the heterocyclic group includes two or more heteroatoms, the two or more heteroatoms may be identical or different from each other. The heterocyclic group may be a monocyclic heterocyclic group or a polycyclic heterocyclic group, and is a concept that includes a heteroaryl group. The number of ring-forming carbons of the heterocyclic group may be 2 or more and 30 or less, 2 or more and 20 or less, or 2 or more and 10 or less.

[0061] In this specification, the aliphatic heterocyclic group may include one or more of B, O, N, P, Si, and S as heteroatoms. The number of ring-forming carbon atoms in the aliphatic heterocyclic group may be 2 or more and 30 or less, 2 or more and 20 or less, or 2 or more and 10 or less. Examples of the aliphatic heterocyclic group include, but are not limited to, oxirane groups, thiran groups, pyrrolidine groups, piperidine groups, tetrahydrofuran groups, tetrahydrothiophene groups, thian groups, tetrahydropyran groups, 1,4-dioxane groups, etc.

[0062] In this specification, the heteroaryl group may include one or more of B, O, N, P, Si, and S as heteroatoms. If the heteroaryl group includes two or more heteroatoms, the two or more heteroatoms may be identical or different from each other. The heteroaryl group may be a monocyclic heterocyclic group or a polycyclic heterocyclic group. The number of ring-forming carbons in the heteroaryl group may be 2 or more and 30 or less, 2 or more and 20 or less, or 2 or more and 10 or less. Examples of heteroaryl groups include thiophene group, furan group, pyrrole group, imidazole group, pyridine group, bipyridine group, pyrimidine group, triazine group, triazole group, acryl group, pyridazine group, pyrazinyl group, quinoline group, quinazolin group, quinoxaline group, phenoxazine group, phthalazine group, pyridopyrimidine group, pyridopyrazine group, pyrazinopyrazine group, isoquinoline group, indole group, carbazole group, N-arylcarbazole group, N-heteroarylcarbazole group, N-alkylcarbazole group, benzoxazole group, benzimidazole group, benzothiazole group, benzocarbazole group, benzothiophen group, dibenzothiophen group, thienothiophene group, benzofuran group, phenanthroline group, thiazole group, There are isooxazole groups, oxazole groups, oxadiazole groups, thiadiaazole groups, phenothiazine groups, dibenzosilol groups and dibenzofuran groups, but are not limited to these.

[0063] In this specification, the description of the aryl group described above may apply except that the arylene group is a divalent group. The description of the heteroaryl group described above may apply except that the heteroarylene group is a divalent group.

[0064] In this specification, silyl groups include alkyl silyl groups and aryl silyl groups. Examples of silyl groups include, but are not limited to, trimethylsilyl groups, triethylsilyl groups, t-butyldimethylsilyl groups, vinyldimethylsilyl groups, propyldimethylsilyl groups, triphenylsilyl groups, diphenylsilyl groups, phenylsilyl groups, etc.

[0065] In this specification, the number of carbon atoms in the carbonyl group is not particularly limited, but may be 1 to 40 or fewer, 1 to 30 or fewer, or 1 to 20 or fewer. For example, it may have the following structure, but is not limited thereto.

[0066]

[0067] In this specification, the number of carbon atoms in the sulfinyl group and the sulfonyl group is not particularly limited, but may be 1 or more and 30 or less. The sulfinyl group may include an alkyl sulfinyl group and an aryl sulfinyl group. The sulfonyl group may include an alkyl sulfonyl group and an aryl sulfonyl group.

[0068] In this specification, the thio group may include alkyl thio groups and aryl thio groups. The thio group may mean that a sulfur atom is bonded to the alkyl or aryl group defined above. Examples of thio groups include, but are not limited to, methyl thio group, ethyl thio group, propyl thio group, pentyl thio group, hexyl thio group, octyl thio group, dodecyl thio group, cyclopentyl thio group, cyclohexyl thio group, phenyl thio group, naphthyl thio group, etc.

[0069] In this specification, an oxy group may refer to an alkyl group or aryl group defined above in which an oxygen atom is bonded. An oxy group may include an alkoxy group and an aryl oxy group. An alkoxy group may be a straight chain, a branched chain, or a cyclic chain. The number of carbon atoms in an alkoxy group is not particularly limited, but may be, for example, 1 or more and 20 or less, or 1 or more and 10 or less. Examples of oxy groups include, but are not limited to, methoxy, ethoxy, n-propoxy, isopropoxy, butoxy, pentyloxy, hexyloxy, octyloxy, nonyloxy, decyloxy, benzyloxy, etc.

[0070] In this specification, a boron group may mean that a boron atom is bonded to the alkyl group or aryl group defined above. Boron groups include alkyl boron groups and aryl boron groups. Examples of boron groups include, but are not limited to, dimethyl boron groups, diethyl boron groups, t-butylmethyl boron groups, diphenyl boron groups, phenyl boron groups, etc.

[0071] In this specification, the number of carbon atoms in the amine group is not particularly limited, but may be 1 or more and 30 or less. The amine group may include alkyl amine groups and aryl amine groups. Examples of amine groups include methylamine groups, dimethylamine groups, phenylamine groups, diphenylamine groups, naphthylamine groups, 9-methyl-anthracenylamine groups, etc., but are not limited thereto.

[0072] In this specification, among alkyl thio groups, alkyl sulfoxy groups, alkyl aryl groups, alkyl amino groups, alkyl boron groups, alkyl silyl groups, and alkyl amine groups, the alkyl groups are the same as the examples of alkyl groups described above.

[0073] In this specification, the aryl group among the aryloxy group, arylthio group, arylsulfoxy group, arylamino group, arylboron group, arylsilyl group, and arylamine group is the same as the examples of aryl groups described above.

[0074] In this specification, direct linkage may mean a single linkage.

[0075] Meanwhile, in this specification " " and " " means the location where it is connected.

[0076] Hereinafter, an embodiment of the present invention will be described with reference to the drawings.

[0077] FIG. 1 is a plan view showing one embodiment of a display device (DD). FIG. 2 is a cross-sectional view of the display device (DD) of one embodiment. FIG. 2 is a cross-sectional view showing the portion corresponding to line I-I' of FIG. 1.

[0078] A 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, ED-3). The display device (DD) may include a plurality of light-emitting elements (ED-1, ED-2, ED-3). The optical layer (PP) is disposed on the display panel (DP) to control reflected light from the display panel (DP) caused by external light. The optical layer (PP) may include, for example, a polarizing layer or a color filter layer. Meanwhile, unlike what is shown in the drawings, the optical layer (PP) may be omitted in the display device (DD) of one embodiment.

[0079] A base substrate (BL) may be disposed on the optical layer (PP). The base substrate (BL) may be a member that provides a base surface on which the optical layer (PP) is disposed. The base substrate (BL) may be a glass substrate, a metal substrate, a plastic substrate, etc. However, the embodiments are not limited thereto, and the base substrate (BL) may be an inorganic layer, an organic layer, or a composite material layer. In addition, unlike what is illustrated, the base substrate (BL) may be omitted in one embodiment.

[0080] A display device (DD) according to one embodiment may further include a filling layer (not shown). The filling layer (not shown) may be disposed between a display element layer (DP-ED) and a base substrate (BL). The filling layer (not shown) may be an organic layer. The filling layer (not shown) may include at least one of an acrylic resin, a silicone resin, and an epoxy resin.

[0081] The display panel (DP) may include a base layer (BS), a circuit layer (DP-CL) provided on the base layer (BS), and a display element layer (DP-ED). The display element layer (DP-ED) may include a pixel defining layer (PDL), light-emitting elements (ED-1, ED-2, ED-3) disposed between the pixel defining layers (PDL), and an encapsulation layer (TFE) disposed on the light-emitting elements (ED-1, ED-2, ED-3).

[0082] The base layer (BS) may be a member that provides a base surface on which the display element layer (DP-ED) is placed. The base layer (BS) may be a glass substrate, a metal substrate, a plastic substrate, etc. However, the embodiments are not limited thereto, and the base layer (BS) may be an inorganic layer, an organic layer, or a composite material layer.

[0083] In one embodiment, the circuit layer (DP-CL) is disposed on the base layer (BS), and the circuit layer (DP-CL) may include a plurality of transistors (not shown). Each of the transistors (not shown) may include a control electrode, an input electrode, and an output electrode. For example, the circuit layer (DP-CL) may include a switching transistor and a driving transistor for driving light-emitting elements (ED-1, ED-2, ED-3) of the display element layer (DP-ED).

[0084] Each of the light-emitting elements (ED-1, ED-2, ED-3) may have the structure of a light-emitting element (ED) according to one embodiment of FIGS. 3 to 6 described below. Each of the light-emitting elements (ED-1, ED-2, ED-3) may include a first electrode (EL1), a hole transport region (HTR), a light-emitting layer (EML-R, EML-G, EML-B), an electron transport region (ETR), and a second electrode (EL2).

[0085] FIG. 2 illustrates an embodiment in which the light-emitting layers (EML-R, EML-G, EML-B) of light-emitting elements (ED-1, ED-2, ED-3) are disposed within an opening (OH) defined in a pixel defining film (PDL), and the hole transport region (HTR), electron transport region (ETR), and second electrode (EL2) are provided as a common layer throughout the light-emitting elements (ED-1, ED-2, ED-3). However, the embodiment is not limited thereto, and unlike FIG. 2, in one embodiment, the hole transport region (HTR) and electron transport region (ETR) may be patterned and provided within the opening (OH) defined in the pixel defining film (PDL). For example, in one embodiment, the hole transport region (HTR), light-emitting layer (EML-R, EML-G, EML-B), and electron transport region (ETR) of the light-emitting element (ED-1, ED-2, ED-3) may be provided by patterning using an inkjet printing method.

[0086] The encapsulation layer (TFE) may cover light-emitting elements (ED-1, ED-2, ED-3). The encapsulation layer (TFE) may seal a display element layer (DP-ED). The encapsulation layer (TFE) may be a thin film encapsulation layer. The encapsulation layer (TFE) may be a single layer or a plurality of layers stacked. The encapsulation layer (TFE) includes at least one insulating layer. The encapsulation layer (TFE) according to one embodiment may include at least one inorganic film (hereinafter, encapsulation inorganic film). Additionally, the encapsulation layer (TFE) according to one embodiment may include at least one organic film (hereinafter, encapsulation organic film) and at least one encapsulation inorganic film.

[0087] The encapsulation inorganic film protects the display device layer (DP-ED) from moisture / oxygen, and the encapsulation organic film protects the display device layer (DP-ED) from foreign substances such as dust particles. The encapsulation inorganic film may include silicon nitride, silicon oxynitride, silicon oxide, titanium oxide, or aluminum oxide, but is not particularly limited thereto. The encapsulation organic film may include acrylic compounds, epoxy compounds, etc. The encapsulation organic film may include photopolymerizable organic materials and is not particularly limited thereto.

[0088] The encapsulation layer (TFE) can be placed on the second electrode (EL2) and can fill the opening (OH).

[0089] Referring to FIGS. 1 and 2, the display device (DD) may include a non-emissive region (NPXA) and emissive regions (PXA-R, PXA-G, PXA-B). Each of the emissive regions (PXA-R, PXA-G, PXA-B) may be a region where light generated from each of the emissive elements (ED-1, ED-2, ED-3) is emitted. The emissive regions (PXA-R, PXA-G, PXA-B) may be spaced apart from each other in a plane.

[0090] Each of the light-emitting regions (PXA-R, PXA-G, PXA-B) may be a region separated by a pixel defining film (PDL). Non-light-emitting regions (NPXA) may be regions between adjacent light-emitting regions (PXA-R, PXA-G, PXA-B) and may be regions corresponding to the pixel defining film (PDL). Meanwhile, in this specification, each of the light-emitting regions (PXA-R, PXA-G, PXA-B) may correspond to a pixel. The pixel defining film (PDL) may separate light-emitting elements (ED-1, ED-2, ED-3). The light-emitting layers (EML-R, EML-G, EML-B) of the light-emitting elements (ED-1, ED-2, ED-3) may be separated by being placed in an opening (OH) defined in the pixel defining film (PDL).

[0091] The light-emitting regions (PXA-R, PXA-G, PXA-B) can be divided into multiple groups according to the color of light generated from the light-emitting elements (ED-1, ED-2, ED-3). In the display device (DD) of one embodiment illustrated in FIGS. 1 and 2, three light-emitting regions (PXA-R, PXA-G, PXA-B) emitting red light, green light, and blue light are illustrated as examples. For example, the display device (DD) of one embodiment may include a red light-emitting region (PXA-R), a green light-emitting region (PXA-G), and a blue light-emitting region (PXA-B) that are distinct from each other.

[0092] In a display device (DD) according to one embodiment, a plurality of light-emitting elements (ED-1, ED-2, ED-3) may emit light in different wavelength regions. For example, in one embodiment, the display device (DD) may include a first light-emitting element (ED-1) that emits red light, a second light-emitting element (ED-2) that emits green light, and a third light-emitting element (ED-3) that emits blue light. That is, the red light-emitting region (PXA-R), the green light-emitting region (PXA-G), and the blue light-emitting region (PXA-B) of the display device (DD) may correspond to the first light-emitting element (ED-1), the second light-emitting element (ED-2), and the third light-emitting element (ED-3), respectively.

[0093] However, the embodiments are not limited thereto, and the first to third light-emitting elements (ED-1, ED-2, ED-3) may emit light in the same wavelength range, or at least one may emit light in a different wavelength range. For example, the first to third light-emitting elements (ED-1, ED-2, ED-3) may all emit blue light.

[0094] In a display device (DD) according to one embodiment, the light-emitting regions (PXA-R, PXA-G, PXA-B) may be arranged in a stripe shape. Referring to FIG. 1, a plurality of red light-emitting regions (PXA-R), a plurality of green light-emitting regions (PXA-G), and a plurality of blue light-emitting regions (PXA-B) may each be aligned along a second directional axis (DR2). Additionally, they may be arranged alternately along a first directional axis (DR1) in the order of red light-emitting regions (PXA-R), green light-emitting regions (PXA-G), and blue light-emitting regions (PXA-B).

[0095] In FIGS. 1 and 2, the areas of the light-emitting regions (PXA-R, PXA-G, PXA-B) are all depicted as similar, but the embodiment is not limited thereto, and the areas of the light-emitting regions (PXA-R, PXA-G, PXA-B) may differ from one another depending on the wavelength range of the emitted light. Meanwhile, the areas of the light-emitting regions (PXA-R, PXA-G, PXA-B) may refer to the area when viewed on a plane defined by the first directional axis (DR1) and the second directional axis (DR2).

[0096] Meanwhile, the arrangement of the light-emitting regions (PXA-R, PXA-G, PXA-B) is not limited to that shown in FIG. 1, and the order in which the red light-emitting region (PXA-R), the green light-emitting region (PXA-G), and the blue light-emitting region (PXA-B) are arranged can be provided in various combinations depending on the characteristics of the display quality required by the display device (DD). For example, the arrangement of the light-emitting regions (PXA-R, PXA-G, PXA-B) may be a Pentile™ arrangement or a Diamond Pixel™ arrangement.

[0097] Additionally, the areas of the light-emitting regions (PXA-R, PXA-G, PXA-B) may differ from each other. For example, in one embodiment, the area of ​​the green light-emitting region (PXA-G) may be smaller than the area of ​​the blue light-emitting region (PXA-B), but the embodiment is not limited thereto.

[0098] Hereinafter, FIGS. 3 to 6 are cross-sectional views schematically illustrating a light-emitting element according to one embodiment. A light-emitting element (ED) according to one embodiment may include a first electrode (EL1), a second electrode (EL2) facing the first electrode (EL1), and at least one functional layer disposed between the first electrode (EL1) and the second electrode (EL2). A light-emitting element (ED) of one embodiment may include a condensed polycyclic compound of one embodiment described below in at least one functional layer.

[0099] The light-emitting element (ED) may include a hole transport region (HTR), an emitting layer (EML), an electron transport region (ETR), etc., which are sequentially stacked as at least one functional layer. That is, the light-emitting element (ED) of one embodiment may include a first electrode (EL1), a hole transport region (HTR), an emitting layer (EML), an electron transport region (ETR), and a second electrode (EL2) which are sequentially stacked.

[0100] FIG. 4 shows a cross-sectional view of a light-emitting device (ED) of an embodiment in which, compared with FIG. 3, the hole transport region (HTR) includes a hole injection layer (HIL) and a hole transport layer (HTL), and the electron transport region (ETR) includes an electron injection layer (EIL) and an electron transport layer (ETL). FIG. 5 also shows a cross-sectional view of a light-emitting device (ED) of an embodiment in which, compared with FIG. 3, the hole transport region (HTR) includes a hole injection layer (HIL), a hole transport layer (HTL), and an electron blocking layer (EBL), and the electron transport region (ETR) includes an electron injection layer (EIL), an electron transport layer (ETL), and a hole blocking layer (HBL). FIG. 6 shows a cross-sectional view of a light-emitting device (ED) of an embodiment in which, compared with FIG. 4, a capping layer (CPL) disposed on a second electrode (EL2).

[0101] A light-emitting element (ED) of one embodiment may include a condensed polycyclic compound of one embodiment described below in at least one functional layer included in the light-emitting element (ED). In the light-emitting element (ED) of one embodiment, the condensed polycyclic compound of one embodiment may be included in at least one of the hole transport region (HTR), the emitting layer (EML), and the electron transport region (ETR). For example, in the light-emitting element (ED) of one embodiment, the emitting layer (EML) may include a condensed polycyclic compound of one embodiment.

[0102] The first electrode (EL1) has conductivity. The first electrode (EL1) may be formed of a metal material, a metal alloy, or a conductive compound. The first electrode (EL1) may be an anode or a cathode. However, the embodiments are not limited thereto. Additionally, the first electrode (EL1) may be a pixel electrode. The first electrode (EL1) may be a transmissive electrode, a semitransmissive electrode, or a reflective electrode. The first electrode (EL1) may comprise 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, at least two mixtures selected from these, or oxides thereof.

[0103] If the first electrode (EL1) is a transparent electrode, the first electrode (EL1) may include a transparent metal oxide, for example, ITO (indium tin oxide), IZO (indium zinc oxide), ZnO (zinc oxide), ITZO (indium tin zinc oxide), etc. If the first electrode (EL1) is a semitransparent electrode or a reflective electrode, the first electrode (EL1) may include Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF / Ca (layered structure of LiF and Ca), LiF / Al (layered structure of LiF and Al), Mo, Ti, W, or a compound or mixture thereof (for example, a mixture of Ag and Mg). Alternatively, the first electrode (EL1) may have a plurality of layer structures including a reflective film or a semi-transparent film formed of the above material and a transparent conductive film formed of ITO (indium tin oxide), IZO (indium zinc oxide), ZnO (zinc oxide), ITZO (indium tin zinc oxide), etc. For example, the first electrode (EL1) may have a three-layer structure of ITO / Ag / ITO, but is not limited thereto. Furthermore, the embodiments are not limited thereto, and the first electrode (EL1) may include the metal material described above, a combination of two or more metal materials selected from the metal materials described above, or oxides of the metal materials described above. The thickness of the first electrode (EL1) may be about 700 Å to about 10000 Å. For example, the thickness of the first electrode (EL1) may be about 1000 Å to about 3000 Å.

[0104] 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 a light-emitting auxiliary layer (not shown), and an electron blocking layer (EBL). The thickness of the hole transport region (HTR) may be, for example, about 50 Å to about 15,000 Å.

[0105] The hole transport region (HTR) may have a multilayer structure consisting of a single layer made of a single material, a single layer made of multiple different materials, or multiple layers made of multiple different materials.

[0106] For example, the hole transport region (HTR) may have a single-layer structure of a hole injection layer (HIL) or a hole transport layer (HTL), or a single-layer structure composed of a hole injection material and a hole transport material. Additionally, the hole transport region (HTR) may have a single-layer structure composed of multiple different materials, or may have a structure of a hole injection layer (HIL) / hole transport layer (HTL), a hole injection layer (HIL) / hole transport layer (HTL) / buffer layer (not shown), a hole injection layer (HIL) / buffer layer (not shown), a hole transport layer (HTL) / buffer layer (not shown), or a hole injection layer (HIL) / hole transport layer (HTL) / electron blocking layer (EBL) stacked sequentially from the first electrode (EL1), but the embodiments are not limited thereto.

[0107] Hole transport regions (HTRs) can be formed using various methods such as vacuum deposition, spin coating, casting, LB method (Langmuir-Blodgett), inkjet printing, laser printing, and laser induced thermal imaging (LITI).

[0108] The hole transport region (HTR) may include a compound represented by the following chemical formula H-1.

[0109] [Chemical Formula H-1]

[0110]

[0111] In the above chemical formula H-1, L1 and L2 may each independently be a direct linkage, substituted or unsubstituted ring-forming arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heteroarylene group having 2 to 30 carbon atoms. a and b may each independently be integers from 0 to 10. Meanwhile, if a or b is an integer of 2 or more, a plurality of L1 and L2 may each independently be a substituted or unsubstituted ring-forming arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heteroarylene group having 2 to 30 carbon atoms.

[0112] In chemical formula H-1, Ar1 and Ar2 may each independently be a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heteroaryl group having 2 to 30 carbon atoms. Additionally, in chemical formula H-1, Ar3 may be a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heteroaryl group having 2 to 30 carbon atoms.

[0113] The compound represented by the above formula H-1 may be a monoamine compound. Alternatively, the compound represented by the above formula H-2 may be a diamine compound in which at least one of Ar-1 to Ar3 comprises an amine group as a substituent. Additionally, the compound represented by the above formula H-1 may be a carbazole compound comprising a carbazole group substituted or unsubstituted on at least one of Ar1 and Ar2, or a fluorene compound comprising a fluorene group substituted or unsubstituted on at least one of Ar1 and Ar2.

[0114] The compound represented by the chemical formula H-1 may be represented as any one of the compounds in the following compound group H. However, the compounds listed in the following compound group H are exemplary, and the compound represented by the chemical formula H-1 is not limited to those listed in the following compound group H.

[0115] [Compound Group H]

[0116]

[0117]

[0118]

[0119] The hole transport region (HTR) is phthalocyanine compounds such as copper phthalocyanine, DNTPD(N 1 ,N 1' -([1,1'-biphenyl]-4,4'-diyl)bis(N 1 -phenyl-N 4 ,N 4-di-m-tolylbenzene-1,4-diamine)), m-MTDATA(4,4',4"-[tris(3-methylphenyl)phenylamino] triphenylamine), TDATA(4,4'4"-Tris(N,N-diphenylamino)triphenylamine), 2-TNATA(4,4',4"-tris[N(2-naphthyl)-N-phenylamino]-triphenylamine), PEDOT / PSS(Poly(3,4-ethylenedioxythiophene) / Poly(4-styrenesulfonate)), PANI / DBSA(Polyaniline / Dodecylbenzenesulfonic acid), PANI / CSA(Polyaniline / Camphor sulfonicacid), PANI / PSS(Polyaniline / Poly(4-styrenesulfonate)), NPB(N,N'-di(naphthalene-l-yl)-N,N'-diphenyl-benzidine), 트리페닐아민을 포함하는 폴리에테르케톤(TPAPEK), 4-Isopropyl-4'-methyldiphenyliodonium [Tetrakis(pentafluorophenyl)borate], HATCN(dipyrazino[2,3-f: 2',3'-h] quinoxaline-2,3,6,7,10,11-hexacarbonitrile) 등을 포함할 수 있다.

[0120] The hole transport region (HTR) may include carbazole derivatives such as N-phenylcarbazole and polyvinylcarbazole, fluorene derivatives, triphenylamine derivatives such as TPD (N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine) and TCTA (4,4',4"-tris(N-carbazolyl)triphenylamine), NPB (N,N'-di(naphthalene-l-yl)-N,N'-diphenyl-benzidine), TAPC (4,4′-Cyclohexylidene bis[N,N-bis(4-methylphenyl)benzenamine]), HMTPD (4,4'-Bis[N,N'-(3-tolyl)amino]-3,3'-dimethylbiphenyl), mCP (1,3-Bis(N-carbazolyl)benzene), etc. there is.

[0121] Additionally, the hole transport region (HTR) may include CzSi (9-(4-tert-Butylphenyl)-3,6-bis(triphenylsilyl)-9H-carbazole), CCP (9-phenyl-9H-3,9'-bicarbazole), or mDCP (1,3-bis(1,8-dimethyl-9H-carbazol-9-yl)benzene), etc.

[0122] The hole transport region (HTR) may include compounds of the hole transport region described above in at least one of the hole injection layer (HIL), hole transport layer (HTL), and electron blocking layer (EBL).

[0123] The thickness of the hole transport region (HTR) may be about 100 Å to about 10000 Å, for example, about 100 Å to about 5000 Å. If the hole transport region (HTR) includes a hole injection layer (HIL), the thickness of the hole injection layer (HIL) may be, for example, about 30 Å to about 1000 Å. If the hole transport region (HTR) includes a hole transport layer (HTL), the thickness of the hole transport layer (HTL) may be about 30 Å to about 1000 Å. For example, if the hole transport region (HTR) includes an electron blocking layer (EBL), the thickness of the electron blocking layer (EBL) may be about 10 Å to about 1000 Å. When the thicknesses of the hole transport region (HTR), hole injection layer (HIL), hole transport layer (HTL), and electron blocking layer (EBL) satisfy the ranges described above, satisfactory hole transport characteristics can be obtained without a substantial increase in driving voltage.

[0124] In addition to the aforementioned materials, the hole transport region (HTR) may further include a charge-generating material to enhance conductivity. The charge-generating material may be uniformly or non-uniformly dispersed within the hole transport region (HTR). The charge-generating material may be, for example, a p-dopant. The p-dopant may include at least one of a metal halide compound, a quinone derivative, a metal oxide, and a cyano group-containing compound, but is not limited thereto. For example, p-dopants may include metal halide compounds such as CuI and RbI, quinone derivatives such as TCNQ (Tetracyanoquinodimethane) and F4-TCNQ (2,3,5,6-tetrafluoro-7,7'8,8-tetracyanoquinodimethane), metal oxides such as tungsten oxide and molybdenum oxide, and cyano group-containing compounds such as HATCN (dipyrazino[2,3-f: 2',3'-h] quinoxaline-2,3,6,7,10,11-hexacarbonitrile) and NDP9 (4-[[2,3-bis[cyano-(4-cyano-2,3,5,6-tetrafluorophenyl)methylidene]cyclopropylidene]-cyanomethyl]-2,3,5,6-tetrafluorobenzonitrile), but the examples are not limited thereto.

[0125] As described above, the hole transport region (HTR) may further include at least one of a buffer layer (not shown) and an electron blocking layer (EBL) in addition to the hole injection layer (HIL) and the hole transport layer (HTL). The buffer layer (not shown) can increase light emission efficiency by compensating for the resonance distance according to the wavelength of light emitted from the light-emitting layer (EML). The material included in the buffer layer (not shown) may be a material that can be included in the hole transport region (HTR). The electron blocking layer (EBL) is a layer that serves to prevent electron injection from the electron transport region (ETR) into the hole transport region (HTR).

[0126] An emissive layer (EML) is provided on a hole transport region (HTR). The emissive layer (EML) may have a thickness of, for example, about 100 Å to about 1000 Å or about 100 Å to about 300 Å. The emissive layer (EML) may have a multilayer structure consisting of a single layer made of a single material, a single layer made of multiple different materials, or multiple layers made of multiple different materials.

[0127] A light-emitting element (ED) of one embodiment may comprise a condensed polycyclic compound represented by the following chemical formula 1 in at least one functional layer disposed between a first electrode (EL1) and a second electrode (EL2). In the light-emitting element (ED) according to one embodiment, the light-emitting layer (EML) may comprise the condensed polycyclic compound of one embodiment. In one embodiment, the light-emitting layer (EML) may comprise the condensed polycyclic compound of one embodiment as a dopant. The condensed polycyclic compound of one embodiment may be a dopant material of the light-emitting layer (EML). Meanwhile, in this specification, the condensed polycyclic compound of one embodiment may be referred to as the first compound.

[0129] A condensed polycyclic compound of one embodiment comprises a condensed ring core comprising five condensed rings, one boron atom, one nitrogen atom, and one heteroatom, and a first substituent connected to the condensed ring core. In one embodiment, the condensed ring core included in the condensed polycyclic compound may form five rings as three substituted or unsubstituted benzene rings are connected through a first boron atom, a first nitrogen atom, and a first heteroatom. More specifically, regarding the three benzene rings included in the condensed ring core, the three benzene rings may be connected around the first boron atom, the first benzene ring and the second benzene ring among the three benzene rings may be connected through the first heteroatom, and the remaining third benzene ring may be connected to the first benzene ring through the first nitrogen atom. The first boron atom, the first nitrogen atom, and the first heteroatom may all be connected to the first benzene ring. In one embodiment, the first heteroatom may be an oxygen (O) atom, a sulfur (S) atom, or a nitrogen (N) atom.

[0130] A condensed polycyclic compound of one embodiment may include a first substituent connected to a condensed ring core. The first substituent may be connected to a first nitrogen atom. The first substituent may include a structure comprising a first benzene moiety connected to the first nitrogen atom, and a first substituent and a second substituent respectively connected to the first benzene moiety. The first substituent may include a second benzene moiety connected at an ortho position carbon relative to the carbon atom connected to the first nitrogen atom among the carbon atoms constituting the first benzene moiety, and a third benzene moiety connected at a para position carbon relative to the carbon atom connected to the first benzene moiety among the carbon atoms constituting the second benzene moiety. The first substituent may include a biphenyl moiety. Alternatively, the second benzene moiety and the third benzene moiety in the first substituent may form a ring by means of a second heteroatom. The second heteroatom may be an oxygen (O) atom or a sulfur (S) atom. The first subsubstituent may include a dibenzofuran moiety or a dibenzothiophene moiety. The second subsubstituent may be a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms. In one embodiment, the second subsubstituent may be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted dibenzofuran group, or a substituted or unsubstituted dibenzothiophene group.

[0131] In the case where the first heteroatom in the condensation ring core of the condensation polycyclic compound of one embodiment is a nitrogen atom, the condensation polycyclic compound of one embodiment may include a second substituent connected to the first heteroatom. The second substituent may be a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heteroaryl group having 2 to 30 carbon atoms. In this case, the second substituent does not include two or more of any one of the dibenzofuran moiety, dibenzothiophen moiety, and carbazole moiety. For example, the second substituent may not include a 2-[3-(dibenzofuranphenyl-2-yl)phenyl]dibenzofuran group or a 2-[3-(dibenzothiophenphenyl-2-yl)phenyl]dibenzothiophen group.

[0132] A condensed polycyclic compound of one embodiment can be represented by the following chemical formula 1.

[0133] [Chemical Formula 1]

[0134]

[0135] A condensed polycyclic compound of one embodiment represented by Chemical Formula 1 may include a condensed ring core formed by the condensation of five rings centered around a first boron atom, a first nitrogen atom, and a first heteroatom, and a first substituent connected to the condensed ring core.

[0136] In Chemical Formula 1, R1 to R 11 Each is independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a hydroxyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cyclic aryl group having 6 to 40 carbon atoms, or a substituted or unsubstituted cyclic heteroaryl group having 2 to 40 carbon atoms. For example, R 1, R 4, R 5, R 8, R9 and R 11 Each is independently a hydrogen atom or a deuterium atom, and R2, R 3, R6 and R7 are each independently a substituted or unsubstituted t-butyl group, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted carbazole group, and R 10 can be a substituted or unsubstituted t-butyl group or a substituted or unsubstituted phenyl group. For example, R 1, R 4, R 5, R 8, R9 and R 11 Each is independently a hydrogen atom or a deuterium atom, and R 2, R 3, R6 and R7 are each independently a substituted or unsubstituted t-butyl group, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted carbazole group, and R 10 It may be a substituted or unsubstituted t-butyl group or a substituted or unsubstituted phenyl group.

[0137] In Chemical Formula 1, X is O, S, or NR 12 am.

[0138] In Chemical Formula 1, R 12 is a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heteroaryl group having 2 to 30 carbon atoms. For example, R 12 may be a substituted or unsubstituted m-terphenyl group. R 12 If is a substituted or unsubstituted ring-forming heteroaryl group having 2 to 30 carbon atoms, R 12 It does not contain two or more of any one of the dibenzofuran moiety, dibenzothiophen moiety, and carbazole moiety. That is, R 12 It may include one each of a dibenzofuran moiety, a dibenzothiophen moiety, and a carbazole moiety, but may not include two or more of any of the dibenzofuran moiety, dibenzothiophen moiety, and carbazole moiety. For example, R 12It may not contain two or more dibenzofuran moietyes, may not contain two or more dibenzothiophen moietyes, and may not contain two or more carbazole moietyes. In addition, R 12 may not correspond to a structure containing both a dibenzofuran moiety and a dibenzothiophen moiety, may not correspond to a structure containing both a dibenzofuran moiety and a carbazole moiety, and may not correspond to a structure containing both a dibenzothiophen moiety and a carbazole moiety. For example, R 12 It may not contain a 2-[3-(dibenzofuranphenyl-2-yl)phenyl]dibenzofuran group.

[0139] In Chemical Formula 1, Ar is a substituent represented by the following Chemical Formula 2. Ar is, optionally, the aforementioned R 12 The structure may be identical to the substituent represented by , or it may be different from the structure.

[0140] [Chemical Formula 2]

[0141]

[0142] In Chemical Formula 2, R x1 to R x4 Each is independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a hydroxyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cyclic aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted cyclic heteroaryl group having 2 to 30 carbon atoms. For example, R x1 to R x4 Each may independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heteroaryl group having 2 to 30 carbon atoms.

[0143] In Chemical Formula 2, R x1to R x3 At least one of them is a substituted or unsubstituted cyclic aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted cyclic aryl group having 2 to 30 carbon atoms. For example, R x1 to R x3 One of them is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted dibenzofuran group, or a substituted or unsubstituted dibenzothiophene group, and R x1 to R x3 The remainder of the group may be hydrogen atoms, deuterium atoms, or unsubstituted t-butyl groups.

[0144] In Chemical Formula 2, R y1 to R y4, and R z1 to R z5 Each is independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a hydroxyl group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thio group, a substituted or unsubstituted boron group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine 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 cyclic aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted cyclic heteroaryl group having 2 to 30 carbon atoms. y1 to R y4, and R z1 to R z5 Each may independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted oxy group, or a substituted or unsubstituted thio group. Or, R y1 to R y4, and R z1 to R z5 Each combines with adjacent tiles to form a ring. For example, R y4 and R z5 Each corresponds independently to a substituted or unsubstituted ox group or a substituted or unsubstituted thi group, and Ry4 and R z5 They can combine with each other to form a heterocycle containing an oxygen atom or a sulfur atom. Or, R y2 or R z1 corresponds to a substituted or unsubstituted ox group, or a substituted or unsubstituted thi group, and R y2 and R z1 They can combine with each other to form heterocycles containing oxygen or sulfur atoms. R y4 and R z5 They combine with each other to form a ring or R y1 and R z1 As they combine with each other to form a ring, in one embodiment, Formula 2 may provide a dibenzofuran moiety or a dibenzothiophen moiety.

[0145] In Chemical Formula 2, is the position connected to the above chemical formula 1.

[0146] Meanwhile, in this specification, the benzene ring substituted with substituents represented by R1 to R4 in Formula 1 corresponds to the aforementioned second benzene ring, the benzene ring substituted with substituents represented by R5 to R8 corresponds to the aforementioned third benzene ring, and R9 to R 11 A benzene ring substituted with a substituent represented by can correspond to the first benzene ring described above. In Chemical Formula 1, the substituent represented by Ar can correspond to the first substituent described above.

[0147] Also, in Chemical Formula 2, R x1 to R x4 The benzene ring substituted with a substituent represented by corresponds to the aforementioned first benzene moiety, and R y1 to R y4 and R z1 to R z5 A biphenyl moiety substituted with a substituent represented by can correspond to the aforementioned first substituent. Specifically, R y1 to R y4The benzene ring substituted with a substituent represented by corresponds to the aforementioned second benzene moiety, and R z1 to R z5 The benzene ring substituted with the substituent denoted by may correspond to the aforementioned third benzene moiety. R x1 to R x4 Any substituent corresponding to a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heteroaryl group having 2 to 30 carbon atoms, among the substituents represented by, may correspond to the aforementioned second sub-substituent.

[0148] In one embodiment, R x1 to R x3 At least one of them may be a substituent represented by any one of the following chemical formulas 3-1 to 3-4. For example, R x1 to R x3 One of them is a substituent represented by any one of the following chemical formulas 3-1 to 3-4, and R x1 to R x3 The remainder of the group may be hydrogen atoms, deuterium atoms, or unsubstituted t-butyl groups.

[0149] [Chemical Formula 3-1]

[0150]

[0151] [Chemical Formula 3-2]

[0152]

[0153] [Chemical Formula 3-3]

[0154]

[0155] [Chemical Formula 3-4]

[0156]

[0157] In Chemical Formulas 3-1 to 3-4, Y1 to Y7 may each independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heteroaryl group having 2 to 30 carbon atoms. For example, Y1 to Y7 may each independently be a hydrogen atom or a deuterium atom.

[0158] In Chemical Formula 3-1, n1 may be an integer from 0 to 5. If n1 is 0, it may mean that the condensed polycyclic compound of one embodiment is not substituted with Y1. If n1 is 5 and all Y1 are hydrogen atoms, it may be the same as the case where n1 is 0. If n1 is an integer of 2 or more, each of the plural Y1s provided may be the same, or at least one of the plural Y1s may be different.

[0159] In Chemical Formula 3-2, n2 may be an integer from 0 to 4. If n2 is 0, it may mean that the condensed polycyclic compound of one embodiment is not substituted with Y2. If n2 is 4 and all Y2 are hydrogen atoms, it may be the same as the case where n2 is 0. If n2 is an integer of 2 or more, each of the plural Y2 may be the same, or at least one of the plural Y2 may be different.

[0160] In Chemical Formula 3-2, n3 may be an integer from 0 to 5. If n3 is 0, it may mean that the condensed polycyclic compound of one embodiment is not substituted with Y3. If n3 is 5 and all Y3 are hydrogen atoms, it may be the same as the case where n3 is 0. If n3 is an integer of 2 or more, each of the plural Y3s provided may be the same, or at least one of the plural Y3s may be different.

[0161] In Chemical Formula 3-3, n4 may be an integer between 0 and 3. If n4 is 0, it may mean that the condensed polycyclic compound of one embodiment is not substituted with Y4. If N4 is 3 and all Y4 are hydrogen atoms, it may be the same as the case where n4 is 0. If N4 is an integer of 2 or more, each of the plural Y4s provided may be the same, or at least one of the plural Y4s may be different.

[0162] In Chemical Formula 3-3, n5 may be an integer between 0 and 4. If n5 is 0, it may mean that the condensed polycyclic compound of one embodiment is not substituted with Y5. If n5 is 4 and all Y5 are hydrogen atoms, it may be the same as the case where n5 is 0. If N5 is an integer of 2 or more, each of the plural Y5 may be the same, or at least one of the plural Y5 may be different.

[0163] In Chemical Formula 3-4, n6 may be an integer between 0 and 3. If n6 ​​is 0, it may mean that the condensed polycyclic compound of one embodiment is not substituted with Y6. If n6 ​​is 3 and all Y6 are hydrogen atoms, it may be the same as the case where n6 is 0. If n6 ​​is an integer of 2 or more, each of the plural Y6s provided may be the same, or at least one of the plural Y6s may be different.

[0164] In Chemical Formula 3-4, n7 may be an integer between 0 and 4. If n7 is 0, it may mean that the condensed polycyclic compound of one embodiment is not substituted with Y7. If n7 is 4 and all Y7 are hydrogen atoms, it may be the same as the case where n7 is 0. If n7 is an integer of 2 or more, each of the plural Y7s provided may be the same, or at least one of the plural Y7s may be different.

[0165] In Chemical Formulas 3-1 to 3-4, may be a position connected to the above chemical formula 1.

[0166] In one embodiment, the substituent represented by Formula 2 may be represented by any one of the following Formulas 2-1 to 2-3.

[0168] [Chemical Formula 2-1]

[0169]

[0170] [Chemical Formula 2-2]

[0171]

[0172] [Chemical Formula 2-3]

[0173]

[0174] In Chemical Formulas 2-1 to 2-3, Z1 to Z6 may each independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms. For example, Z1 to Z6 may each independently be a hydrogen atom or a deuterium atom.

[0175] In Chemical Formula 2-1, m1 may be an integer from 0 to 4. If m1 is 0, it may mean that the condensed polycyclic compound of one embodiment is not substituted with Z1. If m1 is 4 and all Z1s are hydrogen atoms, it may be the same as the case where m1 is 0. If m1 is an integer of 2 or more, each of the Z1s provided in the plurality may be the same, or at least one of the plurality of Z1s may be different.

[0176] In Chemical Formula 2-1, m2 may be an integer from 0 to 5. If m2 is 0, it may mean that the condensed polycyclic compound of one embodiment is not substituted with Z2. If m2 is 5 and all Z2 are hydrogen atoms, it may be the same as the case where m2 is 0. If m2 is an integer of 2 or more, each of the Z2 provided in the plurality may be the same, or at least one of the plurality of Z2 may be different.

[0177] In Chemical Formula 2-2, m3 may be an integer between 0 and 3. If m3 is 0, it may mean that the condensed polycyclic compound of one embodiment is not substituted with Z3. If m3 is 3 and all Z3s are hydrogen atoms, it may be the same as the case where m3 is 0. If m3 is an integer of 2 or more, each of the Z3s provided in the plurality may be the same, or at least one of the Z3s may be different.

[0178] In Chemical Formula 2-2, m4 may be an integer between 0 and 4. If m4 is 0, it may mean that the condensed polycyclic compound of one embodiment is not substituted with Z4. If m4 is 4 and all Z4 are hydrogen atoms, it may be the same as the case where m4 is 0. If m4 is an integer of 2 or more, each of the plural Z4s provided may be the same, or at least one of the plural Z4s may be different.

[0179] In Chemical Formula 2-3, m5 may be an integer between 0 and 3. If m5 is 0, it may mean that the condensed polycyclic compound of one embodiment is not substituted with Z5. If m5 is 3 and all Z5s are hydrogen atoms, it may be the same as the case where m5 is 0. If m5 is an integer of 2 or more, each of the Z5s provided in the plurality may be the same, or at least one of the plurality of Z5s may be different.

[0180] In Chemical Formula 2-3, m6 may be an integer between 0 and 4. If m6 is 0, it may mean that the condensed polycyclic compound of one embodiment is not substituted with Z6. If m6 is 4 and all Z6 are hydrogen atoms, it may be the same as the case where m6 is 0. If m6 is an integer of 2 or more, each of the plural Z6s provided may be the same, or at least one of the plural Z6s may be different.

[0181] In Chemical Formulas 2-1 to 2-3, is the position connected to the above chemical formula 1.

[0182] In Chemical Formulas 2-1 to 2-3, R x1 to R x4 The same content as described in Chemical Formula 2 above may be applied.

[0183] In one embodiment, the substituent represented by Formula 2 may be represented by any one of the following Formulas 2-4 to 2-17.

[0184] [Chemical Formula 2-4]

[0185]

[0186] [Chemical Formula 2-5]

[0187]

[0188] [Chemical Formula 2-6]

[0189]

[0190] [Chemical Formula 2-7]

[0191]

[0192] [Chemical Formula 2-8]

[0193]

[0194] [Chemical Formula 2-9]

[0195]

[0196] [Chemical Formula 2-10]

[0197]

[0198] [Chemical Formula 2-11]

[0199]

[0200] [Chemical Formula 2-12]

[0201]

[0202] [Chemical Formula 2-13]

[0203]

[0204] [Chemical Formula 2-14]

[0205]

[0206] [Chemical Formula 2-15]

[0207]

[0208] [Chemical Formula 2-16]

[0209]

[0210] [Chemical Formula 2-17]

[0211]

[0212] In chemical formulas 2-4 to 2-17, R x11 to R x24 Each can independently be a hydrogen atom, a deuterium atom, an unsubstituted t-butyl group, or an unsubstituted phenyl group. For example, R x11 to R x24 Each can independently be a hydrogen atom, a deuterium atom, or an unsubstituted t-butyl group.

[0213] In Chemical Formulas 2-4 to 2-17, p1 to p14 are each independently integers from 0 to 3. When each of p1 to p14 is 0, the condensed polycyclic compound of one embodiment is R x11 to R x24 It may mean that they are not substituted for each. Each of p1 to p14 is 3, and R x11to R x24 If each is a hydrogen atom, it may be the same as the case where each of p1 to p14 is 0. If each of p1 to p14 is an integer of 2 or more, R provided in the plural x11 to R x24 Each one is either identical or a plurality of R x11 to R x24 At least one of them may be different.

[0214] In chemical formulas 2-4 to 2-17, is the position connected to the above chemical formula 1.

[0215] Meanwhile, any hydrogen atom in Chemical Formulas 2-4 to 2-17 may be substituted with a deuterium atom. Each of Chemical Formulas 2-4 to 2-17 may include a structure in which any hydrogen atom is substituted with a deuterium atom.

[0216] In one embodiment, the condensed polycyclic compound represented by Formula 1 may be represented by any one of the following Formulas 1-1 to 1-6.

[0217] [Chemical Formula 1-1]

[0218]

[0219] [Chemical Formula 1-2]

[0220]

[0221] [Chemical Formula 1-3]

[0222]

[0223] [Chemical Formula 1-4]

[0224]

[0225] [Chemical Formula 1-5]

[0226]

[0227] [Chemical Formula 1-6]

[0228]

[0229] In Chemical Formulas 1-1 to 1-6, R a1 to R a6 Each may independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted t-butyl group, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms. For example, R a1 to R a6 Each can independently be a hydrogen atom, an unsubstituted t-butyl group, or a phenyl group substituted with a t-butyl group.

[0230] In Chemical Formulas 1-1 to 1-6, R b1 to R b17 Each may independently be a hydrogen atom, a deuterium atom, a cyano group, a substituted or unsubstituted t-butyl group, a substituted or unsubstituted cyclic aryl group having 6 to 30 carbon atoms, or an unsubstituted cyclic heteroaryl group having 2 to 30 carbon atoms. For example, R b1 to R b17 Each may independently be a hydrogen atom, a deuterium atom, a cyano group, a substituted or unsubstituted t-butyl group, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted pyridine group.

[0231] In Chemical Formula 1-1, b1 and b2 may each independently be integers from 0 to 5. When b1 and b2 are each 0, the condensed polycyclic compound of one embodiment is R b1 and R b2 It can mean that they are not substituted into each. b1 and b2 are each 5, and R b1 and R b2 If each is a hydrogen atom, it may be equivalent to the case where b1 and b2 are each 0. If b1 and b2 are each integers greater than or equal to 2, R is provided in the plural. b1 and R b2 Each one is either identical or a plurality of R b1 and R b2 At least one of them may be different.

[0232] In Chemical Formula 1-2, b3 and b4 may each independently be integers from 0 to 5. When b3 and b4 are each 0, the condensed polycyclic compound of one embodiment is R b3 and R b4 It may mean that they are not substituted into each. b3 and b4 are each 5, and R b3 and R b4 If each is a hydrogen atom, it may be the same as the case where b3 and b4 are each 0. If b3 and b4 are each integers greater than or equal to 2, R is provided in the plural. b3 and R b4 Each one is either identical or a plurality of R b3 and R b4 At least one of them may be different.

[0233] In Chemical Formula 1-3, b5 may be an integer from 0 to 5. When b5 is 0, the condensed polycyclic compound of one embodiment is R b5 It could mean that it was not substituted. b5 is 5, and R b5 If all are hydrogen atoms, it may be the same as the case where b5 is 0. If b5 is an integer greater than or equal to 2, R provided in the plural b5 Each one is either identical or a plurality of R b5 At least one of them may be different.

[0234] In Chemical Formula 1-3, b6 and b7 may each independently be integers from 0 to 4. When b6 and b7 are each 0, the condensed polycyclic compound of one embodiment is R b6 and R b7 It may mean that they are not substituted into each. b3 and b4 are each 4, and R b6 and R b7 If each is a hydrogen atom, it may be equivalent to the case where b6 and b7 are each 0. If b6 and b7 are each integers greater than or equal to 2, R is provided in the plural. b6and R b7 Each one is either identical or a plurality of R b6 and R b7 At least one of them may be different.

[0235] In Chemical Formula 1-3, b5 may be an integer from 0 to 5. When b5 is 0, the condensed polycyclic compound of one embodiment is R b5 It could mean that it was not substituted. b5 is 5, and R b5 If all are hydrogen atoms, it may be the same as the case where b5 is 0. If b5 is an integer greater than or equal to 2, R provided in the plural b5 Each one is either identical or a plurality of R b5 At least one of them may be different.

[0236] In Chemical Formula 1-3, b6 and b7 may each independently be integers from 0 to 4. When b6 and b7 are each 0, the condensed polycyclic compound of one embodiment is R b6 and R b7 It may mean that they are not substituted into each. b3 and b4 are each 4, and R b6 and R b7 If each is a hydrogen atom, it may be equivalent to the case where b6 and b7 are each 0. If b6 and b7 are each integers greater than or equal to 2, R is provided in the plural. b6 and R b7 Each one is either identical or a plurality of R b6 and R b7 At least one of them may be different.

[0237] In Chemical Formula 1-4, b8 may be an integer from 0 to 5. When b8 is 0, the condensed polycyclic compound of one embodiment is R b8 It could mean that it was not replaced by. b8 is 5, and R b8 If all of these are hydrogen atoms, it may be the same as the case where b8 is 0. If b8 is an integer greater than or equal to 2, R provided in the pluralb8 Each one is either identical or a plurality of R b8 At least one of them may be different.

[0238] In Chemical Formula 1-4, b9 and b10 may each independently be integers from 0 to 4. When b9 and b10 are each 0, the condensed polycyclic compound of one embodiment is R b9 and R b10 It may mean that they are not substituted for each. b9 and b10 are each 4, and R b9 and R b10 If each is a hydrogen atom, it may be equivalent to the case where b9 and b10 are each 0. If b9 and b10 are each integers greater than or equal to 2, R is provided in the plural. b9 and R b10 Each one is either identical or a plurality of R b9 and R b10 At least one of them may be different.

[0239] In Chemical Formula 1-5, b11 may be an integer from 0 to 5. When b11 is 0, the condensed polycyclic compound of one embodiment is R b11 It could mean that it was not substituted with. b11 is 5, and R b11 If all of these are hydrogen atoms, it may be the same as the case where b11 is 0. If b11 is an integer greater than or equal to 2, R provided in the plural b11 Each one is either identical or a plurality of R b11 At least one of them may be different.

[0240] In Chemical Formula 1-5, b12 and b13 may each independently be integers from 0 to 4. When b12 and b13 are each 0, the condensed polycyclic compound of one embodiment is R b12 and R b13 It may mean that they are not substituted into each. b12 and b13 are each 4, and R b12 and R b13If each is a hydrogen atom, it may be equivalent to the case where b12 and b13 are each 0. If b12 and b13 are each integers greater than or equal to 2, R is provided in the plural. b12 and R b13 Each one is either identical or a plurality of R b12 and R b13 At least one of them may be different.

[0241] In Chemical Formula 1-6, b14 to b17 may each independently be an integer from 0 to 4. When each of b14 to b17 is 0, the condensed polycyclic compound of one embodiment is R b14 to R b17 It may mean that they are not substituted for each. Each of b14 to b17 is 4, and R b14 to R b17 If each is a hydrogen atom, it may be the same as the case where each of b14 to b17 is 0. If each of b14 to b17 is an integer of 2 or more, R provided in the plural b14 to R b17 Each one is either identical or a plurality of R b14 to R b17 At least one of them may be different.

[0243] In Chemical Formulas 1-1 to 1-6, X and Ar may be applied in the same way as described in Chemical Formula 1.

[0244] Any hydrogen atom in Chemical Formulas 1-1 to 1-6 may be substituted with a deuterium atom. Each of Chemical Formulas 1-1 to 1-6 may include a structure in which any hydrogen atom is substituted with a deuterium atom.

[0245] In one embodiment, the condensed polycyclic compound represented by Chemical Formula 1 can be represented by the following Chemical Formula 1-7.

[0246] [Chemical Formula 1-7]

[0247]

[0248] In Chemical Formula 1-7, A1 to A5 may 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 cyclic aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted cyclic heteroaryl group having 2 to 30 carbon atoms. However, if two or more of A1 to A5 are each independently a substituted or unsubstituted dibenzofuran group, a substituted or unsubstituted dibenzothiophen group, and a substituted or unsubstituted carbazole group, it may not be included. For example, A1 to A4 may each independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, and A5 may be a hydrogen atom, a deuterium atom, a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heteroaryl group having 2 to 30 carbon atoms.

[0249] In chemical formulas 1-7, Ar and R1 to R 11 The same content as explained in Chemical Formula 1 can be applied.

[0250] In one embodiment, the condensed polycyclic compound represented by Formula 1 may be represented by any one of the following Formulas 1-8 to 1-16.

[0251] [Chemical Formula 1-8]

[0252]

[0253] [Chemical Formula 1-9]

[0255]

[0256] [Chemical Formula 1-10]

[0257]

[0258] [Chemical Formula 1-11]

[0259]

[0260] [Chemical Formula 1-12]

[0261]

[0262] [Chemical Formula 1-13]

[0263]

[0264] [Chemical Formula 1-14]

[0265]

[0266] [Chemical Formula 1-15]

[0267]

[0268] [Chemical Formula 1-16]

[0269]

[0270] In Chemical Formulas 1-8 to 1-16, A 11 , A 13 , A 14 , A 16 , A 18 , A 20 , A 22 , A 24 , A 26 , and A 28 Each can independently be a hydrogen atom, a deuterium atom, or a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms. For example, A 11 , A 13 , A 14 , A 16 , A 18 , A 20 , A 22 , A 24 , A 26 , and A 28 Each can independently be a hydrogen atom or a substituted or unsubstituted phenyl group.

[0271] In Chemical Formulas 1-8 to 1-16, A 12, A 15 , A 17 , A 19 , A 21, A 23 , A 25 , A 27 , and A 29 Each may independently be a hydrogen atom, a deuterium atom, or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms. For example, A 12 is A 12, A 15 , A 17 , A 19 , A 21 , A 23 , A 25 , A 27 , and A 29 Each can independently be a hydrogen atom, a deuterium atom, or a substituted or unsubstituted t-butyl group.

[0272] In Chemical Formulas 1-8 to 1-16, a1, a3, a4, a6, a8, a10, a12, a14, a16, and a18 are each independently integers from 0 to 5. When each of a1, a3, a4, a6, a8, a10, a12, a14, a16, and a18 is 0, the condensed polycyclic compound of one embodiment is A 11 , A 13 , A 14 , A 16 , A 18 , A 20 , A 22 , A 24 , A 26 , and A 28 It can mean that they are not substituted into each. a1, a3, a4, a6, a8, a10, a12, a14, a16, and a18 are each 5, and A 11 , A 13 , A 14 , A 16 , A 18 , A 20 , A 22 , A 24 , A 26 , and A 28If each is a hydrogen atom, it may be equivalent to the case where a1, a3, a4, a6, a8, a10, a12, a14, a16, and a18 are each 0. If a1, a3, a4, a6, a8, a10, a12, a14, a16, and a18 are each integers greater than or equal to 2, A provided in the plural 11 , A 13 , A 14 , A 16 , A 18 , A 20 , A 22 , A 24 , A 26 , and A 28 Each one is either identical or a plurality of A 11 , A 13 , A 14 , A 16 , A 18 , A 20 , A 22 , A 24 , A 26 , and A 28 At least one of them may be different.

[0273] In Chemical Formulas 1-8 to 1-16, a2, a5, a7, a9, a11, a13, a15, a17, and a19 are each independently integers from 0 to 3. When each of a2, a5, a7, a9, a11, a13, a15, a17, and a19 is 0, the condensed polycyclic compound of one embodiment is A 12, A 15 , A 17 , A 19 , A 21 , A 23 , A 25 , A 27 , and A 29 It can mean that they are not substituted into each. a2, a5, a7, a9, a11, a13, a15, a17, and a19 are each 5, and A 12, A 15 , A 17 , A 19 , A 21, A 23 , A 25 , A 27 , and A 29 If each is a hydrogen atom, it may be equivalent to the case where a2, a5, a7, a9, a11, a13, a15, a17, and a19 are each 0. If a2, a5, a7, a9, a11, a13, a15, a17, and a19 are each integers greater than or equal to 2, A provided in the plural 12, A 15 , A 17 , A 19 , A 21 , A 23 , A 25 , A 27 , and A 29 Each one is either identical or a plurality of A 12, A 15 , A 17 , A 19 , A 21 , A 23 , A 25 , A 27 , and A 29 At least one of them may be different.

[0274] In chemical formulas 1-8 to 1-16, Ar and R1 to R 11 The same content as explained in Chemical Formula 1 can be applied.

[0275] Meanwhile, any hydrogen atom in Chemical Formulas 1-8 to 1-16 may be substituted with a deuterium atom. Each of Chemical Formulas 1-8 to 1-16 may include a structure in which any hydrogen atom is substituted with a deuterium atom.

[0277] The condensed polycyclic compound of one embodiment may be any one of the compounds listed in Compound Group 1 below. At least one functional layer included in the light-emitting element (ED) of one embodiment may include at least one condensed polycyclic compound among the compounds listed in Compound Group 1. The light-emitting element (ED) of one embodiment may include at least one condensed polycyclic compound among the compounds listed in Compound Group 1 in the light-emitting layer (EML).

[0278] [Compound Group 1]

[0279]

[0280]

[0281]

[0282]

[0283]

[0284]

[0285]

[0286]

[0287]

[0288]

[0289]

[0290]

[0291]

[0292]

[0293]

[0294]

[0295]

[0296]

[0297]

[0298]

[0299]

[0300]

[0301]

[0302]

[0303]

[0304]

[0305]

[0306]

[0307]

[0308]

[0309]

[0310]

[0311]

[0312]

[0313]

[0314]

[0315]

[0316]

[0317]

[0318]

[0319]

[0320]

[0321]

[0322]

[0323]

[0324]

[0325]

[0326]

[0327] In the specific compounds presented in compound group 1, "D" means a deuterium atom.

[0328] A condensed polycyclic compound of one embodiment can achieve a long lifespan by including a structure in which a first substituent is connected to the condensed polycyclic heterocyclic ring.

[0329] A condensed polycyclic compound of one embodiment comprises a condensed ring core comprising a first boron atom, a first nitrogen atom, and a first heteroatom, wherein five rings are condensed, and a first substituent connected to the first nitrogen atom of the condensed ring core. In one embodiment, the condensed ring core included in the condensed polycyclic compound may form five rings as the first to third benzene rings are connected through the first boron atom, the first nitrogen atom, and the first heteroatom. The first substituent may include a structure comprising a first benzene moiety connected to the first nitrogen atom, and a first sub-substituent and a second sub-substituent respectively connected to the first benzene moiety. The first substituent may have a structure comprising a first benzene moiety connected to the first nitrogen atom, and a first sub-substituent connected to a carbon at an ortho position relative to the carbon atom connected to the first nitrogen atom among the carbon atoms constituting the first benzene moiety. The first sub-substituent may include a second benzene moiety connected at an ortho position carbon with respect to the carbon atom connected to the first nitrogen atom among the carbon atoms constituting the first benzene moiety, and a third benzene moiety connected at an ortho position carbon with respect to the carbon atom connected to the first benzene moiety among the carbon atoms constituting the second benzene moiety. The second sub-substituent may be a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heteroaryl group having 2 to 30 carbon atoms.

[0330] A condensed polycyclic compound according to one embodiment of the present invention can exhibit excellent molecular stability due to the specific structure of the first substituent, thereby contributing to the longevity of a light-emitting device (ED). The condensed polycyclic compound of one embodiment can effectively maintain the trigonal palanar structure of the boron atom through the steric hindrance effect of the first substituent. As the boron atom possesses electron-deficient characteristics due to the empty p-orbital, it may form bonds with other nucleophiles and transform into a tetrahedral structure, which can cause device degradation. According to the present invention, the condensed polycyclic compound represented by Formula 1 includes a first substituent having a steric hindrance structure, so the empty p-orbital of the boron atom can be effectively protected, thereby preventing degradation caused by structural deformation.

[0331] In addition, the condensed polycyclic compound of one embodiment can control the formation of excimers or exciplexes by suppressing intermolecular interactions due to the introduction of the first substituent, thereby increasing luminescence efficiency. Furthermore, the condensed polycyclic compound of one embodiment represented by Chemical Formula 1 includes the first substituent, which can increase the dihedral angle between the plane containing the condensed ring core structure centered on the boron atom and the plane containing the first substituent. Consequently, the intermolecular distance increases, thereby having the effect of reducing dexter energy transfer. Dexter energy transfer is a phenomenon in which triplet excitons move between molecules; it increases when the intermolecular distance is short and can be a factor that increases the quenching phenomenon associated with an increase in triplet concentration. According to the present invention, the condensed polycyclic compound of one embodiment can suppress dexter energy transfer by increasing the distance between adjacent molecules due to a structure with high steric hindrance, thereby suppressing the degradation of lifespan that occurs as the triplet concentration increases. Therefore, when the condensed polycyclic compound of one embodiment is applied to the light-emitting layer (EML) of a light-emitting device (ED), not only can the light-emitting efficiency be increased, but the device lifespan can also be improved.

[0333] The emission spectrum of the condensed polycyclic compound of one embodiment represented by Chemical Formula 1 has a full width at half maximum (FWHM) of 10 nm to 50 nm, and preferably has a full width at half maximum (FWHM) of 20 nm to 40 nm. As the emission spectrum of the first dopant of one embodiment represented by Chemical Formula 1 has a full width at half maximum (FWHM) of the above range, the luminous efficiency can be improved when applied to a device. In addition, the device lifespan can be improved when used as a blue light-emitting device material for a light-emitting device.

[0334] In one embodiment, the condensed polycyclic compound of one embodiment represented by Formula 1 may be a thermally active delayed fluorescent emitting material. Additionally, the condensed polycyclic compound of one embodiment represented by Formula 1 has a difference (△E) between the lowest triplet excitation energy level (T1) and the lowest singlet excitation energy level (S1). ST It may be a thermally activated delayed fluorescent dopant having a value of 0.6 eV or less. The condensed polycyclic compound of one embodiment represented by Chemical Formula 1 has a difference (△E) between the lowest triplet excitation energy level (T1) and the lowest singlet excitation energy level (S1). ST It may be a thermally activated delayed fluorescent dopant having a value of 0.2 eV or less. However, the examples are not limited thereto.

[0335] In one embodiment, the condensed polycyclic compound of one embodiment represented by Chemical Formula 1 may include a first substituent and a second substituent within the compound. By controlling the number of substituents and the substituent positions of the first and second substituents, the singlet energy level and the triplet energy level of the overall compound can be appropriately controlled. Through this, the condensed polycyclic compound according to one embodiment of the present invention can exhibit improved thermally activated delayed fluorescence characteristics.

[0336] The condensed polycyclic compound of one embodiment represented by Chemical Formula 1 may be a light-emitting material having a center wavelength of emission in the wavelength range of 430 nm to 490 nm. For example, the condensed polycyclic compound of one embodiment represented by Chemical Formula 1 may be a blue Thermally Activated Delayed Fluorescence (TADF) dopant. However, the embodiment is not limited thereto, and when the condensed polycyclic compound of one embodiment is used as a light-emitting material, the first dopant may be used as a dopant material that emits light in various wavelength ranges, such as a red light-emitting dopant or a green light-emitting dopant.

[0337] In one embodiment of the light-emitting device (ED), the light-emitting layer (EML) may emit delayed fluorescence. For example, the light-emitting layer (EML) may emit thermally activated delayed fluorescence (TADF).

[0338] Additionally, the light-emitting layer (EML) of the light-emitting device (ED) may emit blue light. For example, the light-emitting layer (EML) of the organic electroluminescent device (ED) of one embodiment may emit blue light in a wavelength range of 490 nm or less. However, the embodiment is not limited thereto, and the light-emitting layer (EML) may emit green light or red light.

[0339] Meanwhile, the condensed polycyclic compound of one embodiment may be included in the emitting layer (EML). The condensed polycyclic compound of one embodiment may be included in the emitting layer (EML) as a dopant material. The condensed polycyclic compound of one embodiment may be a thermally activated delayed fluorescent emitting material. The condensed polycyclic compound of one embodiment may be used as a thermally activated delayed fluorescent dopant. For example, in the light-emitting device (ED) of one embodiment, the emitting layer (EML) may include at least one of the condensed polycyclic compounds listed in the compound group 1 described above as a thermally activated delayed fluorescent dopant. However, the use of the condensed polycyclic compound of one embodiment is not limited thereto.

[0340] In one embodiment, the light-emitting layer (EML) may include a plurality of compounds. The light-emitting layer (EML) of one embodiment may include a condensed polycyclic compound represented by Formula 1, i.e., a first compound, and additionally may include 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.

[0341] In one embodiment, the light-emitting layer (EML) comprises a first compound represented by Formula 1, and may further comprise at least one of a second compound represented by Formula HT-1 and a third compound represented by Formula ET-1.

[0342] In one embodiment, the emitting layer (EML) may include a second compound represented by the following chemical formula HT-1. In one embodiment, the second compound may be used as a hole-transporting host material of the emitting layer (EML).

[0343] [Chemical Formula HT-1]

[0344]

[0345] In the chemical formula HT-1, M1 to M8 are each independently N or CR 51 It can be. For example, M to M8 are all CR 51 It could be. Or, one of M1 to M8 is N, and the rest are CR 51 It could be.

[0346] In the chemical formula HT-1, L1 may be a direct linkage, substituted or unsubstituted cyclic arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted cyclic heteroarylene group having 2 to 30 carbon atoms. For example, L1 may be a direct linkage, substituted or unsubstituted phenylene group, a substituted or unsubstituted divalent biphenyl group, a substituted or unsubstituted divalent carbazole group, etc., but the examples are not limited thereto.

[0347] In the chemical formula HT-1, Y a is direct linkage, CR 52 R 53 , or SiR 54 R 55 It can be. That is, the two benzene rings connected to the nitrogen atom of the chemical formula HT-1 are directly bonded, , or It can mean that it is connected through. In the chemical formula HT-1, Y a In the case of direct bonding, the substituent represented by the chemical formula HT-1 may include a carbazole moiety.

[0348] In the chemical formula HT-1, Ar a may be a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heteroaryl group having 2 to 30 carbon atoms. For example, Ar a The group may be a substituted or unsubstituted carbazole group, a substituted or unsubstituted dibenzofuran group, a substituted or unsubstituted dibenzothiophen group, or a substituted or unsubstituted biphenyl group, but the examples are not limited thereto.

[0349] In the chemical formula HT-1, R 51 to R 55 Each may 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 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms. Or, R 51 to R 55 Each can combine with adjacent tiles to form a ring. For example, R 51 to R 55 Each can independently be a hydrogen atom or a deuterium atom. R 51 to R 55 Each can be an independently unsubstituted methyl group or an unsubstituted phenyl group.

[0350] In one embodiment, the second compound represented by the formula HT-1 may be represented by any one of the compounds listed in the following compound group 2. The emitting layer (EML) may include at least one of the compounds listed in the following compound group 2 as a hole-transporting host material.

[0351] [Compound Group 2]

[0352]

[0353]

[0354]

[0355]

[0356] In the specific compounds presented in Group 2 of compounds, "D" means a deuterium atom, and "Ph" may mean a substituted or unsubstituted phenyl group. For example, in the specific compounds presented in Group 2 of compounds, "Ph" may be an unsubstituted phenyl group.

[0357] In one embodiment, the emitting layer (EML) may include a third compound represented by the following chemical formula ET-1. For example, the third compound may be used as an electron transport host material of the emitting layer (EML).

[0358] [Chemical Formula ET-1]

[0359]

[0360] In the chemical formula ET-1, Z a To Z c At least one is N and the rest are CR 56 is. For example, Z a To Z c One of them is N, and the other two are each independently CR 56 It may be. In this case, the third compound represented by the chemical formula ET-1 may contain a pyridine moiety. Or, Z a To Z c Two of them are N, and the other one is CR56 It may be. In this case, the third compound represented by the chemical formula ET-1 may contain a pyrimidine moiety. Or, Z a To Z c All of them can be N. In this case, the third compound represented by the chemical formula ET-1 may contain a triazine moiety.

[0361] In chemical formula ET-1, R 56 It may be a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted ring-forming aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted ring-forming heteroaryl group having 2 to 60 carbon atoms.

[0362] In the chemical formula ET-1, b1 to b3 can each independently be an integer between 0 and 10.

[0363] In chemical formula ET-1, Ar b or Ar d Each may independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cyclic aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted cyclic heteroaryl group having 2 to 30 carbon atoms. For example, Ar b or Ar d may be a substituted or unsubstituted phenyl group, or a substituted or unsubstituted carbazole group.

[0364] In the chemical formula ET-1, L2 to L4 may each independently be a directly bonded, substituted, or unsubstituted ring-forming arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heteroarylene group having 2 to 30 carbon atoms. Meanwhile, when b1 to b3 are integers of 2 or more, L2 to L4 may each independently be a substituted or unsubstituted ring-forming arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heteroarylene group having 2 to 30 carbon atoms.

[0365] In one embodiment, the third compound may be represented as any one of the compounds of the following compound group 3. The light-emitting element (ED) of one embodiment may include any one of the compounds of the following compound group 3.

[0366] [Compound Group 3]

[0367]

[0368]

[0369]

[0370]

[0371]

[0372]

[0373] In the specific examples of compounds presented in compound group 3, "D" means a deuterium atom and "Ph" means an unsubstituted phenyl group.

[0374] The emitting layer (EML) comprises a second compound and a third compound, and the second compound and the third compound can form an exciplex. In the emitting layer (EML), an exciplex can be formed by a hole-transporting host and an electron-transporting host. At this time, the triplet energy of the exciplex formed by the hole-transporting host and the electron-transporting host may correspond to the difference between the LUMO (Lowest Unoccupied Molecular Orbital) energy level of the electron-transporting host and the HOMO (Highest Occupied Molecular Orbital) energy level of the hole-transporting host.

[0375] For example, the absolute value of the triplet energy level (T1) of the exciplex formed by the hole-transporting host and the electron-transporting host may be 2.4 eV or more and 3.0 eV or less. Additionally, the triplet energy of the exciplex may be a value smaller than the energy gap of each host material. The exciplex may have a triplet energy of 3.0 eV or less, which is the energy gap between the hole-transporting host and the electron-transporting host.

[0376] In one embodiment, the light-emitting layer (EML) may include a fourth compound in addition to the first to third compounds described above. The fourth compound may be used as a phosphorescent sensitizer for the light-emitting layer (EML). Energy may be transferred from the fourth compound to the first compound to cause light emission.

[0377] For example, the light-emitting layer (EML) may include an organometallic complex comprising Pt (platinum) as a central metal atom and ligands bonded to the central metal atom as a fourth compound. In a light-emitting device (ED) of one embodiment, the light-emitting layer (EML) may include a compound represented by the following chemical formula D-1 as a fourth compound.

[0378] [Chemical Formula D-1]

[0379]

[0381] In chemical formula D-1, Q1 to Q4 can each independently be C or N.

[0382] In chemical formula D-1, C1 to C4 may each be an independently substituted or unsubstituted ring-forming hydrocarbon ring with 5 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heterocyclic ring with 2 to 30 carbon atoms.

[0383] In chemical formula D-1, L 11 to L 13 Each is independently directly linked (direct linkage), , , , , may be a substituted or unsubstituted divalent alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted ring-forming arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heteroarylene group having 2 to 30 carbon atoms. 11 to L 13 at, " " refers to the region connected to C1 to C4.

[0384] In chemical formula D-1, b11 to b13 may each be independently 0 or 1. If b11 is 0, C1 and C2 may not be connected to each other. If b12 is 0, C2 and C3 may not be connected to each other. If b13 is 0, C3 and C4 may not be connected to each other.

[0385] In chemical formula D-1, R 61 to R 66Each may 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 cyclic aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted cyclic heteroaryl group having 2 to 60 carbon atoms. Or, R 61 to R 66 Each can combine with adjacent tiles to form a ring. R 61 to R 66 Each can be independently a substituted or unsubstituted methyl group, or a substituted or unsubstituted t-butyl group.

[0386] In Chemical Formula D-1, d1 to d4 are each independently integers from 0 to 4. In Chemical Formula D-1, when each of d1 to d4 is 0, the fourth compound is R 61 to R 64 It may not be substituted with. Each of d1 to d4 is 4, and R 61 to R 64 If each is a hydrogen atom, it may be the same as the case where each of d1 to d4 is 0. If each of d1 to d4 is an integer of 2 or more, R provided in the plural 61 to R 64 Each one is either identical or a plurality of R 61 to R 64 At least one of them may be different.

[0387] In chemical formula D-1, C1 to C4 may each independently be a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocycle represented by any one of the following C-1 to C-4.

[0388]

[0389]

[0390] In C-1 to C-4, P1- is or CR 74 and P2 is or NR 81 and P3 is or NR 82 and P4 is or CR 88 It could be. R 71 to R 88 Each may be an independently substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cyclic aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted cyclic heteroaryl group having 2 to 30 carbon atoms, or may be formed by combining with adjacent groups to form a ring.

[0391] Also, in C-1 to C-4, " " is the part connected to the central metal atom Pt, and " " is adjacent rings (C1 to C4) or linkers (L 11 to L 13 It corresponds to the part connected to ).

[0392] In one embodiment, the light-emitting layer (EML) may include a first compound, which is a condensed polycyclic compound, and at least one of the second to fourth compounds. For example, the light-emitting layer (EML) may include the first compound, the second compound, and the third compound. In the light-emitting layer (EML), the second compound and the third compound form an exciplex, and energy is transferred from the exciplex to the first compound to cause light emission.

[0393] Additionally, the emitting layer (EML) may include a first compound, a second compound, a third compound, and a fourth compound. In the emitting layer (EML), the second compound and the third compound form an exciplex, and energy is transferred from the exciplex to the fourth compound and the first compound, thereby causing light emission. In one embodiment, the fourth compound may be a sensitizer. In the light-emitting device (ED) of one embodiment, the fourth compound included in the emitting layer (EML) can function 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, can accelerate the energy transfer to the first compound, which is a light-emitting dopant, thereby increasing the light emission rate of the first compound. Therefore, the emitting layer (EML) of one embodiment may have improved light emission efficiency. Furthermore, when energy transfer to the first compound is increased, excitons formed in the emitting layer (EML) do not accumulate within the emitting layer (EML) but emit light rapidly, so the degradation of the device may be reduced. Therefore, the lifespan of the light-emitting element (ED) of one embodiment can be increased.

[0394] A light-emitting device (ED) of one embodiment may include a first compound, a second compound, a third compound, and a fourth compound, so that the light-emitting layer (EML) may include a combination of two host materials and two dopant materials. In a light-emitting device (ED) of one embodiment, the light-emitting layer (EML) may simultaneously include two different hosts, a second compound and a third compound, a first compound that emits delayed fluorescence, and a fourth compound including an organometallic complex, thereby exhibiting excellent light-emitting efficiency characteristics.

[0395] In one embodiment, the fourth compound represented by chemical formula D-1 may be represented by at least one of the compounds listed in compound group 4 below. The emitting layer (EML) may include at least one of the compounds listed in compound group 4 below as a sensitizer material.

[0396] [Compound Group 4]

[0397]

[0398]

[0399]

[0400]

[0401] In the specific compounds presented in compound group 4, "D" means a deuterium atom.

[0402] Meanwhile, the light-emitting element (ED) of one embodiment may include a plurality of light-emitting layers. The plurality of light-emitting layers may be provided by stacking them sequentially, and for example, the light-emitting element (ED) including the plurality of light-emitting layers may emit white light. The light-emitting element including the plurality of light-emitting layers may be a light-emitting element with a tandem structure. When the light-emitting element (ED) includes a plurality of light-emitting layers, at least one light-emitting layer (EML) may include a first compound represented by Chemical Formula 1 of one embodiment. Additionally, when the light-emitting element (ED) includes a plurality of light-emitting layers, at least one light-emitting layer (EML) may include all of the first compound, the second compound, the third compound, and the fourth compound as described above.

[0404] In the case where the light-emitting layer (EML) of the light-emitting device (ED) of one embodiment comprises all of the first compound, the second compound, and the third compound described above, the content of the first compound may be 0.1 wt% or more and 5 wt% or less based on the total weight of the first compound, the second compound, and the third compound. However, it is not limited thereto. When the content of the first compound satisfies the aforementioned ratio, energy transfer from the second compound and the third compound to the first compound may be increased, and accordingly, the light-emitting efficiency and device lifespan may be increased.

[0405] The content of the second compound and the third compound in the light-emitting layer (EML) may be the remainder excluding the weight of the first compound mentioned above. For example, the content of the second compound and the third compound in the light-emitting layer (EML) may be 65 wt% or more and 95 wt% or less based on the total weight of the first compound, the second compound, and the third compound.

[0406] The weight ratio of the second compound and the third compound in the total weight of the second compound and the third compound may be about 3:7 to 7:3.

[0407] When the content of the second compound and the third compound satisfies the ratio described above, the charge balance characteristics within the emissive layer (EML) are improved, thereby increasing the luminous efficiency and device lifespan. When the content of the second compound and the third compound deviates from the ratio range described above, the charge balance within the emissive layer (EML) is disrupted, the luminous efficiency decreases, and the device may degrade easily.

[0408] When the emitting layer (EML) includes a fourth compound, the content of the fourth compound may be 4 wt% or more and 30 wt% or less based on the total weight of the first compound, the second compound, the third compound, and the fourth compound in the emitting layer (EML). However, it is not limited thereto. When the content of the fourth compound satisfies the aforementioned content, energy transfer from the host to the first compound, which is the emitting dopant, is increased, thereby improving the luminescence ratio, and accordingly, the luminescence efficiency of the emitting layer (EML) may be improved. When the first compound, the second compound, the third compound, and the fourth compound included in the emitting layer (EML) satisfy the range of the content ratios described above, excellent luminescence efficiency and long lifespan can be achieved.

[0409] In a light-emitting device (ED) of one embodiment, the light-emitting layer (EML) may comprise an anthracene derivative, a pyrene derivative, a fluoranthene derivative, a chrysene derivative, a dihydrobenzanthracene derivative, or a triphenylene derivative. Specifically, the light-emitting layer (EML) may comprise an anthracene derivative or a pyrene derivative.

[0410] In the light-emitting device (ED) of one embodiment illustrated in FIGS. 3 to 6, the light-emitting layer (EML) may further include known hosts and dopants in addition to the hosts and dopants described above, and for example, the light-emitting layer (EML) may include a compound represented by the following chemical formula E-1. The compound represented by the following chemical formula E-1 may be used as a fluorescent host material.

[0411] [Chemical Formula E-1]

[0412]

[0413] In chemical formula E-1, R 31 to R 40 Each may independently be a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted silyl group, a substituted or unsubstituted thio group, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms, a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heteroaryl group having 2 to 30 carbon atoms, or may form a ring by bonding to an adjacent group. Meanwhile, R 31 to R 40 It can combine with adjacent groups to form a saturated hydrocarbon ring, an unsaturated hydrocarbon ring, a saturated heterocyclic ring, or an unsaturated heterocyclic ring.

[0414] In chemical formula E-1, c and d can each independently be integers from 0 to 5.

[0415] Chemical formula E-1 may be represented by any one of the following compounds E1 to E19.

[0416]

[0417]

[0418]

[0419] In one embodiment, the light-emitting layer (EML) may include a compound represented by the following formula E-2a or formula E-2b. The compound represented by the following formula E-2a or formula E-2b may be used as a phosphorescent host material.

[0420] [Chemical Formula E-2a]

[0421]

[0422] In chemical formula E-2a, a is an integer between 0 and 10 inclusive, and L a may be a directly bonded, substituted, or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms. Meanwhile, if a is an integer of 2 or more, multiple L a Each may be an independently substituted or unsubstituted ring-forming arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heteroarylene group having 2 to 30 carbon atoms.

[0423] In addition, in chemical formula E-2a, A1 to A5 are each independently N or CR i It could be. R a to R iEach may independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted amine group, a substituted or unsubstituted thio group, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heteroaryl group having 2 to 30 carbon atoms, or may form a ring by bonding with an adjacent group. a to R i It can combine with adjacent groups to form a hydrocarbon ring or a heteroring containing N, O, S, etc. as ring-forming atoms.

[0424] Meanwhile, in chemical formula E-2a, two or three selected from A1 to A5 are N and the remainder are CR i It could be.

[0425] [Chemical Formula E-2b]

[0426]

[0427] In chemical formula E-2b, Cbz1 and Cbz2 may each independently be an unsubstituted carbazole group, or a carbazole group substituted with a ring-forming aryl group having 6 to 30 carbon atoms. b may be a directly bonded, substituted, or unsubstituted cyclic arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted cyclic arylene group having 2 to 30 carbon atoms. b is an integer from 0 to 10, and if b is an integer of 2 or more, multiple L b Each may be an independently substituted or unsubstituted ring-forming arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heteroarylene group having 2 to 30 carbon atoms.

[0428] A compound represented by chemical formula E-2a or chemical formula E-2b may be represented as any one of the compounds in compound group E-2 below. However, the compounds listed in compound group E-2 below are exemplary, and a compound represented by chemical formula E-2a or chemical formula E-2b is not limited to those listed in compound group E-2 below.

[0429] [Compound Group E-2]

[0430]

[0431]

[0432]

[0433] The emissive layer (EML) may further include common materials known in the art as host materials. For example, the emissive layer (EML) comprises at least one of BCPDS (bis(4-(9H-carbazol-9-yl)phenyl)diphenylsilane), POPCPA ((4-(1-(4-(diphenylamino)phenyl)cyclohexyl)phenyl)diphenyl-phosphine oxide), DPEPO (Bis[2-(diphenylphosphino)phenyl]ether oxide), CBP (4,4'-bis(N-carbazolyl)-1,1'-biphenyl), mCP (1,3-Bis(carbazol-9-yl)benzene), PPF (2,8-Bis(diphenylphosphoryl)dibenzo[b,d]furan), TCTA (4,4',4''-Tris(carbazol-9-yl)-triphenylamine), and TPBi (1,3,5-tris(1-phenyl-1H-benzo[d]imidazole-2-yl)benzene) as a host material. It could be.However, this is not limited thereto, and for example, Alq3 (tris(8-hydroxyquinolino)aluminum), ADN (9,10-di(naphthalene-2-yl)anthracene), TBADN (2-tert-butyl-9,10-di(naphth-2-yl)anthracene), DSA (distyrylarylene), CDBP (4,4′-bis(9-carbazolyl)-2,2′-dimethyl-biphenyl), MADN (2-Methyl-9,10-bis(naphthalen-2-yl)anthracene), CP1 (Hexaphenyl cyclotriphosphazene), UGH2 (1,4-Bis(triphenylsilyl)benzene), DPSiO3 (Hexaphenylcyclotrisiloxane), DPSiO4 (Octaphenylcyclotetrasiloxane), etc. can be used as host materials.

[0434] The emissive layer (EML) may include a compound represented by the following chemical formula Ma. The compound represented by the following chemical formula Ma may be used as a phosphorescent dopant material.

[0435] [Chemical Formula Ma]

[0436]

[0437] In the above formula Ma, Y1 to Y4 and Z1 to Z4 are each independently CR1 or N, and R1 to R4 are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted amine group, a substituted or unsubstituted thio group, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heteroaryl group having 2 to 30 carbon atoms, or may form a ring by bonding with an adjacent group. In the formula Ma, m is 0 or 1, and n is 2 or 3. In the formula Ma, when m is 0, n is 3, and when m is 1, n is 2.

[0438] Compounds represented by the chemical formula Ma can be used as phosphorescent dopants.

[0439] The compound represented by the chemical formula Ma may be represented by any one of the following compounds M-a1 to M-a25. However, the following compounds M-a1 to M-a25 are exemplary, and the compound represented by the chemical formula Ma is not limited to those represented by the following compounds M-a1 to M-a25.

[0440]

[0441]

[0442]

[0443] The emissive layer (EML) may include a compound represented by any one of the following chemical formulas Fa to Fc. Compounds represented by the following chemical formulas Fa to Fc may be used as fluorescent dopant materials.

[0444] [Chemical Formula Fa]

[0445]

[0446] In the above chemical formula Fa, R a to R j The two selected from each are independently It could be replaced by R a to R j middle The remaining elements not substituted may 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 ring-forming aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heteroaryl group having 2 to 30 carbon atoms. In this, Ar1 and Ar2 may each independently be a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heteroaryl group having 2 to 30 carbon atoms. For example, at least one of Ar1 and Ar2 may be a heteroaryl group containing O or S as a ring-forming atom.

[0447] [Chemical Formula Fb]

[0448]

[0449] In the above chemical formula Fb, R a and R b Each may independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heteroaryl group having 2 to 30 carbon atoms, or may form a ring by bonding to an adjacent group. Ar1 to Ar4 may each independently be a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heteroaryl group having 2 to 30 carbon atoms.

[0450] In the chemical formula Fb, U and V may each be independently a substituted or unsubstituted cyclic hydrocarbon ring with 5 to 30 carbon atoms, or a substituted or unsubstituted cyclic heterocyclic ring with 2 to 30 carbon atoms. At least one of Ar1 to Ar4 may be a heteroaryl group containing O or S as a cyclic atom.

[0451] In the chemical formula Fb, the number of rings represented by U and V can each be independently 0 or 1. For example, if the number of U or V in the chemical formula Fb is 1, it means that one ring constitutes a condensed ring in the part labeled U or V, and if the number of U or V is 0, it means that there is no ring labeled U or V. Specifically, if the number of U is 0 and the number of V is 1, or if the number of U is 1 and the number of V is 0, the condensed ring having a fluorene core of the chemical formula Fb may be a tetracyclic compound. Additionally, if the number of both U and V is 0, the condensed ring of the chemical formula Fb may be a tricyclic compound. Additionally, if the number of both U and V is 1, the condensed ring having a fluorene core of the chemical formula Fb may be a pentacyclic compound.

[0452] [Chemical Formula Fc]

[0453]

[0454] In the chemical formula Fc, A1 and A2 are each independently O, S, Se, or NR m and R m It may be a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cyclic aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted cyclic heteroaryl group having 2 to 30 carbon atoms. R1 to R 11Each is independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted amine group, a substituted or unsubstituted boryl group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thio group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heteroaryl group having 2 to 30 carbon atoms, or forms a ring by bonding with an adjacent group.

[0455] In the chemical formula Fc, A1 and A2 can each independently bond with substituents of adjacent rings to form condensation rings. For example, A1 and A2 each independently NR m In this case, A1 may combine with R4 or R5 to form a ring. Additionally, A2 may combine with R7 or R8 to form a ring.

[0457] In one embodiment, the light-emitting layer (EML) is a known dopant material, styryl derivative (e.g., 1,4-bis[2-(3-N-ethylcarbazoryl)vinyl]benzene (BCzVB), 4-(di-p-tolylamino)-4'-[(di-p-tolylamino)styryl]stilbene (DPAVB), N-(4-((E)-2-(6-((E)-4-(diphenylamino)styryl)naphthalen-2-yl)vinyl)phenyl)-N-phenylbenzenamine (N-BDAVBi)), 4,4'-bis[2-(4-(N,N-diphenylamino)phenyl)vinyl]biphenyl (DPAVBi), perylene and its derivatives (e.g., 2,5,8,11-Tetra-t-butylperylene (TBP)), pyrene and its derivatives (e.g., It may further include 1,1-dipyrene, 1,4-dipyrenylbenzene, 1,4-Bis(N,N-Diphenylamino)pyrene, etc.

[0458] The emissive layer (EML) may further comprise a known phosphorescent dopant material. For example, the phosphorescent dopant may be a metal complex comprising iridium (Ir), platinum (Pt), osmium (Os), gold (Au), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), or thulium (Tm). Specifically, FIrpic(iridium(III) bis(4,6-difluorophenylpyridinato-N,C2 ), Fir6 (Bis(2,4-difluorophenylpyridinato)-tetrakis(1-pyrazolyl)borate iridium(III)), or PtOEP (platinum octaethyl porphyrin) can be used as phosphorescent dopants. However, the examples are not limited thereto.

[0459] The above-mentioned light-emitting layer may include quantum dots.

[0460] In this specification, a quantum dot refers to a crystal of a semiconductor compound. A quantum dot can emit light of various emission wavelengths depending on the size of the crystal. A quantum dot may also emit light of various emission wavelengths by controlling the elemental ratio within the quantum dot compound.

[0461] The diameter of the above quantum dots may be, for example, about 1 nm to 10 nm.

[0462] The above quantum dots can be synthesized by a wet chemical process, an organometallic chemical vapor deposition process, a molecular beam epitaxy process, or a similar process.

[0463] The above wet chemical process is a method of growing quantum dot particle crystals after mixing an organic solvent and a precursor material. When the crystals grow, the organic solvent naturally acts as a dispersant coordinated to the surface of the quantum dot crystals and can control the growth of the crystals. Therefore, the wet chemical process can control the growth of quantum dot particles through a process that is easier and lower cost than vapor deposition methods such as Metal Organic Chemical Vapor Deposition (MOCVD) or Molecular Beam Epitaxy (MBE).

[0464] The light-emitting layer of the present invention may include a quantum dot material. The core of the quantum dot may be selected from group II-VI compounds, group III-V compounds, group III-VI compounds, group I-III-VI compounds, group IV-VI compounds, group IV elements, group IV compounds, and combinations thereof.

[0465] Group II-VI compounds are diatomic compounds selected from the group consisting of CdSe, CdTe, CdS, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, MgSe, MgS, and mixtures thereof; ternary compounds selected from the group consisting of CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, CdZnSe, CdZnTe, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, MgZnSe, MgZnS, and mixtures thereof; and may be selected from the group consisting of four-element compounds selected from the group consisting of HgZnTeS, CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe, and mixtures thereof. Meanwhile, the II-VI semiconductor compound may further include a Group I metal and / or a Group IV element. The I-II-VI compound may be selected from CuSnS or CuZnS, and the II-IV-VI compound may be selected from ZnSnS, etc. The I-II-IV-VI compound may be selected from four-element compounds selected from the group consisting of Cu2ZnSnS2, Cu2ZnSnS4, Cu2ZnSnSe4, Ag2ZnSnS2, and mixtures thereof.

[0466] Group III-VI compounds include binary compounds such as In2S3 and In2Se3, and InGaS 3 It may include ternary compounds such as InGaSe3, or any combination thereof.

[0467] Group I-III-VI compounds are ternary compounds selected from the group consisting of AgInS, AgInS2, CuInS, CuInS2, AgGaS2, CuGaS2CuGaO2, AgGaO2, AgAlO2, and mixtures thereof, or AgInGaS2, It can be selected from four-element compounds such as CuInGaS2.

[0468] III-V group compounds may be selected from the group consisting of diatomic compounds selected from the group consisting of GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, InSb, and mixtures thereof; ternary compounds selected from the group consisting of GaNP, GaNAs, GaNSb, GaPAs, GaPSb, AlNP, AlNAs, AlNSb, AlPAs, AlPSb, InGaP, InAlP, InNP, InNAs, InNSb, InPAs, InPSb, and mixtures thereof; and quaternary compounds selected from the group consisting of GaAlNP, GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNP, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs, InAlPSb, and mixtures thereof. Meanwhile, III-V group compounds may further include a group II metal. For example, InZnP, etc., can be selected as a Group III-II-V compound.

[0469] Group IV-VI compounds may be selected from the group consisting of diatomic compounds selected from SnS, SnSe, SnTe, PbS, PbSe, PbTe and mixtures thereof; ternary compounds selected from the group consisting of SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, SnPbTe and mixtures thereof; and quaternary compounds selected from the group consisting of SnPbSSe, SnPbSeTe, SnPbSTe and mixtures thereof.

[0470] Examples of the above II-IV-V semiconductor compounds may be ternary compounds selected from the group consisting of ZnSnP, ZnSnP2, ZnSnAs2, ZnGeP2, ZnGeAs2, CdSnP2, CdGeP2, and mixtures thereof.

[0471] Group IV elements may be selected from the group consisting of Si, Ge, and mixtures thereof. Group IV compounds may be diatomic compounds selected from the group consisting of SiC, SiGe, and mixtures thereof.

[0472] Each element included in the above-mentioned multi-element compounds, such as the binary, ternary, and quaternary compounds, may exist within the particles at a uniform or non-uniform concentration. That is, the above chemical formula indicates the type of element included in the compound, and the ratio of elements within the compound may vary. For example, AgInGaS2 is AgIn x Ga 1-x S2 (where x is a real number between 0 and 1) can mean.

[0473] In this case, the binary, ternary, or quaternary compounds may exist within the particle at a uniform concentration, or they may exist within the same particle with their concentration distributions partially divided into different states. Additionally, they may have a core / shell structure in which one quantum dot surrounds another. In a core / shell structure, there may be a concentration gradient in which the concentration of the element in the shell decreases as it moves toward the core.

[0474] In some embodiments, the quantum dot may have a core-shell structure comprising a core containing the aforementioned nanocrystal and a shell surrounding the core. The shell of the quantum dot may serve as a protective layer to maintain semiconductor properties by preventing chemical degradation of the core and / or as a charging layer to impart electrophoretic properties to the quantum dot. The shell may be a single layer or a multilayer. Examples of the shell of the quantum dot include oxides of metals or non-metals, semiconductor compounds, or combinations thereof.

[0475] For example, the oxide of the metal or nonmetal mentioned above may be exemplified as a binary compound such as SiO2, Al2O3, TiO2, ZnO, MnO, Mn2O3, Mn3O4, CuO, FeO, Fe2O3, Fe3O4, CoO, Co3O4, NiO, or a ternary compound such as MgAl2O4, CoFe2O4, NiFe2O4, CoMn2O4, but the present invention is not limited thereto.

[0476] In addition, the above semiconductor compounds may be examples of CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnSeS, ZnTeS, GaAs, GaP, GaSb, HgS, HgSe, HgTe, InAs, InP, InGaP, InSb, AlAs, AlP, AlSb, etc., but the present invention is not limited thereto.

[0477] Quantum dots can have a full width of half maximum (FWHM) of the emission wavelength spectrum of about 45 nm or less, preferably about 40 nm or less, and more preferably about 30 nm or less, and color purity or color reproducibility can be improved in this range. In addition, since the light emitted through these quantum dots is emitted in all directions, the viewing angle can be improved.

[0478] In addition, the shape of the quantum dots is not specifically limited to shapes commonly used in the field, but more specifically, shapes such as spherical, pyramidal, multi-arm, or cubic nanoparticles, nanotubes, nanowires, nanofibers, and nanoplate particles may be used.

[0479] Since the energy band gap of quantum dots can be controlled by adjusting the size of the quantum dots or the elemental ratio within the quantum dot compound, light of various wavelengths can be obtained from the quantum dot emissive layer. Therefore, by using quantum dots as described above (using quantum dots of different sizes or different elemental ratios within the quantum dot compound), a light-emitting device that emits light of various wavelengths can be realized. Specifically, the size of the quantum dots or the elemental ratio within the quantum dot compound can be selected to emit red, green, and / or blue light. Additionally, the quantum dots can be configured to emit white light by combining light of various colors.

[0480] In the light-emitting device (ED) of one embodiment illustrated in FIGS. 3 to 6, an electron transport region (ETR) is provided on the light-emitting layer (EML). The electron transport region (ETR) may include at least one of a hole blocking layer (HBL), an electron transport layer (ETL), and an electron injection layer (EIL), but the embodiment is not limited thereto.

[0481] The electron transport region (ETR) may have a multilayer structure consisting of a single layer made of a single material, a single layer made of multiple different materials, or multiple layers made of multiple different materials.

[0482] For example, the electron transport region (ETR) may have a single-layer structure of an electron injection layer (EIL) or an electron transport layer (ETL), or it may have a single-layer structure composed of an electron injection material and an electron transport material. Additionally, the electron transport region (ETR) may have a single-layer structure composed of multiple different materials, or it may have an electron transport layer (ETL) / electron injection layer (EIL) or hole blocking layer (HBL) / electron transport layer (ETL) / electron injection layer (EIL) structure stacked sequentially from the emitting layer (EML), but is not limited thereto. The thickness of the electron transport region (ETR) may be, for example, about 1000 Å to about 1500 Å.

[0483] The electron transport region (ETR) can be formed using various methods such as vacuum deposition, spin coating, casting, the Langmuir-Blodgett (LB) method, inkjet printing, laser printing, and laser induced thermal imaging (LITI).

[0484] The electron transport domain (ETR) may include a compound represented by the following chemical formula ET-2.

[0485] [Chemical Formula ET-2]

[0486]

[0487] In chemical formula ET-2, at least one of X1 to X3 is N and the rest are CR a is. R a may be a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heteroaryl group having 2 to 30 carbon atoms. Ar1 to Ar3 may 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 ring-forming aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heteroaryl group having 2 to 30 carbon atoms.

[0488] In the formula ET-2, a to c may each be an integer from 0 to 10 or less, independently. In the formula ET-2, L1 to L3 may each be a direct linkage, a substituted or unsubstituted ring-forming arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heteroarylene group having 2 to 30 carbon atoms. Meanwhile, when a to c is an integer of 2 or more, L1 to L3 may each be a substituted or unsubstituted ring-forming arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heteroarylene group having 2 to 30 carbon atoms.

[0489] The electron transport domain (ETR) may include anthracene compounds. However, it is not limited thereto, and the electron transport domain (ETR) may include, for example, Alq3(Tris(8-hydroxyquinolinato)aluminum), 1,3,5-tri[(3-pyridyl)-phen-3-yl]benzene, 2,4,6-tris(3'-(pyridin-3-yl)biphenyl-3-yl)-1,3,5-triazine, 2-(4-(N-phenylbenzoimidazol-1-yl)phenyl)-9,10-dinaphthylanthracene, TPBi(1,3,5-Tri(1-phenyl-1H-benzo[d]imidazol-2-yl)benzene), BCP(2,9-Dimethyl-4,7-diphenyl-1,10-phenanthroline), Bphen(4,7-Diphenyl-1,10-phenanthroline), TAZ(3-(4-Biphenylyl)-4-phenyl-5-tert-butylphenyl-1,2,4-triazole), NTAZ(4-(Naphthalen-1-yl)-3,5-diphenyl-4H-1,2,4-triazole), tBu-PBD(2-(4-Biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole), BAlq(Bis(2-methyl-8-quinolinolato-N1,O8)-(1,1'-Biphenyl-4-olato)aluminum), Bebq2(berylliumbis(benzoquinolin-10-olate)), ADN(9,10-di(naphthalene-2-yl)anthracene), BmPyPhB(1,3-Bis[3,5-di(pyridin-3-yl)phenyl]benzene),

[0490] It may include CNNPTRZ(4'-(4-(4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)naphthalen-1-yl)-[1,1'-biphenyl]-4-carbonitrile) and mixtures thereof.

[0491] In one embodiment, the electron transport region (ETR) may include any one of the compounds of compound group 3.

[0492] The electron transport region (ETR) may include at least one of the following compounds ET1 to ET36.

[0493]

[0494]

[0495]

[0497] Additionally, the electron transport region (ETR) may include metal halides such as LiF, NaCl, CsF, RbCl, RbI, CuI, and KI, lanthanide metals such as Yb, and co-deposited materials of the above metal halides and lanthanide metals. For example, the electron transport region (ETR) may include KI:Yb, RbI:Yb, LiF:Yb, etc. as co-deposited materials. Meanwhile, metal oxides such as Li2O and BaO, or Liq(8-hydroxyl-Lithium quinolate), etc., may be used for the electron transport region (ETR), but the examples are not limited thereto. The electron transport region (ETR) may also be composed of a material in which an electron transport material and an insulating organometal salt are mixed. The organometal salt may be a material having an energy band gap of approximately 4 eV or more. Specifically, for example, organometallic salts may include metal acetate, metal benzoate, metal acetoacetate, metal acetylacetonate, or metal stearate.

[0498] The electron transport region (ETR) may further include at least one of BCP (2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline), TSPO1 (diphenyl(4-(triphenylsilyl)phenyl)phosphine oxide) and Bphen (4,7-diphenyl-1,10-phenanthroline) in addition to the aforementioned materials, but the examples are not limited thereto.

[0499] The electron transport region (ETR) may include compounds of the electron transport region described above in at least one of the electron injection layer (EIL), electron transport layer (ETL), and hole blocking layer (HBL).

[0500] If the electron transport region (ETR) includes an electron transport layer (ETL), the thickness of the electron transport layer (ETL) may be about 100 Å to about 1000 Å, for example, about 150 Å to about 500 Å. If the thickness of the electron transport layer (ETL) satisfies the range described above, satisfactory electron transport characteristics can be obtained without a substantial increase in driving voltage. If the electron transport region (ETR) includes an electron injection layer (EIL), the thickness of the electron injection layer (EIL) may be about 1 Å to about 100 Å, or about 3 Å to about 90 Å. If the thickness of the electron injection layer (EIL) satisfies the range described above, satisfactory electron injection characteristics can be obtained without a substantial increase in driving voltage.

[0501] The second electrode (EL2) is provided on the electron transport region (ETR). The second electrode (EL2) may be a common electrode. The second electrode (EL2) may be a cathode or an anode, but the embodiments are not limited thereto. For example, if the first electrode (EL1) is an anode, the second electrode (EL2) may be a cathode, and if the first electrode (EL1) is a cathode, the second electrode (EL2) may be an anode.

[0502] The second electrode (EL2) may be a transmissive electrode, a semitransmissive electrode, or a reflective electrode. If the second electrode (EL2) is a transmissive electrode, the second electrode (EL2) may be made of a transparent metal oxide, for example, ITO (indium tin oxide), IZO (indium zinc oxide), ZnO (zinc oxide), ITZO (indium tin zinc oxide), etc.

[0503] When the second electrode (EL2) is a semi-transparent electrode or a reflective electrode, the second electrode (EL2) may include Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF / Ca, LiF / Al, Mo, Ti, Yb, W, or a compound or mixture containing these (e.g., AgMg, AgYb, or MgYb). Alternatively, the second electrode (EL2) may have a plurality of layer structures including a reflective film or semi-transparent film formed of the above material and a transparent conductive film formed of ITO (indium tin oxide), IZO (indium zinc oxide), ZnO (zinc oxide), ITZO (indium tin zinc oxide), etc. For example, the second electrode (EL2) may include the metal material described above, a combination of two or more metal materials selected from the metal materials described above, or oxides of the metal materials described above.

[0504] Although not illustrated, the second electrode (EL2) can be connected to an auxiliary electrode. When the second electrode (EL2) is connected to an auxiliary electrode, the resistance of the second electrode (EL2) can be reduced.

[0505] Meanwhile, a capping layer (CPL) may be further disposed on the second electrode (EL2) of the light-emitting element (ED) of one embodiment. The capping layer (CPL) may include a multilayer or a single layer.

[0506] In one embodiment, the capping layer (CPL) may be an organic layer or an inorganic layer. For example, if the capping layer (CPL) includes an inorganic material, the inorganic material may be an alkali metal compound such as LiF, an alkaline earth metal compound such as MgF2, SiON, or SiN X It may include SiOy, etc.

[0507] For example, when the capping layer (CPL) contains an organic material, the organic material may include α-NPD, NPB, TPD, m-MTDATA, Alq3, CuPc, TPD15 (N4,N4,N4',N4'-tetra (biphenyl-4-yl) biphenyl-4,4'-diamine), TCTA (4,4',4"- Tris (carbazol-9-yl) triphenylamine), etc., or may include an epoxy resin or an acrylate such as methacrylate. However, the examples are not limited thereto, and the capping layer (CPL) may include at least one of the following compounds P1 to P5.

[0508]

[0509]

[0510] Meanwhile, the refractive index of the capping layer (CPL) may be 1.6 or higher. Specifically, for light in a wavelength range of 550 nm or more and 660 nm or less, the refractive index of the capping layer (CPL) may be 1.6 or higher.

[0511] FIGS. 7 to 10 are cross-sectional views of a display device according to one embodiment. In the following description of the display device according to one embodiment with reference to FIGS. 7 to 10, details that overlap with those described in FIGS. 1 to 6 above will not be explained again, and the differences will be explained primarily.

[0512] Referring to FIG. 7, a display device (DD-a) according to one embodiment may include a display panel (DP) including a display element layer (DP-ED), a light control layer (CCL) and a color filter layer (CFL) disposed on the display panel (DP). In one embodiment illustrated in FIG. 7, the display panel (DP) may include a base layer (BS), a circuit layer (DP-CL) and a display element layer (DP-ED) provided on the base layer (BS), and the display element layer (DP-ED) may include a light-emitting element (ED).

[0513] The light-emitting element (ED) may include a first electrode (EL1), a hole transport region (HTR) disposed on the first electrode (EL1), a light-emitting layer (EML) disposed on the hole transport region (HTR), an electron transport region (ETR) disposed on the light-emitting layer (EML), and a second electrode (EL2) disposed on the electron transport region (ETR). Meanwhile, the structure of the light-emitting element (ED) shown in FIG. 7 may be identical to the structure of the light-emitting element of FIG. 3 to FIG. 6 described above.

[0514] The light-emitting layer (EML) of the light-emitting element (ED) included in the display device (DD-a) according to one embodiment may include the condensed polycyclic compound of the above-described embodiment.

[0515] Referring to FIG. 7, the light-emitting layer (EML) may be disposed within an opening (OH) defined in the pixel defining film (PDL). For example, the light-emitting layer (EML) provided corresponding to each light-emitting region (PXA-R, PXA-G, PXA-B) separated by the pixel defining film (PDL) may emit light of the same wavelength range. In the display device (DD-a) of one embodiment, the light-emitting layer (EML) may emit blue light. Meanwhile, unlike illustrated, in one embodiment, the light-emitting layer (EML) may be provided as a common layer over the entire light-emitting regions (PXA-R, PXA-G, PXA-B).

[0516] A light control layer (CCL) may be placed on a display panel (DP). The light control layer (CCL) may include a light converter. The light converter may be a quantum dot or a phosphor. The light converter may emit light by converting the wavelength of the provided light. That is, the light control layer (CCL) may be a layer containing quantum dots or a layer containing a phosphor.

[0517] The optical control layer (CCL) may include a plurality of optical control units (CCP1, CCP2, CCP3). The optical control units (CCP1, CCP2, CCP3) may be spaced apart from each other.

[0518] Referring to FIG. 7, a split pattern (BMP) may be placed between spaced-apart light control units (CCP1, CCP2, CCP3), but the embodiment is not limited thereto. In FIG. 7, the split pattern (BMP) is shown as not overlapping with the light control units (CCP1, CCP2, CCP3), but the edges of the light control units (CCP1, CCP2, CCP3) may overlap with the split pattern (BMP) at least partially.

[0519] The light control layer (CCL) may include a first light control unit (CCP1) comprising a first quantum dot (QD1) that converts a first color light provided by a light-emitting element (ED) into a second color light, a second light control unit (CCP2) comprising a second quantum dot (QD2) that converts the first color light into a third color light, and a third light control unit (CCP3) that transmits the first color light. In one embodiment, the first light control unit (CCP1) may provide red light, which is the second color light, and the second light control unit (CCP2) may provide green light, which is the third color light. The third light control unit (CCP3) may transmit and provide blue light, which is the first color light provided by the light-emitting element (ED). For example, the first quantum dot (QD1) may be a red quantum dot and the second quantum dot (QD2) may be a green quantum dot. The same as described above may apply to quantum dots (QD1, QD2).

[0520] Additionally, the light control layer (CCL) may further include a scatterer (SP). The first light control unit (CCP1) may include a first quantum dot (QD1) and a scatterer (SP), the second light control unit (CCP2) may include a second quantum dot (QD2) and a scatterer (SP), and the third light control unit (CCP3) may not include a quantum dot and may include a scatterer (SP).

[0521] The scatterer (SP) may be an inorganic particle. For example, the scatterer (SP) may comprise at least one of TiO2, ZnO, Al2O3, SiO2, and hollow silica. The scatterer (SP) may comprise any one of TiO2, ZnO, Al2O3, SiO2, and hollow silica, or may be a mixture of two or more materials selected from TiO2, ZnO, Al2O3, SiO2, and hollow silica.

[0522] Each of the first light control unit (CCP1), the second light control unit (CCP2), and the third light control unit (CCP3) may include a base resin (BR1, BR2, BR3) that disperses quantum dots (QD1, QD2) and scatterers (SP). In one embodiment, the first light control unit (CCP1) may include a first quantum dot (QD1) and a scatterer (SP) dispersed within the first base resin (BR1), the second light control unit (CCP2) may include a second quantum dot (QD2) and a scatterer (SP) dispersed within the second base resin (BR2), and the third light control unit (CCP3) may include a scatterer (SP) dispersed within the third base resin (BR3).

[0523] The base resin (BR1, BR2, BR3) is a medium in which quantum dots (QD1, QD2) and scatterers (SP) are dispersed, and can be composed of various resin compositions that can generally be referred to as binders. For example, the base resin (BR1, BR2, BR3) may be an acrylic resin, a urethane resin, a silicone resin, an epoxy resin, etc. The base resin (BR1, BR2, BR3) may be a transparent resin. In one embodiment, the first base resin (BR1), the second base resin (BR2), and the third base resin (BR3) may each be the same or different from one another.

[0524] The light control layer (CCL) may include a barrier layer (BFL1). The barrier layer (BFL1) may serve to prevent the penetration of moisture and / or oxygen (hereinafter referred to as 'moisture / oxygen'). The barrier layer (BFL1) may block the light control units (CCP1, CCP2, CCP3) from being exposed to moisture / oxygen. Meanwhile, the barrier layer (BFL1) may cover the light control units (CCP1, CCP2, CCP3). Additionally, a barrier layer (BFL2) may also be provided between the light control units (CCP1, CCP2, CCP3) and the filters (CF1, CF2, CF3).

[0525] The barrier layer (BFL1, BFL2) may include at least one inorganic layer. That is, the barrier layer (BFL1, BFL2) may be formed by including an inorganic material. For example, the barrier layer (BFL1, BFL2) may be formed by including silicon nitride, aluminum nitride, zirconium nitride, titanium nitride, hafnium nitride, tantalum nitride, silicon oxide, aluminum oxide, titanium oxide, tin oxide, cerium oxide, silicon oxynitride, or a metal thin film with secured light transmittance. Meanwhile, the barrier layer (BFL1, BFL2) may further include an organic film. The barrier layer (BFL1, BFL2) may be composed of a single layer or multiple layers.

[0526] In a display device (DD-a) of one embodiment, a color filter layer (CFL) may be placed on a light control layer (CCL). For example, the color filter layer (CFL) may be placed directly on the light control layer (CCL). In this case, the barrier layer (BFL2) may be omitted.

[0527] The color filter layer (CFL) may include filters (CF1, CF2, CF3). Each of the first to third filters (CF1, CF2, CF3) may be positioned corresponding to a red light-emitting region (PXA-R), a green light-emitting region (PXA-G), and a blue light-emitting region (PXA-B), respectively.

[0528] The color filter layer (CFL) may include a first filter (CF1) that transmits second color light, a second filter (CF2) that transmits third color light, and a third filter (CF3) that transmits first color light. For example, the first filter (CF1) may be a red filter, the second filter (CF2) may be a green filter, and the third filter (CF3) may be a blue filter. Each of the filters (CF1, CF2, CF3) may comprise a polymer photosensitive resin and a pigment or dye. The first filter (CF1) may comprise a red pigment or dye, the second filter (CF2) may comprise a green pigment or dye, and the third filter (CF3) may comprise a blue pigment or dye.

[0529] Meanwhile, the embodiments are not limited thereto, and the third filter (CF3) may not contain pigment or dye. The third filter (CF3) may contain a polymer photosensitive resin and not contain pigment or dye. The third filter (CF3) may be transparent. The third filter (CF3) may be formed of a transparent photosensitive resin.

[0530] Additionally, in one embodiment, the first filter (CF1) and the second filter (CF2) may be yellow filters. The first filter (CF1) and the second filter (CF2) may also be provided as a single unit without being distinguished from each other.

[0531] Although not shown, the color filter layer (CFL) may further include a light-blocking portion (not shown). The light-blocking portion may be a black matrix. The light-blocking portion may be formed by including an organic light-blocking material or an inorganic light-blocking material containing a black pigment or a black dye. The light-blocking portion may prevent light leakage and distinguish the boundaries between adjacent filters (CF1, CF2, CF3).

[0532] A base substrate (BL) may be disposed on the color filter layer (CFL). The base substrate (BL) may be a component that provides a base surface on which the color filter layer (CFL) and the light control layer (CCL) are disposed. The base substrate (BL) may be a glass substrate, a metal substrate, a plastic substrate, etc. However, the embodiments are not limited thereto, and the base substrate (BL) may be an inorganic layer, an organic layer, or a composite material layer. In addition, unlike what is illustrated, the base substrate (BL) may be omitted in one embodiment.

[0533] FIG. 8 is a cross-sectional view showing a part of a display device according to one embodiment. In the display device (DD-TD) of one embodiment, the light-emitting element (ED-BT) may include a plurality of light-emitting structures (OL-B1, OL-B2, OL-B3). The light-emitting element (ED-BT) may include a first electrode (EL1) and a second electrode (EL2) facing each other, and a plurality of light-emitting structures (OL-B1, OL-B2, OL-B3) provided by being sequentially stacked in the thickness direction between the first electrode (EL1) and the second electrode (EL2). Each of the light-emitting structures (OL-B1, OL-B2, OL-B3) may include a light-emitting layer (EML, FIG. 7), a hole transport region (HTR), and an electron transport region (ETR) arranged between the light-emitting layer (EML, FIG. 7).

[0534] That is, the light-emitting element (ED-BT) included in the display device (DD-TD) of one embodiment may be a light-emitting element with a tandem structure including a plurality of light-emitting layers.

[0535] In one embodiment illustrated in FIG. 8, the light emitted from each of the light-emitting structures (OL-B1, OL-B2, OL-B3) may all be blue light. However, the embodiment is not limited thereto, and the wavelength range of the light emitted from each of the light-emitting structures (OL-B1, OL-B2, OL-B3) may differ from one another. For example, a light-emitting device (ED-BT) comprising a plurality of light-emitting structures (OL-B1, OL-B2, OL-B3) that emit light in different wavelength ranges may emit white light.

[0536] A charge generation layer (CGL1, CGL2) may be disposed between adjacent light-emitting structures (OL-B1, OL-B2, OL-B3). The charge generation layer (CGL1, CGL2) may include a p-type charge generation layer and / or an n-type charge generation layer.

[0537] At least one of the light-emitting structures (OL-B1, OL-B2, OL-B3) included in the display device (DD-TD) of one embodiment may include the condensed polycyclic compound of the above-described embodiment. That is, at least one of the plurality of light-emitting layers included in the light-emitting element (ED-BT) may include the condensed polycyclic compound of one embodiment.

[0538] FIG. 9 is a cross-sectional view showing a display device according to an embodiment of the present invention. FIG. 10 is a cross-sectional view showing a display device according to an embodiment of the present invention.

[0539] Referring to FIG. 9, a display device (DD-b) according to one embodiment may include light-emitting elements (ED-1, ED-2, ED-3) in which two light-emitting layers are stacked. Compared to the display device (DD) of one embodiment shown in FIG. 2, the first to third light-emitting elements (ED-1, ED-2, ED-3) in the embodiment shown in FIG. 9 differ in that they each include two light-emitting layers stacked in the thickness direction. In each of the first to third light-emitting elements (ED-1, ED-2, ED-3), the two light-emitting layers may emit light in the same wavelength range.

[0540] The first light-emitting element (ED-1) may include a first red light-emitting layer (EML-R1) and a second red light-emitting layer (EML-R2). The second light-emitting element (ED-2) may include a first green light-emitting layer (EML-G1) and a second green light-emitting layer (EML-G2). Additionally, the third light-emitting element (ED-3) may include a first blue light-emitting layer (EML-B1) and a second blue light-emitting layer (EML-B2). Light-emitting auxiliary members (OG) may be disposed between the first red light-emitting layer (EML-R1) and the second red light-emitting layer (EML-R2), between the first green light-emitting layer (EML-G1) and the second green light-emitting layer (EML-G2), and between the first blue light-emitting layer (EML-B1) and the second blue light-emitting layer (EML-B2).

[0541] The light-emitting auxiliary part (OG) may include a single layer or multiple layers. The light-emitting auxiliary part (OG) may include a charge generation layer. More specifically, the light-emitting auxiliary part (OG) may include sequentially stacked electron transport regions, charge generation layers, and hole transport regions. The light-emitting auxiliary part (OG) may be provided as a common layer across the entire first to third light-emitting elements (ED-1, ED-2, ED-3). However, the embodiments are not limited thereto, and the light-emitting auxiliary part (OG) may be provided by being patterned within an opening (OH) defined in a pixel defining film (PDL).

[0542] The first red emitting layer (EML-R1), the first green emitting layer (EML-G1), and the first blue emitting layer (EML-B1) may be disposed between the light-emitting auxiliary region (OG) and the electron transport region (ETR). The second red emitting layer (EML-R2), the second green emitting layer (EML-G2), and the second blue emitting layer (EML-B2) may be disposed between the hole transport region (HTR) and the light-emitting auxiliary region (OG).

[0543] That is, the first light-emitting element (ED-1) may include a first electrode (EL1), a hole transport region (HTR), a second red light-emitting layer (EML-R2), a light-emitting auxiliary part (OG), a first red light-emitting layer (EML-R1), an electron transport region (ETR), and a second electrode (EL2) that are sequentially stacked. The second light-emitting element (ED-2) may include a first electrode (EL1), a hole transport region (HTR), a second green light-emitting layer (EML-G2), a light-emitting auxiliary part (OG), a first green light-emitting layer (EML-G1), an electron transport region (ETR), and a second electrode (EL2) that are sequentially stacked. The third light-emitting element (ED-3) may include a first electrode (EL1), a hole transport region (HTR), a second blue light-emitting layer (EML-B2), a light-emitting auxiliary part (OG), a first blue light-emitting layer (EML-B1), an electron transport region (ETR), and a second electrode (EL2) that are sequentially stacked.

[0544] Meanwhile, 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) is disposed on the display panel (DP) to control reflected light from the display panel (DP) caused by external light. Unlike what is illustrated, the optical auxiliary layer (PL) may be omitted in a display device according to one embodiment.

[0545] At least one light-emitting layer included in the display device (DD-b) of the embodiment illustrated in FIG. 9 may include the condensed polycyclic compound of the embodiment described above. For example, in one embodiment, at least one of the first blue light-emitting layer (EML-B1) and the second blue light-emitting layer (EML-B2) may include the condensed polycyclic compound of the embodiment.

[0546] Unlike FIGS. 8 and 9, the display device (DD-c) of FIG. 10 is illustrated as including four light-emitting structures (OL-B1, OL-B2, OL-B3, OL-C1). The light-emitting element (ED-CT) may include a first electrode (EL1) and a second electrode (EL2) facing each other, and first to fourth light-emitting structures (OL-B1, OL-B2, OL-B3, OL-C1) sequentially stacked in the thickness direction between the first electrode (EL1) and the second electrode (EL2). A charge generation layer (CGL1, CGL2, CGL3) may be disposed between the first to fourth light-emitting structures (OL-B1, OL-B2, OL-B3, OL-C1). The first charge generation layer (CGL1) may be disposed between the first light-emitting structure (OL-B1) and the fourth light-emitting structure (OL-C1). The second charge generation layer (CGL2) may be disposed between the first light-emitting structure (OL-B1) and the second light-emitting structure (OL-B2). The third charge generation layer (CGL3) may be disposed between the second light-emitting structure (OL-B2) and the third light-emitting structure (OL-B3). Among the four light-emitting structures, the first to third light-emitting structures (OL-B1, OL-B2, OL-B3) may emit blue light, and the fourth light-emitting structure (OL-C1) may emit green light. However, the embodiments are not limited thereto, and the first to fourth light-emitting structures (OL-B1, OL-B2, OL-B3, OL-C1) may emit light in different wavelength regions.

[0547] The charge generation layer (CGL1, CGL2, CGL3) disposed between adjacent light-emitting structures (OL-B1, OL-B2, OL-B3, OL-C1) may include a p-type charge generation layer and / or an n-type charge generation layer.

[0548] At least one of the light-emitting structures (OL-B1, OL-B2, OL-B3, OL-C1) included in the display device (DD-c) of one embodiment may include the condensed polycyclic compound of the above-described embodiment. For example, in one embodiment, at least one of the first to third light-emitting structures (OL-B1, OL-B2, OL-B3) may include the condensed polycyclic compound of the above-described embodiment.

[0549] A light-emitting device (ED) according to one embodiment of the present invention may include a polycyclic compound of one embodiment represented by the above-described chemical formula 1 in at least one functional layer disposed between a first electrode (EL1) and a second electrode (EL2) to exhibit excellent light-emitting efficiency and improved lifespan characteristics. For example, the polycyclic compound according to one embodiment may be included in the light-emitting layer (EML) of the light-emitting device (ED) of one embodiment, and the light-emitting device of one embodiment may exhibit long lifespan characteristics.

[0550] In one embodiment, the electronic device may include a display device comprising a plurality of light-emitting elements and a control unit for controlling the display device. The electronic device of one embodiment may be a device that is activated according to an electrical signal. The electronic device may include display devices of various embodiments. For example, the electronic device may include large display devices such as televisions, monitors, or external billboards, as well as small and medium-sized display devices such as personal computers, laptop computers, personal digital terminals, automotive display devices, game consoles, portable electronic devices, or cameras.

[0551] FIG. 11 is a drawing showing a vehicle (AM) in which first to fourth display devices (DD-1, DD-2, DD-3, DD-4) are installed. At least one of the first to fourth display devices (DD-1, DD-2, DD-3, DD-4) may have the same configuration as the display device (DD, DD-TD, DD-a, DD-b, DD-c) of an embodiment described with reference to FIG. 1, 2 and 7 to 10.

[0552] In FIG. 11, a vehicle (AM) is depicted as an automobile, but this is exemplary, and the first to fourth display devices (DD-1, DD-2, DD-3, DD-4) may be placed on other means of transportation such as bicycles, motorcycles, trains, ships, and airplanes. In addition, at least one of the first to fourth display devices (DD-1, DD-2, DD-3, DD-4) that includes the same configuration as the display device (DD, DD-TD, DD-a, DD-TD, DD-b, DD-c) of one embodiment may be employed in a personal computer, notebook computer, personal digital terminal, game console, portable electronic device, television, monitor, external billboard, etc. Furthermore, these are merely examples and may be display devices employed in other electronic devices without departing from the concept of the present invention.

[0553] At least one of the first to fourth display devices (DD-1, DD-2, DD-3, DD-4) may include a light-emitting element (ED) of an embodiment described with reference to FIGS. 3 to 6. The light-emitting element (ED) of an embodiment may include a condensed polycyclic compound of an embodiment. At least one of the first to fourth display devices (DD-1, DD-2, DD-3, DD-4) may include a light-emitting element (ED) containing a condensed polycyclic compound of an embodiment, thereby improving the display life.

[0554] Referring to FIG. 11, the vehicle (AM) may include a steering wheel (HA) and a gear (GR) for operating the vehicle (AM). Additionally, the vehicle (AM) may include a front window (GL) positioned to face the driver.

[0555] The first display device (DD-1) may be positioned in a first area that overlaps with the handle (HA). For example, the first display device (DD-1) may be a digital cluster that displays first information of the vehicle (AM). The first information may include a first scale indicating the driving speed of the vehicle (AM), a second scale indicating the engine rotational speed (i.e., RPM (revolutions per minute)), and an image indicating the fuel status. The first scale and the second scale may be displayed as digital images.

[0556] The second display device (DD-2) may be positioned in a second area facing the driver's seat and overlapping with the front window (GL). The driver's seat may be a seat with a steering wheel (HA). For example, the second display device (DD-2) may be a Head-Up Display (HUD) that displays second information of the vehicle (AM). The second display device (DD-2) may be optically transparent. The second information includes digital numbers representing the driving speed of the vehicle (AM) and may further include information such as the current time. Unlike what is illustrated, the second information of the second display device (DD-2) may be projected onto the front window (GL) for display.

[0557] The third display device (DD-3) may be positioned in a third area adjacent to the gear (GR). For example, the third display device (DD-3) may be a Center Information Display (CID) for vehicles positioned between the driver's seat and the passenger seat and displaying third information. The passenger seat may be a seat spaced apart from the driver's seat with the gear (GR) in between. The third information may include information regarding road conditions (e.g., navigation information), playback of music or radio, playback of dynamic video (or images), temperature inside the vehicle (AM), etc.

[0558] The fourth display device (DD-4) may be spaced apart from the steering wheel (HA) and gear (GR) and positioned in a fourth area adjacent to the side of the vehicle (AM). For example, the fourth display device (DD-4) may be a digital side mirror that displays the fourth information. The fourth display device (DD-4) may display an image of the outside of the vehicle (AM) captured by a camera module (CM) positioned on the outside of the vehicle (AM). The fourth information may include an image of the outside of the vehicle (AM).

[0559] The first to fourth information described above is exemplary, and the first to fourth display devices (DD-1, DD-2, DD-3, DD-4) may further display information regarding the interior and exterior of the vehicle (AM). The first to fourth information may include different information. However, the embodiments are not limited thereto, and some of the first to fourth information may include the same information.

[0561] Hereinafter, a condensed polycyclic compound according to one embodiment of the present invention and a light-emitting element of one embodiment will be described in detail with reference to examples and comparative examples. Furthermore, the examples described below are illustrative examples to aid in understanding the present invention, and the scope of the present invention is not limited thereto.

[0562] [Example]

[0563] 1. Synthesis of condensation polycyclic compounds

[0564] First, regarding the synthesis method of a condensed polycyclic compound according to the present embodiment, the synthesis method of compounds 51, 137, 138, 139, 140, 182, 183, 222, 226, 228, 240, 263, 264, 401, and 543 will be specifically explained by example. In addition, the synthesis method of a condensed polycyclic compound described below is an example, and the synthesis method of a condensed polycyclic compound according to the embodiment of the present invention is not limited to the following examples.

[0565] (1) Synthesis of Compound 51

[0566] (Synthesis of intermediate 51-(1))

[0567]

[0568] Under an Ar atmosphere, 120.24 ml of toluene and 60.12 ml of a 1:1 mixture of EtOH and water were added to 4-bromo-2-chloroaniline (15.03 g, 72.74 mmol), phenylboronic acid (31.04 g, 254.57 mmol), K2CO3 (60.32 g, 436.41 mmol), and Pd(Ph3P)4 (13.03 g, 11.27 mmol), and the mixture was heated for 24 hours while maintaining the ambient temperature at 80°C. The mixture was filtered via Celite and separated, and the organic layer was concentrated. It was purified by silica gel column chromatography to obtain intermediate 51-(1) (12.59 g, yield 85%). FAB MS analysis revealed that the molecular weight of intermediate 51-(1) was 204.

[0569] (Synthesis of intermediate 51-(2))

[0570]

[0571] Under an Ar atmosphere, 96.32 ml of toluene and 48.16 ml of a 1:1 mixture of EtOH and water were added to intermediate 51-(1) (12.04 g, 59.12 mmol), dibenzo[b,d]thiophen-3-ylboronic acid (17.53 g, 76.85 mmol), K3PO4 (25.1 g, 118.23 mmol), and Pd(Amphos)2Cl2 (4.19 g, 5.91 mmol), and heated for 24 hours while maintaining the ambient temperature at 40°C. The mixture was filtered via Celite and separated, and the organic layer was concentrated. It was purified by silica gel column chromatography to obtain intermediate 51-(2) (16.83 g, yield 81%). FAB MS analysis revealed that the molecular weight of intermediate 51-(2) was 351.

[0572] (Synthesis of intermediate 51-(3))

[0573]

[0574] Under an Ar atmosphere, 1,3-dibromo-5-(tert-butyl)benzene (15.22 g, 52.12 mmol), [1,1':3',1''-terphenyl]-2'-amine (14.07 g, 57.33 mmol), Pd(OAc)2 (0.35 g, 1.56 mmol), XantPhos (1.81 g, 3.13 mmol), and tBuONa (6.01 g, 62.55 mmol) were added to 260 ml of toluene and heated and stirred at 100°C for 8 hours. Water was added, filtered via Celite, and separated to concentrate the organic layer. Purified by silica gel column chromatography, intermediate 51-(3) (17.73 g, yield 72%) was obtained. FAB MS measurement revealed that the molecular weight of intermediate 51-(3) was 472.

[0575] (Synthesis of intermediate 51-(4))

[0576]

[0577] Approximately 10 ml of a small amount of toluene was added to intermediate 51-(3) (15.04 g, 31.83 mmol), 4-iodo-1,1'-biphenyl (89.17 g, 318.33 mmol), CuI (15.16 g, 79.58 mmol), and K2CO3 (65.99 g, 477.49 mmol), and heated for 24 hours while maintaining the ambient temperature at 215°C. The mixture was diluted with CH2Cl2, water was added, filtered via Celite, and separated to concentrate the organic layer. It was purified by silica gel column chromatography to obtain intermediate 51-(4) (16.11 g, yield 81%). FAB MS measurement revealed that the molecular weight of intermediate 51-(4) was 625.

[0578] (Synthesis of intermediate 51-(5))

[0579]

[0580] Under an Ar atmosphere, intermediate 51-(4) (7.05 g, 11.29 mmol), intermediate 51-(2) (4.17 g, 11.85 mmol), Pd(dba)2 (0.65 g, 1.13 mmol), P(tBu)3.HBF4 (0.65 g, 2.26 mmol), and tBuONa (2.49 g, 25.96 mmol) were added to 56 ml of toluene and heated and stirred at 100°C for 8 hours. Water was added, filtered via Celite, and separated to concentrate the organic layer. Purified by silica gel column chromatography, intermediate 51-(5) (8.49 g, yield 84%) was obtained. FAB MS measurement revealed that the molecular weight of intermediate 51-(5) was 895.

[0581] (Synthesis of intermediate 51-(6))

[0582]

[0583] Approximately 10 ml of a small amount of toluene was added to intermediate 51-(5) (8.11 g, 9.06 mmol), 1-chloro-3-iodobenzene (21.6 g, 90.59 mmol), CuI (4.31 g, 22.65 mmol), and K2CO3 (18.78 g, 135.89 mmol), and heated for 24 hours while maintaining the ambient temperature at 215°C. The mixture was diluted with CH2Cl2, water was added, filtered via Celite, and separated to concentrate the organic layer. It was purified by silica gel column chromatography to obtain intermediate 51-(6) (7.11 g, yield 78%). FAB MS measurement revealed that the molecular weight of intermediate 51-(6) was 1006.

[0584] (Synthesis of intermediate 51-(7))

[0585]

[0586] Under an Ar atmosphere, intermediate 51-(6) (6.55 g, 6.51 mmol) was dissolved in ODCB (65 ml), BBr3 (3.26 g, 13.02 mmol) was added, and the mixture was heated and stirred at 170°C for 10 hours. After cooling to room temperature, DIPEA (10.08 g, 78.15 mmol) was added, water was added, and the mixture was filtered via Celite and separated to concentrate the organic layer. The mixture was purified by silica gel column chromatography to obtain intermediate 51-(7) (2.51 g, yield 38%). FAB MS measurement revealed that the molecular weight of intermediate 51-(7) was 1014.

[0587] (Synthesis of Compound 51)

[0588]

[0589] Under an Ar atmosphere, intermediate 51-(7) (2.33 g, 2.3 mmol), 9H-carbazole (0.58 g, 3.45 mmol), Pd(dba)2 (0.13 g, 0.23 mmol), P(tBu)3.HBF4 (0.13 g, 0.46 mmol), and tBuONa (0.51 g, 5.29 mmol) were added to 11 ml of toluene and heated and stirred at 100°C for 8 hours. Water was added, filtered via Celite, and separated to concentrate the organic layer. Compound 51 (2.37 g, yield 90%) was obtained by purification using silica gel column chromatography. The molecular weight of Compound 51 was 1144 by FAB MS. Sublimation purification (320°C, 3.3 x 10 -3 The device was evaluated by Pa).

[0591] (1) Synthesis of Compound 137

[0592] (Synthesis of intermediate 137-(1))

[0593]

[0594] Under an Ar atmosphere, 200 ml of toluene and 100 ml of a 1:1 mixture of EtOH and water were added to 2,6-dibromo-4-(tert-butyl)aniline (25 g, 81.43 mmol), phenylboronic acid (9.93 g, 81.43 mmol), K2CO3 (67.52 g, 488.55 mmol), and Pd(Ph3P)4 (14.58 g, 12.62 mmol), and then heated for 24 hours while maintaining the ambient temperature at 80°C. The mixture was filtered via Celite and separated, and the organic layer was concentrated. It was purified by silica gel column chromatography to obtain intermediate 137-(1) (18.58 g, yield 75%). FAB MS analysis revealed that the molecular weight of intermediate 137-(1) was 304.

[0595] (Synthesis of intermediate 137-(2))

[0596]

[0597] Under an Ar atmosphere, 100.4 ml of toluene and 50.2 ml of a 1:1 mixture of EtOH and water were added to intermediate 137-(1) (12.55 g, 41.25 mmol), [1,1'-biphenyl]-4-ylboronic acid (12.25 g, 61.88 mmol), K2CO3 (34.21 g, 247.51 mmol), and Pd(Ph3P)4 (7.39 g, 6.39 mmol), and the mixture was heated for 24 hours while maintaining the ambient temperature at 80°C. The mixture was filtered via Celite and separated, and the organic layer was concentrated. The mixture was purified by silica gel column chromatography to obtain intermediate 137-(2) (13.7 g, yield 88%). FAB MS analysis revealed that the molecular weight of intermediate 137-(2) was 378.

[0598] (Synthesis of intermediate 137-(3))

[0599]

[0600] Under an Ar atmosphere, 1,3-dibromo-5-(tert-butyl)benzene (15.11 g, 51.74 mmol), 5'-(tert-butyl)-[1,1':3',1''-terphenyl]-2'-amine (17.16 g, 56.92 mmol), Pd(OAc)2 (0.35 g, 1.55 mmol), XantPhos (1.8 g, 3.1 mmol), and tBuONa (5.97 g, 62.09 mmol) were added to 258 ml of toluene and heated and stirred at 100°C for 8 hours. Water was added, filtered via Celite, and separated to concentrate the organic layer. Purified by silica gel column chromatography, intermediate 137-(3) (21.22 g, yield 80%) was obtained. In FAB MS measurements, the molecular weight of intermediate 137-(3) was 513.

[0601] (Synthesis of intermediate 137-(4))

[0602]

[0603] Under an Ar atmosphere, intermediate 137-(3) (10.02 g, 19.55 mmol), intermediate 137-(2) (11.07 g, 29.32 mmol), Pd(dba)2 (1.12 g, 1.95 mmol), P(tBu)3.HBF4 (1.13 g, 3.91 mmol), and tBuONa (4.32 g, 44.96 mmol) were added to 97 ml of toluene and heated and stirred at 100°C for 8 hours. Water was added, filtered via Celite, and separated to concentrate the organic layer. Purified by silica gel column chromatography, intermediate 137-(4) (13.13 g, yield 83%) was obtained. FAB MS measurement revealed that the molecular weight of intermediate 137-(4) was 809.

[0604] (Synthesis of intermediate 137-(5))

[0605]

[0606] Approximately 10 ml of a small amount of toluene was added to intermediate 137-(4) (6.02 g, 7.44 mmol), 4-iodo-1,1'-biphenyl (20.84 g, 74.4 mmol), CuI (3.54 g, 18.6 mmol), and K2CO3 (15.42 g, 111.6 mmol), and heated for 24 hours while maintaining the ambient temperature at 215°C. The mixture was diluted with CH2Cl2, water was added, filtered via Celite, and separated to concentrate the organic layer. It was purified by silica gel column chromatography to obtain intermediate 137-(5) (7.12 g, yield 86%). FAB MS measurement revealed that the molecular weight of intermediate 137-(5) was 1114.

[0607] (Synthesis of Compound 137)

[0608]

[0609] Under an Ar atmosphere, intermediate 137-(5) (6.55 g, 5.88 mmol) was dissolved in ODCB (59 ml), BBr3 (2.95 g, 11.76 mmol) was added, and the mixture was heated and stirred at 170°C for 10 hours. After cooling to room temperature, DIPEA (9.11 g, 70.59 mmol) was added, followed by water. The mixture was filtered via Celite and separated to concentrate the organic layer. Compound 137 (2.97 g, yield 45%) was obtained by purification via silica gel column chromatography. The molecular weight of Compound 137 was 1121 according to FAB MS measurements. Sublimation purification (300°C, 2.8 x 10 -3 The device was evaluated by Pa).

[0611] (2) Synthesis of Compound 138

[0612] (Synthesis of intermediate 138-(1))

[0613]

[0614] Under an Ar atmosphere, 88.48 ml of toluene and 44.24 ml of a 1:1 mixture of EtOH and water were added to 2,6-dibromo-4-(tert-butyl)aniline (11.06 g, 36.02 mmol), [1,1'-biphenyl]-4-ylboronic acid (21.4 g, 108.07 mmol), K2CO3 (29.87 g, 216.14 mmol), and Pd(Ph3P)4 (6.45 g, 5.58 mmol), and then heated for 24 hours while maintaining the ambient temperature at 80°C. The mixture was filtered via Celite and separated, and the organic layer was concentrated. It was purified by silica gel column chromatography to obtain intermediate 138-(1) (14.38 g, yield 88%). In FAB MS measurements, the molecular weight of intermediate 138-(1) was 454.

[0615] (Synthesis of intermediate 138-(2))

[0616]

[0617] Under an Ar atmosphere, intermediate 137-(3) (7.04 g, 13.74 mmol), intermediate 138-(1) (7.48 g, 16.48 mmol), Pd(dba)2 (0.79 g, 1.37 mmol), P(tBu)3.HBF4 (0.8 g, 2.75 mmol), and tBuONa (3.04 g, 31.59 mmol) were added to 68 ml of toluene and heated and stirred at 100°C for 8 hours. Water was added, filtered via Celite, and separated to concentrate the organic layer. Purified by silica gel column chromatography, intermediate 138-(2) (9.48 g, yield 78%) was obtained. FAB MS measurement revealed that the molecular weight of intermediate 138-(2) was 885.

[0618] (Synthesis of intermediate 138-(3))

[0619]

[0620] Approximately 10 ml of a small amount of toluene was added to intermediate 138-(2) (9.02 g, 10.19 mmol), 4-iodo-1,1'-biphenyl (28.54 g, 101.89 mmol), CuI (4.85 g, 25.47 mmol), and K2CO3 (21.12 g, 152.84 mmol), and heated for 24 hours while maintaining the ambient temperature at 215°C. The mixture was diluted with CH2Cl2, water was added, filtered via Celite, and separated to concentrate the organic layer. It was purified by silica gel column chromatography to obtain intermediate 138-(3) (10.55 g, yield 87%). FAB MS measurement revealed that the molecular weight of intermediate 138-(3) was 1190.

[0621] (Synthesis of Compound 138)

[0622]

[0623] Under an Ar atmosphere, intermediate 138-(3) (5.01 g, 4.21 mmol) was dissolved in ODCB (42 ml), BBr3 (2.11 g, 8.42 mmol) was added, and the mixture was heated and stirred at 170°C for 10 hours. After cooling to room temperature, DIPEA (6.52 g, 50.54 mmol) was added, followed by water. The mixture was filtered via Celite and separated to concentrate the organic layer. Compound 138 (2.07 g, yield 41%) was obtained by purification via silica gel column chromatography. The molecular weight of Compound 138 was 1197 according to FAB MS measurements. Sublimation purification (320°C, 2.5 x 10 -3 The device was evaluated by Pa).

[0624] (3) Synthesis of Compound 139

[0625] (Synthesis of intermediate 139-(1))

[0626]

[0627] Under an Ar atmosphere, 64.16 ml of toluene and 32.08 ml of a 1:1 mixture of EtOH and water were added to 2,6-dibromo-4-(tert-butyl)aniline (8.02 g, 26.12 mmol), dibenzo[b,d]furan-3-ylboronic acid (15.52 g, 78.36 mmol), K2CO3 (21.66 g, 156.73 mmol), and Pd(Ph3P)4 (4.68 g, 4.05 mmol), and then heated for 24 hours while maintaining the ambient temperature at 80°C. The mixture was filtered via Celite and separated, and the organic layer was concentrated. It was purified by silica gel column chromatography to obtain intermediate 139-(1) (9.72 g, yield 82%). FAB MS analysis revealed that the molecular weight of intermediate 139-(1) was 454.

[0628] (Synthesis of intermediate 139-(2))

[0629]

[0630] Under an Ar atmosphere, intermediate 137-(3) (9.52 g, 18.57 mmol), intermediate 139-(1) (10.73 g, 22.29 mmol), Pd(dba)2 (1.07 g, 1.86 mmol), P(tBu)3.HBF4 (1.08 g, 3.71 mmol), and tBuONa (4.11 g, 42.72 mmol) were added to 92 ml of toluene and heated and stirred at 100°C for 8 hours. Water was added, filtered via Celite, and separated to concentrate the organic layer. The mixture was purified by silica gel column chromatography to obtain intermediate 139-(2) (12.89 g, yield 76%). FAB MS analysis revealed that the molecular weight of intermediate 139-(2) was 913.

[0631] (Synthesis of intermediate 139-(3))

[0632]

[0633] Approximately 10 ml of a small amount of toluene was added to intermediate 139-(2) (9.53 g, 10.44 mmol), 4-iodo-1,1'-biphenyl (29.23 g, 104.36 mmol), CuI (4.97 g, 26.09 mmol), and K2CO3 (21.63 g, 156.53 mmol), and heated for 24 hours while maintaining the ambient temperature at 215°C. The mixture was diluted with CH2Cl2, water was added, filtered via Celite, and separated to concentrate the organic layer. It was purified by silica gel column chromatography to obtain intermediate 139-(3) (10.42 g, yield 82%). FAB MS measurement revealed that the molecular weight of intermediate 139-(3) was 1218.

[0634] (Synthesis of Compound 139)

[0635]

[0636] Under an Ar atmosphere, intermediate 139-(3) (5.21 g, 4.38 mmol) was dissolved in ODCB (44 ml), BBr3 (2.19 g, 8.76 mmol) was added, and the mixture was heated and stirred at 170°C for 10 hours. After cooling to room temperature, DIPEA (6.78 g, 52.55 mmol) was added, followed by water. The mixture was filtered via Celite and separated to concentrate the organic layer. Compound 139 (2.52 g, yield 47%) was obtained by purification via silica gel column chromatography. The molecular weight of Compound 139 was 1225 according to FAB MS measurements. Sublimation purification (310°C, 2.5 x 10 -3 The device was evaluated by Pa).

[0638] (4) Synthesis of Compound 140

[0639] (Synthesis of intermediate 140-(1))

[0640]

[0641] Under an Ar atmosphere, 60.4 ml of toluene and 30.2 ml of a 1:1 mixture of EtOH and water were added to 2,6-dibromo-4-(tert-butyl)aniline (7.55 g, 24.59 mmol), dibenzo[b,d]thiophen-3-ylboronic acid (16.83 g, 73.77 mmol), K2CO3 (20.39 g, 147.54 mmol), and Pd(Ph3P)4 (4.40 g, 3.81 mmol), and then heated for 24 hours while maintaining the ambient temperature at 80°C. The mixture was filtered via Celite and separated, and the organic layer was concentrated. It was purified by silica gel column chromatography to obtain intermediate 140-(1) (10.99 g, yield 87%). FAB MS analysis revealed that the molecular weight of intermediate 140-(1) was 514.

[0642] (Synthesis of intermediate 140-(2))

[0643]

[0644] Under an Ar atmosphere, intermediate 137-(3) (7.05 g, 13.76 mmol), intermediate 140-(1) (8.48 g, 16.51 mmol), Pd(dba)2 (0.79 g, 1.38 mmol), P(tBu)3.HBF4 (0.80 g, 2.75 mmol), and tBuONa (3.04 g, 31.64 mmol) were added to 68 ml of toluene and heated and stirred at 100°C for 8 hours. Water was added, filtered via Celite, and separated to concentrate the organic layer. Purified by silica gel column chromatography, intermediate 140-(2) (11.05 g, yield 85%) was obtained. FAB MS measurement revealed that the molecular weight of intermediate 140-(2) was 945.

[0645] (Synthesis of intermediate 140-(3))

[0646]

[0647] Approximately 10 ml of a small amount of toluene was added to intermediate 140-(2) (10.02 g, 10.6 mmol), 4-iodo-1,1'-biphenyl (29.69 g, 105.99 mmol), CuI (5.05 g, 26.5 mmol), and K2CO3 (21.97 g, 158.99 mmol), and heated for 24 hours while maintaining the ambient temperature at 215°C. The mixture was diluted with CH2Cl2, water was added, filtered via Celite, and separated to concentrate the organic layer. It was purified by silica gel column chromatography to obtain intermediate 140-(3) (11.13 g, yield 84%). FAB MS measurement revealed that the molecular weight of intermediate 140-(3) was 1250.

[0648] (Synthesis of Compound 140)

[0649]

[0650] Under an Ar atmosphere, intermediate 140-(3) (6.01 g, 4.81 mmol) was dissolved in ODCB (48 ml), BBr3 (2.41 g, 9.62 mmol) was added, and the mixture was heated and stirred at 170°C for 10 hours. After cooling to room temperature, DIPEA (7.44 g, 57.71 mmol) was added, followed by water. The mixture was filtered via Celite and separated to concentrate the organic layer. Compound 140 (1.94 g, yield 32%) was obtained by purification via silica gel column chromatography. The molecular weight of Compound 140 was 1258 according to FAB MS measurements. Sublimation purification (320°C, 3.1 x 10 -3 The device was evaluated by Pa).

[0652] (5) Synthesis of Compound 182

[0653] (Synthesis of intermediate 182-(1))

[0654]

[0655] Under an Ar atmosphere, 59.84 ml of toluene and 29.92 ml of a 1:1 mixture of EtOH and water were added to 2-bromo-5-chloroaniline (7.48 g, 36.23 mmol), [1,1'-biphenyl]-4-ylboronic acid (7.89 g, 39.85 mmol), K2CO3 (30.04 g, 217.37 mmol), and Pd(Ph3P)4 (6.49 g, 5.62 mmol), and the mixture was heated for 24 hours while maintaining the ambient temperature at 80°C. The mixture was filtered via Celite and separated, and the organic layer was concentrated. It was purified by silica gel column chromatography to obtain intermediate 182-(1) (8.31 g, yield 82%). FAB MS analysis revealed that the molecular weight of intermediate 182-(1) was 280.

[0656] (Synthesis of intermediate 182-(2))

[0657]

[0658] Under an Ar atmosphere, 64.88 ml of toluene and 32.44 ml of a 1:1 mixture of EtOH and water were added to intermediate 182-(1) (8.11 g, 28.99 mmol), phenylboronic acid (10.6 g, 86.96 mmol), K3PO4 (12.31 g, 57.98 mmol), and Pd(Amphos)2Cl2 (2.05 g, 2.9 mmol), and then heated for 24 hours while maintaining the ambient temperature at 40°C. The mixture was filtered via Celite and separated, and the organic layer was concentrated. It was purified by silica gel column chromatography to obtain intermediate 182-(2) (8.39 g, yield 90%). FAB MS analysis revealed that the molecular weight of intermediate 182-(2) was 321.

[0660] (Synthesis of intermediate 182-(3))

[0661]

[0662] Under an Ar atmosphere, intermediate 51-(3) (8.02 g, 17.57 mmol), intermediate 182-(2) (6.78 g, 21.09 mmol), Pd(dba)2 (1.01 g, 1.76 mmol), P(tBu)3.HBF4 (1.02 g, 3.51 mmol), and tBuONa (3.88 g, 40.41 mmol) were added to 87 ml of toluene and heated and stirred at 100°C for 8 hours. Water was added, filtered via Celite, and separated to concentrate the organic layer. Purified by silica gel column chromatography, intermediate 182-(3) (11.14 g, yield 91%) was obtained. FAB MS measurement revealed that the molecular weight of intermediate 182-(3) was 697.

[0663] (Synthesis of intermediate 182-(4))

[0664]

[0665] Approximately 10 ml of a small amount of toluene was added to intermediate 182-(3) (8.16 g, 11.71 mmol), 1-chloro-3-iodobenzene (27.92 g, 117.08 mmol), CuI (5.57 g, 29.27 mmol), and K2CO3 (24.27 g, 175.62 mmol), and heated for 24 hours while maintaining the ambient temperature at 215°C. The mixture was diluted with CH2Cl2, water was added, filtered via Celite, and separated to concentrate the organic layer. It was purified by silica gel column chromatography to obtain intermediate 182-(4) (7.31 g, yield 68%). FAB MS measurement revealed that the molecular weight of intermediate 182-(4) was 918.

[0666] (Synthesis of intermediate 182-(5))

[0667]

[0668] Under an Ar atmosphere, intermediate 182-(4) (7.03 g, 7.66 mmol) was dissolved in ODCB (77 ml), BBr3 (3.84 g, 15.32 mmol) was added, and the mixture was heated and stirred at 170°C for 10 hours. After cooling to room temperature, DIPEA (11.85 g, 91.89 mmol) was added, water was added, and the mixture was filtered via Celite and separated to concentrate the organic layer. The mixture was purified by silica gel column chromatography to obtain intermediate 182-(5) (2.55 g, yield 36%). FAB MS measurement revealed that the molecular weight of intermediate 182-(5) was 926.

[0669] (Synthesis of Compound 182)

[0670]

[0671] Under an Ar atmosphere, intermediate 182-(5) (1.51 g, 1.63 mmol), 9H-carbazole (0.68 g, 4.08 mmol), Pd(dba)2 (0.09 g, 0.16 mmol), P(tBu)3.HBF4 (0.09 g, 0.33 mmol), and tBuONa (0.63 g, 6.52 mmol) were added to 8 ml of toluene and heated and stirred at 100°C for 8 hours. Water was added, filtered via Celite, and separated to concentrate the organic layer. Compound 182 (1.57 g, yield 81%) was obtained by purification using silica gel column chromatography. The molecular weight of compound 182 was 1187 by FAB MS. Sublimation purification (340°C, 2.5 x 10 -3 The device was evaluated by Pa).

[0673] (6) Synthesis of Compound 183

[0674] (Synthesis of intermediate 183-(1))

[0675]

[0676] Under an Ar atmosphere, 64.4 ml of toluene and 32.2 ml of a 1:1 mixture of EtOH and water were added to 2-bromo-4-chloroaniline (8.05 g, 38.99 mmol), [1,1'-biphenyl]-4-ylboronic acid (8.49 g, 42.89 mmol), K2CO3 (32.33 g, 233.93 mmol), and Pd(Ph3P)4 (6.98 g, 6.04 mmol), and heated for 24 hours while maintaining the ambient temperature at 80°C. The mixture was filtered via Celite and separated, and the organic layer was concentrated. It was purified by silica gel column chromatography to obtain intermediate 183-(1) (9.60 g, yield 88%). FAB MS analysis revealed that the molecular weight of intermediate 183-(1) was 280.

[0677] (Synthesis of intermediate 183-(2))

[0678]

[0679] Under an Ar atmosphere, 75.36 ml of toluene and 37.68 ml of a 1:1 mixture of EtOH and water were added to intermediate 183-(1) (9.42 g, 33.67 mmol), phenylboronic acid (12.32 g, 101.01 mmol), K3PO4 (14.29 g, 67.34 mmol), and Pd(Amphos)2Cl2 (2.38 g, 3.37 mmol), and the mixture was heated for 24 hours while maintaining the ambient temperature at 90°C. The mixture was filtered via Celite and separated, and the organic layer was concentrated. The mixture was purified by silica gel column chromatography to obtain intermediate 183-(2) (9.42 g, yield 87%). FAB MS analysis revealed that the molecular weight of intermediate 183-(2) was 321.

[0680] (Synthesis of intermediate 183-(3))

[0681]

[0682] Under an Ar atmosphere, intermediate 51-(3) (9.31 g, 20.4 mmol), intermediate 183-(2) (7.87 g, 24.48 mmol), Pd(dba)2 (1.17 g, 2.04 mmol), P(tBu)3.HBF4 (1.18 g, 4.08 mmol), and tBuONa (4.51 g, 46.91 mmol) were added to 101 ml of toluene and heated and stirred at 100°C for 8 hours. Water was added, filtered via Celite, and separated to concentrate the organic layer. Purified by silica gel column chromatography, intermediate 183-(3) (12.08 g, yield 85%) was obtained. FAB MS measurement revealed that the molecular weight of intermediate 183-(3) was 697.

[0683] (Synthesis of intermediate 183-(4))

[0684]

[0685] Approximately 10 ml of a small amount of toluene was added to intermediate 183-(3) (6.21 g, 8.91 mmol), 1-chloro-3-iodobenzene (21.25 g, 89.1 mmol), CuI (4.24 g, 22.28 mmol), and K2CO3 (18.47 g, 133.66 mmol), and heated for 24 hours while maintaining the ambient temperature at 215°C. The mixture was diluted with CH2Cl2, water was added, filtered via Celite, and separated to concentrate the organic layer. It was purified by silica gel column chromatography to obtain intermediate 183-(4) (5.89 g, yield 72%). FAB MS measurement revealed that the molecular weight of intermediate 183-(4) was 918.

[0686] (Synthesis of intermediate 183-(5))

[0687]

[0688] Under an Ar atmosphere, intermediate 183-(4) (5.54 g, 6.03 mmol) was dissolved in ODCB (60 ml), BBr3 (3.02 g, 12.07 mmol) was added, and the mixture was heated and stirred at 170°C for 10 hours. After cooling to room temperature, DIPEA (9.34 g, 72.42 mmol) was added, water was added, and the mixture was filtered via Celite and separated to concentrate the organic layer. The mixture was purified by silica gel column chromatography to obtain intermediate 183-(5) (3.97 g, yield 71%). FAB MS measurement revealed that the molecular weight of intermediate 183-(5) was 926.

[0689] (Synthesis of Compound 183)

[0690]

[0691] Under an Ar atmosphere, intermediate 183-(5) (1.51 g, 1.63 mmol), 9H-carbazole (0.68 g, 4.08 mmol), Pd(dba)2 (0.09 g, 0.16 mmol), P(tBu)3.HBF4 (0.09 g, 0.33 mmol), and tBuONa (0.63 g, 6.52 mmol) were added to 8 ml of toluene and heated and stirred at 100°C for 8 hours. Water was added, filtered via Celite, and separated to concentrate the organic layer. Compound 183 (1.47 g, yield 76%) was obtained by purification using silica gel column chromatography. The molecular weight of Compound 183 was 1187 by FAB MS. Sublimation purification (320°C, 2.610 -3 The device was evaluated by Pa).

[0692] (7) Synthesis of Compound 222

[0693] (Synthesis of intermediate 222-(1))

[0694]

[0695] Approximately 10 ml of a small amount of toluene was added to intermediate 138-(2) (4.11 g, 5.9 mmol), 1-chloro-3-iodobenzene (14.06 g, 58.97 mmol), CuI (2.81 g, 14.74 mmol), and K2CO3 (12.23 g, 88.46 mmol), and heated for 24 hours while maintaining the ambient temperature at 215°C. The mixture was diluted with CH2Cl2, water was added, filtered via Celite, and separated to concentrate the organic layer. It was purified by silica gel column chromatography to obtain intermediate 222-(1) (5.69 g, yield 87%). FAB MS measurement revealed that the molecular weight of intermediate 222-(1) was 1108.

[0696] (Synthesis of intermediate 222-(2))

[0697]

[0698] Under an Ar atmosphere, intermediate 222-(1) (5.44 g, 4.91 mmol) was dissolved in ODCB (49 ml), BBr3 (2.46 g, 9.82 mmol) was added, and the mixture was heated and stirred at 170°C for 10 hours. After cooling to room temperature, DIPEA (7.6 g, 58.9 mmol) was added, water was added, and the mixture was filtered via Celite and separated to concentrate the organic layer. The mixture was purified by silica gel column chromatography to obtain intermediate 222-(2) (3.61 g, yield 65%). FAB MS measurement revealed that the molecular weight of intermediate 222-(2) was 1130.

[0699] (Synthesis of Compound 222)

[0700]

[0701] Under an Ar atmosphere, intermediate 222-(2) (3.22 g, 2.85 mmol), 9H-carbazole (1.19 g, 7.12 mmol), Pd(dba)2 (0.16 g, 0.28 mmol), P(tBu)3.HBF4 (0.17 g, 0.57 mmol), and tBuONa (1.1 g, 11.4 mmol) were added to 14 ml of toluene and heated and stirred at 100°C for 8 hours. Water was added, filtered via Celite, and separated to concentrate the organic layer. Compound 222 (3.33 g, yield 84%) was obtained by purification using silica gel column chromatography. The molecular weight of Compound 222 was 1392 by FAB MS. Sublimation purification (330°C, 2.9 x 10 -3 The device was evaluated by Pa).

[0703] (8) Synthesis of Compound 226

[0704] (Synthesis of intermediate 226-(1))

[0705]

[0706] Under an Ar atmosphere, 1,3-dibromo-5-(tert-butyl)benzene (4.18 g, 14.31 mmol), intermediate 138-(1) (16.23 g, 35.79 mmol), Pd(dba)2 (0.82 g, 1.43 mmol), P(tBu)3.HBF4 (0.83 g, 2.86 mmol), and tBuONa (5.5 g, 57.26 mmol) were added to 71 ml of toluene and heated and stirred at 100°C for 8 hours. Water was added, filtered via Celite, and separated to concentrate the organic layer. Purified by silica gel column chromatography, intermediate 226-(1) (12.03 g, yield 81%) was obtained. FAB MS measurement revealed that the molecular weight of intermediate 226-(1) was 1037.

[0707] (Synthesis of intermediate 226-(2))

[0708]

[0709] Approximately 10 ml of a small amount of toluene was added to intermediate 226-(1) (12.08 g, 11.64 mmol), 1-chloro-3-iodobenzene (27.76 g, 116.44 mmol), CuI (5.54 g, 29.11 mmol), and K2CO3 (24.14 g, 174.66 mmol), and heated for 24 hours while maintaining the ambient temperature at 215°C. The mixture was diluted with CH2Cl2, water was added, filtered via Celite, and separated to concentrate the organic layer. It was purified by silica gel column chromatography to obtain intermediate 226-(2) (10.84 g, yield 74%). FAB MS measurement revealed that the molecular weight of intermediate 226-(2) was 1259.

[0710] (Synthesis of intermediate 226-(3))

[0711]

[0712] Under an Ar atmosphere, intermediate 226-(2) (5.17 g, 4.11 mmol) was dissolved in ODCB (41 ml), BBr3 (2.06 g, 8.22 mmol) was added, and the mixture was heated and stirred at 170°C for 10 hours. After cooling to room temperature, DIPEA (6.36 g, 49.3 mmol) was added, water was added, and the mixture was filtered via Celite and separated to concentrate the organic layer. The mixture was purified by silica gel column chromatography to obtain intermediate 226-(3) (4.06 g, yield 78%). FAB MS measurement revealed that the molecular weight of intermediate 226-(3) was 1266.

[0713] (Synthesis of Compound 226)

[0714]

[0715] Under an Ar atmosphere, intermediate 226-(3) (3.88 g, 3.06 mmol) was added to 15 ml of 9H-carbazole (1.28 g, 7.66 mmol), Pd(dba)2 (0.18 g, 0.31 mmol), P(tBu)3.HBF4 (0.18 g, 0.61 mmol), tBuONa (1.18 g, 12.26 mmol), and toluene, and heated and stirred at 100°C for 8 hours. Water was added, filtered via Celite, and separated to concentrate the organic layer. Purification by silica gel column chromatography yielded compound 226 (2.85 g, yield 4%). FAB MS analysis revealed the molecular weight of compound 226 to be 1259. Sublimation purification (340°C, 3.1 x 10 -3 The device was evaluated by Pa).

[0716] (10) Synthesis of Compound 228

[0717] (Synthesis of intermediate 228-(1))

[0718]

[0719] Under an Ar atmosphere, 56.32 ml of toluene and 28.16 ml of a 1:1 mixture of EtOH and water were added to 2,6-dibromoaniline (7.04 g, 28.06 mmol), [1,1'-biphenyl]-4-ylboronic acid (13.33 g, 67.34 mmol), K2CO3 (23.27 g, 168.34 mmol), and Pd(Ph3P)4 (5.03 g, 4.35 mmol), and the mixture was heated for 24 hours while maintaining the ambient temperature at 80°C. The mixture was filtered via Celite and separated, and the organic layer was concentrated. It was purified by silica gel column chromatography to obtain intermediate 228-(1) (9.03 g, yield 81%). FAB MS analysis revealed that the molecular weight of intermediate 228-(1) was 398.

[0720] (Synthesis of intermediate 228-(2))

[0721]

[0722] Under an Ar atmosphere, 1,3-dibromo-5-chlorobenzene (4.63 g, 17.13 mmol), intermediate 228-(1) (8.17 g, 20.55 mmol), Pd(dba)2 (0.98 g, 1.71 mmol), P(tBu)3.HBF4 (0.99 g, 3.43 mmol), and tBuONa (3.79 g, 39.39 mmol) were added to 85 ml of toluene and heated and stirred at 100°C for 8 hours. Water was added, filtered via Celite, and separated to concentrate the organic layer. The mixture was purified by silica gel column chromatography to obtain intermediate 228-(2) (11.92 g, yield 77%). FAB MS analysis revealed that the molecular weight of intermediate 228-(2) was 904.

[0723] (Synthesis of intermediate 228-(3))

[0724]

[0725] Under an Ar atmosphere, 92.4 ml of toluene and 46.2 ml of a 1:1 mixture of EtOH and water were added to intermediate 228-(2) (11.55 g, 12.78 mmol), phenylboronic acid (4.68 g, 38.35 mmol), K3PO4 (5.43 g, 25.57 mmol), and Pd(Amphos)2Cl2 (0.91 g, 1.28 mmol), and then heated for 24 hours while maintaining the ambient temperature at 90°C. The mixture was filtered via Celite and separated, and the organic layer was concentrated. It was purified by silica gel column chromatography to obtain intermediate 228-(3) (9.06 g, yield 75%). FAB MS analysis revealed that the molecular weight of intermediate 228-(3) was 945.

[0726] (Synthesis of intermediate 228-(4))

[0727]

[0728] Approximately 10 ml of a small amount of toluene was added to intermediate 228-(3) (8.54 g, 9.03 mmol), 1-chloro-3-iodobenzene (21.54 g, 90.35 mmol), CuI (4.3 g, 22.59 mmol), and K2CO3 (18.73 g, 135.52 mmol), and heated for 24 hours while maintaining the ambient temperature at 215°C. The mixture was diluted with CH2Cl2, water was added, filtered via Celite, and separated to concentrate the organic layer. It was purified by silica gel column chromatography to obtain intermediate 228-(4) (7.38 g, yield 70%). FAB MS measurement revealed that the molecular weight of intermediate 228-(4) was 1166.

[0729] (Synthesis of intermediate 228-(5))

[0730]

[0731] Under an Ar atmosphere, intermediate 228-(4) (6.88 g, 5.9 mmol) was dissolved in ODCB (59 ml), BBr3 (2.96 g, 11.8 mmol) was added, and the mixture was heated and stirred at 170°C for 10 hours. After cooling to room temperature, DIPEA (9.13 g, 70.79 mmol) was added, water was added, and the mixture was filtered via Celite and separated to concentrate the organic layer. The mixture was purified by silica gel column chromatography to obtain intermediate 228-(5) (2.49 g, yield 36%). FAB MS measurement revealed that the molecular weight of intermediate 228-(5) was 1174.

[0732] (Synthesis of Compound 228)

[0733]

[0734] Under an Ar atmosphere, intermediate 228-(5) (2.11 g, 1.8 mmol), 9H-carbazole (0.75 g, 4.49 mmol), Pd(dba)2 (0.1 g, 0.18 mmol), P(tBu)3.HBF4 (0.1 g, 0.36 mmol), and tBuONa (0.69 g, 7.19 mmol) were added to 8 ml of toluene and heated and stirred at 100°C for 8 hours. Water was added, filtered via Celite, and separated to concentrate the organic layer. Compound 228 (2.22 g, yield 86%) was obtained by purification using silica gel column chromatography. The molecular weight of compound 228 was 1436 by FAB MS. Sublimation purification (340°C, 2.6 x 10 -3 The device was evaluated by Pa).

[0735] (11) Synthesis of Compound 240

[0736] (Synthesis of intermediate 240-(1))

[0737]

[0738] Under an Ar atmosphere, 89.84 ml of toluene and 44.92 ml of a 1:1 mixture of EtOH and water were added to intermediate 228-(2) (11.23 g, 12.43 mmol), (3,5-di-tert-butylphenyl)boronic acid (8.73 g, 37.29 mmol), K3PO4 (5.28 g, 24.86 mmol), and Pd(Amphos)2Cl2 (0.88 g, 1.24 mmol), and the mixture was heated for 24 hours while maintaining the ambient temperature at 90°C. The mixture was filtered via Celite and separated, and the organic layer was concentrated. The mixture was purified by silica gel column chromatography to obtain intermediate 240-(1) (9.73 g, yield 74%). FAB MS analysis revealed that the molecular weight of intermediate 240-(1) was 1057.

[0739] (Synthesis of intermediate 240-(2))

[0740]

[0741] Approximately 10 ml of a small amount of toluene was added to intermediate 240-(1) (8.54 g, 9.52 mmol), 1-chloro-3-iodobenzene (22.7 g, 95.2 mmol), CuI (4.53 g, 23.8 mmol), and K2CO3 (19.74 g, 142.8 mmol), and heated for 24 hours while maintaining the ambient temperature at 215°C. The mixture was diluted with CH2Cl2, water was added, filtered via Celite, and separated to concentrate the organic layer. It was purified by silica gel column chromatography to obtain intermediate 240-(2) (10.22 g, yield 84%). FAB MS measurement revealed that the molecular weight of intermediate 240-(2) was 1279.

[0742] (Synthesis of intermediate 240-(3))

[0743]

[0744] Under an Ar atmosphere, intermediate 240-(2) (9.88 g, 7.73 mmol) was dissolved in ODCB (77 ml), BBr3 (3.87 g, 15.46 mmol) was added, and the mixture was heated and stirred at 170°C for 10 hours. After cooling to room temperature, DIPEA (11.96 g, 92.73 mmol) was added, water was added, and the mixture was filtered via Celite and separated to concentrate the organic layer. The mixture was purified by silica gel column chromatography to obtain intermediate 240-(3) (3.08 g, yield 31%). FAB MS measurement revealed that the molecular weight of intermediate 240-(3) was 1286.

[0745] (Synthesis of Compound 240)

[0746]

[0747] Under an Ar atmosphere, intermediate 240-(3) (2.55 g, 1.98 mmol), 9H-carbazole (0.83 g, 4.96 mmol), Pd(dba)2 (0.11 g, 0.2 mmol), P(tBu)3.HBF4 (0.12 g, 0.4 mmol), and tBuONa (0.76 g, 7.93 mmol) were added to 9 ml of toluene and heated and stirred at 100°C for 8 hours. Water was added, filtered via Celite, and separated to concentrate the organic layer. Compound 240 (2.45 g, yield 80%) was obtained by purification using silica gel column chromatography. The molecular weight of Compound 240 was 1548 by FAB MS. Sublimation purification (350°C, 2.1 x 10 -3 The device was evaluated by Pa).

[0748] (12) Synthesis of Compound 263

[0749] (Synthesis of intermediate 263-(1))

[0750]

[0751] Under an Ar atmosphere, 1,3-dibromo-5-(tert-butyl)benzene (5.01 g, 17.16 mmol) and intermediate 182-(2) (13.79 g, 42.89 mmol), Pd(dba)2 (0.99 g, 1.72 mmol), P(tBu)3.HBF4 (1 g, 3.43 mmol), and tBuONa (6.6 g, 68.63 mmol) were added to 85 ml of toluene and heated and stirred at 100°C for 8 hours. Water was added, filtered via Celite, and separated to concentrate the organic layer. Purified by silica gel column chromatography, intermediate 263-(1) (12.07 g, yield 91%) was obtained. FAB MS measurement revealed that the molecular weight of intermediate 263-(1) was 773.

[0752] (Synthesis of intermediate 263-(2))

[0753]

[0754] Approximately 10 ml of a small amount of toluene was added to intermediate 263-(1) (11.55 g, 9.52 mmol), 1-chloro-3-iodobenzene (22.7 g, 95.2 mmol), CuI (4.53 g, 23.8 mmol), and K2CO3 (19.74 g, 142.8 mmol), and heated for 24 hours while maintaining the ambient temperature at 215°C. The mixture was diluted with CH2Cl2, water was added, filtered via Celite, and separated to concentrate the organic layer. It was purified by silica gel column chromatography to obtain intermediate 263-(1) (7.29 g, yield 77%). FAB MS measurement revealed that the molecular weight of intermediate 263-(1) was 994.

[0755] (Synthesis of intermediate 263-(3))

[0756]

[0757] Under an Ar atmosphere, intermediate 263-(2) (7.01 g, 7.05 mmol) was dissolved in ODCB (71 ml), BBr3 (3.53 g, 14.1 mmol) was added, and the mixture was heated and stirred at 170°C for 10 hours. After cooling to room temperature, DIPEA (10.92 g, 84.62 mmol) was added, water was added, and the mixture was filtered via Celite and separated to concentrate the organic layer. The mixture was purified by silica gel column chromatography to obtain intermediate 263-(3) (1.98 g, yield 28%). FAB MS measurement revealed that the molecular weight of intermediate 263-(3) was 1002.

[0758] (Synthesis of Compound 263)

[0759]

[0760] Under an Ar atmosphere, intermediate 263-(3) (1.85 g, 6.34 mmol), 3-(tert-butyl)-9H-carbazole (5.09 g, 15.84 mmol), Pd(dba)2 (0.36 g, 0.63 mmol), P(tBu)3.HBF4 (0.37 g, 1.27 mmol), and tBuONa (2.44 g, 25.34 mmol) were added to 31 ml of toluene and heated and stirred at 100°C for 8 hours. Water was added, filtered via Celite, and separated to concentrate the organic layer. Compound 263 (3.62 g, yield 74%) was obtained by purification via silica gel column chromatography. The molecular weight of compound 263 was 773 by FAB MS. Sublimation purification (320°C, 2.7 x 10 -3 The device was evaluated by Pa).

[0761] (13) Synthesis of Compound 264

[0762] (Synthesis of intermediate 264-(1))

[0763]

[0764] Under an Ar atmosphere, 1,3-dibromo-5-chlorobenzene (5.22 g, 19.31 mmol) and intermediate 182-(2) (15.52 g, 48.27 mmol), Pd(dba)2 (1.11 g, 1.93 mmol), P(tBu)3.HBF4 (1.12 g, 3.86 mmol), and tBuONa (7.42 g, 77.23 mmol) were added to 96 ml of toluene and heated and stirred at 100°C for 8 hours. Water was added, filtered via Celite, and separated to concentrate the organic layer. Purified by silica gel column chromatography, intermediate 264-(1) (12.77 g, yield 88%) was obtained. FAB MS measurement revealed that the molecular weight of intermediate 264-(1) was 751.

[0765] (Synthesis of intermediate 264-(2))

[0766]

[0767] Under an Ar atmosphere, 1,3-dibromo-5-chlorobenzene (5.22 g, 19.31 mmol) and intermediate 182-(2) (15.52 g, 48.27 mmol), Pd(dba)2 (1.11 g, 1.93 mmol), P(tBu)3.HBF4 (1.12 g, 3.86 mmol), and tBuONa (7.42 g, 77.23 mmol) were added to 96 ml of toluene and heated and stirred at 100°C for 8 hours. Water was added, filtered via Celite, and separated to concentrate the organic layer. Purified by silica gel column chromatography, intermediate 264-(1) (12.77 g, yield 88%) was obtained. FAB MS measurement revealed that the molecular weight of intermediate 264-(1) was 751.

[0768] (Synthesis of intermediate 264-(3))

[0769]

[0770] Approximately 10 ml of a small amount of toluene was added to intermediate 264-(2) (12.44 g, 9.52 mmol), 1-chloro-3-iodobenzene (22.7 g, 95.2 mmol), CuI (4.53 g, 23.8 mmol), and K2CO3 (19.74 g, 142.8 mmol), and heated for 24 hours while maintaining the ambient temperature at 215°C. The mixture was diluted with CH2Cl2, water was added, filtered via Celite, and separated to concentrate the organic layer. It was purified by silica gel column chromatography to obtain intermediate 264-(3) (8.90 g, yield 83%). FAB MS measurement revealed that the molecular weight of intermediate 264-(3) was 1126.

[0771] (Synthesis of intermediate 264-(4))

[0772]

[0773] Under an Ar atmosphere, intermediate 264-(3) (8.71 g, 7.73 mmol) was dissolved in ODCB (77 ml), BBr3 (3.87 g, 15.47 mmol) was added, and the mixture was heated and stirred at 170°C for 10 hours. After cooling to room temperature, DIPEA (11.97 g, 92.8 mmol) was added, water was added, and the mixture was filtered via Celite and separated to concentrate the organic layer. The mixture was purified by silica gel column chromatography to obtain intermediate 264-(4) (3.24 g, yield 37%). FAB MS measurement revealed that the molecular weight of intermediate 264-(4) was 1134.

[0774] (Synthesis of Compound 264)

[0775]

[0776] Under an Ar atmosphere, intermediate 264-(4) (3.01 g, 2.65 mmol), 3-(tert-butyl)-9H-carbazole (1.48 g, 6.64 mmol), Pd(dba)2 (0.15 g, 0.27 mmol), P(tBu)3.HBF4 (0.15 g, 0.53 mmol), and tBuONa (1.02 g, 10.62 mmol) were added to 13 ml of toluene and heated and stirred at 100°C for 8 hours. Water was added, filtered via Celite, and separated to concentrate the organic layer. Compound 264 (3.08 g, yield 77%) was obtained by purification using silica gel column chromatography. The molecular weight of Compound 264 was 1508 by FAB MS. Sublimation purification (350°C, 3.3 x 10 -3 The device was evaluated by Pa).

[0777] (14) Synthesis of Compound 401

[0778] (Synthesis of intermediate 401-(1))

[0779]

[0780] Under an Ar atmosphere, 1-bromo-3-(tert-butyl)-5-fluorobenzene (10.22 g, 44.22 mmol), [1,1'-biphenyl]-4-ol (9.03 g, 53.07 mmol), and K2CO3 (27.5 g, 199 mmol) were combined with 102 ml of NMP and heated for 24 hours while maintaining the ambient temperature at 140°C. The mixture was diluted with CH2Cl2, water was added, filtered via Celite, and separated to concentrate the organic layer. It was purified by silica gel column chromatography to obtain intermediate 401-(1) (14.16 g, yield 84%). FAB MS analysis revealed that the molecular weight of intermediate 401-(1) was 381.

[0781] (Synthesis of intermediate 401-(2))

[0782]

[0783] Under an Ar atmosphere, intermediate 401-(1) (13.22 g, 34.67 mmol), intermediate 139-(1) (20.04 g, 41.6 mmol), Pd(dba)2 (1.99 g, 3.47 mmol), P(tBu)3.HBF4 (2.01 g, 6.93 mmol), and tBuONa (7.66 g, 79.74 mmol) were added to 173 ml of toluene and heated and stirred at 100°C for 8 hours. Water was added, filtered via Celite, and separated to concentrate the organic layer. The mixture was purified by silica gel column chromatography to obtain intermediate 401-(2) (21.96 g, yield 81%). FAB MS analysis revealed that the molecular weight of intermediate 401-(2) was 782.

[0784] (Synthesis of intermediate 401-(3))

[0785]

[0786] Approximately 10 ml of a small amount of toluene was added to intermediate 401-(2) (10.05 g, 9.52 mmol), 4-iodo-1,1'-biphenyl (26.67 g, 95.2 mmol), CuI (4.53 g, 23.8 mmol), and K2CO3 (19.74 g, 142.8 mmol), and heated for 24 hours while maintaining the ambient temperature at 215°C. The mixture was diluted with CH2Cl2, water was added, filtered via Celite, and separated to concentrate the organic layer. It was purified by silica gel column chromatography to obtain intermediate 401-(3) (7.74 g, yield 87%). FAB MS measurement revealed that the molecular weight of intermediate 401-(3) was 934.

[0787] (Synthesis of Compound 401)

[0788]

[0789] Under an Ar atmosphere, intermediate 401-(3) (7.51 g, 8.04 mmol) was dissolved in ODCB (80 ml), BBr3 (4.03 g, 16.08 mmol) was added, and the mixture was heated and stirred at 170°C for 10 hours. After cooling to room temperature, DIPEA (12.44 g, 96.47 mmol) was added, followed by water. The mixture was filtered via Celite and separated to concentrate the organic layer. Compound 401 (1.82 g, yield 24%) was obtained by purification via silica gel column chromatography. The molecular weight of Compound 401 was 942 according to FAB MS measurements. Sublimation purification (280°C, 2.3 x 10 -3 The device was evaluated by Pa).

[0790] (15) Synthesis of Compound 543

[0791] (Synthesis of intermediate 543-(1))

[0792]

[0793] Under an Ar atmosphere, 1-bromo-3-(tert-butyl)-5-fluorobenzene (8.66 g, 37.47 mmol), [1,1'-biphenyl]-4-thio (7.65 g, 44.97 mmol), and K2CO3 (23.31 g, 168.62 mmol) were combined with 86 ml of NMP and heated for 24 hours while maintaining the ambient temperature at 140°C. The mixture was diluted with CH2Cl2, water was added, filtered via Celite, and separated to concentrate the organic layer. It was purified by silica gel column chromatography to obtain intermediate 543-(1) (8.34 g, yield 56%). FAB MS analysis revealed that the molecular weight of intermediate 543-(1) was 397.

[0794] (Synthesis of intermediate 543-(2))

[0795]

[0796] Under an Ar atmosphere, intermediate 543-(1) (7.75 g, 19.5 mmol), intermediate 137-(2) (8.84 g, 23.4 mmol), Pd(dba)2 (1.12 g, 1.95 mmol), P(tBu)3.HBF4 (1.13 g, 3.9 mmol), and tBuONa (4.31 g, 44.86 mmol) were added to 97 ml of toluene and heated and stirred at 100°C for 8 hours. Water was added, filtered via Celite, and separated to concentrate the organic layer. Purified by silica gel column chromatography, intermediate 543-(2) (11.37 g, yield 84%) was obtained. FAB MS measurement revealed that the molecular weight of intermediate 543-(2) was 694.

[0797] (Synthesis of intermediate 543-(3))

[0798]

[0799] Approximately 10 ml of a small amount of toluene was added to intermediate 543-(2) (11.02 g, 9.52 mmol), 4-iodo-1,1'-biphenyl (26.67 g, 95.2 mmol), CuI (4.53 g, 23.8 mmol), and K2CO3 (19.74 g, 142.8 mmol), and heated for 24 hours while maintaining the ambient temperature at 215°C. The mixture was diluted with CH2Cl2, water was added, filtered via Celite, and separated to concentrate the organic layer. It was purified by silica gel column chromatography to obtain intermediate 543-(3) (5.72 g, yield 71%). FAB MS measurement revealed that the molecular weight of intermediate 543-(3) was 846.

[0800] (Synthesis of Compound 543)

[0801]

[0802] Under an Ar atmosphere, intermediate 543-(3) (5.54 g, 6.55 mmol) was dissolved in ODCB (65 ml), BBr3 (3.28 g, 13.09 mmol) was added, and the mixture was heated and stirred at 170°C for 10 hours. After cooling to room temperature, DIPEA (10.13 g, 78.56 mmol) was added, followed by water. The mixture was filtered via Celite and separated to concentrate the organic layer. Compound 543 (1.45 g, yield 26%) was obtained by purification via silica gel column chromatography. The molecular weight of compound 543 was 854 according to FAB MS measurements. Sublimation purification (320°C, 2.5 x 10 -3 The device was evaluated by Pa).

[0803] 2. Fabrication and Evaluation of Light Emitting Devices

[0804] A light-emitting device of one embodiment containing a condensed polycyclic compound of one embodiment in the light-emitting layer was manufactured by the following method. Light-emitting devices of Examples 1 to 15 were fabricated using the condensed polycyclic compounds of the above-described examples, compounds 51, 137, 138, 139, 140, 182, 183, 222, 226, 228, 240, 263, 264, 401, and 543, as light-emitting layer dopant materials. Comparative Examples 1 to 9 correspond to light-emitting devices fabricated using Comparative Compound X1 to Comparative Compound X9 as light-emitting layer dopant materials.

[0805] [Example Compound]

[0806]

[0807]

[0808] [Comparative Example Compound]

[0809]

[0810]

[0811] (Fabrication of light-emitting devices)

[0812] A first electrode with a thickness of 150 nm is formed using ITO, a hole injection layer with a thickness of 10 nm is formed on the first electrode using HATCN (dipyrazino[2,3-f: 2',3'-h] quinox aline-2,3,6,7,10,11-hexacarbonitrile), a hole transport layer with a thickness of 80 nm is formed on the hole injection layer using NPD (N,N′-Di(1-naphthyl)-N,N′-diphenyl-(1,1′-biphenyl)-4,4′-diamine), a light emission auxiliary layer with a thickness of 5 nm is formed on the hole transport layer using mCP (1,3-Bis(N-carbazolyl)benzene), and a light-emitting layer with a thickness of 20 nm is formed on the light emission auxiliary layer by doping mCBP (3,3′-Di(9H-carbazol-9-yl)-1,1′-biphenyl) with 1% of the compound of the example or the compound of the comparative example. An electron transport layer with a thickness of 30 nm was formed on the emissive layer using TPBi (2,2',2''-(1,3,5-Benzinetriyl)-tris(1-phenyl-1-H-benzimidazole)), an electron injection layer with a thickness of 0.5 nm was formed on the electron transport layer using LiF, and a second electrode with a thickness of 100 nm was formed on the electron injection layer using Al. Each layer was formed by deposition under vacuum conditions.

[0813] The compounds used in the fabrication of the light-emitting devices of the examples and comparative examples are disclosed below. The following materials are known materials, and commercially available products were sublimated and purified for use in device fabrication.

[0814]

[0815] (Evaluation of light-emitting device characteristics)

[0816] Table 1 shows the evaluation results of the light-emitting devices for Examples 1 to 15 and Comparative Examples 1 to 9. Table 1 shows the maximum emission wavelength (λ) of the fabricated light-emitting devices. max The delayed fluorescence lifetime and relative lifetime (LT50) were compared and presented.

[0817] In the characteristic evaluation results for the examples and comparative examples shown in Table 1, the maximum emission wavelength (λ max ) represented the maximum emission wavelength value in the emission spectrum of the light-emitting device, and the relative lifetime was an initial luminance of 100 cd / m² 2 The luminance half-life was evaluated and expressed. The relative lifespan was expressed relatively based on the results of Comparative Example 3.

[0818] Example of device fabrication Dopant λmax LT50 (nm) Relative lifespan Example 1 Compound 51 462 4.1 Example 2 Compound 137 463 5.2 Example 3 Compound 138 463 6.2 Example 4 Compound 139 462 3.8 Example 5 Compound 140 460 3.0 Example 6 Compound 182 463 6.0 Example 7 Compound 183 463 6.2 Example 8 Compound 222 461 7.5 Example 9 Compound 226 461 7.3 Example 10 Compound 228 460 6.8 Example 11 Compound 240 463 7.1 Example 12 Compound 263 463 7.0 Example 13 Compound 264 464 6.5 Example 14 Compound 401 455 2.8 Example 15 Compound 543 460 3.3 Comparative Example 1 Comparative Example Compound X1 457 0.3 Comparative Example 2 Comparative Example Compound X2 446 0.2 Comparative Example 3 Comparative Example Compound X3 467 1.0 Comparative Example 4 Comparative Example Compound X4 456 0.1 Comparative Example 5 Comparative Example Compound X5 457 0.2 Comparative Example 6 Comparative Example Compound X6 461 2.3 Comparative Example 7 Comparative Example Compound X7 463 2.0 Comparative Example 8 Comparative Example Compound X8 463 1.6 Comparative Example 9 Comparative Example Compound X9 465 1.3

[0819] Referring to the results in Table 1, it can be seen that the lifespan characteristics of the light-emitting devices using a condensed polycyclic compound according to one embodiment of the present invention as a light-emitting material are improved compared to the comparative example. The compounds of the examples can achieve a long lifespan by including a condensed ring core in which five rings are condensed around a first boron atom, a first nitrogen atom, and a first heteroatom, and a first substituent connected to the first nitrogen atom of the condensed ring core. The compounds of the examples can exhibit excellent molecular stability due to the specific structure of the first substituent, and thus can contribute to the long lifespan of the light-emitting device (ED).

[0820] The emission wavelengths of Examples 1 to 15 all exhibited color purity close to pure blue around 460 nm, and all showed long lifespans when compared to the LT50 of Comparative Examples 1 to 9.

[0821] Looking at Comparative Examples 1 to 3 in Table 1, Comparative Compounds X1 to X3 include a plate-like framework structure centered on one boron atom and two nitrogen atoms, but the plate-like framework does not include the first substituent proposed in the present invention, so it can be confirmed that the device lifespan of Comparative Examples 1 to 3, which include Comparative Compounds X1 to X3 as dopant materials, is reduced.

[0822] Referring to Comparative Examples 4 and 5 in Table 1, Comparative Compound X4 and Comparative Compound X5 contain a plate-like framework structure centered on one boron atom and two nitrogen atoms, but do not include the first substituent proposed in the present invention in the plate-like framework, so it can be confirmed that the device lifespan is significantly reduced. Specifically, Comparative Compound X4 and Comparative Compound X5 contain the first benzene moiety and the first substituent of the first substituent proposed in the present invention, but do not include the second substituent. Consequently, it is understood that the degradation of the material is increased due to increased intermolecular interactions caused by the small volume of the substituent. Accordingly, it is understood that the lifespan-enhancing effect of Comparative Examples 4 and 5, which include Comparative Compound X4 and Comparative Compound X5 as dopant materials, is reduced. In contrast, it is understood that the degradation of the material is reduced because the Example Compounds contain the first substituent proposed in the present invention, thereby increasing the protective effect on the condensed ring core. Accordingly, it is understood that a light-emitting device of one embodiment of the present invention, comprising the compounds of the examples as dopant materials, has achieved a long lifespan.

[0823] Referring to Comparative Examples 6 and 7 in Table 1, Comparative Compound X6 and Comparative Compound X7 contain a plate-like framework structure centered on one boron atom and two nitrogen atoms, but the plate-like framework does not contain the first substituent proposed in the present invention, so it can be confirmed that the device lifespan is reduced. Specifically, Comparative Compound X6 and Comparative Compound X7 do not contain a third benzene moiety that bonds to a carbon at the para position relative to the first benzene moiety among the carbon atoms constituting the second benzene moiety of the first substituent proposed in the present invention. Consequently, it is understood that the material stability is reduced electronically, physically, and structurally, leading to increased material degradation. Accordingly, it is understood that the lifespan-enhancing effect of Comparative Examples 6 and 7, which include Comparative Compound X6 and Comparative Compound X7 respectively as dopant materials, is reduced.

[0824] Referring to Comparative Examples 8 and 9 in Table 1, Comparative Compound X8 and Comparative Compound X9 include a plate-like framework structure centered on one boron atom and two nitrogen atoms, and it can be confirmed that the device lifespan is reduced because the plate-like framework does not include the first substituent proposed in the present invention or the second substituent proposed in the present invention. Specifically, Comparative Compound X8 and Comparative Compound X9 do not include the second substituent proposed in the present invention, and since they include four or more heterocyclic moieties such as dibenzofuran in the substituents connected to the condensed ring core, it is understood that the material stability is reduced due to increased intermolecular stacking. Accordingly, it is understood that the lifespan-enhancing effect of Comparative Examples 8 and 9, which include Comparative Compound X8 and Comparative Compound X9 as dopant materials, is reduced.

[0825] Hereinafter, with reference to FIG. 12 and Table 1 above, a condensed polycyclic compound of one embodiment according to the present invention and a light-emitting element of one embodiment according to the present invention will be described.

[0826] FIG. 12 is a graph showing the lowest singlet excitation energy level (S1 level) and the lowest triplet excitation energy level (T1 level) for each of the light-emitting devices containing the example compounds and comparative example compounds as dopant materials. FIG. 12 is a graph showing the lowest singlet excitation energy level (S1 level) and the lowest triplet excitation energy level (T1 level) for each of the light-emitting devices containing the following substituent C1 connected to the first nitrogen atom of the condensed ring core, the following substituent C2 connected to the first nitrogen atom of the condensed ring core, and the following substituent E1 connected to the first nitrogen atom of the condensed ring core as dopant materials. Meanwhile, the lowest singlet excitation energy level (S1 level) and the lowest triplet excitation energy level (T1 level) were calculated using non-experimental molecular orbital theory, and the calculations were performed using the Gaussian 09 program via B3LYP / 6-31G(d)(TD-DFT).

[0827] [Substituent C1]

[0828]

[0829] [Substituent C2]

[0830]

[0831] [Substituent E1]

[0832]

[0833] In the above substituents C1, C2, and E1 represents the position connected to the first nitrogen atom of the condensed ring core.

[0834] Referring to FIG. 12, Example Compound 222 has relatively satisfactory values ​​for the lowest singlet excitation energy level and the lowest triplet excitation energy level compared to Comparative Example Compound Q1 and Comparative Example Compound Q2, so material degradation can be prevented. Substituent E1 has a relatively expanded conjugation structure compared to substituents C1 and C2. It is thought that as the conjugation structure of the substituent expands, the entire molecule containing it becomes stabilized, thereby stabilizing the values ​​for the lowest singlet excitation energy level and the lowest triplet excitation energy level. Accordingly, it is thought that a light-emitting device containing the Example Compound containing substituent E1 can achieve a long lifespan effect.

[0835] Referring to FIG. 12 and Table 1, Example 8, containing Example Compound 222, exhibits a relatively long-life effect compared to Comparative Example 6, containing Comparative Example Compound X6. It is understood that the long-life effect is reduced because Comparative Example Compound 6 does not contain a p-terphenyl moiety unlike the first substituent, and thus the degree of expansion of the conjugated structure is similar to that of substituent C2 rather than substituent E1, resulting in relatively unstable lowest singlet excitation energy level and lowest triplet excitation energy level values. Although there is a difference in that the substituent of Comparative Example Compound 6 additionally contains a phenyl group in the m-terphenyl moiety compared to substituent C2, this does not contribute to resonance stabilization and thus cannot realize the effect of protecting the condensed ring core; therefore, it is thought that Comparative Example Compound 6 and Comparative Example Compound Q2, which contains substituent C2, exhibit substantially similar effects.

[0836] In Table 2, to provide a specific explanation of the effects of the present invention, the number of benzene rings involved in protecting the condensed ring core and the number of benzene rings not involved in protecting the condensed ring core are compared in Example Compound 222 and Comparative Compound X6, respectively, within the first partial structure. In Table 2, "first partial structure" may refer collectively to the substituent structure surrounding the condensed ring core. For example, "first partial structure" may refer to a region containing a first substituent connected to the first nitrogen atom of the condensed ring core and a second substituent bonded thereto when the first heteroatom of the condensed ring core corresponds to the nitrogen atom.

[0837] compound Benzene ring within the structure of Part 1 Benzene ring number involved in protecting the condensed ring core Benzene ring numbers that do not participate in protecting the condensed ring core Example Compound 222 8 0 Comparative Example Compound X6 6 2

[0838] Referring to Tables 1 and 2, although both Example Compound 222 and Comparative Compound X6 have eight benzene rings in the first substructure, it can be confirmed that Example Compound 222 has a relatively larger number of benzene rings involved in protecting the condensed ring core compared to Comparative Compound X6. Comparative Compound X6 contains a phenyl group additionally connected to the moiety of the m-terphenyl, but it is understood that the effect of protecting the condensed ring core is relatively reduced because the additionally connected phenyl group is not arranged in a linear fashion. In contrast, Example Compound 222 is understood to have an enhanced effect of protecting the condensed ring core and reduced material degradation as the first substituent is arranged in a manner that surrounds the condensed ring core. Accordingly, it is understood that a light-emitting device of one embodiment of the present invention containing Example Compound 222 as a dopant material achieves a long lifespan.

[0840] A condensed polycyclic compound according to one embodiment of the present invention is used in a light-emitting layer to contribute to extending the lifespan of a light-emitting device. The condensed polycyclic compound according to one embodiment of the present invention comprises a condensed ring core centered on a boron atom, a first nitrogen atom, and a first heteroatom, and includes a structure in which a first substituent is substituted on the first nitrogen atom of the condensed ring core, thereby having high material stability. Accordingly, when the first compound of one embodiment is introduced into the light-emitting layer of a light-emitting device, an extended lifespan can be achieved.

[0841] Although the present invention has been described above 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 to the present invention without departing from the spirit and technical scope of the invention as described in the claims set forth below.

[0842] Therefore, the technical scope of the present invention should not be limited to the contents described in the detailed description of the specification, but should be determined by the claims. Explanation of the symbols

[0843] DD, DD-TD: Display device ED: Light-emitting element EL1: First electrode EL2: Second electrode HTR: Air Transport Area EML: Emissive layer ETR: Electronic Transport Area

Claims

Claim 1 A light-emitting element comprising: a first electrode; a second electrode disposed on the first electrode; and at least one functional layer disposed between the first electrode and the second electrode and comprising a first compound represented by the following chemical formula 1: [Chemical Formula 1] In the above Chemical Formula 1, X is O, S, or NR 12 and, R1 to R 11 Each is independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a hydroxyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cyclic aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted cyclic heteroaryl group having 2 to 30 carbon atoms, and R 12 Is A substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heteroaryl group having 2 to 30 carbon atoms, provided that R 12 If is a substituted or unsubstituted ring-forming heteroaryl group having 2 to 30 carbon atoms, R 12 It does not contain two or more of any one of a dibenzofuran moiety, a dibenzothiophen moiety, and a carbazole moiety, and Ar is a substituent represented by the following chemical formula 2: [Chemical Formula 2] In the above chemical formula 2, R x1 to R x4 Each is independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a hydroxyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cyclic aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted cyclic heteroaryl group having 2 to 30 carbon atoms, and R x1 to R x3 At least one of them is a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heteroaryl group having 2 to 30 carbon atoms, and R y1 to R y4, and R z1 to R z5 Each is independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a hydroxyl group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thio group, a substituted or unsubstituted boron group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heteroaryl group having 2 to 30 carbon atoms, or forms a ring by bonding to an adjacent group, and is the position connected to the above chemical formula 1. Claim 2 In claim 1, the at least one functional layer comprises a light-emitting layer, a hole transport region disposed between the first electrode and the light-emitting layer, and an electron transport region disposed between the light-emitting layer and the second electrode, and the light-emitting layer comprises the first compound. Claim 3 In paragraph 2, the light-emitting layer is a light-emitting device that emits delayed fluorescence with a light emission center wavelength of 430 nm or more and 490 nm or less. Claim 4 In paragraph 1, R x1 to R x4 Each is independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted aryl group having 2 to 30 carbon atoms, and R x1 to R x3 A light-emitting element in which at least one of the following is a substituent represented by any one of the following chemical formulas 3-1 to 3-4: [Chemical Formula 3-1] [Chemical Formula 3-2] [Chemical Formula 3-3] [Chemical Formula 3-4] In the above chemical formulas 3-1 to 3-4, Y1 to Y7 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cyclic aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted cyclic heteroaryl group having 2 to 30 carbon atoms, n1 and n3 are each independently integers from 0 to 5, n2, n5, and n7 are each independently integers from 0 to 4, and n4 and n6 are each independently integers from 0 to 3. is the position connected to the above chemical formula 2. Claim 5 In Paragraph 4, R x1 to R x3 Any one of them is a substituent represented by any one of the above chemical formulas 3-1 to 3-4, and R x1 to R x3 The rest of the light-emitting elements are hydrogen atoms, deuterium atoms, or unsubstituted t-butyl groups. Claim 6 In claim 1, the substituent represented by Chemical Formula 2 is a light-emitting element represented by any one of the following Chemical Formulas 2-1 to 2-3: [Chemical Formula 2-1] [Chemical Formula 2-2] [Chemical Formula 2-3] In the above chemical formulas 2-1 to 2-3, Z1 to Z6 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, m1, m4, and m6 are each independently an integer from 0 to 4, m2 is an integer from 0 to 5, m3 and m5 are each independently an integer from 0 to 3, and R x1 to R x4 It is the same as defined in Chemical Formula 2 above. Claim 7 In claim 1, the substituent represented by Chemical Formula 2 is a light-emitting element represented by any one of the following Chemical Formulas 2-4 to 2-17: [Chemical Formula 2-4] [Chemical Formula 2-5] [Chemical Formula 2-6] [Chemical Formula 2-7] [Chemical Formula 2-8] [Chemical Formula 2-9] [Chemical Formula 2-10] [Chemical Formula 2-11] [Chemical Formula 2-12] [Chemical Formula 2-13] [Chemical Formula 2-14] [Chemical Formula 2-15] [Chemical Formula 2-16] [Chemical Formula 2-17] In the above chemical formulas 2-4 to 2-17, R x11 to R x24 Each is independently a hydrogen atom, a deuterium atom, an unsubstituted t-butyl group, or an unsubstituted phenyl group, and p1 to p14 are each independently integers from 0 to 3. Claim 8 In claim 1, the first compound represented by Chemical Formula 1 is a light-emitting element represented by any one of the following Chemical Formulas 1-1 to 1-6: [Chemical Formula 1-1] [Chemical Formula 1-2] [Chemical Formula 1-3] [Chemical Formula 1-4] [Chemical Formula 1-5] [Chemical Formula 1-6] In the above chemical formulas 1-1 to 1-6, R a1 to R a6 Each is independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted t-butyl group, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and R b1 to R b17 Each is independently a hydrogen atom, a deuterium atom, a cyano group, a substituted or unsubstituted t-butyl group, a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, or an unsubstituted ring-forming heteroaryl group having 2 to 30 carbon atoms, b1 to b5, b8 and b11 are each independently integers from 0 to 5, b6, b7, b9, b10, and b12 to b17 are each independently integers from 0 to 4, X and Ar are the same as defined in Formula 1 above, and Formulas 1-1 to 1-6 include a structure in which any hydrogen atom is substituted with a deuterium atom. Claim 9 In claim 1, the first compound represented by Chemical Formula 1 is a light-emitting element represented by the following Chemical Formula 1-7: [Chemical Formula 1-7] A1 to A5 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 cyclic aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted cyclic heteroaryl group having 2 to 30 carbon atoms, provided that the case in which two or more of A1 to A5 are each independently a substituted or unsubstituted dibenzofuran group, a substituted or unsubstituted dibenzothiophen group, and a substituted or unsubstituted carbazole group is not included, and Ar and R1 to R 11 It is the same as defined in Chemical Formula 1 above. Claim 10 In claim 1, the first compound represented by Chemical Formula 1 is a light-emitting element represented by any one of the following Chemical Formulas 1-8 to 1-16: [Chemical Formula 1-8] [Chemical Formula 1-9] [Chemical Formula 1-10] [Chemical Formula 1-11] [Chemical Formula 1-12] [Chemical Formula 1-13] [Chemical Formula 1-14] [Chemical Formula 1-15] [Chemical Formula 1-16] In the above chemical formulas 1-8 to 1-16, A 11 , A 13 , A 14 , A 16 , A 18 , A 20 , A 22 , A 24 , A 26 , and A 28 Each is independently a hydrogen atom, a deuterium atom, or a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, and A 12, A 15 , A 17 , A 19 , A 21 , A 23 , A 25 , A 27 , and A 29 are each independently a hydrogen atom, a deuterium atom, or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a1, a3, a4, a6, a8, a10, a12, a14, a16, and a18 are each independently integers from 0 to 5, a2, a5, a7, a9, a11, a13, a15, a17, and a19 are each independently integers from 0 to 3, and Ar and R1 to R 11 It is the same as defined in Chemical Formula 1 above. Claim 11 In claim 1, the first compound represented by the above chemical formula 1 is a light-emitting device comprising at least one of the compounds of the following compound group 1: [Compound group 1] In the specific compounds presented in compound group 1, "D" means a deuterium atom. Claim 12 Condensed polycyclic compound represented by the following chemical formula 1: [Chemical Formula 1] In the above Chemical Formula 1, X is O, S, or NR 12 and, R1 to R 11 Each is independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a hydroxyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cyclic aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted cyclic heteroaryl group having 2 to 30 carbon atoms, and R 12 Is A substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heteroaryl group having 2 to 30 carbon atoms, provided that R 12 If is a substituted or unsubstituted ring-forming heteroaryl group having 2 to 30 carbon atoms, R 12 It does not contain two or more of any one of a dibenzofuran moiety, a dibenzothiophen moiety, and a carbazole moiety, and Ar is a substituent represented by the following chemical formula 2: [Chemical Formula 2] In the above chemical formula 2, R x1 to R x4 Each is independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a hydroxyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cyclic aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted cyclic heteroaryl group having 2 to 30 carbon atoms, and R x1 to R x3 At least one of them is a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heteroaryl group having 2 to 30 carbon atoms, and R y1 to R y4, and R z1 to R z5 Each is independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a hydroxyl group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thio group, a substituted or unsubstituted boron group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heteroaryl group having 2 to 30 carbon atoms, or forms a ring by bonding to an adjacent group, and is the position connected to the above chemical formula 1. Claim 13 In Paragraph 12, R x1 to R x4 Each is independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted aryl group having 2 to 30 carbon atoms, and R x1 to R x3 Condensed polycyclic compound in which at least one of the following is a substituent represented by any one of Formulas 3-1 to 3-4: [Formula 3-1] [Chemical Formula 3-2] [Chemical Formula 3-3] [Chemical Formula 3-4] In the above chemical formulas 3-1 to 3-4, Y1 to Y7 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cyclic aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted cyclic heteroaryl group having 2 to 30 carbon atoms, n1 and n3 are each independently integers from 0 to 5, n2, n5, and n7 are each independently integers from 0 to 4, and n4 and n6 are each independently integers from 0 to 3. is the position connected to the above chemical formula 2. Claim 14 In claim 12, the substituent represented by the above chemical formula 2 is a condensed polycyclic compound represented by any one of the following chemical formulas 2-1 to 2-3: [Chemical formula 2-1] [Chemical Formula 2-2] [Chemical Formula 2-3] In the above chemical formulas 2-1 to 2-3, Z1 to Z6 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, m1, m4, and m6 are each independently an integer from 0 to 4, m2 is an integer from 0 to 5, m3 and m5 are each independently an integer from 0 to 3, and R x1 to R x4 It is the same as defined in Chemical Formula 2 above. Claim 15 In claim 12, the substituent represented by Chemical Formula 2 is a condensed polycyclic compound represented by any one of the following Chemical Formulas 2-4 to 2-17: [Chemical Formula 2-4] [Chemical Formula 2-5] [Chemical Formula 2-6] [Chemical Formula 2-7] [Chemical Formula 2-8] [Chemical Formula 2-9] [Chemical Formula 2-10] [Chemical Formula 2-11] [Chemical Formula 2-12] [Chemical Formula 2-13] [Chemical Formula 2-14] [Chemical Formula 2-15] [Chemical Formula 2-16] [Chemical Formula 2-17] In the above chemical formulas 2-4 to 2-17, R x11 to R x24 Each is independently a hydrogen atom, a deuterium atom, an unsubstituted t-butyl group, or an unsubstituted phenyl group, and p1 to p14 are each independently integers from 0 to 3, and is the position connected to the above chemical formula 1. Claim 16 In claim 12, the condensed polycyclic compound represented by Chemical Formula 1 is a condensed polycyclic compound represented by any one of the following Chemical Formulas 1-1 to 1-6: [Chemical Formula 1-1] [Chemical Formula 1-2] [Chemical Formula 1-3] [Chemical Formula 1-4] [Chemical Formula 1-5] [Chemical Formula 1-6] In the above chemical formulas 1-1 to 1-6, R a1 to R a6 Each is independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted t-butyl group, or a substituted or unsubstituted cyclic aryl group having 6 to 30 carbon atoms, and R b1 to R b17 Each is independently a hydrogen atom, a deuterium atom, a cyano group, a substituted or unsubstituted t-butyl group, a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, or an unsubstituted ring-forming heteroaryl group having 2 to 30 carbon atoms, b1 to b5, b8 and b11 are each independently integers from 0 to 5, b6, b7, b9, b10, and b12 to b17 are each independently integers from 0 to 4, X and Ar are the same as defined in Formula 1 above, and Formulas 1-1 to 1-6 include a structure in which any hydrogen atom is substituted with a deuterium atom. Claim 17 In claim 12, the condensed polycyclic compound represented by Chemical Formula 1 is a condensed polycyclic compound represented by the following Chemical Formula 1-7: [Chemical Formula 1-7] A1 to A5 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 cyclic aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted cyclic heteroaryl group having 2 to 30 carbon atoms, provided that the case in which two or more of A1 to A5 are each independently a substituted or unsubstituted dibenzofuran group, a substituted or unsubstituted dibenzothiophen group, and a substituted or unsubstituted carbazole group is not included, and Ar and R1 to R 11 It is the same as defined in Chemical Formula 1 above. Claim 18 In claim 1, the first compound represented by Chemical Formula 1 is a condensed polycyclic compound represented by any one of the following Chemical Formulas 1-8 to 1-16: [Chemical Formula 1-8] [Chemical Formula 1-9] [Chemical Formula 1-10] [Chemical Formula 1-11] [Chemical Formula 1-12] [Chemical Formula 1-13] [Chemical Formula 1-14] [Chemical Formula 1-15] [Chemical Formula 1-16] In the above chemical formulas 1-8 to 1-16, A 11 , A 13 , A 14 , A 16 , A 18 , A 20 , A 22 , A 24 , A 26 , and A 28 Each is independently a hydrogen atom, a deuterium atom, or a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, and A 12, A 15 , A 17 , A 19 , A 21 , A 23 , A 25 , A 27 , and A 29 are each independently a hydrogen atom, a deuterium atom, or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a1, a3, a4, a6, a8, a10, a12, a14, a16, and a18 are each independently integers from 0 to 5, a2, a5, a7, a9, a11, a13, a15, a17, and a19 are each independently integers from 0 to 3, and Ar and R1 to R 11 It is the same as defined in Chemical Formula 1 above. Claim 19 In claim 12, the condensed polycyclic compound represented by the above chemical formula 1 is a condensed polycyclic compound comprising at least one of the compounds of the following compound group 1: [Compound group 1] In the specific compounds presented in compound group 1, "D" means a deuterium atom. Claim 20 An electronic device comprising: a base layer; a circuit layer disposed on the base layer; and a display element layer disposed on the circuit layer and comprising a light-emitting element, wherein the light-emitting element comprises a first electrode, a second electrode disposed on the first electrode, and a light-emitting layer disposed between the first electrode and the second electrode and comprising a first compound represented by the following chemical formula 1: [Chemical Formula 1] In the above Chemical Formula 1, X is O, S, or NR 12 and, R1 to R 11 Each is independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a hydroxyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cyclic aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted cyclic heteroaryl group having 2 to 30 carbon atoms, and R 12 Is A substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heteroaryl group having 2 to 30 carbon atoms, provided that R 12 If is a substituted or unsubstituted ring-forming heteroaryl group having 2 to 30 carbon atoms, R 12 It does not contain two or more of any one of a dibenzofuran moiety, a dibenzothiophen moiety, and a carbazole moiety, and Ar is a substituent represented by the following chemical formula 2: [Chemical Formula 2] In the above chemical formula 2, R x1 to R x4 Each is independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a hydroxyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cyclic aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted cyclic heteroaryl group having 2 to 30 carbon atoms, and R x1 to R x3 At least one of them is a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heteroaryl group having 2 to 30 carbon atoms, and R y1 to R y4, and R z1 to R z5 Each is independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a hydroxyl group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thio group, a substituted or unsubstituted boron group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heteroaryl group having 2 to 30 carbon atoms, or forms a ring by bonding to an adjacent group, and is the position connected to the above chemical formula 1. Claim 21 In paragraph 20, the electronic device is an electronic device selected from large display devices such as televisions, monitors, and external billboards, personal computers, notebook computers, personal digital terminals, automotive display devices, game consoles, portable electronic devices, and small and medium-sized display devices such as cameras.

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