Fused polycyclic compound and light emitting device including the same

Abstract

A light-emitting element according to one embodiment of the present invention comprises a first electrode, a second electrode facing the first electrode, and a light-emitting layer disposed between the first electrode and the second electrode, wherein the light-emitting layer comprises a host and a dopant, wherein the host comprises a compound represented by the formula E-2a or the formula E-2b, and the dopant comprises a condensed polycyclic compound represented by the following formula 1. [Chemical Formula 1]

Description

Technology Field

[0001] The present invention relates to a condensed polycyclic compound and a light-emitting device comprising the same, and more specifically, to a light-emitting device comprising a novel condensed polycyclic compound used as a light-emitting material. 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 triplet energy or delayed 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 luminous efficiency and device lifespan.

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

[0007] A light-emitting element according to one embodiment of the present invention comprises a first electrode, a second electrode facing the first electrode, and a light-emitting layer disposed between the first electrode and the second electrode, wherein the light-emitting layer comprises a host and a dopant, wherein the host comprises a compound represented by the following chemical formula E-2a or chemical formula E-2b, and the dopant comprises a condensed polycyclic compound represented by the following chemical formula 1.

[0008] [Chemical Formula 1]

[0009]

[0010] In the above Chemical Formula 1, C1 to C5 are each independently a ring-forming single-ring aromatic hydrocarbon ring having 6 to 30 carbon atoms, or a ring-forming single-ring aromatic heterocyclic ring having 2 to 30 carbon atoms, and R1 to R5 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted boron group, a substituted or unsubstituted amine group, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heteroaryl group having 2 to 30 carbon atoms, or a group that forms a ring by bonding to an adjacent group, or a substituent represented by the following Chemical Formula 2, or a substituent represented by the following Chemical Formula 3, and all of R1 to R3 are represented by the following Chemical Formula 2, or among R1 to R5 At least one is represented by the following chemical formula 3, n1 and n5 are each independently integers from 1 to 4, n2 and n4 are each independently integers from 1 to 5, and n3 is an integer from 1 to 3.

[0011] [Chemical Formula 2]

[0012]

[0013] In the above chemical formula 2, A1 and A2 are each independently an alkyl group having 1 to 20 carbon atoms, and R a1 to R a3 Each is independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted 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.

[0014] [Chemical Formula 3]

[0015]

[0016] In the above chemical formula 3, a is 0 or 1, and when a is 1, Y is a direct linkage, Z1 and Z2 are each independently represented by the above chemical formula 2, R6 and R7 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted 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 n6 and n7 are each independently integers from 0 to 4.

[0017] [Chemical Formula E-2a]

[0018]

[0019] [Chemical Formula E-2b]

[0020]

[0021] In the above chemical formula E-2a, b is an integer between 0 and 10 inclusive, and L ais a direct linkage, 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, and A a To A e Each independently N or CR i and R a to R i Each is 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 can form a ring by bonding with an adjacent group, and A a To A e Two or three selected are N, and the rest are CR i And, in the above formula E-2b, Cbz1 and Cbz2 are each independently an unsubstituted carbazole group, or a carbazole group substituted with a ring-forming aryl group having 6 to 30 carbon atoms, and L b is 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, and c is an integer from 0 to 10.

[0022] The above-mentioned light-emitting layer can emit delayed fluorescence.

[0023] The above-mentioned light-emitting layer can emit light with a center wavelength of 430 nm or more and 490 nm or less.

[0024] The condensed polycyclic compound represented by the above chemical formula 1 can be represented by the following chemical formula 1-1.

[0025] [Chemical Formula 1-1]

[0026]

[0027] In the above chemical formula 1-1, R 1-1 to R 3-1 Each is independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted 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 R 1-1a to R 3-1a Each is independently represented by the above chemical formula 2, where m1 is an integer between 0 and 3, m2 is an integer between 0 and 4, and m3 is an integer between 0 and 2.

[0028] In the above chemical formula 1-1, R4, R5, n4, and n5 may be described in the same way as defined in the above chemical formula 1.

[0029] The condensed polycyclic compound represented by the above chemical formula 1-1 may be represented by the following chemical formula 1-2-1 or chemical formula 1-2-2.

[0030] [Chemical Formula 1-2-1]

[0031]

[0032] [Chemical Formula 1-2-2]

[0033]

[0034] In the above chemical formulas 1-2-1 and 1-2-2, R 1-1 to R 3-1 , R 1-1a to R 3-1a , m1 to m3, R4, R5, n4, and n5 may be described in the same way as defined in Chemical Formula 1 and Chemical Formula 1-1 above.

[0035] The condensed polycyclic compound represented by the above chemical formula 1 may be represented by the following chemical formula 1-3-1 or chemical formula 1-3-2.

[0036] [Chemical Formula 1-3-1]

[0037]

[0038] [Chemical Formula 1-3-2]

[0039]

[0040] In the above chemical formulas 1-3-1 and 1-3-2, R 4-1 and R 5-1 Each is independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted 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 R 5-1a is represented by the above chemical formula 3, and R 21 and R 22 Each is independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted 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 m4 is an integer from 0 to 4, m5 is an integer from 0 to 3, and n21 and n22 are each independently integers from 0 to 5.

[0041] In the above chemical formulas 1-3-1 and 1-3-2, R 1-1 to R 3-1 , R 1-1a to R 3-1a , m1 to m3 may be described in the same way as defined in Chemical Formula 1 and Chemical Formula 1-1 above.

[0042] The substituent represented by the above chemical formula 2 may be represented by the following chemical formula 2-1 or chemical formula 2-2.

[0043] [Chemical Formula 2-1]

[0044]

[0045] [Chemical Formula 2-2]

[0046]

[0047] In the above Chemical Formulas 2-1 and 2-2, A 1-1 and A 2-1 Each is an independently substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, and A 1-2 , A 2-2 , and A3 may each be independently substituted or unsubstituted alkyl groups having 3 to 10 carbon atoms.

[0048] In the above Chemical Formulas 2-1 and 2-2, R a1 to R a3 The same description as defined in Chemical Formula 2 above may be applied.

[0049] The substituent represented by the above chemical formula 3 may be represented by the following chemical formula 3-1 or chemical formula 3-2.

[0050] [Chemical Formula 3-1]

[0051]

[0052] [Chemical Formula 3-2]

[0053]

[0054] In the above chemical formulas 3-1 and 3-2, n 6-1 and n 7-1 are each independently integers from 0 to 3, and n 6-2 and n 7-2 Each is an independent integer between 0 and 4 inclusive.

[0055] In the above chemical formulas 3-1 and 3-2, Z1, Z2, R6, and R7 may be described in the same way as defined in the above chemical formula 3.

[0056] The condensed polycyclic compound represented by the above chemical formula 1 may be represented by the following chemical formula 1-4-1 or chemical formula 1-4-2.

[0057] [Chemical Formula 1-4-1]

[0058]

[0059] [Chemical Formula 1-4-2]

[0060]

[0061] In the above chemical formulas 1-4-1 and 1-4-2, R 3-2 and R 5-2 Each is independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted 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 R 3-1b and R 5-1b Each is independently represented by the above chemical formula 3, where b3 is an integer between 0 and 2, and b5 is an integer between 0 and 3.

[0062] In the above chemical formulas 1-4-1 and 1-4-2, R1 to R5 and n1 to n5 may be described in the same way as defined in chemical formula 1.

[0063] The condensed polycyclic compound represented by the above chemical formula 1 may be represented by the following chemical formula 1-5-1 or chemical formula 1-5-2.

[0064] [Chemical Formula 1-5-1]

[0065]

[0066] [Chemical Formula 1-5-2]

[0067]

[0068] In the above chemical formulas 1-5-1 and 1-5-2, R 1-2 , R 3-2 , and R 5-2 Each is independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted 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 R 1-1b , R 3-1b and R 5-1b Each is independently represented by the above chemical formula 3, b1 and b5 are each independently integers from 0 to 3, and b3 is an integer from 0 to 2.

[0069] In the above chemical formulas 1-5-1 and 1-5-2, R2 to R4 and n2 to n4 may be described in the same way as defined in the above chemical formula 1.

[0070] The condensed polycyclic compound represented by the above chemical formula 1 can be represented by the following chemical formula 1-6.

[0071] [Chemical Formula 1-6]

[0072]

[0073] In the above chemical formulas 1-6, X1 and X2 are each independently NR 13 , or O and, R 5-3 , and R 11 to R 13Each is independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted ring-forming heteroaryl group having 2 to 30 carbon atoms, a substituent represented by the above formula 2, or a substituent represented by the above formula 3, and n11 is an integer from 0 to 4, n12 is an integer from 0 to 3, and g5 is an integer from 0 to 2.

[0074] In the above chemical formulas 1-6, R1 to R4 and n1 to n4 may be described in the same way as defined in chemical formula 1.

[0075] The condensed polycyclic compound represented by the above chemical formula 1-6 may be represented by the following chemical formula 1-7-1 or chemical formula 1-7-2.

[0076] [Chemical Formula 1-7-1]

[0077]

[0078] [Chemical Formula 1-7-2]

[0079]

[0080] In the above chemical formulas 1-7-1 and 1-7-2, R 13-1 and R 13-2 Each is independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted ring-forming heteroaryl group having 2 to 30 carbon atoms, or a substituent represented by the above formula 2, and n13 and n14 are each independently integers from 0 to 5.

[0081] In the above chemical formulas 1-7-1 and 1-7-2, R1 to R4, R 5-3 , R 11 and R12 , n1 to n4, g5, n11, and n12 may be described in the same way as defined in Chemical Formula 1 and Chemical Formula 1-6 above.

[0082] A condensed polycyclic compound according to one embodiment of the present invention can be represented by the above chemical formula 1. Effects of the invention

[0083] The light-emitting device of one embodiment can exhibit improved device characteristics such as high efficiency and long lifespan.

[0084] A condensed polycyclic compound of one embodiment can be included in the light-emitting layer of a light-emitting device to contribute to increasing the efficiency and extending the lifespan of an organic electroluminescent device. Brief explanation of the drawing

[0085] 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, respectively. FIG. 9 is a cross-sectional view showing a display device according to one embodiment. FIG. 10 is a cross-sectional view showing a display device according to one embodiment. Specific details for implementing the invention

[0086] 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.

[0087] 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.

[0088] 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.

[0089] 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.

[0090] 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.

[0091] 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.

[0092] 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."

[0093] In this specification, examples of halogen atoms include fluorine atoms, chlorine atoms, bromine atoms, or iodine atoms.

[0094] In this specification, the alkyl group may be straight-chain, branched-chain, or cyclic. 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, cyclopentyl 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, cyclohexyl group, 4-methylcyclohexyl group, 4-t-butylcyclohexyl 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, cyclooctyl 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, Examples include, but are not limited to, n-nonadecyl groups, n-icosyl groups, 2-ethylicosyl groups, 2-butylicosyl groups, 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.

[0095] 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 to 30, 2 to 20, or 2 to 10. Examples of alkenyl groups include, but are not limited to, vinyl groups, 1-butenyl groups, 1-pentenyl groups, 1,3-butadienyl aryl groups, styrenyl groups, styrylvinyl groups, etc.

[0096] 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.

[0097] 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.

[0098] 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.

[0099] 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.

[0100] 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, triazole group, pyridine group, bipyridine group, pyrimidine group, triazine 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.

[0101] 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.

[0102] 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, trimethylboron groups, triethylboron groups, t-butyldimethylboron groups, triphenylboron groups, diphenylboron groups, phenylboron groups, etc.

[0103] 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.

[0104] 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, but are not limited to, methylamine groups, dimethylamine groups, phenylamine groups, diphenylamine groups, naphthylamine groups, 9-methyl-anthracenylamine groups, triphenylamine groups, etc.

[0105] In this specification, direct linkage may mean a single linkage.

[0106] Meanwhile, in this specification " " means the location where it is connected.

[0107] Hereinafter, an embodiment of the present invention will be described with reference to the drawings.

[0108] 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.

[0109] 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.

[0110] 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.

[0111] 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.

[0112] 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).

[0113] 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.

[0114] 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).

[0115] 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).

[0116] 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.

[0117] 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.

[0118] 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.

[0119] The encapsulation layer (TFE) can be placed on the second electrode (EL2) and can fill the opening (OH).

[0120] 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.

[0121] 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).

[0122] 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.

[0123] 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.

[0124] 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.

[0125] 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).

[0126] 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).

[0127] 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), green light-emitting region (PXA-G), and 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) is a Pentile ® It may be in the form of an array or have a diamond array shape.

[0128] 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.

[0129] 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 hole transport region (HTR), a light-emitting layer (EML), an electron transport region (ETR), and a second electrode (EL2) that are sequentially stacked.

[0130] 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). Also, FIG. 5 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).

[0131] 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 transmissive electrode, or a reflective electrode. The first electrode (EL1) may be a transmissive electrode, a transmissive 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.

[0132] 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.

[0133] 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.

[0134] 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.

[0135] 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.

[0136] 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).

[0137] The hole transport region (HTR) may include a compound represented by the following chemical formula H-1.

[0138] [Chemical Formula H-1]

[0139]

[0140] 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.

[0141] 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.

[0142] The compound represented by the above formula H-1 may be a monoamine compound. Alternatively, the compound represented by the above formula H-1 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.

[0143] 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.

[0144] [Compound Group H]

[0145]

[0146] 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.

[0147] 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.

[0148] 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.

[0149] 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).

[0150] 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.

[0151] 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.

[0152] 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).

[0153] 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.

[0154] In a light-emitting device (ED) according to one embodiment, the light-emitting layer (EML) may include a condensed polycyclic compound of one embodiment.

[0155] A condensed polycyclic compound of one embodiment may include a structure in which a plurality of first aromatic rings are condensed through at least one boron atom and at least two heteroatoms. Specifically, a condensed polycyclic compound of one embodiment may include a structure in which a plurality of first aromatic rings are condensed through at least one boron atom and at least two nitrogen atoms to form a condensed ring, and a second aromatic ring is connected to the nitrogen atom that is a constituent atom of the condensed ring. Adjacent first aromatic rings and second aromatic rings may be bonded to each other to form a ring. Meanwhile, in this specification, the first aromatic ring and the second aromatic ring included in the condensed polycyclic compound of one embodiment may be referred to as a "condensed ring core."

[0156] Additionally, the condensed polycyclic compound of one embodiment may include a first substituent, which is a sterically hindered substituent, within the condensed ring core. The first substituent is a substituent in which an alkyl group is introduced to a carbon at a specific position of the benzene moiety, and may be directly bonded to the condensed ring core or connected to the condensed ring core through a second substituent different from the first substituent. When the first substituent is directly bonded to the condensed ring core, the first substituent may essentially be connected to a specific ring among the aromatic rings constituting the condensed ring core. Alternatively, when the first substituent is connected to the condensed ring core through a second substituent, the second substituent substituted with the first substituent may be connected to at least one of the aromatic rings constituting the condensed ring core. Meanwhile, in this specification, "first substituent" may mean a substituent represented by the following Chemical Formula 2, and "second substituent" may mean a substituent represented by the following Chemical Formula 3.

[0157] The condensed polycyclic compound of one embodiment is represented by the following chemical formula 1.

[0158] [Chemical Formula 1]

[0159]

[0160] A condensed polycyclic compound of one embodiment represented by Chemical Formula 1 comprises a structure in which three aromatic rings are condensed through one boron atom and two nitrogen atoms. Additionally, based on a structure in which three aromatic rings are condensed around one boron atom, the condensed compound of one embodiment may have a structure in which additional aromatic rings are condensed through additional boron atoms and additional heteroatoms.

[0161] In Chemical Formula 1, C1 to C5 are each independently a ring-forming aromatic hydrocarbon ring having 6 to 30 carbon atoms, or a ring-forming aromatic heterocyclic ring having 2 to 30 carbon atoms. C1 to C5 may each independently be a pentagonal or hexagonal aromatic hydrocarbon ring, or a pentagonal or hexagonal aromatic heterocyclic ring. In one embodiment, C1 to C5 may each independently be a hexagonal aromatic hydrocarbon ring or a hexagonal aromatic heterocyclic ring. For example, C1 to C5 may each independently be a benzene ring. Alternatively, C1 to C5 may each independently form a condensed ring by bonding to an adjacent ring or an adjacent substituent.

[0162] In Chemical Formula 1, R1 to R5 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted boron group, a substituted or unsubstituted amine 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, a substituent represented by Chemical Formula 2 below, or a substituent represented by Chemical Formula 3 below. Alternatively, each of R1 to R5 may bond with an adjacent group to form a ring. For example, R1 to R5 may each independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted arylboro group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted t-butyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituent represented by Formula 2, or a substituent represented by Formula 3.

[0163] In Chemical Formula 1, all of R1 to R3 are represented by Chemical Formula 2, or at least one of R1 to R5 is represented by Chemical Formula 3. In one embodiment of the condensed polycyclic compound represented by Chemical Formula 1, substituents represented by Chemical Formula 2 are connected to all of C1 to C3, or substituents represented by Chemical Formula 3 are connected to at least one of C1 to C5 of Chemical Formula 1.

[0164] For example, among R1 to R5, R1 to R3 can all be represented by Chemical Formula 2. In this case, R4 and R5 may each independently be a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted boron group, a substituted or unsubstituted amine group, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted aryl group having 2 to 30 carbon atoms, a substituent represented by Chemical Formula 2, or a substituent represented by Chemical Formula 3.

[0165] In addition, at least one of R1 to R5 of Formula 1 may be represented by Formula 3. In this case, the substituent among R1 to R5 that is not represented by Formula 3 may be a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted boron group, a substituted or unsubstituted amine 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 cyclic aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted cyclic heteroaryl group having 2 to 30 carbon atoms, or a substituent represented by Formula 2.

[0166] In Chemical Formula 1, n1 and n5 are each independently integers from 1 to 4, n2 and n4 are each independently integers from 1 to 5, and n3 is an integer from 1 to 3. When each of n1 to n5 is an integer of 2 or more, each of the plurality of R1 to R5 may be the same, or at least one of the plurality of R1 to R5 may be different.

[0167] In one embodiment, the first substituent may be represented by the following Chemical Formula 2. The first substituent comprises a benzene moiety and includes a structure in which an alkyl group is substituted on a carbon at a specific position of the benzene moiety. That is, the first substituent is of Chemical Formula 2. It may include a structure in which an alkyl group is introduced at an ortho position based on the position.

[0168] [Chemical Formula 2]

[0169]

[0170] In Chemical Formula 2, A1 and A2 are each independently an alkyl group having 1 to 20 carbon atoms. In one embodiment, A1 and A2 may each independently be a substituted or unsubstituted methyl group or a substituted or unsubstituted isopropyl group. For example, A1 and A2 may each independently be an unsubstituted methyl group or an unsubstituted isopropyl group.

[0171] In Chemical Formula 2, R a1 to R a3 Each is independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cyclic aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted cyclic aryl group having 2 to 30 carbon atoms. In one embodiment, R a1 to R a3 Each can independently be a hydrogen atom, a deuterium atom, or a substituted or unsubstituted isopropyl group. For example, Ra1 to R a3 Each can independently be a hydrogen atom, a deuterium atom, or an unsubstituted isopropyl group.

[0172] In Chemical Formula 2, " " may be a portion bonded to the aromatic ring of Chemical Formula 1. Or, in Chemical Formula 2, " " may be a part that is bonded to the benzene ring of Chemical Formula 3, which will be described later.

[0173] In one embodiment, the second substituent may be represented by the following chemical formula 3. The second substituent includes a structure in which two aromatic rings are each connected to a nitrogen atom. The two aromatic rings of the second substituent may be connected to each other to form a ring. Additionally, the second substituent includes substituents represented by Z1 and Z2, each connected to the two aromatic rings, and the substituents represented by Z1 and Z2 may be substituted at the para position of the nitrogen atom of chemical formula 3.

[0174] [Chemical Formula 3]

[0175]

[0176] In Chemical Formula 3, a is 0 or 1, and when a is 1, Y is a direct linkage. For example, if a is 0, it may mean that the two benzene rings attached to the nitrogen atom in Chemical Formula 3 are not connected through Y. That is, if a is 0, the substituent represented by Chemical Formula 3 may include a diphenylamine moiety. Also, if a is 1, it may mean that the two benzene rings attached to the nitrogen atom in Chemical Formula 3 are connected through a direct linkage. That is, if a is 1, the substituent represented by Chemical Formula 3 may include a carbazole moiety.

[0177] In Chemical Formula 3, Z1 and Z2 are each independently represented by Chemical Formula 2.

[0178] In Chemical Formula 3, R6 and R7 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted 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, R6 and R7 may each independently be a hydrogen atom or a deuterium atom.

[0179] In Chemical Formula 3, n6 and n7 are each independently integers from 0 to 4. When n6 and n7 are each 0, the condensed polycyclic compound of one embodiment may not be substituted with R6 and R7, respectively. When n6 and n7 are each 4 in Chemical Formula 3 and R6 and R7 are both hydrogen atoms, it may be the same as when n6 and n7 are each 0 in Chemical Formula 3. When n6 and n7 are each integers of 2 or more, the plurality of R6 and R7 may all be the same, or at least one of the plurality of R6 and R7 may be different.

[0180] In Chemical Formula 3, " " may be a part that is bonded to an aromatic ring of chemical formula 1.

[0181] In one embodiment, the condensed polycyclic compound represented by Chemical Formula 1 can be represented by the following Chemical Formula 1-1.

[0182] [Chemical Formula 1-1]

[0183]

[0184] A condensed polycyclic compound of one embodiment may include a structure in which a substituent represented by Formula 2 is bonded at a specific position to a central backbone represented by Formula 1-1. Formula 1-1 indicates that C1 to C5 in Formula 1 are specified as a benzene ring that is substituted or unsubstituted, and that the types of substituents R1 to R3 are specified. That is, Formula 1-1 indicates a case in which all substituents represented by R1 to R3 in Formula 1 are substituents represented by Formula 2.

[0185] In chemical formula 1-1, R 1-1 to R 3-1 Each may independently be a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted 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. Or R 1-1 to R 3-1 Each can combine with an adjacent tile to form a ring. For example, R 1-1 to R 3-1 Each can independently be a hydrogen atom or a deuterium atom.

[0186] In chemical formula 1-1, R 1-1a to R 3-1a Each can be independently represented by Chemical Formula 2. R 1-1a to R 3-1a All of them can be represented by Chemical Formula 2.

[0187] In chemical formula 1-1, m1 is an integer between 0 and 3, m2 is an integer between 0 and 4, and m3 is an integer between 0 and 2.

[0188] When m1 is 0, the condensed polycyclic compound of one embodiment is R 1-1 It may not be substituted with . In Chemical Formula 1-1, m1 is 3, and R 1-1If all of these are hydrogen atoms, it may be the same as the case where m1 is 0 in Chemical Formula 1-1. If m1 is an integer greater than or equal to 2, R is provided in the plural. 1-1 are all the same, or multiple R 1-1 At least one of them may be different.

[0189] When m2 is 0, the condensed polycyclic compound of one embodiment is R 2-1 It may not be substituted with . In Chemical Formula 1-1, m2 is 4, and R 2-1 If all of these are hydrogen atoms, it may be the same as the case where m2 is 0 in Chemical Formula 1-1. If m2 is an integer greater than or equal to 2, R is provided in the plural. 2-1 are all the same, or multiple R 2-1 At least one of them may be different.

[0190] When m3 is 0, the condensed polycyclic compound of one embodiment is R 3-1 It may not be substituted with . In Chemical Formula 1-1, m3 is 2, and R 3-1 If all of these are hydrogen atoms, it may be the same as the case where m3 is 0 in Chemical Formula 1-1. If m3 is 2, R provided in the plural 3-1 are all the same, or multiple R 3-1 At least one of them may be different.

[0191] Meanwhile, regarding Chemical Formula 1-1, the same definition as in Chemical Formula 1 may apply to R4, R5, n4, and n5.

[0192] In one embodiment, the condensed polycyclic compound represented by Formula 1-1 may be represented by the following Formula 1-2-1 or Formula 1-2-2.

[0193] [Chemical Formula 1-2-1]

[0194]

[0195] [Chemical Formula 1-2-2]

[0196]

[0197] Chemical formulas 1-2-1 and 1-2-2 are R in chemical formula 1-1. 1-1a to R 3-1a This represents the case where the substitution position of is specified. Chemical formula 1-2-1 is R in chemical formula 1-1. 1-1a ga is substituted at the meta position with the boron atom, and R 2-1a is substituted with a nitrogen atom at the para position, and R 3-1a represents the case where is substituted with a boron atom at the para position. Chemical formula 1-2-2 is R in chemical formula 1-1. 1-1a ga is substituted with a boron atom at the para position, and R 2-1a is substituted at the meta position with the nitrogen atom, and R 3-1a This represents the case where a boron atom is substituted at the para position.

[0198] In chemical formulas 1-2-1 and 1-2-2, R 1-1 to R 3-1 , R 1-1a to R 3-1a For m1 to m3, R4, R5, n4, and n5, the same as defined in Chemical Formula 1 and Chemical Formula 1-1 above may apply.

[0199] In one embodiment, the condensed polycyclic compound represented by Formula 1 may be represented by the following Formula 1-3-1 or Formula 1-3-2.

[0200] [Chemical Formula 1-3-1]

[0201]

[0202] [Chemical Formula 1-3-2]

[0203]

[0204] Formulas 1-3-1 and 1-3-2 indicate that in Formula 1, C1 to C5 are specified as substituted or unsubstituted benzene rings, and the types of substituents R1 to R5 are specified. Formulas 1-3-1 and 1-3-2 indicate that the substituents represented by R1 to R3 are all substituents represented by Formula 2, and the substituents represented by R4 and R5 are substituted or unsubstituted phenyl groups, or are substituents represented by Formula 3.

[0205] In chemical formulas 1-3-1 and 1-3-2, R 4-1 and R 5-1 Each may independently be a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted 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. Or R 4-1 and R 5-1 Each can combine with an adjacent tile to form a ring. For example, R 4-1 and R 5-1 Each can independently be a hydrogen atom, a deuterium atom, or a substituted or unsubstituted phenyl group.

[0206] In chemical formula 1-3-2, R 5-1a It can be represented by the above chemical formula 3.

[0207] In chemical formulas 1-3-1 and 1-3-2, R 21 and R 22 Each may independently be a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted 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 21 and R22 Each may independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted methyl group, a substituted or unsubstituted isopropyl group, or a substituted or unsubstituted phenyl group.

[0208] In chemical formulas 1-3-1 and 1-3-2, m4 is an integer between 0 and 4, m5 is an integer between 0 and 3, and n21 and n22 are each independently integers between 0 and 5.

[0209] When m4 is 0, the condensed polycyclic compound of one embodiment is R 4-1 It might not have been substituted. m4 is 4, and R 4-1 If all of these are hydrogen atoms, it may be the same as the case where m4 is 0. If m4 is an integer greater than or equal to 2, R provided in the plural 4-1 are all the same, or multiple R 4-1 At least one of them may be different.

[0210] When m5 is 0, the condensed polycyclic compound of one embodiment is R 5-1 It might not have been substituted. m5 is 3, and R 5-1 If all of these are hydrogen atoms, it may be the same as the case where m5 is 0. If m5 is an integer greater than or equal to 2, R provided in the plural 5-1 are all the same, or multiple R 5-1 At least one of them may be different.

[0211] When n21 and n22 are each 0, the condensed polycyclic compound of one embodiment is R 21 and R 22 They may not have been substituted into each. n21 and n22 are each 5, and R 21 and R 22 If each is a hydrogen atom, it may be the same as the case where n21 and n22 are each 0. If n21 and n22 are each integers greater than or equal to 2, R provided in the plural 21 and R 22Each one is either identical or a plurality of R 21 and R 22 At least one of them may be different.

[0212] In chemical formulas 1-3-1 and 1-3-2, R 1-1 to R 3-1 , R 1-1a to R 3-1a For m1 to m3, the same as defined in Chemical Formula 1 and Chemical Formula 1-1 above may apply.

[0213] In one embodiment, the substituent represented by Formula 2 may be represented by Formula 2-1 or Formula 2-2 below.

[0214] [Chemical Formula 2-1]

[0215]

[0216] [Chemical Formula 2-2]

[0217]

[0218] In Chemical Formula 2-1, A 1-1 and A 2-1 Each may be an independently substituted or unsubstituted alkyl group having 1 to 10 carbon atoms. In one embodiment, A 1-1 and A 2-1 Each may independently be a substituted or unsubstituted methyl group, or a substituted or unsubstituted isopropyl group. For example, A 1-1 and A 2-1 Each can be an independently unsubstituted methyl group or an unsubstituted isopropyl group.

[0219] In Chemical Formula 2-2, A 1-2 , A 2-2 , and A3 may each be independently substituted or unsubstituted alkyl groups having 3 to 10 carbon atoms. In one embodiment, A 1-2 , A 2-2 , and A3 may each be independently substituted or unsubstituted isopropyl groups. For example, A 1-1 and A2-1 Each can be an independently unsubstituted isopropyl group.

[0220] In Chemical Formula 2-1 and Chemical Formula 2-2, " " may be a portion bonded to the aromatic ring of Formula 1. Or, in Formulas 2-1 and 2-2, " " can be a part that bonds to the benzene ring of chemical formula 3.

[0221] In Chemical Formulas 2-1 and 2-2, R a1 to R a3 The same content as defined in Chemical Formula 2 above may apply to .

[0222] In one embodiment, the substituent represented by Formula 3 may be represented by Formula 3-1 or Formula 3-2 below.

[0223] [Chemical Formula 3-1]

[0224]

[0225] [Chemical Formula 3-2]

[0226]

[0227] In Chemical Formula 3-1, n 6-1 and n 7-1 n are each independently integers between 0 and 3 inclusive. 6-1 and n 7-1 When each is 0, the condensed polycyclic compound of one embodiment may not be substituted with R6 and R7, respectively. In Formula 3-1, n 6-1 and n 7-1 In the case where each is 3 and R6 and R7 are both hydrogen atoms, n in Chemical Formula 3-1 6-1 and n 7-1 It can be the same as the case where each is 0. n 6-1 and n 7-1 If each is an integer of 2 or more, each of the multiple R6 and R7 provided may be identical, or at least one of the multiple R6 and R7 may be different.

[0228] In chemical formula 3-2, n 6-2 and n 7-2 n are each independently integers between 0 and 4 inclusive. 6-2 and n 7-2 When each is 0, the condensed polycyclic compound of one embodiment may not be substituted with R6 and R7, respectively. In Chemical Formula 3-2, n 6-2 and n 7-2 In the case where each is 4 and R6 and R7 are both hydrogen atoms, n in Chemical Formula 3-2 6-2 and n 7-2 It can be the same as the case where each is 0. n 6-2 and n 7-2 If each is an integer of 2 or more, each of the multiple R6 and R7 provided may be identical, or at least one of the multiple R6 and R7 may be different.

[0229] In Chemical Formulas 3-1 and 3-2, " " may be a part that is bonded to an aromatic ring of chemical formula 1.

[0230] In Chemical Formulas 3-1 and 3-2, the same definition as in Chemical Formula 3 may apply to Z1, Z2, R6, and R7.

[0231] In one embodiment, the condensed polycyclic compound represented by Formula 1 may be represented by the following Formula 1-4-1 or Formula 1-4-2.

[0232] [Chemical Formula 1-4-1]

[0233]

[0234] [Chemical Formula 1-4-2]

[0235]

[0236] Chemical formulas 1-4-1 and 1-4-2 indicate that in Chemical Formula 1, C1 to C5 are specified as a benzene ring in which the groups are substituted or unsubstituted, and the type of substituent R3 or R5 is specified. That is, Chemical formulas 1-4-1 and 1-4-2 indicate the case where any one of the substituents represented by R1 to R5 in Chemical Formula 1 is essentially a substituent represented by Chemical Formula 3. Chemical formula 1-4-1 indicates the case where the substituent represented by R3 in Chemical Formula 1 is a substituent represented by Chemical Formula 3. Chemical formula 1-4-2 indicates the case where the substituent represented by R5 in Chemical Formula 1 is a substituent represented by Chemical Formula 3.

[0237] In chemical formulas 1-4-1 and 1-4-2, R 3-2 and R 5-2 Each may independently be a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted 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. Or, R 3-2 and R 5-2 Each can combine with an adjacent tile to form a ring. For example, R 3-2 and R 5-2 Each can independently be a hydrogen atom or a deuterium atom.

[0238] In chemical formulas 1-4-1 and 1-4-2, R 3-1b and R 5-1b Each can be independently represented by the above chemical formula 3.

[0239] In Chemical Formula 1-4-1, b3 is an integer between 0 and 2. When b3 is 0, the condensed polycyclic compound of one example is R 3-2 It may not be substituted with . In chemical formula 1-4-1, b3 is 2, and R 3-2If these are all hydrogen atoms, it may be the same as the case where b3 is 0 in Chemical Formula 1-4-1. If b3 is 2, R provided in the plural 3-2 are all the same, or multiple R 3-2 At least one of them may be different.

[0240] In Chemical Formula 1-4-2, b5 is an integer from 0 to 3. When b5 is 0, the condensed polycyclic compound of one example is R 5-2 It may not be substituted with . In chemical formula 1-4-2, b5 is 3, and R 5-2 If all are hydrogen atoms, it may be equivalent to the case where b5 is 0 in Chemical Formula 1-4-2. If b5 is an integer greater than or equal to 2, R is provided in the plural. 5-2 are all the same, or multiple R 5-2 At least one of them may be different.

[0241] In Chemical Formulas 1-4-1 and 1-4-2, the same definition as in Chemical Formula 1 may apply to R1 to R5 and n1 to n5.

[0242] In one embodiment, the condensed polycyclic compound represented by Formula 1 may be represented by the following Formula 1-5-1 or Formula 1-5-2.

[0243] [Chemical Formula 1-5-1]

[0244]

[0245] [Chemical Formula 1-5-2]

[0246]

[0247] Chemical formulas 1-5-1 and 1-5-2 indicate that in Chemical Formula 1, C1 to C5 are specified as a benzene ring in which the groups are substituted or unsubstituted, and the type of substituent R1, R3, or R5 is specified. That is, Chemical formulas 1-5-1 and 1-5-2 indicate the case where at least two of the substituents represented by R1 to R5 in Chemical Formula 1 are substituents represented by Chemical Formula 3. Chemical formula 1-5-1 indicates the case where the substituents represented by R1 and R5 in Chemical Formula 1 are substituents represented by Chemical Formula 3. Chemical formula 1-5-2 indicates the case where the substituents represented by R1, R3, and R5 in Chemical Formula 1 are substituents represented by Chemical Formula 3.

[0248] In chemical formulas 1-5-1 and 1-5-2, R 1-2 , R 3-2 , and R 5-2 Each may independently be a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted 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. Or, R 1-2 , R 3-2 , and R 5-2 Each can combine with an adjacent tile to form a ring. For example, R 1-2 , R 3-2 , and R 5-2 Each can independently be a hydrogen atom or a deuterium atom.

[0249] In chemical formulas 1-5-1 and 1-5-2, R 1-1b , R 3-1b and R 5-1b Each can be independently represented by Chemical Formula 3.

[0250] In Chemical Formulas 1-5-1 and 1-5-2, b1 and b5 are each independently integers from 0 to 3. When b1 and b5 are each 0, the condensed polycyclic compound of one embodiment is R 1-2 and R 5-2 They may each be unsubstituted. In chemical formulas 1-5-1 and 1-5-2, b1 and b5 are each 3, and R 1-2 and R 5-2 When each is a hydrogen atom, it may be the same as when b1 and b5 are each 0 in Formulas 1-5-1 and 1-5-2. When b1 and b5 are each integers greater than or equal to 2, R is provided in the plural. 1-2 and R 5-2 Each one is either identical or a plurality of R 1-2 and R 5-2 At least one of them may be different.

[0251] In Chemical Formula 1-5-2, b3 is an integer between 0 and 2. When b3 is 0, the condensed polycyclic compound of one example is R 3-2 It may not be substituted with . In chemical formula 1-5-2, b3 is 2, and R 3-2 If these are all hydrogen atoms, it may be equivalent to the case where b3 is 0 in Chemical Formula 1-5-2. If b3 is 2, R provided in the plural 3-2 are all the same, or multiple R 3-2 At least one of them may be different.

[0252] In Chemical Formulas 1-5-1 and 1-5-2, the same definition as in Chemical Formula 1 may apply to R2 to R4 and n2 to n4.

[0253] In one embodiment, the condensed polycyclic compound represented by Chemical Formula 1 can be represented by the following Chemical Formulas 1-6.

[0254] [Chemical Formula 1-6]

[0255]

[0256] Chemical Formula 1-6 represents a case where R5 is provided in multiple numbers in Chemical Formula 1, connected to the boron atoms at the para and meta positions, and bonded to each other to form additional rings. Chemical Formula 1-6 represents a structure in which two rings are additionally condensed through additional boron atoms, X1 and X2, in the condensed ring structure of Chemical Formula 1.

[0257] In Chemical Formula 1-6, X1 and X2 are each independently NR 13 , or it can be O.

[0258] In chemical formula 1-6, R 5-3 , and R 11 to R 13 Each may independently be a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cyclic aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted cyclic heteroaryl group having 2 to 30 carbon atoms, a substituent represented by Formula 2, or a substituent represented by Formula 3. For example, R 5-3 , and R 11 to R 13 Each may independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted t-butyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted carbazole group, a substituent represented by Formula 2, or a substituent represented by Formula 3.

[0259] In chemical formula 1-6, n11 is an integer between 0 and 4, n12 is an integer between 0 and 3, and g5 is an integer between 0 and 2.

[0260] When n11 is 0, the condensed polycyclic compound of one embodiment is R 11It might not have been substituted. n11 is 4, and R 11 If all of these are hydrogen atoms, it may be the same as the case where n11 is 0. If n11 is an integer greater than or equal to 2, R provided in the plural 11 are all the same, or multiple R 11 At least one of them may be different.

[0261] When n12 is 0, the condensed polycyclic compound of one embodiment is R 12 It might not have been substituted. n12 is 3, and R 12 If all are hydrogen atoms, it may be the same as the case where n12 is 0. If n12 is an integer greater than or equal to 2, R provided in the plural 12 are all the same, or multiple R 12 At least one of them may be different.

[0262] When g5 is 0, the condensed polycyclic compound of one example is R 5-3 It may not have been substituted with. g5 is 2, and R 5-3 If all of these are hydrogen atoms, it can be the same as the case where g5 is 0. If g5 is 2, R provided in the plural 5-3 are all the same, or multiple R 5-3 At least one of them may be different.

[0263] As previously stated in the description of Chemical Formula 1 above, in Chemical Formulas 1-6, all of R1 to R3 are represented by Chemical Formula 2, or at least one of R1 to R5 is represented by Chemical Formula 3.

[0264] In Chemical Formula 1-6, the same definition as in Chemical Formula 1 may apply to R1 to R4 and n1 to n4.

[0265] In one embodiment, the condensed polycyclic compound represented by Formula 1-6 may be represented by the following Formula 1-7-1 or Formula 1-7-2.

[0266] [Chemical Formula 1-7-1]

[0267]

[0268] [Chemical Formula 1-7-2]

[0269]

[0270] Chemical formulas 1-7-1 and 1-7-2 represent cases where the types of substituents of X1 and X2 in chemical formula 1-6 are specified.

[0271] In chemical formulas 1-7-1 and 1-7-2, R 13-1 and R 13-2 Each may independently be a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cyclic aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted cyclic heteroaryl group having 2 to 30 carbon atoms, or a substituent represented by Formula 2. For example, R 13-1 and R 13-2 Each may independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted phenyl group, or a substituent represented by Formula 2.

[0272] In Chemical Formulas 1-7-1 and 1-7-2, n13 and n14 are each independently integers from 0 to 5. When n13 and n14 are each 0, the condensed polycyclic compound of one embodiment is R 13-1 and R 13-2 They may not have been substituted into each. n13 and n14 are each 5, and R 13-1 and R 13-2 If each is a hydrogen atom, it may be the same as the case where n13 and n14 are each 0. If n13 and n14 are each integers greater than or equal to 2, R provided in the plural 13-1 and R 13-2 Each one is either identical or a plurality of R 13-1 and R 13-2At least one of them may be different.

[0273] In Chemical Formulas 1-7-1 and 1-7-2, R1 to R4, R 5-3 , R 11 and R 12 For n1 to n4, g5, n11, and n12, the same as defined in Chemical Formula 1 and Chemical Formula 1-6 above may apply.

[0274] The condensed polycyclic compound of one embodiment may be any one of the compounds listed in Compound Group 1 below. 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). [Compound Group 1]

[0275]

[0276]

[0277]

[0278]

[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] In the structures of the above compounds, D may represent a deuterium atom.

[0307] A condensed polycyclic compound represented by Formula 1 according to one embodiment can achieve a long lifespan by introducing a first substituent represented by Formula 2 or a second substituent represented by Formula 3 into the condensed ring core, and has the advantage of being able to shorten the emission wavelength (blue shift) and simultaneously finely control the emission wavelength.

[0308] A condensed polycyclic compound of one embodiment comprises a structure in which a first substituent represented by Formula 2 is necessarily connected to a specific ring among the aromatic rings constituting the condensed ring core, or comprises a structure in which at least one second substituent represented by Formula 3 is included in the condensed ring core. Accordingly, the condensed polycyclic compound of one embodiment can control the formation of excimers or exciplexes by suppressing intermolecular interactions through the steric hindrance effect caused by the first or second substituent, thereby increasing luminescence efficiency. In addition, the condensed polycyclic compound of one embodiment represented by Formula 1 has a bulky structure, which can widen the intermolecular distance and reduce 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 its bulky structure, 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.

[0309] In addition, the condensed polycyclic compound of one embodiment represented by Chemical Formula 1 includes a first substituent represented by Chemical Formula 2 in the condensed ring core, thereby increasing the dihedral angle between the plane containing the condensed ring core structure centered on the boron atom and the plane containing the first substituent. Accordingly, the effective conjugation length of the condensed polycyclic compound represented by Chemical Formula 1 is shortened, and as a result, the emission wavelength can be blue-shifted. Furthermore, the conjugation length of the entire molecule can be controlled according to the position or number of the first substituent represented by Chemical Formula 2 substituted on the condensed ring core and the steric hindrance characteristics according to the molecular structure, and thereby the emission wavelength can be finely controlled.

[0310] 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 to 50 nm, and preferably has a full width at half maximum (FWHM) of 20 to 40 nm. As the emission spectrum of the condensed polycyclic compound of one embodiment represented by Chemical Formula 1 has a full width at half maximum (FWHM) within 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.

[0311] The condensed polycyclic compound of one embodiment represented by Chemical Formula 1 may be a thermally active delayed fluorescent emitting material. In addition, the condensed polycyclic compound of one embodiment represented by Chemical Formula 1 has a difference (βE) between the lowest triplet excitation energy level (T1 level) and the lowest singlet excitation energy level (S1 level). ST It may be a thermally active delayed fluorescent dopant having a β-value of 0.3 eV or less. For example, the β-value of the condensed polycyclic compound of one embodiment represented by Chemical Formula 1. ST It can be 0.1 eV or less.

[0312] 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 condensed polycyclic compound 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.

[0313] 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).

[0314] 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 light-emitting device (ED) of one embodiment may emit blue light in a 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.

[0315] Meanwhile, although not illustrated in the drawings, the light-emitting element (ED) of one embodiment may include a plurality of light-emitting layers. The plurality of light-emitting layers may be stacked sequentially, and, for example, the light-emitting element (ED) including the plurality of light-emitting layers may emit white light. The organic electroluminescent element including the plurality of light-emitting layers may be an organic electroluminescent 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 the condensed polycyclic compound of the above-described embodiment.

[0316] In one embodiment, the emitting layer (EML) comprises a host and a dopant, and may include the above-described condensed polycyclic compound as a dopant. For example, in a light-emitting device (ED) of one embodiment, the emitting layer (EML) may include a host for delayed fluorescence emission and a dopant for delayed fluorescence emission, and may include the above-described condensed polycyclic compound as a dopant for delayed fluorescence emission. The emitting layer (EML) may include at least one of the condensed polycyclic compounds listed in the above-described compound group 1 as a thermally active delayed fluorescence dopant.

[0317] 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.

[0318] 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 host and dopant described above, and 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.

[0319] [Chemical Formula E-1]

[0320]

[0321] In chemical formula E-1, R 31 to R 40Each 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 1 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.

[0322] In chemical formula E-1, c and d can each independently be integers from 0 to 5.

[0323] Chemical formula E-1 may be represented by any one of the following compounds E1 to E19.

[0324]

[0325]

[0326]

[0327]

[0328]

[0329] 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.

[0330] [Chemical Formula E-2a]

[0331]

[0332] In chemical formula E-2a, b 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 b 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.

[0333] Also, in chemical formula E-2a, A a To A e Each independently N or CR i It could be. R a to R i Each 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.

[0334] Meanwhile, in chemical formula E-2a, A a To A e Two or three selected are N, and the rest are CR i It could be.

[0335] [Chemical Formula E-2b]

[0336]

[0337] 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. c is an integer from 0 to 10, and if c 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.

[0338] 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.

[0339] [Compound Group E-2]

[0340]

[0341]

[0342]

[0343]

[0344] 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.

[0345] The emissive layer (EML) may further include a compound represented by the following chemical formula Ma or chemical formula Mb. The compound represented by the following chemical formula Ma or chemical formula Mb may be used as a phosphorescent dopant material.

[0346] [Chemical Formula Ma]

[0347]

[0348] 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.

[0349] Compounds represented by the chemical formula Ma can be used as phosphorescent dopants.

[0350] 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.

[0351]

[0352]

[0353]

[0354]

[0355] [Chemical Formula Mb]

[0356]

[0357] In the chemical formula Mb, Q1 to Q4 are each independently C or N, and C1 to C4 are each independently a substituted or unsubstituted cyclic hydrocarbon ring having 5 to 30 carbon atoms, or a substituted or unsubstituted cyclic heterocycle having 2 to 30 carbon atoms. L 21 to L 24 Each directly combines independently, , , , , , , a substituted or unsubstituted divalent alkyl group having 1 to 20 carbon atoms, a 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, and e1 to e4 are each independently 0 or 1. R 31 to R 39 Each is independently 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, or forms a ring by bonding to adjacent groups, and d1 to d4 are each independently integers from 0 to 4.

[0358] Compounds represented by the chemical formula Mb can be used as blue phosphorescent dopants or green phosphorescent dopants.

[0359] A compound represented by the chemical formula Mb may be represented by any one of the following compounds. However, the following compounds are exemplary, and the compound represented by the chemical formula Mb is not limited to those represented by the following compounds.

[0360]

[0361] In the above compounds, R, R38 , and R 39 Each may 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.

[0362] The emissive layer (EML) may further 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.

[0363] [Chemical Formula Fa]

[0364]

[0365] In the above chemical formula Fa, R a to R j The two selected from among them are each 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.

[0366] [Chemical Formula Fb]

[0367]

[0368] 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 be formed by bonding with adjacent groups.

[0369] In the chemical formula Fb, U and V may each be independently a 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. At least one of Ar1 to Ar4 may be a heteroaryl group containing O or S as a ring-forming atom.

[0370] 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.

[0371] [Chemical Formula Fc]

[0372]

[0373] 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 11 Each 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.

[0374] 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.

[0375] 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.

[0376] 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')picolinate), Fir6 (Bis(2,4-difluorophenylpyridinato)-tetrakis(1-pyrazolyl)borate iridium(III)), or PtOEP (platinum octaethyl porphyrin) may be used as the phosphorescent dopant. However, the examples are not limited thereto.

[0377] The emissive layer (EML) may contain a quantum dot material. The core of the quantum dot may be selected from group II-VI compounds, group III-VI compounds, group I-III-VI compounds, group III-V compounds, group III-II-V compounds, group IV-VI compounds, group IV elements, group IV compounds, and combinations thereof.

[0378] 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, HgZnSTe and mixtures thereof.

[0379] 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.

[0380] 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.

[0381] 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.

[0382] Group IV-VI compounds may be selected from the group consisting of SnS, SnSe, SnTe, PbS, PbSe, PbTe, and mixtures thereof; ternary compounds selected from the group consisting of SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, SnPbTe, and mixtures thereof; and quaternary compounds selected from the group consisting of SnPbSSe, SnPbSeTe, SnPbSTe, and mixtures thereof. Group IV elements may be selected from the group consisting of Si, Ge, and mixtures thereof. Group IV compounds may be ternary compounds selected from the group consisting of SiC, SiGe, and mixtures thereof.

[0383] 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.

[0384] 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.

[0385] 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.

[0386] 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.

[0387] 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 wide viewing angle can be improved.

[0388] 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.

[0389] Quantum dots can control the color of the light they emit depending on their particle size, and accordingly, they can have various emission colors such as blue, red, and green.

[0390] 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.

[0391] 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.

[0392] 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 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 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.

[0393] 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).

[0394] The electron transport domain (ETR) may include a compound represented by the following chemical formula ET-1.

[0395] [Chemical Formula ET-1]

[0396]

[0397] In the chemical formula ET-1, at least one of X1 to X3 is N and the rest are CR a is. R amay 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.

[0398] In the formula ET-1, a to c may each be an integer from 0 to 10 or less, independently. In the formula ET-1, 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.

[0399] 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), It may include 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) and mixtures thereof.

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

[0401]

[0402] 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.

[0403] 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.

[0404] 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).

[0405] 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.

[0406] 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. The second electrode 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, two or more compounds selected from these, two or more mixtures selected from these, or oxides thereof.

[0407] 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.

[0408] 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 MgAg). 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.

[0409] 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.

[0410] 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.

[0411] 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.

[0412] 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 sol-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.

[0413]

[0414]

[0415] 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.

[0416] 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.

[0417] 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).

[0418] In one embodiment illustrated in FIG. 7, the display panel (DP) includes a base layer (BS), a circuit layer (DP-CL) provided on the base layer (BS), and a display element layer (DP-ED), and the display element layer (DP-ED) may include a light-emitting element (ED).

[0419] 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.

[0420] The light-emitting layer (EML) of the light-emitting element (ED) included in the display device (DD-a) of one embodiment may include the condensed polycyclic compound of the above-described embodiment.

[0421] 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 a display device (DD) 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).

[0422] 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.

[0423] 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.

[0424] 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.

[0425] 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.

[0426] 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 the quantum dots (QD1, QD2).

[0427] 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).

[0428] 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.

[0429] 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). 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.

[0430] 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 be placed on the light control units (CCP1, CCP2, CCP3) to 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 be provided between the light control units (CCP1, CCP2, CCP3) and the color filter layer (CFL).

[0431] 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.

[0432] In a display device (DD) 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.

[0433] The color filter layer (CFL) may include filters (CF1, CF2, CF3). 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 include a polymer photosensitive resin and a pigment or dye. The first filter (CF1) may include a red pigment or dye, the second filter (CF2) may include a green pigment or dye, and the third filter (CF3) may include a blue pigment or dye. Meanwhile, the embodiments are not limited thereto, and the third filter (CF3) may not include a pigment or dye. The third filter (CF3) may contain a polymer photosensitive resin and may not contain pigments or dyes. The third filter (CF3) may be transparent. The third filter (CF3) may be formed of a transparent photosensitive resin.

[0434] 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 be provided as a single unit without being distinguished from each other. Each of the first to third filters (CF1, CF2, CF3) may be positioned corresponding to the red light emission region (PXA-R), the green light emission region (PXA-G), and the blue light emission region (PXA-B), respectively.

[0435] Meanwhile, although not illustrated, the color filter layer (CFL) may include a light-blocking portion (not illustrated). The color filter layer (CFL) may include a light-blocking portion (not illustrated) arranged to overlap the boundary of adjacent filters (CF1, CF2, CF3). The light-blocking portion (not illustrated) may be a black matrix. The light-blocking portion (not illustrated) may be formed by including an organic light-blocking material or an inorganic light-blocking material comprising a black pigment or a black dye. The light-blocking portion (not illustrated) may distinguish the boundary between adjacent filters (CF1, CF2, CF3). Additionally, in one embodiment, the light-blocking portion (not illustrated) may be formed of a blue filter.

[0436] 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.

[0437] 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).

[0438] 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.

[0439] 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.

[0440] 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.

[0441] 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.

[0442] 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.

[0443] 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).

[0444] 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).

[0445] 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 hole transport region (HTR) and the light-emitting auxiliary region (OG). 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 light-emitting auxiliary region (OG) and the electron transport region (ETR).

[0446] 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.

[0447] 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.

[0448] 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). Charge generating layers (CGL1, CGL2, CGL3) may be disposed between the first to fourth light-emitting structures (OL-B1, OL-B2, OL-B3, OL-C1). 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.

[0449] 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.

[0450] 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.

[0451] 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.

[0452] [Example]

[0453] 1. Synthesis of Condensed Polycyclic Compounds

[0454] First, regarding the synthesis method of a condensed polycyclic compound according to the present embodiment, the synthesis method of compounds 1, 2, 3, 13, 34, 41, 42, 59, 81, 90, and 121 will be specifically explained by example. In addition, the synthesis method of a condensed polycyclic compound described below is one 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.

[0455] (1) Synthesis of Compound 1

[0456] A condensed polycyclic compound 1 according to one embodiment can be synthesized, for example, by the following reaction.

[0457] (Synthesis of Intermediate A)

[0458]

[0459] Under an Ar atmosphere, Bis(4-bromophenyl)amine (15.0 g, 45.9 mmol), 2,6-Dimethylphenylboronic Acid (15.1 g, 100 mmol), Pd(PPh3)4 (5.3 g, 4.59 mmol), and K3PO4 (19.5 g, 91.7 mmol) were added to 100 ml of toluene and reacted at 80°C for 6 hours. After cooling, water was added, and the mixture was separated by filtration using Celite. The organic layer was concentrated. It was purified by silica gel column chromatography to obtain intermediate A (13.9 g, yield 80%). FAB MS measurement revealed that the molecular weight of intermediate A was 377.

[0460] (Synthesis of Intermediate B)

[0461]

[0462] Intermediate B was synthesized in the same manner as Intermediate A, except that 1,3-dibromo-5-chlorobenzene (15.0 g, 66.4 mmol) was used instead of Bis(4-bromophenyl)amine in the synthesis of Intermediate A, and Intermediate B (15.0 g, yield 90%) was obtained. The molecular weight of Intermediate B was 251 according to FAB MS measurements.

[0463] (Synthesis of intermediate C)

[0464]

[0465] Under an Ar atmosphere, intermediate A (21.0 g, 55.7 mmol), intermediate B (7.0 g, 27.9 mmol), Pd(dba)2 (1.60 g, 2.79 mmol), P(t-Bu)3HBF4 (1.62 g, 5.57 mmol), and tBuONa (6.16 g, 64.1 mmol) were added to 300 ml of toluene and heated and stirred at 80°C for 2 hours. Water was added, and the mixture was separated by Celite filtration to concentrate the organic layer. The mixture was purified by silica gel column chromatography to obtain intermediate C (22.9 g, yield 88%). FAB MS measurement revealed that the molecular weight of intermediate C was 933.

[0466] (Synthesis of Compound 1)

[0467]

[0468] Under an Ar atmosphere, intermediate C (12.0 g, 12.9 mmol) was dissolved in 1,2-Dichlorobenzene (ODCB, 200 ml), BBr3 (8.0 g, 32.1 mmol) was added, and the mixture was heated and stirred at 170°C for 10 hours. After cooling to room temperature, N,N-Diisopropylethylamine (19.9 g, 154 mmol) and water were added, separated by Celite filtration, and the organic layer was concentrated. Compound 1 (3.39 g, yield 28%) was obtained by purification using silica gel column chromatography. The molecular weight of Compound 1 was 941 according to FAB MS measurements. Sublimation purification (380°C, 2.6 x 10⁻⁶ -3 Pa) conducted a device evaluation.

[0469] (2) Synthesis of Compound 2

[0470] A condensed polycyclic compound 2 according to one embodiment can be synthesized, for example, by the following reaction.

[0471] (Synthesis of intermediate D)

[0472]

[0473] Intermediate D was synthesized in the same manner as Intermediate A, except that 2,6-diisopropylphenylboronic acid (20.8 g, 101 mmol) was used instead of 2,6-dimethylphenylboronic acid in the synthesis of Intermediate A, and Intermediate D (18.0 g, yield 80%) was obtained. The molecular weight of Intermediate D was 489 according to FAB MS measurements.

[0474] (Synthesis of intermediate E)

[0475]

[0476] Intermediate E was synthesized in the same manner as Intermediate D, except that 1-bromo-3,5-dichlorobenzene (20.0 g, 88.5 mmol) was used instead of Bis(4-bromophenyl)amine in the synthesis of Intermediate D, and Intermediate E (27.2 g, yield 75%) was obtained. The molecular weight of Intermediate E was 307 according to FAB MS measurements.

[0477] (Synthesis of intermediate F)

[0478]

[0479] Intermediate F (16.8 g, yield 85%) was obtained by synthesizing intermediate C in the same manner as intermediate C, except that compound D (15.9 g, 32.6 mmol) was used instead of intermediate A and intermediate E (5.0 g, 16.3 mmol) was used instead of intermediate B. FAB MS measurement showed that the molecular weight of intermediate F was 1213.

[0480] (Synthesis of Compound 2)

[0481]

[0482] Compound 2 (3.22 g, yield 32%) was obtained by the same method as the synthesis of Compound 1, except that intermediate F (10.0 g, 8.24 mmol) was used instead of intermediate C in the synthesis of Compound 1. The molecular weight of Compound 2 was 1221 by FAB MS measurement. Sublimation purification (340°C, 2.8 x 10⁻⁶ -3 Pa) conducted a device evaluation.

[0483] (3) Synthesis of Compound 3

[0484] A condensed polycyclic compound 3 according to one embodiment can be synthesized, for example, by the following reaction.

[0485] (Synthesis of intermediate G)

[0486]

[0487] Intermediate G was synthesized in the same manner as Intermediate A, except that 2,4,6-Triisopropylphenylboronic Acid (16.7 g, 67.3 mmol) was used instead of 2,6-Dimethylphenylboronic Acid in the synthesis of Intermediate A, and Intermediate G (12.9 g, yield 74%) was obtained. The molecular weight of Intermediate G was 574 according to FAB MS measurements.

[0488] (Synthesis of intermediate H)

[0489]

[0490] Intermediate H was synthesized in the same manner as intermediate G, except that 1-bromo-3,5-dichlorobenzene (15.0 g, 66.4 mmol) was used instead of Bis(4-bromophenyl)amine in the synthesis of intermediate G, and intermediate H (16.2 g, yield 70%) was obtained. The molecular weight of intermediate H was 349 according to FAB MS measurements.

[0491] (Synthesis of Intermediate I)

[0492]

[0493] Intermediate I (17.7g, yield 87%) was obtained by synthesizing intermediate C in the same manner as intermediate C, except that intermediate G (16.4g, 28.6 mmol) was used instead of intermediate A and intermediate H (5.0g, 14.3 mmol) was used instead of intermediate B. FAB MS measurement showed that the molecular weight of intermediate I was 1424.

[0494] (Synthesis of Compound 3)

[0495]

[0496] Compound 3 (3.52 g, yield 35%) was obtained by synthesizing it in the same manner as Compound 1, except that Intermediate I (10.0 g, 7.02 mmol) was used instead of Intermediate C. FAB MS measurements showed that the molecular weight of Compound 3 was 1432. Sublimation purification (320°C, 3.0 x 10⁻⁶ -3 Pa) conducted a device evaluation.

[0497] (4) Synthesis of Compound 13

[0498] A condensed polycyclic compound 13 according to one embodiment can be synthesized, for example, by the following reaction.

[0499] (Synthesis of intermediate J)

[0500]

[0501] Intermediate J was synthesized in the same manner as Intermediate A, except that 3,6-Dibromocarbazole (10.0 g, 30.8 mmol) was used instead of Bis(4-bromophenyl)amine in the synthesis of Intermediate A, and Intermediate J (10.6 g, yield 92%) was obtained. The molecular weight of Intermediate J was 375 according to FAB MS measurements.

[0502] (Synthesis of intermediate K)

[0503]

[0504] Under an Ar atmosphere, intermediate A (23.9 g, 63.7 mmol), intermediate B (8.0 g, 31.9 mmol), Pd(dba)2 (1.83 g, 63.7 mmol), P(t-Bu)3HBF4 (1.84 g, 6.37 mmol), and tBuONa (7.04 g, 73.3 mmol) were added to 200 ml of toluene and heated and stirred at 80°C for 2 hours. Water was added, separated by Celite filtration, and the organic layer was concentrated. The mixture was purified by silica gel column chromatography to obtain intermediate K (13.2 g, yield 70%). FAB MS measurement revealed that the molecular weight of intermediate K was 592.

[0505] (Synthesis of intermediate L)

[0506]

[0507] Under an Ar atmosphere, intermediate K (12.0 g, 20.6 mmol), 2,6-Diphenylaniline (6.46 g, 26.3 mmol), Pd(dba)2 (1.17 g, 2.03 mmol), P(t-Bu)3HBF4 (1.18 g, 4.05 mmol), and tBuONa (4.48 g, 46.6 mmol) were added to 100 ml of toluene and heated and stirred at 80°C for 2 hours. Water was added, and the mixture was separated by Celite filtration to concentrate the organic layer. The mixture was purified by silica gel column chromatography to obtain intermediate L (14.6 g, yield 90%). FAB MS measurement revealed that the molecular weight of intermediate L was 801.

[0508] (Synthesis of intermediate M)

[0509]

[0510] Approximately 10 ml of toluene was added to intermediate L (14.0 g, 17.5 mmol), 3-Chloro-1-iodebenzene (62.5 g, 262 mmol), CuI (6.99 g, 36.7 mmol), and K2CO3 (19.3 g, 140 mmol), and heated for 24 hours while maintaining the ambient temperature at 215°C. The mixture was diluted with CH2Cl2, water was added, and the solution was separated by Celite filtration to concentrate the organic layer. It was purified by silica gel column chromatography to obtain intermediate M (11.2 gg, yield 70%). FAB MS measurement revealed that the molecular weight of intermediate M was 911.

[0511] (Synthesis of intermediate N)

[0512]

[0513] Under an Ar atmosphere, intermediate M (12.0 g, 13.2 mmol), intermediate J (6.43 g, 17.1 mmol), Pd(dba)2 (757 mg, 1.32 mmol), P(t-Bu)3HBF4 (764 mg, 2.63 mmol), and tBuONa (2.91 g, 30.3 mmol) were added to 100 ml of toluene and heated and stirred at 80°C for 2 hours. Water was added, and the mixture was separated by Celite filtration to concentrate the organic layer. The mixture was purified by silica gel column chromatography to obtain intermediate N (12.3 g, yield 75%). FAB MS measurement revealed that the molecular weight of intermediate N was 1250.

[0514] (Synthesis of Compound 13)

[0515]

[0516] Compound 13 (4.13 g, yield 41%) was obtained by synthesizing the compound in the same manner as Compound 1, except that intermediate N (10.0 g, 8.00 mmol) was used instead of intermediate C. FAB MS measurement revealed that the molecular weight of Compound 13 was 1258. Sublimation purification (380°C, 2.5 x 10⁻⁶-3 Pa) conducted a device evaluation.

[0517] (5) Synthesis of Compound 34

[0518] A condensed polycyclic compound 34 according to one embodiment can be synthesized, for example, by the following reaction.

[0519] (Synthesis of intermediate O)

[0520]

[0521] Intermediate O was synthesized in the same manner as Intermediate A, except that Bis(3-bromophenyl)amine (10.0 g, 30.6 mmol) was used instead of Bis(4-bromophenyl)amine in the synthesis of Intermediate A, and Intermediate O (9.47 g, yield 82%) was obtained. The molecular weight of Intermediate O was 377 according to FAB MS measurements.

[0522] (Synthesis of intermediate P)

[0523]

[0524] Under an Ar atmosphere, intermediate O (24.1 g, 63.1 mmol), intermediate B (8.0 g, 31.9 mmol), Pd(dba)2 (1.83 g, 63.7 mmol), P(t-Bu)3HBF4 (1.84 g, 6.37 mmol), and tBuONa (7.04 g, 73.3 mmol) were added to 200 ml of toluene and heated and stirred at 80°C for 2 hours. Water was added, and the mixture was separated by Celite filtration to concentrate the organic layer. The mixture was purified by silica gel column chromatography to obtain intermediate P (14.1 g, yield 75%). FAB MS measurement revealed that the molecular weight of intermediate P was 592.

[0525] (Synthesis of intermediate Q)

[0526]

[0527] Under an Ar atmosphere, intermediate P (13.0 g, 22.0 mmol), 2,6-Diphenylaniline (7.00 g, 28.5 mmol), Pd(dba)2 (1.26 g, 2.20 mmol), P(t-Bu)3HBF4 (1.27 g, 4.39 mmol), and tBuONa (4.85 g, 50.5 mmol) were added to 120 ml of toluene and heated and stirred at 80°C for 2 hours. Water was added, separated by Celite filtration, and the organic layer was concentrated. The mixture was purified by silica gel column chromatography to obtain intermediate Q (16.0 g, yield 91%). FAB MS measurement revealed that the molecular weight of intermediate Q was 801.

[0528] (Synthesis of intermediate R)

[0529]

[0530] Approximately 10 ml of toluene was added to intermediate Q (14.0 g, 17.5 mmol), 3-Chloro-1-iodebenzene (62.5 g, 262 mmol), CuI (6.99 g, 36.7 mmol), and K2CO3 (19.3 g, 140 mmol), and heated for 24 hours while maintaining the ambient temperature at 215°C. The mixture was diluted with CH2Cl2, water was added, and the liquids were separated by Celite filtration to concentrate the organic layer. The intermediate R (10.4 g, yield 65%) was obtained by purification using silica gel column chromatography. The molecular weight of intermediate R was 911 as measured by FAB MS.

[0531] (Synthesis of intermediate S)

[0532]

[0533] Under an Ar atmosphere, intermediate R (10.0 g, 11.0 mmol), intermediate J (5.36 g, 14.3 mmol), Pd(dba)2 (631 mg, 1.10 mmol), P(t-Bu)3HBF4 (637 mg, 2.19 mmol), and tBuONa (2.43 g, 25.2 mmol) were added to 100 ml of toluene and heated and stirred at 80°C for 2 hours. Water was added, separated by Celite filtration, and the organic layer was concentrated. The mixture was purified by silica gel column chromatography to obtain intermediate S (9.88 g, yield 72%). FAB MS measurement revealed that the molecular weight of intermediate S was 1250.

[0534] (Synthesis of Compound 34)

[0535]

[0536] Compound 34 (3.44 g, yield 38%) was obtained by synthesizing the compound in the same manner as Compound 1, except that intermediate S (9.0 g, 7.20 mmol) was used instead of intermediate C. FAB MS measurements showed that the molecular weight of Compound 34 was 1258. Sublimation purification (370°C, 2.8 x 10⁻⁶ -3 Pa) conducted a device evaluation.

[0537] (6) Synthesis of Compound 41

[0538] A condensed polycyclic compound 41 according to one embodiment can be synthesized, for example, by the following reaction.

[0539] (Synthesis of intermediate T)

[0540]

[0541] Under an Ar atmosphere, intermediate K (13.0 g, 22.0 mmol), Aniline (2.66 g, 28.5 mmol), Pd(dba)2 (1.26 g, 2.20 mmol), P(t-Bu)3HBF4 (1.27 g, 4.39 mmol), and tBuONa (4.85 g, 50.5 mmol) were added to 200 ml of toluene and heated and stirred at 80°C for 2 hours. Water was added, and the mixture was separated by Celite filtration to concentrate the organic layer. The mixture was purified by silica gel column chromatography to obtain intermediate T (11.8 g, yield 83%). FAB MS measurement revealed that the molecular weight of intermediate T was 648.

[0542] (Synthesis of intermediate U)

[0543]

[0544] Under an Ar atmosphere, intermediate T (5.00 g, 7.71 mmol), intermediate M (7.02 g, 7.71 mmol), Pd(dba)2 (443 mg, 0.77 mmol), P(t-Bu)3HBF4 (447 mg, 1.54 mmol), and tBuONa (1.70 g, 17.7 mmol) were added to 100 ml of toluene and heated and stirred at 80°C for 2 hours. Water was added, and the mixture was separated by Celite filtration to concentrate the organic layer. The mixture was purified by silica gel column chromatography to obtain intermediate U (9.86 g, yield 84%). FAB MS measurement revealed that the molecular weight of intermediate U was 1524.

[0545] (Synthesis of Compound 41)

[0546]

[0547] Compound 41 (2.27 g, yield 25%) was obtained by synthesizing the compound in the same manner as Compound 1, except that intermediate U (9.0 g, 5.91 mmol) was used instead of intermediate C. FAB MS measurement revealed that the molecular weight of Compound 41 was 1539. Sublimation purification (410°C, 1.8 x 10⁻⁶ -3 Pa) conducted a device evaluation.

[0548] (7) Synthesis of Compound 42

[0549] A condensed polycyclic compound 42 according to one embodiment can be synthesized, for example, by the following reaction.

[0550] (Synthesis of intermediate V)

[0551]

[0552] Under an Ar atmosphere, 1-bromo-3,5-dichlorobenzene (8.0 g, 35.4 mmol) and intermediates J (14.6 g, 39.0 mmol), Pd(dba)2 (2.04 g, 3.54 mmol), P(t-Bu)3HBF4 (2.06 g, 7.08 mmol), and tBuONa (7.83 g, 81.5 mmol) were added to 250 ml of toluene and heated and stirred at 80°C for 2 hours. Water was added, separated by Celite filtration, and the organic layer was concentrated. The mixture was purified by silica gel column chromatography to obtain intermediate V (14.9 g, yield 81%). FAB MS measurement revealed that the molecular weight of intermediate V was 520.

[0553] (Synthesis of intermediate W)

[0554]

[0555] Under an Ar atmosphere, intermediate V (14.0 g, 26.9 mmol), diphenylamine (5.00 g, 29.6 mmol), Pd(dba)2 (1.54 g, 2.69 mmol), P(t-Bu)3HBF4 (1.56 g, 2.69 mmol), and tBuONa (5.95 g, 61.9 mmol) were added to 250 ml of toluene and heated and stirred at 80°C for 2 hours. Water was added, and the mixture was separated by Celite filtration to concentrate the organic layer. The mixture was purified by silica gel column chromatography to obtain intermediate W (13.2 g, yield 75%). FAB MS measurement revealed that the molecular weight of intermediate W was 653.

[0556] (Synthesis of intermediate X)

[0557]

[0558] The synthesis of intermediate X was carried out in the same manner as that of intermediate Q, except that intermediate W (13.0 g, 22.0 mmol) was used instead of intermediate P in the synthesis of intermediate Q, and intermediate X (16.0 g, yield 91%) was obtained. The molecular weight of intermediate X was 862 according to FAB MS measurements.

[0559] (Synthesis of intermediate Y)

[0560]

[0561] The synthesis of intermediate Y was carried out in the same manner as that of intermediate R, except that intermediate X (14.0 g, 17.5 mmol) was used instead of intermediate Q in the synthesis of intermediate R, and intermediate Y (9.35 g, yield 55%) was obtained. The molecular weight of intermediate Y was 972 according to FAB MS measurements.

[0562] (Synthesis of intermediate Z)

[0563]

[0564] Intermediate Z (13.5 g, yield 79%) was obtained by proceeding in the same manner as intermediate U, except that intermediate T (7.00 g, 10.8 mmol) was used instead of intermediate M and intermediate Y (10.5 g, 10.8 mmol) was used instead of intermediate T. FAB MS measurement revealed that the molecular weight of intermediate Z was 1585.

[0565] (Synthesis of Compound 42)

[0566]

[0567] Compound 42 (3.27 g, yield 27%) was obtained by synthesizing the compound in the same manner as Compound 1, except that intermediate Z (12.0 g, 7.57 mmol) was used instead of intermediate C. FAB MS measurement revealed that the molecular weight of Compound 42 was 1600. Sublimation purification (420°C, 1.5 x 10⁻⁶ -3 Pa) conducted a device evaluation.

[0568] (8) Synthesis of Compound 59

[0569] A condensed polycyclic compound 59 according to one embodiment can be synthesized, for example, by the following reaction.

[0570] (Synthesis of intermediate AA)

[0571]

[0572] Under an Ar atmosphere, 3,5-Dibromoanisole (5.00 g, 18.8 mmol), intermediate A (15.6 g, 41.4 mmol), Pd(dba)2 (1.08 g, 1.88 mmol), P(t-Bu)3HBF4 (1.09 g, 3.76 mmol), and tBuONa (4.16 g, 43.2 mmol) were added to 200 ml of toluene and heated and stirred at 80°C for 2 hours. Water was added, and the mixture was separated by Celite filtration to concentrate the organic layer. The mixture was purified by silica gel column chromatography to obtain intermediate AA (14.7 g, yield 91%). FAB MS measurement revealed that the molecular weight of intermediate AA was 859.

[0573] (Synthesis of intermediate AB)

[0574]

[0575] Under an Ar atmosphere, intermediate AA (12.0 g, 14.0 mmol) was dissolved in CH2Cl2 (200 ml), and BBr3 (8.0 g, 32.1 mmol) was added at 0°C. The mixture was heated to room temperature and stirred for 24 hours. The reaction was cooled to 0°C, 100 ml of water was added and stirred for 1 hour, then separated by Celite filtration, and the organic layer was concentrated. The mixture was purified by silica gel column chromatography to obtain intermediate AB (9.44 g, yield 80%). FAB MS measurement showed that the molecular weight of intermediate AB was 845.

[0576] (Synthesis of intermediate AC)

[0577]

[0578] The synthesis of intermediate AC was carried out in the same manner as that of intermediate R, except that intermediate L (10.0 g, 12.5 mmol) was used instead of intermediate Q and 3-Fluoro-1-iodebenzene (41.6 g, 187 mmol) was used instead of 3-Chloro-1-iodebenzene, and intermediate AC (7.82 g, yield 70%) was obtained. The molecular weight of intermediate AC was 895 according to FAB MS measurements.

[0579] (Synthesis of the intermediate AD)

[0580]

[0581] Under an Ar atmosphere, intermediate AC (7.00 g, 7.82 mmol) and intermediate AB (7.93 g, 9.38 mmol) were added to 1-Methyl-2-pyrrolidone (NMP, 150 ml) and 0 After maintaining, add 60% NaH (0.63g, 15.6mmol) and stir for 30 minutes, then 100 The mixture was stirred for 6 hours, water and toluene were added and stirred for 1 hour, then separated by Celite filtration, and the organic layer was concentrated. It was purified by silica gel column chromatography to obtain the intermediate AD (11.7 g, yield 87%). The molecular weight of the intermediate AD was 1720 according to FAB MS measurement.

[0582] (Synthesis of Compound 59)

[0583]

[0584] Compound 59 (1.81 g, yield 18%) was obtained by the same method as the synthesis of Compound 1, except that intermediate AD (10.0 g, 5.81 mmol) was used instead of intermediate C in the synthesis of Compound 1. The molecular weight of Compound 59 was 1735 by FAB MS measurement. Sublimation purification (415°C, 1.7 x 10⁻⁶ -3 Pa) conducted a device evaluation.

[0585] (9) Synthesis of Compound 81

[0586] A condensed polycyclic compound 81 according to one embodiment can be synthesized, for example, by the following reaction.

[0587] (Synthesis of intermediate AE)

[0588]

[0589] The synthesis of intermediate AE was carried out in the same manner as intermediate A, except that 3,6-Dibromocarbazole (10.0 g, 30.8 mmol) was used instead of Bis(4-bromophenyl)amine and 2,4,6-Triisopropylbenzeneboronic acid (16.8 g, 67.7 mmol) was used instead of 2,6-Dimethylphenylboronic acid, thereby obtaining intermediate AE (14.6 g, yield 83%). FAB MS measurement showed that the molecular weight of intermediate AE was 571.

[0590] (Synthesis of intermediate AF)

[0591]

[0592] Under an Ar atmosphere, 3,5-Dibromo-chlorobenzene (5.00 g, 18.5 mmol), Bis(4-biphenylyl)amine (13.1 g, 46.7 mmol), Pd(dba)2 (1.06 g, 1.85 mmol), P(t-Bu)3HBF4 (1.07 g, 3.70 mmol), and tBuONa (4.09 g, 42.5 mmol) were added to 200 ml of toluene and heated and stirred at 80°C for 2 hours. Water was added, and the mixture was separated by Celite filtration to concentrate the organic layer. The mixture was purified by silica gel column chromatography to obtain the intermediate AF (13.9 g, yield 88%). FAB MS measurement revealed that the molecular weight of the intermediate AF was 751.

[0593] (Synthesis of intermediate AG)

[0594]

[0595] Intermediate AG (4.12 g, yield 40%) was obtained in the same manner as in the synthesis of Compound 1, except that intermediate AF (10.0 g, 13.3 mmol) was used instead of intermediate C in the synthesis of Compound 1. The molecular weight of intermediate AG was 775 according to FAB MS measurements.

[0596] (Synthesis of Compound 81)

[0597]

[0598] Under an Ar atmosphere, intermediate AG (5.00 g, 6.45 mmol), intermediate AE (5.53 g, 9.67 mmol), Pd(dba)2 (0.37 g, 0.64 mmol), P(t-Bu)3HBF4 (0.37 g, 1.29 mmol), and tBuONa (1.43 g, 14.8 mmol) were added to 100 ml of toluene and heated and stirred at 80°C for 2 hours. Water was added, separated by Celite filtration, and the organic layer was concentrated. Compound 81 (7.09 g, yield 85%) was obtained by purification using silica gel column chromatography. The molecular weight of Compound 81 was 1294 by FAB MS measurement. Sublimation purification (370°C, 2.7 x 10⁻⁶ -3 Pa) conducted a device evaluation.

[0599] (10) Synthesis of Compound 90

[0600] A condensed polycyclic compound 90 according to one embodiment can be synthesized, for example, by the following reaction.

[0601] (Synthesis of intermediate AH)

[0602]

[0603] Under an Ar atmosphere, 3,5-Dibromo-chlorobenzene (5.0 g, 18.5 mmol), 2,6-Diphenylaniline (9.98 g, 40.7 mmol), Pd(dba)2 (1.06 g, 1.85 mmol), P(t-Bu)3HBF4 (1.07 g, 3.70 mmol), and tBuONa (4.09 g, 42.5 mmol) were added to 100 ml of toluene and heated and stirred at 80°C for 2 hours. Water was added, and the mixture was separated by Celite filtration to concentrate the organic layer. The mixture was purified by silica gel column chromatography to obtain the intermediate AH (9.75 g, yield 88%). FAB MS measurement revealed that the molecular weight of the intermediate AH was 599.

[0604] (Synthesis of intermediate AI)

[0605]

[0606] The synthesis of intermediate AI was carried out in the same manner as that of intermediate R, except that intermediate AH (9.50 g, 15.9 mmol) was used instead of intermediate Q and 4-Iodebiphenyl (66.6 g, 238 mmol) was used instead of 3-Chloro-1-iodebenzene, thereby obtaining intermediate AI (10.0 g, yield 70%). The molecular weight of intermediate AI was 903 according to FAB MS measurements.

[0607] (Synthesis of intermediate AJ)

[0608]

[0609] Intermediate AJ (4.79 g, yield 50%) was obtained in the same manner as in the synthesis of Compound 1, except that intermediate AI (9.50 g, 10.5 mmol) was used instead of intermediate C in the synthesis of Compound 1. The molecular weight of intermediate AJ was 911 according to FAB MS measurements.

[0610] (Synthesis of Compound 90)

[0611]

[0612] Under an Ar atmosphere, intermediate AJ (3.00 g, 3.29 mmol), intermediate AE (2.82 g, 4.94 mmol), Pd(dba)2 (189 mg, 0.33 mmol), P(t-Bu)3HBF4 (191 g, 0.66 mmol), and tBuONa (723 mg, 7.57 mmol) were added to 50 ml of toluene and heated and stirred at 80°C for 2 hours. Water was added, separated by Celite filtration, and the organic layer was concentrated. Compound 90 (4.24 g, yield 89%) was obtained by purification using silica gel column chromatography. The molecular weight of Compound 90 was 1446 by FAB MS measurement. Sublimation purification (350°C, 2.6 x 10⁻⁶) -3 Pa) conducted a device evaluation.

[0613] (11) Synthesis of Compound 121

[0614] A condensed polycyclic compound 121 according to one embodiment can be synthesized, for example, by the following reaction.

[0615] (Synthesis of the intermediate AK)

[0616]

[0617] Under an Ar atmosphere, intermediate V (14.0 g, 26.9 mmol), intermediate O (11.2 g, 29.6 mmol), Pd(dba)2 (1.54 g, 2.69 mmol), P(t-Bu)3HBF4 (1.56 g, 2.69 mmol), and tBuONa (5.95 g, 61.9 mmol) were added to 250 ml of toluene and heated and stirred at 80°C for 2 hours. Water was added, separated by Celite filtration, and the organic layer was concentrated. The mixture was purified by silica gel column chromatography to obtain intermediate AK (18.1 g, yield 78%). FAB MS measurement revealed that the molecular weight of intermediate AK was 861.

[0618] (Synthesis of intermediate AL)

[0619]

[0620] Under an Ar atmosphere, intermediate AK (12.0 g, 13.9 mmol), Aniline (1.69 g, 18.1 mmol), Pd(dba)2 (0.80 g, 1.39 mmol), P(t-Bu)3HBF4 (808 mg, 2.79 mmol), and tBuONa (3.08 g, 32.0 mmol) were added to 200 ml of toluene and heated and stirred at 80°C for 2 hours. Water was added, and the mixture was separated by Celite filtration to concentrate the organic layer. The mixture was purified by silica gel column chromatography to obtain intermediate AL (10.5 g, yield 82%). FAB MS measurement revealed that the molecular weight of intermediate AL was 918.

[0621] (Synthesis of the intermediate AM)

[0622]

[0623] Under an Ar atmosphere, intermediate AL (7.78 g, 8.48 mmol), 1,3-dibromobenzene (1.00 g, 4.24 mmol), Pd(dba)2 (244 mg, 0.42 mmol), P(t-Bu)3HBF4 (246 g, 0.85 mmol), and tBuONa (937 mg, 9.75 mmol) were added to 100 ml of toluene and heated and stirred at 80°C for 2 hours. Water was added, separated by Celite filtration, and the organic layer was concentrated. Purified by silica gel column chromatography, intermediate AM (7.53 g, yield 93%) was obtained. FAB MS measurement showed that the molecular weight of intermediate AM was 1910.

[0624] (Synthesis of Compound 121)

[0625]

[0626] Compound 121 (1.61 g, yield 32%) was obtained by the same method as the synthesis of Compound 1, except that intermediate AM (5.0 g, 2.62 mmol) was used instead of intermediate C in the synthesis of Compound 1. The molecular weight of Compound 121 was 1928 by FAB MS measurement. Sublimation purification (410°C, 1.3 x 10⁻⁶ -3 Pa) conducted a device evaluation.

[0627] 2. Fabrication and Evaluation of Light Emitting Devices Containing Condensed Polycyclic Compounds

[0628] (Fabrication of light-emitting devices)

[0629] The light-emitting devices of Examples 1 to 11 were fabricated using the above-described compounds 1, 2, 3, 13, 34, 41, 42, 59, 81, 90, and 121 as light-emitting layer dopant materials.

[0630] [Example Compound]

[0631]

[0633]

[0634] Comparative examples X61 to X6 below were used in the manufacture of devices for Comparative Examples 1 to 6.

[0635] [Comparative Example Compound]

[0636]

[0637] A light-emitting device of one embodiment comprising a condensed polycyclic compound of one embodiment in a light-emitting layer was manufactured by the following method. Examples 1 to 11 correspond to light-emitting devices fabricated using the above-described example compounds 1, 2, 3, 13, 34, 41, 42, 59, 81, 90, and 121 as light-emitting materials. Comparative Examples 1 to 6 correspond to light-emitting devices fabricated using comparative example compounds X1 to X6 as light-emitting materials.

[0638] 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] quinoxaline-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-emitting 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-emitting 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 300 nm was formed on the electron injection layer using Al. Each layer was formed by deposition under vacuum conditions.

[0639] 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.

[0640]

[0641] (Experimental Example)

[0642] The device efficiency of light-emitting devices fabricated with the aforementioned experimental example compounds 1, 2, 3, 13, 34, 41, 42, 59, 81, 90, and 121, and comparative example compounds X1 to X6 was evaluated. The evaluation results are shown in Table 1 below. In the device evaluation, the current density was evaluated, and 1000 cd / m²2 The luminous efficiency and device lifetime of the light-emitting device were measured and indicated. In addition, for the device evaluation, the maximum emission wavelength of the emission spectrum was set to λmax. LT50 represents the relative lifetime value when the half-life of Comparative Example Compound X3 of Comparative Example 3 is set to 1.

[0643] Example of device fabrication Dopant Emission wavelength (λmax, nm) Delayed fluorescence lifetime (μs) Roll-off (%) LT50 Relative Life Example 1 Example Compound 1 457 90 25.6 2.8 Example 2 Example Compound 2 458 110 27.0 3.3 Example 3 Example Compound 3 459 120 32.0 4.2 Example 4 Example Compound 13 458 80 21.0 4.8 Example 5 Example Compound 34 459 85 23.0 5.2 Example 6 Example Compound 41 460 12 18.1 6.1 Example 7 Example Compound 42 459 8.0 16.2 6.2 Example 8 Example Compound 59 460 5.0 12.2 7.2 Example 9 Example Compound 81 457 50 17.2 4.2 Example 10 Example Compound 90 458 55 18.2 4.9 Example 11 Example Compound 121 459 4.2 10.2 8.2 Comparative Example 1 Comparative Example Compound X1 457 130 33.2 0.3 Comparative Example 2 Comparative Example Compound X2 446 11.2 30.5 0.2 Comparative Example 3 Comparative Example Compound X3 467 5.5 13.5 1 Comparative Example 4 Comparative Example Compound X4 461 125 45.3 0.28 Comparative Example 5 Comparative Example Compound X5 475 15 35.2 0.55 Comparative Example 6 Comparative Example Compound X6 453 105 55.8 0.17

[0644] Referring to the results in Table 1, it can be seen that in the case of the light-emitting device examples using a condensed polycyclic compound according to one embodiment of the present invention as a light-emitting material, the device lifespan is improved compared to the comparative example, and the light emission wavelength is shortened, showing color purity close to pure blue.

[0645] In the case of the compounds in the examples, by having a broad plate-like structure in which multiple aromatic rings are condensed around at least one boron atom and at least two nitrogen atoms, the multiple resonance effect is increased while maintaining a low △E ST It can have. Accordingly, since the occurrence of inverse term crossing from the triplet excited state to the singlet excited state is facilitated, the delayed fluorescence characteristics are enhanced and the luminescence efficiency can be improved.

[0646] In addition, in the case of the compounds of the examples, by introducing a first substituent represented by Formula 2 or a second substituent represented by Formula 3 into the condensed ring core structure, the emission wavelength can be shortened, and at the same time, a long lifespan can be achieved by reducing the degradation of the lifetime due to intermolecular interactions. More specifically, the compounds of the examples include a structure in which a first substituent represented by Formula 2 is necessarily connected to a specific ring among the aromatic rings constituting the condensed ring core, or a structure in which at least one second substituent represented by Formula 3 is included in the condensed ring core. Accordingly, the compounds of the examples have a relatively twisted structural form compared to the comparative example compounds through the steric hindrance effect caused by the first or second substituent, and thus, since non-radiative transitions caused by intermolecular interactions can be prevented, the luminescence efficiency can be further increased. In addition, the compounds of the examples include a first substituent represented by Formula 2 in the condensed ring core, thereby increasing the dihedral angle between the plane containing the condensed ring core centered on the boron atom and the plane containing the first substituent. Accordingly, the effective conjugation length of the compounds of the examples is shortened, and as a result, the emission wavelength can be shortened.

[0647] It can be confirmed that the emission wavelengths of Examples 1 to 11 were all shortened to show a color purity closer to pure blue.

[0648] When comparing Examples 1 to 3 with Comparative Example 1, it can be confirmed that in the case of Examples 1 to 3, the first substituent represented by Chemical Formula 2 is substituted into the condensed ring skeleton structure of Comparative Example 1, but the emission wavelength does not become longer compared to Comparative Example 1. Normally, the emission wavelength shifts toward the longer wavelength side when a substituent is substituted, but it can be seen that the condensed polycyclic compound of one embodiment according to the present invention can prevent the emission wavelength from becoming longer while improving lifetime characteristics by introducing a bulky substituent.

[0649] Examples 1 to 11 show that the roll-off is low in proportion to the luminescence lifetime, and Triplet-Triplet Annihilation (TTA) and Singlet-Triplet Annihilation (STA) are suppressed.

[0650] When comparing Examples 1 to 3 with Comparative Example 1, it can be seen that in Example Compounds 1 to 3, in which a first substituent represented by Chemical Formula 2 is introduced into a condensed ring core, the relative lifetime is increased by more than 10 times compared to Comparative Example Compound X1.

[0651] Meanwhile, looking at Comparative Example 4, Comparative Example Compound X4 contains a bulky substituent similar to the Example Compounds, but its relative lifetime is 0.28, showing almost no change compared to the relative lifetime of Comparative Example 1. It is determined that the lifetime characteristics of Comparative Example Compound X4 are degraded compared to the Example Compounds because it does not contain a bulky substituent in the aryl group portion, which is a terminal substituent connected to the nitrogen atom. On the other hand, as in Example Compound 3, the introduction of the first substituent represented by Chemical Formula 2 into the terminal substituent connected to the nitrogen atom resulted in a relative lifetime of 4.2, which is significantly higher than the relative lifetime of Comparative Example 1. It is possible to effectively improve the lifetime when the first substituent is necessarily substituted at a specific position on the condensed ring core, as in the condensed polycyclic compound of one embodiment of the present invention. Furthermore, a significant improvement in the lifetime can be expected when the structure of the first substituent represented by Chemical Formula 2 includes a substituent with three or more carbon atoms.

[0652]

[0653] When comparing Examples 4, 5, 9, and 10 with Comparative Example 2, it can be seen that the relative lifetime of Comparative Example 2 is 0.2, indicating a significant decrease in lifetime. In the case of Comparative Example Compound X2, a diphenylamine group having electron-donating properties is introduced as a donor into the condensed ring core, resulting in a shorter emission wavelength; however, since it does not contain bulky substituents, the interaction between dopants or between a dopant and a host increases, which is thought to be the reason for the significant decrease in relative lifetime.

[0654] When comparing Examples 4, 5, 9, and 10 with Comparative Example 5, Examples 4, 5, 9, and 10 all exhibit a color purity closer to pure blue with an emission wavelength around 460 nm; however, in Comparative Example 5, the emission wavelength became significantly longer at 475 nm, even though a carbazole group was substituted as a donor. It is believed that the long wavelength was achieved in Comparative Example Compound X5 because the conjugation extends to the phenyl group substituted on the carbazole group. On the other hand, in Examples 13, 34, 81, and 90, the long wavelength was suppressed because the carbazole group and the first substituent are twistedly bonded as the first substituent is connected to the carbazole group, thereby reducing the extension of the conjugation.

[0655]

[0656] When comparing Examples 6, 7, 8, and 11 with Comparative Example 3, it can be seen that Comparative Example Compound X3 included in Comparative Example 3 contains a broad plate-like framework structure centered on two boron atoms, but does not contain bulky steric hindrance substituents in the plate-like framework, so the relative lifetime is reduced.

[0657] When comparing Example 1 and Comparative Example 6, it can be seen that Comparative Example Compound X6 included in Comparative Example 6 contains a structure in which three aromatic rings are condensed around one boron atom and includes bulky substituents in the condensed ring core, but its relative lifetime is 0.17, which is significantly lower than that of the Examples and Comparative Examples 1 to 5. This is because Comparative Example Compound X6 does not necessarily include two nitrogen atoms as the two constituent atoms of the condensed ring, and as two benzene rings connected by bulky substituents in the condensed ring structure are connected to each other, the roll-off increases compared to the Examples and the relative lifetime is significantly reduced.

[0658] 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.

[0659] 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

[0660] DD, DD-TD: Display device ED: Light-emitting element EL1: First electrode EL2: Second electrode HTR: Hole transport region EML: Emissive layer ETR: Electron transport region

Claims

Claim 1 A light-emitting device comprising: a first electrode; a second electrode facing the first electrode; and a light-emitting layer disposed between the first electrode and the second electrode, wherein the light-emitting layer comprises a host and a dopant, wherein the host comprises a compound represented by the following chemical formula E-2a or chemical formula E-2b, and the dopant comprises a condensed polycyclic compound represented by the following chemical formula 1: [Chemical Formula 1] In the above Formula 1, C1 to C5 are each independently a six-membered aromatic hydrocarbon ring, and R1 to R5 are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted arylboro group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted t-butyl group, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted biphenyl group, or form a ring by combining with an adjacent group, or are substituents represented by Formula 2 below, or are substituents represented by Formula 3 below, and all of R1 to R3 are represented by Formula 2 below, or at least one of R1 to R5 is represented by Formula 3 below, and n1 and n5 are each independently integers from 1 to 4, n2 and n4 are each independently integers from 1 to 5, and n3 is an integer from 1 to 3: [Formula 2] In the above Chemical Formula 2, A1 and A2 are each independently a substituted or unsubstituted methyl group, or a substituted or unsubstituted isopropyl group, and R a1 to R a3 Each is independently a hydrogen atom, a deuterium atom, or a substituted or unsubstituted isopropyl group: [Chemical Formula 3] In the above Chemical Formula 3, a is 0 or 1, and when a is 1, Y is a direct linkage, Z1 and Z2 are each independently represented by the above Chemical Formula 2, R6 and R7 are each independently a hydrogen atom or a deuterium atom, and n6 and n7 are each independently integers from 0 to 4: [Chemical Formula E-2a] [Chemical Formula E-2b] In the above chemical formula E-2a, b is an integer from 0 to 10, and L a is a direct linkage, 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, and A a To A e Each independently N or CR i and R a to R i Each is 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 can form a ring by bonding with an adjacent group, and A a To A e Two or three selected are N, and the rest are CR i And, in the above formula E-2b, Cbz1 and Cbz2 are each independently an unsubstituted carbazole group, or a carbazole group substituted with a ring-forming aryl group having 6 to 30 carbon atoms, and L b is 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, and c is an integer from 0 to 10. Claim 2 In claim 1, the light-emitting layer is a light-emitting element that emits delayed fluorescence. Claim 3 In claim 1, the light-emitting layer is a light-emitting element that emits light having a center wavelength of light of 430 nm or more and 490 nm or less. Claim 4 In claim 1, the condensed polycyclic compound represented by Chemical Formula 1 is a light-emitting element represented by the following Chemical Formula 1-1: [Chemical Formula 1-1] In the above chemical formula 1-1, R 1-1 to R 3-1 Each is independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted arylboro group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted t-butyl group, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted biphenyl group, or forms a ring by combining with an adjacent group, and R 1-1a to R 3-1a Each is independently represented by the above chemical formula 2, m1 is an integer from 0 to 3, m2 is an integer from 0 to 4, m3 is an integer from 0 to 2, and R4, R5, n4, and n5 are the same as defined in the above chemical formula 1. Claim 5 In claim 4, the condensed polycyclic compound represented by the above formula 1-1 is a light-emitting element represented by the following formula 1-2-1 or formula 1-2-2: [Formula 1-2-1] [Chemical Formula 1-2-2] In the above chemical formulas 1-2-1 and 1-2-2, R 1-1 to R 3-1 , R 1-1a to R 3-1a , m1 to m3, R4, R5, n4, and n5 are the same as defined in Chemical Formula 1 and Chemical Formula 1-1 above. Claim 6 In claim 4, the condensed polycyclic compound represented by the above chemical formula 1 is a light-emitting element represented by the following chemical formula 1-3-1 or chemical formula 1-3-2: [Chemical formula 1-3-1] [Chemical Formula 1-3-2] In the above chemical formulas 1-3-1 and 1-3-2, R 4-1 and R 5-1 Each is independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted arylboro group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted t-butyl group, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted biphenyl group, or forms a ring by combining with an adjacent group, and R 5-1a is represented by the above chemical formula 3, and R 21 and R 22 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cyclic aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted cyclic heteroaryl group having 2 to 30 carbon atoms, m4 is an integer from 0 to 4, m5 is an integer from 0 to 3, n21 and n22 are each independently integers from 0 to 5, and R 1-1 to R 3-1 , R 1-1a to R 3-1a , m1 to m3 are the same as defined in Chemical Formula 1 and Chemical Formula 1-1 above. Claim 7 In claim 1, the substituent represented by Chemical Formula 2 is a light-emitting element represented by the following Chemical Formula 2-1 or Chemical Formula 2-2: [Chemical Formula 2-1] [Chemical Formula 2-2] In the above Chemical Formulas 2-1 and 2-2, A 1-1 and A 2-1 Each is independently a substituted or unsubstituted methyl group, or a substituted or unsubstituted isopropyl group, and A 1-2 , A 2-2 , and A3 are each independently substituted or unsubstituted isopropyl groups, and R a1 to R a3 It is the same as defined in Chemical Formula 2 above. Claim 8 In claim 1, the substituent represented by Chemical Formula 3 is a light-emitting element represented by the following Chemical Formula 3-1 or Chemical Formula 3-2: [Chemical Formula 3-1] [Chemical Formula 3-2] In the above Chemical Formulas 3-1 and 3-2, n 6-1 and n 7-1 are each independently integers from 0 to 3, and n 6-2 and n 7-2 Each is independently an integer between 0 and 4, and Z1, Z2, R6, and R7 are the same as defined in Chemical Formula 3 above. Claim 9 In claim 1, the condensed polycyclic compound represented by Chemical Formula 1 is a light-emitting element represented by the following Chemical Formula 1-4-1 or Chemical Formula 1-4-2: [Chemical Formula 1-4-1] [Chemical Formula 1-4-2] In the above chemical formulas 1-4-1 and 1-4-2, R 3-2 and R 5-2 Each is independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted arylboro group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted t-butyl group, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted biphenyl group, or forms a ring by combining with an adjacent group, and R 3-1b and R 5-1b Each is independently represented by the above chemical formula 3, b3 is an integer from 0 to 2, b5 is an integer from 0 to 3, and R1 to R5 and n1 to n5 are the same as defined in the above chemical formula 1. Claim 10 In claim 1, the condensed polycyclic compound represented by Chemical Formula 1 is a light-emitting element represented by the following Chemical Formula 1-5-1 or Chemical Formula 1-5-2: [Chemical Formula 1-5-1] [Chemical Formula 1-5-2] In the above chemical formulas 1-5-1 and 1-5-2, R 1-2 , R 3-2 , and R 5-2 Each is independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted arylboro group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted t-butyl group, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted biphenyl group, or forms a ring by combining with an adjacent group, and R 1-1b , R 3-1b and R 5-1b Each is independently represented by the above chemical formula 3, b1 and b5 are each independently integers from 0 to 3, b3 is an integer from 0 to 2, and R2 to R4 and n2 to n4 are the same as defined in the above chemical formula 1. Claim 11 In claim 1, the condensed polycyclic compound represented by Chemical Formula 1 is a light-emitting element represented by the following Chemical Formula 1-6: [Chemical Formula 1-6] In the above chemical formulas 1-6, X1 and X2 are each independently NR 13 , or O and, R 5-3 is a hydrogen atom, a deuterium atom, a substituted or unsubstituted arylamine group, a substituted or unsubstituted t-butyl group, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted biphenyl group, a substituent represented by Formula 2, or a substituent represented by Formula 3, and R 11 to R 13 Each is independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cyclic aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted cyclic heteroaryl group having 2 to 30 carbon atoms, a substituent represented by Formula 2, or a substituent represented by Formula 3, and n11 is an integer from 0 to 4, n12 is an integer from 0 to 3, g5 is an integer from 0 to 2, and R1 to R4, and n1 to n4 are the same as defined in Formula 1. Claim 12 In claim 11, the condensed polycyclic compound represented by the above chemical formula 1-6 is a light-emitting element represented by the following chemical formula 1-7-1 or chemical formula 1-7-2: [Chemical formula 1-7-1] [Chemical Formula 1-7-2] In the above chemical formulas 1-7-1 and 1-7-2, R 13-1 and R 13-2 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cyclic aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted cyclic heteroaryl group having 2 to 30 carbon atoms, or a substituent represented by Formula 2 above, and n13 and n14 are each independently integers from 0 to 5, and R1 to R4, R 5-3 , R 11 and R 12 , n1 to n4, g5, n11, and n12 are the same as defined in Chemical Formula 1 and Chemical Formula 1-6 above. Claim 13 In claim 1, the condensed polycyclic compound represented by the above chemical formula 1 is a light-emitting element represented by one of the compounds of the following compound group 1: [Compound group 1] . Claim 14 Condensed polycyclic compound represented by the following chemical formula 1: [Chemical Formula 1] In the above Formula 1, C1 to C5 are each independently a six-membered aromatic hydrocarbon ring, and R1 to R5 are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted arylboro group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted t-butyl group, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted biphenyl group, or form a ring by combining with an adjacent group, or are substituents represented by Formula 2 below, or are substituents represented by Formula 3 below, and all of R1 to R3 are represented by Formula 2 below, or at least one of R1 to R5 is represented by Formula 3 below, and n1 and n5 are each independently integers from 1 to 4, n2 and n4 are each independently integers from 1 to 5, and n3 is an integer from 1 to 3: [Formula 2] In the above Chemical Formula 2, A1 and A2 are each independently a substituted or unsubstituted methyl group, or a substituted or unsubstituted isopropyl group, and R a1 to R a3 Each is independently a hydrogen atom, a deuterium atom, or a substituted or unsubstituted isopropyl group: [Chemical Formula 3] In the above chemical formula 3, a is 0 or 1, and when a is 1, Y is a direct linkage, Z1 and Z2 are each independently represented by the above chemical formula 2, R6 and R7 are each independently hydrogen atoms or deuterium atoms, and n6 and n7 are each independently integers from 0 to 4. Claim 15 In claim 14, the condensed polycyclic compound represented by the above chemical formula 1 is a condensed polycyclic compound represented by the following chemical formula 1-1: [Chemical Formula 1-1] In the above chemical formula 1-1, R 1-1 to R 3-1 Each is independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted arylboro group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted t-butyl group, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted biphenyl group, or forms a ring by combining with an adjacent group, and R 1-1a to R 3-1a Each is independently represented by the above chemical formula 2, m1 is an integer from 0 to 3, m2 is an integer from 0 to 4, m3 is an integer from 0 to 2, and R4, R5, n4, and n5 are the same as defined in the above chemical formula 1. Claim 16 In claim 15, the condensed polycyclic compound represented by the above chemical formula 1 is a condensed polycyclic compound represented by the following chemical formula 1-3-1 or chemical formula 1-3-2: [Chemical formula 1-3-1] [Chemical Formula 1-3-2] In the above chemical formulas 1-3-1 and 1-3-2, R 4-1 and R 5-1 Each is independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted arylboro group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted t-butyl group, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted biphenyl group, or forms a ring by combining with an adjacent group, and R 5-1a is represented by the above chemical formula 3, and R 21 and R 22 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cyclic aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted cyclic heteroaryl group having 2 to 30 carbon atoms, m4 is an integer from 0 to 4, m5 is an integer from 0 to 3, n21 and n22 are each independently integers from 0 to 5, and R 1-1 to R 3-1 , R 1-1a to R 3-1a , m1 to m3 are the same as defined in Chemical Formula 1 and Chemical Formula 1-1 above. Claim 17 In claim 14, the condensed polycyclic compound represented by the above chemical formula 1 is a condensed polycyclic compound represented by the following chemical formula 1-4-1 or chemical formula 1-4-2: [Chemical formula 1-4-1] [Chemical Formula 1-4-2] In the above chemical formulas 1-4-1 and 1-4-2, R 3-2 and R 5-2 Each is independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted arylboro group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted t-butyl group, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted biphenyl group, or forms a ring by combining with an adjacent group, and R 3-1b and R 5-1b Each is independently represented by the above chemical formula 3, b3 is an integer from 0 to 2, b5 is an integer from 0 to 3, and R1 to R5 and n1 to n5 are the same as defined in the above chemical formula 1. Claim 18 In claim 14, the condensed polycyclic compound represented by the above chemical formula 1 is a condensed polycyclic compound represented by the following chemical formula 1-5-1 or chemical formula 1-5-2: [Chemical formula 1-5-1] [Chemical Formula 1-5-2] In the above chemical formulas 1-5-1 and 1-5-2, R 1-2 , R 3-2 , and R 5-2 Each is independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted arylboro group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted t-butyl group, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted biphenyl group, or forms a ring by combining with an adjacent group, and R 1-1b , R 3-1b and R 5-1b Each is independently represented by the above chemical formula 3, b1 and b5 are each independently integers from 0 to 3, b3 is an integer from 0 to 2, and R2 to R4 and n2 to n4 are the same as defined in the above chemical formula 1. Claim 19 In claim 14, the condensed polycyclic compound represented by the above chemical formula 1 is a condensed polycyclic compound represented by the following chemical formula 1-6: [Chemical formula 1-6] In the above chemical formulas 1-6, X1 and X2 are each independently NR 13 , or O and, R 5-3 is a hydrogen atom, a deuterium atom, a substituted or unsubstituted arylamine group, a substituted or unsubstituted t-butyl group, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted biphenyl group, a substituent represented by Formula 2, or a substituent represented by Formula 3, and R 11 to R 13 Each is independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cyclic aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted cyclic heteroaryl group having 2 to 30 carbon atoms, a substituent represented by Formula 2, or a substituent represented by Formula 3, and n11 is an integer from 0 to 4, n12 is an integer from 0 to 3, g5 is an integer from 0 to 2, and R1 to R4, and n1 to n4 are the same as defined in Formula 1. Claim 20 In claim 1, the condensed polycyclic compound represented by the above chemical formula 1 is a condensed polycyclic compound represented by one of the compounds of the following compound group 1: [Compound group 1] .

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