Light-emitting element, polycyclic compound for light-emitting element, and display device including the light-emitting element

Abstract

To provide a light-emitting element with improved luminous efficiency and lifetime.SOLUTION: A light-emitting element can include a first electrode, a second electrode disposed on the first electrode, and a light-emitting layer disposed between the first electrode and the second electrode. The light-emitting layer contains a first compound represented by Chemical Formula 1 below and can exhibit high efficiency and long-lifespan properties. [Chemical Formula 1]SELECTED DRAWING: Figure 3

Description

[Technical field]

[0001] The present invention relates to a light-emitting element, a polycyclic compound used therein, and a display device including the light-emitting element. [Background technology]

[0002] Recently, organic electroluminescence display devices have been actively developed as image display devices. Organic electroluminescence display devices are display devices including so-called self-emitting light-emitting elements that realize display by recombining holes and electrons injected from a first electrode and a second electrode in a light-emitting layer to cause a light-emitting material in the light-emitting layer to emit light.

[0003] In applying light emitting devices to display devices, there is a demand for improved light efficiency and life span, and there is a continuous demand for development of light emitting device materials that can stably realize these demands.

[0004] In particular, in order to realize highly efficient light-emitting devices, technologies related to phosphorescence emission using triplet state energy and delayed fluorescence emission using the phenomenon in which singlet excitons are generated by the collision of triplet excitons (TTA) have been developed recently, and development of thermally activated delayed fluorescence (TADF) materials using the delayed fluorescence phenomenon is also underway. Summary of the Invention [Problem to be solved by the invention]

[0005] An object of the present invention is to provide a light emitting device having improved luminous efficiency and life span.

[0006] Another object of the present invention is to provide a polycyclic compound having improved quantum efficiency and material stability.

[0007] It is yet another object of the present invention to provide a display device having excellent display quality, including a light emitting device with improved luminous efficiency and life span. [Means for solving the problem]

[0008] One embodiment provides a polycyclic compound represented by the following formula 1:

[0009] [Chemical formula 1] JPEG2025063842000002.jpg48170

[0010] In the above formula 1, R 1 ~R 11 At least one of R is a first substituent which is a cyano group or a substituted or unsubstituted triazine group, and R excluding the first substituent 1 ~R 11 two or more selected from among these are second substituents which are substituted or unsubstituted carbazole groups each bonded to any one ring selected from Ar1 to Ar3, and the remaining groups are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group having from 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having from 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having from 2 to 30 ring carbon atoms.

[0011] The formula 1 may be represented by any one of the following formulas 1-1 to 1-3.

[0012] [Chemical formula 1-1] JPEG2025063842000003.jpg43170 [Chemical formula 1-2] JPEG2025063842000004.jpg47170 [Chemical formula 1-3] JPEG2025063842000005.jpg45170

[0013] In the above Chemical Formulae 1-1 to 1-3, Sb1 is a cyano group or is represented by the following Chemical Formula 2, Sb2 is represented by the following Chemical Formula 3, and Ra to Rc are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms. n1 is 1, n2 is an integer of 1 to 3, n3 is an integer of 1 to 4, m1 is 2 or 3, m2 is an integer of 2 to 4, p1 is 0 or 1, p2 is an integer of 0 to 2, q is an integer of 0 to 2, r is an integer of 0 to 3, R 5 ~R 11 is as defined in Chemical Formula 1 above.

[0014] [Chemical formula 2] JPEG2025063842000006.jpg25170[Chemical formula 3] JPEG2025063842000007.jpg31170

[0015] In Chemical Formula 2 and Chemical Formula 3, W 1 , W 2 , and R 21 ~R 28 each independently represents a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group having from 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having from 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having from 2 to 30 ring carbon atoms, JPEG2025063842000008.jpg11170 is the position where Ar1 to Ar3 are bonded to the rings.

[0016] The formula 1-1 may be represented by the following formula 1-1a.

[0017] [Chemical formula 1-1a] JPEG2025063842000009.jpg50170

[0018] In the formula 1-1a, Sb1 and Sb2 are as defined in the formula 1-1; R 5 ~R 11 is as defined in Chemical Formula 1 above.

[0019] The formula 1-2 may be represented by the following formula 1-2a.

[0020] [Formula 1-2a] JPEG2025063842000010.jpg55170

[0021] In the formula 1-2a, Sb1, Sb2, and Rb are as defined in the formula 1-2; 8 ~R 11 is as defined in Chemical Formula 1 above.

[0022] R of Formula 1 1 ~R 11 At least one of the atoms is a deuterium atom or R 1 ~R 11 At least one hydrogen atom in may be replaced with a deuterium atom.

[0023] The compound represented by Formula 1 may be a blue light-emitting dopant.

[0024] The compound represented by Formula 1 may be a thermally activated delayed fluorescent material.

[0025] Another embodiment provides a light-emitting element including a first electrode, a second electrode disposed on the first electrode, and a light-emitting layer disposed between the first electrode and the second electrode, the light-emitting layer including the polycyclic compound of the above-described embodiment as a first compound.

[0026] The light emitting layer may further include at least one of a second compound represented by the following formula HT-1 and a third compound represented by the following formula ET-1.

[0027] [Chemical formula HT-1] JPEG2025063842000011.jpg38170

[0028] In the above chemical formula HT-1, A 1 or A 8 are each independently N or CR 51 And L 1 is a direct bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms; Y a is direct bond, CR 52 R 53 , or SiR 54 R 55 and Ar 1 R is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms. 51 ~R 55 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted thio group, a substituted or unsubstituted oxy group, a substituted or unsubstituted amine group, a substituted or unsubstituted boron group, a substituted or unsubstituted alkyl group having from 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having from 2 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having from 6 to 60 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having from 2 to 60 ring carbon atoms, or are bonded to adjacent groups to form a ring:

[0029] [Chemical formula ET-1] JPEG2025063842000012.jpg43170

[0030] In the above formula ET-1, X 1 ~X 3 At least one of them is N and the rest is CR 56 and R 56is a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having from 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having from 6 to 60 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having from 2 to 60 ring carbon atoms, and b1 to b3 are each independently an integer of from 0 to 10. 2 ~Ar 4 each independently represents a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having from 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having from 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having from 2 to 30 ring carbon atoms; 2 ~L 4 each independently represents a direct bond, a substituted or unsubstituted arylene group having from 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having from 2 to 30 ring carbon atoms. The light emitting layer may further include a fourth compound represented by the following formula D-1:

[0031] [Chemical formula D-1] JPEG2025063842000013.jpg64170

[0032] In the above chemical formula D-1, Q 1 ~Q 4 are each independently C or N, C1 to C4 are each independently a substituted or unsubstituted hydrocarbon ring having 5 to 30 ring carbon atoms, or a substituted or unsubstituted heterocycle having 2 to 30 ring carbon atoms; L 11 ~L 13 are each independently a direct bond, JPEG2025063842000014.jpg19170 is a substituted or unsubstituted divalent alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms. b11 to b13 are each independently 0 or 1, and R 61 ~R 66are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted thio group, a substituted or unsubstituted oxy group, a substituted or unsubstituted amine group, a substituted or unsubstituted boron group, a substituted or unsubstituted alkyl group having from 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having from 2 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having from 6 to 60 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having from 2 to 60 ring carbon atoms, and d1 to d4 are each independently an integer of from 0 to 4.

[0033] The light-emitting layer can include the first compound, the second compound, the third compound, and the fourth compound.

[0034] The light-emitting layer may emit delayed fluorescence.

[0035] The light-emitting layer may emit blue light.

[0036] Another embodiment provides a display device including a base layer, a circuit layer disposed on the base layer, and a display element layer disposed on the circuit layer and including a light-emitting element, the light-emitting element including a first electrode, a second electrode disposed on the first electrode, and a light-emitting layer disposed between the first electrode and the second electrode and including the polycyclic compound of the embodiment described above.

[0037] The light emitting element may emit blue light.

[0038] The display element may further include a light control layer comprising quantum dots. Effect of the Invention

[0039] The light emitting device of the embodiment can exhibit high efficiency and long life characteristics by including the polycyclic compound of the embodiment in the light emitting layer.

[0040] One embodiment of the polycyclic compound can contribute to improving the light efficiency and extending the life of a light-emitting device.

[0041] The display device of one embodiment may exhibit excellent display quality. [Brief description of the drawings]

[0042] [Figure 1] FIG. 1 is a plan view showing a display device according to an embodiment. [Diagram 2] 2 is a cross-sectional view showing a portion corresponding to line II' in FIG. [Diagram 3] 1 is a cross-sectional view illustrating a light-emitting device according to an embodiment of the present invention. [Figure 4] 1 is a cross-sectional view illustrating a light-emitting device according to an embodiment of the present invention. [Diagram 5] 1 is a cross-sectional view illustrating a light-emitting device according to an embodiment of the present invention. [Figure 6] 1 is a cross-sectional view illustrating a light-emitting device according to an embodiment of the present invention. [Figure 7] 1 is a cross-sectional view illustrating a light-emitting device according to an embodiment of the present invention. [Figure 8] 1 is a cross-sectional view showing a display device according to an embodiment. [Figure 9] 1 is a cross-sectional view showing a display device according to an embodiment. [Figure 10] 1 is a cross-sectional view showing a display device according to an embodiment. [Figure 11] 1 is a cross-sectional view showing a display device according to an embodiment. [Figure 12] 1 is a diagram showing the interior of a vehicle in which a display device according to an embodiment is disposed; DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0043] Since the present invention can be modified in various ways and can have various forms, specific embodiments are shown in the drawings and described in detail in the text, but it is not intended to limit the invention to the particular disclosed forms, but it should be understood that the present invention includes all modifications, equivalents, and alternatives falling within the spirit and technical scope of the present invention.

[0044] Throughout the drawings, like reference numerals are used for like elements. In the accompanying drawings, the dimensions of structures are exaggerated for clarity of the present invention. Terms such as first and second are used to describe various elements, but the elements are not limited to the terms. The terms are used only for the purpose of distinguishing one element from another element. For example, the first element may be named the second element, and similarly the second element may be named the first element, without departing from the scope of the present invention. A singular surface includes a plural expression unless the context clearly indicates otherwise.

[0045] In this application, the terms "comprise" or "have" and the like are intended to specify the presence of any feature, numeral, step, operation, component, part, or combination thereof described hereinabove in the specification, but are to be understood as not precluding the presence or additional possibility of one or more other features, numerals, steps, operations, components, parts, or combinations thereof.

[0046] In this application, when a layer, film, region, plate, or other part is described as being "on" or "above" another part, this includes not only the case where it is "directly above" the other part, but also the case where there is another part in between. Conversely, when a layer, film, region, plate, or other part is described as being "below" or "below" another part, this includes not only the case where it is "directly below" the other part, but also the case where there is another part in between. Also, in this application, being "located on" can include not only the case where it is located at the top, but also the case where it is located at the bottom.

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

[0048] In this specification, "adjacent groups bond together to form a ring" may mean adjacent groups bond together to form a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted hetero ring. 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 a single ring or a polycyclic ring. In addition, the ring formed by bonding together may be connected to another ring to form a spiro structure.

[0049] In this specification, the term "adjacent group" may refer to a substituent substituted on an atom directly connected to the atom on which the corresponding substituent is substituted, another substituent substituted on an atom on which the corresponding substituent is substituted, or a substituent that is sterically most adjacent to the corresponding substituent. For example, two methyl groups in 1,2-dimethylbenzene may be interpreted as "adjacent groups" to each other, and two ethyl groups in 1,1-diethylcyclopentane may be interpreted as "adjacent groups" to each other. Also, two methyl groups in 4,5-dimethylphenanthrene may be interpreted as "adjacent groups" to each other.

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

[0051] In this specification, an alkyl group may be linear or branched. The number of carbon atoms in an alkyl group is 1 to 60, 1 to 30, 1 to 20, 1 to 10, or 1 to 6. Examples of alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, s-butyl, t-butyl, i-butyl, 2-ethylbutyl, 3,3-dimethylbutyl, n-pentyl, i-pentyl, neopentyl, t-pentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl, n-hexyl, and 1-methylhexyl. , 2-ethylhexyl group, 2-butylhexyl group, n-heptyl group, 1-methylheptyl group, 2,2-dimethylheptyl group, 2-ethylheptyl group, 2-butylheptyl group, n-octyl group, t-octyl group, 2-ethyloctyl group, 2-butyloctyl group, 2-hexyloctyl group, 3,7-dimethyloctyl group, n-nonyl group, n-decyl group, adamantyl group, 2-ethyldecyl group, 2-butyldecyl group, 2-heptyl group xyldecyl group, 2-octyldecyl group, n-undecyl group, n-dodecyl group, 2-ethyldodecyl group, 2-butyldodecyl group, 2-hexyldodecyl group, 2-octyldecyl group, n-tridecyl group, n-tetradecyl group, n-pentadecyl group, n-hexadecyl group, 2-ethylhexadecyl group, 2-butylhexadecyl group, 2-hexylhexadecyl group, 2-octylhexadecyl group, n-heptadecyl group, n- Examples of such alkyl groups include, but are not limited to, octadecyl, n-nonadecyl, n-icosyl, 2-ethylicosyl, 2-butylicosyl, 2-hexylicosyl, 2-octylicosyl, n-henicosyl, n-docosyl, n-tricosyl, n-tetracosyl, n-pentacosyl, n-hexacosyl, n-heptacosyl, n-octacosyl, n-nonacosyl, and n-triacontyl.

[0052] In this specification, cycloalkyl group may mean a cyclic alkyl group. The number of carbon atoms in the cycloalkyl group is 3 to 60, 3 to 30, 3 to 20, or 3 to 10. Examples of cycloalkyl groups include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4-t-butylcyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, norbornyl, 1-adamantyl, 2-adamantyl, isonorbornyl, and bicycloheptyl.

[0053] As used herein, an alkenyl group refers to a hydrocarbon group containing one or more carbon double bonds at the middle or end of an alkyl group having two or more carbon atoms. The alkenyl group may be linear or branched. The number of carbon atoms is not particularly limited, but may be 2 to 60, 2 to 30, 2 to 20, or 2 to 10. Examples of alkenyl groups include, but are not limited to, vinyl, 1-butenyl, 1-pentenyl, 1,3-butadienylaryl, styrenyl, and styrylvinyl groups.

[0054] In this specification, an alkynyl group refers to a hydrocarbon group containing one or more carbon triple bonds at the middle or end of an alkyl group having two or more carbon atoms. The alkynyl group may be linear or branched. The number of carbon atoms is not particularly limited, but may be 2 to 30, 2 to 20, or 2 to 10. Specific examples of the alkynyl group include, but are not limited to, an ethynyl group, a propynyl group, and the like.

[0055] In the present specification, the term "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 ring carbon atoms.

[0056] In this specification, aryl group means any functional group or substituent derived from an aromatic hydrocarbon ring. The aryl group is a monocyclic aryl group or a polycyclic aryl group. The number of ring carbon atoms of the aryl group can be 6 to 60, 6 to 30, 6 to 20, or 6 to 15. Examples of aryl groups include, but are not limited to, phenyl, naphthyl, fluorenyl, anthracenyl, phenanthryl, biphenyl, terphenyl, quaterphenyl, quinquephenyl, sexiphenyl, triphenylenyl, pyrenyl, benzofluoranthenyl, and chrysenyl.

[0057] In this specification, the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure. Examples of the fluorenyl group that may be substituted are as follows. However, the examples are not limited thereto. JPEG2025063842000015.jpg24170

[0058] In this specification, heterocyclic group refers to any functional group or substituent derived from a ring containing one or more of B, O, N, P, S, Si, and Se as heteroatoms. Heterocyclic groups include aliphatic heterocyclic groups and aromatic heterocyclic groups. Aromatic heterocyclic groups can be heteroaryl groups. Aliphatic heterocycles and aromatic heterocycles can be monocyclic and polycyclic.

[0059] In this specification, the heterocyclic group may contain one or more of B, O, N, P, S, Si, and Se as a heteroatom. If the heterocyclic group contains two or more heteroatoms, the two or more heteroatoms may be the same or different. The heterocyclic group may be a monocyclic heterocyclic group or a polycyclic heterocyclic group, and is a concept including a heteroaryl group. The number of ring carbon atoms of the heterocyclic group may be 2 to 60, 2 to 30, 2 to 20, or 2 to 10.

[0060] In this specification, the aliphatic heterocyclic group may contain one or more of B, O, N, P, S, Si, and Se as a heteroatom. The number of ring carbon atoms of the aliphatic heterocyclic group may be 2 to 30, 2 to 20, or 2 to 10. Examples of the aliphatic heterocyclic group include, but are not limited to, an oxirane group, a thiirane group, a pyrrolidine group, a piperidine group, a tetrahydrofuran group, a tetrahydrothiophene group, a thiane group, a tetrahydropyran group, and a 1,4-dioxane group.

[0061] In this specification, the heteroaryl group may contain one or more of B, O, N, P, S, Si, and Se as a heteroatom. When the heteroaryl group contains two or more heteroatoms, the two or more heteroatoms may be the same or different. The heteroaryl group may be a monocyclic heterocyclic group or a polycyclic heterocyclic group. The number of ring carbon atoms of the heteroaryl group may be 2 to 60, 2 to 30, 2 to 20, or 2 to 10. Examples of the heteroaryl group include a thiophene group, a furan group, a pyrrole group, an imidazole group, a pyridine group, a bipyridine group, a pyrimidine group, a triazine group, a triazole group, an acridyl group, a pyridazine group, a pyridinyl group, a quinoline group, a quinazoline group, a quinoxaline group, a phenoxazine group, a phthalazine group, a pyridopyrimidine group, a pyridopyrazine group, a pyrazinopyrazine group, an isoquinoline group, an indole group, a carbazole group, an N-arylcarbazole group, an N-heteroaryl Examples of such alkyl groups include, but are not limited to, an alkyl carbazole group, an N-alkyl carbazole group, a benzoxazole group, a benzimidazole group, a benzothiazole group, a benzocarbazole group, a benzothiophene group, a dibenzothiophene group, a thienothiophene group, a benzofuran group, a phenanthroline group, a thiazole group, an isoxazole group, an oxazole group, an oxadiazole group, a thiadiazole group, a phenothiazine group, a dibenzosilole group, and a dibenzofuran group.

[0062] In this specification, the above description of the aryl group may be applied to an arylene group, except that the arylene group is a divalent group. The above description of the heteroaryl group may be applied to a heteroarylene group, except that the heteroarylene group is a divalent group.

[0063] In this specification, the silyl group includes an alkylsilyl group and an arylsilyl group. Examples of the silyl group include, but are not limited to, a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, a phenylsilyl group, and the like.

[0064] In this specification, the number of carbon atoms of the carbonyl group is not particularly limited, but may be 1 to 40, 1 to 30, or 1 to 20. For example, it may have the following structure, but is not limited thereto. JPEG2025063842000016.jpg30170

[0065] In this specification, the number of carbon atoms of the sulfinyl group and the sulfonyl group is not particularly limited, but may be 1 or more and 30 or less. The sulfinyl group may include an alkylsulfinyl group and an arylsulfinyl group. The sulfonyl group may include an alkylsulfonyl group and an arylsulfonyl group.

[0066] In this specification, the thio group may include an alkylthio group and an arylthio group. The thio group may mean an alkyl group or an aryl group as defined above to which a sulfur atom is bonded. Examples of the thio group include, but are not limited to, a methylthio group, an ethylthio group, a propylthio group, a pentylthio group, a hexylthio group, an octylthio group, a dodecylthio group, a cyclopentylthio group, a cyclohexylthio group, a phenylthio group, and a naphthylthio group.

[0067] In this specification, an oxy group may mean an alkyl group or an aryl group defined above to which an oxygen atom is bonded. The oxy group may include an alkoxyoxy group and an aryloxy group. The alkoxy group may be linear, branched, or cyclic. The number of carbon atoms in the alkoxy group is not particularly limited, but may be, for example, 1 to 20 or 1 to 10. Examples of oxy groups include, but are not limited to, methoxy, ethoxy, n-propoxy, isopropoxy, butoxy, pentyloxy, hexyloxy, octyloxy, nonyloxy, decyloxy, and benzyloxy.

[0068] In this specification, the boron group may mean a boron atom bonded to the alkyl group or aryl group defined above. The boron group includes an alkyl boron group and an aryl boron group. Examples of the boron group include, but are not limited to, a dimethyl boron group, a diethyl boron group, a t-butyl methyl boron group, a diphenyl boron group, a phenyl boron group, and the like.

[0069] In this specification, the number of carbon atoms of the amine group is not particularly limited, but may be 1 to 30. The amine group may include an alkylamine group and an arylamine group. Examples of the amine group include, but are not limited to, a methylamine group, a dimethylamine group, a phenylamine group, a diphenylamine group, a naphthylamine group, and a 9-methyl-anthracenylamine group.

[0070] In this specification, among the alkylthio group, alkylsulfoxy group, alkylaryl group, alkylamino group, alkylboron group, alkylsilyl group and alkylamine group, the alkyl group is as exemplified above for the alkyl group.

[0071] In this specification, among the aryloxy group, arylthio group, arylsulfoxy group, arylamino group, arylboron group, arylsilyl group and arylamine group, the aryl group is as exemplified above for the aryl group.

[0072] As used herein, a direct bond can mean a single bond.

[0073] On the other hand, in this specification, JPEG2025063842000017.jpg15170 means the position to be concatenated.

[0074] An embodiment of the present invention will now be described with reference to the drawings.

[0075] Fig. 1 is a plan view showing an embodiment of a display device DD, Fig. 2 is a cross-sectional view of the display device DD of the embodiment, Fig. 2 is a cross-sectional view showing a portion corresponding to the line II' in Fig. 1.

[0076] The display device DD may include a display panel DP and an optical layer PP disposed on the display panel DP. The display panel PP includes light-emitting elements ED-1, ED-2, and ED-3. The display device DD may include a plurality of light-emitting elements ED-1, ED-2, and ED-3. The optical layer PP is disposed on the display panel DP and may control reflected light in the display panel DP due to external light. The optical layer PP may include, for example, a polarizing layer or a color filter layer. Meanwhile, unlike the illustrated embodiment, the optical layer PP may be omitted from the display device DD of one embodiment.

[0077] 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, or the like. However, the embodiment is not limited thereto, and the base substrate BL may be an inorganic layer, an organic layer, or a composite material layer. Also, unlike the illustrated embodiment, the base substrate BL may be omitted.

[0078] The display device DD according to an embodiment may further include a charging layer (not shown). The filling layer (not shown) may be disposed between the display element layer DP-ED and the 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.

[0079] 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 film PDL, light emitting elements ED-1, ED-2, and ED-3 arranged between the pixel defining film PDL, and a sealing layer TFE arranged on the light emitting elements ED-1, ED-2, and ED-3.

[0080] The base layer BS may be a member that provides a base surface on which the display element layers EP-ED are disposed. The base layer BS may be a glass substrate, a metal substrate, a plastic substrate, etc. However, the embodiment is not limited thereto, and the base layer BS may be an inorganic layer, an organic layer, or a composite material layer.

[0081] 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-ED may include a switching transistor and a driving transistor for driving the organic electroluminescent elements ED-1, ED-2, and ED-3.

[0082] Each of the light-emitting elements ED-1, ED-2, and ED-3 may have a structure of an embodiment of the light-emitting element ED shown in Figures 3 to 7 described below. Each of the light-emitting elements ED-1, ED-2, and ED-3 may include a first electrode EL1, a hole transport region HTR, light-emitting layers EML-R, EML-G, and EML-B, an electron transport region ETR, and a second electrode EL2.

[0083] 2 shows an embodiment in which the light emitting layers EML-R, EML-G, and EML-B of the light emitting elements ED-1, ED-2, and ED-3 are disposed within the opening OH defined in the pixel defining layer PDL, and the hole transport region HTR, the electron transport region ETR, and the second electrode EL2 are provided as a common layer for the entire light emitting elements ED-1, ED-2, and ED-3. However, the embodiment is not limited thereto, and unlike the illustration of FIG. 2, in one embodiment, the hole transport region HTR and the electron transport region ETR may be provided by patterning within the opening OH defined in the pixel defining layer PDL. For example, in one embodiment, the hole transport region HTR, the light emitting layers EML-R, EML-G, EML-B, and the electron transport region ETR of the light emitting elements ED-1, ED-2, and ED-3 may be provided by patterning using an inkjet printing method.

[0084] The encapsulating layer TFE may cover the organic electroluminescent elements ED-1, ED-2, and ED-3. The encapsulating layer TFE may seal the display element layer DP-ED. The encapsulating layer TFE may be a thin encapsulating layer. The encapsulating layer TFE may be a single layer or a plurality of layers stacked. The encapsulating layer TFE includes at least one insulating layer. The encapsulating layer TFE according to an embodiment may include at least one inorganic film (hereinafter, encapsulating inorganic film). Also, the encapsulating layer TFE according to an embodiment may include at least one organic film (hereinafter, encapsulating organic film) and at least one encapsulating inorganic film.

[0085] The sealing inorganic film protects the display element layer DP-ED from moisture / oxygen, and the sealing organic film protects the display element layer DP-ED from foreign matter such as dust particles. The sealing inorganic film may include, but is not limited to, silicon nitride, silicon oxynitride, silicon oxide, titanium oxide, aluminum oxide, etc. The sealing organic film may include, but is not limited to, an acrylic compound, an epoxy compound, etc. The sealing organic film may include, but is not limited to, a photopolymerizable organic material.

[0086] The sealing layer TFE may be disposed on the second electrode EL2 and may be disposed to fill the opening OH.

[0087] 1 and 2, the display device DD may include a non-light-emitting area NPXA and light-emitting areas PXA-R, PXA-G, and PXA-B. Each of the light-emitting areas PXA-R, PXA-G, and PXA-B may be an area where light generated from each of the light-emitting elements ED-1, ED-2, and ED-3 is emitted. The light-emitting areas PXA-R, PXA-G, and PXA-B may be spaced apart from each other on a plane.

[0088] Each of the light-emitting regions PXA-R, PXA-G, and PXA-B may be a region divided by a pixel defining layer PPL. The non-light-emitting region NPXA may be a region between adjacent light-emitting regions PXA-R, PXA-G, and PXA-B, and may correspond to a pixel defining layer PDL. Meanwhile, in this specification, each of the light-emitting regions PXA-R, PXA-G, and PXA-B may correspond to a pixel. The pixel defining layer PDL may divide the light-emitting elements ED-1, ED-2, and ED-3. The light-emitting layers EML-R, EML-G, and EML-B of the light-emitting elements ED-1, ED-2, and ED-3 may be disposed in the openings OH defined in the pixel defining layer PDL and divided.

[0089] The light emitting regions PXA-R, PXA-G, and PXA-B may be divided into a plurality of groups according to the colors of the lights generated from the light emitting elements ED-1, ED-2, and ED-3. In the display device DD according to an embodiment shown in Figures 1 and 2, three light emitting regions PXA-R, PXA-G, and PXA-B that emit red light, green light, and blue light are illustrated as an example. For example, the display device DD according to an embodiment may include a red light emitting region PXA-R, a green light emitting region PXA-G, and a blue light emitting region PXA-B that are separated from each other.

[0090] In the display device DD according to an embodiment, the light emitting elements ED-1, ED-2, and ED-3 may emit light of different wavelength regions. For example, in an embodiment, the display device DD may include a light emitting element ED-1 that emits red light, a second light emitting element ED-3 that emits green light, and a third light emitting element ED-3 that emits blue light. 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.

[0091] However, the embodiment is not limited thereto, and the first to third light emitting elements ED-1, ED-2, and ED-3 may emit light in the same wavelength region, or at least one of them may emit light in a different wavelength region. In addition, the first to third light emitting elements ED-1, ED-2, and ED-3 may all emit blue light.

[0092] The light emitting regions PXA-R, PXA-G, and PXA-B in the display device DD according to an embodiment may be arranged in a striped pattern. 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 be aligned along the second directional axis DR2. Also, the red light emitting regions PXA-R, the green light emitting regions PXA-G, and the blue light emitting regions PXA-B may be alternately arranged in this order along the first directional axis DR1.

[0093] 1 and 2, the areas of the light-emitting regions PXA-R, PXA-G, and PXA-B are shown to be similar, but this is not limited to the embodiment, and the areas of the light-emitting regions PXA-R, PXA-G, and PXA-B may differ from each other depending on the wavelength range of the light emitted. Meanwhile, the areas of the light-emitting regions PXA-R, PXA-G, and PXA-B may refer to the areas when viewed from a plane defined by the first direction axis DR1 and the second direction axis DR2.

[0094] Meanwhile, the arrangement of the light emitting regions PXA-R, PXA-G, and PXA-B is not limited to that shown in FIG. 1, and the order in which the red light emitting region PXA-R, the green light emitting region PXA-G, and the blue light emitting region PXA-B are arranged may be provided in various combinations according to the display quality characteristics required by the display device DD. For example, the arrangement of the light emitting regions PXA-R, PXA-G, and PXA-B may be provided in a pentile (PENTILE) pattern. TM ) array or diamond (Diamond Pixel TM ) sequence.

[0095] In addition, the areas of the light emitting regions PXA-R, PXA-G, and PXA-B may be different 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.

[0096] 3 to 7 are cross-sectional views each showing a schematic configuration of a light emitting device according to an embodiment. The light emitting device ED according to an embodiment may include a first electrode EL1, a hole transport region HTR, an emission layer EML, an electron transport region ETR, and a second electrode EL2, which are sequentially stacked.

[0097] FIG. 4 is a cross-sectional view of a light-emitting element ED according to an embodiment in which the hole transport region HTR includes a hole injection layer HIL and a hole transport layer HTL, and the electron transport region ETR includes an electron injection layer EIL and an electron transport layer ETL, in comparison with FIG. 3. FIG. 5 is a cross-sectional view of a light-emitting element ED according to an embodiment in which the hole transport region HTR includes a hole injection layer HIL, a hole transport layer HTL, and an electron blocking layer EBL, and the electron transport region ETR includes an electron injection layer EIL, an electron transport layer ETL, and a hole blocking layer HBL, in comparison with FIG. 3. FIG. 6 is a cross-sectional view of a light-emitting element ED according to an embodiment in which the hole transport region HTR includes a hole injection layer HIL, a hole transport layer HTL, and an electron auxiliary layer EAL, and the electron transport region ETR includes an electron injection layer EIL, an electron transport layer ETL, and a hole blocking layer HBL, in comparison with FIG. 3. FIG. 7 is a cross-sectional view of a light-emitting element ED according to an embodiment in which a capping layer CPL is disposed on the second electrode EL2, in comparison with FIG. 4.

[0098] The first electrode EL1 has conductivity. The first electrode EL1 may be made of a metal material, a metal alloy, or a conductive compound. The first electrode EL1 may be an anode or a cathode. However, the embodiment is not limited thereto. The first electrode EL1 may be a pixel electrode. The first electrode EL1 may be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode. The first electrode EL1 may be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode. The first electrode EL1 may include 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, 22 or more kinds of compounds selected from these, a mixture of two or more kinds selected from these, or oxides thereof.

[0099] If the first electrode EL1 is a transmissive 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 semi-transmissive 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 (a laminated structure of LiF and Ca), LiF / Al (a laminated 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 multi-layer structure including a reflective film or semi-transmissive film made of the above material, and a transparent conductive film made of ITO, IZO, ZnO, ITZO, etc. For example, the first electrode EL1 may have a three-layer structure of ITO / Ag / ITO, but is not limited thereto. In addition, the embodiment is not limited thereto, and the first electrode EL1 may include the above-mentioned metal materials, a combination of two or more metal materials selected from the above-mentioned metal materials, or an oxide of the above-mentioned metal materials, etc. The thickness of the first electrode EL1 may be about 700 Å to about 10,000 Å. For example, the thickness of the first electrode EL1 may be about 1,000 Å to about 3,000 Å.

[0100] A hole transport region HTR may be provided on the first electrode EL1. The hole transport region HTR may include at least one of a hole injection layer HIL, a hole transport layer HTL, a light-emitting auxiliary layer EAL, 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. The light-emitting auxiliary layer EAL may be referred to as a buffer layer.

[0101] The hole transport region HTR may have a single layer of a single material, a single layer of multiple different materials, or a multi-layer structure having multiple layers of multiple different materials.

[0102] 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 may have a single layer structure made of a hole injection material and a hole transport material. Also, the hole transport region HTR may have a single layer structure made of a plurality of 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 / light emitting auxiliary layer EAL, a hole injection layer HIL / light emitting auxiliary layer EAL, a hole transport layer HTL / light emitting auxiliary layer EAL, a hole injection layer HIL / hole transport layer HTL / light emitting auxiliary layer EAL, or a hole injection layer HIL / hole transport layer HTL / electron blocking layer EBL, which are stacked in order from the first electrode EL1, but the embodiment is not limited thereto.

[0103] The hole transport region HTR may be formed using various methods such as vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) method, inkjet printing, laser printing, and laser induced thermal imaging (LITI).

[0104] The hole transport region HTR may include a compound represented by the following chemical formula H-1.

[0105] [Chemical formula H-1] JPEG2025063842000018.jpg31170

[0106] In the chemical formula H-1, L 1 and L 2 may each independently be a direct bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms. a and b may each independently be an integer of 0 to 10. On the other hand, when a or b is an integer of 2 or more, multiple L 1 and L 2 may each independently be a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms.

[0107] In the chemical formula H-1, Ar 1 ~Ar 2 may each independently be a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms. 3 may be a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms.

[0108] The compound represented by the formula H-1 may be a monoamine compound. Alternatively, the compound represented by the formula H-1 may be Ar 1 ~Ar 3 At least one of the compounds represented by the formula H-1 may be a diamine compound having an amine group as a substituent. 1 ~Ar 2 Carbazole-based compounds containing a substituted or unsubstituted carbazole group in at least one of the above, or Ar 1 ~Ar 2 The compound may be a fluorene-based compound containing a substituted or unsubstituted fluorene group in at least one of the above.

[0109] The compound represented by the chemical formula H-1 may be any one of the compounds in the following compound group H. However, the compounds listed in the following compound group H are merely illustrative, and the compound represented by the chemical formula H-1 is not limited to those in the following compound group H.

[0110] [Compound group H] JPEG2025063842000019.jpg206170JPEG2025063842000020.jpg41170

[0111] The hole transport region HTR is made of 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]triphenylamino), TDATA (4,4',4"-tris(N,N-diphenylamino)triphenylamine), 2-TNATA (4,4',4"-tris[N(2-naphthyl)-N-phenylamino]-triphenylamine), PEDOT / PSS (poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate), PANI / DBSA (polyaniline / dodecylbenzenesulfonic acid), PANI / CSA (polyaniline / camphorsulfonic acid), PANI / PSS ((polyaniline) / poly(4-styrenesulfonate)), NPB (N,N'-di(naphthalen-1-yl)-N,N'-diphenyl-benzidine), polyether ketone containing triphenylamine (TPAPEK), 4-isopropyl-4'-methyldiphenyliodonium tetrakis(pentafluorophenyl)borate, HATCN (dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile), and the like.

[0112] The hole transport region HTR may include, for example, carbazole derivatives such as N-phenylcarbazole and polyvinylcarbazole, fluorene derivatives, triphenylamine derivatives such as TPD (N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine), TCTA (4,4',4"-tris(N-carbazolyl)triphenylamine), NPB (N,N'-di(naphthalen-1-yl)-N,N'-diphenyl-benzidine), TAPC (4,4'-cyclohexylidenebis[N,N-bis(4-methylphenyl)benzeneamine]), HMTPD (4,4'-bis[N,N'-(3-tolyl)amino]-3,3'-dimethylbiphenyl), mCP (1,3-bis(N-carbazolyl)benzene), and the like.

[0113] The hole transport region HTR may also 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.

[0114] The hole transport region HTR may contain the above-mentioned compound for the hole transport region in at least one of the hole injection layer HIL, the hole transport layer HTL, the light-emitting auxiliary layer EAL, and the electron blocking layer EBL.

[0115] The thickness of the hole transport region HTR may be about 100 Å to about 10,000 Å, for example, about 100 Å to about 5,000 Å. When 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 1,000 Å. When the hole transport region HTR includes a hole transport layer HTL, the thickness of the hole transport layer HTL may be, for example, about 30 Å to about 1,000 Å. For example, when the hole transport region HTR includes a hole blocking layer EBL, the thickness of the hole blocking layer EBL may be, for example, about 10 Å to about 1,000 Å. If the thicknesses of the hole transport region HTR, the hole injection layer HIL, the hole transport layer HTL, and the electron blocking layer EBL satisfy the above-mentioned ranges, a satisfactory degree of hole transport characteristics can be obtained without a substantial increase in driving voltage.

[0116] The hole transport region HTR may further include a charge generating material to improve conductivity in addition to the above-mentioned materials. The charge generating material may be uniformly or non-uniformly distributed in the hole transport region HTR. The charge generating material may be, for example, a p-dopant. The p-dopant may include at least one of 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 include, but are not limited to, 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).

[0117] As described above, the hole transport region HTR may further include at least one of an emission assisting layer EAL and an electron blocking layer EBL in addition to the hole transport layer HTL and the hole injection layer HIL. The emission assisting layer EAL may compensate for the resonance distance according to the wavelength of light emitted from the emission layer EML and adjust the hole charge balance to increase light emission efficiency. The emission assisting layer EAL may also function to prevent the injection of electrons into the hole transport region HTR. The emission assisting layer EAL may include a material that may be included in the hole transport region HTR. The electron blocking layer EBL is a layer that functions to prevent the injection of electrons from the electron transport region ETR to the hole transport region HTR.

[0118] In the light-emitting device ED of an embodiment, the light-emitting layer EML may include a fused polycyclic compound according to an embodiment. In the light-emitting device ED of an embodiment, the light-emitting layer EML may include at least one compound selected from the first compound, the second compound, and the third compound, which are polycyclic compounds according to an embodiment. In the light-emitting device ED of an embodiment, the light-emitting layer EML may further include a fourth compound. The second compound may include a three-ring fused ring containing a nitrogen atom as a ring-forming atom. The third compound may include a hexagonal ring group containing at least one nitrogen atom as a ring-forming atom. The fourth compound may include an organometallic complex. The second to fourth compounds will be described in more detail later.

[0119] In this specification, the first compound may be referred to as a polycyclic compound of one embodiment. The polycyclic compound of one embodiment includes a fused ring of indolocarbazole as a central structure. For example, the polycyclic compound of one embodiment, which is the first compound, includes indolo(3,2,1-jk)carbazole as a core structure. The polycyclic compound of one embodiment includes at least one electron withdrawing group and a plurality of electron donating groups bonded to the indolocarbazole core structure. In addition, the plurality of electron donating groups may all be bonded to at least one aryl ring among the aryl rings constituting the indolocarbazole core.

[0120] In one embodiment, the electron withdrawing group can be a cyano group or a substituted or unsubstituted triazine group. The cyano group or the substituted or unsubstituted triazine group directly bonded to the indolocarbazole core can be referred to as a first substituent. Also, in one embodiment, the electron donating group can be a substituted or unsubstituted carbazole group. The multiple substituted or unsubstituted carbazole groups directly bonded to one benzene ring forming the indolocarbazole core can be referred to as second substituents.

[0121] The polycyclic compound of the embodiment includes an indolocarbazole core structure, and includes both an electron-withdrawing group and an electron-donating group directly bonded to the indolocarbazole core, and thus may exhibit thermally activated delayed fluorescence (TADF) emission characteristics. In addition, due to such a structure, the polycyclic compound of the embodiment may emit light in the blue wavelength region. Meanwhile, the polycyclic compound of the embodiment may exhibit excellent material stability, since a plurality of electron-donating groups are all bonded to one ring of the indolocarbazole. As a result, the light-emitting device of the embodiment including the polycyclic compound of the embodiment may exhibit high luminous efficiency and long life characteristics.

[0122] The light emitting device ED according to an embodiment may include the polycyclic compound according to an embodiment. The polycyclic compound according to an embodiment may be represented by the following Chemical Formula 1.

[0123] [Chemical formula 1] JPEG2025063842000021.jpg48170

[0124] In Chemical Formula 1, R 1 ~R 11 At least one of R is a first substituent which is a cyano group or a substituted or unsubstituted triazine group, and R excluding the first substituent 1 ~R 11 Two or more selected from among the above are second substituents which are substituted or unsubstituted carbazole groups each bonded to one ring selected from Ar1 to Ar3.

[0125] R 1 ~R 11Among these, the remainder excluding the first and second substituents are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group having from 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having from 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having from 2 to 30 ring carbon atoms.

[0126] In one embodiment, two or more of the substituted or unsubstituted carbazole groups may be bonded to any one of the rings selected from Ar1 to Ar3. For example, the number of second substituents that are substituted or unsubstituted carbazole groups bonded directly to any one of the rings selected from Ar1 to Ar3 may be three or more.

[0127] In one embodiment of the polycyclic compound represented by Formula 1, at least one of the hydrogen atoms may be replaced with a deuterium atom. 1 ~R 11 At least one of the remaining substituents other than the first and second substituents may be a deuterium atom, or at least one of the hydrogen atoms of the first and second substituents may be substituted with a deuterium atom.

[0128] The polycyclic compound of one embodiment represented by Chemical Formula 1 may be represented by any one of the following Chemical Formulas 1-1 to 1-3. In the following Chemical Formulas 1-1 to 1-3, Sb1 corresponds to the first substituent and Sb2 corresponds to the second substituent.

[0129] The following chemical formula 1-1 shows a case where the first and second substituents are both bonded to one aryl ring, and the following chemical formulas 1-2 and 1-3 show a case where the first and second substituents are bonded to different aryl rings, respectively.

[0130] [Chemical formula 1-1] JPEG2025063842000022.jpg42170[Chemical formula 1-2] JPEG2025063842000023.jpg46170[Chemical formula 1-3] JPEG2025063842000024.jpg42170

[0131] In Chemical Formulae 1-1 to 1-3, Sb1 may be a cyano group or a substituted or unsubstituted triazine group represented by the following Chemical Formula 2. In Chemical Formulae 1-1 to 1-3, Sb2 may be a substituted or unsubstituted carbazole group represented by the following Chemical Formula 3.

[0132] In Chemical Formulae 1-1 to 1-3, Ra to Rc may each independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group having from 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having from 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having from 2 to 30 ring carbon atoms.

[0133] In Chemical Formulae 1-1 to 1-3, R 5 ~R 11 The same explanation as in Chemical Formula 1 above may be applied to

[0134] In Chemical Formula 1-1, n1 can be 1, m1 can be 2 or 3, and p1 can be 0 or 1. For example, in one embodiment of the polycyclic compound represented by Chemical Formula 1-1, n1 can be 1, m1 can be 3, and p1 can be 0. Meanwhile, all of the multiple Sb2 can be the same or at least one can be different from the rest.

[0135] In Chemical Formula 1-2, n2 may be an integer of 1 or more and 3 or less, m2 may be an integer of 2 or more and 4 or less, p2 may be an integer of 0 or more and 2 or less, and q may be an integer of 0 or more and 2 or less. For example, in one embodiment of the polycyclic compound represented by Chemical Formula 1-2, n2 may be 1, m2 may be 4, p2 may be 0, and q may be 2. Meanwhile, multiple Sb2 may be all the same or at least one may be different from the rest. In addition, if p2 is 2, Ra may be the same or different from each other, and if q is 2, Rb may be the same or different from each other.

[0136] In Chemical Formula 1-3, n3 may be an integer of 1 or more and 4 or less, m2 may be an integer of 2 or more and 4 or less, p2 may be an integer of 0 or more and 2 or less, and r may be an integer of 0 or more and 3 or less. For example, in one embodiment of the polycyclic compound represented by Chemical Formula 1-3, n3 may be 1, m2 may be 4, p2 may be 0, and r may be 3. Meanwhile, the multiple Sb2 may all be the same or at least one may be different from the rest. In addition, if p2 is 2, Ra may be the same or different from each other, and if r is 2 or more, Rc may be the same or different from each other.

[0137] The triazine group which is the first substituent may be represented by the following Chemical Formula 2.

[0138] [Chemical formula 2] JPEG2025063842000025.jpg25170

[0139] In Chemical Formula 2, W 1 and W 2 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group having from 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having from 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having from 2 to 30 ring carbon atoms. 1 and W 2 For example, in one embodiment, W 1 and W 2 may be a substituted or unsubstituted phenyl group. However, the examples are not limited thereto. Meanwhile, in Chemical Formula 2, JPEG2025063842000026.jpg11170 The moiety corresponds to the moiety bonded to the rings Ar1 to Ar3 of the indolocarbazole core of Formula 1.

[0140] The carbazole group which is the second substituent may be represented by the following Chemical Formula 3.

[0141] [Chemical formula 3] JPEG2025063842000027.jpg32170

[0142] In Chemical Formula 3, R 21 ~R 28 may each independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group having from 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having from 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having from 2 to 30 ring carbon atoms. JPEG2025063842000028.jpg6170 The moiety corresponds to the moiety bonded to the rings Ar1 to Ar3 of the indolocarbazole core of Formula 1.

[0143] In one embodiment, formula 1-1 may be represented by the following formula 1-1a:

[0144] [Chemical formula 1-1a] JPEG2025063842000029.jpg42170

[0145] In the formula 1-1a, Sb1 is a cyano group or a substituted or unsubstituted triazine group, and Sb2 is a substituted or unsubstituted carbazole group. All three sb's may be the same, or one of them may be different from the remaining two. In the formula 1-1a, R 5 ~R 11 The same content as that described in Chemical Formula 1 above may be applied to

[0146] In one embodiment, Formula 1-2 may be represented by the following Formula 1-2a:

[0147] [Formula 1-2a] JPEG2025063842000030.jpg46170

[0148] In formula 1-2a, Sb1 is a cyano group or a substituted or unsubstituted triazine group, and Sb2 is a substituted or unsubstituted carbazole group. All four sb's may be the same or at least one may be different from the rest. In formula 1-2a, R 8 ~R 11 The same content as that described in Chemical Formula 1 above may be applied to

[0149] The polycyclic compound of an embodiment may be represented by any one of the compounds in the following first compound group. The light-emitting device ED according to an embodiment may include at least one of the compounds in the following first compound group. In the following first compound group, d (in italics) is a deuterium atom.

[0150] [First compound group] JPEG2025063842000031.jpg166170 JPEG2025063842000032.jpg157170 JPEG2025063842000033.jpg186170 JPEG2025063842000034.jpg194170 JPEG2025063842000035.jpg194170

[0151] The polycyclic compound of one embodiment includes an indolocarbazole core, a first substituent that is a cyano group or a triazine group directly bonded to the core, and a second substituent that is a carbazole group directly bonded to the core, and may be used as a delayed fluorescence material. For example, the polycyclic compound of one embodiment may be used as a thermally activated delayed fluorescence (TADF) material. The polycyclic compound of one embodiment may exhibit high fluorescence quantum yield.

[0152] In addition, the polycyclic compound of one embodiment includes a plurality of second substituents, and the carbazole groups, which are the plurality of second substituents, are bonded to one aryl ring of the fused rings constituting the core, and the carbazole groups are prevented from rotating with each other, thereby exhibiting excellent material stability. In addition, the polycyclic compound of one embodiment includes an indolocarbazole core, a cyano group or a triazine group directly bonded to the core, and a plurality of carbazole groups directly bonded from the core to one aryl ring, and can be used as a light-emitting material that emits light in the blue light wavelength region. The polycyclic compound of one embodiment can exhibit high luminous efficiency in the blue light wavelength region, and can emit light with a narrow half-width, thereby exhibiting luminous characteristics with excellent color purity.

[0153] The light emitting device according to the embodiment including the polycyclic compound according to the embodiment may exhibit high efficiency and long life characteristics. The light emitting device according to the embodiment including the polycyclic compound according to the embodiment having excellent luminous efficiency and improved material stability in the light emitting layer may exhibit high light efficiency and excellent life characteristics.

[0154] In the light emitting device according to an embodiment, the emission layer EML may be a delayed fluorescent emission layer including a host and a dopant. More specifically, the emission layer EML may emit thermally activated delayed fluorescence (TADF). The polycyclic compound according to an embodiment may be a thermally activated delayed fluorescent dopant.

[0155] The light-emitting layer EML may include the polycyclic compound of one embodiment as a dopant. The polycyclic compound of one embodiment may emit blue light. For example, the polycyclic compound of one embodiment may be a light-emitting material having a maximum emission wavelength in a wavelength range of 430 nm to 490 nm. In particular, the polycyclic compound of one embodiment may be a light-emitting material having a maximum emission wavelength in a wavelength range of 440 nm to 470 nm.

[0156] In one embodiment, the emitting layer EML includes the polycyclic compound of one embodiment, and may include at least one of the second to fourth compounds. In one embodiment, the emitting layer EML may include a second compound represented by the following chemical formula HT-1. For example, the second compound may be used as a hole-transporting host material of the emitting layer EML.

[0157] [Chemical formula HT-1] JPEG2025063842000036.jpg42170

[0158] In the chemical formula HT-1, A 1 or A 8 are each independently N or CR 51 For example, A 1 or A 8 All are CR 51 Or, A 1 or A 8 One of them is N and the rest is CR 51 may be also possible.

[0159] In the chemical formula HT-1, L 1 may be a direct bond, a substituted or unsubstituted arylene group having from 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having from 2 to 30 ring carbon atoms. For example, L 1 may be a direct bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted divalent biphenyl group, a substituted or unsubstituted divalent carbazole group, and the like, but examples are not limited thereto.

[0160] In the chemical formula HT-1, Y a is direct bond, CR 52 R 53 , or SiR 54 R 55 That is, the two benzene rings connected to the nitrogen atom of the formula HT-1 can be directly bonded, In the chemical formula HT-1, Y a is a direct bond, then the second compound of formula HT-1 can include a carbazole moiety.

[0161] In the chemical formula HT-1, Ar 1may be a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms. For example, Ar 1 may be, but is not limited to, a substituted or unsubstituted carbazole group, a substituted or unsubstituted dibenzofuran group, a substituted or unsubstituted dibenzothiophene group, or a substituted or unsubstituted biphenyl group.

[0162] In the chemical formula HT-1, R 51 ~R 55 may each independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted thio group, a substituted or unsubstituted oxy group, a substituted or unsubstituted amine group, a substituted or unsubstituted boron group, a substituted or unsubstituted alkyl group having from 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having from 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having from 6 to 60 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having from 2 to 60 ring carbon atoms. 51 ~R 55 Each may be linked to adjacent groups to form a ring. For example, R 51 ~R 55 Each R can independently be a hydrogen atom or a deuterium atom. 51 ~R 55 may each independently be an unsubstituted methyl group or an unsubstituted phenyl group.

[0163] In one embodiment, the second compound represented by the formula HT-1 may be any one of the compounds shown in the following compound group 2. The emitting layer EML may include at least one of the compounds shown in the following compound group 2 as a hole transporting host material.

[0164] [Second compound group] JPEG2025063842000038.jpg174170JPEG2025063842000039.jpg198170JPEG2025063842000040.jpg190170JPEG2025063842000041.jpg83170

[0165] In the exemplary compounds presented in the second group of compounds, "D" may represent a deuterium atom, and "Ph" may represent a substituted or unsubstituted phenyl group. For example, in the exemplary compounds presented in the second group of compounds, "Ph" may represent an unsubstituted phenyl group.

[0166] In one embodiment, the emitting layer EML may include a third compound represented by the following formula ET-1: For example, the third compound may be used as an electron transporting host material of the emitting layer EML.

[0167] [Chemical formula ET-1] JPEG2025063842000042.jpg40170

[0168] In the chemical formula ET-1, X 1 ~X 3 At least one of them is N and the rest are CR 56 For example, X 1 ~X 3 One of them is N, and the other two are independently CR 56 In this case, the third compound represented by the formula ET-1 may include a pyridine moiety. 1 ~X 3 Two of them are N and the remaining one is CR. 56 In this case, the third compound of formula ET-1 may include a pyrimidine moiety. 1 ~X 3 may each be N. In this case, the third compound represented by formula ET-1 may include a triazine moiety.

[0169] In the chemical formula ET-1, R 56may be a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having from 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having from 6 to 60 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having from 2 to 60 ring carbon atoms.

[0170] In the formula ET-1, b1 to b3 may each independently be an integer of 0 or more and 10 or less.

[0171] In the chemical formula ET-1, Ar 2 ~Ar 4 may each independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having from 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having from 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having from 2 to 30 ring carbon atoms. For example, Ar 2 ~Ar 4 can be a substituted or unsubstituted phenyl group, or a substituted or unsubstituted carbazole group.

[0172] In the chemical formula ET-1, L 2 ~L 4 may each independently be a direct bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms. 2 ~L 4 may each independently be a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms.

[0173] In an embodiment, the third compound may be any one of the compounds in the following third compound group: The light emitting device ED in an embodiment may include any one of the compounds in the following third compound group:

[0174] [Third compound group] JPEG2025063842000043.jpg135170JPEG2025063842000044.jpg144170JPEG2025063842000045.jpg140170JPEG20250638420 00046.jpg136170JPEG2025063842000047.jpg160170JPEG2025063842000048.jpg156170JPEG2025063842000049.jpg212170

[0175] In the exemplary compounds presented in the third group of compounds, "D" means a deuterium atom, and "Ph" means an unsubstituted phenyl group.

[0176] The emission layer EML includes a second compound and a third compound, and the second compound and the third compound may form an exciplex. In the emission layer EML, an exciplex may be formed by a hole transporting host and an electron transporting host. In this case, the triplet energy of the exciplex formed by the hole transporting host and the electron transporting host may correspond to the difference between the LUMO (Lowest Unoccupied Molecular Orbital) energy level of the electron transporting host and the HOMO (Highest Occupied Molecular Orbital) energy level of the hole transporting host.

[0177] For example, the absolute value of the triplet (T1) energy of the exciplex formed by the hole-transporting host and the electron-transporting host may be 2.4 eV or more and 3.0 eV or less. The triplet energy of the exciplex may be smaller than the energy gap of each host material. The exciplex may have a triplet energy of 3.0 eV or less, which is the energy gap between the hole-transporting host and the electron-transporting host.

[0178] In one embodiment, the emitting layer EML may further include a fourth compound in addition to the first to third compounds described above. The fourth compound may be used as a phosphorescence sensitizer of the emitting layer EML. Energy may be transferred from the fourth compound to the first compound to cause light emission.

[0179] For example, the light-emitting layer EML may include Pt (platinum) as a central metal atom, and an organometallic complex including a ligand bonded to the central metal atom as a fourth compound. In one embodiment of the light-emitting element ED, the light-emitting layer EML may include a compound represented by the following chemical formula D-1 as a fourth compound.

[0180] [Chemical formula D-1] JPEG2025063842000050.jpg64170

[0181] In the chemical formula D-1, Q 1 ~Q 4 may each independently be C or N. C1 to C4 may each independently be a substituted or unsubstituted hydrocarbon ring having from 5 to 30 ring carbon atoms, or a substituted or unsubstituted heterocycle having from 2 to 30 ring carbon atoms.

[0182] In the chemical formula D-1, L 11 ~L 13 are each independently a direct bond, L may be a substituted or unsubstituted divalent alkyl group having from 1 to 20 carbon atoms, a substituted or unsubstituted arylene group having from 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having from 2 to 30 ring carbon atoms. 11 ~L 13 In JPEG2025063842000052.jpg5170 means the portion linked to C1 to C4.

[0183] In Chemical Formula D-1, b11 to b13 may each independently be 0 or 1. When b11 is 0, C1 and C2 may not be linked to each other. When b12 is 0, C2 and C3 may not be linked to each other. When b13 is 0, C3 and C4 may not be linked to each other.

[0184] In the chemical formula D-1, R 61 ~R 66 may each independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted thio group, a substituted or unsubstituted oxy group, a substituted or unsubstituted amine group, a substituted or unsubstituted boron group, a substituted or unsubstituted alkyl group having from 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having from 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having from 6 to 60 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having from 2 to 60 ring carbon atoms. 61 ~R 66 Each of the R groups may be linked to the adjacent groups to form a ring. 61 ~R 66 may each independently be a substituted or unsubstituted methyl group, or a substituted or unsubstituted t-butyl group.

[0185] In the chemical formula D-1, d1 and d4 may each independently be an integer of 0 to 4. In the chemical formula D-1, when d1 to d4 are each 0, the fourth compound is R 61 ~R 66 Each of d1 to d4 may be unsubstituted. 61 ~R 66 When each of d1 to d4 is a hydrogen atom, it may be the same as when each of d1 to d4 is 0. When each of d1 to d4 is an integer of 2 or more, R 61 ~R 66 Each may be the same or multiple R 61 ~R 66 At least one of the may be different.

[0186] In the chemical formula D-1, C1 to C4 may each independently be a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocycle represented by any one of the following C-1 to C-4. JPEG2025063842000053.jpg53170

[0187] In C-1 to C-4, P 1 teeth, JPEG2025063842000054.jpg5170 or CR 74 and P 2 teeth, JPEG2025063842000055.jpg5170 or NR 81 and P 3 teeth, JPEG2025063842000056.jpg5170 or NR 82 and P 4 teeth, JPEG2025063842000057.jpg6170 or CR 88 It can be. R 71 ~R 88 are each independently a substituted or unsubstituted alkyl group having from 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having from 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having from 2 to 30 ring carbon atoms, or may be bonded to each other with adjacent groups to form a ring.

[0188] In addition, in C-1 to C-4, JPEG2025063842000058.jpg14170 is the part that is linked to the central metal atom, Pt, JPEG2025063842000059.jpg5170 is adjacent ring groups (C1 to C4) or linkers (L 11 ~L 13 ) may correspond to the part connected to

[0189] In one embodiment, the emitting layer EML may include a first compound which is a polycyclic compound and at least one of the second compound to the fourth compound. For example, the emitting layer EML may include a first compound, a second compound, and a third compound. In the emitting layer EML, the second compound and the third compound form an exciplex, and energy may be transferred from the exciplex to the first compound to emit light.

[0190] Also, the emission layer EML may include a first compound, a second compound, a third compound, and a fourth compound. In the emission layer EML, the second compound and the third compound form an exciplex, and energy may be transferred from the exciplex to the fourth compound and the first compound to cause emission. In one embodiment, the fourth chemical formula may be a sensitizer. In the light-emitting device ED of one embodiment, the fourth compound included in the emission layer EML may function as a sensitizer and may play a role in transferring energy from the host to the first compound, which is an emission dopant. That is, the fourth compound, which plays the role of an auxiliary dopant, may accelerate the transfer of energy to the first compound, which is an emission dopant, and increase the emission ratio of the first compound. Thus, the emission efficiency of the emission layer EML of one embodiment may be improved. Furthermore, if the transfer of energy to the first compound is increased, excitons formed in the emission layer EML may emit light quickly without being accumulated inside the emission layer EML, and deterioration of the light-emitting device may be reduced. Thus, the life of the light-emitting device ED of one embodiment may be improved.

[0191] The light-emitting device ED according to an embodiment may include the first compound, the second compound, the third compound, and the fourth compound, and the light-emitting layer EML may include a combination of two host materials and two dopant materials. In the light-emitting device ED according to an embodiment, the light-emitting layer EML may simultaneously include the second compound and the third compound, which are two different hosts, the first compound emitting delayed fluorescence, and the fourth compound including an organometallic complex, thereby providing excellent light-emitting efficiency.

[0192] In one embodiment, the fourth compound represented by the chemical formula D-1 may be represented by at least one of the compounds shown in the following fourth compound group. The light emitting layer EML may include at least one of the compounds shown in the following fourth compound group as a sensitizer material.

[0193] [Fourth compound group] JPEG2025063842000060.jpg135170JPEG2025063842000061.jpg126170JPEG2025063842000062.jpg148170

[0194] In the exemplary compounds presented in the fourth group of compounds, "D" refers to a deuterium atom.

[0195] In the light emitting device ED according to an embodiment, when the emission layer EML includes the first compound, the second compound, and the third compound as described above, the content of the first compound may be 0.1 wt% or more and 5 wt% or less based on the total weight of the first compound, the second compound, and the third compound. However, this is not limited thereto. When the content of the first compound satisfies the above ratio, the transfer of energy from the second compound and the third compound to the first compound is increased, and thus the light emitting efficiency and the life of the device may be improved.

[0196] In the emission layer EML, the content of the second compound and the third compound is the remainder excluding the weight of the above-mentioned first compound. For example, in the emission layer EML, the content of the second compound and the third compound may be 95 wt% or more and 99.9 wt% or less based on the total weight of the first compound, the second compound, and the third compound.

[0197] In the total weight of the second compound and the third compound, the weight ratio of the second compound to the third compound can be from about 3:7 to 7:3.

[0198] If the contents of the second compound and the third compound satisfy the above ratio, the charge balance characteristic in the emission layer EML is improved, so that the luminous efficiency and the device life can be increased. If the contents of the second compound and the third compound deviate from the above ratio range, the charge balance in the emission layer EML is lost, so that the luminous efficiency is reduced, and the device may be deteriorated.

[0199] When the emission layer EML includes the fourth compound, the content of the fourth compound may be about 10 wt% or more and 30 wt% or less based on the total weight of the first compound, the second compound, the third compound, and the fourth compound in the emission layer EML. However, it is not limited thereto. If the content of the fourth compound satisfies the above content, the energy transfer from the host to the first compound, which is the light-emitting dopant, is increased, and the emission rate is improved, thereby improving the luminous efficiency of the emission layer EML. If the first compound, the second compound, the third compound, and the fourth compound included in the emission layer EML satisfy the above content ratio range, excellent luminous efficiency and long life can be achieved.

[0200] The light-emitting layer EML can have a thickness of, for example, about 100 Å to about 1000 Å, or about 100 Å to about 300 Å. The light-emitting layer EML can have a single layer of a single material, a single layer of multiple different materials, or a multilayer structure having multiple layers of multiple different materials.

[0201] In the light-emitting device ED according to an embodiment shown in Figures 3 to 7, the emission layer EML may contain the polycyclic compound according to the embodiment as a dopant. Also, in the light-emitting device ED according to an embodiment shown in Figures 3 to 7, the emission layer EML may contain at least one of a first compound which is a polycyclic compound according to an embodiment, a second compound represented by a chemical formula HT-1, and a third compound represented by a chemical formula ET-1. Also, in the light-emitting device ED according to an embodiment shown in Figures 3 to 7, the emission layer EML may contain a first compound which is a polycyclic compound according to an embodiment, a second compound represented by a chemical formula HT-1, a third compound represented by a chemical formula ET-1, and a fourth compound represented by a chemical formula D-1.

[0202] In one embodiment of the light emitting element ED, the light emitting layer EML may further include an anthracene derivative, a pyrene derivative, a fluoranthene derivative, a chrysene derivative, a dihydrobenzanthracene derivative, or a triphenylene derivative. In particular, the light emitting layer EML may further include an anthracene derivative or a pyrene derivative.

[0203] In the light-emitting device ED according to an embodiment shown in Figures 3 to 7, the light-emitting layer EML may include a host and a dopant, and the light-emitting layer EML may further include a compound represented by the following formula E-1. The compound represented by the following formula E-1 may be used as a fluorescent host material.

[0204] [Chemical formula E-1] JPEG2025063842000063.jpg53170

[0205] In the chemical formula E-1, R 31 ~R 40 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted silyl group, a substituted or unsubstituted thio group, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group having from 1 to 10 carbon atoms, a substituted or unsubstituted alkenyl group having from 2 to 10 carbon atoms, a substituted or unsubstituted aryl group having from 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having from 2 to 30 ring carbon atoms, or may be bonded to adjacent groups to form a ring. 31 ~R 40 may be bonded to adjacent groups to form a saturated hydrocarbon ring, an unsaturated hydrocarbon ring, a saturated heterocycle, or an unsaturated heterocycle.

[0206] In Chemical Formula E-1, c and d may each independently be an integer of 0 to 5.

[0207] Chemical formula E-1 may be represented by any one of the following compounds E1 to E19. JPEG2025063842000064.jpg214170JPEG2025063842000065.jpg104170

[0208] In one embodiment, the light-emitting layer EML may further include a compound represented by the following formula E-2a or E-2b: The compound represented by the following formula E-2a or E-2b may be used as a phosphorescent host material.

[0209] [Chemical formula E-2a] JPEG2025063842000066.jpg47170

[0210] In the chemical formula E-2a, a is an integer of 0 to 10, and L a may be a direct bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms. a may each independently be a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms.

[0211] In the chemical formula E-2a, A 1 or A 5 are each independently N or CR i It can be. R a ~R i 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 from 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having from 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having from 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having from 2 to 30 ring carbon atoms, or may be bonded to adjacent groups to form a ring. a ~R i may be bonded to adjacent groups to form a hydrocarbon ring or a heterocycle containing N, O, S, or the like as ring-forming atoms.

[0212] On the other hand, in the chemical formula E-2a, A 1 or A 5 Two or three of the selected items are N and the rest are CR. i It could be.

[0213] [Chemical formula E-2b] JPEG2025063842000067.jpg15170

[0214] In the above formula E-2b, Cbz1 and Cbz2 may each independently be a carbazole group or a carbazole group substituted with an aryl group having 6 to 30 ring carbon atoms. b may be a direct bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms. On the other hand, b is an integer of 0 to 10, and when b is an integer of 2 or more, multiple L b may each independently be a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms.

[0215] Compounds represented by chemical formula E-2a and E-2b may be represented by any one of the compounds in the following compound group E-2. However, the compounds listed in the following compound group E-2 are merely illustrative, and compounds represented by chemical formula E-2a or E-2b are not limited to those in the following compound group E-2.

[0216] [Compound group E-2] JPEG2025063842000068.jpg134170JPEG2025063842000069.jpg199170JPEG2025063842000070.jpg59170

[0217] The light-emitting layer EML may further include a compound represented by the following chemical formula Ma: The compound represented by the following chemical formula Ma may be used as a phosphorescent dopant material.

[0218] [Chemical formula Ma] JPEG2025063842000071.jpg50170

[0219] In the above chemical formula Ma, Y 1 or Y 4 , and Z 1 ~Z 4 are each independently CR 1 or N and R 1 ~R 4 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 from 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having from 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having from 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having from 2 to 30 ring carbon atoms, or may be bonded to adjacent groups to form a ring. In the chemical formula Ma, m is 0 or 1, and n is 2 or 3. In the chemical formula Ma, if m is 0, n is 3, and if m is 1, n is 2.

[0220] The compound represented by formula Ma can be used as a phosphorescent dopant.

[0221] The compound represented by the chemical formula Ma is represented by any one of the compounds of the following compound group M-a1 to M-a25. However, the following compounds M-a1 to M-a25 are merely illustrative, and the compound represented by the chemical formula Ma is not limited to the compounds M-a1 to M-a25. JPEG2025063842000072.jpg159170JPEG2025063842000073.jpg218170

[0222] The light emitting layer EML may further include a compound represented by any one of the following chemical formulas Fa to Fc: The compounds represented by the following chemical formulas Fa to Fc may be used as a fluorescent dopant material.

[0223] [Chemical formula Fa] JPEG2025063842000074.jpg45170

[0224] In the chemical formula Fa, R a ~R j Two of the following are selected independently: It may be replaced with JPEG2025063842000075.jpg7170. a ~R j Of The remainder that is not substituted in JPEG2025063842000076.jpg7170 can each independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having from 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having from 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having from 2 to 30 ring carbon atoms.

[0225] In JPEG2025063842000077.jpg7170, Ar 1 ~Ar 2 may each independently be a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms. For example, Ar 1 and Ar 2 At least one of the groups may be a heteroaryl group containing O or S as a ring-forming atom.

[0226] [Chemical formula Fb] JPEG2025063842000078.jpg34170

[0227] In the chemical formula Fb, R a and R bare each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having from 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having from 2 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having from 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having from 2 to 30 ring carbon atoms, or may be bonded to adjacent groups to form a ring. 1 ~Ar 4 may each independently be a substituted or unsubstituted aryl group having from 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having from 2 to 30 ring carbon atoms.

[0228] In the chemical formula Fb, U and V may each independently be a substituted or unsubstituted hydrocarbon ring having 5 to 30 ring carbon atoms, or a substituted or unsubstituted heterocycle having 2 to 30 ring carbon atoms. 1 ~Ar 4 At least one of the groups may be a heteroaryl group containing O or S as a ring-forming atom.

[0229] In the chemical formula Fb, the number of rings represented by U and V may be 0 or 1, independently. For example, in the chemical formula Fb, if the number of U or V is 1, one fused ring is constituted in the part described by U or V, and if the number of U or V is 0, it means that the ring described by U or V does not exist. In detail, 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 fused ring having a fluorene core of the chemical formula Fb may be a cyclic compound having 4 rings. In addition, if the numbers of U and V are both 0, the fused ring having a fluorene core of the chemical formula Fb may be a cyclic compound having 3 rings. In addition, if the numbers of U and V are both 1, the fused ring having a fluorene core of the chemical formula Fb may be a cyclic compound having 5 rings.

[0230] [Chemical formula Fc] JPEG2025063842000079.jpg58170

[0231] In the above formula Fc, A 1and A 2 are each independently O, S, Se, or NR m and R m R may be a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having from 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having from 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having from 2 to 30 ring carbon atoms. 1 ~R 11 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted amine group, a substituted or unsubstituted boron group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thio group, a substituted or unsubstituted alkyl group having from 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having from 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having from 2 to 30 ring carbon atoms, or are bonded to each other with adjacent groups to form a ring.

[0232] In the chemical formula Fc, A 1 and A 2 may each independently bond to a substituent of an adjacent ring to form a fused ring. For example, A 1 and A 2 are each independently NR m If so, A 1 is R 4 or R 5 and may be bonded to form a ring. 2 is R 7 or R 8 may be linked to form a ring.

[0233] In one embodiment, the light-emitting layer EML is formed of a known dopant material, such as a styryl derivative (e.g., 1,4-bis[2-(3-N-ethylcarbazolyl)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)- They may further include 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., 1,1-dipyrene, 1,4-dipyrenylbenzene, 1,4-bis(N,N-diphenylamino)pyrene, and the like.

[0234] The light-emitting layer EML may further include a known phosphorescent dopant material. For example, a metal complex containing iridium (Ir), platinum (Pt), osmium (Os), gold (Au), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), or thulium (Tm) may be used as the phosphorescent dopant. In particular, Flrpic (iridium (III) bis (4,6-difluorophenylpyridinato-N,C2') picolinate, Fir6 (bis (2,4-difluorophenylpyridinato)-tetrakis (1-pyrazolyl) borate iridium (III)), or PtOEP (platinum-octaethylporphyrin) may be used as the phosphorescent dopant. However, the embodiment is not limited thereto.

[0235] The light-emitting layer EML may include a quantum dot material, and the core of the quantum dot may be selected from a II-VI compound, a I-II-VI compound, a II-IV-VI compound, a I-II-IV-VI compound, a II-IV-V compound, a III-VI compound, a I-III-VI, a III-V compound, a III-II-V compound, a IV-VI compound, a Group IV element, a Group IV compound, and combinations thereof.

[0236] The II-VI compounds include binary compounds selected from the group consisting of CdSe, CdTe, CdS, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, MgSe, MgS, and mixtures thereof, CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, CdZnSe, CdZnTe, CdHgS, CdHgSe, Cd ternary compounds selected from the group consisting of HgZnTeS, CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe, and mixtures thereof; and quaternary compounds selected from the group consisting of HgZnTeS, CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe, and mixtures thereof.

[0237] III-VI compounds include In 2 S 3 , In 2 Se 3 Two-element compounds such as InGaS 3 , InGaSe 3 etc., or any combination thereof.

[0238] Group I-III-VI compounds include AgInS, AgInS 2 , CuInS, CuInS 2 , AgGaS 2 , CuGaS 2 ,CuGaO 2 , AgGaO 2 , AgAlO 2 and mixtures thereof, or AgInGaS 2 , CuInGaS 2 The compound may be selected from quaternary compounds such as:

[0239] The III-V compound may be selected from the group consisting of binary compounds selected from the group consisting of GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, InSb, and mixtures thereof, ternary compounds selected from the group consisting of GaNP, GaNAs, GaNSb, GaPAs, GaPSb, AlNP, AlNAs, AlNSb, AlPAs, AlPSb, InGaP, InAlP, InNP, InNAs, InNSb, InPAs, InPSb, and mixtures thereof, and quaternary compounds selected from the group consisting of GaAlNP, GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNP, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs, InAlPSb, and mixtures thereof, while the III-V compound may further comprise a group II metal. For example, InZnP may be selected as the III-II-V compound.

[0240] The IV-VI compound may be selected from the group consisting of binary compounds selected from the group consisting of SnS, SnSe, SnTe, PbS, PbSe, PbTe, and mixtures thereof, ternary compounds selected from the group consisting of SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, SnPbTe, and mixtures thereof, and quaternary compounds selected from the group consisting of SnPbSSe, SnPbSeTe, SnPbSTe, and mixtures thereof. The group IV element may be selected from the group consisting of Si, Ge, and mixtures thereof. The group IV compound may be a binary compound selected from the group consisting of SiC, SiGe, and mixtures thereof.

[0241] Each element in the multi-element compounds such as the binary, ternary, and quaternary compounds may be present in the particles in a uniform or non-uniform concentration. That is, the chemical formula indicates the type of elements in the compound, and the element ratios in the compound may vary. For example, AgInGaS 2 is AgIn x Ga 1-x S2 (X is a real number between 0 and 1).

[0242] Meanwhile, the quantum dots may have a single structure in which the concentration of each element contained in the quantum dot is uniform, or a core-shell dual structure, for example, the material contained in the core and the material contained in the shell may be different from each other.

[0243] The shell of the quantum dot may act as a protective layer to prevent chemical denaturation of the core and maintain the semiconductor properties, and / or as a charging layer to impart electrophoretic properties to the quantum dot. The shell may be a single layer or multiple layers. The interface between the core and the shell may have a concentration gradient in which the concentration of elements present in the shell decreases toward the center.

[0244] Examples of the shell of the quantum dot include a metal or nonmetal oxide, a semiconductor compound, or a combination thereof. For example, the metal or nonmetal oxide is SiO 2 , Al 2 O 3 , TiO 2 , ZnO, MnO, Mn 2 O 3 , Mn 3 O 4 , CuO, FeO, Fe 2 O 3 , Fe 3 O 4 , CoO, Co 3 O 4 , binary compounds such as NiO, or MgAl 2 O 4 , CoFe 2 O 4 , NiFe 2 O 4 , CoMn 2 O 4 However, the present invention is not limited thereto.

[0245] Examples of the semiconductor compound include CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnSeS, ZnTeS, GaAs, GaP, GaSb, HgS, HgSe, HgTe, InAs, InP, InGaP, InSb, AlAs, AlP, and AlSb, but the present invention is not limited to these.

[0246] Each element contained in the multi-element compound such as the binary or ternary compound may be present in the particle in a uniform or non-uniform concentration, i.e., the chemical formula indicates the type of elements contained in the compound, and the element ratio within the compound may vary.

[0247] The quantum dots 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 in this range, color purity and color reproducibility can be improved. In addition, since the light emitted through such quantum dots is emitted in all directions, the light viewing angle can be improved.

[0248] The shape of the quantum dots is not particularly limited and may be any shape commonly used in the art. More specifically, the quantum dots may be in the form of spherical, pyramidal, multi-arm, or cubic nanoparticles, nanotubes, nanowires, nanofibers, or nanoplate-like particles.

[0249] The size of the quantum dots or the element ratio in the quantum dot compound can be adjusted to adjust the energy band gap, so that light of various wavelengths can be obtained from the quantum dot light emitting layer. Thus, by using quantum dots as described above (using quantum dots of different sizes or varying the element ratio in the quantum dot compound), a light emitting device that emits light of various wavelengths can be realized. In particular, the size of the quantum dots or the element ratio in the quantum dot compound can be adjusted to select red, green and / or blue light to be emitted. In addition, the quantum dots can be configured to emit white light by combining various colors of light.

[0250] 3 to 7, an electron transport region ETR is provided on the light emitting layer EML. The electron transport region ETR includes 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.

[0251] The electron transport region ETR can have a single layer of a single material, a single layer of multiple different materials, or a multi-layer structure having multiple layers of multiple different materials.

[0252] 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 may have a single layer structure of an electron injection material and an electron transport material. The electron transport region ETR may have a single layer structure of a plurality of different materials, or may have a structure of an electron transport layer ETL / electron injection layer EIL or a hole blocking layer HBL / electron transport layer ETL / electron injection layer EIL stacked in order from the light 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.

[0253] The electron transport region ETR can be formed using various methods such as vacuum deposition, spin coating, casting, LB method, inkjet printing, laser printing, laser thermal transfer (LITI), and the like.

[0254] The electron transport region ETR may include a compound represented by the following chemical formula ET-2.

[0255] [Chemical formula ET-2] JPEG2025063842000080.jpg45170

[0256] In the chemical formula ET-2, X 1 ~X 3 At least one of them is N and the rest is CR a R amay be a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having from 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having from 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having from 2 to 30 ring carbon atoms. 1 ~Ar 3 may each independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having from 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having from 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having from 2 to 30 ring carbon atoms.

[0257] In the formula ET-2, a to c may each independently be an integer of 0 to 10. 1 and L 3 may each independently be a direct bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms. 1 and L 3 may each independently be a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms.

[0258] The electron transport region ETR may include an anthracene-based compound. However, the electron transport region ETR is not limited thereto. For example, the electron transport region ETR may include Alq 3(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-phenylbenzimidazol-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), Bph en (4,7-diphenyl-1,10-phenanthroline), TAZ (3-(4-biphenylyl)-4-phenyl-5-tert-butylphenyl-1,2,4-triazole), NTAZ (4-(naphthalen-1-yl)-3,5-diphenyl-4H-1,2,4-triazole), tBu-PBD (2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole), BAlq (bis(2-methyl-8-quinolinolato-N1,O8)-(1,1'-biphenyl-4-olato)aluminum), Bebq 2 (beryllium bis(benzoquinolin-10-olato), ADN (9,10-di(naphthalen-2-yl)anthracene), BmPyPhB (1,3-bis[3,5-di(pyridin-3-yl)phenyl]benzene), and mixtures thereof.

[0259] The electron transport region ETR may include at least one of the following compounds ET1 to ET36. JPEG2025063842000081.jpg160170JPEG2025063842000082.jpg241170JPEG2025063842000083.jpg201170JPEG2025063842000084.jpg53170

[0260] The electron transport region ETR may also include a metal halide such as LiF, NaCl, CsF, RbCl, RbI, CuI, or KI, a lanthanum group metal such as Yb, or a co-deposition material of the metal halide and a lanthanum group metal. For example, the electron transport region ETR may include co-deposition materials such as KI:Yb, RbI:Yb, or LiF:Yb. 2 Metal oxides such as O, BaO, or Liq (8-hydroxy-lithium quinolate) may be used, but examples are not limited thereto. The electron transport region ETR may also be made of a material in which an electron transport material and an insulating organo metal salt are mixed. The organo metal salt may be a material having an energy band gap of about 4 eV or more. In more detail, for example, the organo metal salt may include metal acetate, metal benzoate, metal acetoacetate, metal acetylacetonate, or metal stearate.

[0261] In addition to the above-mentioned materials, 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), but is not limited thereto.

[0262] The electron transport region ETR may include at least one of the above-mentioned compounds of the electron transport region in the electron injection layer EIL, the electron transport layer ETL, and the hole blocking layer HBL.

[0263] When 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 HTL satisfies the above-mentioned range, a satisfactory level of electron transport characteristics can be obtained without a substantial increase in driving voltage. When 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, for example, about 3 Å to about 90 Å. If the thickness of the electron injection layer EIL satisfies the above-mentioned range, a satisfactory level of electron injection characteristics can be obtained without a substantial increase in driving voltage.

[0264] The second electrode EL2 is provided on the electron transport region ETR. The second electrode EL2 can be a common electrode. The second electrode EL2 can be a cathode or an anode, but the embodiment is not limited thereto. For example, if the first electrode EL1 is an anode, the second electrode can be a cathode, and if the first electrode EL1 is a cathode, the second electrode EL2 can be an anode.

[0265] The second electrode EL2 may be a transmissive electrode, a semi-transmissive 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, such as indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), or indium tin zinc oxide (ITZO).

[0266] If the second electrode EL2 is a semi-transmissive electrode or a reflective electrode, the second electrode EL2 may include Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF / Ca, LiF / Al, Mo, Ti, Yb, W, or a compound or mixture containing these (e.g., AgMg, AgYb, or MgYb). Alternatively, the second electrode EL2 may have a multi-layer structure including a reflective film or semi-transmissive film made of the above material, and a transparent conductive film made of ITO, IZO, ZnO, ITZO, or the like. For example, the second electrode EL2 may include the above-mentioned metal materials, a combination of two or more metal materials selected from the above-mentioned metal materials, or an oxide of the above-mentioned metal materials.

[0267] Although not shown, the second electrode EL2 may be connected to an auxiliary electrode, which may reduce the resistance of the second electrode EL2.

[0268] Meanwhile, in one embodiment, a capping layer CPL may be further disposed on the second electrode EL2 of the light emitting element ED. The capping layer CPL may include multiple layers or a single layer.

[0269] In one embodiment, the capping layer CPL can be an organic layer or an inorganic layer. For example, if the capping layer CPL includes an inorganic material, the inorganic material can be an alkali metal compound such as LiF, MgF 2 The material may include alkaline earth compounds such as SiON, SiNx, and SiOy.

[0270] For example, if the capping layer CPL contains an organic material, the organic material may be α-NPD, NPB, TPD, m-MTDATA, Alq 3 , CuPc, TPD15 (N4,N4,N4',N4'-tetra(biphenyl-4-yl)biphenyl-4,4'-diamine), TCTA (4,4',4"-tris(carbazolesol-9-yl)triphenylamine), or the like, or an epoxy resin, or an acrylate such as methacrylate. However, embodiments are not limited thereto, and the capping layer CPL may include at least one of compounds P1 to P5 as follows. JPEG2025063842000085.jpg168170

[0271] Meanwhile, the refractive index of the capping layer CPL may be 1.6 or more. Specifically, the refractive index of the capping layer CPL may be 1.6 or more for light in the wavelength range of 550 nm or more and 660 nm or less.

[0272] 8 and 11 are cross-sectional views of a display device according to an embodiment. In the following description of the display device according to an embodiment, the same contents as those described in the above-mentioned FIGS. 1 to 7 will not be described again, and differences will be mainly described.

[0273] 8, a display device DD-a according to an embodiment may include a display panel DP including a display element layer DP-ED, a light control layer CCL disposed on the display panel DP, and a color filter layer CFL. In the embodiment shown in FIG. 8, 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, and the display element layer DP-ED may include a light-emitting element ED.

[0274] The light emitting device ED may include a first electrode EL1, a hole transport region HTR disposed on the first electrode EL1, an emitting layer EML disposed on the hole transport region HTR, an electron transport region ETR disposed on the emitting layer EML, and a second electrode EL2 disposed on the electron transport region ETR. Meanwhile, the structure of the light emitting device ED shown in FIG. 8 may be the same as the structures of the light emitting devices shown in FIGS. 3 to 7. The light emitting device ED shown in FIG. 8 may include a polycyclic compound of an embodiment. Thereby, the light emitting device ED may exhibit high efficiency and long life characteristics. In addition, the light emitting device ED of an embodiment may exhibit high light efficiency characteristics with high color purity. The light emitting device ED of an embodiment may exhibit high light efficiency characteristics in a blue light emitting region.

[0275] 8, the emitting layer EML may be disposed within an opening OH defined in the pixel defining layer DPL. For example, the emitting layers EML provided corresponding to each of the emitting regions PXA-R, PXA-G, and PXA-B, which are separated by the pixel defining layer PDL, may emit light in the same wavelength range. In the display device DD-a according to an embodiment, the emitting layer EML may emit blue light. Meanwhile, unlike the drawing, in an embodiment, the emitting layer EML may be provided as a common layer for the entire emitting regions PXA-R, PXA-G, and PXA-B.

[0276] The light control layer CCL may be disposed on the display panel DP. Meanwhile, although the light control layer CCL is shown to be disposed above the display element layer DP-ED, the embodiment is not limited thereto, and the light control layer CCL may be disposed below the display element layer DP-ED. The light control layer CCL may include a light converter. The light converter may be a quantum dot or a phosphor, etc. The light converter may convert the wavelength of the provided light and emit it. That is, the light control layer CCL may be a layer including quantum dots or a phosphor.

[0277] The light control layer CCL may include a plurality of light control parts CCP1, CCP2, CCP3. The light control parts CCP1, CCP2, CCP3 may be spaced apart from each other.

[0278] 8, a division pattern BMP is provided between the light control parts CCP1, CCP2, and CCP3 that are spaced apart from each other, but the embodiment is not limited thereto. In FIG. 8, the division pattern BMP is shown not to overlap with the light control parts CCP1, CCP2, and CCP3, but the edges of the light control parts CCP1, CCP2, and CCP3 may at least partially overlap with the division pattern BMP.

[0279] The light control layer CCL may include a first light control unit CCP1 including a first quantum dot QD1 that converts a first color light provided from the light-emitting element ED into a second color light, a second light control unit CCP2 including 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.

[0280] In one embodiment, the first light controller CCP1 may provide red light, which is the second color light, and the second light controller CCP2 may provide green light, which is the third color light. The third light controller CCP3 may transmit and provide blue light, which is the first color light, provided from 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 contents as described above may be applied to the quantum dots QD1 and QD2.

[0281] In addition, 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 include a scatterer SP without including a quantum dot.

[0282] The scatterer SP may be an inorganic particle. For example, the scatterer SP may be TiO 2 , ZnO, Al 2 O 3 , SiO 2 The scatterer SP may include at least one of TiO 2 , ZnO, Al 2 O 3 , SiO 2 or hollow silica, or TiO 2 , ZnO, Al 2 O 3 , SiO 2 and hollow silica.

[0283] The first light controller CCP1, the second light controller CCP2, and the third light controller CCP3 may each include a base resin BR1, BR2, or BR3 in which quantum dots QD1, QD2, and a scatterer SP are dispersed. In one embodiment, the first light controller CCP1 may include the first quantum dots QD1 and the scatterer SP dispersed in the first base resin BR1, the second light controller CCP2 may include the second quantum dots QD2 and the scatterer SP dispersed in the second base resin BR2, and the third light controller CCP1 may include the scatterer SP dispersed in the third base resin BR3.

[0284] The base resins BR1, BR2, and BR3 are media in which the quantum dots QD1, QD2, and the scatterers SP are dispersed, and may be made of various resin compositions generally called binders. For example, the base resins BR1, BR2, and BR3 may be acrylic resins, urethane resins, silicone resins, epoxy resins, etc. The base resins BR1, BR2, and BR3 may be transparent resins. In one embodiment, the first base resin BR1, the second base resin BR2, and the third base resin BR3 may be the same or different from each other.

[0285] The light control layer CCL may include a barrier layer BFL1. The barrier layer BFL1 may function to prevent the penetration of moisture and / or oxygen (hereinafter referred to as "moisture / oxygen"). The barrier layer BFL1 may be disposed on the light control units CCP1, CCP2, and CCP3 to prevent the light control units CCP1, CCP2, and CCP3 from being exposed to moisture / oxygen. Meanwhile, the barrier layer BFL1 may cover the light control units CCP1, CCP2, and CCP3. In addition, a barrier layer BLF2 may be provided between the light control units CCP1, CCP2, and CCP3 and the color filter layer CFL.

[0286] The barrier layers BFL1 and BFL2 may include at least one inorganic layer. That is, the barrier layers BFL1 and BFL2 may be formed including an inorganic material. For example, the barrier layers BFL1 and BFL2 may be formed 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 having a high light transmittance. Meanwhile, the barrier layers BFL1 and BFL2 may further include an organic film. The barrier layers BFL1 and BFL2 may be formed of a single layer or multiple layers.

[0287] In one embodiment of the display device DD-a, the color filter layer CFL is disposed on the light control layer CCL. For example, the color filter layer CFL can be disposed directly on the color control layer CCL. In this case, the barrier layer BFL2 can be omitted.

[0288] The color filter layer CFL may include filters CF1, CF2, and CF3. The color filter CFL may include a first filter CF1 that transmits a second color light, a second filter CF2 that transmits a third color light, and a third filter CF3 that transmits the 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, and 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.

[0289] However, the embodiment is not limited thereto, and the third filter CF3 may not include a pigment or a dye. The third filter CF3 may include a polymer photosensitive resin and not include a pigment or a dye. The third filter CF3 may be transparent. The third filter CF3 may be made of a transparent photosensitive resin.

[0290] 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 integrally without being separated from each other.

[0291] Although not shown, the color filter layer CFL may further include a light-shielding portion (not shown). The light-shielding portion may be a black matrix. The light-shielding portion may be formed including an organic light-shielding material or an inorganic light-shielding material including a black pigment or a black dye. The light-shielding portion may prevent light leakage and distinguish the boundaries between the adjacent filters CF1, CF2, and CF3. In one embodiment, the light-shielding portion may be formed of a blue filter.

[0292] The first to third filters CF1, CF2, and CF3 may be arranged corresponding to the red light emitting region PXA-R, the green light emitting region PXA-G, and the blue light emitting region PXA-B, respectively.

[0293] A base substrate BL may be disposed on the color filter layer CFL. The base substrate BL may be a member that provides a base surface on which the color filter layer CFL, the light control layer CCL, etc. are disposed. The base substrate BL may be a glass substrate, a metal substrate, a plastic substrate, etc. However, the embodiment is not limited thereto, and the base substrate BL may be an inorganic layer, an organic layer, or a composite material layer. Also, unlike the illustrated embodiment, the base substrate BL may be omitted.

[0294] 9 is a cross-sectional view showing a part of a display device according to an embodiment. In the display device DD-TD of the embodiment, the light emitting device ED-BT may include a plurality of light emitting structures OL-B1, OL-B2, and OL-B3. At least one of the plurality of light emitting structures OL-B1, OL-B2, and OL-B3 may include the polycyclic compound of the embodiment. As a result, the light emitting device ED-BT may exhibit high efficiency and long life characteristics. In addition, the light emitting device ED-BT of the embodiment may exhibit high light efficiency characteristics with high color purity, for example, the light emitting device ED-BT of the embodiment may exhibit high light efficiency characteristics in the blue light emission region.

[0295] The light emitting element ED-BT may include a first electrode EL1 and a second electrode EL2 facing each other, and a plurality of light emitting structures OL-B1, OL-B2, and OL-B3 provided by sequentially stacking in the thickness direction between the first electrode EL1 and the second electrode EL2. Each of the light emitting structures OL-B1, OL-B2, and OL-B3 may include an emitting layer EML (FIG. 8), a hole transport region HTR, and an electron transport region ETR arranged with the emitting layer EML (FIG. 8) sandwiched therebetween. In other words, the light emitting element ED-BT included in the display device DD-TD of one embodiment may be a light emitting element having a tandem structure including a plurality of light emitting layers.

[0296] In the embodiment shown in Fig. 9, the light emitted from each of the light emitting structures OL-B1, OL-B2, and OL-B3 may be blue light. However, the embodiment is not limited thereto, and the wavelength regions of the light emitted from each of the light emitting structures OL-B1, OL-B2, and OL-B3 may be different from each other. For example, a light emitting device ED-BT including a plurality of light emitting structures OL-B1, OL-B2, and OL-B3 emitting light in different wavelength regions may emit white light.

[0297] A charge generation layer CGL may be disposed between adjacent light emitting structures OL-B1, OL-B2, and OL-B3. The charge generation layer CGL may include a p-type charge generation layer and / or an n-type charge generation layer.

[0298] Referring to FIG. 10, the display device DD-b according to an embodiment may include light emitting devices ED-1, ED-2, and ED-3 in which two light emitting layers are stacked. At least one of the light emitting devices ED-1, ED-2, and ED-3 may include the polycyclic compound of an embodiment. As a result, the light emitting devices ED-1, ED-2, and ED-3 may exhibit high efficiency and long life characteristics. In addition, the light emitting devices ED-1, ED-2, and ED-3 of an embodiment may exhibit high light efficiency characteristics with high color purity. For example, the light emitting device ED-3 of an embodiment may exhibit high light efficiency characteristics in a blue light emission region.

[0299] 2, the display device DD of the embodiment shown in FIG 10 is different in that the first to third light emitting elements ED-1, ED-2, and ED-3 each include two light emitting layers stacked in the thickness direction. In each of the first to third light emitting elements ED-1, ED-2, and ED-3, the two light emitting layers may emit light in the same wavelength range.

[0300] The first light-emitting element ED-1 may include a first red light-emitting layer EML-R1 and a second red light-emitting layer EML-R2. The second light-emitting element ED-2 may include a first green light-emitting layer EML-G1 and a second green light-emitting layer EML-G2. The third light-emitting element ED-3 may include a first blue light-emitting layer EML-B1 and a second blue light-emitting layer EML-B2. A light-emitting auxiliary part 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.

[0301] 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 an electron transport region, a charge generation layer, and a hole transport region, which are sequentially stacked. The light-emitting auxiliary part OG may be commonly provided for the first to third light-emitting elements ED-1, ED-2, and ED-3. However, the embodiment is not limited thereto, and the light-emitting auxiliary part OG may be provided by being patterned in an opening OH defined in the pixel defining layer PDL.

[0302] The first red light-emitting layer EML-R1, the first green light-emitting layer EML-G1, and the first blue light-emitting layer EML-B1 may be disposed between the light-emitting auxiliary part OG and the electron transporting region ETR. The second red light-emitting layer EML-R2, the second green light-emitting layer EML-G2, and the second blue light-emitting layer EML-B2 may be disposed between the hole transporting region HTR and the light-emitting auxiliary part OG.

[0303] 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 portion OG, a first red light-emitting layer EML-R1, an electron transport region ETR, and a second electrode EL2, which are stacked in this order. 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 portion OG, a first green light-emitting layer EML-G1, an electron transport region ETR, and a second electrode EL2, which are stacked in this order. 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 portion OG, a first blue light-emitting layer EML-B1, an electron transport region ETR, and a second electrode EL2, which are stacked in this order.

[0304] 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 and may control reflected light in the display panel DP due to external light. Unlike the illustration, the optical auxiliary layer PL may be omitted in the display device according to an embodiment.

[0305] Unlike Figs. 9 and 10, the display device DD-c of Fig. 11 is shown to include four light emitting structures OL-B1, OL-B2, OL-B3, and OL-C1. The light emitting device ED-CT may include a first electrode EL1 and a second electrode EL2 facing each other, and first to fourth light emitting structures OL-B1, OL-B2, OL-B3, and OL-C1 sequentially stacked in a thickness direction between the first electrode EL1 and the second electrode EL2. At least one of the first to fourth display devices OL-B1, OL-B2, OL-B3, and OL-C1 may include a polycyclic compound of an embodiment. As a result, the light emitting device ED-CT may exhibit high efficiency and long life characteristics. In addition, the light emitting device ED-CT of an embodiment may exhibit high light efficiency characteristics with high color purity. For example, the light emitting device ED-CT of an embodiment may exhibit high light efficiency characteristics in a blue light emission region.

[0306] Charge generation layers CGL1, CGL2, and CGL3 may be disposed between the first to fourth light emitting structures OL-B1, OL-B2, OL-B3, and OL-C1. Of the four light emitting structures, the first to third light emitting structures OL-B1, OL-B2, and OL-B3 may emit blue light, and the fourth light emitting structure OL-C1 may emit green light. However, the embodiment is not limited thereto, and the first to fourth light emitting structures OL-B1, OL-B2, OL-B3, and OL-C1 may emit light in different wavelength regions. The charge generation layers GCL1, CGL2, and CGL3 disposed between the adjacent light emitting structures OL-B1, OL-B2, OL-B3, and OL-C1 may include a p-type charge generation layer and / or an n-type charge generation layer.

[0307] In one embodiment, the electronic device may include a display device including a plurality of light emitting elements, and a controller for controlling the display device. The electronic device of the embodiment may be a device that is activated by an electrical signal. The electronic device may include various electronic devices of various embodiments. For example, the display device may include large electronic devices such as televisions, monitors, and external billboards, as well as small and medium-sized display devices such as personal computers, notebook computers, PDAs, vehicle displays, game consoles, portable electronic devices, and cameras.

[0308] 12 is a diagram showing a vehicle AM ​​in which the first to fourth display devices DD-1, DD-2, DD-3, and DD-4 are arranged. At least one of the first to fourth display devices DD-1, DD-2, DD-3, and DD-4 may include the same configuration as the display devices DD, DD-TD, DD-a, DD-b, and DD-c of the embodiment described with reference to FIGS. 1 and 2 and FIGS. 8 to 11.

[0309] 12 shows a car as the vehicle AM, this is merely an example, and the first to fourth display devices DD-1, DD-2, DD-3, and DD-4 may be installed in other means of transportation such as bicycles, motorcycles, trains, ships, and airplanes. At least one of the first to fourth display devices DD-1, DD-2, DD-3, and DD-4 including the same configurations of the display devices DD, DD-TD, DD-a, DD-b, and DD-c of the embodiment may be adopted in a personal computer, a notebook computer, a PDA, a game machine, a portable electronic device, a television, a monitor, an external billboard, and the like. These are merely presented as examples, and may be display devices adopted in other electronic devices without departing from the concept of the present invention.

[0310] At least one of the first to fourth display devices DD-1, DD-2, DD-3, and DD-4 may include the light-emitting element ED described with reference to Figures 3 to 7. At least one of the first to fourth display devices DD-1, DD-2, DD-3, and DD-4 may include the polycyclic compound of an embodiment. As a result, the first to fourth display devices DD-1, DD-2, DD-3, and DD-4 including the polycyclic compound of an embodiment may have improved display efficiency and display life. In addition, the first to fourth display devices DD-1, DD-2, DD-3, and DD-4 including the polycyclic compound of an embodiment may exhibit excellent display quality.

[0311] Referring to FIG. 12, the vehicle AM ​​includes a handle HA and a gear GR for operating the vehicle AM, and a front window GL may be positioned to face the driver.

[0312] The first display device DD-1 may be disposed in a first area overlapping the steering wheel HA. For example, the first display device DD-1 may be a digital cluster displaying first information of the vehicle AM. The first information may include a first scale indicating the traveling speed of the vehicle AM, a second scale indicating the engine revolutions (i.e., RPM (revolutions per minute)), and an image indicating the fuel status. The first scale and the second scale may be displayed as digital images.

[0313] The second display device DD-2 faces the driver's seat and is disposed in a second region overlapping the front window WD. The driver's seat may be a seat where the steering wheel HA is disposed. For example, the second display device DD-2 may be a Head Up Display (HUD) that displays second information of the vehicle AM. The second display device DD-2 may be optically transparent. The second information may include digital numbers indicating the traveling speed of the vehicle AM ​​and may further include information such as the current time. Unlike the illustration, the second information of the second display device DD-2 may be projected and displayed on the front window GL.

[0314] The third display device DD-3 may be disposed in a third area adjacent to the gear GR. For example, the third display device DD-3 may be a Center Information Display (CID) disposed between the driver's seat and the passenger seat and displaying the third information. The passenger seat may be a seat separated from the driver's seat with the gear GR in between. The third information may include information regarding road conditions (e.g., navigation information), music or radio playback, dynamic video playback, temperature inside the vehicle AM, etc.

[0315] The fourth display device DD-4 may be spaced apart from the handle HA and the gear GR and disposed in a fourth region adjacent to the side of the vehicle AM. For example, the fourth display device DD-4 may be a digital side mirror that displays the fourth information. The fourth display device DD-4 may display an image of the outside of the vehicle AM ​​captured by a camera module CM disposed on the outside of the vehicle AM. The fourth information may include an image of the outside of the vehicle AM.

[0316] The above-mentioned first to fourth information are merely exemplary, and the first to fourth display devices DD-1, DD-2, DD-3, and DD-4 may further display information related to the interior and exterior of the vehicle. The first to fourth information may include different information from each other. However, the embodiment is not limited thereto, and some of the first to fourth information may include the same information.

[0317] Hereinafter, a polycyclic compound according to an embodiment of the present invention and a light emitting device according to an embodiment will be described in detail with reference to examples and comparative examples. Note that the following examples are merely illustrative examples for aiding understanding of the present invention, and the scope of the present invention is not limited thereto.

[0318] [Example] 1. Synthesis of polycyclic compounds according to one embodiment The synthesis method of the polycyclic compound according to the present embodiment will be specifically described by taking as examples the synthesis methods of compounds 25, 26, 29, 30, 41, 44, 57, and 61. The synthesis method of the polycyclic compound described below is an example, and the synthesis method of the compound according to the embodiment of the present invention is not limited to the following example.

[0319] (1) Method for synthesizing intermediates A method for synthesizing intermediates used in a synthesis example of a polycyclic compound according to one embodiment will be described with reference to reaction formulas M1 to M14.

[0320] <Synthesis of intermediate M1> The intermediate layer M1 can be synthesized by the steps of the following reaction formula M1.

[0321] [Reaction formula M1] JPEG2025063842000086.jpg37170

[0322] In a 500 mL three-neck flask, add 10 g of 1-bromocarbazole, 13 g of 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane), 8.8 g of potassium acetate, and Pd(dppf)Cl. 21.2g was added and the inside of the flask was replaced with Ar (argon). Next, 200mL of dioxane was added to the flask and stirred at 80°C for 5 hours. After the reaction, the resulting reaction solution was concentrated with an evaporator, the organic matter was dissolved with toluene, and the inorganic matter was removed with a silica gel pad. Next, the crude product was concentrated with an evaporator and purified with a silica gel column (ethyl acetate / hexane = 1 / 3) to obtain 11g of a white solid. The resulting solid was measured by FAB-MS and confirmed to have an m / z of 293, confirming the intermediate M1 of the target product.

[0323] <Synthesis of intermediate M2> The intermediate layer M2 can be synthesized by the steps of the following reaction formula M2.

[0324] [Reaction formula M2] JPEG2025063842000087.jpg41170

[0325] In a 500 mL three-neck flask, add 10 g of 1-bromo-3,6-di-tert-butylcarbazole, 9.2 g of 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane), 6.0 g of potassium acetate, and Pd(dppf)Cl. 2 0.82g was added and the inside of the flask was replaced with Ar (argon). Next, 140mL of dioxane was added and stirred at 80°C for 5 hours. After the reaction, the resulting reaction solution was concentrated with an evaporative concentrator, the organic matter was dissolved with toluene, and the inorganic matter was removed with a silica gel pad. Next, the crude product was concentrated with an evaporative concentrator and purified with a silica gel column (ethyl acetate / hexane = 1 / 3) to obtain 11g of a white solid. The obtained solid was measured by FAB-MS and confirmed to be 405m / z, confirming that it was the intermediate M2 of the target product.

[0326] <Synthesis of intermediate M3> The intermediate layer M3 can be synthesized by the steps of the following reaction formula M3.

[0327] [Reaction formula M3] JPEG2025063842000088.jpg61170

[0328] In a 500 mL three-neck flask, add 10 g of intermediate M1, 10 g of 4-bromo-2,3,5,6-tetrafluorocyanobenzene, 16 g of potassium carbonate, and Pd(PPh 3 ) 4 4.5g was added and the inside of the flask was replaced with Ar (argon). Next, 200mL of THF and 100mL of water were added and stirred while heating and refluxing for 5 hours. The organic layer of the resulting reaction solution was extracted with toluene, washed with water, dried with magnesium sulfate, the solid was filtered, and then concentrated with an evaporative concentrator. Next, the crude product was purified with a silica gel column (ethyl acetate / hexane = 1 / 2) to obtain 8g of a pale yellow solid. The obtained solid was measured by FAB-MS and confirmed to have an m / z of 340, confirming the target intermediate M3.

[0329] <Synthesis of intermediate M4> The intermediate layer M4 can be synthesized by the steps of the following reaction formula M4.

[0330] [Reaction formula M4] JPEG2025063842000089.jpg57170

[0331] In a 500 mL three-neck flask, 9.2 g of intermediate M1, 8.0 g of 1,3-dibromo-2,4,5,6-tetrafluorobenzene, 13 g of potassium carbonate, and Pd(PPh 3 ) 4 3.8g was added and the inside of the flask was replaced with Ar (argon). Next, 160mL of THF and 80mL of water were added and stirred while heating and refluxing for 5 hours. The organic layer of the resulting reaction solution was extracted with toluene, washed with water, dried with magnesium sulfate, filtered, and then concentrated with an evaporative concentrator. Next, the crude product was purified with a silica gel column (ethyl acetate / hexane = 1 / 2) to obtain 10g of a white solid. The obtained solid was measured by FAB-MS and confirmed to have an m / z of 394, confirming the intermediate M4 of the target product.

[0332] <Synthesis of intermediate M5> The intermediate layer M5 can be synthesized by the steps of the following reaction formula M5.

[0333] [Reaction formula M5] JPEG2025063842000090.jpg52170

[0334] In a 500 mL three-neck flask, add 11 g of intermediate M2, 7.0 g of 4-bromo-2,3,5,6-tetrafluorocyanobenzene, 11 g of potassium carbonate, and Pd(PPh 3 ) 4 3.2g was added and the inside of the flask was replaced with Ar (argon). Next, 140mL of THF and 70mL of water were added and stirred while heating and refluxing for 5 hours. The organic layer of the resulting reaction solution was extracted with toluene, washed with water, dried with magnesium sulfate, filtered, and concentrated with an evaporative concentrator. Next, the crude product was purified with a silica gel column (ethyl acetate / hexane = 1 / 2) to obtain 10g of a pale yellow solid. The obtained solid was measured by FAB-MS and confirmed to have an m / z of 453, confirming the intermediate M5 of the target product.

[0335] <Synthesis of intermediate M6> The intermediate layer M6 can be synthesized by the steps of the following reaction formula M6.

[0336] [Reaction formula M6] JPEG2025063842000091.jpg50170

[0337] In a 500 mL three-neck flask, 6.4 g of intermediate M1, 10 g of 2-(4-bromo-2,3,5,6-tetrafluorophenyl)-4,6-diphenyl-1,3,5-triazine, 9.0 g of potassium carbonate, and Pd(PPh 3 ) 42.5g was added and the inside of the flask was replaced with Ar (argon). Next, 100mL of THF and 50mL of water were added and stirred while heating and refluxing for 5 hours. The organic layer of the resulting reaction solution was extracted with toluene, washed with water, dried with magnesium sulfate, filtered, and concentrated in an evaporative concentrator. Next, the crude product was purified with a silica gel column (ethyl acetate / hexane = 1 / 2) to obtain 10g of a pale yellow solid. The obtained solid was measured by FAB-MS and confirmed to have an m / z of 547, confirming the intermediate M6 of the target product.

[0338] <Synthesis of intermediate M7> The intermediate layer M7 can be synthesized by the steps of the following reaction formula M7.

[0339] [Reaction formula M7] JPEG2025063842000092.jpg49170

[0340] In a 500 mL three-neck flask, add 10 g of intermediate M4, 8.4 g of 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane), 5.5 g of potassium acetate, and Pd(dppf)Cl. 2 0.74g was added and the inside of the flask was replaced with Ar (argon). Next, 130mL of dioxane was added and stirred at 80°C for 5 hours. The resulting reaction solution was concentrated with an evaporative concentrator, and then the organic matter was dissolved with toluene and the inorganic matter was removed with a silica gel pad. Next, the crude product was concentrated with an evaporative concentrator and purified with a silica gel column (ethyl acetate / hexane = 1 / 3) to obtain 11g of a white solid. The resulting solid was measured by FAB-MS and confirmed to have an m / z of 441, confirming that it was the intermediate M7 of interest.

[0341] <Synthesis of intermediate M8> The intermediate layer M8 can be synthesized by the steps of the following reaction formula M8.

[0342] [Reaction formula M8] JPEG2025063842000093.jpg64170

[0343] In a 500 mL three-neck flask, add 11 g of intermediate M7, 6.5 g of 2-chloro-4,6-diphenyl-1,3,5-triazine, 10 g of potassium carbonate, and Pd(PPh 3 ) 4 2.8g was added and the inside of the flask was replaced with Ar (argon). Next, 120mL of THF and 60mL of water were added and stirred while heating and refluxing for 5 hours. The organic layer of the resulting reaction solution was extracted with toluene, washed with water, dried with magnesium sulfate, filtered, and concentrated with an evaporative concentrator. Next, the crude product was purified with a silica gel column (ethyl acetate / hexane = 1 / 2) to obtain 11g of a pale yellow solid. The obtained solid was measured by FAB-MS and confirmed to have an m / z of 547, confirming the intermediate M8 of the target product.

[0344] <Synthesis of intermediate M9> The intermediate layer M9 can be synthesized by the steps of the following reaction formula M9.

[0345] [Reaction formula M9] JPEG2025063842000094.jpg39170

[0346] In a 500 mL three-neck flask, add 10 g of 1-bromo-3-chlorocarbazole, 12 g of 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane), 7.7 g of potassium acetate, and Pd(dppf)Cl. 2 1.0g was added and the inside of the flask was replaced with Ar (argon). Next, 180mL of dioxane was added and stirred at 80°C for 5 hours. The obtained reaction solution was concentrated with an evaporative concentrator, and then the organic matter was dissolved with toluene and the inorganic matter was removed with a silica gel pad. The crude product was concentrated with an evaporative concentrator and purified with a silica gel column (ethyl acetate / hexane = 1 / 3) to obtain 7.9g of a white solid. The obtained solid was measured by FAB-MS and confirmed to have an m / z of 328, confirming that the intermediate M9 was the target product.

[0347] <Synthesis of intermediate M10> The intermediate layer M10 can be synthesized by the steps of the following reaction formula M10.

[0348] [Reaction formula M10] JPEG2025063842000095.jpg56170

[0349] In a 300 mL three-neck flask, 5.0 g of 1-bromo-2,3,4,5,6-pentafluorobenzene, 6.6 g of intermediate M9, 8.4 g of potassium carbonate, and Pd(PPh 3 ) 4 2.3g was added and the inside of the flask was replaced with Ar (argon). Next, 100mL of THF and 50mL of water were added and stirred while heating and refluxing for 5 hours. The organic layer of the resulting reaction solution was extracted with toluene, washed with water, and then dried with magnesium sulfate. The resulting solid was filtered and then concentrated with an evaporative concentrator. The crude product was purified with a silica gel column (ethyl acetate / hexane = 1 / 2) to obtain 7.1g of a pale yellow solid. The resulting solid was measured by FAB-MS and confirmed to have an m / z of 452, confirming that the intermediate M10 was the target product.

[0350] <Synthesis of intermediate M11> The intermediate layer M11 can be synthesized by the steps of the following reaction formula M11.

[0351] [Reaction formula M11] JPEG2025063842000096.jpg41170

[0352] 7.1 g of intermediate M10 and 40 mL of NMP were added to a 100 mL three-neck flask, and then K 3 PO 4 12g was added and stirred for 4 hours while heating at 160℃. After cooling the resulting reaction solution to room temperature, water was added and stirred for 10 minutes, and then saline and dichloromethane were added. Next, the organic layer was extracted with dichloromethane, washed with water and dried with magnesium sulfate. The resulting solid was filtered and then concentrated with an evaporative concentrator. Next, the crude product was recrystallized with toluene and ethanol to obtain 4.3g of a white solid. FAB-MS measurement of the resulting solid confirmed that it had an m / z of 348, confirming the target intermediate M11.

[0353] <Synthesis of intermediate M12> The intermediate layer M12 can be synthesized by the steps of the following reaction formula M12.

[0354] [Reaction formula M12] JPEG2025063842000097.jpg43170

[0355] In a 100 mL three-neck flask, add 2.0 g of intermediate M11 and K 4 [Fe(CN) 6 ] 8.5g, sodium carbonate 9.8g, Pd(amphos) 2 Cl 2 0.4g was added and the inside of the flask was replaced with Ar (argon). Next, 60mL of DMA was added and stirred for 5 hours while heating at 140°C. The organic layer of the resulting reaction solution was extracted with dichloromethane, washed with water, dried with magnesium sulfate, filtered, and then concentrated with an evaporative concentrator. The crude product was filtered through a silica gel column (ethyl acetate / hexane = 1 / 2) to obtain 1.4g of a pale yellow solid. The FAB-MS measurement of the resulting solid confirmed that it had m / z of 338, confirming the intermediate M12 of the target product.

[0356] <Synthesis of intermediate M13> The intermediate layer M13 can be synthesized by the steps of the following reaction formula M13.

[0357] [Reaction formula M13] JPEG2025063842000098.jpg47170

[0358] In a 100 mL three-neck flask, add 2.0 g of intermediate M11, 1.9 g of 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane), 1.2 g of potassium acetate, and Pd(OAc). 252 mg and XPhos 0.21 g were added, and the inside of the flask was replaced with Ar (argon). Next, 30 mL of dioxane was added, and the mixture was stirred at 120°C for 5 hours. The resulting reaction solution was concentrated using an evaporative concentrator, and then the organic matter was dissolved in toluene, and the inorganic matter was removed using a silica gel pad. The crude product was concentrated using an evaporative concentrator and filtered through a silica gel column (ethyl acetate / hexane = 1 / 3) to obtain 1.7 g of a white solid. The FAB-MS measurement of the resulting solid confirmed that it had an m / z of 439, and the intermediate M13 of the target product was identified.

[0359] <Synthesis of intermediate M14> The intermediate layer M14 can be synthesized by the steps of the following reaction formula M14.

[0360] [Reaction formula M14] JPEG2025063842000099.jpg73170

[0361] In a 50 mL three-neck flask, add 1.6 g of intermediate M13, 1.0 g of 2-chloro-4,6-diphenyl-1,3,5-triazine, 1.5 g of potassium carbonate, and Pd(PPh 3 ) 4 0.43g was added, the inside of the flask was replaced with Ar (argon), 20mL of THF and 10mL of water were added, and the mixture was stirred while being heated under reflux for 5 hours. The organic layer of the resulting reaction solution was extracted with toluene, washed with water, dried with magnesium sulfate, and the solid was filtered and then concentrated with an evaporative concentrator. The crude product was filtered with a silica gel column (ethyl acetate / hexane = 1 / 2) to obtain 1.7g of a pale yellow solid. The FAB-MS measurement of the resulting solid confirmed that it had m / z of 545, confirming the intermediate M14 of the target product.

[0362] (2) Synthesis of Compounds 25 and 41 Polycyclic compounds 25 and 41 according to one embodiment can be synthesized, for example, by the steps of Reaction Scheme 1 below.

[0363] [Reaction Scheme 1] JPEG2025063842000100.jpg56170

[0364] 3.3g of carbazole and 220mL of NMP were placed in a 500mL three-neck flask, and then 1.1g of NaH was added while immersed in ice, followed by 3.6g of intermediate M8. The mixture was then stirred at room temperature for 2 hours, then the temperature was raised to 180°C and stirred for 4 hours. The resulting reaction solution was cooled to room temperature, water was added, and the mixture was stirred for 10 minutes, after which brine and dichloromethane were added. The organic layer was then extracted with dichloromethane, washed with water, dried with magnesium sulfate, filtered, and concentrated in an evaporative concentrator. The crude product was then recrystallized with toluene and ethanol to obtain 8g of a yellow solid. The solid obtained was confirmed to have an m / z of 968 by FAB-MS measurement, and a mixture of compound 25 and compound 41 was obtained. Compound 25 and compound 41 were then separated by preparative HPLC, and 1.3g and 3.9g of compound 25 and compound 41 were obtained, respectively. Each compound was then purified by sublimation and used for characterization.

[0365] (3) Synthesis of compound 26 Polycyclic compound 26 according to one embodiment can be synthesized, for example, by the steps of Reaction Scheme 2 below.

[0366] [Reaction Scheme 2] JPEG2025063842000101.jpg52170

[0367] 3.3g of carbazole e and 220mL of NMP were placed in a 500mL three-neck flask, and 1.1g of NaH was added while immersed in ice, followed by 3.6g of intermediate M6. The mixture was then stirred at room temperature for 2 hours, and then heated to reflux and stirred for 4 hours. The resulting reaction solution was cooled to room temperature, and water was added and stirred for 10 minutes. Next, saline and dichloromethane were added, and the organic matter was extracted with dichloromethane, washed with water, and then dried with magnesium sulfate. The solid was then filtered and concentrated with an evaporative concentrator. The crude product was then recrystallized with toluene and ethanol to obtain 4.5g of a yellow solid. The resulting solid was measured by FAB-MS and confirmed to have an m / z of 968, confirming the target compound 26. The compound was then purified by sublimation and used for characterization.

[0368] (4) Synthesis of compound 29 The polycyclic compound 29 according to one embodiment can be synthesized, for example, by the steps of the following reaction scheme 3.

[0369] [Reaction Scheme 3] JPEG2025063842000102.jpg54170

[0370] 5.4g of carbazole and 360mL of THF were added to a 500mL three-neck flask, then 1.7g of NaH was added while immersed in ice, and 3.6g of intermediate M3 was added. Next, the mixture was stirred at room temperature for 2 hours, and then stirred for 4 hours while heating and refluxing. The resulting reaction solution was cooled to room temperature, water was added, and the mixture was stirred for 10 minutes, after which saline and dichloromethane were added. Next, the organic layer was extracted with dichloromethane, washed with water, and dried with magnesium sulfate. Next, the solid was filtered and concentrated with an evaporative concentrator. The obtained crude product was recrystallized with toluene and ethanol to obtain 8g of a yellow solid. The obtained solid was measured by FAB-MS and confirmed to have an m / z of 762, confirming the target compound 29. Next, the compound was purified by sublimation and used for characterization.

[0371] (5) Synthesis of compound 30 The polycyclic compound 30 according to one embodiment can be synthesized, for example, by the steps of Reaction Scheme 4 below.

[0372] [Reaction Scheme 4] JPEG2025063842000103.jpg66170

[0373] 10g of 3,6-diphenylcarbazole and 360mL of THF were added to a 500mL three-neck flask, then 1.7g of NaH was added while immersed in ice, and 3.6g of intermediate M3 was added. Next, the mixture was stirred at room temperature for 2 hours, and then stirred for 4 hours while heating and refluxing. The resulting reaction solution was cooled to room temperature, water was added, and the mixture was stirred for 10 minutes, after which saline and dichloromethane were added. Next, the organic layer was extracted with dichloromethane, washed with water, and then dried with magnesium sulfate. The solid was filtered and concentrated with an evaporative concentrator. Next, the crude product was recrystallized with toluene and ethanol to obtain 7.4g of a yellow solid. The obtained solid was measured by FAB-MS and confirmed to have an m / z of 762, confirming the target compound 30. Next, the compound was purified by sublimation and used for characterization.

[0374] (6) Synthesis of compound 44 The polycyclic compound 44 according to one embodiment can be synthesized, for example, by the steps of Reaction Scheme 5 below.

[0375] [Reaction Scheme 5] JPEG2025063842000104.jpg56170

[0376] 6.7g of 3,6-di-tert-butylcarbazole and 270mL of THF were added to a 500mL three-neck flask, then 1.3g of NaH was added while immersed in ice, and 3.6g of intermediate M5 was added. Next, the mixture was stirred at room temperature for 2 hours, and then stirred for 4 hours while heating and refluxing. The resulting reaction solution was cooled to room temperature, water was added, and the mixture was stirred for 10 minutes, after which saline and dichloromethane were added. Next, the organic layer was extracted with dichloromethane, washed with water, dried with magnesium sulfate, filtered, and concentrated in an evaporative concentrator. Next, the crude product was recrystallized with toluene and ethanol to obtain 6.2g of a yellow solid. The obtained solid was measured by FAB-MS and confirmed to have an m / z of 1211, confirming the target compound 44. Next, the compound was purified by sublimation and used for characterization.

[0377] (7) Synthesis of compound 57 The polycyclic compound 57 according to one embodiment can be synthesized, for example, by the steps of Reaction Scheme 6 below.

[0378] [Reaction Scheme 6] JPEG2025063842000105.jpg65170

[0379] In a 300 mL three-neck flask, add 2.8 g of carbazole and 140 mL of DMF. 3 PO 4 3.5g of toluene and 1.4g of intermediate M12 were added. Then, the mixture was heated at 160°C and stirred for 4 hours. After cooling to room temperature, water was added and the mixture was stirred for 10 minutes, and then saline and dichloromethane were added. Next, the organic layer was extracted with dichloromethane, washed with water, dried with magnesium sulfate, and the obtained solid was filtered and then concentrated with an evaporative concentrator. The obtained crude product was recrystallized with toluene and ethanol to obtain 2.0g of a yellow solid. The obtained solid was confirmed to have an m / z of 927 by FAB-MS measurement, confirming the target product, 57. Next, the compound was purified by sublimation and used for characterization.

[0380] (8) Synthesis of Compound 61 The polycyclic compound 61 according to one embodiment can be synthesized, for example, by the steps of Reaction Scheme 7 below.

[0381] [Reaction Scheme 7] JPEG2025063842000106.jpg72170

[0382] 2.1 g of carbazole and 110 mL of DMF were added to a 300 mL three-neck flask, and then K 3 PO 42.7g of M14 was added, followed by 1.7g of intermediate M14. The mixture was then heated to 160°C and stirred for 4 hours. After cooling to room temperature, water was added and the mixture was stirred for 10 minutes, after which saline and dichloromethane were added and the organic layer was extracted with dichloromethane. The extracted organic layer was then washed with water, dried over magnesium sulfate, the solid was filtered and then concentrated in an evaporative concentrator. The crude product was then recrystallized with toluene and ethanol to obtain 1.4g of a yellow solid. The FAB-MS measurement of the obtained solid confirmed that it was 1133m / z, confirming the target product, 61. The compound was then purified by sublimation and used for characterization.

[0383] 2. Evaluation of polycyclic compounds Table 1 below shows the polycyclic compounds used in the examples and comparative examples.

[0384] [Table 1] JPEG2025063842000108.jpg234170JPEG2025063842000109.jpg121170

[0385] Table 2 below shows the results of evaluating the luminescence characteristics of the polycyclic compounds used in the examples and comparative examples. Table 2 shows the maximum emission wavelength (PLλ max), fluorescence quantum yield (PLQY), Z-stimulus value, blue fluorescence efficiency index, and full width at half maximum (FWHM) of the emission spectrum were evaluated and shown. The emission characteristics of the maximum emission wavelength and full width at half maximum of the compounds of the examples and comparative examples were measured using a Hitachi High-Tech F-7000 spectrofluorophotometer under an inert gas atmosphere. The fluorescence quantum yield was measured using a Quantaurus QY manufactured by Hamamatsu Photonics. In addition, the Z-stimulus value (the CIE tristimulus value Z) of the CIE equation function (Color matching functions) at the maximum emission wavelength was a value based on the CIE 1931 color space. The blue fluorescence efficiency index corresponds to a value defined as the product of the fluorescence quantum yield and the Z-stimulus value at each maximum emission wavelength. The spectral luminance of each material was compared relatively according to the value of the blue fluorescence efficiency index. The emission characteristics evaluation of the compounds shown in Table 2 was performed in a toluene solution state of the compounds of the examples and comparative examples.

[0386] [Table 2]

[0387] Referring to Table 2, it can be seen that the polycyclic compounds of the examples emit blue light having a maximum emission wavelength of 470 nm or less. The compounds of the examples show higher quantum efficiency characteristics and higher blue luminous efficiency index characteristics than the compounds of the comparative examples. In addition, the compounds of the examples show narrower half-width characteristics than the compounds of the comparative examples. In other words, when considering the results of the evaluation of the luminous properties of the compounds, it can be seen that the compounds of the examples, which include an indolocarbazole core, a cyano group or a triazine group, and a plurality of carbazole groups, each of which is bonded to one aryl ring, show higher luminous efficiency, excellent color characteristics, and high color purity characteristics than the compounds of the comparative examples that do not have such a compound structure.

[0388] 3. Fabrication and evaluation of light-emitting devices (1) Fabrication of light-emitting element Light-emitting devices containing the polycyclic compound of one embodiment or the comparative compound in the light-emitting layer were manufactured by the following method. The polycyclic compound of one embodiment was used as a dopant material in the light-emitting layer to manufacture the light-emitting devices of Examples 1 to 8. The light-emitting devices of Comparative Examples 1 to 7 were manufactured by using the comparative compounds X1 to X7 as dopant materials in the light-emitting layer, respectively.

[0389] A glass substrate with ITO patterned as the first electrode was ultrasonically cleaned with isopropyl alcohol and pure water for 5 minutes each. After ultrasonic cleaning, it was irradiated with UV for 30 minutes and then treated with ozone. Next, HAT-CN was deposited in a thickness of 10 nm, TrisPCz in a thickness of 30 nm, and mCBP in a thickness of 5 nm in sequence to form a hole transport region.

[0390] Next, the example compound or the comparative example compound and mCBP were co-deposited to form a light-emitting layer having a thickness of 30 nm. The example compound or the comparative example compound and mCBP were co-deposited in a weight ratio of 10:90. In the manufacture of the light-emitting device, the example compound or the comparative example compound was used as a dopant material.

[0391] Next, SF3-TRZ was deposited to a thickness of 10 nm, SF3-TRZ:Liq was deposited to a thickness of 20 nm in a weight ratio of 50:50, and Liq was deposited to a thickness of 2 nm to form an electron transport region.

[0392] Next, Al was evaporated to a thickness of 100 nm to form a second electrode.

[0393] In the examples, the hole transport region, the light emitting layer, the electron transport region, and the second electrode were formed using a vacuum deposition apparatus.

[0394] The compounds used in the production of the light-emitting device are as follows:

[0395] (Materials used in manufacturing the light-emitting element) JPEG2025063842000111.jpg107170

[0396] (2) Evaluation of light-emitting elements The following Table 3 shows the evaluation results of the light emitting devices of the Examples and Comparative Examples. Table 3 shows the maximum emission wavelength (λmax), maximum external quantum yield (EQEmax), blue device efficiency index, and relative device life for the light emitting devices of the Examples and Comparative Examples. The blue device efficiency index is defined as the product of the maximum external quantum yield and the Z stimulus value at each maximum emission wavelength, and the Z stimulus value is a value in the CIE equation function at each maximum emission wavelength, and a value based on the CIE 1931 color space is used. The relative device life is 1000cd / m 2 The time it takes for the brightness to decrease to 50% from the initial brightness value when the device is continuously driven at 100 is shown as a relative element lifespan, with the value of Comparative Example 1 being 100.

[0397] [Table 3]

[0398] Referring to the results in Table 3, it can be seen that the light emitting device of the embodiment emits blue light having a maximum emission wavelength of 470 nm or less. In addition, in terms of the characteristics of the blue device efficiency index evaluation taking into account color characteristics, it can be said that the light emitting device of the embodiment shows superior efficiency characteristics compared to the light emitting device of the comparative example. In addition, in terms of relative device life characteristics, the embodiment shows superior results compared to the comparative example. That is, in the case of the polycyclic compound of the embodiment used in the light emitting device of the embodiment of the present invention, since it has a specific bonding structure of indolocarbazole-triazine (or cyano group)-carbazole that is different from that of the comparative example, it can have characteristics such as superior maximum quantum yield, half width of the compound, and material stability compared to the compound of the comparative example, and it can be said that the device including the same also shows superior efficiency and life characteristics.

[0399] The comparative compound X1 used in Comparative Example 1 has similar bonding characteristics of the substituents as the polycyclic compounds of the Examples of the present invention, but is different in that the core portion, which is the central skeleton, contains carbazole instead of indolocarbazole. The comparative compound X1 shows properties lower than the compounds of the Examples of the present invention in terms of fluorescence quantum yield and emission half width. In addition, the comparative compound X1 contains carbazole, which has a smaller number of condensed rings than indolocarbazole, in the core portion, so that the mobility of the central skeleton is high, and therefore deterioration of the material occurs easily. It is considered that the light-emitting device of Comparative Example 1 containing the comparative compound X1 shows a reduced element life characteristic compared to the Examples.

[0400] The comparative compounds X2 and X3 do not contain a cyano group or a triazine group, which are electron-withdrawing groups that are essential for the compounds of the examples of the present invention. As a result, the comparative compounds X2 and X3 do not exhibit thermally activated delayed fluorescence (TADF) or have weak TADF characteristics, and therefore cannot effectively utilize triplet excitons for light emission, and exhibit low external quantum yield characteristics. In addition, it is believed that the lifetime of the light-emitting elements of Comparative Examples 2 and 3 is also reduced compared to the light-emitting elements of the examples, due to the deterioration caused by triplet excitation.

[0401] The light-emitting device of Comparative Example 4 using Comparative Example Compound X4 has a maximum emission wavelength of 505 nm, and exhibits light emission characteristics of light with a wavelength longer than blue light, and exhibits poor device life characteristics compared to the Examples. In the case of Comparative Example Compound X4, it is considered that green light is emitted because a strong charge separation state is formed between the carbazole group, which is an electron-donating group, and the triazine group, which is an electron-withdrawing group. In addition, in the case of Comparative Example Compound X4, the carbazole group is not directly substituted with indolocarbazole, and therefore the effect of suppressing the rotational motion of the carbazole group is lower than in the Example compounds, and the material stability is reduced, which is considered to have led to the deterioration of the light-emitting device life characteristics of Comparative Example 4.

[0402] The comparative compounds X5, X6, and X7 have a structure in which an electron-withdrawing group and an indolocarbazole group are directly bonded, and this structural feature results in a charge separation state suitable for blue light emission. However, the comparative compounds X5, X6, and X7 show lower fluorescence quantum yields and wider half-width characteristics than the compounds of the examples. This is because, in the compounds of the examples, multiple carbazole groups are all bonded to one ring, suppressing the rotation of the carbazole groups, whereas the mobility of the carbazole groups cannot be suppressed in the compounds of the comparative examples X5, X6, and X7, and the light-emitting devices of the comparative examples 5 to 7 show reduced external quantum efficiency and life characteristics.

[0403] The polycyclic compound of one embodiment has a structure including a fused ring core of indolocarbazole, at least one electron-withdrawing group directly bonded to the fused ring core, and a plurality of carbazole groups each bonded to one of the rings of the fused ring core. The polycyclic compound of one embodiment may exhibit excellent luminous efficiency and excellent material stability characteristics. In addition, the polycyclic compound of one embodiment may be used as a thermally activated delayed fluorescent material. In addition, the light-emitting device of one embodiment including the polycyclic compound of one embodiment in the light-emitting layer may exhibit excellent luminous efficiency characteristics in the blue light-emitting region and long life characteristics.

[0404] Although the present invention has been described above with reference to preferred embodiments thereof, it will be understood by those skilled in the art or those having ordinary knowledge in the art that various modifications and variations of the present invention can be made without departing from the spirit and technical scope of the present invention as set forth in the claims below.

[0405] Therefore, the technical scope of the present invention should be determined not by the contents described in the detailed description of the specification, but by the claims. [Explanation of symbols]

[0406] DD, DD-TD, DD-b, DD-c: Display device ED: Light emitting element EL1: First electrode EL2: 2nd electrode EML: Light-emitting layer

Claims

1. A first electrode; A second electrode disposed on the first electrode; A light-emitting device comprising: a light-emitting layer disposed between the first electrode and the second electrode, the light-emitting layer comprising a first compound represented by the following Chemical Formula 1: [Chemical formula 1] In the above Chemical Formula 1, R １ ~R １１ At least one of R is a first substituent which is a cyano group or a substituted or unsubstituted triazine group, and R excluding the first substituent １ ~R １１ two or more selected from the above are second substituents each being a substituted or unsubstituted carbazole group bonded to any one ring selected from Ar1 to Ar3; The remainders are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group having from 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having from 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having from 2 to 30 ring carbon atoms.

2. The light emitting device according to claim 1, wherein the formula 1 is represented by any one of the following formulas 1-1 to 1-3: [Chemical formula 1-1] [Chemical formula 1-2] [Chemical formula 1-3] In the Chemical Formulas 1-1 to 1-3, Sb1 is a cyano group or is represented by the following chemical formula 2, and Sb2 is represented by the following chemical formula 3: Ra to Rc each independently represent a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group having from 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having from 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having from 2 to 30 ring carbon atoms, n1 is 1, n2 is an integer between 1 and 3, and n3 is an integer between 1 and 4, m1 is 2 or 3, m2 is an integer of 2 to 4, p1 is 0 or 1, p2 is an integer of 0 to 2, q is an integer of 0 to 2, and r is an integer of 0 to 3, R ５ ~R １１ is as defined in Chemical Formula 1 above: [Chemical formula 2] [Chemical formula 3] In the above Chemical Formula 2 and Chemical Formula 3, W １ , W ２ , and R ２１ ~R ２８ each independently represents a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group having from 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having from 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having from 2 to 30 ring carbon atoms, is the position at which Ar1 to Ar3 are bonded to the rings.

3. The light-emitting device according to claim 2, wherein the chemical formula 1-1 is represented by the following chemical formula 1-1a: [Chemical formula 1-1a] In the formula 1-1a, Sb1 and Sb2 are as defined in the formula 1-1; R ５ ~R １１ is as defined in Chemical Formula 1 above.

4. The light-emitting device according to claim 2, wherein the chemical formula 1-2 is represented by the following chemical formula 1-2a: [Chemical formula 1-2a] In the formula 1-2a, Sb1, Sb2, and Rb are as defined in the formula 1-2; ８ ~R １１ is as defined in Chemical Formula 1 above.

5. The light-emitting device according to claim 1 , wherein at least one hydrogen atom of the first compound is substituted with a deuterium atom.

6. 2. The light emitting device of claim 1, wherein the light emitting layer further comprises at least one of a second compound represented by the following chemical formula HT-1 and a third compound represented by the following chemical formula ET-1: [Chemical formula HT-1] In the above chemical formula HT-1, A １ or A ８ each independently represents N or CR ５１ and L １ represents a direct bond, a substituted or unsubstituted arylene group having from 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having from 2 to 30 ring carbon atoms, Y ａ is a direct bond, CR ５２ R ５３ , or SiR ５４ R ５５ and Ar １ is a substituted or unsubstituted aryl group having from 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having from 2 to 30 ring carbon atoms, R ５１ ~R ５５ are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted thio group, a substituted or unsubstituted oxy group, a substituted or unsubstituted amine group, a substituted or unsubstituted boron group, a substituted or unsubstituted alkyl group having from 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having from 2 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having from 6 to 60 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having from 2 to 60 ring carbon atoms, or are bonded to adjacent groups to form a ring: [Chemical formula ET-1] In the above chemical formula ET-1, X １ ~X ３ At least one of them is N and the rest is CR ５６ and R ５６ is a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having from 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having from 6 to 60 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having from 2 to 60 ring carbon atoms, b1 to b3 each independently represents an integer of 0 to 10, Ar ２ ~Ar ４ each independently represents a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having from 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having from 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having from 2 to 30 ring carbon atoms, L ２ ~L ４ each independently represents a direct bond, a substituted or unsubstituted arylene group having from 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having from 2 to 30 ring carbon atoms.

7. The light-emitting device according to claim 6, wherein the light-emitting layer further comprises a fourth compound represented by the following chemical formula D-1: [Chemical formula D-1] In the above chemical formula D-1, Q １ ~Q ４ are each independently C or N; C1 to C4 each independently represent a substituted or unsubstituted hydrocarbon ring having from 5 to 30 ring carbon atoms, or a substituted or unsubstituted heterocycle having from 2 to 30 ring carbon atoms; L １１ ~L １３ are each independently a direct bond, a substituted or unsubstituted divalent alkyl group having from 1 to 20 carbon atoms, a substituted or unsubstituted arylene group having from 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having from 2 to 30 ring carbon atoms, b11 to b13 each independently represent 0 or 1; R ６１ ~R ６６ each independently represents a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted thio group, a substituted or unsubstituted oxy group, a substituted or unsubstituted amine group, a substituted or unsubstituted boron group, a substituted or unsubstituted alkyl group having from 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having from 2 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having from 6 to 60 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having from 2 to 60 ring carbon atoms, Each of d1 to d4 independently represents an integer of 0 or more and 4 or less.

8. The light-emitting element according to claim 7 , wherein the light-emitting layer comprises the first compound, the second compound, the third compound, and the fourth compound.

9. The light-emitting device according to claim 1 , wherein the light-emitting layer emits delayed fluorescence.

10. The light-emitting device of claim 1 , wherein the light-emitting layer emits blue light.

11. The light-emitting device according to claim 1 , wherein the first compound is any one of the compounds in the following first compound group: [First compound group] In the first group of compounds, d (in italics) is a deuterium atom.

12. A polycyclic compound represented by the following chemical formula 1: [Chemical formula 1] In the above Chemical Formula 1, R １ ~R １１ At least one of R is a first substituent which is a cyano group or a substituted or unsubstituted triazine group, and R excluding the first substituent １ ~R １１ two or more selected from the above are second substituents each being a substituted or unsubstituted carbazole group bonded to any one ring selected from Ar1 to Ar3; The remainders are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group having from 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having from 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having from 2 to 30 ring carbon atoms.

13. The polycyclic compound according to claim 12, wherein the formula 1 is represented by any one of the following formulas 1-1 to 1-3: [Chemical formula 1-1] [Chemical formula 1-2] [Chemical formula 1-3] In the Chemical Formulas 1-1 to 1-3, Sb1 is a cyano group or is represented by the following chemical formula 2, and Sb2 is represented by the following chemical formula 3: Ra to Rc each independently represent a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group having from 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having from 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having from 2 to 30 ring carbon atoms, n1 is 1, n2 is an integer between 1 and 3, and n3 is an integer between 1 and 4, m1 is 2 or 3, m2 is an integer of 2 to 4, p1 is 0 or 1, p2 is an integer of 0 to 2, q is an integer of 0 to 2, and r is an integer of 0 to 3, R ５ ~R １１ is as defined in Chemical Formula 1 above: [Chemical formula 2] [Chemical formula 3] In the above Chemical Formula 2 and Chemical Formula 3, W １ , W ２ , and R ２１ ~R ２８ each independently represents a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group having from 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having from 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having from 2 to 30 ring carbon atoms, is the position at which Ar1 to Ar3 are bonded to the rings.

14. The polycyclic compound according to claim 13, wherein the chemical formula 1-1 is represented by the following chemical formula 1-1a: [Chemical formula 1-1a] In the formula 1-1a, Sb1 and Sb2 are as defined in the formula 1-1; R ５ ~R １１ is as defined in Chemical Formula 1 above.

15. The polycyclic compound according to claim 13, wherein the chemical formula 1-2 is represented by the following chemical formula 1-2a: [Chemical formula 1-2a] In the formula 1-2a, Sb1, Sb2, and Rb are as defined in the formula 1-2; ８ ~R １１ is as defined in Chemical Formula 1 above.

16. R of Formula 1 １ ~R １１ At least one of the groups is a deuterium atom or R １ ~R １１ The polycyclic compound according to claim 12, wherein at least one hydrogen atom of the formula (I) is substituted with a deuterium atom.

17. The polycyclic compound according to claim 12, wherein the compound represented by Chemical Formula 1 is a blue light-emitting dopant.

18. The polycyclic compound according to claim 12, wherein the compound represented by Chemical Formula 1 is a thermally activated delayed fluorescent material.

19. The polycyclic compound according to claim 12, wherein the first compound is any one of the compounds in the following first compound group: [First compound group] In the first group of compounds, d (in italics) is a deuterium atom.

20. A base layer; a circuit layer disposed on the base layer; a display element layer disposed on the circuit layer and including a light-emitting element; The light-emitting element includes a first electrode, a second electrode disposed on the first electrode, and a light-emitting layer disposed between the first electrode and the second electrode, the light-emitting layer including a polycyclic compound represented by the following chemical formula 1: [Chemical formula 1] In the above Chemical Formula 1, R １ ~R １１ At least one of R is a first substituent which is a cyano group or a substituted or unsubstituted triazine group, and R excluding the first substituent １ ~R １１ two or more selected from the above are second substituents each being a substituted or unsubstituted carbazole group bonded to any one ring selected from Ar1 to Ar3; The remainders are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group having from 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having from 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having from 2 to 30 ring carbon atoms.

21. The display device of claim 20, wherein the light emitting element emits blue light.

22. The display device of claim 20 further comprising a light control layer comprising quantum dots.

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