Light-emitting element and polycyclic compound for light-emitting element

Abstract

Embodiments provide a polycyclic compound and a light-emitting element including the polycyclic compound. The light emitting element includes a first electrode, a second electrode disposed on the first electrode, and an emission layer disposed between the first electrode and the second electrode and including a polycyclic compound. The polycyclic compound is represented by Formula 1, which is explained in the specification. [Formula 1] # imgabs0 #

Description

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS

[0002] This application claims priority to and the benefit of Korean Patent Application No. 10-2023-0082104 filed in the Korean Intellectual Property Office on June 26, 2023, the entire contents of which are incorporated herein by reference. Technical Field

[0003] The disclosure herein relates to a light-emitting element and a polycyclic compound used in the light-emitting element. Background Art

[0004] Active development of organic electroluminescent display devices as image display devices is continuing. The organic electroluminescent display device is different from the liquid crystal display device and is a so-called self-luminous display device in which holes and electrons injected from the first electrode and the second electrode are recombined in the emission layer so that the light-emitting material including the organic compound in the emission layer emits light to achieve display.

[0005] When a light-emitting element is applied to a display device, it is necessary to improve driving voltage, emission efficiency, and lifespan, and continuous development of materials for light-emitting elements that can stably achieve these characteristics is required.

[0006] It is to be understood that this background technology section is intended, in part, to provide a useful background for understanding the technology. However, this background technology section may also include ideas, concepts, or cognitions that were not part of the known or understood by a person skilled in the relevant art before the corresponding effective filing date of the subject matter disclosed herein. Summary of the invention

[0007] The present disclosure provides a light emitting element that can have low driving voltage characteristics and long life characteristics.

[0008] The present disclosure provides a polycyclic compound that can reduce the driving voltage of a light-emitting element and improve the life of the light-emitting element.

[0009] Embodiments provide a light emitting element, which may include a first electrode, a second electrode disposed on the first electrode, and an emission layer disposed between the first electrode and the second electrode. The emission layer may include a polycyclic compound represented by Formula 1 as the first compound.

[0010] [Formula 1]

[0011]

[0012] In Formula 1, L may be a substituted or unsubstituted polycyclic aromatic hydrocarbon group of 12 to 25 ring-forming carbon atoms; and X and Y may each independently be N(R 7 ), O, S or Se. In Formula 1, R 1 To R 4Each of them may be independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 60 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 60 ring carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 ring carbon atoms. In Formula 1, R 5 To R 7 Each of n1 and n4 may be independently selected from an integer of 0 to 4; and n2 and n3 may be independently selected from an integer of 0 to 3.

[0013] In an embodiment, the first compound may be represented by any one of Formula 2-1 to Formula 2-5.

[0014] [Formula 2-1]

[0015]

[0016] [Formula 2-2]

[0017]

[0018] [Formula 2-3]

[0019]

[0020] [Formula 2-4]

[0021]

[0022] [Formula 2-5]

[0023]

[0024] In Formula 2-1 to Formula 2-5, R a1 To R a6 , R b1 To R b6 , R c1 To R c4 , R d1 To R d4 and R e1 To R e6Each of c1, c2, d1 and d3 may be independently selected from an integer of 0 to 4; c3, c4, d2 and d4 may be independently selected from an integer of 0 to 2; and X, Y, R 1 To R 6 and n1 to n4 may be the same as defined in Formula 1.

[0025] In an embodiment, the first compound may be represented by Formula 2-1A.

[0026] [Formula 2-1A]

[0027]

[0028] In formula 2-1A, R 21 ′ and R 31 ' can each independently be a hydrogen atom or a deuterium atom; and R 22 ′ and R 32 ' may each independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 15 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 15 ring carbon atoms. In Formula 2-1A, R 51 ' to R 55 ′ and R 61 ' to R 65 ' may each independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group of 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group of 6 to 10 ring-forming carbon atoms. In Formula 2-1A, n21' and n31' may each independently be an integer selected from 0 to 2; and R 1 , R 4 , R a1 To R a6 , n1, n4, X, and Y may be the same as defined in Formula 1 and Formula 2-1.

[0029] In an embodiment, the first compound may be represented by Formula 2-2A.

[0030] [Formula 2-2A]

[0031]

[0032] In formula 2-2A, R 21 ′ and R 31 ' can each independently be a hydrogen atom or a deuterium atom; and R 22 ′ and R 32' may each independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 15 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 15 ring carbon atoms. In Formula 2-2A, R 51 ' to R 55 ′ and R 61 ' to R 65 ' may each independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group of 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group of 6 to 10 ring carbon atoms. In Formula 2-2A, n21' and n31' may each independently be an integer selected from 0 to 2; and R 1 , R 4 , R b1 To R b6 , n1, n4, X, and Y may be the same as defined in Formula 1 and Formula 2-2.

[0033] In an embodiment, in Formula 1, L may have a lowest triplet energy level (T1) in the range of about 1.5 eV to about 2.4 eV.

[0034] In an embodiment, the first compound may be represented by Formula 3.

[0035] [Formula 3]

[0036]

[0037] In formula 3, R 5a To R 5e and R 6a To R 6e may each independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group of 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group of 6 to 10 ring carbon atoms; and R 1 To R 4 , n1 to n4, L, X, and Y may be the same as defined in Formula 1.

[0038] In an embodiment, the first compound may be represented by Formula 4.

[0039] [Formula 4]

[0040]

[0041] In formula 4, R 21 and R 31 can each independently be a hydrogen atom or a deuterium atom; and R 22 and R 32Each of n21 and n31 may be independently selected from an integer of 0 to 2; and R 1 , R 4 To R 6 , n1, n4, L, X and Y may be the same as defined in Formula 1.

[0042] In an embodiment, the first compound may be represented by any one of Formula 5-1 to Formula 5-4.

[0043] [Formula 5-1]

[0044]

[0045] [Formula 5-2]

[0046]

[0047] [Formula 5-3]

[0048]

[0049] [Formula 5-4]

[0050]

[0051] In Formula 5-1 to Formula 5-4, R 71 To R 75 Each of them may be independently a substituted or unsubstituted aryl group having 6 to 20 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 20 ring carbon atoms. 1 To R 6 , n1 to n4 and L may be the same as defined in Formula 1.

[0052] In an embodiment, in Formula 1, the substituents of L and R 1 To R 7 At least one of may each independently be a deuterium atom or a substituent including a deuterium atom.

[0053] In an embodiment, the emission layer may further include at least one of a second compound represented by Formula HT-1, a third compound represented by Formula ET-1, and a fourth compound represented by Formula S-1, wherein Formula HT-1, Formula ET-1, and Formula S-1 are explained below.

[0054] In an embodiment, the emission layer may include a first compound, a second compound, and a third compound.

[0055] In an embodiment, the emission layer may include a first compound, a second compound, a third compound, and a fourth compound.

[0056] In an embodiment, the first compound may include at least one compound selected from Compound Group 1, which is explained below.

[0057] Embodiments provide polycyclic compounds that may be represented by Formula 1, which is explained herein.

[0058] In an embodiment, L may be a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, or a substituted or unsubstituted fluorenyl group.

[0059] In an embodiment, the polycyclic compound represented by Formula 1 may be represented by any one of Formula 2-1 to Formula 2-5, which are explained herein.

[0060] In an embodiment, the polycyclic compound represented by Formula 2-1 may be represented by Formula 2-1A, which is explained herein.

[0061] In an embodiment, the polycyclic compound represented by Formula 2-2 may be represented by Formula 2-2A, which is explained herein.

[0062] In an embodiment, the polycyclic compound represented by Formula 1 may be represented by Formula 3, which is explained herein.

[0063] In an embodiment, the polycyclic compound represented by Formula 1 may be represented by Formula 4, which is explained herein.

[0064] In an embodiment, the polycyclic compound represented by Formula 1 may be represented by any one of Formula 5-1 to Formula 5-4, which are explained herein.

[0065] In an embodiment, at least one of X and Y may be each independently N(R 7 ).

[0066] In an embodiment, the polycyclic compound represented by Formula 1 may be selected from Compound Group 1, which is explained below.

[0067] In an embodiment, wherein in the polycyclic compound represented by Formula 1, a difference between the lowest singlet energy level and the second lowest triplet energy level may be greater than a difference between the second lowest triplet energy level and the lowest triplet energy level.

[0068] It is to be understood that the above embodiments have been described in a general and explanatory sense only and not for purposes of limitation, and the present disclosure is not limited to the above embodiments. BRIEF DESCRIPTION OF THE DRAWINGS

[0069] The attached drawings are included to provide a further understanding of the embodiments, and are incorporated into and constitute a part of this specification. The drawings illustrate the embodiments of the present disclosure and its principles. The above and other aspects and features of the present disclosure will become more apparent by describing the embodiments of the present disclosure in detail with reference to the attached drawings, in which:

[0070] Figure 1 is a schematic plan view of a display device according to an embodiment;

[0071] Figure 2 is a schematic cross-sectional view of a display device according to an embodiment;

[0072] Figure 3 is a schematic cross-sectional view of a light emitting element according to an embodiment;

[0073] Figure 4 is a schematic cross-sectional view of a light emitting element according to an embodiment;

[0074] Figure 5 is a schematic cross-sectional view of a light emitting element according to an embodiment;

[0075] Figure 6 is a schematic cross-sectional view of a light emitting element according to an embodiment;

[0076] 7A to 7C They are schematic diagrams of the energy levels of polycyclic compounds;

[0077] Figure 8 is a schematic cross-sectional view of a display device according to an embodiment;

[0078] Fig. 9 is a schematic cross-sectional view of a display device according to an embodiment;

[0079] Fig.10 is a schematic cross-sectional view of a display device according to an embodiment;

[0080] Fig.11 is a schematic cross-sectional view of a display device according to an embodiment; and

[0081] Fig.12 is a schematic perspective view of an interior of a vehicle including a display device according to an embodiment. DETAILED DESCRIPTION

[0082] The present disclosure will now be described more fully below with reference to the attached drawings in which embodiments are shown. However, the present disclosure may be embodied in different forms and should not be construed as limited to the embodiments set forth herein. Rather, these embodiments are provided so that the present disclosure will be thorough and complete and will fully convey the scope of the present disclosure to those skilled in the art.

[0083] In the drawings, the size, ratio, and dimensions (eg, thickness) of elements may be exaggerated for ease of description and for clarity. Like reference numerals and reference characters refer to like elements throughout.

[0084] In the specification, it will be understood that when an element (or region, layer, portion, etc.) is referred to as being "on", "connected to" or "coupled to" another element (or region, layer, portion, etc.), it may be directly on, directly connected to or directly coupled to the other element (or region, layer, portion, etc.), or one or more intervening elements may be present between them. In a similar sense, when an element (or region, layer, portion, etc.) is described as "covering" another element (or region, layer, portion, etc.), it may directly cover the other element (or region, layer, portion, etc.), or one or more intervening elements may be present between them.

[0085] In the specification, when an element is "directly on," "directly connected to," or "directly coupled to" another element, there are no intervening elements. For example, "directly on" may mean that two layers or two elements are disposed without another element (such as an adhesive element) between them.

[0086] As used herein, expressions used in the singular such as “a”, “an” and “the” are intended to include the plural forms as well, unless the context clearly indicates otherwise.

[0087] As used herein, the term "and / or" includes any and all combinations of one or more of the associated listed items. For example, "A and / or B" may be understood to mean "A, B, or A and B". The terms "and" and "or" may be used in a conjunctive sense or a disjunctive sense and may be understood to be equivalent to "and / or".

[0088] In the specification and claims, the term "at least one of" is intended to include the meaning of "at least one selected from the group consisting of" for the purposes of its meaning and interpretation. For example, "at least one of A, B, and C" may be understood to mean only A, only B, only C, or any combination of two or more of A, B, and C, such as ABC, ACC, BC, or CC. When following a list of elements, the term "at least one of" modifies the entire list of elements and does not modify the individual elements of the list.

[0089] It will be understood that although the terms first, second, etc. may be used to describe various elements in this article, these elements should not be limited by these terms. These terms are only used to distinguish one element from another element. Therefore, without departing from the teachings of the present disclosure, the first element may be referred to as the second element. Similarly, without departing from the scope of the present disclosure, the second element may be referred to as the first element.

[0090] For ease of description, spatially relative terms such as "below," "under," "down," "above," or "on" may be used herein to describe the relationship between one element or component and another element or component as illustrated in the accompanying drawings. It will be understood that the spatially relative terms are intended to encompass different orientations of the device in use or operation in addition to the orientation depicted in the accompanying drawings. For example, in the case where the device illustrated in the accompanying drawings is turned over, a device that is "below" or "below" another device may be placed "above" the other device. Accordingly, the illustrative term "below" may include both a lower position and an upper position. The device may also be oriented in other directions, and therefore the spatially relative terms may be interpreted differently depending on the orientation.

[0091] As used herein, the term "about" or "approximately" includes the stated value and means within an acceptable range of deviation of the stated value determined by one of ordinary skill in the art taking into account the measurement in question and the errors associated with the measurement of the stated quantity (i.e., the limitations of the measurement system). For example, "about" can mean within one or more standard deviations of the stated value, or within ±20%, ±10%, or ±5% of the stated value.

[0092] It should be understood that the terms “comprise,” “comprising,” “include,” “including,” “have,” “having,” “contains,” and “containing” and the like are intended to indicate the presence of the recited features, integers, steps, operations, elements, components, or combinations thereof in the present disclosure, but do not preclude the presence or addition of one or more other features, integers, steps, operations, elements, components, or combinations thereof.

[0093] Unless otherwise defined or implied herein, all terms (including technical terms and scientific terms) used have the same meaning as those commonly understood by those skilled in the art to which the present disclosure belongs. It will be further understood that terms, such as those defined in commonly used dictionaries, should be interpreted as having a meaning consistent with their meaning in the context of the relevant art and should not be interpreted in an ideal or overly formal sense unless clearly defined in the specification.

[0094] In the specification, the term "substituted or unsubstituted" can describe a group that is unsubstituted or substituted by at least one substituent selected from the group consisting of: a deuterium atom, a halogen atom, a cyano group, a nitro group, an amino group, an amine group, a silyl group, an oxy group, a sulfenyl 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. Each of the substituents listed above can itself be substituted or unsubstituted. For example, a biphenyl group can be interpreted as an aryl group, or it can be interpreted as a phenyl group substituted by a phenyl group.

[0095] In the specification, the term "bonded to an adjacent group to form a ring" may be interpreted as a group bonded to an adjacent group to form a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocyclic ring. The hydrocarbon ring may be aliphatic or aromatic. The heterocyclic ring may be aliphatic or aromatic. The hydrocarbon ring and the heterocyclic ring may each independently be a monocyclic or polycyclic ring. The ring formed by adjacent groups bonded to each other may itself be connected to another ring to form a spiro structure.

[0096] In the specification, the term "adjacent group" may be interpreted as a substituent replacing an atom directly connected to the atom substituted by the corresponding substituent, as another substituent replacing the atom substituted by the corresponding substituent, or as a substituent located closest to the corresponding substituent in space. For example, the two methyl groups in 1,2-dimethylbenzene may be interpreted as "adjacent groups" to each other, and the two ethyl groups in 1,1-diethylcyclopentane may be interpreted as "adjacent groups" to each other. For example, the two methyl groups in 4,5-dimethylphenanthrene may be interpreted as "adjacent groups" to each other.

[0097] In the specification, examples of the halogen atom may include a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom.

[0098] In the specification, the alkyl group may be linear or branched. The number of carbon atoms in the alkyl group may be 1 to 60, 1 to 50, 1 to 30, 1 to 20, 1 to 10, or 1 to 6. Examples of the alkyl group may include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, isobutyl, 2-ethylbutyl, 3,3-dimethylbutyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 2-butylhexyl, n-heptyl, 1-methylheptyl, 2,2-dimethylheptyl, 2-ethylheptyl, 2-butylheptyl, n-octyl, tert-octyl, 2-ethyloctyl, 2-butyloctyl, 2-hexyloctyl, 3,7-dimethyloctyl, n-nonyl, n-decyl, adamantyl, 2-ethyldecyl, 2-butyldecyl, 2-hexyldecyl, 2-octyldecyl, n-undecyl, alkyl, n-dodecyl, 2-ethyldodecyl, 2-butyldodecyl, 2-hexyldodecyl, 2-octyldodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, 2-ethylhexadecyl, 2-butylhexadecyl, 2-hexylhexadecyl, 2-octylhexadecyl, n-heptadecyl, n-octadecyl, n-nonadecyl, n-eicosyl, 2-ethyleicosyl, 2-butyleicosyl, 2-hexyleicosyl, 2-octyleicosyl, n-heonicosyl, n-docosyl, n-tricosyl, n-tetracosyl, n-pentacosyl, n-hexacosyl, n-heptacosyl, n-octacosyl, n-nonacosyl, n-triacontyl, and the like, but the embodiment is not limited thereto.

[0099] In the specification, the cycloalkyl group may be a cyclic alkyl group. The number of carbon atoms in the cycloalkyl group may be 3 to 60, 3 to 50, 3 to 30, 3 to 20, or 3 to 10. Examples of the cycloalkyl group may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, norbornyl, 1-adamantyl, 2-adamantyl, isobornyl, bicycloheptyl, etc., but the embodiment is not limited thereto.

[0100] In the specification, the alkenyl group may be a hydrocarbon group including at least one carbon-carbon double bond in the middle or at the end of an alkyl group having 2 or more carbon atoms. The alkenyl group may be linear or branched. The number of carbon atoms in the alkenyl group is not particularly limited, but may be 2 to 60, 2 to 30, 2 to 20, or 2 to 10. Examples of alkenyl groups may include vinyl, 1-butenyl, 1-pentenyl, 1,3-butadienyl, styryl, styrylvinyl, etc., but embodiments are not limited thereto.

[0101] In the specification, the alkynyl group may be a hydrocarbon group including at least one carbon-carbon triple bond in the middle or at the end of an alkyl group having 2 or more carbon atoms. The alkynyl group may be straight chain or branched. The number of carbon atoms in the alkynyl group is not particularly limited, but may be 2 to 60, 2 to 30, 2 to 20, or 2 to 10. Examples of the alkynyl group may include ethynyl, propynyl, etc., but embodiments are not limited thereto.

[0102] In the specification, the hydrocarbon ring group may be any functional group or substituent derived from an aliphatic hydrocarbon ring. For example, the hydrocarbon ring group may be a saturated hydrocarbon ring group having 5 to 30 or 5 to 20 ring-forming carbon atoms.

[0103] In the specification, the aryl group may be any functional group or substituent derived from an aromatic hydrocarbon ring. The aryl group may be monocyclic or polycyclic. The number of ring carbon atoms in the aryl group may be 6 to 60, 6 to 30, 6 to 20, 6 to 15 or 6 to 10. Examples of aryl groups may include phenyl, naphthyl, fluorenyl, anthracenyl, phenanthrenyl, biphenyl, terphenyl, quaterphenyl, pentaphenyl, hexaphenyl, triphenylene, pyrenyl, benzofluoranthenyl, 1,2-triphenylenyl, etc., but embodiments are not limited thereto.

[0104] In the specification, the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure. Examples of the substituted fluorenyl group may include the groups shown below. However, the embodiment is not limited thereto.

[0105]

[0106] In the specification, the heterocyclic group may be any functional group or substituent derived from a ring including at least one of B, O, N, P, Si, S and Se as a heteroatom. The heterocyclic group may be an aliphatic heterocyclic group or an aromatic heterocyclic group. The aromatic heterocyclic group may be a heteroaryl group. The aliphatic heterocyclic group and the aromatic heterocyclic group may each independently be monocyclic or polycyclic.

[0107] In the specification, the heterocyclic group may include at least one of B, O, N, P, Si, S and Se as a heteroatom. If the heterocyclic group includes two or more heteroatoms, the two or more heteroatoms may be the same or different from each other. The heterocyclic group may be a monocyclic heterocycle or a polycyclic heterocycle. The heterocyclic group may be a heteroaryl. The number of ring carbon atoms in the heterocyclic group may be 2 to 60, 2 to 30, 2 to 20 or 2 to 10.

[0108] In the specification, the aliphatic heterocyclic group may include at least one of B, O, N, P, Si, S and Se as a heteroatom. The number of ring-forming carbon atoms in the aliphatic heterocyclic group may be 2 to 60, 2 to 30, 2 to 20 or 2 to 10. Examples of the aliphatic heterocyclic group may include an oxirane group, a thiirane group, a pyrrolidinyl group, a piperidinyl group, a tetrahydrofuranyl group, a tetrahydrothienyl group, a thianyl group, a tetrahydropyranyl group, a 1,4-dioxanyl group and the like, but the embodiment is not limited thereto.

[0109] In the specification, the heteroaryl group may include at least one of B, O, N, P, Si, S and Se as a heteroatom. If the heteroaryl group includes two or more heteroatoms, the two or more heteroatoms may be the same or different from each other. The heteroaryl group may be monocyclic or polycyclic. The number of ring carbon atoms in the heteroaryl group may be 2 to 60, 2 to 30, 2 to 20, 2 to 15 or 2 to 10. Examples of heteroaryl groups may include thienyl, furanyl, pyrrolyl, imidazolyl, pyridyl, bipyridyl, pyrimidyl, triazine, triazolyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, quinazolinyl, quinoxalinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolyl, indolyl, carbazolyl, N-arylcarbazolyl, N-heteroarylcarbazolyl, N-alkylcarbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, thienothiphenyl, benzofuranyl, phenanthrolinyl, thiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, thiadiazolyl, phenothiazinyl, dibenzothirolyl, dibenzofuranyl, and the like, but embodiments are not limited thereto.

[0110] In the specification, the above description of the aryl group can be applied to the arylene group, except that the arylene group is a divalent group. The description of the heteroaryl group can be applied to the heteroarylene group, except that the heteroarylene group is a divalent group.

[0111] In the specification, the silyl group may be an alkylsilyl group or an arylsilyl group. The alkyl group in the alkylsilyl group may be linear, branched or cyclic. The number of carbon atoms in the alkylsilyl group is not specifically limited, but may be, for example, 1 to 20 or 1 to 10. The number of carbon atoms in the arylsilyl group is not specifically limited, but may be, for example, 6 to 30, 6 to 20 or 6 to 15. Examples of silyl groups may include trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, etc., but embodiments are not limited thereto.

[0112] In the specification, the number of carbon atoms in the carbonyl group is not particularly limited, but may be 1 to 40, 1 to 30, or 1 to 20. For example, the carbonyl group may have one of the following structures, but the embodiment is not limited thereto.

[0113]

[0114] In the specification, the number of carbon atoms in the sulfinyl group or the sulfonyl group is not particularly limited, but may be 1 to 30. The sulfinyl group may be an alkylsulfinyl group or an arylsulfinyl group. The sulfonyl group may be an alkylsulfonyl group or an arylsulfonyl group.

[0115] In the specification, the thio group may be an alkylthio group or an arylthio group. The thio group may be a sulfur atom bonded to an alkyl group or an aryl group as defined above. The alkyl group in the alkylthio group may be linear, branched or cyclic. The number of carbon atoms in the alkylthio group is not specifically limited, but may be, for example, 1 to 20 or 1 to 10. The number of carbon atoms in the arylthio group is not specifically limited, but may be, for example, 6 to 30, 6 to 20 or 6 to 15. Examples of thio groups may include methylthio, ethylthio, propylthio, pentylthio, hexylthio, octylthio, dodecylthio, cyclopentylthio, cyclohexylthio, phenylthio or naphthylthio, but embodiments are not limited thereto.

[0116] In the specification, the oxy group may be an oxygen atom bonded to an alkyl group or an aryl group as defined above. The oxy group may be an alkoxy group or 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. The number of carbon atoms in the aryloxy group is not specifically limited, but may be, for example, 6 to 30, 6 to 20 or 6 to 15. Examples of oxy groups may include methoxy, ethoxy, n-propoxy, isopropoxy, butoxy, pentyloxy, hexyloxy, octyloxy, nonyloxy, decyloxy, benzyloxy, etc., but embodiments are not limited thereto.

[0117] In the specification, the boryl group herein may be a boron atom bonded to an alkyl group or an aryl group as defined above. The boryl group may be an alkyl boryl group or an aryl boryl group. The alkyl group in the alkyl boryl group may be linear, branched or cyclic. The number of carbon atoms in the alkyl boryl group is not specifically limited, but may be, for example, 1 to 20 or 1 to 10. The number of carbon atoms in the aryl boryl group is not specifically limited, but may be, for example, 6 to 30, 6 to 20 or 6 to 15. Examples of boryl groups may include dimethyl boryl, tert-butyl methyl boryl, diphenyl boryl, phenyl boryl, etc., but embodiments are not limited thereto.

[0118] In the specification, the amine group may be an alkylamine group or an arylamine group. The alkyl group in the alkylamine group may be linear, branched or cyclic. The number of carbon atoms in the alkylamine group is not specifically limited, but may be, for example, 1 to 20 or 1 to 10. The number of carbon atoms in the arylamine group is not specifically limited, but may be, for example, 6 to 30, 6 to 20 or 6 to 15. Examples of the amine group may include methylamine, dimethylamine, phenylamine, diphenylamine, naphthylamine, 9-methyl-anthrylamine, etc., but the embodiment is not limited thereto.

[0119] In the specification, the phosphine oxide group may mean an alkyl group or an aryl group defined above combined with -P(=O)-. The number of carbon atoms of the phosphine oxide group is not particularly limited, but may be 1 to 30, 1 to 20, or 1 to 10. The phosphine oxide group may include an alkyl phosphine oxide group and an aryl phosphine oxide group. For example, the phosphine oxide group may have the following structure, but is not limited thereto.

[0120]

[0121] In the specification, the phosphinosulfide group may mean an alkyl or aryl group defined above combined with -P(=S)-. The number of carbon atoms of the phosphinosulfide group is not particularly limited, but may be 1 to 30, 1 to 20, or 1 to 10. The phosphinosulfide group may include an alkylphosphinosulfide group and an arylphosphinosulfide group. For example, the phosphinosulfide group may have the following structure, but is not limited thereto.

[0122]

[0123] In the specification, the alkyl group in the alkoxy group, alkylthio group, alkylsulfinyl group, alkylsulfonyl group, alkylaryl group, alkylamino group, alkylboryl group, alkylsilyl group, alkylphosphine oxide group, alkylphosphine sulfide group or alkylamine group may be the same as the examples of the alkyl group described above.

[0124] In the specification, the aryl group in the aryloxy group, arylthio group, arylsulfinyl group, arylsulfonyl group, arylamino group, arylboryl group, arylsilyl group, arylphosphine oxide group, arylphosphine sulfide group or arylamine group may be the same as the examples of the aryl group described above.

[0125] In the specification, a direct connection may be a single bond.

[0126] In this manual, the symbol and -* each represent a bond to the adjacent atoms in the corresponding formula or moiety.

[0127] Hereinafter, embodiments will be described with reference to the accompanying drawings.

[0128] Figure 1 is a schematic plan view of a display device DD according to an embodiment. Figure 2 is a schematic cross-sectional view of a display device DD according to an embodiment. Figure 2 For along Figure 1 A cross-sectional view of a portion taken along line II′ in FIG.

[0129] The display device DD may include a display panel DP and an optical layer PP disposed on the display panel DP. The display panel DP includes light emitting elements ED-1, ED-2, and 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 may be disposed on the display panel DP to control light reflected from external light at the display panel DP. The optical layer PP may include, for example, a polarizing layer or a color filter layer. Although not shown in the drawings, in an embodiment, the optical layer PP may be omitted from the display device DD.

[0130] In an embodiment, the base substrate BL may be disposed on the optical layer PP. The base substrate BL may provide a base surface on which the optical layer PP is disposed. The base substrate BL may be a glass substrate, a metal substrate, a plastic substrate, etc. However, the embodiment is not limited thereto, and the base substrate BL may include an inorganic layer, an organic layer, or a composite material layer. Although not shown in the drawings, in an embodiment, the base substrate BL may be omitted.

[0131] The display device DD according to the embodiment may further include a filling layer (not shown). The filling layer (not shown) may be provided between the display device layer DP-ED and the base substrate BL. The filling layer (not shown) may be an organic material layer. The filling layer (not shown) may include at least one of an acrylic resin, a silicone resin, and an epoxy resin.

[0132] In an embodiment, the display panel DP may include a base layer BS, a circuit layer DP-CL provided on the base layer BS, and a display device layer DP-ED. The display device layer DP-ED may include a pixel defining film PDL, light emitting elements ED-1, ED-2, and ED-3 disposed between portions of the pixel defining film PDL, and an encapsulation layer TFE disposed on the light emitting elements ED-1, ED-2, and ED-3.

[0133] In an embodiment, the base layer BS may provide a base surface on which the display device layer DP-ED is 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 include an inorganic layer, an organic layer, or a composite material layer.

[0134] In an embodiment, the circuit layer DP-CL is disposed on the base layer BS, and the circuit layer DP-CL may include transistors (not shown). The transistors (not shown) may each include a control electrode, an input electrode, and an output electrode. For example, the circuit layer DP-CL may include a switching transistor and a driving transistor for driving the light emitting elements ED-1, ED-2, and ED-3 of the display device layer DP-ED.

[0135] The light emitting elements ED-1, ED-2 and ED-3 may each have Figures 3 to 6 The structure of the light-emitting element ED of any one of the embodiments of the present invention will be described later. The light-emitting elements ED-1, ED-2 and ED-3 may each include a first electrode EL1, a hole transport region HTR, emission layers EML-R, EML-G and EML-B, an electron transport region ETR, and a second electrode EL2.

[0136] Figure 2An embodiment is shown in which the emission layers EML-R, EML-G and EML-B of the light emitting elements ED-1, ED-2 and ED-3 are disposed in the opening OH defined by the pixel defining film PDL, and the hole transport region HTR, the electron transport region ETR and the second electrode EL2 are each provided as a common layer for all the light emitting elements ED-1, ED-2 and ED-3. However, the embodiment is not limited thereto. Although Figure 2 Although not shown in the figure, in an embodiment, the hole transport region HTR and the electron transport region ETR may each be provided by being patterned in the opening OH defined by the pixel defining film PDL. In an embodiment, the hole transport region HTR, the emission layers EML-R, EML-G and EML-B, and the electron transport region ETR of the light emitting elements ED-1, ED-2 and ED-3 may each be provided by being patterned by an inkjet printing method.

[0137] The encapsulation layer TFE may cover the light emitting elements ED-1, ED-2 and ED-3. The encapsulation layer TFE may seal the light emitting elements ED-1, ED-2 and ED-3 in the display device layer DP-ED. The encapsulation layer TFE may be a thin film encapsulation layer. The encapsulation layer TFE may be formed of a single layer or multiple layers. The encapsulation layer TFE may include at least one insulating layer. The encapsulation layer TFE may include at least one inorganic film (hereinafter, encapsulation inorganic film). In an embodiment, the encapsulation layer TFE may include at least one organic film (hereinafter, encapsulation organic film) and at least one encapsulation inorganic film.

[0138] The encapsulated inorganic film protects the display device layer DP-ED from moisture and / or oxygen, and the encapsulated organic film protects the display device layer DP-ED from foreign matter (such as dust particles). The encapsulated inorganic film may include silicon nitride, silicon oxynitride, silicon oxide, titanium oxide, or aluminum oxide, etc., but the embodiment is not limited thereto. The encapsulated organic film may include an acrylic compound or an epoxy compound, etc. The encapsulated organic film may include a photopolymerizable organic material, but the embodiment is not particularly limited thereto.

[0139] The encapsulation layer TFE may be disposed on the second electrode EL2 , and may be disposed to fill the opening OH.

[0140] refer to Figure 1 and Figure 2 , the display device DD may include a non-light emitting area NPXA and light emitting areas PXA-R, PXA-G, and PXA-B. The light emitting areas PXA-R, PXA-G, and PXA-B may each be an area that emits light generated from each of the light emitting elements ED-1, ED-2, and ED-3. In a plan view, the light emitting areas PXA-R, PXA-G, and PXA-B may be spaced apart from each other.

[0141] The light-emitting areas PXA-R, PXA-G, and PXA-B may each be an area separated by a pixel-defining film PDL. The non-light-emitting area NPXA may be an area between adjacent light-emitting areas PXA-R, PXA-G, and PXA-B, and corresponds to the pixel-defining film PDL. In an embodiment, the light-emitting areas PXA-R, PXA-G, and PXA-B may each correspond to a pixel. The pixel-defining film PDL may separate the light-emitting elements ED-1, ED-2, and ED-3. The emission 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 opening OH defined by the pixel-defining film PDL and separated from each other.

[0142] The light emitting areas PXA-R, PXA-G, and PXA-B may be arranged into a plurality of groups according to the colors of the lights generated by the light emitting elements ED-1, ED-2, and ED-3. Figure 1 and Figure 2 In the display device DD according to the embodiment explained in , three light emitting areas PXA-R, PXA-G and PXA-B emitting red light, green light and blue light respectively are explained as examples. For example, the display device DD may include a red light emitting area PXA-R, a green light emitting area PXA-G and a blue light emitting area PXA-B which are different from each other.

[0143] In the display device DD according to the embodiment, the light emitting elements ED-1, ED-2, and ED-3 may emit light having wavelength ranges different from each other. For example, in the embodiment, the display device DD may include a first light emitting element ED-1 emitting red light, a second light emitting element ED-2 emitting green light, and a third light emitting element ED-3 emitting blue light. For example, the red light emitting area PXA-R, the green light emitting area PXA-G, and the blue light emitting area 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.

[0144] 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 range, or at least one light emitting element may emit light in a wavelength range different from the rest. For example, the first to third light emitting elements ED-1, ED-2, and ED-3 may each emit blue light.

[0145] The light emitting areas PXA-R, PXA-G, and PXA-B in the display device DD according to the embodiment may be arranged in a stripe configuration. Figure 1, the red light emitting area PXA-R, the green light emitting area PXA-G and the blue light emitting area PXA-B may be arranged along the second direction axis DR2, respectively. In another embodiment, the red light emitting area PXA-R, the green light emitting area PXA-G and the blue light emitting area PXA-B may be alternately arranged in this repeating order along the first direction axis DR1.

[0146] Figure 1 and Figure 2 It is explained that the light-emitting regions PXA-R, PXA-G, and PXA-B all have the same area, but the embodiment is not limited thereto. In an embodiment, the light-emitting regions PXA-R, PXA-G, and PXA-B may be different in size and shape from each other according to the wavelength range of the emitted light. The areas of the light-emitting regions PXA-R, PXA-G, and PXA-B may be areas in a plane view defined by the first direction axis DR1 and the second direction axis DR2. The third direction axis DR3 may be perpendicular to the plane defined by the first direction axis DR1 and the second direction axis DR2.

[0147] The arrangement of the light emitting areas PXA-R, PXA-G and PXA-B is not limited to Figure 1 The arrangement of the red light emitting area PXA-R, the green light emitting area PXA-G and the blue light emitting area PXA-B can be provided in various combinations according to the display quality characteristics required by the display device DD. For example, the light emitting areas PXA-R, PXA-G and PXA-B can be arranged in a honeycomb shape (e.g. ) or in a diamond configuration (such as Diamond )arrangement.

[0148] The areas of the light emitting regions PXA-R, PXA-G, and PXA-B may be different in size from each other. For example, in an 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.

[0149] Figures 3 to 6 Each is a schematic cross-sectional view of a light emitting element ED according to an embodiment. The light emitting element ED according to an embodiment may include a first electrode EL1, a second electrode EL2 disposed opposite to the first electrode EL1, and at least one functional layer disposed between the first electrode EL1 and the second electrode EL2. The light emitting element ED according to an embodiment may include a polycyclic compound according to an embodiment in at least one functional layer, which will be explained later.

[0150] The light emitting element ED may include a hole transport region HTR, an emission layer EML, an electron transport region ETR, etc. stacked in sequence as at least one functional layer. The light emitting element ED according to the 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 stacked in sequence.

[0151] and Figure 3 compared to, Figure 4 Schematic cross-sectional view of a light emitting element ED according to an embodiment, wherein the hole transport region HTR includes a hole injection layer HIL and a hole transport layer HTL, and the electron transport region ETR includes an electron injection layer EIL and an electron transport layer ETL. Figure 3 compared to, Figure 5 Schematic cross-sectional view of a light emitting element ED according to an embodiment, wherein the hole transport region HTR includes a hole injection layer HIL, a hole transport layer HTL and an electron blocking layer EBL, and the electron transport region ETR includes an electron injection layer EIL, an electron transport layer ETL and a hole blocking layer HBL. Figure 4 compared to, Figure 6 2 is a schematic cross-sectional view of a light emitting element ED according to an embodiment including a capping layer CPL provided on the second electrode EL2 .

[0152] The first electrode EL1 has conductivity. The first electrode EL1 may be formed of a metal material, a metal alloy, or a conductive compound. The first electrode EL1 may be an anode or a cathode. However, the embodiment is not limited thereto. In an embodiment, the first electrode EL1 may be a pixel electrode. The first electrode EL1 may be a transmissive electrode, a transflective electrode, or a reflective electrode. The first electrode EL1 may include at least one of Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF, Mo, Ti, W, In, Sn, and Zn, an oxide thereof, a compound thereof, or a mixture thereof.

[0153] If the first electrode EL1 is a transmissive electrode, the first electrode EL1 may include a transparent metal oxide such as indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), or indium tin zinc oxide (ITZO). If the first electrode EL1 is a transflective electrode or a reflective electrode, the first electrode EL1 may include at least one of Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF, Mo, Ti, and W, a compound thereof, or a mixture thereof (e.g., a mixture of Ag and Mg), or a multilayer structure material such as LiF / Ca (a stacking structure of LiF and Ca) or LiF / Al (a stacking structure of LiF and Al). In another example, the first electrode EL1 may have a multilayer structure including a reflective film or a transflective film formed of the above materials, and a transparent conductive film formed of ITO, IZO, ZnO, ITZO, etc. For example, the first electrode EL1 may have a three-layer structure of ITO / Ag / ITO, but the embodiment is not limited thereto. In an embodiment, the first electrode EL1 may include the above metal material, a combination of at least two of the above metal materials, or an oxide of the above metal materials. The thickness of the first electrode EL1 may be about 1000 nm. to about For example, the thickness of the first electrode EL1 may be about to about within the range.

[0154] The 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 buffer layer (not shown), an emission auxiliary layer (not shown), and an electron blocking layer EBL. The thickness of the hole transport region HTR may be about 1000 Å. to about within the range.

[0155] The hole transport region HTR may have a single-layer structure composed of a single material, a single-layer structure including different materials, or a multi-layer structure including a plurality of layers including different materials.

[0156] In an embodiment, 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 formed of a hole injection material and a hole transport material. In an embodiment, the hole transport region HTR may have a single-layer structure formed of different materials, or may have a structure in which a hole injection layer HIL / hole transport layer HTL, a hole injection layer HIL / hole transport layer HTL / buffer layer (not shown), a hole injection layer HIL / buffer layer (not shown), a hole transport layer HTL / buffer layer (not shown), or a hole injection layer HIL / hole transport layer HTL / electron blocking layer EBL are stacked from the first electrode EL1 in the order described in each of them, but the embodiment is not limited thereto.

[0157] The hole transport region HTR may be formed using various methods such as a vacuum deposition method, a spin coating method, a casting method, a Langmuir-Brokett (LB) method, an inkjet printing method, a laser printing method, and a laser induced thermal imaging (LITI) method.

[0158] In the light emitting element ED according to the embodiment, the hole transport region HTR may include a compound represented by Formula H-1:

[0159] [Formula H-1]

[0160]

[0161] In formula H-1, L 1 and L 2 Each of L is independently a directly connected, 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. In formula H-1, a and b are independently an integer selected from 0 to 10. When a or b is an integer equal to or greater than 2, multiple L 1 Group or multiple L 2 The groups may each independently be a substituted or unsubstituted arylene group having 6 to 30 ring-forming carbon atoms or a substituted or unsubstituted heteroarylene group having 2 to 30 ring-forming carbon atoms.

[0162] In formula H-1, Ar 1 and Ar 2 and Ar may be each independently 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 It may 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.

[0163] In an embodiment, the compound represented by formula H-1 may be a monoamine compound. In an embodiment, the compound represented by formula H-1 may be a compound wherein Ar 1 To Ar 3 In another embodiment, the compound represented by formula H-1 may be a diamine compound wherein Ar 1 and Ar 2 At least one of the carbazole compounds includes a substituted or unsubstituted carbazole group, or may be a carbazole compound in which Ar 1 and Ar 2 At least one of the fluorene compounds includes a substituted or unsubstituted fluorenyl group.

[0164] The compound represented by Formula H-1 may be any compound selected from Compound Group H. However, the compounds listed in Compound Group H are merely examples, and the compound represented by Formula H-1 is not limited to Compound Group H:

[0165] [Compound Group H]

[0166]

[0167]

[0168] The hole transport region HTR may include a phthalocyanine compound (such as copper phthalocyanine), N 1 ,N 1 '-([1,1'-biphenyl]-4,4'-diyl)bis(N 1 -phenyl-N 4 ,N 4 -dimethylphenyl-1,4-diamine)(DNTPD), 4,4',4"-[tri(3-methylphenyl)phenylamino]triphenylamine (m-MTDATA), 4,4',4"-tri(N,N-diphenylamino)triphenylamine (TDATA), 4,4',4"-tri[N-(2-naphthyl)-N-phenylamino]triphenylamine (2-TNATA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / dodecylbenzenesulfonic acid (P ANI / DBSA), polyaniline / camphorsulfonic acid (PANI / CSA), polyaniline / poly(4-styrenesulfonate) (PANI / PSS), N,N'-di(naphthalene-1-yl)-N,N'-diphenyl-benzidine (NPB), triphenylamine-containing polyether ketone (TPAPEK), 4-isopropyl-4'-methyldiphenyliodonium [tetrakis(pentafluorophenyl)borate], dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile (HAT-CN), etc.

[0169] The hole transport region HTR may include carbazole derivatives (such as N-phenylcarbazole or polyvinylcarbazole), fluorene derivatives, triphenylamine derivatives (such as N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (TPD), 4,4',4"-tri(carbazole-9-yl)triphenylamine (TCTA), N,N'-di(naphthalene-1-yl)-N,N'-diphenyl-benzidine (NPB), 4,4'-cyclohexylenebis[N,N-bis(4-methylphenyl]aniline] (TAPC), 4,4'-bis[N,N'-(3-tolyl)amino]-3,3'-dimethylbiphenyl (HMTPD) or 1,3-bis(carbazole-9-yl)benzene (mCP)), etc.

[0170] The hole transport region HTR may include the above-mentioned compound of the hole transport region HTR in at least one of the hole injection layer HIL, the hole transport layer HTL, and the electron blocking layer EBL.

[0171] The thickness of the hole transport region HTR may be about to about For example, about to When the hole transport region HTR includes the hole injection layer HIL, the hole injection layer HIL may have, for example, about to about When the hole transport region HTR includes the hole transport layer HTL, the hole transport layer HTL may have a thickness of about to about For example, when the hole transport layer HTR includes the electron blocking layer EBL, the electron blocking layer EBL may have a thickness of about to about 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 ranges, satisfactory hole transport properties may be achieved without significantly increasing the driving voltage.

[0172] In addition to the above materials, the hole transport region HTR may further include a charge generation material to increase conductivity. The charge generation material may be uniformly or non-uniformly dispersed in the hole transport region HTR. The charge generation material may be, for example, a p-dopant. The p-dopant may include at least one of a metal halide, a quinone derivative, a metal oxide, and a cyano compound, but the embodiment is not limited thereto.

[0173] For example, the p-dopant may include a metal halide (such as CuI or RbI), a quinone derivative (such as tetracyanoquinodimethane (TCNQ) or 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4-TCNQ)), a metal oxide (such as tungsten oxide or molybdenum oxide), a cyano compound (such as dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile (HAT-CN) or 4-[[2,3-bis[cyano-(4-cyano-2,3,5,6-tetrafluorophenyl)methylene]cyclopropyl]-cyanomethyl]-2,3,5,6-tetrafluorobenzonitrile (NDP9)), etc., but the embodiment is not limited thereto.

[0174] As described above, in addition to the hole injection layer HIL and the hole transport layer HTL, the hole transport region HTR may further include at least one of a buffer layer (not shown) and an electron blocking layer EBL. The buffer layer (not shown) may compensate for the resonance distance according to the wavelength of light emitted from the emission layer EML, and thus may increase the luminous efficiency. The material that may be included in the hole transport region HTR may be used as a material in the buffer layer (not shown). The electron blocking layer EBL may prevent electrons from being injected from the electron transport region ETR to the hole transport region HTR.

[0175] The emission layer EML may be provided on the hole transport region HTR. The emission layer EML may have a thickness of about to about For example, the emission layer EML may have a thickness of about to about The emission layer EML may have a single-layer structure consisting of a single material, a single-layer structure including different materials, or a multi-layer structure including a plurality of layers including different materials.

[0176] The light emitting element ED may include a polycyclic compound represented by Formula 1 in at least one functional layer disposed between the first electrode EL1 and the second electrode EL2. In the light emitting element ED, the emission layer EML may include the polycyclic compound according to the embodiment. The emission layer EML may include the polycyclic compound according to the embodiment as a dopant. The polycyclic compound according to the embodiment may be a dopant material in the emission layer EML. In the description, the polycyclic compound according to the embodiment may be referred to as a first compound.

[0177] The polycyclic compound according to the embodiment may include a core portion of a polycyclic aromatic hydrocarbon group (PAH group). The polycyclic aromatic hydrocarbon ring may refer to a fused structure of multiple aromatic rings. The polycyclic compound according to the embodiment may include a fused structure of a fused ring including a boron atom and two heteroatoms as ring-forming atoms at the core portion. For example, the polycyclic compound according to the embodiment may include a fused structure of two fused rings formed by fusing multiple aromatic rings via a boron atom and two heteroatoms at the core portion.

[0178] In an embodiment, the polycyclic compound according to the embodiment may include a fused structure formed by fusing a plurality of aromatic rings through a first boron atom, a second boron atom, a first nitrogen atom, a second nitrogen atom, a first heteroatom, and a second heteroatom. For example, the polycyclic compound according to the embodiment may include a first condensed ring comprising a first boron atom, a first nitrogen atom, and a first heteroatom and a second condensed ring comprising a second boron atom, a second nitrogen atom, and a second heteroatom while sharing a connection structure of a polycyclic aromatic hydrocarbon ring. For example, the polycyclic compound according to the embodiment may include a condensed structure of a first condensed ring and a second condensed ring at a core portion. The core portion may be connected to a first boron atom and a first heteroatom of the first condensed ring and a second boron atom and a second heteroatom of the second condensed ring.

[0179] In an embodiment, the lowest triplet energy level (T1) of the core portion may substantially determine the lowest triplet energy level (T1) of the polycyclic compound according to the embodiment. Accordingly, if the lowest triplet energy level (T1) of the core portion is low, the lowest triplet energy level (T1) of the polycyclic compound according to the embodiment may be low. The polycyclic compound according to the embodiment includes an organic compound (polycyclic aromatic hydrocarbon ring group, PAH group) having a low value of the lowest triplet energy level (T1) in the core portion, and the lowest triplet energy level (T1) of the entire polycyclic compound may be low. For example, the polycyclic compound according to the embodiment may include a polycyclic aromatic hydrocarbon ring having a lowest triplet energy level (T1) of approximately equal to or less than 2.4 eV in the core portion. In an embodiment, the lowest triplet energy level (T1) of the polycyclic aromatic hydrocarbon ring included in the core portion may be from about 1.5 eV to about 2.4 eV. In an embodiment, the polycyclic aromatic hydrocarbon ring having a lowest triplet energy level (T1) in the range of about 1.5 eV to about 2.4 eV may be pyrene, anthracene, phenanthrene, or fluorene, but the embodiment is not limited thereto. Pyrene, anthracene, phenanthrene, and fluorene may each independently be substituted or unsubstituted. In the specification, the lowest triplet energy level (T1) may be referred to as the lowest triplet energy level (T1) or the lowest triplet excited energy level (T1).

[0180] The polycyclic compound according to the embodiment may be represented by Formula 1. In Formula 1, L may correspond to the above-mentioned core part. Substituents X and NR 5 As ring atoms and including 1 and R2 The fused ring of the fused benzene ring substituted with the substituent represented by may correspond to the first fused ring. 6 As ring atoms and including 3 and R 4 The condensed ring of the condensed benzene ring substituted with the substituent represented by may correspond to the second condensed ring.

[0181] [Formula 1]

[0182]

[0183] In Formula 1, L may be a substituted or unsubstituted polycyclic aromatic hydrocarbon group having a low value of the lowest triplet energy level (T1). In an embodiment, in Formula 1, L may be a substituted or unsubstituted polycyclic aromatic hydrocarbon group having a lowest triplet energy level (T1) in the range of about 1.5 eV to about 2.4 eV. In an embodiment, in Formula 1, L may be a substituted or unsubstituted polycyclic aromatic hydrocarbon group of 12 to 25 ring-forming carbon atoms. In an embodiment, L may be a substituted or unsubstituted pyrene group, a substituted or unsubstituted anthracene group, a substituted or unsubstituted phenanthrenyl group, or a substituted or unsubstituted fluorenyl group. If L is a substituted group, the substituent may be a deuterium atom or a substituted or unsubstituted aromatic group of 6 to 15 ring-forming carbon atoms, without limitation.

[0184] In Formula 1, X and Y can each independently be N(R 7 ), O, S or Se. X may correspond to the first heteroatom explained above, and Y may correspond to the second heteroatom explained above. In an embodiment, X and Y may be the same or different. In an embodiment, at least one of X and Y may each independently be N(R 7 For example, X and Y can each independently be N(R 7 As another example, any one of X and Y may be N(R 7 ), and the other may be O, S or Se.

[0185] In formula 1, R 1 To R 4 Each of R and R can be independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 60 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 60 ring carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 ring carbon atoms. For example, R 1 To R 4and R and R are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 15 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 15 ring carbon atoms. 1 To R 4 Each may independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted diphenylamine group, a substituted or unsubstituted tert-butyl group, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted carbazole group, but the embodiment is not limited thereto.

[0186] In formula 1, R 5 To R 7 Each of R and R is independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 30 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. 5 To R 7 Each may independently be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, or a substituted or unsubstituted dibenzofuranyl group.

[0187] In Formula 1, n1 and n4 may each independently be an integer selected from 0 to 4. In Formula 1, if n1 and n4 are 0, the polycyclic compound according to the embodiment may not be 1 and R 4 Where n1 and n4 are 4, and R 1 and R 4 The case where all R atoms are hydrogen atoms may be the same as the case where n1 and n4 are 0 respectively. If n1 and n4 are integers of 2 or more, then the plurality of R 1 and multiple R 4 Each of the R 1 and multiple R 4 At least one of each of may be different.

[0188] In Formula 1, n2 and n3 may each independently be an integer selected from 0 to 3. In Formula 1, if n2 and n3 are 0, the polycyclic compound according to the embodiment may not be 2 and R 3 In Formula 1, wherein n2 and n3 are 3, and R 2 and R 3 The case where n2 and n3 are all hydrogen atoms may be the same as the case where n2 and n3 are each 0. If n2 and n3 are integers of 2 or more, then the plurality of R 2 and multiple R 3 Each of the R 2 and multiple R3 At least one of each of may be different.

[0189] The polycyclic compound represented by Formula 1 includes an organic compound (polycyclic aromatic hydrocarbon group, PAH group) having a low value of the lowest triplet energy level (T1) in the core portion, and may therefore exhibit a low value of the lowest triplet energy level (T1) of the polycyclic compound represented by Formula 1 itself, and may also exhibit a low value of the second lowest triplet energy level (T2 or second lowest triplet excited energy level). Accordingly, the polycyclic compound represented by Formula 1 may have a difference (ΔT) between the lowest singlet energy level (S1 or lowest singlet excited energy level) and the second lowest triplet energy level (T2). S1-T2 ) is greater than the difference (Δ T2-T1 ).

[0190] 7A to 7C Schematic diagrams of the energy levels of polycyclic compounds. Fig. 7A is a schematic diagram of the energy levels of compound X1, and Figure 7B Schematic diagram of the energy levels of compound X2. Figure 7C is a schematic diagram of energy levels of compound X3. Compound X1 and compound X2 are comparative compounds, and compound X3 is a polycyclic compound according to an embodiment.

[0191]

[0192] refer to Fig. 7A , since the compound X1 without introducing an organic compound (polycyclic aromatic hydrocarbon group, PAH group) having a low value of the lowest triplet energy level (T1) has a very narrow energy gap (ΔE) between the lowest singlet energy level (S1) and the lowest triplet energy level (T1). ST ≤0.2eV), so the transition phenomenon of triplet excitons formed in the triplet state to the singlet state by anti-system crossing (RISC) may occur. The transition from the triplet state to the singlet state is a forbidden rule of the selection rule, and the transition rate between states is very slow (μs-ms). Because the triplet excitons with high energy in compound X1 remain in the triplet state during the spin flip of the electron, the degradation of the organic material can be accelerated.

[0193] Compound X2 introduces pyrene having a low value of the lowest triplet energy level (T1), not as a core part but as a substituent. Figure 7B In compound X2, there are competing pathways from the second lowest triplet energy level (T2) to the lowest singlet energy level (S1) and from the second lowest triplet energy level (T2) to the lowest triplet state, and both the lifetime and emission efficiency of the light-emitting element ED are deteriorated.

[0194] refer to Figure 7C , the compound X3 corresponding to the polycyclic compound according to the embodiment introduces a polycyclic aromatic hydrocarbon group (PAH group) having a low value of the lowest triplet energy level (T1) in the core portion, and the second lowest triplet energy level (T2) can be reduced. The polycyclic compound according to the embodiment introduces a polycyclic aromatic hydrocarbon group having a lowest triplet energy level (T1) equal to or less than about 2.4 eV in the core portion. The polycyclic compound according to the embodiment introduces a polycyclic aromatic hydrocarbon group having a lowest triplet energy level (T1) equal to or less than about 2.0 eV in the core portion. In an embodiment, the energy level difference from the lowest singlet energy level (S1) to the second lowest triplet energy level (T2) is greater than the energy level difference from the second lowest triplet energy level (T2) to the lowest triplet energy level (T1). Accordingly, in the polycyclic compound according to the embodiment, RISC of triplet excitons formed in the second lowest triplet state can be maximally suppressed, most of the triplet excitons formed in the triplet state can disappear by non-radiative decay after transitioning to the lowest triplet state, and the lifetime of the light-emitting element ED can be increased.

[0195] The polycyclic compound represented by Formula 1 according to the embodiment can have a plate-type strong binding structure by condensing the first condensed ring and the second condensed ring at the core part, and can improve the chemical stability of the entire molecule. Accordingly, if the polycyclic compound represented by Formula 1 is applied to the emission layer EML of the light-emitting element ED, the life span and emission efficiency can be improved.

[0196] The polycyclic compound represented by Formula 1 may include a deuterium atom as a substituent. In an embodiment, in the polycyclic compound represented by Formula 1, the substituent of L and R 1 To R 7 At least one of may each independently include a deuterium atom or a substituent including a deuterium atom. However, this is only an example, and embodiments are not limited thereto.

[0197] In an embodiment, the polycyclic compound represented by Formula 1 may be represented by any one of Formula 2-1 to Formula 2-5.

[0198] [Formula 2-1]

[0199]

[0200] [Formula 2-2]

[0201]

[0202] [Formula 2-3]

[0203]

[0204] [Formula 2-4]

[0205]

[0206] [Formula 2-5]

[0207]

[0208] In Formula 2-1 to Formula 2-5, R a1 To R a6 , R b1 To R b6 , R c1 To R c4 , R d1 To R d4 and R e1 To R e6 R and R are each independently a hydrogen atom, a deuterium atom or a substituted or unsubstituted aromatic group having 6 to 15 ring carbon atoms. a1 To R a6 , R b1 To R b6 , R c1 To R c4 , R d1 To R d4 and R e1 To R e6 may be each independently a hydrogen atom, a deuterium atom or a substituted or unsubstituted phenyl group. a1 To R a6 , R c1 To R c4 , R d1 To R d4 and R e1 To R e6 can each independently be a hydrogen atom or a deuterium atom. In an embodiment, R b1 , R b3 , R b4 and R b6 can each independently be a hydrogen atom or a deuterium atom, and R b2 and R b5 Each may be an unsubstituted phenyl group.

[0209] In Formula 2-3 and Formula 2-4, c1, c2, d1 and d3 may each independently be an integer selected from 0 to 4; and c3, c4, d2 and d4 may each independently be an integer selected from 0 to 2. If c1 to c4 and d1 to d4 are 0, the polycyclic compound may not be R c1 To R c4 and R d1 To R d4 The case where c1, c2, d1 and d3 are 0 can be replaced by the case where c1, c2, d1 and d3 are 4 and R c1 , R c2 , Rd1 and R d3 The case where four of each of the four are hydrogen atoms is the same. The case where c3, c4, d2 and d4 are 0 can be the same as the case where c3, c4, d2 and d4 are 2, and R c3 , R c4 , R d2 and R d4 The same is true for the case where two of each of R are hydrogen atoms. If c1 to c4 and d1 to d4 are integers of 2 or more, then the plurality of R c1 To multiple R c4 and multiple R d1 To multiple R d4 Each of R can be the same, or multiple R c1 To multiple R c4 and multiple R d1 To multiple R d4 At least one of may be different.

[0210] In equations 2-1 to 2-5, X, Y, and R 1 To R 6 and n1 to n4 may be the same as defined in Formula 1.

[0211] In an embodiment, the polycyclic compound represented by Formula 2-1 may be represented by Formula 2-1A.

[0212] [Formula 2-1A]

[0213]

[0214] In formula 2-1A, R 21 ′ and R 31 ' may each independently be a hydrogen atom or a deuterium atom. In Formula 2-1A, n21' and n31' may each independently be an integer selected from 0 to 2. If n21' and n31' are 0, the polycyclic compound may not be R 21 ′ and R 31 ' are substituted respectively. In Formula 2-1A, wherein R 21 ′ and R 31 ' is 2 and R 21 ′ and R 31 The case where two of each of R ' are hydrogen atoms may be the same as the case where n21' and n31' are 0 respectively. If n21' is 2, then the two R 21 ' can be the same, or two R 21 ' can be different from each other. If n31' is 2, then the two R 31 ' can be the same, or two R 31 ' can be different from each other.

[0215] In formula 2-1A, R22 ′ and R 32 ' may each independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group of 1 to 10 carbon atoms, a substituted or unsubstituted aryl group of 6 to 15 ring carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 15 ring carbon atoms. For example, R 22 ′ and R 32 ' may each independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted diphenylamine group, a substituted or unsubstituted tert-butyl group, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted carbazole group. In an embodiment, R 22 ′ and R 32 Each of ' may be substituted with a deuterium atom, but the embodiment is not limited thereto.

[0216] In formula 2-1A, R 51 ' to R 55 ′ and R 61 ' to R 65 ' may each independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group of 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group of 6 to 10 ring carbon atoms. 51 ' to R 55 ′ and R 61 ' to R 65 ' may each independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted tert-butyl group, or a substituted or unsubstituted phenyl group.

[0217] In formula 2-1A, R 1 , R 4 , R a1 To R a6 , n1, n4, X, and Y may be the same as defined in Formula 1 and Formula 2-1.

[0218] In an embodiment, the polycyclic compound represented by Formula 2-2 may be represented by Formula 2-2A.

[0219] [Formula 2-2A]

[0220]

[0221] In formula 2-2A, R 21 ′ and R 31 ' may each independently be a hydrogen atom or a deuterium atom. In Formula 2-2A, n21' and n31' may each independently be an integer selected from 0 to 2. If n21' and n31' are 0, the polycyclic compound may not be R 21 ′ and R 31 ' are substituted respectively. In Formula 2-2A, wherein R 21 ′ and R 31' is 2 and R 21 ′ and R 31 The case where two of each of R ' are hydrogen atoms may be the same as the case where n21' and n31' are 0 in Formula 2-2A. If n21' is 2, then the two R 21 ' can be the same, or two R 21 ' can be different. If n31' is 2, then the two R 31 ' can be the same, or two R 31 ' can be different.

[0222] In formula 2-2A, R 22 ′ and R 32 ' may each independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group of 1 to 10 carbon atoms, a substituted or unsubstituted aryl group of 6 to 15 ring carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 15 ring carbon atoms. For example, R 22 ′ and R 32 ' may each independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted diphenylamine group, a substituted or unsubstituted tert-butyl group, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted carbazole group. In an embodiment, if substituted, then R 22 ′ and R 32 ' may be substituted with a deuterium atom, but the embodiment is not limited thereto.

[0223] In formula 2-2A, R 51 ' to R 55 ′ and R 61 ' to R 65 ' may each independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group of 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group of 6 to 10 ring carbon atoms. 51 ' to R 55 ′ and R 61 ' to R 65 ' may each independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted tert-butyl group, or a substituted or unsubstituted phenyl group.

[0224] In formula 2-2A, R 1 , R 4 , R b1 To R b6 , n1, n4, X, and Y may be the same as defined in Formula 1 and Formula 2-2.

[0225] In an embodiment, the polycyclic compound represented by Formula 1 may be represented by Formula 3.

[0226] [Formula 3]

[0227]

[0228] In formula 3, R 5a To R 5e and R 6a To R 6e and R are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group of 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group of 6 to 10 ring carbon atoms. 5a To R 5e and R 6a To R 6e They may each independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted tert-butyl group, or a substituted or unsubstituted phenyl group.

[0229] In formula 3, R 1 To R 4 , n1 to n4, L, X, and Y may be the same as defined in Formula 1.

[0230] In an embodiment, the polycyclic compound represented by Formula 1 may be represented by Formula 4.

[0231] [Formula 4]

[0232]

[0233] In formula 4, R 21 and R 31 In Formula 4, n21 and n31 may each independently be an integer selected from 0 to 2. If n21 and n31 are 0, the polycyclic compound may not be R 21 and R 31 In Formula 4, n21 and n31 are 2 and R 21 and R 31 The case where two of each of R are hydrogen atoms may be the same as the case where n21 and n31 are 0 in Formula 4. If n21 is 2, then the two R 21 Can be the same, or two R 21 Can be different. If n31 is 2, then the two R 31 Can be the same, or two R 31 It can be different.

[0234] In formula 4, R 22 and R 32 Each of R and R is independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 15 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 15 ring carbon atoms. 22 and R 32and R are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted diphenylamine group, a substituted or unsubstituted tert-butyl group, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted carbazole group. 22 and R 32 It may be substituted with a deuterium atom, but the embodiment is not limited thereto.

[0235] In formula 4, R 1 , R 4 To R 6 , n1, n4, L, X and Y may be the same as defined in Formula 1.

[0236] In an embodiment, the polycyclic compound represented by Formula 1 may be represented by any one of Formula 5-1 to Formula 5-4.

[0237] [Formula 5-1]

[0238]

[0239] [Formula 5-2]

[0240]

[0241] [Formula 5-3]

[0242]

[0243] [Formula 5-4]

[0244]

[0245] In Formula 5-1 to Formula 5-4, R 71 To R 75 Each of R and R is independently a substituted or unsubstituted aryl group having 6 to 20 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 20 ring carbon atoms. 71 To R 75 Each independently may be a substituted or unsubstituted phenyl group or a substituted or unsubstituted dibenzofuranyl group.

[0246] In Formula 5-1 to Formula 5-4, R 1 To R 6 , n1 to n4 and L may be the same as defined in Formula 1.

[0247] In an embodiment, the polycyclic compound may be any compound selected from compound group 1. In an embodiment, in the light emitting element ED, at least one functional layer (eg, emission layer EML) may include at least one polycyclic compound selected from compound group 1. In compound group 1, D represents a deuterium atom.

[0248] [Compound Group 1]

[0249]

[0250]

[0251]

[0252]

[0253]

[0254]

[0255] In the polycyclic compound represented by Formula 1, the emission spectrum may have a full width at half maximum (FWHM) in the range of about 10 nm to about 50 nm. For example, the emission spectrum may have a full width at half maximum (FWHM) in the range of about 20 nm to about 40 nm. The emission spectrum of the polycyclic compound represented by Formula 1 may have a full width at half maximum in the above range, and if applied to a light-emitting element as a dopant, the emission efficiency may be improved. If the polycyclic compound represented by Formula 1 is used as a blue light-emitting element material for a light-emitting element, the life of the light-emitting element may be improved.

[0256] The polycyclic compound represented by Formula 1 may be a material for emitting thermally activated delayed fluorescence. The polycyclic compound represented by Formula 1 may have a difference (ΔE) between the lowest triplet excitation energy level (T1) and the lowest singlet excitation energy level (S1). ST1 ) is equal to or less than about 1.2 eV of a thermally activated delayed fluorescent dopant.

[0257] The polycyclic compound represented by Formula 1 according to the embodiment may be included in the emission layer EML. The polycyclic compound represented by Formula 1 may be included in the emission layer EML as a dopant material. The polycyclic compound represented by Formula 1 may be a thermally activated delayed fluorescence emission material. The polycyclic compound represented by Formula 1 may be used as a thermally activated delayed fluorescence (TADF) dopant. For example, in the light-emitting element ED, the emission layer EML may include at least one of the polycyclic compounds represented in compound group 1 as a thermally activated delayed fluorescence dopant. However, the use of the polycyclic compound represented by Formula 1 is not limited thereto.

[0258] The polycyclic compound represented by Formula 1 may be a light-emitting material having an emission center wavelength in a wavelength range of about 430 nm to about 490 nm. The polycyclic compound represented by Formula 1 may emit blue light. For example, the polycyclic compound represented by Formula 1 may be a blue thermally activated delayed fluorescence (TADF) dopant. However, the embodiment is not limited thereto.

[0259] In the light emitting element ED, the emission layer EML may emit delayed fluorescence. For example, the emission layer EML may emit thermally activated delayed fluorescence (TADF).

[0260] The emission layer EML of the light emitting element ED may emit blue light. For example, the emission layer EML of the light emitting element ED may emit blue light in a wavelength range equal to or less than about 490 nm. However, the embodiment is not limited thereto, and the emission layer EML may emit green light or red light.

[0261] In an embodiment, the emission layer EML may include a plurality of compounds. In an embodiment, the emission layer EML may include a polycyclic compound represented by Formula 1 as a first compound, and may further include at least one of a second compound represented by Formula HT-1, a third compound represented by Formula ET-1, and a fourth compound represented by Formula S-1. For example, the emission layer EML may include a first compound, a second compound, and a third compound.

[0262] In the emission layer EML, the second compound and the third compound may form an exciplex, and energy may be transferred from the exciplex to the first compound to emit light. In an embodiment, 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 may form an exciplex, and energy may be transferred from the exciplex to the fourth compound and the first compound to emit light. The fourth compound may be referred to as a sensitizer. The fourth compound may emit phosphorescence, or may transfer energy to the first compound as an auxiliary dopant. However, these are merely examples, and embodiments are not limited thereto.

[0263] The light emitting element ED may include a first compound, a second compound, a third compound, and a fourth compound, and the emission layer EML may include two main materials and two dopants in combination. In the light emitting element ED, the emission layer EML may include a first compound emitting delayed fluorescence, a second compound and a third compound as two different main materials, and a fourth compound which is an organic metal complex, and thus the light emitting element ED may exhibit excellent emission efficiency properties.

[0264] In an embodiment, the emission layer EML may further include a second compound represented by Formula HT-1. In an embodiment, the second compound may be used as a hole transport host material in the emission layer EML.

[0265] [Formula HT-1]

[0266]

[0267] In formula HT-1, A 1 To A 8 can be N or C (Rx1 ). For example, A 1 To A 8 can be independently C(R x1 ). In another example, A 1 To A 8 One of can be N, and A 1 To A 8 The remaining groups in may be independently C(R x1 ).

[0268] In formula HT-1, L 1 It may be a directly linked, 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 It may be a direct connection, a substituted or unsubstituted phenylene group, a substituted or unsubstituted divalent biphenyl group, a substituted or unsubstituted divalent carbazole group, or the like, but the embodiment is not limited thereto.

[0269] In formula HT-1, Y a Can be directly connected, C(R x2 )(R x3 ) or Si(R x4 )(R x5 ). For example, the two benzene rings bonded to the nitrogen atom in formula HT-1 can be directly connected, In formula HT-1, when Y a In case of direct connection, the second compound represented by Formula HT-1 may include a carbazole moiety.

[0270] In formula HT-1, Ar 1 It may 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. 1 It may be a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted biphenyl group, or the like, but the embodiment is not limited thereto.

[0271] In formula HT-1, R x1 To R x5Each of the R and R groups may independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted thiol group, a substituted or unsubstituted oxy group, a substituted or unsubstituted amine group, a substituted or unsubstituted boron group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 ring carbon atoms, or may be bonded to an adjacent group to form a ring. For example, R x1 To R x5 can each independently be a hydrogen atom or a deuterium atom. x1 To R x5 Each independently may be an unsubstituted methyl group or an unsubstituted phenyl group.

[0272] In an embodiment, the second compound represented by Formula HT-1 may be selected from Compound Group 2. In an embodiment, in the light emitting element ED, the second compound may include at least one compound selected from Compound Group 2.

[0273] [Compound Group 2]

[0274]

[0275]

[0276]

[0277]

[0278] In compound group 2, D represents a deuterium atom, and Ph represents a substituted or unsubstituted phenyl group. For example, in compound group 2, Ph may represent an unsubstituted phenyl group.

[0279] In an embodiment, the emission layer EML may further include a third compound represented by Formula ET-1. In an embodiment, the third compound may be used as an electron transport host material in the emission layer EML.

[0280] [Formula ET-1]

[0281]

[0282] In formula ET-1, X 1 To X 3 At least one of them may each be N, and X 1 To X 3 The remaining groups in may be independently C(R x6 ). For example, X 1 To X 3 One of can be N, and X1 To X 3 The remaining groups in may be independently C(R x6 ). Therefore, the third compound represented by Formula ET-1 may include a pyridine moiety. As another example, X 1 To X 3 Two of them can be N, and X 1 To X 3 The remaining groups in may be C(R x6 ). Therefore, the third compound represented by Formula ET-1 may include a pyrimidine moiety. As another example, X 1 To X 3 Each may be N. Therefore, the third compound represented by Formula ET-1 may include a triazine moiety.

[0283] In formula ET-1, R x6 It may be a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 ring carbon atoms.

[0284] In Formula ET-1, b1 to b3 may each independently be an integer selected from 0 to 10.

[0285] In formula ET-1, Ar 2 To Ar 4 and R and R are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms. 2 To Ar 4 Each independently may be a substituted or unsubstituted phenyl group or a substituted or unsubstituted carbazolyl group.

[0286] In formula ET-1, L 2 To L 4 Each of them may be independently a directly linked, 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. When b1 to b3 are integers equal to or greater than 2, L 2 To L 4 Each may 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.

[0287] In an embodiment, the third compound represented by Formula ET-1 may be selected from Compound Group 3. In an embodiment, in the light emitting element ED, the third compound may include at least one compound selected from Compound Group 3.

[0288] [Compound Group 3]

[0289]

[0290]

[0291]

[0292]

[0293]

[0294]

[0295]

[0296] In compound group 3, D represents a deuterium atom, and Ph represents an unsubstituted phenyl group.

[0297] In an embodiment, the emission layer EML may include a second compound and a third compound, and the second compound and the third compound may form an exciplex. In the emission layer EML, the exciplex may be formed by a hole transport host and an electron transport host. The triplet energy level of the exciplex formed by the hole transport host and the electron transport host may correspond to the difference between the lowest unoccupied molecular orbital (LUMO) energy level of the electron transport host and the highest occupied molecular orbital (HOMO) energy level of the hole transport host.

[0298] For example, the absolute value of the triplet energy level (T1) of the excited complex formed by the hole transport host and the electron transport host may be in the range of about 2.4 eV to about 3.0 eV. The triplet energy level of the excited complex may have a value less than the energy gap of each host material. The excited complex may have a triplet energy level less than or equal to about 3.0 eV, which is the energy gap between the hole transport host and the electron transport host.

[0299] In an embodiment, the emission layer EML may include a fourth compound in addition to the first compound, the second compound, and the third compound as described above. The fourth compound may serve as a sensitizer in the emission layer EML. Energy may be transferred from the fourth compound to the first compound, thereby emitting light.

[0300] In an embodiment, the emission layer EML may include an organic metal complex as a fourth compound, the organic metal complex including platinum (Pt) as a central metal atom and a ligand connected to the central metal atom. In an embodiment, the emission layer EML may further include a fourth compound represented by Formula S-1:

[0301] [Formula S-1]

[0302]

[0303] In formula S-1, Q 1 To Q 4 They may each independently be C or N.

[0304] In Formula S-1, C1 to C4 may each independently be a substituted or unsubstituted hydrocarbon ring group having 5 to 30 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 2 to 30 ring carbon atoms.

[0305] In formula S-1, L 11 To L 13 Can be directly connected, *—o—*, *—s—*, a substituted or unsubstituted alkylene 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. 11 To L 13 In the formula (a), —* indicates a bond connected to one of C1 to C4.

[0306] In Formula S-1, b11 to b13 may each independently be 0 or 1. If b11 is 0, C1 and C2 may not be directly connected to each other. If b12 is 0, C2 and C3 may not be directly connected to each other. If b13 is 0, C3 and C4 may not be directly connected to each other.

[0307] In formula S-1, R 61 To R 66 Each of the R and R groups may independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted thiol group, a substituted or unsubstituted oxy group, a substituted or unsubstituted amine group, a substituted or unsubstituted boron group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 ring carbon atoms, or may be bonded to an adjacent group to form a ring. For example, R 61 To R 66 Each independently may be a substituted or unsubstituted methyl group or a substituted or unsubstituted tert-butyl group.

[0308] In Formula S-1, d1 to d4 may each independently be an integer selected from 0 to 4. In Formula S-1, if d1 to d4 are each 0, the fourth compound may not be 61 To R 64 wherein d1 to d4 are each 4 and R 61 To R 64 The case where each of the groups in is a hydrogen atom may be the same as the case where d1 to d4 are each 0. When d1 to d4 are each 2 or more, R 61 To R 64 The multiple groups of each of may be the same as each other or at least one group therein may be different from the remaining groups.

[0309] In an embodiment, in Formula S-1, C1 to C4 may each independently be a substituted or unsubstituted hydrocarbon ring group or a substituted or unsubstituted heterocyclic group represented by one of Formulas C-1 to C-4:

[0310]

[0311] In Formula C-1 to Formula C-4, P 1 Can be c-* or C(R 74 ), P 2 Can be N—* or N(R 81 ), P 3 Can be N—* or N(R 82 ), and P 4 Can be c-* or C(R 88 ).

[0312] In Formula C-1 to Formula C-4, R 71 To R 88 They may each independently be 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, or may bond with an adjacent group to form a ring.

[0313] In Formula C-1 to Formula C-4, represents a bond to Pt as a central metal atom, and —* represents a bond to an adjacent cyclic group (C1 to C4) or a linker (L 11 To L 13 ) key to connect.

[0314] In an embodiment, the emission layer EML may include a polycyclic compound represented by Formula 1 as a first compound, and at least one of a second compound, a third compound, and a fourth compound. In an embodiment, the emission layer EML may include the first compound, the second compound, and the third compound. In the emission layer EML, the second compound and the third compound may form an excited complex, and energy may be transferred from the excited complex to the first compound, thereby emitting light.

[0315] In another embodiment, 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 may form an exciplex, and energy may be transferred from the exciplex to the fourth compound and the first compound, thereby emitting light. In an embodiment, the fourth compound may be a sensitizer. The fourth compound included in the emission layer EML of the light-emitting element ED may be used as a sensitizer to transfer energy from the host to the first compound as a light-emitting dopant. For example, the fourth compound used as an auxiliary dopant accelerates the energy transfer to the first compound used as a light-emitting dopant, thereby increasing the emission ratio of the first compound. Therefore, the emission layer EML may have improved emission efficiency. When the energy transferred to the first compound increases, the excitons formed in the emission layer EML may not accumulate inside the emission layer EML and may emit light quickly, so that the degradation of the light-emitting element ED may be reduced. Therefore, the service life of the light-emitting element ED of the embodiment may be increased.

[0316] The light emitting element ED may include a first compound, a second compound, a third compound, and a fourth compound, and the emission layer EML may include a combination of two host materials and two dopant materials. In the light emitting element ED, the emission layer EML may include the second compound and the third compound as two different hosts, the first compound emitting delayed fluorescence, and the fourth compound being an organic metal complex, and thus the light emitting element ED may exhibit excellent emission efficiency characteristics.

[0317] In an embodiment, the fourth compound represented by Formula S-1 may be selected from Compound Group 4. In an embodiment, the fourth compound may include at least one compound selected from Compound Group 4 in the light emitting element ED.

[0318] [Compound Group 4]

[0319]

[0320]

[0321] In compound group 4, D represents a deuterium atom.

[0322] In an embodiment, the light emitting element ED may include a plurality of emission layers EML. The plurality of emission layers EML may be provided as a stack of emission layers EML, so that the light emitting element ED including the plurality of emission layers EML may emit white light. The light emitting element ED including the plurality of emission layers EML may be a light emitting element of a series structure. If the light emitting element ED includes a plurality of emission layers EML, at least one emission layer EML may include a polycyclic compound represented by Formula 1 as a first compound. In an embodiment, if the light emitting element ED includes a plurality of emission layers EML, at least one emission layer EML may include the first compound, the second compound, the third compound, and the fourth compound as described above.

[0323] When the emission layer EML in the light emitting element ED includes a first compound, a second compound, a third compound, and a fourth compound, the amount of the first compound may be in the range of about 0.1 wt % to about 5 wt % relative to the total weight of the first compound, the second compound, the third compound, and the fourth compound. However, the embodiment is not limited thereto. When the amount of the first compound satisfies the above range, the energy transferred from the second compound and the third compound to the first compound may be increased, and thus the emission efficiency and the device lifespan may be increased.

[0324] The total amount of the second compound and the third compound in the emission layer EML may be the remaining amount of the total weight of the first compound, the second compound, the third compound, and the fourth compound excluding the amount of the first compound and the fourth compound. For example, the total amount of the second compound and the third compound in the emission layer EML may be in the range of about 65 wt % to about 95 wt % relative to the total weight of the first compound, the second compound, the third compound, and the fourth compound.

[0325] In the total amount of the second compound and the third compound in the emission layer EML, a weight ratio of the second compound to the third compound may be in the range of about 3:7 to about 7:3.

[0326] When the amounts of the second compound and the third compound satisfy the above ranges and ratios, the charge balance characteristics in the emission layer EML can be improved, and thus the emission efficiency and the device lifespan can be increased. When the amounts of the second compound and the third compound deviate from the above arrangement and ratio, the charge balance in the emission layer EML may not be achieved, and thus the emission efficiency may be reduced, and the device may be easily degraded.

[0327] When the emission layer EML includes the fourth compound, the amount of the fourth compound in the emission layer EML may be in the range of about 4 wt % to about 30 wt % relative to the total weight of the first compound, the second compound, the third compound, and the fourth compound. However, the embodiment is not limited thereto. When the amount of the fourth compound satisfies the above range, the energy transferred from the host to the first compound as a light-emitting dopant may be increased so that the emission ratio may be improved, and thus, the emission efficiency of the emission layer EML may be improved. When the amounts of the first compound, the second compound, the third compound, and the fourth compound included in the emission layer EML satisfy the above range and ratio, excellent emission efficiency and long service life may be achieved.

[0328] In the light emitting element ED, the emission layer EML may include an anthracene derivative, a pyrene derivative, a fluoranthene derivative, a 1,2-triphenylene derivative, a dihydrobenzanthracene derivative, or a triphenylene derivative. For example, the emission layer EML may include an anthracene derivative or a pyrene derivative.

[0329] In accordance with Figures 3 to 6 In the light emitting element ED of each of the embodiments shown in FIG. 1 , the emission layer EML may further include a host and a dopant of the related art in addition to the above-described host and dopant.

[0330] In an embodiment, the emission layer EML may include a compound represented by Formula E-1. The compound represented by Formula E-1 may be used as a fluorescent host material.

[0331] [Formula E-1]

[0332]

[0333] In formula E-1, R 31 To R 40 Each of the above may be independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted silyl group, a substituted or unsubstituted thiol group, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, or may be bonded to an adjacent group to form a ring. For example, in Formula E-1, R 31 To R 40 It may bond with an adjacent group to form a saturated hydrocarbon ring, an unsaturated hydrocarbon ring, a saturated heterocyclic ring, or an unsaturated heterocyclic ring.

[0334] In Formula E-1, c and d may be an integer selected from 0 to 5, each independently.

[0335] In an embodiment, the compound represented by Formula E-1 may be any compound selected from Compound E1 to Compound E19:

[0336]

[0337]

[0338] In an embodiment, the emission layer EML may include a compound represented by Formula E-2a or Formula E-2b. The compound represented by Formula E-2a or Formula E-2b may be used as a phosphorescent host material.

[0339] [Formula E-2a]

[0340]

[0341] In Formula E-2a, a may be an integer selected from 0 to 10; and L a It may be a directly linked, 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 The groups may each independently be a substituted or unsubstituted arylene group having 6 to 30 ring-forming carbon atoms or a substituted or unsubstituted heteroarylene group having 2 to 30 ring-forming carbon atoms.

[0342] In formula E-2a, A 1 To A 5 can be N or C (R i ). In Formula E-2a, R a To R i Each of the R and R groups may independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted amine group, a substituted or unsubstituted thiol group, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, or may be bonded to an adjacent group to form a ring. For example, R a To R i It may bond with an adjacent group to form a hydrocarbon ring or a heterocyclic ring including N, O, S, etc. as a ring-constituting atom.

[0343] In formula E-2a, A 1 To A 5 Two or three of them can each be N, and A 1 To A 5 The remaining groups in may be independently C(R i ).

[0344] [Formula E-2b]

[0345]

[0346] In Formula E-2b, Cbz1 and Cbz2 may each independently be an unsubstituted carbazole group or a carbazole group substituted with an aryl group having 6 to 30 ring carbon atoms. b It may be a directly connected, 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. In Formula E-2b, b may be an integer selected from 0 to 10, and when b is 2 or more, a plurality of L b The groups may each independently be a substituted or unsubstituted arylene group having 6 to 30 ring-forming carbon atoms or a substituted or unsubstituted heteroarylene group having 2 to 30 ring-forming carbon atoms.

[0347] The compound represented by Formula E-2a or Formula E-2b may be any compound selected from Compound Group E-2. However, the compounds listed in Compound Group E-2 are only examples, and the compounds represented by Formula E-2a or Formula E-2b are not limited to Compound Group E-2.

[0348] [Compound Group E-2]

[0349]

[0350]

[0351]

[0352] The emission layer EML may further include a material of the related art as a host material. For example, the emission layer EML may include at least one of the following as a host material: bis(4-(9H-carbazole-9-yl)phenyl)diphenylsilane (BCPDS), (4-(1-(4-(diphenylamino)phenyl)cyclohexyl)phenyl)diphenyl-phosphine oxide (POPCPA), bis[2-(diphenylphosphino)phenyl]ether oxide (DPEPO), 4,4'-bis(N-carbazolyl)-1,1'-biphenyl (CBP), 1,3-bis(carbazole-9-yl)benzene (mCP), 2,8-bis(diphenylphosphoryl)dibenzo[b,d]furan (PPF), 4,4',4"-tri(carbazole-9-yl)triphenylamine (TCTA), and 1,3,5-tri(1-phenyl-1H-benzo[d]imidazol-2-yl)benzene (TPBi). However, the embodiment is not limited thereto. For example, tris(8-hydroxyquinoline)aluminum (Alq 3), 9,10-di(naphthalene-2-yl)anthracene (ADN), 2-tert-butyl-9,10-di(naphthalene-2-yl)anthracene (TBADN), distyrylarene (DSA), 4,4'-bis(9-carbazolyl)-2,2'-dimethyl-biphenyl (CDBP), 2-methyl-9,10-bis(naphthalene-2-yl)anthracene (MADN), hexaphenylcyclotriphosphazene (CP1), 1,4-bis(triphenylsilyl)benzene (UGH2), hexaphenylcyclotrisiloxane (DPSiO 3 ), octaphenylcyclotetrasiloxane (DPSiO 4 ) etc. can be used as the main material.

[0353] In an embodiment, the emission layer EML may include a compound represented by Formula Ma. The compound represented by Formula Ma may be used as a phosphorescent dopant material.

[0354] [Formula Ma]

[0355]

[0356] In formula Ma, Y 1 To Y 4 and Z 1 To Z 4 can be independently C(R 1 ) or N; and R 1 To R 4 Each independently may be a hydrogen atom, a deuterium atom, a substituted or unsubstituted amine group, a substituted or unsubstituted sulfenyl group, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, or bonded to an adjacent group to form a ring. In formula Ma, m may be 0 or 1, and n may be 2 or 3. In formula Ma, when m is 0, n may be 3, and when m is 1, n may be 2.

[0357] The compound represented by formula Ma may be any compound selected from compound M-a1 to compound M-a25. However, compound M-a1 to compound M-a25 are merely examples, and the compound represented by formula Ma is not limited to compound M-a1 to compound M-a25.

[0358]

[0359]

[0360] In an embodiment, the emission layer EML may include a compound represented by one of Formulas Fa to Fc. The compound represented by one of Formulas Fa to Fc may be used as a fluorescent dopant material.

[0361] [Formula]

[0362]

[0363] In formula Fa, R a To R j The two of them can be independently represented by *-NAr 1 Ar 2 The group represented by R is substituted. a To R j Not by *-NAr 1 Ar 2 The remaining groups substituted by the groups represented may each independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms.

[0364] In *-NAr 1 Ar 2 In the group represented by 1 and Ar 2 and Ar 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. 1 and Ar 2 At least one of may be a heteroaryl group including O or S as a ring-forming atom.

[0365] [Formula Fb]

[0366]

[0367] In formula Fb, R a and R b Each of Ar and Ar may be independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, or may be bonded to an adjacent group to form a ring. 1 To Ar 4and Ar 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. 1 To Ar 4 At least one of may be a heteroaryl group including O or S as a ring-forming atom.

[0368] In Formula Fb, U and V may each independently be a substituted or unsubstituted hydrocarbon ring group having 5 to 30 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 2 to 30 ring carbon atoms.

[0369] In formula Fb, the number of rings represented by U and V may be 0 or 1 independently of each other. When the number of U or V is 1, a condensed ring may be present at the portion indicated by U or V, and when the number of U or V is 0, a condensed ring may not be present at the portion indicated by U or V. When the number of U is 0 and the number of V is 1, or when the number of U is 1 and the number of V is 0, the condensed ring having a fluorene core of formula Fb may be a cyclic compound having four rings. When the number of U and V is each 0, the condensed ring having a fluorene core of formula Fb may be a cyclic compound having three rings. When the number of U and V is each 1, the condensed ring having a fluorene core of formula Fb may be a cyclic compound having five rings.

[0370] [Formula Fc]

[0371]

[0372] In Formula Fc, A 1 and A 2 can be independently O, S, Se or N (R m ), and R m It may be a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms. 1 To R 11 Each may independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted amine group, a substituted or unsubstituted boron group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thiol group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, or may be bonded to an adjacent group to form a ring.

[0373] In Formula Fc, A 1 and A 2 Each of A and B may independently bond to a substituent of an adjacent ring to form a condensed ring.1 and A 2 Each independently is N(R m ), A 1 Can be used with R 4 or R 5 bond to form a ring. For example, A 2 Can be used with R 7 or R 8 bonded to form a ring.

[0374] In an embodiment, the emission layer EML may further include styryl derivatives (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)naphthalene-2-yl)vinyl)phenyl)-N-phenylaniline (N-BDAVBi) and 4,4'-bis[2-(4-(N,N-diphenylamino)phenyl)vinyl]biphenyl (DPAVBi)), perylene or its derivatives (e.g., 2,5,8,11-tetra-tert-butylperylene (TBP)), pyrene or its derivatives (e.g., 1,1'-dipyrene, 1,4-dipyrenylbenzene, 1,4-bis(N,N-diphenylamino)pyrene), etc. as dopant materials known in the related art.

[0375] The emission layer EML may further include a phosphorescent dopant material of the related art. 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 a phosphorescent dopant. For example, bis (4,6-difluorophenylpyridyl-N, C2) pyridine carboxylate iridium (III) (FIrpic), bis (2,4-difluorophenylpyridyl)-tetrakis (1-pyrazolyl) borate iridium (III) (FIr6) or octaethylporphyrin platinum (PtOEP) may be used as a phosphorescent dopant. However, the embodiment is not limited thereto.

[0376] In an embodiment, the emission layer EML may include quantum dots. The quantum dots may be crystals of semiconductor compounds. The quantum dots may emit light of various emission wavelengths according to the size of the crystals. By adjusting the ratio of elements in the quantum dot compound, the quantum dots may emit light of various emission wavelengths.

[0377] The diameter of the quantum dots may range from about 1 nm to about 10 nm.

[0378] Quantum dots can be synthesized by chemical bath deposition, metal organic chemical vapor deposition (MOCVD), molecular beam epitaxy (MBE) or similar processes. Chemical bath deposition is a method of mixing an organic solvent and a precursor material and growing quantum dot particle crystals. While growing the quantum dot particle crystals, the organic solvent can be used as a dispersant coordinated to the surface of the quantum dot particle crystals, and the organic solvent can control the growth of the quantum dot particle crystals. Accordingly, when compared with the metal organic chemical vapor deposition (MOCVD) process or the molecular beam epitaxy (MBE) process, chemical bath deposition may be more advantageous and the growth of quantum dot particle crystals can be controlled by a low-cost process.

[0379] In an embodiment, the emission layer EML may include quantum dots. The quantum dots may be group II-VI compounds, group III-VI compounds, group I-III-VI compounds, group III-V compounds, group III-II-V compounds, group IV-VI compounds, group IV elements, group IV compounds, or any combination thereof.

[0380] Examples of Group II-VI compounds may include: binary compounds selected from the group consisting of CdSe, CdTe, CdS, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, MgSe, MgS, and mixtures thereof; binary compounds selected from the group consisting of CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, CdZnSe, CdZnTe , a ternary compound selected from the group consisting of CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, MgZnSe, MgZnS and mixtures thereof; a quaternary compound selected from the group consisting of CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe, HgZnSTe and mixtures thereof; or any combination thereof.

[0381] Examples of Group II-VI semiconductor compounds may further include metals in Group I and / or elements in Group IV. Examples of Group I-II-VI compounds may include CuSnS or CuZnS. Examples of Group II-IV-VI compounds may include ZnSnS, etc. Examples of Group I-II-IV-VI compounds may include a metal selected from Cu 2 ZnSnS 2 , Cu 2 ZnSnS 4 , Cu 2 ZnSnSe 4 、Ag 2ZnSnS 2 A quaternary compound from the group consisting of and mixtures thereof.

[0382] Examples of III-VI compounds may include: binary compounds (such as In 2 S 3 or In 2 Se 3 ), ternary compounds such as (InGaS 3 or InGaSe 3 ); or any combination thereof.

[0383] Examples of Group I-III-VI compounds may include: selected from AgInS, AgInS 2 、CuInS、CuInS 2 、AgGaS 2 、CuGaS 2 、CuGaO 2 、AgGaO 2 、AgAlO 2 Ternary compounds in the group consisting of and mixtures thereof; quaternary compounds, such as AgInGaS 2 or CuInGaS 2 ; or any combination thereof.

[0384] Examples of the III-V group compound may include: a binary compound selected from the group consisting of GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, InSb, and mixtures thereof; a ternary compound 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; a quaternary compound selected from the group consisting of GaAlNP, GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNP, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs, InAlPSb, and mixtures thereof; or any combination thereof. In an embodiment, the III-V group compound may further include a Group II metal. For example, InZnP or the like may be selected as the Group III-II-V compound.

[0385] The IV-VI group compound may be selected from the group consisting of: a binary compound selected from the group consisting of SnS, SnSe, SnTe, PbS, PbSe, PbTe and mixtures thereof, a ternary compound selected from the group consisting of SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, SnPbTe and mixtures thereof, and a quaternary compound selected from the group consisting of SnPbSSe, SnPbSeTe, SnPbSTe and mixtures thereof. The IV group element may be selected from the group consisting of Si, Ge and mixtures thereof. The IV group compound may be a binary compound selected from the group consisting of SiC, SiGe and mixtures thereof.

[0386] Each element included in a multi-component compound (such as a binary compound, a ternary compound, or a quaternary compound) may exist in a particle in a uniform or non-uniform concentration distribution. That is, these formulas mean the type of element included in the compound, and the ratio of the elements in the compound may be different. For example, AgInGaS 2 Can mean AgIn x Ga 1-x S 2 (0 <x<1)。

[0387] In an embodiment, the quantum dot may have a single structure in which the concentration of each element included in the quantum dot is uniform, or the quantum dot may have a core / shell structure in which one quantum dot surrounds another quantum dot. For example, the material included in the core may be different from the material included in the shell.

[0388] The shell of the quantum dot can be used as a protective layer to prevent chemical denaturation of the core to maintain semiconductor properties, and / or can be used as a charging layer to impart electrophoretic properties to the quantum dot. The shell can be a single layer or multiple layers. The interface between the core and the shell can have a concentration gradient in which the concentration of the element present in the shell decreases toward the center of the core.

[0389] In an embodiment, the quantum dot may have the above-mentioned core / shell structure, which includes a core including nanocrystals and a shell surrounding the core. Examples of the shell of the quantum dot may include metal oxides, non-metal oxides, semiconductor compounds, or any combination thereof.

[0390] Examples of metal oxides or non-metal oxides may include: binary compounds such as SiO 2 、Al 2 O 3 、TiO 2 、ZnO、MnO、Mn 2 O 3 , Mn 3 O 4 , CuO, FeO, Fe 2O 3 , Fe 3 O 4 , CoO, Co 3 O 4 or NiO; ternary compounds, such as MgAl 2 O 4 、CoFe 2 O 4 、NiFe 2 O 4 or CoMn 2 O 4 ; or any combination thereof. However, the embodiments are not limited thereto.

[0391] Examples of semiconductor compounds may include CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnSeS, ZnTeS, GaAs, GaP, GaSb, HgS, HgSe, HgTe, InAs, InP, InGaP, InSb, AlAs, AlP, AlSb, etc., but embodiments are not limited thereto.

[0392] The quantum dots may have a full width at half maximum (FWHM) of an emission wavelength spectrum equal to or less than about 45 nm. For example, the quantum dots may have a FWHM of an emission wavelength spectrum equal to or less than about 40 nm. For example, the quantum dots may have a FWHM of an emission wavelength spectrum equal to or less than about 30 nm. Within any of the above ranges, color purity or color reproducibility may be improved. Light emitted by the quantum dots may be emitted in all directions, so that a wide viewing angle may be improved.

[0393] The form of the quantum dot is not particularly limited, and may be any form used in the relevant field. For example, the quantum dot may have a spherical shape, a pyramidal shape, a multi-arm shape, or a cubic shape, or the quantum dot may be in the form of nanoparticles, nanotubes, nanowires, nanofibers, nanoplates, etc.

[0394] As the size of the quantum dots is adjusted or the element ratio of the quantum dot compound is adjusted, the energy band gap can be controlled, and thus light in various wavelength ranges can be obtained from the quantum dot emission layer. Therefore, the quantum dots as described above can be implemented (using quantum dots of different sizes or quantum dot compounds of different element ratios) so that the light emitting element emits light in various wavelength ranges. The size of the quantum dots or the element ratio of the quantum dot compound can be independently adjusted to emit red light, green light and / or blue light. For example, the quantum dots can be configured to emit white light by combining light of various colors.

[0395] In accordance with Figures 3 to 6In each of the light emitting elements ED of the illustrated embodiments, an electron transport region ETR may be provided on the emission layer EML. The electron transport region ETR may include at least one of a hole blocking layer HBL, an electron transport layer ETL, and an electron injection layer EIL, but the embodiments are not limited thereto.

[0396] The electron transport region ETR may have a single-layer structure composed of a single material, a single-layer structure including different materials, or a multi-layer structure including a plurality of layers including different materials.

[0397] 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 formed of an electron injection material and an electron transport material. In other embodiments, the electron transport region ETR may have a single-layer structure formed of different materials, or may have a structure in which an electron transport layer ETL / electron injection layer EIL or a hole blocking layer HBL / electron transport layer ETL / electron injection layer EIL are stacked from the emission layer EML in their respective recited order, but the embodiment is not limited thereto. The electron transport region ETR may have a thickness of about 100 nm. to about The thickness is within the range of .

[0398] The electron transport region ETR may be formed using various methods such as a vacuum deposition method, a spin coating method, a casting method, a Langmuir-Brokett (LB) method, an inkjet printing method, a laser printing method, and a laser induced thermal imaging (LITI) method.

[0399] In the light emitting element ED according to the embodiment, the electron transport region ETR may include a compound represented by Formula ET-2:

[0400] [Formula ET-2]

[0401]

[0402] In formula ET-2, X 1 To X 3 At least one of may each be N; and X 1 To X 3 The remaining groups in may be independently C(R a ). In formula ET-2, R a It may be a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms. 1 To Ar 3Each may independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms.

[0403] In Formula ET-2, a to c may each independently be an integer selected from 0 to 10. In Formula ET-2, L 1 To L 3 Each of L and L is independently a directly linked, 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 To L 3 A plurality of groups of each of may each independently be a substituted or unsubstituted arylene group having 6 to 30 ring-forming carbon atoms or a substituted or unsubstituted heteroarylene group having 2 to 30 ring-forming carbon atoms.

[0404] The electron transport region ETR may include an anthracene-based compound. However, the embodiment is not limited thereto, and the electron transport region ETR may include, for example, tris(8-hydroxyquinoline)aluminum (Alq 3 ), 1,3,5-tris[(3-pyridyl)-phenyl-3-yl]benzene, 2,4,6-tris(3'-(pyridin-3-yl)biphenyl-3-yl)-1,3,5-triazine, 2-(4-(N-phenylbenzimidazol-1-yl)phenyl)-9,10-dinaphthylanthracene, 1,3,5-tris(1-phenyl-1H-benzo[d]imidazol-2-yl)benzene (TPBi), 2,9-dimethyl-4,7-diphenyl 1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), 3-(4-biphenyl)-4-phenyl-5-tert-butylphenyl-1,2,4-triazole (TAZ), 4-(naphthalene-1-yl)-3,5-diphenyl-4H-1,2,4-triazole (NTAZ), 2-(4-biphenyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole ( t Bu-PBD), bis(2-methyl-8-hydroxyquinoline-N1,O8)-(1,1'-biphenyl-4-hydroxy)aluminum (BAlq), bis(benzoquinoline-10-hydroxy)beryllium (Bebq 2 ), 9,10-di(naphthalene-2-yl)anthracene (ADN), 1,3-bis[3,5-di(pyridin-3-yl)phenyl]benzene (BmPyPhB) or a mixture thereof.

[0405] In an embodiment, the electron transport region ETR may include at least one compound selected from the group consisting of Compound ET1 to Compound ET36:

[0406]

[0407]

[0408] In an embodiment, the electron transport region ETR may include a metal halide such as LiF, NaCl, CsF, RbCl, RbI, CuI, and KI; a lanthanide metal such as Yb; or a co-deposited material of a metal halide and a lanthanide metal. For example, the electron transport region ETR may include KI:Yb, RbI:Yb, LiF:Yb, etc. as a co-deposited material. The electron transport region ETR may be made of a metal oxide (such as Li 2 O or BaO) or 8-hydroxy-quinoline lithium (Liq), etc., but the embodiment is not limited thereto. The electron transport region ETR may also be formed of a mixture material of an electron transport material and an insulating organic metal salt. The insulating organic metal salt may be a material with an energy band gap equal to or greater than about 4 eV. For example, the insulating organic metal salt may include a metal acetate, a metal benzoate, a metal acetoacetate, a metal acetylacetonate, or a metal stearate.

[0409] In addition to the above materials, the electron transport region ETR may further include at least one of 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), diphenyl(4-(triphenylsilyl)phenyl)phosphine oxide (TSPO1), and 4,7-diphenyl-1,10-phenanthroline (Bphen), but the embodiment is not limited thereto.

[0410] The electron transport region ETR may include the above-mentioned compound of the electron transport region ETR in at least one of the electron injection layer EIL, the electron transport layer ETL, and the hole blocking layer HBL.

[0411] When the electron transport region ETR includes the electron transport layer ETL, the electron transport layer ETL may have a thickness of about to about For example, the electron transport layer ETL may have a thickness of about to about If the thickness of the electron transport layer ETL satisfies any of the aforementioned ranges, satisfactory electron transport characteristics can be obtained without significantly increasing the driving voltage. When the electron transport region ETR includes the electron injection layer EIL, the electron injection layer EIL may have a thickness of about to about For example, the electron injection layer EIL may have a thickness of about to about If the thickness of the electron injection layer EIL satisfies any of the above ranges, satisfactory electron injection characteristics can be obtained without significantly increasing the driving voltage.

[0412] The second electrode EL2 may be provided on the electron transport region ETR. The second electrode EL2 may be a common electrode. The second electrode EL2 may be a cathode or an anode, but the embodiment is not limited thereto. For example, when the first electrode EL1 is an anode, the second electrode EL2 may be a cathode, and when the first electrode EL1 is a cathode, the second electrode EL2 may be an anode.

[0413] The second electrode EL2 may be a transmissive electrode, a transflective electrode or a reflective electrode. When the second electrode EL2 is a transmissive electrode, the second electrode EL2 may be formed of a transparent metal oxide (e.g., indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), indium tin zinc oxide (ITZO), etc.).

[0414] When the second electrode EL2 is a transflective electrode or a reflective electrode, the second electrode EL2 may include at least one of Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF, Mo, Ti, Yb and W, a compound thereof, or a mixture thereof (e.g., AgMg, AgYb or MgYb), or a multilayer structure material such as LiF / Ca or LiF / Al. In an embodiment, the second electrode EL2 may have a multilayer structure including a reflective film or a transflective film formed of the above materials, and a transparent conductive film formed of ITO, IZO, ZnO, ITZO, etc. For example, the second electrode EL2 may include the above metal materials, a combination of at least two of the above metal materials, or an oxide of the above metal materials, etc.

[0415] Although not shown in the drawings, the second electrode EL2 may be electrically connected to the auxiliary electrode. If the second electrode EL2 is electrically connected to the auxiliary electrode, the resistance of the second electrode EL2 may be reduced.

[0416] In an embodiment, the light emitting element ED may further include a capping layer CPL which may be further disposed on the second electrode EL2. The capping layer CPL may be a multi-layer or a single layer.

[0417] In an embodiment, the capping layer CPL may include an organic layer or an inorganic layer. For example, when the capping layer CPL contains an inorganic material, the inorganic material may include an alkali metal compound (eg, LiF), an alkaline earth metal compound (eg, MgF 2 )、SiON、SiN x 、SiO y wait.

[0418] For example, when the capping layer CPL includes an organic material, the organic material may include 2,2'-dimethyl-N,N'-di[(1-naphthyl)-N,N'-diphenyl]-1,1'-biphenyl-4,4'-diamine (α-NPD), NPB, TPD, m-MTDATA, Alq 3 , CuPc, N4,N4,N4',N4'-tetrakis(biphenyl-4-yl)biphenyl-4,4'-diamine (TPD15), 4,4',4"-tris(carbazole-9-yl)triphenylamine (TCTA), etc., or may be epoxy resin or acrylate (such as methacrylate). However, embodiments are not limited thereto. In embodiments, the capping layer CPL may include at least one of compounds P1 to P5:

[0419]

[0420] The capping layer CPL may have a refractive index equal to or greater than about 1.6. For example, the capping layer CPL may have a refractive index equal to or greater than about 1.6 with respect to light in a wavelength range of about 550 nm to about 660 nm.

[0421] Figures 8 to 11 Each is a cross-sectional view of a display device according to an embodiment. Figures 8 to 11 In the description of the display device according to the embodiment shown in FIG. 1 , the above reference numerals will not be explained again. Figures 1 to 7C Features that have been described, while different features will be described.

[0422] refer to Figure 8 , the display device DD-a according to the embodiment may include: a display panel DP including a display device layer DP-ED, a light control layer CCL disposed on the display panel DP, and a color filter layer CFL.

[0423] exist Figure 8 In the embodiment shown in FIG. 1 , the display panel DP may include a base layer BS, a circuit layer DP-CL and a display device layer DP-ED provided on the base layer BS, and the display device layer DP-ED may include a light emitting element ED.

[0424] The light emitting element ED may include a first electrode EL1, a hole transport region HTR disposed on the first electrode EL1, an emission layer EML disposed on the hole transport region HTR, an electron transport region ETR disposed on the emission layer EML, and a second electrode EL2 disposed on the electron transport region ETR. Figure 8 The structure of the light emitting element ED shown in FIG. Figures 3 to 6 The structure of the light emitting element ED in one of the above is the same.

[0425] In the display device DD-a according to the embodiment, the emission layer EML included in the light emitting element ED may include the polycyclic compound represented by Formula 1.

[0426] refer to Figure 8 , the emission layer EML may be disposed in the opening OH defined by the pixel defining film PDL. For example, the emission layer EML separated by the pixel defining film PDL and correspondingly provided to each of the light emitting regions PXA-R, PXA-G, and PXA-B may emit light within the same wavelength range. In the display device DD-a, the emission layer EML may emit blue light. Although not shown in the drawings, in an embodiment, the emission layer EML may be provided as a common layer of each of the light emitting regions PXA-R, PXA-G, and PXA-B.

[0427] The light control layer CCL may be disposed on the display panel DP. 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 may emit the resulting light. For example, the light control layer CCL may be a layer including quantum dots or a layer including phosphors.

[0428] The light-controlling layer CCL may include light-controlling parts CCP1, CCP2, and CCP3. The light-controlling parts CCP1, CCP2, and CCP3 may be spaced apart from each other.

[0429] refer to Figure 8 , the partition pattern BMP may be disposed between the light-controlling parts CCP1, CCP2, and CCP3 that are spaced apart from each other, but the embodiment is not limited thereto. Figure 8 , it is shown that the partition pattern BMP does not overlap with the light-controlling portions CCP1, CCP2, and CCP3, but edges of the light-controlling portions CCP1, CCP2, and CCP3 may overlap with at least a portion of the partition pattern BMP.

[0430] The light control layer CCL may include: a first light control part CCP1, which includes a first quantum dot QD1 that converts the first color light provided from the light emitting element ED into a second color light; a second light control part CCP2, which includes a second quantum dot QD2 that converts the first color light into a third color light; and a third light control part CCP3 that transmits the first color light.

[0431] In an embodiment, the first light control part CCP1 may provide red light as the second color light, and the second light control part CCP2 may provide green light as the third color light. The third light control part CCP3 may provide blue light by transmitting blue light as 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 quantum dots QD1 and QD2 may each be a quantum dot as described above.

[0432] The light control layer CCL may further include a scatterer SP. The first light control part CCP1 may include first quantum dots QD1 and a scatterer SP, the second light control part CCP2 may include second quantum dots QD2 and a scatterer SP, and the third light control part CCP3 may include no quantum dots but may include a scatterer SP.

[0433] The scatterer SP may be inorganic particles. For example, the scatterer SP may include TiO 2 、ZnO、Al 2 O 3 、SiO 2 and hollow silica. The scatterer SP may include TiO 2 、ZnO、Al 2 O 3 、SiO 2 and hollow silica, or may be selected from TiO 2 、ZnO、Al 2 O 3 、SiO 2 and a mixture of at least two materials selected from hollow silica.

[0434] The first light-control part CCP1, the second light-control part CCP2, and the third light-control part CCP3 may each include base resins BR1, BR2, and BR3 in which quantum dots QD1 and QD2 and scatterers SP are dispersed. In an embodiment, the first light-control part CCP1 may include the first quantum dots QD1 and scatterers SP dispersed in the first base resin BR1, the second light-control part CCP2 may include the second quantum dots QD2 and scatterers SP dispersed in the second base resin BR2, and the third light-control part CCP3 may include the scatterers SP dispersed in the third base resin BR3.

[0435] The base resins BR1, BR2, and BR3 are media in which the quantum dots QD1 and QD2 and the scatterers SP are dispersed, and may be formed of various resin compositions that may be generally referred to as binders. For example, the base resins BR1, BR2, and BR3 may be acrylic resins, urethane resins, silicone resins, epoxy resins, and the like. The base resins BR1, BR2, and BR3 may each be a transparent resin. In an 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.

[0436] The light control layer CCL may include an isolation layer BFL1. The isolation layer BFL1 may prevent the penetration of moisture and / or oxygen (hereinafter, referred to as "moisture / oxygen"). The isolation layer BFL1 may block the light control parts CCP1, CCP2, and CCP3 from being exposed to moisture / oxygen. The isolation layer BFL1 may cover the light control parts CCP1, CCP2, and CCP3. The isolation layer BFL2 may be provided between the light control parts CCP1, CCP2, and CCP3 and the filters CF1, CF2, and CF3.

[0437] The isolation layers BFL1 and BFL2 may each independently include at least one inorganic layer. For example, the isolation layers BFL1 and BFL2 may each independently include an inorganic material. For example, the isolation layers BFL1 and BFL2 may each independently include silicon nitride, aluminum nitride, zirconium nitride, titanium nitride, hafnium nitride, tantalum nitride, silicon oxide, aluminum oxide, titanium oxide, tin oxide, cerium oxide, silicon oxynitride, a metal film ensuring light transmittance, etc. The isolation layers BFL1 and BFL2 may each independently include an organic film. The isolation layers BFL1 and BFL2 may each be formed of a single layer or a multilayer.

[0438] In the display device DD-a, the color filter layer CFL may be disposed on the light control layer CCL. In an embodiment, the color filter layer CFL may be directly disposed on the light control layer CCL. For example, the isolation layer BFL2 may be omitted.

[0439] The color filter layer CFL may include filters CF1, CF2, and CF3. The color filter layer 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. The filters CF1, CF2, and CF3 may each include a polymerized photosensitive resin and / or 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.

[0440] 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 polymerized photosensitive resin and may not include a pigment or a dye. The third filter CF3 may be transparent. The third filter CF3 may be formed of a transparent photosensitive resin.

[0441] In an embodiment, the first filter CF1 and the second filter CF2 may each be a yellow filter. The first filter CF1 and the second filter CF2 may not be separated but may be provided as one filter.

[0442] Although not shown in the drawings, the color filter layer CFL may further include a light shielding portion (not shown). The light shielding portion (not shown) may be a black matrix. The light shielding portion (not shown) may include an organic light shielding material or an inorganic light shielding material each including a black pigment or dye. The light shielding portion (not shown) may prevent light leakage and may separate adjacent filters CF1, CF2, and CF3.

[0443] The first to third filters CF1, CF2, and CF3 may be disposed to correspond to the red light emitting area PXA-R, the green light emitting area PXA-G, and the blue light emitting area PXA-B, respectively.

[0444] The base substrate BL may be disposed on the color filter layer CFL. The base substrate BL may provide a base surface on which the color filter layer CFL, the light control layer CCL, and the like are disposed. The base substrate BL may be a glass substrate, a metal substrate, a plastic substrate, and the like. However, the embodiment is not limited thereto, and the base substrate BL may include an inorganic layer, an organic layer, or a composite material layer. Although not shown in the drawings, in an embodiment, the base substrate BL may be omitted.

[0445] Fig. 9 Schematic cross-sectional view of a portion of a display device according to an embodiment. In the display device DD-TD according to the embodiment, the light emitting element ED-BT may include light emitting structures OL-B1, OL-B2, and OL-B3. The light emitting element ED-BT may include a first electrode EL1 and a second electrode EL2 facing each other, and light emitting structures OL-B1, OL-B2, and OL-B3 stacked in a thickness direction between the first electrode EL1 and the second electrode EL2. The light emitting structures OL-B1, OL-B2, and OL-B3 may each include an emission layer EML ( Figure 8 ) and a hole transport region HTR ( Figure 8 ) and the electron transport region ETR ( Figure 8 ).

[0446] For example, the light emitting elements ED-BT included in the display devices DD-TD may be light emitting elements having a tandem structure and including a plurality of emission layers EML.

[0447] exist Fig. 9 In the embodiment explained in , 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 light emitted from each of the light emitting structures OL-B1, OL-B2, and OL-B3 may have a wavelength range different from each other. For example, the light emitting element ED-BT including the light emitting structures OL-B1, OL-B2, and OL-B3 emitting light having a wavelength range different from each other may emit white light.

[0448] The charge generation layers CGL1 and CGL2 may each be disposed between adjacent ones of the light emitting structures OL-B1, OL-B2, and OL-B3. The charge generation layers CGL1 and CGL2 may each independently include a p-type charge generation layer and / or an n-type charge generation layer.

[0449] At least one of the light emitting structures OL-B1, OL-B2, and OL-B3 included in the display devices DD-TD according to the embodiments may include a polycyclic compound represented by Formula 1. For example, at least one of the plurality of emission layers included in the light emitting elements ED-BT may include a polycyclic compound represented by Formula 1.

[0450] Fig.10 is a schematic cross-sectional view of a display device according to an embodiment. Fig.11 is a schematic cross-sectional view of a display device according to an embodiment.

[0451] refer to Fig.10 , the display device DD-b according to the embodiment may include light emitting elements ED-1, ED-2, and ED-3 in which two emission layers are stacked. Figure 2 When compared with the display device DD shown in Fig.10 The display device DD-b of the embodiment shown in FIG. 1 is different in that at least the first to third light-emitting elements ED-1, ED-2, and ED-3 each include two emission 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 emission layers can emit light in the same wavelength range.

[0452] The first light-emitting element ED-1 may include a first red emission layer EML-R1 and a second red emission layer EML-R2. The second light-emitting element ED-2 may include a first green emission layer EML-G1 and a second green emission layer EML-G2. The third light-emitting element ED-3 may include a first blue emission layer EML-B1 and a second blue emission layer EML-B2. The emission auxiliary portion OG may be disposed between the first red emission layer EML-R1 and the second red emission layer EML-R2, between the first green emission layer EML-G1 and the second green emission layer EML-G2, and between the first blue emission layer EML-B1 and the second blue emission layer EML-B2.

[0453] The emission auxiliary part OG may be a single layer or a multilayer. The emission auxiliary part OG may include a charge generation layer. For example, the emission auxiliary part OG may include an electron transport region (not shown), a charge generation layer (not shown), and a hole transport region (not shown), which may be stacked in this order. The emission auxiliary part OG may be provided as a common layer for all of the first to third light-emitting elements ED-1, ED-2, and ED-3. However, the embodiment is not limited thereto, and the emission auxiliary part OG may be provided by patterning in an opening OH defined by a pixel defining film PDL.

[0454] The first red emission layer EML-R1, the first green emission layer EML-G1, and the first blue emission layer EML-B1 may be disposed between the emission auxiliary portion OG and the electron transport region ETR. The second red emission layer EML-R2, the second green emission layer EML-G2, and the second blue emission layer EML-B2 may be disposed between the hole transport region HTR and the emission auxiliary portion OG.

[0455] For example, the first light-emitting element ED-1 may include a first electrode EL1, a hole transport region HTR, a second red emission layer EML-R2, an emission auxiliary portion OG, a first red emission layer EML-R1, an electron transport region ETR, and a second electrode EL2 stacked in the following order. The second light-emitting element ED-2 may include a first electrode EL1, a hole transport region HTR, a second green emission layer EML-G2, an emission auxiliary portion OG, a first green emission layer EML-G1, an electron transport region ETR, and a second electrode EL2 stacked in the following order. The third light-emitting element ED-3 may include a first electrode EL1, a hole transport region HTR, a second blue emission layer EML-B2, an emission auxiliary portion OG, a first blue emission layer EML-B1, an electron transport region ETR, and a second electrode EL2 stacked in the following order.

[0456] The optical auxiliary layer PL may be disposed on the display device layer DP-ED. The optical auxiliary layer PL may include a polarizing layer. The optical auxiliary layer PL may be disposed on the display panel DP and may control light reflected by external light at the display panel DP. Although not shown in the drawings, in an embodiment, the optical auxiliary layer PL may be omitted from the display device DD-b.

[0457] exist Fig.10 At least one emission layer included in the display device DD-b according to the embodiment shown in FIG. 1 may include a polycyclic compound according to the embodiment. For example, at least one of the first blue emission layer EML-B1 and the second blue emission layer EML-B2 may include a polycyclic compound according to the embodiment.

[0458] and Fig. 9 and Fig.10 compared to, Fig.11A display device DD-c is shown, which differs at least in that it includes four light emitting structures OL-B1, OL-B2, OL-B3, and OL-C1. The light emitting element ED-CT may include a first electrode EL1 and a second electrode EL2 facing each other, and first to fourth light emitting structures OL-B1, OL-B2, OL-B3, and OL-C1 stacked in a thickness direction between the first electrode EL1 and the second electrode EL2. The light emitting structures OL-C1, OL-B1, OL-B2, and OL-B3 are stacked in sequence, and a charge generation layer CGL1 is disposed between the light emitting structures OL-B1 and OL-C1, a charge generation layer CGL2 is disposed between the light emitting structures OL-B1 and OL-B2, and a charge generation layer CGL3 is disposed between the light emitting structures OL-B2 and OL-B3. Among the four light emitting structures, the first to third light emitting structures OL-B1, OL-B2, and OL-B3 may each 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 having different wavelength ranges from each other.

[0459] The charge generation layers CGL1, CGL2, and CGL3 disposed between adjacent light emitting structures among the first to fourth light emitting structures OL-B1, OL-B2, OL-B3, and OL-C1 may each include a p-type charge generation layer and / or an n-type charge generation layer.

[0460] In the display device DD-c, at least one of the light emitting structures OL-B1, OL-B2, OL-B3 and OL-C1 may each independently include the polycyclic compound according to the embodiment. For example, in the embodiment, at least one of the first to third light emitting structures OL-B1, OL-B2 and OL-B3 may each independently include the polycyclic compound according to the embodiment.

[0461] The light emitting element ED according to the embodiment may include a polycyclic compound represented by Formula 1 in at least one functional layer disposed between the first electrode EL1 and the second electrode EL2, and may exhibit excellent emission efficiency and improved life characteristics. For example, the emission layer EML of the light emitting element ED may include a polycyclic compound represented by Formula 1, and the light emitting element may exhibit long life characteristics.

[0462] In an embodiment, the electronic device may include a display device including a light emitting element and a control portion for controlling the display device. The electronic device may be a device activated according to an electrical signal. The electronic device may include a display device of various embodiments. For example, the electronic device may include not only large electronic devices such as televisions, monitors, or outdoor billboards, but also small and medium-sized electronic devices such as personal computers, laptop computers, personal digital terminals, display devices for vehicles, game consoles, portable electronic devices, or cameras.

[0463] Fig.12 is a schematic perspective view of the interior of a vehicle AM ​​including first to fourth display devices DD-1, DD-2, DD-3 and DD-4. At least one of the first to fourth display devices DD-1, DD-2, DD-3 and DD-4 may have a display device according to the reference Figure 1 , Figure 2 and Figures 8 to 11 The structure of one of the display devices DD, DD-TD, DD-a, DD-b, and DD-c is described.

[0464] Fig.12 Schematic perspective view of the interior of a vehicle AM ​​including first to fourth display devices DD-1, DD-2, DD-3 and DD-4 in various vehicles such as bicycles, motorcycles, trains, ships and airplanes. In an embodiment, at least one of the first to fourth display devices DD-1, DD-2, DD-3 and DD-4 having a structure according to one of the display devices DD, DD-TD, DD-a, DD-b and DD-c can be used for a personal computer, a laptop computer, a personal digital terminal, a game console, a portable electronic device, a television, a monitor or an outdoor billboard, etc. However, these are presented only as examples and can therefore be used in other electronic devices.

[0465] At least one of the first to fourth display devices DD-1, DD-2, DD-3 and DD-4 may each independently include a Figures 3 to 6 Described light emitting element ED.

[0466] refer to Fig.12 The vehicle AM ​​may include a steering wheel HA and a shift lever GR for driving the vehicle AM. The vehicle AM ​​may include a front window GL disposed to face the driver.

[0467] 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 instrument panel displaying first information of the vehicle AM. The first information may include a first scale indicating a driving speed of the vehicle AM, a second scale indicating an engine speed (e.g., revolutions per minute (RPM)), a fuel status, etc. The first scale and the second scale may each be displayed as a digital image.

[0468] It can be arranged in a second zone facing the driver's seat and overlapping with the front window GL. The driver's seat can be a seat provided with a steering wheel HA. For example, the second display device DD-2 can be a head-up display (HUD) that displays the second information of the vehicle AM. The second display device DD-2 can be optically transparent. The second information can include a digital value indicating the driving speed and can further include information such as the current time. Although not shown in the accompanying drawings, in an embodiment, the second information of the second display device DD-2 can be projected onto the front window GL to be displayed.

[0469] The third display device DD-3 may be arranged in a third zone adjacent to the shift lever GR. For example, the third display device DD-3 may be a center information display (CID) for the vehicle that displays the third information, and the third display device DD-3 may be arranged between the driver's seat and the passenger seat. The passenger seat may be a seat spaced apart from the driver's seat, with the shift lever GR arranged between them. The third information may include information about traffic (e.g., navigation information), information about playing music or radio broadcasts or videos (or images), information about the temperature in the vehicle AM, etc.

[0470] The fourth display device DD-4 may be spaced apart from the steering wheel HA and the shift lever GR, and may be disposed in a fourth zone adjacent to the side of the vehicle AM. For example, the fourth display device DD-4 may be a digital side mirror 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 outside the vehicle AM. The fourth information may include an image of the outside of the vehicle AM.

[0471] The first to fourth information as described above are presented only as examples, and the first to fourth display devices DD-1, DD-2, DD-3, and DD-4 may further display information about the interior and exterior of the vehicle AM. The first to fourth information may include information different from each other. However, the embodiment is not limited thereto, and a portion of the first to fourth information may include information identical to each other.

[0472] Hereinafter, a polycyclic compound according to an embodiment and a light emitting element according to an embodiment will be described with reference to Examples and Comparative Examples.The Examples described below are provided only as illustrations to help understand the present disclosure, and the scope thereof is not limited thereto.

[0473] [Example]

[0474] 1. Synthesis of polycyclic compounds

[0475] The synthesis method of the polycyclic compound according to the embodiment will be explained by illustrating the synthesis methods of Compound 4, Compound 10 and Compound 23. The synthesis method of the polycyclic compound explained below is provided only as an example, and the synthesis method of the polycyclic compound according to the embodiment is not limited to the following examples.

[0476] (1) Synthesis of Compound 4

[0477] Compound 4 according to an embodiment can be synthesized, for example, through Reaction 1.

[0478] [Reaction 1]

[0479]

[0480] 1) Synthesis of intermediate compound 4-a

[0481] Under argon atmosphere, 1,3-dibromo-5-(tert-butyl)benzene (24 g, 38 mmol), diphenylamine (13 g, 76 mmol), Pd 2 dba 3 (1.0 g, 1.1 mmol), tri-tert-butylphosphine (P(tbu) 3 , 1.1 mL, 2.2 mmol) and sodium tert-butoxide (STB, 11 g, 114 mmol) were added to a 2 L flask and dissolved in 400 mL of toluene. The reaction solution was stirred at about 100 ° C for about 12 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added and extracted. The organic layer was collected and filtered through MgSO 4 The solvent of the filtrate solution was removed under reduced pressure, and the solid thus obtained was purified by using silica gel and using CH 2 Cl 2 The resulting product was purified and separated by column chromatography using 4-nitropropene and hexane as a developing solvent to obtain an intermediate compound 4-a (white solid, 24 g, yield 81%).

[0482] ESI-LCMS:[M] + :C 22 H 22 BrN, m / z: 379.0911.

[0483] 2) Synthesis of intermediate compound 4-b

[0484] Under argon atmosphere, intermediate compound 4-a (24 g, 38 mmol), aniline (13 g, 76 mmol), Pd 2 dba3 (1.0 g, 1.1 mmol), tri-tert-butylphosphine (P(tbu) 3 , 1.1 mL, 2.2 mmol) and sodium tert-butoxide (11 g, 114 mmol) were added to a 2 L flask and dissolved in 400 mL of toluene. The reaction solution was stirred at about 100 ° C for about 12 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added and extracted. The organic layer was collected and filtered through MgSO 4 The solvent of the filtrate solution was removed under reduced pressure, and the solid thus obtained was purified by using silica gel and using CH 2 Cl 2 The resulting product was purified and separated by column chromatography using 4-nitropropene and hexane as a developing solvent to obtain an intermediate compound 4-b (white solid, 24 g, yield 81%).

[0485] ESI-LCMS:[M] + :C 28 H 28 N 2 , m / z:392.2387.

[0486] 3) Synthesis of intermediate compound 4-c

[0487] Under argon atmosphere, intermediate compound 4-b (24 g, 30 mmol), 1,6-dibromopyrene (10 g, 30 mmol), Pd 2 dba 3 (0.8 g, 0.9 mmol), tri-tert-butylphosphine (0.8 mL, 1.8 mmol) and sodium tert-butoxide (8.6 g, 90 mmol) were added to a 2 L flask and dissolved in 300 mL of toluene. The reaction solution was stirred at about 100 ° C for about 12 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added and extracted. The organic layer was collected and filtered through MgSO 4 The solvent of the filtrate solution was removed under reduced pressure, and the solid thus obtained was purified by using silica gel and using CH 2 Cl 2 The resulting product was purified and separated by column chromatography using 4-nitropropene and hexane as a developing solvent to obtain an intermediate compound 4-c (white solid, 18 g, yield 62%).

[0488] ESI-LCMS:[M] + :C 72 H 62 N 4 , m / z:982.5053.

[0489] 4) Synthesis of Compound 4

[0490] Under an argon atmosphere, the intermediate compound 4-c (8 g, 5.7 mmol) was added to a 1 L flask and dissolved in 200 mL of o-dichlorobenzene, and BI was added thereto. 3 (1.5 equivalents). The reaction solution was stirred at about 140° C. for about 12 hours. After cooling, triethylamine was added to quench the reaction, the solvent was removed under reduced pressure, and the solid thus obtained was purified by using silica gel and using CH 2 Cl 2 The resulting product was purified and separated by column chromatography using 4% pyrrolidone and hexane as a developing solvent to obtain Compound 4 (yellow solid, 1.6 g, yield 21%).

[0491] ESI-LCMS:[M] + :C 72 H 56 B 2 N 4 , m / z:998.4712.

[0492] NMR- 1 H: 8.57(s,2H),8.38(d,2H),7.94(d,2H),7.88(m,8H),7.35(m,10H),7.24(m,4H),7.08(d,8H),6.15(s,4H),1.77(s,18H).

[0493] (2) Synthesis of Compound 10

[0494] Compound 10 according to an embodiment can be synthesized, for example, through Reaction 2.

[0495] [Reaction 2]

[0496]

[0497] 1) Synthesis of intermediate compound 10-a

[0498] Intermediate compound 10-a was obtained by using substantially the same method as the synthesis method of intermediate compound 4-a, except that 3-bromo-5-chloro-1,1′-biphenyl was used instead of 1,3-dibromo-5-(tert-butyl)benzene as a starting material.

[0499] 2) Synthesis of intermediate compound 10-b

[0500] Intermediate Compound 10-b is obtained by using substantially the same method as the synthesis method of Intermediate Compound 4-b, except that Intermediate Compound 10-a is used as a starting material instead of Intermediate Compound 4-a.

[0501] 3) Synthesis of intermediate compound 10-c

[0502] Intermediate compound 10-c was obtained by using substantially the same method as the synthesis method of intermediate compound 4-c, except that intermediate compound 10-b was used instead of intermediate compound 4-b and 2,6-dibromo-9,10-diphenylanthracene was used instead of 1,6-dibromopyrene as a starting material.

[0503] 4) Synthesis of Compound 10

[0504] Under an argon atmosphere, the intermediate compound 10-c (5 g, 4.3 mmol) was added to a 1 L flask and dissolved in 100 mL of o-dichlorobenzene, and BI was added thereto. 3 (1.5 equivalents). The reaction solution was stirred at about 150° C. for about 24 hours. After cooling, triethylamine was added to quench the reaction, the solvent was removed under reduced pressure, and the solid thus obtained was purified by using silica gel and using CH 2 Cl 2 The resulting product was purified and separated by column chromatography using 4% iodine and hexane as a developing solvent to obtain Compound 10 (yellow solid, 1.5 g, yield 29%).

[0505] ESI-LCMS:[M] + :C 86 H 56 B 2 N 4 , m / z:1166.47.

[0506] NMR- 1 H: 8.78(s,2H),8.39(d,2H),8.03(d,4H),7.84(m,4H),7.75(m,4H),7.63(m,10H),7.43(d,8H),7.35(m,16H),7.08(s,2H),6.84(s,4H).

[0507] (3) Synthesis of Compound 23

[0508] Compound 23 according to an embodiment can be synthesized, for example, through Reaction 3.

[0509] [Reaction 3]

[0510]

[0511] 1) Synthesis of intermediate compound 23-c

[0512] Intermediate compound 23-c was obtained by using substantially the same method as the synthesis method of intermediate compound 4-c, except that 2,2′-dibromo-9,9′-spiro[fluorene] was used instead of 1,6-dibromopyrene as a starting material.

[0513] 2) Synthesis of compound 23

[0514] Under an argon atmosphere, the intermediate compound 23-c (5 g, 4.3 mmol) was added to a 1 L flask and dissolved in 100 mL of o-dichlorobenzene, and BI was added thereto. 3 (1.5 equivalents). The reaction solution was stirred at about 150° C. for about 24 hours. After cooling, triethylamine was added to quench the reaction, the solvent was removed under reduced pressure, and the solid thus obtained was purified by using silica gel and using CH 2 Cl 2 The resulting product was purified and separated by column chromatography using 4% iodine and hexane as a developing solvent to obtain Compound 23 (yellow solid, 1.5 g, yield 29%).

[0515] ESI-LCMS:[M] + :C 81 H 62 B 2 N 4 , m / z:1112.52.

[0516] NMR- 1 H: 8.44(s,2H),8.23(d,2H),7.77(d,4H),7.65(m,4H),7.57(m,12H),7.38(m,10H),7.24(m,2H),7.08(d,4H),6.43(s,4H),1.68(s,18H).

[0517] 2. Manufacturing and evaluation of light-emitting components

[0518] The light-emitting element of the embodiment is manufactured by the method, and the light-emitting element includes the polycyclic compound of the embodiment in the emission layer. The light-emitting elements of Examples 1 to 3 are manufactured using Compound 4, Compound 10 and Compound 23 as the dopant material of the emission layer. Comparative Examples 1 to 3 correspond to light-emitting elements manufactured using Compounds A to C as dopant materials of the emission layer.

[0519] [Example Compounds]

[0520]

[0521] [Comparative Compounds]

[0522]

[0523] 1) Manufacturing of light-emitting components

[0524] In order to manufacture the light-emitting elements of the examples and comparative examples, a 15 Ω / cm 2 A glass substrate with an ITO electrode (product of Corning Incorporated) was cut into a size of 50 mm × 50 mm × 0.7 mm, rinsed with isopropyl alcohol and pure water by ultrasonic wave for about 5 minutes each, cleaned by exposure to ultraviolet rays for about 30 minutes and exposure to ozone, and mounted on a vacuum deposition apparatus.

[0525] NPD is deposited on the anode to form a A hole injection layer with a thickness of about 1000 mm was formed, and H-1-19 was deposited on the hole injection layer to form a hole injection layer with a thickness of about 1000 mm. On the hole transport layer, CzSi is deposited to form a hole transport layer having a thickness of about The thickness of the buffer layer.

[0526] Then, a main mixture of the second compound and the third compound in a ratio of about 1:1, the fourth compound, and the example compound or the comparative example compound are co-deposited in a weight ratio of about 85:14:1 to form a TSPO1 is deposited on the emission layer to form an emission layer having a thickness of about An electron transport layer with a thickness of about 1000 nm is formed, and TPBi is deposited on the electron transport layer to form a Yb is deposited on the buffer layer to form a buffer layer having a thickness of about An electron injection layer with a thickness of about 1000 nm was formed, and MgAg was deposited to form an electron injection layer with a thickness of about 1000 nm. Compound P4 is deposited on the cathode to form a Yb / MgAg cathode having a thickness of about A capping layer with a thickness of is used to manufacture a light-emitting element.

[0527] All the layers were formed by vacuum deposition. The second compound used compound HT35 in compound group 2, the third compound used compound ETH66 in compound group 3, and the fourth compound used compound AD-38 in compound group 4.

[0528] Compounds used for manufacturing light-emitting elements of Examples and Comparative Examples are shown. These materials were used for manufacturing light-emitting elements after purification by sublimation of commercial products.

[0529]

[0530]

[0531] 2) Evaluation of physical properties of example compounds and comparative compounds

[0532] In Table 1, physical properties of Compound 4, Compound 10, and Compound 23 as Example compounds and Compound A to Compound C as Comparative compounds were evaluated and shown.

[0533] In Table 1, the lowest unoccupied molecular orbital (LUMO) energy level, the highest occupied molecular orbital (HOMO) energy level, the lowest excited singlet energy level (S1), the lowest excited triplet energy level (T1), and the difference between the lowest excited singlet energy level (S1) and the lowest excited triplet energy level (T1) (S1-T1, hereinafter, ΔE ST1 In Table 1, the photoluminescence quantum yield (PLQY), the maximum absorption wavelength (λ Abs ), maximum emission wavelength (λ emi ), Stokes shift (λ Abs and λ emi The difference between λ and λ is the difference between λ and λ, and the full width quarter maximum (FWQM). emi is the maximum emission wavelength of the example compounds and comparative compounds in solution.

[0534] [Table 1]

[0535]

[0536] 3) Evaluation of properties of light-emitting elements

[0537] In Table 2, there are shown the evaluation results of the light emitting elements of Examples 1 to 3 and Comparative Examples 1 to 3. The evaluation of the properties of the light emitting elements was performed using a luminance directional characteristics measuring device.

[0538] In Table 2, driving voltage, emission efficiency, maximum emission wavelength, lifetime (T95), color coordinates (CIE), and quantum efficiency (QE) of the light emitting elements according to the embodiment and the comparative example were measured and shown.

[0539] In Table 2, the light emitting element was measured at about 10 mA / cm 2 The driving voltage (V) and emission efficiency (cd / A) at the current density of . In order to evaluate the lifetime (T95) of the light-emitting element, the maximum emission wavelength (λ max ), quantum efficiency (QE) and 10mA / cm 2 The lifespan (T95) is the time taken for the luminance to degrade from the initial value to 5% when the luminance is continuously driven under the same conditions. Specifically, the lifespan (T95) is obtained by measuring the time taken for the initial luminance to decrease from 100% to 95%.

[0540] [Table 2]

[0541]

[0542] Referring to Table 2, it can be confirmed that the light-emitting element of the example uses the polycyclic compound according to the embodiment as a light-emitting material and shows lower driving voltage and improved emission efficiency and / or lifetime characteristics compared with the comparative example.

[0543] In more detail, the light emitting element of the example showed a driving voltage reduced by about 0.5 V or more and improved lifespan characteristics, compared with the light emitting elements of Comparative Examples 1 to 3.

[0544] The polycyclic compound used in the light-emitting element of the embodiment introduces a polycyclic aromatic hydrocarbon group (PAH group) in the core part, and the second lowest triplet energy level (T2) and the lowest triplet energy level (T1) can be reduced. Accordingly, compared with Comparative Example 1 and Comparative Example 2, the light-emitting element of the embodiment including the polycyclic compound shows a slightly lower emission efficiency, but shows an improved lifespan characteristic of about 10 times. From such a result, it can be found that the polycyclic compound according to the embodiment shows an excellent effect as a light-emitting material.

[0545] The light emitting element according to the embodiment includes the polycyclic compound according to the embodiment in an emission layer, and may exhibit low driving voltage characteristics and long life characteristics.

[0546] The polycyclic compound according to the embodiment includes an organic compound having a low lowest triplet energy level value in the core portion and includes a condensed structure of a first condensed ring and a second condensed ring at the core portion, and can help reduce the driving voltage of the light-emitting element and increase the life of the light-emitting element.

[0547] Embodiments have been disclosed herein, and although terms are employed, they are used and interpreted in a general and descriptive sense only and not for purposes of limitation. In some cases, as will be apparent to one of ordinary skill in the art, features, characteristics, and / or elements described in conjunction with an embodiment may be used alone or in combination with features, characteristics, and / or elements described in conjunction with other embodiments, unless specifically indicated otherwise. Accordingly, one of ordinary skill in the art will understand that various changes in form and details may be made without departing from the spirit and scope of the present disclosure as set forth in the claims.

Claims

1. A polycyclic compound represented by Formula 1: Formula 1 In formula 1, L is a substituted or unsubstituted polycyclic aromatic hydrocarbon group having 12 to 25 ring carbon atoms, X and Y are each independently N(R7), O, S or Se, R1 to R4 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 60 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 60 ring carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 ring carbon atoms, R5 to R7 are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group of 1 to 30 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring carbon atoms, n1 and n4 are each independently an integer selected from 0 to 4, and n2 and n3 are each independently an integer selected from 0 to 3.

2. The polycyclic compound according to claim 1, wherein L is a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group or a substituted or unsubstituted fluorenyl group.

3. The polycyclic compound according to claim 2, wherein the polycyclic compound represented by Formula 1 is represented by any one of Formula 2-1 to Formula 2-5: Formula 2-1 Formula 2-2 Formula 2-3 Formula 2-4 Formula 2-5 In Formula 2-1 to Formula 2-5, R a1 To R a6 , R b1 To R b6 , R c1 To R c4 , R d1 To R d4 and R e1 To R e6 are each independently a hydrogen atom, a deuterium atom or a substituted or unsubstituted aryl group having 6 to 15 ring carbon atoms, c1, c2, d1 and d3 are each independently an integer selected from 0 to 4, c3, c4, d2 and d4 are each independently an integer selected from 0 to 2, and X, Y, R1 to R6, and n1 to n4 are the same as defined in Formula 1.

4. The polycyclic compound according to claim 3, wherein the polycyclic compound represented by Formula 2-1 is represented by Formula 2-1A: Formula 2-1A In Formula 2-1A, R 21 ′ and R 31 ' are each independently a hydrogen atom or a deuterium atom, R 22 ′ and R 32 ' are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 15 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 15 ring carbon atoms, R 51 ' to R 55 ′ and R 61 ' to R 65 ' are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group of 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group of 6 to 10 ring carbon atoms, n21′ and n31′ are each independently an integer selected from 0 to 2, and R1, R4, R a1 To R a6 , n1, n4, X and Y are the same as defined in Formula 1 and Formula 2-1.

5. The polycyclic compound according to claim 3, wherein the polycyclic compound represented by Formula 2-2 is represented by Formula 2-2A: Formula 2-2A Wherein in Formula 2-2A, R 21 ′ and R 31 ' are each independently a hydrogen atom or a deuterium atom, R 22 ′ and R 32 ' are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 15 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 15 ring carbon atoms, R 51 ' to R 55 ′ and R 61 ' to R 65 ' are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group of 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group of 6 to 10 ring carbon atoms, n21′ and n31′ are each independently an integer selected from 0 to 2, and R1, R4, R b1 To R b6 , n1, n4, X and Y are the same as defined in Formula 1 and Formula 2-2.

6. The polycyclic compound according to claim 1, wherein the polycyclic compound represented by Formula 1 is represented by Formula 3: Formula 3 In formula 3, R 5a To R 5e and R 6a To R 6e are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group of 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group of 6 to 10 ring carbon atoms, and R1 to R4, n1 to n4, L, X, and Y are the same as defined in Formula 1.

7. The polycyclic compound according to claim 1, wherein the polycyclic compound represented by Formula 1 is represented by Formula 4: Formula 4 In formula 4, R 21 and R 31 are each independently a hydrogen atom or a deuterium atom, R 22 and R 32 are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 15 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 15 ring carbon atoms, n21 and n31 are each independently an integer selected from 0 to 2, and R1, R4 to R6, n1, n4, L, X and Y are the same as defined in Formula 1.

8. The polycyclic compound according to claim 1, wherein the polycyclic compound represented by Formula 1 is represented by any one of Formula 5-1 to Formula 5-4: Formula 5-1 Formula 5-2 Formula 5-3 Formula 5-4 In Formula 5-1 to Formula 5-4, R 71 To R 75 are each independently a substituted or unsubstituted aryl group having 6 to 20 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 20 ring carbon atoms, and R1 to R6, n1 to n4 and L are the same as defined in Formula 1.

9. The polycyclic compound according to claim 1, wherein the polycyclic compound represented by Formula 1 is selected from Compound Group 1: Compound Group 1 Among them, in compound group 1, D indicates a deuterium atom. 10 . The polycyclic compound according to claim 1 , wherein in the polycyclic compound represented by Formula 1, a difference between a lowest singlet energy level and a second lowest triplet energy level is greater than a difference between the second lowest triplet energy level and a lowest triplet energy level.

11. A light emitting element, comprising: a first electrode; a second electrode disposed on the first electrode; as well as an emission layer disposed between the first electrode and the second electrode, wherein The emission layer includes the polycyclic compound according to any one of claims 1 to 10 as a first compound. 12 . The light-emitting element according to claim 11 , wherein L has a lowest triplet energy level in the range of 1.5 eV to 2.4 eV.

13. The light-emitting element according to claim 11, wherein the emission layer further comprises at least one of a second compound represented by Formula HT-1, a third compound represented by Formula ET-1, and a fourth compound represented by Formula S-1: Formula HT-1 Wherein in formula HT-1, A1 to A8 are each independently N or C (R x1 ), L1 is a directly linked, 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 For direct connection, C(R x2 )(R x3 ) or Si(R x4 )(R x5 ), Ar1 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, and R x1 To R x5 Each is independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted thiol group, a substituted or unsubstituted oxy group, a substituted or unsubstituted amine group, a substituted or unsubstituted boron group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 ring carbon atoms, or bonds to an adjacent group to form a ring; Formula ET-1 Wherein in formula ET-1, At least one of X1 to X3 is each N, The remaining groups in X1 to X3 are each independently C(R x6 ), R x6 is a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 60 ring carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 60 ring carbon atoms, b1 to b3 are each independently an integer selected from 0 to 10, Ar2 to Ar4 are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring carbon atoms, and L2 to L4 are each independently a directly linked, 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; Formula S-1 Wherein in formula S-1, Q1 to Q4 are each independently C or N, C1 to C4 are each independently a substituted or unsubstituted hydrocarbon ring group of 5 to 30 ring carbon atoms or a substituted or unsubstituted heterocyclic group of 2 to 30 ring carbon atoms, L 11 To L 13 Each is independently connected to the A substituted or unsubstituted alkylene group of 1 to 20 carbon atoms, a substituted or unsubstituted arylene group of 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group of 2 to 30 ring carbon atoms, wherein represents a bond connected to one of C1 to C4, b11 to b13 are each independently 0 or 1, R 61 To 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 thiol group, a substituted or unsubstituted oxy group, a substituted or unsubstituted amine group, a substituted or unsubstituted boron group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 ring carbon atoms, or bonds to an adjacent group to form a ring, and d1 to d4 are each independently an integer selected from 0 to 4.

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