Light-emitting element, polycyclic compound, and electronic device

Abstract

Embodiments provide a polycyclic compound, a light-emitting element, and an electronic device. The light emitting element includes a first electrode, a second electrode facing the first electrode, and an emission layer disposed between the first electrode and the second electrode and including the polycyclic compound. The polycyclic compound is represented by Formula 1 described 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. 10-2024-0031552 filed in the Korean Intellectual Property Office on March 5, 2024, the entire contents of which are incorporated herein by reference. Technical Field

[0003] The present disclosure relates to a light-emitting element, a polycyclic compound for a light-emitting element, and an electronic device including the light-emitting element. Background Art

[0004] Development of organic electroluminescent displays (OLEDs) as image display devices continues. Unlike liquid crystal displays (LCDs), OLEDs are self-emissive displays, where holes and electrons injected from a first electrode and a second electrode recombine in an emissive layer, causing the luminescent material in the layer to emit light, thereby achieving display.

[0005] When light-emitting elements are applied to display devices, there is a continuous demand for increasing emission efficiency and lifetime, and therefore, there is a continuous development of materials for light-emitting elements that stably achieve such characteristics. For example, the development of thermally activated delayed fluorescence (TADF) materials that utilize the delayed fluorescence phenomenon is underway.

[0006] It should be understood that this background section is intended, in part, to provide a useful context for understanding the technology. However, this background section may also include ideas, concepts, or realizations that were not part of what was known or understood by those 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 having improved emission efficiency and lifetime.

[0008] The present disclosure also provides polycyclic compounds with improved material lifetimes.

[0009] The present disclosure also provides a display device including a light emitting element having improved emission efficiency and lifetime, thereby having excellent display quality.

[0010] According to the embodiment, a light emitting element may include: a first electrode; a second electrode facing the first electrode; and an emission layer disposed between the first electrode and the second electrode and including a first compound represented by Formula 1.

[0011] [Formula 1]

[0012]

[0013] In Formula 1, X can be O, S or N (R 12 );R 1 to R 12 may each independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted amino group, a substituted or unsubstituted oxy group, a substituted or unsubstituted sulfinyl group, a substituted or unsubstituted boron group, an 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 R 1 to R 4 Can bond to adjacent groups to form 1 to R 4 Form a ring between, or R 5 to R 8 Can bond to adjacent groups to form 5 to R 8 A ring is formed between them; and R a to R e Each of them may independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, an 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.

[0014] In formula 1, R a to R e At least one of may be a cyano group; and R a to R e At least one of the remaining groups in may each independently be a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms.

[0015] In an embodiment, the emission layer may further include at least one of a second compound represented by Formula HT-1 and a third compound represented by Formula ET-1.

[0016] [Formula HT-1]

[0017]

[0018] In formula HT-1, A1 to A8 may each independently be N or C(R 51 ); L1 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; Y a Can be directly connected, C(R 52 )(R 53 ) or Si(R 54 )(R 55); Ar1 ​​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; and R 51 to R 55 Each of the 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 amino 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 30 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.

[0019] [Formula ET-1]

[0020]

[0021] In formula ET-1, Z a to Z c At least one of them can be N; Z a to Z c The remaining groups can each independently be C(R 56 );R 56 It can be a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 ring carbon atoms; e1 to e3 can each independently be an integer from 0 to 10; Ar2 to Ar4 can each independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms; and L2 to L4 can each independently 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.

[0022] In an embodiment, the emission layer may further include a fourth compound represented by Formula D-1.

[0023] [Formula D-1]

[0024]

[0025] In formula D-1, Q1 to Q4 may each independently be C or N; C1 to C4 may each independently be a substituted or unsubstituted hydrocarbon ring having 5 to 30 ring carbon atoms, or a substituted or unsubstituted heterocycle having 2 to 30 ring carbon atoms; L11 To L 13 Can be independently connected for direct connection, 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; b11 to b13 may each independently be 0 or 1; R 61 to R 66 Each of d1 to d4 may be 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 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; and d1 to d4 may each independently be an integer from 0 to 4.

[0026] In an embodiment, in the a to R e Of the two, one may be a cyano group, and the other may be a substituted or unsubstituted phenyl group; and R a to R e The remaining groups other than the cyano group or the substituted or unsubstituted phenyl group in may each independently be a hydrogen atom, a deuterium atom, or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms.

[0027] In an embodiment, the first compound represented by Formula 1 may be represented by one of Formula 2-1 to Formula 2-3.

[0028] [Formula 2-1]

[0029]

[0030] [Formula 2-2]

[0031]

[0032] [Formula 2-3]

[0033]

[0034] In formula 2-1 to formula 2-3, R a 、R b 、R d and R e One or two of them may be independently substituted or unsubstituted phenyl; R a 、R b 、Rd and R e The remaining groups in may each independently be a hydrogen atom or a deuterium atom; and R 1 to R 11 Each may be the same as defined in Formula 1. In Formula 2-3, R f 、R g 、R h 、R i and R j Each of them may independently be a hydrogen atom, a deuterium atom, a cyano group, an unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms.

[0035] In an embodiment, the first compound represented by Formula 1 may be represented by one of Formula 3-1 to Formula 3-5.

[0036] [Formula 3-1]

[0037]

[0038] [Formula 3-2]

[0039]

[0040] [Formula 3-3]

[0041]

[0042] [Formula 3-4]

[0043]

[0044] [Formula 3-5]

[0045]

[0046] In formulas 3-1 to 3-5, R 21 to R 36 may each independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted amino group, a substituted or unsubstituted oxy 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; and X, R a 、R b 、R c 、R d and R e Each may be the same as defined in Formula 1. In Formulas 3-2 to 3-5, n1, n3, and n5 may each independently be an integer from 0 to 4; n2 and n4 may each independently be an integer from 0 to 3; Y 1 To Y4 can be independently O, S or N(R 37 );Y 5 and Y 6 can be independently O, S, N(R 38 ) or B(R 39 ); and R 37 to R 39 Each independently may be a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms.

[0047] In an embodiment, at least one hydrogen atom in the first compound represented by Formula 1 may be substituted with a deuterium atom.

[0048] In an embodiment, the emission layer may emit delayed fluorescence.

[0049] In an embodiment, the emitting layer may emit blue light.

[0050] In embodiments, the first compound can be selected from Compound Group 1 described herein.

[0051] According to an embodiment, the polycyclic compound may be represented by Formula 1 described herein.

[0052] In an embodiment, in the a to R e Of the two, one may be a cyano group, and the other may be a substituted or unsubstituted phenyl group; and R a to R e The remaining groups other than the cyano group or the substituted or unsubstituted phenyl group in may each independently be a hydrogen atom, a deuterium atom, or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms.

[0053] In an embodiment, X may be N(R 12 ); and R 12 The aryl group may be substituted or unsubstituted and may have 6 to 30 ring carbon atoms.

[0054] In an embodiment, the polycyclic compound represented by Formula 1 may be represented by one of Formulas 2-1 to 2-3 described herein.

[0055] In an embodiment, the polycyclic compound represented by Formula 2-3 may be represented by Formula 2-3-1 described herein.

[0056] In an embodiment, the polycyclic compound represented by Formula 1 may be represented by one of Formulas 3-1 to 3-5 described herein.

[0057] In an embodiment, the polycyclic compound represented by Formula 1 may be a compound selected from Compound Group 1 described herein.

[0058] According to an embodiment, an electronic device includes a display device, which may include: a circuit layer arranged on a base layer; and a display element layer arranged on the circuit layer and including a light-emitting element, wherein the light-emitting element may include: a first electrode; a second electrode facing the first electrode; and an emission layer arranged between the first electrode and the second electrode and including a polycyclic compound represented by Formula 1 described herein.

[0059] In an embodiment, the light emitting element may emit blue light.

[0060] In an embodiment, the display device may further include a light control layer, wherein the light control layer includes quantum dots.

[0061] It should be understood that the above embodiments have been described in a general and illustrative sense only, and not for purposes of limitation, and the present disclosure is not limited to the above embodiments. BRIEF DESCRIPTION OF THE DRAWINGS

[0062] The accompanying drawings are included to provide a further understanding of the embodiments and are incorporated into and constitute a part of this specification. The accompanying drawings illustrate 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 accompanying drawings, in which:

[0063] Figure 1 is a block diagram of an electronic device according to an embodiment;

[0064] Figure 2 shows a schematic diagram of an electronic device according to various embodiments;

[0065] Figure 3 is a schematic plan view of a display device according to an embodiment;

[0066] Figure 4 It is along Figure 3 A schematic cross-sectional view of a portion of the display device taken along a virtual line II' in FIG.

[0067] Figure 5 is a schematic cross-sectional view of a light emitting element according to an embodiment;

[0068] Figure 6 is a schematic cross-sectional view of a light emitting element according to an embodiment;

[0069] Figure 7 is a schematic cross-sectional view of a light emitting element according to an embodiment;

[0070] Figure 8 is a schematic cross-sectional view of a light emitting element according to an embodiment;

[0071] Figure 9 is a schematic cross-sectional view of a light emitting element according to an embodiment;

[0072] Figure 10 is a schematic cross-sectional view of a display device according to an embodiment;

[0073] Figure 11 is a schematic cross-sectional view of a display device according to an embodiment;

[0074] Figure 12 is a schematic cross-sectional view of a display device according to an embodiment;

[0075] Figure 13 is a schematic cross-sectional view of a display device according to an embodiment; and

[0076] Figure 14 is a schematic diagram of the interior of a vehicle in which the display device according to the embodiment is provided. DETAILED DESCRIPTION

[0077] The present disclosure will now be described more fully hereinafter with reference to the accompanying 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 this disclosure will be thorough and complete and will fully convey the scope of the disclosure to those skilled in the art.

[0078] In the drawings, the size, thickness, ratio, and dimensions of elements may be exaggerated for ease of description and clarity. The same reference numerals and / or reference letters refer to the same elements throughout.

[0079] In the description, it will be understood that when an element (or region, layer, component, etc.) is referred to as being “on”, “connected to” or “coupled to” another element, the element may be directly on, directly connected to or coupled to the other element, or one or more intervening elements may be present between the element and the other element. In a similar sense, when an element (or region, layer, component, etc.) is described as “overlying” another element, the element may directly overly the other element, or one or more intervening elements may be present between the element and the other element.

[0080] In the description, 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 additional elements, such as adhesive elements, between them.

[0081] As used herein, expressions in the singular such as “a,” “an,” and “the” are intended to include the plural forms as well, unless the context clearly indicates otherwise.

[0082] 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 conjunction or disjunction sense and may be understood to be equivalent to "and / or."

[0083] In the specification and claims, for purposes of its meaning and interpretation, the term "at least one of" is intended to include the meaning of "at least one selected from the group consisting of." 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, AC, BC, or AB. When the term "at least one of" follows a list of elements, it modifies the entire list of elements and does not modify the individual elements in the list.

[0084] It will be understood that although the terms "first," "second," etc. may be used herein to describe various elements, these elements should not be limited by these terms. These terms are only used to distinguish one element from another. Therefore, without departing from the teachings of the present disclosure, a first element may be referred to as a second element. Similarly, without departing from the scope of the present disclosure, a second element may be referred to as a first element.

[0085] For ease of description, spatially relative terms such as "below," "beneath," "below," "above," or "on" may be used herein to describe the relationship between one element or component and another element or component as shown in the figures. It will be understood that, in addition to the orientation depicted in the figures, the spatially relative terms are intended to cover different orientations of the device in use or operation. For example, where the device shown in the figures is flipped, a device that is "below" or "below" another device may be "above" another device. Thus, the exemplary term "below" can include both a lower position and an upper position. The device may also be oriented in other directions, and thus the spatially relative terms may be interpreted differently depending on the orientation.

[0086] As used herein, the terms "about" or "approximately" are inclusive of the stated value and mean within an acceptable range of deviation from the stated value as determined by one of ordinary skill in the art, taking into account the measurements in question and errors associated with the measurement of the stated quantity (i.e., limitations of the measurement system). For example, "about" can mean within one or more standard deviations, or within ±20%, ±10%, or ±5% of the stated value.

[0087] It should be understood that the terms “comprises / comprising,” “inclues / including,” “have / having,” and “contains / containing” are intended to illustrate the presence of stated features, integers, steps, operations, elements (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 (elements), components, or combinations thereof.

[0088] Unless otherwise defined or implied herein, all terms (including technical and scientific terms) used have the same meaning as commonly understood by those skilled in the art to which the present disclosure belongs. It will be further understood that, unless expressly defined in the specification, 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.

[0089] In the specification, the term "substituted or unsubstituted" can describe a group substituted or unsubstituted by at least one substituent, wherein the substituent is selected from the group consisting of a deuterium atom, a halogen atom, a cyano group, a nitro group, an amino group, an amido group, a silyl group, an oxy group, a sulfenyl group, a sulfinyl group, a sulfonyl group, a carbonyl group, a boron group, a phosphine oxide group, a phosphine sulfide group, an alkyl group, an alkenyl group, an alkynyl group, a hydrocarbon ring group, an aryl group, and a heterocyclic group. Each substituent 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.

[0090] In the specification, the term "bonded to an adjacent group to form a ring" may refer to a group in which adjacent groups are bonded 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 monocyclic or polycyclic. The ring formed by adjacent groups bonded to each other may itself be connected to another ring to form a spirocyclic structure.

[0091] In the specification, the term "adjacent group" can be interpreted as a substituent that replaces an atom directly connected to the atom substituted by the corresponding substituent, another substituent that replaces the atom substituted by the corresponding substituent, or a substituent that is spatially located closest to the corresponding substituent. For example, the two methyl groups in 1,2-dimethylbenzene can be interpreted as "adjacent groups" to each other, and the two ethyl groups in 1,1-diethylcyclopentane can be interpreted as "adjacent groups" to each other. For example, the two methyl groups in 4,5-dimethylphenanthrene can be interpreted as "adjacent groups" to each other.

[0092] In the specification, examples of the halogen atom may include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0093] In the specification, the alkyl group may be linear or branched. The number of carbon atoms in the alkyl group may be 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-decyl The following examples include monodecyl, 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-heneicosyl, n-docosyl, n-tricosyl, n-tetracosyl, n-pentacosyl, n-hexacosyl, n-heptacosyl, n-octacosyl, n-nonacosyl, n-triacontyl, etc., but the embodiments are not limited thereto.

[0094] 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 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.

[0095] In the specification, an 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. An alkenyl group may be linear or branched. The number of carbon atoms in the alkenyl group is not particularly limited and may be 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.

[0096] In the specification, an alkynyl group may be a hydrocarbon group having at least one carbon-carbon triple bond in the middle or at the end of an alkyl group having 2 or more carbon atoms. An alkynyl group may be straight-chain or branched. Although the number of carbon atoms is not particularly limited, it may be 2 to 30, 2 to 20, or 2 to 10. Examples of alkynyl groups may include ethynyl, propynyl, etc., but embodiments are not limited thereto.

[0097] 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 20 ring-forming carbon atoms.

[0098] In the specification, an aryl group may be any functional group or substituent derived from an aromatic hydrocarbon ring. An aryl group may be monocyclic or polycyclic. The number of ring carbon atoms in the aryl group may be 6 to 30, 6 to 20, or 6 to 15. Examples of aryl groups may include phenyl, naphthyl, fluorenyl, anthracenyl, phenanthrenyl, biphenyl, terphenyl, quaterphenyl, pentaphenyl, hexaphenyl, triphenylenyl, pyrenyl, benzofluoranthenyl, However, the embodiment is not limited thereto.

[0099] In the specification, the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spirocyclic structure. Examples of substituted fluorenyl groups may include the groups shown below. However, the embodiment is not limited thereto.

[0100]

[0101] In the specification, a heterocyclic group may be any functional group or substituent derived from a ring containing at least one of B, O, N, P, Si, S, and Se as a heteroatom. A heterocyclic group may be aliphatic or aromatic. An aromatic heterocyclic group may be a heteroaryl group. The aliphatic heterocycle and the aromatic heterocycle may each independently be monocyclic or polycyclic.

[0102] If the heterocyclic group includes two or more heteroatoms, the two or more heteroatoms may be the same as or different from each other.The number of ring-forming carbon atoms in the heterocyclic group may be 2 to 30, 2 to 20, or 2 to 10.

[0103] Examples of the aliphatic heterocyclic group may include an oxirane group, a thiirane group, a pyrrolidinyl group, a piperidinyl group, a tetrahydrofuranyl group, a tetrahydrothiophenyl group, a thiocyclopentanyl group, a tetrahydropyranyl group, a 1,4-dioxanyl group, and the like, but the embodiment is not limited thereto.

[0104] Examples of heteroaryl groups may include thienyl, furyl, pyrrolyl, imidazolyl, pyridyl, bipyridyl, pyrimidyl, triazinyl, 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, dibenzothiorol, dibenzofuranyl, and the like, but embodiments are not limited thereto.

[0105] In the specification, the above description of the aryl group may be applied to the arylene group, except that the arylene group is a divalent group. In the specification, the above description of the heteroaryl group may be applied to the heteroarylene group, except that the heteroarylene group is a divalent group.

[0106] In the specification, the silyl group may be an alkylsilyl group or an arylsilyl group. Examples of the silyl group may include trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, etc., but the embodiment is not limited thereto.

[0107] In the specification, the number of carbon atoms in the carbonyl group is not particularly limited and 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.

[0108]

[0109] In the specification, the number of carbon atoms in the sulfinyl group or the sulfonyl group is not particularly limited and 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.

[0110] In the specification, a thio group may be an alkylthio group or an arylthio group. A thio group may be a sulfur atom bonded to an alkyl group or an aryl group as defined above. Examples of thio groups may include methylthio, ethylthio, propylthio, pentylthio, hexylthio, octylthio, dodecylthio, cyclopentylthio, cyclohexylthio, phenylthio, and naphthylthio, but embodiments are not limited thereto.

[0111] In the specification, an oxy group may be an oxygen atom bonded to an alkyl group or an aryl group as defined above. An oxy group may be an alkoxy group or an aryloxy group. An alkoxy group may be linear, branched, or cyclic. The number of carbon atoms in the alkoxy group is not particularly limited and may be, for example, 1 to 20 or 1 to 10. 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.

[0112] In the specification, a boryl group 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. Examples of boryl groups may include dimethyl boryl, tert-butyl methyl boryl, diphenyl boryl, phenyl boryl, etc., but embodiments are not limited thereto.

[0113] In the specification, the number of carbon atoms in the amino group is not particularly limited and may be 1 to 30. The amino group may be an alkylamino group or an arylamino group. Examples of the amino group may include methylamino, dimethylamino, anilino, diphenylamino, naphthylamino, 9-methyl-anthrylamino, etc., but the embodiment is not limited thereto.

[0114] In the specification, the alkyl group in the alkylthio group, the alkylthiooxy group, the alkylaryl group, the alkylamino group, the alkylboryl group, the alkylsilyl group, or the alkylamino group may be the same as exemplified in the above-described alkyl group.

[0115] In the specification, the aryl group in the aryloxy group, the arylthio group, the arylthiooxy group, the arylamino group, the arylboryl group, the arylsilyl group, or the arylamine group may be the same as the examples of the aryl group described above.

[0116] In the specification, a direct connection may be a single bond.

[0117] In this manual, the symbol Each represents a bond to an adjacent atom in the corresponding formula or moiety.

[0118] Hereinafter, embodiments will be described with reference to the accompanying drawings.

[0119] Figure 1 is a block diagram of an electronic device EA according to an embodiment. Figure 1 , the electronic device EA according to the embodiment may include a display module 11 , a processor 12 , a memory 13 , and a power module 14 .

[0120] The processor 12 may include at least one of a central processing unit (CPU), an application processor (AP), a graphics processing unit (GPU), a communication processor (CP), an image signal processor (ISP), and a controller.

[0121] The memory 13 may store data information required for the operation of the processor 12 or the display module 11. When the processor 12 runs an application stored in the memory 13, an image data signal and / or an input control signal may be transmitted to the display module 11, and the display module 11 may process the provided signals and output image information through a display screen.

[0122] The power module 14 may include a power module such as a power adapter or a battery device, and a power conversion module that converts power supplied from the power module and generates power required for the operation of the electronic device EA.

[0123] At least one of the components of the electronic device EA described above may be included in the display device according to the embodiment. In addition, some of the modules included as functional modules in one module may be included in the display device, and other modules may be provided separately from the display device. For example, the display device may include the display module 11, and the processor 12, memory 13, and power module 14 may not be provided in the display device but may be provided in another type of device in the electronic device EA.

[0124] Figure 2 An electronic device EA according to various embodiments is shown (see Figure 1 ) schematic diagram.

[0125] refer to Figure 2 The various electronic devices to which the display device according to the embodiment is applied may include not only electronic devices for displaying images, such as a smart phone 10_1a, a tablet computer (PC) 10_1b, a laptop computer 10_1c, a television (TV) set 10_1d, and a monitor 10_1e for a desktop computer, but may also include wearable electronic devices with a display module (such as smart glasses 10_2a, a head-mounted display 10_2b, and a smart watch 10_2c) and a vehicle electronic device 10_3 with a display module (such as a vehicle instrument panel, a central control instrument panel, a center information display (CID) set on the dashboard, and a room mirror display).

[0126] Figure 3 is a schematic plan view of a display device DD according to an embodiment. Figure 4 is a schematic cross-sectional view of a display device DD according to an embodiment. Figure 4 It is along Figure 3 Schematic cross-sectional view of a portion of the display device DD taken along the imaginary line II' in FIG. The display device DD of one embodiment may be included in the electronic device EA described above. The display device DD may be a component that provides an image in the electronic device EA.

[0127] 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 external light reflected from 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, the optical layer PP may be omitted from the display device DD.

[0128] A 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, or the like. However, embodiments are not limited thereto and the base substrate BL may be an inorganic layer, an organic layer, or a composite material layer. Although not shown in the drawings, in embodiments, the base substrate BL may be omitted.

[0129] The display device DD according to an embodiment may further include a filling layer (not shown). The filling layer (not shown) may be disposed 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 siloxane resin, and an epoxy resin.

[0130] 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.

[0131] 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.

[0132] In an embodiment, the circuit layer DP-CL is disposed on the base layer BS and 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 switching transistors and driving transistors for driving the light-emitting elements ED-1, ED-2, and ED-3 of the display device layer DP-ED.

[0133] The light emitting elements ED-1, ED-2, and ED-3 may each have a light emitting element having ... Figures 5 to 9The light-emitting elements ED-1, ED-2, and ED-3 may each include a first electrode EL1, a hole transport region HTR, an emission layer EML-R, an electron transport region ETR, and a second electrode EL2.

[0134] Figure 4 An 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 in the pixel definition 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 not shown in FIG. Figure 4 , but the hole transport region HTR and the electron transport region ETR can each be provided by patterning in the opening OH defined in the pixel definition film PDL. For example, in the 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 can be provided by patterning through an inkjet printing method.

[0135] The encapsulation layer TFE may cover the light-emitting elements ED-1, ED-2, and ED-3. The encapsulation layer TFE may seal 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 according to an embodiment may include at least one inorganic film (hereinafter referred to as an encapsulation-inorganic film). The encapsulation layer TFE according to an embodiment may also include at least one organic film (hereinafter referred to as an encapsulation-organic film) and at least one encapsulation-inorganic film.

[0136] The encapsulation-inorganic film can protect the display device layer DP-ED from moisture and / or oxygen, and the encapsulation-organic film can protect the display device layer DP-ED from foreign substances such as dust particles. The encapsulation-inorganic film may include silicon nitride, silicon oxynitride, silicon oxide, titanium oxide, or aluminum oxide, etc., but the embodiment is not particularly limited thereto. The encapsulation-organic film may include an acrylic compound or an epoxy compound, etc. The encapsulation-organic film may include a photopolymerizable organic material, but the embodiment is not particularly limited thereto.

[0137] The encapsulation layer TFE may be disposed on the second electrode EL2 and may be disposed to fill the opening OH.

[0138] refer to Figure 3 and Figure 4The display device DD may include a non-emission area NPXA and emission areas PXA-R, PXA-G, and PXA-B. The emission areas PXA-R, PXA-G, and PXA-B may be areas that emit light generated by the light-emitting elements ED-1, ED-2, and ED-3, respectively. The emission areas PXA-R, PXA-G, and PXA-B may be spaced apart from each other in a plan view.

[0139] The light-emitting regions PXA-R, PXA-G, and PXA-B may be regions separated from each other by a pixel-defining film PDL. The non-light-emitting region NPXA may be a region between adjacent light-emitting regions PXA-R, PXA-G, and PXA-B, and it may correspond to the pixel-defining film PDL. In an embodiment, the light-emitting regions 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 arranged in an opening OH defined in the pixel-defining film PDL and separated from each other.

[0140] The light emitting regions PXA-R, PXA-G, and PXA-B may be arranged into groups according to the colors of the lights generated from the light emitting elements ED-1, ED-2, and ED-3. Figure 3 and Figure 4 In the display device DD of the embodiment shown in FIG, three light-emitting regions PXA-R, PXA-G, and PXA-B that emit red, green, and blue light, respectively, are shown as examples. For example, the display device DD according to the embodiment may include a red light-emitting region PXA-R, a green light-emitting region PXA-G, and a blue light-emitting region PXA-B that are different from each other.

[0141] In a display device DD according to an embodiment, the light-emitting elements ED-1, ED-2, and ED-3 may emit light having different wavelengths. For example, in an embodiment, the display device DD may include a first light-emitting element ED-1 that emits red light, a second light-emitting element ED-2 that emits green light, and a third light-emitting element ED-3 that emits blue light. For example, the red light-emitting region PXA-R, the green light-emitting region PXA-G, and the blue light-emitting region PXA-B of the display device DD may correspond to the first light-emitting element ED-1, the second light-emitting element ED-2, and the third light-emitting element ED-3, respectively.

[0142] However, the embodiment is not limited thereto, and the first light-emitting element ED-1, the second light-emitting element ED-2, and the third light-emitting element ED-3 may emit light within the same wavelength range, or at least one light-emitting element may emit a light beam within a wavelength range different from the wavelength range of light emitted by the remaining light-emitting elements. For example, the first light-emitting element ED-1, the second light-emitting element ED-2, and the third light-emitting element ED-3 may all emit blue light.

[0143] The light emitting regions PXA-R, PXA-G, and PXA-B in the display device DD according to the embodiment may be arranged in a stripe configuration. Figure 3 The red light emitting region PXA-R, the green light emitting region PXA-G, and the blue light emitting region PXA-B may be arranged along the second direction axis DR2, respectively. In another embodiment, the red light emitting region PXA-R, the green light emitting region PXA-G, and the blue light emitting region PXA-B may be arranged in this order along the first direction axis DR1.

[0144] Figure 3 and Figure 4 While the light-emitting regions PXA-R, PXA-G, and PXA-B are shown as having similar areas, embodiments are not limited thereto. In embodiments, the light-emitting regions PXA-R, PXA-G, and PXA-B may differ in shape or size depending on the wavelength range of the emitted light. The areas of the light-emitting regions PXA-R, PXA-G, and PXA-B may be defined by the first and second directional axes DR1 and DR2 in a plan view. The third directional axis DR3 may be perpendicular to the plane defined by the first and second directional axes DR1 and DR2.

[0145] The arrangement of the light emitting regions PXA-R, PXA-G, and PXA-B is not limited to Figure 3 The configuration shown in FIG, and the order of arranging the red light emitting region PXA-R, the green light emitting region PXA-G, and the blue light emitting region PXA-B can be provided in various combinations according to the display quality characteristics required in the display device DD. For example, the light emitting regions PXA-R, PXA-G, and PXA-B can be arranged in a five-tile configuration (such as ) or in diamond configuration (such as Diamond ) arrangement.

[0146] 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.

[0147] In the following, Figures 5 to 9Each is a schematic cross-sectional view of a light emitting element ED according to an embodiment. The light emitting element ED according to the embodiment may include a first electrode EL1, a second electrode EL2 facing the first electrode EL1, and an emission layer EML disposed between the first electrode EL1 and the second electrode EL2. The light emitting element ED according to the embodiment may include a polycyclic compound according to the embodiment, which will be described later, in at least one functional layer.

[0148] The light-emitting element ED may include a hole transport region HTR or an electron transport region ETR between the first electrode EL1 and the emission layer EML and between the emission layer EML and the second electrode EL2. For example, the light-emitting element ED 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 the following order.

[0149] and Figure 5 compared to, Figure 6 1 is a 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 5 compared to, Figure 7 is a 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 auxiliary emission layer EAL, and the electron transport region ETR includes an electron injection layer EIL, an electron transport layer ETL and a hole blocking layer HBL. Figure 5 compared to, Figure 8 : is a 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 6 compared to, Figure 9 is a schematic cross-sectional view of a light emitting element ED including a cover layer CPL disposed on the second electrode EL2 according to an embodiment.

[0150] The first electrode EL1 has electrical 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, embodiments are not limited thereto. In embodiments, the first electrode EL1 may be a pixel electrode. The first electrode EL1 may be a transmissive electrode, a semi-transmissive reflective 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, or oxides thereof, compounds thereof, or mixtures thereof.

[0151] 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 Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF, Mo, Ti, W, a compound thereof, or a mixture thereof (e.g., a mixture of Ag and Mg), or a material having a multilayer structure such as LiF / Ca (a stacked structure of LiF and Ca) or LiF / Al (a stacked structure of LiF and Al). In another embodiment, 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, or the like. 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 material. The thickness of the first electrode EL1 may be about 1000 nm. to approximately For example, the thickness of the first electrode EL1 can be about to approximately within the range.

[0152] A hole transport region HTR may be provided on the first electrode EL1. The hole transport region HTR may include at least one of a hole injection layer HIL, a hole transport layer HTL, a buffer layer (not shown), an auxiliary emission layer EAL, and an electron blocking layer EBL. The thickness of the hole transport region HTR may be, for example, about 1000 Å. to approximately within the range.

[0153] The hole transport region HTR may have a structure consisting of a layer including a single material, a structure consisting of layers including different materials, or a structure including a plurality of layers including different materials.

[0154] For example, the hole transport region HTR may have a single-layer structure of a hole injection layer HIL or a hole transport layer HTL, or may have a single-layer structure 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 including different materials, or may have a structure in which hole injection layer HIL / hole transport layer HTL, hole injection layer HIL / hole transport layer HTL / auxiliary emission layer EAL, hole injection layer HIL / auxiliary emission layer EAL, hole transport layer HTL / auxiliary emission layer EAL, hole injection layer HIL / hole transport layer HTL / auxiliary emission layer EAL, hole injection layer HIL / hole transport layer HTL / auxiliary emission layer EAL, or hole injection layer HIL / hole transport layer HTL / electron blocking layer EBL are stacked from the first electrode EL1 in the order of their respective statements, but the embodiment is not limited thereto.

[0155] 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-Blodgett (LB) method, an inkjet printing method, a laser printing method, and a laser induced thermal imaging (LITI) method.

[0156] In the light emitting element ED according to the embodiment, the hole transport region HTR may include a compound represented by Formula H-1:

[0157] [Formula H-1]

[0158]

[0159] In formula H-1, L1 and L2 may each independently 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. In formula H-1, a and b may each independently be an integer from 0 to 10. When a or b is 2 or greater, multiple L1 and multiple L2 may each independently be a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms.

[0160] In formula H-1, Ar1 and Ar2 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. In formula H-1, Ar3 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.

[0161] In an embodiment, the compound represented by formula H-1 may be a monoamine compound. In another embodiment, the compound represented by formula H-2 may be a diamine compound in which at least one of Ar1 to Ar3 includes an amino group as a substituent. In an embodiment, the compound represented by formula H-1 may be a carbazole compound in which at least one of Ar1 and Ar2 includes a substituted or unsubstituted carbazole group, or may be a fluorene compound in which at least one of Ar1 or Ar2 includes a substituted or unsubstituted fluorene group.

[0162] The compound represented by formula H-1 may be a compound selected from compound group H. However, the compounds listed in compound group H are only examples, and the compound represented by formula H-1 is not limited to compound group H:

[0163] [Compound Group H]

[0164]

[0165] 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 -di-m-tolylphenyl-1,4-diamine)(DNTPD), 4,4',4"-[tris(3-methylphenyl)phenylamino]triphenylamine (m-MTDATA), 4,4',4"-tris(N,N-diphenylamino)triphenylamine (TDATA), 4,4',4"-tris[N-(2-naphthyl)-N-phenylamino]-triphenylamine (2-TNATA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / dodecylbenzenesulfonic acid ( The main products include PANI / 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], dipyrazine[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexanitrile (HAT-CN), etc.

[0166] The hole transport region HTR may include: carbazole derivatives such as 1,3-bis(H-carbazolyl)benzene (mCP), N-phenylcarbazole or polyvinylcarbazole; fluorene derivatives; triphenylamine derivatives such as N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1-biphenyl]-4,4'-diamine (TDN) or 4,4',4"-tris(N-carbazolyl)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-methylphenyl)amino]-3,3'-dimethylbiphenyl (HMTPD); etc.

[0167] In embodiments, the hole transport region HTR may include 9-(4-tert-butylphenyl)-3,6-bis(triphenylsilyl)-9H-carbazole (CzSi), 9-phenyl-9H-3,9'-bicarbazole (CCP), 1,3-bis(1,8-dimethyl-9H-carbazole-9-yl)benzene (mDCP), or the like.

[0168] The hole transport region HTR may include the above-mentioned compound of the hole transport region in at least one of the hole injection layer HIL, the hole transport layer HTL, the auxiliary emission layer EAL, and the electron blocking layer EBL.

[0169] The thickness of the hole transport region HTR can be about to approximately For example, the thickness of the hole transport region HTR can be about to approximately When the hole transport region HTR includes the hole injection layer HIL, the hole injection layer HIL may have a thickness of, for example, about to approximately When the hole transport region HTR includes the hole transport layer HTL, the hole transport layer HTL may have a thickness in the range of about to approximately For example, when the hole transport region HTR includes the electron blocking layer EBL, the electron blocking layer EBL may have a thickness in the range of about to approximately 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.

[0170] In addition to the above materials, the hole transport region HTR may further include a charge generating material to increase conductivity. The charge generating material may be uniformly or non-uniformly dispersed in the hole transport region HTR. The charge generating material may be, for example, a p-dopant. The p-dopant may include at least one of a metal halide, a quinone derivative, a metal oxide, and a cyano group-containing compound, but the embodiment is not limited thereto. 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 group-containing compound such as dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexanitrile (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.

[0171] 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, thereby increasing luminous efficiency. The material that may be included in the hole transport region HTR may be used as the material to be included in the buffer layer (not shown). The electron blocking layer EBL may prevent electrons from being injected from the electron transport region ETR into the hole transport region HTR.

[0172] 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 an auxiliary emission layer EAL and an electron blocking layer EBL. The auxiliary emission layer EAL can compensate for the resonance distance according to the wavelength of light emitted from the emission layer EML and can increase the luminous efficiency by controlling the hole charge balance. In an embodiment, the auxiliary emission layer EAL can prevent electrons from being injected into the hole transport region HTR. Materials that can be included in the hole transport region HTR can be used as materials to be included in the auxiliary emission layer EAL. The electron blocking layer EBL can prevent electrons from being injected from the electron transport region ETR into the hole transport region HTR.

[0173] In the light emitting element ED according to the embodiment, the emission layer EML may include a polycyclic compound. 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 of the emission layer EML. In the specification, the polycyclic compound may be referred to as a first compound.

[0174] The polycyclic compound according to the embodiment may include a fused ring having five rings as a core structure, the five rings including one heteroatom, one nitrogen atom (N) and one boron atom (B) as ring-forming atoms. In an embodiment, the polycyclic compound may include a fused ring having seven rings or a fused ring having nine rings as a core structure, wherein two rings including two heteroatoms as ring-forming atoms or four rings including four heteroatoms as ring-forming atoms are respectively fused to the core structure of the fused ring of five rings.

[0175] In the polycyclic compound according to the embodiment, the first benzene ring may be connected to the nitrogen atom of the core structure, and at least one first substituent or at least one second substituent may be bonded to the first benzene ring. The first substituent may be a cyano group, and the second substituent may be a substituted or unsubstituted aryl group. The polycyclic compound according to the embodiment may exhibit a molecular type in which the first benzene ring is connected to the nitrogen atom constituting the core structure and at least one cyano group and at least one aryl group are connected to the first benzene ring, thereby protecting the core structure. In an embodiment, in the polycyclic compound, due to the first substituent and the second substituent, solvation and association with a solvent or a host material may be suppressed, and therefore high efficiency and excellent element life may be achieved during the driving element.

[0176] In an embodiment, the light emitting element ED may include a polycyclic compound. The polycyclic compound may be represented by Formula 1.

[0177] [Formula 1]

[0178]

[0179] In Formula 1, X can be O, S or N (R 12 ); and R 1 to R 12 may each independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted amino group, a substituted or unsubstituted oxy group, a substituted or unsubstituted sulfinyl group, a substituted or unsubstituted boron group, an 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 R 1 to R 4 Can bond to adjacent groups to form 1 to R 4 Form a ring between, or R 5 to R 8 Can bond with adjacent groups to form ring R 5 to R 8 In an embodiment, R 1 to R 11may each independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted arylsulfinyl group, a substituted or unsubstituted arylboronyl group, an 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; and R 12 It may be a substituted or unsubstituted aryl group having a ring carbon number of 6 to 30. For example, R 1 to R 11 can each independently be a hydrogen atom, a deuterium atom or a group selected from Substituent Group 1, and R 12 The group may be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted terphenyl group, but the embodiment is not limited thereto.

[0180] [Substituent Group 1]

[0181]

[0182] As mentioned above, in Formula 1, R 1 to R 4 Can bond to adjacent groups to form 1 to R 4 Form a ring between, or R 5 to R 8 Can bond to adjacent groups to form 5 to R 8 For example, R 1 to R 4 A consecutive pair of them can be combined with each other to form a ring, and R 5 to R 8 Consecutive pairs of R can be combined with each other to form a ring. 1 and R 2 、R 2 and R 3 or R 3 and R 4 can each combine with each other to form a ring, or R 5 and R 6 、R 6 and R 7 or R 7 and R 8 Each can be combined with each other to form a ring. For example, R 2 and R 3 can be combined with each other to form a substituted or unsubstituted heterocycle, and R 6 and R 7 They may combine with each other to form a substituted or unsubstituted heterocycle.

[0183] In formula 1, with R a to R e The connected benzene ring may correspond to the first benzene ring described above. In Formula 1, R a to R e Each of them may be independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, an 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. a to R e Among them, at least one may be the first substituent, and R a to R e At least one of the remaining groups other than the first substituent in the formula may be a second substituent. For example, in Formula 1, R a to R e At least one of the groups may be a cyano group, and at least one of the remaining groups in Ra to Re may be a substituted or unsubstituted aryl group having a ring carbon number of 6 to 30. For example, R a to R e One of them may be a cyano group, and R a to R e The other group other than the cyano group in may be a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms.

[0184] In an embodiment, in Formula 1, in the a to R e Of the two, one may be a cyano group, and the other may be a substituted or unsubstituted phenyl group, and R a to R e The remaining groups except the cyano group and the substituted or unsubstituted phenyl group may each independently be a hydrogen atom, a deuterium atom, or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms.

[0185] For example, in Formula 1, R a to R e Among them, R a Can be cyano, R b 、R c 、R d and R e One of them may be a substituted or unsubstituted phenyl group, and R b 、R c 、R d and R e The remaining groups except the substituted or unsubstituted phenyl groups in the formula (1) may each independently be a hydrogen atom or a deuterium atom. a to Re Among them, R b Can be cyano, R a 、R c 、R d and R e One of them may be a substituted or unsubstituted phenyl group, and R a 、R c 、R d and R e The remaining groups except the substituted or unsubstituted phenyl groups in the formula (1) may each independently be a hydrogen atom or a deuterium atom. a to R e Among them, R c Can be cyano, R a 、R b 、R d and R e One of them may be a substituted or unsubstituted phenyl group, and R a 、R b 、R d and R e The remaining groups except the substituted or unsubstituted phenyl groups in the formula (1) may each independently be a hydrogen atom or a deuterium atom. a to R e Among them, R c Can be cyano, selected from R a 、R b 、R d and R e The two of them may be independently substituted or unsubstituted phenyl, and R a 、R b 、R d and R e The remaining groups except the substituted or unsubstituted phenyl group in may each independently be a hydrogen atom or a deuterium atom.

[0186] In an embodiment, in the polycyclic compound represented by Formula 1, at least one hydrogen atom may be substituted by a deuterium atom. For example, in the polycyclic compound represented by Formula 1, R 1 to R 12 and R a to R e The hydrogen atoms in the molecule or the hydrogen atoms in its substituents may be replaced by deuterium atoms.

[0187] In an embodiment, the polycyclic compound represented by Formula 1 may include a cyano group bonded to the first benzene ring at a para position relative to the nitrogen atom constituting the core structure. Therefore, the polycyclic compound represented by Formula 1 may be represented by one of Formulas 2-1 to 2-3. Formulas 2-1 to 2-3 each represent that R c In the case of cyano.

[0188] [Formula 2-1]

[0189]

[0190] [Formula 2-2]

[0191]

[0192] [Formula 2-3]

[0193]

[0194] In formula 2-1 to formula 2-3, R a 、R b 、R d and R e One or two of them may be independently substituted or unsubstituted phenyl, and R a 、R b 、R d and R e The remaining groups in can each independently be a hydrogen atom or a deuterium atom. For example, R a or R b may be substituted or unsubstituted phenyl, and R a and R b The remaining groups other than substituted or unsubstituted phenyl groups and R d and R e can be independently a hydrogen atom or a deuterium atom. a and R e can be each independently substituted or unsubstituted phenyl, R b and R d They may each independently be a hydrogen atom or a deuterium atom.

[0195] In formula 2-1 to formula 2-3, R 1 to R 11 It may be the same as described in Formula 1.

[0196] In formula 2-3, R f 、R g 、R h 、R i and R j Each of them may independently be a hydrogen atom, a deuterium atom, a cyano group, an unsubstituted alkyl group having a carbon number of 1 to 20, or a substituted or unsubstituted aryl group having a ring carbon number of 6 to 30. For example, R f 、R g 、R h 、R i and R jEach independently may be a hydrogen atom, a deuterium atom, an unsubstituted tert-butyl group, or a substituted or unsubstituted phenyl group.

[0197] In an embodiment, the polycyclic compound represented by Formula 2-3 may be represented by Formula 2-3-1. The polycyclic compound represented by Formula 2-3-1 may be represented by R a and R f Each is independently a substituted or unsubstituted phenyl group.

[0198] [Formula 2-3-1]

[0199]

[0200] In formula 2-3-1, R a1 to R a5 and R f1 to R f5 and R and R are each independently a hydrogen atom, a deuterium atom, or a substituted or unsubstituted alkyl group having a carbon number of 1 to 10. For example, R a1 to R a5 and R f1 to R f5 Each may independently be a hydrogen atom, a deuterium atom, or an unsubstituted tert-butyl group, but the embodiment is not limited thereto.

[0201] In formula 2-3-1, R b 、R d and R e One of them may be a substituted or unsubstituted phenyl group, and R b 、R d and R e The remaining groups in can be independently hydrogen atoms or deuterium atoms. g 、R i and R j may each independently be a hydrogen atom, a deuterium atom, an unsubstituted alkyl group having a carbon number of 1 to 20, or a substituted or unsubstituted aryl group having a ring carbon number of 6 to 30; and R h It may be a hydrogen atom, a deuterium atom or a cyano group.

[0202] In formula 2-3-1, R1 to R 11 It may be the same as described in Formula 1.

[0203] In an embodiment, the polycyclic compound represented by Formula 1 may be represented by one of Formulas 3-1 to 3-5. Formulas 3-1 to 3-5 each represent a compound further defined as R in Formula 1. 1 to R 11 situation.

[0204] [Formula 3-1]

[0205]

[0206] [Formula 3-2]

[0207]

[0208] [Formula 3-3]

[0209]

[0210] [Formula 3-4]

[0211]

[0212] [Formula 3-5]

[0213]

[0214] In formulas 3-1 to 3-5, R 21 to R 36 Each of them may independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted amino group, a substituted or unsubstituted oxy 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. For example, R 21 to R 31 Each of them may independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted arylsulfinyl group, a substituted or unsubstituted arylboronyl group, an unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heteroaryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms. For example, R 21 to R 31 Each of them may be independently a hydrogen atom, a deuterium atom, or a group selected from Substituent Group 1. For example, R 32 to R 36 Each may independently be a hydrogen atom, a deuterium atom, or a substituted or unsubstituted phenyl group, but is not limited thereto.

[0215] In formula 3-1 to formula 3-5, X, R a 、R b 、R c 、R d and R e and R = 1 and R = 2. Each may be the same as described in Formula 1.

[0216] In Formula 3-2 to Formula 3-5, n1, n3, and n5 may each independently be an integer of 0 to 4. If n1, n3, and n5 are each 0, the polycyclic compound according to the embodiment may not be separated by R 32 、R 34 and R 36 In Formula 3-2 to Formula 3-5, n1, n3 and n5 are each 4 and R 32 、R 34 and R 36 The case where all are hydrogen atoms may be the same as the case where n1, n3, and n5 are each 0 in Formula 3-2 to Formula 3-5. If n1, n3, and n5 are each 2 or greater, then multiple R 32 , multiple R 34 and multiple R 36 may be the same, or at least one of them may be different.

[0217] In Formula 3-2 to Formula 3-5, n2 and n4 may each independently be an integer of 0 to 3. If n2 and n4 are each 0, the polycyclic compound according to the embodiment may not be 33 and R 35 In Formula 3-2 to Formula 3-5, n2 and n4 are each 3 and R 33 and R 35 The case where all are hydrogen atoms may be the same as the case where n2 and n4 are each 0 in Formula 3-2 to Formula 3-5. If b2 and b4 are each 2 or greater, then multiple R 33 and multiple R 35 All may be the same, or at least one of them may be different.

[0218] In formula 3-2 to formula 3-5, Y 1 To Y 4 can be independently O, S or N(R 37 ); and Y 5 and Y 6 can be independently O, S, N(R 38 ) or B(R 39 ). For example, in Formula 3-2, Y 1 Can be O or N(R 37 ), and Y 2 Can be O, S or N(R 37 ). In formula 3-3, Y 1 and Y 2 Each of them may be O, but the embodiment is not limited thereto. In Formula 3-4, Y 3 Can be N(R 37 ), and Y 4 Can be O, S or N(R37 ). In formula 3-5, Y 5 Can be O or S, and Y 6 Can be N(R 38 ) or B(R 39 ).

[0219] In formula 3-2 to formula 3-5, R 37 to R 39 Each may be independently a substituted or unsubstituted aryl group having a ring carbon number of 6 to 30. For example, R 37 to R 39 Each may independently be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted terphenyl group.

[0220] In the polycyclic compound according to the embodiment, the first benzene ring may be connected to the nitrogen atom constituting the core structure, and at least one cyano group or at least one aryl group may be additionally connected to the first benzene ring, thereby contributing to achieving high efficiency and long life improvement of the light emitting element ED.

[0221] In the polycyclic compound according to the embodiment, at least one cyano group bonded to the first benzene ring serves as an electron-withdrawing group to reduce the electron-donating ability of the polycyclic compound according to the embodiment and reduce the polarization of the core structure, thereby suppressing its electrostatic interaction with molecules having high polarity. In the polycyclic compound according to the embodiment, because at least one cyano group is located relatively outside the core structure, conjugation with the core structure does not occur. Therefore, in the polycyclic compound according to the embodiment, due to the introduction of the cyano group, a significant change in emission color and an expansion of the full width at half maximum can be suppressed, and properties suitable for use as a blue light-emitting material can be provided.

[0222] In the polycyclic compound according to the embodiment, at least one aryl group may be connected to the first benzene ring. Because it is located on the relatively outer side of the core structure, the aryl group serves as a robust substituent without being conjugated with the core structure, and thus the association between the surrounding molecules and the core structure can be suppressed. In the polycyclic compound according to the embodiment, because the aryl group connected to the first benzene ring is a robust substituent, the structural relaxation caused by the mobility of the substituent during luminescence is not significant, and thus the polycyclic compound can exhibit high color purity. Therefore, the light-emitting element ED including the polycyclic compound in the emission layer EML can emit deep blue, and at the same time, in addition to the increase in emission efficiency, the element life can also be improved.

[0223] In an embodiment, the polycyclic compound may be selected from compound group 1. In an embodiment, the light emitting element ED may include at least one compound selected from compound group 1. In an embodiment, the emission layer EML may include at least one compound selected from compound group 1.

[0224] [Compound Group 1]

[0225]

[0226]

[0227]

[0228]

[0229]

[0230]

[0231]

[0232] In the light-emitting element ED according to the embodiment, the emission layer EML may be a delayed fluorescence emission layer including a host and a dopant. For example, the emission layer EML may emit thermally activated delayed fluorescence (TADF). A polycyclic compound may be a delayed fluorescence dopant. For example, a polycyclic compound may be a thermally activated delayed fluorescence dopant.

[0233] The emission layer EML may include a polycyclic compound according to an embodiment as a dopant. The polycyclic compound may emit blue light. For example, the polycyclic compound may be a luminescent material having a peak emission wavelength in the range of about 430 nm to about 490 nm. For example, the polycyclic compound may be a luminescent material having a peak emission wavelength in the range of about 450 nm to about 470 nm.

[0234] In an embodiment, the emission layer EML may include the polycyclic compound according to an embodiment, and may further include at least one of the second compound, the third compound, and the fourth compound. In an embodiment, the emission layer EML may further include a second compound represented by Formula 2. In an embodiment, the second compound may serve as a hole transport host material in the emission layer EML.

[0235] [Formula HT-1]

[0236]

[0237] In formula HT-1, A1 to A8 may each independently be N or C(R 51 For example, A1 to A8 can each independently be C(R 51 For another example, one of A1 to A8 may be N, and the remaining groups in A1 to A8 may each independently be C(R 51 ).

[0238] In Formula HT-1, L1 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. For example, L1 may be a directly linked, substituted or unsubstituted phenylene group, a substituted or unsubstituted divalent biphenyl group, a substituted or unsubstituted divalent carbazolyl group, or the like, but the embodiment is not limited thereto.

[0239] In formula HT-1, Y a Can be directly connected, C(R 52 )(R 53 ) or Si(R 54 )(R 55 ). For example, the two rings connected to the nitrogen atom in formula HT-1 can be directly connected, In formula HT-1, when Y a In the case of direct attachment, the second compound represented by Formula HT-1 may include a carbazole moiety.

[0240] In Formula HT-1, Ar1 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. For example, Ar1 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.

[0241] In formula HT-1, R 51 to R 55 Each of the R-1 and R-2 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 amino 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 51 to R 55 can be independently a hydrogen atom or a deuterium atom. 51 to R 55 Each independently may be an unsubstituted methyl group or an unsubstituted phenyl group.

[0242] In the embodiment, the second compound represented by Formula HT-1 may be selected from Compound Group 2. In the embodiment, in the light emitting element ED, the second compound may include at least one compound selected from Compound Group 2.

[0243] [Compound Group 2]

[0244]

[0245]

[0246]

[0247] 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.

[0248] 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 serve as an electron transport host material of the emission layer EML.

[0249] [Formula ET-1]

[0250]

[0251] In formula ET-1, Z a to Z c At least one of them can each be N, and Z a to Z c The remaining groups in the group may each independently be C(R 56 ). For example, Z a to Z c One of them can be N, and Z a to Z c The remaining groups in the group may each independently be C(R 56 ). Thus, the third compound represented by Formula ET-1 may include a pyridine moiety. In another embodiment, Z a to Z c Two of them can be N, and Z a to Z c The remaining groups in can be C(R 56 ). Thus, the third compound represented by Formula ET-1 may include a pyrimidine moiety. In another embodiment, X1 to X3 may each be N. Thus, the third compound represented by Formula ET-1 may include a triazine moiety.

[0252] In formula ET-1, R 56 It may be a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 ring carbon atoms.

[0253] In Formula ET-1, e1 to e3 may each independently be an integer of 0 to 10.

[0254] In Formula ET-1, Ar2 to Ar4 may each independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms. For example, Ar2 to Ar4 may each independently be a substituted or unsubstituted phenyl group, or a substituted or unsubstituted carbazolyl group.

[0255] In Formula ET-1, L2 to L4 may each independently 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. When e1 to e3 are each 2 or greater, L2 to L4 may each independently be a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms.

[0256] 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.

[0257] [Compound Group 3]

[0258]

[0259]

[0260]

[0261]

[0262]

[0263] In compound group 3, "D" represents a deuterium atom, and "Ph" represents an unsubstituted phenyl group.

[0264] 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 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.

[0265] For example, the absolute value of the triplet energy (T1) of the exciplex 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 exciplex may be a value smaller than the energy gap of each host material. The exciplex may have a triplet energy level of less than or equal to about 3.0 eV, which is the energy gap between the hole transport host and the electron transport host.

[0266] In an embodiment, in addition to the first, second, and third compounds described above, the emission layer EML may further include a fourth compound. The fourth compound may function as a phosphorescent sensitizer in the emission layer EML. Energy may be transferred from the fourth compound to the first compound, thereby emitting light.

[0267] In an embodiment, the emission layer EML may further 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 include a fourth compound represented by Formula D-1:

[0268] [Formula D-1]

[0269]

[0270] In formula D-1, Q1 to Q4 may each independently be C or N.

[0271] In formula D-1, C1 to C4 may each independently be a substituted or unsubstituted hydrocarbon ring having 5 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic ring having 2 to 30 ring carbon atoms.

[0272] In formula D-1, L 11 To L 13 Can be independently connected for direct connection, 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 middle, represents a bond with one of C1 to C4.

[0273] In Formula D-1, b11 to b13 may each independently be 0 or 1. If b11 is 0, C1 and C2 may not be directly bonded to each other. If b12 is 0, C2 and C3 may not be directly bonded to each other. If b13 is 0, C3 and C4 may not be directly bonded to each other.

[0274] In formula D-1, R61 to R 66 Each of the R-1 and R-2 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 amino 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.

[0275] In an embodiment, in Formula D-1, d1 to d4 may each independently be an integer from 0 to 4. In Formula D-1, if d1 to d4 are each 0, the fourth compound may not be respectively R 61 to R 64 d1 to d4 are each 4 and multiple R 61 to R 64 The case where each of R is a hydrogen atom may be the same as the case where each of d1 to d4 is 0. When each of d1 to d4 is 2 or more, the plurality of R 61 to R 64 They may be identical to each other, or at least one of them may be different from the others.

[0276] In an embodiment, in Formula D-1, C1 to C4 may each independently be a substituted or unsubstituted hydrocarbon ring, or a substituted or unsubstituted heterocycle represented by one of Formulas C-1 to C-4:

[0277]

[0278] In formula C-1 to formula C-4, P1 can be or C(R 74 ), P2 can be or N(R 81 ), P3 can be or N(R 82 ), and P4 can be or C(R 88 ). In Formula C-1 to Formula C-4, R 71 to R 88 Each may 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 be bonded to an adjacent group to form a ring.

[0279] In Formula C-1 to Formula C-4, represents a bond to Pt as the central metal atom, and Represents the adjacent cyclic group (C1 to C4) or the connecting part (L 11 To L 13 ) key.

[0280] In an embodiment, the emission layer (EML) may include a first compound that is a polycyclic 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 exciplex, and energy may be transferred from the exciplex to the first compound, thereby emitting light.

[0281] 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 in the light-emitting element ED may serve as a sensitizer that transfers energy from the host to the first compound as a light-emitting dopant. For example, the fourth compound used as an auxiliary dopant may accelerate energy transfer to the first compound as a light-emitting dopant, thereby increasing the emission ratio of the first compound. Therefore, the emission layer EML may have improved luminous efficiency. When the energy transfer to the first compound increases, the excitons formed in the emission layer EML will not accumulate in the emission layer EML and can emit light quickly, so that the degradation of the light-emitting element ED is small. Therefore, the service life of the light-emitting element ED according to the embodiment can be extended.

[0282] In the embodiment, 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 and third compounds as two different hosts, the first compound emitting delayed fluorescence, and the fourth compound including an organic metal complex, thereby exhibiting excellent luminous efficiency characteristics.

[0283] In the embodiment, the fourth compound represented by Formula D-1 may be selected from Compound Group 4. In the embodiment, in the light emitting element ED, the fourth compound may include at least one compound selected from Compound Group 4.

[0284] [Compound Group 4]

[0285]

[0286]

[0287]

[0288] In compound group 4, "D" represents a deuterium atom.

[0289] In an embodiment, in a light-emitting element ED, when the emission layer EML includes a first compound, a second compound, and a third compound, the amount of the first compound may be in a range of about 0.1 wt % to about 5 wt % based on the total weight of the first, second, and third compounds. However, embodiments are not limited thereto. When the amount of the first compound satisfies the above range, energy transfer from the second and third compounds to the first compound may be increased, thereby increasing luminous efficiency and device lifespan.

[0290] In the emission layer (EML), the combined amount of the second compound and the third compound may be a remainder of the total weight of the first, second, and third compounds, excluding the amount of the first compound. For example, the combined amount of the second and third compounds in the emission layer (EML) may be in a range of approximately 65 wt % to approximately 95 wt % based on the total weight of the first, second, and third compounds.

[0291] Within the combined amount of the second compound and the third compound, a weight ratio of the second compound to the third compound may be in a range of about 3:7 to about 7:3.

[0292] 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 luminous efficiency and device life can be increased. When the amounts of the second compound and the third compound deviate from the above ranges and ratios, the charge balance in the emission layer (EML) may not be achieved, and thus, the luminous efficiency may be reduced and the device may be easily degraded.

[0293] When the emission layer EML includes the fourth compound, the amount of the fourth compound in the emission layer EML may be in a range of about 4 wt % to about 30 wt % based on the total weight of the first, second, third, and fourth compounds. However, embodiments are not limited thereto. When the amount of the fourth compound satisfies the above range, energy transfer from the host to the first compound as a light-emitting dopant may increase, thereby improving the emission ratio and, therefore, improving the luminous efficiency of the emission layer EML. When the first, second, third, and fourth compounds included in the emission layer EML meet the above ranges and ratios, excellent luminous efficiency and a long service life may be achieved.

[0294] An emission layer EML may be provided on the hole transport region HTR. The emission layer EML may have a thickness of, for example, about to approximately For example, the emission layer EML may have a thickness in the range of about to approximately The emission layer EML may have a structure consisting of a layer including a single material, a structure consisting of layers including different materials, or a structure including a plurality of layers including different materials.

[0295] In such Figures 5 to 9 In each light emitting element ED shown in each figure, the emission layer EML may further include the above-described polycyclic compound according to the embodiment as a dopant. Figures 5 to 9 In the light emitting element ED shown in each figure, the emission layer EML may include a first compound that is a polycyclic compound, and may further include at least one of a second compound represented by Formula HT-1 and a third compound represented by Formula ET-1. Figures 5 to 9 In the light emitting element ED shown in each figure, the emission layer EML may include a first compound which is a polycyclic compound, a second compound represented by Formula HT-1, a third compound represented by Formula ET-1, and a fourth compound represented by Formula D-1.

[0296] In the light emitting element ED, the emission layer EML may include anthracene derivatives, pyrene derivatives, fluoranthene derivatives, Derivatives, dihydrobenzanthracene derivatives or triphenylene derivatives. For example, the emission layer EML may include anthracene derivatives or pyrene derivatives.

[0297] In accordance with Figures 5 to 9In each light-emitting element ED of the embodiment shown in FIG, in addition to the above-mentioned host and dopant, the emission layer EML may further include a host and dopant in the related art, and for example, 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.

[0298] [Formula E-1]

[0299]

[0300] In formula E-1, R 31 to R 40 Each of the R groups may independently be 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, R 31 to R 40 It may bond with an adjacent group to form a saturated hydrocarbon ring or an unsaturated hydrocarbon ring, or a saturated heterocyclic ring or an unsaturated heterocyclic ring.

[0301] In Formula E-1, c and d may each independently be an integer from 0 to 5.

[0302] In an embodiment, the compound represented by Formula E-1 may be any compound selected from Compound E1 to Compound E19:

[0303]

[0304]

[0305] 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 host material of a phosphorescent light-emitting element.

[0306] [Formula E-2a]

[0307]

[0308] In Formula E-2a, a may be an integer 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. aEach independently may 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.

[0309] In formula E-2a, A1 to A5 may each independently be N or C(R i ). In formula E-2a, R a to R i Each of the R groups may independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted amino 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 heterocyclic ring containing N, O, S, etc. as a ring-constituting atom.

[0310] In formula E-2a, two or three of A1 to A5 may be N, and the remaining groups of A1 to A5 may each independently be C(R i ).

[0311] [Formula E-2b]

[0312]

[0313] In Formula E-2b, Cbz1 and Cbz2 may each independently be an unsubstituted carbazolyl group or a carbazolyl group substituted with an aryl group having 6 to 30 ring carbon atoms. b 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. In Formula E-2b, b may be an integer from 0 to 10, and when b is 2 or greater, multiple L b Each independently may 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.

[0314] In an embodiment, 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 below are merely examples, and the compounds represented by Formula E-2a or Formula E-2b are not limited to Compound Group E-2.

[0315] [Compound Group E-2]

[0316]

[0317]

[0318] In an embodiment, the emission layer EML may include a compound represented by Formula Ma. The compound represented by Formula Ma may serve as a phosphorescent dopant material.

[0319] [Formula]

[0320]

[0321] In formula Ma, Y1 to Y4 and Z1 to Z4 can each independently be C(R1) or N, and R1 to R4 can each 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-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 can be 0 or 1, and n can be 2 or 3. In formula Ma, when m is 0, n can be 3, and when m is 1, n can be 2.

[0322] The compound represented by the formula Ma can be used as a phosphorescent dopant.

[0323] In the embodiment, 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.

[0324]

[0325]

[0326] In an embodiment, the emission layer EML may include a compound represented by any one of Formulas Fa to Fc. The compounds represented by Formulas Fa to Fc may be used as a fluorescent dopant material.

[0327] [Formula]

[0328]

[0329] In formula Fa, R a to R j The two of them can be independently The group represented by R is substituted. a to R j The unresolved The remaining groups substituted by the groups represented by may each independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted amino 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.

[0330] In by In the group represented by, Ar1 and Ar2 may each independently be a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms. For example, at least one of Ar1 and Ar2 may be a heteroaryl group containing O or S as a ring atom.

[0331] [Formula Fb]

[0332]

[0333] In formula Fb, R a and R b Can be each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group with 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group with 2 to 20 carbon atoms, a substituted or unsubstituted aryl group with 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group with 2 to 30 ring-forming carbon atoms, or bonded to form a ring with an adjacent group. In formula Fb, Ar1 to Ar4 can each independently be a substituted or unsubstituted aryl group with 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group with 2 to 30 ring-forming carbon atoms. For example, at least one of Ar1 to Ar4 can each independently be a heteroaryl group including O or S as a ring atom.

[0334] In formula Fb, U and V may each independently be a substituted or unsubstituted hydrocarbon ring having 5 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic ring having 2 to 30 ring carbon atoms.

[0335] In formula Fb, the number of the ring represented by U and V (hereinafter referred to as the number of U and the number of V) can be 0 or 1 independently of each other. When the number of U or V is 1, there can be a fused ring at the part indicated by U or V respectively, and when the number of U or V is 0, there can be no fused ring at the part indicated by U or V respectively. When the number of U is 0 and the number of V is 1, or when the number of U is 1 and the number of V is 0, the fused ring with fluorene core in formula Fb can be a cyclic compound with four rings. When U and V are each 0, the fused ring with fluorene core in formula Fb can be a cyclic compound with three rings. When U and V are each 1, the fused ring with fluorene core in formula Fb can be a cyclic compound with five rings.

[0336] [Formula Fc]

[0337]

[0338] In Formula Fc, A1 and A2 can each independently be 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. 11 Each may independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted amino 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 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.

[0339] In Formula Fc, A1 and A2 can each independently bond to a substituent of an adjacent ring to form a fused ring. For example, when A1 and A2 are each independently N(R m ), A1 may be bonded to R4 or R5 to form a ring, and / or A2 may be bonded to R7 or R8 to form a ring.

[0340] In an embodiment, the emission layer EML may further include styrene derivatives (e.g., 1,4-bis[2-(3-N-ethylcarbazolyl)vinyl]benzene (BCzVB), 4-(di-p-tolylamino)-4'-[(di-p-tolylamino)styrene]stilbene (DPAVB) and N-(4-((E)-2-(6-((E)-4-(diphenylamino)styrene)naphthalene-2-yl)vinyl)phenyl)-N-phenylaniline (N-BDAVBi), 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 and 1,4-bis(N,N-diphenylamino)pyrene), etc. as dopant materials in the related art.

[0341] The emission layer EML may further include a phosphorescent dopant material of the related art. For example, a metal complex including 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-difluorophenylpyridine-N,C2)iridium (III) (FIrpic), bis(2,4-difluorophenylpyridine)-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.

[0342] In an embodiment, the emission layer EML may include a quantum dot material. The quantum dots may include a II-VI compound, a III-VI compound, an I-III-VI compound, a III-V compound, a III-II-V compound, a IV-VI compound, a Group IV element, a Group IV compound, or any combination thereof.

[0343] Examples of II-VI compounds may include binary compounds such as CdSe, CdTe, CdS, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, MgSe, MgS, and mixtures thereof; ternary compounds such as CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, CdZnSe, Cd ZnTe, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, MgZnSe, MgZnS and mixtures thereof; and quaternary compounds such as HgZnTeS, CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe and mixtures thereof; and any combinations thereof.

[0344] Examples of Group 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 ; and any combination thereof.

[0345] Examples of Group I-III-VI compounds may include: ternary compounds such as AgInS, AgInS2, CuInS, CuInS2, AgGaS2, CuGaS2, CuGaO2, AgGaO2, AgAlO2 and mixtures thereof; quaternary compounds such as AgInGaS2 or CuInGaS2; and any combination thereof.

[0346] Examples of III-V compounds may include binary compounds such as GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, InSb, and mixtures thereof; ternary compounds such as GaNPs, GaNAs, GaNSb, GaPAs, GaPSb, AlNPs, AlNAs, AlNSb, AlPAs, AlPSb, InGaP, InAlP, InNP, InNAs, InNSb, InPAs, InPSb, and mixtures thereof; quaternary compounds such as GaAlNPs, GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNPs, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNPs, InAlNAs, InAlNSb, InAlPAs, InAlPSb, and mixtures thereof; and any combination thereof. In an embodiment, the III-V compound may also include a Group II metal. Examples of III-II-V compounds may include InZnP, etc.

[0347] Examples of Group IV-VI compounds may include binary compounds such as SnS, SnSe, SnTe, PbS, PbSe, PbTe, and mixtures thereof; ternary compounds such as SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, SnPbTe, and mixtures thereof; and quaternary compounds such as SnPbSSe, SnPbSeTe, SnPbSTe, and mixtures thereof.

[0348] Examples of Group IV elements may include Si, Ge, and mixtures thereof. Examples of Group IV compounds may include binary compounds such as SiC, SiGe, and mixtures thereof.

[0349] Each element included in a compound such as a binary compound, a ternary compound, or a quaternary compound may be present in a particle in a uniform concentration distribution or in a non-uniform concentration distribution. For example, a formula may indicate the elements included in the compound, but the ratio of the elements in the compound may vary. For example, AgInGaS2 may mean AgIn x Ga 1-x S2 (where x is a real number between 0 and 1).

[0350] In an embodiment, the quantum dot may have a single structure or a core-shell structure in which the concentration of each element included in the quantum dot is uniform. For example, the material included in the core may be different from the material included in the shell.

[0351] The shell of a quantum dot can serve as a protective layer to prevent chemical denaturation of the core to maintain semiconductor properties, and / or can serve as a charging layer to impart electrophoretic properties to the quantum dot. The shell can be monolayer or multilayer. The interface between the core and the shell can have a concentration gradient, where the concentration of the element present in the shell decreases toward the core.

[0352] The shell of the quantum dot may include a metal oxide, a non-metal oxide, a semiconductor compound, or any combination thereof. Examples of the metal oxide and the non-metal oxide may include binary compounds such as SiO2, Al2O3, TiO2, ZnO, MnO, Mn2O3, Mn3O4, CuO, FeO, Fe2O3, Fe3O4, CoO, Co3O4, and NiO; or ternary compounds such as MgAl2O4, CoFe2O4, NiFe2O4, and CoMn2O4, but the embodiment is not limited thereto.

[0353] Examples of semiconductor compounds may include CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnSeS, ZnTeS, GaAs, GaP, GaSb, HgS, HgSe, HgTe, InAs, InP, InGaP, InSb, AlAs, AlP, AlSb, etc., but the embodiment is not limited thereto.

[0354] The quantum dots may have a full width at half maximum (FWHM) of an emission wavelength spectrum less than or equal to about 45 nm. For example, the quantum dots may have a FWHM of an emission wavelength spectrum less than or equal to about 40 nm. For example, the quantum dots may have a FWHM of an emission wavelength spectrum less than or equal to 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, thereby improving a wide viewing angle.

[0355] The form of the quantum dots may be a form used in related fields, but the embodiment is not limited thereto. For example, the quantum dots may have a spherical form, a pyramidal form, a multi-arm form, or a cubic form, or the quantum dots may be in the form of nanoparticles, nanotubes, nanowires, nanofibers, nanoplates, etc.

[0356] When the size of the quantum dots is adjusted or the ratio of elements in the quantum dot compound is adjusted, the band gap can be controlled, and thus light in various wavelength ranges can be obtained in the quantum dot emission layer. Therefore, using quantum dots as described above (using quantum dots of different sizes or different ratios of elements in the quantum dot compound), the light-emitting element can emit light in various wavelengths. The size of the quantum dots or the ratio of elements in the quantum dot compound can be selected to emit red light, green light and / or blue light. In an embodiment, the quantum dots can be configured to emit white light by combining light of various colors.

[0357] In such Figures 5 to 9 In the light emitting element ED according to the embodiment shown in each figure, the electron transport region ETR may be provided on the emission layer EML. The electron transport region ETR may include at least one of the hole blocking layer HBL, the electron transport layer ETL, and the electron injection layer EIL, but the embodiment is not limited thereto.

[0358] The electron transport region ETR may have a structure composed of a layer including a single material, a structure composed of layers including different materials, or a structure including a plurality of layers including different materials.

[0359] 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 including an electron injection material and an electron transport material. The electron transport region ETR may have a single-layer structure including different materials. In an embodiment, the electron transport region ETR may have a structure in which an electron transport layer ETL / electron injection layer EIL, a hole blocking layer HBL / electron transport layer ETL / electron injection layer EIL are stacked in sequence from the emission layer EML, but the embodiment is not limited thereto. The electron transport region ETR may have a structure in which, for example, about to approximately The thickness is within the range of .

[0360] 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-Blodgett (LB) method, an inkjet printing method, a laser printing method, and a laser induced thermal imaging (LITI) method.

[0361] In an embodiment, the electron transport region ETR may include a compound represented by Formula ET-2:

[0362] [Formula ET-2]

[0363]

[0364] In formula ET-2, at least one of X1 to X3 is N, and the remaining groups of X1 to X3 may each independently be C(R a ). R aIt 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. In Formula ET-2, Ar1 to Ar3 may each independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms.

[0365] In Formula ET-2, a to c may each independently be an integer from 0 to 10. In Formula ET-2, L1 to L3 may each independently 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. When a to c are each independently 2 or greater, multiple L1 to L3 may each independently be a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms.

[0366] The electron transport region ETR may include an anthracene compound. However, the embodiment is not limited thereto, and the electron transport region ETR may include, for example, tris(8-hydroxyquinoline)aluminum (Alq3), 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 (tBu-PBD), bis(2-methyl-8-hydroxyquinolinolato-N1,O8)-(1,1'-biphenyl-4-hydroxy)aluminum (BAlq), bis(10-hydroxybenzoquinolinolato)beryllium (Bebq2), 9,10-di(naphthalene-2-yl)anthracene (ADN), 1,3-bis[3,5-di(pyridin-3-yl)phenyl]benzene (BmPyPhB) or a mixture thereof.

[0367] In an embodiment, the electron transport region ETR may include a compound selected from compound group 3.

[0368] In an embodiment, the electron transport region ETR may include at least one compound selected from compound ET1 to compound ET36:

[0369]

[0370]

[0371]

[0372] In an embodiment, the electron transport region ETR may include: metal halides such as LiF, NaCl, CsF, RbCl, RbI, CuI and KI; lanthanides such as Yb; or co-deposited materials of metal halides and lanthanides. For example, the electron transport region ETR may include KI:Yb, RbI:Yb, LiF:Yb, etc. as co-deposited materials. The electron transport region ETR may be formed using metal oxides such as Li2O and BaO, or 8-hydroxy-quinoline lithium (Liq), etc., but the embodiment is not limited thereto. In another embodiment, the electron transport region ETR may also include a mixture material of an electron transport material and an insulating organic metal salt. The organic metal salt may be a material having an energy band gap greater than or equal to about 4 eV. For example, the organic metal salt may include a metal acetate, a metal benzoate, a metal acetoacetate, a metal acetylacetonate, or a metal stearate.

[0373] 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.

[0374] The electron transport region ETR may include the above-mentioned compound of the hole transport region in at least one of the electron injection layer EIL, the electron transport layer ETL, and the hole blocking layer HBL.

[0375] When the electron transport region ETR includes the electron transport layer ETL, the electron transport layer ETL may have a thickness of about to approximately For example, the thickness of the electron transport layer ETL can be about to approximately 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 approximately to approximately For example, the thickness of the EIL can be in the range of about to approximately 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.

[0376] 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.

[0377] The second electrode EL2 may be a transmissive electrode, a semi-transmissive reflective 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.).

[0378] When the second electrode EL2 is a semi-transmissive reflective electrode or a reflective electrode, the second electrode EL2 may include Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF, Mo, Ti, Yb, W, a compound thereof, or a mixture thereof (e.g., AgMg, AgYb, or MgYb), or a material having a multilayer structure 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 semi-transmissive reflective film formed of the above materials and a transparent conductive film formed of ITO, IZO, ZnO, ITZO, or the like. 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.

[0379] Although not shown in the drawings, the second electrode EL2 may be electrically connected to the auxiliary electrode. If the second electrode EL2 is connected to the auxiliary electrode, the resistance of the second electrode EL2 may be reduced.

[0380] In the embodiment, in the light emitting element ED, a cover layer CPL may be further provided on the second electrode EL2. The cover layer CPL may have a multi-layer structure or a single-layer structure.

[0381] In an embodiment, the cover layer CPL may include an organic layer or an inorganic layer. For example, when the cover layer CPL includes an inorganic material, the inorganic material may include an alkali metal compound (eg, LiF), an alkaline earth metal compound (eg, MgF2), SiON, SiNx 、SiO y wait.

[0382] For example, when the cover layer CPL includes an organic material, the organic material may include α-NPD, NPB, TPD, m-MTDATA, Alq3, CuPc, N4,N4,N4',N4'-tetrakis(biphenyl-4-yl)biphenyl-4,4'-diamine (TPD15), 4,4',4"-tris(carbazol-9-yl)triphenylamine (TCTA), etc., or may include an epoxy resin, or an acrylate resin such as methacrylate. However, the embodiment is not limited thereto, and the cover layer CPL may include at least one of compounds P1 to P5:

[0383]

[0384] The cover layer CPL may have a refractive index greater than or equal to 1.6, and a refractive index greater than or equal to about 1.6 with respect to light in a wavelength range of about 550 nm to about 660 nm.

[0385] Figures 10 to 13 Each is a schematic cross-sectional view of a display device DD-a, DD-TD, DD-b, DD-c according to an embodiment. Figures 10 to 13 When the display devices DD-a, DD-TD, DD-b, and DD-c according to the embodiment are shown in FIG. 1 , the description of the display devices DD-a, DD-TD, DD-b, and DD-c described above will not be repeated. Figures 3 to 6 The duplicate features described will instead describe the different features.

[0386] refer to Figure 10 The display device DD-a according to the embodiment may include a display panel DP, a light control layer CCL disposed on the display panel DP, and a color filter layer CFL, wherein the display panel DP includes a display device layer DP-ED. Figure 10 In the embodiment shown in , 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, and the display device layer DP-ED may include a light emitting element ED.

[0387] 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 11 The structure of the light emitting element ED shown in FIG. 1 may be based on the structure described above. Figures 5 to 9 The same structure of one of the light-emitting elements. Figure 10The light emitting element ED shown in FIG. 1 may include the polycyclic compound according to the embodiment. Therefore, the light emitting element ED may exhibit characteristics of high efficiency and long life.

[0388] refer to Figure 10 , the emission layer EML can be provided in the opening OH defined in the pixel-defining film PDL. For example, the emission layer EML separated by the pixel-defining film PDL and provided corresponding to each of the light-emitting regions PXA-R, PXA-G, and PXA-B can emit light within the same wavelength range. In the display device DD-a, the emission layer EML can emit blue light. Although not shown in the drawings, in an embodiment, the emission layer EML can be provided as a common layer for all the light-emitting regions PXA-R, PXA-G, and PXA-B.

[0389] 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, for example, quantum dots or phosphors. The light converter may emit light by converting its wavelength. For example, the light control layer CCL may be a layer including quantum dots or a layer including phosphors.

[0390] The light-control layer CCL may include a plurality of light-control parts CCP1, CCP2, and CCP3. The light-control parts CCP1, CCP2, and CCP3 may be spaced apart from each other.

[0391] refer to Figure 10 , the separation pattern BMP may be disposed between the light control parts CCP1, CCP2, and CCP3 that are spaced apart from each other, but the embodiment is not limited thereto. Figure 10 , it is shown that the separation pattern BMP does not overlap with the light control parts CCP1 , CCP2 , and CCP3 , but edges of the light control parts CCP1 , CCP2 , and CCP3 may overlap with at least a portion of the separation pattern BMP.

[0392] The light control layer CCL may include a first light control component CCP1, a second light control component CCP2 and a third light control component CCP3, the first light control component CCP1 including a first quantum dot QD1 that converts the first color light provided from the light emitting element ED into a second color light, the second light control component CCP2 including a second quantum dot QD2 that converts the first color light into a third color light, and the third light control component CCP3 transmits the first color light.

[0393] In an embodiment, the first light control component CCP1 can provide red light as the second color light, and the second light control component CCP2 can provide green light as the third color light. The third light control component CCP3 can provide blue light, which transmits the blue light as the first color light provided by the light-emitting element ED. For example, the first quantum dot QD1 can be a red quantum dot, and the second quantum dot QD2 can be a green quantum dot. Quantum dots QD1 and QD2 can each be a quantum dot as described above.

[0394] The light control layer CCL may further include a scatterer SP. The first light control component CCP1 may include first quantum dots QD1 and scatterers SP, the second light control component CCP2 may include second quantum dots QD2 and scatterers SP, and the third light control component CCP3 may not include any quantum dots but may include a scatterer SP.

[0395] The scatterers SP may be inorganic particles. For example, the scatterers SP may include at least one of TiO2, ZnO, Al2O3, and SiO2 (such as hollow spherical silica). The scatterers SP may include one of TiO2, ZnO, Al2O3, and SiO2 (such as hollow spherical silica), or may be a mixture of at least two materials selected from TiO2, ZnO, Al2O3, and SiO2 (such as hollow spherical silica).

[0396] The first light control component CCP1, the second light control component CCP2, and the third light control component CCP3 may each include a base resin BR1, BR2, and BR3 in which quantum dots QD1 and QD2 and a scatterer SP are dispersed. In an embodiment, the first light control component CCP1 may include the first quantum dots QD1 and the scatterer SP dispersed in the first base resin BR1, the second light control component CCP2 may include the second quantum dots QD2 and the scatterer SP dispersed in the second base resin BR2, and the third light control component CCP3 may include the scatterer SP dispersed in the third base resin BR3.

[0397] The matrix resins BR1, BR2, and BR3 may be media in which quantum dots QD1 and QD2 and scatterers SP are dispersed, and may include various resin compositions, which may be referred to as adhesives. For example, the matrix resins BR1, BR2, and BR3 may be acrylic resins, urethane resins, silicone resins, epoxy resins, and the like. The matrix resins BR1, BR2, and BR3 may each be a transparent resin. In an embodiment, the first matrix resin BR1, the second matrix resin BR2, and the third matrix resin BR3 may be the same as or different from each other.

[0398] Barrier layers BFL1 and BFL2 may each independently include at least one inorganic layer. For example, barrier layers BFL1 and BFL2 may include an inorganic material. For example, barrier 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, or a metal film that ensures light transmittance. Barrier layers BFL1 and BFL2 may each independently further include an organic film. Barrier layers BFL1 and BFL2 may be formed of a single layer or multiple layers.

[0399] In the display device DD-a according to the embodiment, the color filter layer CFL may be disposed on the light control layer CCL. For example, the color filter layer CFL may be disposed (eg, directly disposed) on the light control layer CCL. In the embodiment, the blocking layer BFL2 may be omitted.

[0400] The color filter layer CFL may include color filters CF1, CF2, and CF3. The first, second, and third color filters CF1, CF2, and CF3 may be arranged so that they correspond to the red, green, and blue light emitting regions PXA-R, PXA-G, and PXA-B, respectively.

[0401] The color filter layer CFL may include a first color filter CF1 configured to transmit a second color light, a second color filter CF2 configured to transmit a third color light, and a third color filter CF3 configured to transmit the first color light. For example, the first color filter CF1 may be a red color filter, the second color filter CF2 may be a green color filter, and the third color filter CF3 may be a blue color filter. Each of the color filters CF1, CF2, and CF3 may include a polymerized photosensitive resin and a pigment or dye. The first color filter CF1 may include a red pigment or dye, the second color filter CF2 may include a green pigment or dye, and the third color filter CF3 may include a blue pigment or dye.

[0402] However, the embodiment is not limited thereto, and the third color filter CF3 may not include a pigment or dye. The third color filter CF3 may include a polymerized photosensitive resin and may not include a pigment or dye. The third color filter CF3 may be transparent. The third color filter CF3 may be formed of a transparent photosensitive resin.

[0403] In an embodiment, the first color filter CF1 and the second color filter CF2 may be yellow color filters. The first color filter CF1 and the second color filter CF2 may not be provided as separate color filters, and may be provided as one color filter.

[0404] Although not shown in the drawings, the color filter layer CFL may further include a light-blocking member (not shown). The light-blocking member may be a black matrix. The light-blocking member (not shown) may include an organic light-blocking material or an inorganic light-blocking material containing a black pigment or dye. The light-blocking member (not shown) may prevent light leakage and may separate the boundaries between adjacent color filters CF1, CF2, and CF3.

[0405] A 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, or the like. However, embodiments are not limited thereto, and the base substrate BL may be an inorganic layer, an organic layer, or a composite material layer. Although not shown in the drawings, in embodiments, the base substrate BL may be omitted.

[0406] Figure 11 FIG2 is a schematic cross-sectional view of a portion of a display device DD-TD according to an embodiment. In the display device DD-TD according to an embodiment, the light-emitting element ED-BT may include light-emitting structures OL-B1, OL-B2, and OL-B3. At least one of the light-emitting structures OL-B1, OL-B2, and OL-B3 may include a polycyclic compound according to an embodiment. Therefore, the light-emitting element ED-BT may exhibit high efficiency and a long lifespan.

[0407] 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 between the first electrode EL1 and the second electrode EL2 in a thickness direction. The light emitting structures OL-B1, OL-B2, and OL-B3 may each include a hole transport region HTR ( Figure 10 ), Emission layer EML ( Figure 10 ) and electron transport region ETR( Figure 10 ).

[0408] 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.

[0409] exist Figure 11In the embodiment shown in FIG, the light emitted from the light emitting structures OL-B1, OL-B2, and OL-B3 may each be blue light. However, the embodiment is not limited thereto, and the light emitted from the light emitting structures OL-B1, OL-B2, and OL-B3 may each have a different wavelength range. For example, the light emitting elements ED-BT including the light emitting structures OL-B1, OL-B2, and OL-B3 that emit light having different wavelength ranges may each emit white light.

[0410] The charge generation layers CGL1 and CGL2 may each be disposed between two adjacent light emitting structures among 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.

[0411] refer to Figure 12 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. At least one of the light-emitting elements ED-1, ED-2, and ED-3 may include the polycyclic compound according to the embodiment. Therefore, the light-emitting element ED-BT may exhibit high efficiency and long life.

[0412] In contrast, Figure 4 The display device DD shown in FIG. Figure 12 The embodiment shown in FIG. 1 is different in that each of the first light-emitting element ED-1, the second light-emitting element ED-2, and the third light-emitting element ED-3 includes two emission layers stacked in the thickness direction. In each of the first light-emitting element ED-1, the second light-emitting element ED-2, and the third light-emitting element ED-3, the two emission layers can emit light in the same wavelength region.

[0413] 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 component OG may be arranged 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.

[0414] The emission auxiliary component OG may have a single-layer structure or a multi-layer structure. The emission auxiliary component OG may include a charge generation layer. For example, the emission auxiliary component OG may include an electron transport region, a charge generation layer, and a hole transport region that may be stacked in the following order. The emission auxiliary component OG may be provided as a common layer for the first light-emitting element ED-1, the second light-emitting element ED-2, and the third light-emitting element ED-3. However, the embodiment is not limited thereto, and the emission auxiliary component OG may be provided by being patterned within the opening OH defined in the pixel defining film PDL.

[0415] The first red emission layer EML-R1, the first green emission layer EML-G1, and the first blue emission layer EML-B1 may each be disposed between the emission auxiliary component OG and the electron transport region ETR. The second red emission layer EML-R2, the second green emission layer EML-G2, and the second blue emission layer EML-B2 may be disposed between the hole transport region HTR and the emission auxiliary component OG.

[0416] 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 component 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 component 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 component OG, a first blue emission layer EML-B1, an electron transport region ETR, and a second electrode EL2 stacked in the following order.

[0417] An optical auxiliary layer PL may be provided on the display device layer DP-ED. The optical auxiliary layer PL may include a polarizing layer. The optical auxiliary layer PL may be provided on the display panel DP and control the reflection of external light in the display panel DP. Although not shown in the drawings, the optical auxiliary layer PL may be omitted in the display device DD-b.

[0418] Included in Figure 12 At least one emission layer in the display device DD-b shown in FIG may include the polycyclic compound according to the embodiment described above. For example, at least one of the first blue emission layer EML-B1 and the second blue emission layer EML-B2 may include the polycyclic compound according to the embodiment.

[0419] and Figure 11 and Figure 12 compared to, Figure 13 A display device DD-c is shown, differing in that it includes at least 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. The first, second, third, and fourth light-emitting structures OL-B1, OL-B2, OL-B3, and OL-C1 may be stacked in the thickness direction between the first and second electrodes EL1 and EL2. Charge generation layers CGL1, CGL2, and CGL3 may be disposed between the first, second, third, and fourth light-emitting structures OL-B1, OL-B2, OL-B3, and OL-C1. Among the four light-emitting structures, the first, second, and 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 wavelength regions different from each other.

[0420] The charge generation layers CGL1 , CGL2 , and CGL3 disposed between adjacent light emitting structures OL-B1 , OL-B2 , OL-B3 , and OL-C1 may each independently include a p-type charge generation layer and / or an n-type charge generation layer.

[0421] In an embodiment, at least one of the light-emitting structures OL-B1, OL-B2, OL-B3, and OL-C1 included in the display device DD-c may include the polycyclic compound according to the embodiment described above. For example, in an embodiment, at least one of the first light-emitting structure OL-B1, the second light-emitting structure OL-B2, and the third light-emitting structure OL-B3 may each include the polycyclic compound according to the embodiment described above.

[0422] The light-emitting element ED represented by Formula 1 described above according to the embodiment includes the polycyclic compound according to the embodiment in at least one functional layer provided between the first electrode EL1 and the second electrode EL2, and thus can exhibit excellent luminous efficiency and improved lifespan. For example, the polycyclic compound according to the embodiment can be included in the emission layer EML of the light-emitting element ED, and the light-emitting element can exhibit a long lifespan.

[0423] In an embodiment, an electronic device may include a display device and a control unit for controlling the display device, wherein the display device includes a plurality of light-emitting elements. The electronic device may be a device activated by an electrical signal. The electronic device may include a display device according to various embodiments. Examples of electronic devices may include large, medium, and small electronic devices such as televisions, monitors, billboards, personal computers, laptop computers, personal digital assistants, display devices for vehicles, game consoles, portable electronic devices, smart watches, and cameras.

[0424] Figure 14 1 is a schematic diagram of the interior of a vehicle AM ​​in which a first display device DD-1, a second display device DD-2, a third display device DD-3, and a fourth display device DD-4 according to an embodiment are provided. At least one of the first display device DD-1, the second display device DD-2, the third display device DD-3, and the fourth display device DD-4 may have a display device according to the above reference. Figure 3 and Figure 4 as well as Figures 10 to 13 The structure of one of the display devices DD, DD-TD, DD-a, DD-b, and DD-c is described.

[0425] Figure 14 A vehicle AM ​​is shown, but this is merely an example. The first display device DD-1, second display device DD-2, third display device DD-3, and fourth display device DD-4 can be installed in various vehicles, such as bicycles, motorcycles, trains, ships, and airplanes. In embodiments, at least one of the first display device DD-1, second display device DD-2, third display device DD-3, and fourth display device DD-4, which may have a structure corresponding to one of the display devices DD, DD-TD, DD-a, DD-b, and DD-c, can be employed in a personal computer, laptop computer, personal digital assistant, game console, portable electronic device, television, monitor, or billboard. These are provided herein merely as examples, and the display devices may be included in other electronic devices.

[0426] At least one of the first display device DD-1, the second display device DD-2, the third display device DD-3 and the fourth display device DD-4 may each independently include a Figures 5 to 9 The light-emitting element ED according to the embodiment is described in any of the figures in FIG. The light-emitting element ED may include the polycyclic compound according to the embodiment. At least one of the first display device DD-1, the second display device DD-2, the third display device DD-3, and the fourth display device DD-4 includes the light-emitting element ED including the polycyclic compound according to the embodiment, and thus can have an extended display life.

[0427] refer to Figure 14The 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.

[0428] 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 cluster that displays first information about the vehicle AM. The first information may include a first scale indicating the vehicle AM's speed, a second scale indicating the engine speed (e.g., revolutions per minute (RPM)), an image representing a fuel gauge, and the like. The first scale and the second scale may each be represented as a digital image.

[0429] The second display device DD-2 can be arranged in a second area facing the driver's seat that overlaps with the front window GL. The driver's seat can be the seat where the steering wheel HA is arranged. For example, the second display device DD-2 can be a head-up display (HUD) that displays second information of the vehicle AM. The second display device DD-2 can be optically transparent. The second information can include a digital code indicating the driving speed and can also include information such as the current time. Although not shown in the drawings, the second information of the second display device DD-2 can be displayed by being projected onto the front window GL.

[0430] The third display device DD-3 may be disposed in a third area adjacent to the shift lever GR. For example, the third display device DD-3 may be disposed between the driver's seat and the passenger seat and may be a center information display (CID) for the vehicle for displaying tertiary information. The passenger seat may be spaced apart from the driver's seat, with the shift lever GR disposed between them. The tertiary information may include information regarding traffic conditions (e.g., navigation information), currently playing music or radio, displayed videos (or images), the temperature inside the vehicle AM, and the like.

[0431] 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 area adjacent to a side of the vehicle AM. For example, the fourth display device DD-4 may be a digital side mirror that displays fourth information. The fourth display device DD-4 may display an image of the exterior of the vehicle AM ​​captured by a camera module CM disposed outside the vehicle AM. The fourth information may include an image of the exterior of the vehicle AM.

[0432] The first to fourth information are merely examples, and the first display device DD-1, the second display device DD-2, the third display device DD-3, and the fourth display device DD-4 may further display information about the interior and exterior of the vehicle AM. The first to fourth information may include different information. However, embodiments are not limited thereto, and some of the first to fourth information may include the same information.

[0433] Hereinafter, the polycyclic compound and the light emitting element according to the embodiment will be described in detail with reference to examples and comparative examples. The embodiments shown below are provided only to facilitate understanding of the present disclosure, and the scope thereof is not limited thereto.

[0434] [Example]

[0435] 1. Synthesis of polycyclic compounds according to examples

[0436] The synthesis method of the polycyclic compound according to the embodiment will be described in detail by describing the synthesis methods for Compound 31, Compound 33, Compound 35, Compound 40, Compound 46, Compound 56, and Compound 91. In the following description, the synthesis method of the polycyclic compound is provided as an example, but the synthesis method of the compound according to the embodiment is not limited to the example.

[0437] (1) Synthesis of compound 31

[0438] Compound 31 can be synthesized, for example, according to Reaction Scheme 1.

[0439] [Reaction Scheme 1]

[0440]

[0441] 1) Synthesis of Intermediate 31-a

[0442] 15g 3,5-dibromo-1,1'-biphenyl, 24g N-(3-(9H-carbazol-9-yl)phenyl)-[1,1'-biphenyl]-4-amine, 1.3g bis(dibenzylideneacetone)palladium(0) (Pd(dba)2), 2.7g xanthene (Xantphos), 6.0g sodium tert-butoxide (tBuONa) and 240mL toluene were added to a 500mL two-necked flask and heated and stirred at 120°C for 3 hours. The obtained reaction solution was filtered through diatomaceous earth, concentrated, and purified by column chromatography (eluent: dichloromethane / hexane=1 / 4) to obtain 26g of a white solid (yield 83%). By carrying out fast atom bombardment mass spectrometry (FAB-MS) measurement on the obtained product, m / z=642 was observed, and the white solid was therefore identified as intermediate 31-a.

[0443] 2) Synthesis of Intermediate 31-b

[0444] In a 500 mL two-necked flask, 25 g of intermediate 31-a, 21 g of N-(3-(9H-carbazol-9-yl)phenyl)-5-chloro-[1,1'-biphenyl]-2-amine, 1.1 g of bis(dibenzylideneacetone)palladium(0), 1.1 g of HP(tBu)3BF4, 4.9 g of sodium tert-butoxide, and 200 mL of toluene were added, and the mixture was heated at 120° C. and stirred for 3 hours. The obtained reaction solution was filtered through celite, concentrated, and purified by column chromatography (eluent: dichloromethane / hexane=3 / 1) to obtain 24 g of a white solid (yield 62%). By performing FAB-MS measurement on the obtained product, m / z=1006 was observed, and thus the white solid was identified as intermediate 31-b.

[0445] 3) Synthesis of Intermediate 31-c

[0446] 24g of intermediate 31-b was added to a 1L three-necked flask, 240mL of o-dichlorobenzene (ODCB) was added under an argon (Ar) atmosphere, 36mL of boron tribromide was slowly added, and the mixture was stirred at 180°C overnight. While an ice bath was carried out in the obtained reaction solution, 200mL of N,N-diisopropylethylamine was added, and water was added to extract the organic layer with toluene. The organic layer was concentrated and purified by column chromatography (eluent: dichloromethane / hexane=3 / 1) to obtain 0.73g of a yellow solid (yield 3%). By carrying out FAB-MS measurement on the obtained yellow solid, m / z=1013 was observed, and the yellow solid was therefore identified as intermediate 31-c.

[0447] 4) Synthesis of Compound 31

[0448] 0.72 g of intermediate 31-c, 0.52 g of K4[Fe(CN)6], 0.025 g of bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (PdCl2(amphos)2), 0.30 g of sodium carbonate and 7 mL of dimethylacetamide (DMA) were added to a 20 mL two-necked flask, and the mixture was heated and stirred at 140° C. for 5 hours. The obtained reaction solution was filtered through celite, concentrated, and purified by column chromatography (eluent: dichloromethane / hexane=1 / 1) to obtain 0.52 g of a yellow solid (yield 73%). By performing FAB-MS measurement on the obtained product, m / z=1004 was observed, and thus the yellow solid was identified as compound 31.

[0449] (2) Synthesis of compound 33

[0450] Compound 33 can be synthesized, for example, according to Reaction Scheme 2.

[0451] [Reaction Scheme 2]

[0452]

[0453] 1) Synthesis of Intermediate 33-a

[0454] In a 500mL two-necked flask, 15g of 3,5-dibromo-1,1'-biphenyl, 19g of di([1,1'-biphenyl]-4-yl)amine, 1.3g of bis(dibenzylideneacetone)palladium(0), 2.7g of Xantphos, 6.0g of sodium tert-butoxide and 240mL of toluene were added, and the mixture was heated and stirred at 120°C for 3 hours. The reaction solution obtained was filtered through diatomaceous earth, concentrated, and purified by column chromatography (eluent: dichloromethane / hexane=1 / 4) to obtain 21g of a white solid (yield 79%). By carrying out FAB-MS measurement on the product obtained, m / z=553 was observed, and therefore the white solid was identified as intermediate 33-a.

[0455] 2) Synthesis of Intermediate 33-b

[0456] In a 500 mL two-necked flask, 21 g of intermediate 33-a, 16 g of N-([1,1'-biphenyl]-4-yl)-5-chloro-[1,1'-biphenyl]-2-amine, 1.0 g of bis(dibenzylideneacetone)palladium(0), 41.1 g of HP(tBu)3BF, 4.7 g of sodium tert-butoxide, and 200 mL of toluene were added, and the mixture was heated and stirred at 120° C. for 3 hours. The obtained reaction solution was filtered through celite, concentrated, and purified by column chromatography (eluent: dichloromethane / hexane=3 / 1) to obtain 24 g of a white solid (yield 76%). By performing FAB-MS measurement on the obtained product, m / z=827 was observed, and thus the white solid was identified as intermediate 33-b.

[0457] 3) Synthesis of Intermediate 33-c

[0458] 24g of intermediate 33-b was added to a 1L three-necked flask, 240mL of o-dichlorobenzene was added under an argon (Ar) atmosphere, 44mL of boron tribromide was slowly added, and the mixture was stirred at 180°C overnight. While carrying out an ice bath in the reaction solution obtained, 240mL of N,N-diisopropylethylamine was added, and water was added to extract the organic layer with toluene. The organic layer obtained was concentrated and purified by column chromatography (eluent: dichloromethane / hexane=3 / 1) to obtain 1.9g of a yellow solid (yield 8%). By carrying out FAB-MS measurement on the yellow solid obtained, m / z=835 was observed, and the yellow solid was therefore identified as intermediate 33-c.

[0459] 4) Synthesis of Compound 33

[0460] 1.9 g of intermediate 33-c, 1.7 g of K4[Fe(CN)6], 0.082 g of bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)palladium(II) dichloride, 0.98 g of sodium carbonate (Na2CO3) and 20 mL of dimethylacetamide were added to a 50 mL two-necked flask, and the mixture was heated and stirred at 140°C for 5 hours. The obtained reaction solution was filtered through celite, concentrated, and purified by column chromatography (eluent: dichloromethane / hexane=1 / 1) to obtain 1.3 g of a yellow solid (yield 67%). By performing FAB-MS measurement on the obtained product, m / z=826 was observed, and thus the yellow solid was identified as compound 33.

[0461] (3) Synthesis of compound 35

[0462] Compound 35 can be synthesized, for example, according to Reaction Scheme 3.

[0463] [Reaction Scheme 3]

[0464]

[0465] 1) Synthesis of Intermediate 35-a

[0466] In a 300 mL two-necked flask, 10 g of 3,5-dibromo-1,1'-biphenyl, 23 g of N-([1,1'-biphenyl]-4-yl)-5-chloro-[1,1'-biphenyl]-2-amine, 1.5 g of bis(dibenzylideneacetone)palladium(0), 1.5 g of HP(tBu)3BF4, 8.0 g of sodium tert-butoxide and 160 mL of toluene were added, and the mixture was heated and stirred at 120 ° C for 3 hours. The reaction solution obtained was filtered through diatomaceous earth, concentrated, and purified by column chromatography (eluent: dichloromethane / hexane=3 / 1) to obtain 25 g of a white solid (yield 89%). By performing FAB-MS measurement on the obtained product, m / z=862 was observed, and the white solid was thus identified as intermediate 35-a.

[0467] 2) Synthesis of Intermediate 35-b

[0468] 24g of intermediate 35-a was added to a 1L three-necked flask, 280mL of o-dichlorobenzene was added under an argon (Ar) atmosphere, 42mL of boron tribromide was slowly added, and the mixture was stirred at 180°C overnight. While performing an ice bath in the obtained reaction solution, 232mL of N,N-diisopropylethylamine was added, and water was added to extract the organic layer with toluene. The organic layer obtained was concentrated and purified by column chromatography (eluent: dichloromethane / hexane=3 / 1) to obtain 1.5g of a yellow solid (yield 6%). By performing FAB-MS measurement on the obtained yellow solid, m / z=870 was observed, and the yellow solid was therefore identified as intermediate 35-b.

[0469] 3) Synthesis of compound 35

[0470] 1.5 g of intermediate 33-b, 2.5 g of K4[Fe(CN)6], 0.12 g of bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II), 2.8 g of sodium carbonate and 20 mL of dimethylacetamide were added to a 50 mL two-necked flask, and the mixture was heated and stirred at 140° C. for 5 hours. The obtained reaction solution was filtered through celite, concentrated, and purified by column chromatography (eluent: dichloromethane / hexane=1 / 1) to obtain 0.84 g of a yellow solid (yield 59%). By performing FAB-MS measurement on the obtained product, m / z=851 was observed, and thus the yellow solid was identified as compound 35.

[0471] (4) Synthesis of Compound 40

[0472] Compound 40 can be synthesized, for example, according to Reaction Scheme 4.

[0473] [Reaction Scheme 4]

[0474]

[0475] 1) Synthesis of Intermediate 40-a

[0476] In a 500 mL two-necked flask were added 10 g of 1,3-dibromo-5-tert-butylbenzene, 19 g of 5'-chloro-[1,1':3',1"-terphenyl]-2'-amine, 1.6 g of bis(dibenzylideneacetone)palladium(0), 1.6 g of HP(tBu)3BF4, 8.6 g of sodium tert-butoxide and 170 mL of toluene, and the mixture was heated at 120° C. and stirred for 3 hours. The obtained reaction solution was filtered through celite, concentrated, and purified by column chromatography (eluent: dichloromethane / hexane=1 / 4) to obtain 21 g of a white solid (yield 91%). By performing FAB-MS measurement on the obtained product, m / z=690 was observed, and thus the white solid was identified as intermediate 40-a.

[0477] 2) Synthesis of Intermediate 40-b

[0478] 20g intermediate 40-a, 20g 4-bromo-1,1'-biphenyl, 2.0g bis(dibenzylideneacetone)palladium(0), 4.0g Xantphos, 17g sodium tert-butoxide and 30mL dimethylbenzene were added to a 500mL two-necked flask, and the mixture was heated and stirred at 140°C for 96 hours. The reaction solution obtained was filtered through diatomaceous earth, concentrated, and purified by column chromatography (eluent: dichloromethane / hexane=3 / 1) to obtain 19g of a white solid (yield 65%). By carrying out FAB-MS measurement on the obtained product, m / z=994 was observed, and the white solid was therefore identified as intermediate 40-b.

[0479] 3) Synthesis of Intermediate 40-c

[0480] 19g intermediate 40-b is added to a 1L three-necked flask, 190mL o-dichlorobenzene (ODCB) is added under an argon (Ar) atmosphere, 29mL boron tribromide (BBr3) is slowly added, and the mixture is stirred at 180°C overnight. While carrying out an ice bath in the reaction solution obtained, 160mL N,N-diisopropylethylamine is added, and water is added to extract the organic layer with toluene. The organic layer obtained is concentrated and purified by column chromatography (eluent: dichloromethane / hexane=3 / 1) to obtain 0.57g yellow solid (yield 3%). By carrying out FAB-MS measurement on the yellow solid obtained, m / z=1002 is observed, and therefore the yellow solid is identified as intermediate 40-c.

[0481] 4) Synthesis of Compound 40

[0482] 0.57 g of intermediate 40-c, 0.84 g of K4[Fe(CN)6], 0.040 g of bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II), 0.97 g of sodium carbonate and 6 mL of dimethylacetamide were added to a 20 mL two-necked flask, and the mixture was heated and stirred at 140° C. for 5 hours. The obtained reaction solution was filtered through celite, concentrated, and purified by column chromatography (eluent: dichloromethane / hexane=1 / 1) to obtain 0.33 g of a yellow solid (yield 59%). By performing FAB-MS measurement on the obtained product, m / z=983 was observed, and thus the yellow solid was identified as compound 40.

[0483] (5) Synthesis of Compound 46

[0484] Compound 46 can be synthesized, for example, according to Reaction Scheme 5.

[0485] [Reaction Scheme 5]

[0486]

[0487] 1) Synthesis of Intermediate 46-a

[0488] In a 500 mL two-necked flask, 15 g of 3,5-dibromo-1,1'-biphenyl and 37 g of N 1 ,N 1 -bis([1,1'-biphenyl]-3-yl)-N 3 -([1,1':3',1"-terphenyl]-5'-yl)benzene-1,3-diamine, 1.3 g of bis(dibenzylideneacetone)palladium(0), 2.7 g of Xantphos, 6.0 g of sodium tert-butoxide and 240 mL of toluene were added, and heated at 120°C and stirred for 3 hours. The obtained reaction solution was filtered through celite, concentrated, and purified by column chromatography (eluent: dichloromethane / hexane=1 / 4) to obtain 35 g of a white solid (yield 83%). By performing FAB-MS measurement on the obtained product, m / z=872 was observed, and thus the white solid was identified as intermediate 46-a.

[0489] 2) Synthesis of Intermediate 46-b

[0490] 25 g of intermediate 46-a, 12 g of N-([1,1'-biphenyl]-4-yl)-5-chloro-[1,1'-biphenyl]-2-amine, 0.79 g of bis(dibenzylideneacetone)palladium(0), 0.80 g of HP(tBu)3BF4, 3.6 g of sodium tert-butoxide and 150 mL of toluene were added to a 500 mL two-necked flask, and the mixture was heated and stirred at 120 ° C for 3 hours. The obtained reaction solution was filtered through celite, concentrated, and purified by column chromatography (eluent: dichloromethane / hexane=3 / 1) to obtain 20 g of a white solid (yield 62%). By performing FAB-MS measurement on the obtained product, m / z=1147 was observed, and thus the white solid was identified as intermediate 46-b.

[0491] 3) Synthesis of Intermediate 46-c

[0492] 20g of intermediate 46-B was added to a 1L three-necked flask, 170mL of o-dichlorobenzene was added under an argon (Ar) atmosphere, 26mL of boron tribromide was slowly added, and the mixture was stirred at 180°C overnight. While carrying out an ice bath in the obtained reaction solution, 150mL of N,N-diisopropylethylamine was added, and water was added to extract the organic layer with toluene. The organic layer obtained was concentrated and purified by column chromatography (eluent: dichloromethane / hexane=3 / 1) to obtain 1.6g of a yellow solid (yield 8%). By carrying out FAB-MS measurement on the obtained yellow solid, m / z=1155 was observed, and the yellow solid was therefore identified as intermediate 46-c.

[0493] 4) Synthesis of Compound 46

[0494] 0.72 g of intermediate 46-c, 1.7 g of K4[Fe(CN)6], 0.46 g of K4[Fe(CN)6], 0.025 g of bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)palladium(II) dichloride, 0.26 g of sodium carbonate and 7 mL of dimethylacetamide were added to a 50 mL two-necked flask, and the mixture was heated and stirred at 140° C. for 5 hours. The obtained reaction solution was filtered through celite, concentrated, and purified by column chromatography (eluent: dichloromethane / hexane=1 / 1) to obtain 0.45 g of a yellow solid (yield 63%). By performing FAB-MS measurement on the obtained product, m / z=1145 was observed, and thus the yellow solid was identified as compound 46.

[0495] (6) Synthesis of Compound 56

[0496] Compound 56 can be synthesized, for example, according to Reaction Scheme 6.

[0497] [Reaction Scheme 6]

[0498]

[0499] 1) Synthesis of Intermediate 56-a

[0500] In a 500 mL two-necked flask, 15 g of intermediate 40-a, 21 g of 9-(3-bromophenyl)-9H-carbazole, 1.5 g of bis(dibenzylideneacetone)palladium(0), 3.0 g of Xantphos, 13 g of sodium tert-butoxide, and 20 mL of xylene were added, and the mixture was heated and stirred at 120° C. for 3 hours. The obtained reaction solution was filtered through celite, concentrated, and purified by column chromatography (eluent: dichloromethane / hexane=3 / 1) to obtain 14 g of a white solid (yield 54%). By performing FAB-MS measurement on the obtained product, m / z=1172 was observed, and thus the white solid was identified as intermediate 56-a.

[0501] 2) Synthesis of Intermediate 56-b

[0502] 14g of intermediate 56-A was added to a 1L three-necked flask, 120mL of o-dichlorobenzene was added under an argon (Ar) atmosphere, 18mL of boron tribromide was slowly added, and the mixture was stirred at 180°C overnight. While an ice bath was carried out in the reaction solution obtained, 100mL of N,N-diisopropylethylamine was added, and water was added to extract the organic layer with toluene. The organic layer obtained was concentrated and purified by column chromatography (eluent: dichloromethane / hexane=3 / 1) to obtain 0.42g of a yellow solid (yield 3%). By carrying out FAB-MS measurement on the yellow solid obtained, m / z=1180 was observed, and the yellow solid was therefore identified as intermediate 56-b.

[0503] 3) Synthesis of Compound 56

[0504] To a 20 mL two-necked flask was added 0.42 g of intermediate 56-b, 0.52 g of K4[Fe(CN)6], 0.025 g of bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II), 0.60 g of sodium carbonate and 4 mL of dimethylacetamide, and the mixture was heated and stirred at 140° C. for 5 hours. The obtained reaction solution was filtered through celite, concentrated, and purified by column chromatography (eluent: dichloromethane / hexane=1 / 1) to obtain 0.30 g of a yellow solid (yield 72%). By performing FAB-MS measurement on the obtained product, m / z=1161 was observed, and thus the yellow solid was identified as compound 56.

[0505] (7) Synthesis of Compound 91

[0506] Compound 91 can be synthesized, for example, according to the following Reaction Scheme 7.

[0507] [Reaction Scheme 7]

[0508]

[0509] 1) Synthesis of Intermediate 91-a

[0510] In a 500 mL two-necked flask were added 40 g of 1,3-dibromo-5-tert-butylbenzene, 130 g of N-phenyl-[1,1':3',1"-terphenyl]-2'-amine, 9.5 g of bis(dibenzylideneacetone)palladium(0), 19 g of Xantphos, 79 g of sodium tert-butoxide and 140 mL of xylene, and the mixture was heated at 140° C. and stirred for 96 hours. The obtained reaction solution was filtered through celite, concentrated, and purified by column chromatography (eluent: dichloromethane / hexane=3 / 1) to obtain 47 g of a white solid (yield 65%). By performing FAB-MS measurement on the obtained product, m / z=533 was observed, and thus the white solid was identified as intermediate 91-a.

[0511] 2) Synthesis of Intermediate 91-b

[0512] In a 100 mL two-necked flask, 47 g of intermediate 91-a, 200 g of 3-bromophenol, 73 g of potassium carbonate (K CO ) and 34 g of CuI (I) were added, and the mixture was heated and stirred at 190° C. for 96 hours. The obtained reaction solution was filtered through celite, concentrated, and purified by column chromatography (eluent: dichloromethane / hexane=3 / 1) to obtain 9.4 g of a white solid (yield 17%). By performing FAB-MS measurement on the obtained product, m / z=625 was observed, and thus the white solid was identified as intermediate 91-b.

[0513] 3) Synthesis of Intermediate 91-c

[0514] In a 200 mL two-necked flask, 15 g of intermediate 40-a, 15 g of iodobenzene, 1.5 g of bis(dibenzylideneacetone)palladium(0), 3.0 g of Xantphos, 5.4 g of sodium tert-butoxide and 22 mL of dimethylbenzene were added, and the mixture was heated and stirred at 140° C. for 96 hours. The reaction solution obtained was filtered through diatomaceous earth, concentrated, and purified by column chromatography (eluent: dichloromethane / hexane=3 / 1) to obtain 7.0 g of a white solid (yield 42%). By carrying out FAB-MS measurement on the product obtained, m / z=766 was observed, and the white solid was therefore identified as intermediate 91-c.

[0515] 4) Synthesis of Intermediate 91-d

[0516] In a 200 mL two-necked flask, 9.4 g of intermediate 91-b, 7.0 g of intermediate 91-c, 0.32 g of bis(dibenzylideneacetone)palladium(0), 0.64 g of Xantphos, 5.3 g of sodium tert-butoxide, and 10 mL of xylene were added, and the mixture was heated and stirred at 140° C. for 96 hours. The obtained reaction solution was filtered through celite, concentrated, and purified by column chromatography (eluent: dichloromethane / hexane=3 / 1) to obtain 7.3 g of a white solid (yield 61%). By performing FAB-MS measurement on the obtained product, m / z=1310 was observed, and thus the white solid was identified as intermediate 91-d.

[0517] 5) Synthesis of Intermediate 91-e

[0518] 7.3g of intermediate 91-d was added to a 500mL three-necked flask, 60mL of o-dichlorobenzene was added under an argon (Ar) atmosphere, 17mL of boron tribromide was slowly added, and the mixture was stirred at 180°C overnight. While performing an ice bath in the reaction solution obtained, 90mL of N,N-diisopropylethylamine was added, and water was added to extract the organic layer with toluene. The organic layer obtained was concentrated and purified by column chromatography (eluent: dichloromethane / hexane=3 / 1) to obtain 0.15g of a yellow solid (yield 2%). By performing FAB-MS measurement on the yellow solid obtained, m / z=1325 was observed, and the yellow solid was therefore identified as intermediate 91-e.

[0519] 6) Synthesis of Compound 91

[0520] In a 20 mL two-necked flask, 0.12 g of intermediate 91-e, 0.17 g of K4[Fe(CN)6], 0.0080 g of bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II), 0.19 g of sodium carbonate and 1 mL of dimethylacetamide were added, and the mixture was heated and stirred at 140° C. for 5 hours. The obtained reaction solution was filtered through celite, concentrated, and purified by column chromatography (eluent: dichloromethane / hexane=1 / 1) to obtain 0.12 g (yield 78%) of a yellow solid. By performing FAB-MS measurement on the obtained product, m / z=1306 was observed, and thus the yellow solid was identified as compound 91.

[0521] 2. Evaluation of the Fluorescence Properties of Compounds

[0522] The fluorescent light emission characteristics of the polycyclic compounds according to the examples and the comparative example compounds were evaluated, and the results are shown in Table 1. The maximum photoluminescence wavelength (PLλ) of the emission spectrum was evaluated. max ), photoluminescence quantum yield (PLQY) and full width at half maximum (FWHM), and the results are listed in Table 1.

[0523] The maximum photoluminescence wavelength of the illustrative compounds and comparative example compounds was measured under an inert gas atmosphere using an F-7000 spectrofluorometer manufactured by Hitachi High-Tech Corporation. The photoluminescence quantum yield was measured using a Quantaurus QY manufactured by Hamamatsu Photonics KK. The full width at half maximum (FWHM) of the emission spectrum was measured using a U-3900 spectrofluorometer manufactured by Hitachi High-Tech Corporation. The luminescence characteristics of the compounds listed in Table 1 were evaluated using toluene solutions of the illustrative compounds and comparative example compounds.

[0524] <Example Compounds>

[0525]

[0526] <Comparative Example Compounds>

[0527]

[0528] [Table 1]

[0529] Compound <![CDATA[PLλ max / nm]]> PLQY / % FWHM / nm Example Compound 31 463 87 23 Example Compound 33 466 72 19 Example Compound 35 462 69 20 Example Compound 40 459 84 20 Example Compound 46 464 91 25 Example Compound 56 456 89 21 Example Compound 91 457 93 16 Comparative Example Compound X1 464 48 26 Comparative Example Compound X2 465 56 25 Comparative Example Compound X3 442 65 30 Comparative Example Compound X4 512 82 28 Comparative Example Compound X5 495 76 30

[0530] Referring to Table 1, it was confirmed that the example compound was suitable as a material for a blue light-emitting material because it emitted light in a wavelength region within a range of about 460 nm to about 470 nm, had a measured value of a photoluminescence quantum yield of 65% or more, and exhibited a narrow full width at half maximum of about 25 nm or less of an emission wavelength spectrum.

[0531] Compared to the example compounds, Comparative Example Compounds X1 and X2 exhibited lower photoluminescence quantum yields than the example compounds. Comparative Example Compounds X3 and X5 exhibited expanded full widths at half maximum compared to the example compounds. Comparative Example Compound X4 was confirmed to emit light having a photoluminescence wavelength corresponding to green light.

[0532] 3. Fabrication and evaluation of light-emitting elements

[0533] A light-emitting element including the polycyclic compound according to the embodiment or the comparative example compound in the emission layer was manufactured by the following method. Compound 31, Compound 33, Compound 35, Compound 40, Compound 46, Compound 56, and Compound 91, which are polycyclic compounds according to the embodiment, were used as dopant materials for the emission layer to manufacture the light-emitting elements according to Examples 1 to 7. Comparative Example Compounds X1 to X5 were used as dopant materials in the emission layer to manufacture the light-emitting elements according to Comparative Examples 1 to 5, respectively.

[0534] (1) Manufacturing of light-emitting elements

[0535] A glass substrate with an ITO patterned thereon as a first electrode was ultrasonically cleaned with isopropyl alcohol and pure water for approximately 5 minutes each. After ultrasonic cleaning, the glass substrate was irradiated with ultraviolet light for approximately 30 minutes and then treated with ozone. HAT-CN with a thickness of approximately 10 nm, Tris-PCz with a thickness of approximately 30 nm, and mCBP with a thickness of approximately 5 nm were deposited to form a hole transport region.

[0536] mCBP was co-deposited with the exemplary compound or comparative compound to form an emission layer having a thickness of approximately 30 nm. The exemplary compound and comparative compound were co-deposited at a weight ratio of 2:98. The exemplary compound or comparative compound was used as a dopant material in the manufacture of a light-emitting element.

[0537] SF3-TRZ with a thickness of about 10 nm, SF3-TRZ:Liq with a weight ratio of 50:50 with a thickness of about 20 nm, and Liq with a thickness of about 2 nm were deposited to form an electron transport region.

[0538] Al was deposited to a thickness of approximately 100 nm to form a second electrode.

[0539] In an embodiment, the hole transport region, the emission layer, the electron transport region, and the second electrode are formed using a vacuum deposition apparatus.

[0540] The compounds used for producing the light-emitting element are as follows.

[0541] (Materials used in the manufacture of light-emitting elements)

[0542]

[0543]

[0544] (2) Evaluation of characteristics of light-emitting elements

[0545] The characteristics of the light emitting elements according to Examples 1 to 7 and Comparative Examples 1 to 5 were evaluated, and the evaluation results are listed in Table 2. In Table 2, the maximum photoluminescence wavelength (λ max ), maximum external quantum yield (EQE max The time taken for the initial brightness to decrease from 100% to 50% was measured during continuous operation as the time taken for the initial brightness to decrease from 100% to 50% at 1000 cd / m 2 The lifetime (LT50) under ΔT was calculated, and the relative element lifetime of each light-emitting element was calculated with respect to the value of the light-emitting element according to Comparative Example 1.

[0546] [Table 2]

[0547]

[0548] Referring to Table 2, it can be confirmed that the light-emitting element according to the example emits blue light having a maximum photoluminescence wavelength of less than or equal to about 470 nm. Compared with the light-emitting element according to the comparative example, the light-emitting element according to the example has a higher maximum external quantum yield (EQE max ) properties and relative component life properties showed excellent results.

[0549] As can be seen from the results listed in Table 2, the polycyclic compound used in the light-emitting element according to the example has excellent characteristics such as maximum external quantum yield and material stability compared to the comparative example compound because it has a structure in which a benzene ring is connected to a nitrogen atom constituting a core structure and a cyano group and an aryl group are additionally connected to the benzene ring. Therefore, the light-emitting element using the polycyclic compound according to the embodiment as an emission material exhibits excellent efficiency and long life.

[0550] In Comparative Example Compounds X1 and X2 used in Comparative Examples 1 and 2, a cyano group is attached to the phenyl group connected to the nitrogen atom constituting the core structure, but an aliphatic substituent is included, compared to the polycyclic compounds according to Examples. In Comparative Example Compound X1, a substituted piperidinyl group is attached to the first benzene ring, and in Comparative Example Compound X2, a substituted methyl group is attached to the first benzene ring. Even in the evaluation of the physical properties of the polycyclic compounds in Table 1, Comparative Example Compounds X1 and X2 exhibited lower photoluminescence quantum yields than the Example compounds, and Comparative Example Compound X1 exhibited a broadened full width at half maximum of the emission spectrum. Therefore, the light-emitting elements according to Comparative Examples 1 and 2 exhibited lower external quantum yields and shorter element lifetimes than the light-emitting elements according to Examples.

[0551] In the comparative example compound X3 used in comparative example 3, an aryl group is not additionally attached to the first benzene ring, and R in Formula 1 4 and R5 The core structure that is connected to each other and thus contributes to the emission characteristics is different from the core structure of the example compound. Comparative Example Compound X3 does not have an association inhibitory effect due to the structural characteristics in which the aryl group is not additionally connected to the first benzene ring and the high planarity caused by the core structure, and an expanded full width at half maximum is confirmed, and significantly low efficiency and life are observed when the device is driven.

[0552] Comparative Example Compound X4 used in Comparative Example 4 has a structure in which a cyano group is directly bonded to a core structure, and emits light having a wavelength in the green region, as shown in Table 1. These results are caused by the participation of the cyano group in the conjugation of the compound skeleton, and it can be seen that the photoluminescence quantum yield (PLQY) and the element efficiency of the maximum external quantum efficiency (EQE max ) showed a level similar to that of the exemplary compounds, but Comparative Example Compound X4 was not suitable for use as a blue light-emitting material. Comparative Example Compound X4 had a highly planar structure, and therefore, even if an aryl group was additionally attached to the benzene ring to which the cyano group was attached, the associated state might not be effectively suppressed, resulting in inferior results in terms of full width at half maximum and device life compared to the exemplary compounds.

[0553] Comparative Example Compound X5 used in Comparative Example 5 has a structure in which a cyano group is bonded to the core structure via a divalent biphenyl arylene group. It is assumed that Comparative Example Compound X5 has a reduced effect of the cyano group on the core structure due to the spatial distance caused by the divalent biphenyl group. Therefore, it can be seen that Comparative Example Compound X5 has a wavelength significantly different from the suitable blue light wavelength observed in the example compounds, and no significant effect on the device life is achieved.

[0554] In the light-emitting element according to the embodiment, the emission layer may include the polycyclic compound according to the embodiment. The polycyclic compound according to the embodiment may include a five-membered fused ring including one heteroatom, one nitrogen (N) atom and one boron (B) atom as a ring-forming atom as a core structure, or may include a two-membered ring including two heteroatoms as ring-forming atoms as a core structure or a four-membered ring including four heteroatoms as ring-forming atoms, which is further fused to a seven-membered fused ring or a nine-membered fused ring of a five-membered fused ring. In the polycyclic compound according to the embodiment, the first benzene ring is connected to the nitrogen atom constituting the core structure, and at least one cyano group and at least one aryl group are connected to the first phenyl group, thereby protecting the five-membered, seven-membered or nine-membered fused ring core and being able to have a structure in which the molecular planarity is relaxed. In the polycyclic compound according to the embodiment, the solvation and association with the solvent or the host material can be suppressed by the cyano group and the aryl group connected to the core structure via the first benzene ring. Therefore, the light-emitting element including the polycyclic compound according to the embodiment in the emission layer can exhibit high efficiency and long life characteristics.

[0555] The light emitting element includes the polycyclic compound according to the embodiment in an emission layer and thus can exhibit characteristics of high efficiency and long life.

[0556] The polycyclic compound according to the embodiment may contribute to improvement of light efficiency and long life of a light emitting element.

[0557] The display element according to the embodiment can exhibit excellent display quality.

[0558] 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 connection with an embodiment may be used alone or in combination with features, characteristics, and / or elements described in connection with other embodiments, unless otherwise specifically stated. Accordingly, it will be understood by one of ordinary skill in the art 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, wherein The polycyclic compound is represented by Formula 1: Formula 1 In formula 1, X is O, S or N (R 12 ), R 1 to R 12 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted amino group, a substituted or unsubstituted oxy group, a substituted or unsubstituted sulfinyl group, a substituted or unsubstituted boron group, an 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 R 1 to R 4 Bond to adjacent groups to form bonds only on R 1 to R 4 Form a ring between, or R 5 to R 8 Bond to adjacent groups to form bonds only on R 5 to R 8 A ring is formed between R a to R e are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, an 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, R a to R e At least one of is a cyano group, R a to R e At least one of the remaining groups in is each independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms.

2. The polycyclic compound according to claim 1, wherein In the selection of R a to R e Of the two, one is a cyano group, and the other is a substituted or unsubstituted phenyl group, and R a to R e The remaining groups other than the cyano group or the substituted or unsubstituted phenyl group in are each independently a hydrogen atom, a deuterium atom, or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms.

3. The polycyclic compound according to claim 1, wherein X is N(R 12 ),and R 12 is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms.

4. The polycyclic compound according to claim 1, wherein The polycyclic compound is represented by one of Formula 2-1 to Formula 2-3: Formula 2-1 Formula 2-2 Formula 2-3 Among them, in formula 2-1 to formula 2-3, R a 、R b 、R d and R e One or two of them are independently substituted or unsubstituted phenyl, R a 、R b 、R d and R e The remaining groups in are each independently a hydrogen atom or a deuterium atom, and R 1 to R 11 are each the same as defined in Formula 1, and Among them, in formula 2-3, R f 、R g 、R h 、R i and R j Each is independently a hydrogen atom, a deuterium atom, a cyano group, an unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms.

5. The polycyclic compound according to claim 4, wherein The polycyclic compound represented by Formula 2-3 is represented by Formula 2-3-1: Formula 2-3-1 Among them, in formula 2-3-1, R a1 to R a5 and R f1 to R f5 are each independently a hydrogen atom, a deuterium atom, or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, R b 、R d and R e One of them is a substituted or unsubstituted phenyl group, R b 、R d and R e The remaining groups in are each independently a hydrogen atom or a deuterium atom, R g 、R i and R j are each independently a hydrogen atom, a deuterium atom, an unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, R h is a hydrogen atom, a deuterium atom or a cyano group, and R 1 to R 11 Each is the same as defined in Formula 1. The polycyclic compound according to claim 5, wherein The polycyclic compound is represented by one of Formula 3-1 to Formula 3-5: Formula 3-1 Formula 3-2 Formula 3-3 Formula 3-4 Formula 3-5 Among them, in formula 3-1 to formula 3-5, R 21 to R 36 are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted amino group, a substituted or unsubstituted oxy 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, and X, R a 、R b 、R c 、R d and R e are each the same as defined in Formula 1, and Among them, in formula 3-2 to formula 3-5, n1, n3 and n5 are each independently an integer from 0 to 4, n2 and n4 are each independently an integer from 0 to 3, Y 1 To Y 4 are each independently O, S or N(R 37 ), Y 5 and Y 6 Each independently is O, S, N(R 38 ) or B(R 39 ),and R 37 to R 39 Each is independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms.

7. The polycyclic compound according to claim 1, wherein The polycyclic compound is a compound selected from compound group 1: Compound Group 1 Among them, in compound group 1, D is a deuterium atom.

8. A light-emitting element, wherein: The light emitting element comprises: a first electrode; a second electrode facing the first electrode; and An emission layer is provided between the first electrode and the second electrode and includes a first compound which is the polycyclic compound according to any one of claims 1 to 7.

9. The light-emitting element according to claim 8, wherein The emissive layer further includes at least one of a second compound represented by Formula HT-1 and a third compound represented by Formula ET-1: Formula HT-1 Wherein, in formula HT-1, A1 to A8 are each independently N or C(R 51 ), 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 52 )(R 53 ) or Si(R 54 )(R 55 ), 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 51 to R 55 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 amino 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 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 ring carbon atoms, or bonds with an adjacent group to form a ring; Formula ET-1 Wherein, in formula ET-1, Z a to Z c At least one of them is N, Z a to Z c The remaining groups in are each independently C(R 56 ), R 56 is a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 ring carbon atoms, e1 to e3 are each independently an integer from 0 to 10, Ar2 to Ar4 are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 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.

10. An electronic device comprising a display device, wherein: The display device includes: a circuit layer disposed on the base layer; and The display element layer is provided on the circuit layer and includes a light emitting element, wherein: The light-emitting element is the light-emitting element according to any one of claims 8 to 9.

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