Fused polycyclic compounds and light-emitting devices comprising the same

Abstract

Provided is a fused polycyclic compound and a light-emitting device including the same, the light-emitting device including: a first electrode; a second electrode facing the first electrode; and a plurality of organic layers between the first electrode and the second electrode, wherein at least one organic layer selected from the plurality of organic layers includes a fused polycyclic compound represented by Formula 1, and the first electrode and the second electrode each independently include at least one selected from Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF, Mo, Ti, In, Sn, Zn, Yb, and W, a compound of two or more thereof, a mixture of two or more thereof, or an oxide thereof, or the first electrode and the second electrode each independently include a material having a multi-layer structure of LiF / Ca or LiF / Al. Formula 1

Description

[0001] Cross-references to related applications

[0002] This application claims priority and benefit to Korean Patent Application No. 10-2020-0150280, filed with the Korean Intellectual Property Office on November 11, 2020, the entire contents of which are incorporated herein by reference. Technical Field

[0003] Embodiments of this disclosure relate to light-emitting devices, for example, to light-emitting devices comprising fused polycyclic compounds used as light-emitting materials. Background Technology

[0004] Recently, the development of organic electroluminescent displays (OLEDs) as image display devices has been actively underway. Unlike liquid crystal displays (LCDs), OLEDs are so-called self-emissive display devices, in which holes and electrons injected from the first and second electrodes recombine in the emitting layer, thus enabling the emitting material, which comprises organic compounds, to emit light and achieve display.

[0005] When applying light-emitting devices to display devices, there is a need for light-emitting devices with low driving voltage, high luminous efficiency and long service life, and the development of light-emitting device materials that can stably obtain these characteristics is being studied extensively and continuously.

[0006] In recent years, in particular, in order to achieve high-efficiency light-emitting devices, technologies related to phosphorescence emission utilizing triplet energy or delayed fluorescence utilizing triplet-triplet annihilation (TTA) in which singlet excitons are generated through collisions of triplet excitons are developed. Summary of the Invention

[0007] The embodiments of this disclosure provide a light-emitting device with high efficiency.

[0008] Embodiments of this disclosure provide a light-emitting device comprising: a first electrode; a second electrode facing the first electrode; and a plurality of organic layers between the first electrode and the second electrode, wherein at least one organic layer selected from the plurality of organic layers comprises a fused polycyclic compound represented by Formula 1, and the first electrode and the second electrode each independently comprise at least one selected from Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, Li, Mo, Ti, In, Sn, Zn, Yb and W, two or more of these compounds, mixtures of two or more of these compounds, or oxides thereof, or the first electrode and the second electrode each independently comprise a material having a multilayer structure of LiF / Ca or LiF / Al.

[0009] Formula 1

[0010]

[0011] In Formula 1, X1 to X5 are each independently NR9, O, S or Se, R1 to R9 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted amino group, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, or bonded to an adjacent group to form a ring, a is an integer selected from 0 to 3, b and c are each independently an integer selected from 0 to 2, d is an integer selected from 0 to 3, and e, f, g and h are each independently an integer selected from 0 to 4.

[0012] In one embodiment, the multiple organic layers may include a hole transport region, an emitter layer, and an electron transport region, and the emitter layer may include a fused polycyclic compound.

[0013] In one implementation, the emitting layer can emit thermally activated delayed fluorescence.

[0014] In an embodiment, the emitting layer can emit light with a center wavelength of about 420 nm to about 470 nm.

[0015] In one embodiment, the emitter layer may include a host and a dopant, and the dopant may include a fused polycyclic compound.

[0016] In an embodiment, the lowest triplet excitation level (T1 level) of the fused polycyclic compound may be about 2.60 eV or higher.

[0017] In this implementation, each of R2 and R3 may be a hydrogen atom.

[0018] In this implementation, each of R6 and R7 may be a hydrogen atom.

[0019] In this implementation, each of R5 and R8 may be a hydrogen atom.

[0020] In an embodiment, at least one of R1 and R4 may be a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms.

[0021] In an embodiment, at least one of R1 and R4 may be a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.

[0022] In the implementation, the fused polycyclic ring represented by Equation 1 can be represented by Equation 1-1a or Equation 1-1b:

[0023] Formula 1-1a

[0024]

[0025] Formula 1-1b

[0026]

[0027] In Equations 1-1a and 1-1b, X1 to X5, R1 to R9, and a to h are the same as those defined in Equation 1.

[0028] In embodiments, the fused polycyclic compound represented by Formula 1 may be represented by any one selected from Formulas 1-2a to 1-2d:

[0029] Formula 1-2a

[0030]

[0031] Formula 1-2b

[0032]

[0033] Formula 1-2c

[0034]

[0035] Equation 1-2d

[0036]

[0037] In equations 1-2a to 1-2d,

[0038] X1, X3 to X5, R1 to R9, and a to h are the same as those defined in Equation 1. Attached Figure Description

[0039] The accompanying drawings are included to provide a further understanding of the subject matter of this disclosure and are incorporated into and constitute a part of this specification. The drawings illustrate embodiments of this disclosure and, together with the description, serve to explain the principles of this disclosure.

[0040] In the attached diagram:

[0041] Figure 1 A plan view of a display device according to an embodiment of the present disclosure;

[0042] Figure 2 A cross-sectional view of a display device according to an embodiment of the present disclosure;

[0043] Figure 3 , Figure 4 , Figure 5 and Figure 6 A schematic cross-sectional view of a light-emitting device according to an embodiment of the present disclosure; and

[0044] Figure 7 and Figure 8 Each of these is a cross-sectional view of a display device according to an embodiment of the present disclosure. Detailed Implementation

[0045] The subject matter of this disclosure can be modified in many alternative forms, and therefore exemplary embodiments will be illustrated and described in the accompanying drawings. However, it should be understood that this is not intended to limit this disclosure to the specific forms disclosed, but rather to cover all modifications, equivalents, and alternatives that fall within the spirit and scope of this disclosure.

[0046] When interpreting each drawing, the same reference numerals are used to refer to the same elements. In the drawings, the dimensions of each structure may be exaggerated for clarity of this disclosure. It should be understood that although the terms "first," "second," etc., may be used to describe various elements, these elements should not be limited by these terms. These terms are used only to distinguish one element from another. For example, without departing from the scope of this disclosure, a first element may be referred to as a second element, and similarly, a second element may be referred to as a first element. Singular terms may include plural forms unless the context clearly indicates otherwise.

[0047] The term "and / or" includes all combinations of one or more associated configurations that can be defined.

[0048] In this specification, it should be understood that "comprising" or "having" means specifying the presence of features, fixed quantities, steps, processes, elements, components or combinations thereof disclosed in the specification, but does not exclude the possibility of the presence or addition of one or more other features, fixed quantities, steps, processes, elements, components or combinations thereof.

[0049] In this specification, when a layer, film, region, or plate is referred to as being "above" or "upper" another layer, film, region, or plate, it can be directly on the layer, film, region, or plate, or an intermediate layer, film, region, or plate may also be present. Furthermore, when a layer, film, region, or plate is referred to as being "below" or "lower" another layer, film, region, or plate, it can be directly below the layer, film, region, or plate, or an intermediate layer, film, region, or plate may also be present. Moreover, it should be understood that when a layer, film, region, or plate is referred to as being "on" another layer, film, region, or plate, it can be not only on the layer, film, region, or plate, but also below the layer, film, region, or plate.

[0050] In this specification, the term "substituted or unsubstituted" may mean unsubstituted or substituted with at least one substituent selected from the group consisting of: deuterium, halogen, cyano, nitro, amino, silyl, oxy, thio, sulfinyl, sulfonyl, carbonyl, boron, phosphonyl oxide, phosphonyl sulfide, alkyl, alkenyl, alkynyl, alkoxy, cycloalkyl, aryl, and heterocyclic groups. Furthermore, each of the above substituents may be substituted or unsubstituted. For example, biphenyl can be interpreted as aryl or a phenyl group substituted with a phenyl group.

[0051] In the specification, the phrase "bonded to an adjacent group to form a ring" indicates bonding to an adjacent group to form a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocycle. Hydrocarbon rings include aliphatic and aromatic hydrocarbon rings. Heterocycles include aliphatic and aromatic heterocycles. The ring formed by bonding to an adjacent group can be monocyclic or polycyclic. Furthermore, rings formed by bonding to each other can connect to another ring to form a spirostructure.

[0052] In the specification, the term "adjacent group" can mean a substituent that is directly attached to an atom substituted by the corresponding substituent, another substituent that is substituted on an atom substituted by the corresponding substituent, or a substituent that is spatially 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. Additionally, the two methyl groups in 4,5-dimethylphenanthrene can be interpreted as "adjacent groups" to each other.

[0053] In the specification, examples of halogen atoms may include fluorine atoms, chlorine atoms, bromine atoms and / or iodine atoms.

[0054] In the specification, the alkyl group may be straight-chain, branched, or cyclic (e.g., straight-chain alkyl, branched alkyl, or cycloalkyl). 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 alkyl groups 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, cyclopentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 2-butylhexyl, cyclohexyl, 4-methylcyclohexyl, 4-tert-butylcyclohexyl, n-heptyl, 1-methylheptyl, 2,2-dimethylheptyl, 2-ethylheptyl, 2-butylheptyl, n-octyl, tert-octyl, 2-ethyloctyl, 2-butyloctyl, 2-hexyloctyl, 3,7-dimethyloctyl, cyclooctyl, n-nonyl, n-decyl, adamantyl, 2-ethyldecyl, 2-butyldecyl, 2- Hexyldecyl, 2-octyldecyl, undecyl, dodecyl, 2-ethyldodecyl, 2-butyldodecyl, 2-hexyldodecyl, 2-octyldodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, 2-ethylhexadecyl, 2-butylhexadecyl, 2-hexylhexadecyl, 2-octylhexadecyl, heptadecanyl, octadecyl, nonadecanyl, eicosyl, 2-ethyleicosyl, 2-butyleicosyl, 2-hexyleicosyl, 2-octyleicosyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecanyl, hexadecyl, octadecyl, nonadecanyl, triadecyl, etc., but this disclosure is not limited thereto.

[0055] As used herein, the term "hydrocyclotridecyl" means any functional group or substituent derived from an aliphatic hydrocarbon ring. Hydrocyclotridecyl can be a saturated hydrocarbon cyclotridecyl having 5 to 20 cyclic carbon atoms.

[0056] As used herein, the term "aryl" means any functional group or substituent derived from an aromatic hydrocarbon ring. Aryl groups can be monocyclic or polycyclic. The number of cyclic carbon atoms in an aryl group can be 6 to 30, 6 to 20, or 6 to 15. Examples of aryl groups include phenyl, naphthyl, fluorenyl, anthraceneyl, phenanthryl, biphenyl, terphenyl, tetraphenyl, pentaphenyl, hexaphenyl, benzo[a]phenanthryl, pyrene, benzo[a]fluoranyl, 1,2-benzo[a]phenanthryl, etc., but this disclosure is not limited thereto.

[0057] In this specification, the fluorene group may be substituted, and two substituents may bond together to form a spirostructure. Examples of fluorene group substitution are given below. However, this disclosure is not limited thereto.

[0058]

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

[0060] In the specification, the heterocyclic group may include at least one of B, O, N, P, Si, S, and Se as a heteroatom. If the heterocyclic group includes two or more heteroatoms, the two or more heteroatoms may be the same or different. The heterocyclic group may be a monocyclic or polycyclic heterocyclic group and has the concept of including a heteroaryl group. The number of cyclic carbon atoms in the heterocyclic group may be 2 to 30, 2 to 20, or 2 to 10.

[0061] In this specification, the aliphatic heterocyclic group may include one or more of B, O, N, P, Si, S, and Se as heteroatoms. The number of cyclic carbon atoms in the aliphatic heterocyclic group may be 2 to 30, 2 to 20, or 2 to 10. Examples of aliphatic heterocyclic groups may include ethylene oxide, thiohexacyclopropane, pyrrolyl, piperidinyl, tetrahydrofuranyl, tetrahydrothiophenyl, thiaalkyl, tetrahydropyranyl, 1,4-dioxane, etc., but this disclosure is not limited thereto.

[0062] In the specification, the heteroaryl group may include at least one of B, O, N, P, Si, S, and Se as a heteroatom. When the heteroaryl group contains two or more heteroatoms, the two or more heteroatoms may be the same or different from each other. The heteroaryl group may be a monocyclic heteroaryl or a polycyclic heteroaryl. The number of cyclic carbon atoms in the heteroaryl group may be 2 to 60, 2 to 30, 2 to 20, or 2 to 10. Examples of heteroaryl groups may include thiophene, furanyl, pyrrole, imidazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinel, pyridazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, isoquinolinyl, indolyl, carbazole, N-arylcarbazole, N-heteroyl Arylcarbazolyl, N-alkylcarbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothiophene, dibenzothiophene, thiophene-thiophene, benzofuranyl, phenanthrolinel, thiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, thiazolyl, phenthiazinyl, dibenzosilicyclopentadienyl, dibenzofuranyl, etc., but this disclosure is not limited thereto.

[0063] The above description of aryl groups in the specification applies to arylene groups, except that arylene groups are divalent groups. The above explanation of heteroaryl groups applies to heteroarylene groups, except that heteroarylene groups are divalent groups.

[0064] In this specification, the term "silyl" includes alkylsilyl and arylsilyl. Examples of silyl may include trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, etc. However, this disclosure is not limited thereto.

[0065] As used herein, the term "oxygen group" may mean an oxygen atom bonded to an alkyl or aryl group as defined above. Oxide groups may include alkoxy and aryloxy groups. Alkoxy groups may be straight-chain, branched, or cyclic (e.g., straight-chain alkoxy, branched alkoxy, or cycloalkoxy). There is no specific limitation on the number of carbon atoms in an alkoxy group, but it may be, for example, 1 to 20 or 1 to 10. Examples of oxygen groups may include, but are not limited to, methoxy, ethoxy, n-propoxy, isopropoxy, butoxy, pentoxy, hexoxy, octoxy, nonoxy, decoxy, benzyloxy, etc.

[0066] As used herein, the term "boron-based" may mean a boron atom bonded to an alkyl or aryl group as defined above. Boron-based groups include alkylboron-based and arylboron-based groups. Examples of boron-based groups may include dimethylboron-based, diethylboron-based, tert-butylmethylboron-based, diphenylboron-based, phenylboron-based, etc., but this disclosure is not limited thereto.

[0067] In the specification, the alkenyl group can be straight-chain or branched (e.g., straight-chain alkenyl or branched alkenyl). There is no specific limitation on the number of carbon atoms in the alkenyl group, but it can be 2 to 30, 2 to 20, or 2 to 10. Examples of alkenyl groups include vinyl, 1-butenyl, 1-pentenyl, 1,3-butadienyl, styryl, styrylvinyl, etc., but this disclosure is not limited thereto.

[0068] In this specification, there is no specific limitation on the number of carbon atoms in the amino group, but it can be from 1 to 30. The amino group can include alkylamino and arylamino. Examples of amino groups include methylamino, dimethylamino, phenylamino, diphenylamino, naphthylamino, 9-methyl-anthraylamino, etc., but this disclosure is not limited thereto.

[0069] In the specification, the alkyl groups in alkylthio, alkylsulfonyl, alkylaryl, alkylboronyl, alkylsilyl, and alkylamine are the same as the examples of the alkyl groups mentioned above.

[0070] In the specification, the aryl groups in aryloxy, arylthio, arylsulfonyl, arylboryl, arylsilyl, and arylamino are the same as the examples of the aryl groups mentioned above.

[0071] The direct link in this article can mean a single bond (e.g., a single covalent bond).

[0072] As used in this article, "--*" indicates the position to be connected.

[0073] Embodiments of this disclosure will now be described with reference to the accompanying drawings.

[0074] Figure 1 A plan view of the display device DD for illustrating the implementation method. Figure 2 This is a cross-sectional view of the display device DD according to the embodiment. Figure 2 To explain along Figure 1 A cross-sectional view of a portion of the line I-I'.

[0075] The display device DD may include a display panel DP and an optical layer PP on the display panel DP. The display panel DP includes a plurality of light-emitting devices ED-1, ED-2, and ED-3, and thus the display device DD may include a plurality of light-emitting devices ED-1, ED-2, and ED-3. The optical layer PP may be on the display panel DP and control the light reflected from the display panel DP by external light. The optical layer PP may include, for example, a polarizing layer and / or a color filter layer. Unlike the views illustrated in the accompanying drawings, the optical layer PP may be omitted from the display device DD of the embodiment.

[0076] The substrate BL may be on the optical layer PP. The substrate BL may be a component providing a substrate surface, with the optical layer PP located on the substrate surface. The substrate BL may be a glass substrate, a metal substrate, a plastic substrate, etc. However, this disclosure is not limited thereto, and the substrate BL may be an inorganic layer, an organic layer, or a composite material layer including inorganic and organic materials. In addition, unlike what is shown in the figures, the substrate BL may be omitted in the embodiment.

[0077] The display device DD according to an embodiment may further include a filler layer. The filler layer may be located between the display device layer DP-ED and the substrate BL. The filler layer may be an organic material layer. The filler layer may include at least one selected from acrylic resins, silicone resins, and epoxy resins.

[0078] The display panel DP may include a substrate layer BS, a circuit layer DP-CL provided on the substrate layer BS, and a display device layer DP-ED. The display device layer DP-ED may include a pixel defining film PDL, light-emitting devices ED-1, ED-2, and ED-3 between portions of the pixel defining film PDL, and an encapsulation layer TFE on the light-emitting devices ED-1, ED-2, and ED-3.

[0079] The substrate layer BS can be a component providing a substrate surface, and the display device layer DP-ED is located on the substrate surface. The substrate layer BS can be a glass substrate, a metal substrate, a plastic substrate, etc. However, this disclosure is not limited to this, and the substrate layer BS can be an inorganic layer, an organic layer, or a composite material layer including inorganic and organic materials.

[0080] In this embodiment, the circuit layer DP-CL is on the substrate layer BS, and the circuit layer DP-CL may include multiple transistors. Each transistor may include a control electrode, an input electrode, and an output electrode. For example, the circuit layer DP-CL may include a switching transistor and a driving transistor to drive the light-emitting devices ED-1, ED-2, and ED-3 of the display device layer DP-ED.

[0081] Each of the light-emitting devices ED-1, ED-2, and ED-3 may have according to Figures 3 to 6 The structure of the light-emitting device ED according to the embodiments will be further described below. Each of the light-emitting devices ED-1, ED-2 and ED-3 may include a first electrode EL1, a hole transport region HTR, a corresponding one of the emitter layers EML-R, EML-G and EML-B, an electron transport region ETR and a second electrode EL2.

[0082] Figure 2 The embodiments of the emitting layers EML-R, EML-G, and EML-B of the light-emitting devices ED-1, ED-2, and ED-3, respectively, are described, each located within an opening OH defined by a pixel-defining film PDL. Furthermore, the hole transport region HTR, the electron transport region ETR, and the second electrode EL2 are provided as common layers throughout the light-emitting devices ED-1, ED-2, and ED-3. However, this disclosure is not limited thereto, and... Figure 2 Unlike the features described in the original text, the hole transport region (HTR) and electron transport region (ETR) in the embodiments can be provided by patterning inside the opening OH defined by the pixel defining film (PDL). For example, the hole transport region (HTR), one of the emitting layers (EML-R, EML-G, and EML-B), and the electron transport region (ETR) of the light-emitting devices ED-1, ED-2, and ED-3 in the embodiments can be provided by patterning using an inkjet printing method.

[0083] The encapsulation layer TFE can cover the light-emitting devices ED-1, ED-2, and ED-3. The encapsulation layer TFE can be a thin-film encapsulation layer. The encapsulation layer TFE can be formed by laminating one or more layers. The encapsulation layer TFE includes at least one insulating layer. The encapsulation layer TFE according to an embodiment may include at least one inorganic film (hereinafter, encapsulation-inorganic film). The encapsulation layer TFE according to an embodiment may also include at least one organic film (hereinafter, encapsulation-organic film) and at least one encapsulation-inorganic film.

[0084] The encapsulation-inorganic film protects the display device layer DP-ED from moisture / oxygen, while the encapsulation-organic film protects the display device layer DP-ED from foreign substances such as dust particles. The encapsulation-inorganic film may include silicon nitrides, silicon oxide nitrides, silicon oxides, titanium oxides, and / or aluminum oxides, but this disclosure is not particularly limited thereto. The encapsulation-organic film may include acrylic compounds and / or epoxy compounds, etc. The encapsulation-organic film may include photopolymerizable organic materials, but this disclosure is not particularly limited thereto.

[0085] The encapsulation layer TFE can be on the second electrode EL2 and can fill the opening OH.

[0086] refer to Figure 1 and Figure 2 The display device DD may include a non-emitting area NPXA and emitting areas PXA-R, PXA-G, and PXA-B. Each of the emitting areas PXA-R, PXA-G, and PXA-B may be a region that emits light generated from emitting devices ED-1, ED-2, and ED-3, respectively. The emitting areas PXA-R, PXA-G, and PXA-B may be separated from each other in a plane.

[0087] Each of the luminescent regions PXA-R, PXA-G, and PXA-B may be a region defined by a pixel-defining film PDL. The non-luminescent region NPXA may be the region between adjacent luminescent regions PXA-R, PXA-G, and PXA-B, corresponding to a portion of the pixel-defining film PDL. In one or more embodiments, each of the luminescent regions PXA-R, PXA-G, and PXA-B may correspond to a pixel. The pixel-defining film PDL may separate the light-emitting devices ED-1, ED-2, and ED-3. A corresponding one of the emitting layers EML-R, EML-G, and EML-B of the light-emitting devices ED-1, ED-2, and ED-3 may be within an opening OH defined by the pixel-defining film PDL and separated from each other.

[0088] The luminescent areas PXA-R, PXA-G, and PXA-B can be divided into multiple groups based on the color of the light generated from multiple luminescent devices ED-1, ED-2, and ED-3. Figure 1 and Figure 2 In the display device DD of the illustrated embodiment, three light-emitting areas PXA-R, PXA-G, and PXA-B, which emit red, green, and blue light respectively, are explained as examples. For instance, the display device DD of the embodiment may include different red light-emitting areas PXA-R, green light-emitting areas PXA-G, and blue light-emitting areas PXA-B.

[0089] In the display device DD according to an embodiment, a plurality of light-emitting devices ED-1, ED-2, and ED-3 can emit light in different wavelength ranges. For example, in an embodiment, the display device DD may include a first light-emitting device ED-1 that emits red light, a second light-emitting device ED-2 that emits green light, and a third light-emitting device ED-3 that emits blue light. In one or more embodiments, the red light-emitting area PXA-R, the green light-emitting area PXA-G, and the blue light-emitting area PXA-B of the display device DD may correspond to the first light-emitting device ED-1, the second light-emitting device ED-2, and the third light-emitting device ED-3, respectively.

[0090] However, this disclosure is not limited thereto, and the first to third light-emitting devices ED-1, ED-2 and ED-3 may emit light within the same wavelength range or at least one light-emitting device may emit light within a wavelength range different from that of the other light-emitting devices. For example, the first to third light-emitting devices ED-1, ED-2 and ED-3 may all emit blue light.

[0091] According to the embodiment, the light-emitting areas PXA-R, PXA-G, and PXA-B in the display device DD can be arranged in a stripe pattern. (Reference) Figure 1 Multiple red emitting areas PXA-R, multiple green emitting areas PXA-G, and multiple blue emitting areas PXA-B can each be arranged along the second direction DR2. Additionally, the red emitting areas PXA-R, green emitting areas PXA-G, and blue emitting areas PXA-B can be arranged alternately in this order along the first direction DR1.

[0092] Figure 1 and Figure 2 It is explained that all emitting regions PXA-R, PXA-G, and PXA-B have the same area; however, this disclosure is not limited to this, and the emitting regions PXA-R, PXA-G, and PXA-B may have different areas depending on the wavelength range of the emitted light. In this case, the area of ​​the emitting regions PXA-R, PXA-G, and PXA-B may represent the area when viewed in a plane defined by the first direction DR1 and the second direction DR2.

[0093] The arrangement of the luminescent regions PXA-R, PXA-G, and PXA-B is not limited to... Figure 1 The features described herein, and the arrangement order of the red emitting areas PXA-R, green emitting areas PXA-G, and blue emitting areas PXA-B, are combined and provided in different ways according to the characteristics of the display quality required in the display device DD. For example, the arrangement of the emitting areas PXA-R, PXA-G, and PXA-B can be as follows: Arrangement structure (e.g., RGBG matrix, RGBG structure or RGBG matrix structure) or diamond arrangement. It is a registered trademark of Samsung Display Co., Ltd.

[0094] Furthermore, the areas of the light-emitting regions PXA-R, PXA-G, and PXA-B may be different 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 this disclosure is not limited thereto.

[0095] The following text, Figures 3 to 6 A cross-sectional view of a light-emitting device according to an embodiment is shown for illustrative purposes. Each of the light-emitting devices ED according to the embodiment may include a first electrode EL1, a hole transport region HTR, an emitter layer EML, an electron transport region ETR, and a second electrode EL2, which are stacked in sequence.

[0096] and Figure 3 Compare, Figure 4 A cross-sectional view of the light-emitting device ED according to an embodiment is illustrated, 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. Additionally, with Figure 3 Compare, Figure 5 A cross-sectional view of the light-emitting device ED according to an embodiment is illustrated, wherein the hole transport region HTR includes a hole injection layer HIL, a hole transport layer HTL, and an electron blocking layer EBL, and the electron transport region ETR includes an electron injection layer EIL, an electron transport layer ETL, and a hole blocking layer HBL. Figure 4 Compare, Figure 6 A cross-sectional view of a light-emitting device ED, illustrating an embodiment including a capping layer CPL on the second electrode EL2.

[0097] The first electrode EL1 is conductive (e.g., electrically conductive). The first electrode EL1 may be formed of a metallic material, a metal alloy, and / or a conductive compound (e.g., an electrically conductive compound). The first electrode EL1 may be an anode or a cathode. However, this disclosure is not limited thereto. Additionally, the first electrode EL1 may be a pixel electrode. The first electrode EL1 may be a transmissive electrode, a transmissive-reflective electrode, or a reflective electrode. If the first electrode EL1 is a transmissive electrode, it may be formed using a transparent metal oxide such as indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), and indium tin zinc oxide (ITZO). If the first electrode EL1 is a transmissive / reflective electrode or a reflective electrode, then 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, In, Sn, Zn, Yb, and W, compounds of two or more of them, mixtures of two or more of them (e.g., a mixture of Ag and Mg), or oxides thereof, or the first electrode EL1 may include a multilayer material of LiF / Ca or LiF / Al. In one or more embodiments, the first electrode EL1 may have a multilayer structure, which includes a reflective or transmissive film formed from the above-mentioned materials, and a transparent conductive film formed from ITO, IZO, ZnO, ITZO, etc. For example, the first electrode EL1 may have a three-layer structure of ITO / Ag / ITO, but this disclosure is not limited thereto. In addition, this disclosure is not limited thereto, and the first electrode EL1 may include the above-mentioned metallic materials, combinations of at least two of the above-mentioned metallic materials, and / or oxides of the above-mentioned metallic materials, etc. The thickness of the first electrode EL1 may be approximately to approximately For example, the thickness of the first electrode EL1 can be approximately to approximately

[0098] A hole transport region (HTR) is provided on the first electrode EL1. The HTR may include at least one of a hole injection layer (HIL), a hole transport layer (HTL), a buffer layer, an emission assist layer, and an electron blocking layer (EBL). The thickness of the HTR may be, for example, approximately [missing information]. to approximately

[0099] The hole transport region (HTR) can have a single layer formed of a single material, a single layer formed of multiple different materials, or a multilayer structure including multiple layers formed of multiple different materials.

[0100] 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, and may have a single-layer structure formed of a hole injection material and a hole transport material. Alternatively, the hole transport region HTR may have a single-layer structure formed of multiple different materials, or a structure in which hole injection layer HIL / hole transport layer HTL / buffer layer, hole injection layer HIL / buffer layer, hole transport layer HTL / buffer layer, or hole injection layer HIL / hole transport layer HTL / electron blocking layer EBL are sequentially stacked from the first electrode EL1, but this disclosure is not limited thereto.

[0101] Hole transport regions (HTRs) can be formed using various suitable methods such as vacuum deposition, spin coating, casting, Langmuir-Brookett (LB) methods, inkjet printing, laser printing, and / or laser-induced thermal imaging (LITI).

[0102] The hole transport region (HTR) may include a compound represented by the following formula H-1:

[0103] Formula H-1

[0104]

[0105] In formula H-1 above, L1 and L2 can each independently be a directly linked (e.g., a single covalent bond), substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms. a and b can each independently be an integer selected from 0 to 10. In one or more embodiments, when a or b is an integer selected from 2 or greater, the plurality of L1 and L2 can each independently be a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms.

[0106] In formula H-1, Ar1 and Ar2 can each be independently a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms. Additionally, in formula H-1, Ar3 can be a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms.

[0107] The compound represented by formula H-1 above can be a monoamine compound. In one or more embodiments, the compound represented by formula H-1 above can be a diamine compound in which at least one of Ar1 to Ar3 includes an amino group as a substituent. Alternatively, the compound represented by formula H-1 above can be a carbazole compound comprising a substituted or unsubstituted carbazole group in at least one of Ar1 and Ar2, or a fluorene compound comprising a substituted or unsubstituted fluorene group in at least one of Ar1 and Ar2.

[0108] The compound represented by formula H-1 may be represented by any of the compounds selected from the following group of compounds H. However, the compounds listed in the following group of compounds H are examples, and the compound represented by formula H-1 is not limited to the compounds represented by the following group of compounds H:

[0109] Compound group H

[0110]

[0111]

[0112] Hole transport region (HTR) may include phthalocyanine compounds 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 (P ANI / DBSA), polyaniline / camphor sulfonic acid (PANI / CSA), polyaniline / poly(4-styrene sulfonate) (PANI / PSS), N,N'-di(l-naphthyl)-N,N'-diphenyl-benzidine (NPB), triphenylamine-containing polyether ketone (TPAPEK), 4-isopropyl-4'-methyldiphenyliodonium [tetra(pentafluorophenyl)borate], dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarboxylonitrile (HAT-CN), etc.

[0113] Hole transport regions (HTRs) may include carbazole derivatives such as N-phenylcarbazole and / or polyvinylcarbazole, fluorene derivatives, triphenylamine derivatives such as N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (TPD) and 4,4',4”-tris(N-carbazolyl)triphenylamine (TCTA), N,N'-bis(l-naphthyl)-N,N'-diphenyl-benzidine (NPB), 4,4'-cyclohexylbis[N,N-bis(4-methylphenyl)aniline] (TAPC), 4,4'-bis[N,N'-(3-tolyl)amino]-3,3'-dimethylbiphenyl (HMTPD), 1,3-bis(N-carbazolyl)benzene (mCP), etc.

[0114] In addition, 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), etc.

[0115] The hole transport region HTR may include the above-mentioned compound of hole transport region HTR in at least one of hole injection layer HIL, hole transport layer HTL and electron blocking layer EBL.

[0116] The thickness of the hole transport region (HTR) can be approximately to approximately For example, about to approximately When the hole transport region (HTR) includes the hole injection layer (HIL), the hole injection layer (HIL) may have, for example, approximately to approximately The thickness. When the hole transport region (HTR) includes the hole transport layer (HTL), the hole transport layer (HTL) can have approximately [a certain thickness]. to approximately The thickness. For example, when the hole transport region HTR includes an electron blocking layer EBL, the electron blocking layer EBL can have approximately [a certain thickness]. to approximately The thickness of the hole transport region (HTR), hole injection layer (HIL), hole transport layer (HTL), and electron blocking layer (EBL) should be within the range specified above. Appropriate or satisfactory hole transport characteristics can be achieved without a significant increase in the driving voltage.

[0117] In addition to the materials described above, the hole transport region (HTR) may further include a charge-generating material to increase conductivity (e.g., electrical 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 selected from metal halide compounds, quinone derivatives, metal oxides, and cyano-containing compounds, but this disclosure is not limited thereto. For example, p-dopers may include metal halides such as CuI and / or RbI, quinone derivatives such as tetracyanoquinone dimethyl ether (TCNQ) and / or 2,3,5,6-tetrafluoro-7,7',8,8'-tetracyanoquinone dimethyl ether (F4-TCNQ), metal oxides such as tungsten oxide and / or molybdenum oxide, cyano-containing compounds such as dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarboxynitrile (HAT-CN) and / or 4-[[2,3-bis[cyano-(4-cyano-2,3,5,6-tetrafluorophenyl)methylene]cyclopropyl]-cyanomethyl]-2,3,5,6-tetrafluorobenzonitrile, etc., but this disclosure is not limited thereto.

[0118] 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 selected from a buffer layer and an electron blocking layer (EBL). The buffer layer can compensate for the resonant distance according to the wavelength of light emitted from the emission layer (EML), thereby increasing the light emission efficiency. Materials that can be included in the hole transport region (HTR) may be used as materials to be included in the buffer layer. The electron blocking layer (EBL) is a layer used to prevent or reduce electron injection from the electron transport region (ETR) into the hole transport region (HTR).

[0119] The emitter layer EML is provided in the hole transport region (HTR). The emitter layer EML may have, for example, approximately to approximately or about to approximately The thickness of the emitter layer (EML) is as follows. The EML can be a single layer formed of a single material, a single layer formed of multiple different materials, or a multilayer structure with multiple layers formed of multiple different materials.

[0120] The emitting layer EML in the light-emitting device ED of the embodiment may include the fused polycyclic compound represented by Formula 1 of the embodiment.

[0121] Formula 1

[0122]

[0123] In Equation 1, X1 to X5 are each independently NR9, O, S or Se.

[0124] R1 to R9 may each be independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, or may be bonded to adjacent groups to form a ring. For example, R1 may be a substituted or unsubstituted amino group. In one or more embodiments, R1 may be a substituted or unsubstituted diphenylamino group.

[0125] For example, each of R2 and R3 could be a hydrogen atom.

[0126] For example, R4 may be a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms. In one or more embodiments, R4 may be an unsubstituted tert-butyl group.

[0127] For example, each of R5 to R8 can be a hydrogen atom.

[0128] For example, R9 may be a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms. In one or more embodiments, R9 may be a substituted or unsubstituted phenyl group. For example, R9 may be an unsubstituted phenyl group or a phenyl group substituted with a phenyl group. In one or more embodiments, when any of X1 to X3 is represented by NR9, R9 may be an unsubstituted phenyl group or an unsubstituted terphenyl group. For example, R9 may be composed of... It indicates that it comprises three phenyl groups bonded together.

[0129] In one or more embodiments, when X4 and X5 are represented by NR9, R9 may be an unsubstituted phenyl or an unsubstituted biphenyl. For example, R9 may be derived from... This means that, however, this disclosure is not limited thereto.

[0130] a is an integer selected from 0 to 3. For example, a can be 1.

[0131] b and c are each independently an integer selected from 0 to 2. For example, each of b and c can be 0. In an embodiment, when b is 0, the fused polycyclic compound may have the same structure as in the case where R2 is a hydrogen atom. In an embodiment, when c is 0, the fused polycyclic compound may have the same structure as in the case where R3 is a hydrogen atom.

[0132] d is an integer selected from 0 to 3. For example, a can be 1.

[0133] e, f, g, and h are each independently an integer selected from 0 to 4. For example, each of e to h can be 0. As with b, when each of e to h is 0, the fused polycyclic compound can have the same structure as when each of R5 to R8 is a hydrogen atom.

[0134] The fused polycyclic compounds of the embodiments can be formed by connecting two fused polycyclic compounds (each containing a boron atom) via a helical structure. For example, in embodiments of the fused polycyclic compounds of this disclosure, a hexagonal ring containing an X2 atom and a fluorene group can form a helical structure, and at the helical structure, heteroatoms including boron atoms and multiple rings can be fused (e.g., combined together with each other).

[0135] In embodiments, the fused polycyclic compound represented by Formula 1 may be represented by Formula 1-1a or Formula 1-1b:

[0136] Formula 1-1a

[0137]

[0138] Formula 1-1b

[0139]

[0140] Formula 1-1a represents a specific case where a in Formula 1 is 1. For example, in an embodiment, R1 can be substituted at the para position of the boron atom that is substituted on the benzene ring substituted by R1.

[0141] Formula 1-1b represents a specific case where d in Formula 1 is 1. For example, in an embodiment, R4 can be substituted at the para position of the boron atom that is substituted on the benzene ring substituted by R4.

[0142] In Equations 1-1a and 1-1b, X1 to X5, R1 to R9, and a to h are the same as those defined in Equation 1.

[0143] In the fused polycyclic compounds of the embodiments, at least one selected from R1 to R4 is substituted at the para position relative to the boron atom, thereby increasing the multiple resonance effect and electron mobility of the molecule.

[0144] In embodiments, the fused polycyclic compound represented by Formula 1 may be represented by any one of Formulas 1-2a to 1-2d:

[0145] Formula 1-2a

[0146]

[0147] Formula 1-2b

[0148]

[0149] Formula 1-2c

[0150]

[0151] Equation 1-2d

[0152]

[0153] Equations 1-2a to 1-2d represent the cases where X2 is specified in Equation 1.

[0154] In Equations 1-2a and 1-2d, X1, X3 to X5, R1 to R9, and a to h are the same as those defined in Equation 1.

[0155] Compared to the case where X2 is a carbon atom, the fused polycyclic compounds according to embodiments of the present disclosure may have an improved level of overlap between the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO) in the helical structure because heteroatoms such as NR9, O, S or Se are located at the X2 position in the helical structure.

[0156] Furthermore, the fused polycyclic compounds in the embodiments include spiro structures, thus the conjugation in the molecule can be expanded, thereby reducing the ΔE of the fused polycyclic compounds. ST value.

[0157] Therefore, in embodiments of the fused polycyclic compounds of this disclosure, bond dissociation energy and multiple resonance effects can be increased, thereby increasing molecular stability. When the fused polycyclic compounds of this disclosure are applied to any one of the multiple organic layers selected from a light-emitting device (ED), interactions with adjacent molecules are reduced, thus improving the luminescence efficiency of the device.

[0158] In the embodiments, the fused polycyclic compound represented by Formula 1 can be represented by Formulas 1-3:

[0159] Formula 1-3

[0160]

[0161] Equations 1-3 specify the cases where R2 and R3 are defined in Equation 1. In the embodiments, each of R2 and R3 may be a hydrogen atom. Equations 1-3 may have the same structure as the cases where b and c are each 0 in Equation 1.

[0162] X1 to X5, R1, R4 to R9, a and d to h are the same as those defined in Equation 1.

[0163] In the embodiments, the fused polycyclic compound represented by Formula 1 can be represented by Formulas 1-4:

[0164] Formula 1-4

[0165]

[0166] Equations 1-4 specify the cases where R6 and R7 are defined in Equation 1. In the embodiments, each of R6 and R7 can be a hydrogen atom. Equations 1-4 can have the same structure as the cases where f and g are each 0 in Equation 1.

[0167] In the embodiments, the fused polycyclic compound represented by Formula 1 can be represented by Formulas 1-5:

[0168] Formula 1-5

[0169]

[0170] Equations 1-5 specify the cases where R5 and R8 are defined in Equation 1. In the embodiments, each of R5 and R8 may be a hydrogen atom. Equations 1-5 may have the same structure as the cases where e and h are each 0 in Equation 1.

[0171] In the embodiments, the fused polycyclic compound represented by Formula 1 can be represented by Formulas 1-6:

[0172] Formula 1-6

[0173]

[0174] Equations 1-6 specify the cases where R2, R3, and R5 through R8 are designated in Equation 1. In the embodiments, each of R2, R3, and R5 through R8 may be a hydrogen atom. Equations 1-6 may be the same structure as the cases where b, c, and e through h in Equation 1 are each 0.

[0175] X1 to X5, R1, R4, R9, a and d are the same as those defined in Equation 1.

[0176] In embodiments, the fused polycyclic compound represented by Formula 1 may include any one of the compounds selected from group 1 of compounds:

[0177] Compound group 1

[0178]

[0179]

[0180]

[0181]

[0182]

[0183]

[0184]

[0185] The emitting layer EML in the light-emitting device ED of the embodiment can emit fluorescence, phosphorescence, and / or delayed fluorescence. For example, the emitting layer EML can emit thermally activated delayed fluorescence (TADF).

[0186] The emitting layer EML in the light-emitting device ED of the embodiment can emit blue light. For example, the emitting layer EML can emit light with a center wavelength of about 420 nm to about 470 nm.

[0187] exist Figures 3 to 6 In the light-emitting device ED of the embodiments described herein, the emission layer EML may include a host and a dopant. The emission layer EML of the embodiments may include the fused polycyclic compound of the above embodiments as a dopant.

[0188] In the light-emitting device ED of the embodiments, the emitting layer EML may comprise any suitable host material commonly used or available in the art. For example, the emitting layer EML may comprise anthracene derivatives, pyrene derivatives, fluoranthene derivatives, 1,2-benzophenanthrene derivatives, dihydrobenzanthene derivatives, and / or triphenylene derivatives. In one or more embodiments, the emitting layer EML may comprise anthracene derivatives and / or pyrene derivatives.

[0189] The emitting layer (EML) may include compounds represented by the following formula E-1. Compounds represented by the following formula E-1 can be used as fluorescent host materials.

[0190] E-1

[0191]

[0192] In equation E-1, R 31 To R 40 Each of these can be independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, or can be bonded to adjacent groups to form a ring. In one embodiment, R 31 To R 40 It can bond to adjacent groups to form saturated or unsaturated hydrocarbon rings.

[0193] In E-1, c and d can each be an integer selected from 0 to 5 independently.

[0194] Formula E-1 can be represented by any one of the following compounds E1 to E19:

[0195]

[0196] In an embodiment, the emitting layer EML may include a compound represented by formula E-2a or E-2b. The compound represented by formula E-2a or E-2b may be used as a phosphorescent host material.

[0197] E-2a

[0198]

[0199] In equation E-2a, a can be an integer selected from 0 to 10, L a It can be a directly linked, substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms. In one or more embodiments, when a is an integer of 2 or greater, a plurality of L a Each can be independently a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms.

[0200] Furthermore, in E-2a, A1 to A5 can each be N or CR independently. i R a To R i Each group may independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted amino group, a substituted or unsubstituted thio group, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, or may be bonded to an adjacent group to form a ring. R a To R i It can bond to adjacent groups to form hydrocarbon rings or heterocycles containing N, O, S, etc. as cyclic atoms.

[0201] In one or more embodiments, in formula E-2a, two or three selected from A1 to A5 may be N, and the others A1 to A5 may be CR. i .

[0202] E-2b

[0203]

[0204] In formula E-2b, Cbz1 and Cbz2 can each be independently an unsubstituted carbazole group or a carbazole group substituted with an aryl group having 6 to 30 cyclic carbon atoms. bThe L group is a directly linked (e.g., a single covalent bond), substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms. In one or more embodiments, b is an integer selected from 0 to 10, and when b is an integer of 2 or greater, the plurality of L groups... b Each can be independently a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms.

[0205] The compound represented by formula E-2a or E-2b may be represented by any of the compounds selected from the following group of compounds E-2. However, the compounds listed in the following group of compounds E-2 are examples, and the compound represented by formula E-2a or E-2b is not limited to the compound represented by the following group of compounds E-2.

[0206] Compound group E-2

[0207]

[0208]

[0209]

[0210] The emitter layer EML may further include any suitable material commonly used or available in the art as the host material. For example, the emitter layer EML may include at least one selected from bis[2-(diphenylphosphine)phenyl]ether oxide (DPEPO), 4,4'-bis(carbazole-9-yl)biphenyl (CBP), 1,3-bis(carbazole-9-yl)benzene (mCP), 2,8-bis(diphenylphospho)dibenzo[b,d]furan (PPF), 4,4',4”-tris(carbazole-9-yl)triphenylamine (TCTA), and 1,3,5-tris(1-phenyl-1H-benzo[d]imidazol-2-yl)benzene (TPBi) as the host material. However, this disclosure is not limited thereto; for example, tris(8-hydroxyquinolinyl)aluminum (Al) q3), poly(N-vinylcarbazole) (PVK), 9,10-bis(naphthyl-2-yl)anthracene (ADN), 2-tert-butyl-9,10-bis(naphthyl-2-yl)anthracene (TBADN), stilbene aromatic hydrocarbon (DSA), 4,4'-bis(9-carbazolyl)-2,2'-dimethylbiphenyl (CDBP), 2-methyl-9,10-bis(naphthyl-2-yl)anthracene (MADN), hexaphenylcyclotriphosphazene (CP1), 1,4-bis(triphenylsilyl)benzene (UGH2), hexaphenylcyclotrisiloxane (DPSiO3), octaphenylcyclotetrasiloxane (DPSiO4), etc., can be used as main materials.

[0211] The emitter layer EML may further include any suitable dopant material commonly used or available in the art.

[0212] For example, the emitter layer EML may include compounds represented by the formula Ma or Mb. Compounds represented by the formula Ma or Mb can be used as phosphorescent dopant materials.

[0213] Formula Ma

[0214]

[0215] In the above formula Ma, Y1 to Y4 and Z1 to Z4 can each independently be CR1 or N, and R1 to R4 can each independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted amino group, a substituted or unsubstituted thio group, a substituted or unsubstituted oxygen 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 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, or can be bonded to adjacent groups to form a ring. In formula Ma, m is 0 or 1, and n is 2 or 3. In formula Ma, when m is 0, n is 3, and when m is 1, n is 2.

[0216] Compounds represented by the formula Ma can be used as red or green phosphorescent dopants.

[0217] Compounds represented by formula Ma can be represented by any one of compounds selected from M-a1 to M-a19. However, compounds M-a1 to M-a19 are examples, and compounds represented by formula Ma are not limited to those represented by compounds M-a1 to M-a19.

[0218]

[0219]

[0220] Compounds M-a1 and M-a2 can be used as red dopant materials, while compounds M-a3 and M-a4 can be used as green dopant materials.

[0221] Formula Mb

[0222]

[0223] In formula Mb, Q1 to Q4 are each independently C or N, and C1 to C4 are each independently a substituted or unsubstituted hydrocarbon ring having 5 to 30 cyclic carbon atoms or a substituted or unsubstituted heterocycle having 2 to 30 cyclic carbon atoms. L 21 To L24 Each is independently a direct connection (e.g., a single covalent bond). The substituted or unsubstituted divalent alkyl group having 1 to 20 carbon atoms, the substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or the substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, wherein e1 to e4 are each independently 0 or 1. R 31 To R 39 Each of the following groups is independently 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 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, or is bonded to an adjacent group to form a ring, and d1 to d4 are each independently an integer selected from 0 to 4.

[0224] Compounds represented by the formula Mb can be used as blue or green phosphorescent dopants.

[0225] Compounds represented by the formula Mb can be represented by any of the compounds selected from the following. However, the following compounds are examples, and compounds represented by the formula Mb are not limited to those represented by the following compounds.

[0226]

[0227]

[0228] In compounds, R, R 38 and R 39 Each of the following can be independently 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 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms.

[0229] The emitter layer (EML) may comprise a compound represented by any one of the following formulas: Fa to Fc. A compound represented by any one of the following formulas: Fa to Fc can be used as a fluorescent dopant material.

[0230] Formula Fa

[0231]

[0232] In the formula Fa, the formula is selected from R. a To R j The two in can be independently... Replace. R a To R jChina was not The other substituted groups can 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 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms. In this context, Ar1 and Ar2 can each be independently a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms. For example, at least one selected from Ar1 and Ar2 can be a heteroaryl group containing O or S as a cyclic atom.

[0233] Formula Fb

[0234]

[0235] In equation Fb, R a and R b Each of the following can be independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, or can be bonded to an adjacent group to form a ring.

[0236] In formula Fb, U and V can each be independently a substituted or unsubstituted hydrocarbon ring having 5 to 30 cyclic carbon atoms or a substituted or unsubstituted heterocycle having 2 to 30 cyclic carbon atoms.

[0237] In formula Fb, the number of rings represented by U and V can each be 0 or 1 independently. For example, in formula Fb, it means that when the number of U or V is 1, a ring forms a fused ring in the part described as U or V, and when the number of U or V is 0, the ring described as U or V does not exist. In one or more embodiments, 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 of the fluorene core having formula Fb can be a tetracyclic cyclic compound. Additionally, when the number of each of U and V is 0, the fused ring of the fluorene core having formula Fb can be a tricyclic cyclic compound. Furthermore, when the number of each of U and V is 1, the fused ring of the fluorene core having formula Fb can be a pentacyclic cyclic compound.

[0238] Formula Fc

[0239]

[0240] In equation Fc, A1 and A2 can be independently O, S, Se, or NR. m And Rm 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 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms. R1 to R 11 Each of the following groups is independently 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 oxygen group, a substituted or unsubstituted thio group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, or is bonded to an adjacent group to form a ring.

[0241] In formula Fc, A1 and A2 can each independently bond to substituents of adjacent rings to form fused rings. For example, when A1 and A2 are each independently NR m In this case, A1 can be bonded to R4 or R5 to form a ring. Additionally, A2 can be bonded to R7 or R8 to form a ring.

[0242] In an implementation, the emitter layer EML may comprise any suitable dopant material commonly used or available in the art. For example, the emitter layer (EML) may 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), N-(4-((E)-2-(6-((E)-4-(diphenylamino)styrene)naphth-2-yl)vinyl)phenyl)-N-phenylaniline (N-BDAVBi), 4,4'-bis[2-(4-(N,N-diphenylamino)phenyl)vinyl]biphenyl (DPAVBi)), perylene and / or its derivatives (e.g., 2,5,8,11-tetra-tert-butylperylene (TBP)), pyrene and / or its derivatives (e.g., 1,1'-dipyrene, 1,4-dipyrenebenzene, 1,4-bis(N,N-diphenylamino)pyrene), etc.

[0243] The emitter layer EML may comprise any suitable phosphorescent dopant material commonly used or available in the art. For example, metal composites comprising 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 phosphorescent dopant. In one or more embodiments, bis(4,6-difluorophenylpyridinyl-N,C2')pyridinecarboxyiridium(III) (FIrpic), bis(2,4-difluorophenylpyridinyl)tetra(1-pyrazolyl)boronate(III) (FIr6), and / or octaethylporphyrin platinum (PtOEP) may be used as phosphorescent dopant. However, this disclosure is not limited thereto.

[0244] The emitter layer (EML) may include quantum dot materials. The core of the quantum dots may be selected from group II-VI compounds, group III-VI compounds, group I-III-IV compounds, group III-V compounds, group III-II-V compounds, group IV-VI compounds, group IV elements, group IV compounds, and combinations thereof.

[0245] Group II-VI compounds may be selected from the following groups: binary compounds selected from the group consisting of CdSe, CdTe, CdS, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, MgSe, MgS and mixtures thereof; and compounds selected from the group consisting of CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, CdZnSe, and CdZnT. Ternary compounds selected from the group consisting of e, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, MgZnSe, MgZnS and mixtures thereof, and quaternary compounds selected from the group consisting of HgZnTeS, CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe, HgZnSTe and mixtures thereof.

[0246] Group III-VI compounds may include binary compounds such as In2S3 and / or In2Se3, ternary compounds such as InGaS3 and / or InGaSe3, or any combination thereof.

[0247] Group I-III-VI compounds may be selected from: ternary compounds selected from the group consisting of AgInS, AgInS2, CuInS, CuInS2, AgGaS2, CuGaS2, CuGaO2, AgGaO2, AgAlO2 and mixtures thereof, and / or quaternary compounds such as AgInGaS2 and / or CuInGaS2.

[0248] Group III-V compounds may be selected from the group consisting of: binary compounds selected from the group consisting of GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, InSb, and mixtures thereof; ternary compounds selected from the group consisting of GaNP, GaNAs, GaNSb, GaPAs, GaPSb, AlNP, AlNAs, AlNSb, AlPAs, AlPSb, InGaP, InAlP, InNP, InNAs, InNSb, InPAs, InPSb, and mixtures thereof; and quaternary compounds selected from the group consisting of GaAlNP, GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNP, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs, InAlPSb, and mixtures thereof. In one or more embodiments, the Group III-V compounds may further comprise Group II metals. For example, InZnP and the like can be selected as group III-II-V compounds.

[0249] Group IV-VI compounds may be selected from the following groups: binary compounds selected from the group consisting of SnS, SnSe, SnTe, PbS, PbSe, PbTe, and mixtures thereof; ternary compounds selected from the group consisting of SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, SnPbTe, and mixtures thereof; and quaternary compounds selected from the group consisting of SnPbSSe, SnPbSeTe, SnPbSTe, and mixtures thereof. Group IV elements may be selected from the group consisting of Si, Ge, and mixtures thereof. Group IV compounds may be binary compounds selected from the group consisting of SiC, SiGe, and mixtures thereof.

[0250] In this case, binary, ternary, or quaternary compounds can exist in the particles with a uniform (e.g., substantially uniform) concentration distribution, or they can exist in the same particle with partially different concentration distributions. Additionally, the quantum dots can have a core / shell structure, where one quantum dot surrounds another. In the core / shell structure, the shell interface can have a concentration gradient, where the concentration of the element present in the shell decreases along the direction towards the core.

[0251] In some embodiments, quantum dots may have the aforementioned core / shell structure, comprising a core containing nanocrystals and a shell surrounding the core. The shell of the quantum dot may serve as a protective layer to prevent or reduce chemical degradation of the core, thereby maintaining semiconductor properties, and / or as a charging layer to impart electrophoretic properties to the quantum dot. The shell may be a single layer or multiple layers. Examples of shells for quantum dots may include metal and / or non-metal oxides, semiconductor compounds, or combinations thereof.

[0252] For example, metal and / or non-metal oxides may be binary compounds such as SiO2, Al2O3, TiO2, ZnO, MnO, Mn2O3, Mn3O4, CuO, FeO, Fe2O3, Fe3O4, CoO, Co3O4 and / or NiO, and / or ternary compounds such as MgAl2O4, CoFe2O4, NiFe2O4 and / or CoMn2O4, but this disclosure is not limited thereto.

[0253] In addition, the semiconductor compound may be, for example, CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnSeS, ZnTeS, GaAs, GaP, GaSb, HgS, HgSe, HgTe, InAs, InP, InGaP, InSb, AlAs, AlP, AlSb, etc., but this disclosure is not limited thereto.

[0254] Quantum dots can have a full width at half maximum (FWHM) of a light emission wavelength spectrum of about 45 nm or less, about 40 nm or less, or, for example, about 30 nm or less, and color purity and / or color reproducibility can be improved within the aforementioned range. Furthermore, light emitted through such quantum dots is emitted in all directions (e.g., substantially in all directions), thus improving wide viewing angles.

[0255] Furthermore, there are no particular limitations on the form of quantum dots, as long as it is a form commonly used or available in the art. In one or more embodiments, quantum dots can be used in the form of spherical, conical, multi-armed or cubic nanoparticles, nanotubes, nanowires, nanofibers, nanoplates, etc.

[0256] Quantum dots can emit light in colors that can be controlled by their particle size. Therefore, quantum dots can emit a variety of suitable colors, such as blue, red, and green.

[0257] exist Figures 3 to 6 In each of the light-emitting devices (EDs) described in the embodiments, an electron transport region (ETR) is provided on an emitter layer (EML). The electron transport region (ETR) may include at least one selected from a hole blocking layer (HBL), an electron transport layer (ETL), and an electron injection layer (EIL), but this disclosure is not limited thereto.

[0258] The electron transport region (ETR) can have a single layer formed of a single material, a single layer formed of multiple different materials, or a multilayer structure comprising multiple layers formed of multiple different materials.

[0259] 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), and may have a single-layer structure formed of an electron injection material and an electron transport material. Alternatively, the ETR may have a single-layer structure formed of multiple different materials, or may have a structure in which the electron transport layer (ETL) / electron injection layer (EIL) and the hole blocking layer (HBL) / electron transport layer (ETL) / electron injection layer (EIL) are sequentially stacked from the emitter layer (EML), but this disclosure is not limited thereto. The ETR may have, for example, approximately to approximately The thickness.

[0260] Electron transport regions (ETRs) can be formed using various appropriate methods such as vacuum deposition, spin coating, casting, Langmuir-Brockett (LB) methods, inkjet printing, laser printing, and laser-induced thermal imaging (LITI).

[0261] The electron transport region (ETR) may include compounds represented by the following formula:

[0262] ET-1

[0263]

[0264] In Equation ET-1, at least one of X1 to X3 is N, and the remaining X1 to X3 are CR. a R a Ar1 to Ar3 can each 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 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms.

[0265] In Formula ET-1, a to c can each be an integer selected from 0 to 10. In Formula ET-1, L1 to L3 can each be a directly linked (e.g., a single covalent bond), substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms. In one or more embodiments, when a to c are integers 2 or greater, L1 to L3 can each be a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms.

[0266] The electron transport region (ETR) may include anthracene compounds. However, this disclosure is not limited thereto, and the ETR may include, for example, tris(8-hydroxyquinoline)aluminum (Alq3), 1,3,5-tris[(3-pyridyl)-benzene-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, and 1,3,5-tris(1-phenyl-1H-benzimidazol-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-(naphthyl-1-yl)-3,5-diphenyl-4H-1,2,4-triazole (NTAZ), 2-(4-biphenyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole ( t Bu-PBD), bis(2-methyl-8-quinolinyl-N1,O8)-(1,1'-biphenyl-4-hydroxy)aluminum (BAlq), bis(benzoquinoline-10-hydroxy)beryllium (Bebq2), 9,10-bis(naphthyl-2-yl)anthracene (ADN), 1,3-bis[3,5-bis(pyridin-3-yl)phenyl]benzene (BmPyPhB) or mixtures thereof.

[0267] Additionally, the electron transport region (ETR) may include metal halides such as LiF, NaCl, CsF, RbCl, RbI, CuI, and / or KI, lanthanides such as Yb, and / or co-deposited materials of metal halides and lanthanides. For example, the ETR may include KI:Yb, RbI:Yb, etc., as co-deposited materials. In one or more embodiments, the ETR may be formed using metal oxides such as Li₂O and / or BaO, and / or lithium 8-hydroxyquinoline (Liq), but this disclosure is not limited thereto. The ETR may also be formed from a mixture of an electron transport material and an insulating organometallic salt. The insulating organometallic salt may be a material with a band gap of about 4 eV or higher. In one or more embodiments, the insulating organometallic salt may include, for example, metal acetates, metal benzoates, metal acetoacetates, metal acetylacetonates, and / or metal stearates.

[0268] In addition to the materials described above, the electron transport region (ETR) may further include at least one selected from 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP) and 4,7-diphenyl-1,10-phenanthroline (Bphen), but this disclosure is not limited thereto.

[0269] The electron transport region ETR may include the above-mentioned compound selected from at least one of the electron injection layer EIL, the electron transport layer ETL, and the hole blocking layer HBL.

[0270] When the electron transport region (ETR) includes the electron transport layer (ETL), the ETL can have approximately to approximately For example, about to approximately The thickness of the electron transport layer (ETL) is considered. If the thickness of the ETL meets the above-mentioned range, suitable or satisfactory electron transport characteristics can be obtained without a significant increase in the driving voltage. When the electron transport region (ETR) includes the electron injection layer (EIL), the EIL can have approximately [missing information - likely a thickness value]. to approximately For example, about to approximately The thickness of the electron injection layer (EIL) is crucial. If the thickness of the EIL meets the above range, appropriate or satisfactory electron injection characteristics can be obtained without a significant increase in the driving voltage.

[0271] The second electrode EL2 is provided on the electron transport region ETR. The second electrode EL2 may be a common electrode. The second electrode EL2 may be a cathode or an anode, but this disclosure 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.

[0272] The second electrode EL2 can be a transmission electrode, a transmission-reflection electrode, or a reflection electrode. When the second electrode EL2 is a transmission electrode, it can be formed of a transparent metal oxide, such as indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), indium tin zinc oxide (ITZO), etc.

[0273] When the second electrode EL2 is a transmissive or reflective electrode, it may include at least one of Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF, Mo, Ti, Yb, and W, two or more compounds thereof (e.g., AgYb or MgAg), mixtures of two or more thereof, and / or oxides thereof. Alternatively, the second electrode EL2 may include a multilayered material of LiF / Ca or LiF / Al. In one or more embodiments, the second electrode EL2 may have a multilayered structure, including a reflective or transmissive film formed from the aforementioned materials, and a transparent conductive film formed from ITO, IZO, ZnO, ITZO, etc. For example, the second electrode EL2 may include the aforementioned metallic materials, combinations of at least two of the aforementioned metallic materials, and / or oxides of the aforementioned metallic materials.

[0274] In one or more embodiments, the second electrode EL2 may be coupled to an auxiliary electrode. If the second electrode EL2 is coupled to the auxiliary electrode, the resistance of the second electrode EL2 may be reduced.

[0275] In one or more embodiments, the capping layer CPL may further be on the second electrode EL2 of the light-emitting device ED of the embodiment. The capping layer CPL may include multiple layers or a single layer.

[0276] In this embodiment, the capping layer CPL can be an organic layer and / or an inorganic layer. For example, when the capping layer CPL includes an inorganic material, the inorganic material may include alkali metal compounds such as LiF, alkaline earth metal compounds such as MgF2, SiON, and SiN. x SiO y wait.

[0277] For example, when the capping layer CPL comprises an organic material, the organic material may include 2,2'-dimethyl-N,N'-di-[(1-naphthyl)-N,N'-diphenyl]-1,1'-biphenyl-4,4'-diamine (α-NPD), NPB, TPD, m-MTDATA, Alq3, CuPc, N4,N4,N4',N4'-tetra(biphenyl-4-yl)biphenyl-4,4'-diamine (TPD15), 4,4',4"-tris(carbazole-9-yl)triphenylamine (TCTA), etc., and / or epoxy resin, and / or acrylate such as methacrylate. However, this disclosure is not limited thereto, and the capping layer CPL may include at least one selected from the following compounds P1 to P5:

[0278]

[0279]

[0280] In one or more embodiments, the refractive index of the capping layer CPL may be about 1.6 or greater. For example, the refractive index of the capping layer CPL may be about 1.6 or greater for light with a wavelength range of about 550 nm to about 660 nm.

[0281] Figure 7 and Figure 8 Each of these is a cross-sectional view of a display device according to an embodiment. Hereinafter, in the description references... Figure 7 and Figure 8 In the display device of the embodiment described above, the existing implementation will not be described here. Figures 1 to 6 The description will focus on the repetitive features, but will primarily describe their differences.

[0282] refer to Figure 7 According to the embodiments, the display device DD may include a display panel DP including a display device layer DP-ED, a light control layer CCL on the display panel DP, and a color filter layer CFL.

[0283] exist Figure 7 In the embodiments described herein, the display panel DP may include a substrate layer BS, a circuit layer DP-CL provided on the substrate layer BS, and a display device layer DP-ED, and the display device layer DP-ED may include a light-emitting device ED.

[0284] A light-emitting device (ED) may include a first electrode EL1, a hole transport region (HTR) on the first electrode EL1, an emitter layer (EML) on the hole transport region HTR, an electron transport region (ETR) on the emitter layer EML, and a second electrode EL2 on the electron transport region ETR. According to one or more embodiments, as described above... Figures 3 to 6 The structure of the light-emitting device can be equivalently applied to Figure 7 The structure of the light-emitting device ED shown in the figure.

[0285] refer to Figure 7 The emitting layer EML can be located within the opening OH defined by the pixel-defining film PDL. For example, the emitting layer EML provided by the pixel-defining film PDL and corresponding to each of the light-emitting areas PXA-R, PXA-G, and PXA-B can emit light within the same wavelength range. In the display device DD of the embodiment, the emitting layer EML can emit blue light. In one or more embodiments, the emitting layer EML can be provided as a common layer in the entire light-emitting areas PXA-R, PXA-G, and PXA-B.

[0286] A light control layer (CCL) may be present on a display panel (DP). The CCL may include a light converter, which may be a quantum dot or a phosphor, etc. The light converter emits the supplied light by converting its wavelength. For example, the CCL may include a layer containing quantum dots and / or a layer containing phosphors.

[0287] The optical control layer (CCL) may include multiple optical control units CCP1, CCP2, and CCP3. The optical control units CCP1, CCP2, and CCP3 may be separated from each other.

[0288] refer to Figure 7 The segmented pattern BMP may be located between two adjacent optical control units CCP1, CCP2 and CCP3 that are separated from each other, but this disclosure is not limited thereto. Figure 7 It is explained that the segmentation pattern BMP does not overlap with the optical control units CCP1, CCP2, and CCP3, but at least a portion of the edges of the optical control units CCP1, CCP2, and CCP3 may overlap with the segmentation pattern BMP.

[0289] The light control layer CCL may include a first light control unit CCP1 containing a first quantum dot QD1 that converts a first color light provided by the light-emitting device ED into a second color light, a second light control unit CCP2 containing a second quantum dot QD2 that converts the first color light into a third color light, and a third light control unit CCP3 that transmits the first color light.

[0290] In this embodiment, the first light control unit CCP1 can provide red light as the second color light, and the second light control unit CCP2 can provide green light as the third color light. The third light control unit CCP3 can transmit blue light as the first color light provided in the light-emitting device 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. The same principles as described above can be applied to quantum dots QD1 and QD2.

[0291] Additionally, the optical control layer CCL may further include a scatterer SP (e.g., a light scatterer SP). The first optical control unit CCP1 may include a first quantum dot QD1 and a scatterer SP, the second optical control unit CCP2 may include a second quantum dot QD2 and a scatterer SP, and the third optical control unit CCP3 may not include any quantum dots, but may include a scatterer SP.

[0292] The scatterer SP can be inorganic particles. For example, the scatterer SP may include at least one selected from TiO2, ZnO, Al2O3, SiO2, and hollow silica. The scatterer SP may include any one selected from TiO2, ZnO, Al2O3, SiO2, and hollow silica, or may be a mixture of at least two materials selected from TiO2, ZnO, Al2O3, SiO2, and hollow silica.

[0293] The first optical control unit CCP1, the second optical control unit CCP2, and the third optical control unit CCP3 may each comprise a substrate resin BR1, BR2, and BR3 in which quantum dots QD1 and QD2 and a scatterer SP are dispersed. In an embodiment, the first optical control unit CCP1 may comprise the first quantum dot QD1 and the scatterer SP dispersed in the first substrate resin BR1, the second optical control unit CCP2 may comprise the second quantum dot QD2 and the scatterer SP dispersed in the second substrate resin BR2, and the third optical control unit CCP3 may comprise the scatterer SP dispersed in the third substrate resin BR3. The substrate resins BR1, BR2, and BR3 are the medium in which the quantum dots QD1 and QD2 and the scatterer SP are dispersed, and may be formed from various suitable resin compositions, which are commonly referred to as adhesives. For example, the substrate resins BR1, BR2, and BR3 may be acrylic resins, urethane resins, silicone resins, epoxy resins, etc. The substrate resins BR1, BR2, and BR3 may be transparent resins. In the embodiments, the first base resin BR1, the second base resin BR2, and the third base resin BR3 may be the same as or different from each other.

[0294] The optical control layer CCL may include an isolation layer BFL1. Isolation layer BFL1 is used to prevent or reduce the penetration of moisture and / or oxygen (hereinafter referred to as "moisture / oxygen"). Isolation layer BFL1 may be present on optical control units CCP1, CCP2, and CCP3 to block or reduce their exposure to moisture / oxygen. In one or more embodiments, isolation layer BFL1 may cover optical control units CCP1, CCP2, and CCP3. Additionally, isolation layer BFL2 may be provided on the optical control layer CCL.

[0295] The isolation layers BFL1 and BFL2 may include at least one inorganic layer. In one or more embodiments, the isolation layers BFL1 and BFL2 may include inorganic materials. For example, the isolation layers BFL1 and BFL2 may include silicon nitride, aluminum nitride, zirconium nitride, titanium nitride, hafnium nitride, tantalum nitride, silicon oxide, aluminum oxide, titanium oxide, tin oxide, cerium oxide, silicon nitride, metal thin films that ensure light transmittance, etc. In one or more embodiments, the isolation layers BFL1 and BFL2 may further include an organic film. The isolation layers BFL1 and BFL2 may be formed from a single layer or multiple layers.

[0296] In the display device DD of this embodiment, the color filter layer CFL can be on the light control layer CCL. For example, the color filter layer CFL can be directly on the light control layer CCL. In this case, the isolation layer BFL2 can be omitted.

[0297] The color filter layer CFL may include a light-shielding unit BM and filters CF1, CF2, and CF3. The color filter layer CFL may include a first filter CF1 that transmits a second color of light, a second filter CF2 that transmits a third color of light, and a third filter CF3 that transmits a first color of light. For example, the first filter CF1 may be a red filter, the second filter CF2 may be a green filter, and the third filter CF3 may be a blue filter. Filters CF1, CF2, and CF3 may each include a polymerized photosensitive resin and a pigment and / or dye. The first filter CF1 may include a red pigment and / or dye, the second filter CF2 may include a green pigment and / or dye, and the third filter CF3 may include a blue pigment and / or dye. However, this disclosure is not limited thereto, and the third filter CF3 may not include any pigment or dye. The third filter CF3 may include a polymerized photosensitive resin and may not include any pigment or dye. The third filter CF3 may be transparent. The third filter CF3 may be formed of a transparent photosensitive resin.

[0298] Furthermore, in the embodiment, the first filter CF1 and the second filter CF2 can be yellow filters. The first filter CF1 and the second filter CF2 can be provided as a single filter, without separation.

[0299] The light-shielding unit BM can be a black matrix. The light-shielding unit BM may include organic and / or inorganic light-shielding materials containing black pigments and / or dyes. The light-shielding unit BM can prevent or reduce light leakage and can separate the boundaries between adjacent filters CF1, CF2, and CF3. Alternatively, in an embodiment, the light-shielding unit BM may be formed from a blue filter.

[0300] The first to third filters CF1, CF2 and CF3 can correspond to the red emitting area PXA-R, the green emitting area PXA-G and the blue emitting area PXA-B, respectively.

[0301] The substrate BL may be located on the color filter layer CFL. The substrate BL may be a component providing a substrate surface, with the color filter layer CFL and light control layer CCL located on the substrate surface. The substrate BL may be a glass substrate, a metal substrate, a plastic substrate, etc. However, this disclosure is not limited thereto, and the substrate BL may be an inorganic layer, an organic layer, or a composite material layer including inorganic and organic materials. Furthermore, unlike what is shown in the accompanying drawings, the substrate BL may be omitted in this embodiment.

[0302] Figure 8 A cross-sectional view illustrating a portion of a display device according to an embodiment is shown. In the display device DD-TD of the embodiment, the light-emitting device ED-BT may include a plurality of light-emitting structures OL-B1, OL-B2, and OL-B3. The light-emitting device ED-BT may include a first electrode EL1 and a second electrode EL2 facing each other, and the plurality of light-emitting structures OL-B1, OL-B2, and OL-B3 are sequentially stacked in the thickness direction between the first electrode EL1 and the second electrode EL2. Each of the light-emitting structures OL-B1, OL-B2, and OL-B3 may include an emission layer EML (Emitting Layer). Figure 7 ) and the emission layer EML ( Figure 7 The hole transport region (HTR) and electron transport region (ETR) of the electron transport region.

[0303] In one or more embodiments, the light-emitting device ED-BT included in the display device DD-TD of the embodiment may be a light-emitting device having a series structure and including multiple emitting layers.

[0304] exist Figure 8 In the embodiments described herein, all light beams emitted from the light-emitting structures OL-B1, OL-B2, and OL-B3 may be blue light. However, this disclosure is not limited thereto, and the light beams emitted from the light-emitting structures OL-B1, OL-B2, and OL-B3 may have different wavelength ranges from each other. For example, a light-emitting device ED-BT comprising multiple light-emitting structures OL-B1, OL-B2, and OL-B3 that emit light beams with different wavelength ranges may emit white light.

[0305] The charge generation layers CGL1 and CGL2 may be located between adjacent light-emitting structures OL-B1, OL-B2, and OL-B3. The charge generation layers CGL1 and CGL2 may include p-type charge generation layers and / or n-type charge generation layers.

[0306] The light-emitting device ED according to embodiments of the present disclosure may include the fused polycyclic compound of the above embodiments in the emission layer EML between the first electrode EL1 and the second electrode EL2 to exhibit excellent luminous efficiency. Furthermore, the fused polycyclic compound according to the embodiments may be a thermally activated delayed fluorescence dopant, and the emission layer EML may include the fused polycyclic compound of the embodiments to emit thermally activated delayed fluorescence, thereby exhibiting excellent luminous efficiency characteristics.

[0307] In addition to the emitting layer EML, the fused polycyclic compound of one or more of the above embodiments can be included in the organic layer as a material for the light-emitting device ED. For example, the light-emitting device ED according to the embodiments of this disclosure may include the above-mentioned fused polycyclic compound in at least one functional layer between the first electrode EL1 and the second electrode EL2, and / or in the capping layer CPL on the second electrode EL2.

[0308] The fused polycyclic compounds of the above embodiments may have a fused polycyclic compound containing two boron atoms, including a helical backbone.

[0309] Spiral structures, including those in fused polycyclic compounds, contain heteroatoms such as N, O, S, and Se instead of carbon atoms, thus improving the overlap levels of HOMO and LUMO in spirostructures. Furthermore, conjugation in spirostructures can be expanded, thereby providing lower ΔE. ST Value-enhanced fused polycyclic compounds.

[0310] Therefore, the fused polycyclic compounds disclosed herein can have strong bond dissociation energies, exhibit multiple resonance effects, and have stable molecular structures.

[0311] The light-emitting device comprising the fused polycyclic compound of the embodiment in the emitting layer can emit blue light and exhibits high efficiency characteristics.

[0312] The fused polycyclic compounds and light-emitting devices according to embodiments of the present disclosure will be described in more detail below with reference to examples and comparative examples. Furthermore, the examples illustrated below are for understanding the subject matter of the present disclosure only, and the scope of the present disclosure is not limited thereto.

[0313] 1. Synthesis of fused polycyclic compounds according to the examples

[0314] First, the synthesis methods of fused polycyclic compounds according to embodiments of the present disclosure will be described in more detail by describing the synthesis methods of compounds 1, 2, 3, 7, 8, 9, 16, 24, 37, and 56 of Examples. Furthermore, in the following description, the synthesis methods of fused polycyclic compounds are provided as examples, but the synthesis methods of fused polycyclic compounds of the present disclosure are not limited to the following examples.

[0315] (1) Synthesis of compound 1

[0316] Compound 1 according to the embodiments can be synthesized via the following reaction process 1:

[0317] Reaction process 1

[0318]

[0319] Synthetic intermediate 1-1

[0320] 3,6-Dibromo-10-phenyl-10H-spiro[acridin-9,9'-fluorene] (1 eq), N1,N1,N3,N3,N5-pentaphenylbenzene-1,3,5-triamine (2.1 eq), tris(dibenzylacetone)dipalladium (0) (0.1 eq), tri-tert-butylphosphine (0.2 eq), and sodium tert-butoxide (4 eq) were dissolved in xylene and stirred at about 150 °C under a nitrogen atmosphere for about 20 hours. After cooling, the resulting mixture was dried under reduced pressure to remove xylene. The product was then washed three times with ethyl acetate and water to obtain an organic layer. The obtained organic layer was dried over MgSO4 and then under reduced pressure. The product was purified by column chromatography (dichloromethane:n-hexane) and recrystallized to obtain intermediate 1-1 (yield: 53%).

[0321] Synthetic compound 1

[0322] Intermediate 1-1 (1 eq) was dissolved in o-dichlorobenzene, and the flask was cooled to approximately 0 °C under a nitrogen atmosphere. BBr3 (4 eq) was then slowly added. After the addition was complete, the temperature was raised to approximately 190 °C, and the mixture was stirred for approximately 24 hours. After cooling to approximately 0 °C, triethylamine was slowly added dropwise to the flask until heating was stopped to terminate the reaction. Hexane was then added to the flask, and the solid was extracted. The extracted solid was obtained by filtration. The obtained solid was purified using a silica filter, and then further purified by recrystallization in MC / Hex to obtain compound 1. The resulting product was then finally purified by sublimation (yield after sublimation: 2.1%).

[0323] (2) Synthesis of compound 2

[0324] Compound 2 according to the embodiments can be synthesized via the following reaction process 2:

[0325] Reaction process 2

[0326]

[0327] Synthetic intermediate 2-1

[0328] 3,6-Dibromo-10-phenyl-10H-spiro[acridin-9,9'-fluorene] (1 eq), 3,5-bis(diphenylamino)phenol (1 eq), CuI (0.2 eq), K₂CO₃ (3 eq), and pyridinecarboxylic acid (0.4 eq) were dissolved in DMF and stirred at approximately 160 °C for approximately 20 hours. After cooling, the resulting mixture was dried under reduced pressure to remove the DMF. The product was then washed with ethyl acetate and water to obtain an organic layer. The obtained organic layer was dried over MgSO₄ and then under reduced pressure. The product was purified by column chromatography (dichloromethane:n-hexane) and recrystallized to obtain intermediate 2-1 (yield: 72%).

[0329] Synthetic intermediate 2-2

[0330] Intermediate 2-1 (1 eq), N1,N1,N3,N3,N5-pentaphenylbenzyl-1,3,5-triamine (2.1 eq), tris(dibenzylacetone)dipalladium (0) (0.05 eq), tri-tert-butylphosphine (0.1 eq), and sodium tert-butoxide (3 eq) were dissolved in toluene and stirred at about 110 °C under a nitrogen atmosphere for about 20 hours. After cooling, the resulting mixture was dried under reduced pressure to remove toluene. The product was then washed three times with ethyl acetate and water to obtain an organic layer. The obtained organic layer was dried over MgSO4 and then under reduced pressure. The product was purified by column chromatography (dichloromethane:n-hexane) and recrystallized to obtain intermediate 2-2. (Yield: 61%)

[0331] Synthetic compound 2

[0332] Compound 2 was obtained in essentially the same manner as compound 1, except that intermediate 2-2 was used.

[0333] (Yield after sublimation: 3%)

[0334] (3) Synthesis of compound 3

[0335] Compound 3 according to the embodiments can be synthesized via the following reaction process 3:

[0336] Reaction process 3

[0337]

[0338] Synthetic intermediate 3-1

[0339] 3,6-Dibromo-10-phenyl-10H-spiro[acridin-9,9'-fluorene] (1 eq), 5-phenoxy-N1,N1,N3-triphenylphenyl-1,3-diamine (1 eq), tris(dibenzylacetone)dipalladium (0) (0.05 eq), tri-tert-butylphosphine (0.1 eq), and sodium tert-butoxide (3 eq) were dissolved in toluene and stirred at about 110 °C under a nitrogen atmosphere for about 20 hours. After cooling, the resulting mixture was dried under reduced pressure to remove toluene. The product was then washed three times with ethyl acetate and water to obtain an organic layer. The obtained organic layer was dried over MgSO4 and then under reduced pressure. The product was purified by column chromatography (dichloromethane:n-hexane) and recrystallized to obtain intermediate 3-1 (yield: 75%).

[0340] Synthetic intermediate 3-2

[0341] Intermediate 3-1 (1 eq), N1,N1,N3,N3,N5-pentaphenylbenzyl-1,3,5-triamine (1.1 eq), tris(dibenzylacetone)dipalladium (0) (0.05 eq), tri-tert-butylphosphine (0.1 eq), and sodium tert-butoxide (3 eq) were dissolved in toluene and stirred at about 110 °C under a nitrogen atmosphere for about 20 hours. After cooling, the resulting mixture was dried under reduced pressure to remove toluene. The product was then washed three times with ethyl acetate and water to obtain an organic layer. The obtained organic layer was dried over MgSO4 and then under reduced pressure. The product was purified by column chromatography (dichloromethane:n-hexane) and recrystallized to obtain intermediate 3-2. (Yield: 66%)

[0342] Synthetic compound 3

[0343] Compound 3 was obtained in essentially the same manner as compound 1, except that intermediate 3-2 was used.

[0344] (Yield after sublimation: 1.5%)

[0345] (4) Synthesis of compound 7

[0346] Compound 7 according to the embodiments can be synthesized via the following reaction procedure 4:

[0347] Reaction process 4

[0348]

[0349] Synthetic intermediate 7-1

[0350] 3',6'-dibromospiro[fluorene-9,9'-xanthon] (1 eq), N1,N1,N3,N3,N5-pentaphenylbenzene-1,3,5-triamine (2.1 eq), tris(dibenzylacetone)dipalladium (0) (0.1 eq), tri-tert-butylphosphine (0.2 eq), and sodium tert-butoxide (4 eq) were dissolved in xylene and stirred at about 150 °C under a nitrogen atmosphere for about 20 hours. After cooling, the resulting mixture was dried under reduced pressure to remove xylene. The product was then washed three times with ethyl acetate and water to obtain an organic layer. The obtained organic layer was dried over MgSO4 and then under reduced pressure. The product was purified by column chromatography (dichloromethane:n-hexane) and recrystallized to obtain intermediate 7-1 (yield: 62%).

[0351] Synthetic compound 7

[0352] Compound 7 was obtained in essentially the same manner as compound 1, except that intermediate 7-1 was used.

[0353] (Yield after sublimation: 3.7%)

[0354] (5) Synthesize compound 8

[0355] Compound 8 according to the embodiments can be synthesized via the following reaction process 5:

[0356] Reaction process 5

[0357]

[0358] Synthetic intermediate 8-1

[0359] 3',6'-dibromospiro[fluorene-9,9'-xanthon] (1 eq), 3,5-bis(diphenylamino)phenol (1 eq), CuI (0.2 eq), K₂CO₃ (3 eq), and pyridinecarboxylic acid (0.4 eq) were dissolved in DMF and stirred at approximately 160 °C for approximately 20 hours. After cooling, the resulting mixture was dried under reduced pressure to remove the DMF. The product was then washed with ethyl acetate and water to obtain an organic layer. The obtained organic layer was dried over MgSO₄ and then under reduced pressure. The product was purified by column chromatography (dichloromethane:n-hexane) and recrystallized to obtain intermediate 8-1 (yield: 63%).

[0360] Synthetic intermediate 8-2

[0361] Intermediate material 8-1 (1 eq), N1,N1,N3,N3,N5-pentaphenylbenzyl-1,3,5-triamine (2.1 eq), tris(dibenzylacetone)dipalladium (0) (0.05 eq), tri-tert-butylphosphine (0.1 eq), and sodium tert-butoxide (3 eq) were dissolved in toluene and stirred at about 110 °C under a nitrogen atmosphere for about 20 hours. After cooling, the resulting mixture was dried under reduced pressure to remove toluene. The product was then washed three times with ethyl acetate and water to obtain an organic layer. The obtained organic layer was dried over MgSO4 and then under reduced pressure. The product was purified by column chromatography (dichloromethane:n-hexane) and recrystallized to obtain intermediate 8-2. (Yield: 59%)

[0362] Synthetic compound 8

[0363] Compound 8 was obtained in essentially the same manner as the synthesis of compound 1, except that intermediate 8-2 was used.

[0364] (Yield after sublimation: 4.2%)

[0365] (6) Synthesis of compound 9

[0366] Compound 9 according to the embodiments can be synthesized via the following reaction process 6:

[0367] Reaction process 6

[0368]

[0369] Synthetic intermediate 9-1

[0370] 3',6'-dibromospiro[fluorene-9,9'-xanthon] (1 eq), 5-phenoxy-N1,N1,N3-triphenylbenzene-1,3-diamine (1 eq), tris(dibenzylacetone)dipalladium (0) (0.05 eq), tri-tert-butylphosphine (0.1 eq), and sodium tert-butoxide (3 eq) were dissolved in toluene and stirred at about 110 °C under a nitrogen atmosphere for about 20 hours. After cooling, the resulting mixture was dried under reduced pressure to remove toluene. The product was then washed three times with ethyl acetate and water to obtain an organic layer. The obtained organic layer was dried over MgSO4 and then under reduced pressure. The product was purified by column chromatography (dichloromethane:n-hexane) and recrystallized to obtain intermediate 9-1 (yield: 79%).

[0371] Synthetic intermediate 9-2

[0372] Intermediate 9-1 (1 eq), N1,N1,N3,N3,N5-pentaphenylbenzyl-1,3,5-triamine (1.1 eq), tris(dibenzylacetone)dipalladium (0) (0.05 eq), tri-tert-butylphosphine (0.1 eq), and sodium tert-butoxide (3 eq) were dissolved in toluene and stirred at about 110 °C under a nitrogen atmosphere for about 20 hours. After cooling, the resulting mixture was dried under reduced pressure to remove toluene. The product was then washed three times with ethyl acetate and water to obtain an organic layer. The obtained organic layer was dried over MgSO4 and then under reduced pressure. The product was purified by column chromatography (dichloromethane:n-hexane) and recrystallized to obtain intermediate 9-2. (Yield: 65%)

[0373] Synthetic compound 9

[0374] Compound 9 was obtained in essentially the same manner as compound 1, except that intermediate 9-2 was used.

[0375] (Yield after sublimation: 1.7%)

[0376] (7) Synthesize compound 16

[0377] Compound 16 according to the embodiments can be synthesized via, for example, the steps shown in the following reaction flow 7:

[0378] Reaction process 7

[0379]

[0380] Synthetic intermediate 16-1

[0381] 3',6'-dibromospiro[fluorene-9,9'-thioxanthracene] (1 eq), N1,N3-bis([1,1'-biphenyl]-2-yl)-N1,N3,N5-triphenylbenzene-1,3,5-triamine (1 eq), CuI (0.2 eq), K2CO3 (3 eq), and pyridinecarboxylic acid (0.4 eq) were dissolved in DMF and stirred at approximately 160 °C for approximately 20 hours. After cooling, the resulting mixture was dried under reduced pressure to remove the DMF. The product was then washed with ethyl acetate and water to obtain an organic layer. The obtained organic layer was dried over MgSO4 and then under reduced pressure. The product was purified by column chromatography (dichloromethane:n-hexane) and recrystallized to obtain intermediate 16-1 (yield: 52%).

[0382] Synthetic intermediate 16-2

[0383] N1,N3-bis([1,1'-biphenyl]-2-yl)-N5-(3'-bromospiro[fluorene-9,9'-thioxanthracene]-6'-yl)-N1,N3,N5-triphenylphenyl-1,3,5-triamine (intermediate 16-1) (1 eq), N1,N1,N3,N3,N5-pentaphenylphenyl-1,3,5-triamine (1 eq), tris(dibenzylacetone)dipalladium (0) (0.05 eq), tri-tert-butylphosphine (0.1 eq), and sodium tert-butoxide (3 eq) were dissolved in toluene and then stirred at about 110 °C under a nitrogen atmosphere for about 20 hours. After cooling, the resulting mixture was dried under reduced pressure to remove toluene. The product was then washed three times with ethyl acetate and water to obtain an organic layer. The obtained organic layer was dried over MgSO4 and then under reduced pressure. The product was purified by column chromatography (dichloromethane:n-hexane) and recrystallized to obtain intermediate 16-2. (Yield: 70%)

[0384] Synthetic compound 16

[0385] Compound 16 was obtained in essentially the same manner as compound 1, except for the use of intermediate 16-2. (Yield after sublimation: 2.7%)

[0386] (8) Synthesize compound 24

[0387] Compound 24 according to the embodiments can be synthesized via, for example, the steps shown in the following reaction flow 8:

[0388] Reaction process 8

[0389]

[0390] Synthetic intermediate 24-1

[0391] 3,6-Dibromo-10-phenyl-10H-spiro[acridin-9,9'-fluorene] (1 eq), N1-([1,1'-biphenyl]-2-yl)-5-phenoxy-N1,N3-diphenylphenyl-1,3-diamine (1 eq), tris(dibenzylacetone)dipalladium (0) (0.05 eq), tri-tert-butylphosphine (0.1 eq), and sodium tert-butoxide (3 eq) were dissolved in toluene and stirred at about 110 °C under a nitrogen atmosphere for about 20 hours. After cooling, the resulting mixture was dried under reduced pressure to remove toluene. The product was then washed three times with ethyl acetate and water to obtain an organic layer. The obtained organic layer was dried over MgSO4 and then under reduced pressure. The product was purified by column chromatography (dichloromethane:n-hexane) and recrystallized to obtain intermediate 24-1 (yield: 65%).

[0392] Synthetic intermediate 24-2

[0393] N1-([1,1'-biphenyl]-2-yl)-N3-(3-bromo-10-phenyl-10H-spiro[acridin-9,9'-fluorene]-6-yl)-5-phenoxy-N1,N3-diphenylphenyl-1,3-diamine (intermediate 24-1) (1 eq), 5-(tert-butyl)-N1,N1,N3-triphenylphenyl-1,3-diamine (1 eq), tris(dibenzylacetone)dipalladium (0) (0.05 eq), tri-tert-butylphosphine (0.1 eq), and sodium tert-butoxide (3 eq) were dissolved in toluene and then stirred at about 110 °C under a nitrogen atmosphere for about 20 hours. After cooling, the resulting mixture was dried under reduced pressure to remove toluene. The product was then washed three times with ethyl acetate and water to obtain an organic layer. The obtained organic layer was dried over MgSO4 and then under reduced pressure. The product was purified by column chromatography (dichloromethane:n-hexane) to obtain intermediate 24-2. (Yield: 55%)

[0394] Synthetic compound 24

[0395] Intermediate 24-2 (1 eq) was dissolved in o-dichlorobenzene, and the flask was cooled to approximately 0°C under a nitrogen atmosphere. BBr3 (4 eq) was then slowly added. After the dropwise addition of BBr3 was complete, the temperature was raised to approximately 150°C, and the mixture was stirred for approximately 6 hours. After cooling to 0°C, triethylamine was slowly added dropwise to the flask until heating was stopped to terminate the reaction. Hexane was then added to the flask, and the solid was extracted. The extracted solid was obtained by filtration. The obtained solid was purified using a silica filter, and then further purified by recrystallization in MC / Hex to obtain compound 24. The resulting product was then finally purified by sublimation purification. (Yield after sublimation: 1.1%)

[0396] (9) Synthetic compound 37

[0397] Compound 37 according to the embodiments can be synthesized via, for example, the steps shown in the following reaction flow 9:

[0398] Reaction process 9

[0399]

[0400] Synthetic intermediate 37-1

[0401] 3,6-Dibromo-10H-spiro[acridin-9,9'-fluorene] (1 eq), 2'-fluoro-1,1':3',1”-terphenyl (1.3 eq), and Cs₂CO₃ (3 eq) were dissolved in DMF and then stirred in a high-pressure reactor at approximately 150 °C for approximately 20 hours. After cooling, the resulting mixture was dried under reduced pressure to remove DMF. The product was then washed three times with ethyl acetate and water to obtain an organic layer. The obtained organic layer was dried over MgSO₄ and then under reduced pressure. The product was purified by column chromatography (dichloromethane:n-hexane) to obtain intermediate 37-1 (yield: 42%).

[0402] Synthetic intermediate 37-2

[0403] 10-([1,1':3',1”-terphenyl]-2'-yl)-3,6-dibromo-10H-spiro[acridin-9,9'-fluorene](intermediate 37-1) (1 eq), N1,N1,N3,N3,N5-pentaphenylbenzene-1,3,5-triamine (2.1 eq), tris(dibenzylacetone)dipalladium (0) (0.05 eq), tri-tert-butylphosphine (0.1 eq), and sodium tert-butoxide (3 eq) were dissolved in toluene and stirred at about 110 °C under a nitrogen atmosphere for about 20 hours. After cooling, the resulting mixture was dried under reduced pressure to remove toluene. The product was then washed three times with ethyl acetate and water to obtain an organic layer. The obtained organic layer was dried over MgSO4 and then under reduced pressure. The product was purified by column chromatography (dichloromethane:n-hexane) and recrystallized to obtain intermediate 37-2. (Yield: 61%)

[0404] Synthetic compound 37

[0405] Compound 37 was obtained in essentially the same manner as compound 1, except for the use of intermediate 37-2. (Yield after sublimation: 1.4%)

[0406] (10) Synthetic compound 56

[0407] Compound 56 according to the embodiments can be synthesized via, for example, the steps shown in the following reaction flow 10:

[0408] Reaction process 10

[0409]

[0410] Synthetic intermediate 56-1

[0411] 3',6'-dibromospiro[fluorene-9,9'-xanthon] (1 eq), 3,5-bis([1,1'-biphenyl]-2-yl(phenyl)amino)phenol (1 eq), CuI (0.2 eq), K₂CO₃ (3 eq), and pyridinecarboxylic acid (0.4 eq) were dissolved in DMF and stirred at approximately 160 °C for approximately 20 hours. After cooling, the resulting mixture was dried under reduced pressure to remove DMF. The product was then washed with ethyl acetate and water to obtain an organic layer. The obtained organic layer was dried over MgSO₄ and then under reduced pressure. The product was purified by column chromatography (dichloromethane:n-hexane) and recrystallized to obtain intermediate 56-1 (yield: 59%).

[0412] Synthetic intermediate 56-2

[0413] The following compounds were prepared: N1,N3-bis([1,1'-biphenyl]-2-yl)-5-((3'-bromospiro[fluorene-9,9'-xanthon]-6'-yl)oxy)-N1,N3-diphenylphenyl-1,3-diamine (intermediate 56-1) (1 eq), N1-([1,1':3',1”-terphenyl]-2'-yl)-N3,N3,N5,N5-tetraphenylphenyl-1,3,5-triamine (1.2 eq), and tris(dibenzylacetone)dipalladium (0) (0.05 eq). 0.1 eq of tri-tert-butylphosphine and 3 eq of sodium tert-butoxide were dissolved in xylene and then stirred in a high-pressure reactor at approximately 150 °C for about 20 hours. After cooling, the resulting mixture was dried under reduced pressure to remove the xylene. The product was then washed three times with ethyl acetate and water to obtain an organic layer. The obtained organic layer was dried over MgSO4 and then under reduced pressure. The product was purified by column chromatography (dichloromethane:n-hexane) and recrystallized to obtain intermediate 56-2 (yield: 36%).

[0414] Synthetic compound 56

[0415] Compound 56 was obtained in essentially the same manner as compound 1, except for the use of intermediate 56-2. (Yield after sublimation: 1.2%)

[0416] The molecular weights and NMR analysis results of the synthesized compounds 1, 2, 3, 7, 8, 9, 16, 24, 37 and 56 are shown in Table 1 below.

[0417] Table 1

[0418]

[0419] 2. Manufacturing light-emitting devices

[0420] As the anode, approximately 15Ω / cm will be manufactured by Corning Incorporated. 2 (about The ITO glass substrate was cut into 50mm x 50mm x 0.7mm dimensions, ultrasonically cleaned with isopropyl alcohol and pure water for about 5 minutes, then irradiated with ultraviolet light for about 30 minutes and exposed to ozone for cleaning. The ITO glass substrate was then mounted on a vacuum deposition equipment.

[0421] NPB is vacuum deposited on top of an ITO anode formed on a glass substrate to form... A thick hole injection layer is formed, and then TCTA is vacuum deposited on top of the hole injection layer to create a thick hole injection layer. A thick hole transport layer.

[0422] CzSi, serving as a hole transport compound, was vacuum deposited on top of the hole transport layer to form... A thick launch aid layer.

[0423] Next, when forming the emitter layer, mCP is used as the host material, and the fused polycyclic compound of the embodiment or the comparative compound is used as the dopant material. The host and dopant are co-deposited at a weight ratio of approximately 99:1 to form A thick emission layer. That is, the emission layer formed by co-deposition is deposited by mixing mCBP with each of the compound compounds 1, 2, 3, 7, 8, 9, 16, 24, 37 and 56 of Examples 1 to 10, respectively, and by mixing mCP with each of the comparative compound compounds C1 to C4 of Comparative Examples 1 to 4, respectively.

[0424] Subsequently, TSPO1 was deposited on the upper part of the emitter layer to form A thick electron transport layer is formed, and then TPBi, as a buffer electron transport compound, is deposited on top of the electron transport layer to form a thick electron transport layer. A thick buffer layer.

[0425] LiF, as an alkali halide metal, is deposited on the upper part of the buffer layer to form... A thick electron-injected layer is formed, and Al is vacuum-deposited to create... Thick LiF / Al electrodes are used to fabricate light-emitting devices.

[0426] Some of the materials used in the above-mentioned light-emitting device can be represented by the following formula:

[0427]

[0428] The compounds used in Examples 1 to 10 and Comparative Examples 1 to 4 are listed in Table 2.

[0429] Table 2

[0430]

[0431]

[0432]

[0433] 3. Evaluate the energy levels of the compound.

[0434] Table 3 shows the lowest triplet excitation level (hereinafter, T1 level), lowest singlet excitation level (hereinafter, S1 level), and energy level difference (S1-T1, hereinafter, ΔE) between S1 and T1 for the compounds of Examples 1 to 10 and Comparative Examples 1 to 4. ST ).

[0435] Table 3

[0436]

[0437]

[0438] Referring to the results in Table 3, the T1 levels of the compounds in Examples 1 to 10 were 2.60 eV or higher, and the T1 levels of the compounds in Comparative Examples 1 to 4 were 2.59 eV or lower. Therefore, the compounds in Examples 1 to 10 have a higher T1 level than the compounds in Comparative Examples 1 to 4. l Higher level T l level.

[0439] The compounds of Examples 1 to 10 had an S1 level of 2.77 eV or higher, while the compounds of Comparative Examples 1 to 4 had an S1 level of 2.74 eV or lower. Therefore, the compounds of Examples 1 to 10 have a higher S1 level than the compounds of Comparative Examples 1 to 4. l Higher level S l level.

[0440] The compounds in Examples 1 to 10 have a ΔE of 0.142 eV. ST The average value, and the compounds of Comparative Examples 1 to 4 have a ΔE of 0.15 eV. ST average value.

[0441] Although this disclosure is not limited to any particular mechanism or theory, it is believed that the comparative example compounds C1 to C3 do not include a spirostructure capable of increasing the multiple resonance effect, and therefore have a lower T1 level and a larger ΔE compared to the embodiments of this disclosure. ST Furthermore, it is believed that comparative compound C4 includes a spirostructure but only one boron atom, and therefore has a lower T1 level and a larger ΔE compared to embodiments of this disclosure that include a spirostructure and two boron atoms. ST value.

[0442] The compounds of Examples 1 to 10 comprise fused structures containing a spirostructure and two boron atoms, thus allowing for increased conjugation within the molecule (fused polycyclic compound) and enhanced multiple resonance effects. Consequently, the compounds of Examples 1 to 10 exhibit high T1 levels and low ΔE. ST It has an average value and can exhibit high luminous efficiency when applied to light-emitting devices.

[0443] 4. Evaluate the properties of the light-emitting device

[0444] The emission characteristics of the fused polycyclic compounds of the embodiments and the light-emitting devices of the embodiments including the fused polycyclic compounds of the embodiments in the emission layer are evaluated as follows. A method for manufacturing the light-emitting device used for device evaluation is described below.

[0445] The fused polycyclic compounds of Examples 1, 2, 3, 7, 8, 9, 16, 24, 37 and 56 were used as dopant materials for the emission layer to manufacture the light-emitting devices of Examples 1 to 10.

[0446] Comparative compound C1, C2, C3 and C4 were used as dopant materials for the emission layer to manufacture the light-emitting devices of Comparative Examples 1 to 4.

[0447] The evaluation results of the light-emitting devices of Examples 1 to 10 and Comparative Examples 1 to 4 are listed in Table 4. Table 4 lists the driving voltage (V), luminous efficiency (Cd / A), maximum quantum efficiency (%), and emission color of the manufactured light-emitting devices in the emission wavelength region.

[0448] The materials used for the hole transport layer in Table 4 are the same as those below.

[0449]

[0450] Table 4

[0451]

[0452]

[0453] Referring to the results in Table 4, it can be seen that, compared with the light-emitting devices of Comparative Examples 1 to 3, the light-emitting devices of Examples 1 to 10 have a lower average driving voltage, higher luminous efficiency, and higher maximum quantum efficiency. Comparative Example compounds C1, C2, and C3 each have a fused polycyclic structure containing boron atoms, but do not contain a separate helical structure. Therefore, compared with the embodiments of this disclosure that include helical structures, Comparative Example compounds C1, C2, and C3 exhibit lower multiple resonance effects and molecular stabilization effects.

[0454] Compared to the example compounds that include two boron atoms, comparative example compound C1 includes one boron atom, and therefore can have lower molecular multiple resonance effects and stabilizing effects than the example compounds of the embodiments of the present disclosure. As can be seen in Table 4, comparative example compound C1 has a higher driving voltage than the example compounds of the embodiments of the present disclosure, and lower luminous efficiency and maximum quantum efficiency than the example compounds of the embodiments of the present disclosure.

[0455] The fused polycyclic compound included in the light-emitting device of the embodiments of this disclosure includes two boron atoms, heteroatoms such as N, O, S and Se, and a spiro structure to reduce intramolecular interactions and increase bond dissociation energy, thereby increasing molecular stability and improving device characteristics such as luminous efficiency and maximum quantum efficiency.

[0456] The light-emitting device of the embodiment may include the fused polycyclic compound of the embodiment in the emitting layer to exhibit high luminous efficiency in the blue emission wavelength region.

[0457] The light-emitting device according to embodiments of this disclosure may have low driving voltage, excellent luminous efficiency, and improved maximum quantum efficiency.

[0458] Although the subject matter of this disclosure has been described with reference to exemplary embodiments thereof, it should be understood that this disclosure should not be limited to the exemplary embodiments, but that various changes and modifications can be made by those skilled in the art without departing from the spirit and scope of this disclosure.

[0459] Therefore, the scope of this disclosure is not intended to be limited to what is set forth in the detailed description of the specification, but is intended to be defined by the appended claims and their equivalents.

Claims

1. A fused polycyclic compound represented by Formula 1: Formula 1 in, In Equation 1, X1 to X5 are each independently NR9, O, S or Se. R1 to R9 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted amino group, or a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms. a is an integer selected from 0 to 3. b and c are each an independent integer selected from 0 to 2. d is an integer selected from 0 to 3. e, f, g, and h are each independently an integer selected from 0 to 4, and The term "substituted or unsubstituted" means either unsubstituted or substituted with at least one substituent selected from the group consisting of: deuterium atom, halogen atom, straight-chain alkyl having 1 to 50 carbon atoms, branched alkyl having 1 to 50 carbon atoms, straight-chain alkoxy having 1 to 20 carbon atoms, branched alkoxy having 1 to 20 carbon atoms, and aryl having 6 to 30 cyclic carbon atoms.

2. The fused polycyclic compound of claim 1, wherein the fused polycyclic compound represented by formula 1 is represented by formula 1-1a or formula 1-1b: Formula 1-1a Formula 1-1b in, In equations 1-1a and 1-1b, X1 to X5, R1 to R -9 a to h are the same as those defined in Equation 1.

3. The fused polycyclic compound of claim 1, wherein the fused polycyclic compound represented by formula 1 is represented by any one selected from formulas 1-2a to 1-2d: Formula 1-2a Formula 1-2b Formula 1-2c Equation 1-2d in, In equations 1-2a to 1-2d, X1, X3 to X5, R1 to R9 and a to h are the same as those defined in Equation 1.

4. The fused polycyclic compound of claim 1, wherein the fused polycyclic compound represented by formula 1 is represented by formulas 1-3: Formula 1-3 in, In Equation 1-3, X1 to X5, R1, R4 to R9, a and d to h are the same as those defined in Equation 1.

5. The fused polycyclic compound of claim 1, wherein the fused polycyclic compound represented by formula 1 is represented by formulas 1-4: Formula 1-4 in, In equation 1-4, X1 to X5, R1 to R5, R8, R9, a to e, and h are the same as those defined in Equation 1.

6. The fused polycyclic compound of claim 1, wherein the fused polycyclic compound represented by formula 1 is represented by formulas 1-5: Formula 1-5 in, In Equation 1-5, X1 to X5, R1 to R4, R6, R7, R9, a to d, f and g are the same as those defined in Equation 1.

7. The fused polycyclic compound of claim 1, wherein the fused polycyclic compound represented by formula 1 is represented by formulas 1-6: Formula 1-6 in, In Equations 1-6, X1 to X5, R1, R4, R9, a and d are the same as those defined in Equation 1.

8. The fused polycyclic compound of claim 1, wherein at least one selected from R1 and R4 is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms or a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, and Each of R2, R3, R5, R6, R7, and R8 is a hydrogen atom.

9. The fused polycyclic compound of claim 1, wherein the fused polycyclic compound represented by formula 1 is at least one selected from the group of compounds represented by compound group 1: Compound group 1 10. A light-emitting device, comprising: First electrode; The second electrode facing the first electrode; as well as Multiple organic layers between the first electrode and the second electrode The first electrode and the second electrode each independently comprise at least one selected from Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF, Mo, Ti, In, Sn, Zn, Yb, and W, two or more of these compounds, mixtures of two or more of these compounds, or oxides thereof, or the first electrode and the second electrode each independently comprise a material with a multilayer structure of LiF / Ca or LiF / Al. At least one organic layer selected from the plurality of organic layers includes a fused polycyclic compound represented by Formula 1 as described in any one of claims 1 to 9.

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