Light-emitting device

Abstract

The light-emitting device includes a first electrode, a second electrode, and an emitting layer between the first electrode and the second electrode, comprising at least one polycyclic compound represented by Formula 1, thereby exhibiting a long lifespan. In Formula 1, the substituents are the same as defined in the detailed description. Formula 1

Description

[0001] Cross-references to related applications

[0002] This application claims priority and benefit to Korean Patent Application No. 10-2020-0150493, filed with the Korean Intellectual Property Office on November 11, 2020, the entire contents of which are incorporated herein by reference. Technical Field

[0003] This disclosure relates to light-emitting devices. Background Technology

[0004] Recently, there has been active development of organic electroluminescent displays as image display devices. Unlike liquid crystal displays, organic electroluminescent displays are so-called self-emissive display devices, in which holes and electrons injected from the first and second electrodes recombine in the emitting layer, and thus the luminescent material containing organic compounds in the emitting layer emits light to achieve display (e.g., displaying images).

[0005] In applications from light-emitting devices to display devices, there is an expectation (e.g., demand) for light-emitting devices with low driving voltage, high luminous efficiency, and long lifespan, and the development of materials for light-emitting devices that can reliably achieve such characteristics is ongoing. Summary of the Invention

[0006] The implementation of the present disclosure relates to a light-emitting device with a long service life.

[0007] According to an embodiment of this disclosure, the light-emitting device includes: a first electrode; a second electrode on the first electrode; and an emitting layer between the first electrode and the second electrode, comprising a polycyclic compound represented by Formula 1, wherein the first electrode and the second electrode each independently comprise any one, two or more compounds, a mixture of two or more compounds, or oxides of Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF, Mo, Ti, W, In, Sn, Zn.

[0008] Formula 1

[0009]

[0010] In Equation 1, X1 to X4 are each independently O, S, Se, or NR1, Z1 and Z2 are each independently CR2, a1 and a2 are each independently integers from 0 to 2, and R y1 and R y2Each of the following is independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkoxy 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.

[0011] R1 and R2 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted oxy group, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, a substituted or unsubstituted thio group, or a portion represented by Formula A, and / or bonded to adjacent groups to form a ring, and at least one selected from X1 to X4, Z1, and Z2 containing the portion represented by Formula A:

[0012] Formula A

[0013]

[0014] In formula A, Ra is a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkoxy 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; L1 is a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, or a substituted or unsubstituted divalent amine group; p can be 0 or 1; and "--*" indicates the position to be connected.

[0015] In the implementation scheme, the portion represented by formula A can be represented by any one of formulas A-1 to A-4:

[0016] Formula A-1

[0017]

[0018] Formula A-2

[0019]

[0020] Formula A-3

[0021]

[0022] Formula A-4

[0023]

[0024] In Equation A-3, m is 0 or 1, and in Equations A-1 to A-4, Ra and “--*” are the same as defined with respect to Equation A.

[0025] In the implementation scheme, the portion represented by formula A-1 can be represented by formula AA-1 or formula AA-2:

[0026] Formula AA-1

[0027]

[0028] Formula AA-2

[0029]

[0030] In equations AA-1 and AA-2, Ra and “——*” are the same as those defined with respect to equation A.

[0031] In the implementation scheme, the portion represented by formula A-2 can be represented by any one of formulas B-1 to B-3:

[0032] Formula B-1

[0033]

[0034] Formula B-2

[0035]

[0036] Formula B-3

[0037]

[0038] In equations B-1 to B-3, Ra and "--*" are the same as those defined with respect to equation A.

[0039] The portion represented by equation A-3 can be represented by equation C-1 or equation C-2:

[0040] Formula C-1

[0041]

[0042] Formula C-2

[0043]

[0044] In equations C-1 and C-2, Ra and "--*" are the same as those defined with respect to equation A.

[0045] In the implementation scheme, Ra can be an unsubstituted phenyl group or an unsubstituted naphthyl group.

[0046] In the embodiments, the lowest triplet excitation energy of the polycyclic compound may be about 1.8 eV or less.

[0047] In an implementation, the emitter layer may comprise a dopant and a host, and the dopant may comprise the polycyclic compound represented by Formula 1.

[0048] In an embodiment, the light-emitting device may further include a capping layer on the second electrode, wherein the capping layer may have a refractive index of about 1.6 or greater than 1.6.

[0049] In an embodiment, the polycyclic compound represented by Formula 1 can emit thermally activated delayed fluorescence.

[0050] In the implementation scheme, the emitting layer can emit blue light.

[0051] In an embodiment, the emission layer may comprise at least one compound represented by compound group 1:

[0052] Compound group 1

[0053]

[0054]

[0055]

[0056]

[0057]

[0058]

[0059]

[0060]

[0061]

[0062] In embodiments of this disclosure, the light-emitting device includes: a first electrode; a second electrode on the first electrode; and an emitting layer between the first electrode and the second electrode comprising a polycyclic compound represented by Formula 2, wherein the first electrode and the second electrode each independently comprise any one, two or more compounds, mixtures of two or more compounds, or oxides of Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF, Mo, Ti, W, In, Sn, Zn.

[0063] Formula 2

[0064]

[0065] In Equation 2, X1 to X4 are each independently O, S, Se, or NR1, and R1 is... Hydrogen atom, deuterium atom, cyano group, nitro group, substituted or unsubstituted silyl group, substituted or unsubstituted amine group, substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, and n is an integer from 0 to 8, and when R1 is not in NR1 When n is an integer from 1 to 8, and when n is 0, at least one of X1 to X4 is NR1, where R1 is And a is an integer from 0 to 8-n, p is 0 or 1, L1 is a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, or a substituted or unsubstituted divalent amine group, and R y Each of Ra is independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkoxy 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, and / or bonded to an adjacent group to form a ring, and “—*” indicates the position to be connected.

[0066] In the implementation scheme, the compound represented by Formula 2 may be represented by any one of Formulas 3 to 5:

[0067] Formula 3

[0068]

[0069] Formula 4

[0070]

[0071] Formula 5

[0072]

[0073] In Formulas 4 and 5, L2 and L3 can each independently be a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, or a substituted or unsubstituted divalent amine group. In Formula 5, Ra1 and Ra2 can each independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkoxy 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. In Formulas 3 to 5, a, R y X1 to X4 are the same as those defined with respect to Equation 2, and in Equation 4, Ra is the same as those defined with respect to Equation 2.

[0074] In the implementation plan, in Equation 2, It can be represented by any one of Equations 6 to 9:

[0075] Formula 6

[0076]

[0077] Formula 7

[0078]

[0079] Formula 8

[0080] as well as

[0081] Formula 9

[0082]

[0083] In Equation 8, m is 0 or 1, and in Equations 6 through 9, Ra and “--*” are the same as defined with respect to Equation 2.

[0084] In the implementation scheme, the portion represented by Equation 6 can be represented by Equation 6-1 or Equation 6-2:

[0085] Formula 6-1

[0086]

[0087] Formula 6-2

[0088]

[0089] In Equations 6-1 and 6-2, Ra and “——*” are the same as those defined with respect to Equation 2.

[0090] In the implementation scheme, the portion represented by Equation 7 can be represented by any one of Equations 7-1 to 7-3:

[0091] Equation 7-1

[0092]

[0093] Equation 7-2

[0094]

[0095] Formula 7-3

[0096]

[0097] In Equations 7-1 to 7-3, Ra and “——*” are the same as those defined with respect to Equation 2.

[0098] In the implementation scheme, the portion represented by Equation 8 can be represented by Equation 8-1 or Equation 8-2:

[0099] Formula 8-1

[0100]

[0101] Formula 8-2

[0102]

[0103] In Equations 8-1 and 8-2, Ra and “——*” are the same as those defined with respect to Equation 2.

[0104] In the implementation scheme, in Formula 2, Ra can be an unsubstituted phenyl group or an unsubstituted naphthyl group.

[0105] In the embodiments, the lowest triplet excitation energy of the polycyclic compound may be about 1.8 eV or less.

[0106] In an embodiment, the emission layer may comprise at least one compound represented by compound group 1:

[0107] Compound group 1

[0108]

[0109]

[0110]

[0111]

[0112]

[0113]

[0114]

[0115]

[0116] Attached Figure Description

[0117] The accompanying drawings are included to provide a further understanding of the subject matter of this disclosure, and are incorporated in and form part of this specification. The drawings illustrate exemplary embodiments of this disclosure and, together with the description, serve to explain the principles of this disclosure.

[0118] In the attached diagram:

[0119] Figure 1 This is a plan view of a display device according to an embodiment of this disclosure;

[0120] Figure 2 This is a cross-sectional view of a display device according to an embodiment of this disclosure;

[0121] Figure 3 This is a schematic cross-sectional view illustrating an embodiment of the light-emitting device according to the present disclosure;

[0122] Figure 4 This is a schematic cross-sectional view illustrating an embodiment of the light-emitting device according to the present disclosure;

[0123] Figure 5 This is a schematic cross-sectional view illustrating an embodiment of the light-emitting device according to the present disclosure;

[0124] Figure 6 This is a schematic cross-sectional view illustrating an embodiment of the light-emitting device according to the present disclosure;

[0125] Figure 7 This is a cross-sectional view of a display device according to an embodiment of this disclosure; and

[0126] Figure 8This is a cross-sectional view of a display device according to an embodiment of the present disclosure. Detailed Implementation

[0127] The subject matter of this disclosure can be modified in many alternative forms, and therefore specific embodiments will be shown and described in more detail in the accompanying drawings. However, it should be understood that this disclosure is not intended to limit it to the specific forms disclosed, but rather to cover all modifications, equivalents, and substitutions falling within the spirit and scope of this invention.

[0128] When interpreting each drawing, the same reference numerals are used to refer to the same elements. In the drawings, for clarity of this disclosure, the dimensions of each structure may be illustrated enlarged. It should be understood that although the terms "first," "second," etc., may be used herein to describe various elements, these elements should not be limited by these terms. These terms are 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.

[0129] In this application, it should be understood that terms such as “comprising” or “having” indicate the presence of features, fixed figures, steps, processes, elements, components or combinations thereof disclosed in this specification, but do not preclude the presence or addition of one or more other features, fixed figures, steps, processes, elements, components or combinations thereof.

[0130] In this application, when a layer, film, region, or plate is referred to as being "above" or "in the upper part" of another layer, film, region, or plate, it can be located not only directly on the layer, film, region, or plate, but also in an intermediate layer, film, region, or plate. Conversely, when a layer, film, region, or plate is referred to as being "below" or "in the lower part" of another layer, film, region, or plate, it can be located not only directly below the layer, film, region, or plate, but also in an intermediate layer, film, region, or plate. Furthermore, 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 located not only on the layer, film, region, or plate, but also below the layer, film, region, or plate.

[0131] In this specification, the term "substituted or unsubstituted" can refer to a substance substituted or unsubstituted by at least one substituent selected from the group consisting of deuterium, halogen, cyano, nitro, amino, silyl, oxy, thio, sulfinyl, sulfonyl, carbonyl, boron, phosphine oxide, phosphine sulfide, alkyl, alkenyl, alkynyl, alkoxy, cyclic, aryl, and heterocyclic groups. Furthermore, each of the described substituents can be substituted or unsubstituted. For example, a biphenyl group can be interpreted as an aryl group or a phenyl group substituted with a phenyl group.

[0132] In the specification, the phrase "bonded to adjacent groups to form a ring" can mean that a group bonds to an adjacent group to form a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocycle. Hydrocarbon rings include aliphatic hydrocarbon rings and aromatic hydrocarbon rings. Heterocycles include aliphatic heterocycles and aromatic heterocycles. Hydrocarbon rings and heterocycles can be monocyclic or polycyclic. Furthermore, a ring formed by bonding adjacent groups to each other can connect to another ring to form a spirostructure.

[0133] In this specification, the term "adjacent group" can refer to a substituent that substitutes for an atom directly bonded to the atom substituted by the corresponding substituent, another substituent that substitutes for the atom substituted by the corresponding substituent, or a substituent spatially located at the position 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. Furthermore, the two methyl groups in 4,5-dimethylphenanthrene can be interpreted as "adjacent groups" to each other.

[0134] In the specification, examples of halogen atoms may include fluorine atoms, chlorine atoms, bromine atoms, or iodine atoms.

[0135] In the specification, the alkyl group can be straight-chain, branched, or cyclic (e.g., straight-chain alkyl group, branched alkyl group, or cyclic alkyl group). The number of carbon atoms in the alkyl group is 1 to 50, 1 to 30, 1 to 20, 1 to 10, or 1 to 6. Examples of alkyl groups may include methyl groups, ethyl groups, n-propyl groups, isopropyl groups, n-butyl groups, sec-butyl groups, tert-butyl groups, isobutyl groups, 2-ethylbutyl groups, 3,3-dimethylbutyl groups, n-pentyl groups, isopentyl groups, neopentyl groups, tert-pentyl groups, cyclopentyl groups, 1-methylpentyl groups, 3-methylpentyl groups, 2-ethylpentyl groups, 4-methyl-2-pentyl groups, n-hexyl groups, 1-methylhexyl groups, and 2-ethylhexyl groups. 2-Butylhexyl group, cyclohexyl group, 4-methylcyclohexyl group, 4-tert-butylcyclohexyl group, n-heptyl group, 1-methylheptyl group, 2,2-dimethylheptyl group, 2-ethylheptyl group, 2-butylheptyl group, n-octyl group, tert-octyl group, 2-ethyloctyl group, 2-butyloctyl group, 2-hexyloctyl group, 3,7-dimethyloctyl group, cyclooctyl group, n-nonyl group, n-decyl group, adamantyl group, 2-ethyldecyl group, 2-butyl Decyl groups, 2-hexyldecyl groups, 2-octyldecyl groups, n-undecyl groups, n-dodecyl groups, 2-ethyldodecyl groups, 2-butyldodecyl groups, 2-hexyldodecyl groups, 2-octyldodecyl groups, n-tridecyl groups, n-tetradecyl groups, n-pentadecanyl groups, n-hexadecyl groups, 2-ethylhexadecyl groups, 2-butylhexadecyl groups, 2-hexylhexadecyl groups, 2-octylhexadecyl groups, n-heptadecyl groups, n-octadecyl groups, n-octadecyl groups, n-heptadecyl groups, n-octadecyl groups, n-heptadecyl groups, n-octadecyl groups, n-hexa ...

[0136] As used herein, the term "hydrocyclic group" can refer to any functional group or substituent derived from an aliphatic hydrocarbon ring. A hydrocyclic group can be a saturated hydrocyclic group having 5 to 20 cyclic carbon atoms.

[0137] As used herein, the term "aryl group" can refer to any functional group or substituent derived from an aromatic hydrocarbon ring. An aryl group can be a monocyclic or polycyclic aryl group. 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 groups, naphthyl groups, fluorenyl groups, anthraceneyl groups, phenanthrene groups, biphenyl groups, triphenyl groups, tetraphenyl groups, pentaphenyl groups, hexaphenyl groups, benzo[a]phenanthrene groups, pyrene groups, benzo[a]fluoranyl anthracene groups, etc. The embodiments disclosed herein are not limited to basic groups, etc.

[0138] In the specification, the fluorenyl group may be substituted, and two substituents may bond to each other to form a spirostructure. Examples of substituted fluorenyl groups are as follows. However, embodiments of this disclosure are not limited thereto.

[0139]

[0140] As used herein, the term "heterocyclic group" can refer to any functional group or substituent derived from a ring containing at least one of B, O, N, P, Si, and S (e.g., 1 to 15, 1 to 10, 1 to 5, or 1 to 3 heteroatoms) as a heteroatom. Heterocyclic groups include aliphatic heterocyclic groups and aromatic heterocyclic groups. Aromatic heterocyclic groups can be heteroaryl groups. Aliphatic and aromatic heterocycles can be monocyclic or polycyclic.

[0141] In the specification, the heterocyclic group may contain at least one of B, O, N, P, Si, and S as a heteroatom. If the heterocyclic group contains two or more heteroatoms, the two or more heteroatoms may be the same or different from each other. The heterocyclic group may be a monocyclic or polycyclic heterocyclic group, and has the concept of including a heteroaryl group. The number of carbon atoms in the ring of the heterocyclic group may be 2 to 30, 2 to 20, or 2 to 10.

[0142] In the specification, the aliphatic heterocyclic group may contain one or more of B, O, N, P, Si, and S 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 oxetane propane groups, thiohexane propane groups, pyrrolidinyl groups, piperidinyl groups, tetrahydrofuran groups, tetrahydrothiophene groups, thiohexane groups, tetrahydropyran groups, 1,4-dioxane groups, etc., but the embodiments of this disclosure are not limited thereto.

[0143] As used herein, the term "heteroaryl group" may include at least one of B, O, N, P, Si, and S as a heteroatom. When a heteroaryl group contains two or more heteroatoms, the two or more heteroatoms may be the same or different from each other. A heteroaryl group may be a monocyclic heteroaryl group or a polycyclic heteroaryl group. The number of cyclic carbon atoms in a heteroaryl group may be 2 to 30, 2 to 20, or 2 to 10. Examples of heteroaryl groups may include thiophene groups, furan groups, pyrrole groups, imidazole groups, triazole groups, pyridine groups, bipyridine groups, pyrimidine groups, triazine groups, acridine groups, pyridazine groups, pyrazinyl groups, quinoline groups, quinazoline groups, quinoxaline groups, phenoxazine groups, phthalazine groups, pyridopyrimidine groups, pyridopyrazine groups, pyrazinopyrazine groups, isoquinoline groups, indole groups, carbazole groups, and N-arylcarbazole groups. The groups include N-heteroarylcarbazole groups, N-alkylcarbazole groups, benzoxazole groups, benzimidazole groups, benzothiazole groups, benzocarbazole groups, benzothiophene groups, dibenzothiophene groups, thiophene-thiophene groups, benzofuran groups, phenanthroline groups, thiazole groups, isoxazole groups, oxazole groups, oxadiazole groups, thiadiazole groups, phenothiazine groups, dibenzothiophene groups, and dibenzofuran groups, but the embodiments disclosed herein are not limited to these.

[0144] In the specification, the description of aryl groups can be applied to arylene groups, but arylene groups are divalent groups. Similarly, the explanation of heteroaryl groups can be applied to heteroarylene groups, but heteroarylene groups are divalent groups.

[0145] In this specification, silyl groups include alkylsilyl groups and arylsilyl groups. Examples of silyl groups may include trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, etc. However, embodiments of this disclosure are not limited thereto.

[0146] In this specification, the number of carbon atoms in the amino group is not particularly limited, but can be 1 to 30 (e.g., 1 to 20, 1 to 15, 1 to 10, or 1 to 5). The amino group can include alkylamino groups, arylamino groups, or heteroarylamino groups. Examples of amino groups include methylamino groups, dimethylamino groups, phenylamino groups, diphenylamino groups, naphthylamino groups, 9-methyl-anthraylamino groups, etc., but embodiments of this disclosure are not limited thereto.

[0147] A carbonyl group is a functional group in which carbon atoms and oxygen atoms are bonded by a double bond. In the specification, the number of cyclic carbon atoms in the carbonyl group can be 1 to 40, 1 to 30, or 1 to 20. For example, the carbonyl group can have the following structures, but the embodiments of this disclosure are not limited thereto.

[0148]

[0149] In the specification, the number of carbon atoms in the sulfinyl group and sulfonyl group is not particularly limited, but can be 1 to 30 (e.g., 1 to 20, 1 to 15, 1 to 10, or 1 to 5). The sulfinyl group can include alkyl sulfinyl groups and aryl sulfinyl groups. The sulfonyl group can include alkyl sulfonyl groups and aryl sulfonyl groups.

[0150] In this specification, a thio group may include an alkylthio group and an arylthio group. A thio group can refer to a sulfur atom bonded to an alkyl group or an aryl group as defined above. Examples of thio groups may include methylthio groups, ethylthio groups, propylthio groups, pentylthio groups, hexylthio groups, octylthio groups, dodecylthio groups, cyclopentylthio groups, cyclohexylthio groups, phenylthio groups, naphthylthio groups, etc., but the embodiments of this disclosure are not limited thereto.

[0151] As used herein, the term "oxygen group" can refer to an oxygen atom bonded to an alkyl or aryl group as defined above. Oxygen groups can include alkoxy groups and aryloxy groups. Alkoxy groups can be straight-chain, branched, or cyclic. The number of carbon atoms in an alkoxy group is not particularly limited, but can be, for example, 1 to 20 or 1 to 10. Examples of oxy groups include methoxy, ethoxy, n-propoxy, isopropoxy, butoxy, pentoxy, hexoxy, octoxy, nonoxy, decoxy, benzyloxy, etc., but embodiments of this disclosure are not limited thereto.

[0152] As used herein, the term "boron group" can refer to a boron atom bonded to an alkyl or aryl group as defined above. Boron groups can include alkylboron groups and arylboron groups. Examples of boron groups include trimethylboron groups, triethylboron groups, tert-butyldimethylboron groups, triphenylboron groups, diphenylboron groups, phenylboron groups, etc., but embodiments of this disclosure are not limited thereto.

[0153] In the specification, the alkenyl group can be straight-chain or branched. The number of carbon atoms in the alkenyl group is not particularly limited, but can be 2 to 30, 2 to 20, or 2 to 10. Examples of alkenyl groups may include vinyl groups, 1-butenyl groups, 1-pentenyl groups, 1,3-butadienyl groups, styryl groups, styrylvinyl groups, etc., but the embodiments of this disclosure are not limited thereto.

[0154] In this specification, the number of carbon atoms in the amine group is not particularly limited, but can be from 1 to 30 (e.g., 1 to 20, 1 to 15, 1 to 10, or 1 to 5). The amine group can include alkylamine groups and arylamine groups. Examples of amine groups include methylamine groups, dimethylamine groups, phenylamine groups, diphenylamine groups, naphthylamine groups, 9-methyl-anthraylamine groups, etc., but embodiments of this disclosure are not limited thereto.

[0155] In the specification, the alkyl groups in alkylthio groups, alkylsulfonyl groups, alkylaryl groups, alkylamino groups, alkylboron groups, alkylsilyl groups, and alkylamine groups are the same as the examples of alkyl groups described above.

[0156] In the specification, the aryl groups in the aryloxy group, arylthio group, arylsulfonyl group, arylamino group, arylboronic group, arylsilyl group and arylamine group are the same as the examples of aryl groups described above.

[0157] As used in this article, the term "direct bond" can refer to a single bond (e.g., a single covalent bond).

[0158] In the instruction manual, as used herein The symbols “——*” and “——” each represent the positions to be connected.

[0159] In the following description, embodiments of the present disclosure will be described with reference to the accompanying drawings.

[0160] Figure 1 This is a plan view illustrating an implementation of a display device DD. Figure 2 This is a cross-sectional view of the display device DD of the implementation scheme. Figure 2 This is an example along Figure 1 A cross-sectional view of the portion cut off by line I-I'.

[0161] 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 light-emitting devices ED-1, ED-2, and ED-3. The display device DD may include multiple light-emitting devices ED-1, ED-2, and ED-3. The optical layer PP may be on the display panel DP and control the reflected light in the display panel DP due to external light. The optical layer PP may include, for example, a polarizing layer and / or a color filter layer. In one or more embodiments, unlike the views illustrated in the figures, the optical layer PP may be omitted from the display device DD.

[0162] The substrate BL can be on the optical layer PP. The substrate BL can be a component providing a substrate surface on which the optical layer PP is disposed. The substrate BL can be a glass substrate, a metal substrate, a plastic substrate, etc. However, embodiments of this disclosure are not limited thereto, and the substrate BL can be an inorganic layer, an organic layer, or a composite material layer (e.g., a composite material layer comprising inorganic and organic materials). Furthermore, unlike what is shown, in embodiments, the substrate BL can be omitted.

[0163] The display device DD according to the 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 contain at least one of acrylic-based resin, silicone-based resin, and epoxy-based resin.

[0164] 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.

[0165] The substrate layer BS can be a component that provides a substrate surface on which the display device layer DP-ED is disposed. The substrate layer BS can be a glass substrate, a metal substrate, a plastic substrate, etc. However, embodiments of this disclosure are not limited to these, and the substrate layer BS can be an inorganic layer, an organic layer, or a composite material layer.

[0166] In this embodiment, the circuit layer DP-CL is on the substrate layer BS, and the circuit layer DP-CL may include a plurality of transistors. Each of the transistors may include a control electrode, an input electrode, and an output electrode. For example, the circuit layer DP-CL may include switching transistors and driving transistors to drive the light-emitting devices ED-1, ED-2, and ED-3 of the display device layer DP-ED.

[0167] Each of the light-emitting devices ED-1, ED-2, and ED-3 may have the following characteristics, which will be described in more detail later: Figures 3 to 6 The structure of the light-emitting device ED according to the implementation scheme. Each of the light-emitting devices ED-1, ED-2 and ED-3 may include a first electrode EL1, a hole transport region HTR, an emitter layer EML-R, EML-G and EML-B, an electron transport region ETR and a second electrode EL2.

[0168] Figure 2An example is shown in which the emitting layers EML-R, EML-G, and EML-B of light-emitting devices ED-1, ED-2, and ED-3 are located in openings OH defined in a pixel-defined film PDL, and the hole transport region HTR, electron transport region ETR, and second electrode EL2 are provided as common layers in the entire light-emitting device ED-1, ED-2, and ED-3. However, embodiments of this disclosure are not limited thereto, and are related to... Figure 2 Unlike the features illustrated, the hole transport region HTR and electron transport region ETR in the embodiments can be provided by patterning within an opening OH defined in the pixel-defining film PDL. For example, the hole transport region HTR, emitting layers EML-R, EML-G and EML-B, and electron transport region ETR of the light-emitting devices ED-1, ED-2 and ED-3 in the embodiments can be patterned using inkjet printing (e.g., provided as one or more patterns).

[0169] The encapsulation layer TFE can cover the light-emitting devices ED-1, ED-2, and ED-3. The encapsulation layer TFE can seal the display device layer DP-ED. 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 may include at least one insulating layer. According to an embodiment, the encapsulation layer TFE may include at least one inorganic film (hereinafter, encapsulated inorganic film). According to an embodiment, the encapsulation layer TFE may also include at least one organic film (hereinafter, encapsulated organic film) and at least one encapsulated inorganic film.

[0170] An inorganic encapsulation film protects the display device layer DP-ED from moisture / oxygen, while an organic encapsulation film protects the DP-ED from foreign substances such as dust particles. The inorganic encapsulation film may comprise silicon nitrides, silicon oxide nitrides, silicon oxides, titanium oxides, aluminum oxides, etc., but embodiments of this disclosure are not particularly limited thereto. The organic encapsulation film may comprise acrylic-based compounds, epoxy-based compounds, etc. The organic encapsulation film may comprise photopolymerizable organic materials, but embodiments of this disclosure are not particularly limited thereto.

[0171] The encapsulation layer TFE can be on the second electrode EL2 and can fill the opening OH.

[0172] 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. The emitting areas PXA-R, PXA-G, and PXA-B may each be an area that emits light generated by light-emitting devices ED-1, ED-2, and ED-3, respectively. The emitting areas PXA-R, PXA-G, and PXA-B may be spaced apart from each other in a plan view (e.g., on a plane).

[0173] Each of the light-emitting regions PXA-R, PXA-G, and PXA-B can be a region separated by a pixel-defining film PDL. The non-light-emitting region NPXA can be the region between adjacent light-emitting regions PXA-R, PXA-G, and PXA-B, corresponding to a portion of the pixel-defining film PDL. In one or more embodiments, as described in the specification, each of the light-emitting regions PXA-R, PXA-G, and PXA-B can correspond to a pixel. The pixel-defining film PDL can separate the light-emitting devices ED-1, ED-2, and ED-3. The emitting layers EML-R, EML-G, and EML-B of the light-emitting devices ED-1, ED-2, and ED-3 can be within an opening OH defined by the pixel-defining film PDL and separated from each other.

[0174] Based on the color of the light produced by multiple light-emitting devices ED-1, ED-2, and ED-3, the light-emitting areas PXA-R, PXA-G, and PXA-B can be divided into multiple groups. Figure 1 and Figure 2 In the display device DD of the embodiment shown, three light-emitting areas PXA-R, PXA-G, and PXA-B, which emit red light, green light, and blue light respectively, are exemplified as examples. For example, the display device DD of the embodiment may include red light-emitting area PXA-R, green light-emitting area PXA-G, and blue light-emitting area PXA-B that are different from each other.

[0175] In the display device DD according to the embodiment, multiple light-emitting devices ED-1, ED-2, and ED-3 can emit light in different wavelength regions. For example, in the 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. That is, 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 can 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.

[0176] However, the embodiments of this disclosure are 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 different wavelength range. For example, the first to third light-emitting devices ED-1, ED-2, and ED-3 may all emit blue light.

[0177] According to the implementation scheme, 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 1Multiple red emitting areas PXA-R can be arranged relative to each other along the second direction axis DR2, multiple green emitting areas PXA-G can be arranged relative to each other along the second direction axis DR2, and multiple blue emitting areas PXA-B can be arranged relative to each other along the second direction axis DR2. Furthermore, the red emitting areas PXA-R, green emitting areas PXA-G, and blue emitting areas PXA-B can be arranged alternately along the first direction axis DR1 in this order.

[0178] Figure 1 and Figure 2 Examples show that all emitting regions PXA-R, PXA-G, and PXA-B have similar areas, but embodiments of this disclosure are not limited thereto, 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 one or more embodiments, the area of ​​the emitting regions PXA-R, PXA-G, and PXA-B may refer to the area in a plan view (e.g., when viewed in or on a plane defined by a first directional axis DR1 and a second directional axis DR2).

[0179] In one or more embodiments, the arrangement of the light-emitting regions PXA-R, PXA-G, and PXA-B is not limited to... Figure 1 The features illustrated herein, and the order in which the red emitting areas PXA-R, green emitting areas PXA-G, and blue emitting areas PXA-B are arranged, can be appropriately combined and provided in various 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... Arrangement (e.g., RGBG matrix, RGBG structure, or RGBG matrix structure) or diamond arrangement. It is a trademark officially registered by Samsung Display Co., Ltd.

[0180] Furthermore, the areas of the luminescent regions PXA-R, PXA-G, and PXA-B can be different from each other. For example, in one embodiment, the area of ​​the green luminescent region PXA-G can be smaller than the area of ​​the blue luminescent region PXA-B, but the embodiments of this disclosure are not limited thereto.

[0181] In the following text, Figures 3 to 6 This is a schematic cross-sectional view illustrating a light-emitting device according to an embodiment. The light-emitting device ED according to the embodiment may each 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 sequentially.

[0182] and Figure 3 compared to, Figure 4A cross-sectional view of a light-emitting device ED according to an embodiment is shown, 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. Furthermore, with Figure 3 compared to, Figure 5 A cross-sectional view of a light-emitting device ED according to an embodiment is shown, wherein the hole transport region HTR includes a hole injection layer HIL, a hole transport layer HTL, and an electron blocking layer EBL, and the electron transport region ETR includes an electron injection layer EIL, an electron transport layer ETL, and a hole blocking layer HBL. Figure 4 compared to, Figure 6 A cross-sectional view of an embodiment of a light-emitting device ED including a cover layer CPL on a second electrode EL2 is shown.

[0183] The first electrode EL1 is conductive (e.g., electrically conductive). The first electrode EL1 can be formed from a metallic material, a metal alloy, and / or a conductive compound. The first electrode EL1 can be an anode or a cathode. However, embodiments of this disclosure are not limited thereto. Furthermore, the first electrode EL1 can be a pixel electrode. The first electrode EL1 can be a transmissive electrode, a semi-transmissive reflective electrode, or a reflective electrode. If the first electrode EL1 is a transmissive electrode, it can be formed using a transparent metal oxide (e.g., indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), and / or indium tin zinc oxide (ITZO)). If the first electrode EL1 is a semi-transmissive reflective electrode or a reflective electrode, it can contain Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF, Mo, Ti, W, In, Sn, Zn, their compounds, or mixtures thereof (e.g., a mixture of Ag and Mg). In one or more embodiments, the first electrode EL1 may have a multilayer structure, including a reflective or semi-transparent reflective film formed of the materials described above, and a transparent conductive film formed of ITO, IZO, ZnO, ITZO, etc. For example, the first electrode EL1 may have a three-layer structure of ITO / Ag / ITO, but the embodiments of this disclosure are not limited to this. Furthermore, the embodiments of this disclosure are not limited to this; for example, the first electrode EL1 may contain the metallic materials described above, a combination of at least two of the metallic materials described above, oxides of the metallic materials described above, 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

[0184] 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 [thickness value missing]. to approximately

[0185] The hole transport region (HTR) can have a single layer made of a single material, a single layer made of multiple different materials, or a multilayer structure including multiple layers made of multiple different materials.

[0186] For example, the hole transport region HTR can have a single-layer structure of a hole injection layer HIL or a hole transport layer HTL, or it can have a single-layer structure formed of a hole injection material and a hole transport material. Furthermore, the hole transport region HTR can 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 stacked sequentially from the first electrode EL1, but the embodiments of this disclosure are not limited thereto.

[0187] Hole transport regions (HTRs) can be formed using various suitable methods (e.g., vacuum deposition, spin coating, tape casting, Langmuir-Blodgett (LB) method, inkjet printing, laser printing and / or laser-induced thermal imaging (LITI) method).

[0188] The hole transport region (HTR) may contain a compound represented by the following formula H-1:

[0189] Formula H-1

[0190]

[0191] In formula H-1 above, L1 and L2 can each independently be a straight-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. a and b can each independently be an integer from 0 to 10. In one or more embodiments, when a or b is an integer of 2 or greater than 2, multiple 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.

[0192] 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. Furthermore, in formula H-1, Ar3 can be a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms.

[0193] The compound represented by formula H-1 can be a monoamine compound. In one or more embodiments, the compound represented by formula H-1 can be a diamine compound, wherein at least one selected from Ar1 to Ar3 includes an amine group as a substituent. Furthermore, the compound represented by formula H-1 can be a carbazole-based compound comprising a substituted or unsubstituted carbazole group in at least one of Ar1 and Ar2, or a fluorene-based compound comprising a substituted or unsubstituted fluorene group in at least one of Ar1 and Ar2.

[0194] The compound represented by formula H-1 can be represented by any compound 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 those represented by the following group of compounds H:

[0195] Compound group H

[0196]

[0197] Hole transport region (HTR) may contain phthalocyanine compounds (e.g., 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(naphthyl-1-yl)-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.

[0198] Hole transport regions (HTRs) can contain carbazole derivatives (e.g., N-phenylcarbazole and / or polyvinylcarbazole), fluorene derivatives, N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (TPD), triphenylamine derivatives (e.g., 4,4',4”-tris(N-carbazolyl)triphenylamine (TCTA)), N,N'-bis(naphthyl-l-yl)-N,N'-diphenyl-benzidine (NPB), 4,4'-cyclohexylenebis[N,N-bis(4-methylphenyl)aniline] (TAPC), 4,4'-bis[N,N'-bis(3-tolyl)amino]-3,3'-dimethylbiphenyl (HMTPD), 1,3-bis(N-carbazolyl)benzene (mCP), etc.

[0199] In addition, the hole transport region (HTR) can contain 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.

[0200] The hole transport region HTR may contain a compound with the hole transport region described above in at least one of the hole injection layer HIL, the hole transport layer HTL, and the electron blocking layer EBL.

[0201] 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) can have, for example, approximately to approximately The thickness. When the hole transport region (HTR) includes the hole transport layer (HTL), the 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) can be determined if the thicknesses meet the ranges described above. Satisfactory hole transport characteristics can be achieved without a significant increase in driving voltage.

[0202] 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 of halide metal compounds, quinone derivatives, metal oxides, and compounds containing cyano groups, but embodiments of this disclosure are not limited thereto. For example, p-dopers may include metal halides (e.g., CuI and / or RbI), quinone derivatives (e.g., tetracyanoquinone dimethyl ether (TCNQ) and / or 2,3,5,6-tetrafluoro-7,7',8,8'-tetracyanoquinone dimethyl ether (F4-TCNQ)), metal oxides (e.g., tungsten oxide and / or molybdenum oxide), dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarboxynitrile (HAT-CN), 4-[[2,3-bis[cyano-(4-cyano-2,3,5,6-tetrafluorophenyl)methylene]cyclopropyl]-cyanomethyl]-2,3,5,6-tetrafluorobenzylnitrile, etc., but embodiments of this disclosure are not limited thereto.

[0203] As described above, in addition to the hole injection layer (HIL) and the hole transport layer (HTL), the hole transport region (HTR) may further include at least one of a buffer layer and an electron blocking layer (EBL). The buffer layer can compensate for the resonant distance based on the wavelength of light emitted from the emitter layer (EML) and can thus increase the light emission efficiency. Materials that can be included in the hole transport region (HTR) can be used as materials 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).

[0204] The emitter layer EML is provided on the hole transport region HTR. The emitter layer EML can 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 made of a single material, a single layer made of multiple different materials, or a multilayer structure with multiple layers made of multiple different materials.

[0205] The emitting layer EML in the light-emitting device ED of the embodiment may contain a polycyclic compound represented by the following formula 1:

[0206] Formula 1

[0207]

[0208] The compound represented by Formula 1 may contain at least one anthracene derivative represented by Formula A:

[0209] Formula A

[0210]

[0211] In Formula A, Ra can be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkoxy 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. For example, in an embodiment, Ra can be an unsubstituted phenyl group or an unsubstituted anthracene group, but the embodiments of this disclosure are not limited thereto.

[0212] L1 can be a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, or a substituted or unsubstituted divalent amine group. p can be 0 or 1. When p is 0, the anthracene derivative can be directly bonded to the backbone, and when p is 1, the anthracene derivative can be bonded to the backbone via L1.

[0213] In the implementation scheme, formula A can be represented by any one of the following formulas A-1 to A-4:

[0214] Formula A-1

[0215]

[0216] Formula A-2

[0217]

[0218] Formula A-3

[0219]

[0220] Formula A-4

[0221]

[0222] Formula A-1 represents the case where p is 0. Formula A-2 represents the case where p is 1 and L1 is a phenylene group. Formula A-3 represents the case where p is 1 and L1 is... In this case, equation A-4 is where p is 1 and L1 is... In equation A-3, m is either 0 or 1, and It refers to the position where the anthracene derivative is substituted.

[0223] Equation A-1 can be represented by either Equation AA-1 or Equation AA-2:

[0224] Formula AA-1

[0225]

[0226] Formula AA-2

[0227]

[0228] Formula AA-1 is the case where, in Formula A-1, the anthracene is bonded to a benzene ring located at the middle position of the anthracene skeleton, and Ra is substituted at a benzene ring located at the middle position of the anthracene skeleton. Formula AA-2 is the case where, in Formula A-1, the anthracene is bonded to a benzene ring located at one side of the anthracene skeleton, and Ra is substituted at a benzene ring located at the other side of the anthracene skeleton. In Formulas AA-1 and AA-2, Ra is the same as defined with respect to Formula 1 above.

[0229] Equation A-2 can be represented by any of the following equations B-1 to B-3:

[0230] Formula B-1

[0231]

[0232] Formula B-2

[0233]

[0234] Formula B-3

[0235]

[0236] Formula B-1 is the one in which the phenylene group is substituted in Formula A-2. The case exists in the adjacent position relative to the skeleton. Formula B-2 is where, in Formula A-2, the substituted phenylene group... This exists in the meta position relative to the skeleton. Formula B-3 is where, in Formula A-2, the substituted phenylene group... It exists in the case of alignment relative to the skeleton.

[0237] Equation A-3 can be represented by either Equation C-1 or Equation C-2:

[0238] Formula C-1

[0239]

[0240] Formula C-2

[0241]

[0242] Equation C-1 is where, in Equation A-3, m is 0 and The case of direct bonding to the nitrogen atom of the amine. Formula C-2 is where, in Formula A-3, m is 1 and The case of a phenylene group bonded to the nitrogen atom of an amine.

[0243] In Formula 1, X1 to X4 may each be independently O, S, Se, or NR1, and Z1 and Z2 may each be independently CR2. R1 and R2 may each be independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted oxy group, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, a substituted or unsubstituted thio group, or a portion represented by Formula A, and / or may be bonded to adjacent groups to form a ring, wherein at least one selected from X1 to X4, Z1, and Z2 includes a portion represented by Formula A.

[0244] a1 and a2 can each be an integer from 0 to 2, and R y1 and R y2 Each of these can be independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkoxy 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.

[0245] When a1 is 0, R y1Unsubstituted benzene ring containing Z1, and when a2 is 0, R y2 Unsubstituted benzene ring containing Z2. When a1 is 1, an R y1 It can replace the benzene ring containing Z1 and can bond to the R2 of the adjacent CR2 to form a ring. When a2 is 1, one R y2 It can replace the benzene ring containing Z2 and can bond to the R2 of the adjacent CR2 to form a ring. When a1 is 2, the two R2s... y1 It can replace the benzene ring containing Z1, and the two Rs y1 They can bond to form a ring. When a2 is 2, the two Rs y2 It can replace the benzene ring containing Z2, and the two Rs y2 They can be bonded to form a ring. However, this is merely an example, and embodiments of this disclosure are not limited thereto, and R y1 and R y2 They can be bonded in various suitable ways to form rings.

[0246] The polycyclic compound represented by Formula 1 in the embodiments comprises an anthracene group having a low minimum triplet excitation energy, and therefore can have a minimum triplet excitation energy (T1) of about 1.8 eV or less. By comprising a polycyclic compound having a low minimum triplet excitation energy, the lifespan of the light-emitting device can be improved. In the embodiments, the polycyclic compound represented by Formula 1 can emit blue light.

[0247] The emitting layer EML in the light-emitting device ED of the embodiment may contain a polycyclic compound represented by the following formula 2:

[0248] Formula 2

[0249]

[0250] X1 to X4 can each be independently O, S, Se, or NR1, and R1 can be... Hydrogen atom, deuterium atom, halogen atom, cyano group, nitro group, substituted or unsubstituted silyl group, substituted or unsubstituted amine group, substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms.

[0251] In Equation 2 above, n can be an integer from 0 to 8. That is, the polycyclic compound represented by Equation 2 can contain at least one As a substituent, and may contain up to eight. As a substituent.

[0252] When n is 0, at least one of X1 to X4 can be NR1, where R1 is And when in NR1, R1 is not In this case, n can be an integer from 1 to 8. That is, in one implementation, n is 0, and at least one selected from X1 to X4 can be NR1, where R1 is... In another implementation, in NR1, R1 is not And n can be an integer from 1 to 8.

[0253] In Formula 2, L1 can be a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, or a substituted or unsubstituted divalent amine group. In Formula 2, p can be 0 or 1. When p is 0, the anthracene derivative can be directly bonded to the backbone, and when p is 1 or greater than 1, the anthracene derivative can be bonded to the backbone with L1 in between.

[0254] Equation 2 can be expressed by any of the following equations 3 to 5:

[0255] Formula 3

[0256]

[0257] Formula 4

[0258]

[0259] Formula 5

[0260]

[0261] Equation 3 is for the case where n is 0 in Equation 2. Equation 4 is for the case where n is 1 and p is 1. Equation 5 is for the case where n is 2 and p is 1.

[0262] In Equation 3, at least one selected from X1 to X4 can be NR1, where R1 is

[0263] In Formula 4, L2 can be a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, or a substituted or unsubstituted divalent amine group.

[0264] In Formula 5, L2 and L3 can each be independently a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, or a substituted or unsubstituted divalent amine group.

[0265] In Equation 2, It can be represented by one of the following equations 6 to 9:

[0266] Formula 6

[0267]

[0268] Formula 7

[0269]

[0270] Formula 8

[0271]

[0272] Formula 9

[0273]

[0274] Equation 6 is one of the equations in Equation 2. In the case where p is 0; Equation 7 is the case where p is 0 in Equation 2. In the case where p is 1 and L1 is a phenylene group; and Formula 8 is where in Formula 2 In the equation, p is 1 and L1 is... The situation. It represents the position of the anthracene group substitution. Formula 9 is the case where p is 1 and L1 is a phenanthrene group.

[0275] Equation 6 can be represented by either Equation 6-1 or Equation 6-2:

[0276] Formula 6-1

[0277]

[0278] Formula 6-2

[0279]

[0280] Formula 6-1 is the case in Formula 6 where the benzene ring at the intermediate position of the anthracene substitutes for the backbone, and Ra substitutes for the benzene ring at the intermediate position of the anthracene. Formula 6-2 is the case in Formula 6 where the benzene ring at one side of the anthracene substitutes for the backbone, and Ra substitutes for the benzene ring at the other side of the anthracene. In Formulas 6-1 and 6-2, Ra is the same as defined with respect to Formula 2 above.

[0281] Equation 7 can be represented by any of the following equations: 7-1 to 7-3

[0282] Equation 7-1

[0283]

[0284] Equation 7-2

[0285]

[0286] Formula 7-3

[0287]

[0288] Formula 7-1 is where, in Formula 7, the substituted phenylene group is... The case exists in the adjacent position relative to the skeleton. Formula 7-2 is where, in Formula 7, the substituted phenyl group... The case exists in the meta position relative to the skeleton. Formula 7-3 is where, in Formula 7, the substituted phenylene group... It exists in the case of alignment relative to the skeleton.

[0289] Equation 8 can be represented by either Equation 8-1 or Equation 8-2:

[0290] Formula 8-1

[0291]

[0292] Formula 8-2

[0293]

[0294] Equation 8-1 is where, in Equation 8, m is 0 and The case of direct bonding to the nitrogen atom of the amine. Equation 8-2 is where, in Equation 8, m is 1 and The case of a phenylene group bonded to the nitrogen atom of an amine.

[0295] In Equation 2, R y Ra can each independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkoxy 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, and / or can be bonded to adjacent groups to form a ring. For example, Ra can be an unsubstituted phenyl group or an unsubstituted naphthyl group, but embodiments of this disclosure are not limited thereto. a can be an integer from 0 to 8-n.

[0296] The polycyclic compound represented by Formula 2 in the embodiments comprises anthracene having a low minimum triplet excitation energy, and therefore can have a minimum triplet excitation energy (T1) of about 1.8 eV or less. By comprising a polycyclic compound having a low minimum triplet excitation energy, the lifespan of the light-emitting device can be improved.

[0297] In an embodiment, the emitter layer may contain at least one compound selected from the group of compounds represented by compound group 1.

[0298] Compound group 1

[0299]

[0300]

[0301]

[0302]

[0303]

[0304]

[0305]

[0306]

[0307]

[0308] exist Figures 3 to 6 In the light-emitting device ED of the illustrated embodiment, the emitting layer EML may comprise a host and a dopant. A polycyclic compound according to the embodiment can be used as the dopant material. For example, a polycyclic compound according to the embodiment can be used as the dopant material for an emitting layer that emits thermally activated delayed fluorescence.

[0309] In addition to the polycyclic compound of the implementation scheme, the emitter layer EML may further comprise the emitter layer material described below.

[0310] The emission layer EML may further contain a compound represented by the following formula E-1. The compound represented by the following formula E-1 can be used as a fluorescent host material.

[0311] E-1

[0312]

[0313] In equation E-1, R 31 To R 40Each of the following can independently be 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, and / or can be bonded to adjacent groups to form a ring. In one or more embodiments, R 31 To R 40 It can bond to adjacent groups to form saturated or unsaturated hydrocarbon rings.

[0314] In E-1, c and d can each be an integer from 0 to 5 independently.

[0315] Formula E-1 can be represented by any one of the following compounds E1 to E19:

[0316]

[0317]

[0318] In an embodiment, the emitting layer EML may further comprise a compound represented by formula E-2a or E-2b. The compound represented by formula E-2a or E-2b can be used as a phosphorescent host material.

[0319] E-2a

[0320]

[0321] In formula E-2a, a can be an integer from 0 to 10, and La can be a direct bond, 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 one or more embodiments, when a is an integer of 2 or greater than 2, the plurality of La 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.

[0322] Furthermore, in E-2a, A1 to A5 can each be N or CR independently. i R a To R iEach group may independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted amine group, a substituted or unsubstituted thio group, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, and / or may be bonded to adjacent groups 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.

[0323] In one or more embodiments, in formula E-2a, two or three groups selected from A1 to A5 may be N, and the remainder may be CR. i .

[0324] E-2b

[0325]

[0326] In formula E-2b, Cbz1 and Cbz2 can each be an unsubstituted carbazole group or a carbazole group substituted with an aryl group having 6 to 30 cyclic carbon atoms. b It is 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, b is an integer from 0 to 10, and when b is an integer of 2 or greater than 2, multiple L b Each can be an arylene group, either substituted or unsubstituted, having 6 to 30 cyclic carbon atoms, or a heteroarylene group, either substituted or unsubstituted, having 2 to 30 cyclic carbon atoms.

[0327] The compound represented by formula E-2a or E-2b may be 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 compounds represented by formula E-2a or E-2b are not limited to those represented by the following group of compounds E-2.

[0328] Compound group E-2

[0329]

[0330]

[0331] The emitter layer EML may further comprise materials commonly used in the art as the host material. For example, the emitter layer EML may comprise at least one of bis[2-(diphenylphosphino)phenyl]ether oxide (DPEPO), 4,4'-bis(carbazole-9-yl)biphenyl (CBP), 1,3-bis(carbazole-9-yl)benzene (mCP), 2,8-bis(diphenylphosphino)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, embodiments of this disclosure are not limited thereto, and for example, tris(8-hydroxyquinoline alkyl)aluminum (Alq3), 4,4'-bis(N-carbazole)-1,1'-biphenyl (CBP), poly(N-vinylcarbazole) (PVK), 9,10- Di(naphthyl-2-yl)anthracene (ADN), 4,4',4”-tris(carbazole-9-yl)-triphenylamine (TCTA), 1,3,5-tris(N-phenylbenzimidazol-2-yl)benzene (TPBi), 2-tert-butyl-9,10-di(naphthyl-2-yl)anthracene (TBADN), stilbeneyl arylene (DSA), 4,4'-bis(9-carbazole)-2,2'-dimethyl-biphenyl (CDBP), 2-methyl-9,10-bis(naphthyl-2-yl)anthracene (MADN), hexaphenylcyclotriphosphazene (CP1), 1,4-bis(triphenylsilyl)benzene (UGH2), hexaphenylcyclotrisiloxane (DPSiO3), octaphenylcyclotetrasiloxane (DPSiO4), 2,8-bis(diphenylphospho)dibenzofuran (PPF) and others can be used as host materials.

[0332] The emitter layer EML may further contain compounds represented by the formula Ma or Mb. Compounds represented by the formula Ma or Mb can be used as phosphorescent dopant materials.

[0333] Formula Ma

[0334]

[0335] 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 amine group, a substituted or unsubstituted thio group, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, and / 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.

[0336] Compounds represented by the formula Ma can be used as red or green phosphorescent dopants.

[0337] 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:

[0338]

[0339]

[0340] Compounds M-a1 and M-a2 can be used as red dopant materials, and compounds M-a3 to M-a5 can be used as green dopant materials.

[0341] Formula Mb

[0342]

[0343] 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 L 24 Each is independently a direct-connect key, *-O-*, *-S-*, 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 39Each of the following is independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, and / or bonded to an adjacent group to form a ring, and d1 to d4 are each independently an integer from 0 to 4.

[0344] Compounds represented by the formula Mb can be used as blue or green phosphorescent dopants.

[0345] Compounds represented by formula Mb can be represented by any of the following compounds. However, the following compounds are examples, and compounds represented by formula Mb are not limited to those represented by the following compounds.

[0346]

[0347] In the compound, 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 amine 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.

[0348] The emitter layer (EML) may further comprise a compound represented by any one of the following formulas: Fa to Fc. Compounds represented by the following formulas: Fa to Fc can be used as fluorescent dopant materials.

[0349] Formula Fa

[0350]

[0351] In the formula Fa, the formula is selected from R. a To R j The two values ​​can be independently replaced by *-NAr1Ar2. (From R) a To R jThe unsubstituted elements of *-NAr1Ar2 can each independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 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 *-NAr1Ar2, Ar1 and Ar2 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. For example, at least one of Ar1 and Ar2 can be a heteroaryl group containing O or S as a cyclic atom.

[0352] Formula Fb

[0353]

[0354] 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, and / or can be bonded to adjacent groups to form a ring.

[0355] 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.

[0356] In formula Fb, the number of rings represented by U and V can each be 0 or 1 independently. For example, in formula Fb, when the number of U or V is 1, it indicates that a ring forms a fused ring at the part described as U or V, and when the number of U or V is 0, there is no ring described as U or V. For example, when the number of U is 0 and the number of V is 1, or when the number of U is 1 and the number of V is 0, the fused ring with a fluorene core in formula Fb can be a tetracyclic compound. Furthermore, when the number of each of U and V is 0, the fused ring with a fluorene core in formula Fb can be a tricyclic compound. Furthermore, when the number of each of U and V is 1, the fused ring with a fluorene core in formula Fb can be a pentacyclic compound.

[0357] Formula Fc

[0358]

[0359] In equation Fc, A1 and A2 can each be independently O, S, Se, or NR. m And R m 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 is independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted amine group, a substituted or unsubstituted boron group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thio group, a substituted or unsubstituted alkyl group having 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, and / or bonded to an adjacent group to form a ring.

[0360] 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.

[0361] In the implementation, the emitter layer EML may further comprise styrene derivatives (e.g., 1,4-bis[2-(3-N-ethylcarbazolyl)vinyl]benzene (BCzVB), 4-(di-p-tolylamino)-4'-[(di-p-tolylamino)styrene]stilbene (DPAVB) and N-(4-((E)-2-(6-((E)-4-(diphenylamino)styrene)naphth-2-yl)vinyl)phenyl)-N-phenylaniline (N-BDAVBi)), 4,4'-bis[2-(4-(N,N-diphenylamino)phenyl)vinyl]biphenyl (DPAVBi), perylene and its derivatives (e.g., 2,5,8,11-tetra-tert-butylperylene (TBP)), pyrene and its derivatives (e.g., 1,1'-dipyrene, 1,4-dipyrenebenzene, 1,4-bis(N,N-diphenylamino)pyrene) as general dopant materials).

[0362] The emitter layer (EML) may further comprise a general phosphorescent dopant material. For example, metal complexes comprising iridium (Ir), platinum (Pt), osmium (Os), gold (Au), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), or thulium (Tm) can be used as phosphorescent dopant. For instance, iridium(III) bis(4,6-difluorophenylpyridyl-N,C2)-pyridinecarboxylate (FIrpic), iridium(III) bis(2,4-difluorophenylpyridyl)tetra(1-pyrazolyl)borate (Fir6), and / or octaethylporphyrin platinum (PtOEP) can be used as phosphorescent dopant. However, embodiments of this disclosure are not limited thereto.

[0363] The emitter layer (EML) can contain quantum dot materials. The core of the quantum dots can be selected from group II-VI compounds, group III-VI compounds, group I-III-VI compounds, group III-V compounds, group III-II-V compounds, group IV-VI compounds, group IV elements, group IV compounds, and combinations thereof.

[0364] Group II-VI compounds may be selected from the group consisting of: binary compounds selected from CdSe, CdTe, CdS, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, MgSe, MgS, and mixtures thereof; and ternary compounds selected from CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, CdZnS, and CdZnO. The group consisting of nSe, CdZnTe, 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.

[0365] 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.

[0366] 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.

[0367] III-V group compounds may be selected from the group consisting of: binary compounds selected from GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, InSb and mixtures thereof; ternary compounds selected from 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 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 compound may further comprise a group II metal. For example, InZnP or similar materials may be selected as group III-II-V compounds.

[0368] Group IV-VI compounds may be selected from the group consisting of: binary compounds selected from SnS, SnSe, SnTe, PbS, PbSe, PbTe, and mixtures thereof; ternary compounds selected from SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, SnPbTe, and mixtures thereof; and quaternary compounds selected from SnPbSSe, SnPbSeTe, SnPbSTe, and mixtures thereof. Group IV elements may be selected from Si, Ge, and mixtures thereof. Group IV compounds may be binary compounds selected from the group consisting of SiC, SiGe, and mixtures thereof.

[0369] In one or more embodiments, binary, ternary, and / or quaternary compounds may exist in the particles with a uniform (e.g., substantially uniform) concentration distribution, or they may exist in the same particle with partially different concentration distributions. Furthermore, the quantum dots may have a core / shell structure, where one quantum dot surrounds another. In a core / shell structure, the shell interface may have a concentration gradient, where the concentration of the element present in the shell decreases towards the core. For example, in a core / shell structure, a concentration gradient may exist where the concentration of the element present in the shell decreases towards the center of the core.

[0370] In some embodiments, quantum dots may have the core-shell structure described above, comprising a core containing nanocrystals and a shell surrounding the core. The shell of the quantum dot can act as a protective layer to prevent or reduce chemical degradation of the core in order to maintain semiconductor properties, and / or can act as a charging layer to impart electrophoretic properties to the quantum dot. The shell can be single-layered or multi-layered. Examples of shells for quantum dots may include metal oxides, non-metal oxides, semiconductor compounds, or combinations thereof.

[0371] For example, metal oxides and / or non-metal oxides can be binary compounds (e.g., SiO2, Al2O3, TiO2, ZnO, MnO, Mn2O3, Mn3O4, CuO, FeO, Fe2O3, Fe3O4, CoO, Co3O4 and / or NiO); and / or ternary compounds (e.g., MgAl2O4, CoFe2O4, NiFe2O4 and / or CoMn2O4), but embodiments of this disclosure are not limited thereto.

[0372] 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 the embodiments of this disclosure are not limited thereto.

[0373] Quantum dots can have a full width at half maximum (FWHM) of light emission wavelengths of about 45 nm or less, about 40 nm or less, or about 30 nm or less, and can improve color purity or color reproducibility within these ranges. Furthermore, light emitted through such quantum dots is emitted in all directions, and therefore a wide viewing angle can be improved.

[0374] Furthermore, although the form of quantum dots is not particularly limited, as long as it is a form commonly used in the field, quantum dots in the form of spherical, pyramidal, multi-armed and / or cubic nanoparticles, nanotubes, nanowires, nanofibers, nanoplates, etc., can be used.

[0375] Quantum dots can be used to control the color of emitted light based on their particle size. Therefore, quantum dots can have a variety of suitable light emission colors, such as blue, red, and / or green.

[0376] exist Figures 3 to 6 In each of the illustrated embodiments of the light-emitting device ED, an electron transport region (ETR) is provided on the emitter layer (EML). The electron transport region (ETR) may include at least one of a hole blocking layer (HBL), an electron transport layer (ETL), and an electron injection layer (EIL), but embodiments of this disclosure are not limited thereto.

[0377] The electronic transport region (ETR) can have a single layer made of a single material, a single layer made of multiple different materials, or a multi-layer structure including multiple layers made of multiple different materials.

[0378] For example, the electron transport region (ETR) can have a single-layer structure of an electron injection layer (EIL) or an electron transport layer (ETL), or it can have a single-layer structure formed of an electron injection material and an electron transport material. Furthermore, the electron transport region (ETR) can have a single-layer structure formed of a variety of different materials, or it can have a structure in which the electron transport layer (ETL) / electron injection layer (EIL) or hole blocking layer (HBL) / electron transport layer (ETL) / electron injection layer (EIL) are stacked from the emitter layer (EML) in a predetermined order, but embodiments of this disclosure are not limited thereto. The electron transport region (ETR) can have, for example, approximately to approximately The thickness.

[0379] Electron transport regions (ETRs) can be formed using various suitable methods, such as vacuum deposition, spin coating, tape casting, Langmuir-Blodgett (LB) method, inkjet printing, laser printing, laser-induced thermal imaging (LITI), etc.

[0380] The electron transport region (ETR) may contain a compound represented by the following formula: ET-1

[0381] ET-1

[0382]

[0383] In Equation ET-1, at least one selected from X1 to X3 is N, and the remainder can be CR. a R aIt 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. Ar1 to Ar3 can each independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms.

[0384] In Formula ET-1, a to c can each be an integer from 0 to 10 independently. In Formula ET-1, L1 to L3 can each be a straight-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 to c are each an integer of 2 or greater than 2, L1 to L3 can each be an 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.

[0385] The electron transport region (ETR) may comprise anthracene-based compounds. However, embodiments of this disclosure are not limited thereto, and the ETR may comprise, 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, 1,3,5-tris(1-phenyl-1H-benzimidazol-2-yl)benzene (TPBi), 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), and 4,7-diphenyl-1,10-phenanthroline (Bphen). 3-(4-biphenyl)-4-phenyl-5-tert-butylphenyl-1,2,4-triazole (TAZ), 4-(naphth-1-yl)-3,5-diphenyl-4H-1,2,4-triazole (NTAZ), 2-(4-biphenyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (tBu-PBD), bis(2-methyl-8-quinoline-N1,O8)-(1,1'-biphenyl-4-oline)aluminum (BAlq), bis(benzoquinoline-10-oline)beryllium (Bebq2), 9,10-bis(naphth-2-yl)anthracene (ADN), 1,3-bis[3,5-bis(pyridin-3-yl)phenyl]benzene (BmPyPhB), or mixtures thereof.

[0386] Furthermore, the electron transport region (ETR) can comprise metal halides (e.g., LiF, NaCl, CsF, RbCl, RbI, CuI, and / or KI), lanthanides (e.g., Yb), and / or co-deposited materials of metal halides and lanthanides. For example, the ETR can comprise KI:Yb, RbI:Yb, etc., as co-deposited materials. In one or more embodiments, the ETR can be formed using metal oxides such as Li₂O and / or BaO, lithium 8-hydroxyquinoline (Liq), etc., but embodiments of this disclosure are not limited thereto. The ETR can also be formed from a mixture of an electron transport material and an insulating organometallic salt. The organometallic salt can be a material having a band gap of about 4 eV or greater than 4 eV. For example, the organometallic salt can include, for example, metal acetates, metal benzoates, metal acetoacetates, metal acetylacetonates, and / or metal stearates.

[0387] In addition to the materials described above, the electron transport region (ETR) may further comprise 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP) and / or 4,7-diphenyl-1,10-phenanthroline (Bphen), but embodiments of this disclosure are not limited thereto.

[0388] The electron transport region (ETR) may contain a compound of the electron transport region described above in at least one of the electron injection layer (EIL), the electron transport layer (ETL), and the hole blocking layer (HBL).

[0389] 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 within the aforementioned range. If the thickness of the ETL meets these requirements, satisfactory electron transport characteristics can be obtained without a significant increase in the driving voltage. When the ETL includes an electron injection layer (EIL), the EIL can have approximately [missing information - likely a specific thickness]. 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 range described above, satisfactory electron injection characteristics can be obtained without a significant increase in the driving voltage.

[0390] The second electrode EL2 is provided on the electron transport region ETR. The second electrode EL2 can be a common electrode. The second electrode EL2 can be a cathode or an anode, but embodiments of this disclosure are not limited thereto. For example, when the first electrode EL1 is an anode, the second electrode EL2 can be a cathode, and when the first electrode EL1 is a cathode, the second electrode EL2 can be an anode.

[0391] The second electrode EL2 can be a transmission electrode, a semi-transmissive reflection electrode, or a reflection electrode. When the second electrode EL2 is a transmission electrode, it can be formed from a transparent metal oxide (e.g., indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), indium tin zinc oxide (ITZO), etc.).

[0392] When the second electrode EL2 is a semi-transparent reflective electrode or a reflective electrode, the second electrode EL2 may contain Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF, Mo, Ti, Yb, W, In, Sn, Zn, or compounds or mixtures thereof (e.g., AgYb and / or MgAg). In one or more embodiments, the second electrode EL2 may have a multilayer structure, the multilayer structure including a reflective or semi-transparent reflective film formed of the materials described above, and a transparent conductive film formed of ITO, IZO, ZnO, ITZO, etc. For example, the second electrode EL2 may contain the metallic materials described above, a combination of at least two of the metallic materials described above, oxides of the metallic materials described above, etc.

[0393] In one or more embodiments, the second electrode EL2 may be connected to an auxiliary electrode. Connecting the second electrode EL2 to the auxiliary electrode can reduce its resistance.

[0394] 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 comprise multiple layers or a single layer.

[0395] In the implementation scheme, the capping layer CPL can be an organic layer or an inorganic layer. For example, when the capping layer CPL contains inorganic materials, the inorganic materials may include alkali metal compounds, such as LiF; and alkaline earth metal compounds, such as MgF2, SiON, and SiN. x SiO y wait.

[0396] For example, when the capping layer CPL contains organic materials, the organic materials may include 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), epoxy resins, and / or acrylates (e.g., methacrylates). However, embodiments of this disclosure are not limited thereto, and the capping layer CPL may contain at least one selected from compounds P1 to P5:

[0397]

[0398]

[0399] In one or more embodiments, the refractive index of the capping layer CPL may be about 1.6 or greater than 1.6. For example, the refractive index of the capping layer CPL may be about 1.6 or greater than 1.6 relative to light in the wavelength range of about 550 nm to about 660 nm.

[0400] Figure 7 and Figure 8 Each is a cross-sectional view of the display device according to the implementation scheme. In the following, in reference... Figure 7 and Figure 8 When describing the display device of the implementation scheme, the description of... Figures 1 to 6 The repetitive features already described will be discussed, but the main focus will be on their differences.

[0401] refer to Figure 7 According to the implementation scheme, the display device DD may include a display panel DP including a display device layer DP-ED, a light control layer CCL and a color filter layer CFL on the display panel DP.

[0402] exist Figure 7 In the illustrated embodiments, 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.

[0403] The 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. In one or more embodiments, as described above... Figures 3 to 6 The structure of the light-emitting device can be applied in the same way. Figure 7 The structure of the light-emitting device ED is shown in the figure.

[0404] refer to Figure 7 The emitting layer EML can be located within an opening OH defined in the pixel-defining film PDL. For example, emitting layer EMLs separated by the pixel-defining film PDL and provided corresponding to each emitting region 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 for the entire emitting region PXA-R, PXA-G, and PXA-B.

[0405] The light control layer (CCL) can be on the display panel (DP). The CCL may include a light converter, such as a quantum dot or phosphor. The light converter emits light by converting the wavelength of light supplied to it into light with different wavelengths. That is, the CCL may include a layer containing quantum dots and / or a layer containing phosphors.

[0406] 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 spaced apart from each other.

[0407] refer to Figure 7 The separated pattern BMP can be between the various optical control units in the optical control units CCP1, CCP2 and CCP3 that are spaced apart from each other, but the embodiments of this disclosure are not limited thereto. Figure 7 The example shows that the separated 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 separated pattern BMP.

[0408] The light control layer CCL may include: a first light control unit CCP1 containing a first quantum dot QD1 that converts first color light provided by the light-emitting device ED into second color light, a second light control unit CCP2 containing a second quantum dot QD2 that converts first color light into third color light, and a third light control unit CCP3 that transmits first color light.

[0409] In this implementation, 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 provide the first color light by transmitting blue light (which is 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 above description applies to quantum dots QD1 and QD2.

[0410] Furthermore, the optical control layer CCL may further include a 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 contain any quantum dots but may contain a scatterer SP.

[0411] The scatterer SP can be inorganic particles. For example, the scatterer SP can include at least one of TiO2, ZnO, Al2O3, SiO2, and hollow silica. The scatterer SP can contain any one of TiO2, ZnO, Al2O3, SiO2, and hollow silica, or it can be a mixture of at least two materials selected from TiO2, ZnO, Al2O3, SiO2, and hollow silica.

[0412] The first optical control unit CCP1, the second optical control unit CCP2, and the third optical control unit CCP3 may each comprise a matrix resin BR1, BR2, and BR3 in which quantum dots QD1, QD2, and / or scatterers SP are dispersed. In an embodiment, the first optical control unit CCP1 may comprise a first quantum dot QD1 and a scatterer SP dispersed in a first matrix resin BR1, the second optical control unit CCP2 may comprise a second quantum dot QD2 and a scatterer SP dispersed in a second matrix resin BR2, and the third optical control unit CCP3 may comprise a scatterer SP dispersed in a third matrix resin BR3. The matrix resins BR1, BR2, and BR3 are the medium in which quantum dots QD1 and QD2 and scatterers SP are dispersed, and may be formed from various suitable resin compositions, generally referred to as adhesives. For example, the matrix resins BR1, BR2, and BR3 may be acrylic-based resins, urethane-based resins, silicone-based resins, epoxy-based resins, etc. The matrix resins BR1, BR2, and BR3 may be transparent resins. In the implementation scheme, the first matrix resin BR1, the second matrix resin BR2, and the third matrix resin BR3 may each be the same as or different from each other.

[0413] The light control layer CCL may include a barrier layer BFL1. The barrier layer BFL1 serves to prevent or reduce the penetration of moisture and / or oxygen (hereinafter referred to as "moisture / oxygen"). The barrier layer BFL1 may be located above or below the light control units CCP1, CCP2, and CCP3 to block or reduce their exposure to moisture / oxygen. In one or more embodiments, the barrier layer BFL1 may cover the light control units CCP1, CCP2, and CCP3. Furthermore, the barrier layer BFL1 may be provided between the light control units CCP1, CCP2, and CCP3 and the color filter layer CFL.

[0414] Barrier layers BFL1 and BFL2 may include at least one inorganic layer. That is, barrier layers BFL1 and BFL2 may contain inorganic materials. For example, barrier layers BFL1 and BFL2 may contain silicon nitride, aluminum nitride, zirconium nitride, titanium nitride, hafnium nitride, tantalum nitride, silicon oxide, aluminum oxide, titanium oxide, tin oxide, cerium oxide, silicon oxynitride, metal films that ensure light transmittance, etc. In one or more embodiments, barrier layers BFL1 and BFL2 may further include organic films. Barrier layers BFL1 and BFL2 may be formed from a single layer or multiple layers.

[0415] In the display device DD of the implementation scheme, 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 blocking layer BFL2 can be omitted.

[0416] The color filter layer CFL may include a light-shielding unit BM and color filters CF1, CF2, and CF3. The color filter layer CFL may include a first color filter CF1 configured to transmit a second color light, a second color filter CF2 configured to transmit a third color light, and a third color filter CF3 configured to transmit a first color light. For example, the first color filter CF1 may be a red color filter, the second color filter CF2 may be a green color filter, and the third color filter CF3 may be a blue color filter. Color filters CF1, CF2, and CF3 may each contain a polymer photosensitive resin and pigments and / or dyes. The first color filter CF1 may contain red pigments and / or dyes, the second color filter CF2 may contain green pigments and / or dyes, and the third color filter CF3 may contain blue pigments and / or dyes. In one or more embodiments, and not limited to these embodiments, the third color filter CF3 may not contain pigments and / or dyes. The third color filter CF3 may contain a polymer photosensitive resin and may not contain pigments and / or dyes. The third color filter CF3 may be transparent. The third color filter CF3 can be formed from a transparent photosensitive resin.

[0417] Furthermore, in the implementation scheme, the first color filter CF1 and the second color filter CF2 can each be a yellow color filter. The first color filter CF1 and the second color filter CF2 can not be separate but can be provided as a single color filter.

[0418] The light-shielding unit BM can be a black matrix. The light-shielding unit BM can comprise organic and / or inorganic light-shielding materials including black pigments and / or dyes. The light-shielding unit BM can prevent or reduce light leakage and can separate the boundaries between adjacent color filters CF1, CF2, and CF3. Furthermore, in an embodiment, the light-shielding unit BM can be formed from a blue color filter.

[0419] The first to the third color filters CF1, CF2 and CF3 can correspond to the red luminous area PXA-R, the green luminous area PXA-G and the blue luminous area PXA-B, respectively.

[0420] The substrate BL can be on the color filter layer CFL. The substrate BL can be a component providing the color filter layer CFL, light control layer CCL, etc., disposed thereon on a substrate surface. The substrate BL can be a glass substrate, a metal substrate, a plastic substrate, etc. However, embodiments of this disclosure are not limited thereto, and the substrate BL can be an inorganic layer, an organic layer, or a composite material layer (e.g., a composite material layer comprising inorganic and organic materials). In embodiments, the substrate BL can be omitted.

[0421] Figure 8 This is a cross-sectional view illustrating a portion of a display device according to an embodiment. Figure 8 Examples are shown corresponding to Figure 7 A cross-sectional view of a portion of the display panel DP. 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 a plurality of light-emitting structures OL-B1, OL-B2, and OL-B3 stacked sequentially in the thickness direction between the first electrode EL1 and the second electrode EL2. The light-emitting structures OL-B1, OL-B2, and OL-B3 may each include an emission layer EML (Emitting Layer). Figure 7 ), and the hole transport region HTR and electron transport region ETR with the emitter layer EML in between. Figure 7 ).

[0422] That is, the light-emitting device ED-BT included in the display device DD-TD in the implementation scheme can be a light-emitting device with a series structure and including multiple emission layers.

[0423] exist Figure 8 In the illustrated embodiment, the light emitted from each of the light-emitting structures OL-B1, OL-B2, and OL-B3 can all be blue light. However, embodiments of this disclosure are not limited to this, and the light emitted from each of the light-emitting structures OL-B1, OL-B2, and OL-B3 can be in 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 emitting light in different wavelength ranges from each other can emit white light.

[0424] The charge generation layer can be located between adjacent light-emitting structures OL-B1, OL-B2, and OL-B3. For example, charge generation layer CGL1 can be located between light-emitting structures OL-B1 and OL-B2, and charge generation layer CGL2 can be located between light-emitting structures OL-B2 and OL-B3. The charge generation layer can include a p-type charge generation layer and / or an n-type charge generation layer.

[0425] The following description, with reference to embodiments and comparative examples, will depict in more detail the polycyclic compounds according to the present disclosure and the light-emitting devices comprising the polycyclic compounds of the present disclosure. Furthermore, the embodiments illustrated below are provided for illustrative purposes only, and the scope of the present disclosure is not limited thereto.

[0426] Example

[0427] 1. Synthesis of the polycyclic compounds in the examples

[0428] First, the synthesis methods of the polycyclic compounds according to the embodiments will be described in more detail by illustrating the synthesis methods of compounds 20, 25, 51, 79, 94, 101, 110, and 122. Furthermore, in the following description, the compound synthesis methods are provided as examples, but the synthesis methods of the compounds according to the embodiments of this disclosure are not limited to the following examples.

[0429] Synthesis of Compound 20

[0430] Compound 20 according to the embodiments can be synthesized by, for example, the steps shown in reaction scheme 1 below.

[0431] Reaction Scheme 1

[0432]

[0433] Compound 20-a

[0434] In an argon atmosphere, in a 2 L flask, (10-phenylanthracene-9-yl)boric acid (50 g, 168 mmol), 4-bromo-N-phenylaniline (42 g, 168 mmol), K₂CO₃ (70 g, 500 mmol), and Pd(PPh₃)₄ (5.8 g, 5 mmol) were added and dissolved in a mixture of toluene (700 mL) and water (300 mL), and the reaction solution was stirred at about 120 °C for about 12 hours. After cooling, the reaction solution was extracted with water (1 L) and ethyl acetate (300 mL) to collect the organic layer, which was dried over MgSO₄ and then filtered. In the filtrate, the solvent was removed under reduced pressure to obtain a solid. The solid obtained therefrom was separated and purified by silica gel column chromatography using CH₂Cl₂ and hexane as eluents to obtain compound 20-a (yellow solid, 52 g, yield: 74%).

[0435] ESI-LCMS: [M+H] + :C 32 H 23 N.421.1763.

[0436] 1 H-NMR (400MHz, CDCl3): 8.21 (d, 4H), 7.65 (d, 2H), 7.55 (m, 4H), 7.37 (m, 7H), 7.02 (m, 3H).

[0437] Compound 20-b

[0438] In an argon atmosphere, in a 2 L flask, compound 20-a (50 g, 119 mmol), 3,5-dibromo-tert-butylbenzene (35 g, 119 mmol), BINAP (7.4 g, 12 mmol), sodium tert-butoxide (34.3 g, 357 mmol), and Pd₂dba₃ (5.4 g, 5.95 mmol) were added and dissolved in 1 L of toluene, and the reaction solution was stirred at about 85 °C for about 12 hours. After cooling, the reaction solution was extracted with water (1 L) and ethyl acetate (300 mL) to collect the organic layer, which was dried over MgSO₄ and then filtered. The solvent was removed from the filtrate under reduced pressure to obtain a solid. The solid obtained was separated and purified by silica gel column chromatography using CH₂Cl₂ and hexane as eluents to obtain compound 20-b (white solid, 40 g, yield: 54%).

[0439] ESI-LCMS: [M+H] + :C 42 H 34 NBr.631.1664.

[0440] 1 H-NMR (400MHz, CDCl3): 8.21 (d, 4H), 7.65 (d, 2H), 7.55 (m, 4H), 7.37 (m, 8H), 7.24 (m, 3H), 7.08 (d, 2H), 7.02 (m, 2H), 1.32 (s, 9H).

[0441] Compound 20-c

[0442] In an argon atmosphere, in a 2 L flask, compound 20-b (40 g, 63 mmol), aniline (8.8 g, 95 mmol), tri-tert-butylphosphine (6 mL, 6.3 mmol), sodium tert-butoxide (17.7 g, 189 mmol), and Pd₂dba₃ (2.9 g, 3.15 mmol) were added and dissolved in 600 mL of toluene, and the reaction solution was stirred at about 100 °C for about 6 hours. After cooling, the reaction solution was extracted with water (1 L) and ethyl acetate (300 mL) to collect the organic layer, which was dried over MgSO₄ and then filtered. The solvent was removed from the filtrate under reduced pressure to obtain a solid. The obtained solid was separated and purified by silica gel column chromatography using CH₂Cl₂ and hexane as eluents to obtain compound 20-c (white solid, 33 g, yield: 82%).

[0443] ESI-LCMS: [M+H] + :C 48 H 41 N2.645.1212.

[0444] 1 H-NMR (400MHz, CDCl3): 8.21 (d, 4H), 7.65 (d, 2H), 7.55 (m, 9H), 7.24 (m, 2H), 7.00 (m, 8H), 6.63 (s, 1H), 1.35 (s, 9H).

[0445] Compound 20-d

[0446] In an argon atmosphere, in a 1 L flask, compound 20-c (33 g, 51 mmol), 3-iodobromobenzene (14.5 g, 51 mmol), tri-tert-butylphosphine (4.6 mL, 5.0 mmol), sodium tert-butoxide (14.7 g, 153 mmol), and Pd2dba3 (2.3 g, 2.55 mmol) were added and dissolved in 400 mL of toluene, and the reaction solution was stirred at about 100 °C for about 6 hours. After cooling, the reaction solution was extracted with water (1 L) and ethyl acetate (300 mL) to collect the organic layer, which was dried over MgSO4 and then filtered. In the filtrate, the solvent was removed under reduced pressure to obtain a solid. The solid obtained therefrom was separated and purified by silica gel column chromatography using CH2Cl2 and hexane as eluents to obtain compound 20-d (white solid, 31 g, yield: 77%).

[0447] ESI-LCMS: [M+H] + :C 54 H 44 N2Br.799.2245.

[0448] 1 H-NMR (400MHz, CDCl3): 8.23(d,4H),7.61(d,2H),7.53(m,4H),7.41(m,7H),7.24(m,6H),7.03(m,10H),6.32(s,1H),1.31(s,9H).

[0449] Compound 20-e

[0450] In an argon atmosphere, in a 1 L flask, compound 20-d (30 g, 37.5 mmol), aniline (5.2 g, 56 mmol), tri-tert-butylphosphine (6 mL, 3.6 mmol), sodium tert-butoxide (10.8 g, 112.5 mmol), and Pd₂dba₃ (1.7 g, 1.8 mmol) were added and dissolved in 400 mL of toluene, and the reaction solution was stirred at about 100 °C for about 6 hours. After cooling, the reaction solution was extracted with water (1 L) and ethyl acetate (300 mL) to collect the organic layer, which was dried over MgSO₄ and then filtered. In the filtrate, the solvent was removed under reduced pressure to obtain a solid. The solid obtained therefrom was separated and purified by silica gel column chromatography using CH₂Cl₂ and hexane as eluents to obtain compound 20-e (white solid, 24 g, yield: 79%).

[0451] ESI-LCMS: [M+H] + :C 60 H 50 N3.812.3331.

[0452] 1 H-NMR (400MHz, CDCl3): 8.24(d,4H),7.61(d,2H),7.53(m,4H),7.37(m,15H),7.08(m,11H),6.84(s,1H),6.76(m,1H),6.55(s,1H),1.31(s,9H).

[0453] Compound 20-f

[0454] In an argon atmosphere, in a 1 L flask, compound 20-e (24 g, 29.5 mmol), 3,5-dibromo-tert-butylbenzene (8.6 g, 29.5 mmol), BINAP (1.9 g, 3.0 mmol), sodium tert-butoxide (9.2 g, 88.5 mmol), and Pd2dba3 (1.35 g, 1.5 mmol) were added and dissolved in 400 mL of toluene, and the reaction solution was stirred at about 100 °C for about 6 hours. After cooling, the reaction solution was extracted with water (1 L) and ethyl acetate (300 mL) to collect the organic layer, which was dried over MgSO4 and then filtered. The solvent was removed from the filtrate under reduced pressure to obtain a solid. The obtained solid was separated and purified by silica gel column chromatography using CH2Cl2 and hexane as eluents to obtain compound 20-f (white solid, 17 g, yield: 57%).

[0455] ESI-LCMS: [M+H] + :C 70 H 61 N3Br.1022.3982.

[0456] 1 H-NMR(400MHz, CDCl3):8.24(d,4H),7.61(d,2H),7.53(m,4H),7.34(m,6H),7.21(m, 6H),7.02(m,12H),6.83(s,1H),6.76(d,2H),6.63(s,1H),1.31(s,9H),1.26(s,9H).

[0457] Compound 20-g

[0458] In an argon atmosphere, in a 1 L flask, compound 20-f (17 g, 29.5 mmol), diphenylamine (2.8 g, 29.5 mmol), BINAP (1.9 g, 3.0 mmol), sodium tert-butoxide (9.2 g, 88.5 mmol), and Pd2dba3 (1.35 g, 1.4 mmol) were added and dissolved in 300 mL of toluene, and the reaction solution was stirred at about 100 °C for about 6 hours. After cooling, the reaction solution was extracted with water (1 L) and ethyl acetate (300 mL) to collect the organic layer, which was dried over MgSO4 and then filtered. In the filtrate, the solvent was removed under reduced pressure to obtain a solid. The solid obtained therefrom was separated and purified by silica gel column chromatography using CH2Cl2 and hexane as eluents to obtain compound 20-g (white solid, 22 g, yield: 69%).

[0459] ESI-LCMS: [M+H] + :C 82 H 71 N 4. 1111.4431.

[0460] 1 H-NMR(400MHz, CDCl3):8.24(d,4H),7.61(d,2H),7.53(m,4H),7.34(m,7H),7.22(m, 10H),7.09(m,19H),6.83(s,1H),6.76(d,2H),6.63(s,2H),1.31(s,9H),1.26(s,9H).

[0461] Compound 20

[0462] In an argon atmosphere, compound 20-g (20 g, 18 mmol) was dissolved in 500 mL of o-dichlorobenzene in a 1 L flask and cooled to approximately 0 °C in an ice-water bath. Boron triiodide (5 equivalents) was slowly added dropwise to the reaction solution, and the reaction solution was slowly heated to room temperature and then stirred for approximately 20 minutes. The reaction solution was then heated to approximately 150 °C and then stirred for approximately 12 hours. After cooling, triethylamine (5 mL) was slowly added dropwise to terminate the reaction, and the solvent was completely removed under reduced pressure to obtain a solid. The solid obtained was washed with MeOH and then separated and purified by silica gel column chromatography using CH2Cl2 and hexane as eluents to obtain compound 20 (yellow solid, 2.4 g, yield: 12%).

[0463] ESI-LCMS: [M+H] + :C 82 H 65 B2N 4.1127.5153.

[0464] 1 H-NMR(400MHz, CDCl3):10.03(s,1H),9.63(d,2H),8.24(d,4H),7.61(d,2H),7.47(m,6H),7.34(m, 7H),7.22(m,10H),7.03(m,15H),6.83(s,1H),6.76(d,2H),6.63(s,2H),1.31(s,9H),1.26(s,9H).

[0465] Synthesis of Compound 25

[0466] Compound 25 according to the embodiments can be synthesized by, for example, the steps shown in reaction scheme 2 below.

[0467] Reaction Scheme 2

[0468]

[0469] Compound 25-a

[0470] In an argon atmosphere, in a 2 L flask, (10-phenylanthracene-9-yl)boric acid (50 g, 168 mmol), 3-iodobromobenzene (48 g, 168 mmol), K₂CO₃ (70 g, 500 mmol), and Pd(PPh₃)₄ (5.8 g, 5 mmol) were added and dissolved in a mixture of toluene (700 mL) and water (300 mL), and the reaction solution was stirred at about 120 °C for about 12 hours. After cooling, the reaction solution was extracted with water (1 L) and ethyl acetate (300 mL) to collect the organic layer, which was dried over MgSO₄ and then filtered. In the filtrate, the solvent was removed under reduced pressure to obtain a solid. The solid obtained therefrom was separated and purified by silica gel column chromatography using CH₂Cl₂ and hexane as eluents to obtain compound 25-a (yellow solid, 45 g, yield: 66%).

[0471] ESI-LCMS: [M+H] + :C 26 H 18 Br.409.0432.

[0472] 1 H-NMR (400MHz, CDCl3): 8.21 (m, 4H), 7.65 (m, 3H), 7.55 (t, 2H), 7.41 (m, 8H).

[0473] Compound 25-b

[0474] In an argon atmosphere, in a 2L flask, compound 25-a (45g, 110mmol) and N... 1 N 1 N 3 N 3 Tetraphenylbenzene-1,3,5-triamine (47 g, 110 mmol), tri-tert-butylphosphine (10 mL, 11.0 mmol), sodium tert-butoxide (32 g, 330 mmol), and Pd₂dba₃ (5.0 g, 5.5 mmol) were added and dissolved in 600 mL of toluene, and the reaction solution was stirred at about 100 °C for about 6 hours. After cooling, the reaction solution was extracted with water (1 L) and ethyl acetate (300 mL) to collect the organic layer, which was dried over MgSO₄ and then filtered. The solvent was removed from the filtrate under reduced pressure to obtain a solid. The solid obtained therefrom was separated and purified by silica gel column chromatography using CH₂Cl₂ and hexane as eluents to obtain compound 25-b (white solid, 56 g, yield: 68%).

[0475] ESI-LCMS: [M+H] + :C 56 H 42 N3.756.3221.

[0476] 1 H-NMR (400MHz, CDCl3): 8.23(m,4H),7.73(d,1H),7.66(d,2H),7.53(t,3H),7.37(m,5H),7.17(m,10H),7.08(m,12H),6.49(s,3H).

[0477] Compound 25-c

[0478] In an argon atmosphere, in a 2 L flask, compound 25-b (55 g, 72 mmol), 3-bromophenol (12.6 g, 72 mmol), tri-tert-butylphosphine (6.6 mL, 7.2 mmol), sodium tert-butoxide (21 g, 216 mmol), and Pd2dba3 (3.3 g, 3.6 mmol) were added and dissolved in 600 mL of toluene, and the reaction solution was stirred at about 100 °C for about 6 hours. After cooling, the reaction solution was extracted with water (1 L) and ethyl acetate (300 mL) to collect the organic layer, which was dried over MgSO4 and then filtered. In the filtrate, the solvent was removed under reduced pressure to obtain a solid. The solid obtained therefrom was separated and purified by silica gel column chromatography using CH2Cl2 and hexane as eluents to obtain compound 25-c (white solid, 44.5 g, yield: 73%).

[0479] ESI-LCMS: [M+H] + :C 62 H 46 N3O.848.2119.

[0480] 1 H-NMR (400MHz, CDCl3): 8.23 ​​(m, 4H), 7.66 (d, 2H), 7.55 (t, 3H), 7.24 (m, 16H), 7.12 (m, 8H), 6.62 (m, 3H), 6.49 (s, 3H).

[0481] Compound 25-d

[0482] In an argon atmosphere, in a 1 L flask, compound 25-c (44 g, 52 mmol) and 5-bromo-N... 1 N 1 N 3 N 3 Tetraphenylphenyl-1,3-diamine (25.5 g, 52 mmol), CuI (9.88 g, 52 mmol), and 2-pyridinecarboxylic acid (6.4 g, 52 mmol) were added and dissolved in 500 mL of DMF, and the reaction solution was stirred at about 180 °C for about 12 hours. After cooling, the reaction solution was poured into water (1 L), and the resulting solid was filtered. The obtained solid was dissolved again with CH2Cl2 and washed several times with water to collect the organic layer, which was dried over MgSO4 and then filtered. In the filtrate, the solvent was removed under reduced pressure to obtain the solid. The obtained solid was separated and purified by silica gel column chromatography using CH2Cl2 and hexane as eluents to obtain compound 25-d (white solid, 28 g, yield: 43%).

[0483] ESI-LCMS: [M+H] + :C 92 H 68 N5O.1258.0439.

[0484] 1 H-NMR(400MHz, CDCl3):8.22(m,4H),7.66(d,2H),7.55(t,3H),7.37(t,5H),7.24(m, 24H),7.12(m,20H),6.86(s,1H),6.80(d,1H),6.49(m,6H),6.62(m,3H),6.49(s,3H).

[0485] Compound 25

[0486] In an argon atmosphere, compound 25-d (28 g, 22 mmol) was dissolved in 500 mL of o-dichlorobenzene in a 1 L flask and cooled to approximately 0 °C in an ice-water bath. Boron tribromide (5 equivalents) was slowly added dropwise to the reaction solution, and the reaction solution was slowly heated to room temperature and then stirred for approximately 20 minutes. The reaction solution was then heated to approximately 150 °C and then stirred for approximately 12 hours. After cooling, triethylamine (5 mL) was slowly added dropwise to terminate the reaction, and the solvent was completely removed under reduced pressure to obtain a solid. The solid obtained was washed with MeOH and then separated and purified by silica gel column chromatography using CH2Cl2 and hexane as eluents to obtain compound 25 (yellow solid, 2.5 g, yield: 9%).

[0487] ESI-LCMS: [M+H] + :C 72 H 62 B2N5O.1274.0947.

[0488] 1 H-NMR (400MHz, CDCl3): 10.2(s,1H),9.42(d,2H),8.23(d,4H),7.65(d,2H),7.24(m,21H),7.07(m,20H),6.86(s,1H),6.52(m,4H).

[0489] Synthesis of Compound 51

[0490] Compound 51 according to the embodiments can be synthesized by, for example, the steps shown in reaction scheme 3 below.

[0491] Reaction scheme 3

[0492]

[0493] Compound 51-a

[0494] In an argon atmosphere, in a 2L flask, 50g of 9-amino-10-phenylanthracene (186mmol) and 5-chloro-N... 1 N 1 N 3 N 3Tetraphenylphenyl-1,3-diamine (83 g, 186 mmol), tri-tert-butylphosphine (17 mL, 18.6 mmol), sodium tert-butoxide (53 g, 558 mmol), and Pd2dba3 (8.5 g, 9.3 mmol) were added and dissolved in 1 L of o-xylene, and the reaction solution was then stirred at about 140 °C for about 6 hours. After cooling, the reaction solution was extracted with water (1 L) and ethyl acetate (300 mL) to collect the organic layer, which was dried over MgSO4 and then filtered. The solvent was removed from the filtrate under reduced pressure to obtain a solid. The solid obtained therefrom was separated and purified by silica gel column chromatography using CH2Cl2 and hexane as eluents to obtain compound 51-a (white solid, 83 g, yield: 66%).

[0495] ESI-LCMS: [M+H] + :C 50 H 38 N3.680.0115.

[0496] 1 H-NMR (400MHz, CDCl3): 8.19 (d, 4H), 7.65 (d, 2H), 7.55 (t, 2H), 7.42 (m, 5H), 7.24 (m, 8H), 7.00 (m, 12H), 6.49 (s, 3H).

[0497] Compound 51-b

[0498] In an argon atmosphere, in a 2 L flask, compound 51-a (80 g, 118 mmol), 3-bromo-thiophenol (22 g, 118 mmol), tri-tert-butylphosphine (11 mL, 12 mmol), sodium tert-butoxide (34 g, 354 mmol), and Pd2dba3 (5.4 g, 5.9 mmol) were added and dissolved in 1 L of toluene, and the reaction solution was stirred at about 100 °C for about 6 hours. After cooling, the reaction solution was extracted with water (1 L) and ethyl acetate (300 mL) to collect the organic layer, which was dried over MgSO4 and then filtered. In the filtrate, the solvent was removed under reduced pressure to obtain a solid. The solid obtained therefrom was separated and purified by silica gel column chromatography using CH2Cl2 and hexane as eluents to obtain compound 51-b (white solid, 59 g, yield: 63%).

[0499] ESI-LCMS: [M+H] + :C 56 H 42 N3S.788.2224.

[0500] 1H-NMR (400MHz, CDCl3): 8.22(m,4H),7.72(s,1H),7.65(d,2H),7.55(t,2H),7.41(m,5H),7.24(m,9H),7.00(m,12H),6.84(m,2H),6.52(s,3H).

[0501] Compound 51-c

[0502] In an argon atmosphere, in a 1 L flask, compound 51-b (59 g, 75 mmol) and 5-chloro-N... 1 N 1 N 3 N 3 Tetraphenylphenyl-1,3-diamine (33.5 g, 75 mmol), CuI (14 g, 75 mmol), and 2-pyridinecarboxylic acid (9.2 g, 75 mmol) were added and dissolved in 700 mL of DMF, and the reaction solution was stirred at about 180 °C for about 12 hours. After cooling, the reaction solution was poured into water (1 L), and the resulting solid was filtered. The obtained solid was dissolved again with CH2Cl2 and washed several times with water to collect the organic layer, which was dried over MgSO4 and then filtered. In the filtrate, the solvent was removed under reduced pressure to obtain a solid. The obtained solid was separated and purified by silica gel column chromatography using CH2Cl2 and hexane as eluents to obtain compound 51-c (white solid, 47 g, yield: 52%).

[0503] ESI-LCMS: [M+H] + :C 86 H 64 N5S.1198.4434.

[0504] 1 H-NMR(400MHz, CDCl3):8.19(m,4H),7.76(s,1H),7.65(d,2H),7.55(t,2H),7. 42(m,7H),7.22(m,17H),7.08(m,25H),6.89(m,1H),6.57(s,1H),6.52(m,3H).

[0505] Compound 51

[0506] In an argon atmosphere, compound 51-c (45 g, 38 mmol) was dissolved in 1 L of o-dichlorobenzene in a 1 L flask and cooled to approximately 0 °C in an ice-water bath. Boron tribromide (5 equivalents) was slowly added dropwise to the reaction solution, and the reaction solution was slowly heated to room temperature and then stirred for approximately 20 minutes. The reaction solution was heated to approximately 150 °C and then stirred for approximately 12 hours. After cooling, triethylamine (10 mL) was slowly added dropwise to terminate the reaction, and the solvent was completely removed under reduced pressure to obtain a solid. The solid obtained was washed with MeOH and then separated and purified by silica gel column chromatography using CH2Cl2 and hexane as eluents to obtain compound 51 (yellow solid, 2.7 g, yield: 6%).

[0507] ESI-LCMS: [M+H] + :C 86 H 57 B2N5S.1214.4321.

[0508] 1 H-NMR(400MHz, CDCl3):10.2(s,1H),9.42(d,2H),8.19(m,4H),7.76(s,1H),7.65(d,2H),7. 55(t,2H),7.42(m,7H),7.22(m,15H),7.08(m,24H),6.89(m,1H),6.57(s,1H),6.52(m,3H).

[0509] Synthesis of Compound 79

[0510] Compound 79 according to the embodiments can be synthesized by, for example, the steps shown in reaction scheme 4 below.

[0511] Reaction scheme 4

[0512]

[0513]

[0514] Compound 79-a

[0515] In an argon atmosphere, in a 2 L flask, 3,5-dibromo-biphenyl (50 g, 160 mmol), compound 20-a (67.5 g, 160 mmol), BINAP (9.9 mL, 16 mmol), sodium tert-butoxide (46 g, 480 mmol), and Pd₂dba₃ (7.3 g, 8.0 mmol) were added and dissolved in 1 L of toluene, and the reaction solution was stirred at about 100 °C for about 6 hours. After cooling, the reaction solution was extracted with water (1 L) and ethyl acetate (300 mL) to collect the organic layer, which was dried over MgSO₄ and then filtered. The solvent was removed from the filtrate under reduced pressure to obtain a solid. The solid obtained was separated and purified by silica gel column chromatography using CH₂Cl₂ and hexane as eluents to obtain compound 79-a (white solid, 64 g, yield: 61%).

[0516] ESI-LCMS: [M+H] + :C 44 H 31 NBr.652.1515.

[0517] 1 H-NMR (400MHz, CDCl3): 8.25(m,4H),7.75(d,2H),7.65(d,2H),7.55(m,6H),7.37(m,9H),7.21(m,3H),7.00(m,4H).

[0518] Compound 79-b

[0519] In an argon atmosphere, in a 1 L flask, Mg (2.3 g, 98 mmol) was dissolved in 500 mL of anhydrous THF, and a solution of compound 79-a (64 g, 98 mmol) dissolved in 300 mL of anhydrous THF was slowly added dropwise to the solution at room temperature. Iodine (50 mg, catalyst) was added to the reaction solution, and the solution was then heated to approximately 80 °C. The reaction solution was stirred at the same temperature for approximately 30 minutes, and when the color of the reaction solution changed from brown to gray, the solution was cooled to room temperature, and selenium powder (15 g, 98 mmol) was added partically. The reaction solution was reheated to approximately 80 °C and then stirred for approximately 2 hours, and after cooling, 1 M HCl was slowly added dropwise until the pH of the reaction solution became neutral. The reaction solution was extracted with ethyl acetate and water to obtain an organic layer. The obtained organic layer was passed through a diatomaceous earth filter to remove undissolved solids, and the filtrate was then concentrated to obtain a solid. The solid obtained therefrom was separated and purified by silica gel column chromatography using CH2Cl2 and hexane as eluents to obtain compound 79-b (yellow solid, 27 g, yield: 43%).

[0520] ESI-LCMS: [M+H] + :C 44 H 31 NSe.654.0047.

[0521] 1 H-NMR (400MHz, CDCl3): 8.25(m,4H),7.75(d,2H),7.65(d,2H),7.55(m,6H),7.37(m,9H),7.21(m,3H),7.00(m,3H).

[0522] Compound 79-c

[0523] In an argon atmosphere, in a 1 L flask, compound 79-b (25 g, 38 mmol), 3-bromoaniline (6.5 g, 38 mmol), CuI (7.2 g, 38 mmol), and 2-pyridinecarboxylic acid (4.6 g, 38 mmol) were added and dissolved in 300 mL of DMF, and the reaction solution was stirred at approximately 180 °C for approximately 12 hours. After cooling, the reaction solution was poured into water (1 L), and the resulting solid was filtered. The obtained solid was dissolved again with CH₂Cl₂ and washed several times with water to collect the organic layer, which was dried over MgSO₄ and then filtered. In the filtrate, the solvent was removed under reduced pressure to obtain a solid. The obtained solid was separated and purified by silica gel column chromatography using ethyl acetate and hexane as eluents to obtain compound 79-c (white solid, 17 g, yield: 59%).

[0524] ESI-LCMS: [M+H] + :C 50 H 37 N2Se.745.1117.

[0525] 1 H-NMR (400MHz, CDCl3): 8.21(m,4H),7.75(d,2H),7.65(d,2H),7.37(m,15H),7.20(m,5H),7.08(m,3H),6.73(m,2H),6.64(d,1H),5.28(br,2H).

[0526] Compound 79-d

[0527] In an argon atmosphere, in a 1 L flask, compound 79-c (17 g, 23 mmol), bromobenzene (3.7 g, 23 mmol), BINAP (1.4 g, 2.3 mmol), sodium tert-butoxide (6.6 g, 69 mmol), and Pd2dba3 (1.1 g, 1.15 mmol) were added and dissolved in 200 mL of toluene, and the reaction solution was stirred at about 100 °C for about 6 hours. After cooling, the reaction solution was extracted with water (1 L) and ethyl acetate (300 mL) to collect the organic layer, which was dried over MgSO4 and then filtered. In the filtrate, the solvent was removed under reduced pressure to obtain a solid. The solid obtained therefrom was separated and purified by silica gel column chromatography using CH2Cl2 and hexane as eluents to obtain compound 79-d (white solid, 15 g, yield: 77%).

[0528] ESI-LCMS: [M+H] + :C 56 H 41 N2Se.821.2424.

[0529] 1 H-NMR (400MHz, CDCl3): 8.21 (m, 4H), 7.75 (d, 2H), 7.65 (d, 2H), 7.37 (m, 17H), 7.20 (m, 5H), 7.08 (m, 8H).

[0530] Compound 79-e

[0531] In an argon atmosphere, in a 1 L flask, compound 79-d (17 g, 18 mmol) and 5-chloro-N... 1 N 1 N 3 N 3 Tetraphenylphenyl-1,3-diamine (8.0 g, 18 mmol), tri-tert-butylphosphine (1.6 g, 1.8 mmol), sodium tert-butoxide (5.2 g, 54 mmol), and Pd₂dba₃ (0.8 g, 0.9 mmol) were added and dissolved in 200 mL of toluene, and the reaction solution was stirred at about 100 °C for about 6 hours. After cooling, the reaction solution was extracted with water (1 L) and ethyl acetate (300 mL) to collect the organic layer, which was dried over MgSO₄ and then filtered. The solvent was removed from the filtrate under reduced pressure to obtain a solid. The solid obtained therefrom was separated and purified by silica gel column chromatography using CH₂Cl₂ and hexane as eluents to obtain compound 79-e (white solid, 15 g, yield: 75%).

[0532] ESI-LCMS: [M+H] + :C80 H 58 N3Se.1140.3741.

[0533] 1 H-NMR (400MHz, CDCl3): 8.21 (m, 4H), 7.75 (d, 2H), 7.65 (d, 2H), 7.37 (m, 29H), 7.20 (m, 18H).

[0534] Compound 79

[0535] In an argon atmosphere, compound 79-e (15 g, 13 mmol) was dissolved in 400 mL of o-dichlorobenzene in a 1 L flask and cooled to approximately 0 °C in an ice-water bath. Boron tribromide (5 equivalents) was slowly added dropwise to the reaction solution, and the reaction solution was slowly heated to room temperature and then stirred for approximately 20 minutes. The reaction solution was then heated to approximately 150 °C and then stirred for approximately 12 hours. After cooling, triethylamine (5 mL) was slowly added dropwise to terminate the reaction, and the solvent was completely removed under reduced pressure to obtain a solid. The solid obtained was washed with MeOH and then separated and purified by silica gel column chromatography using CH2Cl2 and hexane as eluents to obtain compound 79 (yellow solid, 1.8 g, yield: 12%).

[0536] ESI-LCMS: [M+H] + :C 80 H 52 B2N3Se.1156.3370.

[0537] 1 H-NMR (400MHz, CDCl3): 10.2(s,1H),9.42(d,2H),8.21(m,4H),7.75(d,2H),7.65(d,2H),7.37(m,21H),7.20(m,17H).

[0538] Synthesis of Compound 94

[0539] Compound 94 according to the embodiments can be synthesized by, for example, the steps shown in reaction scheme 5 below.

[0540] Reaction scheme 5

[0541]

[0542]

[0543] Compound 94-a

[0544] In an argon atmosphere, in a 2 L flask, (10-phenylanthracene-9-yl)boric acid (50 g, 168 mmol), 4-bromo-N-phenylaniline (42 g, 168 mmol), K₂CO₃ (70 g, 500 mmol), and Pd(PPh₃)₄ (5.8 g, 5 mmol) were added and dissolved in a mixture of toluene (700 mL) and water (300 mL), and the reaction solution was stirred at about 120 °C for about 12 hours. After cooling, the reaction solution was extracted with water (1 L) and ethyl acetate (300 mL) to collect the organic layer, which was dried over MgSO₄ and then filtered. In the filtrate, the solvent was removed under reduced pressure to obtain a solid. The solid obtained therefrom was separated and purified by silica gel column chromatography using CH₂Cl₂ and hexane as eluents to obtain compound 94-a (yellow solid, 52 g, yield: 74%).

[0545] ESI-LCMS: [M+H] + :C 32 H 23 N.421.1763.

[0546] 1 H-NMR (400MHz, CDCl3): 8.21 (d, 4H), 7.65 (d, 2H), 7.55 (m, 4H), 7.37 (m, 7H), 7.02 (m, 3H).

[0547] Compound 94-b

[0548] In an argon atmosphere, in a 2 L flask, compound 94-a (50 g, 119 mmol), 3,5-dibromo-methoxybenzene (32.0 g, 119 mmol), BINAP (7.5 g, 12.0 mmol), sodium tert-butoxide (34 g, 357 mmol), and Pd2dba3 (5.5 g, 6.0 mmol) were added and dissolved in 1 L of toluene, and the reaction solution was stirred at about 100 °C for about 6 hours. After cooling, the reaction solution was extracted with water (1 L) and ethyl acetate (300 mL) to collect the organic layer, which was dried over MgSO4 and then filtered. In the filtrate, the solvent was removed under reduced pressure to obtain a solid. The solid obtained therefrom was separated and purified by silica gel column chromatography using CH2Cl2 and hexane as eluents to obtain compound 94-b (white solid, 48 g, yield: 66%).

[0549] ESI-LCMS: [M+H] + :C 39 H 29 NBrO.606.1237.

[0550] 1 H-NMR(400MHz, CDCl3):8.21(m,4H),7.65(d,2H),7.55(m,4H),7.37(m,7H),7 .24(m,2H),7.00(m,3H),6.96(s,1H),6.90(s,1H),6.76(s,1H),3.81(s,3H).

[0551] Compound 94-c

[0552] In an argon atmosphere, in a 2 L flask, compound 94-b (48 g, 79 mmol), N-phenyl-[1,1'-biphenyl]-2-amine (19.4 g, 79 mmol), tri-tert-butylphosphine (7.2 mL, 8.0 mmol), sodium tert-butoxide (23 g, 237 mmol), and Pd2dba3 (3.6 g, 4.0 mmol) were added and dissolved in 600 mL of toluene, and the reaction solution was stirred at about 100 °C for about 6 hours. After cooling, the reaction solution was extracted with water (1 L) and ethyl acetate (300 mL) to collect the organic layer, which was dried over MgSO4 and then filtered. In the filtrate, the solvent was removed under reduced pressure to obtain a solid. The solid obtained therefrom was separated and purified by silica gel column chromatography using CH2Cl2 and hexane as eluents to obtain compound 94-c (white solid, 44 g, yield: 73%).

[0553] ESI-LCMS: [M+H] + :C 57 H 42 N2O.771.3321.

[0554] 1 H-NMR (400MHz, CDCl3): 8.23(m,4H),8.10(d,1H),7.65(d,2H),7.55(m,4H),7.37(m,12H),7.24(m,4H),7.00(m,9H),6.48(s,3H),3.81(s,3H).

[0555] Compound 94-d

[0556] In an argon atmosphere, compound 94-c (44 g, 57 mmol) was added to and dissolved in 600 mL of anhydrous CH2Cl2 in a 2 L flask, and the reaction solution was then cooled to approximately 0 °C. BBr3 (1.5 equivalents) was slowly added dropwise to the reaction solution, and the reaction solution was heated to room temperature and then stirred for approximately 24 hours. The reaction solution was slowly poured into water (1 L), and the organic layer was collected by extraction with ethyl acetate (300 mL). The organic layer was dried over MgSO4 and then filtered. The solvent was removed from the filtrate under reduced pressure to obtain a solid. The solid obtained was separated and purified by silica gel column chromatography using CH2Cl2 and hexane as eluents to obtain compound 94-d (dark brown solid, 26 g, yield: 61%).

[0557] ESI-LCMS: [M+H] + :C 56 H 41 N2O.757.1267.

[0558] 1 H-NMR (400MHz, CDCl3): 8.23 ​​(m, 4H), 8.10 (d, 1H), 7.65 (d, 2H), 7.55 (m, 4H), 7.37 (m, 12H), 7.24 (m, 4H), 7.00 (m, 9H), 6.48 (s, 3H).

[0559] Compound 94-e

[0560] In an argon atmosphere, in a 2L flask, 5-chloro-N 1 N 1 N 3 N 3 Tetraphenylphenyl-1,3-diamine (50 g, 111 mmol), [1,1':3',1”-triphenyl]-2'-amine (27 g, 111 mmol), tri-tert-butylphosphine (10 mL, 11.2 mmol), sodium tert-butoxide (32 g, 333 mmol), and Pd2dba3 (5.0 g, 5.6 mmol) were added and dissolved in 1 L of o-xylene, and the reaction solution was stirred at about 140 °C for about 6 hours. After cooling, the reaction solution was extracted with water (1 L) and ethyl acetate (300 mL) to collect the organic layer, which was dried over MgSO4 and then filtered. The solvent was removed from the filtrate under reduced pressure to obtain a solid. The solid obtained therefrom was separated and purified by silica gel column chromatography using CH2Cl2 and hexane as eluents to obtain compound 94-e (white solid, 59 g, yield: 82%).

[0561] ESI-LCMS: [M+H]+ :C 48 H 38 N3.656.0887.

[0562] 1 H-NMR (400MHz, CDCl3): 8.20 (d, 2H), 7.43 (m, 7H), 7.24 (m, 8H), 7.08 (m, 16H), 6.49 (s, 3H).

[0563] Compound 94-f

[0564] In an argon atmosphere, in a 1 L flask, compound 94-e (50 g, 76 mmol), 3-iodobromobenzene (22 g, 76 mmol), CuI (14.4 g, 76 mmol), and K₂CO₃ (104 g, 760 mmol) were added and dissolved in 500 mL of o-dichlorobenzene, and the reaction solution was stirred at about 180 °C for about 3 days. After cooling, the reaction solution was extracted with water (1 L) and ethyl acetate (300 mL) to collect the organic layer, which was dried over MgSO₄ and then filtered. In the filtrate, the solvent was removed under reduced pressure to obtain a solid. The solid obtained therefrom was separated and purified by silica gel column chromatography using CH₂Cl₂ and hexane as eluents to obtain compound 94-f (white solid, 30 g, yield: 49%).

[0565] ESI-LCMS: [M+H] + :C 54 H 41 N3.810.1217.

[0566] 1 H-NMR (400MHz, CDCl3): 8.20 (d, 2H), 7.43 (m, 7H), 7.27 (m, 10H), 7.08 (m, 18H), 6.49 (s, 3H).

[0567] Compound 94-g

[0568] In an argon atmosphere, in a 1 L flask, compound 94-f (27 g, 33 mmol), compound 94-d (25 g, 33 mmol), 3-iodobromobenzene (22 g, 33 mmol), CuI (6.3 g, 33 mmol), 2-pyridinecarboxylic acid (4.1 g, 33 mmol), and K₂CO₃ (14 g, 99 mmol) were added and dissolved in 500 mL of DMF, and the reaction solution was stirred at about 180 °C for about 24 hours. After cooling, the reaction solution was extracted with water (1 L) and ethyl acetate (300 mL) to collect the organic layer, which was dried over MgSO₄ and then filtered. In the filtrate, the solvent was removed under reduced pressure to obtain a solid. The solid obtained therefrom was separated and purified by silica gel column chromatography using CH₂Cl₂ and hexane as eluents to obtain compound 94-g (white solid, 31 g, yield: 63%).

[0569] ESI-LCMS: [M+H] + :C 110 H 80 N5O.1486.5119.

[0570] 1 H-NMR (400MHz, CDCl3): 8.24(m,6H),8.11(d,1H),7.65(d,1H),7.55(m,4H),7.43(m,19H),7.27(m,17H),7.08(m,20H),6.87(d,1H),6.72(m,1H).

[0571] Compound 94

[0572] In an argon atmosphere, compound 94-g (30 g, 20 mmol) was dissolved in 500 mL of o-dichlorobenzene in a 1 L flask and cooled to approximately 0 °C in an ice-water bath. Boron tribromide (5 equivalents) was slowly added dropwise to the reaction solution, and the reaction solution was slowly heated to room temperature and then stirred for approximately 20 minutes. The reaction solution was then heated to approximately 150 °C and then stirred for approximately 12 hours. After cooling, triethylamine (5 mL) was slowly added dropwise to terminate the reaction, and the solvent was completely removed under reduced pressure to obtain a solid. The solid obtained was washed with MeOH and then separated and purified by silica gel column chromatography using CH2Cl2 and hexane as eluents to obtain compound 94 (yellow solid, 3.3 g, yield: 11%).

[0573] ESI-LCMS: [M+H] + :C 110 H 73 N5OB2.1502.7812.

[0574] 1 H-NMR (400MHz, CDCl3): 10.42(s,1H),9.37(d,2H),8.24(m,6H),7.55(m,4H),7.43(m,19H),7.27(m,16H),7.08(m,20H),6.87(d,1H),6.72(m,1H).

[0575] Synthesis of Compound 101

[0576] Compound 101 according to the embodiments can be synthesized by, for example, the steps shown in reaction scheme 6 below.

[0577] Reaction scheme 6

[0578]

[0579] Compound 101-a

[0580] In an argon atmosphere, in a 2 L flask, anthracene-9-boronic acid (50 g, 225 mmol), 3,5-dichlorobromobenzene (50 g, 225 mmol), K₂CO₃ (93 g, 675 mmol), and Pd(PPh₃)₄ (13 g, 11 mmol) were added and dissolved in a mixed solution of toluene (700 mL), EtOH (200 mL), and water (300 mL). The reaction solution was then stirred at approximately 120 °C for approximately 12 hours. After cooling, the reaction solution was extracted with water (1 L) and ethyl acetate (300 mL) to collect the organic layer, which was dried over MgSO₄ and then filtered. The solvent was removed from the filtrate under reduced pressure to obtain a solid. The solid obtained was separated and purified by silica gel column chromatography using CH₂Cl₂ and hexane as eluents to obtain compound 101-a (white solid, 52 g, yield: 74%).

[0581] ESI-LCMS: [M+H] + :C 20 H 13 Cl2.323.0099.

[0582] 1 H-NMR (400MHz, CDCl3): 8.39 (s, 1H), 8.19 (d, 2H), 8.03 (d, 2H), 7.85 (s, 2H), 7.71 (s, 1H), 7.43 (m, 4H).

[0583] Compound 101-b

[0584] In an argon atmosphere, in a 2 L flask, compound 101-a (50 g, 155 mmol), diphenylamine (26 g, 155 mmol), tri-tert-butylphosphine (14 mL, 15 mmol), sodium tert-butoxide (45 g, 465 mmol), and Pd2dba3 (7.0 g, 7.8 mmol) were added and dissolved in 1 L of o-xylene, and the reaction solution was stirred at about 140 °C for about 6 hours. After cooling, the reaction solution was extracted with water (1 L) and ethyl acetate (300 mL) to collect the organic layer, which was dried over MgSO4 and then filtered. The solvent was removed from the filtrate under reduced pressure to obtain a solid. The solid obtained was separated and purified by silica gel column chromatography using CH2Cl2 and hexane as eluents to obtain compound 101-b (white solid, 40 g, yield: 56%).

[0585] ESI-LCMS: [M+H] + :C 32 H 23 NCl.456.1515.

[0586] 1 H-NMR (400MHz, CDCl3): 8.29 (s, 1H), 8.09 (d, 2H), 8.03 (d, 2H), 7.63 (s, 1H), 7.50 (s, 1H), 7.43 (m, 4H), 7.24 (m, 4H), 7.03 (m, 7H).

[0587] Compound 101-c

[0588] In an argon atmosphere, in a 2 L flask, compound 101-b (40 g, 88 mmol), aniline (10.6 g, 114 mmol), tri-tert-butylphosphine (8 mL, 8.8 mmol), sodium tert-butoxide (25 g, 264 mmol), and Pd2dba3 (4.0 g, 4.4 mmol) were added and dissolved in 600 mL of o-xylene, and the reaction solution was stirred at about 140 °C for about 6 hours. After cooling, the reaction solution was extracted with water (1 L) and ethyl acetate (300 mL) to collect the organic layer, which was dried over MgSO4 and then filtered. In the filtrate, the solvent was removed under reduced pressure to obtain a solid. The obtained solid was separated and purified by silica gel column chromatography using CH2Cl2 and hexane as eluents to obtain compound 101-c (white solid, 26 g, yield: 59%).

[0589] ESI-LCMS: [M+H] + :C 38 H 28 N2.513.2121.

[0590] 1 H-NMR (400MHz, CDCl3): 8.39 (br, 1H), 8.12 (d, 2H), 8.03 (d, 2H), 7.42 (m, 2H), 7.24 (m, 4H), 7.08 (m, 4H), 6.93 (s, 3H).

[0591] Compound 101-d

[0592] In an argon atmosphere, in a 1 L flask, compound 101-c (26 g, 50 mmol), 1,3-dibromobenzene (5.9 g, 25 mmol), tri-tert-butylphosphine (2.2 mL, 2.6 mmol), sodium tert-butoxide (7.2 g, 75 mmol), and Pd₂dba₃ (1.1 g, 1.3 mmol) were added and dissolved in 6 mL of o-xylene, and the reaction solution was stirred at about 100 °C for about 12 hours. After cooling, the reaction solution was extracted with water (1 L) and ethyl acetate (300 mL) to collect the organic layer, which was dried over MgSO₄ and then filtered. In the filtrate, the solvent was removed under reduced pressure to obtain a solid. The solid obtained therefrom was separated and purified by silica gel column chromatography using CH₂Cl₂ and hexane as eluents to obtain compound 101-d (white solid, 18 g, yield: 66%).

[0593] ESI-LCMS: [M+H] + :C 82 H 59 N4.1099.4327.

[0594] 1 H-NMR (400MHz, CDCl3): 8.39(s,2H),8.19(d,4H),8.03(d,4H),7.42(m,8H),7.24(m,13H),7.08(m,15H),6.93(s,6H),6.83(s,1H),6.64(d,2H).

[0595] Compound 101

[0596] In an argon atmosphere, compound 101-d (18 g, 16 mmol) was dissolved in 400 mL of o-dichlorobenzene in a 1 L flask and cooled to approximately 0 °C in an ice-water bath. Boron tribromide (5 equivalents) was slowly added dropwise to the reaction solution, and the reaction solution was slowly heated to room temperature and then stirred for approximately 20 minutes. The reaction solution was then heated to approximately 150 °C and then stirred for approximately 12 hours. After cooling, triethylamine (5 mL) was slowly added dropwise to terminate the reaction, and the solvent was completely removed under reduced pressure to obtain a solid. The solid obtained was washed with MeOH and then separated and purified by silica gel column chromatography using CH2Cl2 and hexane as eluents to obtain compound 101 (yellow solid, 1.6 g, yield: 9%).

[0597] ESI-LCMS: [M+H] + :C 82 H 53 N4B2.1115.5623.

[0598] 1 H-NMR(400MHz, CDCl3):10.42(s,1H),9.37(d,2H),8.39(s,2H),8.19(d,4H),8 .03(d,4H),7.42(m,8H),7.24(m,13H),7.08(m,15H),7.01(s,4H),6.83(s,1H).

[0599] Synthesis of Compound 110

[0600] Compound 110 according to the embodiments can be synthesized by, for example, the steps shown in reaction scheme 7 below.

[0601] Reaction Scheme 7

[0602]

[0603] Compound 110-a

[0604] In an argon atmosphere, in a 2 L flask, 9-phenyl-anthracene-10-boric acid (50 g, 168 mmol), 3,5-dichloro-bromobenzene (38 g, 168 mmol), K₂CO₃ (70 g, 504 mmol), and Pd(PPh₃)₄ (9.7 g, 8.4 mmol) were added and dissolved in a mixture of toluene (700 mL), EtOH (200 mL), and water (300 mL). The reaction solution was then stirred at approximately 120 °C for approximately 12 hours. After cooling, the reaction solution was extracted with water (1 L) and ethyl acetate (300 mL) to collect the organic layer, which was dried over MgSO₄ and then filtered. The solvent was removed from the filtrate under reduced pressure to obtain a solid. The solid obtained was separated and purified by silica gel column chromatography using CH₂Cl₂ and hexane as eluents to obtain compound 110-a (white solid, 48 g, yield: 72%).

[0605] ESI-LCMS: [M+H] + :C 26 H 17 Cl2.399.0973.

[0606] 1 H-NMR (400MHz, CDCl3): 8.21 (m, 4H), 7.85 (s, 2H), 7.71 (s, 1H), 7.65 (d, 2H), 7.55 (m, 2H), 7.37 (m, 4H).

[0607] Compound 110-b

[0608] In an argon atmosphere, in a 2 L flask, compound 110-a (48 g, 120 mmol), diphenylamine (20 g, 120 mmol), BINAP (7.5 g, 12 mmol), sodium tert-butoxide (35 g, 360 mmol), and Pd2dba3 (5.5 g, 6.0 mmol) were added and dissolved in 1 L of o-xylene, and the reaction solution was stirred at about 140 °C for about 6 hours. After cooling, the reaction solution was extracted with water (1 L) and ethyl acetate (300 mL) to collect the organic layer, which was dried over MgSO4 and then filtered. In the filtrate, the solvent was removed under reduced pressure to obtain a solid. The solid obtained therefrom was separated and purified by silica gel column chromatography using CH2Cl2 and hexane as eluents to obtain compound 110-b (white solid, 42 g, yield: 67%).

[0609] ESI-LCMS: [M+H] + :C 38 H 26 ClN.532.1258.

[0610] 1 H-NMR (400MHz, CDCl3): 8.21 (m, 4H), 7.35 (m, 3H), 7.55 (m, 3H), 7.41 (m, 5H), 7.24 (m, 4H), 7.00 (m, 7H).

[0611] Compound 110-c

[0612] In an argon atmosphere, in a 2 L flask, compound 110-b (42 g, 79 mmol), aniline (9.6 g, 102 mmol), tri-tert-butylphosphine (7.2 mL, 7.8 mmol), sodium tert-butoxide (23 g, 237 mmol), and Pd2dba3 (3.6 g, 3.9 mmol) were added and dissolved in 600 mL of o-xylene, and the reaction solution was stirred at about 140 °C for about 6 hours. After cooling, the reaction solution was extracted with water (1 L) and ethyl acetate (300 mL) to collect the organic layer, which was dried over MgSO4 and then filtered. In the filtrate, the solvent was removed under reduced pressure to obtain a solid. The obtained solid was separated and purified by silica gel column chromatography using CH2Cl2 and hexane as eluents to obtain compound 110-c (white solid, 36 g, yield: 76%).

[0613] ESI-LCMS: [M+H] + :C 44 H 33 N2.589.2612.

[0614] 1 H-NMR (400MHz, CDCl3): 8.21 (m, 4H), 7.65 (d, 2H), 7.55 (t, 2H), 7.37 (m, 6H), 7.24 (m, 4H), 7.08 (m, 9H), 6.94 (m, 3H).

[0615] Compound 110-d

[0616] In an argon atmosphere, in a 2 L flask, compound 110-c (36 g, 61 mmol), 3-iodobromobenzene (17 g, 61 mmol), tri-tert-butylphosphine (5.6 mL, 6.1 mmol), sodium tert-butoxide (17.5 g, 183 mmol), and Pd2dba3 (2.8 g, 3.1 mmol) were added and dissolved in 400 mL of toluene, and the reaction solution was stirred at about 100 °C for about 6 hours. After cooling, the reaction solution was extracted with water (1 L) and ethyl acetate (300 mL) to collect the organic layer, which was dried over MgSO4 and then filtered. In the filtrate, the solvent was removed under reduced pressure to obtain a solid. The solid obtained therefrom was separated and purified by silica gel column chromatography using CH2Cl2 and hexane as eluents to obtain compound 110-d (white solid, 36 g, yield: 76%).

[0617] ESI-LCMS: [M+H] + :C 50 H 36 N2Br.743.2017.

[0618] 1 H-NMR (400MHz, CDCl3): 8.21 (m, 4H), 7.65 (d, 2H), 7.55 (t, 2H), 7.37 (m, 6H), 7.24 (m, 8H), 7.03 (m, 11H), 6.94 (m, 3H).

[0619] Compound 110-e

[0620] In an argon atmosphere, in a 2 L flask, compound 110-d (36 g, 49 mmol), aniline (6.1 g, 65 mmol), tri-tert-butylphosphine (4.4 mL, 5.0 mmol), sodium tert-butoxide (14 g, 147 mmol), and Pd2dba3 (2.2 g, 2.5 mmol) were added and dissolved in 400 mL of toluene, and the reaction solution was stirred at about 100 °C for about 6 hours. After cooling, the reaction solution was extracted with water (1 L) and ethyl acetate (300 mL) to collect the organic layer, which was dried over MgSO4 and then filtered. In the filtrate, the solvent was removed under reduced pressure to obtain a solid. The solid obtained therefrom was separated and purified by silica gel column chromatography using CH2Cl2 and hexane as eluents to obtain compound 110-e (white solid, 28 g, yield: 78%).

[0621] ESI-LCMS: [M+H] + :C 56 H 42 N3.756.3030.

[0622] 1 H-NMR (400MHz, CDCl3): 8.21 (m, 4H), 7.65 (d, 2H), 7.55 (t, 2H), 7.40 (m, 7H), 7.24 (m, 8H), 7.03 (m, 12H), 6.83 (s, 1H), 6.71 (m, 2H).

[0623] Compound 110-f

[0624] In an argon atmosphere, in a 2L flask, compound 110-e (36g, 37mmol) and 5-chloro-N... 1 N 1 N 3 N 3 Tetraphenylphenyl-1,3-diamine (17 g, 37 mmol), tri-tert-butylphosphine (3.4 mL, 3.8 mmol), sodium tert-butoxide (10.6 g, 111 mmol), and Pd2dba3 (1.7 g, 1.9 mmol) were added and dissolved in 400 mL of o-xylene, and the reaction solution was then stirred at about 140 °C for about 6 hours. After cooling, the reaction solution was extracted with water (1 L) and ethyl acetate (300 mL) to collect the organic layer, which was dried over MgSO4 and then filtered. The solvent was removed from the filtrate under reduced pressure to obtain a solid. The solid obtained therefrom was separated and purified by silica gel column chromatography using CH2Cl2 and hexane as eluents to obtain compound 110-f (white solid, 23 g, yield: 54%).

[0625] ESI-LCMS: [M+H] + :C 86 H 63 N5.1166.5017.

[0626] 1 H-NMR(400MHz, CDCl3):8.32(m,4H),7.65(d,2H),7.55(t,2H),7.38(m,5H),7. 26(m,17H),7.08(m,24H),6.93(s,3H),6.83(s,1H),6.74(d,2H),6.49(m,3H).

[0627] Compound 110

[0628] In an argon atmosphere, compound 110-f (23 g, 20 mmol) was dissolved in 400 mL of o-dichlorobenzene in a 1 L flask and cooled to approximately 0 °C in an ice-water bath. Boron tribromide (5 equivalents) was slowly added dropwise to the reaction solution, and the reaction solution was slowly heated to room temperature and then stirred for approximately 20 minutes. The reaction solution was then heated to approximately 150 °C and then stirred for approximately 12 hours. After cooling, triethylamine (5 mL) was slowly added dropwise to terminate the reaction, and the solvent was completely removed under reduced pressure to obtain a solid. The solid obtained was washed with MeOH and then separated and purified by silica gel column chromatography using CH2Cl2 and hexane as eluents to obtain compound 110 (yellow solid, 1.8 g, yield: 8%).

[0629] ESI-LCMS: [M+H] + :C 86 H 57 N5B2.1182.4327.

[0630] 1 H-NMR(400MHz, CDCl3):10.44(s,1H),9.26(d,2H),8.32(m,4H),7.65(d,2H),7.55(t,2H),7 .38(m,5H),7.26(m,15H),7.08(m,20H),6.93(s,2H),6.83(s,1H),6.74(d,2H),6.49(m,2H).

[0631] Synthesis of Compound 122

[0632] Compound 122 according to the embodiments can be synthesized by, for example, the steps shown in reaction scheme 8 below.

[0633] Reaction Scheme 8

[0634]

[0635] Compound 122-a

[0636] In an argon atmosphere, compound 101-a (50 g, 155 mmol), thiophene (17 g, 155 mmol), and Cs₂CO₃ (150 g, 465 mmol) were added to 1 L of NMP in a 2 L flask, and the reaction solution was stirred at approximately 180 °C for approximately 24 hours. After cooling, the reaction solution was slowly poured into water (1 L), and the resulting solid was filtered. The solid was redissolved in ethyl acetate (300 mL), washed several times with water, and extracted to collect the organic layer. The organic layer was dried over MgSO₄ and then filtered. The solvent was removed from the filtrate under reduced pressure to obtain a solid. The obtained solid was separated and purified by silica gel column chromatography using CH₂Cl₂ and hexane as eluents to obtain compound 122-a (white solid, 35 g, yield: 58%).

[0637] ESI-LCMS: [M+H] + :C 26 H 18 ClS.397.0712.

[0638] 1 H-NMR (400MHz, CDCl3): 8.39 (s, 1H), 8.19 (d, 2H), 8.03 (m, 2H), 7.71 (m, 2H), 7.43 (m, 10H).

[0639] Compound 122-b

[0640] In an argon atmosphere, in a 2 L flask, compound 122-a (35 g, 88 mmol), aniline (10.7 g, 114 mmol), tri-tert-butylphosphine (8.0 mL, 8.8 mmol), sodium tert-butoxide (25.3 g, 264 mmol), and Pd2dba3 (4.0 g, 4.4 mmol) were added and dissolved in 600 mL of o-xylene, and the reaction solution was stirred at about 140 °C for about 6 hours. After cooling, the reaction solution was extracted with water (1 L) and ethyl acetate (300 mL) to collect the organic layer, which was dried over MgSO4 and then filtered. In the filtrate, the solvent was removed under reduced pressure to obtain a solid. The solid obtained therefrom was separated and purified by silica gel column chromatography using CH2Cl2 and hexane as eluents to obtain compound 122-b (white solid, 24 g, yield: 61%).

[0641] ESI-LCMS: [M+H] + :C 32 H 24 SN.454.1612.

[0642] 1H-NMR (400MHz, CDCl3): 8.39 (s, 1H), 8.19 (d, 2H), 8.03 (m, 2H), 7.86 (s, 1H), 7.44 (m, 11H), 7.20 (s, 1H), 7.03 (m, 4H).

[0643] Compound 122-c

[0644] In an argon atmosphere, in a 2 L flask, compound 122-b (24 g, 53 mmol), 1,3-dibromobenzene (6.3 g, 26 mmol), tri-tert-butylphosphine (4.8 mL, 5.4 mmol), sodium tert-butoxide (15 g, 159 mmol), and Pd2dba3 (2.4 g, 2.7 mmol) were added and dissolved in 400 mL of toluene, and the reaction solution was stirred at about 100 °C for about 12 hours. After cooling, the reaction solution was extracted with water (1 L) and ethyl acetate (300 mL) to collect the organic layer, which was dried over MgSO4 and then filtered. In the filtrate, the solvent was removed under reduced pressure to obtain a solid. The solid obtained therefrom was separated and purified by silica gel column chromatography using CH2Cl2 and hexane as eluents to obtain compound 122-c (white solid, 43 g, yield: 63%).

[0645] ESI-LCMS: [M+H] + :C 70 H 49 S2N2.981.3227.

[0646] 1 H-NMR (400MHz, CDCl3): 8.41(s,2H),8.21(d,4H),8.10(m,4H),7.88(s,2H),7.42(m,28H),7.24(m,7H),7.03(m,8H),6.83(s,1H),6.68(d,2H).

[0647] Compound 122

[0648] In an argon atmosphere, compound 122-c (40 g, 40 mmol) was dissolved in 1 L of o-dichlorobenzene in a 1 L flask and cooled to approximately 0 °C in an ice-water bath. Boron tribromide (5 equivalents) was slowly added dropwise to the reaction solution, and the reaction solution was slowly heated to room temperature and then stirred for approximately 20 minutes. The reaction solution was then heated to approximately 150 °C and then stirred for approximately 12 hours. After cooling, triethylamine (5 mL) was slowly added dropwise to terminate the reaction, and the solvent was completely removed under reduced pressure to obtain a solid. The solid obtained was washed with MeOH and then separated and purified by silica gel column chromatography using CH2Cl2 and hexane as eluents to obtain compound 122 (yellow solid, 2.0 g, yield: 5%).

[0649] ESI-LCMS: [M+H] + :C 70 H 43 N2B2S2.997.9090.

[0650] 1 H-NMR (400MHz, CDCl3): 10.44(s,1H),9.26(d,2H),8.32(m,4H),7.65(d,2H),7.55(d,2H),7.42(m,8H),7.24(m,8H),7.02(m,10H),6.83(s,1H).

[0651] 2. Manufacturing and evaluation of light-emitting devices

[0652] Manufacturing of light-emitting devices

[0653] Patterning on a glass substrate A thick ITO layer is formed, and then NPD vacuum deposition is performed on top of the ITO (e.g., the upper surface) to form A thick hole injection layer. HT6 is vacuum deposited on top of the hole injection layer (e.g., the upper surface) to form... A thick hole transport layer. CzSi, serving as the hole transport region compound, is vacuum-deposited on the upper part (e.g., the upper surface) of the hole transport layer to form... A thick emission-aid layer. After the emission-aid layer is formed, mCP and the example compound or comparative example compound are co-deposited at a weight ratio of 99:1 to form... A thick emission layer. TSPO 1 is deposited on the upper part (e.g., the upper surface) of the emission layer to form a thick emission layer. A thick electron transport layer is formed, and then TPBi is deposited on top of the electron transport layer (e.g., the upper surface) to form A thick buffer layer. LiF is deposited on top of the electron transport layer (e.g., the upper surface) to form... A thick electron-injected layer is formed, and Al is vacuum-deposited to create... Thick LiF / Al electrode. HT28 is vacuum deposited on the upper part (e.g., the upper surface) of the electrode to form... A thick overlay is used to fabricate a light-emitting device. In an embodiment, a hole injection layer, a hole transport layer, an emission aid layer, an emission layer, an electron transport layer, a buffer layer, an electron injection layer, and electrodes are formed using a vacuum deposition apparatus.

[0654] The following are examples of compounds used in the manufacture of light-emitting devices.

[0655]

[0656] Evaluation of the characteristics of light-emitting devices

[0657] Examples 1 to 8, and Comparative Examples 1 and 2, each contain a host material in their emitting layer, and their properties are evaluated. To evaluate the properties of each of the light-emitting devices manufactured according to embodiments of the present disclosure, each containing a compound or compound X-1 or compound X-2 as its host material, measurements were taken at 10 mA / cm². 2 The driving voltage and luminous efficiency (cd / A) at the given current density, and the relative device lifetime ratio (T) 95 The value is calculated as a relative value compared to Comparative Example 1, where the device lifespan is determined by the device operating at 10 mA / cm. 2 The time taken for the brightness to degrade from the initial brightness (100%) to 95% brightness during continuous operation at a given current density is represented.

[0658] The following shows compound X-1 contained in Comparative Example 1 and compound X-2 contained in Comparative Example 2.

[0659] To evaluate the luminous efficiency of the light-emitting devices of Examples 1 to 8, and Comparative Examples 1 and 2, the luminous efficiency was measured using an external quantum efficiency measurement device C9920-12 manufactured by Hamamatsu Photonics, Co., Ltd., Japan. The device lifetime LT50 indicates the time taken for the brightness to decrease to approximately 50% of its initial brightness.

[0660] Compound X-1

[0661]

[0662] Compound X-2

[0663]

[0664] Table 1

[0665]

[0666] When Examples 1 to 8 are compared with Comparative Examples 1 and 2, Examples 1 to 8 each exhibit comparable or high luminous efficiency characteristics and long lifespan of the light-emitting device. This is believed to be because the compounds contained in Examples 1 to 8 each have a minimum triplet excitation energy (T1) of less than about 1.8 eV. When anthracene is included as a substituent as in Examples 1 to 8, the compounds can have a minimum triplet excitation energy of about 1.8 eV or less. Anthracene has a long conjugated structure and therefore has a minimum triplet excitation energy of about 1.7 eV, and the compounds containing anthracene as a substituent have a low minimum triplet excitation energy due to anthracene.

[0667] As the lifetime increases in the high-energy triplet state, excitons break weak bonds in the molecule, or degrade and decompose the organic material in the emitter layer through mechanisms such as triplet-triplet annihilation (TTA) and / or triplet-polaron quenching (TPQ), thereby reducing the lifetime of the light-emitting device. Examples 1 to 8 each contain compounds with low minimum triplet excitation energies and are therefore stabilized by the rapid internal conversion of excitons from high triplet states to minimum triplet excitation energies. Therefore, it is believed that in Examples 1 to 8, the degradation and decomposition of the organic material in the emitter layer are reduced due to excitons in high-energy states, thereby increasing the lifetime of the light-emitting device.

[0668] Therefore, compared with Comparative Examples 1 and 2, Examples 1 to 8 demonstrate improved lifespan of the light-emitting device. That is, by using a polycyclic compound substituted with at least one anthracene group, the lifespan of the light-emitting device in these examples can be improved.

[0669] The light-emitting device of the embodiment comprises a polycyclic compound having a low minimum triplet excitation energy by including at least one anthracene group, thereby improving its lifespan.

[0670] The light-emitting device of the embodiment can contain the polycyclic compound of the embodiment in the emitting layer, thereby exhibiting a long service life.

[0671] Although this disclosure has been described with reference to exemplary embodiments thereof, it should be understood that this disclosure should not be limited to these embodiments, and various appropriate changes and modifications may be made by those skilled in the art without departing from the spirit and scope of this disclosure.

[0672] Therefore, the technical 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 light-emitting device, comprising: First electrode; The second electrode on the first electrode; as well as An emission layer consisting of a polycyclic compound represented by Formula 1 is disposed between the first electrode and the second electrode. The first electrode and the second electrode each independently comprise any one, two or more compounds, a mixture of two or more compounds, or oxides of Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF, Mo, Ti, W, In, Sn, and Zn. Formula 1 as well as In Equation 1, X1 to X4 are each independently O, S, Se or NR1. Z1 and Z2 are each independently CR2. a1 and a2 are each independent integers from 0 to 2. R y1 and R y2 Each of the following is independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkoxy 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. R1 and R2 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted oxy group, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, a substituted or unsubstituted thio group, or a part represented by formula A, and / or bonded to adjacent groups to form a ring. At least one of X1 to X4, Z1 and Z2 contains the portion represented by equation A: Formula A as well as In equation A, Ra is a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkoxy 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. L1 is a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, or a substituted or unsubstituted divalent amine group. p is 0 or 1, and "-*" indicates the position to be connected.

2. The light-emitting device as claimed in claim 1, wherein the portion represented by formula A is represented by any one of formulas selected from A-1 to A-4: Formula A-1 Formula A-2 Formula A-3 Formula A-4 as well as in, In equation A-3, m is 0 or 1, and In Equations A-1 to A-4, Ra and "-*" are the same as those defined with respect to Equation A.

3. The light-emitting device as claimed in claim 2, wherein the portion represented by formula A-1 is represented by formula AA-1 or formula AA-2: Formula AA-1 Formula AA-2 as well as in, In equations AA-1 and AA-2, Ra and "-*" are the same as those defined with respect to equation A.

4. The light-emitting device as claimed in claim 2, wherein the portion represented by formula A-2 is represented by any one of formulas B-1 to B-3: Formula B-1 Formula B-2 Formula B-3 as well as in, In equations B-1 to B-3, Ra and "-*" are the same as those defined with respect to equation A.

5. The light-emitting device as claimed in claim 2, wherein the portion represented by formula A-3 is represented by formula C-1 or formula C-2: Formula C-1 Formula C-2 as well as in, In equations C-1 and C-2, Ra and "-*" are the same as those defined with respect to equation A.

6. The light-emitting device of claim 1, wherein Ra is an unsubstituted phenyl group or an unsubstituted naphthyl group.

7. The light-emitting device of claim 1, wherein the lowest triplet excitation energy of the polycyclic compound is 1.8 eV or less.

8. The light-emitting device of claim 1, wherein the emitting layer comprises at least one compound represented by group 1 of compounds: Compound group 1 9. A light-emitting device, comprising: First electrode; The second electrode on the first electrode; as well as An emission layer consisting of a polycyclic compound represented by Formula 2 is disposed between the first electrode and the second electrode. The first electrode and the second electrode each independently comprise any one, two or more compounds, a mixture of two or more compounds, or oxides of Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF, Mo, Ti, W, In, Sn, and Zn. Formula 2 And in Equation 2, X1 to X4 are each independently O, S, Se or NR1. R1 is Hydrogen atom, deuterium atom, halogen atom, cyano group, nitro group, substituted or unsubstituted silyl group, substituted or unsubstituted amine group, substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms. n is an integer from 0 to 8. When in NR1, R1 is not When n is an integer from 1 to 8, When n is 0, at least one of X1 to X4 is NR1, where R1 is a is an integer from 0 to 8-n. p is 0 or 1. L1 is a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, or a substituted or unsubstituted divalent amine group. R y Each of Ra is independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkoxy 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, and / or bonded to an adjacent group to form a ring. "-*" indicates the position to be connected.

10. The light-emitting device of claim 9, wherein the compound represented by formula 2 is represented by any one selected from formulas 3 to 5: Formula 3 Formula 4 Formula 5 as well as in, In Formulas 4 and 5, L2 and L3 are each independently a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, or a substituted or unsubstituted divalent amine group. In Formula 5, Ra1 and Ra2 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkoxy 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. In equations 3 to 5, a and R y And X1 to X4 are the same as those defined with respect to Equation 2, and In Equation 4, Ra is the same as that defined with respect to Equation 2.

11. The light-emitting device as claimed in claim 10, wherein, In Equation 2, The expression can be selected from any one of Equations 6 to 9: Formula 6 Formula 7 Formula 8 as well as Formula 9 In Equation 8, m is either 0 or 1, and In Equations 6 through 9, Ra and "-*" are the same as those defined with respect to Equation 2.

12. The light-emitting device as claimed in claim 11, wherein the portion represented by formula 6 is represented by formula 6-1 or formula 6-2: Formula 6-1 Formula 6-2 as well as in, In Equations 6-1 and 6-2, Ra and "-*" are the same as those defined with respect to Equation 2.

13. The light-emitting device of claim 11, wherein the portion represented by formula 7 is represented by any one of formulas 7-1 to 7-3: Equation 7-1 Equation 7-2 Formula 7-3 as well as in, In Equations 7-1 to 7-3, Ra and "-*" are the same as those defined with respect to Equation 2.

14. The light-emitting device as claimed in claim 11, wherein the portion represented by formula 8 is represented by formula 8-1 or formula 8-2: Formula 8-1 Formula 8-2 as well as in, In Equations 8-1 and 8-2, Ra and "-*" are the same as those defined with respect to Equation 2.

15. The light-emitting device of claim 9, wherein the emitting layer comprises at least one compound represented by group 1 of compounds: Compound group 1

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