Light emitting device

Abstract

A light-emitting element of one embodiment may exhibit long life characteristics by including a first electrode, a second electrode, and at least one light-emitting layer disposed between the first electrode and the second electrode and comprising at least one polycyclic compound represented by the following chemical formula 1. [Chemical Formula 1]

Description

Technology Field

[0001] The present invention relates to a light-emitting element. Background Technology

[0002] Recently, there has been active development of organic electroluminescence displays as image display devices. Unlike liquid crystal displays, organic electroluminescence displays are so-called self-emissive display devices that realize a display by causing a light-emitting material containing an organic compound in the light-emitting layer to emit light by recombining holes and electrons injected from a first electrode and a second electrode in the light-emitting layer.

[0003] In applying light-emitting devices to display devices, there is a demand for lower driving voltage, higher luminous efficiency, and longer lifespan of the light-emitting devices, and there is a continuous need for the development of materials for light-emitting devices that can stably realize these requirements. The problem to be solved

[0004] The objective of the present invention is to provide a long-life light-emitting element. means of solving the problem

[0005] One embodiment provides a light-emitting element comprising a first electrode, a second electrode disposed on the first electrode, and a light-emitting layer disposed between the first electrode and the second electrode and comprising a polycyclic compound represented by the following chemical formula 1, wherein the first electrode and the second electrode each independently comprise at least one selected from Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF / Ca, LiF / Al, Mo, Ti, W, In, Sn, and Zn, two or more compounds selected from these, a mixture of two or more selected from these, or oxides thereof.

[0006] [Chemical Formula 1]

[0007]

[0008] In the above Chemical Formula 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 , R y2 Each 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 cyclic aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted cyclic heteroaryl group having 2 to 30 carbon atoms.

[0009] 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 cyclic aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted cyclic heteroaryl group having 2 to 30 carbon atoms, a substituted or unsubstituted thio group, a compound represented by the following chemical formula A, or they form a ring by bonding with adjacent groups, and the X1 to X 4, At least one of Z1 and Z2 comprises a compound represented by the following chemical formula A, and

[0010] [Chemical Formula A]

[0011]

[0012] In the above chemical 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 cyclic aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted cyclic heteroaryl group having 2 to 30 carbon atoms, and L1 is a substituted or unsubstituted cyclic arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted cyclic heteroarylene group having 2 to 30 carbon atoms, or a substituted or unsubstituted divalent amine group, and p may be 0 or 1.

[0013] The above chemical formula A can be represented by any one of the following chemical formulas A-1 to A-4.

[0014] [Chemical Formula A-1]

[0015]

[0016] [Chemical Formula A-2]

[0017]

[0018] [Chemical Formula A-3]

[0019]

[0020] [Chemical Formula A-4]

[0021]

[0022] In the above formula A-3, m is 0 or 1, and in formulas A-1 to A-4, Ra may be the same as defined in the above formula A.

[0023] The above chemical formula A-1 can be represented by either the following chemical formula AA-1 or chemical formula AA-2.

[0024] [Chemical Formula AA-1]

[0025]

[0026] [Chemical Formula AA-2]

[0027]

[0028] In the above chemical formulas AA-1 and AA-2, Ra may be as defined in the above chemical formula 1.

[0029] The above chemical formula A-2 can be represented by any one of the following chemical formulas B-1 to B-3.

[0030] [Chemical Formula B-1]

[0031]

[0032] [Chemical Formula B-2]

[0033]

[0034] [Chemical Formula B-3]

[0035]

[0036] In chemical formulas B-1 to B-3, Ra may be the same as defined in chemical formula A above.

[0037] The above chemical formula A-3 can be represented by the following chemical formula C-1 or chemical formula C-2.

[0038] [Chemical Formula C-1]

[0039]

[0040] [Chemical Formula C-2]

[0041]

[0042] In chemical formulas C-1 and C-2, Ra may be the same as defined in chemical formula A above.

[0043] The above Ra may be an unsubstituted phenyl group or an unsubstituted naphthyl group.

[0044] The lowest triplet excitation energy of the above polycyclic compound may be 1.8 eV or less.

[0045] The light-emitting layer comprises a dopant and a host, and the dopant may comprise the polycyclic compound.

[0046] It further includes a capping layer disposed on the second electrode, and the refractive index of the capping layer may be 1.6 or higher.

[0047] The above polycyclic compound can emit heat-activated delayed fluorescence.

[0048] The above-mentioned light-emitting layer can emit blue light.

[0049] The above-mentioned light-emitting layer may include at least one of the compounds listed in the following compound group 1.

[0050] [Compound Group 1]

[0051]

[0053]

[0054]

[0055]

[0056]

[0057]

[0058]

[0059]

[0060]

[0061] .

[0062] One embodiment provides a light-emitting element comprising a first electrode, a second electrode disposed on the first electrode, and a light-emitting layer disposed between the first electrode and the second electrode and comprising a polycyclic compound represented by the following chemical formula 2, wherein the first electrode and the second electrode each independently comprise at least one selected from Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF / Ca, LiF / Al, Mo, Ti, W, In, Sn, and Zn, two or more compounds selected from these, a mixture of two or more selected from these, or oxides thereof.

[0063] [Chemical Formula 2]

[0064]

[0065] In the above chemical formula 2, X1 to X4 are each independently O, S, Se, or NR1, and 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 cyclic aryl group having 6 to 30 carbon atoms, or substituted or unsubstituted cyclic heteroaryl group having 2 to 30 carbon atoms, and n is an integer from 0 to 8, and when n is 0, at least one of X1 to X4 is R1 is NR1 and

[0066] R1 is In the case of NR1 other than, n is an integer between 1 and 8 inclusive, a is an integer between 0 and 8-n inclusive, p is 0 or 1, L1 is a substituted or unsubstituted cyclic arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted cyclic heteroarylene group having 2 to 30 carbon atoms, or a substituted or unsubstituted divalent amine group, and Ry and R a Each independently It may 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 ring-forming aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heteroaryl group having 2 to 30 carbon atoms, or it may form a ring by bonding with an adjacent group.

[0067] The above chemical formula 2 can be represented by any one of the following chemical formulas 3 to 5.

[0068] [Chemical Formula 3]

[0069]

[0070] [Chemical Formula 4]

[0071]

[0072] [Chemical Formula 5]

[0073]

[0074] In the above Chemical Formulas 4 and 5, L2 and L3 are each independently a substituted or unsubstituted cyclic arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted cyclic heteroarylene group having 2 to 30 carbon atoms, or a substituted or unsubstituted divalent amine group, and in Chemical Formulas 3 to 5, a, R y, X1 to X4 are the same as defined in Chemical Formula 2 above, and Ra in Chemical Formulas 4 and 5 may be the same as defined in Chemical Formula 2 above.

[0075] In the above chemical formula 2, the above It can be represented by any one of the following chemical formulas 6 to 8.

[0076] [Chemical Formula 6]

[0077]

[0078] [Chemical Formula 7]

[0079]

[0080] [Chemical Formula 8]

[0081]

[0082] [Chemical Formula 9]

[0083]

[0084] In the above chemical formula 8, m is 0 or 1, and in the above chemical formulas 6 to 9, R a It may be the same as defined in Chemical Formula 2 above.

[0085] The above chemical formula 6 can be represented by either the following chemical formula 6-1 or chemical formula 6-2.

[0086] [Chemical Formula 6-1]

[0087]

[0088] [Chemical Formula 6-2]

[0089]

[0090] In the above chemical formulas 6-1 and 6-2, Ra may be as defined in the above chemical formula 1.

[0091] The above chemical formula 7 can be represented by any one of the following chemical formulas 7-1 to 7-3.

[0092] [Chemical Formula 7-1]

[0093]

[0094] [Chemical Formula 7-2]

[0095]

[0096] [Chemical Formula 7-3]

[0097]

[0098] R in the above chemical formulas 7-1 to 7-3 a It may be the same as defined in Chemical Formula 2 above.

[0099] The above chemical formula 8 can be represented by the following chemical formula 8-1 or chemical formula 8-2.

[0100] [Chemical Formula 8-1]

[0101]

[0102] [Chemical Formula 8-2]

[0103]

[0104] R in the above chemical formulas 8-1 and 8-2 a It may be the same as defined in Chemical Formula 2 above.

[0105] In the above chemical formula 2, Ra may be an unsubstituted phenyl group or an unsubstituted naphthyl group.

[0106] In Paragraph 13,

[0107] The lowest triplet excitation energy of the above polycyclic compound may be 1.8 eV or less.

[0108] In Paragraph 13,

[0109] The above-mentioned light-emitting layer may include at least one of the compounds listed in the following compound group 1.

[0110] [Compound Group 1]

[0111]

[0113]

[0114]

[0115]

[0116]

[0117]

[0118]

[0119]

[0120]

[0121] . Effects of the invention

[0122] A light-emitting device of one embodiment may include a polycyclic compound of one embodiment in the light-emitting layer to exhibit long life characteristics. Brief explanation of the drawing

[0123] FIG. 1 is a plan view showing one embodiment of a display device. FIG. 2 is a cross-sectional view of a display device of one embodiment. FIG. 3 is a cross-sectional view schematically showing a light-emitting element according to one embodiment. FIG. 4 is a cross-sectional view schematically showing a light-emitting element according to one embodiment. FIG. 5 is a cross-sectional view schematically showing a light-emitting element according to one embodiment. FIG. 6 is a cross-sectional view schematically showing a light-emitting element according to one embodiment. FIG. 7 is a cross-sectional view of a display device according to one embodiment. FIG. 8 is a cross-sectional view of a display device according to one embodiment. Specific details for implementing the invention

[0124] The present invention is capable of various modifications and may take various forms, and specific embodiments are illustrated in the drawings and described in detail in the text. However, this is not intended to limit the invention to the specific disclosed forms, and it should be understood that the invention includes all modifications, equivalents, and substitutions that fall within the spirit and scope of the invention.

[0125] In describing each drawing, similar reference numerals have been used for similar components. In the attached drawings, the dimensions of the structures are depicted enlarged from their actual size for clarity of the invention. Terms such as "first," "second," etc., may be used to describe various components, but said components should not be limited by said terms. These terms are used solely for the purpose of distinguishing one component from another. For example, without departing from the scope of the invention, the first component may be named the second component, and similarly, the second component may be named the first component. A singular expression includes a plural expression unless the context clearly indicates otherwise.

[0126] In this application, terms such as "comprising" or "having" are intended to specify the existence of the features, numbers, steps, actions, components, parts, or combinations thereof described in the specification, and should be understood as not precluding the existence or addition of one or more other features, numbers, steps, actions, components, parts, or combinations thereof.

[0127] In this application, when a part such as a layer, film, region, or plate is described as being "on" or "upper" to another part, this includes not only cases where it is "immediately above" the other part, but also cases where there is another part in between. Conversely, when a part such as a layer, film, region, or plate is described as being "under" or "lower" to another part, this includes not only cases where it is "immediately below" the other part, but also cases where there is another part in between. Furthermore, in this application, being "placed on" may include cases where it is placed not only on the upper part but also on the lower part.

[0128] In this specification, "substituted or unsubstituted" may mean substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium atoms, halogen atoms, cyano groups, nitro groups, amino groups, silyl groups, oxy groups, thio groups, sulfinyl groups, sulfonyl groups, carbonyl groups, boron groups, phosphine oxide groups, phosphine sulfide groups, alkyl groups, alkenyl groups, alkynyl groups, alkoxy groups, hydrocarbon ring groups, aryl groups, and heterocyclic groups. Additionally, each of the substituents exemplified above may be substituted or unsubstituted. For example, a biphenyl group may be interpreted as an aryl group or as a phenyl group substituted with a phenyl group.

[0129] In this specification, "forming a ring by combining with adjacent groups" may mean forming a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted hetero ring by combining with adjacent groups. The hydrocarbon ring includes an aliphatic hydrocarbon ring and an aromatic hydrocarbon ring. The hetero ring includes an aliphatic hetero ring and an aromatic hetero ring. The hydrocarbon ring and the hetero ring may be monocyclic or polycyclic. Additionally, the ring formed by combining with each other may be connected to another ring to form a spiro structure.

[0130] In this specification, "adjacent group" may mean a substituent substituted on an atom directly connected to the atom on which the substituent is substituted, another substituent substituted on the atom on which the substituent is substituted, or a substituent that is stereostructively closest to the substituent. For example, in 1,2-dimethylbenzene, two methyl groups may be interpreted as "adjacent groups," and in 1,1-diethylcyclopentane, two ethyl groups may be interpreted as "adjacent groups." Additionally, in 4,5-dimethylphenanthrene, two methyl groups may be interpreted as "adjacent groups."

[0131] In this specification, examples of halogen atoms include fluorine atoms, chlorine atoms, bromine atoms, or iodine atoms.

[0132] In this specification, the alkyl group may be straight-chain, branched-chain, or cyclic. The number of carbon atoms in the alkyl group is 1 or more and 50 or less, 1 or more and 30 or less, 1 or more and 20 or less, 1 or more and 10 or less, or 1 or more and 6 or less. Examples of alkyl groups include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, s-butyl group, t-butyl group, i-butyl group, 2-ethylbutyl group, 3,3-dimethylbutyl group, n-pentyl group, i-pentyl group, neopentyl group, t-pentyl group, cyclopentyl group, 1-methylpentyl group, 3-methylpentyl group, 2-ethylpentyl group, 4-methyl-2-pentyl group, n-hexyl group, 1-methylhexyl group, 2-ethylhexyl group, 2-butylhexyl group, cyclohexyl group, 4-methylcyclohexyl group, 4-t-butylcyclohexyl group, n-heptyl group, 1-methylheptyl group, 2,2-dimethylheptyl group, 2-ethylheptyl group, 2-butylheptyl group, n-octyl group, t-octyl group, 2-ethyloctyl group, 2-butyloctyl group, 2-hexyloctyl group, 3,7-dimethyloctyl group, cyclooctyl group, n-nonyl group, n-decyl group, adamantyl group, 2-ethyldecyl group, 2-butyldecyl group, 2-hexyldecyl group, 2-octyldecyl group, n-undecyl group, n-dodecyl group, 2-ethyldodecyl group, 2-butyldodecyl group, 2-hexyldodecyl group, 2-octyldodecyl group, n-tridecyl group, n-tetradecyl group, n-pentadecyl group, n-hexadecyl group, 2-ethylhexadecyl group, 2-butylhexadecyl group, 2-hexylhexadecyl group, 2-octylhexadecyl group, n-heptadecyl group, n-octadecyl group, Examples include, but are not limited to, n-nonadecyl groups, n-icosyl groups, 2-ethylicosyl groups, 2-butylicosyl groups, 2-hexylicosyl groups, 2-octylicosyl groups, n-henicosyl groups, n-docosyl groups, n-tricosyl groups, n-tetracosyl groups, n-pentacosyl groups, n-hexacosyl groups, n-heptacosyl groups, n-octacosyl groups, n-nonacosyl groups, and n-triacontyl groups.

[0133] In this specification, a hydrocarbon ring group refers to any functional group or substituent derived from an aliphatic hydrocarbon ring. The hydrocarbon ring group may be a saturated hydrocarbon ring group having 5 to 20 carbon atoms forming the ring.

[0134] In this specification, an aryl group refers to any functional group or substituent derived from an aromatic hydrocarbon ring. The aryl group may be a monocyclic aryl group or a polycyclic aryl group. The number of ring-forming carbon atoms in the aryl group may be 6 or more and 30 or less, 6 or more and 20 or less, or 6 or more and 15 or less. Examples of aryl groups may include, but are not limited to, phenyl groups, naphthyl groups, fluorenyl groups, anthracenyl groups, phenanthryl groups, biphenyl groups, terphenyl groups, quarterphenyl groups, quinquephenyl groups, sexphenyl groups, triphenylenyl groups, pyrenyl groups, benzofluranthenyl groups, crisenyl groups, etc.

[0135] In this specification, the fluorenyl group may be substituted, and two substituents may be combined to form a spiro structure. Examples of cases where the fluorenyl group is substituted are as follows. However, it is not limited thereto.

[0136]

[0137] In this specification, a heterocyclic group refers to any functional group or substituent derived from a ring comprising one or more of B, O, N, P, Si, and S as heteroatoms. Heterocyclic groups include aliphatic heterocyclic groups and aromatic heterocyclic groups. Aromatic heterocyclic groups may be heteroaryl groups. Aliphatic heterocyclic groups and aromatic heterocyclic groups may be monocyclic or polycyclic.

[0138] In this specification, a heterocyclic group may include one or more of B, O, N, P, Si, and S as heteroatoms. If the heterocyclic group includes two or more heteroatoms, the two or more heteroatoms may be identical or different from each other. The heterocyclic group may be a monocyclic heterocyclic group or a polycyclic heterocyclic group, and is a concept that includes a heteroaryl group. The number of ring-forming carbons of the heterocyclic group may be 2 or more and 30 or less, 2 or more and 20 or less, or 2 or more and 10 or less.

[0139] In this specification, the aliphatic heterocyclic group may include one or more of B, O, N, P, Si, and S as heteroatoms. The number of ring-forming carbon atoms in the aliphatic heterocyclic group may be 2 or more and 30 or less, 2 or more and 20 or less, or 2 or more and 10 or less. Examples of the aliphatic heterocyclic group include, but are not limited to, oxirane groups, thiran groups, pyrrolidine groups, piperidine groups, tetrahydrofuran groups, tetrahydrothiophene groups, thian groups, tetrahydropyran groups, 1,4-dioxane groups, etc.

[0140] In this specification, the heteroaryl group may include one or more of B, O, N, P, Si, and S as heteroatoms. If the heteroaryl group includes two or more heteroatoms, the two or more heteroatoms may be identical or different from each other. The heteroaryl group may be a monocyclic heterocyclic group or a polycyclic heterocyclic group. The number of ring-forming carbons in the heteroaryl group may be 2 or more and 30 or less, 2 or more and 20 or less, or 2 or more and 10 or less. Examples of heteroaryl groups include thiophene group, furan group, pyrrole group, imidazole group, triazole group, pyridine group, bipyridine group, pyrimidine group, triazine group, triazole group, acryl group, pyridazine group, pyrazinyl group, quinoline group, quinazolin group, quinoxaline group, phenoxazine group, phthalazine group, pyridopyrimidine group, pyridopyrazine group, pyrazinopyrazine group, isoquinoline group, indole group, carbazole group, N-arylcarbazole group, N-heteroarylcarbazole group, N-alkylcarbazole group, benzoxazole group, benzimidazole group, benzothiazole group, benzocarbazole group, benzothiophen group, dibenzothiophen group, thienothiophene group, benzofuran group, phenanthroline group. Thiazol groups, isooxazole groups, oxazole groups, oxadiazole groups, thiadiazol groups, phenothiazine groups, dibenzosilol groups and dibenzofuran groups, etc., are included but are not limited to these.

[0141] In this specification, the description of the aryl group described above may apply except that the arylene group is a divalent group. The description of the heteroaryl group described above may apply except that the heteroarylene group is a divalent group.

[0142] In this specification, silyl groups include alkyl silyl groups and aryl silyl groups. Examples of silyl groups include, but are not limited to, trimethylsilyl groups, triethylsilyl groups, t-butyldimethylsilyl groups, vinyldimethylsilyl groups, propyldimethylsilyl groups, triphenylsilyl groups, diphenylsilyl groups, phenylsilyl groups, etc.

[0143] In this specification, the number of carbon atoms in the amino group is not particularly limited, but may be 1 or more and 30 or less. The amino group may include an alkyl amino group, an aryl amino group, or a heteroaryl amino group. Examples of amino groups include, but are not limited to, methylamino groups, dimethylamino groups, phenylamino groups, diphenylamino groups, naphthylamino groups, 9-methyl-anthracenylamino groups, triphenylamino groups, etc.

[0144] In this specification, the number of carbon atoms in the carbonyl group is not particularly limited, but may be 1 to 40 or fewer, 1 to 30 or fewer, or 1 to 20 or fewer. For example, it may have the following structure, but is not limited thereto.

[0145]

[0146] In this specification, the number of carbon atoms in the sulfinyl group and the sulfonyl group is not particularly limited, but may be 1 or more and 30 or less. The sulfinyl group may include an alkyl sulfinyl group and an aryl sulfinyl group. The sulfonyl group may include an alkyl sulfonyl group and an aryl sulfonyl group.

[0147] In this specification, thiol groups may include alkyl thio groups and aryl thio groups. A thiol group may mean that a sulfur atom is bonded to the alkyl or aryl group defined above. Examples of thiol groups include, but are not limited to, methyl thio groups, ethyl thio groups, propyl thio groups, pentyl thio groups, hexyl thio groups, octyl thio groups, dodecyl thio groups, cyclopentyl thio groups, cyclohexyl thio groups, phenyl thio groups, naphthyl thio groups, etc.

[0148] In this specification, an oxy group may refer to an alkyl group or aryl group defined above in which an oxygen atom is bonded. An oxy group may include an alkoxy group and an aryl oxy group. An alkoxy group may be a straight chain, a branched chain, or a cyclic chain. The number of carbon atoms in an alkoxy group is not particularly limited, but may be, for example, 1 or more and 20 or less, or 1 or more and 10 or less. Examples of oxy groups include, but are not limited to, methoxy, ethoxy, n-propoxy, isopropoxy, butoxy, pentyloxy, hexyloxy, octyloxy, nonyloxy, decyloxy, benzyloxy, etc.

[0149] In this specification, a boron group may mean that a boron atom is bonded to the alkyl group or aryl group defined above. Boron groups include alkyl boron groups and aryl boron groups. Examples of boron groups include, but are not limited to, trimethylboron groups, triethylboron groups, t-butyldimethylboron groups, triphenylboron groups, diphenylboron groups, phenylboron groups, etc.

[0150] In this specification, the alkenyl group may be a straight chain or a branched chain. The number of carbon atoms is not particularly limited, but is 2 to 30, 2 to 20, or 2 to 10. Examples of alkenyl groups include, butenyl, 1-pentenyl, 1,3-butadienyl aryl, styrenyl, styrylvinyl, etc., but are not limited to these.

[0151] In this specification, the number of carbon atoms in the amine group is not particularly limited, but may be 1 or more and 30 or less. The amine group may include alkyl amine groups and aryl amine groups. Examples of amine groups include, but are not limited to, methylamine groups, dimethylamine groups, phenylamine groups, diphenylamine groups, naphthylamine groups, 9-methyl-anthracenylamine groups, triphenylamine groups, etc.

[0152] In this specification, among alkyl thio groups, alkyl sulfoxy groups, alkyl aryl groups, alkyl amino groups, alkyl boron groups, alkyl silyl groups, and alkyl amine groups, the alkyl groups are the same as the examples of alkyl groups described above.

[0153] In this specification, the aryl group among the aryloxy group, arylthio group, arylsulfoxy group, arylamino group, arylboron group, arylsilyl group, and arylamine group is the same as the examples of aryl groups described above.

[0154] In this specification, direct linkage may mean a single linkage.

[0155] Meanwhile, in this specification " " and " " means the location where it is connected.

[0156] Hereinafter, an embodiment of the present invention will be described with reference to the drawings.

[0157] FIG. 1 is a plan view showing one embodiment of a display device (DD). FIG. 2 is a cross-sectional view of the display device (DD) of one embodiment. FIG. 2 is a cross-sectional view showing the portion corresponding to line I-I' of FIG. 1.

[0158] A display device (DD) may include a display panel (DP) and an optical layer (PP) disposed on the display panel (DP). The display panel (DP) includes light-emitting elements (ED-1, ED-2, ED-3). The display device (DD) may include a plurality of light-emitting elements (ED-1, ED-2, ED-3). The optical layer (PP) is disposed on the display panel (DP) to control reflected light from the display panel (DP) caused by external light. The optical layer (PP) may include, for example, a polarizing layer or a color filter layer. Meanwhile, unlike what is shown in the drawings, the optical layer (PP) may be omitted in the display device (DD) of one embodiment.

[0159] A base substrate (BL) may be disposed on the optical layer (PP). The base substrate (BL) may be a member that provides a base surface on which the optical layer (PP) is disposed. The base substrate (BL) may be a glass substrate, a metal substrate, a plastic substrate, etc. However, the embodiments are not limited thereto, and the base substrate (BL) may be an inorganic layer, an organic layer, or a composite material layer. In addition, unlike what is illustrated, the base substrate (BL) may be omitted in one embodiment.

[0160] A display device (DD) according to one embodiment may further include a filling layer (not shown). The filling layer (not shown) may be disposed between a display element layer (DP-ED) and a base substrate (BL). The filling layer (not shown) may be an organic layer. The filling layer (not shown) may include at least one of an acrylic resin, a silicone resin, and an epoxy resin.

[0161] The display panel (DP) may include a base layer (BS), a circuit layer (DP-CL) provided on the base layer (BS), and a display element layer (DP-ED). The display element layer (DP-ED) may include a pixel defining layer (PDL), light-emitting elements (ED-1, ED-2, ED-3) disposed between the pixel defining layers (PDL), and an encapsulation layer (TFE) disposed on the light-emitting elements (ED-1, ED-2, ED-3).

[0162] The base layer (BS) may be a member that provides a base surface on which the display element layer (DP-ED) is placed. The base layer (BS) may be a glass substrate, a metal substrate, a plastic substrate, etc. However, the embodiments are not limited thereto, and the base layer (BS) may be an inorganic layer, an organic layer, or a composite material layer.

[0163] In one embodiment, the circuit layer (DP-CL) is disposed on the base layer (BS), and the circuit layer (DP-CL) may include a plurality of transistors (not shown). Each of the transistors (not shown) may include a control electrode, an input electrode, and an output electrode. For example, the circuit layer (DP-CL) may include a switching transistor and a driving transistor for driving light-emitting elements (ED-1, ED-2, ED-3) of the display element layer (DP-ED).

[0164] Each of the light-emitting elements (ED-1, ED-2, ED-3) may have the structure of a light-emitting element (ED) according to one embodiment of FIGS. 3 to 6 described below. Each of the light-emitting elements (ED-1, ED-2, ED-3) may include a first electrode (EL1), a hole transport region (HTR), a light-emitting layer (EML-R, EML-G, EML-B), an electron transport region (ETR), and a second electrode (EL2).

[0165] FIG. 2 illustrates an embodiment in which the light-emitting layers (EML-R, EML-G, EML-B) of light-emitting elements (ED-1, ED-2, ED-3) are disposed within an opening (OH) defined in a pixel defining film (PDL), and the hole transport region (HTR), electron transport region (ETR), and second electrode (EL2) are provided as a common layer throughout the light-emitting elements (ED-1, ED-2, ED-3). However, the embodiment is not limited thereto, and unlike FIG. 2, in one embodiment, the hole transport region (HTR) and electron transport region (ETR) may be patterned and provided within the opening (OH) defined in the pixel defining film (PDL). For example, in one embodiment, the hole transport region (HTR), light-emitting layer (EML-R, EML-G, EML-B), and electron transport region (ETR) of the light-emitting element (ED-1, ED-2, ED-3) may be provided by patterning using an inkjet printing method.

[0166] The encapsulation layer (TFE) may cover light-emitting elements (ED-1, ED-2, ED-3). The encapsulation layer (TFE) may seal a display element layer (DP-ED). The encapsulation layer (TFE) may be a thin film encapsulation layer. The encapsulation layer (TFE) may be a single layer or a plurality of layers stacked. The encapsulation layer (TFE) includes at least one insulating layer. The encapsulation layer (TFE) according to one embodiment may include at least one inorganic film (hereinafter, encapsulation inorganic film). Additionally, the encapsulation layer (TFE) according to one embodiment may include at least one organic film (hereinafter, encapsulation organic film) and at least one encapsulation inorganic film.

[0167] The encapsulation inorganic film protects the display device layer (DP-ED) from moisture / oxygen, and the encapsulation organic film protects the display device layer (DP-ED) from foreign substances such as dust particles. The encapsulation inorganic film may include silicon nitride, silicon oxynitride, silicon oxide, titanium oxide, or aluminum oxide, but is not particularly limited thereto. The encapsulation organic film may include acrylic compounds, epoxy compounds, etc. The encapsulation organic film may include photopolymerizable organic materials and is not particularly limited thereto.

[0168] The encapsulation layer (TFE) can be placed on the second electrode (EL2) and can fill the opening (OH).

[0169] Referring to FIGS. 1 and 2, the display device (DD) may include a non-emissive region (NPXA) and emissive regions (PXA-R, PXA-G, PXA-B). Each of the emissive regions (PXA-R, PXA-G, PXA-B) may be a region where light generated from each of the emissive elements (ED-1, ED-2, ED-3) is emitted. The emissive regions (PXA-R, PXA-G, PXA-B) may be spaced apart from each other in a plane.

[0170] Each of the light-emitting regions (PXA-R, PXA-G, PXA-B) may be a region separated by a pixel defining film (PDL). Non-light-emitting regions (NPXA) may be regions between adjacent light-emitting regions (PXA-R, PXA-G, PXA-B) and may be regions corresponding to the pixel defining film (PDL). Meanwhile, in this specification, each of the light-emitting regions (PXA-R, PXA-G, PXA-B) may correspond to a pixel. The pixel defining film (PDL) may separate light-emitting elements (ED-1, ED-2, ED-3). The light-emitting layers (EML-R, EML-G, EML-B) of the light-emitting elements (ED-1, ED-2, ED-3) may be separated by being placed in an opening (OH) defined in the pixel defining film (PDL).

[0171] The light-emitting regions (PXA-R, PXA-G, PXA-B) can be divided into multiple groups according to the color of light generated from the light-emitting elements (ED-1, ED-2, ED-3). In the display device (DD) of one embodiment illustrated in FIGS. 1 and 2, three light-emitting regions (PXA-R, PXA-G, PXA-B) emitting red light, green light, and blue light are illustrated as examples. For example, the display device (DD) of one embodiment may include a red light-emitting region (PXA-R), a green light-emitting region (PXA-G), and a blue light-emitting region (PXA-B) that are distinct from each other.

[0172] In a display device (DD) according to one embodiment, a plurality of light-emitting elements (ED-1, ED-2, ED-3) may emit light in different wavelength regions. For example, in one embodiment, the display device (DD) may include a first light-emitting element (ED-1) that emits red light, a second light-emitting element (ED-2) that emits green light, and a third light-emitting element (ED-3) that emits blue light. That is, the red light-emitting region (PXA-R), the green light-emitting region (PXA-G), and the blue light-emitting region (PXA-B) of the display device (DD) may correspond to the first light-emitting element (ED-1), the second light-emitting element (ED-2), and the third light-emitting element (ED-3), respectively.

[0173] However, the embodiments are not limited thereto, and the first to third light-emitting elements (ED-1, ED-2, ED-3) may emit light in the same wavelength range, or at least one may emit light in a different wavelength range. For example, the first to third light-emitting elements (ED-1, ED-2, ED-3) may all emit blue light.

[0174] In a display device (DD) according to one embodiment, the light-emitting regions (PXA-R, PXA-G, PXA-B) may be arranged in a stripe shape. Referring to FIG. 1, a plurality of red light-emitting regions (PXA-R), a plurality of green light-emitting regions (PXA-G), and a plurality of blue light-emitting regions (PXA-B) may each be aligned along a second directional axis (DR2). Additionally, they may be arranged alternately along a first directional axis (DR1) in the order of red light-emitting regions (PXA-R), green light-emitting regions (PXA-G), and blue light-emitting regions (PXA-B).

[0175] In FIGS. 1 and 2, the areas of the light-emitting regions (PXA-R, PXA-G, PXA-B) are all depicted as similar, but the embodiment is not limited thereto, and the areas of the light-emitting regions (PXA-R, PXA-G, PXA-B) may differ from one another depending on the wavelength range of the emitted light. Meanwhile, the areas of the light-emitting regions (PXA-R, PXA-G, PXA-B) may refer to the area when viewed on a plane defined by the first directional axis (DR1) and the second directional axis (DR2).

[0176] Meanwhile, the arrangement of the light-emitting regions (PXA-R, PXA-G, PXA-B) is not limited to that shown in FIG. 1, and the order in which the red light-emitting region (PXA-R), the green light-emitting region (PXA-G), and the blue light-emitting region (PXA-B) are arranged can be provided in various combinations according to the characteristics of the display quality required by the display device (DD). For example, the arrangement of the light-emitting regions (PXA-R, PXA-G, PXA-B) may be a pentile arrangement or a diamond arrangement.

[0177] Additionally, the areas of the light-emitting regions (PXA-R, PXA-G, PXA-B) may differ from each other. For example, in one embodiment, the area of ​​the green light-emitting region (PXA-G) may be smaller than the area of ​​the blue light-emitting region (PXA-B), but the embodiment is not limited thereto.

[0178] Hereinafter, FIGS. 3 to 6 are cross-sectional views schematically illustrating a light-emitting element according to one embodiment. A light-emitting element (ED) according to one embodiment may include a first electrode (EL1), a hole transport region (HTR), a light-emitting layer (EML), an electron transport region (ETR), and a second electrode (EL2) that are sequentially stacked.

[0179] FIG. 4 shows a cross-sectional view of a light-emitting device (ED) of an embodiment in which, compared with FIG. 3, 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). FIG. 5 also shows a cross-sectional view of a light-emitting device (ED) of an embodiment in which, compared with FIG. 3, 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). FIG. 6 shows a cross-sectional view of a light-emitting device (ED) of an embodiment in which, compared with FIG. 4, a capping layer (CPL) disposed on a second electrode (EL2).

[0180] The first electrode (EL1) has conductivity. The first electrode (EL1) may be formed of a metal material, a metal alloy, or a conductive compound. The first electrode (EL1) may be an anode or a cathode. However, the embodiments are not limited thereto. Additionally, the first electrode (EL1) may be a pixel electrode. The first electrode (EL1) may be a transmissive electrode, a semitransmissive electrode, or a reflective electrode. If the first electrode (EL1) is a transmissive electrode, the first electrode (EL1) may include a transparent metal oxide, for example, ITO (indium tin oxide), IZO (indium zinc oxide), ZnO (zinc oxide), ITZO (indium tin zinc oxide), etc. When the first electrode (EL1) is a semi-transparent electrode or a reflective electrode, the first electrode (EL1) may include Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF / Ca, LiF / Al, Mo, Ti, W, In, Sn, Zn, or compounds or mixtures thereof (e.g., a mixture of Ag and Mg). Alternatively, the first electrode (EL1) may have a plurality of layer structures including a reflective film or semi-transparent film formed of the above materials and a transparent conductive film formed of ITO (indium tin oxide), IZO (indium zinc oxide), ZnO (zinc oxide), ITZO (indium tin zinc oxide), etc. For example, the first electrode (EL1) may have a three-layer structure of ITO / Ag / ITO, but is not limited thereto. In addition, the embodiments are not limited thereto, and the first electrode (EL1) may include the metal material described above, a combination of two or more metal materials selected from the metal materials described above, or oxides of the metal materials described above. The thickness of the first electrode (EL1) may be about 700 Å to about 10,000 Å. For example, the thickness of the first electrode (EL1) may be about 1,000 Å to about 3,000 Å.

[0181] A hole transport region (HTR) is provided on the first electrode (EL1). The hole transport region (HTR) may include at least one of a hole injection layer (HIL), a hole transport layer (HTL), a buffer layer or a light-emitting auxiliary layer (not shown), and an electron blocking layer (EBL). The thickness of the hole transport region (HTR) may be, for example, about 50 Å to about 15,000 Å.

[0182] The hole transport region (HTR) may have a multilayer structure consisting of a single layer made of a single material, a single layer made of multiple different materials, or multiple layers made of multiple different materials.

[0183] For example, the hole transport region (HTR) may have a single-layer structure of a hole injection layer (HIL) or a hole transport layer (HTL), or a single-layer structure composed of a hole injection material and a hole transport material. Additionally, the hole transport region (HTR) may have a single-layer structure composed of multiple different materials, or may have a structure of a hole injection layer (HIL) / hole transport layer (HTL), a hole injection layer (HIL) / hole transport layer (HTL) / buffer layer (not shown), a hole injection layer (HIL) / buffer layer (not shown), a hole transport layer (HTL) / buffer layer (not shown), or a hole injection layer (HIL) / hole transport layer (HTL) / electron blocking layer (EBL) stacked sequentially from the first electrode (EL1), but the embodiments are not limited thereto.

[0184] Hole transport regions (HTRs) can be formed using various methods such as vacuum deposition, spin coating, casting, LB method (Langmuir-Blodgett), inkjet printing, laser printing, and laser induced thermal imaging (LITI).

[0185] The hole transport region (HTR) may include a compound represented by the following chemical formula H-1.

[0186] [Chemical Formula H-1]

[0187]

[0188] In the above chemical formula H-1, L1 and L2 may each independently be a direct linkage, substituted or unsubstituted ring-forming arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heteroarylene group having 2 to 30 carbon atoms. a and b may each independently be integers from 0 to 10. Meanwhile, if a or b is an integer of 2 or more, a plurality of L1 and L2 may each independently be a substituted or unsubstituted ring-forming arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heteroarylene group having 2 to 30 carbon atoms.

[0189] In chemical formula H-1, Ar1 and Ar2 may each independently be a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heteroaryl group having 2 to 30 carbon atoms. Additionally, in chemical formula H-1, Ar3 may be a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms.

[0190] The compound represented by the above formula H-1 may be a monoamine compound. Alternatively, the compound represented by the above formula H-1 may be a diamine compound in which at least one of Ar-1 to Ar3 comprises an amine group as a substituent. Additionally, the compound represented by the above formula H-1 may be a carbazole compound comprising a carbazole group substituted or unsubstituted on at least one of Ar1 and Ar2, or a fluorene compound comprising a fluorene group substituted or unsubstituted on at least one of Ar1 and Ar2.

[0191] The compound represented by the chemical formula H-1 may be represented as any one of the compounds in the following compound group H. However, the compounds listed in the following compound group H are exemplary, and the compound represented by the chemical formula H-1 is not limited to those listed in the following compound group H.

[0192] [Compound Group H]

[0193]

[0194] The hole transport region (HTR) is phthalocyanine compounds such as copper phthalocyanine, DNTPD(N 1 ,N 1' -([1,1'-biphenyl]-4,4'-diyl)bis(N 1 -phenyl-N 4 ,N 4-di-m-tolylbenzene-1,4-diamine)), m-MTDATA(4,4',4"-[tris(3-methylphenyl)phenylamino] triphenylamine), TDATA(4,4'4"-Tris(N,N-diphenylamino)triphenylamine), 2-TNATA(4,4',4"-tris[N(2-naphthyl)-N-phenylamino]-triphenylamine), PEDOT / PSS(Poly(3,4-ethylenedioxythiophene) / Poly(4-styrenesulfonate)), PANI / DBSA(Polyaniline / Dodecylbenzenesulfonic acid), PANI / CSA(Polyaniline / Camphor sulfonicacid), PANI / PSS(Polyaniline / Poly(4-styrenesulfonate)), NPB(N,N'-di(naphthalene-l-yl)-N,N'-diphenyl-benzidine), 트리페닐아민을 포함하는 폴리에테르케톤(TPAPEK), 4-Isopropyl-4'-methyldiphenyliodonium [Tetrakis(pentafluorophenyl)borate], HATCN(dipyrazino[2,3-f: 2',3'-h] quinoxaline-2,3,6,7,10,11-hexacarbonitrile) 등을 포함할 수 있다.

[0195] The hole transport region (HTR) may include carbazole derivatives such as N-phenylcarbazole and polyvinylcarbazole, fluorene derivatives, triphenylamine derivatives such as TPD (N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine) and TCTA (4,4',4"-tris(N-carbazolyl)triphenylamine), NPB (N,N'-di(naphthalene-l-yl)-N,N'-diphenyl-benzidine), TAPC (4,4′-Cyclohexylidene bis[N,N-bis(4-methylphenyl)benzenamine]), HMTPD (4,4'-Bis[N,N'-(3-tolyl)amino]-3,3'-dimethylbiphenyl), mCP (1,3-Bis(N-carbazolyl)benzene), etc. there is.

[0196] Additionally, the hole transport region (HTR) may include CzSi (9-(4-tert-Butylphenyl)-3,6-bis(triphenylsilyl)-9H-carbazole), CCP (9-phenyl-9H-3,9'-bicarbazole), or mDCP (1,3-bis(1,8-dimethyl-9H-carbazol-9-yl)benzene), etc.

[0197] The hole transport region (HTR) may include compounds of the hole transport region described above in at least one of the hole injection layer (HIL), hole transport layer (HTL), and electron blocking layer (EBL).

[0198] The thickness of the hole transport region (HTR) may be about 100 Å to about 10000 Å, for example, about 100 Å to about 5000 Å. If the hole transport region (HTR) includes a hole injection layer (HIL), the thickness of the hole injection layer (HIL) may be, for example, about 30 Å to about 1000 Å. If the hole transport region (HTR) includes a hole transport layer (HTL), the thickness of the hole transport layer (HTL) may be about 30 Å to about 1000 Å. For example, if the hole transport region (HTR) includes an electron blocking layer (EBL), the thickness of the electron blocking layer (EBL) may be about 10 Å to about 1000 Å. When the thicknesses of the hole transport region (HTR), hole injection layer (HIL), hole transport layer (HTL), and electron blocking layer (EBL) satisfy the ranges described above, satisfactory hole transport characteristics can be obtained without a substantial increase in driving voltage.

[0199] In addition to the aforementioned materials, the hole transport region (HTR) may further include a charge-generating material to enhance conductivity. The charge-generating material may be uniformly or non-uniformly dispersed within the hole transport region (HTR). The charge-generating material may be, for example, a p-dopant. The p-dopant may include at least one of a metal halide compound, a quinone derivative, a metal oxide, and a cyano group-containing compound, but is not limited thereto. For example, p-dopants may include metal halide compounds such as CuI and RbI, quinone derivatives such as TCNQ (Tetracyanoquinodimethane) and F4-TCNQ (2,3,5,6-tetrafluoro-7,7'8,8-tetracyanoquinodimethane), metal oxides such as tungsten oxide and molybdenum oxide, and cyano group-containing compounds such as HATCN (dipyrazino[2,3-f: 2',3'-h] quinoxaline-2,3,6,7,10,11-hexacarbonitrile) and 4-[[2,3-bis[cyano-(4-cyano-2,3,5,6-tetrafluorophenyl)methylidene]cyclopropylidene]-cyanomethyl]-2,3,5,6-tetrafluorobenzonitrile, but the examples are not limited thereto.

[0200] As described above, the hole transport region (HTR) may further include at least one of a buffer layer (not shown) and an electron blocking layer (EBL) in addition to the hole injection layer (HIL) and the hole transport layer (HTL). The buffer layer (not shown) can increase light emission efficiency by compensating for the resonance distance according to the wavelength of light emitted from the light-emitting layer (EML). The material included in the buffer layer (not shown) may be a material that can be included in the hole transport region (HTR). The electron blocking layer (EBL) is a layer that serves to prevent electron injection from the electron transport region (ETR) into the hole transport region (HTR).

[0201] An emissive layer (EML) is provided on a hole transport region (HTR). The emissive layer (EML) may have a thickness of, for example, about 100 Å to about 1000 Å or about 100 Å to about 300 Å. The emissive layer (EML) may have a multilayer structure consisting of a single layer made of a single material, a single layer made of multiple different materials, or multiple layers made of multiple different materials.

[0202] In one embodiment of the light-emitting device (ED), the light-emitting layer (EML) may include a polycyclic compound represented by the following chemical formula 1.

[0203] [Chemical Formula 1]

[0204]

[0205] The compound represented by the above chemical formula 1 may include at least one anthracene derivative represented by the following chemical formula A.

[0206] [Chemical Formula A]

[0207]

[0208] In Formula A, Ra may 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 cyclic aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted cyclic heteroaryl group having 2 to 30 carbon atoms. For example, in one embodiment, Ra may be an unsubstituted phenyl group or an unsubstituted anthracenyl group, but the examples are not limited thereto.

[0209] L1 may be a substituted or unsubstituted cyclic arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted cyclic heteroarylene group having 2 to 30 carbon atoms, or a substituted or unsubstituted amine group. p may be 0 or 1. When p is 0, the anthracene derivative is directly bound to the core structure, and when p is 1, the anthracene derivative may be bound to the core structure through L1.

[0210] In one embodiment, Formula A may be represented by any one of the following Formulas A-1 to A-3.

[0211] [Chemical Formula A-1]

[0212]

[0213] [Chemical Formula A-2]

[0214]

[0215] [Chemical Formula A-3]

[0216]

[0217] [Chemical Formula A-4]

[0218]

[0219] Chemical formula A-1 is the case where p is 0. Chemical formula A-2 is the case where p is 1 and L1 is a phenylene group. Chemical formula A-3 is the case where p is 1 and L1 is This is the case. In chemical formula A-4, p is 1 and L1 is This is the case. In chemical formula A-3, m is 0 or 1, and This is the site where an anthracene derivative is substituted.

[0220] Chemical formula A-1 can be represented by either of the following chemical formulas AA-1 and AA-2.

[0221] [Chemical Formula AA-1]

[0222]

[0223] [Chemical Formula AA-2]

[0224]

[0225] Chemical formula AA-1 is the case where, in chemical formula A-1, the site where anthracene is bound to the core structure is the benzene ring located in the middle of anthracene, and the site where Ra is substituted is the benzene ring located in the middle of anthracene. Chemical formula AA-2 is the case where, in chemical formula A-1, the site where anthracene is bound to the core structure is located on the benzene ring on one side of anthracene, and the site where Ra is substituted is the benzene ring on the other side of anthracene. In chemical formulas AA-1 and AA-2, Ra is as defined in the above chemical formula 1.

[0226] Chemical formula A-2 can be represented by any one of the following chemical formulas B-1 to B-3.

[0227] [Chemical Formula B-1]

[0228]

[0229] [Chemical Formula B-2]

[0230]

[0231] [Chemical Formula B-3]

[0232]

[0233] Chemical formula B-1 is substituted for the phenylene group in chemical formula A-2 This is the case where the core structure is in the ortho position. Chemical formula B-2 is substituted for the phenylene group in chemical formula A-2. This is the case where the core structure is at the meta position. Chemical formula B-3 is substituted for the phenylene group in chemical formula A-2. This is the case where the parent nucleus structure is in the para position.

[0234] Chemical formula A-3 can be represented by the following chemical formula C-1 or chemical formula C-2.

[0235] [Chemical Formula C-1]

[0236]

[0237] [Chemical Formula C-2]

[0238]

[0239] In chemical formula C-1, m is 0 in chemical formula A-3, and This is the case where it is directly bonded to the nitrogen atom of this amine. Chemical formula C-2 is the case where m is 1 in chemical formula A-3, and This is the case where it is bonded to a phenylene group bonded to the nitrogen atom of this amine.

[0240] In Chemical Formula 1, X1 to X4 may each independently be O, S, Se, or NR1, and Z1 and Z2 may each independently be CR2. R1 and R2 may 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 oxy group, a substituted or unsubstituted cyclic aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted cyclic heteroaryl group having 2 to 30 carbon atoms, a substituted or unsubstituted thio group, a compound represented by the following Chemical Formula A, or may form a ring by bonding with adjacent groups, and X1 to X 4, At least one of Z1 and Z2 may include a compound represented by the following chemical formula A.

[0241] a1 and a2 are each independently integers from 0 to 2, and R y1 , R y2 Each of the following may 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 cyclic aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted cyclic heteroaryl group having 2 to 30 carbon atoms.

[0242] When a1 is 0, R in the benzene ring containing Z1 y1 When this is unsubstituted and a2 is 0, in the benzene ring containing Z2, R y2 It may be unsubstituted. When a1 is 1, in the benzene ring containing Z1, R y1This can be substituted once and can bond with the R2 of an adjacent CR2 to form a ring. When a2 is 1, the benzene ring containing Z2 has R y2 This can be substituted once and can combine with the R2 of an adjacent CR2 to form a ring. When a1 is 2, the benzene ring containing Z1 has R y1 These two can be substituted, and two Rs y1 These can combine with each other to form a ring. When A2 is 2, the benzene ring containing Z2 contains R y2 These two can be substituted, and two Rs y2 They can combine with each other to form a ring. However, this is merely illustrative, and the embodiments are not limited thereto, and R y1 and R y2 It can be combined in various ways to form a ring.

[0243] In one embodiment, the polycyclic compound represented by Formula 1 may have a minimum triplet excitation energy (T1) of 1.8 eV or less by including anthracene, which has a low minimum triplet excitation energy, as a substituent. By including a polycyclic compound with a low minimum triplet excitation energy, the lifespan of the light-emitting device can be improved. In one embodiment, the polycyclic compound represented by Formula 1 may emit blue light.

[0244] In one embodiment of the light-emitting device (ED), the light-emitting layer (EML) may include a polycyclic compound represented by the following chemical formula 2.

[0245] [Chemical Formula 2]

[0246]

[0247] X1 to X4 are each independently O, S, Se, or NR1, and R1 is, It may 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 cyclic aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted cyclic heteroaryl group having 2 to 30 carbon atoms.

[0248] In the above Chemical Formula 2, n may be an integer from 0 to 8. That is, the polycyclic compound represented by Chemical Formula 2 is at least one It can include as a substituent, and up to 8 It can include as a substituent.

[0249] If n is 0, at least one of X1 to X4 is R1 It is NR1, and

[0250] R1 is In the case of NR1, n can be an integer between 1 and 8.

[0251] In Formula 2, L1- may be a substituted or unsubstituted cyclic arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted cyclic heteroarylene group having 2 to 30 carbon atoms, or a substituted or unsubstituted divalent amine group. In Formula 2, p may be 0 or 1. When p is 0, the anthracene derivative is directly bonded to the core structure, and when p is 1 or more, the anthracene derivative may be bonded to the core structure with L1 in between.

[0252] Chemical formula 2 can be represented by any one of the following chemical formulas 3 to 5.

[0253] [Chemical Formula 3]

[0254]

[0255] [Chemical Formula 4]

[0257]

[0258] [Chemical Formula 5]

[0259]

[0260] .

[0261] Chemical formula 3 is the case where n is 0 in chemical formula 2. Chemical formula 4 is the case where n is 1 and p is 1. Chemical formula 5 is the case where n is 2 and p is 1 in chemical formula 2.

[0262] In Chemical Formula 3, at least one of X1 to X4 is R1 It can be NR1.

[0263] In Chemical Formula 4, L2 may be a substituted or unsubstituted ring-forming arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heteroarylene group having 2 to 30 carbon atoms, or a substituted or unsubstituted divalent amine group.

[0264] In Chemical Formula 5, L2 and L3 may each be independently a substituted or unsubstituted ring-forming arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heteroarylene group having 2 to 30 carbon atoms, or a substituted or unsubstituted divalent amine group.

[0265] In Chemical Formula 2 It can be represented by the following chemical formulas 6 to 9.

[0266] [Chemical Formula 6]

[0267]

[0268] [Chemical Formula 7]

[0269]

[0270] [Chemical Formula 8]

[0271] .

[0272] [Chemical Formula 9]

[0273]

[0274] Chemical formula 6 is of chemical formula 2. In this case, p is 0, and Chemical Formula 7 is of Chemical Formula 2. In this case, p is 1 and L1 is a phenylene group, and Chemical Formula 8 is of Chemical Formula 2. In this case, p is 1, and L1 is This is the case. is the site where the anthracenyl group is substituted. Chemical formula 9 is the case where p is 1 and L1 is phenanthrene.

[0275] Chemical formula 6 can be represented by either Chemical formula 6-1 or Chemical formula 6-2 below.

[0276] [Chemical Formula 6-1]

[0277]

[0278] [Chemical Formula 6-2]

[0279]

[0280] Chemical formula 6-1 is the case where the benzene ring located in the middle of anthracene in Chemical formula 6 is substituted into the core structure, and Ra is substituted into the benzene ring located in the middle of anthracene. Chemical formula 6-2 is the case where the benzene ring on one side of anthracene in Chemical formula 6 is substituted into the core structure, and Ra is substituted into the benzene ring on the other side of anthracene. In Chemical formulas 6-1 and 6-2, Ra is as defined in Chemical formula 1 above.

[0281] Chemical formula 7 can be represented by any one of the following chemical formulas 7-1 to 7-3.

[0282] [Chemical Formula 7-1]

[0283]

[0284] [Chemical Formula 7-2]

[0285]

[0286] [Chemical Formula 7-3]

[0287] .

[0288] Chemical formula 7-1 is substituted for the phenylene group in chemical formula 7 This is the case where the parent core structure is in the ortho position. Chemical formula 7-2 is substituted for the phenylene group in chemical formula 7. This is the case where the core structure is at the meta position. Chemical formula 7-3 is substituted for the phenylene group in chemical formula 7. This is the case where the parent nucleus structure is in the para position.

[0290] Chemical formula 8 can be represented by the following chemical formula 8-1 or chemical formula 8-2.

[0291] [Chemical Formula 8-1]

[0292]

[0293] [Chemical Formula 8-2]

[0294] .

[0295] In Chemical Formula 8-1, m is 0 in Chemical Formula 6, and This is the case where it is directly bonded to the nitrogen atom of this amine. In Chemical Formula 8-2, m is 1 in Chemical Formula 5, and This is the case where it is bonded to a phenylene group bonded to the nitrogen atom of this amine.

[0296] R in Chemical Formula 2 y and R a Each independently It may 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 cyclic aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted cyclic heteroaryl group having 2 to 30 carbon atoms, or it may form a ring by bonding with an adjacent group. For example, Ra may be an unsubstituted phenyl group or an unsubstituted naphthyl group, but the examples are not limited thereto. a may be an integer from 0 to 8-n.

[0297] In one embodiment, the polycyclic compound represented by Formula 2 may have a minimum triplet excitation energy (T1) of 1.8 eV or less by including anthracene, which has a low minimum triplet excitation energy, as a substituent. By including a polycyclic compound with a low minimum triplet excitation energy, the lifespan of the light-emitting device can be improved.

[0298] In one embodiment, the light-emitting layer may include at least one of the compounds listed in the following compound group 1.

[0299] [Compound Group 1]

[0300]

[0302]

[0303]

[0304]

[0305]

[0306]

[0307]

[0308]

[0309]

[0310]

[0311] In the light-emitting device (ED) of one embodiment illustrated in FIGS. 3 to 6, the light-emitting layer (EML) may include a host and a dopant. A polycyclic compound according to one embodiment may be used as a dopant material. For example, a polycyclic compound according to one embodiment may be used as a dopant material for a light-emitting layer that emits thermally activated delayed fluorescence.

[0312] The light-emitting layer (EML) may further include light-emitting layer materials described below in addition to the polycyclic compound of one embodiment.

[0313] The emissive layer (EML) may further include a compound represented by the following chemical formula E-1. The compound represented by the following chemical formula E-1 may be used as a fluorescent host material.

[0314] [Chemical Formula E-1]

[0315]

[0316] In chemical formula E-1, R 31 to R 40 Each may 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 ring-forming aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heteroaryl group having 2 to 30 carbon atoms, or may form a ring by bonding to an adjacent group. Meanwhile, R 31 to R 40 It can combine with adjacent groups to form a saturated hydrocarbon ring or an unsaturated hydrocarbon ring.

[0317] In chemical formula E-1, c and d can each independently be integers from 0 to 5.

[0318] Chemical formula E-1 may be represented by any one of the following compounds E1 to E19.

[0319]

[0320]

[0321]

[0322]

[0323] In one embodiment, the light-emitting layer (EML) may further comprise a compound represented by the following formula E-2a or formula E-2b. The compound represented by the following formula E-2a or formula E-2b may be used as a phosphorescent host material.

[0324] [Chemical Formula E-2a]

[0325]

[0326] In chemical formula E-2a, a is an integer between 0 and 10 inclusive, and L a may be a directly bonded, substituted, or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms. Meanwhile, if a is an integer of 2 or more, multiple L a Each may be an independently substituted or unsubstituted ring-forming arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heteroarylene group having 2 to 30 carbon atoms.

[0327] In addition, in chemical formula E-2a, A1 to A5 are each independently N or CR i It could be. R a to R iEach 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 ring-forming aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heteroaryl group having 2 to 30 carbon atoms, or may form a ring by bonding with an adjacent group. a to R i It can combine with adjacent groups to form a hydrocarbon ring or a heteroring containing N, O, S, etc. as ring-forming atoms.

[0328] Meanwhile, in chemical formula E-2a, two or three selected from A1 to A5 are N and the remainder are CR i It could be.

[0329] [Chemical Formula E-2b]

[0330]

[0331] In chemical formula E-2b, Cbz1 and Cbz2 may each independently be an unsubstituted carbazole group, or a carbazole group substituted with a ring-forming aryl group having 6 to 30 carbon atoms. b may be a directly bonded, substituted, or unsubstituted cyclic arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted cyclic arylene group having 2 to 30 carbon atoms. b is an integer from 0 to 10, and if b is an integer of 2 or more, multiple L b Each may be an independently substituted or unsubstituted ring-forming arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heteroarylene group having 2 to 30 carbon atoms.

[0332] A compound represented by chemical formula E-2a or chemical formula E-2b may be represented as any one of the compounds in compound group E-2 below. However, the compounds listed in compound group E-2 below are exemplary, and a compound represented by chemical formula E-2a or chemical formula E-2b is not limited to those listed in compound group E-2 below.

[0333] [Compound Group E-2]

[0334]

[0335]

[0336]

[0337]

[0338] The emitting layer (EML) may further include general materials known in the art as host materials. For example, the emitting layer (EML) may include at least one of DPEPO (Bis[2-(diphenylphosphino)phenyl] ether oxide), CBP (4,4'-Bis(carbazol-9-yl)biphenyl), mCP (1,3-Bis(carbazol-9-yl)benzene), PPF (2,8-Bis(diphenylphosphoryl)dibenzo[b,d]furan), TCTA (4,4',4''-Tris(carbazol-9-yl)-triphenylamine) and TPBi (1,3,5-tris(1-phenyl-1H-benzo[d]imidazole-2-yl)benzene) as host materials.However, this is not limited thereto, and examples include Alq3 (tris(8-hydroxyquinolino)aluminum), CBP (4,4'-bis(N-carbazolyl)-1,1'-biphenyl), PVK (poly(N-vinylcarbazole), ADN (9,10-di(naphthalene-2-yl)anthracene), TCTA (4,4',4''-Tris(carbazol-9-yl)-triphenylamine), TPBi (1,3,5-tris(N-phenylbenzimidazole-2-yl)benzene), TBADN (2-tert-butyl-9,10-di(naphth-2-yl)anthracene), DSA (distyrylarylene), CDBP (4,4′-bis(9-carbazolyl)-2,2′-dimethyl-biphenyl), MADN (2-Methyl-9,10-bis(naphthalen-2-yl)anthracene), CP1 (Hexaphenyl cyclotriphosphazene), UGH2 (1,4-Bis(triphenylsilyl)benzene), DPSiO3 (Hexaphenylcyclotrisiloxane), DPSiO4 (Octaphenylcyclotetrasiloxane), PPF (2,8-Bis(diphenylphosphoryl)dibenzofuran), etc. can be used as host materials.

[0339] The emissive layer (EML) may further include a compound represented by the following chemical formula Ma or chemical formula Mb. The compound represented by the following chemical formula Ma or chemical formula Mb may be used as a phosphorescent dopant material.

[0340] [Chemical Formula Ma]

[0341]

[0342] In the above formula Ma, Y1 to Y4 and Z1 to Z4 are each independently CR1 or N, and R1 to R4 are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted amine group, a substituted or unsubstituted thio group, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heteroaryl group having 2 to 30 carbon atoms, or may form a ring by bonding with an adjacent group. In the formula Ma, m is 0 or 1, and n is 2 or 3. In the formula Ma, when m is 0, n is 3, and when m is 1, n is 2.

[0343] Compounds represented by the chemical formula Ma can be used as red phosphorescent dopants or green phosphorescent dopants.

[0344] The compound represented by the chemical formula Ma may be represented by any one of the following compounds M-a1 to M-a19. However, the following compounds M-a1 to M-a19 are exemplary, and the compound represented by the chemical formula Ma is not limited to those represented by the following compounds M-a1 to M-a19.

[0345]

[0346]

[0347]

[0349] 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.

[0350] [Chemical Formula Mb]

[0351]

[0352] In the chemical formula Mb, Q1 to Q4 are each independently C or N, and C1 to C4 are each independently a substituted or unsubstituted cyclic hydrocarbon ring having 5 to 30 carbon atoms, or a substituted or unsubstituted cyclic heterocycle having 2 to 30 carbon atoms. L 21 to L 24 Each directly combines independently, , , , , , , a substituted or unsubstituted divalent alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cyclic arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted cyclic arylene group having 2 to 30 carbon atoms, and e1 to e4 are each independently 0 or 1. R 31 to R 39 Each 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 ring-forming aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heteroaryl group having 2 to 30 carbon atoms, or forms a ring by bonding to adjacent groups, and d1 to d4 are each independently integers from 0 to 4.

[0353] Compounds represented by the chemical formula Mb can be used as blue phosphorescent dopants or green phosphorescent dopants.

[0354] A compound represented by the chemical formula Mb may be represented by any one of the following compounds. However, the following compounds are exemplary, and the compound represented by the chemical formula Mb is not limited to those represented by the following compounds.

[0355]

[0356] In the above compounds, R, R 38 , and R 39 Each may independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heteroaryl group having 2 to 30 carbon atoms.

[0357] The emissive layer (EML) may further include a compound represented by any one of the following chemical formulas Fa to Fc. Compounds represented by the following chemical formulas Fa to Fc may be used as fluorescent dopant materials.

[0358] [Chemical Formula Fa]

[0359]

[0360] In the above chemical formula Fa, R a to R j The two selected from each are independently It could be replaced by R a to R j middle The remaining elements not substituted may each independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heteroaryl group having 2 to 30 carbon atoms. In this, Ar1 and Ar2 may each independently be a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heteroaryl group having 2 to 30 carbon atoms. For example, at least one of Ar1 and Ar2 may be a heteroaryl group containing O or S as a ring-forming atom.

[0361] [Chemical Formula Fb]

[0362]

[0363] In the above chemical formula Fb, R a and R b Each may independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heteroaryl group having 2 to 30 carbon atoms, or may be formed by bonding with adjacent groups.

[0364] In the chemical formula Fb, U and V may each be independently a substituted or unsubstituted ring-forming hydrocarbon ring with 5 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heterocyclic ring with 2 to 30 carbon atoms.

[0365] In the chemical formula Fb, the number of rings represented by U and V can each be independently 0 or 1. For example, if the number of U or V in the chemical formula Fb is 1, it means that one ring constitutes a condensed ring in the part labeled U or V, and if the number of U or V is 0, it means that there is no ring labeled U or V. Specifically, if the number of U is 0 and the number of V is 1, or if the number of U is 1 and the number of V is 0, the condensed ring having a fluorene core of the chemical formula Fb may be a tetracyclic compound. Additionally, if the number of both U and V is 0, the condensed ring of the chemical formula Fb may be a tricyclic compound. Additionally, if the number of both U and V is 1, the condensed ring having a fluorene core of the chemical formula Fb may be a pentacyclic compound.

[0367] [Chemical Formula Fc]

[0368]

[0369] In the chemical formula Fc, A1 and A2 are each independently O, S, Se, or NR m and R m It may be a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cyclic aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted cyclic heteroaryl group having 2 to 30 carbon atoms. R1 to R 11 Each is independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted amine group, a substituted or unsubstituted boryl 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 ring-forming aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heteroaryl group having 2 to 30 carbon atoms, or forms a ring by bonding with an adjacent group.

[0370] In the chemical formula Fc, A1 and A2 can each independently bond with substituents of adjacent rings to form condensation rings. For example, A1 and A2 each independently NR m In this case, A1 may combine with R4 or R5 to form a ring. Additionally, A2 may combine with R7 or R8 to form a ring.

[0371] In one embodiment, the light-emitting layer (EML) is a known dopant material, styryl derivative (e.g., 1,4-bis[2-(3-N-ethylcarbazoryl)vinyl]benzene (BCzVB), 4-(di-p-tolylamino)-4'-[(di-p-tolylamino)styryl]stilbene (DPAVB), N-(4-((E)-2-(6-((E)-4-(diphenylamino)styryl)naphthalen-2-yl)vinyl)phenyl)-N-phenylbenzenamine (N-BDAVBi)), 4,4'-bis[2-(4-(N,N-diphenylamino)phenyl)vinyl]biphenyl (DPAVBi), perylene and its derivatives (e.g., 2,5,8,11-Tetra-t-butylperylene (TBP)), pyrene and its derivatives (e.g., It may further include 1,1-dipyrene, 1,4-dipyrenylbenzene, 1,4-Bis(N,N-Diphenylamino)pyrene, etc.

[0372] The emissive layer (EML) may further comprise a known phosphorescent dopant material. For example, the phosphorescent dopant may be a metal complex comprising iridium (Ir), platinum (Pt), osmium (Os), gold (Au), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), or thulium (Tm). Specifically, FIrpic(iridium(III) bis(4,6-difluorophenylpyridinato-N,C2 ), Fir6 (Bis(2,4-difluorophenylpyridinato)-tetrakis(1-pyrazolyl)borate iridium(III)), or PtOEP (platinum octaethyl porphyrin) can be used as phosphorescent dopants. However, the examples are not limited thereto.

[0373] The emissive layer (EML) may contain a quantum dot material. The core of the quantum dot may be selected from group II-VI compounds, group III-V compounds, group IV-VI compounds, group IV elements, group IV compounds, and combinations thereof.

[0374] Group II-VI compounds are diatomic compounds selected from the group consisting of CdSe, CdTe, CdS, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, MgSe, MgS, and mixtures thereof; ternary compounds selected from the group consisting of CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, CdZnSe, CdZnTe, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, MgZnSe, MgZnS, and mixtures thereof; and may be selected from the group consisting of four-element compounds selected from the group consisting of HgZnTeS, CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe, HgZnSTe and mixtures thereof.

[0375] Group III-VI compounds include binary compounds such as In2S3 and In2Se3, and InGaS 3 It may include ternary compounds such as InGaSe3, or any combination thereof.

[0376] Group I-III-VI compounds are ternary compounds selected from the group consisting of AgInS, AgInS2, CuInS, CuInS2, AgGaS2, CuGaS2CuGaO2, AgGaO2, AgAlO2, and mixtures thereof, or AgInGaS2, It can be selected from four-element compounds such as CuInGaS2.

[0377] III-V group compounds may be selected from the group consisting of diatomic compounds selected from the group consisting of GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, InSb, and mixtures thereof; ternary compounds selected from the group consisting of GaNP, GaNAs, GaNSb, GaPAs, GaPSb, AlNP, AlNAs, AlNSb, AlPAs, AlPSb, InGaP, InAlP, InNP, InNAs, InNSb, InPAs, InPSb, and mixtures thereof; and quaternary compounds selected from the group consisting of GaAlNP, GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNP, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs, InAlPSb, and mixtures thereof. Meanwhile, III-V group compounds may further include a group II metal. For example, InZnP, etc., can be selected as a Group III-II-V compound.

[0378] Group IV-VI compounds may be selected from the group consisting of SnS, SnSe, SnTe, PbS, PbSe, PbTe, and mixtures thereof; ternary compounds selected from the group consisting of SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, SnPbTe, and mixtures thereof; and quaternary compounds selected from the group consisting of SnPbSSe, SnPbSeTe, SnPbSTe, and mixtures thereof. Group IV elements may be selected from the group consisting of Si, Ge, and mixtures thereof. Group IV compounds may be ternary compounds selected from the group consisting of SiC, SiGe, and mixtures thereof.

[0379] In this case, the binary, ternary, or quaternary compounds may exist within the particle at a uniform concentration, or they may exist within the same particle with their concentration distributions partially divided into different states. Additionally, they may have a core / shell structure in which one quantum dot surrounds another. In a core / shell structure, there may be a concentration gradient in which the concentration of the element in the shell decreases as it moves toward the core.

[0380] In some embodiments, the quantum dot may have a core-shell structure comprising a core containing the aforementioned nanocrystal and a shell surrounding the core. The shell of the quantum dot may serve as a protective layer to maintain semiconductor properties by preventing chemical degradation of the core and / or as a charging layer to impart electrophoretic properties to the quantum dot. The shell may be a single layer or a multilayer. Examples of the shell of the quantum dot include oxides of metals or non-metals, semiconductor compounds, or combinations thereof.

[0381] For example, the oxide of the metal or nonmetal mentioned above may be exemplified as a binary compound such as SiO2, Al2O3, TiO2, ZnO, MnO, Mn2O3, Mn3O4, CuO, FeO, Fe2O3, Fe3O4, CoO, Co3O4, NiO, or a ternary compound such as MgAl2O4, CoFe2O4, NiFe2O4, CoMn2O4, but the present invention is not limited thereto.

[0382] In addition, the above semiconductor compounds may be examples of CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnSeS, ZnTeS, GaAs, GaP, GaSb, HgS, HgSe, HgTe, InAs, InP, InGaP, InSb, AlAs, AlP, AlSb, etc., but the present invention is not limited thereto.

[0383] Quantum dots can have a full width of half maximum (FWHM) of the emission wavelength spectrum of about 45 nm or less, preferably about 40 nm or less, and more preferably about 30 nm or less, and color purity or color reproducibility can be improved in this range. In addition, since the light emitted through these quantum dots is emitted in all directions, the viewing angle can be improved.

[0384] In addition, the shape of the quantum dots is not specifically limited to shapes commonly used in the field, but more specifically, shapes such as spherical, pyramidal, multi-arm, or cubic nanoparticles, nanotubes, nanowires, nanofibers, and nanoplate particles may be used.

[0385] Quantum dots can control the color of the light they emit depending on their particle size, and accordingly, they can have various emission colors such as blue, red, and green.

[0386] In the light-emitting device (ED) of one embodiment illustrated in FIGS. 3 to 6, an electron transport region (ETR) is provided on the light-emitting layer (EML). The electron transport region (ETR) may include at least one of a hole blocking layer (HBL), an electron transport layer (ETL), and an electron injection layer (EIL), but the embodiment is not limited thereto.

[0387] The electron transport region (ETR) may have a multilayer structure consisting of a single layer made of a single material, a single layer made of multiple different materials, or multiple layers made of multiple different materials.

[0388] For example, the electron transport region (ETR) may have a single-layer structure of an electron injection layer (EIL) or an electron transport layer (ETL), or it may have a single-layer structure composed of an electron injection material and an electron transport material. Additionally, the electron transport region (ETR) may have a single-layer structure composed of multiple different materials, or it may have an electron transport layer (ETL) / electron injection layer (EIL) or hole blocking layer (HBL) / electron transport layer (ETL) / electron injection layer (EIL) structure stacked sequentially from the emitting layer (EML), but is not limited thereto. The thickness of the electron transport region (ETR) may be, for example, about 1000 Å to about 1500 Å.

[0389] The electron transport region (ETR) can be formed using various methods such as vacuum deposition, spin coating, casting, the Langmuir-Blodgett (LB) method, inkjet printing, laser printing, and laser induced thermal imaging (LITI).

[0390] The electron transport domain (ETR) may include a compound represented by the following chemical formula ET-1.

[0391] [Chemical Formula ET-1]

[0392]

[0393] In the chemical formula ET-1, at least one of X1 to X3 is N and the rest are CR a is. R a may be a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heteroaryl group having 2 to 30 carbon atoms. Ar1 to Ar3 may each independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heteroaryl group having 2 to 30 carbon atoms.

[0394] In the formula ET-1, a to c may each be an integer from 0 to 10 or less, independently. In the formula ET-1, L1 to L3 may each be a direct linkage, a substituted or unsubstituted ring-forming arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heteroarylene group having 2 to 30 carbon atoms. Meanwhile, when a to c is an integer of 2 or more, L1 to L3 may each be a substituted or unsubstituted ring-forming arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heteroarylene group having 2 to 30 carbon atoms.

[0395] The electron transport domain (ETR) may include anthracene compounds. However, it is not limited thereto, and the electron transport domain (ETR) may include, for example, Alq3(Tris(8-hydroxyquinolinato)aluminum), 1,3,5-tri[(3-pyridyl)-phen-3-yl]benzene, 2,4,6-tris(3'-(pyridin-3-yl)biphenyl-3-yl)-1,3,5-triazine, 2-(4-(N-phenylbenzoimidazol-1-yl)phenyl)-9,10-dinaphthylanthracene, TPBi(1,3,5-Tri(1-phenyl-1H-benzo[d]imidazol-2-yl)benzene), BCP(2,9-Dimethyl-4,7-diphenyl-1,10-phenanthroline), Bphen(4,7-Diphenyl-1,10-phenanthroline), It may include TAZ(3-(4-Biphenylyl)-4-phenyl-5-tert-butylphenyl-1,2,4-triazole), NTAZ(4-(Naphthalen-1-yl)-3,5-diphenyl-4H-1,2,4-triazole), tBu-PBD(2-(4-Biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole), BAlq(Bis(2-methyl-8-quinolinolato-N1,O8)-(1,1'-Biphenyl-4-olato)aluminum), Bebq2(berylliumbis(benzoquinolin-10-olate)), ADN(9,10-di(naphthalene-2-yl)anthracene), BmPyPhB(1,3-Bis[3,5-di(pyridin-3-yl)phenyl]benzene) and mixtures thereof.

[0396] Additionally, the electron transport region (ETR) may include metal halides such as LiF, NaCl, CsF, RbCl, RbI, CuI, and KI, lanthanide metals such as Yb, and co-deposited materials of the above metal halides and lanthanide metals. For example, the electron transport region (ETR) may include KI:Yb, RbI:Yb, etc. as co-deposited materials. Meanwhile, metal oxides such as Li2O and BaO, or Liq(8-hydroxyl-Lithium quinolate), etc., may be used for the electron transport region (ETR), but the examples are not limited thereto. The electron transport region (ETR) may also be composed of a material in which an electron transport material and an insulating organometal salt are mixed. The organometal salt may be a material having an energy band gap of approximately 4 eV or more. Specifically, for example, organometallic salts may include metal acetate, metal benzoate, metal acetoacetate, metal acetylacetonate, or metal stearate.

[0397] The electron transport region (ETR) may further include at least one of BCP (2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline) and Bphen (4,7-diphenyl-1,10-phenanthroline) in addition to the aforementioned materials, but the examples are not limited thereto.

[0398] The electron transport region (ETR) may include compounds of the electron transport region described above in at least one of the electron injection layer (EIL), electron transport layer (ETL), and hole blocking layer (HBL).

[0399] If the electron transport region (ETR) includes an electron transport layer (ETL), the thickness of the electron transport layer (ETL) may be about 100 Å to about 1000 Å, for example, about 150 Å to about 500 Å. If the thickness of the electron transport layer (ETL) satisfies the range described above, satisfactory electron transport characteristics can be obtained without a substantial increase in driving voltage. If the electron transport region (ETR) includes an electron injection layer (EIL), the thickness of the electron injection layer (EIL) may be about 1 Å to about 100 Å, or about 3 Å to about 90 Å. If the thickness of the electron injection layer (EIL) satisfies the range described above, satisfactory electron injection characteristics can be obtained without a substantial increase in driving voltage.

[0400] The second electrode (EL2) is provided on the electron transport region (ETR). The second electrode (EL2) may be a common electrode. The second electrode (EL2) may be a cathode or an anode, but the embodiments are not limited thereto. For example, if the first electrode (EL1) is an anode, the second electrode (EL2) may be a cathode, and if the first electrode (EL1) is a cathode, the second electrode (EL2) may be an anode.

[0401] The second electrode (EL2) may be a transmissive electrode, a semitransmissive electrode, or a reflective electrode. If the second electrode (EL2) is a transmissive electrode, the second electrode (EL2) may be made of a transparent metal oxide, for example, ITO (indium tin oxide), IZO (indium zinc oxide), ZnO (zinc oxide), ITZO (indium tin zinc oxide), etc.

[0402] When the second electrode (EL2) is a semi-transparent electrode or a reflective electrode, the second electrode (EL2) may include Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF / Ca, LiF / Al, Mo, Ti, Yb, W, In, Sn, Zn, or a compound or mixture containing these (e.g., AgMg, AgYb, or MgAg). Alternatively, the second electrode (EL2) may have a plurality of layer structures including a reflective film or semi-transparent film formed of the above material and a transparent conductive film formed of ITO (indium tin oxide), IZO (indium zinc oxide), ZnO (zinc oxide), ITZO (indium tin zinc oxide), etc. For example, the second electrode (EL2) may include the metal material described above, a combination of two or more metal materials selected from the metal materials described above, or oxides of the metal materials described above.

[0403] Although not illustrated, the second electrode (EL2) can be connected to an auxiliary electrode. When the second electrode (EL2) is connected to an auxiliary electrode, the resistance of the second electrode (EL2) can be reduced.

[0404] Meanwhile, a capping layer (CPL) may be further disposed on the second electrode (EL2) of the light-emitting element (ED) of one embodiment. The capping layer (CPL) may include a multilayer or a single layer.

[0405] In one embodiment, the capping layer (CPL) may be an organic layer or an inorganic layer. For example, if the capping layer (CPL) includes an inorganic material, the inorganic material may be an alkali metal compound such as LiF, an alkaline earth metal compound such as MgF2, SiON, or SiN X It may include SiOy, etc.

[0406] For example, when the capping layer (CPL) contains an organic material, the organic material may include α-NPD, NPB, TPD, m-MTDATA, Alq3, CuPc, TPD15 (N4,N4,N4',N4'-tetra (biphenyl-4-yl) biphenyl-4,4'-diamine), TCTA (4,4',4"- Tris (carbazol sol-9-yl) triphenylamine), etc., or may include an epoxy resin or an acrylate such as methacrylate. However, the examples are not limited thereto, and the capping layer (CPL) may include at least one of the following compounds P1 to P5.

[0407]

[0408]

[0409] Meanwhile, the refractive index of the capping layer (CPL) may be 1.6 or higher. Specifically, for light in a wavelength range of 550 nm or more and 660 nm or less, the refractive index of the capping layer (CPL) may be 1.6 or higher.

[0410] FIGS. 7 and FIGS. 8 are cross-sectional views of a display device according to one embodiment. In the following description of the display device according to one embodiment with reference to FIGS. 7 and FIGS. 8, details that overlap with those described in FIGS. 1 to 6 above will not be explained again, and the differences will be explained primarily.

[0411] Referring to FIG. 7, a display device (DD) according to one embodiment may include a display panel (DP) including a display element layer (DP-ED), a light control layer (CCL) and a color filter layer (CFL) disposed on the display panel (DP).

[0412] In one embodiment illustrated in FIG. 7, the display panel (DP) includes a base layer (BS), a circuit layer (DP-CL) provided on the base layer (BS), and a display element layer (DP-ED), and the display element layer (DP-ED) may include a light-emitting element (ED).

[0413] The light-emitting element (ED) may include a first electrode (EL1), a hole transport region (HTR) disposed on the first electrode (EL1), a light-emitting layer (EML) disposed on the hole transport region (HTR), an electron transport region (ETR) disposed on the light-emitting layer (EML), and a second electrode (EL2) disposed on the electron transport region (ETR). Meanwhile, the structure of the light-emitting element (ED) shown in FIG. 7 may be identical to the structure of the light-emitting element of FIG. 3 to FIG. 6 described above.

[0414] Referring to FIG. 7, the light-emitting layer (EML) may be disposed within an opening (OH) defined in the pixel defining film (PDL). For example, the light-emitting layer (EML) provided corresponding to each light-emitting region (PXA-R, PXA-G, PXA-B) separated by the pixel defining film (PDL) may emit light of the same wavelength range. In a display device (DD) of one embodiment, the light-emitting layer (EML) may emit blue light. Meanwhile, unlike illustrated, in one embodiment, the light-emitting layer (EML) may be provided as a common layer over the entire light-emitting regions (PXA-R, PXA-G, PXA-B).

[0415] A light control layer (CCL) may be placed on a display panel (DP). The light control layer (CCL) may include a light converter. The light converter may be a quantum dot or a phosphor. The light converter may emit light by converting the wavelength of the provided light. That is, the light control layer (CCL) may be a layer containing quantum dots or a layer containing a phosphor.

[0416] The optical control layer (CCL) may include a plurality of optical control units (CCP1, CCP2, CCP3). The optical control units (CCP1, CCP2, CCP3) may be spaced apart from each other.

[0417] Referring to FIG. 7, a split pattern (BMP) may be placed between spaced-apart light control units (CCP1, CCP2, CCP3), but the embodiment is not limited thereto. In FIG. 7, the split pattern (BMP) is shown as not overlapping with the light control units (CCP1, CCP2, CCP3), but the edges of the light control units (CCP1, CCP2, CCP3) may overlap with the split pattern (BMP) at least partially.

[0418] The light control layer (CCL) may include a first light control unit (CCP1) comprising a first quantum dot (QD1) that converts a first color light provided by a light-emitting element (ED) into a second color light, a second light control unit (CCP2) comprising a second quantum dot (QD2) that converts the first color light into a third color light, and a third light control unit (CCP3) that transmits the first color light.

[0419] In one embodiment, the first light control unit (CCP1) may provide red light, which is the second color light, and the second light control unit (CCP2) may provide green light, which is the third color light. The third light control unit (CCP3) may transmit and provide blue light, which is the first color light provided by the light-emitting element (ED). For example, the first quantum dot (QD1) may be a red quantum dot and the second quantum dot (QD2) may be a green quantum dot. The same as described above may apply to the quantum dots (QD1, QD2).

[0420] Additionally, the light control layer (CCL) may further include a scatterer (SP). The first light control unit (CCP1) may include a first quantum dot (QD1) and a scatterer (SP), the second light control unit (CCP2) may include a second quantum dot (QD2) and a scatterer (SP), and the third light control unit (CCP3) may not include a quantum dot and may include a scatterer (SP).

[0421] The scatterer (SP) may be an inorganic particle. For example, the scatterer (SP) may comprise at least one of TiO2, ZnO, Al2O3, SiO2, and hollow silica. The scatterer (SP) may comprise any one of TiO2, ZnO, Al2O3, SiO2, and hollow silica, or may be a mixture of two or more materials selected from TiO2, ZnO, Al2O3, SiO2, and hollow silica.

[0422] Each of the first light control unit (CCP1), the second light control unit (CCP2), and the third light control unit (CCP3) may include a base resin (BR1, BR2, BR3) that disperses quantum dots (QD1, QD2) and scatterers (SP). In one embodiment, the first light control unit (CCP1) may include a first quantum dot (QD1) and a scatterer (SP) dispersed within the first base resin (BR1), the second light control unit (CCP2) may include a second quantum dot (QD2) and a scatterer (SP) dispersed within the second base resin (BR2), and the third light control unit (CCP3) may include a scatterer (SP) dispersed within the third base resin (BR3). The base resin (BR1, BR2, BR3) is a medium in which quantum dots (QD1, QD2) and scatterers (SP) are dispersed, and can be composed of various resin compositions that can generally be referred to as binders. For example, the base resin (BR1, BR2, BR3) may be an acrylic resin, a urethane resin, a silicone resin, an epoxy resin, etc. The base resin (BR1, BR2, BR3) may be a transparent resin. In one embodiment, the first base resin (BR1), the second base resin (BR2), and the third base resin (BR3) may each be the same or different from one another.

[0423] The light control layer (CCL) may include a barrier layer (BFL1). The barrier layer (BFL1) may serve to prevent the penetration of moisture and / or oxygen (hereinafter referred to as 'moisture / oxygen'). The barrier layer (BFL1) may be placed on the light control units (CCP1, CCP2, CCP3) to block the light control units (CCP1, CCP2, CCP3) from being exposed to moisture / oxygen. Meanwhile, the barrier layer (BFL1) may cover the light control units (CCP1, CCP2, CCP3). Additionally, a barrier layer (BFL2) may be provided between the light control units (CCP1, CCP2, CCP3) and the color filter layer (CFL).

[0424] The barrier layer (BFL1, BFL2) may include at least one inorganic layer. That is, the barrier layer (BFL1, BFL2) may be formed by including an inorganic material. For example, the barrier layer (BFL1, BFL2) may be formed by including silicon nitride, aluminum nitride, zirconium nitride, titanium nitride, hafnium nitride, tantalum nitride, silicon oxide, aluminum oxide, titanium oxide, tin oxide, cerium oxide, silicon oxynitride, or a metal thin film with secured light transmittance. Meanwhile, the barrier layer (BFL1, BFL2) may further include an organic film. The barrier layer (BFL1, BFL2) may be composed of a single layer or multiple layers.

[0425] In a display device (DD) of one embodiment, a color filter layer (CFL) may be placed on a light control layer (CCL). For example, the color filter layer (CFL) may be placed directly on the light control layer (CCL). In this case, the barrier layer (BFL2) may be omitted.

[0426] The color filter layer (CFL) may include a light-blocking portion (BM) and filters (CF-B, CF-G, CF-R). The color filter layer (CFL) may include a first filter (CF1) that transmits a second color light, a second filter (CF2) that transmits a third color light, and a third filter (CF3) that transmits a first color light. For example, the first filter (CF1) may be a red filter, the second filter (CF2) may be a green filter, and the third filter (CF3) may be a blue filter. Each of the filters (CF1, CF2, CF3) may include a polymer photosensitive resin and a pigment or dye. The first filter (CF1) may include a red pigment or dye, the second filter (CF2) may include a green pigment or dye, and the third filter (CF3) may include a blue pigment or dye. Meanwhile, the embodiments are not limited thereto, and the third filter (CF3) may not contain pigment or dye. The third filter (CF3) may contain a polymer photosensitive resin and not contain pigment or dye. The third filter (CF3) may be transparent. The third filter (CF3) may be formed of a transparent photosensitive resin.

[0427] Additionally, in one embodiment, the first filter (CF1) and the second filter (CF2) may be yellow filters. The first filter (CF1) and the second filter (CF2) may also be provided as a single unit without being distinguished from each other.

[0428] The light-blocking portion (BM) may be a black matrix. The light-blocking portion (BM) may be formed by including an organic light-blocking material or an inorganic light-blocking material containing a black pigment or a black dye. The light-blocking portion (BM) may prevent light leakage and distinguish the boundaries between adjacent filters (CF1, CF2, CF3). Additionally, in one embodiment, the light-blocking portion (BM) may be formed of a blue filter.

[0429] Each of the first to third filters (CF1, CF2, CF3) can be positioned corresponding to the red light emission region (PXA-R), the green light emission region (PXA-G), and the blue light emission region (PXA-B), respectively.

[0430] A base substrate (BL) may be disposed on the color filter layer (CFL). The base substrate (BL) may be a component that provides a base surface on which the color filter layer (CFL) and the light control layer (CCL) are disposed. The base substrate (BL) may be a glass substrate, a metal substrate, a plastic substrate, etc. However, the embodiments are not limited thereto, and the base substrate (BL) may be an inorganic layer, an organic layer, or a composite material layer. In addition, unlike what is illustrated, the base substrate (BL) may be omitted in one embodiment.

[0431] FIG. 8 is a cross-sectional view showing a part of a display device according to one embodiment. FIG. 8 shows a cross-sectional view of a part corresponding to the display panel (DP) of FIG. 7. In the display device (DD-TD) of one embodiment, the light-emitting element (ED-BT) may include a plurality of light-emitting structures (OL-B1, OL-B2, OL-B3). The light-emitting element (ED-BT) may include a first electrode (EL1) and a second electrode (EL2) facing each other, and a plurality of light-emitting structures (OL-B1, OL-B2, OL-B3) provided by being sequentially stacked in the thickness direction between the first electrode (EL1) and the second electrode (EL2). Each of the light-emitting structures (OL-B1, OL-B2, OL-B3) may include a light-emitting layer (EML, FIG. 7), a hole transport region (HTR), and an electron transport region (ETR) arranged between the light-emitting layer (EML, FIG. 7).

[0432] That is, the light-emitting element (ED-BT) included in the display device (DD-TD) of one embodiment may be a light-emitting element with a tandem structure including a plurality of light-emitting layers.

[0433] In one embodiment illustrated in FIG. 8, the light emitted from each of the light-emitting structures (OL-B1, OL-B2, OL-B3) may all be blue light. However, the embodiment is not limited thereto, and the wavelength range of the light emitted from each of the light-emitting structures (OL-B1, OL-B2, OL-B3) may differ from one another. For example, a light-emitting device (ED-BT) comprising a plurality of light-emitting structures (OL-B1, OL-B2, OL-B3) that emit light in different wavelength ranges may emit white light.

[0434] A charge generation layer (CGL) may be disposed between adjacent light-emitting structures (OL-B1, OL-B2, OL-B3). The charge generation layer (CGL) may include a p-type charge generation layer and / or an n-type charge generation layer.

[0435] Hereinafter, with reference to examples and comparative examples, a polycyclic compound according to one embodiment of the present invention and a light-emitting device of one embodiment comprising a polycyclic amine compound of one embodiment will be described in detail. Furthermore, the examples described below are examples to aid in understanding the present invention, and the scope of the present invention is not limited thereto.

[0436] [Example]

[0437] 1. Synthesis of the polycyclic compound of one example

[0438] First, regarding the synthesis method of a polycyclic compound according to one embodiment, the synthesis method of the compound to the one described below will be specifically explained by exemplifying the synthesis method of the compound. Furthermore, the synthesis method of the compounds described below is one embodiment, and the synthesis method of the compound according to the embodiment of the present invention is not limited to the following examples.

[0439] Synthesis of Compound 20

[0440] Compound 20 according to one embodiment can be synthesized, for example, by the step of Reaction Scheme 1 below.

[0441] [Reaction Equation 1]

[0443]

[0444]

[0445]

[0446] [ Compound 20-a ]

[0447] Under an argon atmosphere, 9-bromo-10-phenylanthracene (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 to a 2 L flask and dissolved in a mixed solution of 700 mL of toluene and 300 mL of water. The reaction solution was then stirred at 120°C for 12 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added for extraction to collect the organic layer. The organic layer was then dried with MgSO4 and filtered. The solvent was removed from the filtered solution under reduced pressure, and the resulting solid was purified and separated by silica gel column chromatography using CH2Cl2 and hexane as developing solvents to obtain compound 20-a (yellow solid, 52 g, 74%).

[0448] ESI-LCMS: [M+H] + : C 32 H 23 N. 421.1763.

[0449] 1 H-NMR (400 MHz, CDCl3): 8.21 (d, 4H), 7.65 (d, 2H), 7.55 (m, 4H), 7.37 (m, 7H), 7.02 (m, 3H).

[0450] [ Compound 20-b ]

[0451] Under an argon atmosphere, 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 to a 2 L flask and dissolved in 1 L of toluene. The reaction solution was then stirred at 85°C for 12 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added for extraction to collect the organic layer. The organic layer was then dried with MgSO4 and filtered. The solvent was removed from the filtered solution under reduced pressure, and the resulting solid was purified and separated by silica gel column chromatography using CH2Cl2 and hexane as developing solvents to obtain compound 20-b (white solid, 40 g, 54%).

[0452] ESI-LCMS: [M+H] + : C 42 H 34 NBr. 631.1664.

[0453] 1 H-NMR (400 MHz, 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).

[0455] [ Compound 20-c ]

[0456] Under an argon atmosphere, compound 20-b (40 g, 63 mmol), aniline (8.8 g, 95 mmol), tris-tert-butyl phosphine (6 mL, 6.3 mmol), sodium tert-butoxide (17.7 g, 189 mmol), and Pd2dba3 (2.9 g, 3.15 mmol) were added to a 2 L flask and dissolved in 600 mL of toluene. The reaction solution was then stirred at 100°C for 6 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added for extraction to collect the organic layer. The organic layer was then dried with MgSO4 and filtered. The solvent was removed from the filtered solution under reduced pressure, and the resulting solid was purified and separated by column chromatography using silica gel with CH2Cl2 and hexane as developing solvents to obtain compound 20-c (white solid, 33 g, 82%).

[0457] ESI-LCMS: [M+H] + : C 48 H 41 N2. 645.1212.

[0458] 1 H-NMR (400 MHz, 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).

[0460] [ Compound 20-d ]

[0461] Under an argon atmosphere, compound 20-c (33 g, 51 mmol), 3-iodo-bromobenzene (14.5 g, 51 mmol), tris-tert-butyl phosphine (4.6 mL, 5.0 mmol), sodium tert-butoxide (14.7 g, 153 mmol), and Pd2dba3 (2.3 g, 2.55 mmol) were added to a 1 L flask and dissolved in 400 mL of toluene. The reaction solution was then stirred at 100°C for 6 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added for extraction to collect the organic layer. The organic layer was then dried with MgSO4 and filtered. The filtered solution was de-pressurized to remove the solvent, and the obtained solid was purified and separated by column chromatography using silica gel with CH2Cl2 and hexane as developing solvents to obtain compound 20-d (white solid, 31 g, 77%).

[0462] ESI-LCMS: [M+H] + : C 54 H 44 N2Br. 799.2245.

[0463] 1 H-NMR (400 MHz, 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).

[0465] [ Compound 20-e ]

[0466] Under an argon atmosphere, compound 20-d (30 g, 37.5 mmol), aniline (5.2 g, 56 mmol), tris-tert-butyl phosphine (3.4 mL, 3.6 mmol), sodium tert-butoxide (10.8 g, 112.5 mmol), and Pd2dba3 (1.7 g, 1.8 mmol) were added to a 1 L flask and dissolved in 400 mL of toluene. The reaction solution was then stirred at 100°C for 6 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added for extraction to collect the organic layer. The organic layer was then dried with MgSO4 and filtered. The solvent was removed from the filtered solution under reduced pressure, and the resulting solid was purified and separated by silica gel column chromatography using CH2Cl2 and hexane as developing solvents to obtain compound 20-e (white solid, 24 g, 79%).

[0467] ESI-LCMS: [M+H] + : C 60 H 50 N3. 812.3331.

[0468] 1 H-NMR (400 MHz, 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).

[0469] [ Compound 20-f ]

[0470] Under an argon atmosphere, 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 to a 1 L flask and dissolved in 400 mL of toluene. The reaction solution was then stirred at 100°C for 6 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added for extraction to collect the organic layer. The organic layer was then dried with MgSO4 and filtered. The filtered solution was de-pressurized to remove the solvent, and the obtained solid was purified and separated by column chromatography using silica gel with CH2Cl2 and hexane as developing solvents to obtain compound 20-f (white solid, 17 g, 57%).

[0471] ESI-LCMS: [M+H] + : C 70 H 61 N3Br. 1022.3982.

[0472] 1 H-NMR (400 MHz, 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).

[0474] [ Compound 20-g ]

[0475] Under an argon atmosphere, 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 to a 1 L flask and dissolved in 300 mL of toluene. The reaction solution was then stirred at 100°C for 6 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added for extraction to collect the organic layer. The organic layer was then dried with MgSO4 and filtered. The solvent was removed from the filtered solution under reduced pressure, and the resulting solid was purified and separated by column chromatography using silica gel with CH2Cl2 and hexane as developing solvents to obtain compound 20-g (white solid, 22 g, 69%).

[0476] ESI-LCMS: [M+H] + : C 82 H 71 N 4. 1111.4431.

[0477] 1 H-NMR (400 MHz, 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).

[0479] [ Compound 20 ]

[0480] Under an argon atmosphere, 20 g (20 g, 18 mmol) of compound was dissolved in 500 mL of o-dichlorobenzene in a 1 L flask and cooled to 0°C in an ice-water bath. Boron tribromide (5 eq) was slowly added dropwise to the reaction solution, and after slowly raising the temperature to room temperature, the mixture was stirred for 20 minutes. The reaction solution was then raised to 150°C and stirred for 12 hours. After cooling, triethylamine (5 mL) was slowly added dropwise to terminate the reaction, and all solvent was removed under reduced pressure. The obtained solid was washed with MeOH, and then purified and separated by column chromatography using silica gel with CH2Cl2 and hexane as developing solvents to obtain compound 20 (yellow solid, 2.4 g, 12%).

[0481] ESI-LCMS: [M+H] + : C 82 H 65 B2N 4. 1127.5153.

[0482] 1 H-NMR (400 MHz, 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).

[0484] Synthesis of Compound 25

[0485] Compound 25 according to one embodiment can be synthesized, for example, by the steps of Reaction Scheme 2 below.

[0486] [Reaction Equation 2]

[0487]

[0489] [ Compound 25-a ]

[0490] Under an argon atmosphere, 9-bromo-10-phenylanthracene (50 g, 168 mmol), 3-iodo-bromobenzene (48 g, 168 mmol), K2CO3 (70 g, 500 mmol), and Pd(PPh3)4 (5.8 g, 5 mmol) were added to a 2 L flask and dissolved in a mixed solution of 700 mL of toluene and 300 mL of water. The reaction solution was then stirred at 120°C for 12 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added for extraction to collect the organic layer. The organic layer was then dried with MgSO4 and filtered. The solvent was removed from the filtered solution under reduced pressure, and the resulting solid was purified and separated by silica gel column chromatography using CH2Cl2 and hexane as developing solvents to obtain compound 25-a (yellow solid, 45 g, 66%).

[0491] ESI-LCMS: [M+H] + : C 26 H 18 Br. 409.0432.

[0492] 1 H-NMR (400 MHz, CDCl3): 8.21 (m, 4H), 7.65 (m, 3H), 7.55 (t, 2H), 7.41 (m, 8H).

[0494] [ Compound 25-b ]

[0495] In a 2 L flask under an argon atmosphere, compound 25-a (45 g, 110 mmol), N 1 ,N 1 ,N 3 ,N 31,3,5-triamine (47 g, 110 mmol), tri-tert-butyl-phosphine (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, after which the reaction solution was stirred at 100°C for 6 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added for extraction to collect the organic layer, which was then dried with MgSO4 and filtered. The solvent was removed from the filtered solution under reduced pressure, and the obtained solid was purified and separated by column chromatography using silica gel with CH2Cl2 and hexane as developing solvents to obtain compound 25-b (white solid, 56 g, 68%).

[0496] ESI-LCMS: [M+H] + : C 56 H 42 N3. 756.3221.

[0497] 1 H-NMR (400 MHz, 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).

[0499] [ Compound 25-c ]

[0500] Under an argon atmosphere, compound 25-b (55 g, 72 mmol), 3-bromophenol (12.6 g, 72 mmol), tri-tert-butyl-phosphine (6.6 ml, 7.2 mmol), sodium tert-butoxide (21 g, 216 mmol), and Pd2dba3 (3.3 g, 3.6 mmol) were added to a 2 L flask and dissolved in 600 mL of toluene. The reaction solution was then stirred at 100°C for 6 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added for extraction to collect the organic layer. The organic layer was then dried with MgSO4 and filtered. The solvent was removed from the filtered solution under reduced pressure, and the resulting solid was purified and separated by column chromatography using silica gel with CH2Cl2 and hexane as developing solvents to obtain compound 25-c (white solid, 44.5 g, 73%).

[0501] ESI-LCMS: [M+H] + : C 62 H 46 N3O. 848.2119.

[0502] 1 H-NMR (400 MHz, 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).

[0505] [ Compound 25-d ]

[0506] In a 1 L flask under an argon atmosphere, 25-c (44 g, 52 mmol), 5-bromo-N 1 ,N 1 ,N 3 ,N 325-tetraphenylbenzene-1,3-diamine (25.5 g, 52 mmol), CuI (9.88 g, 52 mmol), and 2-picolinic acid (6.4 g, 52 mmol) were added and dissolved in 500 mL of DMF, after which the reaction solution was stirred at 180°C for 12 hours. After cooling, the solution was poured into water (1 L), and the formed solid was filtered. The obtained solid was dissolved again in CH2Cl2, washed several times with water, collected the organic layer, dried with MgSO4, and filtered. The solvent was removed from the filtered solution under reduced pressure, and the obtained solid was purified and separated by silica gel column chromatography using CH2Cl2 and hexane as developing solvents to obtain compound 25-d (white solid, 28 g, 43%).

[0507] ESI-LCMS: [M+H] + : C 92 H 68 N5O. 1258.0439.

[0508] 1 H-NMR (400 MHz, 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).

[0510] [ Compound 25 ]

[0511] Under 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 0°C in an ice-water bath. Boron tribromide (5 eq) was slowly added dropwise to the reaction solution, and the temperature was slowly raised to room temperature and stirred for 20 minutes. The reaction solution was then raised to 150°C and stirred for 12 hours. After cooling, triethylamine (5 mL) was slowly added dropwise to terminate the reaction, and all solvent was removed under reduced pressure. The obtained solid was washed with MeOH, and then purified and separated by silica gel column chromatography using CH2Cl2 and hexane as developing solvents to obtain compound 25 (yellow solid, 2.5 g, 9%).

[0512] ESI-LCMS: [M+H] + : C 72 H 62 B2N5O. 1274.0947.

[0513] 1 H-NMR (400 MHz, 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).

[0514] Synthesis of Compound 51

[0515] Compound 51 according to one embodiment can be synthesized, for example, by the step of Reaction Scheme 3 below.

[0516] [Reaction Equation 3]

[0518]

[0520] [ Compound 51-a ]

[0521] In a 2 L flask under an argon atmosphere, 9-amino-10-phenylanthracene (50 g, 186 mmol), 5-chloro-N 1 ,N1 ,N 3 ,N 3 β-tetraphenylbenzene-1,3-diamine (83 g, 186 mmol), tri-tert-butyl-phosphine (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 oxylene, after which the reaction solution was stirred at 140°C for 6 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added for extraction to collect the organic layer, which was then dried with MgSO4 and filtered. The solvent was removed from the filtered solution under reduced pressure, and the resulting solid was purified and separated by column chromatography using silica gel with CH2Cl2 and hexane as developing solvents to obtain compound 51-a (white solid, 83 g, 66%).

[0522] ESI-LCMS: [M+H] + : C 50 H 38 N3. 680.0115.

[0523] 1 H-NMR (400 MHz, 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).

[0525] [ Compound 51-b ]

[0526] Under an argon atmosphere, compound 51-a (80 g, 118 mmol), 3-bromo-thiophenol (22 g, 118 mmol), tri-tert-butyl-phosphine (11 ml, 12 mmol), sodium tert-butoxide (34 g, 354 mmol), and Pd2dba3 (5.4 g, 5.9 mmol) were added to a 2 L flask and dissolved in 1 L of toluene. The reaction solution was then stirred at 100°C for 6 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added for extraction to collect the organic layer. The organic layer was then dried with MgSO4 and filtered. The solvent was removed from the filtered solution under reduced pressure, and the resulting solid was purified and separated by silica gel column chromatography using CH2Cl2 and hexane as developing solvents to obtain compound 51-b (white solid, 59 g, 63%).

[0527] ESI-LCMS: [M+H] + : C 56 H 42 N3S. 788.2224.

[0528] 1 H-NMR (400 MHz, 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).

[0530] [ Compound 51-c ]

[0531] In a 1 L flask under an argon atmosphere, 51-b (59 g, 75 mmol), 5-chloro-N 1 ,N 1 ,N 3 ,N 333.5 g, 75 mmol of tetraphenylbenzene-1,3-diamine, 14 g, 75 mmol of CuI, and 2-picolinic acid (9.2 g, 75 mmol) were added and dissolved in 700 mL of DMF. The reaction solution was then stirred at 180°C for 12 hours. After cooling, the solution was poured into 1 L of water, and the resulting solid was filtered. The obtained solid was dissolved again in CH2Cl2, washed several times with water, and the organic layer was collected, dried with MgSO4, and filtered. The solvent was removed from the filtered solution under reduced pressure, and the obtained solid was purified and separated by silica gel column chromatography using CH2Cl2 and hexane as developing solvents to obtain compound 51-c (white solid, 47 g, 52%).

[0532] ESI-LCMS: [M+H] + : C 86 H 64 N5S. 1198.4434.

[0533] 1 H-NMR (400 MHz, 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).

[0535] [ Compound 51 ]

[0536] Under 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 0°C in an ice-water bath. Boron tribromide (5 eq) was slowly added dropwise to the reaction solution, and the temperature was slowly raised to room temperature and stirred for 20 minutes. The reaction solution was then raised to 150°C and stirred for 12 hours. After cooling, triethylamine (10 mL) was slowly added dropwise to terminate the reaction, and all solvent was removed under reduced pressure. The obtained solid was washed with MeOH, and then purified and separated by silica gel column chromatography using CH2Cl2 and hexane as developing solvents to obtain compound 51 (yellow solid, 2.7 g, 6%).

[0537] ESI-LCMS: [M+H] + : C 86 H 57 B2N5S. 1214.4321.

[0538] 1 H-NMR (400 MHz, 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).

[0540] Synthesis of Compound 79

[0541] Compound 79 according to one embodiment can be synthesized, for example, by the step of Reaction Scheme 4 below.

[0542] [Reaction Equation 4]

[0543]

[0545] [ Compound 79-a ]

[0546] Under an argon atmosphere, 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 to a 2 L flask and dissolved in 1 L of toluene. The reaction solution was then stirred at 100°C for 6 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added for extraction to collect the organic layer. The organic layer was then dried with MgSO4 and filtered. The solvent was removed from the filtered solution under reduced pressure, and the resulting solid was purified and separated by silica gel column chromatography using CH2Cl2 and hexane as developing solvents to obtain compound 79-a (white solid, 64 g, 61%).

[0547] ESI-LCMS: [M+H] + : C 44 H 31 NBr. 652.1515.

[0548] 1 H-NMR (400 MHz, 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).

[0550] [ Compound 79-b ]

[0551] Under an argon atmosphere, Mg (2.3 g, 98 mmol) was dissolved in 500 mL of anhydrous THF in a 1 L flask, and a solution of compound 79-a (64 g, 98 mmol) dissolved in 300 mL of anhydrous THF was slowly added dropwise at room temperature. After adding iodine (50 mg, cat.) to the reaction solution, the temperature was raised to 80°C. After stirring for 30 minutes at the same temperature, when the color of the reaction solution changed from brown to gray, it was cooled to room temperature, and selenium powder (15 g, 98 mmol) was added portionwise. The reaction solution was heated again to 80°C and stirred for 2 hours; after cooling, 1 M HCl was slowly added dropwise until the pH of the reaction solution became neutral. Extraction was performed using ethyl acetate and water, and the resulting organic layer was passed through a celite filter to remove insoluble solids, after which the filtrate was concentrated. The obtained solid was purified and separated by column chromatography using silica gel with CH2Cl2 and hexane as developing solvents to obtain compound 79-b (yellow solid, 27 g, 43%).

[0552] ESI-LCMS: [M+H] + : C 44 H 31 NSe. 654.0047.

[0553] 1 H-NMR (400 MHz, 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).

[0555] [ Compound 79-c ]

[0556] Under an argon atmosphere, compound 79-b (25 g, 38 mmol), 3-bromo-aniline (6.5 g, 38 mmol), CuI (7.2 g, 38 mmol), and 2-picolinic acid (4.6 g, 38 mmol) were added to a 1 L flask and dissolved in 300 mL of DMF. The reaction solution was then stirred at 180°C for 12 hours. After cooling, the mixture was poured into 1 L of water, and the resulting solid was filtered. The obtained solid was dissolved again in CH2Cl2, washed several times with water, and the organic layer was collected, dried with MgSO4, and filtered. The solvent was removed from the filtered solution under reduced pressure, and the resulting solid was purified and separated by silica gel column chromatography using ethyl acetate and hexane as developing solvents to obtain compound 79-c (white solid, 17 g, 59%).

[0557] ESI-LCMS: [M+H] + : C 50 H 37 N2Se. 745.1117.

[0558] 1 H-NMR (400 MHz, 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).

[0560] [ Compound 79-d ]

[0561] Under an argon atmosphere, 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 to a 1 L flask and dissolved in 200 mL of toluene. The reaction solution was then stirred at 100°C for 6 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added for extraction to collect the organic layer. The organic layer was then dried with MgSO4 and filtered. The solvent was removed from the filtered solution under reduced pressure, and the resulting solid was purified and separated by silica gel column chromatography using CH2Cl2 and hexane as developing solvents to obtain compound 79-d (white solid, 15 g, 77%).

[0562] ESI-LCMS: [M+H] + : C 56 H 41 N2Se. 821.2424.

[0563] 1 H-NMR (400 MHz, 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).

[0565] [ Compound 79-e ]

[0566] In a 1 L flask under an argon atmosphere, compound 79-d (17 g, 18 mmol), 5-chloro-N 1 ,N 1 ,N 3 ,N 3β-tetraphenylbenzene-1,3-diamine (8.0 g, 18 mmol), tris-tert-butyl-phosphine (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, after which the reaction solution was stirred at 100°C for 6 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added for extraction to collect the organic layer, which was then dried with MgSO4 and filtered. The solvent was removed from the filtered solution under reduced pressure, and the obtained solid was purified and separated by column chromatography using silica gel with CH2Cl2 and hexane as developing solvents to obtain compound 79-e (white solid, 15 g, 75%).

[0567] ESI-LCMS: [M+H] + : C 80 H 58 N3Se. 1140.3741.

[0568] 1 H-NMR (400 MHz, CDCl3): 8.21 (m, 4H), 7.75 (d, 2H), 7.65 (d, 2H), 7.37 (m, 29H), 7.20 (m, 18H).

[0570] [ Compound 79 ]

[0571] Under 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 0°C in an ice-water bath. Boron tribromide (5 eq) was slowly added dropwise to the reaction solution, and after slowly raising the temperature to room temperature, the mixture was stirred for 20 minutes. The reaction solution was then raised to 150°C and stirred for 12 hours. After cooling, triethylamine (5 mL) was slowly added dropwise to terminate the reaction, and all solvent was removed under reduced pressure. The obtained solid was washed with MeOH, and then purified and separated by silica gel column chromatography using CH2Cl2 and hexane as developing solvents to obtain compound 79 (yellow solid, 1.8 g, 12%).

[0572] ESI-LCMS: [M+H] + : C 80 H 52 B2N3Se. 1156.3370.

[0573] 1 H-NMR (400 MHz, 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).

[0575] Synthesis of Compound 94

[0576] Compound 94 according to one embodiment can be synthesized, for example, by the step of Reaction Scheme 5 below.

[0577] [Reaction Equation 5]

[0578]

[0580] [ Compound 94-a ]

[0581] Under an argon atmosphere, 9-bromo-10-phenylanthracene (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 to a 2 L flask and dissolved in a mixed solution of 700 mL of toluene and 300 mL of water. The reaction solution was then stirred at 120°C for 12 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added for extraction to collect the organic layer. The organic layer was then dried with MgSO4 and filtered. The solvent was removed from the filtered solution under reduced pressure, and the resulting solid was purified and separated by silica gel column chromatography using CH2Cl2 and hexane as developing solvents to obtain compound 94-a (yellow solid, 52 g, 74%).

[0582] ESI-LCMS: [M+H] + : C 32 H 23 N. 421.1763.

[0583] 1 H-NMR (400 MHz, CDCl3): 8.21 (d, 4H), 7.65 (d, 2H), 7.55 (m, 4H), 7.37 (m, 7H), 7.02 (m, 3H).

[0585] [ Compound 94-b ]

[0586] Under an argon atmosphere, 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 to a 2 L flask and dissolved in 1 L of toluene. The reaction solution was then stirred at 100°C for 6 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added for extraction to collect the organic layer. The organic layer was then dried with MgSO4 and filtered. The solvent was removed from the filtered solution under reduced pressure, and the resulting solid was purified and separated by column chromatography using silica gel with CH2Cl2 and hexane as developing solvents to obtain compound 94-b (white solid, 48 g, 66%).

[0587] ESI-LCMS: [M+H] + : C 39 H 29 NBrO. 606.1237.

[0588] 1 H-NMR (400 MHz, 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).

[0590] [ Compound 94-c ]

[0591] Under an argon atmosphere, compound 94-b (48 g, 79 mmol), N-phenyl-[1,1'-biphenyl]-2-amine (19.4 g, 79 mmol), tris-tert-butyl-phosphine (7.2 mL, 8.0 mmol), sodium tert-butoxide (23 g, 237 mmol), and Pd2dba3 (3.6 g, 4.0 mmol) were added to a 2 L flask and dissolved in 600 mL of toluene. The reaction solution was then stirred at 100°C for 6 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added for extraction to collect the organic layer. The organic layer was then dried with MgSO4 and filtered. The filtered solution was de-pressurized to remove the solvent, and the obtained solid was purified and separated by column chromatography using silica gel with CH2Cl2 and hexane as developing solvents to obtain compound 94-c (white solid, 44 g, 73%).

[0592] ESI-LCMS: [M+H] + : C 57 H 42 N2O. 771.3321.

[0593] 1 H-NMR (400 MHz, 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).

[0595] [ Compound 94-d ]

[0596] Under an argon atmosphere, compound 94-c (44 g, 57 mmol) was dissolved in 600 mL of anhydrous CH2Cl2 in a 2 L flask, and the reaction solution was cooled to 0°C. BBr3 (1.5 eq) was slowly added dropwise to the reaction solution, then heated to room temperature and stirred for 24 hours. The solution was slowly poured into water (1 L), and ethyl acetate (300 mL) was added for extraction to collect the organic layer. The organic layer was then dried with MgSO4 and filtered. The solvent was removed from the filtered solution under reduced pressure, and the resulting solid was purified and separated by column chromatography using silica gel with CH2Cl2 and hexane as developing solvents to obtain compound 94-d (dark brown solid, 26 g, 61%).

[0597] ESI-LCMS: [M+H] + : C 56 H 41 N2O. 757.1267.

[0598] 1 H-NMR (400 MHz, 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).

[0600] [ Compound 94-e ]

[0601] In a 2 L flask under an argon atmosphere, 5-chloro-N 1 ,N 1 ,N 3 ,N 3Tetraphenylbenzene-1,3-diamine (50 g, 111 mmol), [1,1':3',1''-terphenyl]-2'-amine (27 g, 111 mmol), tris-tert-butyl-phosphine (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 140°C for 6 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added for extraction to collect the organic layer, which was then dried with MgSO4 and filtered. The filtered solution was de-pressurized to remove the solvent, and the obtained solid was purified and separated by column chromatography using silica gel with CH2Cl2 and hexane as developing solvents to obtain compound 94-e (white solid, 59 g, 82%).

[0602] ESI-LCMS: [M+H] + : C 48 H 38 N3. 656.0887.

[0603] 1 H-NMR (400 MHz, CDCl3): 8.20 (d, 2H), 7.43 (m, 7H), 7.24 (m, 8H), 7.08 (m, 16H), 6.49 (s, 3H).

[0605] [ Compound 94-f ]

[0606] Under an argon atmosphere, compound 94-e (50 g, 76 mmol), 3-iodo-bromobenzene (22 g, 76 mmol), CuI (14.4 g, 76 mmol), and K2CO3 (104 g, 760 mmol) were added to a 1 L flask and dissolved in 500 mL of o-dichlorobenzene. The reaction solution was then stirred at 180°C for 3 days. After cooling, water (1 L) and ethyl acetate (300 mL) were added for extraction to collect the organic layer. The organic layer was then dried with MgSO4 and filtered. The solvent was removed from the filtered solution under reduced pressure, and the resulting solid was purified and separated by column chromatography using silica gel with CH2Cl2 and hexane as developing solvents to obtain compound 94-f (white solid, 30 g, 49%).

[0607] ESI-LCMS: [M+H] + : C 48 H 38 N3. 810.1217.

[0608] 1 H-NMR (400 MHz, CDCl3): 8.20 (d, 2H), 7.43 (m, 7H), 7.27 (m, 10H), 7.08 (m, 18H), 6.49 (s, 3H).

[0610] [ Compound 94-g ]

[0611] Under an argon atmosphere, compound 94-f (27 g, 33 mmol), compound 94-d (25 g, 33 mmol), 3-iodo-bromobenzene (22 g, 33 mmol), CuI (6.3 g, 33 mmol), 2-picolinic acid (4.1 g, 33 mmol), and K2CO3 (14 g, 99 mmol) were added to a 1 L flask and dissolved in 500 mL of DMF. The reaction solution was then stirred at 180°C for 24 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added for extraction to collect the organic layer. The organic layer was then dried with MgSO4 and filtered. The solvent was removed from the filtered solution under reduced pressure, and the resulting solid was purified and separated by column chromatography using silica gel with CH2Cl2 and hexane as developing solvents to obtain compound 94-g (white solid, 31 g, 63%).

[0612] ESI-LCMS: [M+H] + : C 110 H 80 N5O. 1486.5119.

[0613] 1 H-NMR (400 MHz, CDCl3): 8.24 (m, 6H), 8.11 (d, 1H), 7.65 (d, 1H), 7.55 (m, 4 H), 7.43 (m, 19H), 7.27 (m, 17H), 7.08 (m, 20H), 6.87 (d, 1H), 6.72 (m, 1H).

[0615] [ Compound 94 ]

[0616] Under an argon atmosphere, 94 g (30 g, 20 mmol) of compound was dissolved in 500 mL of o-dichlorobenzene in a 1 L flask and cooled to 0°C in an ice-water bath. Boron tribromide (5 eq) was slowly added dropwise to the reaction solution, and the temperature was slowly raised to room temperature and stirred for 20 minutes. The reaction solution was then raised to 150°C and stirred for 12 hours. After cooling, triethylamine (5 mL) was slowly added dropwise to terminate the reaction, and all solvent was removed under reduced pressure. The obtained solid was washed with MeOH, and then purified and separated by column chromatography using silica gel with CH2Cl2 and hexane as developing solvents to obtain compound 94 (yellow solid, 3.3 g, 11%).

[0617] ESI-LCMS: [M+H] + : C 110 H 73 N5OB2. 1502.7812.

[0618] 1 H-NMR (400 MHz, CDCl3): 10.42 (s, 1H), 9.37 (d, 2H), 8.24 (m, 6H), 7.55 (m, 4 H), 7.43 (m, 19H), 7.27 (m, 16H), 7.08 (m, 20H), 6.87 (d, 1H), 6.72 (m, 1H).

[0621] Synthesis of Compound 101

[0622] Compound 94 according to one embodiment can be synthesized, for example, by the step of Reaction Scheme 6 below.

[0623] [Reaction Equation 6]

[0625]

[0627] [ Compound 101-a ]

[0628] Under an argon atmosphere, anthracene-9-boronic acid (50 g, 225 mmol), 3,5-dichloro-bromo-benzene (50 g, 225 mmol), K2CO3 (93 g, 675 mmol), and Pd(PPh3)4 (13 g, 11 mmol) were added to a 2 L flask and dissolved in a mixed solution of 700 mL of toluene, 200 mL of EtOH, and 300 mL of water. The reaction solution was then stirred at 120°C for 12 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added for extraction to collect the organic layer, which was then dried with MgSO4 and filtered. The filtered solution was de-pressurized to remove the solvent, and the obtained solid was purified and separated by column chromatography using silica gel with CH2Cl2 and hexane as developing solvents to obtain compound 101-a (white solid, 52 g, 74%).

[0629] ESI-LCMS: [M+H] + : C 20 H 13 Cl2. 323.0099.

[0630] 1 H-NMR (400 MHz, 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).

[0632] [ Compound 101-b ]

[0633] Under an argon atmosphere, compound 101-a (50 g, 155 mmol), diphenylamine (26 g, 155 mmol), tris-tert-butyl-phosphine (14 mL, 15 mmol), sodium tert-butoxide (45 g, 465 mmol), and Pd2dba3 (7.0 g, 7.8 mmol) were added to a 2 L flask and dissolved in 1 L of o-xylene. The reaction solution was then stirred at 140°C for 6 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added for extraction to collect the organic layer. The organic layer was then dried with MgSO4 and filtered. The solvent was removed from the filtered solution under reduced pressure, and the resulting solid was purified and separated by column chromatography using silica gel with CH2Cl2 and hexane as developing solvents to obtain compound 101-b (white solid, 40 g, 56%).

[0634] ESI-LCMS: [M+H] + : C 32 H 23 NCl. 456.1515.

[0635] 1 H-NMR (400 MHz, 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).

[0637] [ Compound 101-c ]

[0638] Under an argon atmosphere, compound 101-b (40 g, 88 mmol), aniline (10.6 g, 114 mmol), tris-tert-butyl-phosphine (8 mL, 8.8 mmol), sodium tert-butoxide (25 g, 264 mmol), and Pd2dba3 (4.0 g, 4.4 mmol) were added to a 2 L flask and dissolved in 600 mL of o-xylene. The reaction solution was then stirred at 140°C for 6 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added for extraction to collect the organic layer. The organic layer was then dried with MgSO4 and filtered. The solvent was removed from the filtered solution under reduced pressure, and the resulting solid was purified and separated by silica gel column chromatography using CH2Cl2 and hexane as developing solvents to obtain compound 101-c (white solid, 26 g, 59%).

[0639] ESI-LCMS: [M+H] + : C 38 H 28 N2. 513.2121.

[0640] 1 H-NMR (400 MHz, 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).

[0642] [ Compound 101-d ]

[0643] Under an argon atmosphere, compound 101-c (26 g, 50 mmol), 1,3-dibromobenzene (5.9 g, 25 mmol), tris-tert-butyl-phosphine (2.2 mL, 2.6 mmol), sodium tert-butoxide (7.2 g, 75 mmol), and Pd2dba3 (1.1 g, 1.3 mmol) were added to a 1 L flask and dissolved in 6 mL of o-xylene. The reaction solution was then stirred at 100°C for 12 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added for extraction to collect the organic layer. The organic layer was then dried with MgSO4 and filtered. The filtered solution was de-pressurized to remove the solvent, and the obtained solid was purified and separated by column chromatography using silica gel with CH2Cl2 and hexane as developing solvents to obtain compound 101-d (white solid, 18 g, 66%).

[0644] ESI-LCMS: [M+H] + : C 82 H 59 N4. 1099.4327.

[0645] 1 H-NMR (400 MHz, 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).

[0647] [ Compound 101 ]

[0648] Under 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 0°C in an ice-water bath. Boron tribromide (5 eq) was slowly added dropwise to the reaction solution, and the temperature was slowly raised to room temperature and stirred for 20 minutes. The reaction solution was then raised to 150°C and stirred for 12 hours. After cooling, triethylamine (5 mL) was slowly added dropwise to terminate the reaction, and all solvent was removed under reduced pressure. The obtained solid was washed with MeOH, and then purified and separated by silica gel column chromatography using CH2Cl2 and hexane as developing solvents to obtain compound 101 (yellow solid, 1.6 g, 9%).

[0649] ESI-LCMS: [M+H] + : C 82 H 53 N4B2. 1115.5623.

[0650] 1 H-NMR (400 MHz, 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).

[0652] Synthesis of Compound 110

[0653] Compound 94 according to one embodiment can be synthesized, for example, by the step of Reaction Scheme 7 below.

[0654] [Reaction Equation 7]

[0655]

[0657] [ Compound 110-a ]

[0658] Under an argon atmosphere, 9-phenyl-anthracene-10-boronic 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 to a 2 L flask and dissolved in a mixed solution of 700 mL of toluene, 200 mL of EtOH, and 300 mL of water. The reaction solution was then stirred at 120°C for 12 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added for extraction to collect the organic layer, which was then dried with MgSO4 and filtered. The filtered solution was de-pressurized to remove the solvent, and the obtained solid was purified and separated by column chromatography using silica gel with CH2Cl2 and hexane as developing solvents to obtain compound 110-a (white solid, 48 g, 72%).

[0659] ESI-LCMS: [M+H] + : C 26 H 17 Cl2. 399.0973.

[0660] 1 H-NMR (400 MHz, 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).

[0662] [ Compound 110-b ]

[0663] Under an argon atmosphere, 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 to a 2 L flask and dissolved in 1 L of o-xylene. The reaction solution was then stirred at 140°C for 6 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added for extraction to collect the organic layer. The organic layer was then dried with MgSO4 and filtered. The solvent was removed from the filtered solution under reduced pressure, and the resulting solid was purified and separated by column chromatography using silica gel with CH2Cl2 and hexane as developing solvents to obtain compound 110-b (white solid, 42 g, 67%).

[0664] ESI-LCMS: [M+H] + : C 38 H 26 Cl2N. 532.1258.

[0665] 1 H-NMR (400 MHz, 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).

[0667] [ Compound 110-c ]

[0668] Under an argon atmosphere, compound 110-b (42 g, 79 mmol), aniline (9.6 g, 102 mmol), tris-tert-butyl-phosphine (7.2 mL, 7.8 mmol), sodium tert-butoxide (23 g, 237 mmol), and Pd2dba3 (3.6 g, 3.9 mmol) were added to a 2 L flask and dissolved in 600 mL of o-xylene. The reaction solution was then stirred at 140°C for 6 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added for extraction to collect the organic layer. The organic layer was then dried with MgSO4 and filtered. The solvent was removed from the filtered solution under reduced pressure, and the resulting solid was purified and separated by column chromatography using silica gel with CH2Cl2 and hexane as developing solvents to obtain compound 110-c (white solid, 36 g, 76%).

[0669] ESI-LCMS: [M+H] + : C 44 H 33 N2. 589.2612.

[0670] 1 H-NMR (400 MHz, 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).

[0672] [ Compound 110-d ]

[0673] Under an argon atmosphere, compound 110-c (36 g, 61 mmol), 3-iodo-bromobenzene (17 g, 61 mmol), tris-tert-butyl-phosphine (5.6 mL, 6.1 mmol), sodium tert-butoxide (17.5 g, 183 mmol), and Pd2dba3 (2.8 g, 3.1 mmol) were added to a 2 L flask and dissolved in 400 mL of toluene. The reaction solution was then stirred at 100°C for 6 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added for extraction to collect the organic layer. The organic layer was then dried with MgSO4 and filtered. The filtered solution was de-pressurized to remove the solvent, and the obtained solid was purified and separated by column chromatography using silica gel with CH2Cl2 and hexane as developing solvents to obtain compound 110-d (white solid, 36 g, 76%).

[0674] ESI-LCMS: [M+H] + : C 50 H 36 N2Br. 743.2017.

[0675] 1 H-NMR (400 MHz, 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).

[0677] [ Compound 110-e ]

[0678] Under an argon atmosphere, compound 110-d (36 g, 49 mmol), aniline (6.1 g, 65 mmol), tris-tert-butyl-phosphine (4.4 mL, 5.0 mmol), sodium tert-butoxide (14 g, 147 mmol), and Pd2dba3 (2.2 g, 2.5 mmol) were added to a 2 L flask and dissolved in 400 mL of toluene. The reaction solution was then stirred at 100°C for 6 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added for extraction to collect the organic layer. The organic layer was then dried with MgSO4 and filtered. The solvent was removed from the filtered solution under reduced pressure, and the resulting solid was purified and separated by silica gel column chromatography using CH2Cl2 and hexane as developing solvents to obtain compound 110-e (white solid, 28 g, 78%).

[0679] ESI-LCMS: [M+H] + : C 56 H 42 N3. 756.3030.

[0680] 1 H-NMR (400 MHz, 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).

[0682] [ Compound 110-f ]

[0683] In a 2 L flask under an argon atmosphere, compound 110-e (36 g, 37 mmol), 5-chloro-N 1 ,N 1 ,N 3 ,N 3β-tetraphenylbenzene-1,3-diamine (17 g, 37 mmol), tris-tert-butyl-phosphine (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 0-xylene, after which the reaction solution was stirred at 140°C for 6 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added for extraction to collect the organic layer, which was then dried with MgSO4 and filtered. The solvent was removed from the filtered solution under reduced pressure, and the obtained solid was purified and separated by column chromatography using silica gel with CH2Cl2 and hexane as developing solvents to obtain compound 110-f (white solid, 23 g, 54%).

[0684] ESI-LCMS: [M+H] + : C 86 H 63 N5. 1166.5017.

[0685] 1 H-NMR (400 MHz, 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).

[0687] [ Compound 110 ]

[0688] Under 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 0°C in an ice-water bath. Boron tribromide (5 eq) was slowly added dropwise to the reaction solution, and the temperature was slowly raised to room temperature and stirred for 20 minutes. The reaction solution was then raised to 150°C and stirred for 12 hours. After cooling, triethylamine (5 mL) was slowly added dropwise to terminate the reaction, and all solvent was removed under reduced pressure. The obtained solid was washed with MeOH, and then purified and separated by silica gel column chromatography using CH2Cl2 and hexane as developing solvents to obtain compound 110 (yellow solid, 1.8 g, 8%).

[0689] ESI-LCMS: [M+H] + : C 86 H 57 N5B2. 1182.4327.

[0690] 1 H-NMR (400 MHz, 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).

[0691] Synthesis of Compound 122

[0692] Compound 122 according to one embodiment can be synthesized, for example, by the step of Reaction Scheme 8 below.

[0693] [Reaction Equation 8]

[0694]

[0696] [ Compound 122-a ]

[0697] Under an argon atmosphere, compound 101-a (50 g, 155 mmol), thiophenol (17 g, 155 mmol), and Cs2CO3 (150 g, 465 mmol) were placed in a 2 L flask and dissolved in 1 L of NMP. The reaction solution was then stirred at 180°C for 24 hours. After cooling, the mixture was slowly poured into 1 L of water, and the resulting solid was filtered. The solid was dissolved again in ethyl acetate (300 mL), washed several times with water, extracted to collect the organic layer, dried with MgSO4, and filtered. The solvent was removed from the filtered solution under reduced pressure, and the obtained solid was purified and separated by silica gel column chromatography using CH2Cl2 and hexane as developing solvents to obtain compound 122-a (white solid, 35 g, 58%).

[0698] ESI-LCMS: [M+H] + : C 26 H 18 ClS. 397.0712.

[0699] 1 H-NMR (400 MHz, CDCl3): 8.39 (s, 1H), 8.19 (d, 2H), 8.03 (m, 2H), 7.71 (m, 2H), 7.43 (m, 10H).

[0701] [ Compound 122-b ]

[0702] Under an argon atmosphere, compound 122-a (35 g, 88 mmol), aniline (10.7 g, 114 mmol), tris-tert-butyl-phosphine (8.0 mL, 8.8 mmol), sodium tert-butoxide (25.3 g, 264 mmol), and Pd2dba3 (4.0 g, 4.4 mmol) were added to a 2 L flask and dissolved in 600 mL of o-xylene. The reaction solution was then stirred at 140°C for 6 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added for extraction to collect the organic layer. The organic layer was then dried with MgSO4 and filtered. The filtered solution was de-pressurized to remove the solvent, and the obtained solid was purified and separated by column chromatography using silica gel with CH2Cl2 and hexane as developing solvents to obtain compound 122-b (white solid, 24 g, 61%).

[0703] ESI-LCMS: [M+H] + : C 32 H 24 SN. 454.1612.

[0704] 1 H-NMR (400 MHz, 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).

[0706] [ Compound 122-c ]

[0707] Under an argon atmosphere, compound 122-b (24 g, 53 mmol), 1,3-dibromobenzene (6.3 g, 26 mmol), tris-tert-butyl-phosphine (4.8 mL, 5.4 mmol), sodium tert-butoxide (15 g, 159 mmol), and Pd2dba3 (2.4 g, 2.7 mmol) were added to a 2 L flask and dissolved in 400 mL of toluene. The reaction solution was then stirred at 100°C for 12 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added for extraction to collect the organic layer. The organic layer was then dried with MgSO4 and filtered. The filtered solution was de-pressurized to remove the solvent, and the obtained solid was purified and separated by column chromatography using silica gel with CH2Cl2 and hexane as developing solvents to obtain compound 122-c (white solid, 43 g, 63%).

[0708] ESI-LCMS: [M+H] + : C 70 H 49 S2N2. 981.3227.

[0709] 1 H-NMR (400 MHz, 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).

[0711] [ Compound 122 ]

[0712] Under 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 0°C in an ice-water bath. Boron tribromide (5 eq) was slowly added dropwise to the reaction solution, and after slowly raising the temperature to room temperature, the mixture was stirred for 20 minutes. The reaction solution was then raised to 150°C and stirred for 12 hours. After cooling, triethylamine (5 mL) was slowly added dropwise to terminate the reaction, and all solvent was removed under reduced pressure. The obtained solid was washed with MeOH, and then purified and separated by silica gel column chromatography using CH2Cl2 and hexane as developing solvents to obtain compound 122 (yellow solid, 2.0 g, 5%).

[0713] ESI-LCMS: [M+H] + : C 70 H 43 N5B2S2. 997.9090.

[0714] 1 H-NMR (400 MHz, 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).

[0716] 2. Fabrication and Evaluation of Light Emitting Devices

[0717] (Fabrication of light-emitting devices)

[0718] After patterning ITO with a thickness of 300 Å on a glass substrate, NPD was vacuum-deposited on top of the ITO to form a hole injection layer with a thickness of 300 Å. HT6 was vacuum-deposited on top of the hole injection layer to form a hole transport layer with a thickness of 200 Å. A hole-transporting compound CzSi was vacuum-deposited on top of the hole transport layer to form a light-emitting auxiliary layer with a thickness of 100 Å. After forming the light-emitting auxiliary layer, mCP and the compound of the example or the compound of the comparative example were simultaneously deposited in a weight ratio of 99:1 to form a light-emitting layer with a thickness of 200 Å. TSPO1 was deposited on top of the light-emitting layer to form an electron transport layer with a thickness of 200 Å, and then TPBi was deposited on top of the electron transport layer to form a buffer layer with a thickness of 300 Å. LiF was deposited on top of the electron transport layer to form an electron injection layer with a thickness of 10 Å, and Al was vacuum-deposited to form a LiF / Al electrode with a thickness of 3000 Å. A light-emitting device was fabricated by forming a capping layer by vacuum depositing HT28 to a thickness of 700 Å on top of the electrode. In the example, the hole injection layer, hole transport layer, light-emitting auxiliary layer, electron transport layer, buffer layer, electron injection layer, and electrode were formed using a vacuum deposition apparatus.

[0719] The compounds used in the fabrication of the light-emitting device are shown below.

[0720]

[0721] (Evaluation of light-emitting device characteristics)

[0722] The characteristics were evaluated by including Examples 1 to 8 and Comparative Examples 1 and 2 as host materials in each light-emitting layer. To evaluate the characteristics of light-emitting devices fabricated using Examples 1 to 8 or Comparative Examples 1 and 2 as host materials, a current density of 10 mA / cm² was used. 2 The driving voltage and efficiency (cd / A) were measured at a current density of 10 mA / cm². 2The luminous efficiency was evaluated based on the time from the initial value to 50% luminance degradation during continuous operation compared with Comparative Example 1. Compound C1, which is Comparative Example 1, and Compound C2, which is Comparative Example 2, are shown below.

[0723] To evaluate the luminous efficiency of the light-emitting devices including Examples 1 to 8 and Comparative Examples 1 to 2, measurements were taken using the external quantum efficiency measuring device C9920-12 of Hamamatsu Photonics. Device lifetime LT50 represents the time required for the initial brightness to decrease by 50%.

[0724] [Compound X-1]

[0725]

[0726] [Compound X-2]

[0727]

[0728] Example of device creation light-emitting layer material Driving voltage (V) Luminous efficiency (cd / A) Relative component lifetime (T 95 ) Example 1 Example Compound 20 4.2 20.7 5.26 Example 2 Example Compound 25 4.3 18.4 4.78 Example 3 Example Compound 51 4.6 22.6 4.13 Example 4 Example Compound 79 4.5 24.1 3.4 Example 5 Example Compound 94 4.7 21.5 3.9 Example 6 Example Compound 101 4.3 17.8 4.8 Example 7 Example Compound 110 4.5 19.8 4.34 Example 8 Example Compound 122 4.5 22.8 4.3 Comparative Example 1 Comparative Example Compound X-11 5.2 15.7 1.00 Comparative Example 2 Comparative Example Compound X-2 4.8 20.8 2.61

[0729] When comparing Examples 1 to 8 with Comparative Examples 1 and 2, the cases of Examples 1 to 8 exhibited high efficiency characteristics. This is attributed to the fact that the compounds of Examples 1 to 8 have a minimum triplet excitation energy (T1) of less than 1.8 eV. When anthracene is included as a substituent, as in Examples 1 to 8, a minimum triplet excitation energy of 1.8 eV or less can be obtained. Anthracene has a long conjugation structure and has a minimum triplet excitation energy of approximately 1.7 eV, and compounds containing anthracene as a substituent have a low minimum triplet excitation energy derived from anthracene.

[0730] As the lift time of excitons at high energy levels (triplet energy) increases, they break weak bonds within the molecule or degrade and decompose organic materials within the emissive layer through mechanisms such as triplet-triplet annihilation (TTA) and triplet-polaron quenching (TPQ), thereby reducing the lifespan of the light-emitting device. Examples 1 to 8 have a low triplet excitation energy of 1.8 eV, so excitons at high triplet energies rapidly undergo internal conversion to the low triplet excitation energy and become stabilized. Therefore, it is determined that Examples 1 to 8 reduce the degradation and decomposition of organic materials within the emissive layer caused by high-energy excitons, thereby increasing the lifespan of the light-emitting device.

[0731] As such, Examples 1 to 8 show results in improved lifespan of the light-emitting element compared to Comparative Examples 1 and 2. That is, the lifespan of the light-emitting element of one example can be improved by using a polycyclic compound substituted with at least one anthracenyl group.

[0732] A light-emitting device of one embodiment can improve its lifetime by including a polycyclic compound having a low lowest triplet excitation energy that includes at least one anthracenyl group.

[0733] Although the present invention has been described above with reference to preferred embodiments, those skilled in the art or those with ordinary knowledge in the art will understand that various modifications and changes can be made to the invention without departing from the spirit and technical scope of the invention as described in the claims set forth below.

[0734] Therefore, the technical scope of the present invention should not be limited to the contents described in the detailed description of the specification, but should be determined by the claims. Explanation of the symbols

[0735] DD, DD-TD: Display device ED: Light-emitting element EL1: First electrode EL2: Second electrode HTR: Hole transport region EML: Emissive layer ETR: Electron transport region

Claims

Claim 1 A light-emitting device comprising: a first electrode; a second electrode disposed on the first electrode; and a light-emitting layer disposed between the first electrode and the second electrode and comprising a polycyclic compound represented by the following chemical formula 1, wherein the first electrode and the second electrode each independently comprise at least one selected from Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF / Ca, LiF / Al, Mo, Ti, W, In, Sn, and Zn, at least two compounds selected from these, at least two mixtures selected from these, or oxides thereof: [Chemical Formula 1] In the above chemical formula 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 , R y2 Each is independently a hydrogen atom or a deuterium atom, R1 is a substituted or unsubstituted cyclic aryl group having 6 to 30 carbon atoms, or a compound represented by Formula A, R2 is a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cyclic aryl group having 6 to 30 carbon atoms, or a compound represented by the following Formula A, and X1 to X 4, At least one of Z1 and Z2 comprises a compound represented by the following chemical formula A, [Chemical Formula A] In the above chemical formula A, Ra is a hydrogen atom, a deuterium atom, or a substituted or unsubstituted cyclic aryl group having 6 to 30 carbon atoms, L1 is a substituted or unsubstituted cyclic arylene group having 6 to 30 carbon atoms, and p is 0 or 1. Claim 2 In claim 1, the light-emitting element represented by the above chemical formula A is any one of the following chemical formulas A-1, A-2, and A-4: [Chemical Formula A-1] [Chemical Formula A-2] [Chemical Formula A-4] In the above chemical formulas A-1, A-2, and A-4, Ra is the same as defined in the above chemical formula A. Claim 3 In paragraph 2, the above chemical formula A-1 is a light-emitting element represented by either the following chemical formula AA-1 and chemical formula AA-2: [Chemical formula AA-1] [Chemical Formula AA-2] In the above chemical formulas AA-1 and AA-2, Ra is as defined in the above chemical formula A. Claim 4 In paragraph 2, the above chemical formula A-2 is a light-emitting element represented by any one of the following chemical formulas B-1 to B-3: [Chemical Formula B-1] [Chemical Formula B-2] [Chemical Formula B-3] In chemical formulas B-1 to B-3, Ra is the same as defined in chemical formula A above. Claim 5 delete Claim 6 A light-emitting element according to claim 1, wherein Ra is an unsubstituted phenyl group or an unsubstituted naphthyl group. Claim 7 A light-emitting device according to claim 1, wherein the lowest triplet excitation energy of the polycyclic compound is 1.8 eV or less. Claim 8 In claim 1, the light-emitting layer comprises a dopant and a host, and the dopant comprises the polycyclic compound, forming a light-emitting element. Claim 9 A light-emitting element according to claim 1, further comprising a capping layer disposed on the second electrode, wherein the refractive index of the capping layer is 1.6 or higher. Claim 10 In claim 1, the polycyclic compound is a light-emitting device that emits thermally active delayed fluorescence. Claim 11 In claim 1, the light-emitting layer is a light-emitting element that emits blue light. Claim 12 In claim 1, the light-emitting layer comprises at least one of the compounds listed in the following compound group 1, a light-emitting element: [Compound group 1] . Claim 13 A light-emitting device comprising: a first electrode; a second electrode disposed on the first electrode; and a light-emitting layer disposed between the first electrode and the second electrode and comprising a polycyclic compound represented by the following chemical formula 2, wherein the first electrode and the second electrode each independently comprise at least one selected from Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF / Ca, LiF / Al, Mo, Ti, W, In, Sn, and Zn, at least two compounds selected from these, at least two mixtures selected from these, or oxides thereof: [Chemical Formula 2] In the above chemical formula 2, X1 to X4 are each independently O, S, Se, or NR1, and R1 is , or a substituted or unsubstituted cyclic aryl group having 6 to 30 carbon atoms, where n is an integer from 0 to 8, and when n is 0, at least one of X1 to X4 is R1 NR1 and R1 is In the case of NR1 other than, n is an integer between 1 and 8 inclusive, a is an integer between 0 and 8-n inclusive, p is 0 or 1, L1 is a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, and R y is a hydrogen atom, a deuterium atom, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted cyclic aryl group having 6 to 30 carbon atoms, and R a Is It is a hydrogen atom, a deuterium atom, or a substituted or unsubstituted cyclic aryl group having 6 to 30 carbon atoms. Claim 14 In claim 13, the above chemical formula 2 is a light-emitting element represented by any one of the following chemical formulas 3 to 5: [Chemical Formula 3] [Chemical Formula 4] [Chemical Formula 5] In the above Chemical Formulas 4 and 5, L2 and L3 are each independently substituted or unsubstituted arylene groups having 6 to 30 carbon atoms, and in Chemical Formulas 3 to 5, a, R y, X1 to X4 are the same as defined in Chemical Formula 2 above, and Ra in Chemical Formulas 4 and 5 is the same as defined in Chemical Formula 2 above. Claim 15 In claim 14, in the above chemical formula 2, the above A light-emitting element represented by any one of the following chemical formulas 6, 7, and 9: [Chemical Formula 6] [Chemical Formula 7] [Chemical Formula 9] In the above chemical formulas 6, 7, and 9, R a It is the same as defined in Chemical Formula 2 above. Claim 16 In claim 15, the above chemical formula 6 is a light-emitting element represented by either the following chemical formula 6-1 and chemical formula 6-2: [Chemical formula 6-1] [Chemical Formula 6-2] In the above chemical formulas 6-1 and 6-2, Ra is as defined in the above chemical formula 2. Claim 17 In claim 15, the above chemical formula 7 is a light-emitting element represented by any one of the following chemical formulas 7-1 to 7-3: [Chemical Formula 7-1] [Chemical Formula 7-2] [Chemical Formula 7-3] R in the above chemical formulas 7-1 to 7-3 a It is the same as defined in Chemical Formula 2 above. Claim 18 delete Claim 19 A light-emitting element according to claim 13, wherein Ra in the above chemical formula 2 is an unsubstituted phenyl group or an unsubstituted naphthyl group. Claim 20 A light-emitting device according to claim 13, wherein the lowest triplet excitation energy of the polycyclic compound is 1.8 eV or less. Claim 21 In claim 13, the light-emitting layer is a light-emitting element comprising at least one of the compounds listed in the following compound group 1: [Compound group 1] .

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