Light-emitting element

Abstract

To provide a light-emitting element with excellent luminous efficiency and long life characteristic.SOLUTION: A light-emitting element includes a first electrode, a second electrode, and a light-emitting layer disposed between the first electrode and the second electrode and containing a polycyclic compound represented by the following chemical formula. The first electrode and the second electrode independently contain at least one selected from Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF, Mo, Ti, W, In, Sn, and Zn, a compound of two or more kinds selected from these, a mixture of two or more kinds selected from these, or an oxide of any of these.SELECTED DRAWING: Figure 3

Description

[Technical field]

[0001] The present invention relates to a light-emitting device, and more particularly to a light-emitting device containing a novel polycyclic compound in a light-emitting layer. [Background technology]

[0002] Recently, organic electroluminescence display devices and the like have been actively developed as image display devices. Organic electroluminescence display devices and the like are display devices including so-called self-emitting light-emitting elements that realize display by recombining holes and electrons injected from a first electrode and a second electrode in a light-emitting layer to cause a light-emitting material in the light-emitting layer to emit light.

[0003] In order to apply light-emitting devices to display devices, low driving voltages, high luminous efficiency, and long life are required, and there is a constant demand for development of light-emitting device materials that can stably achieve these requirements.

[0004] In particular, in recent years, technologies related to phosphorescence that utilizes the energy of triplet states and delayed fluorescence that utilizes the phenomenon in which singlet excitons are generated by the collision of triplet excitons (TTA) have been developed to realize highly efficient light-emitting devices, and thermally activated delayed fluorescence (TADF) materials that utilize the delayed fluorescence phenomenon are being developed. [Prior art documents] [Patent documents]

[0005] [Patent Document 1] Korean Patent Application Publication No. 10-2020-0062329A [Patent Document 2] Korean Patent No. 10-1707799B1 [Patent Document 3] Korean Patent No. 10-1482559B1 Summary of the Invention [Problem to be solved by the invention]

[0006] An object of the present invention is to provide a light emitting device that exhibits excellent luminous efficiency and long life characteristics. [Means for solving the problem]

[0007] One embodiment provides a light-emitting device including 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 including a polycyclic compound represented by the following chemical formula 1, wherein the first electrode and the second electrode each independently include at least one selected from Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF, Mo, Ti, W, In, Sn, and Zn, a compound of two or more selected from these, a mixture of two or more selected from these, or an oxide thereof.

[0008] [ka] (chemical formula 1)

[0009] In Chemical Formula 1, X 1 ~X 4 are each independently BR a , N.R. b , C.R. c R d , O, S, or Se, and a to d are each independently an integer of 0 to 4. a ~R d , and R 1 ~R 4 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having from 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having from 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having from 2 to 30 ring carbon atoms, and L is a substituted or unsubstituted divalent triptysenylene group, or a substituted or unsubstituted divalent carboranylene group.

[0010] Chemical formula 1 is represented by the following chemical formula 1-1.

[0011] [ka] (Chemical formula 1-1)

[0012] In Chemical Formula 1-1, X 1 ~X 4 , a-d, R 1 ~R 4 and L are as defined in Formula 1.

[0013] L is represented by any one of the following L-1 to L-4.

[0014] [ka]

[0015] JPEG2022160374000005.jpg4108

[0016] R 1 and R 4 are each independently a t-butyl group, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted biphenylyl group.

[0017] X 1 ~X 4 is the same.

[0018] The light-emitting layer is a delayed fluorescent light-emitting layer containing a host and a dopant, and the dopant contains a polycyclic compound.

[0019] Chemical formula 1 is represented by any one of the polycyclic compounds in the first compound group below.

[0020] [First compound group] [ka] [ka]

[0021] In Compounds 4 to 6, "CB" is a divalent carboranylene group.

[0022] The light-emitting layer includes a first host, a second host different from the first host, a supporting dopant including an organometallic complex, and a light-emitting dopant, where the light-emitting dopant includes a polycyclic compound.

[0023] The first host includes at least one of the following compounds HT-01 to HT-09.

[0024] [ka] [ka] [ka]

[0025] The second host contains at least one of the following compounds ET-01 to ET-06.

[0026] [ka]

[0027] The auxiliary dopant includes at least one of the compounds in the following compound group P.

[0028] [Compound group P] [ka] [ka] [ka] [ka] .

[0029] The light emitting layer emits blue light having a central wavelength of 450 nm or more and 470 nm or less.

[0030] The optical element further includes a capping layer disposed over the second electrode, the capping layer having a refractive index of 1.6 or greater.

[0031] One embodiment includes a first electrode, a second electrode disposed on the first electrode, and an emitting layer disposed between the first electrode and the second electrode, the emitting layer including a hole-transporting first host, an electron-transporting second host different from the first host, an auxiliary dopant, and an emitting dopant different from the auxiliary dopant, the emitting dopant being represented by Chemical Formula 1 below.

[0032] [ka] (chemical formula 1)

[0033] In chemical formula 1, X 1 ~X 4 are each independently BR a , N.R. b , C.R. c R d , O, S, or Se, and a to d are each independently an integer of 0 to 4. a ~R d , and R 1 ~R 4 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having from 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having from 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having from 2 to 30 ring carbon atoms, and L is a substituted or unsubstituted divalent triptysenylene group, or a substituted or unsubstituted divalent carboranylene group. Effect of the Invention

[0034] The light-emitting device of the embodiment exhibits high efficiency and long life characteristics by including the polycyclic compound of the embodiment. [Brief description of the drawings]

[0035] [Figure 1] 1 is a plan view showing a display device according to an embodiment. [Diagram 2] 1 is a cross-sectional view of a display device according to an embodiment. [Diagram 3] 1 is a cross-sectional view illustrating a light emitting device according to an embodiment. [Figure 4] 1 is a cross-sectional view illustrating a light emitting device according to an embodiment. [Diagram 5] 1 is a cross-sectional view illustrating a light emitting device according to an embodiment. [Figure 6] 1 is a cross-sectional view illustrating a light emitting device according to an embodiment. [Figure 7] 1 is a cross-sectional view of a display device according to an embodiment. [Figure 8] 1 is a cross-sectional view of a display device according to an embodiment. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0036] Since the present invention can be modified in various ways and can have various forms, specific embodiments are shown in the drawings and described in detail in the text, but it is not intended to limit the present invention to the specific disclosed forms, but it should be understood that the present invention includes all modifications, equivalents, and alternatives falling within the spirit and technical scope of the present invention.

[0037] In the drawings, like reference numerals are used for like elements. In the accompanying drawings, the dimensions of the structures are exaggerated for clarity of the present invention. Terms such as first and second are used to describe various elements, but elements are not limited to the terms. Terms are used only for the purpose of distinguishing one element from another element. For example, the first element may be named the second element, and similarly the second element may be named the first element, without departing from the scope of the present invention. A singular expression includes a plural expression unless the context clearly indicates otherwise.

[0038] In this application, the terms "comprise" or "have" and the like are intended to specify the presence of any feature, numeral, step, operation, component, part, or combination thereof described hereinabove in the specification, but are to be understood as not precluding the presence or additional possibility of one or more other features, numerals, steps, operations, components, parts, or combinations thereof.

[0039] In this application, when a layer, film, region, plate, or other part is described as being "on" or "above" another part, this includes not only when it is "directly above" the other part, but also when there is another part in between. Conversely, when a layer, film, region, plate, or other part is described as being "below" or "below" another part, this includes not only when it is "directly below" the other part, but also when there is another part in between. Also, in this application, being "located on" includes not only when it is located at the top, but also when it is located at the bottom.

[0040] In this specification, "substituted or unsubstituted" means that it is substituted with one or more substituents selected from the group consisting of a deuterium atom, a halogen atom, a cyano group, a nitro group, an amino group, a silyl group, an oxy group, a thio group, a sulfinyl group, a sulfonyl group, a carbonyl group, a boron group, a phosphine oxide group, a phosphine sulfide group, an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, a hydrocarbon ring group, an aryl group, and a heterocyclic group, or is not substituted. In addition, each of the substituents exemplified above may be substituted or unsubstituted. For example, a biphenylyl group may be interpreted as an aryl group, or as a phenyl group substituted with a phenyl group.

[0041] In this specification, "adjacent groups bond together to form a ring" means adjacent groups bond together to form a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted hetero ring. 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 are monocyclic or polycyclic. In addition, the ring formed by bonding together may be bonded to another ring to form a spiro structure.

[0042] In this specification, the term "adjacent group" refers to a substituent substituted on an atom directly bonded to the atom on which the corresponding substituent is substituted, another substituent substituted on an atom on which the corresponding substituent is substituted, or a substituent that is structurally most adjacent to the corresponding substituent. For example, two methyl groups in 1,2-dimethylbenzene are interpreted as "adjacent groups" to each other, and two ethyl groups in 1,1-diethylcyclopentane are interpreted as "adjacent groups" to each other. Also, two methyl groups in 4,5-dimethylphenanthrene are interpreted as "adjacent groups" to each other.

[0043] In this specification, examples of halogen atoms include a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom.

[0044] In this specification, an alkyl group is linear, branched, or cyclic. The number of carbon atoms in an alkyl group is 1 to 50, 1 to 30, 1 to 20, 1 to 10, or 1 to 6. Examples of alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, s-butyl, t-butyl, i-butyl, 2-ethylbutyl, 3,3-dimethylbutyl, n-pentyl, i-pentyl, neopentyl, t-pentyl, cyclopentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl, n-hexyl, 1-methylhexyl, 2-ethylbutyl ... n-Heptyl, 2-butylhexyl, cyclohexyl, 4-methylcyclohexyl, 4-t-butylcyclohexyl, n-heptyl, 1-methylheptyl, 2,2-dimethylheptyl, 2-ethylheptyl, 2-butylheptyl, n-octyl, t-octyl, 2-ethyloctyl, 2-butyloctyl, 2-hexyloctyl, 3,7-dimethyloctyl, cyclooctyl, n-nonyl, n-decyl, ada Mantyl, 2-ethyldecyl, 2-butyldecyl, 2-hexyldecyl, 2-octyldecyl, n-undecyl, n-dodecyl, 2-ethyldodecyl, 2-butyldodecyl, 2-hexyldodecyl, 2-octyldecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, 2-ethylhexadecyl, 2-butylhexadecyl, 2-hexylhexadecyl, 2-octylhexadecyl Examples of such alkyl groups include, but are not limited to, n-heptadecyl, n-octadecyl, n-nonadecyl, n-icosyl, 2-ethylicosyl, 2-butylicosyl, 2-hexylicosyl, 2-octylicosyl, n-henicosyl, n-docosyl, n-tricosyl, n-tetracosyl, n-pentacosyl, n-hexacosyl, n-heptacosyl, n-octacosyl, n-nonacosyl, and n-triacontyl groups.

[0045] In the present specification, the term "hydrocarbon ring group" refers to any functional group or substituent derived from an aliphatic hydrocarbon ring. The hydrocarbon ring group is a saturated hydrocarbon ring group having 5 to 20 ring carbon atoms.

[0046] In this specification, the aryl group means any functional group or substituent derived from an aromatic hydrocarbon ring. The aryl group is a monocyclic aryl group or a polycyclic aryl group. The number of ring carbon atoms of the aryl group is 6 to 30, 6 to 20, or 6 to 15. Examples of the aryl group include, but are not limited to, a phenyl group, a naphthyl group, a fluorenyl group, an anthracenyl group, a phenanthryl group, a biphenylyl group, a terphenylyl group, a quaterphenylyl group, a quinquephenylyl group, a sexiphenylyl group, a triphenylenyl group, a pyrenyl group, a benzofluoranthenyl group, and a chrysenyl group.

[0047] In this specification, the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure. Examples of the fluorenyl group that is substituted are as follows. However, the examples are not limited thereto.

[0048] [ka] [ka] [ka] [ka]

[0049] In this specification, a heterocyclic group means any functional group or substituent derived from a ring containing one or more of B, O, N, P, Si, and S as heteroatoms. The heterocyclic group includes an aliphatic heterocyclic group and an aromatic heterocyclic group. The aromatic heterocyclic group may be a heteroaryl group. The aliphatic heterocyclic ring and the aromatic heterocyclic ring may be monocyclic or polycyclic.

[0050] In this specification, the heterocyclic group includes one or more of B, O, N, P, Si, and S as a heteroatom. When the heterocyclic group includes two or more heteroatoms, the two or more heteroatoms may be the same or different. The heterocyclic group may be a monocyclic heterocyclic group or a polycyclic heterocyclic group, and includes a heteroaryl group. The number of ring carbon atoms of the heterocyclic group is 2 to 30, 2 to 20, or 2 to 10.

[0051] In this specification, an aliphatic heterocyclic group contains one or more heteroatoms selected from B, O, N, P, Si, and S. The number of ring carbon atoms in the aliphatic heterocyclic group is 2 to 30, 2 to 20, or 2 to 10. Examples of the aliphatic heterocyclic group include, but are not limited to, an oxiranyl group, a thiiranyl group, a pyrrolidinyl group, a piperidinyl group, a tetrahydrofuranyl group, a tetrahydrothiophenyl group, a thianyl group, a tetrahydropyranyl group, and a 1,4-dioxanyl group.

[0052] In this specification, the heteroaryl group includes one or more of B, O, N, P, Si, and S as a heteroatom. When the heteroaryl group includes two or more heteroatoms, the two or more heteroatoms may be the same or different from each other. The heteroaryl group is a monocyclic heterocyclic group or a polycyclic heterocyclic group. The number of ring carbon atoms of the heteroaryl group is 2 to 30, 2 to 20, or 2 to 10. Examples of the heteroaryl group include a thiophenyl group, a furanyl group, a pyrrolyl group, an imidazolyl group, a triazolyl group, a pyridinyl group, a bipyridinyl group, a pyrimidinyl group, a triazinyl group, a triazolyl group, an acridinyl group, a pyridazinyl group, a quinolinyl group, a quinazolinyl group, a quinoxalinyl group, a phenoxazinyl group, a phthalazinyl group, a pyridopyrimidinyl group, a pyridopyrazinyl group, a pyrazinopyrazinyl group, an isoquinolinyl group, an indolyl group, a carbazolyl group, an N-arylcarbazolyl group, an N Examples of such alkyl groups include, but are not limited to, -heteroarylcarbazolyl groups, N-alkylcarbazolyl groups, benzoxazolyl groups, benzimidazolyl groups, benzothiazolyl groups, benzocarbazolyl groups, benzothiophenyl groups, dibenzothiophenyl groups, thienothiophenyl groups, benzofuranyl groups, phenanthrolinyl groups, thiazolyl groups, isoxazolyl groups, oxazolyl groups, oxadiazolyl groups, thiadiazolyl groups, phenothiazinyl groups, dibenzosilolyl groups, and dibenzofuranyl groups.

[0053] In this specification, the above explanation of the aryl group applies to the arylene group, except that the arylene group is a divalent group. The above explanation of the heteroaryl group applies to the heteroarylene group, except that the heteroarylene group is a divalent group.

[0054] In this specification, the silyl group includes an alkylsilyl group and an arylsilyl group. Examples of the silyl group include, but are not limited to, a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, a phenylsilyl group, and the like.

[0055] In this specification, the number of carbon atoms of the amino group is not particularly limited, but may be 1 or more and 30 or less. The amino group includes an alkylamino group, an arylamino group, or a heteroarylamino group. Examples of the amino group include, but are not limited to, a methylamino group, a dimethylamino group, a phenylamino group, a diphenylamino group, a naphthylamino group, and a 9-methyl-anthracenylamino group.

[0056] In this specification, the carbonyl group is not particularly limited to the number of carbon atoms, but may be 1 to 40, 1 to 30, or 1 to 20. For example, it may have the following structure, but is not limited thereto.

[0057] [ka]

[0058] In this specification, the number of carbon atoms of the sulfinyl group and the sulfonyl group is not particularly limited, but may be 1 or more and 30 or less. The sulfinyl group includes an alkylsulfinyl group and an arylsulfinyl group. The sulfonyl group includes an alkylsulfonyl group and an arylsulfonyl group.

[0059] In this specification, the thio group includes an alkylthio group and an arylthio group. The thio group means an alkyl group or an aryl group defined above to which a sulfur atom is bonded. Examples of the thio group include, but are not limited to, a methylthio group, an ethylthio group, a propylthio group, a pentylthio group, a hexylthio group, an octylthio group, a dodecylthio group, a cyclopentylthio group, a cyclohexylthio group, a phenylthio group, and a naphthylthio group.

[0060] In this specification, the oxy group means an alkyl group or an aryl group defined above to which an oxygen atom is bonded. The oxy group includes an alkoxyoxy group and an aryloxy group. The alkoxy group is linear, branched, or cyclic. The number of carbon atoms in the alkoxy group is not particularly limited, and may be, for example, 1 to 20 or 1 to 10. Examples of the oxy group include, but are not limited to, a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, a butoxy group, a pentyloxy group, a hexyloxy group, an octyloxy group, a nonyloxy group, a decyloxy group, and a benzyloxy group.

[0061] In this specification, the boron group means a boron atom bonded to the alkyl group or aryl group defined above. The boron group includes an alkyl boron group and an aryl boron group. Examples of the boron group include, but are not limited to, a trimethyl boron group, a triethyl boron group, a t-butyl dimethyl boron group, a triphenyl boron group, a diphenyl boron group, and a phenyl boron group.

[0062] In this specification, the alkenyl group may be linear or branched. The number of carbon atoms is not particularly limited, but may be 2 to 30, 2 to 20, or 2 to 10. Examples of the alkenyl group include, but are not limited to, vinyl, 1-butenyl, 1-pentenyl, 1,3-butadienylaryl, styrenyl, and styrylvinyl groups.

[0063] In this specification, the number of carbon atoms of the amino group is not particularly limited, but may be 1 or more and 30 or less. The amino group includes an alkylamino group and an arylamino group. Examples of the amino group include, but are not limited to, a methylamino group, a dimethylamino group, a phenylamino group, a diphenylamino group, a naphthylamino group, and a 9-methyl-anthracenylamino group.

[0064] In this specification, among the alkylthio group, alkylsulfoxy group, alkylaryl group, alkylamino group, alkylboron group, alkylsilyl group and alkylamino group, the alkyl group is the same as the above-mentioned examples of the alkyl group.

[0065] In the present specification, the aryl group among the aryloxy group, arylthio group, arylsulfoxy group, arylamino group, arylboron group, arylsilyl group, and arylamino group is the same as the aryl group described above.

[0066] In this specification, a direct linkage may mean a single bond.

[0067] TIFF2022160374000022.tif17170

[0068] Hereinafter, an embodiment of the present invention will be described with reference to the drawings.

[0069] Fig. 1 is a plan view showing an embodiment of a display device DD, Fig. 2 is a cross-sectional view of the display device DD according to the embodiment, Fig. 2 is a cross-sectional view showing a portion corresponding to the line II' in Fig. 1.

[0070] The display device DD includes a display panel DP and an optical layer PP disposed on the display panel DP. The display panel DP includes light-emitting elements ED-1, ED-2, and ED-3. The display device DD includes a plurality of light-emitting elements ED-1, ED-2, and ED-3. The optical layer PP is disposed on the display panel DP and controls reflected light in the display panel DP due to external light. The optical layer PP may include, for example, a polarizing layer or a color filter layer. Meanwhile, unlike the illustrated embodiment, the optical layer PP may be omitted from the display device DD of one embodiment.

[0071] A base substrate BL is disposed on the optical layer PP. The base substrate BL is 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 embodiment is not limited thereto, and the base substrate BL may be an inorganic layer, an organic layer, or a composite material layer. Also, unlike the illustrated embodiment, the base substrate BL may be omitted.

[0072] The display device DD according to an embodiment further includes a filling layer (not shown). The filling layer (not shown) is disposed between the display element layer DP-ED and the base substrate BL. The filling layer (not shown) is an organic layer. The filling layer (not shown) includes at least one of an acrylic resin, a silicone resin, and an epoxy resin.

[0073] 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. The display element layer DP-ED includes a pixel definition film PDL, light-emitting elements ED-1, ED-2, and ED-3 arranged between the pixel definition films PDL, and a sealing layer TFE arranged on the light-emitting elements ED-1, ED-2, and ED-3.

[0074] The base layer BS is a member that provides a base surface on which the display element layers DP-ED are disposed. The base layer BS may be a glass substrate, a metal substrate, a plastic substrate, etc. However, the embodiment is not limited thereto, and the base layer BS may be an inorganic layer, an organic layer, or a composite material layer.

[0075] In one embodiment, the circuit layer DP-CL is disposed on the base layer BS, and the circuit layer DP-CL includes a plurality of transistors (not shown). Each of the transistors (not shown) includes a control electrode, an input electrode, and an output electrode. For example, the circuit layer DP-CL may include a switching transistor and a driving transistor for driving the light-emitting elements ED-1, ED-2, and ED-3.

[0076] Each of the light-emitting elements ED-1, ED-2, and ED-3 has a structure of the light-emitting element ED according to an embodiment shown in Figures 3 to 6. Each of the light-emitting elements ED-1, ED-2, and ED-3 includes a first electrode EL1, a hole transport region HTR, light-emitting layers EML-R, EML-G, and EML-B, an electron transport region ETR, and a second electrode EL2.

[0077] 2 shows an embodiment in which the light emitting layers EML-R, EML-G, and EML-B of the light emitting elements ED-1, ED-2, and ED-3 are disposed in the opening OH defined in the pixel defining layer PDL, and the hole transport region HTR, the electron transport region ETR, and the second electrode EL2 are provided as a common layer for the entire light emitting elements ED-1, ED-2, and ED-3. However, the embodiment is not limited thereto, and unlike the illustration of FIG. 2, in one embodiment, the hole transport region HTR and the electron transport region ETR may be provided by patterning inside the opening OH defined in the pixel defining layer PDL. For example, in one embodiment, the hole transport region HTR, the light emitting layers EML-R, EML-G, EML-B, and the electron transport region ETR of the light emitting elements ED-1, ED-2, and ED-3 may be provided by patterning using an inkjet printing method.

[0078] The encapsulating layer TFE covers the light-emitting elements ED-1, ED-2, and ED-3. The encapsulating layer TFE seals the display element layer DP-ED. The encapsulating layer TFE is a thin-film encapsulating layer. The encapsulating layer TFE is formed by laminating one or more layers. The encapsulating layer TFE includes at least one insulating layer. The encapsulating layer TFE according to an embodiment includes at least one inorganic film (hereinafter, encapsulating inorganic film). Also, the encapsulating layer TFE according to an embodiment includes at least one organic film (hereinafter, encapsulating organic film) and at least one encapsulating inorganic film.

[0079] The sealing inorganic film protects the display element layer DP-ED from moisture / oxygen, and the sealing organic film protects the display element layer DP-ED from foreign matter such as dust particles. The sealing inorganic film may include, but is not limited to, silicon nitride, silicon nitride, silicon oxide, titanium oxide, aluminum oxide, etc. The sealing organic film includes, but is not limited to, an acrylic compound, an epoxy compound, etc. The sealing organic film includes, but is not limited to, a photopolymerizable organic material.

[0080] The sealing layer TFE is disposed on the second electrode EL2 so as to fill the opening OH.

[0081] 1 and 2, the display device DD includes a non-light-emitting area NPXA and light-emitting areas PXA-R, PXA-G, and PXA-B. The light-emitting areas PXA-R, PXA-G, and PXA-B are areas where light generated by light-emitting elements ED-1, ED-2, and ED-3, respectively, is emitted. The light-emitting areas PXA-R, PXA-G, and PXA-B are spaced apart from each other on a plane.

[0082] Each of the light-emitting regions PXA-R, PXA-G, and PXA-B is a region divided by a pixel defining film PDL. The non-light-emitting region NPXA is a region between adjacent light-emitting regions PXA-R, PXA-G, and PXA-B, and corresponds to the pixel defining film PDL. Meanwhile, in this specification, each of the light-emitting regions PXA-R, PXA-G, and PXA-B corresponds to a pixel (Pixel). The pixel defining film PDL divides the light-emitting elements ED-1, ED-2, and ED-3. The light-emitting layers EML-R, EML-G, and EML-B of the light-emitting elements ED-1, ED-2, and ED-3 are disposed in the openings OH defined in the pixel defining film PDL and divided.

[0083] The light emitting regions PXA-R, PXA-G, and PXA-B are divided into a plurality of groups according to the colors of the lights generated from the light emitting elements ED-1, ED-2, and ED-3. In the display device DD according to an embodiment shown in Figures 1 and 2, three light emitting regions PXA-R, PXA-G, and PXA-B that emit red light, green light, and blue light are exemplarily shown. For example, the display device DD according to an 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 separated from each other.

[0084] In the display device DD according to an embodiment, the light emitting elements ED-1, ED-2, and ED-3 emit light of different wavelength regions. For example, in an embodiment, the display device DD may include a light emitting element ED-1 that emits red light, a second light emitting element ED-3 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 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.

[0085] However, the embodiment is not limited thereto, and the first to third light-emitting elements ED-1, ED-2, and ED-3 may emit light in the same wavelength region, or at least one of them may emit light in a different wavelength region. In addition, the first to third light-emitting elements ED-1, ED-2, and ED-3 may all emit blue light.

[0086] In the display device DD according to an embodiment, the light emitting regions PXA-R, PXA-G, and PXA-B are arranged in a striped pattern. 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 are aligned along the second direction axis DR2, respectively. In addition, the red light emitting regions PXA-R, the green light emitting regions PXA-G, and the blue light emitting regions PXA-B are alternately arranged in this order along the first direction axis DR1.

[0087] 1 and 2, the areas of the light-emitting regions PXA-R, PXA-G, and PXA-B are shown to be similar, but the embodiment is not limited thereto, and the areas of the light-emitting regions PXA-R, PXA-G, and PXA-B may differ from each other depending on the wavelength range of the emitted light. Meanwhile, the areas of the light-emitting regions PXA-R, PXA-G, and PXA-B refer to the areas when viewed from a plane defined by the first direction axis DR1 and the second direction axis DR2.

[0088] Meanwhile, the arrangement of the light emitting regions PXA-R, PXA-G, and 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 may be variously combined according to the display quality characteristics required by the display device DD. For example, the arrangement of the light emitting regions PXA-R, PXA-G, and PXA-B may be a pentile arrangement or a diamond arrangement.

[0089] In addition, the areas of the light-emitting regions PXA-R, PXA-G, and PXA-B are different 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.

[0090] 3 to 6 are cross-sectional views each showing a schematic configuration of a light-emitting element according to an embodiment. The light-emitting element ED according to an embodiment includes a first electrode EL1, a second electrode EL2 facing the first electrode EL1, and at least one functional layer disposed between the first electrode EL1 and the second electrode EL2. The at least one functional layer includes a hole transport region HTR, an emission layer EML, and an electron transport region ETR, which are stacked in sequence. That is, the light-emitting element ED according to an embodiment includes a first electrode EL1, a hole transport region HTR, an emission layer EML, an electron transport region ETR, and a second electrode EL2, which are stacked in sequence.

[0091] Fig. 4 shows a cross-sectional view of an embodiment of a light-emitting element ED in which 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, in comparison with Fig. 3. Fig. 5 shows a cross-sectional view of an embodiment of a light-emitting element ED in which 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, in comparison with Fig. 3. Fig. 6 shows a cross-sectional view of an embodiment of a light-emitting element ED in which a capping layer CPL is disposed on the second electrode EL2, in comparison with Fig. 4.

[0092] The light-emitting element ED of one embodiment includes a polycyclic compound according to one embodiment described later in the emission layer EML. Meanwhile, in the display device DD of one embodiment including a plurality of emission regions (FIG. 2), the emission layer EML constituting at least one of the emission regions includes a polycyclic compound according to one embodiment described later.

[0093] In the light emitting element ED according to an embodiment, the first electrode EL1 has conductivity. The first electrode EL1 is made of a metal material, a metal alloy, or a conductive compound. The first electrode EL1 is an anode or a cathode. However, the embodiment is not limited thereto. The first electrode EL1 is a pixel electrode. The first electrode EL1 is a transmissive electrode, a semi-transmissive electrode, or a reflective electrode. The first electrode EL1 includes at least one selected from Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF, Mo, Ti, W, In, Sn, and Zn, a compound of two or more selected from these, a mixture of two or more selected from these, or an oxide thereof.

[0094] When the first electrode EL1 is a transmissive electrode, the first electrode EL1 includes 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-transmissive electrode or a reflective electrode, the first electrode EL1 includes Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF / Ca (a laminated structure of LiF and Ca), LiF / Al (a laminated structure of LiF and Al), Mo, Ti, W, or a compound or mixture thereof (for example, a mixture of Ag and Mg). Alternatively, the first electrode EL1 has a multi-layer structure including a reflective film or semi-transmissive film made of the above material, and a transparent conductive film made of ITO, IZO, ZnO, ITZO, etc. For example, the first electrode EL1 may have a three-layer structure of ITO / Ag / ITO, but is not limited thereto. Also, the embodiment is not limited thereto, and the first electrode EL1 may include the above-mentioned metal material, a combination of two or more metal materials selected from the above-mentioned metal materials, or an oxide of the above-mentioned metal material. The thickness of the first electrode EL1 is about 70 nm to about 1000 nm. For example, the thickness of the first electrode EL1 may be about 100 nm to about 300 nm.

[0095] The hole transport region HTR is provided on the first electrode EL1. The hole transport region HTR includes 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 5 nm to about 1500 nm.

[0096] The hole transport region HTR may have a single layer of a single material, a single layer of multiple different materials, or a multi-layer structure having multiple layers of multiple different materials.

[0097] 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 of a hole injection material and a hole transport material. The hole transport region HTR may have a single layer structure of a plurality of different materials, or 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, which are stacked in order from the first electrode EL1, but the embodiment is not limited thereto.

[0098] The hole transport region HTR can be formed using various methods such as vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) method, inkjet printing, laser printing, and Laser Induced Thermal Imaging (LITI).

[0099] The hole transport region HTR includes a compound represented by the following chemical formula H-1.

[0100] [ka] (Chemical formula H-1)

[0101] In the chemical formula H-1, L 1 and L 2 are each independently a direct bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms. a and b are each independently an integer of 0 to 10. On the other hand, when a or b is an integer of 2 or more, multiple L 1 and L 2 are each independently a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms.

[0102] In the chemical formula H-1, Ar 1 ~Ar 2 are each independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms. 3 is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms.

[0103] The compound represented by the chemical formula H-1 is a monoamine compound. Alternatively, the compound represented by the chemical formula H-1 is Ar -1 ~Ar 3 At least one of the diamine compounds represented by the chemical formula H-1 contains an amino group as a substituent. 1 ~Ar 2 Carbazole compounds containing a substituted or unsubstituted carbazolyl group in at least one of the above, or Ar 1 ~Ar 2 and wherein at least one of the above formulas contains a substituted or unsubstituted fluorenyl group.

[0104] The compound represented by chemical formula H-1 is represented by any one of the compounds in the following compound group H. However, the compounds listed in the following compound group H are merely illustrative, and the compound represented by chemical formula H-1 is not limited to those shown in the following compound group H.

[0105] [Compound group H] [ka] [ka] [ka] [ka] [ka]

[0106] The hole transport region HTR is made of 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 / These may include CSA (polyaniline / camphorsulfonic acid), PANI / PSS ((polyaniline) / poly(4-styrenesulfonate)), NPB (or NPD) (N,N'-di(naphthalen-1-yl)-N,N'-diphenyl-benzidine), polyetherketone with triphenylamine (TPAPEK), 4-isopropyl-4'-methyldiphenyliodonium [tetrakis(pentafluorophenyl)borate], HATCN (dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile), and the like.

[0107] 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), TCTA (4,4',4"-tris(N-carbazolyl)triphenylamine), NPB (N,N'-di(naphthalen-1-yl)-N,N'-diphenyl-benzidine), TAPC (4,4'-cyclohexylidenebis[N,N-bis(4-methylphenyl)benzeneamine]), HMTPD (4,4'-bis[N,N'-(3-tolyl)amino]-3,3'-dimethylbiphenyl), mCP (1,3-bis(N-carbazolyl)benzene), and the like.

[0108] The hole transport region HTR includes CzSi(9-(4-tert-butylphenyl)-3,6-bis(triphenylsilyl)-9H-carbazole), CCP(9-phenyl-9H-3,9′-bicarbazole), mDCP(1,3-bis(1,8-dimethyl-9H-carbazol-9-yl)benzene), or the like.

[0109] The hole transport region HTR includes at least one of the above-mentioned hole transport region compounds in the hole injection layer HIL, the hole transport layer HTL, and the electron blocking layer EBL.

[0110] The thickness of the hole transport region HTR may be about 10 nm to about 1000 nm, for example, about 10 nm to about 500 nm. When the hole transport region HTR includes a hole injection layer HIL, the thickness of the hole injection layer HIL is, for example, about 3 nm to about 100 nm. When the hole transport region HTR includes a hole transport layer HTL, the thickness of the hole transport layer HTL is, for example, about 3 nm to about 100 nm. For example, when the hole transport region HTR includes an electron blocking layer EBL, the thickness of the electron blocking layer EBL is, for example, about 1 nm to about 100 nm. When the thicknesses of the hole transport region HTR, the hole injection layer HIL, the hole transport layer HTL, and the electron blocking layer EBL satisfy the above-mentioned ranges, sufficient hole transport properties can be obtained without a substantial increase in driving voltage.

[0111] In addition to the above-mentioned materials, the hole transport region HTR further includes a charge generating material to improve conductivity. The charge generating material is uniformly or non-uniformly dispersed in the hole transport region HTR. The charge generating material is, 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 include, but are not limited to, 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 NDP9 (4-[[2,3-bis[cyano-(4-cyano-2,3,5,6-tetrafluorophenyl)methylidene]cyclopropylidene]-cyanomethyl]-2,3,5,6-tetrafluorobenzonitrile).

[0112] As described above, the hole transport region HTR includes at least one of a buffer layer (not shown) and an electron blocking layer EBL in addition to the hole transport layer HTL and the hole injection layer HIL. The buffer layer (not shown) increases the luminous efficiency by compensating for the resonance distance according to the wavelength of light emitted from the emission layer EML. The material included in the buffer layer (not shown) is a material that can be included in the hole transport region HTR. The electron blocking layer EBL is a layer that serves to prevent the injection of electrons from the electron transport region ETR to the hole transport region HTR.

[0113] The light-emitting layer EML is provided on the hole-transporting region HTR. The light-emitting layer EML has a thickness of, for example, about 10 nm to about 100 nm, or about 10 nm to about 30 nm. The light-emitting layer EML has a multilayer structure having a single layer made of a single material, a single layer made of a plurality of different materials, or a plurality of layers made of a plurality of different materials.

[0114] The light-emitting device ED according to an embodiment includes the polycyclic compound according to an embodiment in the light-emitting layer EML. The polycyclic compound according to an embodiment is represented by Chemical Formula 1 below.

[0115] [ka] (chemical formula 1)

[0116] In chemical formula 1, X 1 ~X 4 are each independently BR a , N.R. b , C.R. c R d , O, S, or Se. a ~R d are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having from 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having from 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having from 2 to 30 ring carbon atoms.

[0117] For example, in one embodiment, X 1 ~X 4 However, the embodiment is not limited thereto, and at least one may be different from the others.

[0118] Also in one embodiment, R a ~R d may be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenylyl group, etc. However, embodiments are not limited thereto.

[0119] In Chemical Formula 1, a to d are each independently an integer of 0 to 4, 1 ~R 4are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having from 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having from 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having from 2 to 30 ring carbon atoms.

[0120] When a to d are integers of 1 or more, for example, R 1 and R 4 are each independently a t-butyl group, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted biphenylyl group, although embodiments are not limited thereto.

[0121] In Chemical Formula 1, L is a substituted or unsubstituted divalent triptycenyl-ene or a substituted or unsubstituted divalent carboranyl-ene. For example, L may be an unsubstituted divalent triptycenyl-ene group or an unsubstituted carboranyl-ene group.

[0122] In Chemical Formula 1, L is represented by any one of the following formulae L-1 to L-4.

[0123] [ka]

[0124] TIFF2022160374000031.tif36170

[0125] That is, the polycyclic compound of one embodiment has a backbone structure of a dimer-like compound linked by a bulky linker. The polycyclic compound of one embodiment has a structure in which two DABNA derivatives containing a boron (B) atom are linked by a linker. In one embodiment, the two DABNA derivatives linked by the linker are symmetrical with respect to the linker. However, the embodiment is not limited thereto.

[0126] The polycyclic compound of one embodiment of the present invention, which is a dimer bonded by a linker, improves the quality of film formation when forming an organic layer of a light-emitting device by suppressing aggregation between adjacent polycyclic compounds. In addition, the polycyclic compound of one embodiment is used as an auxiliary dopant used as an energy transfer body, and increases Forster energy transfer and suppresses Dexter energy transfer, thereby increasing the device life and improving the efficiency of a light-emitting device including the polycyclic compound of one embodiment in an emission layer.

[0127] The polycyclic compound of one embodiment represented by Chemical Formula 1 is represented by the following Chemical Formula 1-1.

[0128] [ka] (Chemical formula 1-1)

[0129] In the above Chemical Formula 1-1, X 1 ~X 4 , a-d, R 1 ~R 4 For and L, the same contents as those described in the above-mentioned Chemical Formula 1 are applied. That is, the polycyclic compound of one embodiment contains divalent triptysenylene and divalent carboranylene as linkers, and is bonded to each other via the linker at the para position opposite to the B atom of the polycyclic derivative called a DABNA derivative. The two DABNA derivatives bonded by the linker L have the same structure. However, the embodiment is not limited thereto.

[0130] The polycyclic compound represented by Chemical Formula 1 in one embodiment is represented by any one of the compounds in the following first compound group. The light-emitting element ED in one embodiment includes at least one of the polycyclic compounds in the following first compound group in the emission layer EML.

[0131] [First compound group] [ka] [ka]

[0132] In the first compound group, compounds 4 to 6, "CB" represents a divalent carboranylene group. For example, in compounds 4 to 6, "CB" is represented by any one of L-2 to L-4 described above. More specifically, in compounds 4 to 6, "CB" has the structure of L-3 described above.

[0133] The polycyclic compound represented by Chemical Formula 1 according to an embodiment is used as a fluorescent material or a thermally activated delayed fluorescence (TADF) material. For example, the polycyclic compound according to an embodiment may be used as a light-emitting dopant that emits blue light. The polycyclic compound according to an embodiment is also used as a TADF dopant material.

[0134] In one embodiment, the polycyclic compound has a central emission wavelength (λ 2 ) in the wavelength region of 490 nm or less. max ) is a light-emitting material having the above structure. For example, the polycyclic compound of one embodiment represented by Chemical Formula 1 may be a light-emitting material having a central emission wavelength in a wavelength range of 450 nm or more and 470 nm or less. That is, the polycyclic compound of one embodiment is a blue thermally activated delayed fluorescent dopant. However, the embodiment is not limited thereto.

[0135] In the light-emitting element ED of the embodiment shown in FIGS. 3 to 6, the emitting layer EML contains a host and a dopant, and the emitting layer EML contains the polycyclic compound of the embodiment described above as a dopant.

[0136] In one embodiment of the light-emitting element ED, the emission layer EML includes a first host, a second host, an auxiliary dopant, and an emitting dopant. In one embodiment, the first host and the second host are different from each other. The auxiliary dopant includes an organometallic compound. The emitting dopant is a polycyclic compound represented by the above-mentioned Chemical Formula 1.

[0137] In one embodiment, the first host is a hole transporting host, and the second host is an electron transporting host. In one embodiment, the light emitting element ED includes at least one compound selected from the following HT-01 to HT-09 as the first host in the emitting layer EML.

[0138] [ka] [ka] [ka]

[0139] In addition, the light-emitting element ED of one embodiment contains at least one compound selected from the following compounds ET-01 to ET-06 as a second host in the emitting layer EML.

[0140] [ka]

[0141] In one embodiment of the light-emitting device ED, the light-emitting layer EML includes an organometallic complex. For example, in one embodiment of the light-emitting device ED, the light-emitting layer EML may include an organometallic complex as an auxiliary dopant. In one embodiment, the auxiliary dopant included in the light-emitting layer EML is called a phosphorescent sensitizer. In one embodiment of the light-emitting device ED, the phosphorescent sensitizer included in the light-emitting layer EML transfers energy to the light-emitting dopant, increasing the proportion of the light-emitting dopant that emits fluorescent light.

[0142] In the light-emitting element ED, the emitting layer EML contains at least one compound of the following compound group P as an auxiliary dopant.

[0143] [Compound group P] [ka] [ka] [ka] [ka]

[0144] However, the embodiment is not limited thereto, and the light emitting element ED of one embodiment may include a known phosphorescent dopant material of an organometallic complex as an auxiliary dopant.

[0145] The light-emitting element ED of one embodiment exhibits excellent element life and improved luminous efficiency characteristics by including in the emitting layer EML the first host and second host described above, an organometallic complex auxiliary dopant, and an emitting dopant including the polycyclic compound of one embodiment described above.

[0146] The light-emitting device ED of one embodiment further includes the following light-emitting layer material in addition to the polycyclic compound of the one embodiment, the first host, the second host, and the auxiliary dopant material. In the light-emitting device ED of one embodiment, the light-emitting layer EML includes an anthracene derivative, a pyrene derivative, a fluoranthene derivative, a chrysene derivative, a dihydrobenzanthracene derivative, or a triphenylene derivative. In detail, the light-emitting layer EML may include an anthracene derivative or a pyrene derivative.

[0147] 3 to 6, the light-emitting layer EML includes a host and a dopant, and the light-emitting layer EML includes a compound represented by the following chemical formula E-1. The compound represented by the following chemical formula E-1 is used as a fluorescent host material.

[0148] [ka] (Chemical formula E-1)

[0149] In the chemical formula E-1, R 31 ~R 40 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted silyl group, a substituted or unsubstituted thio group, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group having from 1 to 10 carbon atoms, a substituted or unsubstituted alkenyl group having from 2 to 10 carbon atoms, a substituted or unsubstituted aryl group having from 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having from 2 to 30 ring carbon atoms, or are bonded to adjacent groups to form a ring. 31 ~R 40 may be bonded to adjacent groups to form a saturated hydrocarbon ring, an unsaturated hydrocarbon ring, a saturated heterocycle, or an unsaturated heterocycle.

[0150] In the chemical formula E-1, c and d each independently represent an integer of 0 or more and 5 or less.

[0151] Chemical formula E-1 is represented by any one of the following compounds E1 to E19.

[0152] [ka] [ka] [ka] [ka] [ka] [ka] [ka]

[0153] In one embodiment, the light-emitting layer EML includes a compound represented by the following formula E-2a or E-2b: The compound represented by the following formula E-2a or E-2b is used as a phosphorescent host material. [ka] (Chemical formula E-2a)

[0154] In the chemical formula E-2a, a is an integer of 0 to 10, and L a is a direct bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms. a are each independently a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms.

[0155] In the chemical formula E-2a, A 1 ~A 5 are each independently N or CR i R a ~R i are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted amino group, a substituted or unsubstituted thio group, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group having from 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having from 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having from 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having from 2 to 30 ring carbon atoms, or are bonded to adjacent groups to form a ring. a ~R i may combine with adjacent groups to form a hydrocarbon ring or a heterocycle containing N, O, S, or the like as ring-forming atoms.

[0156] On the other hand, in the chemical formula E-2a, A 1 ~A 5 Two or three of the selected items are N and the rest are CR.i It is.

[0157] [ka] (Chemical formula E-2b)

[0158] In the chemical formula E-2b, Cbz1 and Cbz2 are each independently an unsubstituted carbazolyl group or a carbazolyl group substituted with an aryl group having 6 to 30 ring carbon atoms. b is a direct bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms. On the other hand, b is an integer of 0 to 10. If b is an integer of 2 or more, multiple L b are each independently a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms.

[0159] The compound represented by the chemical formula E-2a and the compound represented by the chemical formula E-2b are represented by any one of the compounds in the following compound group E-2. However, the compounds listed in the following compound group E-2 are merely illustrative, and the compounds represented by the chemical formula E-2a or E-2b are not limited to those shown in the following compound group E-2.

[0160] [Compound group E-2] [ka] [ka] [ka] [ka]

[0161] The light-emitting layer EML further includes a common material known in the relevant technical field as a host material. For example, the light-emitting layer EML may include at least one of DPEPO (bis[2-(diphenylphosphino)phenyl]ether oxide), CBP (4,4'-bis(N-carbazolyl)-1,1'-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]imidazol-2-yl)benzene) as a host material. However, the host material may be, for example, Alq 3 (tris(8-hydroxyquinolino)aluminum), ADN (9,10-di(naphthalen-2-yl)anthracene), TBADN (3-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 (hexaphenylcyclotriphosphazene), UGH2 (1,4-bis(triphenylsilyl)benzene), DPSiO 3 (Hexaphenylcyclotrisiloxane), DPSiO 4 (octaphenylcyclotetrasiloxane) may be used as the host material.

[0162] The light-emitting layer EML includes a compound represented by the following chemical formula Ma or Mb. The compound represented by the following chemical formula Ma or Mb is used as a phosphorescent dopant material. In one embodiment, the compound represented by the chemical formula Ma or Mb is used as an auxiliary dopant material.

[0163] [ka] (Chemical formula Ma)

[0164] In the above chemical formula Ma, Y 1 ~Y 4 , and Z 1 ~Z 4 are each independently CR 1 or N and R 1 ~R 4 are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted amino group, a substituted or unsubstituted thio group, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group having from 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having from 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having from 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having from 2 to 30 ring carbon atoms, or are bonded to adjacent groups to form a ring. In the chemical formula Ma, m is 0 or 1, and n is 2 or 3. In the chemical formula Ma, if m is 0, n is 3, and if m is 1, n is 2.

[0165] The compound represented by the chemical formula Ma is used as a phosphorescent dopant. The following compound group M-a1 to M-a25 are used as phosphorescent dopants.

[0166] The compound represented by the chemical formula Ma is represented by any one of the compounds in the following compound group M-a1 to M-a21. However, the following compounds M-a1 to M-a21 are merely illustrative, and the compound represented by the chemical formula Ma is not limited to those represented by the following compounds M-a1 to M-a21.

[0167] [ka] [ka] [ka] [ka] [ka] [ka] [ka]

[0168] The compounds M-a1 and M-a2 are used as red dopant materials, and the compounds M-a3 to M-a7 are used as green dopant materials.

[0169] [ka] (Chemical formula Mb)

[0170] TIFF2022160374000066.tif148170

[0171] The compound represented by formula Mb is used as a blue phosphorescent dopant or a green phosphorescent dopant, and in one embodiment, the compound represented by formula Mb is further included in the emitting layer EML as an auxiliary dopant.

[0172] The compound represented by the chemical formula Mb may be any one of the following compounds: However, the following compounds are merely illustrative, and the compound represented by the chemical formula Mb is not limited to the following compounds:

[0173] [ka] [ka]

[0174] In the above compound, R, R 38 , and R 39are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group having from 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having from 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having from 2 to 30 ring carbon atoms.

[0175] The light emitting layer EML further contains a compound represented by any one of the following chemical formulas Fa to Fc. The compounds represented by the following chemical formulas Fa to Fc are used as fluorescent dopant materials.

[0176] [ka] (Chemical formula: Fa)

[0177] TIFF2022160374000070.tif87170

[0178] [ka] (Chemical formula Fb)

[0179] In the chemical formula Fb, R a and R b are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having from 1 to 20 carbon atoms, a substituted or unsubstituted ring-forming alkenyl group having from 2 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having from 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having from 2 to 30 ring carbon atoms, or are bonded to each other to form a ring with adjacent groups.

[0180] In chemical formula Fb, U and V are each independently a substituted or unsubstituted hydrocarbon ring having from 5 to 30 ring carbon atoms, or a substituted or unsubstituted heterocycle having from 2 to 30 ring carbon atoms.

[0181] In the chemical formula Fb, the number of rings represented by U and V is independently 0 or 1. For example, in the chemical formula Fb, when the number of U or V is 1, one ring constitutes a fused ring in the part represented by U or V, and when the number of U or V is 0, it means that there is no ring represented by U or V. In detail, when the number of U is 0 and the number of V is 1, or when the number of U is 1 and the number of V is 0, the fused ring having a fluorene core of the chemical formula Fb is a cyclic compound having 4 rings. When the numbers of U and V are both 0, the fused ring having a fluorene core of the chemical formula Fb is a cyclic compound having 3 rings. When the numbers of U and V are both 1, the fused ring having a fluorene core of the chemical formula Fb is a cyclic compound having 5 rings.

[0182] [ka] (Chemical formula Fc)

[0183] In the above formula Fc, A 1 and A 2 are each independently O, S, Se, or NR m and R m is a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having from 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having from 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having from 2 to 30 ring carbon atoms. 1 ~R 11 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted amino group, a substituted or unsubstituted boryl group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thio group, a substituted or unsubstituted alkyl group having from 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having from 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having from 2 to 30 ring carbon atoms, or may be bonded to each other to form a ring with adjacent groups.

[0184] In the chemical formula Fc, A 1 and A 2may each independently bond to a substituent of an adjacent ring to form a condensed ring. For example, A 1 and A 2 are each independently NR m When A 1 is R 4 or R 5 A may be bonded to form a ring. 2 is R 7 or R 8 may be bonded to form a ring.

[0185] In one embodiment, the light-emitting layer EML may be formed using a known dopant material such as a styryl derivative (e.g., 1,4-bis[2-(3-N-ethylcarbazolyl)vinyl]benzene (BCzVB), 4-(di-p-tolylamino)-4′-[(di-p-tolylamino)styryl]stilbene (DPAVB), N-(4-((E)-2-(6-((E)-4-(diphenylamino)styryl)naphthalen-2-yl)vinyl)phenyl)styryl). )-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., 1,1-dipyrene, 1,4-dipyrenylbenzene, 1,4-bis(N,N-diphenylamino)pyrene), and the like.

[0186] In one embodiment, when the light emitting layer EML includes a plurality of light emitting layers, at least one of the light emitting layers EML includes a known phosphorescent dopant material. For example, the phosphorescent dopant may be a metal complex including iridium (Ir), platinum (Pt), osmium (Os), gold (Au), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), or thulium (Tm). In particular, Flrpic (iridium (III) bis (4,6-difluorophenylpyridinato-N,C2') picolinate), Fir6 (bis (2,4-difluorophenylpyridinato)-tetrakis (1-pyrazolyl) borate iridium (III)), or PtOEP (platinum-octaethylporphyrin) may be used as the phosphorescent dopant. However, the embodiment is not limited thereto.

[0187] At least one of the light emitting layers EML includes a quantum dot material, the core of which is selected from the group consisting of II-VI compounds, IIIIII-VI compounds, I-III-VI, III-V compounds, III-II-V compounds, IV-VI compounds, group IV elements, group IV compounds, and combinations thereof.

[0188] The II-VI compounds include binary compounds selected from the group consisting of CdSe, CdTe, CdS, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, MgSe, MgS, and mixtures thereof, CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, CdZnSe, CdZnTe, CdHgS, CdHgSe, CdHg ternary compounds selected from the group consisting of Te, HgZnS, HeZnSe, HeZnTe, MgZnSe, MgZnS, and mixtures thereof, and quaternary compounds selected from the group consisting of HgZnTeS, CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe, HgZnSTe, and mixtures thereof.

[0189] III-VI compounds include In 2 S 3 , In 2 Se 3 Binary compounds such as InGaS 3 , InGaSe 3 etc., or any combination thereof.

[0190] Group I-III-VI compounds include AgInS, AgInS 2 , CuInS, CuInS 2 , AgGaS 2 , CuGaS 2 ,CuGaO 2 , AgGaO 2 , AgAlO 2 and mixtures thereof, or a ternary compound selected from the group consisting of AgInGaS 2 , CuInGaS 2 The compound is selected from quaternary compounds such as

[0191] The III-V compound is selected from the group consisting of binary compounds selected from the group consisting of GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, InSb, and mixtures thereof, ternary compounds selected from the group consisting of GaNP, GaNAs, GaNSb, GaPAs, GaPSb, AlNP, AlNAs, AlNSb, AlPAs, AlPSb, InGaP, InAlP, InNP, InNAs, InNSb, InPAs, InPSb, and mixtures thereof, and quaternary compounds selected from the group consisting of GaAlNP, GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNP, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs, InAlPSb, and mixtures thereof, while the III-V compound further comprises a group II metal. For example, InZnP may be selected as the III-II-V compound.

[0192] The IV-VI compound is selected from the group consisting of binary compounds selected from the group consisting of SnS, SnSe, SnTe, PbS, PbSe, PbTe, and mixtures thereof, ternary compounds selected from the group consisting of SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, SnPbTe, and mixtures thereof, and quaternary compounds selected from the group consisting of SnPbSSe, SnPbSeTe, SnPbSTe, and mixtures thereof. The group IV element is selected from the group consisting of Si, Ge, and mixtures thereof. The group IV compound is a binary compound selected from the group consisting of SiC, SiGe, and mixtures thereof.

[0193] In this case, the binary, ternary, or quaternary compounds may be present in a particle with a uniform concentration, or may be present in the same particle with partially different concentration distributions. Also, a quantum dot may have a core / shell structure in which one quantum dot surrounds another quantum dot. In the core / shell structure, the concentration of the element present in the shell decreases toward the core, creating a concentration gradient.

[0194] In some embodiments, the quantum dots have a core / shell structure, including a core comprising the nanocrystals described above, and a shell surrounding the core. The shell of the quantum dot acts as a protective layer to prevent chemical modification of the core and maintain its semiconducting properties, and / or as a charging layer to impart electrophoretic properties to the quantum dot. The shell may be a single layer or multiple layers. Examples of the shell of the quantum dot include metal or nonmetal oxides, semiconducting compounds, or combinations thereof.

[0195] For example, the oxide of a metal or nonmetal is SiO 2 , Al 2 O 3 , TiO 2 , ZnO, MnO, Mn 2 O 3 , Mn 3 O 4 , CuO, FeO, Fe 2 O 3, Fe 3 O 4 , CoO, Co 3 O 4 , binary compounds such as NiO, or MgAl 2 O 4 , CoFe 2 O 4 , NiFe 2 O 4 , CoMn 2 O 4 However, the present invention is not limited thereto.

[0196] Examples of semiconductor compounds include CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnSeS, ZnTeS, GaAs, GaP, GaSb, HgS, HgSe, HgTe, InAs, InP, InGaP, InSb, AlAs, AlP, and AlSb, but the present invention is not limited to these.

[0197] The quantum dots 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 within this range, color purity and color reproducibility can be improved. In addition, since the light emitted through such quantum dots is emitted in all directions, the light viewing angle is improved.

[0198] The shape of the quantum dots is not particularly limited and may be any shape commonly used in the art. More specifically, the quantum dots may be in the form of spherical, pyramidal, multi-arm, or cubic nanoparticles, nanotubes, nanowires, nanofibers, or nanoplate-like particles.

[0199] The hue of light emitted by quantum dots can be adjusted depending on the particle size, and as a result, quantum dots have a variety of emission hues, such as blue, red, and green.

[0200] In the light-emitting element ED according to the embodiment shown in Figures 3 to 6, the electron transport region ETR is provided on the light-emitting layer EML. The electron transport region ETR includes 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.

[0201] The electron transport region ETR has a single layer made of a single material, a single layer made of a plurality of different materials, or a multilayer structure having a plurality of layers made of a plurality of different materials.

[0202] For example, the electron transport region ETR may have a single layer structure of an electron injection layer EIL or an electron transport layer ETL, or may have a single layer structure made of an electron injection material and an electron transport material. The electron transport region ETR may have a single layer structure made of a plurality of different materials, or may have a structure such as an electron transport layer ETL / electron injection layer EIL, a hole blocking layer HBL / electron transport layer ETL / electron injection layer EIL, or an electron transport layer ETL / buffer layer (not shown) / electron injection layer EIL, which are stacked in order from the light emitting layer EML, but is not limited thereto. The thickness of the electron transport region ETR may be, for example, about 100 nm to about 150 nm.

[0203] The electron transport region ETR can be formed using various methods such as vacuum deposition, spin coating, casting, LB method, inkjet printing, laser printing, laser thermal transfer (LITI), and the like.

[0204] The electron transport region ETR includes a compound represented by the following chemical formula ET-1.

[0205] [ka] (Chemical formula ET-1)

[0206] In the chemical formula ET-1, X 1 ~X 3 At least one of them is N and the others are CR a R ais a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having from 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having from 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having from 2 to 30 ring carbon atoms, and Ar 1 ~Ar 3 are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having from 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having from 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having from 2 to 30 ring carbon atoms.

[0207] In the chemical formula ET-1, a to c are each independently an integer of 0 or more and 10 or less. 1 and L 3 are each independently a direct bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms. 1 and L 3 are each independently a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms.

[0208] The electron transport region ETR includes an anthracene-based compound. However, the electron transport region ETR is not limited thereto. For example, the electron transport region ETR may be Alq 3(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-phenylbenzimidazol-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), Bphe n(4,7-diphenyl-1,10-phenanthroline), 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), Bebq 2 (beryllium bis(benzoquinolin-10-olate), ADN (9,10-di(naphthalen-2-yl)anthracene), BmPyPhB (1,3-bis[3,5-di(pyridin-3-yl)phenyl]benzene), TSPO1 (diphenyl(4-(triphenylsilyl)phenyl)phosphine oxide), and mixtures thereof.

[0209] The electron transport region ETR may also include a metal halide such as LiF, NaCl, CsF, RbCl, RbI, CuI, or KI, a lanthanide such as Yb, or a co-deposition material of a metal halide and a lanthanide. For example, the electron transport region ETR may include KI:Yb, RbI:Yb, etc. as a co-deposition material. 2Metal oxides such as O, BaO, or Liq (8-hydroxy-lithium quinolate) may be used, but the embodiment is not limited thereto. The electron transport region ETR may also be made of a material in which an electron transport material is mixed with an insulating organo metal salt. The organo metal salt is a material having an energy band gap of about 4 eV or more. In more detail, for example, the organo metal salt includes metal acetate, metal benzoate, metal acetoacetate, metal acetylacetonate, or metal stearate.

[0210] In addition to the above-mentioned materials, 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), but is not limited thereto.

[0211] The electron transport region ETR includes at least one of the above-mentioned compounds of the electron transport region in the electron injection layer EIL, the electron transport layer ETL, and the hole blocking layer HBL.

[0212] When the electron transport region ETR includes an electron transport layer ETL, the thickness of the electron transport layer ETL may be about 10 nm to about 100 nm, for example, about 15 nm to about 50 nm. When the thickness of the electron transport layer HTL satisfies the above-mentioned range, a sufficient degree of electron transport property is obtained without a substantial increase in driving voltage. When 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 10 nm, or about 3 Å to about 9 nm. When the thickness of the electron injection layer EIL satisfies the above-mentioned range, a sufficient degree of electron injection property is obtained without a substantial increase in driving voltage.

[0213] The second electrode EL2 is provided on the electron transport region ETR. The second electrode EL2 is a common electrode. The second electrode EL2 may be a cathode or an anolondo, but the embodiment is not limited thereto. For example, when the first electrode EL1 is an anode, the second electrode may be a cathode, and when the first electrode EL1 is a cathode, the second electrode may be an anode. The second electrode EL2 includes at least one selected from Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF, Mo, Ti, W, In, Sn, and Zn, a compound of two or more selected from these, a mixture of two or more selected from these, or an oxide thereof.

[0214] The second electrode EL2 is a transmissive electrode, a semi-transmissive electrode, or a reflective electrode. When the second electrode EL2 is a transmissive electrode, the second electrode EL2 is made of a transparent metal oxide, such as ITO, IZO, ZnO, ITZO, etc.

[0215] When the second electrode EL2 is a semi-transmissive 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 (a laminated structure of LiF and Ca), LiF / Al (a laminated structure of LiF and Al), Mo, Ti, Yb, W, or a compound or mixture containing these (e.g., AgMg, AgYb, or MgYb). Alternatively, the second electrode EL2 has a multi-layer structure including a reflective film or semi-transmissive film made of a material, and a transparent conductive film made of ITO, IZO, ZnO, ITZO, or the like. For example, the second electrode EL2 may include the above-mentioned metal materials, a combination of two or more metal materials selected from the above-mentioned metal materials, or an oxide of the above-mentioned metal materials.

[0216] Although not shown, the second electrode EL2 is connected to an auxiliary electrode, and when the second electrode EL2 is connected to the auxiliary electrode, the resistance of the second electrode EL2 is reduced.

[0217] Meanwhile, in one embodiment, a capping layer CPL is further disposed on the second electrode EL2 of the light emitting element ED. The capping layer CPL includes a multi-layer or a single layer.

[0218] In one embodiment, the capping layer CPL is an organic layer or an inorganic layer. For example, when the capping layer CPL includes an inorganic material, the inorganic material is an alkali metal compound such as LiF, MgF 2 The above-mentioned alkaline earth compounds, SiON, SiNx, SiOy, etc. may also be included.

[0219] For example, when the capping layer CPL contains an organic material, the organic material is α-NPD, NPB, TPD, m-MTDATA, Alq 3 , CuPc, TPD15 (N4,N4,N4',N4'-tetra(biphenyl-4-yl)biphenyl-4,4'-diamine), TCTA (4,4',4"-tris(carbazolesol-9-yl)triphenylamine), or the like, or may include an epoxy resin, or an acrylate such as methacrylate. However, the embodiment is not limited thereto, and the capping layer CPL may include at least one of compounds P1 to P5 as follows.

[0220] [ka] [ka] [ka] [ka] [ka]

[0221] On the other hand, the capping layer CPL has a refractive index of 1.6 or more. More specifically, the capping layer CPL has a refractive index of 1.6 or more for light in the wavelength range of 550 nm or more and 660 nm or less.

[0222] Figures 7 and 8 are cross-sectional views corresponding to a display device according to an embodiment. Hereinafter, a description will be given with reference to Figures 7 and 8. In the description of the display device corresponding to an embodiment, the contents that overlap with the contents described in Figures 1 to 6 above will not be described again, and differences will be mainly described.

[0223] Referring to FIG. 7, a display device DD according to an embodiment includes a display panel DP including a display element layer DP-ED, a light control layer CCL disposed on the display panel DP, and a color filter layer CFL.

[0224] In one embodiment shown 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, where the display element layer DP-ED includes light-emitting elements ED.

[0225] The light-emitting element ED includes a first electrode EL1, a hole transport region HTR disposed on the first electrode EL1, an emitting layer EML disposed on the hole transport region HTR, an electron transport region ETR disposed on the 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 is the same as the structures of the light-emitting elements shown in FIG. 3 to FIG. 6.

[0226] 7, the emitting layer EML is disposed in an opening OH defined in the pixel defining layer PDL. For example, the emitting layers EML provided corresponding to each of the emitting regions PXA-R, PXA-G, and PXA-B, which are separated by the pixel defining layer PDL, emit light in the same wavelength region. In the display device DD according to an embodiment, the emitting layer EML emits blue light. Meanwhile, unlike the drawing, the emitting layer EML according to an embodiment may be provided as a common layer for the entire emitting regions PXA-R, PXA-G, and PXA-B.

[0227] At least one of the emission layers ETL provided corresponding to the emission regions PXA-R, PXA-G, and PXA-B includes the polycyclic compound represented by the above-mentioned Chemical Formula 1 according to an embodiment. At least one of the emission layers EML provided corresponding to the emission regions PXA-R, PXA-G, and PXA-B includes the polycyclic compound represented by the above-mentioned Chemical Formula 1 according to an embodiment, and the remaining emission layers EML include a known additional fluorescent light-emitting material, phosphorescent light-emitting material, quantum dots, etc. However, the embodiment is not limited thereto.

[0228] The light control layer CCL is disposed on the display panel DP. The light control layer CCL includes a light converter. The light converter is a quantum dot or a phosphor. The light converter converts the wavelength of the provided light and emits it. That is, the light control layer CCL is a layer including a quantum dot or a layer including a phosphor.

[0229] The light control layer CCL includes a plurality of light control parts CCP1, CCP2, and CCP3. The light control parts CCP1, CCP2, and CCP3 are spaced apart from each other.

[0230] 7, a division pattern BMP is provided between the light control parts CCP1, CCP2, and CCP3 that are spaced apart from each other, but the embodiment is not limited thereto. In FIG. 7, the division pattern BMP is shown not to overlap with the light control parts CCP1, CCP2, and CCP3, but the edges of the light control parts CCP1, CCP2, and CCP3 may at least partially overlap with the division pattern BMP.

[0231] The light control layer CCL includes a first light control unit CCP1 including a first quantum dot QD1 that converts a first color light provided from the light emitting element ED into a second color light, a second light control unit CCP2 including 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.

[0232] In one embodiment, the first light controller CCP1 provides red light, which is the second color light, and the second light controller CCP2 provides green light, which is the third color light. The third light controller CCP3 transmits 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 contents as those described above apply to the quantum dots QD1 and QD2.

[0233] In addition, the light control layer CCL further includes a scatterer SP. The first light control unit CCP1 includes a first quantum dot QD1 and a scatterer SP, the second light control unit CCP2 includes a second quantum dot QD2 and a scatterer SP, and the third light control unit CCP3 includes a scatterer SP without including a quantum dot.

[0234] The scatterer SP is an inorganic particle. For example, the scatterer SP is TiO 2 , ZnO, Al 2 O 3 , SiO 2 The scatterer SP may include at least one of TiO 2 , ZnO, Al 2 O 3 , SiO 2 or hollow silica, or TiO 2 , ZnO, Al 2 O 3 , SiO 2 and hollow silica.

[0235] The first light control unit CCP1, the second light control unit CCP2, and the third light control unit CCP3 each include a base resin BR1, BR2, or BR3 in which the quantum dots QD1, QD2, and the scatterer SP are dispersed. In one embodiment, the first light control unit CCP1 includes the first quantum dots QD1 and the scatterer SP dispersed in the first base resin BR1, the second light control unit CCP2 includes the second quantum dots QD2 and the scatterer SP dispersed in the second base resin BR2, and the third light control unit CCP1 includes the scatterer SP dispersed in the third base resin BR3. The base resins BR1, BR2, and BR3 are media in which the quantum dots QD1, QD2, and the scatterer SP are dispersed, and are generally made of various resin compositions called binders. For example, the base resins BR1, BR2, and BR3 may be acrylic resins, urethane resins, silicone resins, epoxy resins, and the like. The base resins BR1, BR2, and BR3 are transparent resins. In one embodiment, the first base resin BR1, the second base resin BR2, and the third base resin BR3 are each the same or different from each other.

[0236] The light control layer CCL includes a barrier layer BFL1. The barrier layer BFL1 serves to prevent the penetration of moisture and / or oxygen (hereinafter referred to as "moisture / oxygen"). The barrier layer BFL1 is disposed on the light control units CCP1, CCP2, CCP3 to prevent the light control units CCP1, CCP2, CCP3 from being exposed to moisture / oxygen. Meanwhile, the barrier layer BFL1 covers the light control units CCP1, CCP2, CCP3. A barrier layer BLF2 may also be provided between the light control units CCP1, CCP2, CCP3 and the color filter layer CFL.

[0237] The barrier layers BFL1 and BFL2 each include at least one inorganic layer. That is, the barrier layers BFL1 and BFL2 are formed by including an inorganic material. For example, the barrier layers BFL1 and BFL2 are 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 having a high light transmittance. Meanwhile, the barrier layers BFL1 and BFL2 further include an organic film. The barrier layers BFL1 and BFL2 each include a single layer or multiple layers.

[0238] In one embodiment of the display device DD, the color filter layer CFL is disposed on the light control layer CCL. For example, the color filter layer CFL may be disposed directly on the light control layer CCL. In this case, the barrier layer BFL2 is omitted.

[0239] The color filter layer CFL includes a light-shielding portion BM and filters CF-B, CF-G, and CF-R. The color filter layer CFL includes a first filter CF1 that transmits the second color light, a second filter CF2 that transmits the third color light, and a third filter CF3 that transmits the first color light. For example, the first filter CF1 may be a red filter, the second filter CF2 may be a green filter, and the third filter CF3 may be a blue filter. The first filter CF1, the second filter CF2, and the third filter CF3 each include a polymer photosensitive resin and a pigment or dye. The first filter CF1 includes a red pigment or dye, the second filter CF2 includes a green pigment or dye, and the third filter CF3 includes a blue pigment or dye. However, the embodiment is not limited thereto, and the third filter CF3 may not include a pigment or dye. The third filter CF3 includes a polymer photosensitive resin and does not include a pigment or dye. The third filter CF3 is transparent. The third filter CF3 is made of a transparent photosensitive resin.

[0240] In addition, in one embodiment, the first filter CF1 and the second filter CF2 are yellow filters. The first filter CF1 and the second filter CF2 may be provided integrally without being separated from each other.

[0241] The light shielding portion BM is a black matrix. The light shielding portion BM is formed by including an organic light shielding material or an inorganic light shielding material including a black pigment or a black dye. The light shielding portion BM prevents light leakage and distinguishes the boundaries between the adjacent filters CF1, CF2, and CF3. In one embodiment, the light shielding portion BM is formed by a blue filter.

[0242] The first to third filters CF1, CF2, and CF3 are disposed corresponding to the red light emitting region PXA-R, the green light emitting region PXA-G, and the blue light emitting region PXA-B, respectively. A base substrate BL is disposed on the color filter layer CFL. The base substrate BL is a member that provides a base surface on which the color filter layer CFL, the light control layer CCL, and the like are disposed. The base substrate BL is a glass substrate, a metal substrate, a plastic substrate, and the like. However, the embodiment is not limited thereto, and the base substrate BL may be an inorganic layer, an organic layer, or a composite material layer. Also, unlike the illustrated embodiment, the base substrate BL may be omitted.

[0243] 8 is a cross-sectional view showing a part of a display device according to an 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 the embodiment, the light emitting element ED-BT includes a plurality of light emitting structures OL-B1, OL-B2, and OL-B3. The light emitting element ED-BT includes a first electrode EL1 and a second electrode EL2 facing each other, and a plurality of light emitting structures OL-B1, OL-B2, and OL-B3 provided by sequentially stacking in the thickness direction between the first electrode EL1 and the second electrode EL2. Each of the light emitting structures OL-B1, OL-B2, and OL-B3 includes an emitting layer EML (FIG. 7), and a hole transport region HTR and an electron transport region ETR arranged with the emitting layer EML (FIG. 7) sandwiched therebetween.

[0244] That is, the light-emitting element ED-BT included in the display device DD-TD of one embodiment is a light-emitting element having a tandem structure including a plurality of light-emitting layers.

[0245] In the embodiment shown in Fig. 8, the light emitted from each of the light emitting structures OL-B1, OL-B2, and OL-B3 is blue light. However, the embodiment is not limited thereto, and the wavelength regions of the light emitted from each of the light emitting structures OL-B1, OL-B2, and OL-B3 may be different from each other. For example, a light emitting element ED-BT including a plurality of light emitting structures OL-B1, OL-B2, and OL-B3 that emit light in different wavelength regions may emit white light.

[0246] A charge generation layer CGL is disposed between adjacent light emitting structures OL-B1, OL-B2, and OL-B3. The charge generation layer CGL includes a p-type charge generation layer and / or an n-type charge generation layer. At least one of the light emitting structures OL-B1, OL-B2, and OL-B3 included in the display device DD-TD of the embodiment includes the polycyclic compound of the embodiment described above.

[0247] The light-emitting element ED according to one embodiment of the present invention exhibits improved luminous efficiency and improved long-life characteristics by including the polycyclic compound of the above-mentioned embodiment in at least one light-emitting layer EML disposed between the first electrode EL1 and the second electrode EL2.

[0248] The polycyclic compound of the embodiment described above includes bulky ring compounds such as triptycene or carborane as a linker, and has a structure in which two polycyclic rings of DABNA derivatives are linked by such a linker, thereby suppressing the aggregation phenomenon between polycyclic compounds, and when used as a light-emitting material, it shows excellent film properties.In addition, the polycyclic compound of the embodiment emits thermally activated delayed fluorescence, and when the polycyclic compound of the embodiment is used as a light-emitting layer material, the light-emitting device of the embodiment shows excellent luminous efficiency and long life properties.

[0249] In addition, the light-emitting element of one embodiment includes a hole-transporting host, an electron-transporting host, an organometallic complex auxiliary dopant that is a phosphorescence sensitizer, and an emitting dopant that is a polycyclic compound of one embodiment of the present invention in the light-emitting layer, thereby reducing energy loss in the triplet state and increasing the proportion of fluorescent emission, thereby exhibiting improved luminous efficiency and long life characteristics. EXAMPLES

[0250] Hereinafter, a polycyclic compound according to an embodiment of the present invention and a light emitting device according to an embodiment will be described in detail with reference to examples and comparative examples. Note that the following examples are merely illustrative examples for aiding understanding of the present invention, and the scope of the present invention is not limited thereto.

[0251] 1. Synthesis of polycyclic compounds First, the synthesis method of the compound according to the present embodiment will be described in detail by taking as examples the synthesis methods of Compounds 1 to 6. Furthermore, the synthesis method of the polycyclic compound described below is one example, and the synthesis method of the polycyclic compound according to the embodiment of the present invention is not limited to the following example.

[0252] <Synthesis of Compound 1> Polycyclic compound 1 according to one embodiment is synthesized, for example, by the steps of reaction scheme 1 below.

[0253] [Reaction Scheme 1] [ka]

[0254] In a flask, intermediate compound 1-1 (Intermediate 1-1) (10.8 g, 40.0 mmol) and intermediate compound 1-2 (Intermediate 1-2) (22.5 g, 80.0 mmol) were placed, and toluene was added. Next, sodium tert-butoxide, Pd 2 (dba) 3(Tris(dibenzylideneacetone)dipalladium(0)) and tri-tert-butylphosphonium tetrafluoroborate were added, and the mixture was stirred at 110° C. and refluxed for 6 hours. The resulting residue was purified by silica gel chromatography and then recrystallized from a mixed solvent of chloroform and hexane to obtain 21.0 g of intermediate compound 1-3 (Intermediate 1-3) (yield 78%).

[0255] Next, intermediate compound 1-3 (Intermediate 1-3) (6.71 g, 10.0 mmol) and boron triiodide (3.92 g, 10.0 mmol) were placed in a flask, and 1,2-dichlorobenzene was added. The resulting residue was purified by silica gel chromatography and then recrystallized with a mixed solvent of chloroform and hexane to obtain 2.31 g of intermediate compound 1-4 (Intermediate 1-4) (yield 34%).

[0256] Next, intermediate compound 1-4 (Intermediate 1-4) (2.31 g, 3.4 mmol) and intermediate compound 1-5 (Intermediate 1-5) (0.58 g, 1.07 mmol) were placed in a flask, and a mixed solvent of toluene and EtOH (ethanol) was added. Next, 0.3 M Na 2 CO 3 Aqueous solution (sodium carbonate aqueous solution), Pd(PPh 3 ) 4 (Tetrakis(triphenylphosphine)palladium(0)) was added, stirred at 100°C, and refluxed overnight. The resulting residue was purified by silica gel chromatography and then recrystallized from a mixed solvent of chloroform and hexane to obtain 2.10 g of compound 1 of the present invention (yield 80%). [MS: m / z[M]+calcd1539.94; found, 1539.80]

[0257] <Synthesis of compound 2> Polycyclic compound 2 according to one embodiment can be synthesized, for example, by the steps of reaction scheme 2 below.

[0258] [Reaction Scheme 2] [ka]

[0259] In a flask, intermediate compound 2-1 (10.8 g, 40.0 mmol) and intermediate compound 2-2 (25.7 g, 80.0 mmol) were placed, and toluene was added. Next, sodium tert-butoxide, Pd 2 (dba) 3 Then, tri-tert-butylphosphonium tetrafluoroborate was added, and the mixture was stirred at 110° C. and refluxed for 6 hours. The obtained residue was purified by silica gel chromatography and then recrystallized from a mixed solvent of chloroform and hexane to obtain 22.3 g of intermediate compound 2-3 (74% yield).

[0260] Next, intermediate compound 2-3 (7.51 g, 10.0 mmol) and boron triiodide (3.92 g, 10.0 mmol) were placed in a flask, and 1,2-dichlorobenzene was added. The resulting residue was purified by silica gel chromatography and then recrystallized from a mixed solvent of chloroform and hexane to obtain 2.05 g of intermediate compound 2-4 (Intermediate 2-4) (yield 27%).

[0261] Next, intermediate compound 2-4 (3.04 g, 4.00 mmol) and intermediate compound 2-5 (Intermediate 2-5) (0.68 g, 2.00 mmol) were placed in a flask, and a mixed solvent of toluene and EtOH was added. Next, 0.3 M Na 2 CO 3 Aqueous solution, Pd(PPh 3 ) 4 The mixture was stirred at 100°C and refluxed overnight. The resulting residue was purified by silica gel chromatography and then recrystallized from a mixed solvent of chloroform and hexane to obtain 2.31 g of compound 2 of the present invention (yield 68%). [MS: m / z[M]+calcd1699.69; found, 1698.79]

[0262] <Synthesis of compound 3> The polycyclic compound 3 according to one embodiment is synthesized, for example, by the steps of the following reaction scheme 3.

[0263] [Reaction Scheme 3] [ka]

[0264] In a flask, intermediate compound 3-1 (10.8 g, 40.0 mmol) and intermediate compound 3-2 (13.5 g, 80.0 mmol) were placed, and toluene was added. Next, sodium tert-butoxide, Pd 2 (dba) 3 Then, tri-tert-butylphosphonium tetrafluoroborate was added, and the mixture was stirred at 110° C. and refluxed for 6 hours. The obtained residue was purified by silica gel chromatography and then recrystallized from a mixed solvent of chloroform and hexane to obtain 13.8 g of intermediate compound 3-3 (Intermediate 3-3) (yield 77%).

[0265] Next, intermediate compound 3-3 (6.70 g, 15.0 mmol) and boron triiodide (5.87 g, 15.0 mmol) were placed in a flask, and 1,2-dichlorobenzene was added. The resulting residue was purified by silica gel chromatography and then recrystallized from a mixed solvent of chloroform and hexane to obtain 2.59 g of intermediate compound 3-4 (Intermediate 3-4) (yield 38%).

[0266] Next, intermediate compound 3-4 (1.64 g, 3.60 mmol) and intermediate compound 3-5 (Intermediate 3-5) (0.62 g, 1.80 mmol) were placed in a flask, and a mixed solvent of toluene and EtOH was added. Next, 0.3 M Na 2 CO 3 Aqueous solution, Pd(PPh 3 ) 4The mixture was stirred at 100°C and refluxed overnight. The resulting residue was purified by silica gel chromatography and then recrystallized from a mixed solvent of chloroform and hexane to obtain 1.43 g of compound 3 of the present invention (yield 73%). [MS: m / z[M]+calcd1090.44; found, 1090.40]

[0267] <Synthesis of compound 4> The polycyclic compound 4 according to one embodiment is synthesized, for example, by the steps of the following reaction scheme 4.

[0268] [Reaction Scheme 4] [ka]

[0269] In a flask, intermediate compound 4-1 (15.7 g, 50.0 mmol) and intermediate compound 4-2 (28.1 g, 100.0 mmol) were placed, and toluene was added. Next, sodium tert-butoxide, Pd 2 (dba) 3 Then, tri-tert-butylphosphonium tetrafluoroborate was added and the mixture was stirred at 80° C. for 6 hours. The obtained residue was purified by silica gel chromatography and then recrystallized from a mixed solvent of chloroform and hexane to obtain 14.3 g of intermediate compound 4-3 (40% yield).

[0270] Next, intermediate compound 4-3 (14.0 g, 19.6 mmol) and boron triiodide (7.67 g, 19.6 mmol) were placed in a flask, and 1,2-dichlorobenzene was added. The resulting residue was purified by silica gel chromatography and then recrystallized with a mixed solvent of chloroform and hexane to obtain 1.42 g of intermediate compound 4-4 (Intermediate 4-4) (yield 10%).

[0271] Next, intermediate compound 4-4 (7.24 g, 10.0 mmol) was placed in a flask and THF (tetrahydrofuran) was added. Next, CuI, Pd(PPh 3 ) 4 , trimethylsilylacetylene (TMSA; 1.96 g, 20.0 mmol), Et 3 N (triethylamine) was added and stirred for 24 hours at 60° C. The resulting residue was purified by silica gel chromatography and then recrystallized from a mixed solvent of chloroform and hexane to obtain 4.38 g of intermediate compound 4-5 (58% yield).

[0272] Next, intermediate compound 4-5 (22.7 g, 30.0 mmol) was placed in a flask, THF, methanol (MeOH), and KOH (1 M) aqueous solution were added, and the mixture was stirred at room temperature for 1 hour. The resulting residue was purified by silica gel chromatography and then recrystallized with a mixed solvent of chloroform and hexane to obtain 2.41 g of intermediate compound 4-6 (Intermediate 4-6) (yield 12%).

[0273] Next, intermediate compound 4-6 (2.27 g, 3.40 mmol) was placed in a flask, and THF was added. Intermediate compound 4-4 (2.46 g, 3.40 mmol) was placed in the flask, and methanol and KOH (1 M) aqueous solution were added, and the mixture was stirred at 60° C. for 24 hours. The resulting residue was purified by silica gel chromatography to obtain 0.27 g of intermediate compound 4-7 (Intermediate 4-7) (yield 6%).

[0274] Next, decaborane (0.026 g, 0.21 mmol) and N,N-dimethylaniline were added to toluene, and the mixture was stirred at room temperature for 30 minutes and at 100° C. for 2 hours. The temperature was then lowered to room temperature, and intermediate compound 4-7 (0.27 g, 0.21 mmol) was added and refluxed for 16 hours. The resulting residue was purified by silica gel chromatography to obtain 0.10 g of compound 4 (yield 48%).

[0275] <Synthesis of compound 5> The polycyclic compound 5 according to one embodiment is synthesized, for example, by the steps of the following reaction scheme 5.

[0276] [Reaction Scheme 5] [ka]

[0277] In a flask, intermediate compound 5-1 (15.7 g, 50.0 mmol) and intermediate compound 5-2 (32.1 g, 100.0 mmol) were placed, and toluene was added. Next, sodium tert-butoxide, Pd 2 (dba) 3 Then, tri-tert-butylphosphonium tetrafluoroborate was added and the mixture was stirred at 80° C. for 6 hours. The obtained residue was purified by silica gel chromatography and then recrystallized from a mixed solvent of chloroform and hexane to obtain 13.9 g of intermediate compound 5-3 (Intermediate 5-3) (yield 35%).

[0278] Next, intermediate compound 5-3 (13.9 g, 17.5 mmol) and boron triiodide (6.85 g, 17.5 mmol) were placed in a flask, and 1,2-dichlorobenzene was added. The resulting residue was purified by silica gel chromatography and then recrystallized from a mixed solvent of chloroform and hexane to obtain 0.99 g of intermediate compound 5-4 (Intermediate 5-4) (yield 7%).

[0279] Next, intermediate compound 5-4 (8.04 g, 10.0 mmol) was placed in a flask and THF was added. Next, CuI, Pd(PPh 3 ) 4 , trimethylsilylacetylene (TMSAl; 1.96 g, 20.0 mmol), Et 3 N was added, and the mixture was stirred at 60° C. for 24 hours. The obtained residue was purified by silica gel chromatography and then recrystallized from a mixed solvent of chloroform and hexane to obtain 5.18 g of intermediate compound 5-5 (62% yield).

[0280] Next, intermediate compound 5-5 (25.1 g, 30.0 mmol) was placed in a flask, THF, methanol, and KOH (1 M) aqueous solution were added, and the mixture was stirred at room temperature for 1 hour. The resulting residue was purified by silica gel chromatography and then recrystallized with a mixed solvent of chloroform and hexane to obtain 2.03 g of intermediate compound 5-6 (Intermediate 5-6) (yield 9%).

[0281] Next, intermediate compound 5-6 (1.87 g, 2.50 mmol) was placed in a flask, and THF was added. Intermediate compound 5-4 (2.01 g, 2.50 mmol) was placed in the flask, and methanol and KOH (1 M) aqueous solution were added, and the mixture was stirred at 60 ° C. for 24 hours. The obtained residue was purified by silica gel chromatography to obtain 0.29 g of intermediate compound 5-7 (Intermediate 5-7) (yield 8%).

[0282] Next, decaborane (0.03 g, 0.25 mmol) and N,N-dimethylaniline were added to toluene, and the mixture was stirred at room temperature for 30 minutes and at 100° C. for 2 hours. The temperature was then lowered to room temperature, and intermediate compound 5-7 (0.20 g, 0.25 mmol) was added and refluxed for 16 hours. The resulting residue was purified by silica gel chromatography to obtain 0.18 g of compound 5 (yield 45%).

[0283] <Synthesis of compound 6> The polycyclic compound 6 according to one embodiment is synthesized, for example, by the steps of the following reaction scheme 6.

[0284] [Reaction Scheme 6] [ka]

[0285] In a flask, intermediate compound 6-1 (15.7 g, 50.0 mmol) and intermediate compound 6-2 (16.9 g, 100.0 mmol) were placed, and toluene was added. Next, sodium tert-butoxide, Pd 2 (dba) 3Then, tri-tert-butylphosphonium tetrafluoroborate was added and the mixture was stirred at 80° C. for 6 hours. The obtained residue was purified by silica gel chromatography and then recrystallized from a mixed solvent of chloroform and hexane to obtain 7.87 g of intermediate compound 6-3 (Intermediate 6-3) (yield 32%).

[0286] Next, intermediate compound 6-3 (7.86 g, 16.0 mmol) and boron triiodide (6.26 g, 16.0 mmol) were placed in a flask, and 1,2-dichlorobenzene was added. The resulting residue was purified by silica gel chromatography and then recrystallized from a mixed solvent of chloroform and hexane to obtain 0.4 g of intermediate compound 6-4 (Intermediate 6-4) (yield 5%).

[0287] Next, intermediate compound 6-4 (3.00 g, 6.00 mmol) was placed in a flask and THF was added. Then, CuI, Pd(PPh 3 ) 4 , trimethylsilylacetylene (TMSAl; 1.18 g, 12.0 mmol), Et 3 N was added, and the mixture was stirred at 60° C. for 24 hours. The obtained residue was purified by silica gel chromatography and then recrystallized from a mixed solvent of chloroform and hexane to obtain 2.07 g of intermediate compound 6-5 (65% yield).

[0288] Next, intermediate compound 6-5 (15.9 g, 30.0 mmol) was placed in a flask, and THF, methanol, and KOH (1 M) aqueous solution were added and stirred at room temperature for 1 hour. The resulting residue was purified by silica gel chromatography and then recrystallized with a mixed solvent of chloroform and hexane to obtain 1.60 g of intermediate compound 6-6 (Intermediate 6-6) (yield 12%).

[0289] Next, intermediate compound 6-6 (1.60 g, 3.60 mmol) was placed in a flask, and THF was added. Intermediate compound 6-4 (1.80 g, 3.60 mmol) was placed in the flask, and methanol and KOH (1 M) aqueous solution were added, and the mixture was stirred at 60 ° C. for 24 hours. The obtained residue was purified by silica gel chromatography to obtain 0.22 g of intermediate compound 6-7 (Intermediate 6-7) (yield 7%).

[0290] Next, decaborane (0.034 g, 0.28 mmol) and N,N-dimethylaniline were added to toluene, and the mixture was stirred at room temperature for 30 minutes and at 100° C. for 2 hours. The temperature was then lowered to room temperature, and intermediate compound 6-7 (0.22 g, 0.25 mmol) was added and refluxed for 16 hours. The resulting residue was purified by silica gel chromatography to obtain 0.11 g of compound 6 (yield 42%).

[0291] 2. Fabrication and evaluation of light-emitting devices (Fabrication of light-emitting element) The light-emitting device of an example containing the polycyclic compound of an example in the light-emitting layer was manufactured by the following method. The polycyclic compounds of Compound 1 to Compound 4 described above were used as light-emitting dopants in the light-emitting layer to manufacture the light-emitting devices of Examples 1 to 4.

[0292] In Comparative Example 1 and Comparative Example 2, light-emitting devices were fabricated using the following Comparative Compounds C1 and C2, respectively, as light-emitting dopant materials in the light-emitting layer.

[0293] The comparative compounds used in the preparation of the light-emitting device are shown below.

[0294] (Comparative Example Compound) [ka] [ka]

[0295] In addition, the compounds used in the production of the light-emitting element are shown below.

[0296] (Other compounds used in element production) [ka] [ka] [ka] [ka]

[0297] The ITO-patterned glass substrate was cleaned, and NPD was evaporated to a thickness of 30 nm to form a hole injection layer. Next, TCTA was evaporated to a thickness of 20 nm to form a hole transport layer. CzSi was vacuum evaporated on the hole transport layer to form a 10 nm-thick light-emitting auxiliary layer.

[0298] Next, the first host: the second host: the auxiliary dopant: the luminescent dopant were simultaneously evaporated in a weight ratio of 70:30:15:0.5 to form a luminescent layer having a thickness of 25 nm. In the comparative example and the example, when forming the luminescent layer, the compound HT-08 was used as the first host, the compound ET-04 was used as the second host, and the compound 13 was used as the auxiliary dopant. In addition, the comparative example compound and the example compound were used as the luminescent dopant.

[0299] Next, TSPO1 was evaporated to a thickness of 20 nm to form an electron transport layer, TPBi was evaporated to a thickness of 30 nm to form a buffer layer, and LiF was evaporated to a thickness of 1 nm to form an electron injection layer.

[0300] Next, Al was provided to a thickness of 300 nm to form a second electrode.

[0301] (Evaluation of light-emitting device characteristics) Table 1 shows the evaluation results of the light-emitting devices of Examples 1 to 4 and Comparative Examples 1 and 2. Table 1 shows a comparison of the light-emitting efficiency, emission wavelength, and device life of the fabricated light-emitting devices. The results of the characteristic evaluation of the Examples and Comparative Examples shown in Table 1 show that 2 The figure shows the luminous efficiency at a current density of 10 mA / cm. 2 This indicates the time it takes for the brightness to decrease from the initial brightness to 95% (a 5% decrease in brightness) when continuously driven at a current density of

[0302] The current density, driving voltage, and luminous efficiency of the light-emitting elements of the examples and comparative examples were measured in a darkroom using a 2400 series source meter manufactured by Keithley Instruments, a colorimeter CS-200 manufactured by Konica Minolta, and the measurement PC program LabVIEW 2.0 manufactured by National Instruments Japan.

[0303] [Table 1]

[0304] Referring to the results in Table 1, it can be seen that the light emitting devices of the Examples and Comparative Examples emit blue light having an emission wavelength of 461 to 462 nm. Also, referring to the results in Table 1, it can be seen that the light emitting device of the Examples using the polycyclic compound of one embodiment of the present invention as a light emitting dopant material of the light emitting layer exhibits superior luminance efficiency and improved device life characteristics compared to the Comparative Examples.

[0305] In other words, referring to Table 1, it can be seen that Examples 1 to 4 exhibit longer life and higher efficiency characteristics by including a polycyclic compound having a dimer structure bonded by a bulky linker compared to the light-emitting dopants used in the light-emitting layers of the light-emitting devices of Comparative Examples 1 and 2.

[0306] The polycyclic compound according to one embodiment has a dimeric compound structure bonded by a linker having a large volume, and is used as a delayed fluorescent material, which contributes to high efficiency and long life characteristics of a light emitting device. In addition, the light emitting device according to one embodiment simultaneously exhibits long life and high efficiency characteristics by including the polycyclic compound according to one embodiment in the light emitting layer.

[0307] Although the present invention has been described above with reference to preferred embodiments thereof, it will be understood by those skilled in the art or those having ordinary knowledge in the art that various modifications and variations of the present invention can be made without departing from the spirit and technical scope of the present invention as set forth in the claims below.

[0308] Therefore, the technical scope of the present invention should be determined not by the contents described in the detailed description of the specification, but by the claims. [Explanation of symbols]

[0309] DD, DD-TD: display device, ED: light-emitting element, EL1: first electrode, EL2: second electrode, HTR: hole transport region, EML: light-emitting layer, ETR: electron transport region

Claims

1. A first electrode; A second electrode disposed on the first electrode; a light-emitting layer disposed between the first electrode and the second electrode, the light-emitting layer including a polycyclic compound represented by the following Chemical Formula 1: The first electrode and the second electrode are each independently selected from Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF, Mo, Ti, W, In, Sn, and Zn, or a compound of two or more selected from these, a mixture of two or more selected from these, or an oxide thereof. 【Chemistry 1】 (Chemical formula 1) In the above Chemical Formula 1, X １ ~X ４ are each independently BR ａ , N.R. ｂ , C.R. ｃ R ｄ , O, S, or Se; a to d each independently represent an integer of 0 to 4, R ａ ~R ｄ , and R １ ~R ４ each independently represents a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having from 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having from 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having from 2 to 30 ring carbon atoms, L is a substituted or unsubstituted divalent triptysenylene group, or a substituted or unsubstituted divalent carboranylene group.

2. The light emitting device according to claim 1, wherein the chemical formula 1 is represented by the following chemical formula 1-1: 【Chemistry 2】 (Chemical formula 1-1) In the above Chemical Formula 1-1, X １ ~X ４ , a to d, R １ ~R ４ and L are as defined in Formula 1 above.

3. The light-emitting device according to claim 1, wherein L is any one of L-1 to L-4 below: 【Chemistry 3】

4. R １ and R ４ 2. The light-emitting device according to claim 1, wherein each of independently represents a t-butyl group, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted biphenylyl group.

5. X １ ~X ４ The light-emitting device according to claim 1 , wherein

6. The light-emitting layer is a delayed fluorescent light-emitting layer containing a host and a dopant, The light-emitting device according to claim 1 , wherein the dopant comprises the polycyclic compound.

7. 2. The light emitting device according to claim 1, wherein the formula 1 is represented by any one of the polycyclic compounds of the following first compound group: [First compound group] 【Chemistry 4】 【Chemistry 5】 In the fourth to sixth compounds, "CB" is a divalent carboranylene group.

8. the light-emitting layer includes a first host, a second host different from the first host, an auxiliary dopant including an organometallic complex, and an emitting dopant; The light-emitting device according to claim 1 , wherein the light-emitting dopant comprises the polycyclic compound.

9. The light emitting device according to claim 8, wherein the first host comprises at least one of the following compounds HT-01 to HT-09: 【Chemistry 6】 【Chemistry 7】 【Chemistry 8】

10. The light emitting device according to claim 8, wherein the second host comprises at least one of the following compounds ET-01 to ET-06: 【Chemistry 9】

11. The light emitting device according to claim 8 , wherein the assisting dopant includes at least one of the compounds in the following compound group P: [Compound group P] 【Chemistry 10】 【Chemistry 11】 【Chemistry 12】 【Chemistry 13】

12. The light-emitting device according to claim 1 , wherein the light-emitting layer emits blue light having a center wavelength of 450 nm or more and 470 nm or less.

13. The light emitting device according to claim 1 , further comprising a capping layer disposed on the second electrode, the capping layer having a refractive index of 1.6 or more.

14. A first electrode; A second electrode disposed on the first electrode; an emitting layer disposed between the first electrode and the second electrode, the emitting layer including a hole-transporting first host, an electron-transporting second host different from the first host, an auxiliary dopant, and an emitting dopant different from the auxiliary dopant; The light-emitting dopant is a light-emitting device represented by the following Chemical Formula 1: 【Chemistry 14】 (Chemical formula 1) In the above Chemical Formula 1, X １ ~X ４ are each independently BR ａ , N.R. ｂ , C.R. ｃ R ｄ , O, S, or Se; a to d each independently represent an integer of 0 to 4, R ａ ~R ｄ , and R １ ~R ４ each independently represents a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having from 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having from 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having from 2 to 30 ring carbon atoms, L is a substituted or unsubstituted divalent triptysenylene group, or a substituted or unsubstituted divalent carboranylene group.

15. The light-emitting device according to claim 14, wherein the formula 1 is represented by the following formula 1-1: 【Chemistry 15】 (Chemical formula 1-1) In the above Chemical Formula 1-1, X １ ~X ４ , a to d, R １ ~R ４ and L are as defined in Formula 1 above.

16. The light-emitting device according to claim 14, wherein L is any one of the following L-1 to L-4: 【Chemistry 16】

17. The light emitting device according to claim 14 , wherein the formula 1 is represented by any one of the polycyclic compounds of the following first compound group: [First compound group] 【Chemistry 17】 【Chemistry 18】 In the fourth to sixth compounds, "CB" is a divalent carboranylene group.

18. The first host includes at least one of the following compounds HT-01 to HT-09: Item 15. The light-emitting device according to item 14. 【Chemistry 19】 【Chemistry 20】 【Chemistry 21】

19. The light emitting device according to claim 14, wherein the second host comprises at least one of the following compounds ET-01 to ET-06: 【Chemical 22】

20. The light emitting device according to claim 14 , wherein the assisting dopant comprises at least one of the following compounds in compound group P: [Compound group P] 【Chemistry 23】 【Chemistry 24】 【Chemistry 25】 【Chemistry 26】

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