Light emitting element
By employing a polycyclic compound light-emitting layer and a specific metal electrode structure in an organic electroluminescent display device, the problems of high driving voltage, low luminous efficiency, and short lifespan have been solved, resulting in a light-emitting element with low driving voltage, high efficiency, and long lifespan.
Patent Information
- Authority / Receiving Office
- CN · China
- Patent Type
- Patents(China)
- Current Assignee / Owner
- SAMSUNG DISPLAY CO LTD
- Filing Date
- 2021-12-17
- Publication Date
- 2026-06-16
AI Technical Summary
In existing organic electroluminescent display devices, the driving voltage of the light-emitting elements is high, the luminous efficiency is low, and the lifespan is short, making it difficult to achieve a stable long lifespan.
The light-emitting layer employs a polycyclic compound and uses metals such as Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF, Mo, Ti, W, In, Sn, and Zn, or their compounds, oxides, or multilayered electrodes. The light-emitting layer is doped with a polycyclic compound, and the light-emitting layer can emit thermally active delayed fluorescence with a center wavelength of 430 nm to 490 nm.
It achieves low driving voltage, improves luminous efficiency, and extends the lifespan of the light-emitting element, thus possessing long lifespan characteristics.
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Figure CN114649488B_ABST
Abstract
Description
Technical Field
[0001] The present invention relates to a light-emitting element, and more specifically, to a light-emitting element in which the light-emitting layer comprises a polycyclic compound. Background Technology
[0002] Recently, organic electroluminescence displays (OLEDs) have been under vigorous development as image display devices. Unlike liquid crystal displays (LCDs), OLEDs are self-emissive display devices that achieve display by causing holes and electrons injected from the first and second electrodes to recombine in the light-emitting layer, thereby causing the light-emitting material, which contains organic compounds, in the light-emitting layer to emit light.
[0003] When applying light-emitting elements to display devices, there is a need for low driving voltage, high luminous efficiency, and long lifespan for the light-emitting elements, and there is a continuous need to develop materials for light-emitting elements that can reliably achieve these goals. Summary of the Invention
[0004] The purpose of this invention is to provide a long-life light-emitting element.
[0005] One embodiment provides a light-emitting element, comprising: a first electrode; a second electrode disposed on the first electrode; and a light-emitting layer disposed between the first electrode and the second electrode, and comprising a polycyclic compound represented by the following chemical formula 1, wherein the first electrode and the second electrode each independently comprise at least one selected from Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF, Mo, Ti, W, In, Sn and Zn, two or more compounds selected from them, mixtures selected from two or more of them, oxides of them, or materials having a multilayer structure of LiF / Ca or LiF / Al.
[0006] [Chemical Formula 1]
[0007]
[0008] In the aforementioned chemical formula 1, m and n are independently 0 or 1, o is an integer greater than 0 and less than 3, X1 to X4 are independently NRa, CRbRc, O or S, Y1 and Y2 are independently NRd, O or S, and R1 to R 20And Ra to Rd are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted amino group, an alkyl group with 1 to 20 carbon atoms, an aryl group with 6 to 30 cyclic carbon atoms, or a heteroaryl group with 3 to 30 cyclic carbon atoms.
[0009] The chemical formula 1 can be represented by the following chemical formula 2-1 or the following chemical formula 2-2.
[0010] [Chemical Formula 2-1]
[0011]
[0012] [Chemical Formula 2-2]
[0013]
[0014] In chemical formulas 2-1 and 2-2, n, o, X1 to X4, Y1, Y2, and R1 to R 20 It can be the same as the definition in Chemical Formula 1, where o1 can be 0 or 1 in Chemical Formula 2-2.
[0015] The chemical formula 1 can be represented by any one of the following chemical formulas 3-1 to 3-3.
[0016] [Chemical Formula 3-1]
[0017]
[0018] [Chemical Formula 3-2]
[0019]
[0020] [Chemical Formula 3-3]
[0021]
[0022] In the chemical formulas 3-1 to 3-3, m to o, X1 to X4, Y1, Y2, and R1 to R 20 As defined in Chemical Formula 1, in Chemical Formula 3-1 and Chemical Formula 3-2, o1 can be 0 or 1.
[0023] In the chemical formula 3-1, R 11 To R 18 At least one of them can be an unsubstituted phenyl group.
[0024] The chemical formula 1 can be represented by any one of the following chemical formulas 4-1 to 4-3.
[0025] [Chemical Formula 4-1]
[0026]
[0027] [Chemical Formula 4-2]
[0028]
[0029] [Chemical Formula 4-3]
[0030]
[0031] In chemical formulas 4-1 and 4-3, m to n, X1 to X4, and R1 to R 20 As defined in Formula 1, Rd1 and Rd2 can be independently hydrogen atoms, deuterium atoms, halogen atoms, substituted or unsubstituted amino groups, alkyl groups with 1 to 20 carbon atoms, aryl groups with 6 to 30 cyclic carbon atoms, or heteroaryl groups with 2 to 30 cyclic carbon atoms, respectively.
[0032] In the chemical formula 1, at least one of X1 to X4 can be NRa, and Ra can be any one of a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, and a substituted or unsubstituted terphenyl.
[0033] In the chemical formula 1, at least one of Y1 and Y2 can be NRd, and Rd can be a substituted or unsubstituted phenyl group.
[0034] The light-emitting layer may include a dopant and a host, and the dopant may include the polycyclic compound.
[0035] The light-emitting layer can emit thermally active delayed fluorescence.
[0036] The light-emitting layer can emit light with a light-emitting center wavelength of 430nm or higher and 490nm or lower.
[0037] The R1 to R 20 They can all be deuterium atoms.
[0038] One embodiment provides a light-emitting element, comprising: a first electrode; a second electrode disposed on the first electrode; a light-emitting layer disposed between the first electrode and the second electrode, and comprising a polycyclic compound represented by the following chemical formula 1A; and a capping layer disposed on the light-emitting layer, having a refractive index of 1.6 or higher.
[0039] [Chemical Formula 1A]
[0040]
[0041] In the chemical formula 1A, at least one pair of W1 to W6, consisting of two adjacent pairs selected from W1 to W3 and two adjacent pairs selected from W4 to W6, can be connected to the substituent represented by chemical formula 2A, and the remainder can be independently CRe, X1 to X4 can be independently NRa, CRbRc, O or S, and R1 to R 10 Ra to Rc and Re can be independently hydrogen atoms, deuterium atoms, halogen atoms, substituted or unsubstituted amino groups, alkyl groups with 1 to 20 carbon atoms, aryl groups with 6 to 30 cyclic carbon atoms, or heteroaryl groups with 3 to 30 cyclic carbon atoms.
[0042] [Chemical Formula 2A]
[0043]
[0044] In the chemical formula 2A, Y can be NRd, O, or S, and R 11 To R 14 And Rd can be a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted amino group, an alkyl group with 1 to 20 carbon atoms, a substituted or unsubstituted cyclic carbon group with 6 to 30 carbon atoms, or a heteroaryl group with 3 to 30 carbon atoms.
[0045] The chemical formula 2A can be represented by chemical formula 3A-1 or chemical formula 3A-2.
[0046] [Chemical Formula 3A-1]
[0047]
[0048] [Chemical Formula 3A-2]
[0049]
[0050] In the chemical formula 3A-1, Y1 can be NRd1, O, or S, and Y1 can combine with W1 or W2. 11a To R 14aRd1 can be independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted amino group, an alkyl group with 1 to 20 carbon atoms (substituted or unsubstituted), an aryl group with 6 to 30 carbon atoms (substituted or unsubstituted), or a heteroaryl group with 3 to 30 carbon atoms (substituted or unsubstituted). In the chemical formula 3A-2, Y2 can be NRd2, O, or S, and Y2 can be combined with W5 or W6. 11b To R 14b And Rd2 can be independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted amino group, an alkyl group with 1 to 20 carbon atoms, a substituted or unsubstituted cyclic carbon group with 6 to 30 carbon atoms, or a heteroaryl group with 3 to 30 carbon atoms.
[0051] If the chemical formula 3A-1 is combined with W1 and W2, then the chemical formula 3A-2 can be combined with W5 and W6.
[0052] Y1 in chemical formula 3A-1 can be the same as Y2 in chemical formula 3A-2.
[0053] The chemical formula 2A can be represented by the following chemical formulas 4A-1 to 4A-3.
[0054] [Chemical Formula 4A-1]
[0055]
[0056] [Chemical Formula 4A-2]
[0057]
[0058] [Chemical Formula 4A-3]
[0059]
[0060] In chemical formulas 4A-1 to 4A-3, R 11 To R 14 And Rd can be the same as the definition in the chemical formula 2A.
[0061] In the chemical formula 1A, at least one of X1 to X4 can be NRa, and Ra can be any one of a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, and a substituted or unsubstituted terphenyl.
[0062] In the chemical formula 2A, Y can be NRd, and Rd can be a substituted or unsubstituted phenyl group.
[0063] The luminescent layer may include at least one of the compounds shown in compound group 1 below.
[0064] One embodiment of the light-emitting element can exhibit long-lifetime characteristics by including a polycyclic compound of one embodiment in the light-emitting layer. Attached Figure Description
[0065] Figure 1 This is a plan view illustrating one embodiment of the display device.
[0066] Figure 2 This is a cross-sectional view of a display device according to an embodiment.
[0067] Figure 3 This is a schematic cross-sectional view of a light-emitting element according to one embodiment.
[0068] Figure 4 This is a schematic cross-sectional view of a light-emitting element according to one embodiment.
[0069] Figure 5 This is a schematic cross-sectional view of a light-emitting element according to one embodiment.
[0070] Figure 6 This is a schematic cross-sectional view of a light-emitting element according to one embodiment.
[0071] Figure 7 This is a cross-sectional view of a display device according to an embodiment.
[0072] Figure 8 This is a cross-sectional view of a display device according to an embodiment.
[0073] [Explanation of the labels in the attached diagram]
[0074] DD, DD-TD: Display device
[0075] ED: Light-emitting element; EL1: First electrode
[0076] EL2: Second electrode; HTR: Hole transport region
[0077] EML: Emitting Layer; ETR: Electron Transport Region Detailed Implementation
[0078] This invention can be modified in many ways and can have many forms. Specific embodiments are illustrated in the accompanying drawings and described in detail herein. However, it is not intended to limit the invention to the specific disclosed forms, and should be understood to include all modifications, equivalents, and substitutions encompassed by the spirit and scope of the invention.
[0079] In describing the figures, similar reference numerals are used for similar constituent elements. In the figures, the dimensions of the structures are shown enlarged compared to their actual dimensions for clarity of the invention. Terms such as "first," "second," etc., can be used to describe multiple constituent elements, but the constituent elements should not be limited by these terms. These terms are used only to distinguish one constituent element from another. For example, without departing from the scope of the invention, a first constituent element can be named a second constituent element, and similarly, a second constituent element can be named a first constituent element. Singular expressions include plural expressions unless the context clearly indicates a different meaning.
[0080] In this application, terms such as “comprising” or “having” should be understood as being intended to specify the presence of features, figures, steps, operations, constituent elements, components or combinations thereof as described in the specification, rather than precluding the possibility of the presence or addition of one or more other features or figures, steps, operations, constituent elements, components or combinations thereof.
[0081] In this application, when referring to a layer, membrane, region, plate, or other portion as being "above" or "upper" another portion, this includes not only the case where it is "immediately above" the other portion, but also the case where other portions exist in between. Conversely, when referring to a layer, membrane, region, plate, or other portion as being "below" or "lower" of another portion, this includes not only the case where it is "immediately below" the other portion, but also the case where other portions exist in between. Furthermore, in this application, referring to being "arranged above" can include not only the case where it is arranged in the upper part, but also the case where it is arranged in the lower part.
[0082] In this specification, "substituted or unsubstituted" can mean that the substance is substituted or unsubstituted by one or more substituents selected from the group consisting of deuterium, halogen, cyano, nitro, amino, silyl, oxy, thio, sulfinyl, sulfonyl, carbonyl, boron, phosphonyl oxide, phosphonyl sulfide, alkyl, alkenyl, alkynyl, alkylcyclic, aryl, and heterocyclic groups. Furthermore, the substituents exemplified above can be either substituted or unsubstituted. For example, biphenyl can be interpreted as aryl or as a phenyl group substituted with a phenyl group.
[0083] In this specification, "forming a ring by bonding with adjacent groups" can refer to the situation where adjacent groups bond with each other to form a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocycle. Hydrocarbon rings include aliphatic hydrocarbon rings and aromatic hydrocarbon rings. Heterocycles include aliphatic heterocycles and aromatic heterocycles. Hydrocarbon rings and heterocycles can be monocyclic or polycyclic. Furthermore, the rings formed by bonding with each other can connect with other rings to form a spirostructure.
[0084] In this specification, "adjacent group" can mean a substituent that is directly attached to the atom substituted by the corresponding substituent, another substituent that is substituted by the atom substituted by the corresponding substituent, or a substituent that is stereoscopically closest to the corresponding substituent. For example, in 1,2-dimethylbenzene, the two methyl groups can be interpreted as "adjacent groups"; in 1,1-diethylcyclopentane, the two ethyl groups can be interpreted as "adjacent groups"; and in 4,5-dimethylphenanthrene, the two methyl groups can be interpreted as "adjacent groups".
[0085] Examples of halogen atoms in this specification include fluorine, chlorine, bromine, or iodine atoms.
[0086] In this specification, alkyl groups can be straight-chain, 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, sec-butyl, tert-butyl, isobutyl, 2-ethylbutyl, 3,3-dimethylbutyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, cyclopentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 2-butylhexyl, cyclohexyl, 4-methylcyclohexyl, 4-tert-butylcyclohexyl, n-heptyl, 1-methylheptyl, 2,2-dimethylheptyl, 2-ethylheptyl, 2-butylheptyl, n-octyl, tert-octyl, 2-ethyloctyl, 2-butyloctyl, 2-hexyloctyl, 3,7-dimethyloctyl, cyclooctyl, n-nonyl, n-decyl, adamantyl, 2-ethyldecyl, 2-butyldecyl, 2 - Hexyldecyl, 2-octyldecyl, undecyl, dodecyl, 2-ethyldodecyl, 2-butyldodecyl, 2-hexyldodecyl, 2-octyldodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, 2-ethylhexadecyl, 2-butylhexadecyl, 2-hexylhexadecyl, 2-octylhexadecyl, heptadecanyl, octadecyl, nonadecanyl, eicosyl, 2-ethyleicosyl, 2-butyleicosyl, 2-hexyleicosyl, 2-octyleicosyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecanyl, hexadecyl, octadecyl, nonadecanyl, and triadecyl, etc., but not limited to these.
[0087] In this specification, cycloalkyl group refers to any functional group or substituent derived from an aliphatic hydrocarbon ring. The cycloalkyl group can be a saturated cycloalkyl group with 5 to 20 carbon atoms in the ring.
[0088] In this specification, aryl represents any functional group or substituent derived from an aromatic hydrocarbon ring. Aryl groups can be monocyclic or polycyclic. The number of carbon atoms in the cyclic aryl group can be 6 to 30, 6 to 20, or 6 to 15. Examples of aryl groups include phenyl, naphthyl, fluorenyl, anthraceneyl, phenanthryl, biphenyl, terphenyl, tetraphenyl, quinquephenyl, hexaphenyl, benzo[9,10]phenanthryl, pyrene, benzofluoranthracene, etc. It includes, but is not limited to, basic, and advanced technologies.
[0089] In this specification, the fluorene group can be substituted, or two substituents can combine with each other to form a spirostructure. Examples of fluorene group substitution are described below. However, this is not a limitation.
[0090]
[0091] In this specification, a heterocyclic group refers to any functional group or substituent derived from a ring comprising one or more of B, O, N, P, Si, and S as heteroatoms. Heterocyclic groups include aliphatic heterocyclic groups and aromatic heterocyclic groups. Aromatic heterocyclic groups can be heteroaryl groups. Aliphatic and aromatic heterocycles can be monocyclic or polycyclic.
[0092] In this specification, a heterocyclic group may include one or more of B, O, N, P, Si, and S as heteroatoms. When a heterocyclic group includes two or more heteroatoms, the two or more heteroatoms may be the same or different. The heterocyclic group may be a monocyclic or polycyclic heterocyclic group, and includes the concept of a heteroaryl group. The number of cyclic carbon atoms in the heterocyclic group may be 2 to 30, 2 to 20, or 2 to 10.
[0093] In this specification, aliphatic heterocyclic groups may include one or more of B, O, N, P, Si, and S as heteroatoms. The number of cyclic carbon atoms in an aliphatic heterocyclic group may be 2 to 30, 2 to 20, or 2 to 10. Examples of aliphatic heterocyclic groups include ethylene oxide, thiocyclopropane, pyrrolyl, piperidinyl, tetrahydrofuranyl, tetrahydrothiophenyl, thiaalkyl, tetrahydropyranyl, 1,4-dioxane, etc., but are not limited to these.
[0094] In this specification, a heteroaryl group may include one or more of B, O, N, P, Si, and S as a heteroatom. When a heteroaryl group includes two or more heteroatoms, these heteroatoms may be identical or different from each other. A heteroaryl group may be a monocyclic heterocyclic group or a polycyclic heteroaryl group. The number of carbon atoms in the ring-forming structure of the heteroaryl group may be 2 to 30, 2 to 20, or 2 to 10. Examples of heteroaryl groups include thiophene, furanyl, pyrrole, imidazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinel, pyridazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazole, N-arylcarbazole, and N-heteroarylcarbazole. N-alkylcarbazolyl, benzoxazolyl, benzoimidazolyl, benzothiazolyl, benzocarbazolyl, benzothiophene, dibenzothiophene, thiophene-thiophene, benzofuranyl, phenanthrolinel, thiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, thiadiazolyl, phenothiazinyl, dibenzosilole, and dibenzofuranyl, etc., but not limited to these.
[0095] In this specification, except that the arylene group is divalent, the description of the aforementioned aryl group can be applied. Except that the heteroarylene group is divalent, the description of the aforementioned heteroarylene group can be applied.
[0096] In this specification, silane includes alkylsilane and arylsilane. Examples of silanes include trimethylsilane, triethylsilane, tert-butyldimethylsilane, vinyldimethylsilane, propyldimethylsilane, triphenylsilane, diphenylsilane, phenylsilane, etc., but are not limited thereto.
[0097] In this specification, the number of carbon atoms in an amino group is not particularly limited, but can be 1 to 30. Amino groups can include alkylamino, arylamino, or heteroarylamino groups. Examples of amino groups include methylamino, dimethylamino, phenylamino, diphenylamino, naphthylamino, 9-methyl-anthraylamino, etc., but are not limited to these.
[0098] In this specification, the number of carbon atoms in the carbonyl group is not particularly limited, but can be 1 to 40, 1 to 30, or 1 to 20. For example, although the following structures are possible, it is not limited thereto.
[0099]
[0100] In this specification, the number of carbon atoms in the sulfinyl group and sulfonyl group is not particularly limited, but can be more than 1 and less than 30. The sulfinyl group can include alkyl sulfinyl group and aryl sulfinyl group. The sulfonyl group can include alkyl sulfonyl group and aryl sulfonyl group.
[0101] In this specification, a thiol group may include alkylthio and arylthio groups. A thiol group may refer to the case where a sulfur atom is bonded to the defined alkyl or aryl group. Examples of thiol groups include, but are not limited to, methylthio, ethylthio, propylthio, pentylthio, hexylthio, octylthio, dodecylthio, cyclopentylthio, cyclohexylthio, phenylthio, and naphthylthio.
[0102] In this specification, an oxygen group can include alkoxy and aryloxy groups. An oxygen group can represent the combination of an oxygen atom with the defined alkyl or aryl group. An alkoxy group can be straight-chain, branched, or cyclic. The number of carbon atoms in an alkoxy group is not particularly limited, but can be, for example, 1 to 20 or 1 to 10. Examples of oxygen groups include, but are not limited to, methoxy, ethoxy, n-propoxy, isopropoxy, butoxy, pentoxy, hexoxy, octoxy, nonoxy, decoxy, and benzyloxy.
[0103] In this specification, the term "boron group" includes alkylboron group and arylboron group. Boron group can refer to the case where a boron atom is bonded to the defined alkyl or aryl group. Examples of boron groups include, but are not limited to, trimethylboron, triethylboron, tert-butyldimethylboron, triphenylboron, diphenylboron, and phenylboron.
[0104] In this specification, the alkenyl group can be straight-chain or branched. The number of carbon atoms is not particularly limited, but it is 2 to 30, 2 to 20, or 2 to 10. Examples of alkenyl groups include vinyl, 1-butenyl, 1-pentenyl, 1,3-butadienyl, styryl, styrylvinyl, etc., but are not limited to these.
[0105] In this specification, the number of carbon atoms in the amino group is not particularly limited, but can be more than 1 and less than 30. The amino group can include alkylamino and arylamino groups. Examples of amino groups include methylamino, dimethylamino, phenylamino, diphenylamino, naphthylamino, 9-methyl-anthraylamino, triphenylamino, etc., but are not limited to these.
[0106] In this specification, the alkyl groups in alkylthio, alkylthionyl, alkylaryl, alkylamino, alkylboryl, alkylsilyl, and alkylamine are the same as the examples of alkyl groups mentioned above.
[0107] In this specification, the aryl groups in aryloxy (or “aryloxy”), arylthio, arylthionyloxy, arylamino, arylboryl, arylsilyl, and arylamine are the same as those in the examples of the aforementioned aryl groups.
[0108]
[0109] Hereinafter, an embodiment of the present invention will be described with reference to the accompanying drawings.
[0110] Figure 1 This is a plan view showing an embodiment of the display device DD. Figure 2 This is a cross-sectional view of a display device DD according to an embodiment. Figure 2 It is shown that... Figure 1 A cross-sectional view of the portion corresponding to the I-I' line.
[0111] The display device DD may include: a display panel DP; and an optical layer PP disposed on the display panel DP. The display panel DP includes light-emitting elements ED-1, ED-2, and ED-3. The display device DD may include multiple light-emitting elements ED-1, ED-2, and ED-3. The optical layer PP may be disposed on the display panel DP to control reflected light at the display panel DP caused by external light. The optical layer PP may, for example, include a polarizing layer or a color filter layer. Furthermore, unlike the case shown in the figures, in one embodiment of the display device DD, the optical layer PP may be omitted.
[0112] A base substrate BL can be disposed on the optical layer PP. The base substrate BL can be a component that provides a base surface for disposing the optical layer PP. The base substrate BL can be a glass substrate, a metal substrate, a plastic substrate, etc. However, the embodiments are not limited to this; the base substrate BL can be an inorganic layer, an organic layer, or a composite material layer. Furthermore, unlike the illustrated case, in one embodiment, the base substrate BL can be omitted.
[0113] The display device DD according to one embodiment may further include a filler layer (not shown). The filler layer (not shown) may be disposed between the display element layer DP-ED and the base substrate BL. The filler layer (not shown) may be an organic layer. The filler layer (not shown) may include at least one of acrylic resin, silicone resin and epoxy resin.
[0114] The display panel DP may include a base layer BS, a circuit layer DP-CL disposed on the base layer BS, and a display element layer DP-ED. The display element layer DP-ED may include: a pixel defining film PDL; light-emitting elements ED-1, ED-2, and ED-3 disposed between the pixel defining films PDL; and an encapsulation layer TFE disposed on the light-emitting elements ED-1, ED-2, and ED-3.
[0115] The base layer BS can be a component that provides a base surface for arranging the display element layer DP-ED. The base layer BS can be a glass substrate, a metal substrate, a plastic substrate, etc. However, the embodiments are not limited to this; the base layer BS can be an inorganic layer, an organic layer, or a composite material layer.
[0116] In one embodiment, the circuit layer DP-CL is disposed on the base layer BS, and the circuit layer DP-CL may include a plurality of transistors (not shown). The transistors (not shown) may each include a control electrode, an input electrode, and an output electrode. For example, the circuit layer DP-CL may include switching transistors and driving transistors for driving the light-emitting elements ED-1, ED-2, and ED-3 of the display element layer DP-ED.
[0117] Each of the light-emitting elements ED-1, ED-2, and ED-3 may have the following characteristics. Figures 3 to 6 The structure of a light-emitting element ED according to one embodiment. Each of the light-emitting elements ED-1, ED-2, and ED-3 may include a first electrode EL1, a hole transport region HTR, light-emitting layers EML-R, EML-G, EML-B, an electron transport region ETR, and a second electrode EL2.
[0118] exist Figure 2 An embodiment is shown below: the light-emitting layers EML-R, EML-G, and EML-B of light-emitting elements ED-1, ED-2, and ED-3 are arranged within the opening OH defined by the pixel-defining film PDL. The hole transport region HTR, the electron transport region ETR, and the second electrode EL2 are provided as a common layer throughout the light-emitting elements ED-1, ED-2, and ED-3. However, the embodiment is not limited to this, and... Figure 2 In a different embodiment, the hole transport region HTR and electron transport region ETR can be patterned and provided within the opening OH defined by the pixel defining film 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 can be patterned using an inkjet printing method.
[0119] The encapsulation layer TFE can cover the light-emitting elements ED-1, ED-2, and ED-3. The encapsulation layer TFE can seal the display element layer DP-ED. The encapsulation layer TFE can be a thin-film encapsulation layer. The encapsulation layer TFE can be a single layer or composed of multiple stacked layers. The encapsulation layer TFE includes at least one insulating layer. According to one embodiment, the encapsulation layer TFE can include at least one inorganic film (hereinafter referred to as the encapsulation inorganic film). Furthermore, according to one embodiment, the encapsulation layer TFE can include at least one organic film (hereinafter referred to as the encapsulation organic film) and at least one encapsulation inorganic film.
[0120] Inorganic encapsulation films protect the display element layer (DP-ED) from moisture and oxygen, while organic encapsulation films protect the DP-ED from foreign matter such as dust particles. Inorganic encapsulation films may include, but are not specifically limited to, silicon nitride, silicon oxynitride, silicon oxide, titanium dioxide, or aluminum oxide. Organic encapsulation films may include acrylic compounds, epoxy compounds, etc. Organic encapsulation films may include photopolymerizable organic materials, but are not specifically limited to these.
[0121] The encapsulation layer TFE can be disposed on the second electrode EL2, and can be disposed to fill the opening OH.
[0122] Reference Figure 1 and Figure 2 The display device DD may include 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 may be areas that emit light generated from light-emitting elements ED-1, ED-2, and ED-3, respectively. The light-emitting areas PXA-R, PXA-G, and PXA-B may be spaced apart from each other on a plane.
[0123] Each of the light-emitting regions PXA-R, PXA-G, and PXA-B can be a region defined by a pixel-defining film (PDL). The non-light-emitting region NPXA is the region between adjacent light-emitting regions PXA-R, PXA-G, and PXA-B, and can be a region corresponding to the pixel-defining film (PDL). Furthermore, in this specification, the light-emitting regions PXA-R, PXA-G, and PXA-B can each correspond to a pixel. The pixel-defining film (PDL) can divide 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 can be distinguished by being arranged at the opening OH defined by the pixel-defining film (PDL).
[0124] The luminescent regions PXA-R, PXA-G, and PXA-B can be divided into multiple groups based on the color of the light generated by the luminescent elements ED-1, ED-2, and ED-3. Figure 1 and Figure 2 In one embodiment of the display device DD, three light-emitting regions PXA-R, PXA-G, and PXA-B that emit red, green, and blue light are exemplarily shown. For example, one embodiment of the display device DD may include red light-emitting regions PXA-R, green light-emitting regions PXA-G, and blue light-emitting regions PXA-B that can be distinguished from each other.
[0125] In a display device DD according to one embodiment, a plurality of light-emitting elements ED-1, ED-2, and ED-3 can emit light in different wavelengths. For example, in one embodiment, the display device DD may include a first light-emitting element ED-1 that emits red light, a second light-emitting element ED-2 that emits green light, and a third light-emitting element ED-3 that emits blue light. That is, the red light-emitting area PXA-R, the green light-emitting area PXA-G, and the blue light-emitting area PXA-B of the display device DD can correspond to the first light-emitting element ED-1, the second light-emitting element ED-2, and the third light-emitting element ED-3, respectively.
[0126] However, the embodiments are not limited thereto. The first to third light-emitting elements ED-1, ED-2, and ED-3 may emit light of the same wavelength, or at least one of them may emit light of different wavelengths. For example, the first to third light-emitting elements ED-1, ED-2, and ED-3 may all emit blue light.
[0127] According to one embodiment, the light-emitting regions PXA-R, PXA-G, and PXA-B in the display device DD can be arranged in a stripe pattern. (See reference...) Figure 1 Multiple red emitting regions PXA-R, multiple green emitting regions PXA-G, and multiple blue emitting regions PXA-B can be arranged along the second directional axis DR2. Alternatively, they can be arranged along the first directional axis DR1 in an alternating order of red emitting regions PXA-R, green emitting regions PXA-G, and blue emitting regions PXA-B.
[0128] exist Figure 1 and Figure 2 The illustration shows a scenario where the areas of the luminescent regions PXA-R, PXA-G, and PXA-B are all similar, but the embodiment is not limited to this. The areas of the luminescent regions PXA-R, PXA-G, and PXA-B can differ from each other depending on the wavelength of the emitted light. Furthermore, the areas of the luminescent regions PXA-R, PXA-G, and PXA-B can be represented as the areas when viewed from a plane defined by the first direction axis DR1 and the second direction axis DR2.
[0129] Furthermore, the arrangement of the luminescent regions PXA-R, PXA-G, and PXA-B is not limited to... Figure 1 As shown, the arrangement order of the red emitting areas PXA-R, green emitting areas PXA-G, and blue emitting areas PXA-B can be varied and provided according to the display quality characteristics required by the display device DD. For example, the arrangement of the emitting areas PXA-R, PXA-G, and PXA-B can be a pentile arrangement or a diamond arrangement.
[0130] Furthermore, the areas of the light-emitting regions PXA-R, PXA-G, and PXA-B can be different from each other. For example, in one embodiment, the area of the green light-emitting region PXA-G can be smaller than the area of the blue light-emitting region PXA-B, but the embodiment is not limited to this.
[0131] the following, Figures 3 to 6 This is a schematic cross-sectional view of a light-emitting element according to one embodiment. The light-emitting element ED according to one embodiment may include a first electrode EL1, a hole transport region HTR, a light-emitting layer EML, an electron transport region ETR, and a second electrode EL2, stacked sequentially.
[0132] compared to Figure 3 , Figure 4 A cross-sectional view of a light-emitting element (ED) according to an embodiment is shown, wherein the hole transport region (HTR) includes a hole injection layer (HIL) and a hole transport layer (HTL), and the electron transport region (ETR) includes an electron injection layer (EIL) and an electron transport layer (ETL). Furthermore, compared to... Figure 3 , Figure 5 A cross-sectional view of a light-emitting element (ED) according to an embodiment is shown, wherein the hole transport region (HTR) includes a hole injection layer (HIL), a hole transport layer (HTL), and an electron blocking layer (EBL), and the electron transport region (ETR) includes an electron injection layer (EIL), an electron transport layer (ETL), and a hole blocking layer (HBL). Compared to... Figure 4 , Figure 6 A cross-sectional view of a light-emitting element ED, including a capping layer CPL disposed on a second electrode EL2, is shown.
[0133] The first electrode EL1 is conductive. The first electrode EL1 can be formed of a metallic material, a metal alloy, or a conductive compound. The first electrode EL1 can be an anode or a cathode. However, the embodiments are not limited to this. Furthermore, the first electrode EL1 can be a pixel electrode. The first electrode EL1 can be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode. In the case where the first electrode EL1 is a transmissive electrode, the first electrode EL1 can include a transparent metal oxide, such as indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), indium tin zinc oxide (ITZO), etc. When the first electrode EL1 is a semi-transparent or reflective electrode, the first electrode EL1 may include at least one of Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF, Mo, Ti, W, their compounds and mixtures (e.g., a mixture of Ag and Mg), and materials having a multilayer structure such as LiF / Ca or LiF / Al. Alternatively, the first electrode EL1 may be a multilayer structure including a reflective or semi-transparent film formed from the aforementioned materials and a transparent conductive film formed from indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), indium tin zinc oxide (ITZO), etc. For example, the first electrode EL1 may have a three-layer structure of ITO / Ag / ITO, but is not limited thereto. Furthermore, the embodiments are not limited thereto; the first electrode EL1 may include the aforementioned metallic materials, a combination of two or more metallic materials selected from the aforementioned metallic materials, or oxides of the aforementioned metallic materials, etc. The thickness of the first electrode EL1 can be approximately up to approximately For example, the thickness of the first electrode EL1 can be approximately up to approximately
[0134] A hole transport region (HTR) is provided on the first electrode EL1. The hole transport region HTR may include at least one of a hole injection layer (HIL), a hole transport layer (HTL), a buffer layer or a light-emitting auxiliary layer (not shown), and an electron blocking layer (EBL). The thickness of the hole transport region HTR can be, for example, approximately... up to approximately
[0135] The hole transport region (HTR) can have a single-layer structure composed of a single substance, a single-layer structure composed of multiple different substances, or a multi-layer structure composed of multiple different substances.
[0136] For example, the hole transport region HTR can have a single-layer structure of hole injection layer HIL or hole transport layer HTL, or it can have a single-layer structure composed of hole injection material and hole transport material. Furthermore, the hole transport region HTR can have a single-layer structure composed of multiple different materials, or it can have a structure consisting of hole injection layer HIL / hole transport layer HTL, hole injection layer HIL / hole transport layer HTL / buffer layer (not shown), hole injection layer HIL / buffer layer (not shown), hole transport layer HTL / buffer layer (not shown), or hole injection layer HIL / hole transport layer HTL / electron blocking layer EBL, stacked sequentially from the first electrode EL1. However, the embodiments are not limited to these.
[0137] Hole transport regions (HTRs) can be formed using various methods, including vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) method, inkjet printing, laser printing, and laser-induced thermal imaging (LITI).
[0138] The hole transport region (HTR) may include compounds represented by the following chemical formula H-1.
[0139] [Chemical formula H-1]
[0140]
[0141] In the chemical formula H-1, L1 and L2 can each be independently a directly linked aryl group with 6 to 30 cyclic carbon atoms (substituted or unsubstituted) or a heteroaryl group with 2 to 30 cyclic carbon atoms (substituted or unsubstituted). a and b can each be independently an integer from 0 to 10. Furthermore, when a or b is an integer of 2 or more, multiple L1 and L2 can each be independently an aryl group with 6 to 30 cyclic carbon atoms (substituted or unsubstituted) or a heteroaryl group with 2 to 30 cyclic carbon atoms (substituted or unsubstituted).
[0142] In the chemical formula H-1, Ar1 and Ar2 can each be independently an aryl group with 6 to 30 cyclic carbon atoms (substituted or unsubstituted) or a heteroaryl group with 2 to 30 cyclic carbon atoms (substituted or unsubstituted). Furthermore, in the chemical formula H-1, Ar3 can be an aryl group with 6 to 30 cyclic carbon atoms (substituted or unsubstituted).
[0143] The compound represented by the chemical formula H-1 can be a monoamine compound. Alternatively, the compound represented by the chemical formula H-1 can be a diamine compound comprising at least one of Ar1 to Ar3, with an amino group as a substituent. Furthermore, the compound represented by the chemical formula H-1 can be a carbazole compound comprising at least one of Ar1 and Ar2, with a substituted or unsubstituted carbazole group, or a fluorene compound comprising at least one of Ar1 and Ar2, with a substituted or unsubstituted fluorene group.
[0144] A compound represented by the chemical formula H-1 can be represented by any one of the compounds in the following compound group H. However, the compounds listed in the following compound group H are exemplary, and compounds represented by the chemical formula H-1 are not limited to those shown in the following compound group H.
[0145] [Compound Group H]
[0146]
[0147] Hole transport region (HTR) may include phthalocyanine compounds such as copper phthalocyanine, N... 1 N 1 '-([1,1'-biphenyl]-4,4'-diyl)bis(N 1 -Phenyl-N 4 N 4 -di-m-tolylphenyl-1,4-diamine)(DNTPD:N 1 N 1 '-([1,1'-biphenyl]-4,4'-diyl)bis(N 1 -phenyl-N 4 N 4-di-m-tolylbenzene-1,4-diamine), 4,4',4"-[tris(3-methylphenyl)phenylamino]triphenylamine (m-MTDATA: 4,4',4"-[tris(3-methylphenyl)phenylamino]triphenylamine), 4,4',4"-tris(N,N-diphenylamino)triphenylamine (TDATA: 4,4',4"-Tris(N,N-diphenylamino)triphenylamine), 4,4',4"-tris[N-(2-naphthyl)-N-phenyl [Amino]-triphenylamine (2-TNATA: 4,4',4"-tris[N-(2-naphthyl)-N-phenylamino]-triphenylamine), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS: Poly(3,4-ethylenedioxythiophene) / Poly(4-styrenesulfonate)), polyaniline / dodecylbenzenesulfonic acid (PANI / DBSA: Polyaniline / Dodecylbenzenesulfonic acid), polyaniline / camphorsulfonic acid (PANI / CSA: Polyaniline / Camphor sulfonicacid), polyaniline / poly(4-styrenesulfonate) (PANI / PSS: Polyaniline / Poly(4-styrenesulfonate)), N,N'-di(naphthyl-1-yl)-N,N'-diphenyl - Benzidine (NPB: N,N'-di(naphthalene-l-yl)-N,N'-diphenyl-benzidine), triphenylamine-containing polyether ketone (TPAPEK), 4-Isopropyl-4'-methyldiphenyliodonium [Tetrakis(pentafluorophenyl)borate], and dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile, etc.
[0148] Hole transport regions (HTRs) can also include carbazole derivatives such as N-phenylcarbazole and polyvinylcarbazole, fluorene derivatives, triphenylamine derivatives such as N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (TPD: N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine), and N,N'-di(naphthyl-1-yl)-N,N'-diphenyl-benzidine (NPB: N,N'-di (naphthalene-l-yl)-N,N'-diphenyl-benzidine), 4,4'-cyclohexylbis[N,N-bis(4-methylphenyl)aniline] (TAPC: 4,4′-Cyclohexylidenebis[N,N-bis(4-methylphenyl)benzenamine]), 4,4'-bis[N,N'-(3-tolyl)amino]-3,3'-dimethylbiphenyl (HMTPD: 4,4'-Bis[N,N'-(3-tolyl)amino]-3,3'-dimethylbiphenyl), 1,3-bis(N-carbazolyl)benzene (mCP: 1,3-Bis(N-carbazolyl)benzene), etc.
[0149] Furthermore, the hole transport region may include 9-(4-tert-butylphenyl)-3,6-bis(triphenylsilyl)-9H-carbazole (CzSi: 9-(4-tert-Butylphenyl)-3,6-bis(triphenylsilyl)-9H-carbazole), 9-phenyl-9H-3,9'-bicarbazole (CCP: 9-phenyl-9H-3,9'-bicarbazole), or 1,3-bis(1,8-dimethyl-9H-carbazol-9-yl)benzene (mDCP: 1,3-bis(1,8-dimethyl-9H-carbazol-9-yl)benzene), etc.
[0150] The hole transport region HTR can be a compound comprising at least one of the hole injection layer HIL, the hole transport layer HTL, and the electron blocking layer EBL.
[0151] The thickness of the hole transport region (HTR) can be approximately up to approximately For example, it can be approximately up to approximately In the case where the hole transport region (HTR) includes a hole injection layer (HIL), the thickness of the hole injection layer (HIL) can be, for example, approximately... up to approximately In the case where the hole transport region (HTR) includes the hole transport layer (HTL), the thickness of the hole transport layer (HTL) can be approximately... up to approximately For example, in the case where the hole transport region HTR includes an electron blocking layer EBL, the thickness of the electron blocking layer EBL can be approximately up to approximately When the thicknesses of the hole transport region (HTR), hole injection layer (HIL), hole transport layer (HTL), and electron blocking layer (EBL) meet the ranges described above, satisfactory hole transport characteristics can be obtained without substantially increasing the driving voltage.
[0152] In addition to the substances mentioned above, the hole transport region (HTR) may also include a charge-generating substance to improve conductivity. The charge-generating substance may be uniformly or non-uniformly dispersed within the hole transport region (HTR). The charge-generating substance may, for example, be a p-dopant. The p-dopant may include, but is not limited to, at least one of metal halide compounds, quinone derivatives, metal oxides, and cyano-containing compounds. For example, p-dopers can include: metal halide compounds, such as CuI and RbI; quinone derivatives, such as tetracyanoquinone dimethylethane (TCNQ) and 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinone dimethylethane (F4-TCNQ); metal oxides, such as tungsten oxide and molybdenum oxide; and cyano-containing compounds, such as dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexanitrile (HAT-CN: dipyrazino[2, Examples of quinoxaline-2,3,6,7,10,11-hexacarbonitrile include 3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile and 4-[[2,3-bis[cyano-(4-cyano-2,3,5,6-tetrafluorophenyl)methylidene]cyclopropylidene]-cyanomethyl]-2,3,5,6-tetrafluorobenzonitrile, but the examples are not limited thereto.
[0153] As previously mentioned, in addition to the hole injection layer (HIL) and the hole transport layer (HTL), the hole transport region (HTR) may also include at least one of a buffer layer (not shown) and an electron blocking layer (EBL). The buffer layer (not shown) can improve light emission efficiency by compensating for the resonant distance based on the wavelength of light emitted from the light-emitting layer (EML). The material included in the buffer layer (not shown) can be any material capable of being included in the hole transport region (HTR). The electron blocking layer (EBL) is a layer that prevents electrons from being injected from the electron transport region (ETR) into the hole transport region (HTR).
[0154] The emissive layer EML is disposed on the hole transport region HTR. The emissive layer EML can, for example, have approximately... up to approximately Or approximately up to approximately The thickness of the light-emitting layer (EML) is as follows. The EML can have a single-layer structure composed of a single material, a single-layer structure composed of multiple different materials, or a multi-layer structure composed of multiple different materials.
[0155] In one embodiment of the light-emitting element ED, the light-emitting layer EML may include a polycyclic compound represented by the following chemical formula 1.
[0156] [Chemical Formula 1]
[0157]
[0158] In chemical formula 1, m and n can be 0 or 1 independently.
[0159] o can be an integer greater than 0 and less than 3. When m is 0, o can be an integer greater than 0 and less than 3. When m is 1, o can be either 0 or 1.
[0160] X1 to X4 can be NRa, CRbRc, O, or S, respectively. X1 to X4 can be the same or different from each other. For example, X1 to X4 can all be the same, X1 to X4 can all be different, or at least one of X1 to X4 can be different from the others. In one embodiment, at least one of X1 to X4 can be NRa, and Ra can be a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, or a substituted or unsubstituted terphenyl.
[0161] Y1 and Y2 can be independently NRd, O, or S, respectively. Y1 and Y2 can be the same or different from each other. In one embodiment, at least one of Y1 and Y2 can be NRd, and NRd can be a substituted phenyl group.
[0162] R1 to R 20 And Ra to Rd are, independently, hydrogen atoms, deuterium atoms, halogen atoms, substituted or unsubstituted amino groups, alkyl groups with 1 to 20 substituted or unsubstituted carbon atoms, aryl groups with 6 to 30 substituted or unsubstituted cyclic carbon atoms, or heteroaryl groups with 3 to 30 substituted or unsubstituted cyclic carbon atoms. R1 to R 20 They can all be the same or at least one can be different from the rest. In one embodiment, R1 to R 20 It can consist entirely of deuterium atoms. In one embodiment, R1 to R... 20 At least one of them can be an unsubstituted phenyl group. In one embodiment, R1 to R2... 20 At least one of them can be a substituted amino group.
[0163] Chemical formula 1 can be represented by chemical formula 2-1 or chemical formula 2-2.
[0164] [Chemical Formula 2-1]
[0165]
[0166] [Chemical Formula 2-2]
[0167]
[0168] Chemical formula 2-1 represents the case where m is 0 in chemical formula 1, and chemical formula 2-2 represents the case where m is 1 in chemical formula 1. In chemical formula 2-1, o can be an integer greater than 0 and less than 3. In chemical formula 2-2, o1 can be either 0 or 1.
[0169] Chemical formula 1 can be represented by any one of the following chemical formulas 3-1 to 3-3.
[0170] [Chemical Formula 3-1]
[0171]
[0172] [Chemical Formula 3-2]
[0173]
[0174] [Chemical Formula 3-3]
[0175]
[0176] In chemical formula 3-1, m is 0 or 1. When m is 1, Y1 and X1 are adjacent, and Y2 and X4 are adjacent. In chemical formula 3-2, m is 0 or 1. When m is 1, Y1 and X1 are meta-positioned, (R 19 ) n Y1 is adjacent to Y2, and X4 is between Y2 and X4. (R) 20 ) o1 It is adjacent to Y2. In chemical formula 3-3, m is 0, and Y1 and X1 are in the meta position. (R) 19 ) n The case where it is adjacent to X1.
[0177] In the chemical formula 3-1, the R 11 To R 18 At least one of them can be an unsubstituted phenyl group. R 11 To R 18 One of them can be an unsubstituted phenyl group, R 11 To R 18 The two in can be unsubstituted phenyl, R 11 To R 18The three can be unsubstituted phenyl or R 11 To R 18 All of them can be unsubstituted phenyl groups.
[0178] The chemical formula 1 can be represented by any one of the following chemical formulas 4-1 to 4-3.
[0179] [Chemical Formula 4-1]
[0180]
[0181] [Chemical Formula 4-2]
[0182]
[0183] [Chemical Formula 4-3]
[0184]
[0185] Chemical formula 4-1 refers to the case where Y1 is NRd1 and Y2 is NRd2 in chemical formula 1; chemical formula 4-2 refers to the case where Y1 and Y2 are O; and chemical formula 4-3 refers to the case where Y1 is S and Y2 is S.
[0186] In the aforementioned chemical formula 4-1, Rd1 and Rd2 are independently hydrogen atoms, deuterium atoms, halogen atoms, substituted or unsubstituted amino groups, alkyl groups with 1 to 20 carbon atoms (substituted or unsubstituted), aryl groups with 6 to 30 cyclic carbon atoms (substituted or unsubstituted), or heteroaryl groups with 3 to 30 cyclic carbon atoms (substituted or unsubstituted). d1 and R d2 They can be the same or different from each other.
[0187] In one embodiment, the light-emitting layer EML may include a polycyclic compound represented by the following chemical formula 1A.
[0188] [Chemical Formula 1A]
[0189]
[0190] In the chemical formula 1A, at least one pair of W1 to W6, consisting of two adjacent pairs selected from W1 to W3 and two adjacent pairs selected from W4 to W6, can be connected to the substituent represented by chemical formula 2A, and the rest can be independently CRe.
[0191] X1 to X4 can be NRa, CRbRc, O, or S, respectively. In one embodiment, at least one of X1 to X4 can be NRa, and Ra can be any one of a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, or a substituted or unsubstituted terphenyl.
[0192] R1 to R 10 Ra to Rc and Re can each independently be a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted amino group, an alkyl group with 1 to 20 carbon atoms (substituted or unsubstituted), an aryl group with 6 to 30 carbon atoms (substituted or unsubstituted), or a heteroaryl group with 3 to 30 carbon atoms (substituted or unsubstituted). X1 to X4 can be the same or different from each other, R1 to R 10 They can all be the same or at least one can be different from the rest. In one embodiment, R1 to R 10 It can consist entirely of deuterium atoms. In one embodiment, R1 to R... 10 At least one of them can be an unsubstituted phenyl group. In one embodiment, R1 to R2... 10 At least one of them can be a substituted amino group.
[0193] [Chemical Formula 2A]
[0194]
[0195] In the chemical formula 2A, Y can be NRd, O, or S.
[0196] R 11 To R 14 And Rd is independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted amino group, an alkyl group with 1 to 20 carbon atoms, a substituted or unsubstituted cyclic carbon group with 6 to 30 carbon atoms, or a heteroaryl group with 3 to 30 carbon atoms. 11 To R 14 They can be the same or different from each other. Chemical formula 2A It can be a portion that is bonded to any one of W1 to W6 of chemical formula 1A.
[0197] Chemical formula 2A can be represented by chemical formula 3A-1 or chemical formula 3A-2.
[0198] [Chemical Formula 3A-1]
[0199]
[0200] [Chemical Formula 3A-2]
[0201]
[0202] Y1 can be NRd1, O, or S, and can combine with W1 or W2. That is, Y1 can be in the ortho or meta position with X1 in a benzene ring with R2.
[0203] R 11a To R 14a And Rd1 can be independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted amino group, an alkyl group with 1 to 20 carbon atoms (substituted or unsubstituted), an aryl group with 6 to 30 cyclic carbon atoms (substituted or unsubstituted), or a heteroaryl group with 3 to 30 substituted or unsubstituted carbon atoms. R 11a To R 14a They can all be the same, or at least one can be different from the rest.
[0204] In chemical formula 3A-2, Y2 can be NRd2, O, or S, and can be combined with W5 or W6. That is, Y2 can be in the ortho or meta position with X4 in a benzene ring with R3.
[0205] R 11b To R 14b And Rd2 is independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted amino group, an alkyl group with 1 to 20 carbon atoms, a substituted or unsubstituted cyclic carbon group with 6 to 30 carbon atoms, or a heteroaryl group with 3 to 30 carbon atoms. 11b To R 14b They can all be the same, or at least one can be different from the rest.
[0206] If chemical formula 3A-1 is combined with the pair of W1 and W2, then chemical formula 3A-2 is combined with the pair of W5 and W6. If chemical formula 3A-1 is combined with the pair of W2 and W3, then chemical formula 3A-2 may not be combined with a pair consisting of two adjacent pairs selected from W4 to W6.
[0207] Y1 in chemical formula 3A-1 can be the same as Y2 in chemical formula 3A-2. That is, Y1 and Y2 can both be NRd, both be O, or both be S.
[0208] Chemical formula 2A is represented by the following chemical formulas 4A-1 to 4A-3.
[0209] [Chemical Formula 4A-1]
[0210]
[0211] [Chemical Formula 4A-2]
[0212]
[0213] [Chemical Formula 4A-3]
[0214]
[0215] Chemical formula 4A-1 represents the case where Y is NRd in chemical formula 2A, chemical formula 4A-2 represents the case where Y is O in chemical formula 2A, and chemical formula 4A-3 represents the case where Y is S in chemical formula 2A.
[0216] The luminescent layer EML may include at least one of the compounds shown in compound group 1 below.
[0217] [Compound Group 1]
[0218]
[0219]
[0220]
[0221]
[0222]
[0223]
[0224] In one embodiment, the polycyclic compound represented by chemical formula 1 can emit blue light.
[0225] exist Figures 3 to 6 In one embodiment of the light-emitting element (ED), the light-emitting layer (EML) may include a host and a dopant. A polycyclic compound according to one embodiment can be used as the dopant material. For example, a polycyclic compound according to one embodiment can be used as the dopant material for a light-emitting layer that emits thermally active delayed fluorescence.
[0226] In addition to the polycyclic compound of one embodiment, the luminescent layer EML may also include the luminescent layer material described below.
[0227] The luminescent layer (EML) may also include compounds represented by the following chemical formula E-1. Compounds represented by the following chemical formula E-1 can be used as fluorescent host materials.
[0228] [Chemical Formula E-1]
[0229]
[0230] In chemical formula E-1, R 31 To R 40It can be independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted silyl group, an alkyl group with 1 to 10 carbon atoms (substituted or unsubstituted), an aryl group with 6 to 30 carbon atoms (substituted or unsubstituted), or a heteroaryl group with 2 to 30 carbon atoms (substituted or unsubstituted), or it can be combined with adjacent groups to form a ring. Furthermore, R 31 To R 40 It can combine with adjacent groups to form saturated or unsaturated hydrocarbon rings.
[0231] In chemical formula E-1, c and d can each be an integer greater than 0 and less than 5.
[0232] Chemical formula E-1 can be represented by any one of the following compounds E1 to E19.
[0233]
[0234]
[0235] In one embodiment, the luminescent layer EML may further comprise a compound represented by the following chemical formula E-2a or E-2b. The compound represented by the following chemical formula E-2a or E-2b can be used as a phosphorescent host material.
[0236] [Chemical formula E-2a]
[0237]
[0238] In the chemical formula E-2a, 'a' can be an integer from 0 to 10, and 'La' can be a directly bonded, substituted or unsubstituted cyclic aryl group with 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted cyclic aryl group with 2 to 30 cyclic carbon atoms. Furthermore, when 'a' is an integer of 2 or more, multiple 'La's can each independently be a substituted or unsubstituted cyclic aryl group with 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted cyclic aryl group with 2 to 30 cyclic carbon atoms.
[0239] Furthermore, in chemical formula E-2a, A1 to A5 can each be independently N or CR. i R a To R iIt can be 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, an alkyl group with 1 to 20 carbon atoms, an alkenyl group with 2 to 20 carbon atoms, an aryl group with 6 to 30 carbon atoms, or a heteroaryl group with 2 to 30 carbon atoms, or it can be combined with adjacent groups to form a ring. R a To R i It can combine with adjacent groups to form hydrocarbon rings or heterocycles that include N, O, S, etc. as cyclic atoms.
[0240] Furthermore, in chemical formula E-2a, two or three selected from A1 to A5 can be N, and the rest can be CR. i .
[0241] [Chemical formula E-2b]
[0242]
[0243] In chemical formula E-2b, Cbz1 and Cbz2 can be independently either an unsubstituted carbazole group or a carbazole group substituted with an aryl group having 6 to 30 cyclic carbon atoms. b It can be a directly bonded, substituted or unsubstituted cyclic aryl group with 6 to 30 carbon atoms, or a substituted or unsubstituted cyclic aryl group with 2 to 30 carbon atoms. b can be an integer from 0 to 10. When b is an integer of 2 or more, multiple L... b It can be independently a cyclic aryl group with 6 to 30 substituted or unsubstituted carbon atoms, or a heteroaryl group with 2 to 30 substituted or unsubstituted carbon atoms.
[0244] A compound represented by chemical formula E-2a or E-2b may be 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 exemplary, and compounds represented by chemical formula E-2a or E-2b are not limited to those shown in the following compound group E-2.
[0245] [Compound Group E-2]
[0246]
[0247]
[0248] The luminescent layer EML can also include common materials known in the art as the host material. For example, the luminescent layer EML can include bis[2-(diphenylphosphino)phenyl]ether oxide (DPEPO: Bis[2-(diphenylphosphino)phenyl]ether oxide), 4,4'-bis(carbazol-9-yl)biphenyl (CBP: 4,4'-Bis(carbazol-9-yl)biphenyl), 1,3-bis(carbazol-9-yl)benzene (mCP: 1,3-Bis(carbazol-9-yl)benzene), 2,8-bis(diphenylphosphoryl)dibenzo[b,d]furan (PPF: 2,8-Bis(diphenylphosphoryl)dibenzo[b,d]furan). The main substance is at least one of uran), 4,4',4”-tris(carbazol-9-yl)-triphenylamine (TCTA: 4,4',4”-Tris(carbazol-9-yl)-triphenylamine) and 1,3,5-tris(1-phenyl-1H-benzo[d]imidazol-2-yl)benzene (TPBi: 1,3,5-tris(1-phenyl-1H-benzo[d]imidazol-2-yl)benzene).However, it is not limited to this; for example, tris(8-hydroxyquinolino)aluminum (Alq3: tris(8-hydroxyquinolino)aluminum), 4,4'-bis(N-carbazolyl)-1,1'-biphenyl (CBP: 4,4'-bis(N-carbazolyl)-1,1'-biphenyl), poly(N-vinylcabazole) (PVK: poly(N-vinylcabazole)), 9,10-di(naphthalene-2-yl)anthracene (ADN: 9,10-di(naphthalene-2-yl)anthracene), 4,4',4"-tris(carbazol-9-yl)-triphenylamine (TCTA: 4,4',4"-Tris(carbazol-9-yl)-triphenylamine), and 1,3,5-tris(N-phenylbenzimidazol-2-yl)benzene (TP) can be used. Bi: 1,3,5-tris(N-phenylbenzimidazol-2-yl)benzene), 2-tert-butyl-9,10-di(naphth-2-yl)anthracene (TBADN: 2-tert-butyl-9,10-di(naphth-2-yl)anthracene), distyrylarylene (DSA: distyrylarylene), 4,4'-bis(9-carbazolyl)-2,2'-dimethylbiphenyl (CDBP: 4,4′-bis(9-carbazolyl)-2,2′-dimethyl-biphenyl), 2-methyl-9,10-bis(naphth-2-yl)anthracene (MADN: 2-Methyl-9,10-bis(naphthalen-2-yl)anthracene), hexaphenylcyclotriphosphazene (CP1: Hexaphenyl) Cyclotriphosphazene, 1,4-bis(triphenylsilyl)benzene (UGH2: 1,4-Bis(triphenylsilyl)benzene), hexaphenylcyclotrisiloxane (DPSiO3: Hexaphenylcyclotrisiloxane), octaphenylcyclotetrasiloxane (DPSiO4: Octaphenylcyclotetrasiloxane), 2,8-bis(diphenylphosphoryl)dibenzofuran (PPF: 2,8-Bis(diphenylphosphoryl)dibenzofuran) and other similar compounds are used as the main materials.
[0249] The luminescent layer (EML) may also include compounds represented by the chemical formulas Ma or Mb. These compounds can be used as phosphorescent dopant materials.
[0250] [Chemical formula Ma]
[0251]
[0252] In the chemical formula Ma, Y1 to Y4 and Z1 to Z4 are each independently CR1 or N, and R1 to R4 can each be independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted amino group, a substituted or unsubstituted thio group, a substituted or unsubstituted oxygen group, an alkyl group with 1 to 20 carbon atoms, an alkenyl group with 2 to 20 carbon atoms, an aryl group with 6 to 30 carbon atoms, or a heteroaryl group with 2 to 30 carbon atoms, or can be combined with 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, when m is 0, n is 3; when m is 1, n is 2.
[0253] Compounds represented by the chemical formula Ma can be used as red or green phosphorescent dopants.
[0254] Compounds represented by the chemical formula Ma can be represented by any one of the following compounds M-a1 to M-a19. However, compounds M-a1 to M-a19 are exemplary, and compounds represented by the chemical formula Ma are not limited to those represented by compounds M-a1 to M-a19.
[0255]
[0256]
[0257] Compounds M-a1 and M-a2 can be used as red dopant materials, while compounds M-a3 to M-a5 can be used as green dopant materials.
[0258] [Chemical formula Mb]
[0259]
[0260] In the chemical formula Mb, Q1 to Q4 are independently C or N, and C1 to C4 are independently hydrocarbon rings with 5 to 30 substituted or unsubstituted carbon atoms, or heterocycles with 2 to 30 substituted or unsubstituted carbon atoms. 21 To L 24 Each independently constitutes a direct combination, The substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, the substituted or unsubstituted cyclic aryl group having 6 to 30 carbon atoms, or the substituted or unsubstituted cyclic aryl group having 2 to 30 carbon atoms, wherein e1 to e4 are independently 0 or 1. R 31 To R 39 Each of the following groups is independently composed of a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted amino group, an alkyl group with 1 to 20 substituted or unsubstituted carbon atoms, an aryl group with 6 to 30 substituted or unsubstituted cyclic carbon atoms, or a heteroaryl group with 2 to 30 substituted or unsubstituted cyclic carbon atoms, or a ring formed by combining with adjacent groups, wherein d1 to d4 are independently integers of 0 to 4.
[0261] Compounds represented by the chemical formula Mb can be used as blue or green phosphorescent dopants.
[0262] Compounds represented by the chemical formula Mb can be represented by any of the compounds listed below. However, the compounds listed below are exemplary, and compounds represented by the chemical formula Mb are not limited to those represented by the compounds listed below.
[0263]
[0264] In the compound, R, R 38 and R 39 It can be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted amino group, an alkyl group with 1 to 20 carbon atoms, a substituted or unsubstituted cyclic carbon group with 6 to 30 carbon atoms, or a heteroaryl group with 2 to 30 carbon atoms.
[0265] The luminescent layer (EML) may include a compound represented by any one of the following chemical formulas: Fa to Fc. Compounds represented by the following chemical formulas: Fa to Fc can be used as fluorescent dopant materials.
[0266] [Chemical formula Fa]
[0267]
[0268] In the chemical formula Fa, the components are selected from R. a To R j The two in can be replaced independently by *-NAr1Ar2. In R a To R jIn *-NAr1Ar2, the remaining groups not substituted by * can be independently hydrogen atoms, deuterium atoms, halogen atoms, cyano groups, substituted or unsubstituted amino groups, alkyl groups with 1 to 20 carbon atoms (substituted or unsubstituted), aryl groups with 6 to 30 cyclic carbon atoms (substituted or unsubstituted), or heteroaryl groups with 2 to 30 cyclic carbon atoms (substituted or unsubstituted). In *-NAr1Ar2, Ar1 and Ar2 can be independently independently aryl groups with 6 to 30 cyclic carbon atoms (substituted or unsubstituted) or heteroaryl groups with 2 to 30 cyclic carbon atoms (substituted or unsubstituted). For example, at least one of Ar1 and Ar2 can be a heteroaryl group including O or S as a cyclic atom.
[0269] [Chemical formula Fb]
[0270]
[0271] In the chemical formula Fb, R a and R b It can be a hydrogen atom, a deuterium atom, an alkyl group with 1 to 20 carbon atoms (substituted or unsubstituted), an alkenyl group with 2 to 20 carbon atoms (substituted or unsubstituted), an aryl group with 6 to 30 carbon atoms (substituted or unsubstituted), or a heteroaryl group with 2 to 30 carbon atoms (substituted or unsubstituted), or it can be combined with adjacent groups to form a ring.
[0272] In the chemical formula Fb, U and V can be, independently, either substituted or unsubstituted cyclic hydrocarbon rings with 5 to 30 carbon atoms, or substituted or unsubstituted cyclic heterocycles with 2 to 30 carbon atoms.
[0273] In the chemical formula Fb, the number of rings represented by U and V can be independently 0 or 1. For example, in the chemical formula Fb, when the number of U or V is 1, it means that in the part described as U or V, one ring forms a condensed ring; when the number of U or V is 0, it means that there are no rings described as U or V. Specifically, 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 condensed ring of the fluorene core having the chemical formula Fb can be a tetracyclic cyclic compound. Furthermore, when the number of U and V is both 0, the condensed ring of the fluorene core having the chemical formula Fb can be a tricyclic cyclic compound. Furthermore, when the number of U and V is both 1, the condensed ring of the fluorene core having the chemical formula Fb can be a pentacyclic cyclic compound.
[0274] [Chemical formula Fc]
[0275]
[0276] In the chemical formula Fc, A1 and A2 are independently O, S, Se, or NR, respectively. m R m It can be a hydrogen atom, a deuterium atom, an alkyl group with 1 to 20 substituted or unsubstituted carbon atoms, an aryl group with 6 to 30 substituted or unsubstituted cyclic carbon atoms, or a heteroaryl group with 2 to 30 substituted or unsubstituted cyclic carbon atoms. R1 to R 11 It is independently composed of a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted amino group, a substituted or unsubstituted boron group, a substituted or unsubstituted oxygen group, a substituted or unsubstituted thio group, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, or a heteroaryl group having 2 to 30 carbon atoms, or a cyclic group formed by combining with adjacent groups to form a ring.
[0277] In the chemical formula Fc, A1 and A2 can independently combine with substituents of adjacent rings to form condensed rings. For example, when A1 and A2 are independently NR... m In this case, A1 can combine with R4 or R5 to form a ring. Furthermore, A2 can combine with R7 or R8 to form a ring.
[0278] In one embodiment, the light-emitting layer (EML) may include styrene derivatives as known dopant materials (e.g., 1,4-bis[2-(3-N-ethylcarbazolyl)vinyl]benzene (BCzVB: 1,4-bis[2-(3-N-ethylcarbazolyl)vinyl]benzene), 4-(di-p-tolylamino)-4'-[(di-p-tolylamino)styryl]stilbene (DPAVB: 4-(di-p-tolylamino)-4'-[(di-p-tolylamino)styryl]stilbene), N-(4-((E)-2-(6-((E)-4-(diphenylamino)styryl)naphthyl-2-yl)vinyl)phenyl)-N-phenylaniline (N-BDAVBi: N-(4-((E)-2-(6-((E)-4-(diphenylamino)styryl)naphthyl ... Phthalen-2-yl)vinyl)phenyl)-N-phenylbenzenamine), 4,4'-bis[2-(4-(N,N-diphenylamino)phenyl)vinyl]biphenyl (DPAVBi: 4,4'-bis[2-(4-(N,N-diphenylamino)phenyl)vinyl]biphenyl), perylene and its derivatives (e.g., 2,5,8,11-tetra-t-butylperylene (TBP: 2,5,8,11-Tetra-t-butylperylene)), pyrene and its derivatives (e.g., 1,1'-dipyrene, 1,4-dipyrenylbenzene, 1,4-bis(N,N-diphenylamino)pyrene, etc.).
[0279] The light-emitting layer (EML) can include known phosphorescent dopant materials. For example, phosphorescent dopant can 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). Specifically, iridium(III)bis(4,6-difluorophenylpyridinato-N,C2)pyridinecarboxylate (FIrpic: iridium(III)bis(4,6-difluorophenylpyridinato-N,C2)picolinate), iridium(III)bis(2,4-difluorophenylpyridinato)-tetrakis(1-pyrazolyl)borate iridium(III) (FIr6: Bis(2,4-difluorophenylpyridinato)-tetrakis(1-pyrazolyl)borate iridium(III)), or platinum octaethyl porphyrin (PtOEP: platinumoctaethyl porphyrin) can be used as phosphorescent dopants. However, the examples are not limited to these.
[0280] The luminescent layer (EML) can include quantum dot materials. The core of the quantum dots can be selected from group II-VI compounds, group III-VI compounds, group I-III-VI compounds, group III-V compounds, group III-II-V compounds, group IV-VI compounds, group IV elements, group IV compounds, and combinations thereof.
[0281] Group II-VI compounds can be selected from the group consisting of the following compounds: binary compounds, selected from the group consisting of CdSe, CdTe, CdS, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, MgSe, MgS, and mixtures thereof; ternary compounds, selected from the group consisting of CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, and CdZnSe. The group consisting of CdZnTe, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, MgZnSe, MgZnS and mixtures thereof; and quaternary compounds selected from the group consisting of HgZnTeS, CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe, HgZnSTe and mixtures thereof.
[0282] III-VI group compounds may include: binary compounds, such as In2S3, In2Se3, etc.; ternary compounds, such as InGaS3, InGaSe3, etc.; or any combination thereof.
[0283] Group I-III-VI compounds can be selected from: ternary compounds, selected from the group consisting of AgInS, AgInS2, CuInS, CuInS2, AgGaS2, CuGaS2, CuGaO2, AgGaO2, AgAlO2 and mixtures thereof; or quaternary compounds, such as AgInGaS2 and CuInGaS2.
[0284] Group III-V compounds may be selected from the group consisting of: binary compounds selected from GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, InSb, and mixtures thereof; ternary compounds selected from GaNP, GaNAs, GaNSb, GaPAs, GaPSb, AlNP, AlNAs, AlNSb, AlPAs, AlPSb, InGaP, InAlP, InNP, InNAs, InNSb, InPAs, InPSb, and mixtures thereof; and quaternary compounds selected from GaAlNP, GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNP, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs, InAlPSb, and mixtures thereof. Furthermore, Group III-V compounds may also include Group II metals. For example, InZnP, etc., can be selected as a group III-II-V compound.
[0285] Group IV-VI compounds can be selected from the group consisting of: binary compounds selected from SnS, SnSe, SnTe, PbS, PbSe, PbTe, and mixtures thereof; ternary compounds selected from SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, SnPbTe, and mixtures thereof; and quaternary compounds selected from SnPbSSe, SnPbSeTe, SnPbSTe, and mixtures thereof. Group IV elements can be selected from the group consisting of Si, Ge, and mixtures thereof. Group IV compounds can be binary compounds selected from the group consisting of SiC, SiGe, and mixtures thereof.
[0286] At this point, binary, ternary, or quaternary compounds can exist within the particle at a uniform concentration, or they can exist dispersedly within the same particle with locally different concentration distributions. Furthermore, they can possess a core / shell structure with one quantum dot surrounding other quantum dots. In this core / shell structure, the concentration of elements in the shell decreases with increasing proximity to the core, exhibiting a concentration gradient.
[0287] In some embodiments, the quantum dot may have a core-shell structure comprising a core containing the aforementioned nanocrystals and a shell surrounding the core. The shell of the quantum dot may function as a protective layer to prevent chemical degradation of the core and maintain semiconductor properties, and / or as a charging layer to impart electrophoretic properties to the quantum dot. The shell may be a single layer or multiple layers. Examples of the shell of the quantum dot may include metal or non-metal oxides, semiconductor compounds, or combinations thereof.
[0288] For example, the oxides of the metal or nonmetal can be exemplified as: binary compounds, such as SiO2, Al2O3, TiO2, ZnO, MnO, Mn2O3, Mn3O4, CuO, FeO, Fe2O3, Fe3O4, CoO, Co3O4, NiO, etc.; or ternary compounds, such as MgAl2O4, CoFe2O4, NiFe2O4, CoMn2O4, etc., but the present invention is not limited thereto.
[0289] Furthermore, 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, AlSb, etc., but the present invention is not limited thereto.
[0290] Quantum dots can have a full width at half maximum (FWHM) of an emission wavelength spectrum of approximately 45 nm or less, preferably approximately 40 nm or less, and more preferably approximately 30 nm or less. Within this range, color purity or color reproducibility can be improved. Furthermore, light emitted by such quantum dots is emitted in all directions, thereby improving the viewing angle.
[0291] Furthermore, the morphology of quantum dots is not particularly restricted, as long as it is a morphology commonly used in the field. More specifically, spherical, pyramidal, multi-arm, or cubic nanoparticles, nanotubes, nanowires, nanofibers, nanoplate particles, and other morphologies can be used.
[0292] Quantum dots can adjust the color of the emitted light according to their particle size, thus they can have a variety of emitting colors such as blue, red, and green.
[0293] exist Figures 3 to 6 In one embodiment of the light-emitting element ED, an electron transport region (ETR) is provided on the light-emitting layer (EML). The electron transport region (ETR) may include at least one of the hole blocking layer (HBL), the electron transport layer (ETL), and the electron injection layer (EIL), but the embodiment is not limited thereto.
[0294] The electron transport region (ETR) can have a single-layer structure composed of a single substance, a single-layer structure composed of multiple different substances, or a multi-layer structure composed of multiple different substances.
[0295] For example, the electron transport region (ETR) can have a single-layer structure of either the electron injection layer (EIL) or the electron transport layer (ETL), or it can have a single-layer structure composed of an electron injection material and an electron transport material. Furthermore, the ETR can have a single-layer structure composed of multiple different materials, or it can have a structure of electron transport layer ETL / electron injection layer EIL, hole blocking layer HBL / electron transport layer ETL / electron injection layer EIL stacked sequentially from the emitting layer (EML), but it is not limited to these. The thickness of the ETR can, for example, be approximately... up to approximately
[0296] Electron transport regions (ETRs) can be formed using various methods, including vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) method, inkjet printing, laser printing, and laser-induced thermal imaging (LITI).
[0297] The electron transport region (ETR) may include compounds represented by the following chemical formula ET-1.
[0298] [Chemical formula ET-1]
[0299]
[0300] In the chemical formula ET-1, at least one of X1 to X3 is N, and the rest are CR. a R aAr1 to Ar3 can be hydrogen atoms, deuterium atoms, alkyl groups with 1 to 20 substituted or unsubstituted carbon atoms, aryl groups with 6 to 30 substituted or unsubstituted cyclic carbon atoms, or heteroaryl groups with 2 to 30 substituted or unsubstituted cyclic carbon atoms.
[0301] In the chemical formula ET-1, a to c can each be an integer from 0 to 10 independently. In the chemical formula ET-1, L1 to L3 can each be an arylene group with 6 to 30 substituted or unsubstituted cyclic carbon atoms, or a heteroarylene group with 2 to 30 substituted or unsubstituted cyclic carbon atoms, respectively, through direct linkage. Furthermore, when a to c are integers of 2 or more, L1 to L3 can each be an arylene group with 6 to 30 substituted or unsubstituted cyclic carbon atoms, or a heteroarylene group with 2 to 30 substituted or unsubstituted cyclic carbon atoms, respectively.
[0302] Electron transport region (ETR) compounds may include anthracene compounds. However, they are not limited to this; for example, ETRs may include tris(8-hydroxyquinolino)aluminum, 1,3,5-tris[(3-pyridyl)-phen-3-yl]benzene, and 2,4,6-tris(3'-(pyridin-3-yl)biphenyl-3-yl)-1,3,5-triazine. ine), 2-(4-(N-phenylbenzimidazol-1-yl)phenyl)-9,10-dinaphthylanthracene, 1,3,5-tri(1-phenyl-1H-benzo[d]imidazol-2-yl)benzene (TPBi: 1,3,5-tri(1-phenyl-1H-benzo[d]imidazol-2-yl)benzene), 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP: 2,9-Dim ethyl-4,7-diphenyl-1,10-phenanthroline), 4,7-diphenyl-1,10-phenanthroline (Bphen: 4,7-Diphenyl-1,10-phenanthroline), 3-(4-biphenyl)-4-phenyl-5-tert-butylphenyl-1,2,4-triazole (TAZ: 3-(4-Biphenylyl)-4-phenyl-5-tert-butylphenyl-1,2,4-triazole), 4-(naphthyl-1-yl)-3,5-diphenyl-4H-1,2,4-triazole (NTAZ: 4-(Naphthalen-1-yl)-3,5-diphenyl-4H-1,2,4-triazole), 2-(4-biphenyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (tBu-PBD: 2-(4-Biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole), bis(2-methyl-8-quinolinolato-N1,O8)-(1,1'-biphenyl-4-hydroxy)aluminum (BAlq: Bis(2-methyl-8-quinolinolato-N1,O8)-(1,1'-Biphenyl-4-olate)aluminum), bis(benzoquinolin-10-olate)beryllium (Bebq2: berylliumbis(benzoquinolin-10-olate)), 9,10-di(naphthalene-2-yl)anthracene (ADN: 9,10-di(naphthalene-2-yl)anthracene), 1,3-bis[3,5-di(pyridin-3-yl)phenyl]benzene (BmPyPhB: (1,3-Bis[3,5-di(pyridin-3-yl)phenyl]benzene), and mixtures thereof.
[0303] The electron transport region (ETR) may include at least one of the following compounds: ET1 to ET36.
[0304]
[0305]
[0306]
[0307]
[0308] Furthermore, the electron transport region (ETR) can include: metal halides, such as LiF, NaCl, CsF, RbCl, RbI, CuI, KI, etc.; lanthanide group metals, such as Yb, etc., and can include co-deposited materials of said metal halides and lanthanide group metals. For example, the ETR can include KI:Yb, RbI:Yb, etc., as co-deposited materials. In addition, the ETR can use metal oxides such as Li₂O, BaO, or lithium 8-hydroxyl-Lithiumquinolate (Liq), but the embodiments are not limited to these. The ETR can also be composed of a mixture of electron transport material and insulating organometallic salt. The organometallic salt can be a material with an energy band gap of approximately 4 eV or higher. Specifically, for example, organometallic salts may include metal acetate, metal benzoate, metal acetoacetate, metal acetylacetonate, or metal stearate.
[0309] In addition to the materials mentioned above, the electron transport region (ETR) may also include at least one of 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP: 2,9-Dimethyl-4,7-diphenyl-1,10-phenanthroline) and 4,7-diphenyl-1,10-phenanthroline (Bphen: 4,7-Diphenyl-1,10-phenanthroline), but the embodiments are not limited thereto.
[0310] The electron transport region (ETR) can be a compound comprising at least one of the electron injection layer (EIL), the electron transport layer (ETL), and the hole blocking layer (HBL).
[0311] In the case where the electron transport region ETR includes the electron transport layer ETL, the thickness of the electron transport layer ETL can be approximately up to approximately For example, it can be approximately up to approximately When the thickness of the electron transport layer (ETL) meets the range described above, satisfactory electron transport characteristics can be obtained without a substantial increase in the driving voltage. When the electron transport region (ETL) includes an electron injection layer (EIL), the thickness of the EIL can be approximately... up to approximately About up to approximately When the thickness of the electron injection layer (EIL) meets the range described above, satisfactory electron injection characteristics can be obtained without a substantial increase in the driving voltage.
[0312] The second electrode EL2 is provided on the electron transport region ETR. The second electrode EL2 can be a common electrode. The second electrode EL2 can be a cathode or an anode, but the embodiments are not limited thereto. For example, if the first electrode EL1 is an anode, the second electrode EL2 can be a cathode, and if the first electrode EL1 is a cathode, the second electrode EL2 can be an anode.
[0313] The second electrode EL2 can be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode. In the case where the second electrode EL2 is a transmissive electrode, it can be composed of a transparent metal oxide, such as indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), or indium tin zinc oxide (ITZO).
[0314] When the second electrode EL2 is a semi-transparent or reflective electrode, it may include at least one of Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF, Mo, Ti, Yb, W, compounds and mixtures thereof (e.g., AgMg, AgYb, or MgYb), and materials having a multilayer structure such as LiF / Ca or LiF / Al. Alternatively, the second electrode EL2 may be a multilayer structure comprising a reflective or semi-transparent film formed from the aforementioned materials and a transparent conductive film formed from indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), indium tin zinc oxide (ITZO), etc. For example, the second electrode EL2 may include the aforementioned metallic materials, a combination of two or more metallic materials selected from the aforementioned metallic materials, or oxides of the aforementioned metallic materials.
[0315] Although not shown, the second electrode EL2 can be connected to the auxiliary electrode. If the second electrode EL2 is connected to the auxiliary electrode, the resistance of the second electrode EL2 can be reduced.
[0316] Furthermore, in one embodiment, a capping layer CPL may be disposed on the second electrode EL2 of the light-emitting element ED. The capping layer CPL may include multiple layers or a single layer.
[0317] In one embodiment, the capping layer CPL can be an organic layer or an inorganic layer. For example, when the capping layer CPL includes inorganic materials, the inorganic materials may include: alkali metal compounds, such as LiF; alkaline earth metal compounds, such as MgF2; and SiON, SiN. x SiO y wait.
[0318] For example, when the capping layer CPL includes an organic compound, the organic compound may include α-NPD, NPB, TPD, m-MTDATA, Alq3, CuPc, N4,N4,N4',N4'-tetra(biphenyl-4-yl)biphenyl-4,4'-diamine (TPD15: N4,N4,N4',N4'-tetra(biphenyl-4-yl)biphenyl-4,4'-diamine), 4,4',4"-tris(carbazol-9-yl)triphenylamine (TCTA: 4,4',4"-Tris(carbazol-9-yl)triphenylamine), etc., or may include epoxy resins or acrylates such as methacrylates. However, the embodiments are not limited thereto, and the capping layer CPL may include at least one of compounds P1 to P5 as described below.
[0319]
[0320]
[0321] Furthermore, the refractive index of the capping layer CPL can be 1.6 or higher. Specifically, for light in the wavelength range of 550 nm to 660 nm, the refractive index of the capping layer CPL can be 1.6 or higher.
[0322] Figure 7 as well as Figure 8 These are cross-sectional views of a display device according to one embodiment. Hereinafter, in conjunction with the reference... Figure 7 and Figure 8 When describing a display device according to one embodiment, the description will not repeat the descriptions of the above-described display device. Figures 1 to 6 The content repeated in the explanation should be explained mainly based on the differences.
[0323] Reference Figure 7 According to one embodiment, the display device DD may include a display panel DP including a display element layer DP-ED, a light control layer CCL and a color filter layer CFL disposed on the display panel DP.
[0324] exist Figure 7 In one embodiment shown, the display panel DP may include a base layer BS, a circuit layer DP-CL disposed on the base layer BS, and a display element layer DP-ED, wherein the display element layer DP-ED may include a light-emitting element ED.
[0325] The light-emitting element (ED) may include: a first electrode EL1; a hole transport region HTR disposed on the first electrode EL1; a light-emitting layer EML disposed on the hole transport region HTR; an electron transport region ETR disposed on the light-emitting layer EML; and a second electrode EL2 disposed on the electron transport region ETR. Furthermore, Figure 7 The structure of the light-emitting element ED shown can be applied in the same way as described above. Figures 3 to 6 The structure of the light-emitting element.
[0326] Reference Figure 7 The emissive layer EML can be disposed within the opening OH defined by the pixel defining film PDL. For example, the emissive layers EML provided corresponding to each emissive region PXA-R, PXA-G, and PXA-B, divided by the pixel defining film PDL, can emit light of the same wavelength. In a display device DD according to one embodiment, the emissive layer EML can emit blue light. Furthermore, unlike the illustrated case, in one embodiment, the emissive layer EML can be provided as a common layer throughout the entire emissive region PXA-R, PXA-G, and PXA-B.
[0327] The light control layer (CCL) can be disposed on the display panel (DP). The light control layer (CCL) may include a light converter. The light converter may be a quantum dot or a phosphor, etc. The light converter can convert the wavelength of the received light and emit it. That is, the light control layer (CCL) may be a layer including quantum dots or a layer including phosphors.
[0328] The optical control layer (CCL) may include multiple optical control units CCP1, CCP2, and CCP3. The optical control units CCP1, CCP2, and CCP3 may be spaced apart from each other.
[0329] Reference Figure 7 A segmented pattern BMP can be arranged between the light control units CCP1, CCP2, and CCP3 that are spaced apart from each other, but the embodiment is not limited to this. Although in Figure 7 The diagram shows a case where the segmentation pattern BMP does not overlap with the light control units CCP1, CCP2, and CCP3, but the edges of the light control units CCP1, CCP2, and CCP3 may overlap with at least a portion of the segmentation pattern BMP.
[0330] The light control layer CCL may include: a first light control unit CCP1, including a first quantum dot QD1 that converts first-color light provided by the light-emitting element ED into second-color light; a second light control unit CCP2, including a second quantum dot QD2 that converts first-color light into third-color light; and a third light control unit CCP3 that transmits first-color light.
[0331] In one embodiment, the first light control unit CCP1 can provide red light as a second color light, and the second light control unit CCP2 can provide green light as a third color light. The third light control unit CCP3 can transmit blue light, which is the first color light provided from the light-emitting element ED, to provide blue light. For example, the first quantum dot QD1 can be a red quantum dot, and the second quantum dot QD2 can be a green quantum dot. The same content as described above can be applied to quantum dots QD1 and QD2.
[0332] Furthermore, the optical control layer CCL may also include a scatterer SP. The first optical control unit CCP1 may include a first quantum dot QD1 and a scatterer SP, the second optical control unit CCP2 may include a second quantum dot QD2 and a scatterer SP, and the third optical control unit CCP3 may not include a quantum dot but may include a scatterer SP.
[0333] The scatterer SP can be inorganic particles. For example, the scatterer SP can include at least one of TiO2, ZnO, Al2O3, SiO2, and hollow silica. The scatterer SP can include any one of TiO2, ZnO, Al2O3, SiO2, and hollow silica, or it can be a mixture of two or more substances selected from TiO2, ZnO, Al2O3, SiO2, and hollow silica.
[0334] Each of the first light control unit CCP1, the second light control unit CCP2, and the third light control unit CCP3 may include base resins BR1, BR2, and BR3 for dispersing quantum dots QD1, QD2, and scatterers SP. In one embodiment, the first light control unit CCP1 may include the first quantum dots QD1 and scatterers SP dispersed in the first base resin BR1, the second light control unit CCP2 may include the second quantum dots QD2 and scatterers SP dispersed in the second base resin BR2, and the third light control unit CCP3 may include scatterers SP dispersed in the third base resin BR3. The base resins BR1, BR2, and BR3, as media for dispersing quantum dots QD1, QD2, and scatterers SP, may be composed of various resin compositions commonly referred to as binders. For example, the base resins BR1, BR2, and BR3 may be acrylic resins, polyurethane resins, silicone resins, epoxy resins, etc. The base resins BR1, BR2, and BR3 may be transparent resins. In one embodiment, the first base resin BR1, the second base resin BR2, and the third base resin BR3 may be the same or different.
[0335] The light control layer CCL may include 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 may be disposed on the light control units CCP1, CCP2, and CCP3 to prevent them from being exposed to moisture / oxygen. Furthermore, the barrier layer BFL1 may cover the light control units CCP1, CCP2, and CCP3. Additionally, a barrier layer BFL2 may also be provided between the light control units CCP1, CCP2, and CCP3 and the filters CF1, CF2, and CF3 (described later).
[0336] Barrier layers BFL1 and BFL2 may include at least one inorganic layer. That is, barrier layers BFL1 and BFL2 may be formed from inorganic materials. For example, barrier layers BFL1 and BFL2 may be formed from silicon nitride, aluminum nitride, zirconium nitride, titanium nitride, hafnium nitride, tantalum nitride, silicon oxide, aluminum oxide, titanium oxide, tin oxide, cerium oxide, and silicon nitride, or a metal thin film that ensures light transmittance. Furthermore, barrier layers BFL1 and BFL2 may also include an organic film. Barrier layers BFL1 and BFL2 may consist of a single layer or multiple layers.
[0337] In one embodiment of the display device DD, the color filter layer CFL can be disposed on the light control layer CCL. For example, the color filter layer CFL can be disposed directly on the light control layer CCL. In this case, the blocking layer BFL2 can be omitted.
[0338] The color filter layer CFL may include a light-shielding portion BM and filters CF1, CF2, and CF3. Furthermore, the color filter layer CFL may also include a blocking layer BFL2. The color filter layer CFL may include: a first filter CF1 that allows the transmission of a second color light; a second filter CF2 that allows the transmission of a third color light; and a third filter CF3 that allows the transmission of a first color light. For example, the first filter CF1 may be a red filter, the second filter CF2 may be a green filter, and the third filter CF3 may be a blue filter. Each of the filters CF1, CF2, and CF3 may include a photosensitive polymer and a pigment or dye. The first filter CF1 may include a red pigment or dye, the second filter CF2 may include a green pigment or dye, and the third filter CF3 may include a blue pigment or dye. However, the embodiments are not limited thereto; the third filter CF3 may not include any pigment or dye. The third filter CF3 may include a photosensitive polymer and may not include any pigment or dye. The third filter CF3 may be transparent. The third filter CF3 can be formed from a transparent photosensitive resin.
[0339] Furthermore, in one embodiment, the first filter CF1 and the second filter CF2 can be yellow filters. The first filter CF1 and the second filter CF2 can be provided integrally without distinguishing them from each other.
[0340] The light-shielding portion BM can be a black matrix. The light-shielding portion BM can be formed from organic or inorganic light-shielding materials containing black pigments or dyes. The light-shielding portion BM can prevent light leakage and define the boundaries between adjacent filters CF1, CF2, and CF3. Furthermore, in one embodiment, the light-shielding portion BM can be formed from a blue filter.
[0341] The first to the third filters CF1, CF2, and CF3 can be arranged to correspond to the red emitting area PXA-R, the green emitting area PXA-G, and the blue emitting area PXA-B, respectively.
[0342] A base substrate BL can be disposed on the color filter layer CFL. The base substrate BL can be a component that provides a base surface for disposing the color filter layer CFL and the light control layer CCL, etc. The base substrate BL can be a glass substrate, a metal substrate, a plastic substrate, etc. However, the embodiments are not limited to this, and the base substrate BL can be an inorganic layer, an organic layer, or a composite material layer. Furthermore, unlike the illustrated case, in one embodiment, the base substrate BL can be omitted.
[0343] Figure 8 This is a cross-sectional view showing a portion of a display device according to one embodiment. Figure 8 It shows the relationship with Figure 7 A cross-sectional view of a portion of the display panel DP. In a display device DD-TD of one embodiment, the light-emitting element ED-BT may include a plurality of light-emitting structures OL-B1, OL-B2, and OL-B3. The light-emitting element ED-BT may include: a first electrode EL1 and a second electrode EL2 facing each other; and a plurality of light-emitting structures OL-B1, OL-B2, and OL-B3, which are provided by being stacked sequentially in the thickness direction between the first electrode EL1 and the second electrode EL2. Each of the light-emitting structures OL-B1, OL-B2, and OL-B3 may include a light-emitting layer EML (Emitting Material Layer). Figure 7 ), with an EML light-emitting layer sandwiched in the middle ( Figure 7 The hole transmission region (HTR) and electron transmission region (ETR) are arranged accordingly.
[0344] That is, the light-emitting element ED-BT of the display device DD-TD included in one embodiment can be a light-emitting element with a tandem structure including multiple light-emitting layers.
[0345] exist Figure 8In one embodiment shown, the light emitted from each of the light-emitting structures OL-B1, OL-B2, and OL-B3 can all be blue light. However, the embodiment is not limited to this, and the wavelengths of the light emitted from each of the light-emitting structures OL-B1, OL-B2, and OL-B3 can be different from each other. For example, a light-emitting element ED-BT comprising multiple light-emitting structures OL-B1, OL-B2, and OL-B3 that emit light in different wavelengths can emit white light.
[0346] Charge generation layers CGL1 and CGL2 can be arranged between adjacent light-emitting structures OL-B1, OL-B2, and OL-B3. Charge generation layers CGL1 and CGL2 may include p-type charge generation layers and / or n-type charge generation layers.
[0347] Hereinafter, a polycyclic compound according to an embodiment of the present invention and a light-emitting element comprising a polycyclic amine compound according to an embodiment will be specifically described with reference to examples and comparative examples. Furthermore, the examples shown below are merely illustrative to aid in understanding the present invention, and the scope of the present invention is not limited thereto.
[0348] [Example]
[0349] 1. Synthesis of a polycyclic compound according to an embodiment
[0350] First, a method for synthesizing compounds A-8, B-18, and C-17 according to one embodiment will be specifically described by way of example. Furthermore, the method for synthesizing the compounds described below is one embodiment, and the method for synthesizing the compounds according to embodiments of the present invention is not limited to the following embodiment.
[0351] 1-1 Synthesis of Compound A-8
[0352] The polycyclic compound 1 of one embodiment of the present invention can be synthesized, for example, by the following reaction formula 1.
[0353] [Reaction Formula 1]
[0354]
[0355]
[0356] 100 g (404 mmol) of a-1, 56 g (607 mmol) of aniline, 46 g (486 mmol) of sodium tert-butoxide (tBuONa), 12 g (21 mmol) of Pd(dba)2, and 13 g (25 mmol) of 4,5-bis(diphenylphosphine)-9,9-dimethyloxanthracene (XantPhos) were added to a three-necked flask, and Ar was substituted. Then, 1500 mL of toluene was added, and the mixture was stirred at 60 °C for 3 hours. Water was added to the reaction system, and the organic layer was extracted with toluene. The mixture was then dried with magnesium sulfate to remove the solvent. The crude product was purified by silica gel column chromatography (hexane / toluene mixed solvent) and recrystallization (ethanol / toluene mixed solvent) to give 108 g (80% yield) of a white solid. The molecular weight of the purified product was confirmed to be 335 by FAB-MS, thus confirming the yield of compound a-2.
[0357] After adding 100 g (299 mmol) of a-2 to a three-necked flask and replacing Ar, 700 mL of N-methylpyrrolidone (NMP) was added for dissolution, and the mixture was stirred at 190 °C for 5 hours. Water was added to the reaction system, and the organic layer was extracted with toluene, dried with magnesium sulfate, and the solvent was removed. The crude product was purified by silica gel column chromatography (hexane / toluene mixed solvent) and recrystallization (ethanol (Ethanol) / toluene mixed solvent) to give 110 g (75% yield) of a white solid. The molecular weight of the purified product was confirmed to be 493 by FAB-MS, thus confirming the yield of compound a-3.
[0358] 100 g (203 mmol) of a-3, 36 g (213 mmol) of diphenylamine, 23 g (243 mmol) of sodium tert-butoxide (tBuONa), 4.7 g (8.1 mmol) of Pd(dba)2, and 4.7 g (8.1 mmol) of 4,5-bis(diphenylphosphine)-9,9-dimethyloxanthracene (XantPhos) were added to a three-necked flask, and Ar was substituted. Then, 1000 mL of toluene was added, and the mixture was stirred at 60 °C for 2 hours. Water was added to the reaction system, and the organic layer was extracted with toluene. The mixture was then dried with magnesium sulfate to remove the solvent. The crude product was purified by silica gel column chromatography (hexane / toluene mixed solvent) and recrystallization (ethanol (Ethanol) / toluene mixed solvent) to give 111 g (94% yield) of a white solid. The molecular weight of the purified product was confirmed to be 581 by FAB-MS, thus confirming the yield of compound a-4.
[0359] 100 g (172 mmol) of a-4, 17 g (189 mmol) of aniline, 20 g (207 mmol) of sodium tert-butoxide (tBuONa), 5.0 g (8.6 mmol) of Pd(dba)2, and 5.5 g (10 mmol) of 4,5-bis(diphenylphosphine)-9,9-dimethyloxanthracene (XantPhos) were added to a three-necked flask, and Ar was substituted. Then, 800 mL of toluene was added, and the mixture was stirred at 60 °C for 6 hours. Water was added to the reaction system, and the organic layer was extracted with toluene. The mixture was then dried with magnesium sulfate to remove the solvent. The crude product was purified by silica gel column chromatography (hexane / toluene mixed solvent) and recrystallization (ethanol / toluene mixed solvent) to give 70 g (69% yield) of a white solid. The molecular weight of the purified product was confirmed to be 593 by FAB-MS, thus confirming the yield of compound a-5.
[0360] 70 g (118 mmol) of a-5, 19 g (59 mmol) of 1,3-diiodobenzene, 34 g (354 mmol) of sodium tert-butoxide (tBuONa), 5.4 g (9.4 mmol) of Pd(dba)2, and 5.5 g (19 mmol) of tri-tert-butylphosphine tetrafluoroborate (P(tBu)3HBF4) were added to a three-necked flask, and Ar was substituted. 600 mL of toluene was then added, and the mixture was stirred at 80 °C for 1 hour. Water was added to the reaction system, and the organic layer was extracted with toluene. The mixture was then dried with magnesium sulfate to remove the solvent. The crude product was purified by silica gel column chromatography (hexane / toluene mixed solvent) and recrystallization (ethanol / toluene mixed solvent) to give 107 g (72% yield) of a white solid. The molecular weight of the purified product was confirmed to be 1261 by FAB-MS, thus confirming the yield of compound a-6.
[0361] After adding 20 g (16 mmol) of a-6 to a three-necked flask and replacing Ar, 25 g (64 mmol) of BI3 and 160 mL of o-dichlorobenzene (ODCB) were added for dissolution. Then, 11 mL (63 mmol) of N,N-diisopropylethylamine (DIPEA) was added and the mixture was stirred at 160 °C for 20 min. 260 mL (190 mmol) of N,N-diisopropylethylamine (DIPEA) was added to the reaction system, and the mixture was stirred at room temperature for 30 min. After washing the reaction mixture with a large amount of acetonitrile, the solid was recovered by filtration. The crude product was purified by silica gel column chromatography (hexane / dichloromethane mixed solvent) and recrystallization (ethanol / toluene mixed solvent) to give 6.5 g (32% yield) of a yellow solid. The molecular weight of the purified product was confirmed to be 1277 by FAB-MS, thus confirming the yield of compound A-8.
[0362] 1-2. Synthesis of Compound B-18
[0363] The polycyclic compound B-18 of one embodiment of the present invention can be synthesized, for example, by the following reaction formulas 2-1 to 2-3.
[0364] [Reaction 2-1]
[0365]
[0366] 100 g (380 mmol) of b-1, 70 g (760 mmol) of aniline, 44 g (456 mmol) of sodium tert-butoxide (tBuONa), 11 g (19 mmol) of Pd(dba)2, and 12 g (23 mmol) of 4,5-bis(diphenylphosphine)-9,9-dimethyloxanthracene (XantPhos) were added to a three-necked flask, and Ar was substituted. Then, 1900 mL of toluene was added, and the mixture was stirred at 80 °C for 1 hour. Water was added to the reaction system, and the organic layer was extracted with toluene. The mixture was then dried with magnesium sulfate to remove the solvent. The crude product was purified by silica gel column chromatography (hexane / toluene mixed solvent) and recrystallization (ethanol / toluene mixed solvent) to give 90 g (86% yield) of a white solid. The molecular weight of the purified product was confirmed to be 275 by FAB-MS, thus confirming the yield of compound b-2.
[0367] 45 g (163 mmol) of b-2, 50 g (196 mmol) of 1,3-dibromo-5-fluorobenzene, and 80 g (245 mmol) of CsCO3 were added to a three-necked flask, and Ar was substituted. Then, 400 mL of N-methylpyrrolidone (NMP) was added to dissolve the compound, and the mixture was stirred at 180 °C for 3 hours. Water was added to the reaction system, and the organic layer was extracted with toluene. The solvent was removed by drying with magnesium sulfate. The crude product was purified by silica gel column chromatography (hexane / toluene mixed solvent) and recrystallization (ethanol / toluene mixed solvent) to give 67 g (81% yield) of a white solid. The molecular weight of the purified product was confirmed to be 509 by FAB-MS, thus confirming the yield of compound b-3.
[0368] 67 g (132 mmol) of b-3, 23 g (138 mmol) of diphenylamine, 15 g (158 mmol) of sodium tert-butoxide (tBuONa), 3.0 g (5.2 mmol) of Pd(dba)2, and 3.0 g (5.3 mmol) of 4,5-bis(diphenylphosphine)-9,9-dimethyloxanthracene (XantPhos) were added to a three-necked flask to replace Ar. Then, 700 mL of toluene was added, and the mixture was stirred at 60 °C for 6 hours. Water was added to the reaction system, and the organic layer was extracted with toluene. The mixture was then dried with magnesium sulfate to remove the solvent. The crude product was purified by silica gel column chromatography (hexane / toluene mixed solvent) and recrystallization (ethanol / toluene mixed solvent) to give 68 g (87% yield) of a white solid. The molecular weight of the purified product was confirmed to be 598 by FAB-MS, thus confirming the yield of compound b-4.
[0369] 65 g (109 mmol) of b-4, 11 g (120 mmol) of aniline, 12 g (130 mmol) of sodium tert-butoxide (tBuONa), 3.1 g (5.4 mmol) of Pd(dba)2, and 3.4 g (6.5 mmol) of 4,5-bis(diphenylphosphine)-9,9-dimethyloxanthracene (XantPhos) were added to a three-necked flask, and Ar was substituted. Then, 500 mL of toluene was added, and the mixture was stirred at 60 °C for 2 hours. Water was added to the reaction system, and the organic layer was extracted with toluene. The mixture was then dried with magnesium sulfate to remove the solvent. The crude product was purified by silica gel column chromatography (hexane / toluene mixed solvent) and recrystallization (ethanol / toluene mixed solvent) to give 40 g (60% yield) of a white solid. The molecular weight of the purified product was confirmed to be 610 by FAB-MS, thus confirming the yield of compound b-5.
[0370] [Reaction 2-2]
[0371]
[0372] 45 g (163 mmol) of b-2, 40 g (196 mmol) of 3-bromo-5-fluoroanisole, and 80 g (245 mmol) of CsCO3 were added to a three-necked flask, and Ar was substituted. Then, 400 mL of N-methylpyrrolidone (NMP) was added to dissolve the compound, and the mixture was stirred at 190 °C for 5 hours. Water was added to the reaction system, and the organic layer was extracted with toluene. The solvent was removed by drying with magnesium sulfate. The crude product was purified by silica gel column chromatography (hexane / toluene mixed solvent) and recrystallization (ethanol / toluene mixed solvent) to give 67 g (90% yield) of a white solid. The molecular weight of the purified product was confirmed to be 460 by FAB-MS, thus confirming the yield of compound b-3'.
[0373] 60 g (130 mmol) of b-3', 23 g (169 mmol) of diphenylamine, 15 g (156 mmol) of sodium tert-butoxide (tBuONa), 3.0 g (5.2 mmol) of Pd(dba)2, and 3.0 g (5.3 mmol) of 4,5-bis(diphenylphosphine)-9,9-dimethyloxanthracene (XantPhos) were added to a three-necked flask, and Ar was substituted. Then, 500 mL of toluene was added, and the mixture was stirred at 60 °C for 4 hours. Water was added to the reaction system, and the organic layer was extracted with toluene. The solvent was removed by drying with magnesium sulfate. The crude product was purified by silica gel column chromatography (hexane / toluene mixed solvent) and recrystallization (ethanol / toluene mixed solvent) to give 60 g (83% yield) of a white solid. The molecular weight of the purified product was confirmed to be 549 by FAB-MS, thus confirming the yield of compound b-4'.
[0374] After adding 50 g (91 mmol) of b-4' and 57 g (228 mmol) of BBr3 to a three-necked flask and replacing Ar, 500 mL of dichloromethane (DMC) was added and the mixture was stirred at room temperature for 12 hours. Water was added to the reaction system, and the organic layer was extracted with dichloromethane (DMC), dried with magnesium sulfate, and the solvent was removed. The crude product was purified by silica gel column chromatography (hexane / toluene mixture) and recrystallization (ethanol / toluene mixture) to give 46 g (95% yield) of a white solid. The molecular weight of the purified product was confirmed as 535 by FAB-MS, thus confirming the yield of compound b-5'.
[0375] [Reaction 2-3]
[0376]
[0377]
[0378] 50 g (82 mmol) of b-5, 73 g (328 mmol) of 1-fluoro-3-iodobenzene, 57 g (410 mmol) of K₂CO₃, and 78 g (410 mmol) of CuI were added to a three-necked flask, and Ar was substituted. The mixture was stirred at 180 °C for 36 hours. Water was added to the reaction system, and the organic layer was extracted with dichloromethane (DMC). The mixture was then dried with magnesium sulfate to remove the solvent. The crude product was purified by silica gel column chromatography (hexane / toluene mixed solvent) and recrystallization (ethanol (Ethanol) / toluene mixed solvent) to give 40 g (70% yield) of a white solid. The molecular weight of the purified product was confirmed to be 704 by FAB-MS, thus confirming the yield of compound b-6.
[0379] After adding 40 g (56 mmol) of b-6, 36 g (68 mmol) of b-5', and 28 g (85 mmol) of CsCO3 to a three-necked flask and replacing Ar, 400 mL of N-methylpyrrolidone (NMP) was added for dissolution, and the mixture was stirred at 180 °C for 4 hours. Water was added to the reaction system, the organic layer was extracted with toluene, and then dried with magnesium sulfate to remove the solvent. The crude product was purified by silica gel column chromatography (hexane / toluene mixed solvent) and recrystallization (ethanol (Ethanol) / toluene mixed solvent) to give 46 g (67% yield) of a white solid. The molecular weight of the purified product was confirmed to be 1218 by FAB-MS, thus confirming the yield of compound b-7.
[0380] After adding 20 g (16 mmol) of b-7 to a three-necked flask and replacing Ar, 26 g (66 mmol) of BI3 and 160 mL of o-dichlorobenzene (ODCB) were added for dissolution. Then, 11 mL (65 mmol) of N,N-diisopropylethylamine (DIPEA) was added and the mixture was stirred at 160 °C for 10 min. 260 mL (190 mmol) of N,N-diisopropylethylamine (DIPEA) was added to the reaction system, and the mixture was stirred at room temperature for 30 min. After washing the reaction mixture with a large amount of acetonitrile, the solid was recovered by filtration. The crude product was purified by silica gel column chromatography (hexane / dichloromethane mixed solvent) and recrystallization (ethanol / toluene mixed solvent) to give 10 g (52% yield) of a yellow solid. The molecular weight of the purified product was confirmed to be 1234 by FAB-MS, thus confirming the yield of compound B-18.
[0381] 1-3. Synthesis of compound C-17
[0382] The polycyclic compound C-17 of one embodiment of the present invention can be synthesized, for example, by the following reaction formulas 3-1 to 3-3.
[0383] [Reaction 3-1]
[0384]
[0385] 100 g (405 mmol) of c-1, 113 g (1214 mmol) of aniline, 47 g (486 mmol) of sodium tert-butoxide (tBuONa), 12 g (20 mmol) of Pd(dba)2, and 13 g (25 mmol) of 4,5-bis(diphenylphosphine)-9,9-dimethyloxanthracene (XantPhos) were added to a three-necked flask, and Ar was substituted. Then, 2000 mL of toluene was added, and the mixture was stirred at 60 °C for 1 hour. Water was added to the reaction system, and the organic layer was extracted with toluene. The mixture was then dried with magnesium sulfate to remove the solvent. The crude product was purified by silica gel column chromatography (hexane / toluene mixed solvent) and recrystallization (ethanol / toluene mixed solvent) to give 81 g (78% yield) of a white solid. The molecular weight of the purified product was confirmed to be 259 by FAB-MS, thus confirming the yield of compound c-2.
[0386] 50 g (193 mmol) of c-2, 59 g (254 mmol) of 1,3-dibromo-5-fluorobenzene, and 94 g (290 mmol) of CsCO3 were added to a three-necked flask, and Ar was substituted. Then, 500 mL of N-methylpyrrolidone (NMP) was added to dissolve the compound, and the mixture was stirred at 180 °C for 2 hours. Water was added to the reaction system, and the organic layer was extracted with toluene. The solution was then dried with magnesium sulfate to remove the solvent. The crude product was purified by silica gel column chromatography (hexane / toluene mixed solvent) and recrystallization (ethanol / toluene mixed solvent) to give 86 g (90% yield) of a white solid. The molecular weight of the purified product was confirmed to be 493 by FAB-MS, thus confirming the yield of compound c-3.
[0387] 80 g (162 mmol) of c-3, 29 g (170 mmol) of diphenylamine, 19 g (195 mmol) of sodium tert-butoxide (tBuONa), 3.7 g (6.5 mmol) of Pd(dba)2, and 3.7 g (6.5 mmol) of 4,5-bis(diphenylphosphine)-9,9-dimethyloxanthracene (XantPhos) were added to a three-necked flask, and Ar was substituted. Then, 800 mL of xylene was added, and the mixture was stirred at 60 °C for 3 hours. Water was added to the reaction system, and the organic layer was extracted with toluene. The mixture was then dried with magnesium sulfate to remove the solvent. The crude product was purified by silica gel column chromatography (hexane / toluene mixed solvent) and recrystallization (ethanol / toluene mixed solvent) to give 78 g (83% yield) of a white solid. The molecular weight of the purified product was confirmed to be 581 by FAB-MS, thus confirming the yield of compound c-4.
[0388] 75 g (129 mmol) of c-4, 35 g (142 mmol) of terphenylamine, 15 g (155 mmol) of sodium tert-butoxide (tBuONa), 3.7 g (6.5 mmol) of Pd(dba)2, and 4.0 g (7.7 mmol) of 4,5-bis(diphenylphosphine)-9,9-dimethyloxanthracene (XantPhos) were added to a three-necked flask, and Ar was substituted. Then, 500 mL of toluene was added, and the mixture was stirred at 60 °C for 5 hours. Water was added to the reaction system, and the organic layer was extracted with toluene. The mixture was then dried with magnesium sulfate to remove the solvent. The crude product was purified by silica gel column chromatography (hexane / toluene mixed solvent) and recrystallization (ethanol / toluene mixed solvent) to give 51 g (53% yield) of a white solid. The molecular weight of the purified product was confirmed to be 746 by FAB-MS, thus confirming the yield of compound c-5.
[0389] [Reaction 3-2]
[0390]
[0391] 50 g (279 mmol) of 3,5-dichlorobenzenethiol, 236 g (1396 mmol) of diphenylamine, 64 g (670 mmol) of sodium tert-butoxide (tBuONa), 12.8 g (22 mmol) of Pd(dba)2, and 26 g (45 mmol) of 4,5-bis(diphenylphosphine)-9,9-dimethyloxanthracene (XantPhos) were added to a three-necked flask, and Ar was substituted. Then, 1500 mL of xylene was added, and the mixture was stirred at 120 °C for 8 hours. Water was added to the reaction system, and the organic layer was extracted with toluene. The solvent was removed by drying with magnesium sulfate. The crude product was purified by silica gel column chromatography (hexane / toluene mixed solvent) and recrystallization (ethanol / toluene mixed solvent) to give 58 g (47% yield) of a white solid. The molecular weight of the purified extract was confirmed to be 445 by FAB-MS measurement, thus confirming the presence of compound c-1'.
[0392] [Reaction 3-3]
[0393]
[0394] After adding 50 g (84 mmol) of c-5, 75 g (337 mmol) of 1-fluoro-3-iodobenzene, 58 g (422 mmol) of K₂CO₃, and 80 g (422 mmol) of CuI to a three-necked flask and replacing Ar, the mixture was stirred at 180 °C for 50 h. Water was added to the reaction system, and the organic layer was extracted with dichloromethane (DMC), dried with magnesium sulfate, and the solvent was removed. The crude product was purified by silica gel column chromatography (hexane / toluene mixed solvent) and recrystallization (ethanol / toluene mixed solvent) to give 42 g (70% yield) of a white solid. The molecular weight of the purified product was confirmed to be 704 by FAB-MS, thus confirming the yield of compound c-6.
[0395] After adding 40 g (57 mmol) of c-6, 30 g (68 mmol) of c-1', and 28 g (85 mmol) of CsCO3 to a three-necked flask and replacing Ar, 200 mL of N-methylpyrrolidone (NMP) was added for dissolution, and the mixture was stirred at 180 °C for 3 hours. Water was added to the reaction system, and the organic layer was extracted with toluene, dried with magnesium sulfate, and the solvent was removed. The crude product was purified by silica gel column chromatography (hexane / toluene mixed solvent) and recrystallization (ethanol / toluene mixed solvent) to give 44 g (70% yield) of a white solid. The molecular weight of the purified product was confirmed to be 1112 by FAB-MS, thus confirming the yield of compound c-7.
[0396] After adding 20 g (18 mmol) of C-7 to a three-necked flask and replacing Ar, 28 g (72 mmol) of BI3 and 180 mL of o-dichlorobenzene (ODCB) were added for dissolution. Then, 13 mL (72 mmol) of N,N-diisopropylethylamine (DIPEA) was added and the mixture was stirred at 160 °C for 20 min. 290 mL (214 mmol) of N,N-diisopropylethylamine (DIPEA) was added to the reaction system, and the mixture was stirred at room temperature for 30 min. After washing the reaction mixture with a large amount of acetonitrile, the solid was recovered by filtration. The crude product was purified by silica gel column chromatography (hexane / dichloromethane mixed solvent) and recrystallization (ethanol / toluene mixed solvent) to give 5.1 g (25% yield) of a yellow solid. The molecular weight of the purified product was confirmed to be 1127 by FAB-MS, thus confirming the yield of compound C-17.
[0397] 2. Physical property evaluation of polycyclic compounds
[0398] [Calculation of molecular orbitals]
[0399] Table 1 below shows the S1 energy level and T1 energy level for compounds A-8, B-18, C-17 of Examples, and comparative examples X1 to X6. The S1 and T1 energy levels were calculated using a non-empirical molecular orbital method. Specifically, Gaussian 09 was used, with the functional group calculated using B3LYP and the basis function calculated using 6-31G(d).
[0400] Table 1
[0401] compound S1 energy level T1 energy level ΔEst Example Compound A-8 2.91 2.63 0.28 Example Compound B-18 2.89 2.59 0.30 Example Compound C-17 2.87 2.58 0.29 Comparative compound X1 2.90 2.58 0.32 Comparative compound X2 3.04 2.71 0.33 Comparative compound X3 2.92 2.59 0.32 Comparative compound X4 2.28 2.27 0.01 Comparative compound X5 2.73 2.26 0.47 Comparative compound X6 2.89 2.53 0.36
[0402] [Comparative Compounds]
[0403]
[0404] It can be confirmed that the ΔEst of Examples A-8, B-18, and C-17 is smaller than that of Comparative Examples X1 to X3, X5, and X6, and satisfies the range of 0.2 to 0.3. Therefore, the Examples can be used as thermally active delayed fluorescence (TADF) dopant materials. However, unlike Comparative Examples X1 to X3, X5, and X6, the highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) of Comparative Example X4 are separated. Therefore, it is determined that the luminescence principle is different from that of Comparative Examples X1 to X3, X5, and X6, and ΔEst exhibits a small value.
[0405] [Evaluation of Fluorescence Properties]
[0406] In the evaluation of luminescence properties, PPF and a compound from one example were deposited on quartz glass at a weight ratio of 80:20. The fluorescence emission spectra were measured using a JASCO V-670 spectrometer and are shown in Table 2. The fluorescence quantum efficiency was measured using a JASCO ILF-835 integrating sphere system.
[0407]
[0408] Table 2
[0409]
[0410]
[0411] It can be confirmed that the fluorescence quantum efficiency of compounds A-8, B-18, and C-17 in Examples is higher than that of comparative compounds X1 to X6.
[0412] 3. Manufacturing and evaluation of light-emitting elements
[0413] (Manufacturing of light-emitting elements)
[0414] Patterning thickness on a glass substrate After ITO deposition, the material was washed with ultrapure water and subjected to a 10-minute UV ozone treatment to form the first electrode. HAT-CN was then vacuum-deposited onto the first electrode to form... A thick hole injection layer. NPD is formed by vacuum deposition on top of the hole injection layer. A thick hole transport layer. mCP was formed by vacuum deposition on top of the hole transport layer. A thick electron blocking layer was formed by simultaneously depositing mCBP and the compound of the examples or comparative examples on the electron blocking layer at a weight ratio of 80:20. A thick luminescent layer. TBPi is deposited on top of the luminescent layer to form... After a thick electron transport layer, Liq is deposited on top of the electron transport layer to form... A thick electron-injected layer was formed by vacuum deposition of aluminum (Al) on the electron-injected layer. A second electrode of thickness. Compound P5 is formed by vacuum deposition on the second electrode. A thick capping layer is used to fabricate the light-emitting element. In this embodiment, a first electrode, a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, an electron transport layer, an electron injection layer, a second electrode, and a capping layer are formed using a vacuum deposition apparatus.
[0415] The compounds used in manufacturing light-emitting elements are shown below.
[0416]
[0417] (Characteristic evaluation of light-emitting elements)
[0418] To evaluate the characteristics of the light-emitting elements according to Examples 1 to 3 and Comparative Examples 1 to 6, the maximum value of the external quantum efficiency was evaluated and is shown in Table 3. The voltage and current density of the light-emitting elements were measured using a source meter (Keithley Instruments, 2400 series), and the brightness and external quantum efficiency were measured using an external quantum efficiency measurement device C9920-12 from Hamamatsu Photonics Co., Ltd.
[0419] Table 3
[0420]
[0421]
[0422] Comparing Examples 1 to 3 with Comparative Examples 1 to 6, it can be seen that the light-emitting elements including Examples 1 to 3 exhibit long lifetimes. This is believed to be because the molecular orbitals of the compounds in Examples 1 to 3 are wider than those of the compounds in Comparative Examples 1 to 6, thereby improving their electrical stability.
[0423] The compounds of Comparative Examples 1 to 6 were not substituted with dibenzo[a]hexyl groups in the boron-based main skeleton. In contrast, the compounds of Examples 1 to 3 were substituted with at least one dibenzo[a]hexyl group in the boron-based main skeleton, resulting in a long conjugation structure, which improves electrostability.
[0424] As such, the cases including Examples 1 to 3 show an improved lifespan of the light-emitting element compared to the cases including Comparative Examples 1 to 6. That is, the polycyclic compounds of Examples 1 to 3 have dibenzohexyl groups substituted for the boron-substituted benzene rings, resulting in high electrical stability, which in turn improves the lifespan of the light-emitting element including the polycyclic compound.
[0425] One embodiment of the light-emitting element can improve the lifespan of the element by including a polycyclic compound containing a dibenzohexyl group that has a boron-substituted benzene ring.
[0426] Although the above description has been made with reference to preferred embodiments of the present invention, it will be understood by those skilled in the art or those with ordinary knowledge of the art that various modifications and alterations can be made to the present invention without departing from the spirit and technical scope of the invention as set forth in the claims.
[0427] Therefore, the scope of the present invention should not be limited to the contents described in the detailed description of the specification, but should be determined by the claims.
Claims
1. A light-emitting element, comprising: First electrode; The second electrode is disposed on the first electrode; as well as A light-emitting layer is disposed between the first electrode and the second electrode, and comprises a polycyclic compound represented by the following chemical formula 1. [Chemical Formula 1] In the chemical formula 1, m and n are independently 0 or 1. o is an integer greater than 0 and less than 3. X1 to X4 are independently NRa, CRbRc, O, or S, respectively. Y1 and Y2 are independently NRd, O, or S, respectively. R1 to R 20 And Ra to Rd are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted amino group, an alkyl group with 1 to 20 carbon atoms, an aryl group with 6 to 30 cyclic carbon atoms, or a heteroaryl group with 3 to 30 cyclic carbon atoms.
2. The light-emitting element as described in claim 1, wherein, The chemical formula 1 is represented by either the following chemical formula 2-1 or the following chemical formula 2-2: [Chemical Formula 2-1] [Chemical Formula 2-2] In chemical formulas 2-1 and 2-2, n, o, X1 to X4, Y1, Y2, and R1 to R 20 Same as the definition in Chemical Formula 1, In the chemical formula 2-2, o1 is either 0 or 1.
3. The light-emitting element as described in claim 1, wherein, The chemical formula 1 is represented by any one of the following chemical formulas 3-1 to 3-3: [Chemical Formula 3-1] [Chemical Formula 3-2] [Chemical Formula 3-3] In the chemical formulas 3-1 to 3-3, m to o, X1 to X4, Y1, Y2, and R1 to R 20 Same as the definition in Chemical Formula 1, In chemical formulas 3-1 and 3-2, o1 is 0 or 1.
4. The light-emitting element as described in claim 3, wherein, In the chemical formula 3-1, R 11 To R 18 At least one of them is an unsubstituted phenyl group.
5. The light-emitting element as claimed in claim 1, wherein, Chemical formula 1 is represented by any one of the following chemical formulas 4-1 to 4-3: [Chemical Formula 4-1] [Chemical Formula 4-2] [Chemical Formula 4-3] In chemical formulas 4-1 to 4-3, m to n, X1 to X4, and R1 to R 20 Same as the definition in Chemical Formula 1, Rd1 and Rd2 are, independently, a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted amino group, an alkyl group with 1 to 20 carbon atoms, a substituted or unsubstituted cyclic carbon group with 6 to 30 carbon atoms, or a substituted or unsubstituted cyclic carbon group with 2 to 30 carbon atoms.
6. The light-emitting element as claimed in claim 1, wherein, In the chemical formula 1, at least one of X1 to X4 is NRa. Ra is any one of substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, and substituted or unsubstituted terphenyl.
7. The light-emitting element as claimed in claim 1, wherein, In the chemical formula 1, at least one of Y1 and Y2 is NRd. Rd represents a substituted or unsubstituted phenyl group.
8. The light-emitting element as claimed in claim 1, wherein, The light-emitting layer includes a dopant and a substrate. The dopant includes the polycyclic compound.
9. The light-emitting element as claimed in claim 1, wherein, The luminescent layer emits thermally active delayed fluorescence.
10. The light-emitting element as claimed in claim 1, wherein, The light-emitting layer emits light with a central wavelength between 430nm and 490nm.
11. The light-emitting element as claimed in claim 1, wherein, The R1 to R 20 All of them are deuterium atoms.
12. The light-emitting element as claimed in claim 1, wherein, The luminescent layer includes at least one of the compounds shown in compound group 1 below: [Compound Group 1] 13. A light-emitting element, comprising: First electrode; The second electrode is disposed on the first electrode; A light-emitting layer is disposed between the first electrode and the second electrode, and comprises a polycyclic compound represented by the following chemical formula 1A; as well as A capping layer, disposed on the light-emitting layer, has a refractive index of 1.6 or higher. [Chemical Formula 1A] In the chemical formula 1A, In W1 to W6, at least one pair of two adjacent pairs selected from W1 to W3 and one pair of two adjacent pairs selected from W4 to W6 are connected to a substituent represented by chemical formula 2A. The rest are each independently named CRe. X1 to X4 are independently NRa, CRbRc, O, or S, respectively. R1 to R 10 Ra to Rc and Re are, respectively, independently hydrogen atoms, deuterium atoms, halogen atoms, substituted or unsubstituted amino groups, alkyl groups with 1 to 20 substituted or unsubstituted carbon atoms, aryl groups with 6 to 30 substituted or unsubstituted cyclic carbon atoms, or heteroaryl groups with 3 to 30 substituted or unsubstituted cyclic carbon atoms. [Chemical Formula 2A] In the chemical formula 2A, Y is NRd, O, or S. R 11 To R 14 And Rd is independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted amino group, an alkyl group with 1 to 20 carbon atoms, a substituted or unsubstituted cyclic carbon group with 6 to 30 carbon atoms, or a heteroaryl group with 3 to 30 carbon atoms.
14. The light-emitting element as claimed in claim 13, wherein, The chemical formula 2A is represented by chemical formula 3A-1 or chemical formula 3A-2: [Chemical Formula 3A-1] [Chemical Formula 3A-2] In the chemical formula 3A-1, Y1 is NRd1, O, or S, and Y1 combines with W1 or W2. R 11a To R 14a And Rd1 is independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted amino group, an alkyl group with 1 to 20 carbon atoms, a substituted or unsubstituted cyclic carbon group with 6 to 30 carbon atoms, or a heteroaryl group with 3 to 30 carbon atoms. In the chemical formula 3A-2, Y2 is NRd2, O, or S, and Y2 combines with W5 or W6. R 11b To R 14b And Rd2 is independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted amino group, an alkyl group with 1 to 20 carbon atoms, a substituted or unsubstituted cyclic carbon group with 6 to 30 carbon atoms, or a heteroaryl group with 3 to 30 carbon atoms.
15. The light-emitting element as claimed in claim 14, wherein, If the chemical formula 3A-1 is combined with W1 and W2, then the chemical formula 3A-2 is combined with W5 and W6.
16. The light-emitting element as claimed in claim 14, wherein, The Y1 in chemical formula 3A-1 is the same as the Y2 in chemical formula 3A-2.
17. The light-emitting element as claimed in claim 13, wherein, The chemical formula 2A is represented by the following chemical formulas 4A-1 to 4A-3: [Chemical Formula 4A-1] [Chemical Formula 4A-2] [Chemical Formula 4A-3] In the chemical formulas 4A-1 to 4A-3, R 11 To R 14 And Rd is the same as the definition in the chemical formula 2A.
18. The light-emitting element as claimed in claim 13, wherein, In the chemical formula 1A, at least one of X1 to X4 is NRa. Ra is any one of substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, and substituted or unsubstituted terphenyl.
19. The light-emitting element as claimed in claim 13, wherein, In the chemical formula 2A, Y is NRd, and Rd is a substituted or unsubstituted phenyl group.
20. The light-emitting element as claimed in claim 13, wherein, The luminescent layer includes at least one of the compounds shown in compound group 1 below: [Compound Group 1]