Light-emitting element, polycyclic compound for light-emitting element, and electronic device including the light-emitting element.

Abstract

To provide a light-emitting element with improved luminous efficiency and lifespan. [Solution] A light-emitting element containing a compound represented by the following chemical formula in the light-emitting layer between the first electrode and the second electrode. JPEG2026135762000150.jpg7174

Description

[Technical Field]

[0001] The present invention relates to a light-emitting element, a polycyclic compound used therein, and an electronic device including the light-emitting element. [Background technology]

[0002] Organic electroluminescent display devices, which include organic electroluminescent elements, are used as display devices within electronic equipment. Organic electroluminescent displays are display devices that include so-called self-emissive light-emitting elements, which inject holes and electrons injected from the first and second electrodes into the light-emitting layer, causing the light-emitting material of the light-emitting layer to emit light and realize a display.

[0003] When applying light-emitting elements to display devices, improvements in efficiency and lifespan are required, and there is a continuous need for the development of light-emitting element materials that can stably achieve these improvements. [Overview of the project] [Problems that the invention aims to solve]

[0004] The object of the present invention is to provide a light-emitting element with improved luminous efficiency and lifespan.

[0005] Another object of the present invention is to provide polycyclic compounds with improved quantum efficiency and material stability.

[0006] Another object of the present invention is to provide an electronic device that includes a light-emitting element with improved luminous efficiency and lifespan, and has excellent display quality. [Means for solving the problem]

[0007] One embodiment provides a polycyclic compound represented by the following chemical formula 1.

[0008] [Chemical formula 1] JPEG2026135762000001.jpg7277

[0009] In Chemical Formula 1, X1 to X4 are each independently O, S, Se, or represented by the following Chemical Formula 2, and Y1 to Y 16 are each independently CR a or N, and R a is a hydrogen atom, a deuterium atom, a cyano group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms:

[0010] [Chemical Formula 2] JPEG2026135762000002.jpg4658

[0011] In the above Chemical Formula 2, Y 17 to Y 21 are each independently CR b or N, and R b is a hydrogen atom, a deuterium atom, a cyano group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms. When none of X1 to X4 in Chemical Formula 1 is represented by Chemical Formula 2, at least one of Y1 to Y 16 in Chemical Formula 1 is N. When at least one of X1 to X4 in Chemical Formula 1 is represented by Chemical Formula 2, at least one of Y1 to Y 16 in Chemical Formula 1 and Y 17 to Y 21 in Chemical Formula 2 is N.

[0012] The above Chemical Formula 2 is represented by the following Chemical Formula 2-1, or any one of Y 17 to Y 21 in Chemical Formula 2 is N, and the rest can each independently be CR b .

[0013] [Chemical Formula 2-1] JPEG2026135762000003.jpg2939

[0014] In chemical formula 2-1, R b1 ~R b5 Each of these is independently a hydrogen atom, a deuterium atom, a cyano group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms.

[0015] One of Y1 to Y4, one of Y6 to Y8, and Y 13 Y 16 One of these, and one selected from Y5, is N, and the remaining ones are independently CR a Thus, X1 to X4 in the above chemical formula 1 can each be independently represented by O, S, Se, or the following chemical formula 2-1.

[0016] [Chemical formula 2-1] JPEG2026135762000004.jpg3239

[0017] In chemical formula 2-1, R b1 ~R b5 Each of these is independently a hydrogen atom, a deuterium atom, a cyano group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms.

[0018] Y1 to Y of the aforementioned chemical formula 1 16 Each of them operates independently in CR a In this case, at least one of X1 to X4 is represented by the chemical formula 2, and in the chemical formula 2, Y 17 Y 21 One of them is N, and the others are each independently CR b It is possible.

[0019] At least one hydrogen atom in chemical formulas 1 and 2 can be substituted with a deuterium atom.

[0020] The compound represented by the aforementioned chemical formula 1 may be a blue light-emitting dopant.

[0021] The compound represented by the aforementioned chemical formula 1 may be a thermally activated delayed fluorescence material.

[0022] Another 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, the light-emitting layer comprising the polycyclic compound of the embodiment described above.

[0023] The light-emitting layer may further contain at least one of the second compound represented by the following chemical formula HT-1 and the third compound represented by the following chemical formula ET-1.

[0024] [Chemical formula HT-1] JPEG2026135762000005.jpg3751

[0025] In the aforementioned chemical formula HT-1, A1 to A8 are each independently N or CR. 51 L1 is a direct linkage, a substituted or unsubstituted ring-forming arylene group with 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heteroarylene group with 2 to 30 carbon atoms, and Y a Direct coupling, CR 52 R 53 , or SiR 54 R 55 Ar1 is a substituted or unsubstituted aryl group with 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group with 2 to 30 ring-forming carbon atoms, and R 51 ~R 55Each of these groups is independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted thio group, a substituted or unsubstituted oxy group, a substituted or unsubstituted amine group, a substituted or unsubstituted boron group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 ring-forming carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 ring-forming carbon atoms, or is bonded to an adjacent group to form a ring:

[0026] [Chemical formula ET-1] JPEG2026135762000006.jpg4464

[0027] In the aforementioned chemical formula ET-1, at least one of X1 to X3 is N and the rest are CR. 56 And R 56 L2 to L4 are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 ring-forming carbon atoms, and b1 to b3 are each independently an integer between 0 and 10. Ar2 to Ar4 are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, and L2 to L4 are each independently a directly bonded, a substituted or unsubstituted arylene group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring-forming carbon atoms.

[0028] The light-emitting layer may further contain a fourth compound represented by the following chemical formula D-1.

[0029] [Chemical formula D-1] JPEG2026135762000007.jpg6477

[0030] In the chemical formula D-1, Q1 to Q4 are each independently C or N, and C1 to C4 are each independently substituted or unsubstituted hydrocarbon rings with 5 to 30 carbon atoms, or substituted or unsubstituted heterocycles with 2 to 30 carbon atoms, L 11 ~L 13 Each is independently and directly connected. JPEG2026135762000008.jpg21127 It is a substituted or unsubstituted divalent alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring-forming carbon atoms. b11 to b13 are each independently 0 or 1, and R 61 ~R 66 Each of these is independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted thio group, a substituted or unsubstituted oxy group, a substituted or unsubstituted amine group, a substituted or unsubstituted boron group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 ring-forming carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 ring-forming carbon atoms, and each of d1 to d4 is independently an integer between 0 and 4.

[0031] The fluorescence lifetime of the light-emitting element may be 3.0 μs or less.

[0032] The light-emitting layer may emit delayed fluorescence.

[0033] The light-emitting layer can emit blue light.

[0034] Another embodiment provides an electronic device that includes a display module comprising a plurality of light-emitting elements, at least one of which comprises a first electrode, a second electrode positioned on the first electrode, and a light-emitting layer positioned between the first electrode and the second electrode and comprising the polycyclic compound of the embodiment described above.

[0035] The electronic device may further include at least one of a processor, memory, and power supply module. [Effects of the Invention]

[0036] The light-emitting element of one embodiment can exhibit high efficiency and long lifespan characteristics by including the polycyclic compound of one embodiment in the light-emitting layer.

[0037] One example of a polycyclic compound can contribute to improving the light efficiency and extending the lifespan of a light-emitting element.

[0038] The electronic device of one embodiment may exhibit excellent display quality and improved reliability characteristics. [Brief explanation of the drawing]

[0039] [Figure 1] This is a block diagram of an electronic device according to one embodiment. [Figure 2] This is a schematic diagram of an electronic device according to one embodiment. [Figure 3] This is a plan view of a display module according to one embodiment. [Figure 4] This is a cross-sectional view showing the portion corresponding to the line I-I' in Figure 3. [Figure 5] This is a schematic cross-sectional view showing a light-emitting element of one embodiment. [Figure 6] This is a schematic cross-sectional view showing a light-emitting element of one embodiment. [Figure 7] This is a schematic cross-sectional view showing a light-emitting element of one embodiment. [Figure 8] This is a schematic cross-sectional view showing a light-emitting element of one embodiment. [Figure 9] This is a schematic cross-sectional view showing a light-emitting element of one embodiment. [Figure 10] This is a cross-sectional view showing a display module according to one embodiment. [Figure 11] This is a cross-sectional view showing a display module according to one embodiment. [Figure 12] This is a cross-sectional view showing a display module according to one embodiment. [Figure 13]This is a cross-sectional view showing a display module according to one embodiment. [Figure 14] This is a perspective view of an electronic device according to one embodiment. [Figure 15] This is a perspective view of an electronic device according to one embodiment. [Figure 16] This diagram shows the interior of a vehicle in which an electronic device according to one embodiment is installed. [Modes for carrying out the invention]

[0040] In this specification, when a component (or region, layer, part, etc.) is referred to as "on top of," "combined with," or "combined with" another component, it means that it can be directly placed on top of, connected to, or combined with the other component, or that a third component can be placed between them.

[0041] The same drawing symbol refers to the same component. Furthermore, in drawings, the thickness, proportions, and dimensions of components are exaggerated for the sake of effective explanation of the technical content. "and / or" includes all combinations of one or more components defined by the relevant component.

[0042] Terms such as "first," "second," etc., are used to describe a variety of components, but the components are not limited to those terms. The terms are used solely for the purpose of distinguishing one component, part, region, layer, or part from other components, parts, regions, layers, or parts. For example, without departing from the scope of the present invention, a first component, first part, first region, first layer, or first part may be named a second component, second part, second region, second layer, or second part, and similarly, a second component, second part, second region, second layer, or second part may also be named a first component, first part, first region, first layer, or first part. A singular expression includes plural expressions unless the context clearly indicates otherwise.

[0043] Furthermore, terms such as "down," "on the lower side," "up," and "on the upper side" are used to describe the relationships between the components shown in the drawing. These terms are relative concepts and are described in relation to the direction shown in the drawing.

[0044] Terms such as "includes" or "has" indicate the presence of features, figures, steps, actions, components, parts, or combinations thereof described in the specification, and should be understood not to pre-exist to exclude the presence or possibility of adding one or more other features, figures, steps, actions, components, parts, or combinations thereof.

[0045] Unless otherwise defined, all terms used herein (including technical and scientific terms) have the same meaning as those generally understood by those skilled in the art in the field to which the present invention pertains. Furthermore, terms such as those defined in commonly used dictionaries should be interpreted as having the meaning consistent with their meaning in the context of the relevant art, and should not be interpreted in an overly idealistic or formal sense unless expressly defined herein.

[0046] In this specification, "substituted or unsubstituted" may mean substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium atoms, halogen atoms, cyano groups, nitro groups, amino groups, silyl groups, oxy groups, thio groups, sulfinyl groups, sulfonyl groups, carbonyl groups, boron groups, phosphine oxide groups, phosphine sulfide groups, alkyl groups, alkenyl groups, alkynyl groups, hydrocarbon ring groups, aryl groups, and heterocyclic groups. Furthermore, each of the substituents exemplified above may be substituted or unsubstituted. For example, a biphenyl group may be interpreted as an aryl group, or as a phenyl group substituted with a phenyl group.

[0047] In this specification, "bonding with adjacent groups to form a ring" may mean bonding with adjacent groups 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 may be monocyclic or polycyclic. Furthermore, rings formed by bonding with each other may be linked to other rings to form a spirostructure.

[0048] In this specification, "adjacent group" may mean a substituent substituted on an atom directly linked to the atom on which the substituent is substituted, another substituent substituted on the atom on which the substituent is substituted, or the substituent that is most stereostructically adjacent to the substituent in question. For example, the two methyl groups in 1,2-dimethylbenzene may be interpreted as "adjacent groups," and the two ethyl groups in 1,1-diethylcyclopentene may be interpreted as "adjacent groups." Similarly, the two methyl groups in 4,5-dimethylphenanthrene may be interpreted as "adjacent groups."

[0049] Examples of halogen atoms in this specification include fluorine, chlorine, Brom, or iodine atoms.

[0050] In this specification, alkyl groups may be linear or branched. The number of carbon atoms in an alkyl group may be 1 to 60, 1 to 30, 1 to 20, 1 to 10, or 1 to 6. Examples of alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, s-butyl, t-butyl, i-butyl, 2-ethylbutyl, 3,3-dimethylbutyl, n-pentyl, i-pentyl, neopentyl, t-pentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl, n-hexyl, and 1-methylhexyl groups. , 2-ethylhexyl group, 2-butylhexyl group, n-heptyl group, 1-methylpeptyl group, 2,2-dimethylheptyl group, 2-ethylheptyl group, 2-butylheptyl group, n-octyl group, t-octyl group, 2-ethyloctyl group, 2-butyloctyl group, 2-hexyloctyl group, 3,7-dimethyloctyl group, n-nonyl group, n-decyl group, adamantyl group, 2-ethyldecyl group, 2-butyldecyl group, 2- Xyldecyl group, 2-octyldecyl group, n-undecyl group, n-dodecyl group, 2-ethyldodecyl group, 2-butyldodecyl group, 2-hexyldodecyl group, 2-octyldecyl group, n-tridecyl group, n-tetradecyl group, n-pentadecyl group, n-hexadecyl group, 2-ethylhexadecyl group, 2-butylhexadecyl group, 2-hexylhexadecyl group, 2-octylhexadecyl group, n-heptadecyl group, n- Examples of such groups include, but are not limited to, octadecyl group, n-nonadecyl group, n-icosyl group, 2-ethylicosyl group, 2-butylicosyl group, 2-hexylicosyl group, 2-octylicosyl group, n-henicosyl group, n-docosyl group, n-tricosyl group, n-tetracosyl group, n-pentacosyl group, n-hexacosyl group, n-heptacosyl group, n-octacosyl group, n-nonacosyl group, and n-triacontyl group.

[0051] In this specification, the term "cyclohexyl group" may mean a cyclic alkyl group. The number of carbon atoms in a cycloalkyl group is 3 to 60, 3 to 30, 3 to 20, or 3 to 10. Examples of cycloalkyl groups include, but are not limited to, cyclopropyl, cyclobutyl, cyclohexyl, 4-methylcyclohexyl, 4-t-butylcyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, norbornyl, 1-adantyl, 2-adamantyl, isonorbornyl, and bicycloheptyl.

[0052] In this specification, an alkenyl group means a hydrocarbon group containing one or more carbon double bonds in the middle or terminal of an alkyl group having two or more carbon atoms. An alkenyl group may be linear or branched. The number of carbon atoms is not particularly limited, but is 2 to 60, 2 to 30, 2 to 20, or 2 to 10. Examples of alkenyl groups include, but are not limited to, vinyl, 1-butenyl, 1-pentenyl, 1,3-butadienylaryl, styrenyl, and styrylvinyl groups.

[0053] In this specification, an alkynyl group means a hydrocarbon group containing one or more carbon triple bonds in the middle or terminal of an alkyl group having two or more carbon atoms. An alkynyl group may be linear or branched. The number of carbon atoms is not particularly limited, but is typically 2 to 30, 2 to 20, or 2 to 10. Specific examples of alkynyl groups include, but are not limited to, ethynyl and propynyl groups.

[0054] In this specification, a hydrocarbon ring group means any active group or substituent derived from an aliphatic hydrocarbon ring. A hydrocarbon ring group may be a saturated hydrocarbon ring group having 5 to 20 carbon atoms.

[0055] In this specification, an aryl group means any active group or substituent derived from an aromatic hydrocarbon ring. An aryl group may be a monocyclic aryl group or a polycyclic aryl group. The number of ring-forming carbon atoms in an aryl group may be 6 to 60, 6 to 30, 6 to 20, or 6 to 15. Examples of aryl groups include, but are not limited to, phenyl, naphthyl, fluorenyl, anthracenyl, phenanthryl, biphenyl, terphenyl, quarterphenyl, quincphenyl, sexiphenyl, triphenylenyl, pyrenyl, benzofluorantenyl, and chrysenyl groups.

[0056] In this specification, the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure. Examples of substitutions of the fluorenyl group are as follows, but are not limited to these. JPEG2026135762000009.jpg25127

[0057] In this specification, a heterocyclic group means any active group or substituent derived from a ring containing one or more heteroatoms from B, O, N, P, S, Si, and Se. Heterocyclic groups include aliphatic heterocyclic groups and aromatic heterocyclic groups. Aromatic heterocyclic groups may be heteroaryl groups. Aliphatic heterocycles and aromatic heterocycles may be monocyclic and polycyclic.

[0058] In this specification, a heterocyclic group may contain one or more heteroatoms from B, O, N, P, S, Si, and Se. If a heterocyclic group contains two or more heteroatoms, the two or more heteroatoms may be the same or different. A heterocyclic group may be a monocyclic heterocyclic group or a polycyclic heterocyclic group, and is a concept that includes a heteroaryl group. The number of ring-forming carbon atoms in a heterocyclic group may be 2 to 60, 2 to 30, 2 to 20, or 2 to 10.

[0059] In this specification, an aliphatic heterocyclic group may contain one or more heteroatoms from B, O, N, P, S, Si, and Se. The number of ring-forming 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, but are not limited to, oxirane groups, thiirane groups, pyrrolidine groups, piperidine groups, tetrahydrofuran groups, tetrahydrothiophene groups, thian groups, tetrahydropyran groups, and 1,4-dioxane groups.

[0060] In this specification, a heteroaryl group may contain one or more heteroatoms from B, O, N, P, S, Si, and Se. If a heteroaryl group contains two or more heteroatoms, the two or more heteroatoms may be the same or different. A heteroaryl group may be a monocyclic heterocyclic group or a polycyclic heterocyclic group. The number of ring-forming carbon atoms in a heteroaryl group may be 2 to 60, 2 to 30, 2 to 20, or 2 to 10. Examples of heteroaryl groups include thiophene group, furan group, pyrrol group, imidazole group, pyridine group, bipyridine group, pyrimidine group, triazine group, triazole group, acridyl group, pyridazine group, pyridinyl group, quinoline group, quinazoline group, quinoxaline group, phenoxane group, phthalazine group, pyridopyrimidine group, pyridopyrazine group, pyrazinopyrazine group, isoquinoline group, indole group, carbazole group, N-arylcarbazole group, and N-heteroaryl group. Examples include, but are not limited to, a lucarazole group, an N-alkylcarbazole group, a benzoxazole group, a benzimidazole group, a benzothiazole group, a benzocarbazole group, a benzothiophene group, a dibenzothiophene group, a thienthiophene group, a benzofuran group, a phenanthroline group, a thiazole group, an isoxazole group, an oxazole group, an oxadiazole group, a thiadiazole group, a phenothiazine group, a dibenzosilole group, and a dibenzofuran group.

[0061] In this specification, the above description of aryl groups may apply, except that arylene groups are divalent. The above description of heteroaryl groups may apply, except that heteroarylene groups are divalent.

[0062] In this specification, the silyl group includes alkylsilyl groups and arylsilyl groups. Examples of silyl groups include, but are not limited to, trimethylsilyl, triethylsilyl, t-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, and phenylsilyl groups.

[0063] In this specification, the number of carbon atoms in the carbonyl group is not particularly limited, but may be 1 to 40, 1 to 30, or 1 to 20. For example, it may have, but is not limited to, the following structure. JPEG2026135762000010.jpg30153

[0064] In this specification, the number of carbon atoms in the sulfinyl group and the sulfonyl group is not particularly limited, but may be between 1 and 30. The sulfinyl group may include an alkyl sulfinyl group and an aryl sulfinyl group. The sulfonyl group may include an alkyl sulfonyl group and an aryl sulfonyl group.

[0065] In this specification, the thio group may include alkylthio groups and arylthio groups. The thio group may mean a group to which a sulfur atom is bonded to the alkyl or aryl group as defined above. Examples of thio groups include, but are not limited to, methylthio, ethylthio, propylthio, pentylthio, hexylthio, octylthio, dodecylthio, cyclopentylthio, cyclohexylthio, phenylthio, and naphthylthio groups.

[0066] In this specification, an oxy group may mean a group in which an oxygen atom is bonded to an alkyl or aryl group as defined above. Oxy groups may include alkoxy groups and aryloxy groups. Alkoxy groups may be linear, branched, or cyclic. The number of carbon atoms in an alkoxy group is not particularly limited, but may be, for example, 1 to 20 or 1 to 10. Examples of oxy groups include, but are not limited to, methoxy, ethoxy, n-propoxy, isopropoxy, butoxy, pentyloxy, hexyloxy, octyloxy, nonyloxy, decyloxy, and benzyloxy.

[0067] In this specification, a boron group means a group in which a boron atom is bonded to an alkyl or aryl group as defined above. A boron group includes alkylboron groups and arylboron groups. Examples of boron groups include, but are not limited to, dimethylboron groups, diethylboron groups, t-butylmethylboron groups, diphenylboron groups, and phenylboron groups.

[0068] In this specification, the number of carbon atoms in the amine group is not particularly limited, but may be between 1 and 30. The amine group may include alkylamine groups and arylamine groups. Examples of amine groups include, but are not limited to, methylamine groups, dimethylamine groups, phenylamine groups, diphenylamine groups, naphthylamine groups, and 9-methyl-anthracenylamine groups.

[0069] In this specification, among alkylthio groups, alkylsulfoxy groups, alkylaryl groups, alkylamino groups, alkylboron groups, alkylsilyl groups, and alkylamine groups, alkyl groups are as exemplified above.

[0070] In this specification, among the aryloxy group, arylthio group, arylsulfoxy group, arylamino group, arylboron group, arylsilyl group, and arylamine group, the aryl group is as exemplified above.

[0071] In this specification, direct bonding may mean a single bond.

[0072] In this specification, JPEG2026135762000011.jpg1151 This indicates the position where they are connected.

[0073] Hereinafter, an embodiment of the present invention will be described with reference to the drawings.

[0074] Figure 1 is a block diagram of an electronic device according to one embodiment. Referring to Figure 1, the electronic device EA according to one embodiment may include a display module DM, a processor PR, a memory MR, and a power supply module PM.

[0075] A processor PR may include at least one of the following: a central processing unit (CPU), an application processor (AP), a graphics processing unit (GPU), a communication processor (CP), an image signal processor (ISP), or a controller.

[0076] Memory MR may store data information necessary for the operation of the processor PR and the display module DM. When the processor PR executes an application stored in memory MR, video data signals and / or input control signals are transmitted to the display module DM, which can process the provided signals and output video information via a display screen. The display module DM may include a display panel for displaying video.

[0077] The power module PM may include a power supply module such as a power adapter or battery device, and a power conversion module that converts the power supplied by the power supply module to generate the power necessary for the operation of the electronic device EA.

[0078] At least one of the components of the electronic device EA described above may be included in a display module according to one embodiment described later, and in a display device according to one embodiment including the same. Furthermore, some of the individual modules functionally contained within a single module may be included in the display device, while others may be provided separately from the display device. For example, the display device may include a display module DM, while the processor PR, memory MR, and power supply module PM may be provided in the form of other devices within the electronic device EA rather than in the display device.

[0079] Figure 2 is a schematic diagram of one embodiment of various electronic devices.

[0080] Referring to Figure 2, the various electronic devices including the display module according to one embodiment may include not only electronic devices for displaying images such as smartphones EA_1a, tablet PCs EA_1b, laptops EA_1c, televisions EA_1d, and desk monitors EA_1e, but also wearable electronic devices such as smart glasses EA_2a, head-mounted displays EA_2b, and smartwatches EA_2c, as well as automotive electronic devices EA_3 such as CIDs (Center Information Displays) and rearview mirror displays located on the instrument panel, center fascia, and dashboard of an automobile.

[0081] Figure 3 is a plan view showing one embodiment of the display module DM. Figure 4 is a cross-sectional view of the display module DM according to one embodiment. Figure 4 is a cross-sectional view showing the portion corresponding to the line I-I' in Figure 3.

[0082] The display module DM may include a plurality of light-emitting elements ED-1, ED-2, and ED-3. In one embodiment, the display module DM may include a display panel DP containing a plurality of light-emitting elements ED-1, ED-2, and ED-3, and a light-emitting layer PP disposed on the display panel DP.

[0083] The display panel DP may include a base layer BS, a circuit layer DP-CL provided on the base layer BS, and a display element layer DP-ED. The display element layer DP-ED may include a pixel definition film PDL, light-emitting elements ED-1, ED-2, and ED-3 positioned between the pixel definition films PDL, and a sealing layer TFE positioned on top of the light-emitting elements ED-1, ED-2, and ED-3.

[0084] The base layer BS may be a component that provides the base surface on which the display element layer EP-ED is arranged. The base layer BS may be a glass substrate, a metal substrate, a plastic substrate, etc. However, the examples are not limited to these, and the base layer BS may be an inorganic layer, an organic layer, or a composite material layer.

[0085] In one embodiment, the circuit layer DP-CL is located on the base layer BS, but the circuit layer DP-CL may include a plurality of transistors (not shown). Each transistor (not shown) may include a control electrode, an input electrode, and an output electrode. For example, the circuit layer DP-ED may include a switching transistor and a drive transistor for driving the organic electroluminescent elements ED-1, ED-2, and ED-3. Each of the light-emitting elements ED-1, ED-2, and ED-3 may have the structure of one embodiment of the light-emitting element ED shown in Figures 5 to 9, which will be described later. 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.

[0086] The optical layer PP is positioned on the display panel DP and can control the reflected light on the display panel DP from external light. The optical layer PP may include, for example, a polarizing layer or a color filter layer. Unlike the illustration, the optical layer PP may be omitted from the display module DM in one embodiment.

[0087] A base substrate BL may be placed on top of the optical layer PP. The base substrate BL may be a component that provides a base surface on which the optical layer PP is placed. The base substrate BL may be a glass substrate, a metal substrate, a plastic substrate, etc. However, the embodiment is not limited to these, and the base substrate BL may be an inorganic layer, an organic layer, or a composite material layer. Also, contrary to the figures, the base substrate BL may be omitted in one embodiment.

[0088] A display module DM according to one embodiment may further include a charging layer (not shown). A packing layer (not shown) may be disposed between the display element layer DP-ED and the base substrate BL. The packing layer (not shown) may be an organic layer. The packing layer (not shown) may contain at least one of acrylic resin, silicone resin, and epoxy resin.

[0089] Figure 4 shows an embodiment in which the light-emitting layers EML-R, EML-G, and EML-B of the light-emitting elements ED-1, ED-2, and ED-3 are arranged within the opening OH defined in the pixel-defining film PDL, and the hole transport region HTR, electron transport region ETR, and second electrode EL2 are provided as a common layer for all light-emitting elements ED-1, ED-2, and ED-3. However, the embodiments are not limited to this, and in one embodiment, contrary to the illustration in Figure 4, the hole transport region HTR and electron transport region ETR may be patterned and provided inside the opening OH defined in the pixel-defining film PDL. For example, in one embodiment, the hole transport region HTR, light-emitting layers EMLML-R, EMLML-G, EMLML-B, and electron transport region ETR of the light-emitting elements ED-1, ED-2, and ED-3 may be patterned and provided by an inkjet printing method.

[0090] The sealing layer TFE may cover the organic electroluminescent elements ED-1, ED-2, and ED-3. The sealing layer TFE may seal the display element layer DP-ED. The sealing layer TFE may be a thin film sealing layer. The sealing layer TFE may consist of one or more layers stacked together. The sealing layer TFE includes at least one insulating layer. The sealing layer TFE according to one embodiment may include at least one inorganic film (hereinafter referred to as the sealing inorganic film). Furthermore, the sealing layer TFE according to one embodiment may include at least one organic film (hereinafter referred to as the sealing organic film) and at least one sealing inorganic film.

[0091] The encapsulating inorganic film protects the display element layer DP-ED from moisture / oxygen, and the encapsulating organic film protects the display element layer DP-ED from foreign matter such as dust particles. The encapsulating inorganic film may include, but is not limited to, silicon nitride, silicon oxynitride, silicon oxide, titanium oxide, or aluminum oxide. The encapsulating organic film may include acrylic compounds, epoxy compounds, etc. The encapsulating organic film may include, but is not limited to, photopolymerizable organic materials.

[0092] The sealing layer TFE may be placed on top of the second electrode EL2 and fill the opening OH.

[0093] Referring to Figures 3 and 4, the display module DM may include a non-emitting region NPXA and emitting regions PXA-R, PXA-G, and PXA-B. Each of the emitting regions PXA-R, PXA-G, and PXA-B may be a region from which light generated by the light-emitting elements ED-1, ED-2, and ED-3, respectively, is emitted. The display module DM may include a first emitting region PXA-R, a second emitting region PXA-G, and a third emitting region PXA-B that are spaced apart from each other on a plane.

[0094] The first to third light-emitting regions PXA-R, PXA-G, and PXA-B may each be regions separated by a pixel-defining film PPL. The non-light-emitting region NPXA is the region between adjacent light-emitting regions PXA-R, PXA-G, and PXA-B, and may correspond to a pixel-defining film PDL. In this specification, each of the light-emitting regions PXA-R, PXA-G, and PXA-B may correspond to a pixel. The pixel-defining film PDL may separate 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 may be located in and separated by an aperture OH defined in the pixel-defining film PDL.

[0095] The light-emitting regions PXA-R, PXA-G, and PXA-B can be divided into multiple groups according to the color of the light generated from the light-emitting elements ED-1, ED-2, and ED-3. The display module DM of one embodiment shown in Figures 3 and 4 exemplifies three light-emitting regions PXA-R, PXA-G, and PXA-B that emit red, green, and blue light, respectively. For example, the first light-emitting region PXA-R may be called the red light-emitting region, the second light-emitting region PXA-G the green light-emitting region, and the third light-emitting region PXA-B the blue light-emitting region.

[0096] In one embodiment of the display module DM, the multiple light-emitting elements ED-1, ED-2, and ED-3 may emit light of different wavelengths. For example, in one embodiment, the display module DM may include a light-emitting element ED-1 that emits red light, a second light-emitting element ED-3 that emits green light, and a third light-emitting element ED-3 that emits blue light. That is, the red light-emitting region PXA-R, the green light-emitting region PXA-G, and the blue light-emitting region PXA-B may correspond to the first light-emitting element ED-1, the second light-emitting element ED-2, and the third light-emitting element ED-3, respectively.

[0097] However, the examples are not limited to these, and the first to third light-emitting elements ED-1, ED-2, and ED-3 may emit light in the same wavelength range, or at least one of them may emit light in a different wavelength range. Furthermore, all of the first to third light-emitting elements ED-1, ED-2, and ED-3 may emit blue light.

[0098] In one embodiment, the light-emitting regions PXA-R, PXA-G, and PXA-B in the display module DM may be arranged in a striped pattern. Referring to Figure 3, multiple first light-emitting regions PXA-R, multiple second light-emitting regions PXA-G, and multiple third light-emitting regions PXA-B may be aligned along the second directional axis DR2. Alternatively, the first light-emitting region PXA-R, the second light-emitting region PXA-G, and the third light-emitting region PXA-B may be arranged alternately along the first directional axis DR1.

[0099] Although Figures 3 and 4 show that the areas of the light-emitting regions PXA-R, PXA-G, and PXA-B are all similar, the embodiments are not limited to these, and the areas of the light-emitting regions PXA-R, PXA-G, and PXA-B may differ from each other depending on the wavelength range of the emitted light. The areas of the light-emitting regions PXA-R, PXA-G, and PXA-B may represent the area as viewed from the plane defined by the first directional axis DR1 and the second directional axis DR2.

[0100] The arrangement of the light-emitting regions PXA-R, PXA-G, and PXA-B is not limited to that shown in Figure 3. The order in which the first light-emitting region PXA-R, the second light-emitting region PXA-G, and the third light-emitting region PXA-B are arranged is provided in various combinations depending on the display quality characteristics required from the display module DM. For example, the arrangement of the light-emitting regions PXA-R, PXA-G, and PXA-B is Pentile. TM ) Arrangement form, or diamond (Diamond Pixel) TM ) It may have the form of an array.

[0101] Furthermore, the areas of the light-emitting regions PXA-R, PXA-G, and PXA-B may differ from each other. For example, in one embodiment, the area of ​​the second light-emitting region PXA-G, which is a green light-emitting region, may be smaller than the area of ​​the third light-emitting region PXA-B, which is a blue light-emitting region, but the embodiment is not limited to this.

[0102] Figures 5 to 9 below are schematic cross-sectional views showing 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, which are sequentially stacked.

[0103] Figure 6 shows a cross-sectional view of an embodiment of a light-emitting element ED, compared to Figure 5, in which the hole transport region HTR includes a hole injection layer HIL and a hole transport layer HTL, and the electron transport region ETR includes an electron injection layer EIL and an electron transport layer ETL. Figure 7 also shows a cross-sectional view of an embodiment of a light-emitting element ED, compared to Figure 5, in which the hole transport region HTR includes a hole injection layer HIL, a hole transport layer HTL, and an electron blocking layer EBL, and the electron transport region ETR includes an electron injection layer EIL, an electron transport layer ETL, and a hole blocking layer HBL. Figure 8 shows a cross-sectional view of an embodiment of a light-emitting element ED, compared to Figure 5, in which the hole transport region HTR includes a hole injection layer HIL, a hole transport layer HTL, and an electron blocking layer EAL, and the electron transport region ETR includes an electron injection layer EIL, an electron transport layer ETL, and a hole blocking layer HBL. Figure 9 shows a cross-sectional view of an embodiment of the light-emitting element ED, including a capping layer CPL placed on the second electrode EL2, compared to Figure 6.

[0104] The first electrode EL1 is conductive. The first electrode EL1 may consist of a metallic material, a metallic alloy, or a conductive compound. The first electrode EL1 may be an anode or a cathode. However, the examples are not limited to these. The first electrode EL1 may also be a pixel electrode. The first electrode EL1 may be a transmissive electrode, a semitransmissive electrode, or a reflective electrode. The first electrode EL1 may contain at least one selected from Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF, Mo, Ti, W, In, Sn, and Zn, two or more compounds selected from these, a mixture of two or more selected from these, or oxides thereof.

[0105] If the first electrode EL1 is a transmissive electrode, it may contain transparent metal oxides such as ITO (indium tin oxide), IZO (indium zinc oxide), ZnO (zinc oxide), ITZO (indium tin zinc oxide), etc. If the first electrode EL1 is a semi-transmissive or reflective electrode, it may contain Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF / Ca (a layered structure of LiF and Ca), LiF / Al (a layered structure of LiF and Al), Mo, Ti, W, or compounds or mixtures thereof (for example, a mixture of Ag and Mg). Alternatively, the first electrode EL1 may have a multi-layer structure including a reflective or semi-transmissive film made of the above-mentioned material, and a transparent conductive film made of ITO, IZO, ZnO, ITZO, etc. For example, the first electrode EL1 may have a three-layer structure of ITO / Ag / ITO, but is not limited to this. Furthermore, the examples are not limited to those described above, and the first electrode EL1 may include the above-mentioned metal material, a combination of two or more metal materials selected from the above-mentioned metal materials, or an oxide of the above-mentioned metal material. The thickness of the first electrode EL1 may be approximately 700 Å to approximately 10000 Å. For example, the thickness of the first electrode EL1 may be approximately 1000 Å to approximately 3000 Å.

[0106] 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 light emission auxiliary layer (EAL), and an electron blocking layer (EBL). The thickness of the hole transport region (HTR) may be, for example, about 50 Å to about 15,000 Å. The light emission auxiliary layer (EAL) may be referred to as a buffer layer.

[0107] The hole transport region (HTR) may have a single layer made of a single material, a single layer made of multiple different materials, or a multilayer structure having multiple layers made of multiple different materials.

[0108] For example, the hole transport region HTR may have a single-layer structure of a hole injection layer HIL or a hole transport layer HTL, or it may have a single-layer structure consisting of a hole injection material and a hole transport material. Alternatively, the hole transport region HTR may have a single-layer structure consisting of multiple different materials, or it may have a structure of a hole injection layer HIL / hole transport layer HTL, a hole injection layer HIL / hole transport layer HTL / luminescence auxiliary layer EAL, a hole injection layer HIL / luminescence auxiliary layer EAL, a hole transport layer HTL / luminescence auxiliary layer EAL, a hole injection layer HIL / hole transport layer HTL / luminescence auxiliary layer EAL, or a hole injection layer HIL / hole transport layer HTL / electron blocking layer EBL stacked in order from the first electrode EL1, but the examples are not limited to these.

[0109] Hole transport regions (HTRs) can be formed using a variety of methods, including vacuum deposition, spin coating, casting, LB (Langmuir-Blodgett) method, inkjet printing, laser printing, and laser-induced thermal imaging (LITI).

[0110] The hole transport region (HTR) may contain a compound represented by the following chemical formula H-1.

[0111] [Chemical formula H-1] JPEG2026135762000012.jpg3264

[0112] In chemical formula H-1, L1 and L2 can each independently be directly bonded, substituted, or unsubstituted arylene groups with 6 to 30 ring-forming carbon atoms, or substituted or unsubstituted heteroarylene groups with 2 to 30 ring-forming carbon atoms. a and b can each independently be integers from 0 to 10. If a or b is an integer of 2 or more, then multiple L1 and L2 can each independently be substituted or unsubstituted arylene groups with 6 to 30 ring-forming carbon atoms, or substituted or unsubstituted heteroarylene groups with 2 to 30 ring-forming carbon atoms.

[0113] In chemical formula H-1, Ar1 to Ar2 can each independently be a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms. Furthermore, in chemical formula H-1, Ar3 can be a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms.

[0114] The compound represented by the chemical formula H-1 may be a monoamine compound. Alternatively, the compound represented by the chemical formula H-1 may be a diamine compound in which at least one of Ar1 to Ar3 has an amine group as a substituent. Alternatively, the compound represented by the chemical formula H-1 may be a carbazole compound in which at least one of Ar1 to Ar2 has a substituted or unsubstituted carbazole group, or a cafluorene compound in which at least one of Ar1 to Ar2 has a substituted or unsubstituted fluorene group.

[0115] A compound represented by the chemical formula H-1 can be any one of the compounds in compound group H below. However, the compounds listed in compound group H below are illustrative examples, and the compound represented by the chemical formula H-1 is not limited to those shown in compound group H below.

[0116] [Compound group H] JPEG2026135762000013.jpg252170

[0117] The hole transport region (HTR) is used for phthalocyanine compounds such as copper phthalocyanine, and DNTPD(N 1 ,N 1’ -([1,1'-biphenyl]-4,4'-diyl)bis(N 1 -phenyl-N 4 ,N 4 -di-m-tolylbenzene-1,4-diamine), m-MTDATA(4,4',4”-[tris(3-methylphenyl)phenylamino]triphenylamino), TDATA(4,4',4”-tris(N,N-diphenylamino)triphenylamine), 2-TNATA(4,4',4”-tris[N(2-naphthyl)-N-phenylamino]-triphenylamine), PEDOT / PSS(poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate), PANI / DBSA(polyaniline / dodecylbenzenesulfonic acid), PANI / CSA(polyaniline / camphorsulfonic acid), PANI / PSS((polyaniline) / poly(4-styrenesulfonate)), NPB It may contain (N,N'-di(naphthalene-1-yl)-N,N'-diphenyl-benzidine), polyether ketone containing triphenylamine (TPAPEK), 4-isopropyl-4'-methyldiphenyliodonium tetrakis(pentafluorophenyl) borate, HATCN (dipyradino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonnitrile), etc.

[0118] The hole transport region HTR may include, for example, carbazole derivatives such as N-phenylcarbazole and polyvinylcarbazole, fluorene derivatives, triphenylamine derivatives such as TPD (N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1-biphenyl]-4,4'-diamine) and TCTA (4,4',4"-tris(N-carbazolyl)triphenylamine), NPB (N,N'-di(naphthalene-1-yl)-N,N'-diphenyl-benzidine), TAPC (4,4'-cyclohexylidenebis[N,N-bis(4-methylphenyl)benzeneamine]), and HMTPD (4,4'-bis[N,N'-(3-tolyl)amino]-3,3'-dimethylbiphenyl).

[0119] Furthermore, the hole transport region HTR may include CzSi(9-(4-tert-butylphenyl)-3,6-bis(triphenylsilyl)-9H-(carbazole), CCP(9-phenyl-9H-3,9'-bicarbazole), or mDCP(1,3-bis(1,8-dimethyl-9H-carbazole-9-yl)benzene).

[0120] The hole transport region (HTR) may contain the aforementioned hole transport region compound in at least one of the hole injection layer (HIL), hole transport layer (HTL), luminescence auxiliary layer (EAL), and electron blocking layer (EBL).

[0121] The thickness of the hole transport region (HTR) can be approximately 100 Å to approximately 10,000 Å, for example, approximately 100 Å to approximately 5,000 Å. If the hole transport region (HTR) includes a hole injection layer (HIL), the thickness of the hole injection layer (HIL) can be, for example, approximately 30 Å to approximately 1,000 Å. If the hole transport region (HTR) includes a hole transport layer (HTL), the thickness of the hole transport layer (HTL) can be approximately 30 Å to approximately 1,000 Å. For example, if the hole transport region (HTR) includes a hole blocking layer (EBL), the thickness of the hole blocking layer (EBL) can be, for example, approximately 10 Å to approximately 1,000 Å. If the thicknesses of the hole transport region (HTR), hole injection layer (HIL), hole transport layer (HTL), and electron blocking layer (EBL) satisfy the above-described ranges, satisfactory hole transport characteristics can be obtained without a substantial increase in the driving voltage.

[0122] The hole transport region (HTR) may further contain charge-generating materials in addition to the materials described above to improve conductivity. The charge-generating material may be uniformly or non-uniformly dispersed within the hole transport region (HTR). The charge-generating material may be, for example, a p-dopant. The p-dopant may contain, but is not limited to, at least one of metal halide compounds, quinone derivatives, metal oxides, and cyano group-containing compounds. For example, p-dopants include metal halide compounds such as CuI and RBI, quinone derivatives such as TCNQ (tetracyanoquinodimethane) and F4-TCNQ (2,3,5,6-tetrafluoro-7,7',8,8-tetracyanoquinodimethane), metal oxides such as tungsten oxide and molybdenum oxide, and cyano group-containing compounds such as HATCN (dipyradino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonnitrile) and NDP9 (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 to these.

[0123] As described above, the hole transport region (HTR) may further include at least one of the following: an emissive layer (EAL) and an electron blocking layer (EBL), in addition to the hole transport layer (HTL) and the hole injection layer (HIL). The emissive layer (EAL) can guarantee the resonance distance based on the wavelength of light emitted from the emissive layer (EML) and can increase the light emission efficiency by adjusting the hole charge balance. The emissive layer (EAL) may also play a role in preventing electron injection into the hole transport region (HTR). The emissive layer (EAL) may contain materials that can be included in the hole transport region (HTR). The electron blocking layer (EBL) may be a layer that prevents electron injection from the electron transport region (ETR) into the hole transport region (HTR).

[0124] In one embodiment of the light-emitting element ED, the light-emitting layer EML may contain a condensed polycyclic compound according to the embodiment. In one embodiment of the light-emitting element ED, the light-emitting layer EML may contain a first compound, which is a condensed polycyclic compound, and at least one of the second and third compounds. Furthermore, in one embodiment of the light-emitting element ED, the light-emitting layer EML may further contain a fourth compound. The second compound may contain a tricyclic condensed ring with a nitrogen atom as a ring-forming atom. The third compound may contain a hexagonal ring group with at least one nitrogen atom as a ring-forming atom. The fourth compound may contain an organometallic complex. The second to fourth compounds will be described in more detail later.

[0125] In this specification, the first compound may be referred to as the polycyclic compound of one example. The polycyclic compound of one example contains a boron-containing condensed ring as its core structure. The polycyclic compound of one example, which is the first compound, may contain two boron atoms as ring-forming atoms and a core structure that includes heteroatoms as ring-forming atoms in addition to the boron atoms. The core structure of the polycyclic compound of one example may include a boron-containing heterocondensed ring structure in which nine rings are condensed. The core structure of the polycyclic compound of one example may be described as containing a heteroborine skeleton that includes two boron atoms as ring-forming atoms.

[0126] The polycyclic compound of one example may contain at least one nitrogen atom in the constituent rings of a fused ring that does not contain boron as a ring-forming atom, or it may contain a heterocycle containing a nitrogen atom as a ring-forming atom as a substituent. For example, the polycyclic compound of one example may have at least one of the rings forming the fused ring being a pyridine derivative, or it may contain a pyridyl group as a substituent of the amine forming the core structure.

[0127] One example of a polycyclic compound may exhibit thermally activated delayed fluorescence (TADF) emission characteristics through reverse intersystem crossing.

[0128] Furthermore, the polycyclic compound of one example has a structure in which some of the carbon atoms in the heteroborin skeleton are converted to nitrogen, or a structure in which pyridyl groups are substituted for the amine groups forming the heteroborin skeleton. This allows for a balance between electron-donating and electron-withdrawing groups, resulting in a short delayed fluorescence erasure time and excellent material stability. As a result, the light-emitting element of one example, which includes the polycyclic compound of one example, can exhibit high luminous efficiency and long lifetime characteristics.

[0129] The light-emitting element ED of one embodiment may contain the polycyclic compound of one embodiment. The polycyclic compound of one embodiment may be represented by the following chemical formula 1.

[0130] [Chemical formula 1] JPEG2026135762000014.jpg7677

[0131] In chemical formula 1, X1 to X4 can each be independently O, S, Se, or a group represented by chemical formula 2 below. For example, in chemical formula 1, X1 to X4 can each be independently O, S, Se, or an amine group represented by chemical formula 2 below. If X1 to X4 are amine groups represented by chemical formula 2 below, the nitrogen atom of the amine group may be included in the positions of X1 to X4.

[0132] [Chemical formula 2] JPEG2026135762000015.jpg2139

[0133] In the polycyclic compound represented by chemical formula 1, Y1 to Y 16 Each is independently CR a Or it could be N. CR a In R a This can be a hydrogen atom, a deuterium atom, a cyano group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms.

[0134] In the amino group represented by chemical formula 2, Y 17 Y 21Each is independently CR b or N, R b This can be a hydrogen atom, a deuterium atom, a cyano group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms.

[0135] In a polycyclic compound represented by chemical formula 1, if none of X1 to X4 are represented by chemical formula 2, then Y1 to Y of chemical formula 1 16 At least one of them can be N. For example, in a polycyclic compound represented by chemical formula 1, if X1 to X4 are selected from O, S, or Se, then the polycyclic compound represented by chemical formula 1 may have a structure in which one of the ring-forming carbon atoms of the core structure is changed to N. Also, in a polycyclic compound represented by chemical formula 1, if at least one of X1 to X4 is represented by chemical formula 2, then Y1 to Y of chemical formula 1 16 and Y of chemical formula 2 17 Y 21 At least one of them could be N.

[0136] The amine group of chemical formula 2 can be represented by the following chemical formula 2-1.

[0137] [Chemical formula 2-1] JPEG2026135762000016.jpg3339

[0138] Alternatively, the amine derivative represented by chemical formula 2 in one example is Y of chemical formula 2. 17 Y 21 One of them is N, and the others are CR independently. b It can be described as being substituted with a pyridine derivative.

[0139] In chemical formula 2-1, R b1 ~R b5Each of these can independently be a hydrogen atom, a deuterium atom, a cyano group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms.

[0140] In one example of the polycyclic compound, one of Y1 to Y4 of chemical formula 1, one of Y6 to Y8, and Y 13 Y 16 One of these, and one selected from Y5, is N, and the remaining ones are independently CR a It is possible. Also, one of Y1 to Y4 of chemical formula 1, one of Y6 to Y8, Y 13 Y 16 One of these, and one selected from Y5, is N, and the remaining ones are independently CR a In this case, X1 to X4 may each be independently O, S, Se, or represented by the chemical formula 2-1 below.

[0141] For example, the polycyclic compound of one example can be represented by any one of the following chemical formulas 1-1A to 1-1E.

[0142] [Chemical formula 1-1A] [Chemical formula 1-1B] JPEG2026135762000017.jpg86166 [Formula 1-1C] [Formula 1-1D] JPEG2026135762000018.jpg79166 [Chemical formula 1-1E] JPEG2026135762000019.jpg7177

[0143] In the aforementioned chemical formula 1-1A, one of Y1 to Y4 is N and the rest are CR. a Therefore, in the above chemical formula 1-1C, one of Y6 to Y8 is N and the rest are CR. a Therefore, in the above chemical formula 1-1D, Y8 to Y 12One of them is N and the rest are CR a Therefore, in the above chemical formula 1-1E, Y 13 Y 16 One of them is N and the rest are CR a It is possible. In the above chemical formulas 1-1A, 1-1C, 1-1D, and 1-1E, CR a R a This is the same as what was explained in Chemical Formula 1 above.

[0144] In chemical formulas 1-1A to 1-1E, R a1 ~R a16 Each of these can independently be a hydrogen atom, a deuterium atom, a cyano group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms.

[0145] The polycyclic compound of one embodiment can be represented by the following chemical formulas 1-2. In the following chemical formulas 1-2, at least one of X1 to X4 is represented by chemical formula 2, and the remaining ones can each be independently O, S, or Se. Also, when at least one of X1 to X4 is represented by chemical formula 2, Y of chemical formula 2 17 Y 21 One of them is N and the rest are CR b It is possible. R b The same principles described above for chemical formula 2 may apply to this.

[0146] [Chemical formula 1-2] JPEG2026135762000020.jpg7877 [Chemical formula 2] JPEG2026135762000021.jpg2239

[0147] In the polycyclic compound of one example represented by chemical formula 1-2, R a1 ~R a16Each of these can independently be a hydrogen atom, a deuterium atom, a cyano group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms.

[0148] The polycyclic compound of one embodiment may be represented by any one of the compounds in the following first compound group. The light-emitting element ED according to one embodiment may contain at least one of the compounds in the following first compound group. In the following first compound group, D is a deuterium atom.

[0149] [First compound group] JPEG2026135762000022.jpg218170 JPEG2026135762000023.jpg235170 JPEG2026135762000024.jpg229170 JPEG2026135762000025.jpg242170 JPEG2026135762000026.jpg245170 JPEG2026135762000027.jpg212170 JPEG2026135762000028.jpg234170 JPEG2026135762000029.jpg212170 JPEG2026135762000030.jpg229170 JPEG2026135762000031.jpg224170 JPEG2026135762000032.jpg160166

[0150] The polycyclic compound of one embodiment may contain a boron-containing condensed ring core with two boron atoms as ring-forming atoms, and may contain nitrogen as a ring-forming atom of the core, or a nitrogen-containing heteroaryl bonded to the nitrogen of the amine group contained as a ring-forming atom of the core. The polycyclic compound of one embodiment may have a condensed heterocyclic core structure in which nine hexacyclic rings are fused together.

[0151] The nitrogen-containing compound of one example can be used as a delayed fluorescence material. For example, the polycyclic compound of one example can be used as a thermally activated delayed fluorescence (TADF) material. The polycyclic compound of one example can exhibit a high fluorescence quantum yield. For example, the polycyclic compound of one example can exhibit a high fluorescence quantum yield in the blue wavelength region with a maximum central wavelength of 470 nm or less.

[0152] The polycyclic compound of one embodiment may exhibit excellent material stability by having a fused ring core structure in which nine hexacyclic rings are fused together, and by including nitrogen in the core structure or a pyridyl group as a substituent. Furthermore, the polycyclic compound of one embodiment may exhibit high luminescence efficiency and excellent lifetime characteristics in the blue light wavelength region.

[0153] A light-emitting element according to one embodiment, containing a polycyclic compound according to one embodiment, can exhibit high efficiency and long lifespan characteristics. A light-emitting element according to one embodiment, containing a polycyclic compound according to one embodiment, which has excellent luminous efficiency and improved material stability, can exhibit high light efficiency and excellent lifespan characteristics.

[0154] The light-emitting element of one embodiment, which includes a polycyclic compound, may exhibit a short fluorescence lifetime. The light-emitting element of one embodiment may exhibit a fluorescence lifetime of 3.0 μs or less. By having a faster fluorescence lifetime of 3.0 μs or less, the light-emitting element of one embodiment may exhibit improved lifetime characteristics.

[0155] In one embodiment of the light-emitting element, the light-emitting layer EML may be a delayed fluorescence light-emitting layer containing a host and a dopant. More specifically, the light-emitting layer EML may emit thermally activated delayed fluorescence. The polycyclic compound in one embodiment may be a thermally activated delayed fluorescence dopant.

[0156] The light-emitting layer EML may contain a polycyclic compound of an embodiment as a dopant. The polycyclic compound of an embodiment may emit blue light. For example, the polycyclic compound of an embodiment may be a light-emitting material having a maximum emission wavelength in a wavelength region of 430 nm or more and 490 nm or less. Specifically, the polycyclic compound of an embodiment may be a light-emitting material having a maximum emission wavelength in a wavelength region of 440 nm or more and 470 nm or less.

[0157] In one embodiment, the light-emitting layer EML contains a polycyclic compound of an embodiment and may contain at least one of the second to fourth compounds. In one embodiment, the light-emitting layer EML may contain the second compound represented by the following chemical formula HT-1. For example, the second compound may be used as a hole-transporting host material of the light-emitting layer EML.

[0158] [Chemical formula HT-1] JPEG2026135762000033.jpg4364

[0159] In Chemical formula HT-1, A1 to A8 may each independently be N or CR 51 For example, A1 to A8 may all be CR 51 Alternatively, any one of A1 to A8 may be N and the rest may be CR 51 For example, A1 to A8 may all be CR

[0160] In Chemical formula HT-1, L1 may be a direct bond, a substituted or unsubstituted arylene group having 6 or more and 30 or less ring-forming carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 or more and 30 or less ring-forming carbon atoms. For example, L1 may be a direct bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted divalent biphenyl group, a substituted or unsubstituted divalent carbazole group, etc., but the examples are not limited thereto.

[0161] In Chemical formula HT-1, Y a is a direct bond, CR 52 R 53 , or SiR 54 R 55It is possible. That is, the two benzene rings linked to the nitrogen atom of Chemical Formula HT-1 may be directly bonded, JPEG2026135762000034.jpg2377 or may be linked via. In Chemical Formula HT-1, Y a If it is a direct bond, the second compound represented by Chemical Formula HT-1 may contain a carbazole partial structure.

[0162] In Chemical Formula HT-1, Ar1 may be a substituted or unsubstituted aryl group having 6 or more and 30 or less ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 or more and 30 or less ring-forming carbon atoms. For example, Ar1 may be a substituted or unsubstituted carbazole group, a substituted or unsubstituted dibenzofuran group, a substituted or unsubstituted dibenzothiophene group, or a substituted or unsubstituted biphenyl group, etc., but the examples are not limited thereto.

[0163] In Chemical Formula HT-1, R 51 to R 55 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted thio group, a substituted or unsubstituted oxy group, a substituted or unsubstituted amine group, a substituted or unsubstituted boron group, a substituted or unsubstituted alkyl group having 1 or more and 20 or less carbon atoms, a substituted or unsubstituted alkenyl group having 2 or more and 20 or less carbon atoms, a substituted or unsubstituted aryl group having 6 or more and 60 or less ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 or more and 60 or less ring-forming carbon atoms. Or, each of R 51 to R 55 may combine with adjacent groups to form a ring with each other. For example, each of R 51 to R 55 may be independently a hydrogen atom or a deuterium atom. Each of R 51 to R 55 may be independently an unsubstituted methyl group or an unsubstituted phenyl group.

[0164] In one embodiment, the second compound represented by the chemical formula HT-1 may be any one of the compounds shown in the second compound group below. The light-emitting layer EML may contain at least one of the compounds shown in the second compound group below as a hole-transporting host material.

[0165] [Second compound group] JPEG2026135762000035.jpg167170 JPEG2026135762000036.jpg121170 JPEG2026135762000037.jpg66170 JPEG2026135762000038.jpg109170 JPEG2026135762000039.jpg68170 JPEG2026135762000040.jpg76170

[0166] In the specific compounds presented in the second group of compounds, "D" can represent a deuterium atom, and "Ph" can represent a substituted or unsubstituted phenyl group. For example, in the specific compounds presented in the second group of compounds, "Ph" may represent an unsubstituted phenyl group.

[0167] In one embodiment, the luminescent layer EML may contain a third compound represented by the following chemical formula ET-1. For example, the third compound can be used as an electron-transporting host material for the luminescent layer EML.

[0168] [Chemical formula ET-1] JPEG2026135762000041.jpg5677

[0169] In chemical formula ET-1, at least one of X1 to X3 is N, and the rest are CR. 56 It is possible. For example, one of X1 through X3 is N, and the remaining two are each independently CR. 56 This is possible. In this case, the third compound represented by chemical formula ET-1 may include a pyridine substructure. Alternatively, two of X1 to X3 are N and the remaining one is CR. 56This is possible. In this case, the third compound represented by chemical formula ET-1 may include a pyrimidine substructure. Alternatively, X1 to X3 may all be N. In this case, the third compound represented by chemical formula ET-1 may include a triazine substructure.

[0170] In chemical formula ET-1, R 56 This can be a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 ring-forming carbon atoms.

[0171] In chemical formula ET-1, b1 to b3 can each be an independent integer between 0 and 10.

[0172] In chemical formula ET-1, Ar2 to Ar4 can each independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms. For example, Ar2 to Ar4 can be a substituted or unsubstituted phenyl group, or a substituted or unsubstituted carbazole group.

[0173] In chemical formula ET-1, L2 to L4 can each independently be a directly bonded, substituted, or unsubstituted arylene group with 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroarylene group with 2 to 30 ring-forming carbon atoms. If b1 to b3 are integers of 2 or more, L2 to L4 can each independently be a substituted or unsubstituted arylene group with 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroarylene group with 2 to 30 ring-forming carbon atoms.

[0174] In one embodiment, the third compound may be represented by any one of the compounds in the third compound group described below. The light-emitting element ED in one embodiment may contain any one of the compounds in the third compound group described below.

[0175] [Third compound group] JPEG2026135762000042.jpg134170 JPEG2026135762000043.jpg139170 JPEG2026135762000044.jpg137170 JPEG2026135762000045.jpg134170 JPEG2026135762000046.jpg157170 JPEG2026135762000047.jpg155170 JPEG2026135762000048.jpg131170 JPEG2026135762000049.jpg76170

[0176] In the specific compounds presented in the third group of compounds, "D" represents a deuterium atom, and "Ph" represents an unsubstituted phenyl group.

[0177] The luminescent layer EML contains a second compound and a third compound, and the second and third compounds can form an exciplex. In the luminescent layer EML, an exciplex can be formed by a hole-transporting host and an electron-transporting host. In this case, the triplet energy of the exciplex formed by the hole-transporting host and the electron-transporting host may correspond to the difference between the LUMO (Lowest Unoccupied Molecular Orbital) energy level of the electron-transporting host and the HOMO (Highest Occupied Molecular Orbital) energy level of the hole-transporting host.

[0178] For example, the absolute value of the triplet (T1) energy of an exciplex formed by a hole-transporting host and an electron-transporting host may be between 2.4 eV and 3.0 eV. Furthermore, the triplet energy of an exciplex may be smaller than the energy gap of each host material. An exciplex may have a triplet energy of 3.0 eV or less, which is the energy gap between the hole-transporting host and the electron-transporting host.

[0179] In one embodiment, the light-emitting layer EML may further contain a fourth compound in addition to the first to third compounds described above. The fourth compound can be used as a phosphorescent sensitizer for the light-emitting layer EML. Energy can be transferred from the fourth compound to the first compound, causing light emission.

[0180] For example, the light-emitting layer EML may contain Pt (platinum) as the central metal atom and an organometallic complex containing a ligand bound to the central metal atom as the fourth compound. In one embodiment of the light-emitting element ED, the light-emitting layer EML may contain a compound represented by the following chemical formula D-1 as the fourth compound.

[0181] [Chemical formula D-1] JPEG2026135762000050.jpg7377

[0182] In chemical formula D-1, Q1 to Q4 can each independently be C or N. C1 to C4 can each independently be a substituted or unsubstituted hydrocarbon ring with 5 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heterocycle with 2 to 30 ring-forming carbon atoms.

[0183] In chemical formula D-1, L 11 ~L 13 Each is independently and directly connected. JPEG2026135762000051.jpg21127 It may be a substituted or unsubstituted divalent alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted ring-forming arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heteroarylene group having 2 to 30 carbon atoms. 11 ~L 13 In, JPEG2026135762000052.jpg520 This refers to the part connected to C1 through C4.

[0184] In chemical formula D-1, b11 to b13 can each be independently 0 or 1. If b11 is 0, C1 and C2 do not need to be linked to each other. If b12 is 0, C2 and C3 do not need to be linked to each other. If b13 is 0, C3 and C4 do not need to be linked to each other.

[0185] In chemical formula D-1, R 61 ~R 66 Each of these can independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted thio group, a substituted or unsubstituted oxy group, a substituted or unsubstituted amine group, a substituted or unsubstituted boron group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 ring-forming carbon atoms. Or, R 61 ~R 66 Each can bond with an adjacent group to form a ring. 61 ~R 66 Each of these can independently be a substituted or unsubstituted methyl group, or a substituted or unsubstituted t-butyl group.

[0186] In chemical formula D-1, d1 and d4 can each be independent integers between 0 and 4. In chemical formula D-1, if d1 to d4 are all 0, then the fourth compound is R 61 ~R 66 Each of them does not need to be substituted. d1 through d4 are each 4, R 61 ~R 66 If each of them is a hydrogen atom, it can be the same as when d1 to d4 are all 0. If each of d1 to d4 is an integer of 2 or more, multiple R values ​​are provided. 61 ~R 66 Each of them is either the same or multiple Rs. 61 ~R 66 At least one of them may be different.

[0187] In chemical formula D-1, C1 to C4 can each independently be a substituted or unsubstituted hydrocarbon ring, or a substituted or unsubstituted heterocycle, represented by any one of the following C-1 to C-4. JPEG2026135762000053.jpg52170

[0188] In C-1 to C-4, P1 is JPEG2026135762000054.jpg339 or CR 74 Therefore, P2 is JPEG2026135762000055.jpg451 or NR 81 Therefore, P3 is JPEG2026135762000056.jpg451 or NR 82 Therefore, P4 is JPEG2026135762000057.jpg451 or CR 88 It is possible. R 71 and R 88 Each of these groups may independently be a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms forming a ring, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms forming a ring by bonding with adjacent groups.

[0189] Furthermore, in C-1 to C-4, JPEG2026135762000058.jpg1951 This is the part that is connected to the central metal atom, Pt. JPEG2026135762000059.jpg751 The adjacent ring groups (C1 to C4) or linkers (L 11 ~L 13 This could be the part that is connected to ).

[0190] In one embodiment, the luminescent layer EML may include a first compound, which is a polycyclic compound, and at least one of the second to fourth compounds. For example, the luminescent layer EML may include the first compound, the second compound, and the third compound. In the luminescent layer EML, the second and third compounds form an exciplex, and energy can be transferred from the exciplex to the first compound, causing luminescence.

[0191] Furthermore, the light-emitting layer EML may contain a first compound, a second compound, a third compound, and a fourth compound. In the light-emitting layer EML, the second and third compounds form an exciplex, and energy can be transferred from the exciplex to the fourth and first compounds, causing light emission. In one embodiment, the fourth chemical formula may be a sensitizer. In the light-emitting element ED of one embodiment, the fourth compound contained in the light-emitting layer EML may function as a sensitizer and play a role in transferring energy from the host to the first compound, which is a light-emitting dopant. In other words, the fourth compound, which acts as an auxiliary dopant, can accelerate the transfer of energy to the first compound, which is a light-emitting dopant, and increase the light emission ratio of the first compound. Therefore, the light-emitting layer EML of one embodiment may have improved luminescence efficiency. Also, if the transfer of energy to the first compound is increased, the excitons formed in the light-emitting layer EML will not accumulate inside the light-emitting layer EML and will emit light quickly, thus reducing the degradation of the light-emitting element. Therefore, the lifespan of the light-emitting element ED of one embodiment may be improved.

[0192] In one embodiment, the light-emitting element (ED) may contain all of the first, second, third, and fourth compounds, and the light-emitting layer (EML) may contain a combination of two host materials and two dopant materials. In the light-emitting element (ED) of one embodiment, the light-emitting layer (EML) can achieve excellent luminescence efficiency by simultaneously containing two different host compounds, the second and third compounds, the first compound which emits delayed fluorescence, and the fourth compound which contains an organometallic complex.

[0193] In one embodiment, the fourth compound represented by chemical formula D-1 may be represented by at least one of the compounds shown in the fourth compound group below. The luminescent layer EML may contain at least one of the compounds shown in the fourth compound group below as a sensitizer substance.

[0194] [Fourth compound group] JPEG2026135762000060.jpg40170 JPEG2026135762000061.jpg35170 JPEG2026135762000062.jpg43170 JPEG2026135762000063.jpg33170 JPEG2026135762000064.jpg35170 JPEG2026135762000065.jpg35170 JPEG2026135762000066.jpg33170 JPEG2026135762000067.jpg40170 JPEG2026135762000068.jpg30170 JPEG2026135762000069.jpg38170

[0195] In the specific compounds presented in the fourth group of compounds, "D" represents a deuterium atom.

[0196] In one embodiment of the light-emitting element ED, if the light-emitting layer EML contains all three compounds as described above, the content of the first compound may be 0.1 wt% or more and 5 wt% or less based on the total weight of the first, second, and third compounds. However, it is not limited to this. If the content of the first compound satisfies the above-mentioned ratio, the energy transfer from the second and third compounds to the first compound will increase, thereby increasing the luminous efficiency and the device lifetime.

[0197] In the light-emitting layer EML, the contents of the second compound and the third compound can be the remainder excluding the weight of the first compound described above. For example, in the light-emitting layer EML, the contents of the second compound and the third compound can be 65 wt% or more and 95 wt% or less based on the total weight of the first compound, the second compound, and the third compound.

[0198] In the total weight of the second compound and the third compound, the weight ratio of the second compound and the third compound can be about 3:7 to 7:3.

[0199] If the contents of the second compound and the third compound satisfy the above-mentioned ratios, the charge balance characteristics in the light-emitting layer EML are improved, so the light-emitting efficiency and the device lifetime can be increased. If the contents of the second compound and the third compound deviate from the above-mentioned ratios, the charge balance in the light-emitting layer EML is disrupted, the light-emitting efficiency decreases, and the device can be deteriorated.

[0200] When the light-emitting layer EML contains a fourth compound, in the light-emitting layer EML, based on the total weight of the first compound, the second compound, the third compound, and the fourth compound, the content of the fourth compound can be about 10 wt% or more and 30 wt% or less. However, it is not limited to this. If the content of the fourth compound satisfies the above-mentioned content, the energy transfer from the host to the first compound which is the light-emitting dopant increases and the emission efficiency ratio is improved, thereby the light-emitting efficiency of the light-emitting layer EML can be improved. If the first compound, the second compound, the third compound, and the fourth compound contained in the light-emitting layer EML satisfy the range of the above-mentioned content ratios, excellent light-emitting efficiency and long lifetime can be achieved.

[0201] The light-emitting layer EML can have a thickness of, for example, about 100 Å to about 1000 Å, or about 100 Å to about 300 Å. The light-emitting layer EML can have a single-layer structure composed of a single substance, a single-layer structure composed of a plurality of different substances, or a multilayer structure having a plurality of layers composed of a plurality of different substances.

[0202] In the light-emitting element ED of one embodiment shown in Figures 5 to 9, the light-emitting layer EML may contain the polycyclic compound of the embodiment described above as a dopant. In addition, in the light-emitting element ED of one embodiment shown in Figures 5 to 9, the light-emitting layer EML may contain at least one of the first compound, which is the polycyclic compound of the embodiment, the second compound represented by chemical formula HT-1, and the third compound represented by chemical formula ET-1. In addition, in the light-emitting element ED of one embodiment shown in Figures 5 to 9, the light-emitting layer EML may contain the first compound, which is the polycyclic compound of the embodiment, the second compound represented by chemical formula HT-1, the third compound represented by chemical formula ET-1, and the fourth compound represented by chemical formula D-1.

[0203] In one embodiment of the light-emitting element ED, the light-emitting layer EML may further contain an anthracene derivative, a pyrene derivative, a fluorantene derivative, a chrysene derivative, a dihydrobenzanthracene derivative, or a triphenylene derivative. More specifically, the light-emitting layer EML may further contain an anthracene derivative or a pyrene derivative.

[0204] In the light-emitting element ED of one embodiment shown in Figures 5 to 9, the light-emitting layer EML may include a host and a dopant, but the light-emitting layer EML may further include a compound represented by the following chemical formula E-1. The compound represented by the following chemical formula E-1 can be used as a fluorescent host material.

[0205] [Chemical formula E-1] JPEG2026135762000070.jpg7777

[0206] In chemical formula E-1, R 31 ~R 40Each of these groups may independently be a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted silyl group, a substituted or unsubstituted thio group, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms, a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heteroaryl group having 2 to 30 carbon atoms, or a group that forms a ring by bonding with adjacent groups. 31 ~R 40 These groups can bond with adjacent groups to form saturated hydrocarbon rings, unsaturated hydrocarbon rings, saturated heterocycles, or unsaturated heterocycles.

[0207] In chemical formula E-1, c and d can each be independent integers between 0 and 5, inclusive.

[0208] Chemical formula E-1 may be represented by any one of the following compounds E1 through E19. JPEG2026135762000071.jpg61127 JPEG2026135762000072.jpg57127 JPEG2026135762000073.jpg90127 JPEG2026135762000074.jpg3451

[0209] In one embodiment, the light-emitting layer EML may further contain a compound represented by the following chemical formula E-2a or chemical formula E-2b. The compound represented by the following chemical formula E-2a or chemical formula E-2b can be used as a host material for the phosphorescent layer.

[0210] [Chemical formula E-2a] JPEG2026135762000075.jpg5477

[0211] In chemical formula E-2a, a is an integer between 0 and 10, and L ais a directly bonded, substituted, or unsubstituted ring-forming arylene group with 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heteroarylene group with 2 to 30 carbon atoms. If a is an integer of 2 or more, L a Each of these can independently be a substituted or unsubstituted arylene group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring-forming carbon atoms.

[0212] In chemical formula E-2a, A1 to A5 are each independently N or CR. i It is possible. R a ~R i Each of these groups may independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted amine group, a substituted or unsubstituted thio group, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heteroaryl group having 2 to 30 carbon atoms, or a group that forms a ring by bonding with adjacent groups. a ~R i These groups can bond with adjacent groups to form hydrocarbon rings or heterocycles containing N, O, S, etc., as ring-forming atoms.

[0213] In chemical formula E-2a, two or three selected from A1 to A5 are N, and the rest are CR. i It is possible.

[0214] [Chemical formula E-2b] JPEG2026135762000076.jpg1151

[0215] In the chemical formula E-2b, Cbz1 and Cbz2 can each be independently a carbazole group or a carbazole group substituted with an aryl group having 6 to 30 ring-forming carbon atoms. bmay be a direct bond, a substituted or unsubstituted arylene group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring-forming carbon atoms. On the other hand, b is an integer of 0 or more and 10 or less. If b is an integer of 2 or more, a plurality of L b may each independently be a substituted or unsubstituted arylene group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring-forming carbon atoms.

[0216] The compound represented by Chemical Formula E-2a and the compound represented by Chemical Formula 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 the compounds represented by Chemical Formula E-2a or Chemical Formula E-2b are not limited to those shown in the following compound group E-2.

[0217] [Compound Group E-2] JPEG2026135762000077.jpg131170 JPEG2026135762000078.jpg106170 JPEG2026135762000079.jpg86170 JPEG2026135762000080.jpg53153

[0218] The light-emitting layer EML may further contain a compound represented by the following Chemical Formula M-a. The compound represented by the following Chemical Formula M-a can be used as a phosphorescent dopant material.

[0219] [Chemical Formula M-a] JPEG2026135762000081.jpg5189

[0220] In the chemical formula Ma, Y1 to Y4 and Z1 to Z4 are each independently CR1 or N, and R1 to R4 are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted amine group, a substituted or unsubstituted thio group, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heteroaryl group having 2 to 30 carbon atoms, or a group that forms a ring by bonding with an adjacent group. In the chemical formula Ma, m is 0 or 1, and n is 2 or 3. In the chemical formula Ma, if m is 0, then n is 3, and if m is 1, then n is 2.

[0221] The compound represented by the chemical formula Ma can be used as a phosphorescent dopant.

[0222] A compound represented by the chemical formula Ma may be any one of the compounds in the following group of compounds M-a1 to M-a25. However, the following compounds M-a1 to M-a25 are illustrative examples, and the compound represented by the chemical formula Ma is not limited to those represented by the following compounds M-a1 to M-a25. JPEG2026135762000082.jpg5189 JPEG2026135762000083.jpg40153 JPEG2026135762000084.jpg231170 JPEG2026135762000085.jpg38170

[0223] The luminescent layer EML may further contain a compound represented by any one of the following chemical formulas Fa to Fc. The compounds represented by the following chemical formulas Fa to Fc can be used as fluorescent dopant materials.

[0224] [Chemical formula Fa] JPEG2026135762000086.jpg4251

[0225] In the chemical formula Fa, R a ~R j The two selected from among them are independent of each other. JPEG2026135762000087.jpg677 It may be replaced by R. a ~R j among JPEG2026135762000088.jpg677 The remaining unsubstituted atoms may, independently, be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms.

[0226] JPEG2026135762000089.jpg564 In this, Ar1 to Ar2 can each independently be a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms. For example, at least one of Ar1 and Ar2 may be a heteroaryl group containing O or S as a ring-forming atom.

[0227] [Chemical formula Fb] JPEG2026135762000090.jpg3089

[0228] In the chemical formula Fb, R a and R bEach of these groups may independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted ring-forming alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heteroaryl group having 2 to 30 carbon atoms, or a group that forms a ring by bonding with an adjacent group. Each of Ar1 to Ar4 may independently be a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heteroaryl group having 2 to 30 carbon atoms.

[0229] In chemical formula Fb, U and V can each be independently a substituted or unsubstituted hydrocarbon ring having 5 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heterocycle having 2 to 30 ring-forming carbon atoms. At least one of Ar1 to Ar4 may be a heteroaryl group containing O or S as a ring-forming atom.

[0230] In the chemical formula Fb, the number of rings represented by U and V can be 0 or 1 independently. For example, in the chemical formula Fb, if the number of U or V is 1, the part represented by U or V constitutes a single-ring condensed ring, and if the number of U or V is 0, it means that the ring represented by U or V does not exist. More specifically, if the number of U is 0 and the number of V is 1, or if the number of U is 1 and the number of V is 0, the condensed ring with a fluorene core in the chemical formula Fb can be a four-ring cyclic compound. Also, if the number of both U and V is 0, the condensed ring with a fluorene core in the chemical formula Fb can be a three-ring cyclic compound. Furthermore, if the number of U and V is 1, the condensed ring with a fluorene core in the chemical formula Fb can be a five-ring cyclic compound.

[0231] [Chemical formula Fc] JPEG2026135762000091.jpg7877

[0232] In the chemical formula Fc, A1 and A2 are independently O, S, Se, or NR, respectively. m And R mR1 to R 11 Each of these groups is independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted amine group, a substituted or unsubstituted boron group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thio group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, or is bonded to an adjacent group to form a ring.

[0233] In the chemical formula Fc, A1 and A2 can independently bond to substituents on adjacent rings to form fused rings. For example, A1 and A2 can independently form NR m Therefore, A1 may bond with R4 or R5 to form a ring. Also, A2 may bond with R7 or R8 to form a ring.

[0234] In one embodiment, the luminescent layer EML is a known dopant material, and is a styryl derivative (e.g., 1,4-bis[2-(3-N-ethylcarbazol)vinyl]benzene (BCzVB), 4-(di-p-tolylamino)-4'-[(di-p-tolylamino)styryl]stilbene (DPAVB), N-(4-((E)-2-(6-((E)-4-(diphenylamino)styryl)naphthalen-2-yl)vinyl)phenyl)- The following may further be included: N-phenylbenzeneamine (N-BDAVBi), 4,4'-bis[2-(4-(N,N-diphenylamino)phenyl)vinyl]biphenyl (DPAVBi), perylene and its derivatives (e.g., 2,5,8,11-tetra-t-butylperylene (TBP)), pyrene and its derivatives (e.g., 1,1-dipylene, 1,4-dipyrenylbenzene, 1,4-bis(N,N-diphenylamino)pyrene).

[0235] The luminescent layer EML may further contain known phosphorescent dopant materials. For example, metal complexes containing iridium (Ir), platinum (Pt), osmium (Os), gold (Au), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), or thulium (Tm) may be used as phosphorescent dopants. Specifically, Flrpic (iridium(III)bis(4,6-difluorophenylpyridinate-N,C2')picolinate), Fir6 (bis(2,4-difluorophenylpyridinate)-tetrakis(1-pyrazolyl)borate-iridium(III)) or PtOEP (platinum-octaethylporphyrin) may be used as phosphorescent dopants. However, the examples are not limited to these.

[0236] The luminescent layer EMLML may contain quantum dot material. The core of the quantum dot can be selected from group II-VI compounds, group I-II-VI compounds, group II-IV-VI compounds, group I-II-IV-VI compounds, group II-IV-V 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.

[0237] Group II-VI compounds are binary compounds selected from the group consisting of CdSe, CdTe, CdS, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, MgSe, MgS, and mixtures thereof, CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, CdZnSe, CdZnTe, CdHgS, CdHgSe, C A ternary compound selected from the group consisting of dHgTe, HgZnS, HeZnSe, HeZnTe, MgZnSe, MgZnS, and mixtures thereof, and a quaternary compound selected from the group consisting of HgZnTeS, CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe, and mixtures thereof may be selected.

[0238] Group III-VI compounds may include dielemental compounds such as In2S3 and In2Se3, trielemental compounds such as InGaS3 and InGaSe3, or any combination thereof.

[0239] Group I-III-VI compounds are selected from the group consisting of AgInS, AgInS2, CuInS, CuInS2, AgGaS2, CuGaS2, CuGaO2, AgGaO2, AgAlO2, and mixtures thereof, or from tetra-element compounds such as AgInGaS2 and CuInGaS2.

[0240] Group III-V compounds can be selected from the group consisting of binary compounds selected from the group consisting of GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, InSb, and mixtures thereof; ternary compounds selected from the group consisting of GaNP, GaNAs, GaNSb, GaPAs, GaPSb, AlNP, AlNAs, AlNSb, AlPAs, AlPSb, InGaP, InAlP, InNP, InNAs, InNSb, InPAs, InPSb, and mixtures thereof; and quaternary compounds selected from the group consisting of GaAlNP, GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNP, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs, InAlPSb, and mixtures thereof. Group III-V compounds may further contain Group II metals. For example, InZnP could be selected as a III-II-V group compound.

[0241] Group IV-VI compounds may be selected from the group consisting of binary compounds selected from the group consisting of SnS, SnSe, SnTe, PbS, PbSe, PbTe, and mixtures thereof; ternary compounds selected from the group consisting of SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, SnPbTe, and mixtures thereof; and quaternary compounds selected from the group consisting of SnPbSSe, SnPbSeTe, SnPbSTe, and mixtures thereof. Group IV elements may be selected from the group consisting of Si, Ge, and mixtures thereof. Group IV compounds may be binary compounds selected from the group consisting of SiC, SiGe, and mixtures thereof.

[0242] Each element in a multi-element compound, such as the binary, ternary, and quaternary compounds, can exist within the particles at uniform or non-uniform concentrations. In other words, the chemical formula represents the types of elements contained in the compound, and the elemental ratios within the compound can vary. For example, AgInGaS2 is AgIn x Ga 1-x This could mean S² (where X is a real number between 0 and 1).

[0243] The quantum dot may have a single structure in which the concentration of each element contained in the quantum dot is uniform, or a core-shell dual structure. For example, the material contained in the core and the material contained in the shell may be different from each other.

[0244] The shell of the quantum dot may serve as a protective layer to prevent chemical degradation of the core and maintain its 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. The interface between the core and the shell may have a concentration gradient in which the concentration of elements present in the shell decreases towards the center.

[0245] Examples of the shells for the quantum dots include metallic or nonmetallic oxides, semiconductor compounds, or combinations thereof. For example, the metallic or nonmetallic oxides include binary compounds such as SiO2, Al2O3, TiO2, ZnO, MnO, Mn2O3, Mn3O4, CuO, FeO, Fe2O3, Fe3O4, CoO, Co3O4, and NiO, or ternary compounds such as MgAl2O4, CoFe2O4, NiFe2O4, and CoMn2O4, but the present invention is not limited to these.

[0246] Furthermore, examples of the semiconductor compound include CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnSeS, ZnTeS, GaAs, GaP, GaSb, HgS, HgSe, HgTe, InAs, InP, InGaP, InSb, AlAs, AlP, AlSb, and the like, but the present invention is not limited to these.

[0247] Each element in a multi-element compound, such as the binary or ternary compounds, can exist within the particles at uniform or non-uniform concentrations. In other words, the chemical formula represents the types of elements contained in the compound, and the elemental ratios within the compound can vary.

[0248] Quantum dots have an emission wavelength spectrum with a full width at half maximum (FWHM) of approximately 45 nm or less, preferably approximately 40 nm or less, and more preferably approximately 30 nm or less, and within this range, color purity and color reproducibility can be improved. Furthermore, since the light emitted through such quantum dots is emitted in all directions, the optical viewing angle can be improved.

[0249] Furthermore, the form of the quantum dots is not limited to those commonly used in this field, but more specifically, spherical, pyramidal, multi-arm, or cubic nanoparticles, nanotubes, nanowires, nanofibers, or nanoplate-like particles may be used.

[0250] The energy band gap can be adjusted by adjusting the size of the quantum dots or the elemental ratio within the quantum dot compound, thereby obtaining light in a variety of wavelengths from the quantum dot light-emitting layer. Therefore, by using quantum dots as described above (either using quantum dots of different sizes or having different elemental ratios within the quantum dot compound), it is possible to realize a light-emitting element that emits light of various wavelengths. Specifically, the size of the quantum dots and the elemental ratio within the quantum dot compound can be selected to emit red, green, and / or blue light. Furthermore, the quantum dots can be configured to emit white light by combining light of various colors.

[0251] In one embodiment of the light-emitting element ED shown in Figures 5 to 9, the electron transport region ETR is provided on the light-emitting layer EML. The electron transport region ETR includes, but is not limited to, at least one of the hole blocking layer HBL, electron transport layer ETL, and electron injection layer EIL.

[0252] The electron transport region (ETR) may have a single layer made of a single material, a single layer made of multiple different materials, or a multilayer structure having multiple layers made of multiple different materials.

[0253] For example, the electron transport region (ETR) may have a single-layer structure of an electron injection layer (EIL) or electron transport layer (ETL), or a single-layer structure consisting of an electron injection material and an electron transport material. Furthermore, the electron transport region (ETR) may have a single-layer structure consisting of multiple different materials, or it may have a structure of electron transport layer (ETL) / electron injection layer (EIL) or hole blocking layer (HBL) / electron transport layer (ETL) / electron injection layer (EIL) stacked sequentially from the light-emitting layer (EML), but is not limited to these. The thickness of the electron transport region (ETR) may be, for example, about 1000 Å to about 1500 Å.

[0254] Electron transport regions (ETRs) can be formed using a variety of methods, such as vacuum deposition, spin coating, casting, LB, inkjet printing, laser printing, and laser thermal transfer (LITI).

[0255] The electron transport region (ETR) may contain compounds represented by the following chemical formula ET-2.

[0256] [Chemical formula ET-2] JPEG2026135762000092.jpg6477

[0257] In the chemical formula ET-2, at least one of X1 to X3 is N and the rest are CR. a That is. R a Ar1 to Ar3 can each be independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms.

[0258] In chemical formula ET-2, a to c can each be an integer between 0 and 10, independently of each other. In chemical formula ET-2, L1 and L3 can each be an arylene group with 6 to 30 ring-forming carbon atoms, either directly bonded, substituted, or unsubstituted, or a heteroarylene group with 2 to 30 ring-forming carbon atoms, independently of each other. If a to c are integers of 2 or more, then multiple L1 and L3 can each be an arylene group with 6 to 30 ring-forming carbon atoms, either substituted or unsubstituted, or a heteroarylene group with 2 to 30 ring-forming carbon atoms, independently of each other.

[0259] The electron transport region (ETR) may include anthracene compounds. However, it is not limited to these; examples of electron transport region ETRs include Alq3 (tris(8-hydroxyquinolinato)aluminum), 1,3,5-tri[(3-pyridyl)phen-3-yl]benzene, 2,4,6-tris(3'-pyridin-3-yl)biphenyl-3-yl)-1,3,5-triazine, 2-(4-(N-phenylbenzimidazole-1-yl)phenyl)-9,10-dinaphthylanthracene, TPBi (1,3,5-tri(1-phenyl-1H-benzo[d]imidazole-2-yl)benzene), BCP (2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline), Bphen (4,7-diphenyl-1,10-phenanthroline), TAZ (3-(4-biphenylyl This may include ()-4-phenyl-5-terto-butylphenyl-1,2,4-triazole), NTAZ (4-(naphthalene-1-yl)-3,5-diphenyl-4H-1,2,4-triazole), tBu-PBD (2-(4-biphenylyl)-5-(4-terto-butylphenyl)-1,3,4-oxadiazole), BAlq (bis(2-methyl-8-quinolinolato-N1,O8)-(1,1'-biphenyl-4-orato)aluminum), Bebq2 (beryllium bis(benzoquinoline-10-orato), ADN (9,10-di(naphthalene-2-yl)anthracene), BmPyPhB (1,3-bis[3,5-di(pyridine-3-yl)phenyl]benzene), and mixtures thereof.

[0260] The electron transport region (ETR) may contain at least one of the following compounds ET1 to ET36. JPEG2026135762000093.jpg160170 JPEG2026135762000094.jpg240170 JPEG2026135762000095.jpg192127

[0261] Furthermore, the electron transport region (ETR) may include metal halides such as LiF, NaCl, CsF, RbCl, RbI, CuI, and KI, lanthanum group metals such as Yb, or co-deposited materials of the aforementioned metal halides and lanthanum group metals. For example, the electron transport region (ETR) may include KI:Yb, RbI:Yb, LiF:Yb, etc., as co-deposited materials. The electron transport region (ETR) may also be a metal oxide such as Li2O, BaO, or Liq(8-hydroxylithium quinolate), but the examples are not limited to these. The electron transport region (ETR) may also consist of a mixture of an electron transport material and an insulating organometallic salt. The organometallic salt may be a material with an energy band gap of about 4 eV or more. For more details, organometallic salts may include metal acetate, metal benzoate, metal acetoacetate, metal acetylacetonate, or metal stearate.

[0262] The electron transport region (ETR) may, but is not limited to, further contain at least one of the following materials: BCP (2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline), TSPO1 (diphenyl(4-(triphenylsilyl)phenyl)phosphine oxide), and Bphen (4,7-diphenyl-1,10-phenanthroline).

[0263] The electron transport region ETR may contain the aforementioned electron transport region compound in at least one of the electron injection layer EIL, electron transport layer ETL, and hole blocking layer HBL.

[0264] If the electron transport region (ETR) includes an electron transport layer (ETL), the thickness of the electron transport layer (ETL) may be approximately 100 Å to approximately 1000 Å, for example, approximately 150 Å to approximately 500 Å. If the thickness of the electron transport layer (HTL) satisfies the above-mentioned range, satisfactory electron transport characteristics can be obtained without a substantial increase in the driving voltage. If the electron transport region (ETR) includes an electron injection layer (EIL), the thickness of the electron injection layer (EIL) may be approximately 1 Å to approximately 100 Å, or approximately 3 Å to approximately 90 Å. If the thickness of the electron injection layer (EIL) satisfies the above-mentioned range, satisfactory electron injection characteristics can be obtained without a substantial increase in the driving voltage.

[0265] The second electrode EL2 is provided on the electron transport region ETR. The second electrode EL2 may be a common electrode. The second electrode EL2 may be a cathode or an anor rond, but the examples are not limited to these. For example, if the first electrode EL1 is an anode, the second electrode may be a cathode, and if the first electrode EL1 is a cathode, the second electrode EL2 may be an anode.

[0266] The second electrode EL2 can be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode. If the second electrode EL2 is a transmissive electrode, it can be made of a transparent metal oxide, such as ITO (indium tin oxide), IZO (indium zinc oxide), ZnO (zinc oxide), or ITZO (indium tin zinc oxide).

[0267] If the second electrode EL2 is a semi-transparent or reflective electrode, the second electrode EL2 may contain Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF / Ca, LiF / Al, Mo, Ti, Yb, W, or compounds or mixtures containing these (e.g., AgMg, AgYb, or MgYb). Alternatively, the second electrode EL2 may have a multi-layer structure including a reflective or semi-transparent film made of the above-mentioned material, and a transparent conductive film made of ITO, IZO, ZnO, ITZO, etc. For example, the second electrode EL2 may contain the above-mentioned metallic material, a combination of two or more metallic materials selected from the above-mentioned metallic materials, or an oxide of the above-mentioned metallic material.

[0268] Although not shown in the diagram, the second electrode EL2 can be connected to an auxiliary electrode. Connecting the second electrode EL2 to an auxiliary electrode can reduce the resistance of the second electrode EL2.

[0269] A capping layer CPL may be further disposed on the second electrode EL2 of the light-emitting element ED in one embodiment. The capping layer CPL may consist of multiple layers or a single layer.

[0270] In one embodiment, the capping layer CPL may be an organic or inorganic layer. For example, if the capping layer CPL contains inorganic material, the inorganic material may include alkali metal compounds such as LiF, alkaline earth compounds such as MgF2, SiON, SiNx, SiOy, etc.

[0271] For example, if the capping layer CPL contains organic matter, the organic matter may include α-NPD, NPB, TPD, m-MTDATA, Alq3, CuPc, TPD15 (N4,N4,N4',N4'-tetra(biphenyl-4-yl)biphenyl-4,4'-diamine), TCTA (4,4',4"-tris(carbazolesol-9-yl)triphenylamine), or epoxy resin, or acrylates such as methacrylate. However, the examples are not limited to these, and the capping layer CPL may contain at least one of the compounds P1 to P5 described below. JPEG2026135762000096.jpg166170

[0272] The refractive index of the capping layer CPL may be 1.6 or higher. More specifically, for light in the wavelength range of 550 nm to 660 nm, the refractive index of the capping layer CPL may be 1.6 or higher.

[0273] Figures 10 and 13 are cross-sectional views of a display module according to one embodiment, respectively. In the following description of the display module according to one embodiment, with reference to Figures 10 and 13, we will not repeat the content described in Figures 1 to 9 above, but will focus on the differences.

[0274] Referring to Figure 10, a display module DM-a according to one embodiment may include a display panel DP including a display element layer DP-ED, an optical control layer CCL disposed on the display panel DP, and a color filter layer CFL. In the embodiment shown in Figure 10, the display panel DP includes a base layer BS, a circuit layer DP-CL provided on the base layer BS, and a display element layer DP-ED, and the display element layer DP-ED may include a light-emitting element ED.

[0275] The light-emitting element ED may include a first electrode EL1, a hole transport region HTR placed on the first electrode EL1, an emissive layer EML placed on the hole transport region HTR, an electron transport region ETR placed on the emissive layer EML, and a second electrode EL2 placed on the electron transport region ETR. The structure of the light-emitting element ED shown in Figure 10 can also be adapted from the structures of the light-emitting elements shown in Figures 5 to 9 described above. The light-emitting element ED shown in Figure 10 may contain the polycyclic compound of one embodiment. As a result, the light-emitting element ED can exhibit high efficiency and long lifetime characteristics. Furthermore, the light-emitting element ED of one embodiment can exhibit high light efficiency and long lifetime characteristics in the blue light emission region.

[0276] Referring to Figure 10, the light-emitting layer EML may be located within the aperture OH defined in the pixel definition film DPL. For example, the light-emitting layers EML provided corresponding to each light-emitting region PXA-R, PXA-G, and PXA-B, separated by the pixel definition film PDL, may emit light in the same wavelength range. In one embodiment of the display module DM-a, the light-emitting layer EML may emit blue light. Contrary to the illustration, in one embodiment, the light-emitting layer EML may be provided as a common layer across the entire light-emitting regions PXA-R, PXA-G, and PXA-B.

[0277] The optical control layer (CCL) may be located above the display panel (DP). Although the CCL is shown located above the display element layer (DP-ED), the examples are not limited to this, and the CCL may be located below the display element layer (DP-ED). The CCL may contain photoconverters. These photoconverters may be quantum dots or phosphors, etc. The photoconverters may wavelength-convert and emit the provided light. In other words, the CCL may contain quantum dots or may be a layer containing phosphors.

[0278] The optical control layer (CCL) may include multiple optical control units CCP1, CCP2, and CCP3. The optical control units CCP1, CCP2, and CCP3 may be separated from each other.

[0279] Referring to Figure 10, a segmented pattern BMP is provided between the optical control units CCP1, CCP2, and CCP3, which are separated from each other, but the embodiment is not limited to this. In Figure 10, it is shown that the segmented pattern BMP does not overlap with the optical control units CCP1, CCP2, and CCP3, but the edges of the optical control units CCP1, CCP2, and CCP3 may overlap with the segmented pattern BMP in at least part.

[0280] The optical control layer CCL may include a first optical control unit CCP1 which includes a first quantum dot QD1 that converts the first color light provided from the light-emitting element ED into second color light, a second optical control unit CCP2 which includes a second quantum dot QD2 that converts the first color light into third color light, and a third optical control unit CCP3 which transmits the first color light.

[0281] In one embodiment, the first optical control unit CCP1 may provide red light, which is the second color, and the second optical control unit CCP2 may provide green light, which is the third color. The third optical control unit CCP3 may transmit and provide blue light, which is the first color, provided from the light-emitting element ED. For example, the first quantum dot QD1 may be a red quantum dot, and the second quantum dot QD2 may be a green quantum dot. The same provisions as described above may apply to quantum dots QD1 and QD2.

[0282] Furthermore, the optical control layer CCL may further include a scatterer SP. The first optical control unit CCP1 includes a first quantum dot QD1 and a scatterer SP, the second optical control unit CCP2 includes a second quantum dot QD2 and a scatterer SP, and the third optical control unit CCP3 may include a scatterer SP without a quantum dot.

[0283] The scatterer SP may be inorganic particles. For example, the scatterer SP may contain at least one of TiO2, ZnO, Al2O3, SiO2, and hollow silica. The scatterer SP may contain at least one of TiO2, ZnO, Al2O3, SiO2, and hollow silica, or it may be a mixture of two or more substances selected from TiO2, ZnO, Al2O3, SiO2, and hollow silica.

[0284] The first optical control unit CCP1, the second optical control unit CCP2, and the third optical control unit CCP3 may each include base resins BR1, BR2, and BR3 for dispersing quantum dots QD1 and QD2 and scatterers SP. In one embodiment, the first optical control unit CCP1 may include first quantum dots QD1 and scatterers SP dispersed in the first base resin BR1, the second optical control unit CCP2 may include second quantum dots QD2 and scatterers SP dispersed in the second base resin BR2, and the third optical control unit CCP1 may include scatterers SP dispersed in the third base resin BR3.

[0285] The base resins BR1, BR2, and BR3 are the medium in which the quantum dots QD1 and QD2 and the scatterer SP are dispersed, and can consist of various resin compositions generally referred to as binders. For example, the base resins BR1, BR2, and BR3 may be acrylic resins, urethane 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 as or different from each other.

[0286] The light control layer CCL may include a barrier layer BFL1. The barrier layer BFL1 may serve to prevent the penetration of moisture and / or oxygen (hereinafter referred to as "moisture / oxygen"). The barrier layer BFL1 may be placed on top of the light control units CCP1, CCP2, and CCP3 to block them from being exposed to moisture / oxygen. The barrier layer BFL1 may cover the light control units CCP1, CCP2, and CCP3. In addition, a barrier layer BLF2 may be provided between the light control units CCP1, CCP2, and CCP3 and the color filter layer CFL.

[0287] The barrier layers BFL1 and BFL2 may contain at least one inorganic layer. In other words, the barrier layers BFL1 and BFL2 may be formed by including inorganic materials. For example, the barrier layers BFL1 and BFL2 may be formed by including silicon nitride, aluminum nitride, zirconium nitride, titanium nitride, hafnium nitride, tantalum nitride, silicon oxide, aluminum oxide, titanium oxide, tin oxide, cerium oxide, and silicon oxynitride, or a thin metal film with sufficient light transmittance. The barrier layers BFL1 and BFL2 may further contain an organic film. The barrier layers BFL1 and BFL2 may consist of a single layer or multiple layers.

[0288] In one embodiment of the display module DM-a, the color filter layer CFL may be placed on top of the light control layer CCL. For example, the color filter layer CFL may be placed directly on top of the color control layer CCL. In this case, the barrier layer BFL2 may be omitted.

[0289] The color filter layer CFL may include filters CF1, CF2, and CF3. The color filter CFL may include a first filter CF1 that transmits second-color light, a second filter CF2 that transmits third-color light, and a third filter CF3 that transmits first-color light. For example, the first filter CF1 may be a red filter, the second filter CF2 a green filter, and the third filter CF3 a blue filter. Each of the filters CF1, CF2, and CF3 may contain a polymer photosensitive resin and a pigment or dye. The first filter CF1 may contain a red pigment or dye, the second filter CF2 may contain a green pigment or dye, and the third filter CF3 may contain a blue pigment or dye.

[0290] The examples are not limited to these, and the third filter CF3 does not have to contain pigments or dyes. The third filter CF3 contains a polymer photosensitive resin and does not have to contain pigments or dyes. The third filter CF3 may be transparent. The third filter CF3 may be made of a transparent photosensitive resin.

[0291] In one embodiment, the first filter CF1 and the second filter CF2 may be yellow filters. The first filter CF1 and the second filter CF2 may be provided as a single unit without being separated from each other.

[0292] Although not shown, the color filter layer CFL may further include a light-shielding portion (not shown). The light-shielding portion may be a black matrix. The light-shielding portion may be formed by comprising an organic or inorganic light-shielding material containing a black pigment or black dye. The light-shielding portion may prevent light leakage and demarcate the boundaries between adjacent filters CF1, CF2, and CF3. In one embodiment, the light-shielding portion may be formed of a blue filter.

[0293] The first to third color filters CF1, CF2, and CF3 can be arranged to correspond to the first light-emitting region PXA-R, the second light-emitting region PXA-G, and the third light-emitting region PXA-B, respectively.

[0294] A base substrate BL may be placed on top of the color filter layer CFL. The base substrate BL may be a component that provides a base surface on which the color filter layer CFL and the light control layer CCL are placed. The base substrate BL may be a glass substrate, a metal substrate, a plastic substrate, etc. However, the embodiment is not limited to these, and the base substrate BL may be an inorganic layer, an organic layer, or a composite material layer. Also, contrary to the figures, the base substrate BL may be omitted in one embodiment.

[0295] Figure 11 is a cross-sectional view showing a part of a display module according to one embodiment. In the display module DM-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. At least one of the plurality of light-emitting structures OL-B1, OL-B2, and OL-B3 may contain the polycyclic compound of one embodiment. As a result, the light-emitting element ED-BT can exhibit high efficiency and long lifespan characteristics. Furthermore, the light-emitting element ED-BT of one embodiment can exhibit high light efficiency and long lifespan characteristics in the blue light emission region.

[0296] The light-emitting element ED-BT may include a plurality of light-emitting structures OL-B1, OL-B2, and OL-B3, which are sequentially stacked in the thickness direction between a first electrode EL1 and a second electrode EL2 facing each other. Each of the light-emitting structures OL-B1, OL-B2, and OL-B3 may include a light-emitting layer EML (Figure 5) and a hole transport region HTR and an electron transport region ETR arranged between the light-emitting layer EML (Figure 5). In other words, the light-emitting element ED-BT included in the display module DM-TD according to one embodiment may be a light-emitting element with a tandem structure including a plurality of light-emitting layers.

[0297] In one embodiment shown in Figure 11, the light emitted from each of the light-emitting structures OL-B1, OL-B2, and OL-B3 can be blue light. However, the embodiment is not limited to this, and the wavelength ranges 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 containing multiple light-emitting structures OL-B1, OL-B2, and OL-B3 that emit light in different wavelength ranges can emit white light.

[0298] Charge generation layers CGL1 and CGL2 may be arranged between adjacent light-emitting structures OL-B1, OL-B2, and OL-B3. In one embodiment shown in Figure 11, the charge generation layers CGL1 and CGL2 may include a first charge generation layer CGL1 arranged between the first light-emitting structure OL-B1 and the second light-emitting structure OL-B2, and a second charge generation layer CGL2 arranged between the second light-emitting structure OL-B2 and the third light-emitting structure OL-B3. The first and second charge generation layers CGL1 and CGL2 may each independently include a p-type charge generation layer and / or an n-type charge generation layer.

[0299] Referring to Figure 12, the display module DM-b according to one embodiment may include light-emitting elements ED-1, ED-2, and ED-3, each having two stacked light-emitting layers. At least one of the light-emitting elements ED-1, ED-2, and ED-3 may contain the polycyclic compound of one embodiment. As a result, the light-emitting elements ED-1, ED-2, and ED-3 may exhibit high efficiency and long lifespan characteristics. Furthermore, the light-emitting element ED-3 of one embodiment may exhibit high light efficiency and long lifespan characteristics in the blue light emission region.

[0300] Compared to the display module DM according to one embodiment shown in Figure 3, the embodiment shown in Figure 12 differs in that the first to third light-emitting elements ED-1, ED-2, and ED-3 each include two light-emitting layers stacked in the thickness direction. In each of the first to third light-emitting elements ED-1, ED-2, and ED-3, the two light-emitting layers may emit light in the same wavelength range.

[0301] The first light-emitting element ED-1 may include a first red light-emitting layer EML-R1 and a second red light-emitting layer EML-R2. The second light-emitting element ED-2 may include a first green light-emitting layer EML-G1 and a second green light-emitting layer EML-G2. The third light-emitting element ED-3 may include a first blue light-emitting layer EML-B1 and a second blue light-emitting layer EML-B2. Light-emitting auxiliary units OG may be arranged between the first red light-emitting layer EML-R1 and the second red light-emitting layer EML-R2, between the first green light-emitting layer EML-G1 and the second green light-emitting layer EML-G2, and between the first blue light-emitting layer EML-B1 and the second blue light-emitting layer EML-B2.

[0302] The light-emitting auxiliary section OG may include a single layer or a multilayer. The light-emitting auxiliary section OG may include a charge generation layer. More specifically, the light-emitting auxiliary section OG may include sequentially stacked electron transport regions, a charge generation layer, and hole transport regions. The light-emitting auxiliary section OG may be provided in common across the first to third light-emitting elements ED-1, ED-2, and ED-3. However, the examples are not limited thereto, and the light-emitting auxiliary section OG may be provided patterned within an aperture OH defined in the pixel-defining film PDL.

[0303] The first red light-emitting layer EML-R1, the first green light-emitting layer EML-G1, and the first blue light-emitting layer EML-B1 may be positioned between the light-emitting auxiliary region OG and the electron transport region ETR. The second red light-emitting layer EML-R2, the second green light-emitting layer EML-G2, and the second blue light-emitting layer EML-B2 may be positioned between the hole transport region HTR and the light-emitting auxiliary region OG.

[0304] In other words, the first light-emitting element ED-1 may include a first electrode EL1 stacked sequentially, a hole transport region HTR, a second red light-emitting layer EML-R2, a light-emitting auxiliary section OG, a first red light-emitting layer EML-R1, an electron transport region ETR, and a second electrode EL2. The second light-emitting element ED-2 may include a first electrode EL1 stacked sequentially, a hole transport region HTR, a second green light-emitting layer EML-G2, a light-emitting auxiliary section OG, a first green light-emitting layer EML-G1, an electron transport region ETR, and a second electrode EL2. The third light-emitting element ED-3 may include a first electrode EL1 stacked sequentially, a hole transport region HTR, a second blue light-emitting layer EML-B2, a light-emitting auxiliary section OG, a first blue light-emitting layer EML-B1, an electron transport region ETR, and a second electrode EL2.

[0305] An optical auxiliary layer PL may be placed on the display element layer DP-ED. The optical auxiliary layer PL may include a polarizing layer. The optical auxiliary layer PL is placed on the display panel DP and can control the reflected light on the display panel DP due to external light. Unlike the illustration, the optical auxiliary layer PL may be omitted in one embodiment of the display device.

[0306] Unlike Figures 11 and 12, the display module DM-c according to one embodiment shown in Figure 13 is shown to include four light-emitting structures OL-B3, OL-B2, OL-B1, and OL-C1. The light-emitting element ED-CT may include a first electrode EL1 and a second electrode EL2 facing each other, and first to fourth light-emitting structures OL-B1, OL-B2, OL-B3, and OL-C1 sequentially stacked in the thickness direction between the first electrode EL1 and the second electrode EL2. At least one of the first to fourth display devices OL-B1, OL-B2, OL-B3, and OL-C1 may include the adhesive member AP of one embodiment. As a result, the light-emitting element ED-CT can exhibit high efficiency and long life characteristics. Furthermore, the light-emitting element ED-CT of one embodiment can exhibit high light efficiency and long life characteristics in the blue light emission region.

[0307] Charge generation layers CGL3, CGL2, and CGL1 may be arranged between the first to fourth light-emitting structures OL-B1, OL-B2, OL-B3, and OL-C1. Of the four light-emitting structures, the first to third structures OL-B1, OL-B2, and OL-B3 may emit blue light, and the fourth light-emitting structure OL-C1 may emit green light. However, the examples are not limited to this, and the first to fourth light-emitting structures OL-B1, OL-B2, OL-B3, and OL-C1 may emit light in different wavelength regions. The charge generation layers GCL3, CGL2, and CGL1 arranged between adjacent light-emitting structures OL-B1, OL-B2, OL-B3, and OL-C1 may include a p-type charge generation layer and / or an n-type charge generation layer.

[0308] In one embodiment, the electronic device may include a display device containing a plurality of light-emitting elements and a control unit for controlling the display device. In the electronic device of one embodiment, at least one of the plurality of light-emitting elements may contain the polycyclic compound of the embodiment described above in its light-emitting layer.

[0309] The electronic device of one embodiment may be a device that is activated by an electrical signal. The electronic device of one embodiment may include a display device that includes a display module according to one embodiment described with reference to Figures 3 and 10 to 13, etc. For example, the display device may include large electronic devices such as televisions, monitors, or external billboards, as well as small and medium-sized display devices such as personal computers, laptop computers, personal information terminals, vehicle display devices, game consoles, portable electronic devices, and cameras.

[0310] The display device of one embodiment includes a display module containing the polycyclic compound of one embodiment and may exhibit high efficiency and long life characteristics. The electronic device of one embodiment may have improved display efficiency and display life and exhibit excellent display quality.

[0311] Figure 14 shows a tablet terminal as an example of an electronic device EA. The display device EA of one embodiment may include a display module DM according to one embodiment. For example, an electronic module, camera module, or power supply module, which are mounted on the main board together with the display module DM, can be arranged in a bracket / enclosure HAU to constitute a tablet terminal.

[0312] The electronic device EA of one embodiment shown in Figure 14 may include a display module of one embodiment described with reference to Figures 3 and 10 to 13, etc.

[0313] In one embodiment, an electronic device EA is shown that includes a display module DM having a planar display surface, but it is not limited to this. The electronic device EA may include a curved display surface or a three-dimensional display surface. For example, a three-dimensional display surface may include multiple display areas that indicate different directions from each other, and may include a folded display surface. The electronic device EA according to this embodiment may be a flexible electronic device. A flexible electronic device may be a foldable electronic device that can be folded.

[0314] As shown in Figure 14, the display surface EA-IS includes an active area AA where the image is displayed, and a bezel area NAA adjacent to the active area AA. The bezel area NAA is an area where the image is not displayed. Figure 14 shows an icon image as an example of an image. The active area AA may be referred to as the display area of ​​the display module DM, and the bezel area NAA may be referred to as the non-display area of ​​the display module DM.

[0315] Figure 15 shows a portable terminal as an example of the electronic device EA-M of one embodiment. Referring to Figure 15, the electronic device EA-M of one embodiment may include multiple display surfaces. The electronic device EA-M of one embodiment may include display surfaces IS-M, IS-S1, IS-S2, IS-S3, and IS-S4, whose primary display directions are different from each other.

[0316] In one embodiment, the electronic device EA-M may be a stereoscopic display device including an upper display surface IS-M and a plurality of side display surfaces IS-S1, IS-S2, IS-S3, IS-S4. Each of the plurality of side display surfaces IS-S1, IS-S2, IS-S3, IS-S4 may be a display surface extending from one side of the upper display surface IS-M. In one embodiment, the electronic device EA-M may include a main display surface that primarily provides an image in one direction and a plurality of sub-display surfaces that provide images in a direction different from that of the main display surface. In the embodiment of the electronic device EA-M shown in Figure 15, the main display surface is the upper display surface IS-M, and the sub-display surfaces may be the side display surfaces IS-S1, IS-S2, IS-S3, IS-S4.

[0317] The side display surfaces IS-S1, IS-S2, IS-S3, and IS-S4 may have display surfaces that are not parallel to the upper display surface IS-M. On the other hand, the multiple side display surfaces IS-S1, IS-S2, IS-S3, and IS-S4 are display areas that are folded and extended from one side of the upper display surface IS-M, and for example, the multiple side display surfaces IS-S1, IS-S2, IS-S3, and IS-S4 may be folded display areas.

[0318] The electronic device EA-M of one embodiment shown in Figure 15 may include a display module according to one embodiment described with reference to Figures 3 and 10 to 13, etc.

[0319] Figure 16 shows a vehicle AM ​​in which the first to fourth electronic devices EA-1, EA-2, EA-3, and EA-4 are installed. At least one of the first to fourth electronic devices EA-1, EA-2, EA-3, and EA-4 may include a display module of one embodiment described with reference to Figures 3 and 10 to 13.

[0320] Although Figure 16 shows an automobile as the vehicle AM, this is illustrative, and the first to fourth electronic devices EA-1, EA-2, EA-3, and EA-4 may be installed in other means of transport such as bicycles, motorcycles, trains, ships, and airplanes.

[0321] At least one of the first to fourth electronic devices EA-1, EA-2, EA-3, and EA-4 may include a light-emitting element ED of one embodiment described with reference to Figures 5 to 9. At least one of the first to fourth electronic devices EA-1, EA-2, EA-3, and EA-4 may include a polycyclic compound of one embodiment. As a result, the first to fourth electronic devices EA-1, EA-2, EA-3, and EA-4 containing the polycyclic compound of one embodiment may have improved display efficiency and display life. Furthermore, the first to fourth electronic devices EA-1, EA-2, EA-3, and EA-4 containing the polycyclic compound of one embodiment may exhibit excellent display quality.

[0322] Referring to Figure 16, the vehicle AM ​​may include a steering wheel HA and a gear GR for controlling its operation, and may include a forward window GL positioned in front of the driver.

[0323] The first electronic device EA-1 may be a digital cluster that displays first information of the vehicle AM. The first information may include a first scale representing the vehicle AM's speed, a second scale indicating the engine speed (RPM (revolutions per minute)), and an image indicating the fuel status. The first and second scales may be displayed as digital images. In one embodiment shown in Figure 16, the first electronic device EA-1 may be positioned in a first area that overlaps with the steering wheel HA. However, the embodiment is not limited to this, and the first electronic device EA-1 may be positioned across the entire dashboard, or separated and positioned in the portion facing the driver's seat and the portion facing the passenger seat, respectively.

[0324] The second electronic device EA-2 may be positioned in a second area between the driver's seat and the front window GL. For example, the second electronic device EA-2 may be a head-up display (HUD) that displays second information about the vehicle AM. The second electronic device EA-2 may be optically transparent. The second information may include digital figures indicating the vehicle AM's speed and may further include information such as the current time. Contrary to the illustration, the second information of the second electronic device EA-2 may be projected onto the front window GL. The display surface of the second electronic device EA-2 may face the driver's seat. Alternatively, the second electronic device EA-2 may provide an image in the direction of the front window GL.

[0325] The third electronic device EA-3 may be located in a third area adjacent to the gear GR. For example, the third electronic device EA-3 may be located between the driver's seat and the passenger seat and may be a Center Information Display (CID) that displays third information. The passenger seat may be a seat separated from the driver's seat with the gear GR in between. The third information may include information about road conditions (e.g., navigation information), music or radio playback, dynamic video playback, and the temperature inside the vehicle AM.

[0326] The fourth electronic device EA-4 may be located in a fourth area adjacent to the sides of both AMs, separated from the steering wheel HA and gear GR. For example, the fourth electronic device EA-4 may be a digital side mirror that displays fourth information. The fourth electronic device EA-4 may display images of the outside of the vehicle AM ​​captured by a camera module CM located on the outside of the vehicle AM. The fourth information may include images of the outside of the vehicle AM.

[0327] The first to fourth pieces of information described above are illustrative, and the first to fourth electronic devices EA-1, EA-2, EA-3, and EA-4 may further display information relating to the interior and exterior of the vehicle. The first to fourth pieces of information may contain different information from each other. However, the embodiments are not limited thereto, and some of the first to fourth pieces of information may contain the same information from each other.

[0328] Figures 14 to 16 illustrate an example of an electronic device or an example including an electronic device, and a display module including a light-emitting element containing a polycyclic compound of one embodiment can be used in other electronic devices without departing from the concept of the semi-inventive.

[0329] The following describes in detail a polycyclic compound and a light-emitting element of one embodiment according to one embodiment of the present invention, with reference to examples and comparative examples. Furthermore, the following examples are illustrative to aid in understanding the present invention, and the scope of the present invention is not limited thereto.

[0330] [Examples] 1. Synthesis of a polycyclic compound in one example The method for synthesizing polycyclic compounds according to this embodiment will be specifically explained by illustrating the synthesis methods of compounds 1, 2, 3, 21, 31, 36, 51, 61, 69, 71, and 86. Furthermore, the synthesis methods of polycyclic compounds described below are just one example, and the synthesis methods of compounds according to the embodiments of the present invention are not limited to the examples below.

[0331] (1) Synthesis of compound 1 Polycyclic compound 1 according to one example can be synthesized, for example, by the steps of the following reaction formula 1.

[0332] [Reaction Equation 1] JPEG2026135762000097.jpg134170

[0333] <Synthesis of intermediate 1C> Under an argon (Ar) atmosphere, 2,6-dichloropyridine (1A) (20 g), carbazole (1B) (23 g), Cs2CO3 (66 g), and 1-methyl-2-pyrrolidone (270 mL) were added to a 1000 mL three-necked flask and heated and stirred at 150 °C for 16 hours. After cooling to room temperature, water was added and extracted with CH2Cl2. The organic layer was collected, dried over MgSO4, and the solvent was removed by vacuum distillation. Purification by silica gel column chromatography yielded 19.6 g of intermediate 1C (yield 52%). The mass number of intermediate 1C, as measured by FAB-MS, was 279.

[0334] <Synthesis of intermediate 1E> Under an argon atmosphere, intermediate 1C (19.6 g), 2-aminobiphenyl (1D) (18 g), bis(dibenzylideneacetone)palladium(0) (Pd(dba)2, 1.2 g), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (SPhos, 1.7 g), sodium tert-butoxide (NaOtBu, 10 g), and toluene (350 mL) were added to a 1000 mL three-necked flask and heated and stirred at 70°C for 24 hours. After cooling to room temperature, water was added and the mixture was extracted with toluene. The organic layer was collected and dried over MgSO4, and the solvent was removed by vacuum distillation. Purification by silica gel column chromatography yielded 18.2 g of intermediate 1E (63% yield). The mass number of intermediate 1E, as measured by FAB-MS, was 412.

[0335] <Synthesis of intermediate 1H> Under an argon atmosphere, 1,3-difluoro-5-iodobenzene (1F) (30 g), phenol (1 G) (30 g), K2CO3 (52 g), and 1-methyl-2-pyrrolidone (400 mL) were added to a 1000 mL three-necked flask and heated and stirred at 160 °C for 32 hours. After cooling to room temperature, water was added and the mixture was extracted with CH2Cl2. The organic layer was collected, dried over MgSO4, and the solvent was removed by vacuum distillation. Purification by silica gel column chromatography yielded 35 g of intermediate 1H (70% yield). The mass number of intermediate 1H, as measured by FAB-MS, was 404.

[0336] <Synthesis of intermediate 1J> Under an argon atmosphere, intermediate 1H (35 g), intermediate 1I (26 g), bis(dibenzylideneacetone)palladium(0) (Pd(dba)2, 0.52 g), tri-tert-butylphosphine tetrafluoroborate (0.52 g), sodium tert-butoxide (NaOtBu, 13 g), and toluene (400 mL) were added to a 1000 mL three-necked flask and heated and stirred at 100 °C for 6 hours. After cooling to room temperature, water was added and extracted with toluene. The organic layer was collected, dried over MgSO4, and the solvent was removed by vacuum distillation. Purification by silica gel column chromatography yielded 41 g of intermediate 1J (90% yield). The mass number of intermediate 1J, as measured by FAB-MS, was 506.

[0337] <Synthesis of 1L of intermediate> Under an argon atmosphere, 1 J (41 g) of the intermediate, 1,3-dibromo-5-tert-butylbenzene (1 K) (71 g), CuI (15.4 g), and K2CO3 (34 g) were added to a 500 mL three-necked flask and heated and stirred at 230 °C for 32 hours. After cooling to room temperature, water was added and extracted with CH2Cl2. The organic layer was collected, dried over MgSO4, and the solvent was removed by vacuum distillation. Purification by silica gel column chromatography yielded 20.3 g of the intermediate in 1 L (yield 35%). The mass number of the intermediate in 1 L, as measured by FAB-MS, was 717.

[0338] <Synthesis of intermediate 1M> Under an argon atmosphere, 1 L (6 g) of intermediate, intermediate 1E (4.1 g), bis(dibenzylideneacetone)palladium(0) (Pd(dba)2, 0.096 g), tri-tert-butylphosphinetetrafluoroborate (0.097 g), sodium tert-butoxide (NaOtBu, 1.2 g), and toluene (80 mL) were added to a 300 mL three-necked flask and heated and stirred at 100 °C for 6 hours. After cooling to room temperature, water was added and extracted with toluene. The organic layer was collected, dried over MgSO4, and the solvent was removed by vacuum distillation. Purification by silica gel column chromatography yielded 7.2 g of intermediate 1M (82% yield). The mass number of intermediate 1M, as measured by FAB-MS, was 10⁴⁷.

[0339] <Synthesis of Compound 1> Under an argon atmosphere, 1M (7.2g) of the intermediate was placed in a 500mL three-necked flask k, dissolved in o-dichlorobenzene (OBCD, 200mL), and cooled to 0°C in an ice bath. Next, boron triiodide (BI3, 16g) and pyridine (4.9g) were added, and the mixture was heated and stirred at 190°C for 3 hours. After cooling to 0°C in an ice bath, N,N-diisopropylethylamine (DIPEA, 30mL) was added. After returning to room temperature, the reaction solution was filtered through silica gel, and the solvent in the filtrate was removed by vacuum distillation. The resulting crude product was purified by silica gel column chromatography to obtain 1.1g of compound 1 (yield 15%). The molecular weight of compound 1, as measured by FAB-MS, was 1063.

[0340] (2) Synthesis of compound 2 Polycyclic compound 2 according to one example can be synthesized, for example, by the steps of reaction formula 2 below.

[0341] [Reaction Equation 2] JPEG2026135762000098.jpg154170

[0342] <Synthesis of intermediate 2C> Under an argon atmosphere, 2-bromoaniline (2A) (10 g), 3,5-di-tert-butylboronic acid (2B) (27 g), tetrakis(triphenylphosphine)palladium (0) (Pd(PPh3)4, 0.67 g), K2CO3 (16 g), and toluene / ethanol / H2O (150 / 60 / 30 mL) were added to a 500 mL three-necked flask and heated and stirred at 80°C for 24 hours. After returning to room temperature, water was added and extracted with toluene. The organic layer was collected, dried over MgSO4, and the solvent was removed by vacuum distillation. Purification by silica gel column chromatography yielded 13.6 g of intermediate 2C (83% yield). The mass number of intermediate 2C, as measured by FAB-MS, was 281.

[0343] <Synthesis of 2D Intermediates> Under an argon atmosphere, intermediate 2C (13.6 g), intermediate 1C (9 g), bis(dibenzylideneacetone)palladium(0) (Pd(dba)2, 0.56 g), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (SPhos, 0.8 g), sodium tert-butoxide (NaOtBu, 4.7 g), and toluene (150 mL) were added to a 500 mL three-necked flask and heated and stirred at 70°C for 24 hours. After returning to room temperature, water was added and extracted with toluene. The organic layer was collected, dried over MgSO4, and the solvent was removed by vacuum distillation. Purification by silica gel column chromatography yielded 11.3 g of intermediate 2D (yield 67%). The mass number of intermediate 2D, as measured by FAB-MS, was 524.

[0344] <Synthesis of intermediate 2F> Under an argon atmosphere, intermediate 1F (10 g), 4-phenylphenol (17 g), Cs2CO3 (54 g), and 1-methyl-2-pyrrolidone (300 mL) were added to a 1000 mL three-necked flask and heated and stirred at 160 °C for 32 hours. After returning to room temperature, water was added and extracted with CH2Cl2. The organic layer was collected, dried over MgSO4, and the solvent was removed by vacuum distillation. Purification by silica gel column chromatography yielded 18.5 g of intermediate 2F (82% yield). The mass number of intermediate 2F, as measured by FAB-MS, was 540.

[0345] <Synthesis of intermediate 2G> Under an argon atmosphere, intermediate 2F (18.5 g), intermediate 1I (10.1 g), bis(dibenzylideneacetone)palladium(0) (Pd(dba)2, 0.2 g), tri-tert-butylphosphine tetrafluoroborate (0.2 g), sodium tert-butoxide (NaOtBu, 4.9 g), and toluene (200 mL) were added to a 500 mL three-necked flask and heated and stirred at 100 °C for 6 hours. After returning to room temperature, water was added and extracted with toluene. The organic layer was collected, dried over MgSO4, and the solvent was removed by vacuum distillation. Purification by silica gel column chromatography yielded 19.8 g of intermediate 2G (88% yield). The mass number of intermediate 2G, as measured by FAB-MS, was 658.

[0346] <Synthesis of intermediate 2H> Under an argon atmosphere, 19.8 g of intermediate 2G, 26 g of intermediate 1K, 5.7 g of CuI, and 12.5 g of K2CO3 were added to a 300 mL three-necked flask and heated and stirred at 230 °C for 32 hours. After returning to room temperature, water was added and extracted with CH2Cl2. The organic layer was collected, dried over MgSO4, and the solvent was removed by vacuum distillation. Purification by silica gel column chromatography yielded 7.8 g of intermediate 2H (30% yield). The mass number of intermediate 2H, as measured by FAB-MS, was 869.

[0347] <Synthesis of intermediate 2I> Under an argon atmosphere, intermediate 2H (7.8 g), intermediate 2D (5.6 g), bis(dibenzylideneacetone)palladium(0) (Pd(dba)2, 0.010 g), tri-tert-butylphosphine tetrafluoroborate (0.010 g), sodium tert-butoxide (NaOtBu, 1.2 g), and toluene (100 mL) were added to a 300 mL three-necked flask and heated and stirred at 100 °C for 6 hours. After returning to room temperature, water was added and extracted with toluene. The organic layer was collected, dried over MgSO4, and the solvent was removed by vacuum distillation. Purification by silica gel column chromatography yielded 9.4 g of intermediate 2I (80% yield). The mass number of intermediate 2I, as measured by FAB-MS, was 1311.

[0348] <Synthesis of Compound 2> Under an argon atmosphere, intermediate 2I (9.4g) was placed in a 500mL three-necked flask and dissolved in o-dichlorobenzene (OBCD, 200mL). The mixture was cooled to 0°C in an ice bath, and boron triiodide (BI3, 17g) and pyridine (5.1g) were added. The mixture was then heated and stirred at 190°C for 3 hours. Next, the mixture was cooled to 0°C in an ice bath and N,N-diisopropylethylamine (DIPEA, 30mL) was added. After returning to room temperature, the reaction solution was filtered through silica gel, and the solvent in the filtrate was removed by vacuum distillation. The resulting crude product was purified by silica gel column chromatography to obtain 1.7g of compound 2 (yield 18%). The molecular weight of compound 2, as measured by FAB-MS, was 1327.

[0349] (3) Synthesis of compound 3 Polycyclic compound 3 according to one example can be synthesized, for example, by the steps of the following reaction formula 3.

[0350] [Reaction Equation 3] JPEG2026135762000099.jpg127170

[0351] <Synthesis of Intermediate 3B> Under an argon atmosphere, 1-bromo-3-chloro-5-fluorobenzene (3A) (20 g), intermediate 1G (13.4 g), Cs2CO3 (62 g), and 1-methyl-2-pyrrolidone (300 mL) were added to a 1000 mL three-necked flask and heated and stirred at 140 °C for 32 hours. After returning to room temperature, water was added and extracted with CH2Cl2. The organic layer was collected, dried over MgSO4, and the solvent was removed by vacuum distillation. Purification by silica gel column chromatography yielded 23.3 g of intermediate 3B (86% yield). The mass number of intermediate 3B, as measured by FAB-MS, was 284.

[0352] <Synthesis of 3D Intermediate Forms> Under an argon atmosphere, intermediate 3B (10 g), diphenylamine (3C) (9 g), palladium(II) acetate (Pd(OAc)2, 0.24 g), 4,5-bis(diphenylphosphin)-9,9-dimethylxanthene (Xantphos, 0.61 g), sodium tert-butoxide (NaOtBu, 5.1 g), and toluene (150 mL) were added to a 500 mL three-necked flask and heated and stirred at 110 °C for 24 hours. After returning to room temperature, water was added and the mixture was extracted with toluene. The organic layer was collected and dried over MgSO4, and the solvent was removed by vacuum distillation. The mixture was purified by silica gel column chromatography to obtain 12 g of intermediate 3D (yield 92%). The mass number of intermediate 3D, as measured by FAB-MS, was 372.

[0353] <Synthesis of intermediate 3E> Under an argon atmosphere, intermediate 3D (12 g), intermediate 1I (9.5 g), bis(dibenzylideneacetone)palladium(0) (Pd(dba)2, 0.19 g), tri-tert-butylphosphine tetrafluoroborate (0.19 g), sodium tert-butoxide (NaOtBu, 4.6 g), and toluene (150 mL) were added to a 500 mL three-necked flask and heated and stirred at 100 °C for 24 hours. After returning to room temperature, water was added and extracted with toluene. The organic layer was collected, dried over MgSO4, and the solvent was removed by vacuum distillation. Purification by silica gel column chromatography yielded 16.1 g of intermediate 3E (86% yield). The mass number of intermediate 3E, as measured by FAB-MS, was 581.

[0354] <Synthesis of intermediate 3F> Under an argon atmosphere, intermediate 3E (16.1 g), intermediate 1K (24 g), CuI (5.3 g), and K2CO3 (11.5 g) were added to a 300 mL three-necked flask and heated and stirred at 230 °C for 32 hours. After returning to room temperature, water was added and extracted with CH2Cl2. The organic layer was collected, dried over MgSO4, and the solvent was removed by vacuum distillation. Purification by silica gel column chromatography yielded 7.9 g of intermediate 3F (yield 36%). The mass number of intermediate 3F, as measured by FAB-MS, was 792.

[0355] <Synthesis of intermediate 3G> Under an argon atmosphere, intermediate 3F (7.9g), intermediate 1E (4.9g), bis(dibenzylideneacetone)palladium(0) (Pd(dba)2, 0.057g), tri-tert-butylphosphinetetrafluoroborate (0.057g), sodium tert-butoxide (NaOtBu, 1.5g), and toluene (80mL) were added to a 200mL three-necked flask and heated and stirred at 100°C for 6 hours. After returning to room temperature, water was added and extracted with toluene. The organic layer was collected, dried over MgSO4, and the solvent was removed by vacuum distillation. Purification by silica gel column chromatography yielded 10g of 3G (90% yield). The mass number of 8B, measured by FAB-MS, was 1122.

[0356] <Synthesis of Compound 3> Under an Ar atmosphere, 3G (10g) was placed in a 500mL three-necked flask and dissolved in o-dichlorobenzene (ODCB, 200mL). The mixture was cooled to 0°C in an ice bath, and boron triiodide (BI3, 21g) and pyridine (5.3g) were added. The mixture was then heated and stirred at 190°C for 3 hours, cooled to 0°C in an ice bath, and N,N-diisopropylethylamine (DIPEA, 30mL) was added. After returning to room temperature, the reaction solution was filtered through silica gel, and the solvent in the filtrate was removed by vacuum distillation. The resulting crude product was purified by silica gel column chromatography to obtain 1.4g of 3 (yield 14%). The molecular weight of 3, as measured by FAB-MS, was 1138.

[0357] (4) Synthesis of compound 21 The polycyclic compound 21 according to one example can be synthesized, for example, by the steps of the following reaction formula 4.

[0358] [Reaction Equation 4] JPEG2026135762000100.jpg91170

[0359] <Synthesis of intermediate 21B> Under an argon atmosphere, 1-bromo-3-iodobenzene (21A) (30 g), intermediate 1B (17.7 g), palladium(II) acetate (Pd(OAc)2, 0.71 g), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (Xantphos, 1.8 g), sodium tert-butoxide (NaOtBu, 13 g), and toluene (400 mL) were added to a 1000 mL three-necked flask and heated and stirred at 110 °C for 24 hours. After returning to room temperature, water was added and extracted with toluene. The organic layer was collected, dried over MgSO4, and the solvent was removed by vacuum distillation. Purification by silica gel column chromatography yielded 27.2 g of intermediate 21B (80% yield). The mass number of intermediate 21B, as measured by FAB-MS, was 322.

[0360] <Synthesis of intermediate 21D> Under an argon atmosphere, intermediate 21B (27.3g), intermediate 21C (20g), bis(dibenzylideneacetone)palladium(0) (Pd(dba)2, 0.98g), (±)-BINAP (2.1g), sodium tert-butoxide (NaOtBu, 12.2g), and toluene (400mL) were added to a 1000mL three-necked flask and heated and stirred at 100°C for 6 hours. After returning to room temperature, water was added and extracted with toluene. The organic layer was collected, dried over MgSO4, and the solvent was removed by vacuum distillation. Purification by silica gel column chromatography yielded 29.2g of intermediate 21D (84% yield). The mass number of intermediate 21D, as measured by FAB-MS, was 412.

[0361] <Synthesis of intermediate 21E> Under an argon atmosphere, intermediate 21D (4.1 g), intermediate 1 L (6 g), bis(dibenzylideneacetone)palladium(0) (Pd(dba)2, 0.048 g), tri-tert-butylphosphine tetrafluoroborate (0.049 g), sodium tert-butoxide (NaOtBu, 1.2 g), and toluene (80 mL) were added to a 200 mL three-necked flask and heated and stirred at 100 °C for 6 hours. After returning to room temperature, water was added and extracted with toluene. The organic layer was collected, dried over MgSO4, and the solvent was removed by vacuum distillation. Purification by silica gel column chromatography yielded 7.7 g of intermediate 21E (82% yield). The mass number of intermediate 21E, as measured by FAB-MS, was 1122.

[0362] <Synthesis of Compound 21> Under an argon atmosphere, 7.7 g of intermediate 21E was placed in a 500 mL three-necked flask and dissolved in o-dichlorobenzene (OBCD, 200 mL). The mixture was cooled to 0°C in an ice bath, and boron triiodide (BI3, 17 g) and pyridine (5.2 g) were added. The mixture was then heated and stirred at 190°C for 3 hours. Next, the mixture was cooled to 0°C in an ice bath and N,N-diisopropylethylamine (DIPEA, 30 mL) was added. After returning to room temperature, the reaction solution was filtered through silica gel, and the solvent in the filtrate was removed by vacuum distillation. The resulting crude product was purified by silica gel column chromatography to obtain 1.2 g of compound 21 (yield 14%). The molecular weight of compound 21, as measured by FAB-MS, was 1063.

[0363] (5) Synthesis of compound 31 The polycyclic compound 31 according to one example can be synthesized, for example, by the steps of the following reaction formula 5.

[0364] [Reaction Equation 5] JPEG2026135762000101.jpg40170

[0365] <Synthesis of intermediate 31B> Under an argon atmosphere, intermediate 21B (10 g), intermediate 31A (7.4 g), bis(dibenzylideneacetone)palladium(0) (Pd(dba)2, 0.36 g), (±)-BINAP (0.77 g), sodium tert-butoxide (NaOtBu, 4.4 g), and toluene (150 mL) were added to a 500 mL three-necked flask and heated and stirred at 100 °C for 6 hours. After returning to room temperature, water was added and extracted with toluene. The organic layer was collected, dried over MgSO4, and the solvent was removed by vacuum distillation. Purification by silica gel column chromatography yielded 10 g of intermediate 31B (81% yield). The mass number of intermediate 31B, as measured by FAB-MS, was 412.

[0366] <Synthesis of intermediate 31C> Under an argon atmosphere, intermediate 31B (4.1 g), intermediate 1 L (6 g), bis(dibenzylideneacetone)palladium(0) (Pd(dba)2, 0.48 g), tri-tert-butylphosphine tetrafluoroborate (0.49 g), sodium tert-butoxide (NaOtBu, 1.2 g), and toluene (80 mL) were added to a 200 mL three-necked flask and heated and stirred at 100 °C for 6 hours. After returning to room temperature, water was added and extracted with toluene. The organic layer was collected and dried over MgSO4, and the solvent was removed by vacuum distillation. Purification by silica gel column chromatography yielded 8 g of intermediate 31C (yield 85%). The mass number of intermediate 31C, as measured by FAB-MS, was 1122.

[0367] <Synthesis of Compound 31> Under an argon atmosphere, 8 g of intermediate 31C was placed in a 500 mL three-necked flask and dissolved in o-dichlorobenzene (OBCD, 200 mL). The mixture was cooled to 0°C in an ice bath, and boron triiodide (BI3, 18 g) and pyridine (5.4 g) were added. The mixture was then heated and stirred at 190°C for 3 hours. Next, the mixture was cooled to 0°C in an ice bath and N,N-diisopropylethylamine (DIPEA, 30 mL) was added. After returning to room temperature, the reaction solution was filtered through silica gel, and the solvent in the filtrate was removed by vacuum distillation. The resulting crude product was purified by silica gel column chromatography to obtain 1.3 g of compound 31 (yield 16%). The molecular weight of compound 31, as measured by FAB-MS, was 1063.

[0368] (6) Synthesis of compound 36 The polycyclic compound 36 according to one example can be synthesized, for example, by the steps of the following reaction formula 6.

[0369] [Reaction Equation 6] JPEG2026135762000102.jpg81170

[0370] <Synthesis of intermediate 36A> Under an argon atmosphere, intermediate 1H (6 g), intermediate 1D (3.7 g), bis(dibenzylideneacetone)palladium(0) (Pd(dba)2, 0.18 g), (±)-BINAP (0.39 g), sodium tert-butoxide (NaOtBu, 2.2 g), and toluene (100 mL) were added to a 300 mL three-necked flask and heated and stirred at 100 °C for 6 hours. After returning to room temperature, water was added and extracted with toluene. The organic layer was collected, dried over MgSO4, and the solvent was removed by vacuum distillation. Purification by silica gel column chromatography yielded 6.1 g of intermediate 36A (92% yield). The mass number of intermediate 36A, as measured by FAB-MS, was 430.

[0371] <Synthesis of intermediate 36C> Under an argon atmosphere, intermediate 36B (6 g), intermediate 3C (7.5 g), bis(dibenzylideneacetone)palladium(0) (Pd(dba)2, 0.38 g), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (SPhos, 0.54 g), sodium tert-butoxide (NaOtBu, 6.4 g), and toluene (200 mL) were added to a 500 mL three-necked flask and heated and stirred at 60°C for 24 hours. After returning to room temperature, water was added and extracted with toluene. The organic layer was collected, dried over MgSO4, and the solvent was removed by vacuum distillation. Purification by silica gel column chromatography yielded 6.1 g of intermediate 36C (yield 62%). The mass number of intermediate 36C, as measured by FAB-MS, was 448.

[0372] <Synthesis of intermediate 36D> Under an argon atmosphere, intermediate 36C (5 g), intermediate 36A (5.7 g), bis(dibenzylideneacetone)palladium(0) (Pd(dba)2, 0.06 g), tri-tert-butylphosphinetetrafluoroborate (0.06 g), sodium tert-butoxide (NaOtBu, 1.6 g), and toluene (80 mL) were added to a 200 mL three-necked flask and heated and stirred at 110 °C for 6 hours. After returning to room temperature, water was added and extracted with toluene. The organic layer was collected, dried over MgSO4, and the solvent was removed by vacuum distillation. Purification by silica gel column chromatography yielded 8.1 g of intermediate 36D (yield 86%). The mass number of intermediate 36D, as measured by FAB-MS, was 841.

[0373] <Synthesis of Compound 36> Under an argon atmosphere, 8.1 g of intermediate 36D was placed in a 500 mL three-necked flask and dissolved in o-dichlorobenzene (OBCD, 200 mL). The mixture was cooled to 0°C in an ice bath, and boron triiodide (BI3, 22.6 g) and pyridine (6.8 g) were added. The mixture was then heated and stirred at 190°C for 3 hours. Next, the mixture was cooled to 0°C in an ice bath and N,N-diisopropylethylamine (DIPEA, 35 mL) was added. After returning to room temperature, the reaction solution was filtered through silica gel, and the solvent in the filtrate was removed by vacuum distillation. The resulting crude product was purified by silica gel column chromatography to obtain 1.2 g of compound 36 (yield 15%). The molecular weight of compound 36, as measured by FAB-MS, was 857.

[0374] (7) Synthesis of compound 51 The polycyclic compound 51 according to one example can be synthesized, for example, by the steps of the following reaction formula 7.

[0375] [Reaction Equation 7] JPEG2026135762000103.jpg129170

[0376] <Synthesis of intermediate 51A> Under an argon atmosphere, intermediate 1H (5 g), intermediate 21C (3.1 g), bis(dibenzylideneacetone)palladium(0)(Pd(dba)2, 0.15 g), (±)-BINAP (0.32 g), sodium tert-butoxide (NaOtBu, 1.9 g), and toluene (80 mL) were added to a 200 mL three-necked flask and heated and stirred at 100 °C for 6 hours. After returning to room temperature, water was added and extracted with toluene. The organic layer was collected, dried over MgSO4, and the solvent was removed by vacuum distillation. Purification by silica gel column chromatography yielded 4.8 g of intermediate 51A (yield 86%). The mass number of intermediate 51A, as measured by FAB-MS, was 431.

[0377] <Synthesis of intermediate 51C> Under an argon atmosphere, bromobenzene (51B) (15 g), intermediate 1I (26 g), bis(dibenzylideneacetone)palladium (0) (Pd(dba)2, 0.54 g), tri-tert-butylphosphine tetrafluoroborate (0.55 g), sodium tert-butoxide (NaOtBu, 13 g), and toluene (400 mL) were added to a 1000 mL three-necked flask and heated and stirred at 100 °C for 6 hours. After returning to room temperature, water was added and extracted with toluene. The organic layer was collected, dried over MgSO4, and the solvent was removed by vacuum distillation. Purification by silica gel column chromatography yielded 27.6 g of intermediate 51C (90% yield). The mass number of intermediate 51B, as measured by FAB-MS, was 321.

[0378] <Synthesis of intermediate 51D> Under an argon atmosphere, intermediate 51C (75g), intermediate 1K (75g), CuI (16.3g), and K2CO3 (36g) were added to a 300mL three-necked flask and heated and stirred at 230°C for 32 hours. After returning to room temperature, water was added and extracted with CH2Cl2. The organic layer was collected, dried over MgSO4, and the solvent was removed by vacuum distillation. Purification by silica gel column chromatography yielded 14.6g of intermediate 51D (32% yield). The mass number of intermediate 51D, as measured by FAB-MS, was 533.

[0379] <Synthesis of intermediate 51E> Under an argon atmosphere, intermediate 51D (5 g), intermediate 51A (4.8 g), bis(dibenzylideneacetone)palladium(0) (Pd(dba)2, 0.054 g), tri-tert-butylphosphine tetrafluoroborate (0.055 g), sodium tert-butoxide (NaOtBu, 1.3 g), and toluene (80 mL) were added to a 200 mL three-necked flask and heated and stirred at 100 °C for 6 hours. After returning to room temperature, water was added and extracted with toluene. The organic layer was collected, dried over MgSO4, and the solvent was removed by vacuum distillation. Purification by silica gel column chromatography yielded 7 g of intermediate 51E (85% yield). The mass number of intermediate 51E, as measured by FAB-MS, was 882.

[0380] <Synthesis of Compound 51> Under an argon atmosphere, intermediate 51E (7 g) was placed in a 500 mL three-necked flask and dissolved in o-dichlorobenzene (OBCD, 200 mL). The mixture was cooled to 0°C in an ice bath, and boron triiodide (BI3, 18.6 g) and pyridine (5.6 g) were added. The mixture was then heated and stirred at 190°C for 3 hours. Next, the mixture was cooled to 0°C in an ice bath and N,N-diisopropylethylamine (DIPEA, 30 mL) was added. After returning to room temperature, the reaction solution was filtered through silica gel, and the solvent in the filtrate was removed by vacuum distillation. The resulting crude product was purified by silica gel column chromatography to obtain 1.3 g of compound 51 (yield 18%). The molecular weight of compound 51, as measured by FAB-MS, was 898.

[0381] (8) Synthesis of compound 61 The polycyclic compound 61 according to one example can be synthesized, for example, by the steps of the following reaction formula 8.

[0382] [Reaction Equation 8] JPEG2026135762000104.jpg43170

[0383] <Synthesis of intermediate 61A> Under an argon atmosphere, intermediate 1H (5 g), intermediate 31A (3.1 g), bis(dibenzylideneacetone)palladium(0)(Pd(dba)2, 0.15 g), (±)-BINAP (0.32 g), sodium tert-butoxide (NaOtBu, 1.9 g), and toluene (80 mL) were added to a 200 mL three-necked flask and heated and stirred at 100 °C for 6 hours. After returning to room temperature, water was added and extracted with toluene. The organic layer was collected, dried over MgSO4, and the solvent was removed by vacuum distillation. Purification by silica gel column chromatography yielded 4.5 g of intermediate 61A (yield 82%). The mass number of intermediate 61A, as measured by FAB-MS, was 431.

[0384] <Synthesis of intermediate 61B> Under an argon atmosphere, intermediate 61A (4.5 g), intermediate 51D (4.6 g), bis(dibenzylideneacetone)palladium(0) (Pd(dba)2, 0.05 g), tri-tert-butylphosphine tetrafluoroborate (0.05 g), sodium tert-butoxide (NaOtBu, 1.2 g), and toluene (80 mL) were added to a 200 mL three-necked flask and heated and stirred at 100 °C for 6 hours. After returning to room temperature, water was added and extracted with toluene. The organic layer was collected, dried over MgSO4, and the solvent was removed by vacuum distillation. Purification by silica gel column chromatography yielded 5.9 g of intermediate 61B (78% yield). The mass number of intermediate 61B, as measured by FAB-MS, was 882.

[0385] <Synthesis of Compound 61> Under an argon atmosphere, intermediate 51E (5.9 g) was placed in a 500 mL three-necked flask and dissolved in o-dichlorobenzene (OBCD, 200 mL). The mixture was cooled to 0°C in an ice bath, and boron triiodide (BI3, 15.7 g) and pyridine (4.8 g) were added. The mixture was then heated and stirred at 190°C for 3 hours. Next, the mixture was cooled to 0°C in an ice bath and N,N-diisopropylethylamine (DIPEA, 25 mL) was added. After returning to room temperature, the reaction solution was filtered through silica gel, and the solvent in the filtrate was removed by vacuum distillation. The resulting crude product was purified by silica gel column chromatography to obtain 0.9 g of compound 61 (yield 15%). The molecular weight of compound 61, as measured by FAB-MS, was 898.

[0386] (9) Synthesis of compound 69 The polycyclic compound 69 according to one example can be synthesized, for example, by the steps of the following reaction formula 9.

[0387] [Reaction Equation 9] JPEG2026135762000105.jpg144170

[0388] <Synthesis of intermediate 69B> Under an argon atmosphere, intermediate 69A (50 g), intermediate 3C (12.9 g), bis(dibenzylideneacetone)palladium(0) (Pd(dba)2, 2.6 g), tri-tert-butylphosphine tetrafluoroborate (2.6 g), sodium tert-butoxide (NaOtBu, 15 g), and toluene (400 mL) were added to a 1 L three-necked flask and heated and stirred at 80°C for 6 hours. After returning to room temperature, water was added and the mixture was extracted with toluene. The organic layer was dried in one step over MgSO4, and the solvent was removed by vacuum distillation. The mixture was purified by silica gel column chromatography to obtain 22.2 g of intermediate 69B (70% yield). The mass number of 69B, as measured by FAB-MS, was 417.

[0389] <Synthesis of intermediate 69D> Under an argon atmosphere, intermediate 69B (22.2 g), intermediate 69C (9.5 g), CuBr (0.76 g), 1,2,3,4-tetrahydro-8-quinolinol (0.71 g), CsCO3 (26 g), and dimethylformamide (200 mL) were added to a 500 mL three-necked flask and heated and stirred at 130 °C for 32 hours. After returning to room temperature, water was added and extracted with CH2Cl2. The organic layer was dried in one step over MgSO4, and the solvent was removed by vacuum distillation. Purification by silica gel column chromatography yielded 22.3 g of intermediate 69D (82% yield). The mass number of intermediate 69D, as measured by FAB-MS, was 515.

[0390] <Synthesis of intermediate 69F> Under an argon atmosphere, intermediate 69D (22.3 g), intermediate 69E (14 g), bis(dibenzylideneacetone)palladium(0) (Pd(dba)2, 0.50 g), tri-tert-butylphosphine tetrafluoroborate (0.50 g), sodium tert-butoxide (NaOtBu, 6.2 g), and toluene (150 mL) were added to a 500 mL three-necked flask and heated and stirred at 110 °C for 12 hours. After returning to room temperature, water was added and the mixture was extracted with toluene. The organic layer was dried in one step over MgSO4, and the solvent was removed by vacuum distillation. The mixture was purified by silica gel column chromatography to obtain 12 g of intermediate 69F (yield 35%). The mass number of intermediate 69F, as measured by FAB-MS, was 800.

[0391] <Synthesis of intermediate 69H> Under an argon atmosphere, intermediate 69F (12 g), intermediate 69G (3.8 g), bis[di-tert-butyl(4-dimethylaminophenyl)phosphine]dichloropalladium(II) (PdCl2(Amphos)2, 0.11 g), K2CO3 (4.1 g), and toluene / ethanol / H2O (100 / 40 / 20 mL) were added to a 200 mL three-necked flask and heated and stirred at 80°C for 24 hours. After returning to room temperature, water was added and extracted with toluene. The organic layer was dried in one step over MgSO4, and the solvent was removed by vacuum distillation. Purification by silica gel column chromatography yielded 10.5 g of intermediate 69H (yield 83%). The mass number of intermediate 69H, as measured by FAB-MS, was 842.

[0392] <Synthesis of Compound 69> Under an Ar atmosphere, 10.5 g of intermediate 69H was placed in a 1 L three-necked flask and dissolved in o-dichlorobenzene (ODCB, 300 mL). The mixture was cooled to 0°C in an ice bath, and boron triiodide (BI3, 29 g) and pyridine (8.8 g) were added. The mixture was then heated and stirred at 190°C for 3 hours, cooled to 0°C in an ice bath, and N,N-diisopropylethylamine (DIPEA, 45 mL) was added. After returning to room temperature, the reaction solution was filtered through silica gel, and the solvent in the filtrate was removed by vacuum distillation. The resulting crude product was purified by silica gel column chromatography to obtain 1.3 g of compound 69 (yield 12%). The molecular weight of compound 69, as measured by FAB-MS, was 858.

[0393] (10) Synthesis of compound 71 The polycyclic compound 71 according to one example can be synthesized, for example, by the steps of the following reaction formula 10.

[0394] [Reaction Equation 10] JPEG2026135762000106.jpg116170

[0395] <Synthesis of intermediate 71A> Under an argon atmosphere, intermediate 3B (10 g), intermediate 21D (17.4 g), palladium(II) acetate (Pd(OAc)2, 0.23 g), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (Xantphos, 0.61 g), sodium tert-butoxide (NaOtBu, 5 g), and toluene (200 mL) were added to a 500 mL three-necked flask and heated and stirred at 110 °C for 24 hours. After returning to room temperature, water was added and extracted with toluene. The organic layer was collected, dried over MgSO4, and the solvent was removed by vacuum distillation. Purification by silica gel column chromatography yielded 18 g of intermediate 71A (yield 83%). The mass number of intermediate 71A, as measured by FAB-MS, was 614.

[0396] <Synthesis of intermediate 71B> Under an argon atmosphere, intermediate 71A (18 g), intermediate 1I (8.6 g), bis(dibenzylideneacetone)palladium(0) (Pd(dba)2, 0.16 g), tri-tert-butylphosphine tetrafluoroborate (0.17 g), sodium tert-butoxide (NaOtBu, 4.2 g), and toluene (150 mL) were added to a 500 mL three-necked flask and heated and stirred at 110 °C for 6 hours. After returning to room temperature, water was added and extracted with toluene. The organic layer was collected, dried over MgSO4, and the solvent was removed by vacuum distillation. Purification by silica gel column chromatography yielded 19.3 g of intermediate 71B (80% yield). The mass number of intermediate 71B, as measured by FAB-MS, was 823.

[0397] <Synthesis of intermediate 71C> Under an argon atmosphere, intermediate 71B (19.3g), intermediate 51D (18.7g), CuI (4.4g), and K2CO3 (10g) were added to a 300mL three-necked flask and heated and stirred at 230°C for 32 hours. After returning to room temperature, water was added and extracted with CH2Cl2. The organic layer was collected, dried over MgSO4, and the solvent was removed by vacuum distillation. Purification by silica gel column chromatography yielded 6g of intermediate 71C (20% yield). The mass number of intermediate 71C, as measured by FAB-MS, was 1275.

[0398] <Synthesis of Compound 71> Under an argon atmosphere, 6 g of intermediate 71C was placed in a 400 mL three-necked flask and dissolved in o-dichlorobenzene (OBCD, 200 mL). The mixture was cooled to 0°C in an ice bath, and boron triiodide (BI3, 11 g) and pyridine (3.3 g) were added. The mixture was then heated and stirred at 190°C for 3 hours. Next, the mixture was cooled to 0°C in an ice bath and N,N-diisopropylethylamine (DIPEA, 20 mL) was added. After returning to room temperature, the reaction solution was filtered through silica gel, and the solvent in the filtrate was removed by vacuum distillation. The resulting crude product was purified by silica gel column chromatography to obtain 1 g of compound 71 (yield 16%). The molecular weight of compound 71, as measured by FAB-MS, was 1290.

[0399] (11) Synthesis of compound 86 The polycyclic compound 86 according to one example can be synthesized, for example, by the steps of the following reaction formula 11.

[0400] [Reaction Equation 11] JPEG2026135762000107.jpg103170

[0401] <Synthesis of intermediate 86B> Under an argon atmosphere, intermediate 3A (15 g), 3-phenylphenol (86A) (14.6 g), Cs2CO3 (47 g), and 1-methyl-2-pyrrolidone (300 mL) were added to a 1000 mL three-necked flask and heated and stirred at 140 °C for 16 hours. After returning to room temperature, water was added and extracted with CH2Cl2. The organic layer was collected, dried over MgSO4, and the solvent was removed by vacuum distillation. Purification by silica gel column chromatography yielded 21.6 g of intermediate 86B (84% yield). The mass number of intermediate 86B, as measured by FAB-MS, was 360.

[0402] <Synthesis of intermediate 86C> Under an argon atmosphere, intermediate 86B (15 g), intermediate 1E (18.5 g), palladium(II) acetate (Pd(OAc)2, 0.25 g), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (Xantphos, 0.65 g), sodium tert-butoxide (NaOtBu, 5.1 g), and toluene (150 mL) were added to a 500 mL three-necked flask and heated and stirred at 110 °C for 24 hours. After returning to room temperature, water was added and extracted with toluene. The organic layer was collected, dried over MgSO4, and the solvent was removed by vacuum distillation. Purification by silica gel column chromatography yielded 22.3 g of intermediate 86C (yield 86%). The mass number of intermediate 86C, as measured by FAB-MS, was 690.

[0403] <Synthesis of intermediate 86D> Under an argon atmosphere, intermediate 86C (22.3 g), intermediate 1I (8.7 g), bis(dibenzylideneacetone)palladium(0) (Pd(dba)2, 0.19 g), tri-tert-butylphosphine tetrafluoroborate (0.19 g), sodium tert-butoxide (NaOtBu, 4.3 g), and toluene (150 mL) were added to a 500 mL three-necked flask and heated and stirred at 110 °C for 12 hours. After returning to room temperature, water was added and extracted with toluene. The organic layer was collected, dried over MgSO4, and the solvent was removed by vacuum distillation. Purification by silica gel column chromatography yielded 24.4 g of intermediate 86D (yield 84%). The mass number of intermediate 86D, as measured by FAB-MS, was 899.

[0404] <Synthesis of intermediate 86E> Under an argon atmosphere, intermediate 86D (24.4 g), intermediate 51D (21.7 g), CuI (5.2 g), and K2CO3 (11 g) were added to a 300 mL three-necked flask and heated and stirred at 230 °C for 32 hours. After returning to room temperature, water was added and extracted with CH2Cl2. The organic layer was collected, dried over MgSO4, and the solvent was removed by vacuum distillation. Purification by silica gel column chromatography yielded 6.6 g of intermediate 86E (18% yield). The mass number of intermediate 86E, as measured by FAB-MS, was 1351.

[0405] <Synthesis of Compound 86> Under an argon atmosphere, intermediate 86E (6.6 g) was placed in a 300 mL three-necked flask and dissolved in o-dichlorobenzene (OBCD, 200 mL). The mixture was cooled to 0°C in an ice bath, and boron triiodide (BI3, 11.5 g) and pyridine (3.5 g) were added. The mixture was then heated and stirred at 190°C for 3 hours. Next, the mixture was cooled to 0°C in an ice bath and N,N-diisopropylethylamine (DIPEA, 20 mL) was added. After returning to room temperature, the reaction solution was filtered through silica gel, and the solvent in the filtrate was removed by vacuum distillation. The resulting crude product was purified by silica gel column chromatography to obtain 1.1 g of compound 86 (yield 17%). The molecular weight of compound 86, as measured by FAB-MS, was 1366.

[0406] (12) Synthesis of compound 113 The polycyclic compound 113 according to one example can be synthesized, for example, by the steps of the following reaction formula 12.

[0407] [Reaction Equation 12] JPEG2026135762000108.jpg119170

[0408] <Synthesis of intermediate 113B> Under an argon atmosphere, intermediate 113A (25 g), intermediate 3C (6.4 g), bis(dibenzylideneacetone)palladium(0) (Pd(dba)2, 1.3 g), tri-tert-butylphosphine tetrafluoroborate (1.3 g), sodium tert-butoxide (NaOtBu, 7.3 g), and toluene (150 mL) were added to a 500 mL three-necked flask and heated and stirred at 80°C for 8 hours. After returning to room temperature, water was added and the mixture was extracted with toluene. The organic layer was dried in one step over MgSO4, and the solvent was removed by vacuum distillation. The mixture was purified by silica gel column chromatography to obtain 7.9 g of intermediate 113B (50% yield). The mass number of intermediate 113B, as measured by FAB-MS, was 417.

[0409] <Synthesis of intermediate 113D> Under an argon atmosphere, intermediate 113D (7.9 g), intermediate 113E (2.4 g), bis(dibenzylideneacetone)palladium(0) (Pd(dba)2, 0.22 g), (±)-BINAP (0.47 g), sodium tert-butoxide (NaOtBu, 2.7 g), and toluene (80 mL) were added to a 200 mL three-necked flask and heated and stirred at 110 °C for 6 hours. After returning to room temperature, water was added and extracted with toluene. The organic layer was dried in one step over MgSO4, and the solvent was removed by vacuum distillation. Purification by silica gel column chromatography yielded 7.1 g of intermediate 113D (yield 87%). The mass number of intermediate 113D measured by FAB-MS was 412.

[0410] <Synthesis of intermediate 113E> Under an argon atmosphere, intermediate 1K (10 g), intermediate 3C (5.8 g), palladium(II) acetate (Pd(OAc)2, 0.23 g), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (Xantphos, 0.59 g), sodium tert-butoxide (NaOtBu, 5 g), and toluene (130 mL) were added to a 300 mL three-necked flask and heated and stirred at 110 °C for 24 hours. After returning to room temperature, water was added and the mixture was extracted with toluene. The organic layer was dried in one step over MgSO4, and the solvent was removed by vacuum distillation. The mixture was purified by silica gel column chromatography to obtain 9.4 g of intermediate 113E (72% yield). The mass number of intermediate 113E, as measured by FAB-MS, was 380.

[0411] <Synthesis of intermediate 113F> Under an argon atmosphere, intermediate 113D (7g), intermediate 113E (6.2g), bis(dibenzylideneacetone)palladium(0) (Pd(dba)2, 0.19g), tri-tert-butylphosphine tetrafluoroborate (0.19g), sodium tert-butoxide (NaOtBu, 2.4g), and toluene (100mL) were added to a 300mL three-necked flask and heated and stirred at 100°C for 6 hours. After returning to room temperature, water was added and the mixture was extracted with toluene. The organic layer was dried in one step over MgSO4, and the solvent was removed by vacuum distillation. The mixture was purified by silica gel column chromatography to obtain 9.6g of intermediate 113F (yield 81%). The mass number of intermediate 113F, as measured by FAB-MS, was 729.

[0412] <Synthesis of Compound 113> Under an argon atmosphere, 9.6 g of intermediate 113F was placed in a 500 mL three-necked flask and dissolved in o-dichlorobenzene (ODCB, 250 mL). The mixture was cooled to 0°C in an ice bath, and boron triiodide (BI3, 31 g) and pyridine (9.4 g) were added. The mixture was then heated and stirred at 190°C for 3 hours, cooled to 0°C in an ice bath, and N,N-diisopropylethylamine (DIPEA, 45 mL) was added. After returning to room temperature, the reaction solution was filtered through silica gel, and the solvent in the filtrate was removed by vacuum distillation. The resulting crude product was purified by silica gel column chromatography to obtain 1 g of compound 113 (yield 10%). The molecular weight of compound 113, as measured by FAB-MS, was 745.

[0413] (13) Synthesis of compound 126 The polycyclic compound 126 according to one example can be synthesized, for example, by the steps of the following reaction formula 13.

[0414] [Reaction Equation 13] JPEG2026135762000109.jpg102170

[0415] <Synthesis of intermediate 126B> Under an argon atmosphere, 60 g of intermediate 1K, 32 g of intermediate 126A, 35 g of potassium tert-butoxide (KOtBu), and DMSO were added to a 500 mL three-necked flask and heated and stirred at 80°C for 6 hours. After returning to room temperature, water was added and extracted with CH2Cl2. The organic layer was dried in one step over MgSO4, and the solvent was removed by vacuum distillation. Purification by silica gel column chromatography yielded 25.8 g of intermediate 126B (yield 68%). The mass number of intermediate 126B, as measured by FAB-MS, was 368.

[0416] <Synthesis of intermediate 126C> Under an argon atmosphere, intermediate 126B (25.8 g), intermediate 86D (30 g), CuI (6.4 g), and K2CO3 (14 g) were added to a 300 mL three-necked flask and heated and stirred at 230 °C for 32 hours. After returning to room temperature, water was added and extracted with CH2Cl2. The organic layer was dried in one step over MgSO4, and the solvent was removed by vacuum distillation. Purification by silica gel column chromatography yielded 8.3 g of intermediate 126C (yield 21%). The mass number of intermediate 126C, as measured by FAB-MS, was 1186.

[0417] <Synthesis of Compound 126> Under an argon atmosphere, 8.3 g of intermediate 126C was placed in a 500 mL three-necked flask and dissolved in o-dichlorobenzene (ODCB, 200 mL). The mixture was cooled to 0°C in an ice bath, and boron triiodide (BI3, 16.4 g) and pyridine (5 g) were added. The mixture was then heated and stirred at 190°C for 3 hours, cooled to 0°C in an ice bath, and N,N-diisopropylethylamine (DIPEA, 30 mL) was added. After returning to room temperature, the reaction solution was filtered through silica gel, and the solvent in the filtrate was removed by vacuum distillation. The resulting crude product was purified by silica gel column chromatography to obtain 0.78 g of compound 126 (yield 9%). The molecular weight of compound 126, as measured by FAB-MS, was 1202.

[0418] 2. Fabrication and evaluation of light-emitting devices

[0419] (1) Fabrication of light-emitting element A light-emitting element containing the polycyclic compound of one example or the comparative compound in the light-emitting layer was manufactured by the following method. The light-emitting elements of Examples 1 to 10 were manufactured using the polycyclic compound of one example as the dopant material for the light-emitting layer. The light-emitting elements of Comparative Examples 1 to 9 were manufactured using comparative compounds X-1 to X-9 as the dopant material for the light-emitting layer.

[0420] As the first electrode, a glass substrate patterned with ITO to a thickness of 150 nm was ultrasonically cleaned for 5 minutes each using isopropyl alcohol and pure water. After ultrasonic cleaning, it was irradiated with UV light for 30 minutes and then treated with ozone. Next, a hole transport region was formed by sequentially depositing HAT-CN to a thickness of 10 nm, α-NPD to a thickness of 80 nm, and mCP to a thickness of nm.

[0421] Next, the example compound or comparative compound and mCBP were co-deposited to form a light-emitting layer with a thickness of 20 nm. The example compound or comparative compound and mCBP were co-deposited in a weight ratio of 1:99. In the fabrication of the light-emitting device, the example compound or comparative compound was used as a dopant material.

[0422] Next, TPBi was deposited sequentially to a thickness of 30 nm, followed by LiF to a thickness of 0.5 nm, to form an electron transport region.

[0423] Next, a second electrode was formed by depositing Al to a thickness of 100 nm.

[0424] In the example, the hole transport region, light-emitting layer, electron transport region, and second electrode were formed using a vacuum deposition apparatus.

[0425] The compounds used in the luminescent males of the examples and comparative examples are shown in Table 1 below.

[0426] [Table 1] JPEG2026135762000111.jpg213170JPEG2026135762000112.jpg202170

[0427] Other compounds used in the fabrication of the light-emitting element are as follows:

[0428] (Materials used in fabricating the light-emitting element) JPEG2026135762000113.jpg74153

[0429] (2) Evaluation of light-emitting elements Table 2 below shows the evaluation of the light-emitting elements of the examples and comparative examples. Table 2 shows the relative device lifetime (LT50), maximum external quantum yield (EQEmax), and fluorescence lifetime (τ) of the light-emitting elements of the examples and comparative examples.

[0430] The relative element lifespan is 900 cd / m² at half-life. 2 When continuously operated, the time it takes for the brightness to degrade from the initial brightness value to 50% is shown as the relative element lifetime, with the value of Comparative Example 9 set to 1.0. The voltage and current density of the organic electroluminescent element were measured using a source meter (Keithley Instrument, 2400 series), and the brightness and external quantum efficiency were measured using a Hamamatsu Photonics external quantum efficiency measuring instrument C9920-12. The fluorescence lifetime was measured using a Hamamatsu Photonics fluorescence lifetime measuring instrument.

[0431] [Table 2]

[0432] Referring to the results in Table 2, the light-emitting element of the example showed increased relative device lifetime characteristics and higher maximum external quantum yield (EQEmax) characteristics compared to the light-emitting element of the comparative example. Furthermore, the light-emitting element of the example showed shorter fluorescence lifetime characteristics compared to the light-emitting element of the comparative example. In other words, it can be confirmed that the light-emitting element of the example exhibits longer lifetime and higher efficiency characteristics compared to the light-emitting element of the comparative example.

[0433] In the case of the comparative compounds used in Comparative Examples 1 to 5, while they all have the same heteroboline core structure as the example compounds, the difference lies in the fact that some of the carbon atoms in the heteroboline core structure are converted to nitrogen, or that pyridyl groups are not substituted on the amine groups within the heteroboline structure. As a result, Comparative Examples 1 to 5 showed reduced device lifetime and luminous efficiency compared to the example.

[0434] The comparative compounds used in Comparative Examples 6 to 8 differ from the example compounds in that two additional di-oxaborane skeletons are condensed onto the heteroboline core structure. Comparative Examples 6 to 8 showed a significantly reduced device lifetime compared to the example. This reduced lifetime characteristic in the comparative examples is thought to be because the comparative compounds X-6 to X-8 used in Comparative Examples 6 to 8 had relatively larger acceptor characteristics compared to the example compounds, accelerating electron trapping in the comparative example devices.

[0435] Comparative Example 9 differs from the Example Compound in that it has a modified DABNA core structure that is different from the heteroboline core structure skeleton of the Example Compound. Due to the characteristics of Comparative Example Compound X-9, which has a different core structure, the light-emitting element of Comparative Example Compound 9 is thought to have a longer fluorescence lifetime and exhibit reduced lifetime characteristics.

[0436] The polycyclic compound of one embodiment has a boron-containing condensed ring core containing two boron atoms, a structure in which some of the carbon atoms in the condensed ring core skeleton are converted to nitrogen, or a structure in which a pyridyl group is substituted for the amine group forming the boron-containing condensed ring core skeleton. The polycyclic compound of one embodiment contains a condensed ring core structure containing nitrogen as a ring-forming atom, or contains an amine group substituted with a pyridyl group as a core skeleton, and may have a short fluorescence lifetime due to increased absorbance. As a result, the polycyclic compound of one embodiment may exhibit improved lifetime characteristics and excellent luminescence efficiency characteristics. Furthermore, the polycyclic compound of one embodiment can be used as a thermally activated delayed fluorescence material. The light-emitting element of one embodiment, which contains the polycyclic compound of one embodiment in the light-emitting layer, may exhibit excellent luminescence efficiency characteristics in the blue light emission region and long lifetime characteristics.

[0437] An electronic device including a light-emitting element containing the polycyclic compound of one embodiment may exhibit excellent reliability characteristics due to the long lifespan of the light-emitting element. Furthermore, an electronic device including an optical element containing the polycyclic compound of one embodiment with improved luminous efficiency may exhibit improved brightness characteristics and display quality.

[0438] Although preferred embodiments of the present invention have been described so far with reference, a person skilled in the art or a person with ordinary knowledge in the art will understand that the present invention can be modified and altered in various ways without departing from the spirit and art domain of the invention as described in the claims below.

[0439] Therefore, the technical scope of the present invention is not limited to what is described in the detailed description of the specification, but should be determined by the claims. [Explanation of Symbols]

[0440] EA:Electronic equipment DM, DM-TD, DM-a, DM-b, DM-c: Display Modules ED: Light-emitting element EL1: First electrode EL2: Second electrode EML: Light-emitting layer

Claims

1. First electrode and, A second electrode is placed on the first electrode, A light-emitting element comprising a light-emitting layer disposed between the first electrode and the second electrode and containing a first compound represented by the following chemical formula 1: [Chemical formula 1] In the aforementioned chemical formula 1, X １ ~X ４ These are each independently represented as O, S, Se, or by the chemical formula 2 below. Y １ Y １６ Each is independently CR ａ or N, R ａ These are a hydrogen atom, a deuterium atom, a cyano group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms: [Chemical formula 2] In the aforementioned chemical formula 2, Y １７ to Y ２１ are each independently CR ｂ or N, and R ｂ These are a hydrogen atom, a deuterium atom, a cyano group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms. X of the aforementioned chemical formula 1 １ ~X ４ If none of them can be represented by chemical formula 2, then Y of chemical formula 1 １ Y １６ At least one of them is N, X of the aforementioned chemical formula 1 １ ~X ４ If at least one of them is represented by chemical formula 2, then Y of chemical formula 1 １ Y １６ and Y of chemical formula 2 １７ Y ２１ At least one of them is N.

2. The light-emitting element according to claim 1 further comprises a second compound represented by the following chemical formula HT-1 and at least one third compound represented by the following chemical formula ET-1: [Chemical formula HT-1] In the aforementioned chemical formula HT-1, A １ Even A ８ Each is independently N or CR ５１ And, L １ This is a directly linked, substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms. Y ａ Direct bonding, CR ５２ R ５３ , or SiR ５４ R ５５ And, Ar １ This is a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms. R ５１ ~R ５５ Each of these groups is independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted thio group, a substituted or unsubstituted oxy group, a substituted or unsubstituted amine group, a substituted or unsubstituted boron group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 ring-forming carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 ring-forming carbon atoms, or is bonded to an adjacent group to form a ring: [Chemical formula ET-1] In the aforementioned chemical formula ET-1, X １ ~X ３ At least one of them is N and the rest are CR ５６ And, R ５６ This is a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 ring-forming carbon atoms. b1 to b3 are each independent integers between 0 and 10, Ar ２ ~Ar ４ Each of these is independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms. L ２ ~L ４ Each of these is independently a directly bonded, substituted, or unsubstituted arylene group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring-forming carbon atoms.

3. The light-emitting element according to claim 2 further comprises a fourth compound represented by the following chemical formula D-1: [Chemical formula D-1] In the aforementioned chemical formula D-1, Q １ ~Q ４ Each is independently either C or N, C1 to C4 are each independently substituted or unsubstituted hydrocarbon rings with 5 to 30 ring-forming carbon atoms, or substituted or unsubstituted heterocycles with 2 to 30 ring-forming carbon atoms. L １１ ~L １３ Each is independently and directly connected. A substituted or unsubstituted divalent alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted ring-forming arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heteroarylene group having 2 to 30 carbon atoms. b11 to b13 are each independently either 0 or 1. R ６１ ~R ６６ Each of these is independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted thio group, a substituted or unsubstituted oxy group, a substituted or unsubstituted amine group, a substituted or unsubstituted boron group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 ring-forming carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 ring-forming carbon atoms. d1 through d4 are each independent integers between 0 and 4, inclusive.

4. The light-emitting element according to claim 1, wherein the fluorescence lifetime is 3.0 μs or less.

5. The light-emitting element according to claim 1, wherein the light-emitting layer emits delayed fluorescence.

6. The light-emitting layer emits blue light as described in claim 1.

7. Y of the aforementioned chemical formula 1 １ Y ４ One of the following, Y ６ Y ８ One of the following, Y １３ Y １６ Any one of the following, and Y ５ One of the selected options is N, and the remaining ones are each independently CR ａ In the aforementioned polycyclic compound, X of the aforementioned chemical formula 1 １ ~X ４ Each of these independently represents OS, Se, or the light-emitting element according to claim 1, which is represented by the following chemical formula 2-1: [Chemical formula 2-1] In the aforementioned chemical formula 2-1, R ｂ１ ~R ｂ５ Each of these is independently a hydrogen atom, a deuterium atom, a cyano group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms.

8. Y of the aforementioned chemical formula 1 １ Y １６ Each is independently CR ａ In the aforementioned polycyclic compound, X of the aforementioned chemical formula 1 １ ~X ４ At least one of them is represented by the chemical formula 2, In the aforementioned chemical formula 2, Y １７ Y ２１ One of them is N, and the others are CR independently. ｂ The light-emitting element according to claim 1.

9. The light-emitting element according to claim 1, wherein at least one hydrogen atom of the first compound is substituted with a deuterium atom.

10. The first compound is represented by any one of the compounds in the following first group of compounds, according to claim 1: [First compound group] In the first group of compounds described above, D is a deuterium atom.

11. Polycyclic compounds represented by the following chemical formula 1: [Chemical formula 1] In the aforementioned chemical formula 1, X １ ~X ４ These are each independently represented as O, S, Se, or by the chemical formula 2 below. Y １ Y １６ Each is independently CR ａ or N, R ａ These are a hydrogen atom, a deuterium atom, a cyano group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms: [Chemical formula 2] In the aforementioned chemical formula 2, Y １７ Y ２１ Each is independently CR ｂ or N, R ｂ These are a hydrogen atom, a deuterium atom, a cyano group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms. X of the aforementioned chemical formula 1 １ ~X ４ If none of them can be represented by chemical formula 2, then Y of chemical formula 1 １ Y １６ At least one of them is N, X of the aforementioned chemical formula 1 １ ~X ４ If at least one of them is represented by chemical formula 2, then Y of chemical formula 1 １ Y １６ and Y of chemical formula 2 １７ Y ２１ At least one of them is N.

12. The aforementioned chemical formula 2 is represented by the following chemical formula 2-1, or by Y of chemical formula 2. １７ Y ２１ One of them is N, and the others are CR independently ｂ The polycyclic compound according to claim 11: [Chemical formula 2-1] In the aforementioned chemical formula 2-1, R ｂ１ to R ｂ５ is each independently a hydrogen atom, a deuterium atom, a cyano group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms.

13. Y of the chemical formula 1 １ to Y ４ Any one of, Y ６ to Y ８ Any one of, Y １３ to Y １６ Any one of, and Y ５ Any one selected from among is N, and the rest are each independently CR ａ and X of the aforementioned chemical formula 1 １ ~X ４ Each of these is independently OS, Se, or the polycyclic compound according to claim 11, represented by the following chemical formula 2-1: [Chemical formula 2-1] In the aforementioned chemical formula 2-1, R ｂ１ ~R ｂ５ Each of these is independently a hydrogen atom, a deuterium atom, a cyano group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms.

14. Y of the aforementioned chemical formula 1 １ Y １６ Each is independently CR ａ When X １ ~X ４ At least one of them is represented by the chemical formula 2, In the aforementioned chemical formula 2, Y １７ Y ２１ One of them is N, and the others are CR independently. ｂ The polycyclic compound according to claim 11.

15. The polycyclic compound according to claim 11, wherein at least one hydrogen atom of chemical formula 1 and chemical formula 2 is substituted with a deuterium atom.

16. The polycyclic compound according to claim 11, wherein the compound represented by the chemical formula 1 is a blue light-emitting dopant.

17. The polycyclic compound according to claim 11, wherein the compound represented by the chemical formula 1 is a thermally activated delayed fluorescence material.

18. The polycyclic compound according to claim 11, wherein the chemical formula 1 is represented by any one of the compounds in the following first group of compounds: [First compound group] In the first group of compounds described above, D is a deuterium atom.

19. Includes a display module containing multiple light-emitting elements, At least one of the plurality of light-emitting elements is An electronic device comprising a first electrode, a second electrode placed on the first electrode, and a light-emitting layer placed between the first electrode and the second electrode and containing a polycyclic compound represented by the following chemical formula 1: [Chemical formula 1] In the aforementioned chemical formula 1, X １ ~X ４ These are each independently represented as O, S, Se, or by the chemical formula 2 below. Y １ Y １６ Each is independently CR ａ or N, R ａ This includes hydrogen atoms, deuterium atoms, cyano groups, substituted or unsubstituted The group is an amine group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms: [Chemical formula 2] In the aforementioned chemical formula 2, Y １７ Y ２１ Each is independently CR ｂ or N, R ｂ These are a hydrogen atom, a deuterium atom, a cyano group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms. X of the aforementioned chemical formula 1 １ ~X ４ If none of them can be represented by chemical formula 2, then Y of chemical formula 1 １ Y １６ At least one of them is N, X of the aforementioned chemical formula 1 １ ~X ４ If at least one of them is represented by chemical formula 2, then Y of chemical formula 1 １ Y １６ and Y of chemical formula 2 １７ Y ２１ At least one of them is N.

20. The electronic device according to claim 19, further comprising at least one of a processor, memory, and power supply module.

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