Light emitting diode, compound for light emitting diode, and electronic device including light emitting diode

Abstract

The present disclosure provides a light emitting diode including: a first electrode; a second electrode opposed to the first electrode; and at least one functional layer between the first electrode and the second electrode and including a compound represented by Formula 1. In addition, a compound for a light emitting diode and an electronic device including a light emitting diode are also provided. Formula 1.

Description

[0001] Cross-reference to related applications

[0002] This application claims priority and benefit to Korean Patent Application No. 10-2024-0145811, filed on October 23, 2024, with the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference. Technical Field

[0003] One or more embodiments of this disclosure relate to light-emitting diodes, compounds for light-emitting diodes, and electronic devices including light-emitting diodes. Background Technology

[0004] For example, an organic light-emitting diode may have a structure in which a first electrode is disposed on a substrate, followed by a hole functional layer, a light-emitting layer, an electron functional layer, and a second electrode disposed in sequence.

[0005] Holes injected from the first electrode can be transported to the emissive layer through the hole transport layer, while electrons injected from the second electrode can be transported to the emissive layer through the electron transport layer. Charge carriers (e.g., holes and electrons) can recombine in the emissive layer to generate excitons in an excited state. The excitons can decay from the excited state to the ground state and emit light.

[0006] Currently, there is a persistent need to improve the light-emitting characteristics of light-emitting diodes (e.g., improved efficiency, operation, and / or lifetime). To meet these needs, significant efforts have been focused on hole injection layer materials used in hole transport regions (e.g., hole transport layers). Summary of the Invention

[0007] One or more aspects of embodiments of this disclosure relate to light-emitting diodes, electronic devices including light-emitting diodes, and compounds for light-emitting diodes. Further aspects will be set forth in part in the description which follows, and in part will be apparent from the description or may be learned by practice of the embodiments of this disclosure presented.

[0008] Those skilled in the art to which this disclosure pertains should clearly understand that aspects of this disclosure are not limited to this description, and that other undescribed technical purposes can be clearly understood and recognized from this description.

[0009] According to one or more embodiments of the present disclosure, a light-emitting diode may include: a first electrode; a second electrode opposite to the first electrode (e.g., facing the first electrode); and at least one functional layer between the first electrode and the second electrode (e.g., inserted between the first electrode and the second electrode), wherein the at least one functional layer comprises a compound represented by Formula 1:

[0010] Formula 1

[0011] .

[0012] According to one or more embodiments, in Formula 1, X may be O, S, Ga, In, Ge, Sn, Pb, Sb, Bi, Se, or Te, and R1 to R8 may each be independently selected from: hydrogen, deuterium, halogen, haloalkyl having 1 to 10 carbon atoms, hydroxyl, cyano, nitro, trifluoromethyl, amino, amidine, hydrazine, hydrazone, and alkoxy; or each unsubstituted or substituted with the following alkyl groups having 1 to 10 carbon atoms, having Alkenyl groups having 2 to 10 carbon atoms, alkynyl groups having 2 to 10 carbon atoms, aryl groups having 6 to 30 cyclic carbon atoms, heteroaryl groups having 2 to 30 cyclic carbon atoms, or any combination thereof: deuterium, halogen, haloalkyl groups having 1 to 10 carbon atoms, hydroxyl, cyano, nitro, trifluoromethyl, amino, amido, hydrazyl, hydrazone, alkoxy, or any combination thereof, and m and n may each be an integer between 0 and 2, including 0 and 2.

[0013] According to one or more embodiments, the compound represented by Formula 1 may be represented by Formula 1-1 or Formula 1-2:

[0014] Equation 1-1

[0015]

[0016] Formula 1-2

[0017] .

[0018] According to one or more embodiments, in Formulas 1-1 and 1-2, X can be selected from O, S, Ga, In, Ge, Sn, Pb, Sb, Bi, Se, and Te.

[0019] R1, R2 and R9 to R 24 Each of these can be independently: hydrogen; deuterium; halogen; haloalkyl having 1 to 10 carbon atoms; hydroxyl; cyano; nitro; trifluoromethyl; amino; amidin; hydrazine; hydrazone; alkoxy; or each of these unsubstituted or substituted alkyl having 1 to 10 carbon atoms, alkenyl having 2 to 10 carbon atoms, alkynyl having 2 to 10 carbon atoms, aryl having 6 to 30 cyclic carbon atoms, heteroaryl having 2 to 30 cyclic carbon atoms, or any combination thereof: deuterium, halogen, haloalkyl having 1 to 10 carbon atoms, hydroxyl, cyano, nitro, trifluoromethyl, amino, amidin, hydrazine, hydrazone, alkoxy, or any combination thereof (e.g., R1, R2, and R9 to R). 24Each may be independently selected from the group consisting of: hydrogen, deuterium, halogen, haloalkyl, hydroxyl, cyano, nitro, trifluoromethyl, amino, amidinyl, hydrazine, hydrazone, and alkoxy; or each of the following unsubstituted or substituted alkyl, alkenyl, alkynyl, acetyls, aryl, heteroaryl, or any combination thereof having 1 to 10 carbon atoms, cyano, nitro, trifluoromethyl, amino, amidinyl, hydrazine, hydrazone, alkoxy, or any combination thereof having 2 to 30 cyclic carbon atoms; and

[0020] m and n can each be an integer between 0 and 2, inclusive.

[0021] According to one or more implementation methods, R1, R2, R 19 R 20 R 21 and R 22 Each of these can be independently: a haloalkyl, hydroxyl, cyano, nitro, trifluoromethyl, amino, or alkoxy group having 1 to 10 carbon atoms; or an unsubstituted or substituted alkenyl group having 2 to 10 carbon atoms (e.g., R1, R2, R3) substituted with a haloalkyl, hydroxyl, cyano, nitro, trifluoromethyl, amino, alkoxy group, or any combination thereof having 1 to 10 carbon atoms. 19 R 20 R 21 and R 22 Each of these can be independently: a haloalkyl, hydroxyl, cyano, nitro, trifluoromethyl, amino, or alkoxy group having 1 to 10 carbon atoms; or an unsubstituted or substituted alkenyl group having 2 to 10 carbon atoms with a haloalkyl, hydroxyl, cyano, nitro, trifluoromethyl, amino, alkoxy group, or any combination thereof having 1 to 10 carbon atoms.

[0022] According to one or more implementations, X may be O or S.

[0023] According to one or more embodiments, the compound represented by Formula 1 may include at least one compound selected from Group 1 and / or at least one compound selected from Group 2:

[0024] Compound group 1

[0025] Compound group 2 .

[0026] According to one or more embodiments, a light-emitting diode may include at least one functional layer and a charge-generating layer. The at least one functional layer may include: a hole functional layer on a first electrode (e.g., disposed on the first electrode); and a light-emitting layer on the hole functional layer (e.g., disposed on the hole functional layer), and at least one of the hole functional layer, the light-emitting layer, and the charge-generating layer may include a compound represented by Formula 1.

[0027] According to one or more embodiments, the hole functional layer may include a hole injection layer and a hole transport layer, and at least one of the hole injection layer and the hole transport layer may include a compound represented by Formula 1.

[0028] According to one or more embodiments, the thickness of the hole injection layer can be from about 10 Å to about 500 Å.

[0029] According to one or more embodiments, the compound represented by Formula 1 may be a p-type (or similar) dopant.

[0030] According to one or more embodiments, based on 100 parts by weight of the total weight of the compounds constituting the hole functional layer or the charge generation layer, the amount of p-type (or similar) dopant may be from about 0.5 parts by weight to about 15 parts by weight. For example, based on 100 parts by weight of the total weight of the compounds constituting the hole functional layer, the amount of p-type (or similar) dopant may be from about 0.5 parts by weight to about 15 parts by weight. For example, based on 100 parts by weight of the total weight of the compounds constituting the charge generation layer, the amount of p-type (or similar) dopant may be from about 0.5 parts by weight to about 15 parts by weight.

[0031] According to one or more embodiments, the lowest unoccupied molecular orbital (LUMO) level of the p-type (or similar) dopant may be -4.8 eV or less.

[0032] According to one or more embodiments, the electron mobility of the p-type (or similar) dopant can be approximately 1.0 × 10⁻⁶. -5 cm 2 / (V·s) to approximately 1.0×10 -2 cm 2 / (V·s).

[0033] According to one or more embodiments, the hole mobility of the p-type (or similar) dopant can be 1.0 × 10⁻⁶. -6 cm 2 / (V·s) to approximately 1.0×10 -1 cm2 / (V·s).

[0034] According to one or more embodiments of the present disclosure, an electronic device may include a light-emitting diode (LED) provided by the present disclosure. The LED includes: a first electrode; a second electrode disposed on the first electrode (e.g., arranged on the first electrode); and at least one functional layer between the first and second electrodes (e.g., disposed between the first and second electrodes) and comprising a compound represented by Formula 1.

[0035] Formula 1

[0036]

[0037] According to one or more embodiments, in Formula 1, X can be O, S, Ga, In, Ge, Sn, Pb, Sb, Bi, Se, or Te.

[0038] R1 to R8 may be independently selected from: hydrogen, deuterium, halogen, haloalkyl having 1 to 10 carbon atoms, hydroxyl, cyano, nitro, trifluoromethyl, amino, amido, hydrazine, hydrazone, and alkoxy; or each of the following unsubstituted or substituted alkyl having 1 to 10 carbon atoms, alkenyl having 2 to 10 carbon atoms, alkynyl having 2 to 10 carbon atoms, aryl having 6 to 30 cyclic carbon atoms, heteroaryl having 2 to 30 cyclic carbon atoms, or any combination thereof: deuterium, halogen, haloalkyl having 1 to 10 carbon atoms, hydroxyl, cyano, nitro, trifluoromethyl, amino, amido, hydrazine, hydrazone, alkoxy, or any combination thereof (e.g., R1 to R8 may each be independently: hydrogen, deuterium, halogen, haloalkyl having 1 to 10 carbon atoms, hydroxyl, cyano, nitro, trifluoromethyl, amino, amidine, hydrazine, hydrazone, or alkoxy; or each unsubstituted or substituted with one to 10 carbon atoms of an alkyl, two to 10 carbon atoms of an alkenyl, two to 10 carbon atoms of an alkynyl, six to 30 cyclic carbon atoms of an aryl, two to 30 cyclic carbon atoms of a heteroaryl, or any combination thereof (deuterium, halogen, haloalkyl having 1 to 10 carbon atoms, hydroxyl, cyano, nitro, trifluoromethyl, amino, amidine, hydrazine, hydrazone, alkoxy, or any combination thereof), and

[0039] m and n can each be an integer between 0 and 2, inclusive.

[0040] According to one or more embodiments, the electronic device may be selected from at least one of the following: flat panel display, curved display, television, billboard, computer monitor, medical monitor, head-mounted display, indoor light, outdoor light, signal light, wearable device, foldable device, rollable device, bendable device, flexible device, curved device, electronic notebook, e-book, portable multimedia player, personal digital assistant, laser printer, telephone, cellular phone, tablet PC, portable terminal, laptop computer, digital camera, viewfinder, camcorder, 3D display, virtual reality display, augmented reality display, video wall including multiple displays tiled together, vehicle display device, outdoor display device, theater screen, stadium screen, and signboard. According to one or more embodiments, at least one of the color filter layer, light control layer, touch sensor layer, and polarization layer may be further included on a light-emitting diode.

[0041] According to one or more embodiments of this disclosure, a compound represented by Formula 1 can be provided:

[0042] Formula 1

[0043] ,

[0044] In Equation 1, X can be O, S, Ga, In, Ge, Sn, Pb, Sb, Bi, Se, or Te.

[0045] R1 to R8 may each be independently selected from: hydrogen, deuterium, halogen, haloalkyl having 1 to 10 carbon atoms, hydroxyl, cyano, nitro, trifluoromethyl, amino, amidine, hydrazine, hydrazone, and alkoxy; or may each be an unsubstituted or substituted alkyl having 1 to 10 carbon atoms, alkenyl having 2 to 10 carbon atoms, alkynyl having 2 to 10 carbon atoms, aryl having 6 to 30 cyclic carbon atoms, heteroaryl having 2 to 30 cyclic carbon atoms, or any combination thereof: deuterium, halogen, haloalkyl having 1 to 10 carbon atoms, hydroxyl, cyano, nitro, trifluoromethyl, amino, amidine, hydrazine, hydrazone, alkoxy, or any combination thereof.

[0046] m and n can each be an integer between 0 and 2, inclusive.

[0047] According to one or more embodiments, the compound represented by Formula 1 may be represented by Formula 1-1 or Formula 1-2:

[0048] Formula 1-1

[0049]

[0050] Formula 1-2

[0051] .

[0052] In Equations 1-1 and 1-2, X can be selected from O, S, Ga, In, Ge, Sn, Pb, Sb, Bi, Se, and Te.

[0053] R1, R2 and R9 to R 24 Each of the following can be independently selected from: hydrogen, deuterium, halogen, haloalkyl, hydroxyl, cyano, nitro, trifluoromethyl, amino, amidinyl, hydrazine, hydrazone, and alkoxy; or each of the following unsubstituted or substituted alkyl, alkenyl, alkynyl, acetylinyl, aryl, heteroaryl, or any combination thereof having 1 to 10 carbon atoms, cyano, nitro, trifluoromethyl, amino, amidinyl, hydrazine, hydrazone, alkoxy, or any combination thereof having 2 to 30 cyclic carbon atoms: deuterium, halogen, haloalkyl, hydroxyl, cyano, nitro, trifluoromethyl, amino, amidinyl, hydrazine, hydrazone, alkoxy, or any combination thereof having 1 to 10 carbon atoms.

[0054] m and n can each be an integer between 0 and 2, inclusive.

[0055] According to one or more implementation methods, R1, R2, R 19 R 20 R 21 and R 22 It may be independently selected from: haloalkyl, hydroxy, cyano, nitro, trifluoromethyl, amino, and alkoxy groups having 1 to 10 carbon atoms; or unsubstituted or substituted with haloalkyl, hydroxy, cyano, nitro, trifluoromethyl, amino, alkoxy, or any combination thereof having 1 to 10 carbon atoms, alkenyl groups having 2 to 10 carbon atoms.

[0056] According to one or more embodiments, the compound represented by Formula 1 may be at least one selected from the group of compounds 1 or at least one selected from the group of compounds 2:

[0057] Compound group 1

[0058] Compound group 2 .

[0059] A light-emitting diode according to one or more embodiments may include compounds according to one or more embodiments to reduce the driving voltage and improve the maximum quantum efficiency.

[0060] By including compounds comprising one or more embodiments, the compounds of one or more embodiments can help reduce the driving voltage of a light-emitting diode (LED) and improve the maximum quantum efficiency of the LED. Electronic devices can be manufactured using LEDs. However, the aspects of this disclosure are not limited thereto and various extensions can be made without departing from the spirit and scope of this disclosure. Attached Figure Description

[0061] The accompanying drawings are included to provide a further understanding of this disclosure, and are incorporated in and constitute a part of this disclosure. The drawings illustrate embodiments of the disclosure and, together with the description, serve to explain the principles of the disclosure. These and / or other features will become apparent and more readily understood from the following description of one or more embodiments, taken in conjunction with the accompanying drawings, wherein:

[0062] Figure 1 A plan view illustrating a display device according to one or more embodiments of the present disclosure;

[0063] Figure 2 For along Figure 1 A cross-sectional view taken from the I-I' line;

[0064] Figures 3 to 6 Each of the following is a cross-sectional view illustrating one or more embodiments of a light-emitting diode according to the present disclosure;

[0065] Figure 7 and Figure 8 Each of the above is a cross-sectional view illustrating a portion of a display device according to one or more embodiments of the present disclosure; and

[0066] Figure 9 and Figure 10 Figures illustrate electronic devices that utilize display devices according to one or more embodiments of the present disclosure. Detailed Implementation

[0067] Certain embodiments illustrated in the accompanying drawings will now be explained in more detail with reference to examples thereof, wherein the same reference numerals throughout this disclosure refer to the same elements, and for the sake of brevity, their repeated descriptions are omitted. The presented embodiments may have various forms and arrangements, but this disclosure should in no way be construed as limiting itself to the described embodiments. Rather, this disclosure should be construed as encompassing all forms, arrangements, equivalents, and alternatives covered by the technical concept and scope of this disclosure. Accordingly, by referring to the accompanying drawings, only one or more embodiments are described to explain the features of this disclosure and to convey the scope of this disclosure to those skilled in the art.

[0068] Unless otherwise specified, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this disclosure pertains. However, in the event of any inconsistency in meaning, the description (including limitations) of this disclosure shall prevail.

[0069] Terms such as “first” and “second” may be used to describe one or more suitable elements, but the elements should not be limited by the terms. Terms may be used only to distinguish one element from another. For example, without departing from the scope of this disclosure, a first element may be referred to as a second element, and vice versa. Any expression in the singular form may include the meaning of the plural form unless clearly used otherwise. For example, unless the context clearly indicates otherwise, the singular forms “a,” “an,” “one,” and “described” are intended to also include the plural forms. As used herein, the terms “and / or” or “or” should include a combination of or any one of the listed items. Furthermore, when describing embodiments of this disclosure, the use of “may” refers to “one or more embodiments of this disclosure.”

[0070] When a component is described as being "on" another component, "arranged on" another component, "placed on" another component, "connected to" another component, or "connected to" another component, it should be interpreted as not only being directly arranged on, placed on, connected to, or connected to another component, but also potentially having another component in between. In contrast, if (for example, when) a component is described as being "directly on" another component, "directly arranged on" another component, "placed on" another component, "directly connected to" another component, or "connected to" another component, it should be interpreted as no other component being arranged between that component and the other component.

[0071] Expressions such as “comprise(s) / comprising,” “include(s) / including,” or “has(have) / having” are intended to indicate characteristics, quantities, steps (e.g., actions or tasks), operations, elements, components, and / or one or more (e.g., any suitable) combinations thereof, and should not be construed as excluding any possibility of the presence or addition of one or more other characteristics, quantities, steps, operations, elements, components, and / or combinations thereof. Furthermore, the terms “comprise(s) / comprising,” “include(s) / including,” “has(have) / having,” or other similar terms include or support the terms “consisting of,” and “substantially consisting of,” indicating the presence of the described features, integers, steps, operations, elements, components, and / or groups thereof, while other features, integers, steps, operations, elements, components, and / or groups thereof are absent or substantially absent.

[0072] When a component is described as being arranged "on (or below)" or "above (or below)" an element, it should be interpreted as not only being arranged directly on (or below) that element, but also possibly having another element arranged between that component and that element.

[0073] Any reference to “and / or” should be interpreted as including one or more combinations that may be defined by the relevant element.

[0074] For convenience, the dimensions (e.g., thickness) of the various configurations illustrated in the accompanying drawings are shown as examples, and the embodiments of this disclosure are not limited thereto.

[0075] In one or more embodiments, as used herein, and Each can refer to a bonding site.

[0076] As used in this article, a direct link can refer to a chemical bond, such as a single bond.

[0077] Examples of halogens, as used herein, may include fluorine, chlorine, bromine, and iodine.

[0078] As used herein, "substituted or unsubstituted" groups can be unsubstituted groups or groups substituted with at least one substituent selected from the group consisting of: deuterium, halogen, nitro, amino, cyano, silyl, oxy, thio, sulfinyl, sulfonyl, carbonyl, boronyl, alkyl, alkenyl, alkynyl, phosphine sulfide, phosphine oxide, cycloalkyl, aryl, and heterocyclic groups. Additionally, the substituents presented above as examples can each be substituted or unsubstituted. For example, biphenyl can be interpreted as aryl or a phenyl group substituted with a phenyl group.

[0079] As used herein, integers selected from 0 to 3 refer to integers selected from 0, 1, 2, and 3; integers selected from 0 to 4 refer to integers selected from 0, 1, 2, 3, and 4; integers selected from 0 to 5 refer to integers selected from 0, 1, 2, 3, 4, and 5; integers selected from 0 to 7 refer to integers selected from 0, 1, 2, 3, 4, 5, 6, and 7; integers selected from 0 to 8 refer to integers selected from 0, 1, 2, 3, 4, 5, 6, 7, and 8; integers selected from 0 to 9 refer to integers selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, and 9; integers selected from 0 to 10 refer to integers selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, and 10; and integers selected from 0 to 2 refer to integers selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, and 20.

[0080] As used herein, the phrase "forming a ring by bonding with an adjacent group" can refer to the formation of a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocycle by bonding with an adjacent group. Hydrocarbon rings include aliphatic hydrocarbon rings and / or aromatic hydrocarbon rings. Heterocycles include aliphatic heterocycles and / or aromatic heterocycles. Hydrocarbon rings and heterocycles can each be monocyclic or polycyclic. Additionally, the formed ring can bond with another ring to form a spirostructure.

[0081] As used herein, the fluorene group may be substituted, and two substituents may combine to form a spirostructure with the fluorene group.

[0082] As used herein, the phrase “adjacent group” can refer to a substituent that is directly connected to an atom that is substituted by another substituent; a substituent that is connected to an atom that is substituted by another substituent; or a substituent that is spatially closest to another substituent. For example, the two methyl groups in 1,2-xylene can be interpreted as “adjacent groups” to each other.

[0083] As used herein, alkyl groups may have straight or branched chains. The number of carbon atoms in an alkyl group may be 1 to 30, 1 to 20, 1 to 10, or 1 to 6. Non-limiting examples may include methyl, ethyl, propyl (e.g., n-propyl, isopropyl), butyl (e.g., n-butyl, isobutyl, tert-butyl, sec-butyl), pentyl (e.g., n-pentyl, isopentyl, neopentyl, tert-pentyl, 1-methyl-butyl, 1-ethylpropyl), hexyl (e.g., n-hexyl, isohexyl, 1-methylpentyl, 2-methylpentyl, 3,3-dimethylbutyl, 2-ethylbutyl, 1-ethyl-butyl), heptyl (e.g., n-heptyl, 1-methylhexyl, 4-methylhexyl, 5-methylhexyl), octyl (e.g., n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl), and nonyl (n-nonyl, 2,2-dimethylheptyl).

[0084] As used herein, cycloalkyl can refer to a cyclic alkyl group. The number of carbon atoms in a cycloalkyl group can be 3 to 50, 3 to 30, 3 to 10, or 3 to 6. Non-limiting examples of cycloalkyl groups may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, norbornyl, 1-adamantyl, 2-adamantyl, isobornyl, and / or dicycloheptyl.

[0085] As used herein, alkenyl can refer to a hydrocarbon group comprising one or more carbon-carbon double bonds in the middle and / or at the end of an alkyl group having two or more carbon atoms. Alkenyl groups can be straight-chain or branched. The number of carbon atoms in an alkenyl group can be, but is not limited to, 2 to 30, 2 to 20, 2 to 10, or 2 to 6. Non-limiting examples of alkenyl groups may include 1-butenyl, 1-pentenyl, 1,3-butadienyl, and styryl.

[0086] As used herein, alkynyl can refer to a hydrocarbon group comprising one or more carbon-carbon triple bonds in the middle and / or at the end of an alkyl group having two or more carbon atoms. The alkynyl group can be straight-chain or branched. The number of carbon atoms in the alkynyl group can be, but is not limited to, 2 to 30, 2 to 20, 2 to 10, or 2 to 6. Non-limiting examples may include ethynyl and propynyl.

[0087] As used herein, a carbocyclic group refers to a monocyclic or polycyclic group having 3 to 60 cyclic carbon atoms, comprising only carbon as the cyclic atom. Carbocyclic groups having 3 to 60 carbon atoms may include aromatic carbocyclic groups and non-aromatic carbocyclic groups, such as non-aromatic hydrocarbon cyclic groups. Additionally, as used herein, a heterocyclic group is a cyclic group having 1 to 60 cyclic carbon atoms and further comprising heteroatoms other than carbon as cyclic atoms. Heteroatoms may include at least one of B, O, N, P, Si, S, and Se.

[0088] As used herein, the hydrocarbon cyclogroup may be any functional group or substituent derived from an aliphatic hydrocarbon ring or any functional group or substituent derived from an aromatic hydrocarbon ring. The hydrocarbon cyclogroup may be a saturated hydrocarbon cyclogroup having 5 to 30, 5 to 20, or 5 to 10 cyclic carbon atoms.

[0089] As used herein, aryl refers to a functional group or substituent derived from an aromatic hydrocarbon ring. Aryl can be monocyclic or polycyclic. Aryl can have 6 to 60, 6 to 30, 6 to 20, 6 to 15, or 6 to 9 cyclic carbon atoms. Non-limiting examples of aryl may include phenyl, fluorenyl, anthracene, naphthyl, terphenyl, biphenyl, hexaphenyl, triphenylene, and benzofluoranthracene.

[0090] As used herein, a heterocyclic group (i.e., heterocyclic group) may refer to any functional group or substituent derived from a ring comprising at least one of B, O, N, P, Si, S, and Se as a cyclic heteroatom. Heterocyclic groups may include aliphatic heterocyclic groups and / or aromatic heterocyclic groups. Aromatic heterocyclic groups may be heteroaryl. Aliphatic and aromatic heterocycles may each be monocyclic or polycyclic.

[0091] As used herein, if (e.g., when) a heterocyclic group comprises two or more heteroatoms, the two or more heteroatoms may be the same or different. The heterocyclic group may be a monocyclic or polycyclic heterocyclic group and is interpreted to include the concept of a heteroaryl group. The heterocyclic group may have 1 to 30, 1 to 20, 1 to 10, or 1 to 6 cyclic carbon atoms.

[0092] As used herein, aliphatic heterocyclic groups may include at least one of B, O, N, P, Si, S, and Se as cyclic heteroatoms. Aliphatic heterocyclic groups may have 1 to 30, 1 to 20, 1 to 10, or 1 to 6 cyclic carbon atoms. Non-limiting examples of aliphatic heterocyclic groups may include thiopropylcycloyl, pyrrolyl, piperidinyl, tetrahydrofuranyl, and 1,4-dioxyl.

[0093] As used herein, "heteroaryl" refers to an aromatic group in the heterocyclic group. A heteroaryl group may include at least one of B, O, N, P, Si, S, and Se as a cyclic atom. When a heteroaryl group includes two or more heteroatoms, the two or more heteroatoms may be the same or different. A heteroaryl group may be a monocyclic or polycyclic heterocycle. A heteroaryl group may have 2 to 60, 2 to 30, 2 to 20, 2 to 10, or 2 to 6 cyclic carbon atoms. Non-limiting examples may include furanyl, pyrroloyl, imidazolyl, pyridinyl, pyrimidinyl, triazine, pyridazinyl, quinolinyl, isoquinolinyl, pyridopyrimidinyl, benzocarbazolyl, benzofuranyl, and oxazolyl.

[0094] As used herein, the above description of aryl can be applied to arylene groups, except that arylene is a divalent group. The above description of heteroaryl can be applied to heteroarylene groups, except that heteroarylene is a divalent group. The above descriptions of aryl and heteroaryl can be applied to polyvalent aryl and polyvalent heteroaryl groups, respectively, except that polyvalent aryl and polyvalent heteroaryl are polyvalent groups. However, although not limited to the examples, a polyvalent group may refer to a trivalent or tetravalent group, or the description of a trivalent or tetravalent group may be used.

[0095] As used herein, silane may include alkylsilane and / or arylsilane. The alkyl group in an alkylsilane may be straight-chain, branched, or cyclic. The number of carbon atoms in an alkylsilane is not particularly limited, but may be, for example, 1 to 20, 1 to 10, or 1 to 6. The number of carbon atoms in an arylsilane is not particularly limited, but may be, for example, 6 to 30, 6 to 20, 6 to 15, or 6 to 9. Non-limiting examples of silane may include trimethylsilane, triethylsilane, tert-butyldimethylsilane, vinyldimethylsilane, propyldimethylsilane, triphenylsilane, diphenylsilane, and phenylsilane.

[0096] In the specification, the number of carbon atoms in the carbonyl group is not particularly limited, but may be 1 to 40, 1 to 30, 1 to 20, or 1 to 10. For example, the carbonyl group may have the following structure, but one or more embodiments of this disclosure are not limited thereto.

[0097]

[0098] As used herein, a thio group may include an alkylthio group and / or an arylthio group. A thio group may indicate a group in which a sulfur atom is bonded to an alkyl or aryl group as defined above. The alkyl group in an alkylthio group may be straight-chain, branched, or cyclic. The number of carbon atoms in an alkylthio group is not particularly limited, but may be, for example, 1 to 20, 1 to 10, or 1 to 6. The number of carbon atoms in an arylthio group is not particularly limited, but may be, for example, 6 to 30, 6 to 20, 6 to 15, or 6 to 9. Non-limiting examples of thio groups may include methylthio, ethylthio, propanethio, pentylthio, hexylthio, octylthio, dodecylthio, cyclopentylthio, cyclohexylthio, phenylthio, and naphthio.

[0099] As used herein, an oxygen group may indicate a group in which an oxygen atom is bonded to an alkyl or aryl group as defined above. An oxygen group may include alkoxy and / or aryloxy groups. Alkoxy groups may be straight-chain, branched, or cyclic. The number of carbon atoms in an alkoxy group is not particularly limited, but may be, for example, 1 to 20, 1 to 10, or 1 to 6. The number of carbon atoms in an aryloxy group is not particularly limited, but may be, for example, 6 to 30, 6 to 20, 6 to 15, or 6 to 9. Non-limiting examples of oxygen groups may include methoxy, ethoxy, n-propoxy, isopropoxy, butoxy, pentoxy, hexoxy, octoxy, nonoxy, decoxy, and benzyloxy.

[0100] As used herein, boryl group may refer to a group in which a boron atom is bonded to an alkyl or aryl group as defined above. Boryl group may include alkylboryl and / or arylboryl. The alkyl group in an alkylboryl group may be straight-chain, branched, or cyclic. The number of carbon atoms in an alkylboryl group is not particularly limited, but may be, for example, 1 to 20, 1 to 10, or 1 to 6. The number of carbon atoms in an arylboryl group is not particularly limited, but may be, for example, 6 to 30, 6 to 20, 6 to 15, or 6 to 9. Non-limiting examples of boryl group may include dimethylboryl, diethylboryl, tert-butylmethylboryl, diphenylboryl, and phenylboryl.

[0101] As used herein, the number of carbon atoms in the amino group is not particularly limited, but may be from 1 to 30. The amino group may include alkylamino and / or arylamino. The alkyl group in the alkylamino group may be straight-chain, branched, or cyclic. The number of carbon atoms in the alkylamino group is not particularly limited, but may be, for example, 1 to 30, 1 to 20, 1 to 10, or 1 to 6. The number of carbon atoms in the arylamino group is not particularly limited, but may be, for example, 6 to 30, 6 to 20, 6 to 15, or 6 to 9. Non-limiting examples of amino groups may include methylamino, dimethylamino, phenylamino, diphenylamino, naphthylamino, 9-methyl-anthraylamino, and triphenylamino.

[0102] As used herein, sulfinyl group may mean the above-defined alkyl or aryl group bonded to -S (=O)-. The number of carbon atoms in the sulfinyl group is not particularly limited, but may be 1 to 30, 1 to 20, 1 to 10, or 1 to 6. The sulfinyl group may include alkylsulfinyl groups and arylsulfinyl groups. For example, the sulfinyl group may have the following structures, but is not limited thereto.

[0103]

[0104] As used herein, sulfonyl group may mean the above-defined alkyl or aryl group bonded to -S(=O)2-. The number of carbon atoms in the sulfonyl group is not particularly limited, but may be 1 to 30, 1 to 20, 1 to 10, or 1 to 6. The sulfonyl group may include alkylsulfonyl groups and arylsulfonyl groups. For example, the sulfonyl group may have the following structures, but is not limited thereto.

[0105]

[0106] As used herein, phosphine oxide may mean an alkyl or aryl group defined above and bonded to -P (=O)-. The number of carbon atoms in the phosphine oxide group is not particularly limited, but may be 1 to 30, 1 to 20, 1 to 10, or 1 to 6. The phosphine oxide group may include alkylphosphine oxides and arylphosphine oxides. For example, the phosphine oxide group may have the following structures, but is not limited thereto.

[0107]

[0108] As used herein, phosphine sulfide may refer to the above-defined alkyl or aryl group bonded to -P (=S)-. The number of carbon atoms in the phosphine sulfide is not particularly limited, but may be 1 to 30, 1 to 20, 1 to 10, or 1 to 6. Phosphine sulfide may include alkylphosphine sulfide and arylphosphine sulfide. For example, phosphine sulfide may have the following structures, but is not limited thereto.

[0109]

[0110] Hereinafter, certain exemplary embodiments of the present disclosure will be described in more detail with reference to the accompanying drawings.

[0111] Figure 1 To illustrate a plan view of a display device according to one or more embodiments of the present disclosure, and Figure 2 For one or more embodiments of this disclosure along Figure 1 A cross-sectional view of the display device taken by the I-I' line.

[0112] In one or more embodiments of this disclosure, first to third directions DR1, DR2, and DR3 may be defined. The first direction DR1 and the second direction DR2 may be in... Figure 1 The display device 1000 shown is defined on a plane and the directions intersect each other in the same direction. The third direction DR3 can be in... Figure 2 The direction of the thickness of the display device 1000 shown is, for example, a direction perpendicular to the plane defined by the first direction DR1 and the second direction DR2.

[0113] The display device 1000 may include a substrate BS, a circuit layer CL, and a display element layer EDL.

[0114] The circuit layer CL and the display element layer EDL can be arranged on the substrate BS.

[0115] The substrate BS may comprise glass, ceramic, metal, or the polymer resin polyimide. However, embodiments of this disclosure are not limited thereto, and the substrate BS may be an inorganic layer, an organic layer, or a composite material layer, and may consist of a single layer or multiple layers. A circuit layer CL may be disposed on the substrate BS and includes multiple wires and multiple transistors. In one or more embodiments, the circuit layer CL may include pixel transistors configured to drive light-emitting diodes ED1, ED2, and ED3 of the display element layer EDL.

[0116] The circuit layer CL may include peripheral transistors disposed in the peripheral region NA and configured to output signals to control the pixel transistors. The display element layer EDL may include the pixel defining layer PDL, light-emitting diodes ED1, ED2 and ED3, and the encapsulation layer TFE.

[0117] The pixel-defining layer (PDL) may include at least one organic insulating material selected from the group consisting of polyimide resins, polyamide resins, acrylic resins, benzocyclobutene resins, and phenolic resins.

[0118] Light-emitting diodes ED1, ED2 and ED3 may each include a first electrode EL1, a hole functional layer HFL, a light-emitting layer EML1, EML2 or EML3, an electron functional layer EFL and a second electrode EL2.

[0119] The hole functional layer HFL can be configured to facilitate the movement of holes from the first electrode EL1 to the light-emitting layers EML1, EML2 and EML3, and the electron functional layer EFL can be configured to facilitate the movement of electrons from the second electrode EL2 to the light-emitting layers EML1, EML2 and EML3. Figure 2 The present invention describes a hole functional layer (HFL) disposed between the first electrode EL1 and the light-emitting layers EML1, EML2, and EML3, and an electron functional layer (EFL) disposed between the second electrode EL2 and the light-emitting layers EML1, EML2, and EML3. However, embodiments of the present disclosure are not limited thereto, and the positions of the hole functional layer (HFL) and the electron functional layer (EFL) can be interchanged depending on whether each of the first electrode EL1 and the second electrode EL2 is positively or negatively charged.

[0120] Figure 2 One or more embodiments are described, wherein the light-emitting layers EML1, EML2, and EML3 of each of the light-emitting diodes ED1, ED2, and ED3 are disposed in the opening portions OH defined in the pixel defining layer PDL, and the hole functional layer HFL, the electron functional layer EFL, and the second electrode EL2 are each provided as a common layer throughout the light-emitting diodes ED1, ED2, and ED3. However, the embodiments of this disclosure are not limited to those described above. Figure 2 As explained in the text, for example, in relation to Figure 2 In one or more of the different embodiments illustrated herein, at least one of the hole functional layer HFL and the electronic functional layer EFL may be provided to be patterned via an opening portion OH defined in the pixel-defining layer PDL.

[0121] In one or more embodiments, at least some of the light-emitting diodes ED1, ED2, and ED3 may be configured to emit light in different wavelength ranges. For example, in one or more embodiments, the first light-emitting diode ED1 may be configured to emit red light, the second light-emitting diode ED2 may be configured to emit green light, and the third light-emitting diode ED3 may be configured to emit blue light. However, embodiments of this disclosure are not limited to this configuration; for example, the first to third light-emitting diodes ED1, ED2, and ED3 may be configured to emit light in substantially the same wavelength range, such as blue light.

[0122] The structure of each of the light-emitting diodes ED1, ED2 and ED3 and the materials of the layers constituting each of the light-emitting diodes ED1, ED2 and ED3 will be described in more detail below with reference to one or more suitable embodiments.

[0123] The encapsulation layer TFE can be configured to seal the light-emitting diodes ED1, ED2, and ED3 to protect them from moisture, oxygen, and / or foreign matter. In one or more embodiments, the encapsulation layer TFE can be a single layer. In one or more embodiments, the encapsulation layer TFE can be a multilayer comprising an encapsulating organic film and an encapsulating inorganic film.

[0124] The encapsulating organic film may include one or more selected from acrylic compounds and / or epoxy compounds. In one or more embodiments, the encapsulating organic film may include, but is not limited to, one or more photopolymerizable organic materials.

[0125] The encapsulating inorganic film may include, but is not limited to, silicon nitrides, silicon oxynitrides, silicon oxides, titanium oxides, and / or aluminum oxides.

[0126] refer to Figure 1 and Figure 2 The display device 1000 may include a display area DA and a peripheral area NA surrounding the display area DA. The display area DA may be configured to display an image, and the peripheral area NA may be configured not to display an image. In some embodiments, the peripheral area NA may not be provided.

[0127] Pixel regions PA1, PA2, and PA3, and the non-pixel region NPA, can be defined within the display region DA. Since light-emitting diodes ED1, ED2, and ED3 can be arranged to correspond to pixel regions PA1, PA2, and PA3 respectively, pixel regions PA1, PA2, and PA3 can be configured as regions for displaying emitted light. The non-pixel region NPA can be a region defined between pixel regions PA1, PA2, and PA3 and corresponding to the pixel definition layer PDL.

[0128] Despite Figure 1 and Figure 2 The text describes pixel regions PA1, PA2, and PA3 as having the same area, but the embodiments of this disclosure are not limited to these. Figure 1 and Figure 2 As illustrated herein, for example, in one or more embodiments, a portion of pixel regions PA1, PA2, and PA3 may have a different area than another portion.

[0129] In one or more embodiments, the display device 1000 may further include an optical layer disposed on the display element layer (EDL). The optical layer may be configured to reduce reflected light from external light. The optical layer may include, but is not limited to, a color filter layer, a light control layer, a touch sensor layer, or a light polarization layer.

[0130] In one or more embodiments, the display device 1000 may further include a touch sensor layer disposed on the display element layer EDL. The touch sensor layer may be configured to determine the coordinates of a touch at the location where a touch occurs. The touch sensor layer may be disposed between the display element layer EDL and the optical layer.

[0131] Figures 3 to 6 Each of the above is a cross-sectional view illustrating one or more embodiments of a light-emitting diode according to this disclosure. Figure 3 The light-emitting diode (ED) according to one or more embodiments of the present disclosure may include a first electrode EL1, a hole functional layer HFL, a light-emitting layer EML, an electron functional layer EFL, and a second electrode EL2 stacked sequentially (e.g., in the order described).

[0132] exist Figure 4 In the light-emitting diode (ED) according to one or more embodiments of the present disclosure, the hole functional layer HFL may include a hole injection layer HIL and a hole transport layer HTL, and the electronic functional layer EFL may include an electron transport layer ETL and an electron injection layer EIL.

[0133] exist Figure 5 In the light-emitting diode (ED) according to one or more embodiments of the present disclosure, the hole functional layer HFL may include a hole injection layer HIL, a hole transport layer HTL, and an electron blocking layer EBL, and the electron functional layer EFL may include a hole blocking layer HBL, an electron transport layer ETL, and an electron injection layer EIL.

[0134] exist Figure 6 In one or more embodiments of this disclosure shown in the figure, with Figure 4 Compared to the structure in the previous one, the light-emitting diode ED may further include a capping layer CPL disposed on the second electrode EL2.

[0135] The first electrode EL1 may be conductive (e.g., a conductor). The first electrode EL1 may comprise a metallic material, a metallic alloy, or a conductive compound. The first electrode EL1 may be an anode or a cathode.

[0136] The first electrode EL1 can be a reflective electrode, a semi-transparent electrode, or a transmissive electrode. For example, if the first electrode EL1 is a transmissive electrode, it can include materials such as indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), or indium tin zinc oxide (ITZO). If the first electrode EL1 is a semi-transparent electrode or a reflective electrode, it can include silver (Ag), magnesium (Mg), copper (Cu), aluminum (Al), platinum (Pt), palladium (Pd), gold (Au), nickel (Ni), neodymium (Nd), iridium (Ir), chromium (Cr), lithium (Li), calcium (Ca), lithium fluoride (LiF), molybdenum (Mo), titanium (Ti), tungsten (W), and / or combinations thereof and / or mixtures thereof (e.g., any suitable ones) (e.g., a mixture of Ag and Mg), or materials having a multilayer structure, such as a stacked structure of LiF and Ca (LiF / Ca) or a stacked structure of LiF and Al (LiF / Al). In one or more embodiments, the first electrode EL1 may have a multilayer structure, comprising: a reflective or semi-transparent film including one or more of the aforementioned materials, and a transparent conductive film including, for example, indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), and / or indium tin zinc oxide (ITZO). For example, in one or more embodiments, the first electrode EL1 may have a multilayer structure with an ITO / Ag / ITO three-layer structure or an ITO / Al / ITO three-layer structure, but embodiments of this disclosure are not limited to this configuration. A hole functional layer HFL may be provided on the first electrode EL1. The hole functional layer HFL may include at least one of a hole injection layer HIL, a hole transport layer HTL, a buffer layer, a light-emitting auxiliary layer, and an electron blocking layer EBL.

[0137] Hole functional layer (HFL) may have a monolayer structure comprising a single layer (e.g., composed of a single layer) comprising a single material; a monolayer structure comprising a single layer (e.g., composed of a single layer) comprising multiple different materials; or a multilayer structure comprising multiple layers (e.g., composed of multiple layers) comprising multiple different materials.

[0138] For example, in one or more embodiments, the hole functional layer HFL may have a structure in which a hole injection layer HIL / hole transport layer HTL, a hole injection layer HIL / hole transport layer HTL / buffer layer, a hole injection layer HIL / buffer layer, a hole transport layer HIL / buffer layer, or a hole injection layer HIL / hole transport layer HTL / electron blocking layer EBL are stacked sequentially (e.g., in the order described) from a first electrode EL1. However, embodiments of this disclosure are not limited thereto. The hole functional layer HFL may be fabricated using one or more suitable methods (e.g., vacuum deposition, spin coating, Langmuir-Brokett (LB) process, inkjet printing, casting, laser printing, and / or laser-induced thermal imaging (LITI)). In one or more embodiments, the hole functional layer HFL may comprise a compound represented by formula H-1, a compound represented by formula H-2, and / or a combination thereof (e.g., any suitable combination):

[0139] Formula H-1

[0140]

[0141] H-2

[0142] .

[0143] In formulas H-1 and H-2, L1 to L5 can be independently directly linked, substituted or unsubstituted aryl groups having 6 to 30 cyclic carbon atoms, or substituted or unsubstituted heteroaryl groups having 2 to 30 cyclic carbon atoms.

[0144] na1 to na4 can be independent integers between 0 and 5, inclusive.

[0145] In formulas H-1 and H-2, R1 to R4 may independently be hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 10 cyclic carbon atoms, substituted or unsubstituted heterocyclic alkyl having 1 to 10 cyclic carbon atoms, substituted or unsubstituted cycloalkenyl having 3 to 10 cyclic carbon atoms, substituted or unsubstituted heterocyclic alkenyl having 1 to 10 cyclic carbon atoms, substituted or unsubstituted aryl having 6 to 60 cyclic carbon atoms, substituted or unsubstituted aryloxy having 6 to 60 carbon atoms, substituted or unsubstituted arylthio having 6 to 60 carbon atoms, or substituted or unsubstituted heteroaryl having 1 to 60 cyclic carbon atoms.

[0146] For example, in one or more embodiments, R1 to R4 may be, independently, but not limited to, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirodifluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, phenanthryl, fluorenyl, triphenylene, pyrene, perylene, penfenyl, thiophene, furanyl, carbazole, indolyl, isoindolyl, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzocarbazole, dibenzocarbazole, dibenzothiophene, or pyridyl.

[0147] In one or more embodiments, R1 and R2 may optionally be bonded to each other via single bonds, and / or R3 and R4 may optionally be bonded to each other via single bonds.

[0148] In one or more embodiments of this disclosure, the compounds represented by formula H-1 and formula H-2 may be carbazole compounds comprising a substituted or unsubstituted carbazole group in at least one of R1 to R4, or fluorene compounds comprising a substituted or unsubstituted fluorene group in at least one of R1 to R4.

[0149] Compounds represented by any one of formulas H-1 and H-2 may be represented as compound HT3 or compound HT40 in the embodiments of manufacturing light-emitting diodes of this disclosure, however, the embodiments of this disclosure are not limited thereto.

[0150] In one or more embodiments, the hole functional layer (HFL) may include at least one of the following: 4,4',4''-tris{N-(2-naphthyl)-N-phenylamino}triphenylamine (2-TNATA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), 4,4',4''-[tris(3-methylphenyl)phenylamino]triphenylamine (m-MTDATA), 4,4',4''-tris(N,N-diphenylamino)triphenylamine (TDATA), phthalocyanine compounds (e.g., copper phthalocyanine), N,N'- Diphenyl-N,N'-bis-[4-(phenyl-m-tolyl-amino)-phenyl]-biphenyl-4,4'-diamine (DNTPD), polyaniline / dodecylbenzenesulfonic acid (PANI / DBSA), N,N'-bis(naphthyl-1-yl)-N,N'-diphenyl-benzidine (NPB), triphenylamine-containing polyether ketone (TPAPEK), 4-isopropyl-4'-methyldiphenyliodonium [tetra(pentafluorophenyl)borate] and dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarboxylonitrile (HAT-CN).

[0151] In one or more embodiments, the hole functional layer (HFL) may include one or more of the following: carbazole derivatives (e.g., polyvinylcarbazole and / or N-phenylcarbazole), fluorene derivatives, and triphenylamine derivatives (e.g., 4,4',4''-tris(N-carbazolyl)triphenylamine (TCTA), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (TPD), N,N'-bis(naphthyl-1-yl)-N,N'-diphenyl-biphenylamine (NPB), 4,4'-cyclohexylbis[N,N-bis(4-methylphenyl)aniline] (TAPC), 4,4'-bis[N,N'-(3-tolyl)amino]-3,3'-dimethylbiphenyl (HMTPD) and / or 1,3-bis(N-carbazolyl)phenyl (mCP)).

[0152] In one or more embodiments, the hole functional layer (HFL) may include 1,3-bis(1,8-dimethyl-9H-carbazole-9-yl)benzene (mDCP), 9-(4-tert-butylphenyl)-3,6-bis(triphenylsilyl)-9H-carbazole (CzSi) or 9-phenyl-9H-3,9'-bicarbazole (CCP).

[0153] The hole functional layer (HFL) may have a thickness of about 50 Å to about 10,000 Å, for example, about 100 Å to about 5,000 Å. If (for example, when) the hole functional layer (HFL) comprises a hole injection layer (HIL), a hole transport layer (HTL), or any combination thereof, the hole injection layer (HIL) may have a thickness of about 10 Å to about 9,000 Å, for example, about 100 Å to about 1,000 Å, and the hole transport layer (HTL) may have a thickness of about 50 Å to about 2,000 Å, for example, about 100 Å to about 1,500 Å. When the thicknesses of the hole functional layer (HFL), the hole injection layer (HIL), and the hole transport layer (HTL) satisfy their respective ranges described above, a satisfactory level of hole transport characteristics can be obtained without significantly increasing the driving voltage.

[0154] In one or more embodiments, in addition to one or more of the materials described above, the hole functional layer HFL may further include a charge-generating material to increase conductivity. The charge-generating material may be uniformly (e.g., substantially uniformly) or non-uniformly dispersed in the hole functional layer HFL.

[0155] As described above, in one or more embodiments, in addition to the hole injection layer HIL and the hole transport layer HTL, the hole functional layer HFL may include at least one of a buffer layer and an electron blocking layer EBL. The buffer layer may be configured to compensate for the optical resonant distance according to the wavelength of light emitted from the light-emitting layer EML to increase luminous efficiency. Materials that may be included in the hole functional layer HFL may be used as materials included in the buffer layer.

[0156] The electron blocking layer EBL can be configured to prevent or reduce the injection of electrons from the electron functional layer EFL to the hole functional layer HFL.

[0157] The light-emitting auxiliary layer is configured to compensate for the optical resonant distance according to the wavelength of light emitted from the light-emitting layer EML, thereby increasing luminous efficiency, and the electron-blocking layer EBL is configured to prevent or reduce electron leakage from the light-emitting layer EML to the hole-functional layer HFL. Materials that may be included in the described hole-functional layer HFL may be included in both the light-emitting auxiliary layer and the electron-blocking layer EBL.

[0158] According to one or more embodiments, a light-emitting diode (ED) may include one or more compounds represented by Formula 1:

[0159] Formula 1

[0160] .

[0161] According to one or more embodiments, in Formula 1, X can be O, S, Ga, In, Ge, Sn, Pb, Sb, Bi, Se, or Te, and

[0162] R1 to R8 may each be independently selected from: hydrogen, deuterium, halogen, haloalkyl having 1 to 10 carbon atoms, hydroxyl, cyano, nitro, trifluoromethyl, amino, amido, hydrazine, hydrazone, and alkoxy; or each unsubstituted or substituted with the following: alkyl having 1 to 10 carbon atoms, alkenyl having 2 to 10 carbon atoms, alkynyl having 2 to 10 carbon atoms, aryl having 6 to 30 cyclic carbon atoms, heteroaryl having 2 to 30 cyclic carbon atoms, or any combination thereof: deuterium, halogen, haloalkyl having 1 to 10 carbon atoms, hydroxyl, cyano, nitro, trifluoromethyl, amino, amido, hydrazine, hydrazone, alkoxy, or any combination thereof (e.g., R1 to R8 may each be independently:

[0163] Hydrogen, deuterium, halogen, haloalkyl, hydroxyl, cyano, nitro, trifluoromethyl, amino, amidine, hydrazine, hydrazone, or alkoxy groups having 1 to 10 carbon atoms; or

[0164] Each of the following unsubstituted or substituted groups (alkyl groups having 1 to 10 carbon atoms, alkenyl groups having 2 to 10 carbon atoms, alkynyl groups having 2 to 10 carbon atoms, aryl groups having 6 to 30 cyclic carbon atoms, heteroaryl groups having 2 to 30 cyclic carbon atoms, or any combination thereof) includes: deuterium, halogen, haloalkyl groups having 1 to 10 carbon atoms, hydroxyl, cyano, nitro, trifluoromethyl, amino, amidine, hydrazine, hydrazone, alkoxy, or any combination thereof.

[0165] m and n can each be an integer between 0 and 2, inclusive.

[0166] According to one or more embodiments, the compound represented by Formula 1 may be represented by Formula 1-1 or Formula 1-2:

[0167] Equation 1-1

[0168]

[0169] Formula 1-2

[0170] .

[0171] According to one or more embodiments, in Formulas 1-1 and 1-2, X can be selected from O, S, Ga, In, Ge, Sn, Pb, Sb, Bi, Se, and Te.

[0172] R1, R2 and R9 to R 24 Each of these can be independently: hydrogen, deuterium, halogen, haloalkyl, hydroxyl, cyano, nitro, trifluoromethyl, amino, amido, hydrazine, hydrazone, or alkoxy; or each of these can be unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkynyl group having 2 to 10 carbon atoms, an aryl group having 6 to 30 cyclic carbon atoms, a heteroaryl group having 2 to 30 cyclic carbon atoms, or any combination thereof: deuterium, halogen, haloalkyl, hydroxyl, cyano, nitro, trifluoromethyl, amino, amido, hydrazine, hydrazone, alkoxy, or any combination thereof (e.g., as shown in the following two paragraphs:

[0173] Hydrogen, deuterium, halogen, haloalkyl, hydroxyl, cyano, nitro, trifluoromethyl, amino, amidine, hydrazine, hydrazone, or alkoxy groups having 1 to 10 carbon atoms; or

[0174] Each of the following unsubstituted or substituted groups (alkyl groups having 1 to 10 carbon atoms, alkenyl groups having 2 to 10 carbon atoms, alkynyl groups having 2 to 10 carbon atoms, aryl groups having 6 to 30 cyclic carbon atoms, heteroaryl groups having 2 to 30 cyclic carbon atoms, or any combination thereof) includes: deuterium, halogen, haloalkyl groups having 1 to 10 carbon atoms, hydroxyl, cyano, nitro, trifluoromethyl, amino, amidine, hydrazine, hydrazone, alkoxy, or any combination thereof.

[0175] m and n can each be an integer between 0 and 2, inclusive.

[0176] According to one or more implementation methods, R1, R2, R 19 R 20 R 21 and R 22Each can be independently: a haloalkyl, hydroxyl, cyano, nitro, trifluoromethyl, amino, or alkoxy group having 1 to 10 carbon atoms; or an alkenyl group having 2 to 10 carbon atoms that is unsubstituted or substituted with a haloalkyl, hydroxyl, cyano, nitro, trifluoromethyl, amino, alkoxy group, or any combination thereof having 1 to 10 carbon atoms.

[0177] For example, R1, R2, R 19 R 20 R 21 and R 22 Each can be independently:

[0178] Halogenated alkyl, hydroxyl, cyano, nitro, trifluoromethyl, amino, or alkoxy groups having 1 to 10 carbon atoms; or

[0179] An alkenyl group having 2 to 10 carbon atoms, either unsubstituted or substituted with a haloalkyl, hydroxyl, cyano, nitro, trifluoromethyl, amino, alkoxy, or any combination thereof having 1 to 10 carbon atoms.

[0180] According to one or more embodiments, X may be O or S. According to one or more embodiments, the compound represented by Formula 1 may include at least one compound selected from Group 1 and / or at least one compound selected from Group 2:

[0181] Compound group 1

[0182] Compound group 2 .

[0183] According to one or more embodiments, a light-emitting diode (ED) may include at least one functional layer and a charge-generating layer CGL. The at least one functional layer may include a hole functional layer HFL disposed on a first electrode EL1 and a light-emitting layer EML disposed on the hole functional layer HFL. At least one of the hole functional layer HFL, the light-emitting layer EML, and the charge-generating layer CGL may include a compound represented by Formula 1.

[0184] According to one or more embodiments, the hole functional layer HFL may include a hole injection layer HIL and a hole transport layer HTL, and at least one of the hole injection layer HIL and the hole transport layer HTL may include a compound represented by Formula 1.

[0185] According to one or more embodiments, the compound represented by Formula 1 may be a p-type dopant. A p-type dopant is a material added to control the electrical characteristics of a light-emitting diode (ED), and the p-type dopant uses generated holes to carry charge. Accordingly, the layer including the p-type dopant may have increased conductivity. Although not limited thereto, a compound represented by Formula 1 may be included as a p-type dopant and charge-generating material to increase the conductivity of the hole functional layer HFL (e.g., hole injection layer HIL) and charge-generating layer CGL of this disclosure. Additionally, the p-type dopant may be uniformly (e.g., substantially uniformly) or non-uniformly dispersed in the hole functional layer HFL or charge-generating layer CGL. In addition to the p-type dopant, the hole functional layer HFL or charge-generating layer CGL of this disclosure may further include a compound represented by Formula H-1 or Formula H-2.

[0186] The compound represented by formula H-1 or formula H-2 may be selected from compound H3, compound H40 or any combination thereof, but is not limited to compound H3, compound H40 or any combination thereof.

[0187] According to one or more embodiments, based on 100 parts by weight of the total compound constituting the hole functional layer or charge generation layer, the amount of p-type (or similar) dopant may be from about 0.5 parts by weight to about 15 parts by weight (e.g., from about 1 part by weight to about 12 parts by weight, from about 2 parts by weight to about 10 parts by weight, from about 3 parts by weight to about 9 parts by weight, or from about 4 parts by weight to about 8 parts by weight). For example, based on 100 parts by weight of the total compound constituting the hole functional layer, the amount of p-type (or similar) dopant may be from about 0.5 parts by weight to about 15 parts by weight (e.g., from about 1 part by weight to about 12 parts by weight, from about 2 parts by weight to about 10 parts by weight, from about 3 parts by weight to about 9 parts by weight, or from about 4 parts by weight to about 8 parts by weight). For example, based on 100 parts by weight of the total compound constituting the charge generation layer, the amount of p-type (or similar) dopant may be from about 0.5 parts by weight to about 15 parts by weight (e.g., from about 1 part by weight to about 12 parts by weight, from about 2 parts by weight to about 10 parts by weight, from about 3 parts by weight to about 9 parts by weight, or from about 4 parts by weight to about 8 parts by weight). P-type dopant-doped hole transport materials can be used as hole injection layer materials suitable for anodes and configured to facilitate hole injection in materials with more negative highest occupied molecular orbital (HOMO) energy levels. When the doping amount of the p-type dopant is less than 0.5 parts by weight based on 100 parts by weight of the total weight of the compounds constituting the hole functional layer or charge generation layer, the p-type dopant will not improve conductivity. However, when the doping amount of the p-type dopant is greater than 15 parts by weight based on 100 parts by weight of the total weight of the compounds constituting the hole functional layer or charge generation layer, the p-type dopant will have a weak conductivity improvement effect.

[0188] According to one or more embodiments, the lowest unoccupied molecular orbital (LUMO) level of the p-type (or similar) dopant may be -4.8 eV or less.

[0189] According to one or more embodiments, the electron mobility of a p-type (or similar) dopant can be approximately 1.0 × 10⁻⁶. -5 cm 2 / (V·s) to approximately 1.0×10 -2 cm 2 / (V·s). The light-emitting diode disclosed herein can be configured to balance hole mobility and electron mobility to adjust the light-emitting area and reduce the reduction in lifetime.

[0190] According to one or more embodiments, the hole mobility of the p-type (or similar) dopant can be approximately 1.0 × 10⁻⁶. -6 cm 2 / (V·s) to approximately 1.0×10 -1 cm 2 / (V·s).

[0191] An emissive layer (EML) can be provided on the hole functional layer (HFL). The EML can have: a monolayer structure having a single layer comprising a single material (e.g., composed of a single material); a monolayer structure having a single layer comprising multiple different materials (e.g., composed of multiple different materials); or a multilayer structure having multiple layers comprising multiple different materials (e.g., composed of multiple different materials). In one or more embodiments, the EML can include a compound represented by formula HTH-1. In embodiments, the compound represented by formula HTH-1 can be used as a hole transport host material in the EML.

[0192] HTH-1

[0193]

[0194] In one or more embodiments, in formula HTH-1, A1 to A8 may each be N or CR1 independently. For example, in one or more embodiments, all of A1 to A8 (e.g., each of A1 to A8) may be CR1. In one or more embodiments, at least one selected from A1 to A8 may be N, and the rest may be CR1.

[0195] In one or more embodiments, in formula HTH-1, Y a It can be directly connected, O, S, CR2R3, SiR4R5, NR6, or BR7. For example, it can refer to two 6-membered rings (e.g., two benzene rings) connected to the nitrogen atom of formula HTH-1 via direct connection, , , or Connection. In equation HTH-1, if (for example, when) Y a When directly connected, the compound represented by formula HTH-1 may include a carbazole moiety.

[0196] In one or more embodiments, in formula HTH-1, L1 may be a directly linked, substituted or unsubstituted arylene group with 6 to 50 cyclic carbon atoms, or a substituted or unsubstituted heteroarylene group with 2 to 50 cyclic carbon atoms. For example, in one or more embodiments, L1 may be a directly linked, substituted or unsubstituted phenylene, a substituted or unsubstituted divalent carbazole, or a substituted or unsubstituted divalent biphenyl, but the embodiments of this disclosure are not limited thereto.

[0197] In one or more embodiments, in formula HTH-1, Ar1 may be a substituted or unsubstituted aryl group with 6 to 30 cyclic carbon atoms or a substituted or unsubstituted heteroaryl group with 2 to 30 cyclic carbon atoms. For example, in one or more embodiments, Ar1 may be a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted carbazolyl, a substituted or unsubstituted dibenzothiophene, or a substituted or unsubstituted dibenzofuranyl, but the embodiments of this disclosure are not limited thereto.

[0198] In one or more embodiments, in formula HTH-1, R1 to R7 may each independently be hydrogen, deuterium, halogen, cyano, substituted or unsubstituted silyl, substituted or unsubstituted thio, substituted or unsubstituted oxy, substituted or unsubstituted amino, substituted or unsubstituted boron, substituted or unsubstituted alkyl of 1 to 20 carbon atoms, substituted or unsubstituted alkenyl of 2 to 20 carbon atoms, substituted or unsubstituted aryl of 6 to 50 cyclic carbon atoms, or substituted or unsubstituted heteroaryl of 2 to 50 cyclic carbon atoms. In one or more embodiments, one or more selected from R1 to R7 may bond to adjacent groups to form a ring. For example, in one or more embodiments, R1 to R7 may each independently be hydrogen, deuterium, unsubstituted methyl, or unsubstituted phenyl.

[0199] In one or more embodiments, the emissive layer EML may further include a compound represented by formula ETH-1. For example, the compound represented by formula ETH-1 may be used as an electron transport host material in the emissive layer EML.

[0200] Formula ETH-1

[0201] .

[0202] In one or more embodiments, in formula ETH-1, X1 can be N or CR9, and X2 can be N or CR9. 10 X3 can be N or CR 11 And at least one selected from X1 to X3 can be N, and R9 to R 11 Each of them can be independently deuterium, hydrogen, halogen, hydroxyl, cyano, nitro, substituted or unsubstituted alkyl with 1 to 20 carbon atoms, substituted or unsubstituted alkenyl with 2 to 20 carbon atoms, substituted or unsubstituted alkoxy with 1 to 20 carbon atoms, substituted or unsubstituted alkynyl with 2 to 20 carbon atoms, substituted or unsubstituted aryl with 6 to 50 cyclic carbon atoms, or substituted or unsubstituted heteroaryl with 2 to 50 cyclic carbon atoms.

[0203] In one or more embodiments, in formula ETH-1, L2 to L4 may each be independently a directly linked, substituted or unsubstituted aryl group of 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 cyclic carbon atoms. If (for example, when) a1 to a3 may each be an integer of 2 or greater, L2 to L4 may each be independently a substituted or unsubstituted aryl group of 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 cyclic carbon atoms.

[0204] In one or more embodiments, in Equation ETH-1, a1 to a3 can each be an integer between 0 and 10, including 0 and 10.

[0205] In one or more embodiments, in formula ETH-1, Ar2 to Ar4 may each independently be deuterium, hydrogen, a substituted or unsubstituted alkyl group with 1 to 20 carbon atoms, a substituted or unsubstituted aryl group with 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group with 2 to 30 cyclic carbon atoms. For example, in one or more embodiments, Ar2 to Ar4 may be a substituted or unsubstituted phenyl group or a substituted or unsubstituted carbazole group.

[0206] In one or more embodiments, the compound represented by formula ETH-1, which is used as the electron transport host material in the light-emitting layer EML, may be represented as compound H126 in the compounds shown in the embodiments of manufacturing light-emitting diodes of this disclosure, but the embodiments of this disclosure are not limited thereto.

[0207] In one or more embodiments, the light-emitting layer (EML) in the light-emitting diode (ED) of one or more embodiments may include at least one selected from anthracene derivatives, fluoranthene derivatives, 1,2-benzophenanthrene derivatives, pyrene derivatives, dihydrobenzoanthracene derivatives, and triphenylene derivatives. For example, in one or more embodiments, the light-emitting layer (EML) may include anthracene derivatives and / or pyrene derivatives.

[0208] In one or more embodiments, the compound represented by formula EM-1 can be used as a fluorescent host material.

[0209] EM-1

[0210]

[0211] In one or more embodiments, in formula EM-1, L may be a directly linked, substituted or unsubstituted aryl group with 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group with 2 to 30 cyclic carbon atoms. Examples may be phenylene, biphenylene, terphenylene, naphthylene, phenanthylene, pyrene, spirofluorene, fluorene, dibenzofuranyl, dibenzothiopheneyl, or carbazoyl, but the embodiments of this disclosure are not limited thereto.

[0212] In one or more embodiments, in formula EM-1, R5 to R 14 Each of them may be independently hydrogen, deuterium, halogen, substituted or unsubstituted oxy group, substituted or unsubstituted thio group, substituted or unsubstituted silyl group, substituted or unsubstituted alkyl group with 1 to 30 carbon atoms, substituted or unsubstituted alkenyl group with 2 to 30 carbon atoms, substituted or unsubstituted aryl group with 6 to 30 cyclic carbon atoms, or substituted or unsubstituted heteroaryl group with 2 to 30 cyclic carbon atoms, and / or bonded to adjacent groups to form a ring.

[0213] In one or more embodiments, in formula EM-1, a can be an integer between 0 and 5, including 0 and 5.

[0214] In one or more embodiments, the compound represented by formula EM-1 may be any compound of formula E1 to E11 (e.g., any compound selected from formula E1 to E11), but the embodiments of this disclosure are not limited thereto.

[0215]

[0216] In one or more embodiments, the luminescent layer EML may further comprise a compound represented by formula EM-2 or formula EM-3. It may further comprise a compound represented by any of formulas selected from EM-2 and EM-3 as a phosphorescent host material.

[0217] EM-2

[0218]

[0219] EM-3

[0220]

[0221] In one or more embodiments, in Formula EM-2 and Formula EM-3, rings A1 to A4 may each be independently an aryl group with 6 to 30 cyclic carbon atoms, either substituted or unsubstituted, or a heteroaryl group with 2 to 30 cyclic carbon atoms. Non-limiting examples may include phenyl, naphthyl, phenanthryl, fluoranyl, triphenylene, pyrene, pyridyl, pyrimidinyl, indene, fluorenyl, spirodifluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, indolyl, carbazole, benzo[a]carbazole, dibenzo[a]carbazole, furanyl, benzo[a]furanyl, dibenzofuranyl, benzo[a]naphthofuranyl, benzo[a]thiophene, dibenzo[a]thiophene, benzo[a]naphtho[a]thiophene, and dinaphtho[a]thiophene.

[0222] In one or more embodiments, in formulas EM-2 and EM-3, nd1 to nd3 can each be independently 0, 1, or 2, and X1 can be 0, 5, or NL. 12 -R 50 CR 51 R 52 or SiR 53 R 54 In Equations EM-2 and EM-3, L9 to L 12 Each can be an arylene group with 6 to 30 cyclic carbon atoms that are directly connected, substituted or unsubstituted, or a heteroarylene group with 2 to 30 cyclic carbon atoms that are substituted or unsubstituted.

[0223] In one or more embodiments, in formulas EM-2 and EM-3, R 43 To R 49 and R 50 To R 54 Each of them can be independently hydrogen, deuterium, halogen, substituted or unsubstituted amino group, substituted or unsubstituted thio group, substituted or unsubstituted oxy group, substituted or unsubstituted alkyl group with 1 to 20 carbon atoms, substituted or unsubstituted alkenyl group with 2 to 20 carbon atoms, substituted or unsubstituted aryl group with 6 to 30 cyclic carbon atoms, or substituted or unsubstituted heteroaryl group with 2 to 30 cyclic carbon atoms.

[0224] In one or more embodiments, the phosphorescent host material represented by formula EM-2 or EM-3 and included in the emissive layer EML may be represented, but is not limited to, compound H125 among the compounds shown in embodiments of manufacturing light-emitting diodes of this disclosure. In one or more embodiments, the emissive layer EML may further include materials that are generally suitable as host materials in the art.

[0225] In one or more embodiments, for example, the light-emitting layer EML may include at least one of the following as a host material: bis(4-(9H-carbazole-9-yl)phenyl)diphenylsilane (BCPDS), (4-(1-(4-(diphenylamino)phenyl)cyclohexyl)phenyl)diphenylphosphine oxide (POPCPA), bis[2-(diphenylphosphino)phenyl]ether oxide (DPEPO), 4,4'-bis(N-carbazole)-1,1'-biphenyl (CBP), 1,3-bis(N-carbazole)benzene (mCP), 2,8-bis(diphenylphosphino)dibenzo[b,d]furan (PPF), 4,4',4''-tris(N-carbazole)triphenylamine (TCTA), and 1,3,5-tris(1-phenyl-1H-benzo[d]imidazol-2-yl)benzene (TPBi). However, embodiments of this disclosure are not limited thereto, and for example, host materials such as tris(8-hydroxyquinoline)aluminum (Alq3), 9,10-bis(naphthyl-2-yl)anthracene (ADN), 2-tert-butyl-9,10-bis(naphthyl-2-yl)anthracene (TBADN), stilbene aromatics (DSA), 4,4'-bis(9-carbazolyl)-2,2'-dimethylbiphenyl (CDBP), 2-methyl-9,10-bis(naphthyl-2-yl)anthracene (MADN), hexaphenylcyclotriphosphazene (CP1), 1,4-bis(triphenylsilyl)benzene (UGH2), hexaphenylcyclotrisiloxane (DPSiO3), and / or octaphenylcyclotetrasiloxane (DPSiO4) may be used.

[0226] In one or more embodiments, the light-emitting layer EML may include a compound represented by the formula Ma.

[0227] Compounds represented by the formula Ma can be used as phosphorescent dopant materials.

[0228] Formula Ma

[0229] M(L a ) nb1 (L b ) nb2

[0230] Formula Mb

[0231]

[0232] In one or more embodiments, in formula Ma, M may be a transition metal (e.g., iridium (Ir), platinum (Pt), gold (Au), titanium (Ti), hafnium (Hf), tantalum (Ta), tungsten (W), rhenium (Re), or osmium (Os)), and L a It can be a ligand represented by the formula Mb.

[0233] In one or more embodiments, nb1 can be 1, 2, or 3, and when nb1 is 2 or greater, two or more L a They can be the same as or different from each other, and L b It can be, but is not limited to, organic ligands, such as halogen ligands (e.g., Cl and F), diketone ligands (e.g., acetylacetonate, 1,3-diphenyl-1,3-malonate, 2,2,6,6-tetramethyl-3,5-heptanedioneate and / or hexafluoroacetate) and / or carboxylic acid ligands (e.g., pyridinecarboxylate, dimethyl-3-pyridinecarboxylate and / or benzoate), etc.

[0234] In one or more embodiments, nb2 can be 0, 1, 2, 3, or 4, and when b2 is 2 or greater, two or more L b They can be the same or different from each other. T1 can be a direct connection, *-O-*, *-S-*, *-N(Q1)-*, *-C(=O)-*, *-C(Q1)=C(Q2)-*, *-C(Q1)=*, *-C(Q1)(Q2)-* or *=C(Q1)-*.

[0235] In one or more embodiments, X a and X b Each can be independently C or N, and X c and X d They can each be independently chemically linked (e.g., coordinate or covalent bonds), O, S, N(Q3), B(Q3), P(Q3), C(Q3)(Q4), or Si(Q3)(Q4). Cy1 and Cy2 can each be independently selected from substituted or unsubstituted carbon rings of 3 to 60 cyclic carbon atoms and substituted or unsubstituted heterocycles of 1 to 60 cyclic carbon atoms.

[0236] In one or more embodiments, R a and R b Each of them can be independently hydrogen, deuterium, halogen, hydroxyl, cyano, substituted or unsubstituted silyl, substituted or unsubstituted thio, substituted or unsubstituted oxy, substituted or unsubstituted amino, substituted or unsubstituted boron, substituted or unsubstituted alkyl with 1 to 20 carbon atoms, substituted or substituted alkenyl with 2 to 20 carbon atoms, substituted or unsubstituted aryl with 6 to 60 cyclic carbon atoms, or substituted or unsubstituted heteroaryl with 2 to 60 cyclic carbon atoms.

[0237] In one or more embodiments, Q1 to Q4 may each independently be hydrogen, deuterium, halogen, hydroxyl, cyano, nitro, substituted or unsubstituted alkyl with 1 to 30 carbon atoms, substituted or unsubstituted alkenyl with 2 to 30 carbon atoms, substituted or unsubstituted alkoxy with 1 to 30 carbon atoms, substituted or unsubstituted aryl with 6 to 60 cyclic carbon atoms, or substituted or unsubstituted heteroaryl with 2 to 60 cyclic carbon atoms.

[0238] In one or more embodiments, nb3 and nb4 may each be an integer between 0 and 10, including 0 and 10.

[0239] In one or more embodiments, in formulas Ma and Mb, if (for example, when) nb1 is 2 or greater, two or more L a The two Cy1 rings may optionally be linked to each other via T2 as a linking group, and / or the two Cy2 rings may optionally be linked to each other via T3 as a linking group. T2 and T3 may each be the same as those described with reference to T1.

[0240] In one or more embodiments, in formula Mb, * and *' may each be a bonding site with M of formula Ma. A compound represented by formula Ma may be represented as compound D1 in the compounds shown in the embodiments of manufacturing light-emitting diodes of this disclosure, but the embodiments of this disclosure are not limited thereto.

[0241] In one or more embodiments, the luminescent layer (EML) may include a compound represented by the formula Fa. The compound represented by Fa may be a fluorescent dopant material or a delayed fluorescence material.

[0242] Formula Fa

[0243]

[0244] In one or more embodiments, in formula Fa, rings A to C may each be independently an aromatic hydrocarbon ring of 6 to 60 cyclic carbon atoms, substituted or unsubstituted, or an aromatic heterocycle of 2 to 60 cyclic carbon atoms.

[0245] In one or more embodiments, in formula Fa, Y a and Y b Each can be independently selected from O, S, Se, and CR. 58 R 59 NR 60 and SiR 61 R 62 .

[0246] In one or more embodiments, in formula Fa, X1 may be any one selected from B, P, and P=O, and in one or more embodiments, in formula Fa, X1 may be B.

[0247] In one or more embodiments, in formula Fa, R 55 To R 62 They may be the same or different, and each may independently be selected from any of the following: hydrogen, deuterium, substituted or unsubstituted alkyl of 1 to 30 carbon atoms, substituted or unsubstituted aryl of 6 to 60 cyclic carbon atoms, substituted or unsubstituted cycloalkyl of 3 to 30 cyclic carbon atoms, substituted or unsubstituted heteroaryl of 2 to 60 cyclic carbon atoms, substituted or unsubstituted alkoxy of 1 to 30 carbon atoms, substituted or unsubstituted aryloxy of 6 to 30 carbon atoms, substituted or unsubstituted arylthio of 6 to 30 carbon atoms, substituted or unsubstituted arylamino of 5 to 30 carbon atoms, substituted or unsubstituted alkylsilyl of 1 to 30 carbon atoms, substituted or unsubstituted arylsilyl of 5 to 30 carbon atoms, nitro, cyano, and halogen.

[0248] In one or more embodiments, in formula Fa, a55 to a57 may be independently integers between 0 and 20, including 0 and 20.

[0249] In one or more embodiments, the light-emitting layer EML may further comprise one or more of the following as dopant materials: perylene and its derivatives (e.g., 2,5,8,11-tetra-tert-butylperylene (TBP)), pyrene and its derivatives (e.g., 1,1'-dipyrene, 1,4-dipyrenebenzene, and 1,4-bis(N,N-diphenylamino)pyrene) and / or styryl derivatives (e.g., 1,4-bis[2-(3-N-ethylcarbazolyl)vinyl) Benzene (BCzVB), 4-(di-p-tolylamino)-4'-[(di-p-tolylamino)styryl]stilbene (DPAVB), N-(4-((E)-2-(6-((E)-4-(diphenylamino)styryl)naphth-2-yl)vinyl)phenyl)-N-phenylaniline (N-BDAVBi) and 4'-bis[2-(4-(N,N-diphenylamino)phenyl)vinyl]biphenyl (DPAVBi)), etc.

[0250] In one or more embodiments, the emissive layer EML may further comprise a suitable phosphorescent dopant material. For example, metal composites comprising iridium (Ir), platinum (Pt), osmium (Os), gold (Au), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), or thulium (Tm) may be used. For example, bis(4,6-difluorophenylpyridinyl-N,C2')pyridinecarboxyiridium(III) (FIrpic), bis(2,4-difluorophenylpyridinyl)tetra(1-pyrazolyl)boronate(III) (FIr6), or octaethylporphyrin platinum (PtOEP) may be used as phosphorescent dopant. However, embodiments of this disclosure are not limited thereto. In one or more embodiments, the emissive layer EML may comprise a quantum dot (EL-QD) material.

[0251] In one or more embodiments, a quantum dot may refer to a crystal of a semiconductor compound and may emit light of a specific color based on the size of the crystal. Accordingly, a quantum dot may emit light of one or more suitable colors, such as blue, red, or green light.

[0252] In one or more embodiments, the diameter of the quantum dot may be, for example, in the range of 1 nanometer (nm) to 10 nm.

[0253] In this disclosure, when the quantum dots or quantum dot particles are spherical, "diameter" refers to the particle size or average particle size, and when the particles are non-spherical, "diameter" refers to the major axis length or average major axis length. The particle diameter can be measured using a scanning electron microscope or a particle size analyzer. As a particle size analyzer, for example, the HORIBA LA-950 laser particle size analyzer can be used. When the particle size is measured using a particle size analyzer, the average particle size is referred to as D. 50 D 50 It refers to the average diameter of 50% of the particles in a particle size distribution (e.g., cumulative distribution), and refers to the value corresponding to 50% of the particle size from the smallest particle in a distribution curve that accumulates in order from the smallest to the largest particle size when the total number of particles is 100%.

[0254] In addition, quantum dots can be spherical nanoparticles, cone-shaped nanoparticles, multi-armed nanoparticles, cubic nanoparticles, nanotubes, nanowires, nanofibers and / or nanoplates, etc.

[0255] In one or more embodiments, the quantum dots may be selected from group III-VI compounds, group II-VI compounds, group III-V compounds, group I-III-VI compounds, group IV-VI compounds, group IV elements, group IV compounds and / or combinations thereof (e.g., any suitable combination).

[0256] In one or more embodiments, Figures 3 to 6 In one or more embodiments of the light-emitting diode (ED) illustrated herein, an electronic functional layer (EFL) may be provided on the light-emitting layer (EML).

[0257] In one or more embodiments, the electronic functional layer (EFL) may include at least one of the hole blocking layer (HBL), the electron transport layer (ETL), and the electron injection layer (EIL), but the embodiments of this disclosure are not limited to those illustrated in the drawings.

[0258] In one or more embodiments, the electronic functional layer (EFL) may have: a single-layer structure having a single layer comprising a single material (e.g., composed of a single material), a single-layer structure having a single layer comprising a variety of different materials (e.g., composed of a variety of different materials), or a multilayer structure having multiple layers comprising a variety of different materials (e.g., composed of a variety of different materials).

[0259] In one or more embodiments, for example, the electronic functional layer (EFL) may have a monolayer structure of an electron injection layer (EIL) or an electron transport layer (ETL), or a monolayer structure comprising an electron injection material and an electron transport material (e.g., composed of an electron injection material and an electron transport material). In one or more embodiments, the electronic functional layer (EFL) may have a monolayer structure comprising a variety of different materials (e.g., composed of a variety of different materials), or a structure of an electron transport layer (ETL) / electron injection layer (EIL) or a hole blocking layer (HBL) / electron transport layer (ETL) / electron injection layer (EIL), wherein the constituent layers are stacked sequentially from the light-emitting layer (EML), but the embodiments disclosed herein are not limited thereto. The thickness of the electronic functional layer (EFL) may be, for example, from about 1000 Å to about 1500 Å.

[0260] In one or more embodiments, electronic functional layers (EFLs) can be fabricated using methods selected from vacuum deposition, spin coating, Langmuir-Brookett (LB) process, casting, inkjet printing, laser printing, and / or laser-induced thermal imaging (LITI).

[0261] In one or more embodiments, the electronic functional layer (EFL) may include a compound represented by formula ET-1.

[0262] ET-1

[0263]

[0264] In one or more embodiments, in formula ET-1, Ar1 to Ar3 may each be independently hydrogen, deuterium, a substituted or unsubstituted alkyl group with 1 to 20 carbon atoms, a substituted or unsubstituted aryl group with 6 to 60 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group with 2 to 60 cyclic carbon atoms. Examples include phenyl, naphthyl, biphenyl, phenanthryl, fluorenyl, spirofluorenyl, terphenyl, pyridyl, carbazole, and isoquinolinyl, but the embodiments of this disclosure are not limited thereto.

[0265] In one or more embodiments, in formula ET-1, at least one of X2, X3, and X4 is N, and the remainder is CR. c .

[0266] In one or more embodiments, in formula ET-1, R c It may be hydrogen, deuterium, halogen, substituted or unsubstituted alkyl with 1 to 20 carbon atoms, substituted or unsubstituted aryl with 6 to 30 cyclic carbon atoms, or substituted or unsubstituted heteroaryl with 2 to 30 cyclic carbon atoms.

[0267] In one or more embodiments, in formula ET-1, ne1 to ne3 can each be an integer between 0 and 5, inclusive. In formula ET-1, L 12 To L 14 Each can be an arylene group with 6 to 30 cyclic carbon atoms that are directly connected, substituted or unsubstituted, or a heteroarylene group with 2 to 30 cyclic carbon atoms that are substituted or unsubstituted.

[0268] In one or more embodiments, the compound represented by formula ET-1 in the electronic functional layer EFL may be represented as compound ET37 or compound ET46 in the embodiments of manufacturing light-emitting diodes of this disclosure, but the embodiments of this disclosure are not limited thereto.

[0269] In one or more embodiments, the electronic functional layer (EFL) may include anthracene compounds. However, embodiments of this disclosure are not limited thereto, and the EFL may include, for example, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), tris(8-hydroxyquinoline)aluminum (Alq3), bis(2-methyl-8-hydroxyquinoline-N1,O8)-(1,1'-biphenyl-4-hydroxy)aluminum (BAlq), 1,3,5-tris[(3-pyridyl)-phenyl-3-yl]benzene, 2,4,6-tris(3'-(pyridyl-3-yl)biphenyl-3-yl)-1,3,5-triazine, 2-(4-(N- Phenylenolbenzimidazol-1-yl)phenyl)-9,10-dinaphthylanthracene, 1,3,5-tris(1-phenyl-1H-benzimidazol-2-yl)phenyl (TPBi), 4,7-diphenyl-1,10-phenanthroline (Bphen), 3-(biphenyl-4-yl)-4-phenyl-5-tert-butylphenyl-1,2,4-triazole (TAZ), 4-(naphthyl-1-yl)-3,5-diphenyl-4H-1,2,4-triazole (NTAZ), 2-(biphenyl-4-yl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole ( t Bu-PBD), bis(benzoquinoline-10-hydroxy)beryllium (Bebq2), 9,10-bis(naphth-2-yl)anthracene (ADN), 1,3-bis[3,5-bis(pyridin-3-yl)phenyl]benzene (BmPyPhB) or any combination thereof.

[0270] In one or more embodiments, the electronic functional layer (EFL) (e.g., the electron transport layer (ETL) in the electronic functional layer (EFL) may be represented as, but is not limited to, compound ET46 in the embodiments of manufacturing light-emitting diodes shown in this disclosure.

[0271] In one or more embodiments, in addition to one or more of the aforementioned materials, the electronic functional layer (EFL) (e.g., the electron transport layer (ETL) in the electronic functional layer EFL) may include a metallic material.

[0272] In one or more embodiments, for example, the metal-containing material may include a Li complex. The Li complex may include, for example, compounds ET-D1 (Liq) or ET-D2:

[0273] .

[0274] In one or more embodiments, the electronic functional layer EFL may include an electron injection layer EIL configured to allow easy injection of electrons from the second electrode EL2. The electron injection layer EIL may be in direct contact with the second electrode EL2.

[0275] The electronic functional layer (EFL) (e.g., the electron injection layer (EIL)) may have: a single-layer structure having a single layer comprising a single material (e.g., composed of a single material), a single-layer structure having a single layer comprising a variety of different materials (e.g., composed of a variety of different materials), or a multilayer structure comprising multiple layers comprising a variety of different materials (e.g., composed of a variety of different materials).

[0276] The electronic functional layer (EFL) (e.g., the electron injection layer (EIL)) may include alkaline earth metals, rare earth metals, alkali metals, alkaline earth metal compounds, rare earth metal compounds, alkali metal compounds, alkaline earth metal complexes, rare earth metal complexes, alkali metal complexes, or any combination thereof, or further include organic materials (e.g., compounds represented by formula EM-2 or formula EM-3).

[0277] Alkaline earth metals may include magnesium (Mg), calcium (Ca), strontium (Sr), barium (Ba), or any combination thereof.

[0278] Rare earth metals may include scandium (Sc), yttrium (Y), cerium (Ce), terbium (Tb), ytterbium (Yb), gadolinium (Gd), or any combination thereof. Alkali metals may include lithium (Li), sodium (Na), potassium (K), rubidium (Rb), cesium (Cs), or any combination thereof.

[0279] In one or more embodiments, the electronic functional layer (EFL) may comprise a metal halide (e.g., LiF, NaCl, CsF, RbCl, RbI, CuI, and / or KI), a lanthanide (e.g., Yb), or a co-deposited material of a metal halide and a lanthanide. For example, a co-deposited material of a metal halide and a lanthanide may comprise KI:Yb, RbI:Yb, and / or LiF:Yb. In one or more embodiments, metal oxides (e.g., Li₂O and / or BaO) and / or lithium 8-hydroxyquinoline (Liq) may be used in the EFL, but embodiments of this disclosure are not limited thereto. In one or more embodiments, the EFL may also consist of a mixture of an electron transport material and an insulating organometallic salt. The insulating organometallic salt may be a material having a bandgap of about 4 eV or greater. For example, the insulating organometallic salt may comprise, for example, metal acetates, metal benzoates, metal acetoacetates, metal acetylacetonates, and / or metal stearates.

[0280] In one or more embodiments, in addition to one or more of the materials described above, the electronic functional layer (EFL) may include at least one of 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), diphenyl(4-(triphenylsilyl)phenyl)phosphine oxide (TSPO1), and 4,7-diphenyl-1,10-phenanthroline (Bphen), but the embodiments of this disclosure are not limited thereto.

[0281] In one or more embodiments, the electronic functional layer (EFL) may include one or more compounds of the aforementioned electronic functional layer (EFL) in at least one of the electron injection layer (EIL), the electron transport layer (ETL), and the hole blocking layer (HBL).

[0282] In one or more embodiments, if (for example, when) the electronic functional layer (EFL) may include an electron transport layer (ETL), the ETL may have a thickness of about 100 Å to about 1000 Å, such as about 150 Å to about 500 Å. If (for example, when) the thickness of the ETL meets the above range, a satisfactory level of electron transport characteristics can be obtained without significantly increasing the driving voltage.

[0283] In one or more embodiments, if (for example, when) the electronic functional layer EFL includes an electron injection layer EIL, the electron injection layer EIL may have a thickness of about 1 Å to about 100 Å, such as about 3 Å to about 90 Å. If (for example, when) the thickness of the electron injection layer EIL meets the above range, a satisfactory level of electron injection characteristics can be obtained without significantly increasing the driving voltage.

[0284] In one or more embodiments, the second electrode EL2 may be provided on the electronic functional layer (EFL). In one or more embodiments, the second electrode EL2 may be a common electrode. The second electrode EL2 may be a cathode or an anode, but embodiments of this disclosure are not limited thereto. For example, if (e.g., when) the first electrode EL1 is an anode, the second electrode EL2 may be a cathode, and if (e.g., when) the first electrode EL1 is a cathode, the second electrode EL2 may be an anode. Here, at least one of alloys, metals, conductive compounds, or any combination thereof, each having a low work function, may be used as the material for the second electrode EL2.

[0285] In one or more embodiments, the second electrode EL2 may include lithium (Li), silver (Ag), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), ytterbium (Yb), silver-ytterbium (Ag-Yb), ITO, IZO, or any combination thereof. The second electrode EL2 may be a transmission electrode, a semi-transmission electrode, or a reflection electrode.

[0286] In one or more embodiments, the second electrode EL2 may be connected to an auxiliary electrode. If (for example, when) the second electrode EL2 is connected to the auxiliary electrode, the resistance of the second electrode EL2 may be reduced.

[0287] In one or more embodiments, the second electrode EL2 may have a single-layer structure or a multi-layer structure with multiple layers.

[0288] In one or more embodiments, a first capping layer may be disposed outside the first electrode EL1 (e.g., on the first electrode EL1) and / or a second capping layer may be disposed outside the second electrode EL2 (e.g., on the second electrode EL2).

[0289] In one or more embodiments, light generated from the emissive layer EML of the light-emitting diode ED can pass through the first electrode EL1 (as a semi-transparent electrode or a transmissive electrode) and the first capping layer and be extracted toward the outside; in one or more embodiments, light generated from the emissive layer EML of the light-emitting diode ED can pass through the second electrode EL2 (as a semi-transparent electrode or a transmissive electrode) and the second capping layer and be extracted toward the outside.

[0290] In one or more embodiments, the capping layer CPL may be independently an organic capping layer comprising organic materials, an inorganic capping layer comprising inorganic materials, or a composite capping layer comprising both organic and inorganic materials.

[0291] In one or more embodiments, the capping layer CPL may be an organic layer or an inorganic layer. For example, if (e.g., when) the capping layer CPL comprises an inorganic material, the inorganic material may include alkali metal compounds (e.g., LiF), alkaline earth metal compounds (e.g., MgF2), SiON, SiN. x and / or SiO y wait.

[0292] In one or more embodiments, for example, if (e.g., when) the capping layer CPL comprises an organic material, the organic material may include amine compounds (e.g., monoamine compounds and / or diamine compounds). For example, in one or more embodiments, the organic material may include TPD, α-NPD, β-NPB, m-MTDATA, N4,N4,N4',N4'-tetra(biphenyl-4-yl)biphenyl-4,4'-diamine (TPD15) and / or 4,4',4''-tris(N-carbazolyl)triphenylamine (TCTA), etc. However, embodiments of this disclosure are not limited thereto; for example, in one or more embodiments, the capping layer CPL may include Alq3, CuPc, epoxy resin, or acrylate (e.g., methacrylate).

[0293] In one or more embodiments, the capping layer CPL may include at least one of compounds CP1 to CP4 (e.g., selected from compounds CP1 to CP4), but embodiments of this disclosure are not limited thereto. In embodiments of the manufacture of light-emitting diodes disclosed herein, the capping layer CPL includes compound CP4.

[0294]

[0295] In one or more embodiments, the capping layer CPL may have a refractive index of 1.6 or greater. For example, 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 greater, 1.8 or greater, or 2.0 or greater.

[0296] Figure 7 A cross-sectional view illustrating a portion of a display device according to one or more embodiments of the present disclosure.

[0297] The display device 1001 will be described with reference to the first light-emitting diode ED1 among a plurality of light-emitting diodes ED1, ED2, and ED3. The first light-emitting diode ED1 may include n light-emitting structures OL1, ..., OLn-1 and OLn stacked between the first electrode EL1 and the second electrode EL2, and n-1 charge-generating layers CGL1, ... and CGLn-1. Here, n may be a natural number.

[0298] The light-emitting structures OL1, ..., OLn-1 and OLn can each include a hole functional layer (HFL) and an electron functional layer (EFL). Figure 2 The light-emitting layers EML1, EML2 and EML3 can be arranged between the hole functional layer HFL and the electron functional layer EFL.

[0299] In one or more embodiments, for example, the first light-emitting diode ED1 included in the display device 1001 in one or more embodiments may be a light-emitting diode having a series structure including multiple light-emitting layers.

[0300] In one or more embodiments, charge generation layers CGL1, ... and CGLn-1 may each be inserted between adjacent light-emitting structures OL1, ..., OLn-1 and OLn. Each charge generation layer CGL1, ... and CGLn-1 may comprise a p-type (or n-type) charge generation layer and / or an n-type (or n-type) charge generation layer. Figure 7 This describes a display device 1001 comprising three light-emitting structures OL1, OLn-1, and OLn, and two charge-generating layers CGL1 and CGLn-1, if (for example, when) n is 3. Figure 7 The differences described herein mean that in one or more embodiments, if (for example, when) n is 1, the (n-1)th light-emitting structure OLn-1 and the (n-1)th charge-generating layer CGLn-1 may not be provided, and the nth light-emitting structure OLn may be in direct contact with the first charge-generating layer CGL1. Additionally, with Figure 7 As illustrated in the text, in one or more embodiments, if (for example, when) n is 3 or greater, the light-emitting structure and the charge-generating layer may be added sequentially between the first charge-generating layer CGL1 and the (n-1)th light-emitting structure OLn-1.

[0301] In one or more embodiments, the light-emitting structures OL1, ..., OLn-1 and OLn included in the first light-emitting diode ED1 can emit light in substantially the same wavelength range. However, embodiments of this disclosure are not limited thereto, and at least some of the light-emitting structures OL1, ..., OLn-1 and OLn included in the first light-emitting diode ED1 can emit light in different wavelength ranges from other light-emitting structures.

[0302] In one or more embodiments, each of the light-emitting structures OL1, ..., OLn-1 and OLn can emit light in different wavelength ranges depending on the different light-emitting diodes ED1, ED2 and ED3 that respectively include the light-emitting structures OL1, ..., OLn-1 and OLn. For example, the first light-emitting structure OL1 included in the first light-emitting diode ED1 and the first light-emitting structure OL1 included in the second light-emitting diode ED2 can emit light in different wavelength ranges. However, the embodiments of this disclosure are not limited to this; for example, each of the light-emitting structures OL1, ..., OLn-1 and OLn can emit light in substantially the same wavelength range depending on the different light-emitting diodes ED1, ED2 and ED3 that respectively include the light-emitting structures OL1, ..., OLn-1 and OLn.

[0303] although Figure 7 The accompanying drawings illustrate that all (e.g., each) light-emitting diodes ED1, ED2, and ED3 have the same structure; however, embodiments of this disclosure are not limited to those illustrated in the drawings. In one or more embodiments, some of the light-emitting diodes ED1, ED2, and ED3 may include k light-emitting structures (k being a natural number), and others may include m light-emitting structures (m being a natural number different from k).

[0304] Figure 8 A cross-sectional view illustrating a portion of a display device according to one or more embodiments of the present disclosure.

[0305] Based on reference Figure 2 The differences in the described display device 1000 are used to describe Figure 8 A display device 1002 according to one or more embodiments. Configurations not described and... Figure 2 The description is consistent.

[0306] The display device 1002 may further include a light control layer CCL and a color filter layer CFL, each disposed on the display element layer EDL.

[0307] In one or more embodiments, the optical control layer CCL may include multiple optical control components CCP1, CCP2 and CCP3. Figure 8 This disclosure explains that the light control components CCP1, CCP2, and CCP3 can be separated from each other, and the spacer pattern BMP can be arranged between the light control components. However, the embodiments of this disclosure are not limited to those described above. Figure 8 As illustrated herein, for example, in one or more embodiments, the edges of the light control components CCP1, CCP2, and CCP3 may overlap each other or the edges of the light control components CCP1, CCP2, and CCP3 may overlap with the partition pattern BMP.

[0308] In one or more embodiments, the light control layer CCL may include first to third light control components CCP1 to CCP3 that overlap with the first to third light-emitting diodes ED1 to ED3, respectively.

[0309] In one or more embodiments, at least one of the first to third light control components CCP1 to CCP3 can change the wavelength of the incident light (e.g., blue light) and then emit light of a different color (e.g., red or green light). Alternatively, at least one of the first to third light control components CCP1 to CCP3 can transmit the incident light (e.g., blue light) without changing its wavelength.

[0310] In one or more embodiments, at least one of the first to third light control components CCP1 to CCP3 may include a light converter (e.g., a quantum dot or phosphor). The light converter can change the wavelength of the provided light and then emit the changed (converted) light. The first to third light control components CCP1 to CCP3 may each further include a scatterer and a base resin configured to disperse the scatterer. In one or more embodiments, the light control layer CCL may further include an insulating layer configured to prevent or reduce the penetration of moisture and / or oxygen.

[0311] In one or more embodiments, the color filter layer CFL may be disposed on the light control layer CCL.

[0312] The color filter layer CFL may include multiple color filters CF1, CF2 and CF3. Figure 8 The color filters CF1, CF2, and CF3 are described as spaced apart and / or separated (e.g., spaced apart or separate) and have a blocking member BM arranged between the color filters CF1, CF2, and CF3. However, embodiments of this disclosure are not limited to those described herein. Figure 8 As illustrated herein, and in one or more embodiments, the edges of color filters CF1, CF2 and CF3 may overlap each other, and the edges of color filters CF1, CF2 and CF3 may overlap with the blocking member BM.

[0313] The color filter layer CFL may include first to third color filters CF1 to CF3, which overlap with the first to third light-emitting diodes ED1 to ED3, respectively. The first to third color filters CF1 to CF3 may selectively transmit light of a specific color. However, embodiments of the present disclosure are not limited thereto, and at least one of the first to third color filters CF1 to CF3 may be provided to be transparent or translucent.

[0314] Figure 9 and Figure 10 Figures illustrate electronic devices that utilize display devices according to one or more embodiments of the present disclosure.

[0315] refer to Figure 9 The first electronic device ECD1 is defined as a tablet PC including a first display device DDA. The second electronic device ECD2 is defined as a portable terminal including a second display device DDb. The third electronic device ECD3 is defined as a laptop computer including a third display device DDc. The fourth electronic device ECD4 is defined as a TV including a fourth display device DDd.

[0316] The fifth electronic device ECD5 is defined as a head-mounted display device that includes a fifth display device DDe.

[0317] The sixth electronic device, ECD6, is defined as a digital watch that includes a sixth display device, DDf. (Reference) Figure 10 The seventh electronic device ECD7 is defined as a transport vehicle including the seventh to tenth display devices DDg to DDj. The seventh electronic device ECD7 is defined as a car. However, embodiments of this disclosure are not limited thereto, and the transport vehicle may include bicycles, motorcycles, trains, boats, and / or airplanes, etc.

[0318] The seventh display device DDg may be positioned in the driver's field of vision, in front of the steering wheel HN, to display instrument panel information (e.g., vehicle speed). The eighth display device DDh may be positioned on the vehicle's dashboard, separate from the seventh display device DDg, and to display information about the vehicle control interface, audio, temperature, road conditions, and / or video. The ninth display device DDi may be positioned on the side mirror of the driver's or passenger's seat and function as a digital side mirror. The ninth display device DDi may display images taken outside the vehicle. The tenth display device DDj may be positioned behind the driver's or passenger's seat and to display, for example, images recognized by passengers in the rear seats.

[0319] At least one of the first to tenth display devices DDa to DDj may include a reference. Figures 3 to 6 The light-emitting diode (ED) described.

[0320] Apart from Figure 9 and Figure 10The electronic devices shown, and the display devices according to one or more embodiments, are not limited to the example electronic devices and can be applied to one or more suitable electronic devices, such as flat panel displays, curved displays, televisions, billboards, computer monitors, medical monitors, head-mounted displays, indoor lights, outdoor lights, signal lights, wearable devices, foldable devices, rollable devices, bendable devices, flexible devices, curved devices, electronic notebooks, e-books, portable multimedia players, personal digital assistants, laser printers, telephones, cellular phones, tablet PCs, portable terminals, laptop computers, digital cameras, viewfinders, camcorders, 3D displays, virtual reality displays, augmented reality displays, video walls including multiple displays tiled together, vehicle display devices, outdoor display devices, theater screens, stadium screens, and / or signs.

[0321] The embodiments and comparative examples will be described in more detail below. Specifically, compounds according to one or more embodiments and light-emitting diodes according to one or more embodiments will be described. However, the embodiments shown are illustrated to aid in understanding the present disclosure, and the scope of the disclosure is not limited thereto.

[0322] Synthesis example

[0323] Synthesis Examples 1 to 9

[0324] The method for synthesizing compounds according to one or more embodiments is not limited to the examples.

[0325] Synthesis Example 1: Synthesis of Compound O-120

[0326]

[0327] Dimethylacetamide (DMA) was mixed with 2 mol% tris(dibenzylacetone)palladium(O) (Pd2(dba)3), 4 mol% 1,1'-bis(diphenylphosphino)ferrocene (dppf), and 12 mol% Zn. 2-(2-bromo-3-chloro-4-hydroxyphenyl)acetonitrile (10.00 g, 37 mmol) and Zn(CN)2 (5.23 g, 45 mmol) were added, and the mixture was stirred to react at 120 °C. After the reaction was complete, the mixture was washed with ethyl acetate (EtOAc) and H2O, the water was removed with anhydrous MgSO4, and the solvent was removed under reduced pressure. The product was then purified by column chromatography to obtain 8.3 g of intermediate O-120-a (yield: 94.4%).

[0328]

[0329] 2-(2-bromo-3-chlorophenyl)acetonitrile (10.00 g, 43 mmol) and Zn(CN)2 (6.11 g, 52 mmol) were reacted by substantially the same method as that used to synthesize intermediate O-120-a to obtain 8.55 g of intermediate O-120-b (yield: 89.1%).

[0330]

[0331] AbL laccase catalyst (Sigma-Aldrich, product number 40452) was added to phosphate buffer (pH 6.0, 0.2 M), and the obtained intermediates O-120-a (8.00 g, 34 mmol) and O-120-b (8.21 g, 37 mmol) were added and stirred to allow the reaction to proceed. After the reaction was complete, the mixture was washed with EtOAc and H2O, the water was removed with anhydrous MgSO4, the solvent was removed under reduced pressure, and the product was then purified by column chromatography to obtain 10.2 g of intermediate O-120-c (yield: 66.6%).

[0332]

[0333] Acetylene (1.14 g, 44 mmol), PdCl2(PPh3)2 (1.11 g, 2 mmol), CuI (0.30 g, 2 mmol), PPh3 (0.52 g, 2 mmol), and diisopropylamine (4.01 g, 40 mmol) were mixed under an inert gas atmosphere, and intermediate O-120-c (9.00 g, 20 mmol) was added to react at 50 °C for 24 h. After the reaction was complete, the mixture was washed with EtOAc and H2O, water was removed with anhydrous MgSO4, and the solvent was removed under reduced pressure. The product was then purified by column chromatography to obtain 4.9 g of intermediate O-120-d (yield: 71.8%).

[0334]

[0335] Intermediate O-120-d (4.50 g, 13 mmol), PdCl2 (0.46 g, 3 mmol), AgSbF6 (1.35 g, 4 mmol), and Ph2SO4 (15.86 g, 78 mmol) were added to 150 mL of 1,2-dichloroethylene and the mixture was subjected to hot reflux with stirring at 60 °C for 24 h. Cs2CO3 (10.65 g, 33 mmol) was added to continue the reaction for 18 h. Extraction was performed using CH2Cl2, followed by solvent removal under reduced pressure. 15 mL of HCl was added to continue the reaction for 2 h. Extraction was performed using CH2Cl2 and NH4Cl, followed by removal of water from the organic layer with anhydrous MgSO4 and solvent removal under reduced pressure. The product was then purified by column chromatography to obtain 2.35 g of intermediate O-120-e (yield: 48.3%).

[0336]

[0337] Intermediate O-120-e (2.10 g, 6 mmol), malononitrile (2.24 g, 34 mmol), and pyridine (5.35 g, 68 mmol) were dissolved in 300 mL of CH₂Cl₂, and TiCl₄ (6.42 g, 34 mmol) was added. The mixture was stirred at room temperature for 4 hours. After terminating the reaction with water, CH₂Cl₂ was used for extraction, followed by rinsing with brine, removal of water with anhydrous MgSO₄, and removal of the solvent under reduced pressure. The result was dissolved in a small amount of CH₂Cl₂ and purified using a silica filter to obtain 1.8 g of compound O-120 from Synthetic Example 1 (yield: 68.1%).

[0338] Synthesis Example 2: Synthesis of Compound O-117

[0339]

[0340] Under an inert atmosphere, in dichloromethane (DCM) (0.5 M) solvent, trimethylsilyl cyanide (TMSCN) (6.96 g, 70 mmol) and TiCl4 (2.22 g, 12 mmol) were added sequentially to a stirred solution to react at room temperature after the addition of 1,3-dioxo-2,3-dihydro-1H-indene-2-onitrile (10.00 g, 58 mmol). Acetonitrile (0.2 M) and HCl (2 M) were added to the stirred solution and the reaction was continued for 1 hour at room temperature, followed by dilution with water. The solution was extracted with EtOAc, the organic layer was washed with brine, water was removed with anhydrous Na2SO4, and the solvent was removed under vacuum. 9.15 g of intermediate O-117-a (yield: 79.0%) was obtained by rapid column chromatography.

[0341]

[0342] 10.00 g of intermediate O-117-a was dissolved in 5 mL of 1,2-dichloroethane, and then 15.01 g of SOCl2 was slowly added. The reaction was carried out by stirring at 60 °C for 1 hour, and water was added to terminate the reaction. It was extracted with DCM, and the solvent was evaporated to obtain 7.65 g of intermediate O-117-b (yield: 84.1%).

[0343]

[0344] The reaction was initiated by adding 2-(4-chloro-2-iodophenyl)acetonitrile (100 g, 360 mmol) to a solution of acetic anhydride (Ac₂O) containing N,N,N',N'-tetramethyldiaminomethane (TMDAM) (44.19 g, 432 mmol). The solvent was removed under vacuum to obtain 63.5 g of intermediate O-117-c (yield: 60.9%).

[0345]

[0346] After dissolving intermediate O-117-c (60 g, 207 mmol), PdCl2(PPh3)2 (4.36 g, 6 mmol), and CuI (2.37 g, 12 mmol) in triethylamine (Et3N), oxygen was removed using a freeze-pump-thaw method. The solution was stirred at 60 °C under nitrogen atmosphere, with propynenitrile (17.99 g, 352 mmol) added three times at 1-hour intervals. Subsequently, it was concentrated under vacuum. After dissolving in CH2Cl2, it was filtered with silica gel and then concentrated again by column chromatography to obtain 42 g of intermediate O-117-d (yield: 95.3%).

[0347]

[0348] In toluene, InCl3 (13.20 g, 19 mmol) and intermediate O-117-d (40.00 g, 188 mmol) were dissolved and stirred at 80 °C for 1 h to carry out the reaction. After cooling the solution to room temperature, the solution was concentrated under vacuum. The product was purified by rapid silica gel column chromatography to obtain 33.5 g of intermediate O-117-e (yield: 83.8%).

[0349]

[0350] Intermediate O-117-e (30.00 g, 141 mmol) was dissolved in polyethylene glycol dimethyl ether and stirred at 110 °C for 8 hours in an oxygen environment. The solution was cooled to obtain 26.65 g of intermediate O-117-f (yield: 88%) by silica gel column chromatography.

[0351]

[0352] After adding and dissolving [bis(diphenylphosphino)ferrocene]palladium(II) dichloride (PdCl2(dppf)) (2.81 g, 4 mmol) in dioxane, intermediate O-117-f (25.00 g, 116 mmol), Et3N (49.20 g, 384 mmol), and pinacolborane (23.85 g, 186 mmol) were added. After stirring the solution at 80 °C for 3 hours to allow the reaction to proceed, it was extracted with benzene and washed with water. After removing water with anhydrous MgSO4 and concentrating the solution, 26.5 g of intermediate O-117-g (yield: 74.3%) was obtained by Kugelrohr distillation.

[0353]

[0354] Intermediate O-117-g (26.50 g, 87 mmol), L-histidine (0.78 g), and triethylamine (1.01 mg) were added to dimethylformamide (DMF), and the mixture was heated at 90 °C for 24 h to react. After the reaction was complete, the solution was diluted with ethyl acetate and water, and extracted with ethyl acetate. The remaining organic layer was washed with brine, and water was removed with anhydrous Na₂SO₄. The solvent was removed under reduced pressure, and 11.55 g of intermediate O-117-h (68.0% yield) was obtained by silica gel column chromatography.

[0355]

[0356] Two intermediates, O-117-b (7.50 g, 42 mmol) and O-117-h (8.98 g, 46 mmol), were added and mixed in phosphate buffer (pH 7.4). Catecholase (2.16 mL, 125 μM) was added and the mixture was stirred at room temperature for 24 hours. The solution was extracted with chloroform and washed with water. The organic layer was washed with brine and water was removed with anhydrous MgSO4. Subsequently, evaporation was performed under reduced pressure. 8.85 g of intermediate O-117-i (yield: 57.1%) was obtained by rapid silica gel chromatography.

[0357]

[0358] Intermediate O-117-i was treated by essentially the same method as that used to synthesize compound O-120 from intermediate O-120-e to obtain 5.65 g of compound O-117 of Synthesis Example 2 (yield: 59.9%).

[0359] Synthesis Example 3: Synthesis of Compound O-34-1

[0360]

[0361] Silver acetate (12.69 g, 76 mmol) and palladium acetate (0.16 g, 1 mmol) were added to acetic acid and stirred. Then 2-chloro-5-fluoroaniline (10.00 g, 69 mmol) and (E)-4-oxobut-2-enoic acid (7.56 g, 76 mmol) were added and stirred at 110 °C for 30 min. After cooling to room temperature, the mixture was diluted with ethyl acetate, filtered through a filter, and concentrated under vacuum. Column chromatography yielded 14.4 g of intermediate O-34-a (yield: 92.9%).

[0362] In the synthesis of intermediate O-34-a, 10 g of 2-chloro-5-fluorophenol was used instead of 10 g of 2-chloro-5-fluoroaniline as the starting material to obtain 12.5 g of intermediate O-34-b (yield: 81.2%).

[0363] In CHCl3, trifluoroacetic anhydride (TFAA) (78.19 g, 372 mmol) was mixed and intermediate O-34-b (12.00 g, 53 mmol) was dissolved to react at room temperature for 30 min. After cooling with ice, the mixture was alkalized with K2CO3, extracted with CH2Cl2, dehydrated with anhydrous MgSO4, and filtered under vacuum. 10.2 g of intermediate O-34-c (yield: 91.9%) was obtained by silica gel chromatography.

[0364]

[0365] In DMF, intermediate O-34-c (10.00 g, 48 mmol) was stirred and dissolved, and methyl 4-methylbenzenesulfonate (11.61 g, 62 mmol) and K₂CO₃ (15.46 g, 110 mmol) were added. The mixture was then heated at 70 °C under nitrogen for 1 hour and then cooled to room temperature. After adding EtOAc and rinsing with water, the water was removed with anhydrous Na₂SO₄, and the solution was concentrated. It was then rinsed with diethyl ether (Et₂O), and the remaining material was dried to obtain 9.25 g of intermediate O-34-d (yield: 86.7%).

[0366]

[0367] Intermediate O-34-d (9.00 g, 40 mmol), intermediate O-34-a (13.68 g, 61 mmol), tetrakis(triphenylphosphine)palladium (0.44 g, 2 mmol), and Ba(OH)₂ (20.78 g, 121 mmol) were dissolved in an aqueous solution of 1,4-dioxane, and the solution was purged three times with nitrogen. After heating and stirring for 12 hours, the solution was cooled to room temperature and filtered with diatomaceous earth, and the obtained material was extracted with EtOAc. After drying with anhydrous Na₂SO₄ and concentrating under vacuum, 12.65 g of intermediate O-34-e (yield: 82.9%) was obtained by column chromatography.

[0368] After dissolving intermediate O-34-e (12.00 g, 32 mmol) in CH3SO3H and stirring for 3 hours, the solution was cooled with ice water. After filtration, 9.45 g of intermediate O-34-f (yield: 82.7%) was obtained by recrystallization.

[0369]

[0370] After dissolving intermediate O-34-f (9.00 g, 25 mmol) in water, the solution was stirred at room temperature, and 4.85 g of sulfuric acid was added dropwise. The solution was cooled to 0 °C, and sodium nitrite solution was added dropwise over 3 hours. The solution was then heated to room temperature and stirred. The solution was recrystallized by adding water and filtered. The filtrate was extracted with dichloromethane to obtain 6.6 g of intermediate O-34-f (yield: 80.3%) by column chromatography.

[0371]

[0372] Intermediate O-34-g (9.00 g, 27 mmol), malononitrile (7.24 g, 110 mmol), and piperidine (110 mmol) were added to ethanol (EtOH) and stirred under reflux for 1 hour. After cooling to room temperature, the resulting precipitate was filtered and dissolved with KCN (7.14 g, 110 mmol) in a 50% EtOH solution (ethanol:water = 50:50 (v:v)). Excess HCl was then added to react at 0 °C for 2 hours. The compound obtained by filtering the precipitate, washing the precipitate with water, and drying the precipitate, along with N-chlorosuccinimide (NCS) (9.82 g, 110 mmol), was added to diethyl ether and reacted at room temperature for 2 hours. This was then added to cold water to complete the reaction. The solvent was removed under reduced pressure, and hexane was used for recrystallization to obtain 4.65 g of intermediate O-34-h (yield: 35.8%). Subsequently, intermediate O-34-h (4.50 g, 9 mmol) was treated in essentially the same manner as intermediate O-120-e to obtain 2.25 g of compound O-34-1 of Synthesis Example 3 (yield: 41.6%).

[0373] Synthesis Example 4: Synthesis of Compound O-63-1

[0374] In a nitrogen atmosphere, 3,5-dichloro-2-fluorobenzonitrile (10.00 g, 53 mmol) and 4-formylbenzonitrile (7.59 g, 58 mmol) were added to DCM (0.1 M) and stirred. After preparing 1,3-dimethylimidazolium iodide (2.36 g, 11 mmol) and Cs₂CO₃ (25.88 g, 79 mmol) in separate tubes, the above solutions were added and stirred for an additional 18 hours. After the reaction was complete, silica gel column chromatography was used to obtain 14.8 g of intermediate O-63-a (yield: 93.4%).

[0375] Using essentially the same method, 3,5-dichloro-2,6-difluorobenzonitrile (10.00 g, 48 mmol) was used instead of 3,5-dichloro-2-fluorobenzonitrile (10.00 g, 53 mmol) to obtain 13.2 g of intermediate O-63-a' (yield: 86%).

[0376]

[0377] The intermediate O-63-a was prepared by dissolving 12.00 g (40 mmol) in tetrahydrofuran. The prepared O-63-a solution was added dropwise at -78 °C after dissolving t-BuLi (3.06 g, 48 mmol) in pentane to obtain a concentration of 1.7 M. The mixture was stirred at 0 °C for 30 min, then stirred at room temperature for another 30 min. 2-Cyano-N-methoxy-N-methylacetamide (2.55 g, 20 mmol) was slowly added to the solution using a sleeve, and the solution was stirred at room temperature until the reaction was complete. After washing with saturated NH4Cl solution and diluting with water, the mixture was extracted with ethyl acetate (EtOAc). After washing the organic layer with brine, water was removed with anhydrous Na2SO4, and 10.2 g of intermediate O-63-b (yield: 76.7%) was obtained by silica gel chromatography.

[0378]

[0379] A small amount of ReBr(CO)5 was added to intermediate O-63-b (10.00 g, 30 mmol) and the mixture was heated and stirred. The intermediate O-63-c was obtained by vacuum filtration (yield: 87.2%).

[0380] Using essentially the same process, intermediate O-63-b' (9.00 g, 26 mmol) was used as the starting material, and 7.1 g of intermediate O-63-c' was obtained (yield: 83.1%).

[0381]

[0382] Starting with intermediate O-63-c (8.00 g, 25 mmol), the process was substantially the same as that used to obtain compound O-120 from intermediate O-120-e to obtain 8.25 g of intermediate O-63-d (yield: 89.5%).

[0383] Using essentially the same process, intermediate O-63-c' (7.00 g, 21 mmol) was used as the starting material, and 7.1 g of intermediate O-63-d' was obtained (yield: 88.7%).

[0384]

[0385] In a shrink tube under argon atmosphere, intermediate O-63-d' (7.00 g, 18 mmol), Cu(OH)2 (90 mg, 1 mmol), glycolic acid (420 mg, 6 mmol), NaOH (4.40 g, 110 mmol), and dimethyl sulfoxide (DMSO) were added and stirred at 120 °C for 6 hours. After cooling to room temperature, 500 mL of water was added, and 2 M HCl was used to obtain pH=1. After extraction with EtOAc, the mixture was washed with H2O and brine and dried to obtain 6.8 g of intermediate O-63-e (yield: 97.7%) by column chromatography.

[0386]

[0387] Intermediate O-63-d (6.00 g, 16 mmol), intermediate O-63-e (6.26 g, 16 mmol), bis(dibenzylacetone)palladium(0) (Pd(dba)2) (240 mg), and t-Bu3PHBF4 (240 mg) were mixed and heated to 160 °C for 20 min. After adding 0.1 M HCl, the mixture was extracted with CH2Cl2 and 9.1 g of intermediate O-63-f (yield: 82%) was obtained by rapid column chromatography.

[0388]

[0389] Subsequently, using the same method as that used to obtain intermediate O-34-c from intermediate O-34-b, intermediate O-63-f (9.00 g, 13 mmol) was used as the starting material to obtain 7.9 g of compound O-63-1 of Synthetic Example 4 (yield: 88%).

[0390] Synthetic example: Synthesis of compound O-122-1

[0391] In a mixture of 2,5-dichlorobenzonitrile (10.00 g, 58 mmol) and 2-hydroxyacetonitrile (0.66 g, 12 mmol), 30 mL of hexafluoroisopropanol and 10 µL of trifluoromethanesulfonic acid were added, and the mixture was stirred at 80 °C for 24 h. Extraction was performed using NaHCO3 and EtOAc, and the organic layer was washed with brine. The mixture was then dried to obtain 8.85 g of intermediate O-122-a (yield: 72.1%).

[0392] Using essentially the same process, 2,5-dichloro-3-fluorobenzonitrile (10.00 g, 53 mmol) was used instead of 2,5-dichlorobenzonitrile (10.00 g, 58 mmol) to obtain 8.6 g of intermediate O-122-a' (yield: 71.3%).

[0393]

[0394] Intermediate O-122-a (8.50 g, 40 mmol) was dissolved in 5% vanadium acetate (vanadium acetate: dichloromethane (DCM) = 5% w / v) under nitrogen atmosphere, and t-BuOOH (7.26 g, 81 mmol) was added and stirred at room temperature for 24 hours. After the reaction was complete, it was washed with H2O and extracted with dichloromethane. Subsequently, 8.2 g of intermediate O-122-b (yield: 90.5%) was obtained by column chromatography.

[0395] Using essentially the same process, intermediate O-122-a' (8.50 g, 37 mmol) was used instead of intermediate O-122-a (8.50 g, 40 mmol) as the starting material to obtain 7.1 g of intermediate O-122-b' (yield: 85%).

[0396]

[0397] In the subsequent steps, using essentially the same process as that used to obtain compound O-63-1, intermediate O-122-b / b' was used instead of intermediate O-63-a / a' and 2-(4-cyanophenyl)-N-methoxy-N-methylacetamide was used instead of 2-cyano-N-methoxy-N-methylacetamide to obtain 9.5 g of compound O-122-1 of Synthetic Example 5 (yield: 37.5%).

[0398] Synthesis Examples 6 to 9: Synthesis of compounds O-53, O-58, S-58 and S-117

[0399] In the synthesis of compound O-117, 2-(5-chloro-2-iodophenyl)acetonitrile was used instead of 2-(4-chloro-2-iodophenyl)acetonitrile to obtain compound O-53 of Synthetic Example 6.

[0400] Similarly, 5-chloro-3-(cyanomethyl)-2-iodobenzonitrile was used instead of 2-(4-chloro-2-iodophenyl)acetonitrile to obtain compound O-58 of Synthetic Example 7.

[0401] In the synthesis of intermediate O-58-g to intermediate O-58-h of compound O-58, thiol-histidine was used instead of L-histidine to obtain compound S-58 of Synthesis Example 8.

[0402] In the synthesis of compound O-117 from intermediate O-117-g to intermediate O-117-h, thiol-histidine was used instead of L-histidine to obtain compound S-117 of Synthesis Example 9.

[0403] The proton nuclear magnetic resonance (NMR) of each of the compounds synthesized in Synthetic Examples 1 to 9 1 ¹H NMR and mass spectrometry / fast atomic bombardment (MS / FAB) spectra are shown in Table 1. Referring to the above synthetic routes and starting materials, those skilled in the art will recognize methods for synthesizing other compounds.

[0404] Table 1

[0405]

[0406] Examples 1 to 9: Manufacturing of Light Emitting Diodes

[0407] As the anode, it will have 15 Ω / cm 2 The glass substrate (Corning Incorporated) for the ITO electrode (1,300 Å) was cut to a size of 50 mm × 50 mm × 0.7 mm, and cleaned by ultrasonic rinsing with isopropanol and then with pure water for 5 minutes each, followed by irradiation with ultraviolet light for 30 minutes and then exposure to ozone. The ITO glass substrate was then mounted in a vacuum deposition apparatus. On the anode, a hole injection layer with a thickness of 100 Å was fabricated by vacuum deposition of compounds from Synthesis Examples 1 to 9 and compound HT3 as p-type dopants at a weight ratio of 3:97, and compound HT40 was vacuum deposited on the hole injection layer to form a hole transport layer with a thickness of 1,250 Å.

[0408] Compounds H125, H126, and D1 were vacuum-deposited on the hole transport layer in a weight ratio of 45:45:10 to form a luminescent layer with a thickness of 300 Å.

[0409] Compound ET37 was vacuum-deposited onto the emitting layer to form a buffer layer with a thickness of 50 Å, and compounds ET46 and Liq were vacuum-deposited onto the buffer layer in a 5:5 weight ratio to form an electron transport layer with a thickness of 310 Å. Subsequently, Yb was vacuum-deposited onto the electron transport layer to form an electron injection layer with a thickness of 15 Å, and Ag and Mg were vacuum-deposited onto the electron injection layer in a 5:5 weight ratio to form a cathode with a thickness of 1,000 Å, thereby fabricating a light-emitting diode.

[0410]

[0411] Comparative example

[0412] The compounds of Comparative Examples 1 and 2 were used instead of the compounds of Synthetic Examples 1 to 9 for the hole functional layer comprising the hole injection layer. Except as described above, the light-emitting diodes were manufactured using essentially the same method as in Examples 1 to 9.

[0413] Comparative Example 1

[0414]

[0415] Comparative Example 2

[0416]

[0417] result

[0418] Experimental Example 1: Evaluation of Physical Properties

[0419] The HOMO level, LUMO level, hole mobility, electron mobility, and glass transition temperature of each of the compounds synthesized in Synthetic Examples 1 to 9 are shown in Table 2. Those skilled in the art can easily understand the synthesis methods of other compounds by referring to the above synthetic routes and raw materials. 1) HOMO level evaluation method: The voltage (V)-current (A) plots of each compound were obtained using cyclic voltammetry (CV) (electrolyte: 0.1 M Bu4NPF6 / solvent: DMF (dimethylformamide) / electrode: 3-electrode system (working electrode: glassy carbon (GC), reference electrode: Ag / AgCl, auxiliary electrode: Pt)), and the HOMO level of each compound was calculated from the oxidation starting point of the plot. 2) LUMO level assessment method: Cyclic voltammetry (CV) was used to obtain voltage (V)-current (A) plots for each compound (electrolyte: 0.1 M Bu4NPF6 / solvent: DMF (dimethylformamide) / electrode: 3-electrode system (working electrode: GC, reference electrode: Ag / AgCl, auxiliary electrode: Pt)). The LUMO level of each compound was calculated from the reduction starting point of the plot.

[0420] 3) Hole and electron mobility assessment methods: The space charge-limited current (SCLC) method described in “Hole mobility of N,N'-bis(naphthyl-1-yl)-N,N'-bis(phenyl)benzidine studied by using space charge-limited current, Appl. Phys. Lett. 90, 203512 (2007)” (the entire contents of which are incorporated herein by reference) will be used for assessment.

[0421] Table 2

[0422]

[0423] Experiment Example 2: Evaluation of Light Emitting Diodes

[0424] To evaluate the characteristics of each of the light-emitting diodes manufactured in Examples 1 to 9 and Comparative Examples 1 and 2, measurements were taken at 10 mA / cm². 2 The driving voltage and current efficiency at the given current density are shown in Table 3. The driving voltage of the LED was measured using a source measurement unit (Keithley, 2400 series), and the current efficiency was measured using a luminance measurement unit (Konica Minolta, CS-2000). Additionally, the lifetime of the LED was measured based on the time required to reach 95% of its initial luminance. Each evaluation result was compared to Comparative Example 1, and Comparative Example 2 and Examples 1 to 9 were also compared. The compared measurements are shown in Table 3.

[0425] Table 3

[0426]

[0427] Based on Table 3, it can be confirmed that each of the light-emitting diodes according to Examples 1 to 9 exhibits low driving voltage, high current efficiency and excellent lifetime compared with the driving voltage, current efficiency and lifetime according to Comparative Examples 1 and 2.

[0428] As used herein, the terms “substantially,” “about,” or similar terms are used as approximate terms and not as terms of degree, and are intended to take into account the inherent biases in measured or calculated values ​​that would be recognized by one of ordinary skill in the art. As used herein, “about” includes the stated value and means within an acceptable range of deviation for a particular value, determined by one of ordinary skill in the art considering the measurement under discussion and the errors associated with the measurement of the particular quantity (i.e., limitations of the measurement system). For example, “about” may mean within one or more standard deviations of the stated value, or within ±30%, ±20%, ±10%, or ±5% of the stated value.

[0429] In the context of this application and unless otherwise defined, the terms “use,” “using,” and “used” are to be regarded as synonymous with the terms “utilize,” “utilizing,” and “utilized,” respectively.

[0430] Any numerical range set forth herein is intended to include all subranges of the same numerical precision falling within the set forth range. For example, the range “1.0 to 10.0” is intended to include (and inclusive) the range between the stated minimum of 1.0 and the stated maximum of 10.0, i.e., all subranges having a minimum value equal to or greater than 1.0 and a maximum value equal to or less than 10.0, such as, for example, 2.4 to 7.6. Any maximum numerical limit set forth herein is intended to include all lower numerical limits falling within it, and any minimum numerical limit set forth in this specification is intended to include all higher numerical limits falling within it. Accordingly, the applicant reserves the right to modify this disclosure, including the claims, to expressly set forth any subrange falling within the range expressly set forth herein.

[0431] The light-emitting elements, display devices / apparatus, electronic devices, means for manufacturing them, or any other related devices / apparatus or components described herein according to embodiments of this disclosure may be implemented using any suitable hardware, firmware (e.g., application-specific integrated circuits), software, or a combination of software, firmware, and hardware. For example, various components of the device may be formed on an integrated circuit (IC) chip or on a separate IC chip. Furthermore, various components of the device may be implemented on a flexible printed circuit film, a tape-on package (TCP), or a printed circuit board (PCB), or formed on a substrate. Furthermore, various components of the device may be processes or threads that run on one or more processors in one or more computing devices, execute computer program instructions, and interact with other system components to perform the various functions described herein. The computer program instructions are stored in memory, which may be implemented in a computing device using standard memory devices, such as random access memory (RAM). The computer program instructions may also be stored in other non-transitory computer-readable media, such as CD-ROMs or flash drives. Furthermore, those skilled in the art will recognize that, without departing from the scope of the embodiments of this disclosure, the functions of various computing devices may be combined or integrated into a single computing device, or the functions of a particular computing device may be distributed across one or more other computing devices.

[0432] In this disclosure, each suitable feature of the various embodiments of this disclosure may be combined in part or in whole or in combination with each other, and may be technically linked and operated in various suitable ways, and unless otherwise stated or implied, the embodiments may be implemented independently of each other or in combination with each other in any suitable way.

[0433] Although certain embodiments of this disclosure have been described above, it should be understood by any person skilled in the art to which this disclosure pertains that various modifications and arrangements of this disclosure may exist without departing from the technical concept and scope of this disclosure as defined in the appended claims.

[0434] Therefore, the technical scope of this disclosure should be interpreted by the scope of the claims and their equivalents, rather than by the description disclosed in the specific embodiments.

Claims

1. A light-emitting diode, comprising: First electrode; A second electrode opposite to the first electrode; as well as At least one functional layer between the first electrode and the second electrode The at least one functional layer comprises a compound represented by Formula 1: Formula 1 ,and In Equation 1, X is O, S, Ga, In, Ge, Sn, Pb, Sb, Bi, Se or Te, R1 to R8 are each independent of: Hydrogen, deuterium, halogen, haloalkyl, hydroxyl, cyano, nitro, trifluoromethyl, amino, amidine, hydrazine, hydrazone, or alkoxy groups having 1 to 10 carbon atoms; or Each of the following unsubstituted or substituted groups having 1 to 10 carbon atoms: alkyl, alkenyl, alkynyl, aryl, aryl, heteroaryl, or any combination thereof: deuterium, halogen, haloalkyl, hydroxyl, cyano, nitro, trifluoromethyl, amino, amidine, hydrazine, hydrazone, alkoxy, or any combination thereof. m and n are each independent integers between 0 and 2, inclusive.

2. The light-emitting diode according to claim 1, The compound is represented by formula 1-1 or formula 1-2: Equation 1-1 Formula 1-2 ,and in, In Equations 1-1 and 1-2, X is selected from O, S, Ga, In, Ge, Sn, Pb, Sb, Bi, Se and Te, R1, R2 and R9 to R 24 Each independently is: Hydrogen, deuterium, halogen, haloalkyl, hydroxyl, cyano, nitro, trifluoromethyl, amino, amidine, hydrazine, hydrazone, or alkoxy groups having 1 to 10 carbon atoms; or Each of the following unsubstituted or substituted groups having 1 to 10 carbon atoms: alkyl, alkenyl, alkynyl, aryl, aryl, heteroaryl, or any combination thereof: deuterium, halogen, haloalkyl, hydroxyl, cyano, nitro, trifluoromethyl, amino, amidine, hydrazine, hydrazone, alkoxy, or any combination thereof. m and n are each independent integers between 0 and 2, inclusive.

3. The light-emitting diode according to claim 2, Where R1, R2, R 19 R 20 R 21 and R 22 Each independently is: Halogenated alkyl, hydroxyl, cyano, nitro, trifluoromethyl, amino, or alkoxy groups having 1 to 10 carbon atoms; or An alkenyl group having 2 to 10 carbon atoms, either unsubstituted or substituted with a haloalkyl, hydroxyl, cyano, nitro, trifluoromethyl, amino, alkoxy, or any combination thereof having 1 to 10 carbon atoms.

4. The light-emitting diode according to claim 1, Where X is O or S.

5. The light-emitting diode according to claim 1, The compound represented by Formula 1 includes at least one compound selected from Group 1 and / or at least one compound selected from Group 2: Compound group 1 Compound group 2 。 6. The light-emitting diode according to claim 1, The light-emitting diode includes at least one functional layer and a charge generation layer. The at least one functional layer includes: Hole functional layer on the first electrode; as well as The light-emitting layer on the hole functional layer, and At least one of the compounds selected from the hole-functional layer, the light-emitting layer, and the charge-generating layer includes the compound.

7. The light-emitting diode according to claim 6, The compound is a p-type dopant.

8. The light-emitting diode according to claim 7, in: Based on a total weight of 100 parts by weight of the compounds constituting the hole functional layer, the amount of the p-type dopant is from 0.5 parts by weight to 15 parts by weight; and / or Based on a total weight of 100 parts by weight of the compounds constituting the charge generation layer, the amount of the p-type dopant is from 0.5 parts by weight to 15 parts by weight.

9. An electronic device comprising a light-emitting diode according to any one of claims 1 to 8.

10. A compound represented by Formula 1: Formula 1 ， in, In Equation 1, X is O, S, Ga, In, Ge, Sn, Pb, Sb, Bi, Se or Te, R1 to R8 are each independent of: Hydrogen, deuterium, halogen, haloalkyl, hydroxyl, cyano, nitro, trifluoromethyl, amino, amidine, hydrazine, hydrazone, or alkoxy groups having 1 to 10 carbon atoms; or Each of the following unsubstituted or substituted groups having 1 to 10 carbon atoms: alkyl, alkenyl, alkynyl, aryl, aryl, heteroaryl, or any combination thereof: deuterium, halogen, haloalkyl, hydroxyl, cyano, nitro, trifluoromethyl, amino, amidine, hydrazine, hydrazone, alkoxy, or any combination thereof. m and n are each independent integers between 0 and 2, inclusive.

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