Light-emitting element, monoamine compound for light-emitting element, and electronic device including light-emitting element
The integration of a monoamine compound in the hole transport region of a light-emitting element addresses the challenge of low efficiency and short lifespan in display devices, enhancing their performance.
Patent Information
- Authority / Receiving Office
- JP · JP
- Patent Type
- Applications
- Current Assignee / Owner
- SAMSUNG DISPLAY CO LTD
- Filing Date
- 2024-10-16
- Publication Date
- 2026-04-28
AI Technical Summary
Existing light-emitting elements in display devices, such as organic electroluminescence display devices, face challenges in achieving improved light efficiency and lifespan.
A light-emitting element comprising a first electrode, a hole transport region containing a monoamine compound represented by a specific chemical formula, a light-emitting layer, an electron transport region, and a second electrode, with the monoamine compound enhancing the efficiency and lifespan of the element.
The monoamine compound contributes to high efficiency and extended lifespan of the light-emitting element, improving the performance of display devices.
Smart Images

Figure 2026070694000001_ABST
Abstract
Description
[Technical Field]
[0001] The present invention relates to a light-emitting element, a monoamine compound used in the light-emitting element, and an electronic device including the light-emitting element. [Background technology]
[0002] Electronic devices include display devices. Recently, there has been a lot of development on image display devices such as organic electroluminescence display devices. Organic electroluminescence display devices are so-called self-emissive light-emitting devices that achieve display by recombining holes and electrons injected from the first and second electrodes in the light-emitting layer, causing the light-emitting material in the light-emitting layer to emit light.
[0003] When applying light-emitting elements to display devices, improvements in light efficiency and lifespan are required, and there is a continuous need for the development of light-emitting element materials that can stably achieve these improvements. [Overview of the Initiative] [Problems that the invention aims to solve]
[0004] The object of the present invention is to provide a light-emitting element with improved light efficiency and lifespan, and an electronic device including the same.
[0005] Another object of the present invention is to provide a monoamine compound that is a material for light-emitting devices with improved light efficiency and lifespan. [Means for solving the problem]
[0006] One embodiment provides a light-emitting element comprising a first electrode, a hole transport region disposed on the first electrode and containing a monoamine compound represented by the following chemical formula 1, a light-emitting layer disposed on the hole transport region, an electron transport region disposed on the light-emitting layer, and a second electrode disposed on the electron transport region.
[0007] [Chemical formula 1] JPEG2026070694000002.jpg52170
[0008] In the above chemical formula 1, L 1 L is a direct linkage, a substituted or unsubstituted ring-forming arylene group with 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heteroarylene group with 5 to 30 carbon atoms. 2 and L 3 Each of these is independently a directly bonded, unsubstituted phenylene group, a phenylene group substituted with a deuterium atom, or a phenylene group substituted with a phenyl group, and Ar a R is an unsubstituted phenyl group, an unsubstituted naphthalenyl group, a naphthalenyl group substituted with a phenyl group, an unsubstituted phenantrenyl group, a phenantrenyl group substituted with a phenyl group, an unsubstituted dibenzofuranyl group, an unsubstituted dibenzothiophenyl group, an unsubstituted carbazolyl group, a carbazolyl group substituted with a phenyl group, an unsubstituted benzonaphthofuranyl group, or an unsubstituted benzonaphthothiophenyl group. 1 ~R 3 Each of these is independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or an unsubstituted heteroaryl group having 5 to 30 ring-forming carbon atoms, R 4 The elements are a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 carbon atoms, where n1, n2, and n4 are each independently integers between 0 and 7, and n3 is an integer between 0 and 3, and may include a chemical structure in which any hydrogen atom is substituted with a deuterium atom.
[0009] The aforementioned chemical formula 1 can be represented by any one of the following chemical formulas 1-A1 to 1-A3.
[0010] [Chemical formula 1-A1] JPEG2026070694000003.jpg49170
[0011] [Chemical formula 1-A2] JPEG2026070694000004.jpg47170
[0012] [Chemical formula 1-A3] JPEG2026070694000005.jpg48170
[0013] In the following Chemical formulas 1-A1 to 1-A3, L 2 , L 3 , Ar a , R 1 to R 4 , and n1 to n4 are as defined in the Chemical formula 1 above.
[0014] The Chemical formula 1 can be represented by any one of the following Chemical formulas 1-B1 to 1-B3.
[0015] [Chemical formula 1-B1] JPEG2026070694000006.jpg47170
[0016] [Chemical formula 1-B2] JPEG2026070694000007.jpg53170
[0017] [Chemical formula 1-B3] JPEG2026070694000008.jpg58170
[0018] In the Chemical formula 1-B2, n5 is an integer from 0 to 4, and R 5 can be a hydrogen atom or a deuterium atom. In the following Chemical formulas 1-B1 to 1-B3, L 1 , L 2 , Ar a , R 1 to R 4 , and n1 to n4 are as defined in the Chemical formula 1 above.
[0019] In the Chemical formula 1, L 2This can be a direct connection or can be represented by any one of the following L2-1 to L2-4.
[0020] JPEG2026070694000009.jpg35170
[0021] In the above chemical formula 1, Ar a This can be represented by any one of the following AR-1 through AR-38.
[0022] JPEG2026070694000010.jpg123170JPEG2026070694000011.jpg125170JPEG2026070694000012.jpg57170
[0023] In the above chemical formula 1, R 1 ~R 3 Each of these can independently be a hydrogen atom, a deuterium atom, a fluorine atom, or an unsubstituted phenyl group.
[0024] In the above chemical formula 1, R 4 This can be a hydrogen atom, a deuterium atom, a fluorine atom, an unsubstituted phenyl group, or an unsubstituted dibenzofuranyl group.
[0025] In the above chemical formula 1, R 4 A naphthalenyl group containing can be represented by any one of the following R4-1 to R4-6.
[0026] JPEG2026070694000013.jpg67170
[0027] In the above R4-5, D is a deuterium atom.
[0028] The hole transport region includes a hole injection layer, a hole transport layer disposed on the hole injection layer, and an electron blocking layer disposed on the hole transport layer, wherein at least one of the hole injection layer, the hole transport layer, and the electron blocking layer may contain the monoamine compound.
[0029] The light-emitting layer may contain a compound represented by the following chemical formula E-1.
[0030] [Chemical formula E-1] JPEG2026070694000014.jpg61170
[0031] In chemical formula E-1, m1 and m2 are independent integers between 0 and 5, and R 31 ~R 40 Each of these groups is independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted silyl group, a substituted or unsubstituted thio group, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms, a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heteroaryl group having 2 to 30 carbon atoms, or can bond with adjacent groups to form a ring.
[0032] One embodiment provides a monoamine compound represented by the chemical formula 1.
[0033] One embodiment provides an electronic device comprising a base layer, a circuit layer disposed on the base layer, and a display element layer disposed on the circuit layer and including a light-emitting element, wherein the light-emitting element includes a first electrode, a hole transport region disposed on the first electrode and containing a monoamine compound represented by chemical formula 1, a light-emitting layer disposed on the hole transport region, an electron transport region disposed on the light-emitting layer, and a second electrode disposed on the electron transport region.
[0034] The electronic device further includes at least one of the optical control layer and the color filter layer, wherein the optical control layer includes quantum dots and the color filter layer may include pigments or dyes.
[0035] The aforementioned electronic device includes a display device, which may include any one of the following: a television, a monitor, an external billboard, a personal computer, a laptop computer, a personal information terminal, a vehicle display device, a game console, a portable electronic device, and a camera. [Effects of the Invention]
[0036] A light-emitting element of one embodiment and an electronic device containing the same may exhibit high efficiency and long lifespan characteristics by containing the monoamine compound of one embodiment.
[0037] The monoamine compound of one embodiment may contribute to the high efficiency and extended lifespan of the light-emitting element. [Brief explanation of the drawing]
[0038] [Figure 1] This is a plan view showing a display device according to one embodiment. [Figure 2] This is a cross-sectional view showing the portion corresponding to the line I-I' in Figure 1. [Figure 3] This is a schematic cross-sectional view showing a light-emitting element of one embodiment. [Figure 4] This is a schematic cross-sectional view showing a light-emitting element of one embodiment. [Figure 5] This is a schematic cross-sectional view showing a light-emitting element of one embodiment. [Figure 6] This is a schematic cross-sectional view showing a light-emitting element of one embodiment. [Figure 7] This is a cross-sectional view showing a display device according to one embodiment. [Figure 8] This is a cross-sectional view showing a display device according to one embodiment. [Figure 9] This is a cross-sectional view showing a display device according to one embodiment. [Figure 10] This is a cross-sectional view showing a display device according to one embodiment. [Figure 11] This diagram shows the interior of a vehicle in which a display device according to one embodiment is installed. [Figure 12] This is a perspective view showing an electronic device in one embodiment. [Figure 13] This is an exploded perspective view showing an electronic device in one embodiment. [Modes for carrying out the invention]
[0039] Because the present invention can be modified in various ways and take on various forms, specific embodiments are illustrated in the drawings and described in detail in the text. However, this should be understood not as an attempt to limit the present invention to any particular disclosure, but rather as including all modifications, equivalents, or substitutes that fall within the spirit and technical scope of the present invention.
[0040] In this specification, when a component (or region, layer, part, etc.) is referred to as "on top of," "combined with," or "combined with" another component, it means that it can be directly placed on top of, connected to, or combined with the other component, or that a third component can be placed between them.
[0041] The same drawing symbol refers to the same component. Furthermore, in drawings, the thickness, proportions, and dimensions of components are exaggerated for the sake of effective explanation of the technical content. "and / or" includes all combinations of one or more components defined by the relevant component.
[0042] Terms such as "first," "second," etc., are used to describe a variety of components, but the components are not limited to those defined by these terms. These terms are used solely for the purpose of distinguishing one component from another. For example, without departing from the scope of the present invention, the first component may be named the second component, and similarly, the second component may also be named the first component. A singular form may include plural expressions unless the context clearly indicates otherwise.
[0043] Furthermore, terms such as "down," "on the lower side," "up," and "on the upper side" are used to describe the relationships between the components shown in the drawing. These terms are relative concepts and are described in relation to the direction shown in the drawing.
[0044] Terms such as "includes" or "possesses" indicate the presence of features, figures, steps, actions, components, parts, or combinations thereof described in the specification, and should be understood not to pre-exist to exclude the presence or possibility of adding one or more other features, figures, steps, actions, components, parts, or combinations thereof.
[0045] Unless otherwise defined, all terms used herein (including technical and scientific terms) have the same meaning as those generally understood by those skilled in the art in the field to which the present invention pertains. Furthermore, terms defined in commonly used dictionaries should be interpreted as having the same meaning as they do in the context of the relevant art, and should not be interpreted in an overly idealistic or formal sense unless expressly defined herein.
[0046] In this specification, "substituted or unsubstituted" may mean substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium atoms, halogen atoms, cyano groups, nitro groups, amine groups, amino groups, silyl groups, oxy groups, thio groups, sulfinyl groups, sulfonyl groups, carbonyl groups, boron groups, phosphine oxide groups, phosphine sulfide groups, alkyl groups, alkenyl groups, alkynyl groups, hydrocarbon ring groups, aryl groups, and heterocyclic groups. Furthermore, each of the substituents exemplified above may be substituted or unsubstituted. For example, a biphenyl group may be interpreted as an aryl group, or as a phenyl group substituted with a phenyl group.
[0047] In this specification, "bonding with adjacent groups to form a ring" means bonding with adjacent groups to form a substituted or unsubstituted hydrocarbon ring, or a substituted or unsubstituted heterocycle. Hydrocarbon rings include aliphatic hydrocarbon rings and aromatic hydrocarbon rings. Heterocyclic groups include aliphatic heterocyclic groups and aromatic heterocyclic groups. Hydrocarbon rings and heterocycles may be monocyclic or polycyclic. Furthermore, rings formed by bonding with each other may be linked to other rings to form a spirostructure.
[0048] In this specification, "adjacent group" may mean a substituent substituted on an atom directly linked to the atom on which the substituent is substituted, another substituent substituted on the atom on which the substituent is substituted, or the substituent that is most stereostructically adjacent to the substituent in question. For example, the two methyl groups in 1,2-dimethylbenzene may be interpreted as "adjacent groups," and the two ethyl groups in 1,1-diethylcyclopentene may be interpreted as "adjacent groups." Similarly, the two methyl groups in 4,5-dimethylphenanthrene may be interpreted as "adjacent groups."
[0049] In this specification, examples of halogen atoms include fluorine, chlorine, Brom, or iodine atoms.
[0050] In this specification, alkyl groups may be linear or branched. The number of carbon atoms in an alkyl group may be 1 to 60, 1 to 50, 1 to 30, 1 to 20, 1 to 10, or 1 to 6. Examples of alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, s-butyl, t-butyl, i-butyl, 2-ethylbutyl, 3,3-dimethylbutyl, n-pentyl, i-pentyl, neopentyl, t-pentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl, n-hexyl, and 1-methylhexyl 2-ethylhexyl group, 2-butylhexyl group, n-heptyl group, 1-methylpeptyl group, 2,2-dimethylheptyl group, 2-ethylheptyl group, 2-butylheptyl group, n-octyl group, t-octyl group, 2-ethyloctyl group, 2-butyloctyl group, 2-hexyloctyl group, 3,7-dimethyloctyl group, n-nonyl group, n-decyl group, 2-ethyldecyl group, 2-butyldecyl group, 2-hexyldecyl group Syl group, 2-octyldecyl group, n-undecyl group, n-dodecyl group, 2-ethyldodecyl group, 2-butyldodecyl group, 2-hexyldodecyl group, 2-octyldecyl group, n-tridecyl group, n-tetradecyl group, n-pentadecyl group, n-hexadecyl group, 2-ethylhexadecyl group, 2-butylhexadecyl group, 2-hexylhexadecyl group, 2-octylhexadecyl group, n-heptadecyl group, n-oc Examples of such groups include, but are not limited to, tadecyl group, n-nonadecyl group, n-icosyl group, 2-ethylicosyl group, 2-butylicosyl group, 2-hexylicosyl group, 2-octylicosyl group, n-henicosyl group, n-docosyl group, n-tricosyl group, n-tetracosyl group, n-pentacosyl group, n-hexacosyl group, n-heptacosyl group, n-octacosyl group, n-nonacosyl group, and n-triacontyl group.
[0051] In this specification, cycloalkyl groups may mean cyclic alkyl groups. The number of carbon atoms in a cycloalkyl group is 3 to 60, 3 to 50, 3 to 30, 3 to 20, or 3 to 10. Examples of cycloalkyl groups include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4-t-butylcyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, norbornyl, 1-adantyl, 2-adamantyl, isonorbornyl, and bicycloheptyl groups.
[0052] In this specification, an alkenyl group means a hydrocarbon group containing one or more carbon double bonds in the middle or terminal of an alkyl group having two or more carbon atoms. An alkenyl group may be linear or branched. The number of carbon atoms is not particularly limited, but is 2 to 60, 2 to 30, 2 to 20, or 2 to 10. Examples of alkenyl groups include, but are not limited to, vinyl, 1-butenyl, 1-pentenyl, 1,3-butadienylaryl, styrenyl, and styrylvinyl groups.
[0053] In this specification, an alkynyl group refers to a group of hydrocarbons containing one or more carbon triple bonds in the middle or terminal of an alkyl group having two or more carbon atoms. An alkynyl group may be linear or branched. The number of carbon atoms is not particularly limited, but is typically 2 to 30, 2 to 20, or 2 to 10. Typical examples of alkynyl groups include, but are not limited to, ethynyl and propynyl groups.
[0054] In this specification, a hydrocarbon ring group means any active group or substituent derived from an aliphatic hydrocarbon ring. A hydrocarbon ring group may be a saturated hydrocarbon ring group having 6 to 60, 6 to 30, 5 to 30, or 5 to 20 carbon atoms.
[0055] In this specification, an aryl group means any active group or substituent derived from an aromatic hydrocarbon ring. An aryl group may be a monocyclic aryl group or a polycyclic aryl group. The number of ring-forming carbon atoms in an aryl group may be 6 to 60, 6 to 30, 6 to 20, or 6 to 15. Examples of aryl groups include, but are not limited to, phenyl, naphthyl, fluorenyl, anthracenyl, phenanthryl, biphenyl, terphenyl, quarterphenyl, quincphenyl, sexiphenyl, triphenylenyl, pyrenyl, benzofluorantenyl, and chrysenyl groups.
[0056] In this specification, the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure. Examples of substitutions of the fluorenyl group are as follows, but are not limited to these.
[0057] JPEG2026070694000015.jpg27170
[0058] In this specification, a heterocyclic group means any active group or substituent derived from a ring containing one or more heteroatoms from B, O, N, P, Si, and S. Heterocyclic groups include aliphatic heterocyclic groups and aromatic heterocyclic groups. Aromatic heterocyclic groups may be heteroaryl groups. Aliphatic heterocyclic groups and aromatic heterocyclic groups may be monocyclic or polycyclic.
[0059] In this specification, a heterocyclic group may contain one or more heteroatoms from B, O, N, P, Si, and S. If a heterocyclic group contains two or more heteroatoms, the two or more heteroatoms may be the same or different. A heterocyclic group may be a monocyclic heterocyclic group or a polycyclic heterocyclic group, and may contain a heteroaryl group. The number of ring-forming carbon atoms in a heterocyclic group may be 2 to 60, 2 to 30, 5 to 30, 2 to 20, or 2 to 10.
[0060] In this specification, an aliphatic heterocyclic group may contain one or more heteroatoms from B, O, N, P, Si, and S. The number of ring-forming carbon atoms in an aliphatic heterocyclic group may be 2 to 60, 2 to 30, 2 to 20, or 2 to 10. Examples of aliphatic heterocyclic groups include, but are not limited to, oxirane groups, thiirane groups, pyrrolidine groups, piperidine groups, tetrahydrofuran groups, tetrahydrothiophene groups, thian groups, tetrahydropyran groups, and 1,4-dioxane groups.
[0061] In this specification, a heteroaryl group may contain one or more heteroatoms from B, O, N, P, Si, and S. If a heteroaryl group contains two or more heteroatoms, the two or more heteroatoms may be the same or different. A heteroaryl group may be a monocyclic heterocyclic group or a polycyclic heterocyclic group. The number of ring-forming carbon atoms in a heteroaryl group may be 2 to 60, 2 to 30, 2 to 20, or 2 to 10. Examples of heteroaryl groups include thiophene, furan, pyrrole, imidazole, pyridine, bipyridine, pyrimidine, triazine, triazole, acridyl, pyridazine, pyridinyl, quinoline, quinazoline, quinoxaline, phenoxazine, phthalazine, pyridopyrimidine, pyridopyrazine, pyrazinopyrazine, isoquinoline, indole, carbazole, N-arylcarbazole, and N-heteroaryl groups. Examples include, but are not limited to, N-alkylcarbazole groups, benzoxazole groups, benzimidazole groups, benzothiazole groups, benzocarbazole groups, benzothiophene groups, dibenzothiophene groups, thienothiophene groups, benzofuran groups, phenanthroline groups, thiazole groups, isoxazole groups, oxazole groups, oxadiazole groups, thiadiazole groups, phenothiazine groups, dibenzosilol groups, and dibenzofuran groups.
[0062] In this specification, the above description of aryl groups may apply, except that arylene groups are divalent. The above description of heteroaryl groups may apply, except that heteroarylene groups are divalent.
[0063] In this specification, the silyl group includes alkylsilyl groups and arylsilyl groups. Examples of silyl groups include, but are not limited to, trimethylsilyl, triethylsilyl, t-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, and phenylsilyl groups.
[0064] In this specification, the number of carbon atoms in the carbonyl group is not particularly limited, but may be 1 to 40, 1 to 30, or 1 to 20. For example, the carbonyl group may have, but is not limited to, the following structure.
[0065] JPEG2026070694000016.jpg25170
[0066] In this specification, the number of carbon atoms in the sulfinyl group and the sulfonyl group is not particularly limited, but may be between 1 and 30. The sulfinyl group may include an alkyl sulfinyl group and an aryl sulfinyl group. The sulfonyl group may include an alkyl sulfonyl group and an aryl sulfonyl group.
[0067] In this specification, the thio group may include alkylthio groups and arylthio groups. The thio group may mean a group to which a sulfur atom is bonded to the alkyl or aryl group as defined above. Examples of thio groups include, but are not limited to, methylthio, ethylthio, propylthio, pentylthio, hexylthio, octylthio, dodecylthio, cyclopentylthio, cyclohexylthio, phenylthio, and naphthylthio groups.
[0068] In this specification, an oxy group may mean a group in which an oxygen atom is bonded to an alkyl group or aryl group as defined above. Oxy groups may include alkoxy groups and aryloxy groups. Alkoxy groups may be linear, branched, or cyclic. The number of carbon atoms in an alkoxy group is not particularly limited, but may be, for example, 1 to 20 or 1 to 10. Examples of oxy groups include, but are not limited to, ethoxy, methoxy, n-propoxy, isopropoxy, butoxy, pentyloxy, hexyloxy, octyloxy, nonyloxy, decyloxy, and benzyloxy.
[0069] In this specification, a boron group may mean a group in which a boron atom is bonded to an alkyl or aryl group as defined above. A boron group may include alkylboron groups and arylboron groups. Examples of boron groups include, but are not limited to, dimethylboron, diethylboron, t-butylmethylboron, diphenylboron, and phenylboron.
[0070] In this specification, the number of carbon atoms in the amine group is not particularly limited, but may be 1 to 50, 1 to 30, or 1 to 20. The amine group may include alkylamine groups and arylamine groups. Examples of amine groups include, but are not limited to, methylamine groups, dimethylamine groups, phenylamine groups, diphenylamine groups, naphthylamine groups, and 9-methyl-anthracenylamine groups.
[0071] In this specification, among alkylthio groups, alkylsulfoxy groups, alkylaryl groups, alkylamino groups, alkylboron groups, alkylsilyl groups, and alkylamine groups, alkyl groups are as exemplified by the alkyl groups described above.
[0072] In this specification, among the aryloxy group, arylthio group, arylsulfoxy group, arylamino group, arylboron group, arylsilyl group, and arylamine group, the aryl group is as exemplified by the aryl group described above.
[0073] In this specification, direct bonding may mean single bonding.
[0074] JPEG2026070694000017.jpg12170 indicates the position where the images are concatenated.
[0075] An embodiment of the present invention will be described below with reference to the drawings.
[0076] Figure 1 is a plan view showing one embodiment of the display device DD. Figure 2 is a cross-sectional view of the display device DD according to one embodiment. Figure 2 is a cross-sectional view showing the portion corresponding to the line I-I' in Figure 1.
[0077] The display device DD may include a display panel DP and an optical layer PP disposed on the display panel DP. The display panel PP includes light-emitting elements ED-1, ED-2, and ED-3. The display device DD may include multiple light-emitting elements ED-1, ED-2, and ED-3. The optical layer PP is disposed on the display panel DP and can control the reflected light on the display panel DP due to external light. The optical layer PP may include, for example, a polarizing layer or a color filter layer. On the other hand, contrary to the figures, the optical layer PP may be omitted from the display device DD of one embodiment.
[0078] A base substrate BL may be placed on top of the optical layer PP. The base substrate BL may be a component that provides a base surface on which the optical layer PP is placed. The base substrate BL may be a glass substrate, a metal substrate, a plastic substrate, etc. However, the embodiment is not limited to these, and the base substrate BL may be an inorganic layer, an organic layer, or a composite material layer. Also, contrary to the figures, the base substrate BL may be omitted in one embodiment.
[0079] The display device DD according to one embodiment may further include a charging layer (not shown). A packing layer (not shown) may be disposed between the display element layer DP-ED and the base substrate BL. The packing layer (not shown) may be an organic layer. The packing layer (not shown) may contain at least one of acrylic resin, silicone resin, and epoxy resin.
[0080] The display panel DP may include a base layer BS, a circuit layer DP-CL provided on the base layer BS, and a display element layer DP-ED. The display element layer DP-ED may include a pixel definition film PDL, light-emitting elements ED-1, ED-2, and ED-3 disposed between the pixel definition film PDL, and a sealing layer TFE disposed on the light-emitting elements ED-1, ED-2, and ED-3.
[0081] The base layer BS may be a component that provides the base surface on which the display element layer EP-ED is arranged. The base layer BS may be a glass substrate, a metal substrate, a plastic substrate, etc. However, the examples are not limited to these, and the base layer BS may be an inorganic layer, an organic layer, or a composite material layer.
[0082] In one embodiment, the circuit layer DP-CL is placed on the base layer BS, but the circuit layer DP-CL may include a plurality of transistors (not shown). Each transistor (not shown) may include a control electrode, an input electrode, and an output electrode. For example, the circuit layer DP-ED may include a switching transistor and a drive transistor for driving the organic electroluminescent elements ED-1, ED-2, and ED-3.
[0083] Each of the light-emitting elements ED-1, ED-2, and ED-3 may have the structure of one embodiment of the light-emitting element ED shown in Figures 3 to 6, which will be described later. Each of the light-emitting elements ED-1, ED-2, and ED-3 may include a first electrode EL1, a hole transport region HTR, light-emitting layers EML-R, EML-G, and EML-B, an electron transport region ETR, and a second electrode EL2.
[0084] Figure 2 shows an embodiment in which the light-emitting layers EML-R, EML-G, and EML-B of light-emitting elements ED-1, ED-2, and ED-3 are arranged within an opening OH defined in the pixel-defining film PDL, and the hole transport region HTR, electron transport region ETR, and second electrode EL2 are provided as a common layer for all light-emitting elements ED-1, ED-2, and ED-3. However, the embodiment is not limited to this, and in one embodiment, contrary to the illustration in Figure 2, the hole transport region HTR and electron transport region ETR may be patterned and provided inside the opening OH defined in the pixel-defining film PDL. For example, in one embodiment, the hole transport region HTR, light-emitting layers EML-R, EML-G, EML-B, and electron transport region ETR of light-emitting elements ED-1, ED-2, and ED-3 may be patterned and provided by an inkjet printing method.
[0085] The sealing layer TFE may cover the organic electroluminescent elements ED-1, ED-2, and ED-3. The sealing layer TFE may seal the display element layer DP-ED. The sealing layer TFE may be a thin film sealing layer. The sealing layer TFE may consist of one or more layers stacked together. The sealing layer TFE includes at least one insulating layer. The sealing layer TFE according to one embodiment may include at least one inorganic film (hereinafter referred to as the sealing inorganic film). Furthermore, the sealing layer TFE according to one embodiment may include at least one organic film (hereinafter referred to as the sealing organic film) and at least one sealing inorganic film.
[0086] The encapsulating inorganic film protects the display element layer DP-ED from moisture / oxygen, and the encapsulating organic film protects the display element layer DP-ED from foreign matter such as dust particles. The encapsulating inorganic film may include, but is not limited to, silicon nitride, silicon oxynitride, silicon oxide, titanium oxide, or aluminum oxide. The encapsulating organic film may include, but is not limited to, acrylic compounds or epoxy compounds. The encapsulating organic film may include, but is not limited to, photopolymerizable organic materials.
[0087] The sealing layer TFE may be placed on top of the second electrode EL2 and fill the opening OH.
[0088] Referring to Figures 1 and 2, the display device DD may include a non-emitting region NPXA and emitting regions PXA-R, PXA-G, and PXA-B. Each of the emitting regions PXA-R, PXA-G, and PXA-B may be a region from which light generated by the light-emitting elements ED-1, ED-2, and ED-3, respectively, is emitted. The emitting regions PXA-R, PXA-G, and PXA-B may be spaced apart from each other on a plane.
[0089] Each of the light-emitting regions PXA-R, PXA-G, and PXA-B may be a region separated by a pixel-defining film PPL. The non-light-emitting region NPXA is the region between adjacent light-emitting regions PXA-R, PXA-G, and PXA-B, and may correspond to a pixel-defining film PDL. On the other hand, in this specification, each of the light-emitting regions PXA-R, PXA-G, and PXA-B may correspond to a pixel. The pixel-defining film PDL may separate the light-emitting elements ED-1, ED-2, and ED-3. The light-emitting layers EML-R, EML-G, and EML-B of the light-emitting elements ED-1, ED-2, and ED-3 may be located in and separated by an aperture OH defined in the pixel-defining film PDL.
[0090] The light-emitting regions PXA-R, PXA-G, and PXA-B can be divided into multiple groups according to the color of the light generated from the light-emitting elements ED-1, ED-2, and ED-3. The display device DD of one embodiment shown in Figures 1 and 2 exemplifies three light-emitting regions PXA-R, PXA-G, and PXA-B that emit red, green, and blue light, respectively. For example, the display device DD of one embodiment may include a red light-emitting region PXA-R, a green light-emitting region PXA-G, and a blue light-emitting region PXA-B that are separated from each other.
[0091] In one embodiment of the display device DD, the multiple light-emitting elements ED-1, ED-2, and ED-3 may emit light of different wavelengths. For example, in one embodiment, the display device DD may include a light-emitting element ED-1 that emits red light, a second light-emitting element ED-3 that emits green light, and a third light-emitting element ED-3 that emits blue light. In other words, the red light-emitting region PXA-R, the green light-emitting region PXA-G, and the blue light-emitting region PXA-B of the display device DD may correspond to the first light-emitting element ED-1, the second light-emitting element ED-2, and the third light-emitting element ED-3, respectively.
[0092] However, the examples are not limited to these, and the first to third light-emitting elements ED-1, ED-2, and ED-3 may emit light in the same wavelength range, or at least one of them may emit light in a different wavelength range. Furthermore, all of the first to third light-emitting elements ED-1, ED-2, and ED-3 may emit blue light.
[0093] In one embodiment of the display device DD, the light-emitting regions PXA-R, PXA-G, and PXA-B may be arranged in a striped pattern. Referring to Figure 1, multiple red light-emitting regions PXA-R, multiple green light-emitting regions PXA-G, and multiple blue light-emitting regions PXA-B may be aligned along the second directional axis DR2. Alternatively, the red light-emitting regions PXA-R, green light-emitting regions PXA-G, and blue light-emitting regions PXA-B may be arranged alternately along the first directional axis DR1.
[0094] Although Figures 1 and 2 show that the areas of the light-emitting regions PXA-R, PXA-G, and PXA-B are all similar, the examples are not limited to these, and the areas of the light-emitting regions PXA-R, PXA-G, and PXA-B may differ from each other depending on the wavelength range of the emitted light. On the other hand, the areas of the light-emitting regions PXA-R, PXA-G, and PXA-B may represent the area as viewed from the plane defined by the first directional axis DR1 and the second directional axis DR2.
[0095] On the other hand, the arrangement of the light-emitting regions PXA-R, PXA-G, and PXA-B is not limited to that shown in Figure 1, and the order in which the red light-emitting region PXA-R, green light-emitting region PXA-G, and blue light-emitting region PXA-B are arranged can be provided in various combinations depending on the display quality characteristics required by the display device DD. For example, the arrangement of the light-emitting regions PXA-R, PXA-G, and PXA-B can be Pentile. TM ) Arrangement form, or diamond (Diamond Pixel) TM ) It may have the form of an array.
[0096] Furthermore, the areas of the light-emitting regions PXA-R, PXA-G, and PXA-B may differ from each other. For example, in one embodiment, the area of the green light-emitting region PXA-G may be smaller than the area of the blue light-emitting region PXA-B, but the embodiment is not limited to this.
[0097] Figures 3 to 6 below are schematic cross-sectional views showing a light-emitting element according to one embodiment. The light-emitting element ED according to one embodiment may include a first electrode EL1, a hole transport region HTR, a light-emitting layer EML, an electron transport region ETR, and a second electrode EL2, which are stacked sequentially.
[0098] Figure 4 shows a cross-sectional view of an embodiment of a light-emitting element ED, compared to Figure 3, in which the hole transport region HTR includes a hole injection layer HIL and a hole transport layer HTL, and the electron transport region ETR includes an electron injection layer EIL and an electron transport layer ETL. Figure 5 also shows a cross-sectional view of an embodiment of a light-emitting element ED, compared to Figure 3, in which the hole transport region HTR includes a hole injection layer HIL, a hole transport layer HTL and an electron blocking layer EBL, and the electron transport region ETR includes an electron injection layer EIL, an electron transport layer ETL and a hole blocking layer HBL. Figure 6 shows a cross-sectional view of an embodiment of a light-emitting element ED, compared to Figure 4, in which a capping layer CPL is placed on the second electrode EL2.
[0099] The first electrode EL1 is conductive. The first electrode EL1 may consist of a metallic material, a metallic alloy, or a conductive compound. The first electrode EL1 may be an anode or a cathode. However, the examples are not limited to these. The first electrode EL1 may also be a pixel electrode. The first electrode EL1 may be a transmissive electrode, a semitransmissive electrode, or a reflective electrode. The first electrode EL1 may contain at least one selected from Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF, Mo, Ti, W, In, Sn, and Zn, two or more compounds selected from these, a mixture of two or more selected from these, or oxides thereof.
[0100] If the first electrode EL1 is a transmissive electrode, it may contain transparent metal oxides such as ITO (indium tin oxide), IZO (indium zinc oxide), ZnO (zinc oxide), ITZO (indium tin zinc oxide), etc. If the first electrode EL1 is a semi-transmissive or reflective electrode, it may contain Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF / Ca (a layered structure of LiF and Ca), LiF / Al (a layered structure of LiF and Al), Mo, Ti, W, or compounds or mixtures thereof (for example, a mixture of Ag and Mg). Alternatively, the first electrode EL1 may have a multi-layer structure including a reflective or semi-transmissive film made of the above-mentioned material, and a transparent conductive film made of ITO, IZO, ZnO, ITZO, etc. For example, the first electrode EL1 may have a three-layer structure of ITO / Ag / ITO, but is not limited to this. Furthermore, the examples are not limited to those described above, and the first electrode EL1 may include the metal material described above, a combination of two or more metal materials selected from the metal materials described above, or an oxide of the metal material described above. The thickness of the first electrode EL1 may be about 700 Å to about 10000 Å. For example, the thickness of the first electrode EL1 may be about 1000 Å to about 3000 Å.
[0101] In one embodiment, the light-emitting element ED may contain the monoamine compound of one embodiment. In one embodiment, the hole transport region HTR may contain the monoamine compound of one embodiment. At least one of the hole injection layer HIL, the hole transport layer HTL, and the electron blocking layer EBL may contain the monoamine compound of one embodiment. For example, the hole transport layer HTL may contain the monoamine compound of one embodiment.
[0102] The monoamine compound in one example may contain only one amine group. In this specification, substituents (e.g., aryl groups) bonded to an amine group that form a ring (e.g., a carbazole group) are not included in the amine group, and these (e.g., carbazole groups) are included in the heteroaryl group. Ring groups containing a nitrogen atom as a ring-forming atom (e.g., pyridine group, pyrimidine group, triazine group, carbazole group, etc.) are not included in the amine group, but are included in the heterocyclic group.
[0103] The monoamine compound of one embodiment may contain first to third substituents directly or indirectly bonded to the amine group. The first substituent is a 3,5-dinaphthalenylphenyl group, where the dinaphthalenylphenyl group may be a phenyl group substituted with two naphthalenyl groups. The second substituent may be a 2-naphthalenyl group. The third substituent may be an unsubstituted phenyl group, an unsubstituted naphthalenyl group, a naphthalenyl group substituted with a phenyl group, an unsubstituted phenantrenyl group, a phenantrenyl group substituted with a phenyl group, an unsubstituted dibenzofuranyl group, an unsubstituted dibenzothiophenyl group, an unsubstituted carbazolyl group, a carbazolyl group substituted with a phenyl group, an unsubstituted benzonaphthofuranyl group, or an unsubstituted benzonaphthothiophenyl group. As a result, the monoamine compound of one embodiment exhibits excellent hole transport properties and excellent material stability, and the light-emitting element ED of one embodiment containing the monoamine compound may exhibit high luminous efficiency and long lifetime properties.
[0104] The light-emitting element ED may contain the monoamine compound of one embodiment. The monoamine compound of one embodiment may be represented by the following chemical formula 1.
[0105] [Chemical formula 1] JPEG2026070694000018.jpg53170
[0106] In chemical formula 1, R 1 Naphthalenyl group containing R 2 A naphthalenyl group containing R 3 The phenyl group containing can correspond to the first substituent mentioned above (i.e., the dinaphthalenylphenyl group). 4 The naphthalenyl group containing Ar may correspond to the second substituent mentioned above. a This can correspond to the third substituent mentioned above.
[0107] In chemical formula 1, L 1 This can be a directly bonded, substituted, or unsubstituted ring-forming arylene group with 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heteroarylene group with 5 to 30 carbon atoms. For example, L 1 This can be a direct bond.
[0108] L 2 and L 3 Each of these can independently be a directly bonded, unsubstituted phenylene group, a phenylene group substituted with a deuterium atom, or a phenylene group substituted with a phenyl group. For example, L 2 L can be a direct combination or can be represented by any one of the following L2-1 to L2-4. 3 L can be a direct bond or can be represented by either L2-1 or L2-4 below. 3 If represented by L2-1, then any hydrogen atom in L2-1 can be substituted with a deuterium atom.
[0109] JPEG2026070694000019.jpg37170
[0110] In chemical formula 1, Ar aThis can be an unsubstituted phenyl group, an unsubstituted naphthalenyl group, a naphthalenyl group substituted with a phenyl group, an unsubstituted phenantrenyl group, a phenantrenyl group substituted with a phenyl group, an unsubstituted dibenzofuranyl group, an unsubstituted dibenzothiophenyl group, an unsubstituted carbazolyl group, a carbazolyl group substituted with a phenyl group, an unsubstituted benzonaphthofuranyl group, or an unsubstituted benzonaphthothiophenyl group. For example, Ar a This can be represented by any one of the following AR-1 through AR-38.
[0111] JPEG2026070694000020.jpg118170JPEG2026070694000021.jpg119170JPEG2026070694000022.jpg54170
[0112] In chemical formula 1, R 1 ~R 3 Each of these can independently be a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 ring-forming carbon atoms. For example, R 1 ~R 3 These can each be independently a hydrogen atom, a deuterium atom, a fluorine atom, or an unsubstituted phenyl group.
[0113] In chemical formula 1, R 4 Each of these can independently be a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 ring-forming carbon atoms. For example, R 4 This can be a hydrogen atom, a deuterium atom, a fluorine atom, an unsubstituted phenyl group, or an unsubstituted dibenzofuranyl group.
[0114] In chemical formula 1, R 4 A naphthalenyl group containing can be represented by any one of the following R4-1 to R4-6. In R4-5 below, D is a deuterium atom.
[0115] JPEG2026070694000023.jpg72170
[0116] In chemical formula 1, n1, n2, and n4 can each be independent integers between 0 and 7 (inclusive). n3 can be an integer between 0 and 3 (inclusive).
[0117] If n1 is an integer greater than or equal to 2, then multiple R 1 They can be the same or at least one can be different. If n1 is 0, then n1 is 7, and there are 7 R 1 This can be the same as when n is a hydrogen atom. If n2 is an integer greater than or equal to 2, then there can be multiple R 2 They can be the same or at least one can be different. If n2 is 0, then n2 is 7, and there are 7 R 2 This can be the same as when it is a hydrogen atom.
[0118] If n3 is an integer greater than or equal to 2, then multiple R 3 They can be the same or at least one can be different. If n3 is 0, then n3 is 3, and there are three R 3 This can be the same as when it is a hydrogen atom. If n4 is an integer greater than or equal to 2, then multiple R 4 They can be the same or at least one can be different. If n4 is 0, then n4 is 7, and there are 7 R 4 This can be the same as when it is a hydrogen atom.
[0119] In one embodiment, the monoamine compound represented by chemical formula 1 may include a chemical structure in which any hydrogen atom is substituted with a deuterium atom. For example, in chemical formula 1, R 4 L is a deuterium atom, and the monoamine compound of one example may contain a naphthalenyl group substituted with a deuterium atom. Alternatively, in chemical formula 1, L 3 The group is a phenylene group substituted with a deuterium atom, and the monoamine compound in one example may contain a phenylene group substituted with a deuterium atom. However, this is illustrative, and the examples are not limited to this.
[0120] In one embodiment, chemical formula 1 can be represented by any one of the following chemical formulas 1-A1 to 1-A3. Chemical formulas 1-A1 to 1-A3 are those in which R in chemical formula 1 1 Naphthalenyl group and R 2 Identify the bonding position of the naphthalenyl group containing L 1 This may indicate that they are directly bonded. In chemical formulas 1-A1 to 1-A3, L 2 , L 3 Ar a , R 1 ~R 4 The same principles described in Chemical Formula 1 can also be applied to n1 to n4.
[0121] [Chemical formula 1-A1] JPEG2026070694000024.jpg52170
[0122] [Chemical formula 1-A2] JPEG2026070694000025.jpg50170
[0123] [Chemical formula 1-A3] JPEG2026070694000026.jpg51170
[0124] In one embodiment, chemical formula 1 can be represented by any one of the following chemical formulas 1-B1 to 1-B3. Chemical formulas 1-B1 to 1-B3 are, in chemical formula 1, L 3 This could be a specific example of what is being identified and shown.
[0125] [Chemical formula 1-B1] JPEG2026070694000027.jpg50170
[0126] [Chemical formula 1-B2] JPEG2026070694000028.jpg58170
[0127] [Chemical formula 1-B3] JPEG2026070694000029.jpg61170
[0128] In chemical formulas 1-B1 to 1-B3, L 1 , L 2 Ar a , R 1 ~R 4 , and n1 to n4 can also be described in the same way as in Chemical Formula 1. In Chemical Formula 1-B2, n5 is an integer between 0 and 4, and R 5 This can be a hydrogen atom or a deuterium atom. If n5 is an integer greater than or equal to 2, there are multiple R 5 They can be the same or at least one can be different. If n5 is 0, then n5 is 4, and there are 4 R 5 This can be the same as when it is a hydrogen atom.
[0129] Chemical formula 1 may be represented by any one of the compounds in the following first group of compounds. The monoamine compound of one example may be represented by any one of the compounds in the following first group of compounds. The light-emitting element ED of one example may contain at least one of the compounds in the following first group of compounds. In the following first group of compounds, D is a deuterium atom.
[0130] [First compound group] JPEG2026070694000030.jpg167170JPEG2026070694000031.jpg166170JPEG2026070694000032.j pg174170JPEG2026070694000033.jpg159170JPEG2026070694000034.jpg168170JPEG20260706940 00035.jpg168170JPEG2026070694000036.jpg171170JPEG2026070694000037.jpg171170JPEG202 6070694000038.jpg160170JPEG2026070694000039.jpg162170JPEG2026070694000040.jpg247170
[0131] The monoamine compound of one example may contain first to third substituents directly or indirectly bonded to the amine group. The first substituent may be a 3,5-dinaphthalenylphenyl group, and the second substituent may be a naphthalenyl group. The third substituent may be the Ar group of chemical formula 1 described above. a This can correspond to the above chemical formula 1, R 1 Naphthalenyl group containing R 2 A naphthalenyl group containing R 3 A phenyl group containing R can constitute a 3,5-dinaphthalenylphenyl group. In the chemical formula 1 described above, R 4 The naphthalenyl group containing the dinaphthalenylphenyl group and the naphthalenyl group in one embodiment can correspond to the second substituent. The monoamine compound in one embodiment, containing the dinaphthalenylphenyl group and the naphthalenyl group, can exhibit excellent hole transport properties by appropriately adjusting the hole transport and improving the charge balance. Furthermore, the monoamine compound in one embodiment, containing the first to third substituents, can suppress an excessive rise in the deposition temperature, and can prevent material degradation during the deposition process. As a result, the monoamine compound in one embodiment, containing the first to third substituents, can exhibit excellent material stability. The light-emitting element (ED) in one embodiment, containing the monoamine compound in one embodiment, can exhibit high luminous efficiency and long lifetime characteristics.
[0132] The hole transport region (HTR) may include at least one of a hole injection layer (HIL), a hole transport layer (HTL), a buffer layer or luminescence auxiliary layer (not shown), and an electron blocking layer (EBL). The thickness of the hole transport region (HTR) may be, for example, about 50 Å to about 15,000 Å.
[0133] The hole transport region (HTR) may have a single layer made of a single material, a single layer made of multiple different materials, or a multilayer structure having multiple layers made of multiple different materials.
[0134] For example, the hole transport region HTR may have a single-layer structure of a hole injection layer HIL or a hole transport layer HTL, or it may have a single-layer structure consisting of a hole injection material and a hole transport material. Furthermore, the hole transport region HTR may have a single-layer structure consisting of multiple different materials, or it may have a structure of a hole injection layer HIL / hole transport layer HTL, a hole injection layer HIL / hole transport layer HTL / luminescence auxiliary layer (not shown), a hole injection layer HIL / luminescence auxiliary layer (not shown), a hole transport layer HTL / luminescence auxiliary layer (not shown), or a hole injection layer HIL / hole transport layer HTL / electron blocking layer EBL stacked sequentially from the first electrode EL1, but the examples are not limited to these.
[0135] Hole transport regions (HTRs) can be formed using a variety of methods, including vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) method, inkjet printing, laser printing, and laser-induced thermal imaging (LITI).
[0136] The hole transport region (HTR) may further include the compounds described below, in addition to the monoamine compound of one example.
[0137] The hole transport region (HTR) may contain a compound represented by the following chemical formula H-1.
[0138] [Chemical formula H-1] JPEG2026070694000041.jpg33170
[0139] In chemical formula H-1, L1 and L2 can each independently be directly bonded, substituted, or unsubstituted arylene groups with 6 to 30 ring-forming carbon atoms, or substituted or unsubstituted heteroarylene groups with 2 to 30 ring-forming carbon atoms. a and b can each independently be integers between 0 and 10. On the other hand, if a or b is an integer of 2 or more, then multiple L1 and L2 can each independently be substituted or unsubstituted arylene groups with 6 to 30 ring-forming carbon atoms, or substituted or unsubstituted heteroarylene groups with 2 to 30 ring-forming carbon atoms.
[0140] In chemical formula H-1, Ar1 to Ar2 can each independently be a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms. Furthermore, in chemical formula H-1, Ar3 can be a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms.
[0141] The compound represented by the chemical formula H-1 may be a monoamine compound. Alternatively, the compound represented by the chemical formula H-1 may be a diamine compound in which at least one of Ar1 to Ar3 contains an amine group as a substituent. Alternatively, the compound represented by the chemical formula H-1 may be a carbazole compound in which at least one of Ar1 to Ar2 contains a substituted or unsubstituted carbazole group, or a cafluorene compound in which at least one of Ar1 to Ar2 contains a substituted or unsubstituted fluorene group.
[0142] A compound represented by the chemical formula H-1 can be any one of the compounds in compound group H below. However, the compounds listed in compound group H below are illustrative examples, and the compound represented by the chemical formula H-1 is not limited to those shown in compound group H below.
[0143] [Compound group H] JPEG2026070694000042.jpg178170JPEG2026070694000043.jpg108170
[0144] The hole transport region (HTR) is used for phthalocyanine compounds such as copper phthalocyanine, and DNTPD(N 1 ,N 1’ -([1,1'-biphenyl]-4,4'-diyl)bis(N 1 -phenyl-N 4 ,N 4-di-m-tolylbenzene-1,,4-diamine), m-MTDATA(4,4',4”-[tris(3-methylphenyl)phenylamino]triphenylamino), TDATA(4,4',4”-tris(N,N-diphenylamino)triphenylamine), 2-TNATA(4,4',4”-tris[N(2-naphthyl)-N-phenylamino]-triphenylamine), PEDOT / PSS(poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate), PANI / DBSA(polyaniline / dodecylbenzenesulfonic acid) It may contain, among others, PANI / CSA (polyaniline / camphor sulfonic acid), PANI / PSS ((polyaniline) / poly(4-styrene sulfonate)), NPB (N,N'-di(naphthalene-1-yl)-N,N'-diphenyl-benzidine), polyether ketone containing triphenylamine (TPAPEK), 4-isopropyl-4'-methyldiphenyliodonium tetrakis(pentafluorophenyl) borate, HATCN (dipyradino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitride), etc.
[0145] The hole transport region HTR may include, for example, carbazole derivatives such as N-phenylcarbazole and polyvinylcarbazole, fluorene derivatives, triphenylamine derivatives such as TPD (N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine) and TCTA (4,4',4"-tris(N-carbazolyl)triphenylamine), NPB (N,N'-di(naphthalene-1-yl)-N,N'-diphenyl-benzidine), TAPC (4,4'-cyclohexylidenebis[N,N-bis(4-methylphenyl)benzeneamine]), HMTPD (4,4'-bis[N,N'-(3-tolyl)amino]-3,3'-dimethylbiphenyl), and mCP (1,3-bis(N-carbazolyl)benzene).
[0146] Furthermore, the hole transport region HTR may include CzSi(9-(4-tert-butylphenyl)-3,6-bis(triphenylsilyl)-9H-(carbazole), CCP(9-phenyl-9H-3,9'-bicarbazole), or mDCP(1,3-bis(1,8-dimethyl-9H-carbazole-9-yl)benzene).
[0147] The hole transport region HTR may include at least one of the hole injection layer HIL, hole transport layer HTL, and electron blocking layer EBL, which are the hole transport region compounds described above.
[0148] The thickness of the hole transport region (HTR) can be approximately 100 Å to approximately 10,000 Å, for example, approximately 100 Å to approximately 5,000 Å. If the hole transport region (HTR) includes a hole injection layer (HIL), the thickness of the hole injection layer (HIL) can be, for example, approximately 30 Å to approximately 1,000 Å. If the hole transport region (HTR) includes a hole transport layer (HTL), the thickness of the hole transport layer (HTL) can be approximately 30 Å to approximately 1,000 Å. For example, if the hole transport region (HTR) includes a hole blocking layer (EBL), the thickness of the hole blocking layer (EBL) can be, for example, approximately 10 Å to approximately 1,000 Å. If the thicknesses of the hole transport region (HTR), hole injection layer (HIL), hole transport layer (HTL), and electron blocking layer (EBL) satisfy the above-described ranges, satisfactory hole transport characteristics can be obtained without a substantial increase in the driving voltage.
[0149] The hole transport region (HTR) may further contain charge-generating materials in addition to the materials described above to improve conductivity. The charge-generating materials may be uniformly or non-uniformly dispersed within the hole transport region (HTR). The charge-generating materials may be, for example, p-dopant. The p-dopant may contain, but is not limited to, at least one of metal halide compounds, quinone derivatives, metal oxides, and cyano group-containing compounds. For example, p-dopants include metal halide compounds such as CuI and RBI, quinone derivatives such as TCNQ (tetracyanoquinodimethane) and F4-TCNQ (2,3,5,6-tetrafluoro-7,7',8,8-tetracyanoquinodimethane), metal oxides such as tungsten oxide and molybdenum oxide, and cyano group-containing compounds such as HATCN (dipyradino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonnitrile) and NDP9 (4-[[2,3-bis[cyano-(4-cyano-2,3,5,6-tetrafluorophenyl)methylidene]cyclopropylidene]-cyanomethyl]-2,3,5,6-tetrafluorobenzonitrile), but the examples are not limited to these.
[0150] As described above, the hole transport region (HTR) may further include at least one of a buffer layer (not shown) and an electron blocking layer (EBL) in addition to the hole injection layer (HIL) and the hole transport layer (HTL). The buffer layer (not shown) can increase the light emission efficiency by compensating for the resonance distance due to the wavelength of light emitted from the light emission layer (EML). The material included in the buffer layer (not shown) may be a material that can be included in the hole transport region (HTR). The electron blocking layer (EBL) may be a layer that prevents electron injection from the electron transport region (ETR) to the hole transport region (HTR).
[0151] The luminescent layer (EML) is provided on top of the hole transport region (HTR). The luminescent layer (EML) may have a thickness of, for example, about 100 Å to about 1000 Å, or about 100 Å to about 300 Å. The luminescent layer (EML) may have a multilayer structure consisting of a single layer made of a single material, a single layer made of multiple different materials, or multiple layers made of multiple different materials.
[0152] In a light-emitting device ED of an embodiment, the light-emitting layer EML may contain an anthracene derivative, a pyrene derivative, a fluoranthene derivative, a chrysene derivative, a dihydrobenzanthracene derivative, or a triphenylene derivative. Specifically, the light-emitting layer EML may contain an anthracene derivative or a pyrene derivative.
[0153] In the light-emitting device ED of an embodiment shown in FIGS. 3 to 6, the light-emitting layer EML may contain a host and a dopant, and the light-emitting layer EML may contain a compound represented by the following Chemical Formula E-1. The compound represented by the following Chemical Formula E-1 can be used as a fluorescent host material.
[0154] [Chemical Formula E-1] JPEG2026070694000044.jpg61170
[0155] In Chemical Formula E-1, m1 and m2 may each independently be an integer of 0 or more and 5 or less. If m1 is an integer of 2 or more, a plurality of Rs 39 may be the same or at least one may be different. If m1 is 0, it may be the same as the case where m1 is 5 and five Rs 39 are hydrogen atoms. If m2 is an integer of 2 or more, a plurality of Rs 40 may be the same or at least one may be different. If m2 is 0, it may be the same as the case where m2 is 5 and five Rs 40 are hydrogen atoms.
[0156] In Chemical Formula E-1, Rs 31 to Rs 40 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted silyl group, a substituted or unsubstituted thio group, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl having 2 to 30 ring-forming carbon atoms, or may combine with adjacent groups to form a ring.
[0157] Chemical formula E-1 can be represented by any one of the following compounds E1 to E21.
[0158] JPEG2026070694000045.jpg156170JPEG2026070694000046.jpg148170
[0159] In one embodiment, the light-emitting layer EML may contain a compound represented by the following chemical formula E-2a or chemical formula E-2b. The compound represented by the following chemical formula E-2a or chemical formula E-2b can be used as a host material for a phosphorescent element.
[0160] [Chemical formula E-2a] JPEG2026070694000047.jpg48170
[0161] In chemical formula E-2a, a is an integer of 0 or more and 10 or less, and L a can be a direct bond, a substituted or unsubstituted arylene group having 6 or more and 30 or less ring-forming carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 or more and 30 or less ring-forming carbon atoms. On the other hand, if a is an integer of 2 or more, L a can each independently be a substituted or unsubstituted arylene group having 6 or more and 30 or less ring-forming carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 or more and 30 or less ring-forming carbon atoms.
[0162] In chemical formula E-2a, A1 to A5 can each independently be N or CR i respectively. R a to R iEach of these groups may independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted amine group, a substituted or unsubstituted thio group, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heteroaryl group having 2 to 30 carbon atoms, or a group that forms a ring by bonding with adjacent groups. a ~R i These groups can bond with adjacent groups to form hydrocarbon rings or heterocycles containing N, O, S, etc., as ring-forming atoms.
[0163] On the other hand, in chemical formula E-2a, two or three selected from A1 to A5 are N and the rest are CR. i It is possible.
[0164] [Chemical formula E-2b] JPEG2026070694000048.jpg14170
[0165] In the chemical formula E-2b, Cbz1 and Cbz2 can each be independently a carbazole group or a carbazole group substituted with an aryl group having 6 to 30 ring-forming carbon atoms. b can be a directly bonded, substituted, or unsubstituted ring-forming arylene group with 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heteroarylene group with 2 to 30 carbon atoms. On the other hand, b is an integer between 0 and 10, and if b is an integer of 2 or more, multiple L b Each of these can independently be a substituted or unsubstituted arylene group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring-forming carbon atoms.
[0166] The compound represented by chemical formula E-2a and the compound represented by E-2b may be represented by any one of the compounds in compound group E-2 below. However, the compounds listed in compound group E-2 below are illustrative examples, and the compounds represented by chemical formula E-2a or chemical formula E-2b are not limited to those shown in compound group E-2 below.
[0167] [Compound group E-2] JPEG2026070694000049.jpg138170JPEG2026070694000050.jpg109170JPEG2026070694000051.jpg91170JPEG2026070694000052.jpg104170
[0168] The luminescent layer (EML) may further include common materials known in the relevant art as host materials. For example, the luminescent layer EML uses BCPDS (bis(4-(9H-carbazole-9-yl)phenyl)diphenylsilane), POPCPA ((4-(1-(4-(diphenylamino)phenyl)cyclohexyl)phenyl)diphenylphosphine oxide), DPEPO (bis[2-(diphenylphosphino)phenyl]ether oxide), CBP (4,4'-bis(N-carbazolyl)-1,1'-biphenyl), mCP (1,3-bis(carbazole-9-yl)benzene), PPF (2,8-bis(diphenylphosphoryl)dibenzo[b,d]furan), TCTA (4,4',4”-tris(carbazole-9-yl)-triphenylamine), and TPBi (1,3,5-tris(1-phenyl-1H-benzo[d]imidazole-2-yl)benzene) as host materials. It may contain at least one of the following. However, it is not limited to these, and for example, Alq3 (tris(8-hydroxyquinolino)aluminum), ADN (9,10-di(naphthalene-2-yl)anthracene), TBADN (3-tert-butyl-9,10-di(naphtho-2-yl)anthracene), DSA (distylyl arylene), CDBP (4,4'-bis(9-carbazolyl)-2,2'-dimethyl-biphenyl), MADN (2-methyl-9,10-bis(naphthalene-2-yl)anthracene), CP1 (hexaphenylcyclotriphosphazene), UGH2 (1,4-bis(triphenylsilyl)benzene), DPSiO3 (hexaphenylcyclotrisiloxane), DPSiO4 (octaphenylcyclotetrasiloxane), etc. can be used as host materials.
[0169] In one embodiment, the light-emitting layer EML may contain a compound represented by the following chemical formula Ma or chemical formula Mb. The compound represented by the following chemical formula Ma or chemical formula Mb can be used as a phosphorescent dopant material.
[0170] [Chemical formula Ma] JPEG2026070694000053.jpg48170
[0171] In the chemical formula Ma, Y1 to Y4 and Z1 to Z4 are each independently CR1 or N, and R1 to R4 are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted amine group, a substituted or unsubstituted thio group, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heteroaryl group having 2 to 30 carbon atoms, or are bonded to adjacent groups to form a ring. In the chemical formula Ma, m is 0 or 1, and n is 2 or 3. In the chemical formula Ma, if m is 0, then n is 3, and if m is 1, then n is 2.
[0172] The compound represented by the chemical formula Ma can be used as a phosphorescent dopant.
[0173] A compound represented by the chemical formula Ma may be any one of the compounds in the following group of compounds M-a1 to M-a25. However, the following compounds M-a1 to M-a25 are illustrative examples, and the compound represented by the chemical formula Ma is not limited to those represented by the following compounds M-a1 to M-a25.
[0174] JPEG2026070694000054.jpg160170JPEG2026070694000055.jpg235170
[0175] Compounds M-a1 and M-a2 can be used as red dopant materials, and compounds M-a3 to M-a5 can be used as green dopant materials.
[0176] [Chemical formula Mb] JPEG2026070694000056.jpg66170
[0177] In chemical formula Mb, Q1 to Q4 can each be independently C or N. C1 to C4 can each be independently a substituted or unsubstituted hydrocarbon ring having 5 to 30 ring-forming carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms.
[0178] L 21 ~L 24 Each is independently and directly connected.
[0179] JPEG2026070694000057.jpg38170 It may be a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring-forming carbon atoms. e1 to e4 may each be independently 0 or 1.
[0180] R 31 ~R 39 Each of these groups can independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, or can bond with adjacent groups to form a ring. d1 to d4 can each independently be an integer between 0 and 4. If d1 is an integer of 2 or more, multiple R groups can be formed. 31 If d2 is an integer greater than or equal to 2, then multiple R 32 They can be the same or at least one can be different. If d3 is an integer greater than or equal to 2, then multiple R 33 If d4 is an integer greater than or equal to 2, then multiple R 34 They may be the same or at least one of them may be different.
[0181] Compounds represented by the chemical formula Mb can be used as blue phosphorescent dopants or green phosphorescent dopants. The compound represented by the chemical formula Mb may be any one of the following compounds. However, these compounds are illustrative, and the compound represented by the chemical formula Mb is not limited to those listed below. In compounds AD-01 to AD-53, D represents a deuterium atom.
[0182] JPEG2026070694000058.jpg175170JPEG2026070694000059.jpg168170JPEG20260706940 00060.jpg177170JPEG2026070694000061.jpg151170JPEG2026070694000062.jpg151170
[0183] The luminescent layer EML may contain a compound represented by any one of the following chemical formulas: Fa to Fc. These compounds can be used as fluorescent dopant materials.
[0184] [Chemical formula Fa] JPEG2026070694000063.jpg44170
[0185] In the aforementioned chemical formula Fa, R a ~R j The two selected from among them are independent of each other.
[0186] Replaced with JPEG2026070694000064.jpg5170. R a ~R j among
[0187] The remaining unsubstituted atoms in JPEG2026070694000065.jpg5170 may each independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms.
[0188] In JPEG2026070694000066.jpg5170, Ar1 and Ar2 are each independently substituted or unsubstituted aryl groups with 6 to 30 ring-forming carbon atoms, or substituted or unsubstituted heteroaryl groups with 2 to 30 ring-forming carbon atoms. For example, at least one of Ar1 and Ar2 may be a heteroaryl group containing O or S as a ring-forming atom.
[0189] [Chemical formula Fb] JPEG2026070694000067.jpg33170
[0190] In the chemical formula Fb, R a and R b Each of these groups is independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted ring-forming alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heteroaryl group having 2 to 30 carbon atoms, or they bond with adjacent groups to form a ring. Ar1 and Ar4 can each independently be a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heteroaryl group having 2 to 30 carbon atoms.
[0191] In chemical formula Fb, U and V are each independently substituted or unsubstituted hydrocarbon rings having 5 to 30 ring-forming carbon atoms, or substituted or unsubstituted heterocycles having 2 to 30 ring-forming carbon atoms. At least one of Ar1 to Ar4 may be a heteroaryl group containing O or S as a ring-forming atom.
[0192] In the chemical formula Fb, the number of rings represented by U and V can be 0 or 1 independently. For example, in the chemical formula Fb, if the number of U or V is 1, the part represented by U or V constitutes a single-ring condensed ring, and if the number of U or V is 0, it means that the ring represented by U or V does not exist. More specifically, if the number of U is 0 and the number of V is 1, or if the number of U is 1 and the number of V is 0, the condensed ring with a fluorene core in the chemical formula Fb can be a four-ring cyclic compound. Also, if the number of both U and V is 0, the condensed ring with a fluorene core in the chemical formula Fb can be a three-ring cyclic compound. Furthermore, if the number of U and V is 1, the condensed ring with a fluorene core in the chemical formula Fb can be a five-ring cyclic compound.
[0193] [Chemical formula Fc] JPEG2026070694000068.jpg56170
[0194] In the chemical formula Fc, A1 and A2 are independently O, S, Se, or NR, respectively. m And R m R1 to R 11 Each of these groups is independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted amine group, a substituted or unsubstituted boryl group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thio group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, or is bonded to an adjacent group to form a ring.
[0195] In the chemical formula Fc, A1 and A2 can independently bond to substituents on adjacent rings to form fused rings. For example, A1 and A2 can independently form NR mTherefore, A1 may bond with R4 or R5 to form a ring. Also, A2 may bond with R7 or R8 to form a ring.
[0196] In one embodiment, the luminescent layer EML is a known dopant material, and is a styryl derivative (e.g., 1,4-bis[2-(3-N-ethylcarbazol)vinyl]benzene (BCzVB), 4-(di-p-tolylamino)-4'-[(di-p-tolylamino)styryl]stilbene (DPAVB), N-(4-((E)-2-(6-((E)-4-(diphenylamino)styryl)naphthalen-2-yl)vinyl)phenyl)- It may include N-phenylbenzeneamine (N-BDAVBi), 4,4'-bis[2-(4-(N,N-diphenylamino)phenyl)vinyl]biphenyl (DPAVBi), perylene and its derivatives (e.g., 2,5,8,11-tetra-t-butylperylene (TBP)), pyrene and its derivatives (e.g., 1,1'-dipylene, 1,4-dipyrenylbenzene, 1,4-bis(N,N'-diphenylamino)pyrene, etc.).
[0197] The luminescent layer EML may contain known phosphorescent dopant materials. For example, metal complexes containing iridium (Ir), platinum (Pt), osmium (Os), gold (Au), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), or thulium (Tm) may be used as phosphorescent dopants. Specifically, Flrpic (iridium(III)bis(4,6-difluorophenylpyridinate-N,C2')picolinate), Fir6 (bis(2,4-difluorophenylpyridinate)-tetrakis(1-pyrazolyl)borate-iridium(III)) or PtOEP (platinum-octaethylporphyrin) can be used as phosphorescent dopants. However, the examples are not limited to these.
[0198] The luminescent layer EML may contain quantum dot material. The core of the quantum dot can be selected from group II-VI compounds, group I-II-VI compounds, group II-IV-VI compounds, group I-II-IV-VI compounds, group II-IV-V compounds, group III-VI compounds, group I-III-VI compounds, group III-V compounds, group III-II-V compounds, group IV-VI compounds, group IV elements, group IV compounds, and combinations thereof.
[0199] Group II-VI compounds are binary compounds selected from the group consisting of CdSe, CdTe, CdS, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, MgSe, MgS, and mixtures thereof, CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, CdZnSe, CdZnTe, CdHgS, CdHgSe, C A ternary compound selected from the group consisting of dHgTe, HgZnS, HeZnSe, HeZnTe, MgZnSe, MgZnS, and mixtures thereof, and a quaternary compound selected from the group consisting of HgZnTeS, CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe, and mixtures thereof may be selected.
[0200] On the other hand, group II-VI compounds may further contain group I metals and / or group IV elements. Group I-II-VI compounds are selected from CuSnS or CuZnS, and group II-IV-VI compounds may be selected from ZnSnS, etc. Group I-II-IV-VI compounds may be selected from quaternary compounds selected from the group consisting of Cu2ZnSnS2, Cu2ZnSnS4, Cu2ZnSnSe4, Ag2ZnSnS2, and mixtures thereof.
[0201] The II-IV-V group compounds can be selected from ternary compounds selected from the group consisting of ZnSnP, ZnSnP2, ZnSnAs2, ZnGeP2, ZnGeAs2, CdSnP2, and CdGeP2, and mixtures thereof.
[0202] Group III-VI compounds may include binary compounds such as GaS, Ga2S3, GaSe, Ga2Se3, GaTe, InTe, InS, InSe, In2S3, In2Se3, ternary compounds such as InGaS3, InGaSe3, or any combination thereof.
[0203] Group I-III-VI compounds may be selected from the group consisting of AgInS, AgInS2, CuInS, CuInS2, AgGaS2, CuGaS2, CuGaO2, AgGaO2, AgAlO2, and mixtures thereof, or from quaternary compounds such as AgInGaS2 and CuInGaS2.
[0204] Group III-V compounds can be selected from the group consisting of binary compounds selected from the group consisting of GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, InSb, and mixtures thereof; ternary compounds selected from the group consisting of GaNP, GaNAs, GaNSb, GaPAs, GaPSb, AlNP, AlNAs, AlNSb, AlPAs, AlPSb, InGaP, InAlP, InNP, InNAs, InNSb, InPAs, InPSb, and mixtures thereof; and quaternary compounds selected from the group consisting of GaAlNP, GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNP, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs, InAlPSb, and mixtures thereof. On the other hand, Group III-V compounds may further contain Group II metals. For example, InZnP may be selected as a III-II-V group compound.
[0205] Group IV-VI compounds may be selected from the group consisting of binary compounds selected from the group consisting of SnS, SnSe, SnTe, PbS, PbSe, PbTe, and mixtures thereof; ternary compounds selected from the group consisting of SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, SnPbTe, and mixtures thereof; and quaternary compounds selected from the group consisting of SnPbSSe, SnPbSeTe, SnPbSTe, and mixtures thereof. Group IV elements may be selected from the group consisting of Si, Ge, and mixtures thereof. Group IV compounds may be binary compounds selected from the group consisting of SiC, SiGe, and mixtures thereof.
[0206] Each element in a multicomponent compound, such as the binary, ternary, and quaternary compounds, can exist within the particles at uniform or non-uniform concentrations. In other words, the chemical formula represents the types of elements contained in the compound, and the elemental ratios within the compound can vary. For example, AgInGaS2 is AgIn x Ga 1-x This can mean S² (where X is a real number between 0 and 1).
[0207] On the other hand, the quantum dot may have a single structure in which the concentration of each element contained in the quantum dot is uniform, or a core-shell dual structure. For example, the material contained in the core and the material contained in the shell may be different from each other.
[0208] The shell of the quantum dot may serve as a protective layer to prevent chemical degradation of the core and maintain its semiconductor properties, and / or as a charging layer to impart electrophoretic properties to the quantum dot. The shell may be a single layer or multiple layers. The interface between the core and the shell may have a concentration gradient in which the concentration of elements present in the shell decreases towards the center.
[0209] In some embodiments, the quantum dot may have a core-shell structure comprising a core containing the nanocrystals described above, and a shell surrounding the core. Examples of the shell of the quantum dot include metallic or nonmetallic oxides, semiconductor compounds, or combinations thereof.
[0210] For example, the metal or nonmetal oxides include binary compounds such as SiO2, Al2O3, TiO2, ZnO, MnO, Mn2O3, Mn3O4, CuO, FeO, Fe2O3, Fe3O4, CoO, Co3O4, and NiO, or ternary compounds such as MgAl2O4, CoFe2O4, NiFe2O4, and CoMn2O4, but the present invention is not limited to these.
[0211] Furthermore, examples of the semiconductor compound include CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnSeS, ZnTeS, GaAs, GaP, GaSb, HgS, HgSe, HgTe, InAs, InP, InGaP, InSb, AlAs, AlP, AlSb, and the like, but the present invention is not limited to these.
[0212] Each element in a multicomponent compound, such as a binary or ternary compound, can exist within the particles at uniform or non-uniform concentrations. In other words, the chemical formula represents the types of elements contained in the compound, and the elemental ratios within the compound can vary.
[0213] Quantum dots have an emission wavelength spectrum with a full width at half maximum (FWHM) of approximately 45 nm or less, preferably approximately 40 nm or less, and more preferably approximately 30 nm or less, and within this range, color purity and color reproducibility can be improved. Furthermore, since the light emitted through such quantum dots is emitted in all directions, the optical viewing angle can be improved.
[0214] Furthermore, the form of the quantum dots is not limited to those commonly used in this field, but more specifically, spherical, pyramidal, multi-arm, or cubic nanoparticles, nanotubes, nanowires, nanofibers, or nanoplate-like particles may be used.
[0215] The energy band gap can be adjusted by adjusting the size of the quantum dots or the elemental ratio within the quantum dot compound, thereby obtaining light in a variety of wavelengths from the quantum dot light-emitting layer. Therefore, by using quantum dots as described above (either using quantum dots of different sizes or having different elemental ratios within the quantum dot compound), it is possible to realize a light-emitting element that emits light of various wavelengths. Specifically, the size of the quantum dots and the elemental ratio within the quantum dot compound can be selected to emit red, green, and / or blue light. Furthermore, the quantum dots can be configured to emit white light by combining light of various colors.
[0216] In one embodiment of the light-emitting element ED shown in Figures 3 to 6, the electron transport region ETR is provided on the light-emitting layer EML. The electron transport region ETR includes, but is not limited to, at least one of the hole blocking layer HBL, electron transport layer ETL, and electron injection layer EIL.
[0217] The electron transport region (ETR) may have a single layer made of a single material, a single layer made of multiple different materials, or a multilayer structure having multiple layers made of multiple different materials.
[0218] For example, the electron transport region (ETR) may have a single-layer structure of an electron injection layer (EIL) or electron transport layer (ETL), or a single-layer structure consisting of an electron injection material and an electron transport material. Furthermore, the electron transport region (ETR) may have a single-layer structure consisting of multiple different materials, or it may have a structure of electron transport layer (ETL) / electron injection layer (EIL) or hole blocking layer (HBL) / electron transport layer (ETL) / electron injection layer (EIL) stacked sequentially from the light-emitting layer (EML), but is not limited to these. The thickness of the electron transport region (ETR) may be, for example, about 1000 Å to about 1500 Å.
[0219] Electron transport regions (ETRs) can be formed using a variety of methods, such as vacuum deposition, spin coating, casting, LB, inkjet printing, laser printing, and laser thermal transfer (LITI).
[0220] The electron transport region (ETR) may contain compounds represented by the following chemical formula ET-2.
[0221] [Chemical formula ET-2] JPEG2026070694000069.jpg49170
[0222] In the chemical formula ET-2, at least one of X1 to X3 is N, and the rest are CR. a It is possible. R a Ar1 to Ar3 can each be independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms.
[0223] In chemical formula ET-2, a to c can each be an integer between 0 and 10, independently of each other. In chemical formula ET-2, L1 and L3 can each be an arylene group with 6 to 30 directly bonded, substituted, or unsubstituted ring-forming carbon atoms, or a heteroarylene group with 2 to 30 substituted ring-forming carbon atoms, independently of each other. On the other hand, if a to c are integers of 2 or more, then multiple L1 and L3 can each be an arylene group with 6 to 30 substituted ring-forming carbon atoms, independently of each other, or a heteroarylene group with 2 to 30 substituted ring-forming carbon atoms, independently of each other.
[0224] The electron transport region (ETR) may include anthracene compounds. However, it is not limited to these; examples of electron transport region ETRs include Alq3 (tris(8-hydroxyquinolinato)aluminum), 1,3,5-tri[(3-pyridyl)phen-3-yl]benzene, 2,4,6-tris(3'-pyridin-3-yl)biphenyl-3-yl)-1,3,5-triazine, 2-(4-(N-phenylbenzimidazole-1-yl)phenyl)-9,10-dinaphthylanthracene, TPBi (1,3,5-tri(1-phenyl-1H-benzo[d]imidazole-2-yl)benzene), BCP (2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline), Bphen (4,7-diphenyl-1,10-phenanthroline), TAZ (3-(4-biphenylyl This may include ()-4-phenyl-5-terto-butylphenyl-1,2,4-triazole), NTAZ (4-(naphthalene-1-yl)-3,5-diphenyl-4H-1,2,4-triazole), tBu-PBD (2-(4-biphenylyl)-5-(4-terto-butylphenyl)-1,3,4-oxadiazole), BAlq (bis(2-methyl-8-quinolinolato-N1,O8)-(1,1'-biphenyl-4-orato)aluminum), Bebq2 (beryllium bis(benzoquinoline-10-orato), ADN (9,10-di(naphthalene-2-yl)anthracene), BmPyPhB (1,3-bis[3,5-di(pyridine-3-yl)phenyl]benzene), and mixtures thereof.
[0225] The electron transport region (ETR) may contain at least one of the following compounds ET1 to ET36.
[0226] JPEG2026070694000070.jpg214170JPEG2026070694000071.jpg156170JPEG2026070694000072.jpg251170
[0227] Furthermore, the electron transport region (ETR) may include metal halides such as LiF, NaCl, CsF, RbCl, RbI, CuI, and KI, lanthanum group metals such as Yb, or co-deposited materials of the aforementioned metal halides and lanthanum group metals. For example, the electron transport region (ETR) may include KI:Yb, RbI:Yb, LiF:Yb, etc., as co-deposited materials. On the other hand, the electron transport region (ETR) may also be a metal oxide such as Li2O, BaO, or Liq(8-hydroxylithium quinolate), but the examples are not limited to these. The electron transport region (ETR) may also consist of a mixture of an electron transport material and an insulating organometallic salt. The organometallic salt may be a material with an energy band gap of about 4 eV or more. For more details, organometallic salts may include metal acetate, metal benzoate, metal acetoacetate, metal acetylacetonate, or metal stearate.
[0228] The electron transport region (ETR) may, but is not limited to, further contain at least one of the following materials: BCP (2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline), TSPO1 (diphenyl(4-(triphenylsilyl)phenyl)phosphine oxide), and Bphen (4,7-diphenyl-1,10-phenanthroline).
[0229] The electron transport region ETR may include at least one of the electron injection layer EIL, electron transport layer ETL, and hole blocking layer HBL, as described above.
[0230] When the electron transport region ETR includes the electron transport layer ETL, the thickness of the electron transport layer ETL can be about 100 Å to about 1000 Å, for example, about 150 Å to about 500 Å. When the thickness of the electron transport layer ETL satisfies the above range, satisfactory electron transport characteristics can be obtained without substantial increase in driving voltage. When the electron transport region ETR includes the electron injection layer EIL, the thickness of the electron injection layer EIL can be about 1 Å to about 100 Å, about 3 Å to about 90 Å. When the thickness of the electron injection layer EIL satisfies the above range, satisfactory electron injection characteristics can be obtained without substantial increase in driving voltage.
[0231] The second electrode EL2 is provided on the electron transport region ETR. The second electrode EL2 can be a common electrode. The second electrode EL2 can be a cathode or an anode, but the embodiments are not limited thereto. For example, if the first electrode EL1 is an anode, the second electrode can be a cathode, and if the first electrode EL1 is a cathode, the second electrode EL2 can be an anode.
[0232] The second electrode EL2 can be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode. If the second electrode EL2 is a transmissive electrode, the second electrode EL2 can be made of a transparent metal oxide, such as ITO, IZO, ZnO, ITZO, etc.
[0233] If the second electrode EL2 is a semi-transmissive electrode or a reflective electrode, the second electrode EL2 can include Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF / Ca, LiF / Al, Mo, Ti, Yb, W, or a compound or mixture containing these (for example, AgMg, AgYb, or MgYb). Alternatively, the second electrode EL2 can have a multi-layer structure including a reflective film or a semi-transmissive film made of the above substances and a transparent conductive film made of ITO, IZO, ZnO, ITZO, etc. For example, the second electrode EL2 can include the above-mentioned metal materials, a combination of two or more metal materials selected from the above-mentioned metal materials, or an oxide of the above-mentioned metal materials.
[0234] Although not shown, the second electrode EL2 can be connected to an auxiliary electrode. If the second electrode EL2 is connected to the auxiliary electrode, the resistance of the second electrode EL2 is reduced.
[0235] On the other hand, a capping layer CPL can be further disposed on the second electrode EL2 of the light-emitting element ED of one embodiment. The capping layer CPL can include multiple layers or a single layer.
[0236] In one embodiment, the capping layer CPL can be an organic layer or an inorganic layer. For example, if the capping layer CPL includes an inorganic substance, the inorganic substance can include an alkali metal compound such as LiF, an alkaline earth compound such as MgF2, SiON, SiNx, SiOy, and the like.
[0237] For example, if the capping layer CPL includes an organic substance, the organic substance can include α-NPD, NPB, TPD, m-MTDATA, Alq3, CuPc, TPD15 (N4, N4, N4’, N4’-tetra (biphenyl-4-yl) biphenyl-4,4’-diamine), TCTA (4,4’,4”-tris (carbazol-9-yl) triphenylamine), etc., or can include an acrylate such as an epoxy resin or methacrylate. However, the embodiments are not limited thereto, and the capping layer CPL may include at least one of the following compounds P1 to P5.
[0238] JPEG2026070694000073.jpg168170
[0239] On the other hand, the refractive index of the capping layer CPL can be 1.6 or more. Specifically, for light in the wavelength range of 550 nm or more and 660 nm or less, the refractive index of the capping layer CPL can be 1.6 or more.
[0240] FIG. 7 and FIG. 10 are cross-sectional views of a display device according to one embodiment. Hereinafter, in the description of the display device according to one embodiment described with reference to FIGS. 7 and 10, the contents overlapping with those described in FIGS. 1 to 6 described above will not be described again, and the description will be centered on the differences.
[0241] Referring to Figure 7, one embodiment of the display device DD-a may include a display panel DP including a display element layer DP-ED, an optical control layer CCL disposed on the display panel DP, and a color filter layer CFL. In the embodiment shown in Figure 7, the display panel DP includes a base layer BS, a circuit layer DP-CL provided on the base layer BS, and a display element layer DP-ED, and the display element layer DP-ED may include a light-emitting element ED.
[0242] The light-emitting element ED may include a first electrode EL1, a hole transport region HTR placed on the first electrode EL1, an emissive layer EML placed on the hole transport region HTR, an electron transport region ETR placed on the emissive layer EML, and a second electrode EL2 placed on the electron transport region ETR. On the other hand, the structure of the light-emitting element ED shown in Figure 7 can also be adapted from the structures of the light-emitting elements shown in Figures 3 to 6 described above. The light-emitting element ED shown in Figure 7 may include the polycyclic compound of one embodiment. The light-emitting element ED including the monoamine compound of one embodiment may exhibit high luminous efficiency and long lifetime characteristics.
[0243] Referring to Figure 7, the light-emitting layer EML may be located within the aperture OH defined in the pixel definition film DPL. For example, the light-emitting layers EML provided corresponding to each light-emitting region PXA-R, PXA-G, and PXA-B, separated by the pixel definition film PDL, may emit light in the same wavelength range. In one embodiment of the display device DD-a, the light-emitting layer EML may emit blue light. On the other hand, contrary to the illustration, in one embodiment, the light-emitting layer EML may be provided as a common layer for the entire light-emitting regions PXA-R, PXA-G, and PXA-B.
[0244] The optical control layer (CCL) may be placed on top of the display panel (DP). The optical control layer (CCL) may contain photoconverters. These photoconverters may be quantum dots or phosphors, etc. The photoconverters may wavelength-convert the provided light and emit it. In other words, the optical control layer (CCL) may contain quantum dots or may be a layer containing phosphors.
[0245] The optical control layer (CCL) may include multiple optical control units CCP1, CCP2, and CCP3. The optical control units CCP1, CCP2, and CCP3 may be separated from each other.
[0246] Referring to Figure 7, a segmentation pattern BMP is provided between the optical control units CCP1, CCP2, and CCP3, which are separated from each other, but the embodiment is not limited to this. In Figure 7, it is shown that the segmentation pattern BMP does not overlap with the optical control units CCP1, CCP2, and CCP3, but the edges of the optical control units CCP1, CCP2, and CCP3 may overlap with the segmentation pattern BMP in at least part.
[0247] The optical control layer CCL may include a first optical control unit CCP1 which includes a first quantum dot QD1 that converts the first color light provided from the light-emitting element ED into second color light, a second optical control unit CCP2 which includes a second quantum dot QD2 that converts the first color light into third color light, and a third optical control unit CCP3 which transmits the first color light.
[0248] In one embodiment, the first optical control unit CCP1 may provide red light, which is the second color, and the second optical control unit CCP2 may provide green light, which is the third color. The third optical control unit CCP3 may transmit and provide blue light, which is the first color, provided from the light-emitting element ED. For example, the first quantum dot QD1 may be a red quantum dot, and the second quantum dot QD2 may be a green quantum dot. The same provisions as described above may apply to quantum dots QD1 and QD2.
[0249] Furthermore, the optical control layer CCL may further include a scatterer SP. The first optical control unit CCP1 includes a first quantum dot QD1 and a scatterer SP, the second optical control unit CCP2 includes a second quantum dot QD2 and a scatterer SP, and the third optical control unit CCP3 may include a scatterer SP without a quantum dot.
[0250] The scatterer SP may be inorganic particles. For example, the scatterer SP may contain at least one of TiO2, ZnO, Al2O3, SiO2, and hollow silica. The scatterer SP may contain at least one of TiO2, ZnO, Al2O3, SiO2, and hollow silica, or it may be a mixture of two or more substances selected from TiO2, ZnO, Al2O3, SiO2, and hollow silica.
[0251] The first optical control unit CCP1, the second optical control unit CCP2, and the third optical control unit CCP3 may each include base resins BR1, BR2, and BR3 for dispersing quantum dots QD1 and QD2 and scatterers SP. In one embodiment, the first optical control unit CCP1 may include first quantum dots QD1 and scatterers SP dispersed in the first base resin BR1, the second optical control unit CCP2 may include second quantum dots QD2 and scatterers SP dispersed in the second base resin BR2, and the third optical control unit CCP1 may include scatterers SP dispersed in the third base resin BR3.
[0252] The base resins BR1, BR2, and BR3 are the medium in which the quantum dots QD1 and QD2 and the scatterer SP are dispersed, and can consist of various resin compositions generally referred to as binders. For example, the base resins BR1, BR2, and BR3 can be acrylic resins, urethane resins, silicone resins, epoxy resins, etc. The base resins BR1, BR2, and BR3 are transparent resins. In one embodiment, the first base resin BR1, the second base resin BR2, and the third base resin BR3 may be the same as or different from each other.
[0253] The light control layer CCL may include a barrier layer BFL1. The barrier layer BFL1 may serve to prevent the penetration of moisture and / or oxygen (hereinafter referred to as "moisture / oxygen"). The barrier layer BFL1 may be placed on top of the light control units CCP1, CCP2, and CCP3 to block them from being exposed to moisture / oxygen. On the other hand, the barrier layer BFL1 may cover the light control units CCP1, CCP2, and CCP3. Furthermore, a barrier layer BLF2 may be provided between the light control units CCP1, CCP2, and CCP3 and the color filter layer CFL.
[0254] The barrier layers BFL1 and BFL2 may include at least one inorganic layer. That is, the barrier layers BFL1 and BFL2 may be formed by including an inorganic substance. For example, the barrier layers BFL1 and BFL2 may be formed by including silicon nitride, aluminum nitride, zirconium nitride, titanium nitride, hafnium nitride, tantalum nitride, silicon oxide, aluminum oxide, titanium oxide, tin oxide, cerium oxide, silicon oxynitride, a metal thin film with ensured light transmittance, etc. On the other hand, the barrier layers BFL1 and BFL2 may further include an organic film. The barrier layers BFL1 and BFL2 may be composed of a single layer or a plurality of layers.
[0255] In the display device DD-a of one embodiment, the color filter layer CFL is disposed on the light control layer CCL. For example, the color filter layer CFL may be directly disposed on the color control layer CCL. In this case, the barrier layer BFL2 may be omitted.
[0256] The color filter layer CFL may include filters CF1, CF2, and CF3. The color filter CFL may include a first filter CF1 that transmits second-color light, a second filter CF2 that transmits third-color light, and a third filter CF3 that transmits first-color light. For example, the first filter CF1 may be a red filter, the second filter CF2 may be a green filter, and the third filter CF3 may be a blue filter. Each of the filters CF1, CF2, and CF3 may include a polymer photosensitive resin and a pigment or a dye. The first filter CF1 includes a red pigment or dye, the second filter CF2 includes a green pigment or dye, and the third filter CF3 may include a blue pigment or dye.
[0257] On the other hand, the embodiment is not limited thereto, and the third filter CF3 may not include a pigment or a dye. The third filter CF3 may include a polymer photosensitive resin and may not include a pigment or a dye. The third filter CF3 may be transparent. The third filter CF3 may be made of a transparent photosensitive resin.
[0258] In one embodiment, the first filter CF1 and the second filter CF2 may be yellow filters. The first filter CF1 and the second filter CF2 may be provided as a single unit without being separated from each other.
[0259] Although not shown, the color filter layer CFL may further include a light-shielding portion (not shown). The light-shielding portion may be a black matrix. The light-shielding portion may be formed by comprising an organic or inorganic light-shielding material containing a black pigment or black dye. The light-shielding portion may prevent light leakage and demarcate the boundaries between adjacent filters CF1, CF2, and CF3. In one embodiment, the light-shielding portion may consist of a blue filter.
[0260] The first to third filters CF1, CF2, and CF3 may be arranged to correspond to the red emission region PXA-R, the green emission region PXA-G, and the blue emission region PXA-B, respectively.
[0261] A base substrate BL may be placed on top of the color filter layer CFL. The base substrate BL may be a component that provides a base surface on which the color filter layer CFL and the light control layer CCL are placed. The base substrate BL may be a glass substrate, a metal substrate, a plastic substrate, etc. However, the embodiment is not limited to these, and the base substrate BL may be an inorganic layer, an organic layer, or a composite material layer. Also, contrary to the figures, the base substrate BL may be omitted in one embodiment.
[0262] Figure 8 is a cross-sectional view showing a part of a display device according to one embodiment. In the display device DD-TD of one embodiment, the light-emitting element ED-BT may include a plurality of light-emitting structures OL-B1, OL-B2, and OL-B3. The light-emitting element ED-BT may include a plurality of light-emitting structures OL-B1, OL-B2, and OL-B3 that are sequentially stacked in the thickness direction between a first electrode EL1 and a second electrode EL2 facing each other, and between the first electrode EL1 and the second electrode EL2. Each of the light-emitting structures OL-B1, OL-B2, and OL-B3 may include a light-emitting layer EML (Figure 7) and a hole transport region HTR and an electron transport region ETR arranged with the light-emitting layer EML (Figure 7) in between. In other words, the light-emitting element ED-BT included in the display device DD-TD of one embodiment may be a light-emitting element with a tandem structure including a plurality of light-emitting layers.
[0263] The light-emitting element ED-BT shown in Figure 8 may contain the monoamine compound of one embodiment. The light-emitting element ED-BT containing the monoamine compound of one embodiment may exhibit high luminous efficiency and long lifetime characteristics.
[0264] In one embodiment shown in Figure 8, the light emitted from each of the light-emitting structures OL-B1, OL-B2, and OL-B3 can be blue light. However, the embodiment is not limited to this, and the wavelength ranges of the light emitted from each of the light-emitting structures OL-B1, OL-B2, and OL-B3 can be different from each other. For example, a light-emitting element ED-BT containing multiple light-emitting structures OL-B1, OL-B2, and OL-B3 that emit light in different wavelength ranges from each other can emit white light.
[0265] Charge generation layers CGL1 and CGL2 may be arranged between adjacent light-emitting structures OL-B1, OL-B2, and OL-B3. Charge generation layers CGL1 and CGL2 may include a p-type charge generation layer and / or an n-type charge generation layer.
[0266] Referring to Figure 9, the display device DD-b according to one embodiment includes light-emitting elements ED-1, ED-2, and ED-3, each having two stacked light-emitting layers. Compared to the display device DD of one embodiment shown in Figure 2, the difference in the embodiment shown in Figure 9 is that each of the first to third light-emitting elements ED-1, ED-2, and ED-3 includes two light-emitting layers stacked in the thickness direction. In each of the first to third light-emitting elements ED-1, ED-2, and ED-3, the two light-emitting layers may emit light in the same wavelength region. At least one of the first to third light-emitting elements ED-1, ED-2, and ED-3 may contain the monoamine compound of one embodiment. The light-emitting element containing the monoamine compound of one embodiment (at least one of ED-1, ED-2, and ED-3) may exhibit high luminous efficiency and long lifetime characteristics.
[0267] The first light-emitting element ED-1 may include a first red light-emitting layer EML-R1 and a second red light-emitting layer EML-R2. The second light-emitting element ED-2 may include a first green light-emitting layer EML-G1 and a second green light-emitting layer EML-G2. The third light-emitting element ED-3 may include a first blue light-emitting layer EML-B1 and a second blue light-emitting layer EML-B2. Light-emitting auxiliary units OG may be arranged between the first red light-emitting layer EML-R1 and the second red light-emitting layer EML-R2, between the first green light-emitting layer EML-G1 and the second green light-emitting layer EML-G2, and between the first blue light-emitting layer EML-B1 and the second blue light-emitting layer EML-B2.
[0268] The light-emitting auxiliary section OG may include a single layer or a multilayer. The light-emitting auxiliary section OG may include a charge generation layer. More specifically, the light-emitting auxiliary section OG may include sequentially stacked electron transport regions, a charge generation layer, and hole transport regions. The light-emitting auxiliary section OG may be provided in common across the first to third light-emitting elements ED-1, ED-2, and ED-3. However, the examples are not limited thereto, and the light-emitting auxiliary section OG may be provided patterned within an aperture OH defined in the pixel-defining film PDL.
[0269] The first red light-emitting layer EML-R1, the first green light-emitting layer EML-G1, and the first blue light-emitting layer EML-B1 may be positioned between the light-emitting auxiliary region OG and the electron transport region ETR. The second red light-emitting layer EML-R2, the second green light-emitting layer EML-G2, and the second blue light-emitting layer EML-B2 may be positioned between the hole transport region HTR and the light-emitting auxiliary region OG.
[0270] In other words, the first light-emitting element ED-1 may include a first electrode EL1 stacked sequentially, a hole transport region HTR, a second red light-emitting layer EML-R2, a light-emitting auxiliary section OG, a first red light-emitting layer EML-R1, an electron transport region ETR, and a second electrode EL2. The second light-emitting element ED-2 may include a first electrode EL1 stacked sequentially, a hole transport region HTR, a second green light-emitting layer EML-G2, a light-emitting auxiliary section OG, a first green light-emitting layer EML-G1, an electron transport region ETR, and a second electrode EL2. The third light-emitting element ED-3 may include a first electrode EL1 stacked sequentially, a hole transport region HTR, a second blue light-emitting layer EML-B2, a light-emitting auxiliary section OG, a first blue light-emitting layer EML-B1, an electron transport region ETR, and a second electrode EL2.
[0271] On the other hand, an optical auxiliary layer PL may be placed on the display element layer DP-ED. The optical auxiliary layer PL may include a polarizing layer. The optical auxiliary layer PL is placed on the display panel DP and can control the reflected light on the display panel DP due to external light. In one embodiment of the display device, the optical auxiliary layer PL may be omitted, contrary to the illustration.
[0272] Unlike Figures 8 and 9, the display device DD-c in Figure 10 is shown to include four light-emitting structures OL-B1, OL-B2, OL-B3, and OL-C1. The light-emitting element ED-CT may include a first electrode EL1 and a second electrode EL2 facing each other, and first to fourth light-emitting structures OL-B1, OL-B2, OL-B3, and OL-C1 sequentially stacked in the thickness direction between the first electrode EL1 and the second electrode EL2. Charge generation layers CGL1, CGL2, and CGL3 may be arranged between the first to fourth light-emitting structures OL-B1, OL-B2, OL-B3, and OL-C1. The light-emitting element ED-CT shown in Figure 10 may include the monoamine compound of one embodiment. The light-emitting element ED-CT including the monoamine compound of one embodiment may exhibit high luminous efficiency and long lifetime characteristics.
[0273] Of the four light-emitting structures, the first to third structures OL-B1, OL-B2, and OL-B3 may emit blue light, and the fourth light-emitting structure OL-C1 may emit green light. However, the examples are not limited to this, and the first to fourth light-emitting structures OL-B1, OL-B2, OL-B3, and OL-C1 may emit light in different wavelength regions.
[0274] The charge generation layers GCL1, CGL2, and CGL3, positioned between adjacent light-emitting structures OL-B1, OL-B2, OL-B3, and OL-C1, may include p-type charge generation layers and / or n-type charge generation layers.
[0275] Figure 11 shows a vehicle AM in which the first to fourth display devices DD-1, DD-2, DD-3, and DD-4 are arranged. At least one of the first to fourth display devices DD-1, DD-2, DD-3, and DD-4 may also include the same configuration as the display devices DD, DD-TD, DD-a, DD-b, and DD-c of one embodiment described with reference to Figures 1, 2, and 7 to 10.
[0276] Although Figure 11 shows an automobile as the vehicle AM, this is illustrative, and the first to fourth display devices DD-1, DD-2, DD-3, and DD-4 may be placed in other means of transport such as bicycles, motorcycles, trains, ships, and airplanes. Furthermore, at least one of the first to fourth display devices DD-1, DD-2, DD-3, and DD-4, which also include the same configuration as the display devices DD, DD-TD, DD-a, DD-b, and DD-c of one embodiment, may be used in personal computers, laptop computers, PDAs, game consoles, portable electronic devices, televisions, monitors, external advertising boards, etc. Moreover, these are merely presented as embodiments, and they may be display devices used in other electronic devices as long as they do not deviate from the concept of the present invention.
[0277] At least one of the first to fourth display devices DD-1, DD-2, DD-3, and DD-4 may include a light-emitting element ED as described with reference to Figures 3 to 6. At least one of the first to fourth display devices DD-1, DD-2, DD-3, and DD-4 may include the monoamine compound of one embodiment. A light-emitting element containing the monoamine compound of one embodiment (at least one of DD-1, DD-2, DD-3, and DD-4) may exhibit excellent display efficiency and display life characteristics.
[0278] Referring to Figure 11, the vehicle AM may include a steering wheel HA and a gear GR for operating the vehicle AM, and a forward window GL may be positioned to face the driver.
[0279] The first display device DD-1 may be positioned in a first area that overlaps with the steering wheel HA. For example, the first display device DD-1 may be a digital cluster that displays first information of the vehicle AM. The first information may include a first scale representing the vehicle AM's speed, a second scale indicating the engine speed (i.e., RPM (revolutions per minute)), and an image indicating the fuel status. The first and second scales may be displayed as digital images. Contrary to the illustration, the second information of the second display device DD-2 may be projected and displayed on the front window GL.
[0280] The second display device DD-2 may be positioned in a second area facing the driver's seat and superimposed on the front window GL. The driver's seat may be the seat on which the steering wheel HA is located. For example, the second display device DD-2 may be a head-up display (HUD) that displays second information about the vehicle AM. The second display device DD-2 may be optically transparent. The second information may include a digital digit DN indicating the vehicle AM's speed and may further include information such as the current time.
[0281] The third display device DD-3 may be located in a third area adjacent to the gear GR. For example, the third display device DD-3 may be located between the driver's seat and the passenger seat and may be a vehicle information guidance display (CID, Center Information Display) that displays third information. The passenger seat may be a seat separated from the driver's seat with the gear GR in between. The third information may include information about road conditions (e.g., navigation information), music or radio playback, dynamic video playback, and the temperature inside the vehicle AM.
[0282] The fourth display device DD-4 may be located in a fourth area adjacent to the side of the vehicle AM, separated from the steering wheel HA and gear GR. For example, the fourth display device DD-4 may be a digital side mirror that displays fourth information. The fourth display device DD-4 may display images of the area outside the vehicle AM captured by a camera module CM located outside the vehicle AM. The fourth information may include images of the area outside the vehicle AM.
[0283] The first to fourth pieces of information described above are illustrative, and the first to fourth display devices DD-1, DD-2, DD-3, and DD-4 may further display information about the interior and exterior of the vehicle. The first to fourth pieces of information may contain different information from each other. However, the embodiments are not limited to these, and some of the first to fourth pieces of information may contain the same information from each other.
[0284] In one embodiment, the electronic device may include a display device containing a plurality of light-emitting elements and a control unit that controls the display device. The electronic device in one embodiment may be a device that is activated by an electrical signal. The electronic device may include display devices of various embodiments. For example, the display device may include large display devices such as televisions, monitors, or external billboards, as well as medium- and small-sized display devices such as personal computers, laptop computers, personal information terminals, vehicle display devices, game consoles, portable electronic devices, and cameras.
[0285] Figure 12 is a perspective view showing an electronic device of one embodiment. Figure 13 is an exploded perspective view showing an electronic device of one embodiment.
[0286] The display device EA can display video IM via the display surface EA-IS. Video IM may include both dynamic and static images. The display surface EA-IS may be aligned with the plane defined by the first directional axis DR1 and the second directional axis DR2. Figure 12 shows an electronic device EA equipped with a planar display surface EA-IS, but the embodiment is not limited to this. For example, the electronic device EA may include a curved display surface or a three-dimensional display surface. The three-dimensional display surface may include multiple display areas that indicate different directions from each other.
[0287] The display surface EA-IS may include a display area EA-DA and a non-display area EA-NDA. The display surface EA-IS may further include a sub-area MH. The electronic device EA may display an image IM via the display area EA-DA.
[0288] The non-display area EA-NDA may have a predetermined color. The non-display area EA-NDA may be adjacent to the display area EA-DA. The non-display area EA-NDA may surround the display area EA-DA. Thus, the shape of the display area EA-DA may be substantially defined by the non-display area EA-NDA. However, Figure 12 is an illustrative diagram, and the non-display area EA-NDA may be located adjacent to only one side of the display area EA-DA, or it may be omitted.
[0289] The sub-region MH may sense external objects received via the display surface EA-IS, or it may provide audio signals such as sound to the outside via the display surface EA-IS. Optical signals such as visible light or infrared light may travel to the sub-region MH.
[0290] Sub-region MH may be located within the display region EA-DA. However, this is illustrative, and the arrangement of sub-region MH is not limited to just one embodiment. For example, sub-region MH may be surrounded by the non-display region EA-NDA, or by both the display region EA-DA and the non-display region EA-NDA. Although one sub-region MH is shown in Figure 12, multiple sub-regions MH may be provided.
[0291] Various electronic modules ELM (Figure 13) can be arranged to correspond to the sub-region MH. For example, an electronic module ELM (Figure 13) may include at least one of a camera, speaker, light-sensing sensor, and thermal-sensing sensor. The electronic device EA may include an electronic module ELM (Figure 13) that captures an external image via visible light passing through the sub-region MH, or determines the proximity of an external object via infrared light. An electronic module ELM (Figure 13) may include multiple configurations and is not limited to any one embodiment.
[0292] Referring to Figure 13, the electronic device EA may include a display device DD. The display device EA may further include a display module ELM, a window member WM, and a housing HAU.
[0293] The window member WM may cover the entire outside of the display device EA. The window member WM may include a transparent region TA and a bezel region BZA. The front surface of the window member WM, including the transparent region TA and the bezel region BZA, may be the front surface of the display device EA. The transparent region TA may correspond to the display region EA-DA of the electronic device EA shown in Figure 12, and the bezel region BZA may correspond to the non-display region EA-NDA of the electronic device EA shown in Figure 12.
[0294] The transparent region TA may be an optically transparent region. The bezel region BZA may be a region with relatively lower light transmittance compared to the transparent region TA. The bezel region BZA may have a predetermined color. The bezel region BZA may be adjacent to and surround the transparent region TA. The bezel region BZA may define the shape of the transparent region TA. However, the embodiment is not limited to this, and the bezel region BZA may be located adjacent to only one side of the transparent region TA, or a portion of it may be omitted.
[0295] The housing (HAU) may include materials with relatively high rigidity. For example, the housing (HAU) may include frames and / or plates made of glass, plastic, or metal. The frames and / or plates may be supplied in multiple units. The housing (HAU) may provide a predetermined housing space. The display device (DD) may be housed within the housing space and protected from external impacts.
[0296] The display device DD may include the same configuration as at least one of the display devices DD, DD-TD, DD-a, DD-b, and DD-c described with reference to Figures 1, 2, and 7 to 10 of one embodiment. The display device DD may include the light-emitting element ED described with reference to Figures 3 to 6. Thus, the electronic device EA including the display device DD according to one embodiment can exhibit excellent reliability.
[0297] The display device DD may have an active area DM-AA, a peripheral area DM-NAA, and a module area DM-MH. The active area DM-AA may be superimposed on the display area EA-DA shown in Figure 12, and the peripheral area DM-NAA may be superimposed on the non-display area EA-NDA shown in Figure 12. The module area DM-MH may be superimposed on the sub-area MH shown in Figure 12.
[0298] The active region DM-AA may be a region activated by an electrical signal. The peripheral region DM-NAA may be a region located adjacent to at least one side of the active region DM-AA. The active region DM-AA may include the illustrated non-emitting region NPXA and the emitting regions PXA-R, PXA-G, and PXA-B. The peripheral region DM-NAA may be arranged surrounding the active region DM-AA. However, the embodiment is not limited to this, and some parts of the peripheral region DM-NAA may be omitted from the illustration. The peripheral region DM-NAA may contain drive circuits and drive wiring for driving the active region DM-AA.
[0299] Optical signals such as visible light or infrared light can be transmitted to the module region DM-MH. The module region DM-MH may be located within the active region DM-AA. Alternatively, the module region DM-MH may be surrounded by the peripheral region DM-NAA, or surrounded by the active region DM-AA and the peripheral region DM-NAA.
[0300] An electronic module (ELM) can be an electronic component that outputs or receives optical signals. An electronic module (ELM) may include a camera module and / or a proximity sensor. The camera module may capture external images via the module region DM-MH. However, the embodiments are not limited thereto, and an electronic module (ELM) may further include an internal module and / or an external module. An internal module may include a sensor module, an antenna module, and an acoustic output module. An external module may include a light module and a communication module.
[0301] The following describes in detail a monoamine compound and a light-emitting element of one embodiment according to one embodiment of the present invention, with reference to examples and comparative examples. Furthermore, the following examples are illustrative to aid in understanding the present invention, and the scope of the present invention is not limited thereto.
[0302] [Examples] 1. Synthesis of a monoamine compound in one example The method for synthesizing monoamine compounds according to this embodiment will be specifically explained with examples of the synthesis methods for monoamine compounds 3, 8, 18, 39, 71, and 94. Furthermore, the synthesis methods for monoamine compounds described below are just one example, and the synthesis methods for compounds according to the embodiments of the present invention are not limited to the examples below.
[0303] (1) Synthesis of intermediate compounds The intermediate compounds used below can be synthesized by the steps of reaction formulas 1-1 to 1-3 below.
[0304] [Reaction Equation 1-1] JPEG2026070694000074.jpg39170
[0305] <Synthesis of Intermediate Compound 3-A> Under an Ar atmosphere, 1,3-dibromo-5-chlorobenzene (30.0 g), naphthalene-1-ylboronic acid (38.2 g), tetrakis(triphenylphosphine)palladium(0) (Pd(PPh3)4, 6.4 g), and potassium carbonate (K2CO3, 61.3 g) were placed in a 1 L three-necked flask and dissolved in a mixed solvent of toluene, water, and ethanol (EtOH) (volume ratio 10:2:1, 500 mL). The mixture was then heated and stirred at 80°C for 16 hours. Water was added to the solution, and the organic layer was extracted with dichloromethane (CH2Cl2). The obtained organic layer was dried in one go over magnesium sulfate (MgSO4), and the solvent was removed by vacuum distillation. The obtained crude product was purified by recrystallization to obtain 30.8 g of intermediate compound 3-A (yield 76%). The molecular weight of intermediate compound 3-A, as measured by FAB-MS, was 364.
[0306] [Reaction Equation 1-2] JPEG2026070694000075.jpg35170
[0307] <Synthesis of Intermediate Compound 3-B> Intermediate compound 3-B was obtained in 35.1 g (87% yield) using the same method as the synthesis of intermediate compound 3-A, except that naphthalene-2-ylboronic acid (38.2 g) was used instead of naphthalene-1-ylboronic acid (38.2 g). The molecular weight of intermediate compound 3-B, as measured by FAB-MS, was 364.
[0308] [Reaction Equations 1-3] JPEG2026070694000076.jpg67170
[0309] <Synthesis of intermediate compound 3-C> Under an Ar atmosphere, 1,3-dibromo-5-chlorobenzene (30.0 g), naphthalene-2-ylboronic acid (19.2 g), Pd(PPh3)4 (6.4 g), and K2CO3 (31.0 g) were placed in a 1 L three-necked flask and dissolved in a mixed solvent of toluene, water, and ethanol (volume ratio 10:2:1, 500 mL). The mixture was heated and stirred at 80°C for 16 hours. Water was added to the solution, and the organic layer was extracted with CH2Cl2 to obtain the organic layer. The obtained organic layer was dried in one go over MgSO4, and the solvent was removed by vacuum distillation. The obtained crude product was purified by silica gel column chromatography and recrystallization to obtain 18.5 g of intermediate compound 3-C (yield 52%). The molecular weight of intermediate compound 3-C, as measured by FAB-MS, was 317.
[0310] <Synthesis of intermediate compound 3-D> Intermediate compound 3-D was synthesized in the same manner as intermediate compound 3-C, except that intermediate compound 3-C (15.0 g) was used instead of 1,3-dibromo-5-chlorobenzene (30.0 g), and naphthalene-1-ylboronic acid (8.1 g) was used instead of naphthalene-2-ylboronic acid (19.2 g). Intermediate compound 3-D was obtained in 14.8 g (86% yield) by the same method as the synthesis of intermediate compound 3-C. The molecular weight of intermediate compound 3-D, as measured by FAB-MS, was 364.
[0311] (2) Synthesis of monoamine compound 3 The monoamine compound 3 according to one example can be synthesized, for example, by the steps of the following reaction formula 2.
[0312] [Reaction Equation 2] JPEG2026070694000077.jpg84170
[0313] <Synthesis of intermediate compound 3-E> Under an Ar atmosphere, 4-(naphthalene-2-yl)aniline (10.0 g), intermediate compound 3-A (16.6 g), bis(dibenzylideneacetone)palladium(0) (Pd(dba)2, 0.3 g), and sodium tert-butoxide (NaOtBu, 6.6 g) were placed in a 500 mL three-necked flask and dissolved in toluene (200 mL). Tri-tert-butylphosphine (P(tBu)3, 2.0 M in toluene, 0.5 mL) was added, and the mixture was stirred at room temperature for 8 hours. Water was added to the solution, and the organic layer was extracted with CH2Cl2. The obtained organic layer was dried in one go over MgSO4, and the solvent was removed by vacuum distillation. The obtained crude product was purified by silica gel column chromatography and recrystallization to obtain 14.2 g of intermediate compound 3-E (yield 57%). The molecular weight of intermediate compound 3-E, as measured by FAB-MS, was 547.
[0314] <Synthesis of Compound 3> Under an Ar atmosphere, intermediate compound 3-E (5.0 g), 2-bromonaphthalene (1.9 g), Pd(dba)2 (0.05 g), and NaOtBu (1.3 g) were placed in a 300 mL three-necked flask, dissolved in toluene (100 mL), and P(tBu)3 (2.0 M in toluene, 0.1 mL) was added. The mixture was heated under reflux at 100 °C for 4 hours. Water was added to the solution, and the organic layer was extracted with CH2Cl2. The obtained organic layer was dried in one go over MgSO4, and the solvent was removed by vacuum distillation. The obtained crude product was purified by silica gel column chromatography to obtain 5.2 g of compound 3 (yield 85%). The molecular weight of compound 3, as measured by FAB-MS, was 673.
[0315] (3) Synthesis of monoamine compound 8 The monoamine compound 8 according to one example can be synthesized, for example, by the steps of the following reaction formula 3.
[0316] [Reaction Equation 3] JPEG2026070694000078.jpg40170
[0317] Intermediate compound 8 was obtained in 5.5 g (81% yield) by the same method as the synthesis of compound 3, except that 2-bromo-7-phenylnaphthalene (2.6 g) was used instead of 2-bromonaphthalene (1.9 g). The molecular weight of compound 8, as measured by FAB-MS, was 749.
[0318] (4) Synthesis of monoamine compound 18 The monoamine compound 18 according to one example can be synthesized, for example, by the steps of the following reaction formula 4.
[0319] [Reaction Equation 4] JPEG2026070694000079.jpg40170
[0320] Intermediate compound 18 was obtained in 5.4 g (84% yield) by the same method as the synthesis of compound 3, except that 2-bromobenzofuran (2.3 g) was used instead of 2-bromonaphthalene (1.9 g). The molecular weight of compound 18, as measured by FAB-MS, was 713.
[0321] (5) Synthesis of monoamine compound 39 The monoamine compound 39 according to one example can be synthesized, for example, by the steps of the following reaction formula 5.
[0322] [Reaction Equation 5] JPEG2026070694000080.jpg35170
[0323] Intermediate compound 39 was obtained in 5.4 g (80% yield) using the same method as the synthesis of compound 3, except that 2-(4-bromophenyl)naphthalene (2.6 g) was used instead of 2-bromonaphthalene (1.9 g). The molecular weight of compound 39, as measured by FAB-MS, was 749.
[0324] (6) Synthesis of monoamine compound 71 The monoamine compound 71 according to one embodiment can be synthesized, for example, by the steps of the following reaction formula 6.
[0325] [Reaction Equation 6] JPEG2026070694000081.jpg81170
[0326] <Synthesis of intermediate compound 71-F> Intermediate compound 71-F was obtained in 12.2 g (49% yield) using the same method as the synthesis of intermediate compound 3-E, except that intermediate compound 3-B (16.6 g) was used instead of intermediate compound 3-A (16.6 g). The molecular weight of intermediate compound 71-F, as measured by FAB-MS, was 547.
[0327] <Synthesis of Compound 71> Compound 71 was synthesized in the same manner as compound 3, except that intermediate compound 71-F (5.0 g) was used instead of intermediate compound 3-E (5.0 g), and 3-bromophenanthrene (2.4 g) was used instead of 2-bromonaphthalene (1.9 g), to obtain 5.2 g (80% yield). The molecular weight of compound 71, as measured by FAB-MS, was 723.
[0328] (7) Synthesis of monoamine compound 94 The monoamine compound 94 according to one example can be synthesized, for example, by the steps of the following reaction formula 7.
[0329] [Reaction Equation 7] JPEG2026070694000082.jpg43170
[0330] Compound 94 was obtained in 5.1 g (75% yield) using the same method as the synthesis of compound 3, except that intermediate compound 71-F (5.0 g) was used instead of intermediate compound 3-E (5.0 g), and 1-(4-bromophenyl)nanthrene (2.6 g) was used instead of 2-bromonaphthalene (1.9 g). The molecular weight of compound 94, as measured by FAB-MS, was 749.
[0331] (8) Synthesis of monoamine compound 37 The monoamine compound 37 according to one example can be synthesized, for example, by the steps of the following reaction formula 8.
[0332] [Reaction Equation 8] JPEG2026070694000083.jpg38170
[0333] Intermediate compound 37 was obtained in 5.2 g (81% yield) by the same method as the synthesis of compound 3, except that 4-bromoviphenyl (2.2 g) was used instead of 2-bromonaphthalene (1.9 g). The molecular weight of compound 37, as measured by FAB-MS, was 699.
[0334] (9) Synthesis of monoamine compound 44 The monoamine compound 44 according to one example can be synthesized, for example, by the steps of the following reaction formula 9.
[0335] [Reaction Equation 9] JPEG2026070694000084.jpg42170
[0336] Intermediate compound 44 was obtained in 5.4 g (68% yield) by the same method as the synthesis of compound 3, except that 9-(4-chloromophenyl)-10-phenylnaphthalene (3.4 g) was used instead of 2-bromonaphthalene (1.9 g). The molecular weight of compound 44, as measured by FAB-MS, was 876.
[0337] (10) Synthesis of monoamine compound 104 The monoamine compound 104 according to one embodiment can be synthesized, for example, by the steps of the following reaction formula 10.
[0338] [Reaction Equation 10] JPEG2026070694000085.jpg43170
[0339] Compound 104 was obtained in 4.7 g (65% yield) by the same method as the synthesis of compound 3, except that intermediate compound 71-F (5.0 g) was used instead of intermediate compound 3-E (5.0 g), and 9-(4-bromophenyl)-9H-carbazole (2.9 g) was used instead of 2-bromonaphthalene (1.9 g). The molecular weight of compound 104, as measured by FAB-MS, was 788.
[0340] (11) Synthesis of monoamine compound 81 The monoamine compound 81 according to one embodiment can be synthesized, for example, by the steps of the following reaction formula 11.
[0341] [Reaction Equation 11] JPEG2026070694000086.jpg45170
[0342] Compound 81 was obtained in 5.0 g (70% yield) by the same method as the synthesis of compound 3, except that intermediate compound 71-F (5.0 g) was used instead of intermediate compound 3-E (5.0 g), and 2-bromo-9-phenyl-9H-carbazole (3.0 g) was used instead of 2-bromonaphthalene (1.9 g). The molecular weight of compound 81, as measured by FAB-MS, was 788.
[0343] (12) Synthesis of monoamine compound 29 The monoamine compound 29 according to one example can be synthesized, for example, by the steps of the following reaction formula 12.
[0344] [Reaction Equation 12] JPEG2026070694000087.jpg40170
[0345] Intermediate compound 29 was obtained in 5.4 g (77% yield) by the same method as the synthesis of compound 3, except that 9-bromonaphthobenzofuran (2.8 g) was used instead of 2-bromonaphthalene (1.9 g). The molecular weight of compound 29, as measured by FAB-MS, was 763.
[0346] (13) Synthesis of monoamine compound 36 The monoamine compound 36 according to one example can be synthesized, for example, by the steps of the following reaction formula 13.
[0347] [Reaction Equation 13] JPEG2026070694000088.jpg43170
[0348] Intermediate compound 36 was obtained in 4.0 g (50% yield) by the same method as the synthesis of compound 3, except that 10-bromobenzonaphthothiophene (2.9 g) was used instead of 2-bromonaphthalene (1.9 g). The molecular weight of compound 36, as measured by FAB-MS, was 780.
[0349] 2. Fabrication and evaluation of light-emitting devices
[0350] (1) Fabrication of light-emitting element A light-emitting element containing the monoamine compound of one example or the comparative compound in the hole transport layer was manufactured by the following method. The light-emitting elements of Examples 1 to 12 were manufactured using the monoamine compounds 3, 8, 18, 39, 71, 94, 37, 44, 104, 81, 29, and 36 of one example as the material for the hole transport layer. The light-emitting elements of Comparative Examples 1 to 14 were manufactured using the comparative compounds X-1 to X-14 as the material for the hole transport layer.
[0351] A glass substrate patterned with 150 nm of ITO was ultrasonically cleaned for 5 minutes each using isopropyl alcohol and pure water as the first electrode. After ultrasonic cleaning, it was irradiated with UV light for 30 minutes and then treated with ozone. Next, a hole injection layer was formed by depositing 2-TNATA to a thickness of 60 nm. On top of the hole injection layer, the example compound or comparative example compound was deposited to a thickness of 30 nm to form a hole transport layer.
[0352] A light-emitting layer with a thickness of 25 nm was formed by co-depositing TBP and ADN onto a hole transport layer. The TBP and ADN were co-deposited in a weight ratio of 3:97. Next, an electron transport region was formed by sequentially depositing Alq3 to a thickness of 25 nm and LiF to a thickness of 1 nm. Then, a second electrode was formed by depositing Al to a thickness of 100 nm. The hole injection layer, hole transport layer, light-emitting layer, electron transport region, and second electrode were formed using a vacuum deposition apparatus.
[0353] <Materials used in fabricating the light-emitting element> JPEG2026070694000089.jpg54170
[0354] <Example Compounds> JPEG2026070694000090.jpg78170JPEG2026070694000091.jpg81170<Comparative example compound> JPEG2026070694000092.jpg145170JPEG2026070694000093.jpg91170
[0355] (2) Evaluation of light-emitting elements Table 1 below shows the evaluation of the light-emitting elements of the comparative example and the example. Current density: 10 mA / cm² 2 The luminous efficiency and lifetime were evaluated using a Hamamatsu Photonics C9920-11 luminance orientation characteristic measuring device. The lifetime LT50 is the time required for the initial luminance to decrease from 100% to 50%. In Table 1, the luminous efficiency and lifetime are shown as relative values, with the values for Comparative Example 1 set to 100%.
[0356] [Table 1]
[0357] Referring to Table 1, it can be seen that the light-emitting elements of Examples 1 to 12 exhibit higher luminous efficiency and longer lifespan compared to the light-emitting elements of Comparative Examples 1 to 14. In particular, the lifespan of the light-emitting elements of Examples 1 to 8, 11 and 12 is significantly improved. The light-emitting elements of Examples 1 to 12 each contain compounds 3, 8, 18, 39, 71, 94, 37, 44, 104, 81, 29, and 36, respectively, and compounds 3, 8, 18, 39, 71, 94, 37, 44, 104, 81, 29, and 36 are one-example monoamine compounds. Compounds 3, 8, 18, 39, 71, 94, 37, 44, 104, 81, 29, and 36 contain first to third substituents directly or indirectly bonded to the amine group. The first substituent is a 3,5-dinaphthalenylphenyl group, and the second substituent is a naphthalenyl group. This demonstrates that the monoamine compound in one embodiment improves the efficiency and lifespan of the light-emitting element. The light-emitting element containing the monoamine compound in one embodiment exhibits high luminous efficiency and long lifespan characteristics.
[0358] The light-emitting element of Comparative Example 1 contains comparative compound X-1. Comparative compound X-1 is the Ar of chemical formula 1 described above. a Since it is a dimethylfluorenyl group, it differs from the monoamine compound of one example. The monoamine compound of one example represented by chemical formula 1 is Ar a The definition does not include a dimethylfluorenyl group. Comparative example compound X-1, which contains a dimethyl group, is thermally unstable and increases the deposition temperature. Therefore, the light-emitting element of Comparative Example 1 exhibits low luminous efficiency and a short lifetime.
[0359] The light-emitting element of Comparative Example 2 contains comparative compound X-2. Comparative compound X-2 is the L of chemical formula 1 described above. 3 Since it is a phenyl group substituted with a naphthalenyl group, it differs from the monoamine compound of one example. The monoamine compound of one example represented by chemical formula 1 is L 3The definition does not include phenyl groups substituted with naphthalenyl groups. Comparative example compound X-2 introduces two dinaphthalenylphenyl groups, which increases the deposition temperature and causes thermal decomposition during deposition, thus reducing the lifespan of the light-emitting element. Therefore, the light-emitting element of Comparative Example 2 exhibits low luminous efficiency and a short lifespan.
[0360] The light-emitting element of Comparative Example 3 contains Comparative Example Compound X-3. Comparative Example Compound X-3 contains a terphenyl group but does not contain a naphthalenyl group (i.e., the second substituent mentioned above). The presence of a terphenyl group in Comparative Example Compound X-3 increases the deposition temperature, causing thermal decomposition during deposition and reducing the lifespan of the light-emitting element. Therefore, the light-emitting element of Comparative Example 3 exhibits low luminous efficiency and a short lifespan.
[0361] The light-emitting element of Comparative Example 4 contains comparative compound X-4. Comparative compound X-4 is the Ar of chemical formula 1 described above. a Since it is a dibenzofuranyl group substituted with a phenyl group, it differs from the monoamine compound in one example. The monoamine compound in one example represented by chemical formula 1 is Ar a The definition excludes dibenzofuranyl groups substituted with phenyl groups, but includes substituted dibenzofuranyl groups. Comparative example compound X-4, which incorporates dibenzofuranyl groups substituted with phenyl groups, exhibits reduced charge transport properties and decreased efficiency of the light-emitting element. Therefore, the light-emitting element of Comparative Example 4 shows low luminous efficiency and a short lifetime. Furthermore, hole transport materials containing dibenzothiophenyl groups substituted with phenyl groups tend to exhibit reduced charge transport properties compared to hole transport materials containing unsubstituted dibenzothiophenyl groups.
[0362] The light-emitting element of Comparative Example 5 contains Comparative Example Compound X-5. Comparative Example Compound X-5 contains the first substituent (i.e., a dinaphthalenylphenyl group) as described above, but does not contain the second and third substituents. The presence of a phenyl-substituted dibenzofuranyl group and a triphenylenyl group in Comparative Example Compound X-5 increases the deposition temperature, causing thermal decomposition during deposition and reducing the lifespan of the light-emitting element. Therefore, the light-emitting element of Comparative Example 5 exhibits low luminous efficiency and a short lifespan.
[0363] The light-emitting element of Comparative Example 6 contains Comparative Example Compound X-6. Comparative Example Compound X-6 contains a dinaphthalenylphenyl group, but differs from the monoamine compound of Example 1 in the bonding positions of the two naphthalenyl groups. Comparative Example Compound X-6 contains a 2,3-dinaphthalenylphenyl group, while the monoamine compound of Example 1 contains a 3,5-dinaphthalenylphenyl group. Comparative Example Compound X-6, which contains the 2,3-dinaphthalenylphenyl group, a substituent with high steric hindrance, undergoes thermal decomposition during deposition, reducing the lifespan of the light-emitting element. As a result, the light-emitting element of Comparative Example 6 exhibits low luminous efficiency and a short lifespan.
[0364] The light-emitting devices of Comparative Examples 7, 9, and 14 each contain compounds X-7, X-9, and X-14 for comparison. Comparative Examples X-7, X-9, and X-14 differ from the monoamine compound of Example 1 in the bonding position of the naphthalenyl group, which is the second substituent. Comparative Examples X-7, X-9, and X-14 contain a 1-naphthalenyl group, while the monoamine compound of Example 1 contains a 2-naphthalenyl group. The introduction of a 1-naphthalenyl group in Comparative Examples X-7, X-9, and X-14 reduces material stability and shortens the lifespan of the light-emitting devices. As a result, the light-emitting devices of Comparative Examples 7, 9, and 14 exhibit low luminous efficiency and short lifespans.
[0365] The light-emitting element of Comparative Example 8 contains Comparative Example Compound X-8. Comparative Example Compound X-8 does not contain a naphthalenyl group as the second substituent, but contains a phenantrenyl group. The presence of a phenantrenyl group as the second substituent in Comparative Example Compound X-8 increases the deposition temperature, causing thermal decomposition during deposition and reducing the lifespan of the light-emitting element. As a result, the light-emitting element of Comparative Example 8 exhibits low luminous efficiency and a short lifespan.
[0366] The light-emitting devices of Comparative Examples 10 to 12 each contain Comparative Example Compounds X-10 to X-12. Comparative Example Compounds X-10 to X-12 differ from the monoamine compound of Example 1 in that they contain a 2,6-dinaphthalenyl group. The monoamine compound of Example 1 contains a 3,5-dinaphthalenyl group. As a result, the light-emitting devices of Comparative Examples 10 to 12 exhibit low luminous efficiency and short lifetimes.
[0367] The light-emitting element of Comparative Example 13 contains Comparative Example Compound X-13. Comparative Example Compound X-13 does not contain the second substituent, the 2-naphthalenyl group, but contains a t-butyl group. The t-butyl group is a thermally unstable substituent, and the material stability of Comparative Example Compound X-13 containing the t-butyl group is reduced. As a result, the light-emitting element of Comparative Example 13 exhibits low luminous efficiency and a short lifetime.
[0368] In one embodiment, the electronic device may include a light-emitting element. In the light-emitting element of one embodiment, the hole transport region may include the monoamine compound of one embodiment. The monoamine compound of one embodiment may include first to third substituents directly or indirectly bonded to the amine group. The first substituent may be a 3,5-dinaphthalenylphenyl group, and the second substituent may be a 2-naphthalenyl group. As a result, the monoamine compound of one embodiment may exhibit excellent hole transport properties and excellent material stability, and the light-emitting element of one embodiment containing the monoamine compound may exhibit high efficiency and long lifespan. The electronic device of one embodiment may exhibit excellent reliability.
[0369] Although preferred embodiments of the present invention have been described so far with reference, a person skilled in the art or with ordinary knowledge in the art will understand that the present invention can be modified and altered in various ways without departing from the spirit and technical domain of the invention as described in the claims below.
[0370] Therefore, the technical scope of the present invention is not limited to what is described in the detailed description of the specification, but should be determined by the claims. [Explanation of Symbols]
[0371] ED: Light-emitting element EL1: First electrode EL2: Second electrode EML: Light-emitting layer HTR: Hole transport region ETR: Electron transport region
Claims
1. First electrode and A hole transport region is placed on the first electrode and contains a monoamine compound represented by the following chemical formula 1, A light-emitting layer disposed on the hole transport region, An electron transport region disposed on the light-emitting layer, A light-emitting element including a second electrode disposed on the electron transport region: [Chemical formula 1] In the aforementioned chemical formula 1, L 1 This is a directly linked, substituted or unsubstituted ring-forming arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heteroarylene group having 5 to 30 carbon atoms. L 2 and L 3 These are, independently, directly bonded, unsubstituted phenylene groups, phenylene groups substituted with deuterium atoms, or phenylene groups substituted with phenyl groups. Ar a This is an unsubstituted phenyl group, an unsubstituted naphthalenyl group, a naphthalenyl group substituted with a phenyl group, an unsubstituted phenantrenyl group, a phenantrenyl group substituted with a phenyl group, an unsubstituted dibenzofuranyl group, an unsubstituted dibenzothiophenyl group, an unsubstituted carbazolyl group, a carbazolyl group substituted with a phenyl group, an unsubstituted benzonaphthofuranyl group, or an unsubstituted benzonaphthothiophenyl group. R 1 ~R 3 Each of these is independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or an unsubstituted heteroaryl group having 5 to 30 ring-forming carbon atoms. R 4 This is a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 carbon atoms. n1, n2, and n4 are each independent integers between 0 and 7, n3 is an integer between 0 and 3, This includes chemical structures in which any hydrogen atom is replaced by a deuterium atom.
2. The light-emitting element according to claim 1, wherein the aforementioned chemical formula 1 is represented by any one of the following chemical formulas 1-A1 to 1-A3: [Chemical formula 1-A1] [Chemical formula 1-A2] [Chemical formula 1-A3] In the above chemical formulas 1-A1 to 1-A3, L 2 、 L 3 、 Ar a 、 R 1 up to R 4 、 and n1 to n4 are as defined in Chemical Formula 1 above.
3. The light-emitting element according to claim 1, wherein the aforementioned chemical formula 1 is represented by any one of the following chemical formulas 1-B1 to 1-B3: [Chemical formula 1-B1] [Chemical formula 1-B2] [Chemical formula 1-B3] In the aforementioned chemical formula 1-B2, n5 is an integer between 0 and 4, R 5 is a hydrogen atom or a deuterium atom, In the above chemical formulas 1-B1 to 1-B3, L 1 , L 2 Ar a , R 1 ~R 4 , and n1 to n4 are as defined in Chemical Formula 1 above.
4. In the above chemical formula 1, L 2 The light-emitting element according to claim 1 is either directly coupled or represented by any one of L2-1 to L2-4 below: 。
5. In the above chemical formula 1, Ar a The light-emitting element according to claim 1, which is represented by any one of AR-1 to AR-38 below: 。
6. In the above chemical formula 1, R 1 ~R 3 The light-emitting element according to claim 1, wherein each is independently a hydrogen atom, a deuterium atom, a fluorine atom, or an unsubstituted phenyl group.
7. In the above chemical formula 1, R 4 The light-emitting element according to claim 1, wherein is a hydrogen atom, a deuterium atom, a fluorine atom, an unsubstituted phenyl group, or an unsubstituted dibenzofuranyl group.
8. In the above chemical formula 1, R 4 The naphthalenyl group containing is represented by any one of the following R4-1 to R4-6, according to claim 1: In the above R4-5, D is a deuterium atom.
9. The light-emitting element according to claim 1, wherein the monoamine compound is represented by any one of the compounds in the following first group of compounds: [First compound group] In the first group of compounds, D is a deuterium atom.
10. The hole transport region includes a hole injection layer, a hole transport layer disposed on the hole injection layer, and an electron blocking layer disposed on the hole transport layer. The light-emitting element according to claim 1, wherein at least one of the hole injection layer, hole transport layer, and electron blocking layer comprises the monoamine compound.
11. The light-emitting element according to claim 1, comprising a compound represented by the following chemical formula E-1 in the light-emitting layer: [Chemical formula E-1] In the aforementioned chemical formula E-1, m1 and m2 are independent integers between 0 and 5, R 31 ~R 40 Each of these groups is independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted silyl group, a substituted or unsubstituted thio group, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms, a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heteroaryl group having 2 to 30 carbon atoms, or is bonded to an adjacent group to form a ring.
12. Monoamine compounds represented by the following chemical formula 1: [Chemical formula 1] In the aforementioned chemical formula 1, L 1 This is a directly bonded, substituted, or unsubstituted ring-forming arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heteroarylene group having 5 to 30 carbon atoms. L 2 and L 3 These are, independently, directly bonded, unsubstituted phenylene groups, phenylene groups substituted with deuterium atoms, or phenylene groups substituted with phenyl groups. Ar a This is an unsubstituted phenyl group, an unsubstituted naphthalenyl group, a naphthalenyl group substituted with a phenyl group, an unsubstituted phenantrenyl group, a phenantrenyl group substituted with a phenyl group, an unsubstituted dibenzofuranyl group, an unsubstituted dibenzothiophenyl group, an unsubstituted carbazolyl group, a carbazolyl group substituted with a phenyl group, an unsubstituted benzonaphthofuranyl group, or an unsubstituted benzonaphthothiophenyl group. R 1 ~R 3 Each of these is independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or an unsubstituted heteroaryl group having 5 to 30 ring-forming carbon atoms. R 4 This is a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 carbon atoms. n1, n2, and n4 are each independent integers between 0 and 7, n3 is an integer between 0 and 3, This includes chemical structures in which any hydrogen atom is replaced by a deuterium atom.
13. The aforementioned chemical formula 1 is the monoamine compound according to claim 12, which is represented by any one of the following chemical formulas 1-A1 to 1-A3: [Chemical formula 1-A1] [Chemical formula 1-A2] [Chemical formula 1-A3] In the above chemical formulas 1-A1 to 1-A3, L 2 , L 3 Ar a , R 1 ~R 4 , and n1 to n4 are as defined in Chemical Formula 1 above.
14. The aforementioned chemical formula 1 is the monoamine compound according to claim 12, which is represented by any one of the following chemical formulas 1-B1 to 1-B3: [Chemical formula 1-B1] [Chemical formula 1-B2] [Chemical formula 1-B3] In the aforementioned chemical formula 1-B2, n5 is an integer between 0 and 4, R 5 is a hydrogen atom or a deuterium atom, In the above chemical formulas 1-B1 to 1-B3, L 1 , L 2 Ar a , R 1 ~R 4 , and n1 to n4 are as defined in Chemical Formula 1 above.
15. In the above chemical formula 1, L 2 The monoamine compound according to claim 12 is either directly bonded or represented by any one of L2-1 to L2-4 below: 。
16. In the above chemical formula 1, Ar a The monoamine compound according to claim 12, which is represented by any one of AR-1 to AR-38 below: 。
17. In the above chemical formula 1, R 1 ~R 3 The monoamine compound according to claim 12, wherein each is independently a hydrogen atom, a deuterium atom, a fluorine atom, or an unsubstituted phenyl group.
18. In the above chemical formula 1, R 4 The monoamine compound according to claim 12, wherein is a hydrogen atom, a deuterium atom, a fluorine atom, an unsubstituted phenyl group, or an unsubstituted dibenzofuranyl group.
19. In the above chemical formula 1, R 4 The monoamine compound according to claim 12, wherein the naphthalenyl group containing is represented by any one of the following R4-1 to R4-6: In the above R4-5, D is a deuterium atom.
20. The aforementioned chemical formula 1 is represented by any one of the compounds in the following first group of compounds, the monoamine compound according to claim 12: [First compound group] In the first group of compounds, D is a deuterium atom.
21. Base layer and A circuit layer placed on the base layer, The circuit layer includes a display element layer which includes a light-emitting element, The light-emitting element is First electrode and A hole transport region is placed on the first electrode and contains a monoamine compound represented by the following chemical formula 1, A light-emitting layer disposed on the hole transport region, An electron transport region disposed on the light-emitting layer, An electronic device including a second electrode positioned on the electron transport region: [Chemical formula 1] In the aforementioned chemical formula 1, L 1 This is a directly bonded, substituted, or unsubstituted ring-forming arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming heteroarylene group having 5 to 30 carbon atoms. L 2 and L 3 These are, independently, directly bonded, unsubstituted phenylene groups, phenylene groups substituted with deuterium atoms, or phenylene groups substituted with phenyl groups. Ar a This is an unsubstituted phenyl group, an unsubstituted naphthalenyl group, a naphthalenyl group substituted with a phenyl group, an unsubstituted phenantrenyl group, a phenantrenyl group substituted with a phenyl group, an unsubstituted dibenzofuranyl group, an unsubstituted dibenzothiophenyl group, an unsubstituted carbazolyl group, a carbazolyl group substituted with a phenyl group, an unsubstituted benzonaphthofuranyl group, or an unsubstituted benzonaphthothiophenyl group. R 1 ~R 3 Each of these is independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or an unsubstituted heteroaryl group having 5 to 30 ring-forming carbon atoms. R 4 This is a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 carbon atoms. n1, n2, and n4 are each independent integers between 0 and 7, n3 is an integer between 0 and 3, This includes chemical structures in which any hydrogen atom is replaced by a deuterium atom.
22. It further includes at least one of a light control layer and a color filter layer, The electronic device according to claim 21, wherein the light control layer comprises quantum dots and the color filter layer comprises a pigment or dye.
23. The aforementioned electronic device includes a display device, The electronic device according to claim 21, wherein the display device includes one of the following: a television, a monitor, an external billboard, a personal computer, a laptop computer, a personal information terminal, a vehicle display device, a game console, a portable electronic device, and a camera.