Light-emitting element, amine compound for light-emitting element, and display device including light-emitting element.
The use of an amine compound in the functional layers of light-emitting elements addresses the need for high luminous efficiency and long lifespan by enhancing hole transport properties and stability, resulting in improved display device performance.
Patent Information
- Authority / Receiving Office
- JP · JP
- Patent Type
- Applications
- Current Assignee / Owner
- SAMSUNG DISPLAY CO LTD
- Filing Date
- 2024-11-20
- Publication Date
- 2026-06-01
Smart Images

Figure 2026089377000001_ABST
Abstract
Description
[Technical Field]
[0001] The present invention relates to a light-emitting element, an amine compound used in the light-emitting element, and a display device including the light-emitting element, and more particularly to a light-emitting element containing a novel amine compound in a functional layer. [Background technology]
[0002] Recently, there has been a lot of development going on in the field of video display devices, such as organic electroluminescence display devices. Organic electroluminescence display devices are display devices that include so-called self-emissive light-emitting elements 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, high luminous efficiency and long lifespan are required, and there is a continuous need for the development of light-emitting element materials that can stably achieve these requirements. In particular, in order to realize long-life light-emitting elements, development is being carried out on materials in the hole transport region that have excellent hole transport properties and stability. [Prior art documents] [Patent Documents]
[0004] [Patent Document 1] International Publication No. 2023 / 287228 [Patent Document 2] U.S. Patent Application Publication No. 2023 / 0172059 Specification [Patent Document 3] Chinese Patent Application Publication No. 113651785 Specification [Patent Document 4] International Publication No. 2022 / 045743 [Patent Document 5] Korean Registered Patent Publication No. 10-2212965 [Patent Document 6] Korean Registered Patent Publication No. 10-1789998 [Patent Document 7] Korean Published Patent No. 10-2021-0097470 [Patent Document 8] International Publication No. 2017 / 204556 [Patent Document 9] International Publication No. 2015 / 194791 [Patent Document 10] Chinese Patent Application Publication No. 115974822 Specification [Patent Document 11] Korean Registered Patent Publication No. 10-2169568 [Patent Document 12] Korean Registered Patent Publication No. 10-2570243 [Patent Document 13] U.S. Patent Application Publication No. 2023 / 0107477 Specification [Overview of the Initiative] [Problems that the invention aims to solve]
[0005] One object of the present invention is to provide a light-emitting element exhibiting long-life characteristics and a display device including the light-emitting element.
[0006] Another object of the present invention is to provide an amine compound that is a material for light-emitting devices exhibiting long-life characteristics. [Means for solving the problem]
[0007] A light-emitting element according to one embodiment of the present invention includes a first electrode, a second electrode disposed on the first electrode, and at least one functional layer disposed between the first electrode and the second electrode, which contains an amine compound represented by the following chemical formula 1. [Chemical formula 1] [ka] In Chemical Formula 1, L is a direct linkage, 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; Ar1 is a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring-forming carbon atoms, provided that Ar1 does not include a substituted or unsubstituted benzofuranyl group and a substituted or unsubstituted benzothiophenyl group; R1 is represented by the following Chemical Formula 2; R2 is represented by the following Chemical Formula 3. [Chemical Formula 2] [Chemical Structure] In Chemical Formula 2, any one of R a1 ~R a4 is the position linked to Chemical Formula 1, and the rest are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; R a5 ~R a10 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms. [Chemical Formula 3] [Chemical Structure] In Chemical Formula 3, X is O, S, or NAr2; Ar2 is a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms; any one of R b1 ~R b4 is the position linked to Chemical Formula 1; the rest of R b1 ~R b4 are each independently a hydrogen atom, a deuterium atom, a halogen atom, or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; any one of R b5 ~R b8 is a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, provided that R b5 ~R b8This does not include substituted or unsubstituted fluorenyl groups, R b5 ~R b8 The remaining atoms are, independently, a hydrogen atom, a deuterium atom, a halogen atom, or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.
[0008] At least one functional layer includes a light-emitting layer, a hole transport region disposed between the first electrode and the light-emitting layer, and an electron transport region disposed between the light-emitting layer and the second electrode, wherein the hole transport region may contain an amine compound represented by chemical formula 1.
[0009] The hole transport region includes a hole injection layer placed on the first electrode and a hole transport layer placed on the hole injection layer, and the hole transport layer may contain an amine compound represented by chemical formula 1.
[0010] The amine compound represented by chemical formula 1 may also be a monoamine compound.
[0011] In chemical formula 1, L may be a directly bonded, substituted, or unsubstituted phenylene group.
[0012] In chemical formula 1, Ar1 may be a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenantrenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted carbazolyl group.
[0013] The amine compound represented by chemical formula 1 may also be represented by the following chemical formula 1-1. [Chemical formula 1-1] [ka] In chemical formula 1-1, A1 to A3 are each independently a hydrogen atom, a deuterium atom, a halogen atom, or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, and L, Ar1, and R2 may be as defined in chemical formula 1.
[0014] The amine compound represented by chemical formula 1 may also be represented by any one of the following chemical formulas 1-2 to 1-5. [Chemical formula 1-2] [ka] [Chemical formula 1-3] [ka] [Chemical formula 1-4] [ka] [Chemical formula 1-5] [ka] In chemical formulas 1-2 to 1-5, R x1 ~R x4 Each of the following is independently a hydrogen atom, a deuterium atom, or a substituted or unsubstituted alkyl group having 1 to 5 carbon atoms, each of the following is independently an integer between 0 and 6, and L, Ar1, and R2 may be as defined in Chemical Formula 1.
[0015] In chemical formula 3, R b1 ~R b4 One of these is a position that is linked to chemical formula 1, and R b1 ~R b4 The remaining atoms may each be independently hydrogen atoms or deuterium atoms.
[0016] The amine compound represented by chemical formula 1 may also be represented by any one of the following chemical formulas 1-6 to 1-9. [Chemical formula 1-6] [ka] [Chemical formula 1-7] [ka] [Chemical formula 1-8] [ka] [Chemical formula 1-9] [ka] In chemical formulas 1-6 to 1-9, R y1 ~R y4 Each of these is independently a substituted or unsubstituted aryl group having 6 to 12 carbon atoms in a ring, and L, Ar1, and R1 may be as defined in Chemical Formula 1.
[0017] The substituent represented by chemical formula 3 may also be represented by any one of the following chemical formulas 3-1 to 3-3. [Chemical formula 3-1] [ka] [Chemical formula 3-2] [ka] [Chemical formula 3-3] [ka] In chemical formula 3-1, R b9 ~R b12 One of these is a position that is linked to chemical formula 1, and R b9 ~R b12 The remaining atoms are each independently either hydrogen atoms or deuterium atoms, and in chemical formula 3-2, R b13 ~R b16 One of these is a position that is linked to chemical formula 1, and R b13 ~R b16 The remaining atoms are each independently either hydrogen atoms or deuterium atoms, and in chemical formula 3-3, R b17 ~R b20One of these is a position that is linked to chemical formula 1, and R b17 ~R b20 The remaining atoms may each be independently hydrogen atoms or deuterium atoms.
[0018] The amine compound represented by chemical formula 1 may be represented by any one of the compounds in the first group of compounds.
[0019] An amine compound according to one embodiment of the present invention may be represented by any one of the compounds in the first group of compounds.
[0020] A display device according to one embodiment of the present invention includes 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 second electrode disposed on the first electrode, and an amine compound represented by chemical formula 1 disposed between the first electrode and the second electrode. [Effects of the Invention]
[0021] A light-emitting element according to one embodiment and a display device including the same can exhibit long-life characteristics by including the amine compound according to one embodiment.
[0022] The amine compound of one embodiment can exhibit long-life characteristics when applied to a light-emitting element. [Brief explanation of the drawing]
[0023] [Figure 1] This is a plan view showing a display device according to one embodiment. [Figure 2] This is a cross-sectional view of a display device according to one embodiment. [Figure 3] This is a schematic cross-sectional view showing a light-emitting element according to one embodiment. [Figure 4] This is a schematic cross-sectional view showing a light-emitting element according to one embodiment. [Figure 5] This is a schematic cross-sectional view showing a light-emitting element according to one embodiment. [Figure 6]This is a schematic cross-sectional view showing a light-emitting element according to one embodiment. [Figure 7] This is a cross-sectional view of a display device according to one embodiment. [Figure 8] This is a cross-sectional view of 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 figure shows a vehicle equipped with a display device according to one embodiment of the present invention. [Modes for carrying out the invention]
[0024] 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 specific embodiments, but rather as including all modifications, equivalents, or substitutions that fall within the spirit and technical scope of the present invention.
[0025] In describing each drawing, similar reference numerals are used for similar components. In the attached drawings, the dimensions of the structures are shown enlarged for clarity of the invention. Terms such as "first," "second," etc., are used to describe various components, but the components are not limited to these terms. The terms are used solely for the purpose of distinguishing one component from another. For example, without departing from the scope of the invention, the first component may be named the second component, and similarly, the second component may also be named the first component. A singular surface includes plural expressions unless the context clearly indicates otherwise.
[0026] In this application, terms such as “includes” or “having” should be understood to indicate the presence of features, numbers, steps, actions, components, parts, or combinations thereof described in the specification, without prejudice to the presence or possibility of adding one or more other features, numbers, steps, actions, components, parts, or combinations thereof.
[0027] In this application, when a part such as a layer, film, region, or plate is said to be "above" or "above" another part, this includes not only when it is "directly above" the other part, but also when there is another part in between. Conversely, when a part such as a layer, film, region, or plate is said to be "below" or "below" another part, this includes not only when it is "directly below" the other part, but also when there is another part in between. Furthermore, in this application, "positioned above" may include not only when it is positioned above, but also when it is positioned below.
[0028] In this specification, "substituted or unsubstituted" means that a molecule is substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium atoms, halogen atoms, cyano groups, nitro groups, amino groups, silyl groups, oxy groups, thio groups, sulfinyl groups, sulfonyl groups, carbonyl groups, boron groups, phosphine oxide groups, phosphine sulfide groups, alkyl groups, alkenyl groups, alkynyl groups, alkoxy groups, hydrocarbon ring groups, aryl groups, and heterocyclic groups. Furthermore, each of the exemplified substituents may be substituted or unsubstituted. For example, a biphenylyl group may be interpreted as an aryl group, or as a phenyl group substituted with a phenyl group.
[0029] In this specification, "bonding with adjacent groups to form a ring" may mean that adjacent groups bond with each other to form a substituted or unsubstituted hydrocarbon ring, or a substituted or unsubstituted heterocycle. Hydrocarbon rings include aliphatic hydrocarbon rings and aromatic hydrocarbon rings. Heterocycles include aliphatic heterocycles and aromatic heterocycles. Hydrocarbon rings and heterocycles may be monocyclic or polycyclic. Furthermore, rings formed by bonding with each other may be linked with other rings to form a spirostructure.
[0030] In this specification, “adjacent group” means a substituent that is substituted on an atom directly linked to the atom on which the substituent is substituted, another substituent that is substituted on the atom on which the substituent is substituted, or the substituent that is stereostructically adjacent to the substituent. For example, the two methyl groups in 1,2-dimethylbenzene are interpreted as “adjacent groups,” and the two ethyl groups in 1,1-diethylcyclopentene may be interpreted as “adjacent groups.” Also, the two methyl groups in 4,5-dimethylphenanthrene may be interpreted as “adjacent groups.”
[0031] In this specification, examples of halogen atoms include fluorine, chlorine, bromine, or iodine atoms.
[0032] In this specification, alkyl groups are linear, branched, or cyclic. The number of carbon atoms in an alkyl group is 1 to 50, 1 to 30, 1 to 20, 1 to 10, or 1 to 6. Examples of alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, s-butyl, t-butyl, i-butyl, 2-ethylbutyl, 3,3-dimethylbutyl, n-pentyl, i-pentyl, neopentyl, t-pentyl, cyclopentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl, n-hexyl, 1-methylhexyl, and 2-ethyl Hexyl group, 2-butylhexyl group, cyclohexyl group, 4-methylcyclohexyl group, 4-t-butylcyclohexyl 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, cyclooctyl group, n-nonyl group, n-decyl group, adamant Tyl group, 2-ethyldecyl group, 2-butyldecyl group, 2-hexyldecyl 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, Examples of n-heptadecyl groups, n-octadecyl groups, n-nonadecyl groups, n-icosyl groups, 2-ethylicosyl groups, 2-butylicosyl groups, 2-hexylicosyl groups, 2-octylicosyl groups, n-henicosyl groups, n-docosyl groups, n-tricosyl groups, n-tetracosyl groups, n-pentacosyl groups, n-hexacosyl groups, n-heptacosyl groups, n-octacosyl groups, n-nonacosyl groups, and n-triacontyl groups are, but are not limited to, these.
[0033] In this specification, cycloalkyl groups refer to cyclic alkyl groups. The number of carbon atoms in a cycloalkyl group is 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.
[0034] 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. The alkenyl group may be a straight chain or a branched chain. The number of carbon atoms is not particularly limited, but is 2 to 30, 2 to 20, or 2 to 10. Examples of alkenyl groups include, but are not limited to, vinyl groups, 1-butenyl groups, 1-pentenyl groups, 1,3-butadienylaryl groups, styrenyl groups, and styrylvinyl groups.
[0035] In this specification, an aryl group means any active group or substituent derived from an aromatic hydrocarbon ring. The aryl group may be a monocyclic aryl group or a polycyclic aryl group. The number of ring-forming carbon atoms of the aryl group is 6 to 30, 6 to 20, or 6 to 15. Examples of aryl groups include, but are not limited to, phenyl, naphthyl, fluorenyl, anthracenyl, phenantrenyl, biphenylyl, terphenylyl, quarterphenylyl, quincphenylyl, sexiphenylyl, triphenylenyl, pyrenyl, benzofluorantenyl, and crisenyl groups.
[0036] In this specification, the fluorenyl group may be substituted, or 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. [ka]
[0037] 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 heterocyclics and aromatic heterocyclics may be monocyclic or polycyclic.
[0038] 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 is 2 to 30, 2 to 20, or 2 to 10. Examples of heteroaryl groups include thiophenyl group, furanyl group, pyrrolyl group, imidazolyl group, pyridinyl group, bipyridinyl group, pyrimidinyl group, triazinyl group, triazolyl group, acrydilyl group, pyridadinyl group, pyridinyl group, quinolinyl group, quinazolinyl group, quinoxalinyl group, phenoxadinyl group, phthalazinyl group, pyridopyrimidinyl group, pyridopyradinyl group, pyrazinopyradinyl group, isoquinolinyl group, indolyl group, carbazolyl group, N-arylcarbazolyl group, N- Examples of such groups include, but are not limited to, heteroarylcarbazolyl groups, N-alkylcarbazolyl groups, benzoxazolyl groups, benzimidazolyl groups, benzothiazolyl groups, benzocarbazolyl groups, benzothiophenyl groups, dibenzothiophenyl groups, thienothiophenyl groups, benzofuranyl groups, phenanthrolinyl groups, thiazolyl groups, isoxazolyl groups, oxazolyl groups, oxadiazolyl groups, thiadiazolyl groups, phenothiazinyl groups, dibenzosilolyl groups, and dibenzofuranyl groups.
[0039] In this specification, the above-described description of aryl groups applies, except that arylene groups are divalent. The above-described description of heteroaryl groups applies, except that heteroarylene groups are divalent.
[0040] 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.
[0041] In this specification, the thio group may include alkylthio groups and arylthio groups. The thio group may mean a group in which a sulfur atom is bonded to an 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.
[0042] 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. An oxy group may include alkoxy groups and aryl groups. The alkoxy group may be linear, branched, or cyclic. The number of carbon atoms in the alkoxy group is not particularly limited, but may be, for example, 1 to 20, or 1 to 10. Examples of oxy groups include, but are not limited to, methoxy, ethoxy, n-propoxy, isopropoxy, butoxy, pentyloxy, hexyloxy, octyloxy, nonyloxy, decyloxy, and benzyloxy groups.
[0043] In this specification, a boron group may mean a boron atom bonded to an alkyl or aryl group as defined above. Boron groups include alkylboron groups and arylboron groups. Examples of boron groups include, but are not limited to, dimethylboron groups, diethylboron groups, t-butylmethylboron groups, diphenylboron groups, and phenylboron groups.
[0044] In this specification, the number of carbon atoms in an amino group is not particularly limited, but may be between 1 and 30. The amino group may include alkylamino groups and arylamino groups. Examples of amino groups include, but are not limited to, methylamino groups, dimethylamino groups, phenylamino groups, diphenylamino groups, naphthylamino groups, and 9-methyl-anthracenylamino groups.
[0045] In this specification, direct bond means single bond.
[0046] On the other hand, in this specification, JPEG2026089377000018.jpg1011 " and " JPEG2026089377000019.jpg212 " indicates the position where they are connected.
[0047] One embodiment of the present invention will be described below with reference to the drawings.
[0048] 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.
[0049] 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, the optical layer PP may be omitted from the display device DD of one embodiment, contrary to what is shown.
[0050] A base substrate BL can be placed on top of the optical layer PP. The base substrate BL is a component that provides the 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, this 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, unlike the illustrated, the base substrate BL may be omitted in one embodiment.
[0051] A 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.
[0052] 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.
[0053] The base layer BS may be a component that provides the base surface on which the display element layer DP-ED is arranged. The base layer BS may be a glass substrate, a metal substrate, a plastic substrate, etc. However, this embodiment is not limited thereto, and the base layer BS may be an inorganic layer, an organic layer, or a composite material layer.
[0054] In one embodiment, the circuit layer DP-CL is located on the base layer BS, but the circuit layer DP-CL may include a plurality of transistors (not shown). Each transistor (not shown) may include a control electrode, an input electrode, and an output electrode. For example, the circuit layer DP-CL may include a switching transistor and a drive transistor for driving the light-emitting elements ED-1, ED-2, and ED-3.
[0055] 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 as 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, EML-B, an electron transport region ETR, and a second electrode EL2.
[0056] Figure 2 shows an embodiment in which the light-emitting layers EML-R, EML-G, and EML-B of the light-emitting elements ED-1, ED-2, and ED-3 are arranged within the opening OH defined in the pixel-defining film PDL, and the hole transport region HTR, electron transport region ETR, and second electrode EL2 are provided as a common layer for all light-emitting elements ED-1, ED-2, and ED-3. However, this embodiment is not limited thereto, 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 the light-emitting elements ED-1, ED-2, and ED-3 may be patterned and provided by an inkjet printing method.
[0057] The sealing layer TFE may cover the organic electroluminescent elements ED-1, ED-2, and ED-3. The sealing layer TFE can 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.
[0058] 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.
[0059] The sealing layer TFE may be placed on the second electrode EL2 and may fill the opening OH.
[0060] 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 each of the light-emitting elements ED-1, ED-2, and ED-3 is emitted. The emitting regions PXA-R, PXA-G, and PXA-B may be spaced apart from each other on a plane.
[0061] The light-emitting regions PXA-R, PXA-G, and PXA-B may each be regions separated by the pixel-defining film PDL. The non-light-emitting region NPXA is the region between adjacent light-emitting regions PXA-R, PXA-G, and PXA-B, and may be a region corresponding to the pixel-defining film PDL. On the other hand, in this specification, the light-emitting regions PXA-R, PXA-G, and PXA-B may each 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 arranged and separated by the aperture OH defined in the pixel-defining film PDL.
[0062] The light-emitting regions PXA-R, PXA-G, and PXA-B may 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 light, green light, 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.
[0063] 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-2 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.
[0064] However, this embodiment is not limited thereto, and the first to third light-emitting elements ED-1, ED-2, and ED-3 may emit light in the same wavelength 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.
[0065] 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.
[0066] In Figures 1 and 2, the areas of the light-emitting regions PXA-R, PXA-G, and PXA-B are shown to be the same, but the embodiment is not limited to this, 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 refer to the area as viewed from the plane defined by the first directional axis DR1 and the second directional axis DR2.
[0067] 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, the green light-emitting region PXA-G, and the blue light-emitting region PXA-B are arranged may 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 may be a Pentile (PENTILE®) arrangement or a Diamond (DiAmond Pixel®) arrangement.
[0068] 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 this embodiment is not limited to this.
[0069] 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 second electrode EL2 facing the first electrode EL1, and at least one functional layer disposed between the first electrode EL1 and the second electrode EL2. The light-emitting element ED according to one embodiment may also include an amine compound according to one embodiment, described later, in at least one functional layer.
[0070] The light-emitting element ED may include a hole transport region HTR, an emissive layer EML, an electron transport region ETR, etc., which are sequentially stacked as at least one functional layer. Referring to Figure 3, one embodiment of the light-emitting element ED may include a first electrode EL1, a hole transport region HTR, an emissive layer EML, an electron transport region ETR, and a second electrode EL2, which are sequentially stacked.
[0071] Figure 4, compared to Figure 3, shows a cross-sectional view of a light-emitting element ED in one embodiment, 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, compared to Figure 3, shows a cross-sectional view of a light-emitting element ED in one embodiment, 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, compared to Figure 4, shows a cross-sectional view of a light-emitting element ED in one embodiment, in which a capping layer CPL is placed on the second electrode EL2.
[0072] In one embodiment of the light-emitting element ED, the hole transport region HTR may contain the amine compound of the embodiment described later. In one embodiment of the light-emitting element ED, at least one of the hole injection layer HIL, hole transport layer HTL, and electron blocking layer EBL of the hole transport region HTR may contain the amine compound of the embodiment. For example, in one embodiment of the light-emitting element ED, the hole transport layer HTL may contain the amine compound of the embodiment.
[0073] In one embodiment of a light-emitting element ED, the first electrode EL1 is conductive. The first electrode EL1 may be made of a metallic material, a metal alloy, or a conductive compound. The first electrode EL1 may be an anode or a cathode. However, this embodiment is not limited thereto. 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.
[0074] If the first electrode EL1 is a transmissive electrode, it may contain a transparent metal oxide, such as ITO (indium tin oxide), IZO (indium zinc oxide), ZnO (zinc oxide), or ITZO (indium tin zinc oxide). 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 these materials, and a transparent conductive film made of ITO, IZO, ZnO, ITZO, etc. For example, the first electrode EL1 may have a three-compartment structure of ITO / Ag / ITO, but is not limited thereto. Furthermore, this embodiment is not limited thereto, and the first electrode EL1 may include the above-mentioned metal material, a combination of two or more metal materials selected from the above-mentioned metal materials, or an oxide of the above-mentioned metal material. The thickness of the first electrode EL1 may be about 70 nm to about 1,000 nm. For example, the thickness of the first electrode EL1 may be about 100 nm to about 300 nm.
[0075] The hole transport region (HTR) may be provided on the first electrode EL1. 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.
[0076] The hole transport region (HTR) includes at least one of the hole injection layer (HIL), the hole transport layer (HTL), and the electron blocking layer (EBL). Although not shown in the figures, the hole transport region (HTR) may also include multiple stacked hole transport layers.
[0077] Alternatively, the hole transport region HTR may have a single-layer structure of a hole injection layer HIL or a hole transport layer HTL, or a single-layer structure consisting of a hole injection material and a hole transport material. In one embodiment, the hole transport region HTR may have a single-layer structure consisting of multiple different materials, or it may have a structure of hole injection layer HIL / hole transport layer HTL, hole injection layer HIL / hole transport layer HTL / buffer layer (not shown), hole injection layer HIL / buffer layer (not shown), or hole transport layer HTL / buffer layer (not shown) stacked sequentially from the first electrode EL1, but this embodiment is not limited to these.
[0078] The thickness of the hole transport region (HTR) may be, for example, about 5 nm to about 1,500 nm. The hole transport region (HTR) can be formed using a variety of methods such as vacuum deposition, spin coating, casting, LB (Langmuir-Blodgett), inkjet printing, laser printing, and laser-induced thermal imaging (LITI).
[0079] In one embodiment, the light-emitting element ED may contain the amine compound of one embodiment in the hole transport region HTR. In one embodiment, the light-emitting element ED includes an electron injection layer EIL and a hole transport layer HTL, and the hole transport layer HTL may contain the amine compound of one embodiment. The amine compound of one embodiment may be included in a layer adjacent to the light-emitting layer EML among the layers included in the hole transport region HTR.
[0080] The amine compound of one embodiment may include a structure in which a first substituent, a second substituent, and a third substituent are linked to a core nitrogen atom. The amine compound of one embodiment may be a monoamine compound containing a single amino group. The amine compound of one embodiment may be a compound containing a single amino group that does not form a ring in its molecular structure.
[0081] The first substituent may include a benzonaphthothiophene substructure. The first substituent may be a substituted or unsubstituted benzonaphthothiophenyl group. The first substituent may include a benzo[b]naphtho[2,1-d]thiophene substructure. The first substituent may include a substructure represented by the following chemical formula S1. The benzonaphthothiophene substructure of the first substituent may include a benzene substructure and a naphthalene substructure linked to each other via a single sulfur atom. The benzene substructure of the benzonaphthothiophene substructure may be linked to the core nitrogen atom of the amine compound of one embodiment. Any carbon atom constituting the benzene substructure of the benzonaphthothiophene substructure may be linked to the core nitrogen atom of the amine compound of one embodiment. [Chemical formula S1] [ka]
[0082] The second substituent may include any one of the dibenzofuranyl substructure, the dibenzothiophenyl substructure, and the carbazolyl substructure. When the second substituent includes the carbazole substructure, it may also include the 9-carbazole substructure. The second substituent may include a first benzene substructure and a second benzene substructure linked to each other via a first heteroatom. The first heteroatom may be any one of the oxygen atom (O), the sulfur atom (S), and the nitrogen atom (N). The first benzene substructure of the second substituent may be linked to the core nitrogen atom of the amine compound of one embodiment. Any carbon atom constituting the first benzene substructure of the second substituent may be linked to the core nitrogen atom of the amine compound of one embodiment.
[0083] The second substituent further comprises one aryl group having 6 to 30 carbon atoms, which is linked to the second benzene substructure. For example, the second substituent may further comprise one phenyl group linked to the second benzene substructure. Any carbon atom constituting the second benzene substructure of the second substituent may be linked to the phenyl group.
[0084] The third substituent may be linked to the nitrogen atom of the amine compound of one embodiment via a first linker. The first linker may be a directly bonded, substituted, or unsubstituted arylene group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring-forming carbon atoms. The third substituent may be selected from the aryl group of substituted or unsubstituted ring-forming carbon atoms having 6 to 30, or from the heteroaryl group of substituted or unsubstituted ring-forming carbon atoms having 2 to 30. However, cases in which the third substituent includes a substituted or unsubstituted benzofuranyl group and a substituted or unsubstituted benzothiophenyl group are excluded. In other words, in the amine compound of one embodiment, cases in which the third substituent includes the substructure represented by chemical formula S3-1 and the substructure represented by chemical formula S3-2 are excluded. [Chemical formula 3S-1] [ka] [Chemical formula 3S-2] [ka]
[0085] In one embodiment, the amine compound may be represented by the following chemical formula 1. [Chemical formula 1] [ka]
[0086] In chemical formula 1, L is a directly bonded, substituted, or unsubstituted arylene group with 6 to 30 ring-forming carbon atoms, or an unsubstituted heteroarylene group with 2 to 30 ring-forming carbon atoms. For example, L may be a directly bonded, substituted, or unsubstituted phenylene group.
[0087] In chemical formula 1, Ar1 is a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms. However, Ar1 does not include substituted or unsubstituted benzofuranyl groups or substituted or unsubstituted benzothiophenyl groups. For example, Ar1 may be a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenantrenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted carbazolyl group.
[0088] In chemical formula 1, R1 is represented by chemical formula 2 below, and R2 is represented by chemical formula 3 below. [Chemical formula 2] [ka]
[0089] In chemical formula 2, R a1 ~R a4 One of these is a position that is linked to chemical formula 1, and the remaining ones are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms. For example, R a1 R is the position that is linked to chemical formula 1. a2 ~R a4 Each of these may independently be a hydrogen atom or a deuterium atom.
[0090] In chemical formula 2, R a5 ~R a10 Each of these is independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms. For example, R a5 ~R a10 Each of these may independently be a hydrogen atom or a deuterium atom.
[0091] [Chemical formula 3] [ka]
[0092] In chemical formula 3, X is O, S, or NAr2.
[0093] In chemical formula 3, Ar2 is a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms. For example, Ar2 may be a substituted or unsubstituted phenyl group.
[0094] In chemical formula 3, R b1 ~R b4 One of these is a position that is linked to chemical formula 1, and R b1 ~R b4 The remaining atoms are, independently, a hydrogen atom, a deuterium atom, a halogen atom, or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms. For example, R b1 R is the position that is linked to chemical formula 1. b2 ~R b4 Each of these may independently be a hydrogen atom or a deuterium atom.
[0095] In chemical formula 3, R b5 ~R b8 One of these is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms in a ring. However, R b5 ~R b8 This does not contain substituted or unsubstituted fluorenyl groups. b5 ~R b8 The remaining atoms are, independently, a hydrogen atom, a deuterium atom, a halogen atom, or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms. For example, R b8 R is a substituted or unsubstituted phenyl group, b5 ~R b7 Each of these may independently be a hydrogen atom or a deuterium atom. Or, R b6 R is a substituted or unsubstituted phenyl group, b4, R b5 , and R b7 Each of these may independently be a hydrogen atom or a deuterium atom.
[0096] On the other hand, in chemical formula 1, the N atom can correspond to the core nitrogen atom described above, L can correspond to the first linker described above, and Ar1 can correspond to the third substituent described above. The substituent represented by chemical formula 2 can correspond to the first substituent described above, and the substituent represented by chemical formula 3 can correspond to the second substituent described above.
[0097] In one embodiment, the amine compound may be represented by the following chemical formula 1-1. [Chemical formula 1-1] [ka]
[0098] Chemical formula 1-1 shows the case where the position to which R1 is linked in chemical formula 2 is specified in chemical formula 1. Chemical formula 1-1 shows R in chemical formula 2. a1 This shows the case where it is linked to chemical formula 1.
[0099] In chemical formula 1-1, A1 to A9 may each independently be a hydrogen atom, a deuterium atom, a halogen atom, or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms. For example, A1 to A9 may each independently be a hydrogen atom or a deuterium atom.
[0100] On the other hand, in chemical formula 1-1, the same principles as those described in chemical formula 1 can be applied to L, Ar1, and R2.
[0101] In one embodiment, the amine compound may be represented by any one of the following chemical formulas 1-2 to 1-5. [Chemical formula 1-2] [ka] [Chemical formula 1-3] [ka] [Chemical formula 1-4] [ka] [Chemical formula 1-5] [ka]
[0102] Chemical formulas 1-2 to 1-5 are when R1 in chemical formula 1 is represented by chemical formula 2, and R in chemical formula 2 is represented by a1 ~R a4 This shows the case where the type of substituent is specified. Chemical formulas 1-2 show that in chemical formula 2, R a1 This is linked to chemical formula 1, R a2 ~R a4 This indicates that it is a hydrogen atom, and chemical formulas 1-3 are shown as R in chemical formula 2. a2 This is linked to chemical formula 1, R a1 , R a3 , and R a4 This shows that is a hydrogen atom, and chemical formulas 1-4 are shown as R in chemical formula 2. a3 This is linked to chemical formula 1, R a1 , R a2 , and R a4 This shows the case where is a hydrogen atom, and chemical formulas 1-5 are R a4 This is linked to chemical formula 1, R a1 ~R a3 This shows the case where it is a hydrogen atom.
[0103] In chemical formulas 1-2 to 1-5, R x1 ~R x4 Each of these may independently be a hydrogen atom, a deuterium atom, or a substituted or unsubstituted alkyl group having 1 to 5 carbon atoms. For example, R x1 ~R x4 Each of these may independently be a hydrogen atom or a deuterium atom.
[0104] In chemical formula 1-2, n1 is an integer between 0 and 6. If n1 is 0, the amine compound of one embodiment is R x1It can be meant that it is not replaced. When n1 is 6 and all of R x1 are hydrogen atoms, it is the same as the case when n1 is 0. If n1 is an integer of 2 or more, each of the plurality of R x1 may be the same as each other, or at least one of the plurality of R x1 may be different.
[0105] In Chemical Formula 1-3, n2 is an integer of 0 or more and 6 or less. If n2 is 0, it can be meant that the amine compound of one embodiment is not substituted with R x2 When n2 is 6 and all of R x2 are hydrogen atoms, it is the same as the case when n2 is 0. If n2 is an integer of 2 or more, each of the plurality of R x2 may be the same as each other, or at least one of the plurality of R x2 may be different.
[0106] In Chemical Formula 1-4, n3 is an integer of 0 or more and 6 or less. If n3 is 0, it means that the amine compound of one embodiment is not substituted with R x3 When n3 is 6 and all of R x3 are hydrogen atoms, it is the same as the case when n3 is 0. If n3 is an integer of 2 or more, each of the plurality of R x3 may be the same as each other, or at least one of the plurality of R x3 may be different.
[0107] In Chemical Formula 1-5, n4 is an integer of 0 or more and 6 or less. If n4 is 0, it means that the amine compound of one embodiment is not substituted with R x4 When n4 is 6 and all of R x4 are hydrogen atoms, it is the same as the case when n4 is 0. If n4 is an integer of 2 or more, each of the plurality of R x4 may be the same as each other, or at least one of the plurality of R x4 may be different.
[0108] On the other hand, in chemical formulas 1-2 to 1-5, the same principles as those explained for chemical formula 1 can be applied to L, Ar1, and R2.
[0109] In one embodiment, the amine compound may be represented by any one of the following chemical formulas 1-6 to 1-9. [Chemical formula 1-6] [ka] [Chemical formula 1-7] [ka] [Chemical formula 1-8] [ka] [Chemical formula 1-9] [ka]
[0110] Chemical formulas 1-6 to 1-9 are when R2 in chemical formula 1 is represented by chemical formula 3, and R in chemical formula 3 is represented by chemical formula 3. b1 ~R b4 This shows the case where the type of substituent is specified. Chemical formulas 1-6 are shown where R in chemical formula 3 b1 This is linked to chemical formula 1, R b2 ~R b4 R is a hydrogen atom, b5 ~R b8 One of the following is R y1 And R b5 ~R b8 This shows the case where the remaining atoms are hydrogen atoms. Chemical formulas 1-7 are shown in chemical formula 3 where R b2 This is linked to chemical formula 1, R b1 , R b3 , and R b4 R is a hydrogen atom, b5 ~R b8 One of the following is Ry2 And R b5 ~R b8 This shows the case where the remaining atoms are hydrogen atoms. Chemical formulas 1-8 are shown in chemical formula 3 where R b3 This is linked to chemical formula 1, R b1 , R b2 , and R b4 R is a hydrogen atom, b5 ~R b8 One of the following is R y3 And R b5 ~R b8 This shows the case where the remaining atoms are hydrogen atoms. Chemical formulas 1-9 are shown in chemical formula 3, where R b4 This is linked to chemical formula 1, R b1 ~R b3 R is a hydrogen atom, b5 ~R b8 One of the following is R y4 And R b5 ~R b8 This shows that the remaining atoms are hydrogen atoms.
[0111] In chemical formulas 1-6 to 1-9, R y1 ~R y4 Each of these may independently be a substituted or unsubstituted aryl group having 6 to 12 carbon atoms in a ring. For example, R y1 ~R y4 Each of these may independently be a substituted or unsubstituted phenyl group.
[0112] On the other hand, in chemical formulas 1-6 to 1-9, the same principles as those explained for chemical formula 1 can be applied to L, Ar1, and R1.
[0113] In one embodiment, the substituent represented by chemical formula 3 in the amine compound may be represented by the following chemical formula 3-1. [Chemical formula 3-1] [ka]
[0114] Chemical formula 3-1 is where X in chemical formula 3 is O, and R in chemical formula 3 is b5 ~Rb7 is a hydrogen atom, and R b8 represents the case where it is an unsubstituted phenyl group.
[0115] In Chemical Formula 3-1, one of R b9 ~R b12 is the position linked to Chemical Formula 1, and the rest of R b9 ~R b12 may each independently be a hydrogen atom or a deuterium atom. For example, R b10 is the position linked to Chemical Formula 1, and R b9 , R b11 , and R b12 may be hydrogen atoms.
[0116] In one embodiment, the substituent represented by Chemical Formula 3 in the amine compound may be represented by the following Chemical Formula 3-2. [Chemical Formula 3-2]
Chemical Structure
[0117] Chemical Formula 3-2 represents the case where X in Chemical Formula 3 is S, R b5 ~R b7 are hydrogen atoms, and R b8 is an unsubstituted phenyl group.
[0118] In Chemical Formula 3-2, one of R b13 ~R b16 is the position linked to Chemical Formula 1, and the rest of R b13 ~R b16 may each independently be a hydrogen atom or a deuterium atom. For example, R b13 is the position linked to Chemical Formula 1, and R b14 ~R b16 may be hydrogen atoms.
[0119] In one embodiment, the substituent represented by Chemical Formula 3 in the amine compound may be represented by the following Chemical Formula 3-3. [Chemical Formula 3-3] [Chemistry]
[0120] Chemical formula 3-3 shows the case where X in Chemical formula 3 is NAr2, Ar2 is an unsubstituted phenyl group, and R in Chemical formula 3 b5 , R b7 , and R b8 are hydrogen atoms, and R b6 is an unsubstituted phenyl group.
[0121] In Chemical formula 3-3, any one of R b17 to R b20 is the position linked to Chemical formula 1, and the rest of R b17 to R b20 may each independently be a hydrogen atom or a deuterium atom. For example, R b19 is the position linked to Chemical formula 1, and R b17 , R b18 , and R b20 may be hydrogen atoms.
[0122] In Chemical formulas 3-1 to 3-3, any hydrogen atom may be substituted with a deuterium atom. Chemical formulas 3-1 to 3-3 may include a structure in which any hydrogen atom is substituted with a deuterium atom.
[0123] The amine compound of one embodiment represented by Chemical formula 1 may be represented by any one of the following Chemical formulas 1-A to 1-D. [Chemistry]
[0124] In Chemical formula 1-A, R A1 and R A2 may be represented by the substituents described in Table 1 below. The amine compound represented by Chemical formula 1-A may be represented by compounds Aa1 to Av46 by the combinations of the substituents described in Table 1 below. In Chemical formula 1-B, R B1 and R B2R may be represented by the substituents listed in Table 2 below. The amine compound represented by chemical formula 1-B may also be represented by compounds Ba1 to Bv46 by the substituent combinations listed in Table 2 below. In chemical formula 1-C, R C1 and R C2 R may be represented by the substituents listed in Table 3 below. The amine compound represented by chemical formula 1-C may also be represented by compounds Ca1 to Cv46 by the substituent combinations listed in Table 3 below. In chemical formula 1-D, R D1 and R D2 The substituents may be represented by those listed in Table 4 below. The amine compounds represented by chemical formula 1-D may also be represented by compounds Da1 to Dv46 by combinations of substituents listed in Table 4 below. On the other hand, in Tables 1 to 4 below, BN1 to BN21 and CN1 to CN46 each represent substituents as shown below. In BN1 to BN21, JPEG2026089377000039.jpg312 The symbols indicate the positions where the N atom is bonded in chemical formulas 1-A to 1-D, and in CN1 to CN46. JPEG2026089377000040.jpg58 The symbol indicates the position where the atom is bonded to the N atom in chemical formulas 1-A to 1-D.
[0125] [ka] [ka] [ka]
[0126] [ka]
[0127] [ka]
[0128]
change
[0129] [Table 1] Table 1 Table 2 Table 3 Table 4 Table 5 Table 6 Table 7 Table 8 Table 9 Table 10 Table 11
[0130] [Table 2] Table 12 Table 13 Table 14 Table 15 Table 16 Table 17 Table 18 Table 19 Table 20 Table 21 Table 22
[0131] [Table 3] Table 23 Table 24 Table 25 Table 26 Table 27 Table 28 Table 29 Table 30 Table 31 Table 32 Table 33
[0132] [Table 4] Table 34 Table 35 Table 36 Table 37 Table 38 Table 39 [Table 40] [Table 41] [Table 42] [Table 43] [Table 44]
[0133] In this specification, compounds Aa1 to Av46 shown in Table 1 are referred to as compound group A, compounds Ba1 to Bv46 shown in Table 2 are referred to as compound group B, compounds Ca1 to Cv46 shown in Table 3 are referred to as compound group C, and compounds Da1 to Dv46 shown in Table 4 are referred to as compound group D.
[0134] The amine compound of one embodiment may be represented by one of compound group A, compound group B, compound group C, and compound group D. The hole transport region HTR of the light-emitting element ED of one embodiment may contain at least one of the amine compounds disclosed in compound group A, compound group B, compound group C, and compound group D. The hole transport layer HTL of the light-emitting element ED may contain at least one of the amine compounds disclosed in compound group A, compound group B, compound group C, and compound group D. For example, the amine compound of one embodiment may contain at least one of the amine compounds disclosed in the following first compound group. Compounds 1 to 12 disclosed in the first compound group represent compounds Aa16, Ab16, Ac16, Ad16, Ae4, Ae16, Ae24, Ae29, Ae34, Ae43, Ai16, and As16 from compound group A described above, respectively, while compounds 13 to 15 disclosed in the first compound group represent Be34 from compound group B, Ce34 from compound group C, and De34 from compound group D described above.
[0135] [First compound group] [ka] [ka]
[0136] The amine compound according to one embodiment, by including a first substituent, a second substituent, and a third substituent, can achieve a longer lifespan for the light-emitting element.
[0137] The amine compound of one embodiment contains an amino group, and the first to third substituents have a structure that is bonded to the amino group of the amine compound of one embodiment. In this case, the first substituent contains a benzonaphthothiophene substructure. The second substituent contains one of the dibenzofuranyl substructure, dibenzothiophenyl substructure, and carbazolyl substructure. The second substituent contains a first benzene substructure and a second benzene substructure linked to each other via a first heteroatom, the first benzene substructure of the second substituent being bonded to an amino group, and the second substituent further contains a phenyl group bonded to the second benzene substructure. The third substituent is selected from the substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or from the substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms. However, the third substituent is excluded if it is a substituted or unsubstituted benzofuranyl group or a substituted or unsubstituted benzothiophenyl group.
[0138] The amine compound of one embodiment can have excellent stability by introducing such substituents. More specifically, the lifespan of the amine compound of one embodiment containing the first substituent can be improved by stacking and intermolecular orientation due to intermolecular interactions relating to the first substituent within the amine compound of one embodiment. Furthermore, the lifespan of the amine compound of one embodiment containing the second substituent can be improved by stacking and intermolecular orientation due to intermolecular interactions relating to the second substituent within the amine compound of one embodiment. If the amine compound according to one embodiment of the present invention is applied to the hole transport region HTR of a light-emitting element ED, a long-life light-emitting element can be realized.
[0139] In one embodiment of the light-emitting element ED, the hole transport region HTR may further contain a compound represented by the following chemical formula H-1. [Chemical formula H-1] [ka]
[0140] In chemical formula H-1, L1 and L2 may each be independently a directly bonded, substituted, or unsubstituted arylene group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring-forming carbon atoms. a and b may each be independently an integer between 0 and 10. On the other hand, if a or b is an integer of 2 or more, multiple L1 and L2 may each be independently 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.
[0141] In the chemical formula H-1, Ar a ~Ar b Each of these may 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. Also, in chemical formula H-1, Ar c This is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms in a ring.
[0142] 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 Ar a ~Ar c At least one of them may be a diamine compound containing an amino group as a substituent. Alternatively, the compound represented by the chemical formula H-1 may be Ar a ~Ar b A carbazole compound containing at least one substituted or unsubstituted carbazolyl group, or Ar a ~Ar b The fluorene compound may contain at least one substituted or unsubstituted fluorenyl group.
[0143] The compound represented by the chemical formula H-1 may 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.
[0144] [Compound group H] [ka] [ka] [ka] [ka] [ka]
[0145] In addition, the hole transport region (HTR) may further include known hole transport materials.
[0146] For example, 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), 1-TNATA(4,4',4”-tris[N(1-naphthyl)-N-phenylamino]-triphenylamine), 2-TNATA(4,4',4”-tris[N(2-naphthyl)-N-phenylamino]-triphenylamine), PEDOT / PSS(poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate), PANI / DBSA(poly This may include polyaniline / dodecylbenzenesulfonic acid, PANI / CSA (polyaniline / camphor sulfonic acid), PANI / PSS ((polyaniline) / poly(4-styrene sulfonate)), NPB (or NPD) (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-hexacarbonitrine), etc.
[0147] The hole transport region HTR may include, for example, carbazole derivatives such as N-phenylcarbazole and polyvinylcarbazole, fluorene derivatives, triphenylamine derivatives such as TCTA (4,4',4"-tris(N-carbazol)triphenylamine), or TPD (N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine), 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), mCP (1,3-bis(N-carbazol)benzene), etc.
[0148] Furthermore, the hole transport region HTR may further contain 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).
[0149] 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 compounds of the hole transport region described above.
[0150] The thickness of the hole transport region HTR may be approximately 10 nm to approximately 1,000 nm, for example, approximately 10 nm to approximately 500 nm. If the hole transport region HTR includes a hole injection layer HIL, the thickness of the hole injection layer HIL may be, for example, approximately 3 nm to approximately 100 nm. If the hole transport region HTR includes a hole transport layer HTL, the thickness of the hole transport layer HTL may be approximately 3 nm to approximately 100 nm. For example, if the hole transport region HTR includes a hole blocking layer EBL, the thickness of the hole blocking layer EBL may be, for example, approximately 1 nm to approximately 100 nm. 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 driving voltage.
[0151] 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-dopants (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. Examples of 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 this embodiment is not limited to these.
[0152] As described above, the hole transport region (HTR) may further include a buffer layer (not shown) in addition to the hole injection layer (HIL), hole transport layer (HTL), and electron blocking layer (EBL). The buffer layer (not shown) compensates for the resonance distance due to the wavelength of light emitted from the light emission layer (EML) and increases the light emission efficiency. The material included in the buffer layer (not shown) can be any material that can be included in the hole transport region (HTR).
[0153] The emissive layer (EML) is provided on top of the hole transport region (HTR). The emissive layer (EML) may have a thickness of, for example, about 10 nm to about 100 nm, or about 10 nm to about 30 nm. The emissive layer (EML) can 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.
[0154] In one embodiment of the light-emitting element ED, the light-emitting layer EML may emit blue light. In one embodiment of the light-emitting element ED, by including the amine compound of the above embodiment in the hole transport region HTR, it can exhibit long lifetime characteristics in the blue light emission region. However, this embodiment is not limited thereto.
[0155] In one embodiment of a light-emitting element (ED), the light-emitting layer (EML) comprises an anthracene derivative, a pyrene derivative, a fluorantene derivative, a chrysene derivative, a dihydrobenzanthracene derivative, or a triphenylene derivative. More specifically, the light-emitting layer (EML) may comprise an anthracene derivative or a pyrene derivative.
[0156] In one embodiment of the light-emitting element ED shown in Figures 3 to 6, the light-emitting layer EML may contain a host and a dopant, and the light-emitting layer EML contains 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. [Chemical formula E-1] [ka]
[0157] In chemical formula E-1, R 31 ~R 40 Each of these 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 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 R 31 ~R 40 In this structure, adjacent groups bond to each other to form a ring. For example, R 31 ~R 40 Adjacent groups within this can bond to each other to form a saturated hydrocarbon ring, an unsaturated hydrocarbon ring, a saturated heterocycle, or an unsaturated heterocycle.
[0158] In chemical formula E-1, c and d may each be independent integers between 0 and 5.
[0159] Chemical formula E-1 may also be represented by any one of the following compounds E1 to E19. [ka] [ka] [ka] [ka] [ka] [ka] [ka]
[0160] 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 phosphorescent host material. [Chemical formula E-2a] [ka]
[0161] In chemical formula E-2a, a is an integer between 0 and 10, and L aa may 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, if a is an integer of 2 or more, L a Each of these may 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.
[0162] In chemical formula E-2a, A1 to A5 are each independently either N or CR. i It is also acceptable. a ~R i Each of these is independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted amino group, a substituted or unsubstituted thio group, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, or R a ~R i Adjacent groups within the ring may bond to each other to form a ring. a ~R i In this structure, adjacent groups can bond to each other to form a hydrocarbon ring or a heterocycle 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 That's fine.
[0164] [Chemical formula E-2b] [ka]
[0165] In chemical formula E-2b, Cbz1 and Cbz2 may each be independently a carbazolyl group or a carbazolyl group substituted with an aryl group having 6 to 30 ring-forming carbon atoms. bmay 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 may 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 compounds represented by chemical formula E-2a and E-2b are each represented by one of the compounds in compound group E-2 below. However, the compounds shown in compound group E-2 below are illustrative examples, and the compounds represented by chemical formula E-2a or E-2b are not limited to those shown in compound group E-2 below.
[0167] [Compound group E-2] [ka] [ka] [ka] [ka] [ka]
[0168] The luminescent layer EML may further contain a common material known in the art as a host material. 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. ) 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. may 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. In another embodiment, the compound represented by the chemical formula Ma or chemical formula Mb can be used as an auxiliary dopant material. [Chemical formula Ma] [ka]
[0170] In the chemical formula Ma, Y1-Y4 and Z1-Z4 are each independently CR1 or N, and R1-R4 are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted amino group, a substituted or unsubstituted thio group, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group having 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 adjacent groups among R1-R4 are bonded to each other 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.
[0171] Compounds represented by the chemical formula Ma can be used as phosphorescent dopants.
[0172] A compound represented by the chemical formula Ma can be any one of the compounds in the group of compounds M-a1 to M-a25 listed below. However, the compounds M-a1 to M-a25 listed below are illustrative examples, and the compound represented by the chemical formula Ma is not limited to those represented by the compounds M-a1 to M-a25 listed below. [ka] [ka] [ka] [ka] [ka] [ka] JPEG2026089377000121.jpg3375
[0173] Compounds M-a1 and M-a2 can be used as red dopant materials, and compounds M-a3 to M-a7 can be used as green dopant materials. [Chemical formula Mb] [ka]
[0174] In chemical formula Mb, Q1 to Q4 are each independently either C or N, and C1 to C4 are each independently substituted or unsubstituted hydrocarbon rings with 5 to 30 ring-forming carbon atoms, or substituted or unsubstituted heterocycles with 2 to 30 ring-forming carbon atoms. 21 ~L 24 Each is independently and directly connected. JPEG2026089377000123.jpg319, JPEG2026089377000124.jpg319, JPEG2026089377000125.jpg1519, JPEG2026089377000126.jpg1319, JPEG2026089377000127.jpg1519, JPEG2026089377000128.jpg1524 , a substituted or unsubstituted divalent alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring-forming carbon atoms, where e1 to e4 are each independently 0 or 1. 31 ~R 39Each of these is independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group having 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 R 31 ~R 39 In this structure, adjacent bases are linked to each other to form a ring, and d1 to d4 are each independent integers between 0 and 4 (inclusive).
[0175] The compound represented by the chemical formula Mb can be used as a blue phosphorescent dopant or a green phosphorescent dopant. In one embodiment, the compound represented by the chemical formula Mb may also be further included in the light-emitting layer EML as an auxiliary dopant.
[0176] A compound represented by the chemical formula Mb may be any one of the compounds in the group of compounds Mb-1 to Mb-11 listed below. However, the compounds listed below are illustrative examples, and the compound represented by the chemical formula Mb is not limited to compounds Mb-1 to Mb-11 listed below.
[0177] [ka]
[0178] In the compound with chemical formula MB-11, R, R 38 , and R 39 Each of these may independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group having 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.
[0179] The luminescent layer EML may further contain a compound represented by any one of the following chemical formulas Fa to Fc. The compounds represented by the following chemical formulas Fa to Fc can be used as fluorescent dopant materials. [Chemical formula Fa] [ka]
[0180] In the chemical formula Fa, R a ~R j The two selected from among them are independent of each other. JPEG2026089377000131.jpg423 It may be replaced with R. a ~R j among JPEG2026089377000132.jpg423 The remaining unsubstituted atoms may each independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group having 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. JPEG2026089377000133.jpg423 In this, Ar1 and Ar2 are each independently substituted or unsubstituted aryl groups having 6 to 30 ring-forming carbon atoms, or substituted or unsubstituted heteroaryl groups having 2 to 30 ring-forming carbon atoms. For example, at least one of Ar1 and Ar2 may be a heteroaryl group containing O or S as a ring-forming atom.
[0181] [Chemical formula Fb] [ka]
[0182] In the chemical formula Fb, R a and R bEach 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 R a and R b These elements may be joined together to form a ring.
[0183] In the chemical formula Fb, Ar1 to Ar4 may each be independently 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.
[0184] In chemical formula Fb, U and V may each be independently a substituted or unsubstituted hydrocarbon ring having 5 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroring having 2 to 30 ring-forming carbon atoms.
[0185] In chemical formula Fb, the number of rings represented by U and V may be 0 or 1 independently. For example, in 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 chemical formula Fb is a tetracyclic compound. Also, if the number of both U and V is 0, the condensed ring with a fluorene core in chemical formula Fb is a tricyclic compound. Also, if the number of U and V is 1, the condensed ring with a fluorene core in chemical formula Fb is a quintic cyclic compound.
[0186] [Chemical formula Fc] [ka]
[0187] In the chemical formula Fc, A1 and A2 are independently O, S, Se, or NR. m And R m R1~R 11 Each of these is independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted amino group, a substituted or unsubstituted boryl group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thio group, a substituted or unsubstituted alkyl group having 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 R1~R 11 Within this structure, adjacent groups bond to each other to form a ring.
[0188] In the chemical formula Fc, A1 and A2 may each independently bond to a substituent on an adjacent ring to form a fused ring. For example, A1 and A2 may each independently form NR m If so, A1 may bond with R4 or R5 to form a ring. Also, A2 may bond with R7 or R8 to form a ring.
[0189] 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-ethylcarbazolyl)vinyl]benzene (BCzVB), 4-(di-p-tolylamino)-4'-[(di-p-tolylamino)styryl]stilbene (DPAVB), N-(4-((E)-2-(6-((E)-4-(diphenylamino)styryl)naphthalen-2-yl)vinyl)phenyl) It may also contain -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.).
[0190] In one embodiment, if a plurality of light-emitting layers (EMLs) are included, at least one of the light-emitting layers (EMLs) may contain a known phosphorescent dopant material. 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. More 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, this embodiment is not limited to these.
[0191] On the other hand, in one embodiment, the emissive layer EML may include a hole-transporting host and an electron-transporting host. The emissive layer EML may also include an auxiliary dopant and a luminescent dopant. On the other hand, the auxiliary dopant may include a phosphorescent dopant material or a thermally activated delayed fluorescence dopant material. In other words, in one embodiment, the emissive layer EML may include a hole-transporting host, an electron-transporting host, an auxiliary dopant, and a luminescent dopant.
[0192] Furthermore, an exciplex may be formed in the EML (Emission-Mounted Layer) by a hole-transporting host and an electron-transporting host. In this case, the triplet energy of the exciplex formed by the hole-transporting host and the electron-transporting host corresponds to T1, which is the interval between the LUMO energy level of the electron-transporting host and the HOMO energy level of the hole-transporting host.
[0193] In one embodiment, the triplet energy (T1) of the exciplex formed by the hole-transporting host and the electron-transporting host may be between 2.4 eV and 3.0 eV. Furthermore, the triplet energy of the exciplex may be smaller than the energy gap of each host material. Therefore, the exciplex may have a triplet energy of 3.0 eV or less, which is the energy gap between the hole-transporting host and the electron-transporting host.
[0194] The luminescent layer EML may contain quantum dot material. The core of the quantum dot may be selected from group II-VI compounds, group III-VI compounds, group I-III-VI compounds, group III-V compounds, group III-II-V compounds, group IV-VI compounds, group IV elements, group IV compounds, and combinations thereof.
[0195] 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, including CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, CdZnSe, CdZnTe, CdHgS, CdHgSe, and CdHgTe. A ternary compound selected from the group consisting of HgZnS, HeZnSe, HeZnTe, MgZnSe, MgZnS, and mixtures thereof may be selected from the group consisting of HgZnTeS, CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe, HgZnSTe, and mixtures thereof.
[0196] Group III-VI compounds may include dielemental compounds such as In2S3 and In2Se3, trielemental compounds such as InGaS3 and InGaSe3, or any combination thereof.
[0197] The 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.
[0198] The group III-V compounds may 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, the group III-V compounds may further contain group II metals. For example, InZnP may be selected as a III-II-V group compound.
[0199] 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.
[0200] Each element in a multi-element compound, such as a binary, ternary, or quaternary compound, may be present within the particles at uniform or heterogeneous concentrations. In other words, the chemical formula indicates the types of elements contained in the compound, and the elemental ratios within the compound may differ. For example, AgInGAs2 is AgIn x Ga 1-xThis can mean S² (where X is a real number between 0 and 1).
[0201] On the other hand, a quantum dot may have a single structure or a core-shell dual structure in which the concentration of each element contained in the quantum dot is uniform. For example, the material contained in the core and the material contained in the shell may be different from each other.
[0202] The shell of a 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.
[0203] 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. 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. Examples of quantum dot shells include metallic or nonmetallic oxides, semiconductor compounds, or combinations thereof.
[0204] For example, metallic or nonmetallic oxides include dielemental compounds such as SiO2, Al2O3, TiO2, ZnO, MnO, Mn2O3, Mn3O4, CuO, FeO, Fe2O3, Fe3O4, CoO, Co3O4, and NiO, or trielemental compounds such as MgAl2O4, CoFe2O4, NiFe2O4, and CoMn2O4, but the present invention is not limited to these.
[0205] Furthermore, while semiconductor compounds include CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnSeS, ZnTeS, GaAs, GaP, GaSb, HgS, HgSe, HgTe, InAs, InP, InGaP, InSb, AlAs, AlP, and AlSb, the present invention is not limited to these.
[0206] In multi-element compounds such as binary and ternary compounds, each element may be present within the particles at a uniform or non-uniform concentration. In other words, the chemical formula represents the types of elements contained in the compound, and the elemental ratios within the compound may differ.
[0207] 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. 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.
[0208] Furthermore, the form of the quantum dots is not particularly limited and is a form 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.
[0209] The energy band gap can be adjusted by controlling the size of the quantum dots or the elemental ratio within the quantum dot compound, thus enabling the emission of light across a wide range of wavelengths in 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 light-emitting devices that emit light at various wavelengths. More 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. Alternatively, the quantum dots may be configured to emit white light by combining light of various colors.
[0210] 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, the electron transport layer ETL, and the electron injection layer EIL.
[0211] 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.
[0212] 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 structures such as an electron transport layer (ETL) / electron injection layer (EIL), a hole blocking layer (HBL) / electron transport layer (ETL) / electron injection layer (EIL), or an electron transport layer (ETL) / buffer layer (not shown) 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 100 nm to about 150 nm.
[0213] Electron transport regions (ETRs) can be formed using a variety of methods, including vacuum deposition, spin coating, casting, LB (Laser-Based) deposition, inkjet printing, laser printing, and laser thermal transfer (LITI).
[0214] The electron transport region (ETR) may include the compound represented by the following chemical formula ET-1. [Chemical formula ET-1] [ka]
[0215] In the chemical formula ET-1, at least one of X1 to X3 is N and the rest are CR. a That is. R aAr1 to Ar3 may 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.
[0216] In chemical formula ET-1, a to c may each be an independent integer between 0 and 10. In chemical formula ET-1, L1 to L3 may each be an independently directly bonded, substituted, or unsubstituted arylene group with 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroarylene group with 2 to 30 ring-forming carbon atoms. On the other hand, if a to c are integers of 2 or more, then multiple L1 to L3 may each be independently a substituted or unsubstituted arylene group with 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroarylene group with 2 to 30 ring-forming carbon atoms.
[0217] The electron transport region (ETR) may include anthracene compounds. However, the electron transport region ETR is not limited to these; for example, 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)-4-phenyl-5-terto-butyl The following may be included: phenyl-1,2,4-triazole, NTAZ (4-(naphthalene-1-yl)-3,5-diphenyl-4H-1,2,4-triazole), tBu-PBD (2-(4-biphenylyl)-5-(4-tertobutylphenyl)-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), TSPO1 (diphenyl(4-(triphenylsilyl)phenyl)phosphine oxide), and mixtures thereof.
[0218] The electron transport region (ETR) may contain at least one of the following compounds ET1 to ET36. [ka] [ka] [ka] [ka] [ka] [ka] [ka]
[0219] 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 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 this embodiment is not limited to these. The electron transport region (ETR) may also be composed 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, the organometallic salt may include, for example, metal acetate, metal benzoate, metal acetoacetate, metal acetylacetonate, or metal stearate.
[0220] 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).
[0221] 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.
[0222] If the electron transport region (ETR) includes an electron transport layer (ETL), the thickness of the electron transport layer (ETL) may be approximately 10 nm to 100 nm, for example, approximately 15 nm to 50 nm. If the thickness of the electron transport layer (HTL) satisfies the above-mentioned range, satisfactory electron transport characteristics can be obtained without a substantial increase in the driving voltage. If the electron transport region (ETR) includes an electron injection layer (EIL), the thickness of the electron injection layer (EIL) may be approximately 0.1 nm to 10 nm, or approximately 0.3 nm to 9 nm. If the thickness of the electron injection layer (EIL) satisfies the above-mentioned range, satisfactory electron injection characteristics can be obtained without a substantial increase in the driving voltage.
[0223] The second electrode EL2 is provided on the electron transport region ETR. The second electrode EL2 may be a common electrode. The second electrode EL2 may be a cathode or an anode, but this embodiment is not limited to these. For example, if the first electrode EL1 is an anode, the second electrode may be a cathode, and if the first electrode EL1 is a cathode, the second electrode EL2 may be an anode. The second electrode EL2 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.
[0224] The second electrode EL2 may be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode. If the second electrode EL2 is a transmissive electrode, it is made of a transparent metal oxide, such as ITO, IZO, ZnO, ITZO, etc.
[0225] If the second electrode EL2 is a semi-transparent or reflective electrode, the second electrode EL2 may contain Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF / Ca (a layered structure of LiF and Ca), LiF / Al (a layered structure of LiF and Al), Mo, Ti, Yb, W, or compounds or mixtures containing these (e.g., AgMg, AgYb, or MgYb). Alternatively, the second electrode EL2 may have a multi-layer structure including a reflective or semi-transparent film made of a material, and a transparent conductive film made of ITO, IZO, ZnO, ITZO, etc. For example, the second electrode EL2 may contain the above-mentioned metallic materials, a combination of two or more metallic materials selected from the above-mentioned metallic materials, or oxides of the above-mentioned metallic materials.
[0226] Although not shown in the diagram, the second electrode EL2 may be connected to an auxiliary electrode. If the second electrode EL2 is connected to an auxiliary electrode, the resistance of the second electrode EL2 may be reduced.
[0227] On the other hand, a capping layer CPL may be further disposed on the second electrode EL2 of the light-emitting element ED in one embodiment. The capping layer CPL may be multilayer or monolayer.
[0228] In one embodiment, the capping layer CPL may be an organic or inorganic layer. For example, if the capping layer CPL contains an inorganic substance, the inorganic substance may include alkali metal compounds such as LiF, alkaline earth compounds such as MgF2, SiON, SiNx, SiOy, etc.
[0229] For example, if the capping layer CPL contains organic matter, it may include α-NPD, NPB, TPD, m-MTDATA, Alq3, CuPc, TPD15 (N4,N4,N4',N4'-tetra(biphenyl-4-yl)biphenyl-4,4'-diamine), TCTA (4,4',4”-tris(carbazole-9-yl)triphenylamine), or epoxy resin, or acrylates such as methacrylate. However, this embodiment is not limited to these, and the capping layer CPL may contain at least one of the compounds P1 to P5 described below. [ka] [ka] [ka] [ka] [ka]
[0230] On the other hand, the refractive index of the capping layer CPL may be 1.6 or higher. More specifically, for light in the wavelength range of 550 nm to 660 nm, the refractive index of the capping layer CPL may be 1.6 or higher.
[0231] Figures 7 and 10 are cross-sectional views of a display device according to one embodiment. In the following description of the display device according to one embodiment, with reference to Figures 7 and 10, we will not repeat the content described in Figures 1 to 6 above, but will focus on the differences.
[0232] 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.
[0233] In one 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, the display element layer DP-ED may include a light-emitting element ED.
[0234] 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 is also to which the structures of the light-emitting elements shown in Figures 3 to 6 described above apply.
[0235] The hole transport region HTR of the light-emitting element ED included in the display device DD-a according to one embodiment contains the amine compound of the above-described embodiment.
[0236] Referring to Figure 7, the light-emitting layer EML may be located within the opening OH defined in the pixel-defining film PDL. 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-defining 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 figures, 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.
[0237] 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. The photoconverters can convert the wavelength of the provided light and emit it. In other words, the optical control layer (CCL) may be a layer containing quantum dots or a layer containing phosphors.
[0238] The optical control layer (CCL) may include multiple optical control units (CCP1, CCP2, CCP3). The optical control units CCP1, CCP2, and CCP3 may be spaced apart from each other.
[0239] Referring to Figure 7, a segmentation pattern BMP is provided between the optical control units CCP1, CCP2, and CCP3, which are spaced apart from each other, but this embodiment is not limited to this. In Figure 8, 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.
[0240] 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.
[0241] In one embodiment, the first optical control unit CCP1 can provide red light, which is the second color light, and the second optical control unit CCP2 can provide green light, which is the third color light. The third optical control unit CCP3 can transmit and provide blue light, which is the first color light, 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 can be applied to quantum dots QD1 and QD2.
[0242] 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 but not a quantum dot.
[0243] 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.
[0244] 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 includes first quantum dots QD1 and scatterers SP dispersed in the first base resin BR1, the second optical control unit CCP2 includes 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. The base resins BR1, BR2, and BR3 are media in which the quantum dots QD1 and QD2 and scatterers SP are dispersed, and can consist of a variety of 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.
[0245] The optical control layer CCL may include a barrier layer BFL1. The barrier layer BFL1 can prevent the penetration of moisture and / or oxygen (hereinafter referred to as "moisture / oxygen"). The barrier layer BFL1 is placed on top of the optical control units CCP1, CCP2, and CCP3 to prevent the optical control units CCP1, CCP2, and CCP3 from being exposed to moisture / oxygen. On the other hand, the barrier layer BFL1 may cover the optical control units CCP1, CCP2, and CCP3. Furthermore, a barrier layer BLF2 may be provided between the optical control units CCP1, CCP2, and CCP3 and the filter layers CF1, CF2, and CF3.
[0246] The barrier layers BFL1 and BFL2 may include at least one inorganic layer. In other words, the barrier layers BFL1 and BFL2 can be formed by including inorganic materials. For example, the barrier layers BFL1 and BFL2 may be formed by including silicon nitride, aluminum nitride, zirconium nitride, titanium nitride, hafnium nitride, tantalum nitride, silicon oxide, aluminum oxide, titanium oxide, tin oxide, cerium oxide, and silicon oxynitride, or a thin metal film with sufficient light transmittance. On the other hand, the barrier layers BFL1 and BFL2 may further include an organic film. The barrier layers BFL1 and BFL2 may consist of a single layer or multiple layers.
[0247] In one embodiment of the display device DD-a, the color filter layer CFL may be placed on top of the light control layer CCL. For example, the color filter layer CFL may be placed directly on top of the color control layer CCL. In this case, the barrier layer BFL2 may be omitted.
[0248] The color filter layer CFL may include filters CF1, CF2, and CF3. The color filter CFL may include a first filter CF1 that transmits second-color light, a second filter CF2 that transmits third-color light, and a third filter CF3 that transmits first-color light. For example, the first filter CF1 may be a red filter, the second filter CF2 a green filter, and the third filter CF3 a blue filter. Each of the filters CF1, CF2, and CF3 may contain a polymer photosensitive resin and a pigment or dye. The first filter CF1 may contain a red pigment or dye, the second filter CF2 may contain a green pigment or dye, and the third filter CF3 may contain a blue pigment or dye. On the other hand, this embodiment is not limited thereto, and the third filter CF3 does not have to contain a pigment or dye. The third filter CF3 may contain a polymer photosensitive resin and not contain a pigment or dye. The third filter CF3 may be transparent. The third filter CF3 may be made of a transparent photosensitive resin.
[0249] 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. 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.
[0250] On the other hand, although not shown, the color filter layer CFL may include a light-shielding portion (not shown). The color filter layer CFL may include a light-shielding portion (not shown) that is arranged to overlap the boundaries of adjacent filters CF1, CF2, and CF3. The light-shielding portion (not shown) may be a black matrix. The light-shielding portion (not shown) may be formed by including an organic light-shielding material or an inorganic light-shielding material containing a black pigment or black dye. The light-shielding portion (not shown) may demarcate the boundaries between adjacent filters CF1, CF2, and CF3. In one embodiment, the light-shielding portion (not shown) may be formed by a blue filter.
[0251] A base substrate BL may be placed on top of the color filter layer CFL. The base substrate BL may be a member 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, this 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, unlike in the figures, the base substrate BL may be omitted in one embodiment.
[0252] 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 provided by sequentially stacking them in the thickness direction between a first electrode EL1 and a second electrode EL2, and between the first electrode EL1 and the second electrode EL2, facing each other. Each of the light-emitting structures OL-B1, OL-B2, and OL-B3 may include a light-emitting layer EML (Figure 7), a hole transport region HTR and an electron transport region ETR arranged with the light-emitting layer EML (Figure 7) in between.
[0253] 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 multiple light-emitting layers.
[0254] In one embodiment shown in Figure 8, the light emitted from each of the light-emitting structures OL-B1, OL-B2, and OL-B3 may all be blue light. However, this 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 may be different from each other. For example, a light-emitting element ED-BT including a plurality of light-emitting structures OL-B1, OL-B2, and OL-B3 that emit light in different wavelength ranges from each other can emit white light.
[0255] Charge generation layers CGL1 and CGL2 are positioned between adjacent light-emitting structures OL-B1, OL-B2, and OL-B3. Charge generation layers CGL1 and CGL2 include a p-type charge generation layer and / or an n-type charge generation layer.
[0256] At least one of the light-emitting structures OL-B1, OL-B2, and OL-B3 included in the display device DD-TD of one embodiment can contain the amine compound of the above embodiment.
[0257] 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 the first to third light-emitting elements ED-1, ED-2, and ED-3 each include two light-emitting layers stacked in the thickness direction. In each of the first to third light-emitting elements ED-1, ED-2, and ED-3, the two light-emitting layers may emit light in the same wavelength range.
[0258] 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.
[0259] 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 for all first to third light-emitting elements ED-1, ED-2, and ED-3. However, this embodiment is 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.
[0260] 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 arranged between the hole transport region HTR and the light-emitting auxiliary region OG. 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 arranged between the light-emitting auxiliary region OG and the electron transport region ETR.
[0261] 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.
[0262] 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.
[0263] Unlike Figures 8 and 9, Figure 10 shows that the display device DD-c includes 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. Of the four light-emitting structures, the first to third light-emitting 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, this embodiment is not limited thereto, and the first to fourth light-emitting structures OL-B1, OL-B2, OL-B3, and OL-C1 may emit light in different wavelength regions.
[0264] The charge generation layers GCL1, CGL2, and CGL3, which are positioned between adjacent light-emitting structures OL-B1, OL-B2, OL-B3, and OL-C1, may include a p-type charge generation layer and / or an n-type charge generation layer.
[0265] At least one of the light-emitting structures OL-B1, OL-B2, OL-B3, and OL-C1 contained in the display device DD-c of one embodiment may contain the amine compound of the embodiment described above.
[0266] A light-emitting element (ED) according to one embodiment of the present invention can exhibit improved long-life characteristics by including the amine compound of the embodiment described above in at least one functional layer disposed between the first electrode EL1 and the second electrode EL2. The light-emitting element (ED) according to one embodiment may include the amine compound of the embodiment described above in at least one of the hole transport region (HTR), light-emitting layer (EML), and electron transport region (ETR) disposed between the first electrode EL1 and the second electrode EL2, or it may be included in the capping layer (CPL). For example, the amine compound of one embodiment can be included in the hole transport region (HTR) of the light-emitting element (ED) according to one embodiment, and the light-emitting element of one embodiment can exhibit long-life characteristics.
[0267] The amine compound of the above embodiment, by including a first core and second and third substituents, can increase the stability of the material and improve hole transport properties. This extends the lifespan of the light-emitting element containing the amine compound of the embodiment. Furthermore, the light-emitting element of the embodiment can exhibit excellent lifespan characteristics by including the amine compound of the embodiment in the hole transport layer.
[0268] Figure 11 shows a vehicle in which a display device according to one embodiment is installed.
[0269] Referring to Figure 11, the electronic equipment of one embodiment may include display devices DD-1, DD-2, DD-3, and DD-4 for vehicle AM. At least one of the first to fourth display devices DD-1, DD-2, DD-3, and DD-4 may similarly include the configuration of 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.
[0270] Figure 11 shows the first to fourth display devices DD-1, DD-2, DD-3, and DD-4 as display devices for vehicle AMs, which are placed inside the vehicle AM. However, this is illustrative, and the first to fourth display devices DD-1, DD-2, DD-3, and DD-4 may be placed in various means of transportation 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 electronic devices selected from large display devices such as televisions, monitors, and outdoor billboards, personal computers (PCs), notebook computers, personal digital devices (PDAs), in-vehicle display devices, game consoles, portable electronic devices, and small to medium-sized display devices such as cameras. 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.
[0271] 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 of one embodiment described with reference to Figures 3 to 6. The light-emitting element ED of one embodiment may include an amine compound of one embodiment. At least one of the first to fourth display devices DD-1, DD-2, DD-3, and DD-4 can have its display life improved by including a light-emitting element ED containing an amine compound of one embodiment.
[0272] Referring to Figure 11, the vehicle AM may include a steering wheel HA and a gear GR for operating the vehicle AM. The vehicle AM may also include a forward window GL positioned to face the driver.
[0273] 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.
[0274] 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 of the vehicle AM. The second display device DD-2 may be optically transparent. The second information includes digital figures indicating the vehicle AM's speed and may further include information such as the current time. Contrary to the illustration, the second information of the second display device DD-2 may be projected onto the front window GL.
[0275] 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 (or image) playback, and the temperature inside the vehicle AM.
[0276] 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 can display images of the outside of the vehicle AM captured by a camera module CM located on the outside of the vehicle AM. The fourth information may include images of the outside of the vehicle AM.
[0277] 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 relating to the interior and exterior of the vehicle AM. The first to fourth pieces of information may contain different information from each other. However, the embodiments are not limited thereto, and some of the first to fourth pieces of information may contain the same information from each other. [Examples]
[0278] The following describes in detail a condensed polycyclic compound and a light-emitting element 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.
[0279] [Examples] 1. Synthesis of amine compounds First, the method for synthesizing amine compounds according to this embodiment will be explained in detail, illustrating the synthesis methods of the first to twelfth compounds disclosed in Table 5 below. Furthermore, the synthesis method of amine compounds described below is just one example, and the synthesis method of amine compounds according to the embodiments of the present invention is not limited to the following examples.
[0280] <Method for synthesizing intermediates used in the synthesis of compounds> (Synthesis of intermediate A3) [ka]
[0281] Intermediate A1 (10 mmol), Intermediate A2 (10 mmol), NaO t Bu (10 mmol) and P(Bu)3HBF4 (1 mmol) were combined with toluene (200 mL) and degassed. Bis(dibenzylideneacetone)palladium (0.5 mmol) was added under an argon atmosphere, and the mixture was heated and stirred at 100°C for 6 hours. After the reaction solution cooled to room temperature, it was extracted with toluene, washed with H2O and brine, and then dried over Na2SO4. The resulting solution was concentrated and purified by column chromatography to obtain intermediate A3 (9.1 mmol, 91%, MS 451.1).
[0282] (Synthesis of intermediate A5) [ka]
[0283] Intermediate A4 (10 mmol), Intermediate A2 (10 mmol), NaO tBu (10 mmol) and P(Bu)3HBF4 (1 mmol) were combined with toluene (200 mL) and degassed. Bis(dibenzylideneacetone)palladium (0.5 mmol) was added under an argon atmosphere, and the mixture was heated and stirred at 100°C for 6 hours. After the reaction solution cooled to room temperature, it was extracted with toluene, washed with H2O and brine, and then dried over Na2SO4. The resulting solution was concentrated and purified by column chromatography to obtain intermediate A5 (8.8 mmol, 88%, MS 451.1).
[0284] (Synthesis of intermediate A7) [ka]
[0285] Intermediate A6 (10 mmol), Intermediate A2 (10 mmol), NaO t Bu (10 mmol) and P(Bu)3HBF4 (1 mmol) were combined with toluene (200 mL) and degassed. Bis(dibenzylideneacetone)palladium (0.5 mmol) was added under an argon atmosphere, and the mixture was heated and stirred at 100°C for 6 hours. After the reaction solution cooled to room temperature, it was extracted with toluene, washed with H2O and brine, and then dried over Na2SO4. The resulting solution was concentrated and purified by column chromatography to obtain intermediate A7 (8.6 mmol, 86%, MS 491.1).
[0286] (Synthesis of intermediate A10) [ka]
[0287] Intermediate A8 (10 mmol), Intermediate A9 (10 mmol), NaO tBu (10 mmol) and P(Bu)3HBF4 (1 mmol) were combined with toluene (200 mL) and degassed. Bis(dibenzylideneacetone)palladium (0.5 mmol) was added under an argon atmosphere, and the mixture was heated and stirred at 100°C for 6 hours. After the reaction solution cooled to room temperature, it was extracted with toluene, washed with H2O and brine, and then dried over Na2SO4. The resulting solution was concentrated and purified by column chromatography to obtain intermediate A10 (8.7 mmol, 87%, MS 500.2).
[0288] <Methods for synthesizing compounds> 1) Synthesis of the first compound [ka]
[0289] Intermediate A3 (10 mmol), Intermediate A11 (10 mmol), NaO t Bu (10 mmol) and P(Bu)3HBF4 (1 mmol) were combined with toluene (200 mL) and degassed. Bis(dibenzylideneacetone)palladium (0.5 mmol) was added under an argon atmosphere, and the mixture was heated and stirred at 100°C for 6 hours. After the reaction solution cooled to room temperature, it was extracted with toluene, washed with H2O and brine, and dried over Na2SO4. The resulting solution was concentrated and purified by column chromatography to obtain compound 1 (8.1 mmol, 81%, MS 693.2).
[0290] 2) Synthesis of the second compound [ka]
[0291] Intermediate A3 (10 mmol), Intermediate A12 (10 mmol), NaO tBu (10 mmol) and P(Bu)3HBF4 (1 mmol) were combined with toluene (200 mL) and degassed. Bis(dibenzylideneacetone)palladium (0.5 mmol) was added under an argon atmosphere, and the mixture was heated and stirred at 100°C for 6 hours. After the reaction solution cooled to room temperature, it was extracted with toluene, washed with H2O and brine, and then dried with Na2SO4. The resulting solution was concentrated and purified by column chromatography to obtain compound 2 (7.8 mmol, 78%, MS 693.2).
[0292] 3) Synthesis of the third compound [ka]
[0293] Intermediate A3 (10 mmol), Intermediate A13 (10 mmol), NaO t Bu (10 mmol) and P(Bu)3HBF4 (1 mmol) were combined with toluene (200 mL) and degassed. Bis(dibenzylideneacetone)palladium (0.5 mmol) was added under an argon atmosphere, and the mixture was heated and stirred at 100°C for 6 hours. After the reaction solution cooled to room temperature, it was extracted with toluene, washed with H2O and brine, and then dried with Na2SO4. The resulting solution was concentrated and purified by column chromatography to obtain compound 3 (6.5 mmol, 65%, MS 693.2).
[0294] 4) Synthesis of the fourth compound [ka]
[0295] Intermediate A3 (10 mmol), Intermediate A14 (10 mmol), NaO tBu (10 mmol) and P(Bu)3HBF4 (1 mmol) were combined with toluene (200 mL) and degassed. Bis(dibenzylideneacetone)palladium (0.5 mmol) was added under an argon atmosphere, and the mixture was heated and stirred at 100°C for 6 hours. After the reaction solution cooled to room temperature, it was extracted with toluene, washed with H2O and brine, and then dried over Na2SO4. The resulting solution was concentrated and purified by column chromatography to obtain compound 4 (6.1 mmol, 61%, MS 693.2).
[0296] 5) Synthesis of the fifth compound [ka]
[0297] Intermediate A5 (10 mmol), Intermediate A9 (10 mmol), NaO t Bu (10 mmol) and P(Bu)3HBF4 (1 mmol) were combined with toluene (200 mL) and degassed. Bis(dibenzylideneacetone)palladium (0.5 mmol) was added under an argon atmosphere, and the mixture was heated and stirred at 100°C for 6 hours. After the reaction solution cooled to room temperature, it was extracted with toluene, washed with H2O and brine, and then dried with Na2SO4. The resulting solution was concentrated and purified by column chromatography to obtain compound 5 (8.3 mmol, 83%, MS 667.2).
[0298] 6) Synthesis of the sixth compound [ka]
[0299] Intermediate A3 (10 mmol), Intermediate A9 (10 mmol), NaO tBu (10 mmol) and P(Bu)3HBF4 (1 mmol) were combined with toluene (200 mL) and degassed. Bis(dibenzylideneacetone)palladium (0.5 mmol) was added under an argon atmosphere, and the mixture was heated and stirred at 100°C for 6 hours. After the reaction solution cooled to room temperature, it was extracted with toluene, washed with H2O and brine, and then dried with Na2SO4. The resulting solution was concentrated and purified by column chromatography to obtain compound 6 (7.8 mmol, 78%, MS 693.2).
[0300] 7) Synthesis of Compound VII [ka]
[0301] Intermediate A7 (10 mmol), Intermediate A15 (10 mmol), NaO t Bu (10 mmol) and P(Bu)3HBF4 (1 mmol) were combined with toluene (200 mL) and degassed. Bis(dibenzylideneacetone)palladium (0.5 mmol) was added under an argon atmosphere, and the mixture was heated and stirred at 100°C for 6 hours. After the reaction solution cooled to room temperature, it was extracted with toluene, washed with H2O and brine, and then dried with Na2SO4. The resulting solution was concentrated and purified by column chromatography to obtain compound VII (6.4 mmol, 64%, MS 733.2).
[0302] 8) Synthesis of Compound VIII [ka]
[0303] Intermediate A7 (10 mmol), Intermediate A16 (10 mmol), NaO tBu (10 mmol) and P(Bu)3HBF4 (1 mmol) were combined with toluene (200 mL) and degassed. Bis(dibenzylideneacetone)palladium (0.5 mmol) was added under an argon atmosphere, and the mixture was heated and stirred at 100°C for 6 hours. After the reaction solution cooled to room temperature, it was extracted with toluene, washed with H2O and brine, and then dried with Na2SO4. The resulting solution was concentrated and purified by column chromatography to obtain compound 8 (7.7 mmol, 77&, MS 673.2).
[0304] 9) Synthesis of Compound Nine [ka]
[0305] Intermediate A7 (10 mmol), Intermediate A17 (10 mmol), NaO t Bu (10 mmol) and P(Bu)3HBF4 (1 mmol) were combined with toluene (200 mL) and degassed. Bis(dibenzylideneacetone)palladium (0.5 mmol) was added under an argon atmosphere, and the mixture was heated and stirred at 100°C for 6 hours. After the reaction solution cooled to room temperature, it was extracted with toluene, washed with H2O and brine, and then dried with Na2SO4. The resulting solution was concentrated and purified by column chromatography to obtain compound 9 (8.3 mmol, 83%, MS 732.9).
[0306] 10) Synthesis of the 10th compound [ka]
[0307] Intermediate A7 (10 mmol), Intermediate A18 (10 mmol), NaO tBu (10 mmol) and P(Bu)3HBF4 (1 mmol) were combined with toluene (200 mL) and degassed. Bis(dibenzylideneacetone)palladium (0.5 mmol) was added under an argon atmosphere, and the mixture was heated and stirred at 100°C for 6 hours. After the reaction solution cooled to room temperature, it was extracted with toluene, washed with H2O and brine, and then dried with Na2SO4. The resulting solution was concentrated and purified by column chromatography to obtain compound 10 (8.2 mmol, 82%, MS 769.2).
[0308] 11) Synthesis of the 11th compound [ka]
[0309] Intermediate A3 (10 mmol), Intermediate A19 (10 mmol), NaO t Bu (10 mmol) and P(Bu)3HBF4 (1 mmol) were combined with toluene (200 mL) and degassed. Bis(dibenzylideneacetone)palladium (0.5 mmol) was added under an argon atmosphere, and the mixture was heated and stirred at 100°C for 6 hours. After the reaction solution cooled to room temperature, it was extracted with toluene, washed with H2O and brine, and then dried with Na2SO4. The resulting solution was concentrated and purified by column chromatography to obtain compound 11 (8.1 mmol, 81%, MS 709.2).
[0310] 12) Synthesis of Compound No. 12 [ka]
[0311] Intermediate A3 (10 mmol), Intermediate A20 (10 mmol), NaO tBu (10 mmol) and P(Bu)3HBF4 (1 mmol) were combined with toluene (200 mL) and degassed. Bis(dibenzylideneacetone)palladium (0.5 mmol) was added under an argon atmosphere, and the mixture was heated and stirred at 100°C for 6 hours. After the reaction solution cooled to room temperature, it was extracted with toluene, washed with H2O and brine, and then dried with Na2SO4. The resulting solution was concentrated and purified by column chromatography to obtain compound 12 (7.9 mmol, 79%, MS 679.0).
[0312] 13) Synthesis of Compound No. 13 [ka]
[0313] Intermediate A10 (10 mmol), Intermediate A21 (10 mmol), NaO t Bu (10 mmol) and P(Bu)3HBF4 (1 mmol) were combined with toluene (200 mL) and degassed. Bis(dibenzylideneacetone)palladium (0.5 mmol) was added under an argon atmosphere, and the mixture was heated and stirred at 100°C for 6 hours. After the reaction solution cooled to room temperature, it was extracted with toluene, washed with H2O and brine, and then dried with Na2SO4. The resulting solution was concentrated and purified by column chromatography to obtain compound 13 (7.6 mmol, 76%, MS 732.2).
[0314] 14) Synthesis of Compound No. 14 [ka]
[0315] Intermediate A10 (10 mmol), Intermediate A22 (10 mmol), NaO tBu (10 mmol) and P(Bu)3HBF4 (1 mmol) were combined with toluene (200 mL) and degassed. Bis(dibenzylideneacetone)palladium (0.5 mmol) was added under an argon atmosphere, and the mixture was heated and stirred at 100°C for 6 hours. After the reaction solution cooled to room temperature, it was extracted with toluene, washed with H2O and brine, and then dried with Na2SO4. The resulting solution was concentrated and purified by column chromatography to obtain compound 14 (6.7 mmol, 67%, MS 732.2).
[0316] 15) Synthesis of Compound No. 15 [ka]
[0317] Intermediate A10 (10 mmol), Intermediate A23 (10 mmol), NaO t Bu (10 mmol) and P(Bu)3HBF4 (1 mmol) were combined with toluene (200 mL) and degassed. Bis(dibenzylideneacetone)palladium (0.5 mmol) was added under an argon atmosphere, and the mixture was heated and stirred at 100°C for 6 hours. After the reaction solution cooled to room temperature, it was extracted with toluene, washed with H2O and brine, and then dried with Na2SO4. The resulting solution was concentrated and purified by column chromatography to obtain compound 15 (6.9 mmol, 69%, MS 732.2).
[0318] 2. Fabrication and evaluation of light-emitting devices An example of a light-emitting device containing the amine compound of one example in the hole transport layer was manufactured by the following method. The amine compounds of the example compounds, compounds 1 to 15 described above, were used as the material for the hole transport layer to produce the light-emitting devices of Examples 1 to 15. Comparative Examples 1 to 12 are light-emitting devices manufactured using comparative compound R1 to comparative compound R12 as the material for the hole transport layer.
[0319] [Example Compounds] [ka] [ka]
[0320] [Comparative Compounds] [ka]
[0321] (Fabrication of light-emitting elements) 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.
[0322] A light-emitting layer with a thickness of 25 nm was formed by co-depositing TBP and ADN on 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 with a thickness of 25 nm and LiF with a thickness of 1 nm.
[0323] Next, a second electrode was formed by depositing Al to a thickness of 100 nm.
[0324] In the example, the hole transport region, light-emitting layer, electron transport region, and second electrode were formed using a vacuum deposition apparatus.
[0325] The compounds used to fabricate the light-emitting element are as follows: (Materials used when fabricating the light-emitting element) [ka]
[0326] (2) Evaluation of light-emitting elements Table 5 below shows the evaluation of the light-emitting elements of the examples and comparative examples. Table 5 shows the element lifetime for the light-emitting elements of the examples and comparative examples. The element lifetime was evaluated using the C9920-11 brightness orientation characteristic measurement equipment manufactured by Hamamatsu Photonics, and the time it took for the brightness to degrade from the initial brightness value to 50% during continuous operation is shown relatively, with the value for Comparative Example 6 set to 100%.
[0327] [Table 5] [Table 45]
[0328] Referring to the results in Table 5, Examples 1 to 13 exhibit longer-life device characteristics compared to Comparative Examples 1 to 12.
[0329] The example compound comprises a first substituent of a benzonaphthothiophene substructure bonded to an amino group, a second substituent of a substructure such as phenyldibenzofuranyl, and a third substituent selected from the aryl group or heteroaryl group. Due to this specific group of substituents and substitution positions, it exhibits superior material stability compared to other comparative compounds. In other words, the molecular structural characteristics of the example compound, which distinguish it from the comparative compounds, result in a superior charge balance, and thus it can be confirmed that the example light-emitting device containing the example amine compound in the hole transport layer exhibits excellent long-life characteristics.
[0330] Comparative compounds R1, R4, R5, and R6 contain a first substituent and a third substituent bonded to the amino group, but do not contain the second substituent proposed in the present invention, which is thought to reduce the effects on stacking and intermolecular orientation due to intermolecular interactions. As a result, it can be confirmed that Comparative Examples 1, 4, 5, and 6, which contain Comparative Examples R1, R4, R5, and R6, respectively, have a relatively shorter device life compared to the example compounds. Comparative Examples R1 and R4 contain 9-phenylcarbazole without a phenyl group instead of a second substituent, Comparative Example R5 contains a dibenzothiophenyl group without a phenyl group instead of a second substituent, and Comparative Example R6 contains a dibenzofuranyl group without a phenyl group instead of a second substituent. Therefore, it is thought that the light-emitting elements of Comparative Examples 1, 4, 5, and 6, which contain Comparative Examples R1, R4, R5, and R6, have a shorter device life.
[0331] Comparative compounds R2, R7, and R8 contain a first and third substituent bonded to an amino group, but do not contain the second substituent proposed in the present invention. This is thought to reduce the effects on stacking and intermolecular orientation due to intermolecular interactions. Consequently, Comparative Examples 2, 7, and 8, which contain Comparative Examples R2, R7, and R8, respectively, show relatively lower device lifetimes compared to the example compounds. In the case of Comparative Example R2, it contains a diphenyldibenzofuranyl group instead of a second substituent, which is thought to have resulted in a reduced device lifetime for the light-emitting element in Comparative Example 2, which contains Comparative Example R2. In the case of Comparative Example R7, it does not contain a second substituent, and the presence of a dibenzofuranyl group substituted with a larger volume fluorenyl group suppresses intermolecular interactions. This is thought to have resulted in a reduced device lifetime for the light-emitting element in Comparative Example 7, which contains Comparative Example R7. In the case of comparative compound R8, the absence of a second substituent and the presence of a dibenzofuranyl group substituted with a highly electron-donating phenazine group strengthens the intermolecular interactions, which is thought to have resulted in a reduced device lifespan for the light-emitting element of comparative example 8, which included comparative compound R8.
[0332] Comparative compounds R3, R11, and R12 contain a third substituent but do not contain the first and second substituents proposed in the present invention, which is thought to reduce the effects on stacking and intermolecular orientation due to intermolecular interactions. As a result, it can be confirmed that Comparative Examples 3, 11, and 12, which contain Comparative Examples R3, R11, and R12, respectively, have a relatively shorter device life compared to the example compounds. In the case of Comparative Example compound R3, the presence of a benzonaphthothiophenyl group substituted with an arylamino group without the first substituent results in different electronic and steric effects around the two amino groups in the diamine compound compared to the example compounds, which is thought to have led to a shorter device life of the light-emitting element in Comparative Example 3, which contains Comparative Example compound R3. In the case of Comparative Example compound R11, the absence of the first substituent and the linkage of the benzonaphthothiophenyl group to the amino group via a phenylene linker is thought to have led to a shorter device life of the light-emitting element in Comparative Example 11, which contains Comparative Example compound R11. In the case of comparative compound R12, the absence of a first substituent and the presence of a benzonaphthothiophenyl group substituted with a larger volume dibenzofuranyl group suppressed intermolecular interactions, and it is thought that the light-emitting element of comparative example 12 containing comparative compound R12 had a reduced device lifespan.
[0333] Comparative compound R9 contains a second substituent but does not contain the first and third substituents proposed in the present invention, and it is thought that the effects on stacking and intermolecular orientation due to intermolecular interactions are reduced. As a result, it can be confirmed that Comparative Example 9, which contains comparative compound R9, has a relatively shorter device lifetime compared to the example compound. In the case of comparative compound R9, unlike the first substituent, the naphthalene substructure of the benzonaphthothiophene substructure is linked to the core nitrogen atom, and because it contains a benzofuranyl group instead of a third substituent, the electronic and steric effects are different from those of the example compound, and it is thought that the light-emitting element of Comparative Example 9, which contains comparative compound R9, has a shorter device lifetime.
[0334] Comparative compound R10 contains a third substituent but does not contain the first and second substituents proposed in the present invention, which is thought to reduce the effects on stacking and intermolecular orientation due to intermolecular interactions. As a result, it can be confirmed that Comparative Example 10, which contains comparative compound R10, has a relatively shorter device lifetime compared to the example compounds. In the case of comparative compound R10, unlike the first substituent, the naphthalene substructure of the benzonaphthothiophene substructure is linked to the core nitrogen atom, and it contains a dibenzofuranyl group that is not substituted with a phenyl group instead of the second substituent, which is thought to have resulted in a shorter device lifetime for the light-emitting element of Comparative Example 10, which contains comparative compound R10.
[0335] Although preferred embodiments of the present invention have been described so far with reference, a person skilled in the art or a person with ordinary knowledge in the art will understand that the present invention can be modified and altered in various ways without departing from the spirit and technical domain of the invention as described in the claims below. Therefore, the technical scope of the present invention should not be limited to what is described in the detailed description of the specification, but should be determined by the claims. [Explanation of Symbols]
[0336] DD, DD-TD, DD-a, DD-b, and DD-c: Display devices ED: Organic electroluminescent element EL1: First electrode EL2: Second electrode HTR: Hole transport region EML: Emitting layer ETR: Electron transport region HTL: Hole Transport Layer
Claims
1. First electrode and A second electrode is placed on the first electrode, A light-emitting element comprising: a functional layer disposed between the first electrode and the second electrode and containing an amine compound represented by the following chemical formula 1: [Chemical formula 1] 【Chemistry 1】 In the aforementioned chemical formula 1, L is 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. Ar 1 is a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, however, Ar 1 This does not include substituted or unsubstituted benzofuranyl groups and substituted or unsubstituted benzothiophenyl groups. R 1 It is represented by the following chemical formula 2, R 2 It is represented by the following chemical formula 3: [Chemical formula 2] 【Chemistry 2】 In the aforementioned chemical formula 2, R a1 ~R a4 One of these is a position that is linked to the chemical formula 1, R a1 ~R a4 The remaining atoms are, independently, a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms. R a5 to R a10 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, [Chemical formula 3] 【Transformation 3】 In the aforementioned chemical formula 3, X is O, S, or NAr 2 And, Ar 2 This is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms in a ring, R b1 ~R b4 One of these is a position that is linked to the chemical formula 1, R b1 ~R b4 The remaining atoms are, independently, a hydrogen atom, a deuterium atom, a halogen atom, or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms. R b5 ~R b8 One of these is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, however, R b5 ~R b8 It does not contain substituted or unsubstituted fluorenyl groups. R b5 ~R b8 The remaining atoms are, independently, a hydrogen atom, a deuterium atom, a halogen atom, or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.
2. The at least one functional layer includes a light-emitting layer, a hole transport region disposed between the first electrode and the light-emitting layer, and an electron transport region disposed between the light-emitting layer and the second electrode. The light-emitting element according to claim 1, wherein the hole transport region comprises an amine compound represented by the chemical formula 1.
3. The hole transport region includes a hole injection layer disposed on the first electrode and a hole transport layer disposed on the hole injection layer. The light-emitting element according to claim 2, wherein the hole transport layer comprises an amine compound represented by the chemical formula 1.
4. The light-emitting element according to claim 1, wherein the amine compound represented by the chemical formula 1 is a monoamine compound.
5. In the aforementioned chemical formula 1, The light-emitting element according to claim 1, wherein L is a directly bonded, substituted, or unsubstituted phenylene group.
6. In the aforementioned chemical formula 1, Ar 1 The light-emitting element according to claim 1, wherein is a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenantrenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted carbazolyl group.
7. The amine compound represented by the chemical formula 1 is the light-emitting element according to claim 1, represented by the following chemical formula 1-1: [Chemical formula 1-1] 【Chemistry 4】 In the above chemical formula 1-1, A 1 ~A 3 Each of these is independently a hydrogen atom, a deuterium atom, a halogen atom, or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms. L, Ar 1 , and R 2 This is as defined in Chemical Formula 1 above.
8. The amine compound represented by chemical formula 1 is the light-emitting element according to claim 1, which is represented by any one of the following chemical formulas 1-2 to 1-5: [Chemical formula 1-2] 【Transformation 5】 [Chemical formula 1-3] 【Transformation 6】 [Chemical formula 1-4] 【Transformation 7】 [Chemical formula 1-5] 【Transformation 8】 In the aforementioned chemical formulas 1-2 to 1-5, R x1 ~R x4 Each of these is independently a hydrogen atom, a deuterium atom, or a substituted or unsubstituted alkyl group having 1 to 5 carbon atoms. n1 to n4 are each independent integers between 0 and 6, L, Ar 1 , and R 2 This is as defined in Chemical Formula 1 above.
9. In the aforementioned chemical formula 3, R b1 ~R b4 One of these is a position that is linked to the chemical formula 1, R b1 ~R b4 The light-emitting element according to claim 1, wherein the remaining elements are each independently hydrogen atoms or deuterium atoms.
10. The amine compound represented by chemical formula 1 is represented by any one of the following chemical formulas 1-6 to 1-9, according to claim 1: [Chemical formula 1-6] 【Chemistry 9】 [Chemical formula 1-7] 【Chemistry 10】 [Chemical formula 1-8] 【Chemistry 11】 [Chemical formula 1-9] 【Chemistry 12】 In the aforementioned chemical formulas 1-6 to 1-9, R y1 ~R y4 Each of these is independently a substituted or unsubstituted aryl group having 6 to 12 carbon atoms in a ring, L, Ar 1 , and R 1 This is as defined in Chemical Formula 1 above.
11. The substituent represented by chemical formula 3 is represented by any one of the following chemical formulas 3-1 to 3-3, according to claim 1: [Chemical formula 3-1] 【Chemistry 13】 [Chemical formula 3-2] 【Chemistry 14】 [Chemical formula 3-3] 【Chemistry 15】 In the above chemical formula 3-1, R b9 ~R b12 One of these is a position that is linked to the chemical formula 1, R b9 ~R b12 The remaining atoms are each independently either hydrogen atoms or deuterium atoms. In the above chemical formula 3-2, R b13 ~R b16 One of these is a position that is linked to the chemical formula 1, R b13 ~R b16 The remaining atoms are each independently either hydrogen atoms or deuterium atoms. In the above chemical formula 3-3, R b17 ~R b20 One of these is a position that is linked to the chemical formula 1, R b17 ~R b20 The remaining atoms are each independently either hydrogen atoms or deuterium atoms.
12. The amine compound represented by the chemical formula 1 is represented by any one of the compounds in the following first group of compounds, as described in claim 1: [First compound group] 【Chemistry 16】 【Chemistry 17】 。
13. Amine compounds represented by the following chemical formula 1: [Chemical formula 1] [Chemistry 18] In the aforementioned chemical formula 1, L is 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. Ar 1 is a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, however, Ar 1 This does not include substituted or unsubstituted benzofuranyl groups and substituted or unsubstituted benzothiophenyl groups. R 1 It is represented by the following chemical formula 2, R 2 It is represented by the following chemical formula 3: [Chemical formula 2] 【Chemistry 19】 In the aforementioned chemical formula 2, R a1 ~R a4 One of these is a position that is linked to the chemical formula 1, R a1 ~R a4 The remaining atoms are, independently, a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms. R a5 ~R a10 Each of these is independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms. [Chemical formula 3] 【Chemistry 20】 In the aforementioned chemical formula 3, X is O, S, or NAr 2 And, Ar 2 This is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms in a ring, R b1 ~R b4 One of these is a position that is linked to the chemical formula 1, R b1 ~R b4 The remaining atoms are, independently, a hydrogen atom, a deuterium atom, a halogen atom, or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms. R b5 ~R b8 One of these is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms in the ring, but it does not include substituted or unsubstituted fluorenyl groups. R b5 ~R b8 The remaining atoms are, independently, a hydrogen atom, a deuterium atom, a halogen atom, or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.
14. The amine compound represented by the chemical formula 1 is the amine compound according to claim 13, represented by the following chemical formula 1-1: [Chemical formula 1-1] 【Chemistry 21】 In the above chemical formula 1-1, A 1 ~A 3 Each of these is independently a hydrogen atom, a deuterium atom, a halogen atom, or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms. L, Ar 1 , and R 2 This is as defined in Chemical Formula 1 above.
15. The amine compound represented by the aforementioned chemical formula 1 is the amine compound according to claim 13, which is represented by any one of the following chemical formulas 1-2 to 1-5: [Chemical formula 1-2] 【Chemistry 22】 [Chemical formula 1-3] 【Chemistry 23】 [Chemical formula 1-4] 【Chemistry 24】 [Chemical formula 1-5] 【Chemistry 25】 In the aforementioned chemical formulas 1-2 to 1-5, R x1 ~R x4 Each of these is independently a hydrogen atom, a deuterium atom, or a substituted or unsubstituted alkyl group having 1 to 5 carbon atoms. n1 to n4 are each independent integers between 0 and 5, and L, Ar 1 , and R 2 This is as defined in Chemical Formula 1 above.
16. In the aforementioned chemical formula 3, R b1 ~R b4 One of these is a position that is linked to the chemical formula 1, R b1 ~R b4 The amine compound according to claim 13, wherein the remaining atoms are each independently a hydrogen atom or a deuterium atom.
17. The amine compound represented by chemical formula 1 is the amine compound according to claim 13, which is represented by any one of the following chemical formulas 1-6 to 1-9: [Chemical formula 1-6] 【Chemistry 26】 [Chemical formula 1-7] 【Chemistry 27】 [Chemical formula 1-8] 【Chemistry 28】 [Chemical formula 1-9] 【Chemistry 29】 In the aforementioned chemical formulas 1-6 to 1-9, R y1 ~R y4 Each of these is independently a substituted or unsubstituted aryl group having 6 to 12 carbon atoms in a ring, L, Ar 1 , and R 1 This is as defined in Chemical Formula 1 above.
18. The substituent represented by chemical formula 3 is the amine compound according to claim 13, which is represented by any one of the following chemical formulas 3-1 to 3-3: [Chemical formula 3-1] 【Transformation 30】 [Chemical formula 3-2] 【Chemistry 31】 [Chemical formula 3-3] 【Chemistry 32】 In the chemical formula 3-1, R b9 ~R b12 Any one of them is a position linked to the chemical formula 1, and R b9 ~R b12 The rest of them are each independently a hydrogen atom or a deuterium atom, In the above chemical formula 3-2, R b13 ~R b16 One of these is a position that is linked to the chemical formula 1, R b13 ~R b16 The remaining atoms are each independently either hydrogen atoms or deuterium atoms. In the chemical formula 3-3, one of R b17 ~R b20 is the position linked to the chemical formula 1, and the rest of R b17 ~R b20 are each independently a hydrogen atom or a deuterium atom.
19. The amine compound represented by the chemical formula 1 is the amine compound according to claim 13, which is represented by any one of the compounds in the following first group of compounds: [First compound group] 【Transformation 33】 【Transformation 34】 。
20. 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 an electronic device comprising a first electrode, a second electrode positioned on the first electrode, and a hole transport region positioned between the first electrode and the second electrode and containing a first compound represented by the following chemical formula 1: [Chemical formula 1] 【Chemistry 35】 In the aforementioned chemical formula 1, L is 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. Ar 1 is a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, however, Ar 1 This does not include substituted or unsubstituted benzofuranyl groups and substituted or unsubstituted benzothiophenyl groups. R 1 It is represented by the following chemical formula 2, R 2 It is represented by the following chemical formula 3: [Chemical formula 2] 【Transformation 36】 In the aforementioned chemical formula 2, R a1 ~R a4 One of these is a position that is linked to the chemical formula 1, R a1 ~R a4 The remaining atoms are, independently, a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms. R a5 ~R a10 Each of these is independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms. [Chemical formula 3] 【Chemistry 37】 In the aforementioned chemical formula 3, X is O, S, or NAr 2 And, Ar 2 This is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms in a ring, R b1 ~R b4 One of these is a position that is linked to the chemical formula 1, R b1 ~R b4 The remaining atoms are, independently, a hydrogen atom, a deuterium atom, a halogen atom, or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms. R b5 ~R b8 One of these is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms in a ring, but substituted or unsubstituted fluorenyl groups are not included. R b5 ~R b8 The remaining atoms are, independently, a hydrogen atom, a deuterium atom, a halogen atom, or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.
21. The electronic device according to claim 20, wherein the electronic device is selected from a large display device selected from televisions, monitors, and outdoor signs, and from a medium-sized display device selected from a personal computer, notebook computer, personal digital terminal, in-vehicle display device, game console, portable electronic device, and camera.