Light-emitting element, condensed polycyclic compound for light-emitting element, and electronic device including light-emitting element
Patent Information
- Application Number
- CN202610582828.5
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Priority Date
- 2025-05-01
- Filing Date
- 2026-04-29
- Publication Date
- 2026-11-03
AI Technical Summary
Existing organic electroluminescent display devices suffer from insufficient lifespan and luminous efficiency of the light-emitting elements.
Fused polycyclic compounds are used as the emission layer material. The specific structure of the compound is represented by Formula 1. It is combined with possible auxiliary compounds such as Formula HT-1, Formula ET-1 and Formula D-1 to form the electrode and emission layer of the light-emitting element.
It improves the luminous efficiency of light-emitting elements and extends their service life, making it suitable for display modules in electronic devices.
Smart Images

Figure CN123026632A_ABST
Abstract
Description
Technical Field
[0001] This disclosure relates herein to light-emitting elements, fused polycyclic compounds used therein, and electronic devices including light-emitting elements. Background Technology
[0002] Recently, organic electroluminescent display devices, etc., have been actively developed as image display devices. Organic electroluminescent display devices, etc., are display devices that include so-called self-emissive light-emitting elements, in which holes and electrons injected from the first electrode and the second electrode recombine in the emitting layer, and thus the light-emitting material in the emitting layer emits light to complete the display.
[0003] In order to apply light-emitting elements to display devices, there is a need for longer element lifespan, and there is an ongoing need to develop materials for light-emitting elements that can reliably achieve this property. Summary of the Invention
[0004] This disclosure provides light-emitting elements exhibiting high luminous efficiency and long element lifespan, as well as electronic devices including the same.
[0005] This disclosure also provides fused polycyclic compounds as materials for light-emitting elements, which improve luminous efficiency and element lifespan.
[0006] One aspect provides a light-emitting element comprising a first electrode, a second electrode disposed on the first electrode, and an emitting layer disposed between the first and second electrodes, wherein the emitting layer comprises a fused polycyclic compound represented by Formula 1 as a first compound:
[0007] Formula 1
[0008] .
[0009] In Formula 1, Y1 and Z1 are each independently a hydrogen atom, a deuterium atom, a cyano group, a nitro group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms; X1 to X4 are each independently O, S, or a group represented by Formula 2; at least two of X1 to X4 are groups represented by Formula 2; R0 to R 13 Each of the following groups is independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro 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 cyclic carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 30 cyclic carbon atoms, or a group represented by Formula 3; at least one of R1 to R4 is a group represented by Formula 3; and R 10 To R 13 At least one of them is a group represented by Formula 3:
[0010] Formula 2
[0011] .
[0012] In Equation 2, R A To R E Each of the following groups is independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 cyclic carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 30 cyclic carbon atoms, or a group represented by Formula 3, and " "and" "Indicates the location to be connected:"
[0013] Formula 3
[0014] .
[0015] In Equation 3, R a To R e Each of the following groups is independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro 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 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 cyclic carbon atoms; wherein at least two of the R groups in Formula 2 are... A To R E It includes four or more substituted or unsubstituted benzene rings. The first compound includes a structure in which any hydrogen atom can be substituted by a deuterium atom, and " "Indicates the location to be connected."
[0016] In one or more embodiments, the emitter layer may further include at least one of a second compound represented by formula HT-1, a third compound represented by formula ET-1, and a fourth compound represented by formula D-1.
[0017] HT-1
[0018]
[0019] In formula HT-1, A1 to A8 can each be N or CR independently. 51 And L1 can be a directly attached, substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, Y a Can be used for direct connection, CR 52 R 53 or SiR54 R 55 Ar1 can be a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, and R 51 To R 55 Each of these can independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted thio group, a substituted or unsubstituted oxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted boron group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 cyclic carbon atoms, or R 51 To R 55 Each group may optionally bond to an adjacent group to form a ring.
[0020] ET-1
[0021]
[0022] In Equation ET-1, at least one of X1 to X3 can be N, and the rest of X1 to X3 can be CR. 56 Each R 56 Each of the following can 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 60 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 cyclic carbon atoms; b1 to b3 can each be independently an integer selected from 0 to 10; Ar2 to Ar4 can each be independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms; and L2 to L4 can each be independently a directly linked, substituted or unsubstituted arylene group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 cyclic carbon atoms.
[0023] Formula D-1
[0024]
[0025] In formula D-1, Q1 to Q4 can each be independently C or N, and ring C1 to ring C4 can each be independently a substituted or unsubstituted aliphatic hydrocarbon cyclic group having 5 to 30 cyclic carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 30 cyclic carbon atoms. 11 To L13 Each can be independently connected directly. , , , substituted or unsubstituted alkylene groups having 1 to 20 carbon atoms, substituted or unsubstituted arylene groups having 6 to 30 cyclic carbon atoms, or substituted or unsubstituted heteroarylene groups having 2 to 30 cyclic carbon atoms, and in L 11 To L 13 middle," "Indicates the sites connected to rings C1 to C4, b11 to b13 can each be independently 0 or 1, R" 61 To R 66 Each of the following groups may be independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted silyl, substituted or unsubstituted thio, substituted or unsubstituted oxy, substituted or unsubstituted amino, substituted or unsubstituted boron, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 60 cyclic carbon atoms, or substituted or unsubstituted heteroaryl having 2 to 60 cyclic carbon atoms, and / or each may be bonded to an adjacent group to form a ring, and d1 to d4 may each be independently an integer selected from 0 to 4.
[0026] In one or more embodiments, Equation 1 above can be represented by any one of Equations 1-A1 to 1-A3.
[0027] Formula 1-A1
[0028]
[0029] Formula 1-A2
[0030]
[0031] Formula 1-A3
[0032]
[0033] In equations 1-A1 to 1-A3, m1 to m6 are each an independent integer selected from 0 to 5, and R a1 To R a6 Each of the following is independently composed of a hydrogen atom, a deuterium atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, and X1 to X4, R0 to R 13 Y1 and Z1 are the same as those defined in Equation 1.
[0034] In one or more embodiments, Formula 1 may be represented by one of Formulas 1-B1 to 1-B3.
[0035] Formula 1-B1
[0036]
[0037] Formula 1-B2
[0038]
[0039] Formula 1-B3
[0040]
[0041] In equations 1-B1 to 1-B3, X 11 and X 12 Each can be independently represented as O or S, R 1A To R 1E and R 2A To R 2E Each of the following groups is independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 cyclic carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 30 cyclic carbon atoms, or a group represented by Formula 3, in R 1A To R 1E and R 2A To R 2E In this case, the number of substituents represented by Formula 3 is 4 or greater, and R0 to R 13 Y1 and Z1 are the same as those defined in Equation 1.
[0042] In one or more embodiments, Equation 2 may be represented by any one of Equations 2-1 to 2-8.
[0043] Equation 2-1
[0044]
[0045] Equation 2-2
[0046]
[0047] Equation 2-3
[0048]
[0049] Equation 2-4
[0050]
[0051] Formula 2-5
[0052]
[0053] Formula 2-6
[0054]
[0055] Formula 2-7
[0056]
[0057] Formula 2-8
[0058]
[0059] In equations 2-1 to 2-8, n1 to n15 can each be an integer selected from 0 to 5 independently, and R b1 To R b15 Each of the following can be independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, R A1 To R D1 Each may independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 10 cyclic carbon atoms, and " "and" "Indicates the location to be connected."
[0060] In one or more embodiments, equation 2-1 may be represented by one of 2-1A to 2-1C, equation 2-2 may be represented by one of 2-2A and 2-2B, equation 2-3 may be represented by one of 2-3A to 2-3G, equation 2-4 may be represented by one of 2-4A and 2-4B, equation 2-5 may be represented by one of 2-5A to 2-5D, equation 2-6 may be represented by 2-6A, equation 2-7 may be represented by 2-7A, and equation 2-8 may be represented by 2-8A, wherein, in 2-1A to 2-8A, " "and" "Indicates the location to be connected."
[0061]
[0062]
[0063]
[0064] In one or more embodiments, in Equation 1, R1 to R4 and R 10 To R 13The remaining groups that are not represented by Formula 3 can each be independently hydrogen atoms or deuterium atoms.
[0065] In one or more embodiments, Formula 3 may be represented by one of R-1 to R-13.
[0066]
[0067] In one or more embodiments, in Formula 1, Y1 and Z1 can each be independently represented by one of W-1 to W-7.
[0068]
[0069] According to another aspect, fused polycyclic compounds represented by Formula 1 are provided:
[0070] Formula 1
[0071] .
[0072] In Formula 1, Y1 and Z1 are each independently a hydrogen atom, a deuterium atom, a cyano group, a nitro group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms; X1 to X4 are each independently O, S, or a group represented by Formula 2; at least two of X1 to X4 are groups represented by Formula 2; R0 to R 13 Each of the following groups is independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro 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 cyclic carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 30 cyclic carbon atoms, or a group represented by Formula 3; at least one of R1 to R4 is a group represented by Formula 3; and R 10 To R 13 At least one of them is a group represented by Formula 3:
[0073] Formula 2
[0074] .
[0075] In Equation 2, R A To R E Each of the following groups is independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 cyclic carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 30 cyclic carbon atoms, or a group represented by Formula 3, and " "and" "Indicates the location to be connected:"
[0076] Formula 3
[0077] .
[0078] In Equation 3, R a To R e Each of the following groups is independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro 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 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 cyclic carbon atoms; wherein at least two of the R groups in Formula 2 are... A To R E It includes four or more substituted or unsubstituted benzene rings. In some embodiments, the fused polycyclic compound includes a structure in which any hydrogen atom can be substituted by a deuterium atom, and " "Indicates the location to be connected."
[0079] In one or more embodiments, the electronic device includes a display module configured to provide an image, wherein the display module includes a substrate layer, a circuit layer disposed on the substrate 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 emitting layer disposed between the first electrode and the second electrode, and the emitting layer includes a fused polycyclic compound represented by Formula 1.
[0080] Formula 1
[0081]
[0082] In Formula 1, Y1 and Z1 are each independently a hydrogen atom, a deuterium atom, a cyano group, a nitro group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms; X1 to X4 are each independently O, S, or a group represented by Formula 2; at least two of X1 to X4 are groups represented by Formula 2; R0 to R 13 Each of the following groups is independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro 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 cyclic carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 30 cyclic carbon atoms, or a group represented by Formula 3; at least one of R1 to R4 is a group represented by Formula 3; and R 10 To R 13 At least one of them is a group represented by Formula 3:
[0083] Formula 2
[0084] .
[0085] In Equation 2, R A To R E Each of the following groups is independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 cyclic carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 30 cyclic carbon atoms, or a group represented by Formula 3, and " "and" "Indicates the location to be connected:"
[0086] Formula 3
[0087] .
[0088] In Equation 3, R a To R e Each of the following groups is independently composed of a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro 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 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 cyclic carbon atoms, wherein at least two of the R groups in Formula 2 are... A To R E It includes four or more substituted or unsubstituted benzene rings. In some embodiments, the fused polycyclic compound represented by Formula 1 includes a structure in which any hydrogen atom can be substituted by a deuterium atom, and " "Indicates the location to be connected."
[0089] In one or more embodiments, the electronic device may further include at least one of a light control layer and a color filter layer, wherein the light control layer may include quantum dots and the color filter layer may include pigments or dyes.
[0090] In one or more embodiments, the electronic device may further include at least one of a processor, a memory, and a power module. Attached Figure Description
[0091] The accompanying drawings are included to provide a further understanding of this disclosure, and are incorporated in and form a part of this specification. The drawings illustrate embodiments of the disclosure and, together with the detailed description, serve to explain the principles of the disclosure. In the drawings:
[0092] Figure 1 A plan view illustrating a display module according to one or more embodiments;
[0093] Figure 2 To show the corresponding Figure 1 A cross-sectional view of the section of line I-I';
[0094] Figure 3 A cross-sectional view of a light-emitting element according to one or more embodiments is shown for illustrative purposes;
[0095] Figure 4 A cross-sectional view of a light-emitting element according to one or more embodiments is shown for illustrative purposes;
[0096] Figure 5 A cross-sectional view of a light-emitting element according to one or more embodiments is shown for illustrative purposes;
[0097] Figure 6 A cross-sectional view of a light-emitting element according to one or more embodiments is shown for illustrative purposes;
[0098] Figure 7 A cross-sectional view illustrating a display module according to one or more embodiments;
[0099] Figure 8 A cross-sectional view illustrating a display module according to one or more embodiments;
[0100] Figure 9 A cross-sectional view illustrating a display module according to one or more embodiments;
[0101] Figure 10 A cross-sectional view illustrating a display module according to one or more embodiments;
[0102] Figure 11 A view showing the interior of a vehicle in which electronic devices according to one or more embodiments are provided;
[0103] Figure 12 A perspective view illustrating an electronic device according to one or more embodiments;
[0104] Figure 13 An exploded perspective view of an electronic device according to one or more embodiments is shown;
[0105] Figure 14 This is a block diagram of an electronic device according to one or more embodiments; and
[0106] Figure 15 Schematic diagrams of electronic devices according to various embodiments are shown. Detailed Implementation
[0107] This disclosure can be modified in many alternative forms, and therefore specific embodiments will be illustrated and described in further detail with reference to the accompanying drawings. However, it should be understood that this disclosure is not intended to be limited to the specific forms disclosed, but rather to cover all modifications, equivalents, and alternatives falling within the spirit and scope of this disclosure.
[0108] In this specification, it will be understood that when an element (or area, layer, or part, etc.) is referred to as being "on", "connected to", or "attached to" another element (or area, layer, or part, etc.), it may be directly disposed on, directly connected to, or directly attached to another element (or area, layer, or part, etc.), or other elements may be disposed between them.
[0109] The same reference numerals or symbols refer to the same elements throughout the drawings. In the drawings, the scale and dimensions (e.g., thickness) of the elements are enlarged for effective description of the technical content. The term "and / or" includes any and all combinations of one or more of the related listed elements.
[0110] It will be understood that although the terms first, second, etc., may be used herein to describe various elements, the elements are not limited by these terms. These terms are used only to distinguish one element from another. For example, without departing from the scope of the inventive concept, a first element may be referred to as a second element. Similarly, a second element may be referred to as a first element. Unless the context clearly indicates otherwise, the singular expressions “a,” “an,” and “the” are intended to also include the plural forms.
[0111] Additionally, terms such as "below," "underneath," "on the lower side," "above," "above," or "on the upper side" can be used to describe the relationships between the elements illustrated in the accompanying drawings. These terms are relative concepts and are described based on the directions indicated in the drawings.
[0112] It will be further understood that, when used in this specification, the terms “comprises,” “includes,” “has,” and / or “comprising,” “including,” “having” indicate the presence of the described features, quantities, steps, operations, elements, components, and / or combinations thereof, but do not preclude the possibility of the presence or addition of one or more other features, quantities, steps, operations, elements, components, and / or combinations thereof.
[0113] Unless otherwise defined, all terms used herein (including technical and scientific terms) shall have the same meaning as commonly understood by one of ordinary skill in the art to which this invention pertains. It will be further understood that terms (such as those defined in commonly used dictionaries) shall be interpreted as having the same meaning as they have in the context of the relevant field and shall not be interpreted in an ideal or overly formal sense unless expressly so defined herein.
[0114] As used herein, “about” or “approximately” includes stated values and means within an acceptable range of deviations from a particular value determined by a person skilled in the art, taking into account the measurement under discussion and the errors associated with the measurement of the particular quantity (i.e., the limitations of the measurement system). For example, “about” may mean within one or more standard deviations, or within ±30%, ±20%, ±10%, or ±5% of the stated value.
[0115] In this disclosure, "integers selected from 0 to 10" refers to integers selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, and 10. The above description of numerical ranges also applies to any other numerical ranges appearing in the specification, such as integers selected from 0 and 1, integers selected from 0 to 2, integers selected from 0 to 3, integers selected from 0 to 4, integers selected from 0 to 5, integers selected from 0 to 6, integers selected from 0 to 7, integers selected from 0 to 8, integers selected from 0 to 9, and integers selected from 0 to 10, etc.
[0116] As used herein, the term "substituted or unsubstituted" may indicate an unsubstituted group or a group substituted by at least one substituent selected from the group consisting of: deuterium, halogen, cyano, nitro, amino, amino, silyl, oxy, thio, sulfinyl, sulfonyl, carbonyl, boron, phosphonyl oxide, phosphonyl sulfide, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, and heterocyclic groups. Furthermore, each of the substituents presented above as examples may be substituted or unsubstituted. For example, biphenyl may be interpreted as aryl or as a phenyl group substituted with a phenyl group.
[0117] As used herein, the term "bonded with an adjacent group to form a ring" indicates that a group is bonded to an adjacent group to form a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocycle. Hydrocarbon rings include aliphatic hydrocarbon rings and aromatic hydrocarbon rings. Heterocycles include aliphatic heterocycles and aromatic heterocycles. Hydrocarbon rings and heterocycles can be monocyclic or polycyclic. Additionally, rings formed by bonding with each other can be linked to another ring to form a spirostructure.
[0118] As used herein, the term "adjacent group" may refer to a substituent that replaces an atom directly bonded to the atom substituted by the corresponding substituent, another substituent that replaces the atom substituted by the corresponding substituent, or a substituent spatially closest to the corresponding substituent. For example, the two methyl groups in 1,2-xylene can be interpreted as "adjacent groups," and the two ethyl groups in 1,1-diethylcyclopentane can be interpreted as "adjacent groups." Additionally, the two methyl groups in 4,5-dimethylphenanthrene can be interpreted as "adjacent groups."
[0119] Examples of halogen atoms, as used herein, may include fluorine, chlorine, bromine, or iodine atoms.
[0120] As used herein, "alkyl" can be straight-chain or branched. The number of carbon atoms in an alkyl group is 1 to 60, 1 to 50, 1 to 30, 1 to 20, 1 to 10, or 1 to 6. Non-limiting examples of alkyl groups may include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, isobutyl, 2-ethylbutyl, 3,3-dimethylbutyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 2-butylhexyl, n-heptyl, 1-methylheptyl, 2,2-dimethylheptyl, 2-ethylheptyl, 2-butylheptyl, n-octyl, tert-octyl, 2-ethyloctyl, 2-butyloctyl, 2-hexyloctyl, 3,7-dimethyloctyl, n-nonyl, n-decyl, 2-ethyldecyl, 2-butyldecyl, 2-hexyldecyl, 2-octyldecyl, n-undecane The formulation may include, but is not limited to, 2-ethyldodecyl, 2-butyldodecyl, 2-hexyldodecyl, 2-octyldodecyl, 2-tridecyl, 2-tetradecyl, 2-pentadecanyl, 2-hexadecyl, 2-ethylhexadecyl, 2-butylhexadecyl, 2-hexylhexadecyl, 2-octylhexadecyl, 2-heptadecyl, 2-octylhexadecyl, 2-heptadecyl, 2-octylhexadecyl, 2-heptadecyl, 2-ethylhexadecyl, 2-butylhexadecyl, 2-hexylhexadecyl, 2-octylhexadecyl, 2-heptadecyl, 2-ethylhexadecyl, 2-butylhexadecyl, 2-hexylhexadecyl, 2-octylhexadecyl, 2-heptadecyl, 2-hexadecyl, 2-hexadecyl, 2-hexadecyl, 2-hexadecyl, 2-hexadecyl, or 2-trianedecyl, etc., but the embodiments are not limited to these.
[0121] As used herein, "cycloalkyl" refers to a cyclic alkyl group. The number of carbon atoms in a cycloalkyl group is 3 to 60, 3 to 50, 3 to 30, 3 to 20, or 3 to 10. Non-limiting examples of cycloalkyl groups include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, norbornyl, 1-adamantyl, 2-adamantyl, isobornyl, or dicycloheptyl, etc., but the implementation is not limited thereto.
[0122] As used herein, "alkenyl" refers to a hydrocarbon group comprising at least one carbon-carbon double bond in the middle or at the end of an alkyl group having two or more carbon atoms. The alkenyl group can be straight-chain or branched. The number of carbon atoms in the alkenyl group is not particularly limited, but is 2 to 60, 2 to 30, 2 to 20, or 2 to 10. Non-limiting examples of alkenyl groups include vinyl, 1-butenyl, 1-pentenyl, 1,3-butadienyl, styryl, or styrylvinyl, etc., but implementation is not limited thereto.
[0123] As used herein, "alkynyl" indicates a hydrocarbon group comprising at least one carbon-carbon triple bond in the middle or at the end of an alkyl group having two or more carbon atoms. The alkynyl group can be straight-chain or branched. The number of carbon atoms in the alkynyl group is not particularly limited, but is 2 to 30, 2 to 20, or 2 to 10. Non-limiting examples of alkynyl groups may include ethynyl or propynyl, but implementation is not limited thereto.
[0124] As used herein, “cycloalkyl group” refers to any functional group or substituent derived from an aliphatic or aromatic hydrocarbon ring. The number of cyclic carbon atoms in the cycloalkyl group can be 5 to 60, 5 to 30, 5 to 20, or 5 to 10.
[0125] As used herein, "aryl" refers to any functional group or substituent derived from an aromatic hydrocarbon ring. The aryl group can be monocyclic or polycyclic. The number of cyclic carbon atoms in the aryl group can be 6 to 60, 6 to 30, 6 to 20, or 6 to 15. Non-limiting examples of aryl groups may include phenyl, naphthyl, fluorenyl, anthraceneyl, phenanthryl, biphenyl, terphenyl, tetraphenyl, pentaphenyl, hexaphenyl, triphenylene, pyrene, benzofluoranthracene, or 1,2-benzophenanthryl, but the implementation is not limited thereto.
[0126] As used herein, the "fluorene group" can be substituted, and two substituents can bond together to form a spirostructure. Examples of substituted fluorene groups are shown below. However, implementation is not limited to these examples.
[0127]
[0128] As used herein, "heterocyclic group" refers to any functional group or substituent derived from a ring containing at least one of B, O, N, P, Si, and S as a heteroatom. Heterocyclic groups include aliphatic heterocyclic groups and aromatic heterocyclic groups. Aromatic heterocyclic groups may be heteroaryl. Aliphatic and aromatic heterocyclic groups may be monocyclic or polycyclic.
[0129] As used herein, a heterocyclic group may contain at least one of B, O, N, P, Si, and S as a heteroatom. When a heterocyclic group contains two or more heteroatoms, the two or more heteroatoms may be the same or different from each other. The heterocyclic group may be a monocyclic or polycyclic heterocyclic group, and may include heteroaryl groups. The number of cyclic carbon atoms in the heterocyclic group may be 2 to 60, 2 to 30, 2 to 20, or 2 to 10.
[0130] As used herein, the aliphatic heterocyclic group may contain at least one of B, O, N, P, Si, and S as a heteroatom. The number of cyclic carbon atoms in the aliphatic heterocyclic group may be 2 to 60, 2 to 30, 2 to 20, or 2 to 10. Non-limiting examples of aliphatic heterocyclic groups include ethylene oxide, thiopropylcycloyl, pyrrolyl, piperidinyl, tetrahydrofuranyl, tetrahydrothiophenyl, thiaalkyl, tetrahydropyranyl, or 1,4-dioxane, etc., but the embodiments are not limited thereto.
[0131] As used herein, "heteroaryl" includes at least one of B, O, N, P, Si, and S as a heteroatom. When a heteroaryl contains two or more heteroatoms, the two or more heteroatoms may be the same or different from each other. A heteroaryl can be a monocyclic heteroaryl or a polycyclic heteroaryl. The number of cyclic carbon atoms in a heteroaryl can be 2 to 60, 2 to 30, 2 to 20, or 2 to 10. Non-limiting examples of heteroaryl groups include thienyl, furanyl, pyrrolyl, imidazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, triazolyl, acridineyl, pyridazinyl, quinolinyl, quinazolinyl, quinoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazoleyl, N-arylcarbazoleyl, N-heteroarylcarbazoleyl, N-alkylcarbazoleyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazoleyl, benzothiaphenyl, dibenzothiaphenyl, thienzothiaphenyl, benzofuranyl, phenanthrololinyl, thiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, thiadiazolyl, phenthiazolyl, dibenzothiaryl, or dibenzofuranyl, but the embodiments are not limited to these.
[0132] As used herein, the above description of aryl groups can also be applied to arylene groups, except that arylene groups are divalent groups. The above description of heteroaryl groups can also be applied to heteroarylene groups, except that heteroarylene groups are divalent groups.
[0133] As used herein, "silyl" includes alkylsilyl and arylsilyl. The alkyl group in an alkylsilyl group may be straight-chain, branched, or cyclic. The number of carbon atoms in an alkylsilyl group is not specifically limited, but may be, for example, 1 to 20 or 1 to 10. The number of carbon atoms in an arylsilyl group is not specifically limited, but may be, for example, 6 to 30, 6 to 20, or 6 to 15. Non-limiting examples of silyl groups include trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, or phenylsilyl, but the implementation is not limited thereto.
[0134] As used herein, the number of carbon atoms in a "carbonyl" group is not particularly limited, but can be 1 to 40, 1 to 30, or 1 to 20. For example, a carbonyl group can have the following structure, but the implementation is not limited thereto:
[0135] .
[0136] As used herein, there is no particular limitation on the number of carbon atoms in "sulfinyl" and "sulfonyl", but it can be from 1 to 30. Sulfinyl groups may include alkylsulfinyl groups and arylsulfinyl groups. Sulfonyl groups may include alkylsulfonyl groups and arylsulfonyl groups.
[0137] As used herein, "thio group" may include alkylthio and arylthio. A thio group may indicate that a sulfur atom is bonded to an alkyl or aryl group as defined above. The alkyl group in an alkylthio group may be straight-chain, branched, or cyclic. The number of carbon atoms in an alkylthio group is not specifically limited, but may be, for example, 1 to 20 or 1 to 10. The number of carbon atoms in an arylthio group is not specifically limited, but may be, for example, 6 to 30, 6 to 20, or 6 to 15. Non-limiting examples of thio groups include methylthio, ethylthio, propanethio, pentylthio, hexylthio, octylthio, dodecylthio, cyclopentylthio, cyclohexylthio, phenylthio, or naphthio, etc., but implementation is not limited thereto.
[0138] As used herein, "oxygen group" may indicate that an oxygen atom is bonded to an alkyl or aryl group as defined above. Oxide groups may include alkoxy groups and aryloxy groups. Alkoxy groups may be straight-chain, branched, or cyclic. The number of carbon atoms in an alkoxy group is not particularly limited, but may be, for example, 1 to 20 or 1 to 10. The number of cyclic carbon atoms in an aryloxy group is not particularly limited, but may be, for example, 6 to 30, 6 to 20, or 6 to 15. Non-limiting examples of oxygen groups include methoxy, ethoxy, n-propoxy, isopropoxy, butoxy, pentoxy, hexoxy, octoxy, nonoxy, decoxy, or benzyloxy, etc., but the embodiments are not limited thereto.
[0139] As used herein, "boron group" can indicate that a boron atom is bonded to an alkyl or aryl group as defined above. Boron groups include alkylboron groups and arylboron groups. The alkyl group in an alkylboron group can be straight-chain, branched, or cyclic. The number of carbon atoms in an alkylboron group is not specifically limited, but can be, for example, 1 to 20 or 1 to 10. The number of carbon atoms in an arylboron group is not specifically limited, but can be, for example, 6 to 30, 6 to 20, or 6 to 15. Non-limiting examples of boron groups include dimethylboron, diethylboron, tert-butylmethylboron, diphenylboron, or phenylboron, etc., but embodiments are not limited thereto.
[0140] As used herein, the number of carbon atoms in an "amine group" is not particularly limited, but can be from 1 to 50, 1 to 30, or 1 to 20. An amine group may include alkylamine and arylamine groups. The alkyl group in an alkylamine group may be straight-chain, branched, or cyclic. The number of carbon atoms in an alkylamine group is not specifically limited, but can be, for example, from 1 to 20 or 1 to 10. The number of carbon atoms in an arylamine group is not specifically limited, but can be, for example, from 6 to 30, 6 to 20, or 6 to 15. Non-limiting examples of amine groups include methylamine, dimethylamine, phenylamine, diphenylamine, naphthylamine, or 9-methyl-anthraylamine, etc., but the implementation is not limited thereto.
[0141] In this disclosure, the sulfinyl group may indicate the combination of the alkyl or aryl group defined above with -S (=O)-. The number of carbon atoms in the sulfinyl group is not specifically limited, but may be 1 to 30, 1 to 20, or 1 to 10. The sulfinyl group may include alkylsulfinyl groups and arylsulfinyl groups. For example, the sulfinyl group may have the following structures, but is not limited thereto.
[0142]
[0143] In this disclosure, the sulfonyl group may indicate the combination of the alkyl or aryl group defined above with -S(=O)2-. The number of carbon atoms in the sulfonyl group is not specifically limited, but may be 1 to 30, 1 to 20, or 1 to 10. The sulfonyl group may include alkylsulfonyl groups and arylsulfonyl groups. For example, the sulfonyl group may have the following structures, but is not limited thereto.
[0144]
[0145] In this disclosure, the phosphine oxide group may indicate the combination of the alkyl or aryl group defined above with -P (=O)-. The number of carbon atoms in the phosphine oxide group is not specifically limited, but may be 1 to 30, 1 to 20, or 1 to 10. The phosphine oxide group may include alkylphosphine oxide groups and arylphosphine oxide groups. For example, the phosphine oxide group may have the following structures, but is not limited thereto.
[0146]
[0147] In this disclosure, the phosphine sulfide group may indicate that the alkyl or aryl group defined above is bonded to -P (=S)-. The number of carbon atoms in the phosphine sulfide group is not specifically limited, but may be 1 to 30, 1 to 20, or 1 to 10. The phosphine sulfide group may include alkylphosphine sulfide groups and arylphosphine sulfide groups. For example, the phosphine sulfide group may have the following structures, but is not limited thereto.
[0148]
[0149] As used herein, the examples of the above alkyl groups also apply to alkyl groups derived from alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylaryl, alkylamino, alkylboronyl, alkylsilyl, alkylphosphine oxide, alkylphosphine sulfide, and alkylamine groups.
[0150] As used herein, the examples of aryl groups described above also apply to aryl groups derived from aryloxy, arylthio, arylsulfinyl, arylsulfonyl, arylamino, arylboryl, arylsilyl, arylphosphine oxide, arylphosphine sulfide, and arylamine groups.
[0151] As used herein, a direct connection indicates a single key. In this document, " "", "", "", "", "and" "Indicates the location to be connected."
[0152] Embodiments of this disclosure will now be described in further detail with reference to the accompanying drawings.
[0153] Figure 1 This is a plan view illustrating a display module DM according to one or more embodiments. Figure 2 This is a cross-sectional view illustrating a display module DM according to one or more embodiments. Figure 2 To show the corresponding Figure 1 A cross-sectional view of the section of line I-I'.
[0154] The display module DM may include a display panel DP and an optical layer PP disposed on the display panel DP. The display panel DP includes multiple light-emitting elements ED-1, ED-2, and ED-3. The optical layer PP may be disposed on the display panel DP to control reflected light in the display panel DP due to external light. The optical layer PP may include, for example, a polarizing layer or a color filter layer. Figure 1 As shown, the optical layer PP may not be provided in the display module DM according to one or more embodiments.
[0155] The substrate BL can be disposed on the optical layer PP. The substrate BL can be a component providing a substrate surface, and the optical layer PP is disposed on the substrate surface. The substrate BL can be a glass substrate, a metal substrate, or a plastic substrate, etc. However, the embodiments are not limited to this, and the substrate BL can be an inorganic layer, an organic layer, or a composite material layer. In addition, unlike what is shown, in one or more embodiments, the substrate BL may not be provided.
[0156] The display module DM according to one or more embodiments may further include a filler layer (not shown). The filler layer (not shown) may be disposed between the display element layer DP-ED and the substrate BL. The filler layer (not shown) may be an organic material layer. The filler layer (not shown) may include at least one of acrylic resin, silicone resin and epoxy resin.
[0157] The display panel DP may include a substrate layer BS, a circuit layer DP-CL provided on the substrate layer BS, and a display element layer DP-ED. The display element layer DP-ED may include a pixel defining film PDL, a plurality of light-emitting elements ED-1, ED-2, and ED-3 disposed between the pixel defining films PDL, and an encapsulation layer TFE disposed on the plurality of light-emitting elements ED-1, ED-2, and ED-3.
[0158] The substrate layer BS can be a component providing a substrate surface, and the display element layer DP-ED is disposed on the substrate surface. The substrate layer BS can be a glass substrate, a metal substrate, or a plastic substrate, etc. However, the embodiments are not limited to these, and the substrate layer BS can be an inorganic layer, an organic layer, or a composite material layer.
[0159] In one or more embodiments, the circuit layer DP-CL may be disposed on the substrate layer BS, and 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 switching transistors and driving transistors for driving the light-emitting elements ED-1, ED-2, and ED-3 of the display element layer DP-ED.
[0160] The light-emitting elements ED-1, ED-2, and ED-3 may each have the features described herein from Figures 3 to 6 The structure of a light-emitting element (ED) according to one or more embodiments. Light-emitting elements ED-1, ED-2 and ED-3 may each include a first electrode EL1, a hole transport region HTR, an emitter layer EML-R, EML-G and EML-B, an electron transport region ETR and a second electrode EL2.
[0161] Figure 2One or more embodiments are shown, wherein the emitting layers EML-R, EML-G, and EML-B of light-emitting elements ED-1, ED-2, and ED-3 are disposed in an opening OH defined by a pixel-defining film PDL, and the hole transport region HTR, the electron transport region ETR, and the second electrode EL2 are provided as a common layer throughout the light-emitting elements ED-1, ED-2, and ED-3. However, the embodiments are not limited thereto, and are related to... Figure 2 As shown in the embodiments, in one or more implementations, the hole transport region HTR and electron transport region ETR can be provided as patterned within an opening OH defined by a pixel-defined film PDL. For example, in one or more implementations, the hole transport region HTR, emitting layers EML-R, EML-G, and EML-B, and electron transport region ETR of light-emitting elements ED-1, ED-2, and ED-3 can be patterned and provided by inkjet printing.
[0162] The encapsulation layer TFE may cover light-emitting elements ED-1, ED-2, and ED-3. The encapsulation layer TFE may seal light-emitting elements ED-1, ED-2, and ED-3 in the display element layer DP-ED. The encapsulation layer TFE may be a thin-film encapsulation layer. The encapsulation layer TFE may be a single layer or a stack of multiple layers. The encapsulation layer TFE includes at least one insulating layer. According to one or more embodiments, the encapsulation layer TFE may include at least one inorganic film (hereinafter, encapsulated inorganic film). Alternatively, according to one or more embodiments, the encapsulation layer TFE may include at least one organic film (hereinafter, encapsulated organic film) and at least one encapsulated inorganic film.
[0163] An inorganic encapsulation film protects the display element layer (DP-ED) from moisture and / or oxygen, while an organic encapsulation film protects the DP-ED from foreign matter (such as dust particles). The inorganic encapsulation film may include silicon nitride, silicon oxynitride, silicon oxide, titanium dioxide, or aluminum oxide, but the implementation is not limited to these. The organic encapsulation film may include acrylic compounds or epoxy compounds. The organic encapsulation film may include photopolymerizable organic materials, and there are no particular limitations.
[0164] The encapsulation layer TFE can be disposed on the second electrode EL2, and can be configured to fill the opening OH.
[0165] refer to Figure 1 and Figure 2 The display module DM may include a non-emitting area NPXA and emitting areas PXA-R, PXA-G, and PXA-B. Each of the emitting areas PXA-R, PXA-G, and PXA-B may be a region that emits light generated from each of the light-emitting elements ED-1, ED-2, and ED-3. When viewed on a plane, the emitting areas PXA-R, PXA-G, and PXA-B may be spaced apart from each other.
[0166] The light-emitting regions PXA-R, PXA-G, and PXA-B can each be a region separated by a pixel-defining film PDL. The non-light-emitting region NPXA can be the region between adjacent light-emitting regions PXA-R, PXA-G, and PXA-B, and can correspond to the pixel-defining film PDL. In some embodiments, the light-emitting regions PXA-R, PXA-G, and PXA-B can each correspond to a pixel. The pixel-defining film PDL can separate the light-emitting elements ED-1, ED-2, and ED-3. The emitting layers EML-R, EML-G, and EML-B of the light-emitting elements ED-1, ED-2, and ED-3 can be disposed in the opening OH defined by the pixel-defining film PDL, and are therefore separated.
[0167] The luminescent regions PXA-R, PXA-G, and PXA-B can be divided into multiple groups based on the color of the light generated from luminescent elements ED-1, ED-2, and ED-3. Figure 1 and Figure 2 The display module DM shown in the figure, according to one or more embodiments, illustrates three light-emitting areas PXA-R, PXA-G, and PXA-B emitting red, green, and blue light as examples. For instance, the display module DM according to one or more embodiments may include red light-emitting area PXA-R, green light-emitting area PXA-G, and blue light-emitting area PXA-B, which are distinct from each other.
[0168] In a display module DM according to one or more embodiments, a plurality of light-emitting elements ED-1, ED-2, and ED-3 may emit light with different wavelength ranges. For example, in one or more embodiments, the display module DM may include a first light-emitting element ED-1 emitting red light, a second light-emitting element ED-2 emitting green light, and a third light-emitting element ED-3 emitting blue light. That is, the red light-emitting area PXA-R, the green light-emitting area PXA-G, and the blue light-emitting area PXA-B of the display module DM 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.
[0169] However, the implementation is not limited to this, and the first to third light-emitting elements ED-1, ED-2, and ED-3 may emit light within the same wavelength range, or at least one of them may emit light within a different wavelength range. For example, the first to third light-emitting elements ED-1, ED-2, and ED-3 may all emit blue light.
[0170] According to one or more embodiments, the light-emitting areas PXA-R, PXA-G, and PXA-B in the display module DM can be arranged in the form of stripes. (Reference) Figure 1Multiple red emitting areas PXA-R, multiple green emitting areas PXA-G, and multiple blue emitting areas PXA-B can each be arranged along the second directional axis DR2. Optionally, the red emitting areas PXA-R, green emitting areas PXA-G, and blue emitting areas PXA-B can be arranged alternately along the first directional axis DR1 in this order.
[0171] Figure 1 and Figure 2 The luminescent regions PXA-R, PXA-G, and PXA-B are shown to be identical in size, but the implementation is not limited to this, and the luminescent regions PXA-R, PXA-G, and PXA-B may differ in size depending on the wavelength range of the emitted light. The area of the luminescent regions PXA-R, PXA-G, and PXA-B indicates the area when viewed in a plane defined by the first directional axis DR1 and the second directional axis DR2. The third directional axis DR3 may be perpendicular to the plane defined by the first directional axis DR1 and the second directional axis DR2.
[0172] The arrangement of the luminescent regions PXA-R, PXA-G, and PXA-B is not limited to... Figure 1 As shown, the order in which the red emitting areas PXA-R, green emitting areas PXA-G, and blue emitting areas PXA-B are arranged varies depending on the display quality characteristics required by the display module DM. For example, the emitting areas PXA-R, PXA-G, and PXA-B can be arranged in a honeycomb pattern (PENTILE). ® ) or diamond (Diamond Pixel) ® Arranged in the form of ).
[0173] Furthermore, the light-emitting areas PXA-R, PXA-G, and PXA-B may differ in size from each other. For example, in one or more embodiments, the green light-emitting area PXA-G may be smaller in size than the blue light-emitting area PXA-B, but the embodiments are not limited to this.
[0174] The following text, Figures 3 to 6 Each of the above schematically illustrates a cross-sectional view of a light-emitting element (ED) according to one or more embodiments. The light-emitting element (ED) according to one or more embodiments may include a first electrode EL1, a hole transport region HTR, an emitter layer EML, an electron transport region ETR, and a second electrode EL2, stacked sequentially.
[0175] and Figure 3 compared to, Figure 4 A cross-sectional view of a light-emitting element (ED) according to one or more embodiments is shown, wherein the hole transport region (HTR) includes a hole injection layer (HIL) and a hole transport layer (HTL), and the electron transport region (ETR) includes an electron injection layer (EIL) and an electron transport layer (ETL). Additionally, with Figure 3 compared to, Figure 5A cross-sectional view of a light-emitting element (ED) according to one or more embodiments is shown, wherein the hole transport region (HTR) includes a hole injection layer (HIL), a hole transport layer (HTL), and an electron blocking layer (EBL), and the electron transport region (ETR) includes an electron injection layer (EIL), an electron transport layer (ETL), and a hole blocking layer (HBL). Figure 4 compared to, Figure 6 A cross-sectional view of a light-emitting element ED according to one or more embodiments is shown, wherein a capping layer CPL is provided on a second electrode EL2.
[0176] The first electrode EL1 is conductive. The first electrode EL1 may be formed of a metallic material, a metal alloy, or a conductive compound. The first electrode EL1 may be an anode or a cathode. However, the embodiments are not limited thereto. Additionally, the first electrode EL1 may be a pixel electrode. The first electrode EL1 may be a transmission electrode, a transmission-reflection electrode, or a reflection electrode. The first electrode EL1 may include at least one of Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF, Mo, Ti, W, In, Sn, and Zn, a compound selected from at least two of these, a mixture selected from at least two of these, or an oxide thereof.
[0177] When the first electrode EL1 is a transmission electrode, it may comprise a transparent metal oxide, such as indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), or indium tin zinc oxide (ITZO). When the first electrode EL1 is a transmissive-reflective electrode or a reflective electrode, it may comprise Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF, Mo, Ti, and / or W, or compounds thereof or mixtures thereof (e.g., a mixture of Ag and Mg), or multilayer materials such as LiF / Ca (a stacked structure of LiF and Ca) or LiF / Al (a stacked structure of LiF and Al). Optionally, the first electrode EL1 may have a multilayer structure, comprising a reflective or transmissive-reflective film formed from the above materials, and a transparent conductive film formed from indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), or indium tin zinc oxide (ITZO). For example, the first electrode EL1 may have a three-layer structure of ITO / Ag / ITO, but the implementation is not limited to this. Furthermore, the implementation is not limited to this, and the first electrode EL1 may include the aforementioned metallic material, a combination of two or more metallic materials selected from the aforementioned metallic materials, or an oxide of the aforementioned metallic materials. The first electrode EL1 may have a thickness of approximately 700 Å to approximately 10,000 Å. For example, the first electrode EL1 may have a thickness of approximately 1,000 Å to approximately 3,000 Å.
[0178] A hole transport region (HTR) is provided on the first electrode EL1. The hole transport region (HTR) may include at least one of a hole injection layer (HIL), a hole transport layer (HTL), a buffer layer (i.e., a light-emitting auxiliary layer (not shown)), and an electron blocking layer (EBL). The hole transport region (HTR) may have a thickness of, for example, from about 50 Å to about 15,000 Å.
[0179] The hole transport region (HTR) can have a single-layer structure formed by a single material, a single-layer structure formed by a variety of different materials, or a multi-layer structure formed by multiple layers of various different materials.
[0180] For example, the hole transport region HTR may have a single-layer structure formed by a hole injection layer HIL or a hole transport layer HTL, or a single-layer structure formed by a hole injection material and a hole transport material. For example, the hole transport region HTR may have a single-layer structure formed by a variety of different materials, or a structure in which the hole injection layer HIL / hole transport layer HTL, the hole injection layer HIL / hole transport layer HTL / buffer layer (not shown), the hole injection layer HIL / buffer layer (not shown), the hole transport layer HTL / buffer layer (not shown), or the hole injection layer HIL / hole transport layer HTL / electron blocking layer EBL are stacked sequentially from the first electrode EL1, but the implementation is not limited to this.
[0181] Hole transport regions (HTRs) can be formed using various methods (such as vacuum deposition, spin coating, casting, Langmuir-Brookett (LB) method, inkjet printing, laser printing, or laser-induced thermal imaging (LITI) method), but the implementation methods are not limited to these.
[0182] The hole transport region (HTR) may include a compound represented by formula H-1:
[0183] Formula H-1
[0184] .
[0185] In formula H-1, L1 and L2 can each independently be a directly linked, substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms. a and b can each independently be an integer selected from 0 to 10. When a or b is an integer of 2 or greater, the plurality of L1 and the plurality of L2 can each independently be a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms.
[0186] In formula H-1, Ar1 and Ar2 can each be independently a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms. Additionally, in formula H-1, Ar3 can be a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms.
[0187] The compound represented by formula H-1 may be a monoamine compound. Optionally, the compound represented by formula H-1 may be a diamine compound in which at least one of Ar1 to Ar3 includes an amino group as a substituent. Alternatively, the compound represented by formula H-1 may be a carbazole-containing compound in which at least one of Ar1 and Ar2 includes a substituted or unsubstituted carbazole group, or a fluorene-containing compound in which at least one of Ar1 and Ar2 includes a substituted or unsubstituted fluorene group.
[0188] The compound represented by formula H-1 may be represented by one of the compounds from compound group H. However, the compounds listed in compound group H are presented as examples, and the compound represented by formula H-1 is not limited to the compounds listed in compound group H.
[0189] Compound group H
[0190]
[0191]
[0192] .
[0193] Hole transport region (HTR) may include at least one of the following: phthalocyanine compounds (such as copper phthalocyanine), N 1 N 1' -([1,1'-biphenyl]-4,4'-diyl)bis(N) 1 -Phenyl-N 4 N 4-Di-m-Tolylphenyl-1,4-Diamine (DNTPD), 4,4',4"-[Tris(3-methylphenyl)phenylamino]triphenylamine (m-MTDATA), 4,4',4"-Tris(N,N-diphenylamino)triphenylamine (TDATA), 4,4',4"-Tris[N-(2-naphthyl)-N-phenylamino]triphenylamine (2-TNATA), Poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), Polyaniline / dodecylbenzenesulfonic acid (PANI / DB) SA), polyaniline / camphor sulfonic acid (PANI / CSA), polyaniline / poly(4-styrene sulfonate) (PANI / PSS), N,N'-di(naphthyl-1-yl)-N,N'-diphenyl-benzidine (NPB), triphenylamine-containing polyether ketone (TPAPEK), 4-isopropyl-4'-methyldiphenyliodonium tetra(pentafluorophenyl)borate and dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarboxynitrile (HAT-CN), etc., but the implementation methods are not limited to these.
[0194] The hole transport region (HTR) may include at least one of the following: containing carbazole derivatives (such as N-phenylcarbazole or polyvinylcarbazole), containing fluorene derivatives, triphenylamine derivatives (such as N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (TPD), 4,4',4"-tris(carbazole-9-yl)triphenylamine (TCTA), N,N'-bis(naphthyl-1-yl)-N,N'-diphenyl-benzidine (NPB), 4,4'-cyclohexylenebis[N,N-bis(4-methylphenyl)aniline] (TAPC), 4,4'-bis[N,N'-(3-tolyl)amino]-3,3'-dimethylbiphenyl (HMTPD) and 1,3-bis(carbazole-9-yl)benzene (mCP)), etc., but the implementation is not limited to these.
[0195] In addition, the hole transport region (HTR) may include at least one of the following: 9-(4-tert-butylphenyl)-3,6-bis(triphenylsilyl)-9H-carbazole (CzSi), 9-phenyl-9H-3,9'-bicarbazole (CCP), and 1,3-bis(1,8-dimethyl-9H-carbazole-9-yl)benzene (mDCP), but the implementation is not limited thereto.
[0196] The hole transport region HTR may include a compound of the aforementioned hole transport region HTR in at least one of the hole injection layer HIL, the hole transport layer HTL, and the electron blocking layer EBL.
[0197] The hole transport region (HTR) can have a thickness of about 100 Å to about 10,000 Å (e.g., about 100 Å to about 5,000 Å). When the hole transport region (HTR) includes a hole injection layer (HIL), the hole injection layer (HIL) can have a thickness of, for example, about 30 Å to about 1,000 Å. When the hole transport region (HTR) includes a hole transport layer (HTL), the hole transport layer (HTL) can have a thickness of about 30 Å to about 1,000 Å. When the hole transport region (HTR) includes an electron blocking layer (EBL), the electron blocking layer (EBL) can have a thickness of, for example, about 10 Å to about 1,000 Å. When the thicknesses of the hole transport region (HTR), the hole injection layer (HIL), the hole transport layer (HTL), and the electron blocking layer (EBL) meet the above ranges, satisfactory hole transport characteristics can be obtained without significantly increasing the driving voltage.
[0198] In addition to the materials described above, the hole transport region (HTR) may further include a charge-generating material to increase conductivity. The charge-generating material may be uniformly or non-uniformly dispersed in the hole transport region (HTR). The charge-generating material may be, for example, a p-dopant. The p-dopant may include at least one of metal halides, quinone derivatives, metal oxides, and cyano-containing compounds, but the implementation is not limited thereto. For example, p-dopers may include metal halides (such as CuI or RbI), quinone derivatives (such as tetracyanoquinone dimethyl ether (TCNQ) or 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinone dimethyl ether (F4-TCNQ)), metal oxides (such as tungsten oxide or molybdenum oxide), or cyano-containing compounds (such as dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarboxynitrile (HAT-CN) or 4-[[2,3-bis[cyano-(4-cyano-2,3,5,6-tetrafluorophenyl)methylene]cyclopropylidene]-cyanomethyl]-2,3,5,6-tetrafluorobenzonitrile (NDP9)), etc., but the implementation is not limited to these.
[0199] As described herein, in addition to the hole injection layer HIL and the hole transport layer HTL, the hole transport region HTR may further include at least one of a buffer layer (not shown) and an electron blocking layer EBL. The buffer layer (not shown) can compensate for the resonant distance according to the wavelength of light emitted from the emitter layer EML, and can thus increase luminous efficiency. Materials that may be included in the hole transport region HTR can be used as materials included in the buffer layer (not shown). The electron blocking layer EBL is a layer used to prevent electrons from being injected from the electron transport region ETR into the hole transport region HTR.
[0200] In one or more embodiments, the emitter layer EML may include a first compound according to one or more embodiments. The emitter layer EML according to one or more embodiments may further include at least one of a second to a fourth compound. The second compound may include a fused ring of three rings containing a nitrogen atom as a cyclizing atom. The third compound may include a six-membered ring group containing at least one nitrogen atom as a cyclizing atom. The fourth compound may include an organometallic complex. The second to fourth compounds are as described herein.
[0201] In this document, the first compound may be referred to as a fused polycyclic compound represented by Formula 1 according to one or more embodiments. A fused polycyclic compound represented by Formula 1 according to one or more embodiments may comprise a fused ring as a core structure containing nine rings with two boron atoms, at least two nitrogen atoms, and at least one oxygen or sulfur atom as cyclic atoms. Additionally, in the fused polycyclic compound represented by Formula 1 according to one or more embodiments, the benzene ring bonded to at least two nitrogen atoms of the core structure may comprise at least four substituted or unsubstituted phenyl groups. Furthermore, the benzene ring bonded to the two boron atoms may each independently comprise a substituted or unsubstituted phenyl group bonded at the para or immediately adjacent para position to the carbon atom bonded to the boron atom. The immediately adjacent para position refers to the ortho or meta position. For example, the benzene rings bonded to the two boron atoms may each independently include substituted or unsubstituted phenyl groups bonded to the para and / or meta positions of the carbon atoms connected to the boron atoms (i.e., the substituted or unsubstituted phenyl groups on the two benzene rings respectively bonded to the two boron atoms may be substituted at the para and / or meta positions of the carbon atoms of the benzene rings connected to the boron atoms). Accordingly, the fused polycyclic compounds represented by Formula 1 according to one or more embodiments can exhibit excellent material stability and contribute to improving the luminous efficiency and lifespan of light-emitting elements (EDs).
[0202] A light-emitting element (ED) according to one or more embodiments may include a fused polycyclic compound according to one or more embodiments. The fused polycyclic compound is represented by Formula 1.
[0203] Formula 1
[0204]
[0205] In Formula 1, Y1 and Z1 are each independently a hydrogen atom, a deuterium atom, a cyano group, a nitro group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms. For example, Y1 and Z1 may each independently be a hydrogen atom, a deuterium atom, a cyano group, a substituted or unsubstituted methyl group, a substituted or unsubstituted tert-butyl group, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted biphenyl group. In one or more embodiments, Y1 and Z1 may each independently be represented by any one of W-1 to W-7:
[0206] .
[0207] In Formula 1, X1 to X4 are each independently O, S, or a group represented by Formula 2. At least two of X1 to X4 are represented by Formula 2.
[0208] In Equation 1, R0 to R 13 Each of the following groups is independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro 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 cyclic carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 30 cyclic carbon atoms, or a group represented by Formula 3. In Formula 1, at least one of R1 to R4 is a group represented by Formula 3, and R 10 To R 13 At least one of them is a group represented by Formula 3. In some embodiments, R1 to R4 and R 10 To R 13 The remaining groups that are not represented by Formula 3 can each be independently hydrogen atoms or deuterium atoms.
[0209] Formula 2
[0210]
[0211] In Equation 2, R A To R E Each of the following groups is independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 cyclic carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 30 cyclic carbon atoms, or a group represented by Formula 3. At least two R groups from Formula 2 A To R E It includes four or more substituted or unsubstituted benzene rings.
[0212] In both Equations 2, R A To RE Each is provided as two, and the two equations 2 may include 10 by R A To R E Any of the groups represented by R. For example, in 10 groups represented by R A To R E Of any of the represented groups, 4 are substituted or unsubstituted benzene rings. 10 are represented by R. A To R E One of the groups represented may include four substituted or unsubstituted benzene rings. In the case of 10 groups consisting of R... A To R E Of any of the represented groups, one may include three substituted or unsubstituted benzene rings, and the other may include one substituted or unsubstituted benzene ring. 10 groups are represented by R. A To R E Any two of the groups represented may each independently comprise two substituted or unsubstituted benzene rings. In this case, the two substituted or unsubstituted benzene rings may form a substituted or unsubstituted biphenyl. Optionally, in 10 groups composed of R A To R E In any one of the represented groups, any two may be independently substituted or unsubstituted benzene rings, and the other may include two substituted or unsubstituted benzene rings. In this case, the two substituted or unsubstituted benzene rings may form a substituted or unsubstituted biphenyl group.
[0213] Formula 3
[0214]
[0215] In Equation 3, R a To R e Each of these can independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro 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 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 cyclic carbon atoms. For example, R a To R e Each of these can independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted tert-butylphenyl group, a substituted or unsubstituted cyanophenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted alkyl biphenyl group, a substituted or unsubstituted dimethylphenyl group, or a substituted or unsubstituted ditert-butylphenyl group. In one or more embodiments, Formula 3 can be represented by one of R-1 to R-13:
[0216] .
[0217] In one or more embodiments, the fused polycyclic compound represented by Formula 1 may include a structure in which any hydrogen atom in the molecule is replaced by a deuterium atom. For example, the deuterium atom may be directly bonded to a fused ring of nine rings containing two boron atoms, at least two nitrogen atoms, and at least one oxygen or sulfur atom as cyclic atoms. Optionally, the substituent substituted with the deuterium atom may be bonded to a fused ring of nine rings containing two boron atoms, at least two nitrogen atoms, and at least one oxygen or sulfur atom.
[0218] In one or more embodiments, Equation 1 may be represented by any one of Equations 1-A1 to 1-A3. Equation 1-A1 may be R3 and R in Equation 1. 11 Each can be a substituted or unsubstituted phenyl group, independently. Formula 1-A2 can be any of R4 and R in Formula 1. 11 Each can be a substituted or unsubstituted phenyl group, independently. Formula 1-A3 can be any of R4 and R in Formula 1. 10 The cases where each is an independently substituted or unsubstituted phenyl group.
[0219] Formula 1-A1
[0220]
[0221] Formula 1-A2
[0222]
[0223] Formula 1-A3
[0224]
[0225] In Equations 1-A1 to 1-A3, the same descriptions as in Equation 1 above can also be applied to X1 to X4 and R0 to R. 13 Y1 and Z1.
[0226] In equations 1-A1 to 1-A3, R a1 To R a6 Each of the following can be independently a hydrogen atom, a deuterium atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms. In Formulas 1-A1 to 1-A3, m1 to m6 can each be independently an integer selected from 0 to 5.
[0227] When m1 is an integer of 2 or greater, multiple R a1 They can all be the same, or at least one can be different from the rest. When m1 is 5 and there are five R's... a1 When m2 is a hydrogen atom, the situation is the same as when m1 is 0. When m2 is an integer of 2 or greater, multiple R... a2They can all be the same, or at least one can be different from the rest. When m² is 5 and there are five R's... a2 When m3 is a hydrogen atom, the situation is the same as when m2 is 0. When m3 is 2 or a larger integer, multiple R... a3 They can all be the same, or at least one can be different from the rest. When m3 is 5 and there are five R's... a3 When the atom is hydrogen, the situation is the same as when m3 is 0.
[0228] When m4 is an integer of 2 or greater, multiple R a4 They can all be the same, or at least one can be different from the rest. When m4 is 5 and there are five R's... a4 When m5 is a hydrogen atom, the situation is the same as when m4 is 0. When m5 is a 2 or larger integer, multiple R... a5 They can all be the same, or at least one can be different from the rest. When m5 is 5 and there are five R's... a5 When m6 is a hydrogen atom, the situation is the same as when m5 is 0. When m6 is an integer of 2 or greater, multiple R... a6 They can all be the same, or at least one can be different from the rest. When m6 is 5 and there are five R's... a6 When the atom is hydrogen, the situation is the same as when m6 is 0.
[0229] In one or more embodiments, Equation 1 may be represented by one of Equations 1-B1 to 1-B3. Equations 1-B1 to 1-B3 may be cases where two of X1 to X4 in Equation 1 are Equations 2. Equation 1-B1 may be cases where X3 and X4 in Equation 1 are each independently Equation 2. Equation 1-B2 may be cases where X1 and X4 in Equation 1 are each independently Equation 2. Equation 1-B3 may be cases where X1 and X3 in Equation 1 are each independently Equation 2.
[0230] Formula 1-B1
[0231]
[0232] Formula 1-B2
[0233]
[0234] Formula 1-B3
[0235]
[0236] In Equations 1-B1 to 1-B3, the same descriptions as in Equation 1 above can also be applied to R0 to R... 13 Y1 and Z1. In equations 1-B1 to 1-B3, X 11 and X 12Each can be O or S independently. For example, in Equation 1-B1, X 11 and X 12 It can be O. In Equation 1-B2, X 11 and X 12 It can be O. In Equation 1-B2, X 11 and X 12 It can be S. In equation 1-B2, X 11 It can be O and X 12 It can be S. In equation 1-B3, X 11 and X 12 It can be O. In Equation 1-B3, X 11 It can be O and X 12 It can be S.
[0237] In equations 1-B1 to 1-B3, R 1A To R 1E and R 2A To R 2E Each of these groups may be independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 cyclic carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 30 cyclic carbon atoms, or a group represented by Formula 3.
[0238] In equations 1-B1 to 1-B3, R 1A To R 1E and R 2A To R 2E The number of benzene rings in it is 4 or more. In both formulas 2, R 1A To R 1E and R 2A To R 2E Each can be provided once, and both Equations 2 can include 10 units from R. 1A To R 1E and R 2A To R 2E Any of the groups represented by R. For example, in 10 groups represented by R 1A To R 1E and R 2A To R 2E Of any of the represented groups, four can be substituted or unsubstituted benzene rings. Ten are formed by R. 1A To R 1E and R 2A To R 2E One of the groups represented may include four substituted or unsubstituted benzene rings. In the case of 10 groups consisting of R... 1A To R 1Eand R 2A To R 2E Of any of the represented groups, one may include three substituted or unsubstituted benzene rings, and the other may include one substituted or unsubstituted benzene ring. 10 groups are represented by R. 1A To R 1E and R 2A To R 2E Any two of the groups represented may each independently comprise two substituted or unsubstituted benzene rings. In this case, the two substituted or unsubstituted benzene rings may form a substituted or unsubstituted biphenyl. Optionally, in 10 groups composed of R 1A To R 1E and R 2A To R 2E In any one of the represented groups, any two may be independently substituted or unsubstituted benzene rings, and the other may include two substituted or unsubstituted benzene rings. In this case, the two substituted or unsubstituted benzene rings may form a substituted or unsubstituted biphenyl group.
[0239] In one or more embodiments, Equation 2 may be represented by any one of Equations 2-1 to 2-8. Equation 2-1 may be R in Equation 2. C For substituted or unsubstituted phenyl groups. Formula 2-2 can be where R in Formula 2 is... A and R C Each can be a substituted or unsubstituted phenyl group, independently. Formulas 2-3 can be where R in Formula 2 is... A and R E Each can be a substituted or unsubstituted phenyl group, independently. Formulas 2-4 can be R in formula 2. B and R D Each can be an independently substituted or unsubstituted phenyl group. Formulas 2-5 can be where R in Formula 2 is... A R C and R E Each can be an independently substituted or unsubstituted phenyl group. Formulas 2-6 can be in which R in Formula 2 A R B and R C Each can be a substituted or unsubstituted phenyl group, independently. Formula 2-7 can be any of the substituted or unsubstituted phenyl groups in Formula 2. A For substituted or unsubstituted phenyl groups. Formulas 2-8 can be where R in Formula 2 is... B The case of substituted or unsubstituted phenyl groups.
[0240] Equation 2-1
[0241]
[0242] Equation 2-2
[0243]
[0244] Equation 2-3
[0245]
[0246] Equation 2-4
[0247]
[0248] Formula 2-5
[0249]
[0250] Formula 2-6
[0251]
[0252] Formula 2-7
[0253]
[0254] Formula 2-8
[0255]
[0256] In equations 2-1 to 2-8, R A1 To R D1 Each of the following can be independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 10 cyclic carbon atoms. R b1 To R b15 Each of the following can be a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms. n1 to n15 can each be an integer selected from 0 to 5.
[0257] When n1 is an integer of 2 or greater, multiple R b1 They can all be the same, or at least one can be different from the rest. When n1 is 5 and there are five R's... b1 When n is a hydrogen atom, the case is the same as when n1 is 0. When n2 is an integer of 2 or greater, multiple R... b2 They can all be the same, or at least one can be different from the rest. When n² is 5 and there are five R's... b2 When n is a hydrogen atom, the case is the same as when n2 is 0. When n3 is an integer of 2 or greater, multiple R... b3 They can all be the same, or at least one can be different from the rest. When n3 is 5 and there are five R's... b3 When the atom is hydrogen, the situation is the same as when n3 is 0.
[0258] When n4 is an integer of 2 or greater, multiple R b4 They can all be the same, or at least one can be different from the rest. When n4 is 5 and there are five R's... b4 When n is a hydrogen atom, the case is the same as when n4 is 0. When n5 is an integer of 2 or greater, multiple R... b5 They can all be the same, or at least one can be different from the rest. When n5 is 5 and there are five R's... b5 When n is a hydrogen atom, the case is the same as when n5 is 0. When n6 is an integer of 2 or greater, multiple R... b6 They can all be the same, or at least one can be different from the rest. When n = 5 and there are five R's... b6 When the atom is hydrogen, the situation is the same as when n6 is 0.
[0259] When n7 is an integer of 2 or greater, multiple R b7 They can all be the same, or at least one can be different from the rest. When n7 is 5 and there are five R's... b7 When n is a hydrogen atom, the case is the same as when n7 is 0. When n8 is an integer of 2 or greater, multiple R... b8 They can all be the same, or at least one can be different from the rest. When n = 5 and there are five R's... b8 When n is a hydrogen atom, the case is the same as when n8 is 0. When n9 is an integer of 2 or greater, multiple R... b9 They can all be the same, or at least one can be different from the rest. When n9 is 5 and there are five R's... b9 When the atom is hydrogen, the situation is the same as when n9 is 0.
[0260] When n10 is an integer of 2 or greater, multiple R b10 They can all be the same, or at least one can be different from the rest. When n10 is 5 and there are five R's... b10 When n11 is a hydrogen atom, the case is the same as when n10 is 0. When n11 is an integer of 2 or greater, multiple R... b11 They can all be the same, or at least one can be different from the rest. When n11 is 5 and there are five R's... b11 When n12 is a hydrogen atom, the case is the same as when n11 is 0. When n12 is an integer of 2 or greater, multiple R... b12 They can all be the same, or at least one can be different from the rest. When n12 is 5 and there are five R's... b12 When the atom is hydrogen, the situation is the same as when n12 is 0.
[0261] When n13 is an integer of 2 or greater, multiple R b13 They can all be the same, or at least one can be different from the rest. When n13 is 5 and there are five R's...b13 When n is a hydrogen atom, the case is the same as when n13 is 0. When n14 is an integer of 2 or greater, multiple R... b14 They can all be the same, or at least one can be different from the rest. When n14 is 5 and there are five R's... b14 When n is a hydrogen atom, the case is the same as when n14 is 0. When n15 is an integer of 2 or greater, multiple R... b15 They can all be the same, or at least one can be different from the rest. When n15 is 5 and there are five R's... b15 When the atom is hydrogen, the situation is the same as when n15 is 0.
[0262] In one or more embodiments, Equation 2-1 may be represented by one of 2-1A to 2-1C, Equation 2-2 may be represented by one of 2-2A and 2-2B, Equation 2-3 may be represented by one of 2-3A to 2-3G, Equation 2-4 may be represented by one of 2-4A and 2-4B, Equation 2-5 may be represented by one of 2-5A to 2-5D, Equation 2-6 may be represented by 2-6A, Equation 2-7 may be represented by 2-7A, and Equation 2-8 may be represented by 2-8A.
[0263]
[0264]
[0265]
[0266] The fused polycyclic compound of Formula 1 may be represented by one of the compounds from Group 1. A light-emitting element (ED) according to one or more embodiments may include at least one of the compounds from Group 1.
[0267] Compound group 1
[0268]
[0269]
[0270]
[0271]
[0272]
[0273]
[0274]
[0275]
[0276]
[0277]
[0278]
[0279]
[0280]
[0281]
[0282]
[0283]
[0284]
[0285]
[0286]
[0287]
[0288]
[0289]
[0290]
[0291]
[0292]
[0293]
[0294]
[0295] A light-emitting element ED comprising a fused polycyclic compound represented by Formula 1 according to one or more embodiments may have a maximum emission wavelength in the wavelength range of about 440 nm to about 490 nm. The maximum emission wavelength may indicate the wavelength at the point of maximum emission intensity in the emission spectrum. A light-emitting element ED comprising a fused polycyclic compound represented by Formula 1 according to one or more embodiments may emit blue light. A third light-emitting element ED-3 ( ) emits blue light. Figure 2 It may include fused polycyclic compounds represented by Formula 1 according to one or more embodiments.
[0296] The emission layer EML may include a fused polycyclic compound represented by Formula 1 according to one or more embodiments as a dopant. The fused polycyclic compound represented by Formula 1 according to one or more embodiments may be a delayed fluorescence material. The fused polycyclic compound represented by Formula 1 according to one or more embodiments may be a thermally activated delayed fluorescence (TADF) material. The fused polycyclic compound represented by Formula 1 according to one or more embodiments may emit light via an anti-intersystem crossing (RISC) mechanism that converts triplet excitons into singlet excitons.
[0297] Compounds typically containing one or two phenyl groups on a benzene ring bonded to a nitrogen atom exhibit active intermolecular interactions, leading to reduced device lifetime. Additionally, compounds typically lacking phenyl groups on a benzene ring bonded to a boron atom exhibit high electron density, resulting in reduced device stability. Furthermore, compounds typically containing heterocyclic groups, such as carbazole groups, exhibit reduced heat resistance.
[0298] Including a fused ring of nine rings containing boron and oxygen (or sulfur) atoms as cyclic atoms, and such that at least one of R1 to R4 and R are combined with the aforementioned R 10 To R 13 At least one of the compounds not represented by Formula 3 has an increased electron density in the benzene ring adjacent to an oxygen (or sulfur) atom, allowing the benzene ring adjacent to the oxygen (or sulfur) atom to become a hole trapping site. Accordingly, the compound causes a decrease in the stability of the light-emitting element. In addition, compounds including fused rings of nine rings containing two boron atoms as cyclizing atoms and not containing substituents according to one or more embodiments undergo decomposition when deposited to form a light-emitting element, and intermolecular aggregation needs to be suppressed.
[0299] Conversely, the fused polycyclic compound of Formula 1 according to one or more embodiments may introduce at least four substituted or unsubstituted phenyl groups onto a benzene ring bonded to at least two nitrogen atoms in the core structure, and the benzene ring bonded to the two boron atoms may each independently introduce a substituted or unsubstituted phenyl group at the para or adjacent para position of the carbon atom bonded to the boron atom, resulting in improved heat resistance. The adjacent para position refers to the ortho or meta position. For example, the benzene ring bonded to the two boron atoms may each independently include a substituted or unsubstituted phenyl group bonded to the para and / or meta positions of the boron atom. In one or more embodiments, the fused polycyclic compound of Formula 1 introduces a substituted or unsubstituted phenyl group of Formula 3, and may therefore have improved material stability and can be adapted to emit light suitable for use in display modules (DM). Figure 1 The light emitted is at wavelengths specified in the formula. Furthermore, fused polycyclic compounds represented by Formula 1 according to one or more embodiments, including such chemical structures, can contribute to improved sublimation characteristics, longer lifespan, and higher stability of the light-emitting element.
[0300] In one or more embodiments, the fused polycyclic compound represented by Formula 1 comprises a fused ring as its core structure, consisting of nine rings containing two boron atoms, at least two nitrogen atoms, and at least one oxygen or sulfur atom as cyclic atoms, and may thus result in a reduced molecular weight and improved inter-system crossing rate. The fused polycyclic compound represented by Formula 1 according to one or more embodiments may exhibit improved sublimation properties during compound synthesis.
[0301] The fused polycyclic compound of Formula 1 according to one or more embodiments may include at least two nitrogen atoms as cyclizing atoms in its core structure. The benzene ring bonded to the at least two nitrogen atoms may include at least four substituted or unsubstituted phenyl groups as substituents. The benzene ring and the substituted or unsubstituted phenyl groups bonded thereto may form a sterically bulky substituent. In one or more embodiments, the fused polycyclic compound of Formula 1 introduces a sterically bulky substituent, which can thus prevent intermolecular interactions, thereby suppressing intermolecular aggregation, and light-emitting elements (EDs) including the fused polycyclic compound of Formula 1 according to one or more embodiments may exhibit properties such as high fluorescence quantum yield, narrow full width at half maximum (FWHM), and resistance to degradation in device lifetime.
[0302] The fused polycyclic compound represented by Formula 1 according to one or more embodiments includes two boron atoms as cyclic atoms in its core structure. The benzene ring bonded to the two boron atoms may each independently include a substituted or unsubstituted phenyl group bonded at the para or adjacent para position to the carbon atom bonded to the boron atom. The adjacent para position refers to the ortho or meta position. For example, the benzene ring bonded to the two boron atoms may each independently include a substituted or unsubstituted phenyl group bonded at the para and / or meta position to the boron atom. Accordingly, the fused polycyclic compound represented by Formula 1 according to one or more embodiments can be resonantly stable by having HOMO / LOMO orbitals throughout molecular extension, and light-emitting elements (EDs) comprising the fused polycyclic compound represented by Formula 1 according to one or more embodiments can exhibit high element stability and suppressed material degradation.
[0303] The fused polycyclic compound represented by Formula 1 according to one or more embodiments may not include heterocyclic groups such as carbazole groups. The fused polycyclic compound represented by Formula 1 may not include heterocyclic groups such as carbazole groups at specific positions in Formula 1 (i.e., Y1 and Z1). Accordingly, light-emitting elements (EDs) including the fused polycyclic compound represented by Formula 1 according to one or more embodiments may exhibit improved heat resistance.
[0304] In one or more embodiments, the emitter layer EML may include a fused polycyclic compound represented by Formula 1 according to one or more embodiments, and may further include at least one of a second to a fourth compound. In one or more embodiments, the emitter layer EML may include a second compound represented by Formula HT-1. For example, the second compound may be used as a hole transport host material of the emitter layer EML.
[0305] HT-1
[0306]
[0307] In formula HT-1, A1 to A8 can each be N or CR independently. 51 For example, A1 to A8 can all be CR. 51 Optionally, any one of A1 to A8 can be N, and the rest can be CR. 51 .
[0308] In formula HT-1, L1 can be a directly linked, substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms. For example, L1 can be a directly linked, substituted or unsubstituted phenylene, a substituted or unsubstituted divalent biphenyl, or a substituted or unsubstituted divalent carbazole, etc., but the embodiments are not limited to these.
[0309] In equation HT-1, Y a Can be used for direct connection, CR 52 R 53 or SiR 54 R 55 That is, the two six-membered rings (e.g., benzene rings) connected to the nitrogen atom of formula HT-1 can be directly connected, or Connection. In equation HT-1, when Y a When directly connected, the second compound represented by formula HT-1 may include a carbazole moiety.
[0310] In formula HT-1, Ar1 is a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms. For example, Ar1 may be a substituted or unsubstituted carbazolyl, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted dibenzothiophenel, or a substituted or unsubstituted biphenyl, but the embodiments are not limited thereto.
[0311] In equation HT-1, R 51 To R 55Each of these can independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted thio group, a substituted or unsubstituted oxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted boron group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 cyclic carbon atoms. Optionally, R 51 To R 55 Each can bond with an adjacent group to form a ring. For example, R 51 To R 55 Each can be an independent hydrogen atom or a deuterium atom. In one or more embodiments, R 51 To R 55 Each can be an unsubstituted methyl or an unsubstituted phenyl group, and each can be independently represented by an unsubstituted methyl group or an unsubstituted phenyl group.
[0312] In one or more embodiments, the second compound represented by formula HT-1 may be represented by one of the compounds shown in compound group 2. The emitter layer EML may include at least one of the compounds shown in compound group 2 as a hole transport host material.
[0313] Compound group 2
[0314]
[0315]
[0316]
[0317]
[0318] In the specific example compounds presented in Compound Group 2, “D” may indicate a deuterium atom, and “Ph” may indicate a substituted or unsubstituted phenyl group. For example, in the specific example compounds presented in Compound Group 2, “Ph” may be an unsubstituted phenyl group.
[0319] In one or more embodiments, the emitter layer EML may include a third compound represented by formula ET-1. For example, the third compound may be used as the electron transport host material of the emitter layer EML.
[0320] ET-1
[0321]
[0322] In equation ET-1, at least one of X1 to X3 can be N, and the rest can be CR. 56For example, any one of X1 to X3 can be N, and the other two can each be CR independently. 56 In this case, the third compound represented by formula ET-1 may include a pyridine moiety. Optionally, two of X1 to X3 may be N, and the other may be CR. 56 In this case, the third compound represented by formula ET-1 may include a pyrimidine moiety. Optionally, X1 to X3 may all be N. In this case, the third compound represented by formula ET-1 may include a triazine moiety.
[0323] In equation ET-1, R 56 It may be a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 cyclic carbon atoms.
[0324] In Equation ET-1, b1 to b3 can each be an integer selected from 0 to 10 independently.
[0325] In formula ET-1, Ar2 to Ar4 can each independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms. For example, Ar2 to Ar4 can be a substituted or unsubstituted phenyl group or a substituted or unsubstituted carbazole group.
[0326] In formula ET-1, L2 to L4 can each be independently a directly linked, substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms. When b1 to b3 are integers of 2 or greater, L2 to L4 can each be independently a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms.
[0327] In one or more embodiments, the third compound may be represented by one of the compounds from compound group 3. The light-emitting element ED according to one or more embodiments may include one of the compounds from compound group 3.
[0328] Compound group 3
[0329]
[0330]
[0331]
[0332]
[0333]
[0334]
[0335]
[0336]
[0337]
[0338]
[0339]
[0340] In the specific example compounds presented in compound group 3, “D” indicates a deuterium atom and “Ph” indicates an unsubstituted phenyl group.
[0341] The emitter layer EML may include a second compound and a third compound, and the second and third compounds may form an excited-state complex. In the emitter layer EML, the hole transport host and the electron transport host may form an excited-state complex. In this case, the triplet energy level (T1) of the excited-state complex formed by the hole transport host and the electron transport host corresponds to the difference between the lowest unoccupied molecular orbital (LUMO) energy level of the electron transport host and the highest occupied molecular orbital (HOMO) energy level of the hole transport host.
[0342] For example, the triplet energy level of an excited-state complex formed by a hole transport host and an electron transport host can have an absolute value of about 2.4 eV to about 3.0 eV. Furthermore, the triplet energy level of the excited-state complex can have a value smaller than the bandgap of each host material. The excited-state complex can have a triplet energy level of about 3.0 eV or less, which serves as the bandgap between the hole transport host and the electron transport host.
[0343] In one or more embodiments, in addition to the first to third compounds described herein, the emission layer EML may include a fourth compound. The fourth compound may be used as a sensitizer for the emission layer EML. Energy may be transferred from the fourth compound to the first compound to emit light.
[0344] For example, the emitting layer EML may include an organometallic complex containing platinum (Pt) as a central metal atom and ligands bonded to the central metal atom as a fourth compound. In a light-emitting element (ED) according to one or more embodiments, the emitting layer EML may include a compound represented by formula D-1 as a fourth compound.
[0345] Formula D-1
[0346]
[0347] In equation D-1, Q1 to Q4 can each be C or N independently.
[0348] In formula D-1, rings C1 to C4 can each be independently a substituted or unsubstituted aliphatic hydrocarbon cyclogroup having 5 to 30 cyclic carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 30 cyclic carbon atoms.
[0349] In equation D-1, L 11 To L 13 Each can be independently connected directly. , , , Substituted or unsubstituted alkylene groups having 1 to 20 carbon atoms, substituted or unsubstituted arylene groups having 6 to 30 cyclic carbon atoms, or substituted or unsubstituted heteroarylene groups having 2 to 30 cyclic carbon atoms. In L 11 To L 13 middle," "Indicates the sites connected to rings C1 through C4."
[0350] In equation D-1, b11 to b13 can each be 0 or 1 independently. When b11 is 0, rings C1 and C2 can be disconnected. When b12 is 0, rings C2 and C3 can be disconnected. When b13 is 0, rings C3 and C4 can be disconnected.
[0351] In equation D-1, R 61 To R 66 Each of these can independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted thio group, a substituted or unsubstituted oxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted boron group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 cyclic carbon atoms. Optionally, R 61 To R 66 Each can bond with an adjacent group to form a ring. In one or more embodiments, R 61 To R 66 Each can be independently a substituted or unsubstituted methyl group or a substituted or unsubstituted tert-butyl group.
[0352] In formula D-1, d1 to d4 can each be an integer selected from 0 to 4 independently. In formula D-1, when d1 to d4 are each 0, the fourth compound may not be affected by R. 61 To R 64 Replacement. When d1 to d4 are each 4 and R 61 To R 64 When each d1 to d4 is a hydrogen atom, the situation is the same as when each of d1 to d4 is 0. When each of d1 to d4 is an integer of 2 or greater, multiple provided R... 61 To R 64 They can be the same, or multiple Rs. 61 Up to multiple R 64 At least one of them may be different from the rest.
[0353] In formula D-1, rings C1 to C4 can each be independently a substituted or unsubstituted aliphatic hydrocarbon cyclogroup or a substituted or unsubstituted heterocyclic group represented by any one of C-1 to C-4.
[0354]
[0355]
[0356] In C-1 to C-4, P1 can be... or CR 74 P2 can be or NR 81 P3 can be or NR 82 And P4 can be or CR 88 R 71 To R 88 Each of them may be independently a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, or may be bonded to an adjacent group to form a ring.
[0357] Additionally, in C-1 to C-4, " "Indicates the portion connected to the central metal atom Pt, and" "Indicates connection to adjacent rings C1 to C4 or connecting base L" 11 To the connecting base L 13 The connecting part.
[0358] An emission layer EML according to one or more embodiments may include a first compound, which is a fused polycyclic compound represented by Formula 1, and at least one of a second to a fourth compound. For example, the emission layer EML may include a first compound, a second compound, and a third compound. In the emission layer EML, the second compound and the third compound form an excited-state complex, and energy can be transferred from the excited-state complex to the first compound to emit light.
[0359] Additionally, the emitter layer EML may include a first compound, a second compound, a third compound, and a fourth compound. In the emitter layer EML, the second and third compounds form an excited-state complex, and energy can be transferred from the excited-state complex to the fourth and first compounds to emit light. In one or more embodiments, the fourth compound may be a sensitizer (i.e., an auxiliary dopant). In the light-emitting element ED according to one or more embodiments, the fourth compound included in the emitter layer EML can be used as a sensitizer for transferring energy from the host to the first compound, which is a light-emitting dopant. That is, the fourth compound, acting as an auxiliary dopant, can accelerate the energy transfer to the first compound, which is a light-emitting dopant, thereby increasing the light emission ratio of the first compound. Accordingly, the emitter layer EML according to one or more embodiments may have increased luminous efficiency. Furthermore, when the energy transfer to the first compound increases, excitons formed in the emitter layer EML do not accumulate in the emitter layer EML and emit light rapidly, resulting in less device degradation. Accordingly, the light-emitting element ED according to one or more embodiments may have increased device lifetime.
[0360] A light-emitting element (ED) according to one or more embodiments may include each of a first compound, a second compound, a third compound, and a fourth compound, and the emission layer (EML) may therefore include a combination of two host materials and two dopant materials. In a light-emitting element (ED) according to one or more embodiments, the emission layer (EML) includes a second compound and a third compound as two different hosts, a first compound as a light-emitting dopant that emits delayed fluorescence, and a fourth compound as an auxiliary dopant that is an organometallic complex, and may therefore exhibit excellent luminescent efficiency.
[0361] In one or more embodiments, the fourth compound represented by formula D-1 may be represented by at least one of the compounds shown in compound group 4. The emission layer EML may include at least one of the compounds from compound group 4 as a sensitizer.
[0362] Compound group 4
[0363]
[0364]
[0365]
[0366]
[0367]
[0368] In the specific example compounds presented in compound group 4, “D” indicates a deuterium atom.
[0369] When the emitting layer EML in a light-emitting element (ED) according to one or more embodiments comprises all of the first, second, third, and fourth compounds described above, the first compound may be provided in an amount from about 0.1 wt% to about 5 wt% relative to the total weight of the first, second, third, and fourth compounds. However, the embodiments are not limited thereto. When the amount of the first compound satisfies the above proportions, the energy transfer from the second and third compounds to the first compound can be greater, and correspondingly, the luminous efficiency and device lifespan can be increased.
[0370] In the emitter layer EML, the amount of the second and third compounds may be the remaining weight excluding the weight of the first and fourth compounds described herein. For example, in the emitter layer EML, the second and third compounds may be provided in an amount of about 65 wt% to about 95 wt% relative to the total weight of the first, second, third, and fourth compounds.
[0371] The weight ratio of the second compound to the third compound relative to the total weight of the second compound and the third compound can be from about 3:7 to about 7:3.
[0372] When the amounts of the second and third compounds meet the above-mentioned ratio range, the charge balance in the emitter layer (EML) can be improved, thereby increasing luminous efficiency and device lifespan. When the amounts of the second and third compounds are outside the above-mentioned ratio range, the charge balance in the emitter layer (EML) can be impaired, thereby reducing luminous efficiency and making the light-emitting element (ED) more prone to degradation.
[0373] When the emitter layer EML includes a fourth compound, the fourth compound may be provided in an amount of about 10 wt% to about 30 wt% relative to the total weight of the first, second, third, and fourth compounds. In one or more embodiments, when the emitter layer EML includes a fourth compound, the sum of the content (e.g., amount) of the second compound and the content (e.g., amount) of the third compound may be about 65 wt% to about 89.9 wt% based on the total weight of the first, second, third, and fourth compounds in the emitter layer EML. However, the embodiments are not limited thereto. When the amount of the fourth compound meets the above-described range, energy transfer from the host to the first compound, which is a light-emitting dopant, can be increased, thereby improving the light emission ratio and thus enhancing the luminous efficiency of the emitter layer EML. When the first, second, third, and fourth compounds included in the emitter layer EML meet the above-described range, excellent luminous efficiency and long device lifetime can be achieved.
[0374] An emitter layer (EML) is provided on the hole transport region (HTR). The emitter layer (EML) may have a thickness of, for example, from about 100 Å to about 1000 Å or from about 100 Å to about 300 Å. The emitter layer (EML) may have a monolayer structure consisting of a single layer formed from a single material, a monolayer structure consisting of a single layer formed from multiple different materials, or a multilayer structure consisting of multiple layers formed from multiple different materials.
[0375] In addition to the fused polycyclic compound represented by Formula 1 according to one or more embodiments, the emitter layer EML may further include compounds that will be described herein.
[0376] In a light-emitting element (ED) according to one or more embodiments, the emitting layer (EML) may include anthracene derivatives, pyrene derivatives, fluoranthene derivatives, 1,2-benzophenanthrene derivatives, dihydrobenzanthene derivatives, or triphenylene derivatives. In one or more embodiments, the emitting layer (EML) may include anthracene derivatives or pyrene derivatives.
[0377] exist Figures 3 to 6 In the light-emitting element (ED) according to one or more embodiments shown, the emitting layer (EML) may include a host and a dopant, and the emitting layer (EML) may include a compound represented by Formula E-1. The compound represented by Formula E-1 can be used as a fluorescent host material.
[0378] E-1
[0379]
[0380] In equation E-1, R 31 To R 40Each of the following can independently be a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted silyl group, a substituted or unsubstituted thio group, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, or R 31 To R 40 It can bond with adjacent groups to form a ring. For example, R 31 To R 40 It can bond with adjacent groups to form saturated hydrocarbon rings, unsaturated hydrocarbon rings, saturated heterocycles, or unsaturated heterocycles.
[0381] In E-1, c and d can each be an integer selected from 0 to 5 independently.
[0382] In one or more embodiments, formula E-1 may be represented by one of compounds E1 to E21. In compounds E1 to E21, "D" may indicate a deuterium atom.
[0383]
[0384]
[0385] In one or more embodiments, the emitting layer EML may include a compound represented by formula E-2a or E-2b. The compound represented by formula E-2a or E-2b may be used as a host material for the phosphorescent emitting layer.
[0386] E-2a
[0387]
[0388] In equation E-2a, a can be an integer selected from 0 to 10, and each L a It can be independently a directly linked, substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms. When a is an integer of 2 or greater, multiple L a Each can be independently a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms.
[0389] Furthermore, in E-2a, A1 to A5 can each be independently N or CR. i R a To R iEach of these can independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted amino group, a substituted or unsubstituted thio group, a substituted or unsubstituted oxygen 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 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, or R a To R i It can bond with adjacent groups to form a ring. R a To R i It can bond with adjacent groups to form hydrocarbon rings or heterocycles containing N, O or S as cyclic atoms.
[0390] For example, in equation E-2a, two or three selected from A1 to A5 can be N, and the rest can be CR. i .
[0391] E-2b
[0392]
[0393] In formula E-2b, Cbz1 and Cbz2 can each independently be an unsubstituted carbazole group or a carbazole group substituted with an aryl group having 6 to 30 cyclic carbon atoms. Each L b It can be independently a directly linked, substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms; b can be an integer selected from 0 to 10; and when b is an integer of 2 or greater, multiple L b Each can be independently a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms.
[0394] The compound represented by formula E-2a or E-2b may be represented by one of the compounds from compound group E-2. However, the compounds listed in compound group E-2 are presented as examples, and the compounds represented by formula E-2a or E-2b are not limited to the compounds listed in compound group E-2.
[0395] Compound group E-2
[0396]
[0397]
[0398]
[0399]
[0400] The emitter layer EML may further include materials known in the art as the host material. For example, the emitter layer EML may include at least one of the following: bis(4-(9H-carbazole-9-yl)phenyl)diphenylsilane (BCPDS), (4-(1-(4-(diphenylamino)phenyl)cyclohexyl)phenyl)diphenylphosphine oxide (POPCPA), bis[2-(diphenylphosphino)phenyl]ether oxide (DPEPO), 4,4'-bis(N-carbazole)-1,1'-biphenyl (CBP), 1,3-bis(carbazole-9-yl)phenyl (mCP), 2,8-bis(diphenylphosphino)dibenzofuran (PPF), 4,4',4"-tris(carbazole-9-yl)triphenylamine (TCTA), and 1,3,5-tris(1-phenyl-1H-benzo[d]imidazole-2- (TPBi) . However, the embodiments are not limited to this, and at least one of the following can be used as the host material, for example: tris(8-hydroxyquinoline)aluminum (Alq3), 9,10-bis(naphthyl-2-yl)anthracene (ADN), 3-tert-butyl-9,10-bis(naphthyl-2-yl)anthracene (TBADN), stilbene (DSA), 4,4'-bis(9-carbazolyl)-2,2'-dimethylbiphenyl (CDBP), 2-methyl-9,10-bis(naphthyl-2-yl)anthracene (MADN), hexaphenylcyclotriphosphazene (CP1), 1,4-bis(triphenylsilyl)benzene (UGH2), hexaphenylcyclotrisiloxane (DPSiO3), and octaphenylcyclotetrasiloxane (DPSiO4).
[0401] The emitter layer (EML) may include compounds represented by the formula Ma. Compounds represented by the formula Ma can be used as phosphorescent dopant materials.
[0402] Formula Ma
[0403]
[0404] In formula Ma, Y1 to Y4 and Z1 to Z4 can each independently be CR1 or N, and R1 to R4 can each independently be 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 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, or R1 to R4 can be bonded to adjacent groups to form a ring. In formula Ma, m is 0 or 1, and n is 2 or 3. In formula Ma, when m is 0, n is 3, and when m is 1, n is 2.
[0405] Compounds represented by formula Ma can be represented by one of compounds M-a1 to M-a25. However, compounds M-a1 to M-a25 are presented as examples, and compounds represented by formula Ma are not limited to those represented by compounds M-a1 to M-a25.
[0406]
[0407]
[0408]
[0409]
[0410]
[0411]
[0412]
[0413] The emitter layer (EML) may include a compound represented by one of the formulas Fa to Fc. A compound represented by one of the formulas Fa to Fc can be used as a fluorescent dopant material.
[0414] Formula Fa
[0415]
[0416] In the formula Fa, the formula is selected from R. a To R j The two in can be independently... Replace. R a To R j The un-included The remaining substituted groups may each be 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 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms.
[0417] exist In this context, Ar1 and Ar2 can each be independently a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms. For example, at least one of Ar1 and Ar2 can be a heteroaryl group containing O or S as a cyclic atom.
[0418] Formula Fb
[0419]
[0420] In equation Fb, R a and R b Each of the following can be independently a hydrogen atom, a deuterium atom, 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 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, or R a and R b It can bond with adjacent groups to form a ring. Ar1 to Ar4 can each be independently a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms.
[0421] In formula Fb, ring U and ring V can each be independently a substituted or unsubstituted hydrocarbon cyclic group having 5 to 30 cyclic carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 30 cyclic carbon atoms. At least one of Ar1 to Ar4 can be a heteroaryl group containing O or S as a cyclic atom.
[0422] In formula Fb, the number of rings represented by ring U and ring V can each be independently 0 or 1. For example, in formula Fb, when the number of ring U or ring V is 1, a ring forms a fused ring at the portion indicated by ring U or ring V, and when the number of ring U or ring V is 0, it means that the ring indicated by ring U or ring V does not exist. Specifically, when the number of ring U is 0 and the number of ring V is 1, or when the number of ring U is 1 and the number of ring V is 0, the fused ring with a fluorene core in formula Fb can be a cyclic compound with four rings. Furthermore, when the number of both ring U and ring V is 0, the fused ring with a fluorene core in formula Fb can be a cyclic compound with three rings. Additionally, when the number of both ring U and ring V is 1, the fused ring with a fluorene core in formula Fb can be a cyclic compound with five rings.
[0423] Formula Fc
[0424]
[0425] In equation Fc, A1 and A2 can each be independently O, S, Se, or NR. m And R m It can be a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms. R1 to R 11Each of the following groups is independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted amino group, a substituted or unsubstituted boron group, a substituted or unsubstituted oxygen group, a substituted or unsubstituted thio group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, or R1 to R 11 It can bond with adjacent groups to form a ring.
[0426] In formula Fc, A1 and A2 can each independently bond with substituents of adjacent rings to form fused rings. For example, when A1 and A2 are each independently NR m In this case, A1 can bond with R4 or R5 to form a ring. Additionally, A2 can bond with R7 or R8 to form a ring.
[0427] The emitter layer (EML) may include at least one of the following as a dopant material: styrene derivatives (e.g., 1,4-bis[2-(3-N-ethylcarbazolyl)vinyl]benzene (BCzVB), 4-(di-p-tolylamino)-4'-[(di-p-tolylamino)styrene]stilbene (DPAVB), N-(4-((E)-2-(6-(((E)-4-(diphenylamino)styrene)naphth-2-yl)vinyl) (Phenyl)-N-phenylaniline (N-BDAVBi) or 4,4'-bis[2-(4-(N,N-diphenylamino)phenyl)vinyl]biphenyl (DPAVBi)), perylene and its derivatives (e.g., 2,5,8,11-tetra-tert-butylperylene (TBP)) and pyrene and its derivatives (e.g., 1,1'-dipyrene, 1,4-dipyrenebenzene, 1,4-bis(N,N-diphenylamino)pyrene), etc., but the embodiments are not limited thereto.
[0428] The emitter layer (EML) may include a phosphorescent dopant material. For example, metal composites including iridium (Ir), platinum (Pt), osmium (Os), gold (Au), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), or thulium (Tm) can be used as phosphorescent dopant. For example, bis(4,6-difluorophenylpyridinyl-N,C2')pyridinecarboxyiridium(III) (FIrpic), bis(2,4-difluorophenylpyridinyl)tetra(1-pyrazolyl)boronate(III) (FIr6), or octaethylporphyrin platinum (PtOEP) can be used as phosphorescent dopant. However, the implementation is not limited to these.
[0429] The emitter layer (EML) may include quantum dot materials. The core of the quantum dot may be a group II-VI compound, a group III-VI compound, a group I-III-VI compound, a group III-V compound, a group III-II-V compound, a group IV-VI compound, a group IV element, a group IV compound, or a combination thereof.
[0430] Group II-VI compounds can be: binary compounds, such as CdSe, CdTe, CdS, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, MgSe or MgS, or combinations thereof; ternary compounds, such as CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnTeS, HgSeS, HgSeTe, HgSTe, CdZnS, CdZnSe, etc. CdZnTe, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, MgZnSe or MgZnS, or combinations thereof; quaternary compounds, such as HgZnTeS, CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS or HgZnSeTe, or combinations thereof; or combinations thereof.
[0431] Group III-VI compounds may include: binary compounds, such as In2S3 or In2Se3, or combinations thereof; ternary compounds, such as InGaS3 or InGaSe3, or combinations thereof; or combinations thereof.
[0432] Group I-III-VI compounds may be: ternary compounds, such as AgInS, AgInS2, CuInS, CuInS2, AgGaS2, CuGaS2, CuGaO2, AgGaO2, or AgAlO2, or combinations thereof; quaternary compounds, such as AgInGaS, AgInGaS2, AgInGaSe, AgInGaSe2, CuInGaS, or CuInGaS2, or combinations thereof; or combinations thereof.
[0433] Group III-V compounds may be: binary compounds, such as GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, or InSb, or combinations thereof; ternary compounds, such as GaNP, GaNAs, GaNSb, GaPAs, GaPSb, AlNP, AlNAs, AlNSb, AlPAs, AlPSb, InGaP, InAlP, InNP, InNAs, InNSb, InPAs, or InPSb, or combinations thereof; quaternary compounds, such as GaAlNP, GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNP, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs, or InAlPSb, or combinations thereof; or combinations thereof. Group III-V compounds may further include Group II metals. For example, InZnP and other compounds can be selected as group III-II-V compounds.
[0434] Group IV-VI compounds can be: binary compounds, such as SnS, SnSe, SnTe, PbS, PbSe, or PbTe, or combinations thereof; ternary compounds, such as SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, or SnPbTe, or combinations thereof; quaternary compounds, such as SnPbSSe, SnPbSeTe, or SnPbSTe, or combinations thereof; or combinations thereof. Group IV elements can be Si, Ge, or combinations thereof. Group IV compounds can be binary compounds, such as SiC, SiGe, or combinations thereof.
[0435] Each element included in a multi-element compound (such as a binary, ternary, or quaternary compound) can exist in the particles at a homogeneous or non-homogeneous concentration. That is, the above formula indicates the type of element included in the compound, and the proportions of elements in the compound can vary. For example, AgInGaS2 can indicate AgIn x Ga 1-x S2(0 <x<1)。
[0436] In some embodiments, quantum dots may have a single structure having a uniform concentration of each element included in the corresponding quantum dot, or a core-shell dual structure. For example, the material included in the core may be different from the material included in the shell.
[0437] The shell of a quantum dot can serve as a protective layer to prevent chemical denaturation of the nucleus in order to maintain its semiconductor properties and / or as a charging layer to impart electrophoretic properties to the quantum dot. The shell can be single-layered or multi-layered. The interface between the nucleus and the shell can have a concentration gradient in which the concentration of elements present in the shell decreases towards the center of the nucleus.
[0438] In some embodiments, the quantum dot may have the aforementioned core / shell structure, comprising a core having nanocrystals and a shell surrounding the core. Examples of the shell of the quantum dot may be a metal or non-metal oxide, a semiconductor compound, or a combination thereof.
[0439] For example, the metal or non-metal oxide can be: binary compounds, such as SiO2, Al2O3, TiO2, ZnO, MnO, Mn2O3, Mn3O4, CuO, FeO, Fe2O3, Fe3O4, CoO, Co3O4 or NiO, or combinations thereof; ternary compounds, such as MgAl2O4, CoFe2O4, NiFe2O4 or CoMn2O4, or combinations thereof; or combinations thereof, but the implementation is not limited to these.
[0440] In addition, the semiconductor compound may be, for example, CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnSeS, ZnTeS, GaAs, GaP, GaSb, HgS, HgSe, HgTe, InAs, InP, InGaP, InSb, AlAs, AlP, or AlSb, or combinations thereof, but the implementation is not limited to these.
[0441] Each element included in a multi-element compound (such as binary and ternary compounds) may exist in the particles at a uniform or non-uniform concentration. That is, the above formula indicates the type of element included in the compound, and the proportions of elements in the compound may vary.
[0442] In the emission wavelength spectrum, quantum dots can have a full width at half maximum (FWHM) of about 45 nm or less (preferably about 40 nm or less, and more preferably about 30 nm or less), and within this range, color purity or color reproducibility can be improved. Furthermore, light emitted through quantum dots is emitted in all directions, and thus a wide viewing angle can be improved.
[0443] Furthermore, there are no particular restrictions on the form of quantum dots, as long as they are in a form commonly used in the field. More specifically, quantum dots can be used in the form of spherical, conical, multi-armed or cubic nanoparticles, nanotubes, nanowires, nanofibers or nanosheets, etc.
[0444] By controlling the size of the quantum dots or the elemental ratios in the quantum dot compound, the band gap can be controlled accordingly to obtain light from the quantum dot emitting layer in various wavelength ranges. Therefore, by using quantum dots as described herein (using quantum dots of different sizes or quantum dots with different elemental ratios in the quantum dot compound), light-emitting elements (EDs) emitting light in various wavelength ranges can be obtained. Specifically, the size of the quantum dots or the elemental ratios in the quantum dot compound can be controlled to emit red, green, and / or blue light. Furthermore, quantum dots can be configured to emit white light by combining various colors of light.
[0445] exist Figures 3 to 6 In the light-emitting element (ED) shown according to one or more embodiments, an electron transport region (ETR) is provided on the emitter layer (EML). The electron transport region (ETR) may include at least one of a hole blocking layer (HBL), an electron transport layer (ETL), and an electron injection layer (EIL), but the embodiments are not limited thereto.
[0446] The electron transport region (ETR) can have a single-layer structure made of a single material, a single-layer structure made of a variety of different materials, or a multi-layer structure made of multiple different materials.
[0447] For example, the electron transport region (ETR) may have a monolayer structure of either the electron injection layer (EIL) or the electron transport layer (ETL), or it may have a monolayer structure formed of an electron injection material and an electron transport material. Alternatively, the ETR may have a monolayer structure formed of a variety of different materials, or it may have a structure in which the electron transport layer (ETL) / electron injection layer (EIL) or the hole blocking layer (HBL) / electron transport layer (ETL) / electron injection layer (EIL) are stacked sequentially from the emitter layer (EML), but is not limited thereto. The ETR may have a thickness of, for example, from about 1000 Å to about 1500 Å.
[0448] The electron transport region (ETR) can be formed using various methods (such as vacuum deposition, spin coating, casting, Langmuir-Brookett (LB) method, inkjet printing, laser printing, or laser-induced thermal imaging (LITI) method), but the implementation method is not limited to these.
[0449] The electron transport region (ETR) may include compounds represented by the formula ET-2.
[0450] ET-2
[0451]
[0452] In Equation ET-2, at least one of X1 to X3 is N, and the rest are CR. a R aAr1 to Ar3 can each be a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms.
[0453] In Formula ET-2, a to c can each be an integer selected from 0 to 10. In Formula ET-2, L1 to L3 can each be a directly linked, substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms. When a to c are integers 2 or greater, L1 to L3 can each be a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms.
[0454] The electron transport region (ETR) may include anthracene-containing compounds. However, embodiments are not limited thereto, and the ETR may include at least one of the following: tris(8-hydroxyquinoline)aluminum (Alq3), 1,3,5-tris[(3-pyridyl)-benzyl-3-yl]benzene, 2,4,6-tris(3'-(pyridyl-3-yl)biphenyl-3-yl)-1,3,5-triazine, 2-(4-(N-phenylbenzimidazol-1-yl)phenyl)-9,10-dinaphthylanthracene, 1,3,5-tris(1-phenyl-1H-benzimidazol- 2-(4-dimethyl)phenyl (TPBi), 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), 3-(4-biphenyl)-4-phenyl-5-tert-butylphenyl-1,2,4-triazole (TAZ), 4-(naphthyl-1-yl)-3,5-diphenyl-4H-1,2,4-triazole (NTAZ), 2-(4-biphenyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole ( t Bu-PBD), bis(2-methyl-8-hydroxyquinoline-N1,O8)-(1,1'-biphenyl-4-hydroxy)aluminum (BAlq), bis(benzoquinoline-10-hydroxy)beryllium (Bebq2), 9,10-bis(naphthyl-2-yl)anthracene (ADN), 1,3-bis[3,5-bis(pyridin-3-yl)phenyl]benzene (BmPyPhB), and combinations thereof, but the embodiments are not limited thereto.
[0455] The electron transport region (ETR) may include at least one of compounds ET1 to ET36.
[0456]
[0457]
[0458]
[0459]
[0460] Additionally, the electron transport region ETR may include: metal halides, such as LiF, NaCl, CsF, RbCl, RbI, Cul, or KI; lanthanides, such as Yb; or co-deposited materials of metal halides and lanthanides. For example, the electron transport region ETR may include KI:Yb, RbI:Yb, or LiF:Yb as co-deposited materials. Metal oxides (such as Li₂O or BaO) or lithium 8-hydroxyquinoline (Liq) may be used for the electron transport region ETR, but the implementation is not limited to these. The electron transport region ETR may also be formed from a mixture of an electron transport material and an insulating organometallic salt. The insulating organometallic salt may be a material having a band gap of about 4 eV or greater. Specifically, the insulating organometallic salt may include, for example, metal acetates, metal benzoates, metal acetoacetates, metal acetylacetonates, metal stearates, or combinations thereof.
[0461] In addition to the materials described above, the electron transport region (ETR) may further include at least one of, for example, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), diphenyl(4-(triphenylsilyl)phenyl)phosphine oxide (TSPO1), and 4,7-diphenyl-1,10-phenanthroline (Bphen), but the embodiments are not limited thereto.
[0462] The electron transport region (ETR) may include a compound of the aforementioned electron transport region (ETR) in at least one of the electron injection layer (EIL), the electron transport layer (ETL), and the hole blocking layer (HBL).
[0463] When the electron transport region (ETR) includes an electron transport layer (ETL), the ETL may have a thickness of about 100 Å to about 1000 Å (e.g., about 150 Å to about 500 Å). When the thickness of the ETL meets the above range, satisfactory electron transport characteristics can be obtained without significantly increasing the driving voltage. When the electron transport region (ETR) includes an electron injection layer (EIL), the EIL may have a thickness of about 1 Å to about 100 Å (e.g., about 3 Å to about 90 Å). When the thickness of the EIL meets the above range, satisfactory electron injection characteristics can be obtained without significantly increasing the driving voltage.
[0464] 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 the implementation is not limited thereto. For example, when the first electrode EL1 is an anode, the second electrode EL2 may be a cathode, and when the first electrode EL1 is a cathode, the second electrode EL2 may be an anode.
[0465] The second electrode EL2 can be a transmission electrode, a transmission-reflection electrode, or a reflection electrode. When the second electrode EL2 is a transmission electrode, it can be formed of a transparent metal oxide (e.g., indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), or indium tin zinc oxide (ITZO), or combinations thereof).
[0466] When the second electrode EL2 is a transmissive or reflective electrode, it may comprise Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF, Mo, Ti, Yb, W, Na, or compounds thereof or mixtures thereof (e.g., AgMg, AgYb, AgLi, AgNa, or MgYb), or a material with a multilayer structure, such as LiF / Ca or LiF / Al. Optionally, the second electrode EL2 may have a multilayer structure, including a reflective or transmissive film formed from the aforementioned materials, and a transparent conductive film formed from indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), or indium tin zinc oxide (ITZO). For example, the second electrode EL2 may comprise the aforementioned metallic materials, a combination of two or more metallic materials selected from the aforementioned metallic materials, or oxides of the aforementioned metallic materials.
[0467] Although not shown, the second electrode EL2 can be connected to the auxiliary electrode. When the second electrode EL2 is connected to the auxiliary electrode, the resistance of the second electrode EL2 can be reduced.
[0468] The capping layer CPL may be further disposed on the second electrode EL2 of the light-emitting element ED according to one or more embodiments. The capping layer CPL may comprise multiple layers or a single layer.
[0469] In one or more embodiments, the capping layer CPL may be an organic layer or an inorganic layer. For example, when the capping layer CPL comprises an inorganic material, the inorganic material may include alkali metal compounds (such as LiF), alkaline earth metal compounds (such as MgF2), SiON, SiN. X or SiO y wait.
[0470] For example, when the capping layer CPL comprises an organic material, the organic material may include α-NPD, NPB, TPD, m-MTDATA, Alq3, CuPc, N4,N4,N4',N4'-tetra(biphenyl-4-yl)biphenyl-4,4'-diamine (TPD15) or 4,4',4"-tris(carbazole-9-yl)triphenylamine (TCTA), or may include epoxy resin or acrylate resin (such as methacrylate). However, the embodiments are not limited thereto, and the capping layer CPL may include at least one of compounds P1 to P5.
[0471]
[0472] The capping layer CPL may have a refractive index of about 1.6 or greater. Specifically, the capping layer CPL may have a refractive index of about 1.6 or greater in the wavelength range of about 550 nm to about 660 nm.
[0473] Figures 7 to 10 Cross-sectional views of display modules DM-a, DM-TD, DM-b, and DM-c according to one or more embodiments are shown below. (Referring to...) Figures 7 to 10 In the description of the display modules DM-a, DM-TD, DM-b, and DM-c according to one or more embodiments, the descriptions related to the above references will no longer be included. Figures 1 to 6 The content is repeated, and the main focus will be on describing the differences.
[0474] refer to Figure 7 According to one or more embodiments, the display module DM-a may include a display panel DP having a display element layer DP-ED, a light control layer CCL disposed on the display panel DP, and a color filter layer CFL. Figure 7 In one or more embodiments shown, the display panel DP may include a substrate layer BS, a circuit layer DP-CL provided on the substrate layer BS, and a display element layer DP-ED, wherein the element layer DP-ED may include a light-emitting element ED.
[0475] The light-emitting element ED may include a first electrode EL1, a hole transport region HTR disposed on the first electrode EL1, an emitter layer EML disposed on the hole transport region HTR, an electron transport region ETR disposed on the emitter layer EML, and a second electrode EL2 disposed on the electron transport region ETR. Figure 7 The structure of the light-emitting element ED shown above can be the same as described above. Figures 3 to 6 The structure of the light-emitting element (ED) is the same.
[0476] refer to Figure 7The emitting layer EML can be disposed in the opening OH defined by the pixel-defined film PDL. For example, the emitting layer EML provided separately by the pixel-defined film PDL and corresponding to each of the light-emitting regions PXA-R, PXA-G, and PXA-B can emit light within the same wavelength range. In the display module DM-a according to one or more embodiments, the emitting layer EML can emit blue light. Unlike what is shown, in one or more embodiments, the emitting layer EML can be provided as a common layer covering the light-emitting regions PXA-R, PXA-G, and PXA-B.
[0477] A light control layer (CCL) can be disposed on a display panel (DP). The light control layer (CCL) may include a light converter. The light converter may be a quantum dot or a phosphor. The light converter can convert the wavelength of the supplied light and emit light with the converted wavelength. That is, the light control layer (CCL) may be a layer containing quantum dots or phosphors.
[0478] The optical control layer (CCL) may include multiple optical control units (CCP1, CCP2, and CCP3). These multiple optical control units (CCP1, CCP2, and CCP3) may be spaced apart from each other.
[0479] refer to Figure 7 The segmented pattern BMP can be positioned between the spaced-apart optical control units CCP1, CCP2, and CCP3, but the implementation is not limited to this. Figure 7 In the diagram, the segmentation pattern BMP is shown as not overlapping with the optical control units CCP1, CCP2 and CCP3, but the edges of the optical control units CCP1, CCP2 and / or CCP3 may overlap with at least a portion of the segmentation pattern BMP.
[0480] The light control layer CCL may include: a first light control unit CCP1, including a first quantum dot QD1 for converting first color light provided by the light-emitting element ED into second color light; a second light control unit CCP2, including a second quantum dot QD2 for converting first color light into third color light; and a third light control unit CCP3 for transmitting first color light.
[0481] In one or more embodiments, a first light control unit CCP1 can provide red light as a second color light, and a second light control unit CCP2 can provide green light as a third color light. A third light control unit CCP3 can transmit and provide blue light as a first color light provided from the light-emitting element ED. For example, a first quantum dot QD1 can be a red quantum dot, and a second quantum dot QD2 can be a green quantum dot. The same description above can be applied to quantum dots QD1 and QD2.
[0482] Additionally, the optical control layer CCL may further include a scatterer SP. The first optical control unit CCP1 may include a first quantum dot QD1 and a scatterer SP, the second optical control unit CCP2 may include a second quantum dot QD2 and a scatterer SP, and the third optical control unit CCP3 may not include a quantum dot but may include a scatterer SP.
[0483] The scatterer SP can be inorganic particles. For example, the scatterer SP may include at least one of TiO2, ZnO, Al2O3, SiO2, and hollow silica. The scatterer SP may include one of TiO2, ZnO, Al2O3, SiO2, and hollow silica, or may include a mixture of two or more materials selected from TiO2, ZnO, Al2O3, SiO2, and hollow silica.
[0484] 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 or more embodiments, the first optical control unit CCP1 may include the first quantum dot QD1 and the scatterer SP dispersed in the first base resin BR1, the second optical control unit CCP2 may include the second quantum dot QD2 and the scatterer SP dispersed in the second base resin BR2, and the third optical control unit CCP3 may include the scatterer SP dispersed in the third base resin BR3.
[0485] The base resins BR1, BR2, and BR3 are the media in which quantum dots QD1 and QD2 and scatterers SP are dispersed, and can be formed from various resin compositions, generally referred to as binders. For example, base resins BR1, BR2, and BR3 can be acrylic resins, urethane resins, silicone resins, or epoxy resins, or combinations thereof. Base resins BR1, BR2, and BR3 can be transparent resins. In one or more embodiments, the first base resin BR1, the second base resin BR2, and the third base resin BR3 can be the same as or different from each other.
[0486] The light control layer CCL may include an isolation layer BFL1. Isolation layer BFL1 is used to prevent the introduction of moisture and / or oxygen (hereinafter referred to as "moisture / oxygen"). Isolation layer BFL1 may be disposed on light control units CCP1, CCP2, and CCP3 to prevent them from being exposed to moisture / oxygen. Isolation layer BFL1 may cover light control units CCP1, CCP2, and CCP3. Additionally, isolation layer BFL2 may be provided between light control units CCP1, CCP2, and CCP3 and filters CF1, CF2, and CF3.
[0487] The isolation layers BFL1 and BFL2 may include at least one inorganic layer. That is, the isolation layers BFL1 and BFL2 may be formed of inorganic materials. For example, the isolation layers BFL1 and BFL2 may be formed as silicon nitride, aluminum nitride, zirconium nitride, titanium nitride, hafnium nitride, tantalum nitride, silicon oxide, aluminum oxide, titanium oxide, tin oxide, cerium oxide, silicon oxynitride, or a light-transmitting metal film thereof, or combinations thereof. The isolation layers BFL1 and BFL2 may further include an organic film. The isolation layers BFL1 and BFL2 may be formed of a single layer or multiple layers.
[0488] In the display module DM-a according to one or more embodiments, the color filter layer CFL may be disposed on the light control layer CCL. For example, the color filter layer CFL may be disposed directly on the light control layer CCL. In this case, the isolation layer BFL2 may be omitted.
[0489] The color filter layer (CFL) may include filters CF1, CF2, and CF3. That is, the color filter layer (CFL) may include a first filter CF1 that transmits a second color of light, a second filter CF2 that transmits a third color of light, and a third filter CF3 that transmits a first color of light. For example, the first filter CF1 may be a red filter, the second filter CF2 may be a green filter, and the third filter CF3 may be a blue filter. Filters CF1, CF2, and CF3 may each include a polymer photosensitive resin, a pigment, or a dye. The first filter CF1 may include a red pigment or a red dye, the second filter CF2 may include a green pigment or a green dye, and the third filter CF3 may include a blue pigment or a blue dye.
[0490] The implementation is not limited to this, and the third filter CF3 may not include pigments or dyes. The third filter CF3 may include a polymeric photosensitive resin, but may not include pigments or dyes. The third filter CF3 may be transparent. The third filter CF3 may be formed of a transparent photosensitive resin.
[0491] Additionally, in one or more embodiments, the first filter CF1 and the second filter CF2 may be yellow filters. The first filter CF1 and the second filter CF2 may not be separate and may be provided as a single unit.
[0492] Although not shown, the color filter layer CFL may further include light-blocking units (not shown). The light-blocking units may be a black matrix. The light-blocking units may be formed comprising organic or inorganic light-blocking materials, both of which may include black pigments or black dyes. The light-blocking units prevent light leakage and separate adjacent filters CF1, CF2, and CF3. Additionally, in one or more embodiments, the light-blocking units may be formed from blue filters.
[0493] The first to third filters CF1, CF2 and CF3 can be set to correspond to the red light-emitting area PXA-R, the green light-emitting area PXA-G and the blue light-emitting area PXA-B, respectively.
[0494] The substrate BL may be disposed on the color filter layer CFL. The substrate BL may be a component providing a substrate surface, with the color filter layer CFL and the light control layer CCL disposed on the substrate surface. The substrate BL may be a glass substrate, a metal substrate, or a plastic substrate, etc. However, the embodiments are not limited to these, and the substrate BL may be an inorganic layer, an organic layer, or a composite material layer. Furthermore, unlike what is shown, in one or more embodiments, the substrate BL may not be provided.
[0495] Figure 8 This is a cross-sectional view illustrating a portion of a display module DM-TD according to one or more embodiments. In the display module DM-TD according to one or more embodiments, the light-emitting element ED-BT may include a plurality of light-emitting structures OL-B1, OL-B2, and OL-B3. The light-emitting element ED-BT may include a first electrode EL1 and a second electrode EL2 facing each other, and a plurality of light-emitting structures OL-B1, OL-B2, and OL-B3 provided by sequentially stacking between the first electrode EL1 and the second electrode EL2 in the thickness direction. Each of the light-emitting structures OL-B1, OL-B2, and OL-B3 may include a hole transport region HTR (Hypertransfer Region). Figure 7 Electronic Transfer Zone (ETR) Figure 7 ) and the hole transport region HTR ( Figure 7 ) and Electronic Transfer Zone (ETR) Figure 7 EML (emitting layer) between ) Figure 7 That is, the light-emitting element ED-BT included in the display module DM-TD according to one or more embodiments may be a light-emitting element having a series structure including multiple emitting layers.
[0496] exist Figure 8 In one or more embodiments shown, the light emitted from each of the light-emitting structures OL-B1, OL-B2, and OL-B3 may be blue light. However, the embodiments are not limited to this, and the wavelength range 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 comprising multiple light-emitting structures OL-B1, OL-B2, and OL-B3 emitting light in different wavelength ranges may emit white light.
[0497] Charge generation layers CGL1 and CGL2 may be disposed between adjacent light-emitting structures OL-B1, OL-B2, and OL-B3. Charge generation layers CGL1 and CGL2 may include p-type charge generation layers and / or n-type charge generation layers.
[0498] refer to Figure 9 The display module DM-b according to one or more embodiments may include light-emitting elements ED-1, ED-2, and ED-3 in which two emitting layers are stacked. Figure 2 Compared to the display module DM shown in the figure according to one or more embodiments, the difference lies in that... Figure 9 In one or more embodiments shown, the first to third light-emitting elements ED-1, ED-2, and ED-3 each include two 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 emitting layers can emit light within the same wavelength range.
[0499] The first light-emitting element ED-1 may include a first red emitting layer EML-R1 and a second red emitting layer EML-R2. The second light-emitting element ED-2 may include a first green emitting layer EML-G1 and a second green emitting layer EML-G2. Additionally, the third light-emitting element ED-3 may include a first blue emitting layer EML-B1 and a second blue emitting layer EML-B2. A light-emitting auxiliary portion OG may be disposed between the first red emitting layer EML-R1 and the second red emitting layer EML-R2, between the first green emitting layer EML-G1 and the second green emitting layer EML-G2, and between the first blue emitting layer EML-B1 and the second blue emitting layer EML-B2.
[0500] The light-emitting auxiliary portion (OG) may comprise a single layer or multiple layers. The OG may include a charge generation layer. More specifically, the OG may include an electron transport region (not shown), a charge generation layer (not shown), and a hole transport region (not shown) stacked sequentially. The OG may be provided as a common layer covering the first to third light-emitting elements ED-1, ED-2, and ED-3. However, the implementation is not limited to this, and the OG may be provided as being patterned within an opening OH defined by a pixel-defined film (PDL).
[0501] The first red emitting layer EML-R1, the first green emitting layer EML-G1, and the first blue emitting layer EML-B1 can be disposed between the light-emitting auxiliary region OG and the electron transport region ETR. The second red emitting layer EML-R2, the second green emitting layer EML-G2, and the second blue emitting layer EML-B2 can be disposed between the hole transport region HTR and the light-emitting auxiliary region OG.
[0502] That is, the first light-emitting element ED-1 may include a first electrode EL1, a hole transport region HTR, a second red emitting layer EML-R2, an emission auxiliary portion OG, a first red emitting layer EML-R1, an electron transport region ETR, and a second electrode EL2, stacked sequentially. The second light-emitting element ED-2 may include a first electrode EL1, a hole transport region HTR, a second green emitting layer EML-G2, an emission auxiliary portion OG, a first green emitting layer EML-G1, an electron transport region ETR, and a second electrode EL2, stacked sequentially. The third light-emitting element ED-3 may include a first electrode EL1, a hole transport region HTR, a second blue emitting layer EML-B2, an emission auxiliary portion OG, a first blue emitting layer EML-B1, an electron transport region ETR, and a second electrode EL2, stacked sequentially.
[0503] An optical auxiliary layer PL may be disposed on the display element layer DP-ED. The optical auxiliary layer PL may include a polarizing layer. The optical auxiliary layer PL may be disposed on the display panel DP to control reflected light in the display panel DP due to external light. Unlike what is shown, the optical auxiliary layer PL may not be provided in the display module DM-b according to one or more embodiments.
[0504] and Figure 8 and Figure 9 different, Figure 10 The display module DM-c is shown to include four light-emitting structures OL-B1, OL-B2, OL-B3, and OL-C1. The light-emitting element ED-CT may include a first electrode EL1 and a second electrode EL2 facing each other, and first to fourth light-emitting structures OL-B1, OL-B2, OL-B3, and OL-C1 stacked sequentially in the thickness direction between the first electrode EL1 and the second electrode EL2. Charge-generating layers CGL1, CGL2, and CGL3 may be disposed between the first to fourth light-emitting structures OL-B1, OL-B2, OL-B3, and OL-C1. For example, the first charge-generating layer CGL1 is disposed between the first light-emitting structure OL-B1 and the fourth light-emitting structure OL-C1. The second charge-generating layer CGL2 is disposed between the second light-emitting structure OL-B2 and the first light-emitting structure OL-B1. The third charge-generating layer CGL3 is disposed between the third light-emitting structure OL-B3 and the second light-emitting structure OL-B2. Of the four light-emitting structures, the first to third light-emitting structures OL-B1, OL-B2, and OL-B3 emit blue light, and the fourth light-emitting structure OL-C1 emits green light. However, the implementation is not limited to this, and the first to fourth light-emitting structures OL-B1, OL-B2, OL-B3, and OL-C1 can emit light with different wavelength ranges.
[0505] The charge generation layers CGL1, CGL2, and CGL3 disposed between adjacent light-emitting structures OL-B1, OL-B2, OL-B3, and OL-C1 may include p-type charge generation layers and / or n-type charge generation layers.
[0506] In one or more embodiments, the electronic device may include a display module comprising a plurality of light-emitting elements and a control portion configured to control the display module. The electronic device according to one or more embodiments may be a device activated in response to an electrical signal. The electronic device may include electronic devices of various embodiments. For example, the electronic device may include large electronic devices (such as televisions, monitors, or outdoor billboards) as well as small and medium-sized electronic devices (such as personal computers, laptop computers, personal digital terminals, in-vehicle displays, game consoles, portable electronic devices, or cameras).
[0507] Figure 11 A view showing the interior of a vehicle in which electronic devices according to one or more embodiments are provided. Figure 11 This is a view of the interior of a vehicle AM in which first to fourth electronic devices EA-1, EA-2, EA-3, and EA-4 are installed. At least one of the first to fourth electronic devices EA-1, EA-2, EA-3, and EA-4 may have the same characteristics as referenced... Figure 1 , Figure 2 and Figures 7 to 10 The display modules DM, DM-TD, DM-a, DM-b and / or DM-c described according to one or more embodiments have the same configuration.
[0508] Figure 11 A car is shown as a vehicle AM, but this is presented as an example, and the first to fourth electronic devices EA-1, EA-2, EA-3, and EA-4 can be installed in other means of transportation (such as bicycles, motorcycles, trains, boats, and airplanes). Additionally, at least one of the first to fourth electronic devices EA-1, EA-2, EA-3, and EA-4, having the same configuration as the display modules DM, DM-TD, DM-a, DM-b, and / or DM-c according to one or more embodiments, can be used in personal computers, laptop computers, personal digital terminals, game consoles, portable electronic devices, televisions, monitors, or outdoor billboards, etc. Furthermore, these are presented only as exemplary embodiments, and therefore the electronic devices can be used in other electronic devices without departing from this disclosure.
[0509] At least one of the first to fourth electronic devices EA-1, EA-2, EA-3 and EA-4 may include a reference. Figures 3 to 6 The light-emitting element described is ED.
[0510] refer to Figure 11 The vehicle AM may include a steering wheel HA and a gear shift lever GR for operating the vehicle AM, and has a front window GL set to face the driver.
[0511] The first electronic device EA-1 may be located in a first area overlapping with the steering wheel HA. For example, the first electronic device EA-1 may be a digital instrument panel displaying first information about the vehicle's AM. The first information may include a first scale indicating the vehicle's AM speed, a second scale indicating engine speed (i.e., revolutions per minute (RPM)), or an image indicating fuel status, etc. The first and second scales may be displayed as digital images.
[0512] The second electronic device EA-2 may be disposed in a second area facing the driver's seat and overlapping with the windshield GL. The driver's seat may be a seat with a steering wheel HA. For example, the second electronic device EA-2 may be a head-up display (HUD) that displays second information about the vehicle's AM. The second electronic device EA-2 may be optically transparent. The second information includes a numerical value indicating the vehicle's AM speed, and may further include information such as the current time. Unlike what is shown, the second information of the second electronic device EA-2 may be projected and displayed on the windshield GL.
[0513] The third electronic device EA-3 can be located in a third zone adjacent to the gear shift lever GR. For example, the third display device EA-3 can be a central information display (CID) for the vehicle, located between the driver's seat and the passenger seat, displaying third information. The passenger seat can be a seat spaced apart from the driver's seat, with the gear shift lever GR located between the driver's seat and the passenger seat. The third information may include information about road conditions (e.g., navigation information), information about music or radio broadcasts, information about video playback, or information about the temperature inside the vehicle's AM (Autonomous Vehicles) system.
[0514] The fourth display device EA-4 can be located in a fourth zone, spaced apart from the steering wheel HA and gear shift lever GR, and adjacent to one side of the vehicle AM. For example, the fourth electronic device EA-4 can be a digital side mirror displaying fourth information. The fourth electronic device EA-4 can display an image of the external conditions of the vehicle AM captured by a camera module CM located on the outside of the vehicle AM. The fourth information may include the image of the external conditions of the vehicle AM.
[0515] Presenting the first to fourth information as an example, and the first to fourth electronic devices EA-1, EA-2, EA-3, and EA-4 may further display information about the interior or exterior of the vehicle. The first to fourth information may include different information. However, the implementation is not limited to this, and some of the first to fourth information may include the same information.
[0516] Figure 12A perspective view of an electronic device EA according to one or more embodiments is shown. Figure 13 An exploded perspective view of an electronic device EA according to one or more embodiments is shown.
[0517] The electronic device EA can display an image IM via a display surface EA-IS. The image IM may include still images and moving images. The display surface EA-IS may be parallel to the plane defined by a first directional axis DR1 and a second directional axis DR2. Figure 12 An electronic device EA is shown with a flat display surface EA-IS, but the implementation is not limited thereto. For example, the electronic device EA may include a curved display surface or a three-dimensional display surface. A three-dimensional display surface may include multiple display areas indicating different orientations.
[0518] The display surface EA-IS may include a display area EA-DA and a non-display area EA-NDA. The electronic device EA can display an image IM through the display area EA-DA.
[0519] The non-display area EA-NDA may have a selected color. The non-display area EA-NDA may be adjacent to the display area EA-DA. The non-display area EA-NDA may surround the display area EA-DA. Accordingly, the shape of the display area EA-DA may be substantially defined by the non-display area EA-NDA. However, rendering... Figure 12 As an example, the non-display area EA-NDA may be set only adjacent to one side of the display area EA-DA, or the non-display area EA-NDA may not be provided.
[0520] refer to Figure 13 The electronic device EA may include a display module DM. Additionally, the electronic device EA may further include a window component WM and a housing HAU.
[0521] A window member WM may cover the entire external portion of an electronic device EA. The window member WM may include a transmissive area TA and a border area BZA. The front surface of the window member WM, including the transmissive area TA and the border area BZA, may serve as the front surface of the electronic device EA. The transmissive area TA may correspond to... Figure 12 The electronic device EA shown in the figure has a display area EA-DA, and the border area BZA can correspond to... Figure 12 The non-display area EA-NDA of the electronic device EA shown in the figure.
[0522] The transmissive region TA can be optically transparent. The border region BZA can be a region with relatively lower light transmittance than the transmissive region TA. The border region BZA can have a specified color. The border region BZA can be adjacent to and surround the transmissive region TA. The border region BZA can define the shape of the transmissive region TA. However, the implementation is not limited to what is shown, and the border region BZA may only be adjacent to one side of the transmissive region TA, and a portion of the border region BZA may not be provided.
[0523] The housing HAU may comprise a material with relatively high rigidity. For example, the housing HAU may comprise a frame and / or panel formed of glass, plastic, or metal. Multiple frames and / or panels may be provided. The housing HAU provides a housing space for containment. The display module DM can be housed within this housing space to be protected from external impacts.
[0524] The display module DM can have the same as the reference. Figure 1 , Figure 2 and Figures 7 to 10 The display modules DM, DM-TD, DM-a, DM-b, and DM-c described according to one or more embodiments have the same configuration. The display module DM may include reference... Figures 3 to 6 The light-emitting element ED is described. Accordingly, the electronic device EA, including the display module DM according to one or more embodiments, can exhibit excellent reliability.
[0525] In the display module DM, the active area DM-AA and the peripheral area DM-NAA can be defined. The active area DM-AA can be... Figure 12 The display areas EA-DA shown overlap, and the peripheral area DM-NAA can be... Figure 12 The non-display area EA-NDA overlaps as shown in the image.
[0526] The active region DM-AA can be a region activated by an electrical signal. The peripheral region DM-NAA can be a region adjacent to at least one side of the active region DM-AA. The active region DM-AA may include Figure 1 The diagram shows the non-light-emitting region NPXA and the light-emitting regions PXA-R, PXA-G, and PXA-R. The peripheral region DM-NAA may surround the active region DM-AA. However, the implementation is not limited to this, and unlike what is shown, a portion of the peripheral region DM-NAA may be omitted. A drive circuit or drive line for driving the active region DM-AA may be provided in the peripheral region DM-NAA.
[0527] The display module according to one or more embodiments can be applied to various electronic devices. An electronic device according to one or more embodiments may include the display module described herein, and may further include modules or devices with additional functions in addition to the display module.
[0528] Figure 14 This is a block diagram of an electronic device EA according to one or more embodiments. (Reference) Figure 14 An electronic device EA according to one or more embodiments may include a display module DM, a processor PR, a memory MR, and a power module PM.
[0529] The processor PR may include at least one of a central processing unit (CPU), an application processor (AP), a graphics processing unit (GPU), a communication processor (CP), an image signal processor (ISP), and a controller.
[0530] The memory MR can store the data information required for the operation of the processor PR or the display module DM. When the processor PR executes the application program stored in the memory MR, image data signals and / or input control signals are transmitted to the display module DM, and the display module DM can process the received signals and output image information through the display screen.
[0531] The power module PM may include: a power supply module, such as a power adapter or battery device; and a power conversion module, which converts the power supplied by the power supply module to generate the power required for the operation of the electronic device EA.
[0532] At least one component of the aforementioned electronic device EA may be included in the display device according to the above embodiment. Additionally, some of the individual modules functionally included in a single module may be included in the display device, while the remainder may be provided separately from the display device. For example, the display device may include a display module DM, and the processor PR, memory MR, and power module PM may be provided as other devices within the electronic device EA besides the display device.
[0533] Figure 15 Schematic diagrams of electronic devices according to various embodiments are shown.
[0534] refer to Figure 15 Various electronic devices that apply a display module according to one or more embodiments may include electronic devices for displaying images (such as smartphones EA_1a, tablet PCs EA_1b, laptops EA_1c, TVs EA_1d, and desktop monitors EA_1e), wearable electronic devices that include a display module (such as smart glasses EA_2a, head-mounted displays EA_2b, and smartwatches EA_2c), and vehicle electronic devices that include a display module EA_3 (such as in-vehicle mirror displays, vehicle instrument panels, center consoles, or central information displays (CIDs) mounted on the dashboard).
[0535] Hereinafter, with reference to embodiments and comparative examples, a fused polycyclic compound represented by Formula 1 and a light-emitting element according to one or more embodiments will be specifically described. Furthermore, the following embodiments are shown for illustrative purposes only, and the scope of this disclosure is not limited thereto.
[0536] Example
[0537] 1. Synthesis of fused polycyclic compounds represented by Equation 1
[0538] The processes for synthesizing fused polycyclic compounds represented by Formula 1 according to one or more embodiments will be described in further detail by presenting processes for synthesizing fused polycyclic compounds D-4, B-4, C-3, and G-1 as examples. Furthermore, processes for synthesizing fused polycyclic compounds, which will be described later herein, are provided as examples, and therefore the processes for synthesizing fused polycyclic compounds represented by Formula 1 according to one or more embodiments are not limited to the following examples.
[0539] (1) Synthesis of fused polycyclic compound D-4
[0540] The fused polycyclic compound D-4 was synthesized using the process described in Reaction Formula 1.
[0541] Reaction 1
[0542]
[0543]
[0544] Synthesis of intermediate compound D-4-3
[0545] Intermediate compounds D-4-1 (119 mmol), D-4-2 (125 mmol), and Cs₂CO₃ (179 mmol) were added to a three-necked flask and Ar displacement was performed. Then, 120 mL of N-methylpyrrolidone (NMP) was added, and the mixture was stirred at 120 °C for 4 hours. Water was added to the reaction mixture, and the organic layer was extracted with toluene. The organic layer was dried over magnesium sulfate, and the solvent was removed under reduced pressure. The crude product was purified by silica gel column chromatography (a mixture of hexane / toluene (v / v 2:1)) and recrystallization (a mixture of ethanol / toluene (v / v 4:1)) to obtain 80 mmol of white solid (yield: 55%). The purified product was determined to have a molecular weight of 359 g / mol by rapid atomic impact mass spectrometry (FAB-MS), indicating the acquisition of the target intermediate compound D-4-3.
[0546] Synthesis of intermediate compound D-4-5
[0547] Intermediate compounds D-4-3 (80 mmol), D-4-4 (89 mmol), K₂CO₃ (120 mmol), and tetrakis(triphenylphosphine)palladium(O) (Pd(PPh₃)₄) (8 mmol) were added to a three-necked flask and Ar displacement was performed. Then, 800 mL of toluene was added, and the mixture was stirred at 80 °C for 6 hours. Water was added to the reaction mixture, and the organic layer was extracted with toluene. The organic layer was dried over magnesium sulfate, and the solvent was removed under reduced pressure. The obtained crude product was purified by silica gel column chromatography (a mixture of hexane / toluene (v / v 2:1)) and recrystallization (a mixture of ethanol / toluene (v / v 4:1)) to obtain 40 mmol of white solid (yield: 50%). The molecular weight of the purified product was determined by FAB-MS to be 357 g / mol, indicating the yield of the target intermediate compound D-4-5.
[0548] Synthesis of intermediate compound D-4-7
[0549] Intermediate compounds D-4-5 (40 mmol), D-4-6 (50 mmol), tBuONa (120 mmol), bis(dibenzylacetone)palladium(O) (Pd(dba)2) (8 mmol), and 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (SPhos) (16 mmol) were added to a three-necked flask and Ar displacement was performed. Then, 200 mL of toluene was added, and the mixture was stirred at 100 °C for 3 h. Water was added to the reaction mixture, and the organic layer was extracted with toluene. The organic layer was dried over magnesium sulfate, and the solvent was removed under reduced pressure. The obtained crude product was purified by silica gel column chromatography (a mixture of hexane / toluene (v / v 2:1)) and recrystallization (a mixture of ethanol / toluene (v / v 4:1)) to obtain 23 mmol of white solid (yield: 58%). The purified product was determined to have a molecular weight of 566 g / mol by FAB-MS measurement, indicating the acquisition of the target intermediate compound D-4-7.
[0550] Synthesis of intermediate compound D-4-9
[0551] Intermediate compounds D-4-7 (23 mmol), D-4-8 (23 mmol), K₂CO₃ (230 mmol), and CuI (23 mmol) were added to a three-necked flask and Ar-substituted. The mixture was stirred at 220 °C for 50 h. Water was added to the reaction mixture, and the organic layer was extracted with toluene. The organic layer was dried over magnesium sulfate, and the solvent was removed under reduced pressure. The crude product was purified by silica gel column chromatography (a mixture of hexane and toluene (v / v 2:1)) and recrystallization (a mixture of ethanol and toluene (v / v 4:1)) to obtain 14 mmol of white solid (yield: 60%). The molecular weight of the purified product was determined by FAB-MS to be 1206 g / mol, indicating the yield of the target intermediate compound D-4-9.
[0552] Synthesis of fused polycyclic compound D-4
[0553] Intermediate compound D-4-9 (14 mmol) was added to a three-necked flask and Ar was substituted. Then, 40 mL of o-dichlorobenzene (ODCB) was added and dissolved. BI3 (56 mmol) was then added, and the mixture was stirred at 140 °C for 3 hours. The reaction solution was dispersed and washed with a large amount of acetonitrile, and the solid was collected by filtration. The obtained crude product was purified by silica gel column chromatography (a mixture of hexane / dichloromethane (v / v 2:1)) and recrystallization (a mixture of ethanol / toluene (v / v 4:1)) to obtain 5 mmol of yellow solid (yield: 36%). The purified product was determined to have a molecular weight of 1221 g / mol by FAB-MS, indicating the acquisition of the target fused polycyclic compound D-4.
[0554] (2) Synthesis of fused polycyclic compound B-4
[0555] The fused polycyclic compound B-4 was synthesized using the process described in Reaction Formula 2.
[0556] Reaction 2
[0557]
[0558] Synthesis of intermediate compound B-4-3
[0559] Intermediate compounds B-4-1 (200 mmol), B-4-2 (210 mmol), and Cs₂CO₃ (400 mmol) were added to a three-necked flask and Ar displacement was performed. Then, 400 mL of NMP was added, and the mixture was stirred at 120 °C for 10 h. Water was added to the reaction mixture, and the organic layer was extracted with toluene. The organic layer was dried over magnesium sulfate, and the solvent was removed under reduced pressure. The crude product was purified by silica gel column chromatography (a mixture of hexane / toluene (v / v 2:1)) and recrystallization (a mixture of ethanol / toluene (v / v 4:1)) to obtain 120 mmol of white solid (yield: 60%). The purified product was determined to have a molecular weight of 381 g / mol by FAB-MS, indicating the yield of the target intermediate compound B-4-3.
[0560] Synthesis of intermediate compound B-4-5
[0561] Intermediate compounds B-4-3 (120 mmol), B-4-4 (130 mmol), tBuONa (240 mmol), Pd(dba)2 (12 mmol), and SPhos (24 mmol) were added to a three-necked flask and Ar displacement was performed. Then, 1000 mL of toluene was added, and the mixture was stirred at 100 °C for 5 hours. Water was added to the reaction mixture, and the organic layer was extracted with toluene. The organic layer was dried over magnesium sulfate, and the solvent was removed under reduced pressure. The crude product was purified by silica gel column chromatography (a mixture of hexane / toluene (v / v 2:1)) and recrystallization (a mixture of ethanol / toluene (v / v 4:1)) to obtain 79 mmol of white solid (yield: 66%). The molecular weight of the purified product was determined by FAB-MS to be 546 g / mol, indicating the yield of the target intermediate compound B-4-5.
[0562] Synthesis of intermediate compound B-4-7
[0563] Intermediate compounds B-4-5 (79 mmol), B-4-6 (79 mmol), K₂CO₃ (790 mmol), and CuI (79 mmol) were added to a three-necked flask and Ar-substituted. The mixture was stirred at 210 °C for 36 h. Water was added to the reaction mixture, and the organic layer was extracted with toluene. The organic layer was dried over magnesium sulfate, and the solvent was removed under reduced pressure. The crude product was purified by silica gel column chromatography (a mixture of hexane and toluene (v / v 2:1)) and recrystallization (a mixture of ethanol and toluene (v / v 4:1)) to obtain 26 mmol of white solid (yield: 33%). The molecular weight of the purified product was determined by FAB-MS to be 1166 g / mol, indicating the yield of the target intermediate compound B-4-7.
[0564] Synthesis of fused polycyclic compound B-4
[0565] Intermediate compound B-4-7 (26 mmol) was added to a three-necked flask and Ar was substituted. Then, 60 mL of ODCB was added and dissolved, followed by the addition of BI3 (104 mmol). The mixture was stirred at 140 °C for 4 hours. The reaction solution was dispersed and washed with a large amount of acetonitrile, and the solid was collected by filtration. The obtained crude product was purified by silica gel column chromatography (a mixture of hexane / dichloromethane (v / v 2:1)) and recrystallization (a mixture of ethanol / toluene (v / v 4:1)) to obtain 9 mmol of yellow solid (yield: 35%). The molecular weight of the purified product was determined by FAB-MS to be 1181 g / mol, indicating the acquisition of the target fused polycyclic compound B-4.
[0566] (3) Synthesis of fused polycyclic compound C-3
[0567] The fused polycyclic compound C-3 was synthesized using the process described in reaction formula 3.
[0568] Reaction 3
[0569]
[0570]
[0571] Synthesis of intermediate compound C-3-3
[0572] Intermediate compounds C-3-1 (400 mmol), C-3-2 (200 mmol), K₂CO₃ (400 mmol), and CuI (200 mmol) were added to a three-necked flask and Ar-substituted. The mixture was stirred at 210 °C for 36 h. Water was added to the reaction mixture, and the organic layer was extracted with toluene. The organic layer was dried over magnesium sulfate, and the solvent was removed under reduced pressure. The crude product was purified by silica gel column chromatography (a mixture of hexane and toluene (v / v 2:1)) and recrystallization (a mixture of ethanol and toluene (v / v 4:1)) to obtain 87 mmol of white solid (yield: 44%). The molecular weight of the purified product was determined by FAB-MS to be 360 g / mol, indicating the acquisition of the target intermediate compound C-3-3.
[0573] Synthesis of intermediate compound C-3-5
[0574] Intermediate compounds C-3-3 (87 mmol), C-3-4 (87 mmol), tBuONa (261 mmol), Pd(dba)2 (9 mmol), and SPhos (18 mmol) were added to a three-necked flask and Ar displacement was performed. Then, 500 mL of toluene was added, and the mixture was stirred at 100 °C for 2 hours. Water was added to the reaction mixture, and the organic layer was extracted with toluene. The organic layer was dried over magnesium sulfate, and the solvent was removed under reduced pressure. The crude product was purified by silica gel column chromatography (a mixture of hexane / toluene (v / v 2:1)) and recrystallization (a mixture of ethanol / toluene (v / v 4:1)) to obtain a white solid of 60 mmol (yield: 69%). The purified product was determined to have a molecular weight of 600 g / mol by FAB-MS, indicating the yield of the target intermediate compound C-3-5.
[0575] Synthesis of intermediate compound C-3-7
[0576] Intermediate compounds C-3-5 (60 mmol), C-3-6 (30 mmol), K₂CO₃ (300 mmol), and CuI (60 mmol) were added to a three-necked flask and Ar-substituted. The mixture was stirred at 210 °C for 96 h. Water was added to the reaction mixture, and the organic layer was extracted with toluene. The organic layer was dried over magnesium sulfate, and the solvent was removed under reduced pressure. The crude product was purified by silica gel column chromatography (a mixture of hexane and toluene (v / v 2:1)) and recrystallization (a mixture of ethanol and toluene (v / v 4:1)) to obtain 29 mmol of white solid (yield: 48%). The molecular weight of the purified product was determined by FAB-MS to be 1274 g / mol, indicating the yield of the target intermediate compound C-3-7.
[0577] Synthesis of intermediate compound C-3-8
[0578] Intermediate compound C-3-7 (29 mmol) was added to a three-necked flask and Ar was substituted. Then, 20 mL of ODCB was added and dissolved, followed by the addition of BI3 (76 mmol). The mixture was stirred at 140 °C for 5 hours. The reaction solution was dispersed and washed with a large amount of acetonitrile, and the solid was collected by filtration. The obtained crude product was purified by silica gel column chromatography (a mixture of hexane / dichloromethane (v / v 2:1)) and recrystallization (a mixture of ethanol / toluene (v / v 4:1)) to obtain 18 mmol of yellow solid (yield: 62%). The purified product was determined to have a molecular weight of 1290 g / mol by FAB-MS, indicating the acquisition of the target intermediate compound C-3-8.
[0579] Synthesis of fused polycyclic compound C-3
[0580] Intermediate compound C-3-8 (18 mmol) and CuCN (72 mmol) and NMP (10 mL) were added to a three-necked flask and Ar was substituted. The mixture was stirred at 180 °C for 5 h. Water was added to the reaction mixture, and the organic layer was extracted with toluene. The organic layer was dried over magnesium sulfate and the solvent was removed under reduced pressure. The crude product was purified by silica gel column chromatography (a mixture of hexane / toluene (v / v 2:1)) and recrystallization (a mixture of ethanol / toluene (v / v 4:1)) to obtain 5 mmol of white solid (yield: 28%). The molecular weight of the purified product was determined by FAB-MS to be 1271 g / mol, indicating the acquisition of the target fused polycyclic compound C-3.
[0581] (4) Synthesis of fused polycyclic compound G-1
[0582] The fused polycyclic compound G-1 was synthesized using the process described in reaction formula 4.
[0583] Reaction 4
[0584]
[0585]
[0586]
[0587] Synthesis of intermediate compound G-1_L_3
[0588] Intermediate compounds G-1_L_1 (200 mmol), G-1_L_2 (200 mmol), tBuONa (220 mmol), Pd(dba)2 (30 mmol), and SPhos (30 mmol) were added to a three-necked flask and Ar displacement was performed. Then, 1000 mL of toluene was added, and the mixture was stirred at 80 °C for 5 hours. Water was added to the reaction mixture, and the organic layer was extracted with toluene. The organic layer was dried over magnesium sulfate, and the solvent was removed under reduced pressure. The obtained crude product was purified by silica gel column chromatography (a mixture of hexane / toluene (v / v 2:1)) and recrystallization (a mixture of ethanol / toluene (v / v 4:1)) to obtain 140 mmol of white solid (yield: 70%). The molecular weight of the purified product was determined by FAB-MS to be 398 g / mol, indicating the yield of the target intermediate compound G-1_L_3.
[0589] Synthesis of intermediate compound G-1_L_6
[0590] Intermediate compounds G-1_L_4 (200 mmol), G-1_L_5 (210 mmol), and Cs₂CO₃ (420 mmol) were added to a three-necked flask and Ar displacement was performed. Then, 600 mL of NMP was added, and the mixture was stirred at 120 °C for 5 h. Water was added to the reaction mixture, and the organic layer was extracted with toluene. The organic layer was dried over magnesium sulfate, and the solvent was removed under reduced pressure. The crude product was purified by silica gel column chromatography (a mixture of hexane / toluene (v / v 2:1)) and recrystallization (a mixture of ethanol / toluene (v / v 4:1)) to obtain a white solid of 167 mmol (yield: 84%). The purified product was determined to have a molecular weight of 360 g / mol by FAB-MS, indicating the acquisition of the target intermediate compound G-1_L_6.
[0591] Synthesis of intermediate compound G-1_L
[0592] Intermediate compounds G-1_L_6 (140 mmol), G-1_L_3 (140 mmol), tBuONa (220 mmol), Pd(dba)2 (20 mmol), and SPhos (30 mmol) were added to a three-necked flask and Ar displacement was performed. Then, 1000 mL of toluene was added, and the mixture was stirred at 100 °C for 12 h. Water was added to the reaction mixture, and the organic layer was extracted with toluene. The organic layer was dried over magnesium sulfate, and the solvent was removed under reduced pressure. The crude product was purified by silica gel column chromatography (a mixture of hexane / toluene (v / v 2:1)) and recrystallization (a mixture of ethanol / toluene (v / v 4:1)) to obtain 110 mmol of white solid (yield: 79%). The molecular weight of the purified product was determined by FAB-MS to be 676 g / mol, indicating the yield of the target intermediate compound G-1_L.
[0593] Synthesis of intermediate compound G-1_R_3
[0594] Intermediate compounds G-1_R_1 (200 mmol), G-1_R_2 (210 mmol), and Cs₂CO₃ (420 mmol) were added to a three-necked flask and Ar displacement was performed. Then, 500 mL of NMP was added, and the mixture was stirred at 120 °C for 2 hours. Water was added to the reaction mixture, and the organic layer was extracted with toluene. The organic layer was dried over magnesium sulfate, and the solvent was removed under reduced pressure. The crude product was purified by silica gel column chromatography (a mixture of hexane / toluene (v / v 2:1)) and recrystallization (a mixture of ethanol / toluene (v / v 4:1)) to obtain 134 mmol of white solid (yield: 67%). The purified product was determined to have a molecular weight of 401 g / mol by FAB-MS, indicating the acquisition of the target intermediate compound G-1_R_3.
[0595] Synthesis of intermediate compound G-1_R
[0596] Intermediate compounds G-1_R_3 (134 mmol), G-1_R_4 (134 mmol), tBuONa (201 mmol), Pd(dba)2 (30 mmol), and SPhos (30 mmol) were added to a three-necked flask and Ar displacement was performed. Then, 1000 mL of toluene was added, and the mixture was stirred at 100 °C for 3 hours. Water was added to the reaction mixture, and the organic layer was extracted with toluene. The organic layer was dried over magnesium sulfate, and the solvent was removed under reduced pressure. The crude product was purified by silica gel column chromatography (a mixture of hexane / toluene (v / v 2:1)) and recrystallization (a mixture of ethanol / toluene (v / v 4:1)) to obtain 120 mmol of white solid (yield: 90%). The molecular weight of the purified product was determined by FAB-MS to be 566 g / mol, indicating the yield of the target intermediate compound G-1_R.
[0597] Synthesis of intermediate compound G-1_1
[0598] Intermediate compounds G-1_L (110 mmol), G-1_R (110 mmol), tBuONa (220 mmol), Pd(dba)2 (20 mmol), and SPhos (30 mmol) were added to a three-necked flask and Ar displacement was performed. Then, 1000 mL of toluene was added, and the mixture was stirred at 120 °C for 8 hours. Water was added to the reaction mixture, and the organic layer was extracted with toluene. The organic layer was dried over magnesium sulfate, and the solvent was removed under reduced pressure. The crude product was purified by silica gel column chromatography (a mixture of hexane / toluene (v / v 2:1)) and recrystallization (a mixture of ethanol / toluene (v / v 4:1)) to obtain a white solid of 66 mmol (yield: 60%). The molecular weight of the purified product was determined by FAB-MS to be 1206 g / mol, indicating the yield of the target intermediate compound G-1_1.
[0599] Synthesis of fused polycyclic compound G-1
[0600] Intermediate compound G-1_1 (66 mol) was added to a three-necked flask and Ar was substituted. Then, 50 mL of ODCB was added and dissolved, followed by the addition of BI3 (264 mmol). The mixture was stirred at 140 °C for 5 hours. The reaction solution was dispersed and washed with a large amount of acetonitrile, and the solid was collected by filtration. The crude product was purified by silica gel column chromatography (a mixture of hexane / dichloromethane (v / v 2:1)) and recrystallization (a mixture of ethanol / toluene (v / v 4:1)) to obtain 34 mmol of a yellow solid (yield: 52%). The purified product was determined to have a molecular weight of 1221 g / mol by FAB-MS, indicating the acquisition of the target fused polycyclic compound G-1.
[0601] 2. Evaluation of compounds
[0602] Table 1 shows the evaluation results of the example compounds and comparative example compounds. Fused polycyclic compounds D-4, B-4, C-3, and G-1, which are fused polycyclic compounds represented by Formula 1 according to one or more embodiments, were evaluated as example compounds. Comparative example compounds X-1 to X-9 were used as comparative example compounds.
[0603] Example Compounds
[0604]
[0605] Comparative compounds
[0606]
[0607]
[0608] In Table 1, the maximum emission wavelength (λ) max λ is the wavelength measured at the point of maximum emission intensity in the emission spectrum, and the fluorescence quantum yield is the ratio of the number of emitted quanta to the number of absorbed quanta. In Table 1, λ max The fluorescence emission spectra were determined using a JASCO V-670 spectrometer after a doped film containing 20 wt% of the example or comparative example compounds on a PPF matrix was formed on quartz glass by deposition. The fluorescence quantum yield was measured using a JASCO ILF-835 integrating sphere system.
[0609]
[0610] Table 1
[0611]
[0612] Refer to λ in Table 1 max It was observed that comparative examples X-1 to X-9, as well as fused polycyclic compounds D-4, B-4, C-3, and G-1, emitted light with maximum emission wavelengths in the wavelength range of 440 nm to 490 nm. It was also observed that, compared to comparative examples X-1 to X-9, fused polycyclic compounds D-4, B-4, C-3, and G-1 exhibited high fluorescence quantum yields. This indicates that fused polycyclic compounds D-4, B-4, C-3, and G-1 demonstrate superior luminescent efficiency.
[0613] Fused polycyclic compounds D-4, B-4, C-3, and G-1 are fused polycyclic compounds of Formula 1 according to one or more embodiments, wherein the benzene ring bonded to at least two nitrogen atoms contains at least four substituted or unsubstituted phenyl groups as substituents, and the benzene ring bonded to two boron atoms each independently includes a substituted or unsubstituted phenyl group bonded at the para or adjacent para position to the carbon atom connected to the boron atom. The adjacent para position refers to the ortho or meta position. For example, the benzene ring bonded to the two boron atoms may each independently include a substituted or unsubstituted phenyl group bonded at the para and / or meta position to the boron atom. The two nitrogen atoms and the two boron atoms are cyclizing atoms in a fused ring with nine rings as the core structure. Accordingly, it is observed that the fused polycyclic compounds of Formula 1 according to one or more embodiments can exhibit excellent material stability and contribute to improving the luminous efficiency and lifespan of light-emitting elements (EDs).
[0614] Comparative example compounds X-1 to X-9 comprise a fused ring structure with nine rings as the core, and each benzene ring is independently bonded to a nitrogen atom and a boron atom in the core structure. However, unlike the fused polycyclic compounds according to one or more embodiments, the benzene rings bonded to at least two nitrogen atoms do not include at least four substituted or unsubstituted phenyl groups as substituents, the benzene rings bonded to boron atoms do not independently include substituted or unsubstituted phenyl groups as substituents, or the compounds include a carbazoyl group at a specific position. Accordingly, comparative example compounds X-1 to X-9 exhibit relatively low fluorescence quantum yields.
[0615] 3. Fabrication and evaluation of light-emitting elements
[0616] (1) Fabrication of light-emitting elements
[0617] Light-emitting elements comprising fused polycyclic compounds or comparative example compounds represented by Formula 1 according to one or more embodiments were prepared by the following method. Light-emitting elements of Examples 1 to 4 were prepared using fused polycyclic compounds represented by Formula 1, with fused polycyclic compounds D-4, B-4, C-3, and G-1 as dopant materials for the emission layer. Light-emitting elements of Comparative Examples 1 to 9 were prepared using comparative example compounds X-1 to X-9 as dopant materials for the emission layer. Light-emitting elements having the following layer structures were prepared and evaluated.
[0618] [Layer Structure] ITO / HAT-CN (10 nm) / α-NPD (40 nm) / mCBP (5 nm) / 1wt% dopant:mCBP (20 nm) / TPBi (30 nm) / Liq (0.5 nm) / Al (100 nm)
[0619] Specifically, as the first electrode, ITO with a thickness of 1500 Å was patterned on a glass substrate, rinsed with deionized (DI) water, and treated with UV ozone for 10 minutes. Subsequently, a hole injection layer with a thickness of 100 Å was formed using HAT-CN, and a hole transport layer with a thickness of 400 Å was formed using α-NPD.
[0620] Then, an electron blocking layer with a thickness of 50 Å was formed using mCBP, and an emission layer was formed by providing the respective example compounds (or comparative example compounds) and mCBP at a weight ratio of 1:99. The emission layer was formed to have a thickness of 200 Å. On the emission layer, an electron transport layer with a thickness of 300 Å was formed using TPBi, and an electron injection layer with a thickness of 5 Å was formed using Liq.
[0621] Then, a second electrode with a thickness of 1000 Å is formed using aluminum (Al). In this embodiment, a hole injection layer, a hole transport layer, an electron blocking layer, an emission layer, an electron transport layer, an electron injection layer, and a second electrode are formed using a vacuum deposition apparatus.
[0622] Materials used in the fabrication of light-emitting elements
[0623]
[0624] (2) Evaluation of light-emitting elements
[0625] Table 2 below shows the evaluation results of the light-emitting elements of the embodiments and comparative examples. In Table 2, EQE max Indicates the maximum external quantum efficiency (%), and LT 50 Indicates the relative component lifespan (%) when the half-life of Comparative Example 3 is set to 100%.
[0626] In Table 2, the voltage and current density of the light-emitting element were measured using a source meter (Keithley Instruments, 2400 series), and the luminance and maximum external quantum efficiency were measured using an external quantum efficiency measurement device (Hamamatsu Photonics, C9920-12).
[0627] Table 2
[0628]
[0629] Referring to Table 2, it can be seen that the light-emitting elements of the comparative examples and embodiments emit light having a maximum emission wavelength in the wavelength range of 440 nm to 490 nm. It can be seen that, compared with the light-emitting elements of Comparative Examples 1 to 7 and Comparative Example 9, the light-emitting elements of Examples 1 to 4 exhibit high element stability, high luminous efficiency, and long element lifespan. It can be seen that, compared with the light-emitting element of Comparative Example 8, the light-emitting elements of Examples 1 to 4 exhibit a long element lifespan. The light-emitting elements of Examples 1 to 4 include fused polycyclic compounds D-4, B-4, C-3, and G-1, and fused polycyclic compounds D-4, B-4, C-3, and G-1 are fused polycyclic compounds represented by Formula 1 according to one or more embodiments.
[0630] Fused polycyclic compounds D-4, B-4, C-3, and G-1 are fused polycyclic compounds of Formula 1 according to one or more embodiments, wherein the benzene ring bonded to at least two nitrogen atoms in the core structure contains at least four substituted or unsubstituted phenyl groups as substituents, and the benzene ring bonded to two boron atoms each independently contains substituted or unsubstituted phenyl groups as substituents. The core structure is a fused ring of nine rings containing two boron atoms, at least two nitrogen atoms, and at least one oxygen or sulfur atom as cyclic atoms. Accordingly, it is observed that the fused polycyclic compounds according to one or more embodiments can exhibit excellent material stability and contribute to improving the luminous efficiency and lifespan of light-emitting elements.
[0631] The light-emitting elements of Comparative Examples 1 to 9 each comprise comparative example compounds X-1 to X-9. Unlike the fused polycyclic compounds of Formula 1 according to one or more embodiments, comparative example compounds X-1 to X-4 have a smaller number of phenyl groups protecting the entire molecule and do not include at least four substituted or unsubstituted phenyl groups on the benzene ring bonded to the nitrogen atom. Unlike the fused polycyclic compounds of Formula 1 according to one or more embodiments, comparative example compound X-5 does not include substituted or unsubstituted phenyl groups on the benzene ring bonded to the boron atom. Unlike the fused polycyclic compounds of Formula 1 according to one or more embodiments, comparative example compound X-6 includes a carbazole group at a specific position in the molecule.
[0632] Unlike the fused polycyclic compounds of Formula 1 according to one or more embodiments, Comparative Compound X-7 includes a phenyl group and a carbazole group on the benzene ring bonded to a boron atom. Unlike the fused polycyclic compounds of Formula 1 according to one or more embodiments, Comparative Compounds X-8 and X-9 do not include substituted or unsubstituted phenyl groups on the benzene ring bonded to a boron atom. Accordingly, the light-emitting elements of Comparative Examples 1 to 7 and Comparative Example 9 exhibit low element stability, low luminous efficiency, and short element lifespan, and the light-emitting element of Comparative Example 8 exhibits a short element lifespan.
[0633] Electronic devices according to one or more embodiments may include light-emitting elements. In the light-emitting elements according to one or more embodiments, the emitting layer may include a fused polycyclic compound represented by Formula 1. The fused polycyclic compound represented by Formula 1 according to one or more embodiments comprises a fused ring as a core structure containing nine rings with two boron atoms, at least two nitrogen atoms, and at least one oxygen or sulfur atom as cyclic atoms. Additionally, in the fused polycyclic compound represented by Formula 1 according to one or more embodiments, the benzene ring bonded to at least two nitrogen atoms of the core structure may include at least four substituted or unsubstituted phenyl groups as substituents. Furthermore, the benzene ring bonded to the two boron atoms may each independently include substituted or unsubstituted phenyl groups bonded to the boron atoms at the para or immediately adjacent para positions. The immediately adjacent para position refers to the ortho or meta position. For example, the benzene ring bonded to the two boron atoms may each independently include substituted or unsubstituted phenyl groups bonded to the para and / or meta positions of the boron atoms. Accordingly, the fused polycyclic compound represented by Formula 1 according to one or more embodiments can exhibit excellent material stability, and light-emitting elements comprising the fused polycyclic compound represented by Formula 1 according to one or more embodiments can exhibit improved luminous efficiency and long element life.
[0634] The light-emitting element and the electronic device including the light-emitting element according to one or more embodiments comprise a fused polycyclic compound represented by Formula 1 according to one or more embodiments, and may therefore exhibit high luminous efficiency and long element life.
[0635] Fused polycyclic compounds represented by Formula 1 according to one or more embodiments can help improve the luminous efficiency and lifespan of light-emitting elements.
[0636] In the foregoing description, embodiments of the present disclosure have been referred to. However, it will be understood by those skilled in the art or those of ordinary skill in the art that various modifications and changes can be made to the present disclosure, as long as such modifications and changes do not depart from the spirit and technical scope of the present disclosure as set forth in the claims.
[0637] Therefore, the technical scope of this disclosure is not limited to the content described in the detailed description of the specification, but should be determined by the claims.
Claims
1. A fused polycyclic compound, represented by Formula 1: Formula 1 in, In Equation 1, Y1 and Z1 are each independently a hydrogen atom, a deuterium atom, a cyano group, a nitro group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms. X1 to X4 are each independently O, S, or a group represented by Formula 2. At least two of X1 to X4 are groups represented by Formula 2. R0 to R 13 Each of the following groups is independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro 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 cyclic carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 30 cyclic carbon atoms, or a group represented by Formula 3. At least one of R1 to R4 is a group represented by Formula 3, and R 10 To R 13 At least one of them is a group represented by Formula 3: Formula 2 In Equation 2, R A To R E Each of the following groups is independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 cyclic carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 30 cyclic carbon atoms, or a group represented by Formula 3, and " "and" "Indicates the location to be connected," Formula 3 In Equation 3, R a To R e Each of the following groups is independently composed of a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro 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 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 cyclic carbon atoms, and " "Indicates the location to be connected," Wherein at least two of Equation 2, R A To R E It includes four or more substituted or unsubstituted benzene rings.
2. The fused polycyclic compound according to claim 1, wherein formula 1 is represented by any one of formulas 1-A1 to 1-A3: Formula 1-A1 Formula 1-A2 Formula 1-A3 in, In equations 1-A1 to 1-A3, m1 to m6 are each an independent integer selected from 0 to 5. R a1 To R a6 Each of the following groups is independently composed of a hydrogen atom, a deuterium atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms. X1 to X4, R0 to R 13 Y1 and Z1 are the same as those defined in claim 1.
3. The fused polycyclic compound according to claim 1, wherein formula 1 is represented by any one of formulas 1-B1 to 1-B3: Formula 1-B1 Formula 1-B2 Formula 1-B3 in, In equations 1-B1 to 1-B3, X 11 and X 12 Each can be either O or S independently. R 1A To R 1E and R 2A To R 2E Each of the following groups is independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 cyclic carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 30 cyclic carbon atoms, or a group represented by Formula 3. In R 1A To R 1E and R 2A To R 2E In formula 3, the number of substituents is 4 or greater, and R0 to R 13 Y1 and Z1 are the same as those defined in claim 1.
4. The fused polycyclic compound according to claim 1, wherein formula 2 is represented by any one of formulas 2-1 to 2-8: Equation 2-1 Equation 2-2 Equation 2-3 Equation 2-4 Formula 2-5 Formula 2-6 Formula 2-7 Formula 2-8 in, In equations 2-1 to 2-8, n1 to n15 are each an independent integer selected from 0 to 5. R b1 To R b15 Each of the following is independently composed of a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms. R A1 To R D1 Each is independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 10 cyclic carbon atoms, and " "and" "Indicates the location to be connected." 5. The fused polycyclic compound according to claim 4, wherein... Equation 2-1 is represented by one of 2-1A to 2-1C. Equation 2-2 is represented by one of 2-2A and 2-2B. Equation 2-3 is represented by one of 2-3A to 2-3G. Equation 2-4 is represented by one of 2-4A and 2-4B. Equation 2-5 is represented by one of 2-5A to 2-5D. Equation 2-6 is represented by 2-6A. Equation 2-7 is represented by 2-7A, and Equation 2-8 is represented by 2-8A: in, In 2-1A to 2-8A, " "and" "Indicates the location to be connected." 6. The fused polycyclic compound according to claim 1, wherein in formula 1, R1 to R4 and R 10 To R 13 The remaining groups that are not represented by Formula 3 are each independently either hydrogen atoms or deuterium atoms.
7. The fused polycyclic compound of claim 1, wherein the fused polycyclic compound comprises compounds from group 1: Compound group 1 。 8. A light-emitting element, comprising: First electrode; A second electrode disposed on the first electrode; as well as An emission layer disposed between the first electrode and the second electrode. The emission layer comprises, as a first compound, a fused polycyclic compound represented by Formula 1 as claimed in any one of claims 1 to 7.
9. The light-emitting element according to claim 8, wherein the emitting layer further comprises at least one of a second compound represented by formula HT-1, a third compound represented by formula ET-1, and a fourth compound represented by formula D-1: HT-1 in, In formula HT-1, A1 through A8 are each independently N or CR 51 , L1 is a directly linked, substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms. Y a For direct connection, CR 52 R 53 or SiR 54 R 55 , Ar1 is a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms. R 51 To R 55 Each of the following is independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted thio group, a substituted or unsubstituted oxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted boron group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 cyclic carbon atoms. R 51 To R 55 Each group may optionally bond to an adjacent group to form a ring. ET-1 In Equation ET-1, At least one of X1 to X3 is N, and the rest of X1 to X3 are CR. 56 , Each R 56 Independently comprising a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 cyclic carbon atoms. b1 to b3 are each an independent integer selected from 0 to 10. Ar2 to Ar4 are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms. L2 to L4 are each independently a directly linked, substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms. Formula D-1 In equation D-1, Q1 to Q4 are each independently C or N. The rings C1 to C4 are each independently a substituted or unsubstituted aliphatic hydrocarbon cyclic group having 5 to 30 cyclic carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 30 cyclic carbon atoms. L 11 To L 13 Each is independently a direct connection, , , , substituted or unsubstituted alkylene groups having 1 to 20 carbon atoms, substituted or unsubstituted arylene groups having 6 to 30 cyclic carbon atoms, or substituted or unsubstituted heteroarylene groups having 2 to 30 cyclic carbon atoms, and in L 11 To L 13 middle," "Indicates the sites connected to rings C1 through C4," b11 to b13 are each independently 0 or 1. R 61 To R 66 Each of the following groups is independently composed of a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted thio group, a substituted or unsubstituted oxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted boron group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 cyclic carbon atoms, and / or each is bonded to an adjacent group to form a ring. d1 to d4 are each an independent integer selected from 0 to 4.
10. An electronic device comprising a display module configured to provide an image. The display module includes: basal layer; A circuit layer disposed on the base layer; as well as A display element layer disposed on the circuit layer, wherein the display element layer includes a light-emitting element according to claim 8 or claim 9.
