Electronic device, light-emitting element, and polycyclic compound therefor
By using a polycyclic compound represented by Formula 1 as the emitting layer in the light-emitting element, the problems of insufficient luminous efficiency and lifespan in the prior art are solved, and a highly efficient and stable display effect is achieved.
Patent Information
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- SAMSUNG DISPLAY CO LTD
- Filing Date
- 2025-11-10
- Publication Date
- 2026-05-12
AI Technical Summary
In existing organic electroluminescent display devices, the luminous efficiency and lifespan need to be improved, making it difficult to achieve stable and efficient display.
By employing an emitting layer containing a polycyclic compound represented by Formula 1, the structure of the light-emitting element is improved, thereby enhancing luminous efficiency and lifespan.
This improves the luminous efficiency and lifespan of the light-emitting elements, resulting in excellent display quality.
Smart Images

Figure CN122010991A_ABST
Abstract
Description
[0001] Cross-reference to related applications
[0002] This application claims priority and benefit to Japanese Patent Application No. 2024-197105, filed on November 12, 2024, the entire disclosure of which is incorporated herein by reference. Background Technology
[0003] One or more embodiments of this disclosure relate to electronic devices, light-emitting elements, and polycyclic compounds for said light-emitting elements. Technical Field
[0004] Organic electroluminescent display devices have been developed as image display devices. These organic electroluminescent display devices include self-emissive display devices, which achieve display by recombination of holes and electrons injected from a first electrode and a second electrode, respectively, in an emitting layer, causing a light-emitting material containing an organic compound in the emitting layer to emit light.
[0005] To apply light-emitting elements to display devices, there is a desire to improve or enhance luminous efficiency and lifespan, and to develop materials for light-emitting elements that can stably or appropriately meet the requirements. For example, thermally activated delayed fluorescence (TADF) materials utilizing the delayed fluorescence phenomenon are under development. Summary of the Invention
[0006] One or more aspects of the embodiments of this disclosure relate to electronic devices that have excellent or suitable display quality by including light-emitting elements having improved or enhanced luminous efficiency and lifespan.
[0007] One or more aspects of the embodiments of this disclosure also relate to light-emitting elements having improved or enhanced luminous efficiency and lifespan.
[0008] One or more aspects of the embodiments of this disclosure also relate to polycyclic compounds that have improved or enhanced material lifespan.
[0009] Additional aspects of the implementation scheme will be set forth in part in the following description and will be partly apparent from the description, or may be learned by practice of the implementation scheme presented in this disclosure.
[0010] One or more embodiments of this disclosure provide an electronic device comprising a display panel including a plurality of light-emitting elements, and at least one of the plurality of light-emitting elements comprising a first electrode, a second electrode opposite (e.g. facing) the first electrode, and an emitting layer disposed or provided between the first electrode and the second electrode and comprising a polycyclic compound represented by Formula 1.
[0011] Formula 1
[0012] In Formula 1, rings a, b, c, d, and e can each be independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heterocycle containing heteroatoms other than boron atoms as cyclic atoms and having 2 to 30 cyclic carbon atoms, or can be bonded to adjacent groups to form a ring. In Formula 1, X1, X2, Z1, and Z2 can each be independently O, S, NR, etc. a or NR b And at least one of X1, X2, Z1, and Z2 can be NR. b R a It can be a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or it can be bonded to an adjacent group to form a ring, and R b It can be represented by Equation 2.
[0013] Formula 2
[0014] In Formula 2, R1 to R5 can each independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted amine group, a substituted or unsubstituted silyl 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 can be bonded to adjacent groups to form a ring, or can be represented by Formula 3. It can refer to the position to be connected, and at least two selected from R1 to R5 can be represented by Equation 3: Formula 3 .
[0015] In Formula 3, Q1 to Q5 can each independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, or bonded to adjacent groups to form a ring, and It could refer to the location to be connected.
[0016] In one or more embodiments, the electronic device may include a display device including a display panel, and the display device may include a first emitting region, a second emitting region, and a third emitting region, each of the first emitting region, the second emitting region, and the third emitting region emitting light in different wavelength regions and being distinguishable from each other in a plane (e.g., in a plan view), and the first emitting region, the second emitting region, and the third emitting region may each be a region emitting light generated in each of the plurality of light-emitting elements.
[0017] In one or more embodiments, the plurality of light-emitting elements may each include a first light-emitting element arranged to correspond to a first emission region, a second light-emitting element arranged to correspond to a second emission region, and a third light-emitting element arranged to correspond to a third emission region.
[0018] In one or more embodiments, the display device may include a plurality of display surfaces, each of which has a different primary display orientation or main display direction.
[0019] In one or more embodiments, the electronic device may include a plurality of independently controlled display devices, and at least one of the plurality of display devices may include the display panel.
[0020] In one or more embodiments, the electronic device may further include at least one selected from processor, memory, and power module.
[0021] In one or more embodiments, the electronic device may include the display panel and may be a television, monitor, billboard, personal computer, laptop computer, personal digital assistant, vehicle equipment, game console, smartphone, tablet terminal, smartwatch, or camera.
[0022] In one or more embodiments of this disclosure, the light-emitting element may include a first electrode, a second electrode opposite to the first electrode (e.g., facing the first electrode), and an emitting layer disposed or provided between the first electrode and the second electrode and comprising a first compound represented by Formula 1.
[0023] In one or more embodiments, Equation 2 can be represented by Equation 2-1.
[0024] Equation 2-1
[0025] In Formula 2-1, one or two of R2', R3', R4' and R5' can be represented by Formula 3, and the remainder can each independently be a hydrogen atom, a deuterium atom, or a substituted or unsubstituted alkyl group having one to 20 carbon atoms. In Formula 2-1, Q1 to Q5 can be the same as defined in Formula 3. It could refer to the location to be connected.
[0026] In one or more embodiments, at least one selected from X1, X2, and Z2 may be NR. b Furthermore, Z1, as well as X1, X2, and Z2 are not NR. b The remainder can be O, S, or NR independently. a R a and R b It can be the same as that defined in Equation 1.
[0027] In one or more embodiments, the first compound represented by Formula 1 may be represented by Formula 4.
[0028] Formula 4
[0029] In Equation 4, R6 to R 21 Each of these groups can be independently a hydrogen atom, a deuterium atom, a cyano group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 30 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 can be bonded to adjacent groups to form a ring. In Formula 4, X1, X2, Z1, and Z2 can be the same as those defined in Formula 1.
[0030] In one or more embodiments, the first compound represented by Formula 4 may be represented by any one of Formulas 5-1 to 5-3: Formula 5-1 , Formula 5-2 ,as well as Formula 5-3 .
[0031] In equations 5-1 to 5-3, X 11 X 12 and Z 12 They can be O, S, and NR independently. a or NR b Z 11 It can be O, S, or NR. a R a and R b The values can be the same as those defined in Equation 1, R1 to R5 can be the same as those defined in Equation 2, and R6 to R... 21 It can be the same as that defined in Equation 4.
[0032] In one or more embodiments, the first compound represented by Formula 4 may be represented by any one of Formulas 6-1 to 6-6.
[0033] Formula 6-1
[0034] Formula 6-2
[0035] Formula 6-3
[0036] Formula 6-4
[0037] Formula 6-5
[0038] Formula 6-6
[0039] In equations 6-1 to 6-6, X 21 X 22 Z 21 and Z 22 They can be O, S, or NR independently. a Selected from R a2 To R a5 At least one of them, selected from R b2 To R b5 At least one of and selected from R c2 To R c5 At least one of them can be independently represented by Equation 3, Ra2 To R a5 R b2 To R b5 and R c2 To R c5 The remainder not represented by Formula 3 may each 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 aryl group having 6 to 30 cyclic carbon atoms. In Formulas 6-1 to 6-6, Q 11 To Q 15 Q 21 To Q 25 and Q 31 To Q 35 Each group can be an independent hydrogen atom, deuterium atom, substituted or unsubstituted tert-butyl group, substituted or unsubstituted phenyl group, or can bond with adjacent groups to form a ring, R a It can be the same as defined in Equation 1, and R6 to R 21 It can be the same as that defined in Equation 4.
[0040] In one or more implementations, R6 to R 21 Each of these can be independently a hydrogen atom, a deuterium atom, a cyano group, a substituted or unsubstituted diphenylamine group, a substituted or unsubstituted propyl group, a substituted or unsubstituted tert-butyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted carbazole group, or a substituted or unsubstituted dibenzofuran group.
[0041] In one or more embodiments, at least one of the hydrogen atoms selected from the first compound represented by Formula 1 may be replaced by a deuterium atom.
[0042] In one or more embodiments, the emitting layer can emit blue light.
[0043] In one or more embodiments, the emitter layer may further comprise 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.
[0044] In one or more embodiments, the first compound may be represented by any of the compounds selected from compound group 1.
[0045] In one or more embodiments of this disclosure, the polycyclic compound may be represented by Formula 1.
[0046] In one or more embodiments of this disclosure, the display device may include a substrate layer, a circuit layer disposed or provided on the substrate layer, and a display element layer disposed or provided on the circuit layer and including a light-emitting element, wherein the light-emitting element may include a first electrode, a second electrode opposite to the first electrode (e.g., facing the first electrode), and an emitting layer disposed or provided between the first electrode and the second electrode and comprising a polycyclic compound represented by Formula 1.
[0047] In one or more embodiments, the light-emitting element can emit blue light. Attached Figure Description
[0048] The accompanying drawings are included to provide a further understanding of embodiments of the subject matter of this disclosure, and are incorporated in and form part of this specification. The drawings illustrate embodiments of the subject matter of this disclosure and, together with the description, serve to explain the principles of embodiments of the subject matter of this disclosure. In the drawings: Figure 1 It is a block diagram of an electronic device according to one or more implementation schemes; Figure 2 It is a schematic diagram of an electronic device according to one or more implementation schemes; Figure 3 This is a plan view illustrating a display device according to one or more embodiments; Figure 4 This is an example showing along Figure 1 The cross-sectional view of the portion intercepted by line I-I' in the middle; Figure 5 It is a schematic illustration of a cross-sectional view of a light-emitting element according to one or more embodiments; Figure 6 It is a schematic illustration of a cross-sectional view of a light-emitting element according to one or more embodiments; Figure 7 It is a schematic illustration of a cross-sectional view of a light-emitting element according to one or more embodiments; Figure 8 It is a schematic illustration of a cross-sectional view of a light-emitting element according to one or more embodiments; Figure 9 It is a schematic illustration of a cross-sectional view of a light-emitting element according to one or more embodiments; Figure 10 This is a cross-sectional view illustrating a display device according to one or more embodiments; Figure 11 This is a cross-sectional view illustrating a display device according to one or more embodiments; Figure 12 This is a cross-sectional view illustrating a display device according to one or more embodiments; Figure 13 This is a cross-sectional view illustrating a display device according to one or more embodiments; Figure 14 It is a perspective view of an electronic device according to one or more implementation schemes; Figure 15 It is a perspective view of an electronic device according to one or more embodiments; and Figure 16 This is an example of a view of the interior of a vehicle in which a display device is provided according to one or more embodiments. Detailed Implementation
[0049] The subject matter of this disclosure may be modified in one or more suitable ways and has one or more suitable forms, and therefore exemplary embodiments will be illustrated in the accompanying drawings and described in more detail in the detailed description of this disclosure. However, it should be understood that it is not intended to limit this disclosure to the specific form disclosed, but rather to cover all modifications, equivalents, and substitutions falling within the spirit and scope of this disclosure.
[0050] When interpreting each figure (for example, when interpreting each figure), the same reference numerals are used to refer to the same elements.
[0051] In the accompanying drawings, the dimensions of each structure are illustrated in enlarged form for clarity of this disclosure.
[0052] When describing an implementation of this disclosure (e.g., when describing an implementation of this disclosure), the use of "may" means "one or more implementations of this disclosure".
[0053] In the context of this application and unless otherwise defined, the terms “use,” “using,” and “used” may be considered synonymous with the terms “utilize,” “utilizing,” and “utilized,” respectively.
[0054] As used herein, the terms “substantially,” “about,” or similar terms are used as terms of approximation rather than terms of degree, and are intended to account for inherent biases in measured or calculated values that would be recognized by a person skilled in the art. As used herein, “about” includes a specified value and refers to an acceptable range of deviations from a specific value as determined by a person skilled in the art considering the relevant measurement and errors associated with the measurement of the specific quantity (e.g., limitations of the measurement system). For example, “about” could mean within one or more standard deviations of the specified value, or within ±30%, ±20%, ±10%, or ±5% of the specified value. Furthermore, it should be understood that even if the terms “about,” “approximately,” or “substantially” are not explicitly stated in a given element (e.g., a claim element), such a range is intended to include non-substantial variations or variations as understood by a person skilled in the art. For example, the numerical values and ranges provided herein are intended to include tolerances and measurement uncertainties that would be recognized by a person skilled in the art, and elements (e.g., claim elements) should be interpreted accordingly to cover such equivalences.
[0055] Any numerical ranges listed herein are intended to include all subranges of substantially the same numerical precision falling within the listed range. For example, the range “1.0 to 10.0” is intended to include all subranges between the listed minimum value of 1.0 and the listed maximum value of 10.0 (and including endpoints), such as having a minimum value equal to or greater than 1.0 and a maximum value equal to or less than 10.0, such as 2.4 to 7.6. Any maximum numerical limit listed herein is intended to include all smaller numerical limits falling within it, and any minimum numerical limit listed in this specification is intended to include all larger numerical limits falling within it. Therefore, the applicant reserves the right to modify this disclosure (including the appended claims) to expressly list any subranges falling within the scope expressly listed herein.
[0056] It should be understood that although the terms “first,” “second,” etc., may be used herein to describe one or more suitable components, these components should not be limited by these terms. These terms are used only to distinguish one component from another. For example, without departing from the scope of one or more embodiments of this disclosure, a first component may be referred to as a second component, and similarly, a second component may be referred to as a first component.
[0057] As used herein, the singular forms “a”, “an”, and “the” are intended to also include the plural forms unless the context clearly indicates otherwise.
[0058] In this application, it should be understood that the terms "include," "have," "including," "having," etc., indicate the presence of features, numbers, steps, operations, components, parts, or combinations thereof disclosed in this specification, but do not exclude the presence or addition of one or more other features, numbers, steps, operations, components, parts, or combinations thereof. For example, it should be understood that the terms "comprise(s) / comprising," "include(s) / including," or "have / has / having" indicate the presence of specified features, numbers, steps, operations, elements, and / or components, but do not exclude the presence or addition of one or more other features, numbers, steps, operations, elements, components, and / or groups thereof. Furthermore, the terms “comprise(s) / comprising,” “include(s) / including,” “have / has / having,” or similar terms include or support the terms “composed of…” and “substantially composed of…”, indicating the presence of the specified feature, integer, step, operation, element, and / or component, while other features, integers, steps, operations, elements, components, and / or groups thereof are absent or substantially absent.
[0059] In this application, if a layer, film, region, or plate is referred to as being "on," "above," or "in the upper part" of another layer, film, region, or plate (e.g., when a layer, film, region, or plate is referred to as being "on," "above," or "in the upper part" of another layer, film, region, or plate), it may not only be "directly on" or "directly above" a layer, film, region, or plate, but there may also be intermediate layers, films, regions, or plates therein. Conversely, if a layer, film, region, or plate is referred to as "directly on" another layer, film, region, or plate" or "directly above" another layer, film, region, or plate (e.g., when a layer, film, region, or plate is referred to as "directly on" another layer, film, region, or plate" or "directly above" another layer, film, region, or plate), then there are no intermediate layers, films, regions, or plates therein.
[0060] If a layer, membrane, zone, or plate is referred to as being "below" or "in the lower part" of another layer, membrane, zone, or plate (e.g., when a layer, membrane, zone, or plate is referred to as being "below" or "in the lower part" of another layer, membrane, zone, or plate), it may not only be directly below the layer, membrane, zone, or plate, but may also have intermediate layers, membranes, zones, or plates in between.
[0061] It should be understood that if a component is referred to as being "on" another component (for example, when a component is referred to as being "on" another component), it can be set or provided above the other component, or it can also be set or provided below the other component.
[0062] In the context of this disclosure and unless otherwise defined, a plan view is an orthogonal projection of a three-dimensional object onto a horizontal plane intersecting the object. For example, it is a top view showing the layout and spatial relationships of one or more elements within an object or structure. A plan view based on the z-axis (thickness) direction refers to a top view of the object as if looking directly down at the surface from above (e.g., when looking directly down at the surface from above). In this document, the z-axis direction is perpendicular or orthogonal to the horizontal plane defined by the x-axis and y-axis directions.
[0063] In this specification, the term "substituted or unsubstituted" means substituted or unsubstituted by at least one substituent selected from the group consisting of deuterium, halogen, cyano, nitro, amino, silyl, oxy, thio, sulfinyl, sulfonyl, carbonyl, boron, phosphine oxide, phosphine sulfide, alkyl, alkenyl, alkynyl, cyclic, aryl, and heterocyclic groups. In one or more embodiments, each of the substituents exemplified herein may be substituted or unsubstituted. For example, a biphenyl group may be interpreted as an aryl group or a phenyl group substituted with a phenyl group.
[0064] In the specification, the phrase "bonded to an adjacent group to form a ring" can refer to a group bonding to an adjacent group to form a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocycle. The hydrocarbon ring can include aliphatic hydrocarbon rings and aromatic hydrocarbon rings. The heterocycle can include aliphatic heterocycles and aromatic heterocycles. The hydrocarbon ring and heterocycle can be monocyclic or polycyclic. In one or more embodiments, a ring formed by bonding to each other can be attached to another ring to form a spirocyclic structure.
[0065] In this specification, the term "adjacent group" can 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 located at the position closest to the corresponding substituent. For example, the two methyl groups in 1,2-dimethylbenzene can be interpreted as "adjacent groups" to each other, and the two ethyl groups in 1,1-diethylcyclopentane can be interpreted as "adjacent groups" to each other. In one or more embodiments, the two methyl groups in 4,5-dimethylphenanthrene can be interpreted as "adjacent groups" to each other.
[0066] In the specification, examples of halogen atoms may include fluorine atoms, chlorine atoms, bromine atoms, or iodine atoms.
[0067] In the specification, the alkyl group can be straight-chain or branched. The number of carbon atoms in the alkyl group can be 1 to 60, 1 to 50, 1 to 30, 1 to 20, 1 to 10, or 1 to 6. Examples of alkyl groups may include methyl groups, ethyl groups, n-propyl groups, isopropyl groups, n-butyl groups, sec-butyl groups, tert-butyl groups, isobutyl groups, 2-ethylbutyl groups, 3,3-dimethylbutyl groups, n-pentyl groups, isopentyl groups, neopentyl groups, tert-pentyl groups, 1-methylpentyl groups, 3-methylpentyl groups, 2-ethylpentyl groups, 4-methyl-2-pentyl groups, n-hexyl groups, 1-methylhexyl groups, 2-ethyl... Hexyl group, 2-butylhexyl group, n-heptyl group, 1-methylheptyl group, 2,2-dimethylheptyl group, 2-ethylheptyl group, 2-butylheptyl group, n-octyl group, tert-octyl group, 2-ethyloctyl group, 2-butyloctyl group, 2-hexyloctyl group, 3,7-dimethyloctyl group, n-nonyl group, n-decyl group, 2-ethyldecyl group, 2-butyldecyl group, 2-hexyldecyl group, 2-octyldecyl group Undecyl group, dodecyl group, 2-ethyldodecyl group, 2-butyldodecyl group, 2-hexyldodecyl group, 2-octyldodecyl group, tridecyl group, tetradecyl group, pentadecyl group, hexadecyl group, 2-ethylhexadecyl group, 2-butylhexadecyl group, 2-hexylhexadecyl group, 2-octylhexadecyl group, heptadecanyl group, octadecyl group, nonadecanyl group, eicosyl group, 2-ethyleicosyl group, 2-butyleicosyl group, 2-hexyleicosyl group, 2-octyleicosyl group, dodecyl group, tridecyl group, tetradecyl group, pentadecyl group, hexadecyl group, heptadecanyl group, octadecyl group, nonadecanyl group, triadecyl group, etc., but the embodiments of the present disclosure are not limited to these.
[0068] In this specification, a cycloalkyl group can refer to a cyclic alkyl group. The number of carbon atoms in a cycloalkyl group can be 3 to 50, 3 to 30, 3 to 20, or 3 to 10. Examples of cycloalkyl groups may include cyclopropyl groups, cyclobutyl groups, cyclopentyl groups, cyclohexyl groups, 4-methylcyclohexyl groups, 4-tert-butylcyclohexyl groups, cycloheptyl groups, cyclooctyl groups, cyclononyl groups, cyclodecyl groups, norbornyl groups, 1-adamantyl groups, 2-adamantyl groups, isobornyl groups, bicycloheptyl groups, etc., but the embodiments of this disclosure are not limited thereto.
[0069] In this specification, an alkenyl group can refer to a hydrocarbon group containing at least one carbon-carbon double bond at the middle or 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 can be 2 to 60, 2 to 30, 2 to 20, or 2 to 10. Examples of alkenyl groups include vinyl groups, 1-butenyl groups, 1-pentenyl groups, 1,3-butadienyl groups, styryl groups, styrylvinyl groups, etc., but embodiments of this disclosure are not limited thereto.
[0070] In this specification, an alkynyl group can refer to a hydrocarbon group containing at least one carbon-carbon triple bond at the middle or end of an alkyl group having two or more carbon atoms. The alkynyl group can be straight-chain or branched. Although the number of carbon atoms is not particularly limited, it can be 2 to 60, 2 to 30, 2 to 20, or 2 to 10. Examples of alkynyl groups may include ethynyl groups, propynyl groups, etc., but embodiments of this disclosure are not limited thereto.
[0071] In this specification, the hydrocarbon cyclic group can refer to any suitable functional group or substituent derived from an aliphatic hydrocarbon ring. The hydrocarbon cyclic group can be a saturated hydrocarbon cyclic group having 5 to 20 cyclic carbon atoms.
[0072] In this specification, an aryl group can refer to any suitable functional group or substituent derived from an aromatic hydrocarbon ring. An aryl group can be a monocyclic or polycyclic aryl group. The number of cyclic carbon atoms in an aryl group can be 6 to 60, 6 to 30, 6 to 20, or 6 to 15. Examples of aryl groups may include phenyl groups, naphthyl groups, fluorenyl groups, anthraceneyl groups, phenanthrene groups, biphenyl groups, triphenyl groups, tetraphenyl groups, pentaphenyl groups, hexaphenyl groups, benzo[a]phenanthrene groups, pyrene groups, benzo[a]fluorene anthracene groups, alkyl groups, etc., but the embodiments of this disclosure are not limited thereto.
[0073] In this specification, the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spirocyclic structure. Examples of substituted fluorenyl groups are as follows. However, embodiments of this disclosure are not limited thereto.
[0074]
[0075] In this document, a heterocyclic group can refer to any suitable 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 can include aliphatic heterocyclic groups and aromatic heterocyclic groups. Aromatic heterocyclic groups can be heteroaryl groups. Aliphatic and aromatic heterocycles can be monocyclic or polycyclic.
[0076] In the specification, the heterocyclic group may contain at least one of B, O, N, P, Si, and S as a heteroatom, wherein the number of heteroatoms may be 1 to 10, for example 1, 2, 3, 4, or 5. If the heterocyclic group contains two or more heteroatoms (e.g., when the heterocyclic group contains two or more heteroatoms), the two or more heteroatoms may be the same as or different from each other. The heterocyclic group may be a monocyclic heterocyclic group or a polycyclic heterocyclic group, and may include a heteroaryl group. 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.
[0077] In the specification, 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 30, 2 to 20, or 2 to 10. Examples of aliphatic heterocyclic groups may include oxetane groups, thiohexane groups, pyrrolidinyl groups, piperidinyl groups, tetrahydrofuran groups, tetrahydrothiophene groups, thiohexane groups, tetrahydropyran groups, 1,4-dioxane groups, etc., but the embodiments of this disclosure are not limited thereto.
[0078] In the specification, the heteroaryl group may contain at least one of B, O, N, P, Si, and S as a heteroatom. If the heteroaryl group contains two or more heteroatoms (e.g., when...), the two or more heteroatoms may be the same or different from each other. The heteroaryl group may be a monocyclic heterocyclic group or a polycyclic heterocyclic group. The number of cyclic carbon atoms in the heteroaryl group may be 2 to 30, 2 to 20, or 2 to 10. Examples of heteroaryl groups may include thiophene groups, furan groups, pyrrole groups, imidazole groups, pyridine groups, bipyridine groups, pyrimidine groups, triazine groups, triazole groups, acridine groups, pyridazine groups, pyrazine groups, quinoline groups, quinazoline groups, quinoxaline groups, phenoxazine groups, phthalazine groups, pyridopyrimidine groups, pyridopyrazine groups, pyrazinopyrazine groups, isoquinoline groups, indole groups, carbazole groups, N-arylcarbazole groups, N-heteroarylcarbazole group, N-alkylcarbazole group, benzoxazole group, benzimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, thiophene-thiophene group, benzofuran group, phenanthroline group, thiazole group, isoxazole group, oxazole group, oxadiazole group, thiadiazole group, phenothiazine group, dibenzothiophene group, dibenzofuran group, etc., but the embodiments disclosed herein are not limited to these.
[0079] In this specification, the description of aryl groups can be applied to arylene groups, but arylene groups are divalent groups. Similarly, the description of heteroaryl groups can be applied to heteroarylene groups, but heteroarylene groups are divalent groups.
[0080] In this specification, the silyl group may include alkylsilyl groups and arylsilyl groups. Examples of silyl groups may include trimethylsilyl groups, triethylsilyl groups, tert-butyldimethylsilyl groups, propyldimethylsilyl groups, triphenylsilyl groups, diphenylsilyl groups, phenylsilyl groups, etc., but the embodiments of this disclosure are not limited thereto.
[0081] In the specification, the number of carbon atoms in the carbonyl group is not particularly limited, but can be 1 to 40, 1 to 30, or 1 to 20. For example, the carbonyl group can have the following structure, but the embodiments of this disclosure are not limited thereto.
[0082]
[0083] In the specification, the number of carbon atoms in the sulfinyl group and sulfonyl group is not limited, but can be 1 to 30, 1 to 20, or 1 to 10. The sulfinyl group can include alkylsulfinyl groups and arylsulfinyl groups. The sulfonyl group can include alkylsulfonyl groups and arylsulfonyl groups.
[0084] In this specification, a thio group may include an alkylthio group and an arylthio group. A thio group may refer to a sulfur atom bonded to an alkyl group or an aryl group as defined herein. Examples of thio groups may include methylthio groups, ethylthio groups, propylthio groups, pentylthio groups, hexylthio groups, octylthio groups, dodecylthio groups, cyclopentylthio groups, cyclohexylthio groups, phenylthio groups, and naphthylthio groups, but embodiments of this disclosure are not limited thereto.
[0085] In this specification, an oxy group can refer to an oxygen atom bonded to an alkyl group or an aryl group as defined herein. Oxygen groups can include alkoxy groups and aryloxy groups. Alkoxy groups can be straight-chain, branched, or cyclic. The number of carbon atoms in an alkoxy group is not particularly limited, but can be, for example, 1 to 20 or 1 to 10. Examples of oxy groups can include methoxy groups, ethoxy groups, n-propoxy groups, isopropoxy groups, butoxy groups, pentoxy groups, hexoxy groups, octoxy groups, nonoxy groups, decoxy groups, benzyloxy groups, etc., but embodiments of this disclosure are not limited thereto.
[0086] In this document, a boron group can refer to a boron atom bonded to an alkyl group or an aryl group as defined herein. A boron group can include alkylboron groups and arylboron groups. Examples of boron groups include dimethylboron groups, diphenylboron groups, phenylboron groups, etc., but embodiments of this disclosure are not limited thereto.
[0087] In this specification, the number of carbon atoms in the amine group is not particularly limited, but can be 1 to 30, 1 to 20, or 1 to 10. The amine group can include alkylamine groups and arylamine groups. Examples of amine groups can include methylamine groups, dimethylamine groups, phenylamine groups, diphenylamine groups, naphthylamine groups, 9-methyl-anthraylamine groups, etc., but the embodiments of this disclosure are not limited thereto.
[0088] In this specification, the alkyl groups in alkylthio, alkylsulfonyloxy, alkylaryl, alkylamino, alkylboron, alkylsilyl, and alkylamine groups may be the same as the examples of alkyl groups described herein.
[0089] In this specification, the aryl groups in the aryloxy group, arylthio group, arylsulfonyloxy group, arylamino group, arylboronic group, arylsilyl group, and arylamine group may be the same as the aryl groups described herein.
[0090] In the specification, a direct bond can refer to a single bond (e.g., a single covalent bond).
[0091] In the instruction manual, " "and" "" refers to the position to be connected.
[0092] In the following, one or more embodiments of this disclosure will be described in more detail with reference to the accompanying drawings.
[0093] Figure 1 This is a block diagram of an electronic device according to one or more implementation schemes. (Reference) Figure 1 An electronic device EA according to one or more embodiments may include a display module 11, a processor 12, a memory 13, and a power module 14.
[0094] The processor 12 may include at least one selected from 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.
[0095] The memory 15 may store data information required or desired for the operation of the processor 12 or the display module 11. If the processor 12 executes an application stored in the memory 15 (e.g., when the processor 12 executes an application stored in the memory 15), video data signals and / or input control signals may be sent to the display module 11, and the display module 11 may process the provided signals to output video information through the display screen. The display module 11 may include a display panel for displaying video.
[0096] The power module 14 may include a power supply module, such as a power adapter and / or a battery device, and a power conversion module that converts the power supplied by the power supply module to generate the power required or desired for the operation of the electronic device EA.
[0097] At least one of the components selected from the electronic device EA as described in one or more embodiments may be included in the display panel according to one or more embodiments and the display device including the display panel according to one or more embodiments, which will be described in more detail herein. In one or more embodiments, one or more suitable separate modules functionally included in a module may be included in the display device, and one or more other modules may be provided separately from the display device. For example, the display device may include display module 11, processor 12, memory 13 and power module 14, and may be provided in the form of other means than the display device in the electronic device EA.
[0098] Figure 2 It is a schematic view of an electronic device according to one or more implementation schemes.
[0099] refer to Figure 2 Suitable electronic devices, including one or more display devices according to one or more embodiments, may include not only electronic devices for displaying images, such as smartphones 10_1a, tablet PCs 10_1b, laptops 10_1c, TVs 10_1d, desktop monitors 10_1e, etc., but also wearable electronic devices, such as smart glasses 10_2a, head-mounted displays 10_2b, smartwatches 10_2c, and electronic devices 10_3 for vehicles including display devices, such as central information displays (CIDs), central panels, or dashboards on instrument clusters of vehicles, and interior mirror displays.
[0100] Figure 3 This is a plan view illustrating one or more embodiments of the display device DD. Figure 4 This is a cross-sectional view of a display device DD with one or more implementation schemes. Figure 4 This is an example showing along Figure 3 A cross-sectional view of the portion cut off by line I-I'.
[0101] The display device DD may include a display panel DP and an optical layer PP disposed on or provided on the display panel DP. The display panel DP may include light-emitting elements ED-1, ED-2, and ED-3. The display device DD may include multiple light-emitting elements ED-1, ED-2, and ED-3. The optical layer PP may be disposed on or provided on the display panel DP to control reflected light from the display panel DP due to external light. The optical layer PP may include, for example, a polarizing layer and / or a color filter layer. In one or more embodiments, the optical layer PP may be omitted from the display device DD of one or more embodiments.
[0102] The substrate BL can be disposed or provided on the optical layer PP. The substrate BL can be a component on a substrate surface where the optical layer PP is disposed or provided. The substrate BL can be a glass substrate, a metal substrate, a plastic substrate, etc. However, embodiments of this disclosure are not limited thereto, and the substrate BL can be an inorganic layer, an organic layer, or a composite material layer. In one or more embodiments, the substrate BL may not be provided.
[0103] The display device DD according to one or more embodiments may further include a filler layer. The filler layer may be disposed or provided between the display device layer DP-ED and the substrate BL. The filler layer may be an organic material layer. The filler layer may contain at least one of acrylic-based resins, silicone-based resins, and epoxy-based resins.
[0104] The display panel DP may include a substrate layer BS, a circuit layer DP-CL provided on the substrate layer BS, and a display device layer DP-ED. The display device layer DP-ED may include a pixel defining film PDL, light-emitting elements ED-1, ED-2, and ED-3 disposed or provided between portions of the pixel defining film PDL, and an encapsulation layer TFE disposed or provided on the light-emitting elements ED-1, ED-2, and ED-3.
[0105] The substrate layer BS can be a component that provides a display device layer DP-ED or is provided on a substrate surface thereon. The substrate layer BS can be a glass substrate, a metal substrate, a plastic substrate, etc. However, embodiments of this disclosure are not limited thereto, and the substrate layer BS can be an inorganic layer, an organic layer, or an organic-inorganic composite material layer.
[0106] In one or more embodiments, the circuit layer DP-CL may be disposed or provided on the substrate BS, and the circuit layer DP-CL may include a plurality of transistors. Each of the transistors may include a control electrode, an input electrode, and an output electrode. For example, the circuit layer DP-CL may include a switching transistor and a driving transistor for driving the light-emitting elements ED-1, ED-2, and ED-3 of the display device layer DP-ED.
[0107] Each of the light-emitting elements ED-1, ED-2, and ED-3 may have the following characteristics, which will be described in more detail herein: Figures 3 to 6 The structure of each light-emitting element ED in one or more embodiments. Each of the light-emitting elements ED-1, ED-2 and ED-3 may 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.
[0108] Figure 4 An example is illustrated in which the emitting layers EML-R, EML-G, and EML-B of light-emitting elements ED-1, ED-2, and ED-3 are disposed or provided in openings OH defined in a pixel-defining film PDL, and the hole transport region HTR, electron transport region ETR, and second electrode EL2 are provided as one or more common layers in all light-emitting elements ED-1, ED-2, and ED-3. However, embodiments of this disclosure are not limited thereto, and the hole transport region HTR and electron transport region ETR in one or more embodiments can be provided by patterning within the openings OH defined in the pixel-defining film PDL. For example, 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 in one or more embodiments can be provided by patterning using inkjet printing.
[0109] The encapsulation layer TFE can cover the light-emitting elements ED-1, ED-2, and ED-3. The encapsulation layer TFE can seal the display device layer DP-ED. The encapsulation layer TFE can be a thin-film encapsulation layer. The encapsulation layer TFE can be formed or provided by laminating one or more layers. The encapsulation layer TFE may include at least one insulating (e.g., electrically insulating) layer. According to one or more embodiments, the encapsulation layer TFE may include at least one inorganic film (hereinafter, encapsulated inorganic film). According to one or more embodiments, the encapsulation layer TFE may also include at least one organic film (hereinafter, encapsulated organic film) and at least one encapsulated inorganic film.
[0110] Encapsulating inorganic films can protect the display device layer DP-ED from the effects of moisture / oxygen, while encapsulating organic films can protect the display device layer DP-ED from foreign substances such as dust particles. Encapsulating inorganic films may include silicon nitrides, silicon oxide nitrides, silicon oxides, titanium oxides, aluminum oxides, etc., but the embodiments of this disclosure are not limited to these. Encapsulating organic films may include acrylic-based compounds, epoxy-based compounds, etc. Encapsulating organic films may include photopolymerizable organic materials, but the embodiments of this disclosure are not limited to these.
[0111] The encapsulation layer TFE can be disposed or provided on the second electrode EL2 and can be disposed or provided as filling the opening OH.
[0112] refer to Figure 3 and Figure 4 The display device DD may include a non-emitting area NPXA and emitting areas PXA-R, PXA-G, and PXA-B. The emitting areas PXA-R, PXA-G, and PXA-B may be areas in which light generated by corresponding light-emitting elements ED-1, ED-2, and ED-3 is emitted. The emitting areas PXA-R, PXA-G, and PXA-B may be spaced apart and / or separated from each other in a plane (e.g., in a plan view).
[0113] Each of the light-emitting regions PXA-R, PXA-G, and PXA-B can 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 corresponding to the pixel-defining film PDL. In one or more 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 light-emitting elements ED-1, ED-2, and ED-3. The emitting layers EML-R, EML-G, and EML-B of light-emitting elements ED-1, ED-2, and ED-3 can be disposed or provided in openings OH defined in the pixel-defining film PDL and separated from each other.
[0114] Based on the color of the light produced by the light-emitting elements ED-1, ED-2, and ED-3, the light-emitting areas PXA-R, PXA-G, and PXA-B can be divided into multiple groups. (The remaining text appears to be incomplete and requires further context.) Figure 3 and Figure 4 In one or more embodiments of the device DD illustrated herein, three light-emitting regions PXA-R, PXA-G, and PXA-B, emitting red, green, and blue light respectively, are exemplified as examples. For instance, one or more embodiments of the display device DD may include red light-emitting region PXA-R, green light-emitting region PXA-G, and blue light-emitting region PXA-B, which are separated from each other.
[0115] In a display device DD according to one or more embodiments, multiple light-emitting elements ED-1, ED-2, and ED-3 can emit light beams having different wavelengths from each other. For example, in one or more embodiments, the display device DD 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. For example, 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 device DD may correspond to the first light-emitting element ED-1, the second light-emitting element ED-2, and the third light-emitting element ED-3, respectively.
[0116] However, embodiments of this disclosure are not limited thereto, and the first to third light-emitting elements ED-1, ED-2, and ED-3 may emit light beams within substantially the same wavelength range, or at least one light-emitting element may emit light beams 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.
[0117] According to one or more embodiments, the light-emitting areas PXA-R, PXA-G, and PXA-B in the display device DD can be arranged in a stripe pattern (e.g., essentially a stripe pattern). Reference Figure 3 Multiple 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. In one or more embodiments, 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.
[0118] Figure 3 and Figure 4 Examples show that all luminescent regions PXA-R, PXA-G, and PXA-B have similar areas, but embodiments of this disclosure are not limited thereto. Therefore, luminescent regions PXA-R, PXA-G, and PXA-B can have different areas depending on the wavelength range of the emitted light. In this case, the area of luminescent regions PXA-R, PXA-G, and PXA-B can refer to the area if observed in a plane defined by the first directional axis DR1 and the second directional axis DR2 (e.g., when observed in a plane defined by the first directional axis DR1 and the second directional axis DR2).
[0119] In one or more embodiments, the arrangement of the light-emitting regions PXA-R, PXA-G, and PXA-B is not limited to... Figure 3The configuration or arrangement illustrated herein, wherein the order in which the red emitting areas PXA-R, green emitting areas PXA-G, and blue emitting areas PXA-B are arranged, can be provided in one or more suitable combinations according to the characteristics of the desired or expected display quality in the display device DD. For example, the arrangement of the emitting areas PXA-R, PXA-G, and PXA-B can be pentiform. ® Arrangement (e.g., RGBG matrix, RGBG structure, or RGBG matrix structure) or diamond (DIAMOND PIXEL) ® Layout format. ® DIAMOND PIXEL is a registered trademark of Samsung Display Co., Ltd. ® It is a trademark of Samsung Display Co., Ltd.
[0120] In one or more embodiments, the areas of the luminescent regions PXA-R, PXA-G, and PXA-B may be different from each other. For example, in one or more embodiments, the area of the green luminescent region PXA-G may be smaller than the area of the blue luminescent region PXA-B, but the embodiments of this disclosure are not limited thereto.
[0121] In the following text, Figures 5 to 9 This is a schematic cross-sectional view illustrating a light-emitting element according to one or more embodiments. The light-emitting element ED according to one or more embodiments may include a first electrode EL1, a second electrode EL2 opposite to (e.g., facing the first electrode EL1), and an emission layer EML disposed or provided between the first electrode EL1 and the second electrode EL2. In one or more embodiments, the light-emitting element ED may include a hole transport region HTR or an electron transport region ETR between the first electrode EL1 and the emission layer EML and between the emission layer EML and the second electrode EL2. For example, the light-emitting element ED of one or more embodiments may include a first electrode EL1, a hole transport region HTR, an emission layer EML, an electron transport region ETR, and a second electrode EL2 stacked in sequence.
[0122] and Figure 5 compared to, Figure 6 This is a cross-sectional view of a light-emitting element (ED) according to one or more embodiments, 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). In one or more embodiments, with Figure 5 compared to, Figure 7This is a cross-sectional view of one or more embodiments of a light-emitting element (ED), wherein the hole transport region (HTR) includes a hole injection layer (HIL), a hole transport layer (HTL), and an emission auxiliary layer (EAL), and the electron transport region (ETR) includes an electron injection layer (EIL), an electron transport layer (ETL), and a hole blocking layer (HBL). Figure 6 compared to, Figure 8 This is a cross-sectional view of a light-emitting element (ED) according to one or more embodiments, 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 6 compared to, Figure 9 It is a cross-sectional view of an embodiment of a light-emitting element ED including one or more of a cover layer CPL disposed on or provided on the second electrode EL2.
[0123] The first electrode EL1 may be conductive (e.g., electrically conductive). The first electrode EL1 may be formed or composed of a metallic material, a metallic alloy, or a conductive (e.g., electrically conductive) compound. The first electrode EL1 may be an anode or a cathode. However, embodiments of this disclosure are not limited thereto. In one or more embodiments, the first electrode EL1 may be a pixel electrode. The first electrode EL1 may be a transmissive electrode, a semi-transmissive reflective electrode, or a reflective electrode. The first electrode EL1 may contain at least one selected from Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF, Mo, Ti, W, In, Sn, and Zn, two or more compounds selected from these, mixtures of two or more compounds selected from these, or oxides thereof.
[0124] If the first electrode EL1 is a transmission electrode (e.g., when the first electrode EL1 is a transmission electrode), the first electrode EL1 may contain a transparent (e.g., substantially transparent) metal oxide, such as indium tin oxide (ITO), indium zinc oxide (IZO), or zinc oxide (e.g., ZnO). xWhere 0 < x ≤ 2; for example, ZnO) and / or indium tin zinc oxide (ITZO). If the first electrode EL1 is a semi-transparent reflective electrode or a reflective electrode (e.g., when the first electrode EL1 is a semi-transparent reflective electrode or a reflective electrode), the first electrode EL1 may comprise Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, Mo, Ti, W, compounds or mixtures thereof (e.g., mixtures of Ag and Mg); and / or LiF / Ca (a stacked structure of LiF and Ca), or LiF / Al (a stacked structure of LiF and Al). In one or more embodiments, the first electrode EL1 may have a multilayer structure comprising a reflective or semi-transparent reflective film formed or composed of materials as described in one or more embodiments, and a transparent (e.g., substantially transparent) conductive (e.g., conductive) film formed or composed of ITO, IZO, ZnO, ITZO, etc. For example, the first electrode EL1 may have a three-layer structure of ITO / Ag / ITO, but the embodiments of this disclosure are not limited thereto. In one or more embodiments, the embodiments of this disclosure are not limited thereto, and the first electrode EL1 may comprise a metallic material as described in one or more embodiments, a combination of at least two metallic materials as described in one or more embodiments, an oxide of a metallic material as described in one or more embodiments, etc. The thickness of the first electrode EL1 may be from about 700 Å to about 10,000 Å. For example, the thickness of the first electrode EL1 may be from about 1,000 Å to about 3,000 Å.
[0125] A hole transport region (HTR) can be 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 or emitter assist layer (EAL), or an electron blocking layer (EBL). The thickness of the hole transport region (HTR) may be, for example, from about 50 Å to about 15,000 Å.
[0126] The hole transport region (HTR) can have a single-layer structure formed or composed of a single material, a single-layer structure formed or composed of multiple different materials, or a multi-layer structure including multiple layers formed or composed of multiple different materials.
[0127] For example, the hole transport region HTR can have a single-layer structure of a hole injection layer HIL or a hole transport layer HTL, or it can have a single-layer structure formed or composed of a hole injection material and a hole transport material. In one or more embodiments, the hole transport region HTR can have a single-layer structure formed or composed of a variety of different materials, or a structure in which hole injection layer HIL / hole transport layer HTL / buffer layer, hole injection layer HIL / buffer layer, hole transport layer HTL / buffer layer, or hole injection layer HIL / hole transport layer HTL / electron blocking layer EBL are stacked sequentially from the first electrode EL1, but the embodiments of this disclosure are not limited thereto.
[0128] Hole transport regions (HTRs) can be formed or provided using one or more suitable methods (e.g., vacuum deposition, spin coating, tape casting, Langmuir-Blodgett (LB) method, inkjet printing, laser printing and / or laser-induced thermal imaging (LITI) method).
[0129] The hole transport region (HTR) may contain a compound represented by formula H-1: Formula H-1 .
[0130] In formula H-1, L1 and L2 can each independently be a straight bond (e.g., a monovalent bond), 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. a and b can each independently be an integer from 0 to 10. In one or more embodiments, if a or b is an integer of 2 or greater (e.g., when a or b is an integer of 2 or greater), multiple L1 and 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.
[0131] In formula H-1, Ar1 and Ar2 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. In one or more embodiments, in formula H-1, Ar3 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.
[0132] The compound represented by formula H-1 can be a monoamine compound. In one or more embodiments, the compound represented by formula H-1 can be a diamine compound, wherein at least one selected from Ar1 to Ar3 includes an amine group as a substituent. In one or more embodiments, the compound represented by formula H-1 can be a carbazole-based compound comprising a substituted or unsubstituted carbazole group in at least one of Ar1 and Ar2, or a fluorene-based compound comprising a substituted or unsubstituted fluorene group in at least one of Ar1 and Ar2.
[0133] The compound represented by formula H-1 can be represented by any of the compounds selected from group H. However, the compounds listed in group H are examples, and the compound represented by formula H-1 is not limited to those represented by group H: Compound group H .
[0134] Hole transport region (HTR) can contain phthalocyanine compounds, such as copper phthalocyanine; N 1 N 1 '-([1,1'-biphenyl]-4,4'-diyl)bis(N 1 -Phenyl-N 4 N 4 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 / DBSA), polyaniline / camphorsulfonic acid (PANI / CSA), polyaniline / poly(4-styrenesulfonate) (PANI / PSS), N,N'-bis(naphthyl-1-yl)-N,N'-diphenyl-benzidine (NPB), triphenylamine-containing polyether ketone (TPAPEK), 4-isopropyl-4'-methyldiphenyliodonium [tetra(pentafluorophenyl)borate], dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarboxylonitrile (HAT-CN), etc.
[0135] Hole transport regions (HTRs) can contain carbazole-based derivatives (e.g., N-phenylcarbazole and / or polyvinylcarbazole), fluorene-based derivatives, triphenylamine-based derivatives (e.g., N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1-biphenyl]-4,4'-diamine (TPD) and / or 4,4',4''-tris(N-carbazolyl)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), 1,3-bis(N-carbazolyl)benzene (mCP), etc.
[0136] In one or more embodiments, the hole transport region (HTR) may comprise 9-(4-tert-butylphenyl)-3,6-bis(triphenylsilyl)-9H-carbazole (CzSi), 9-phenyl-9H-3,9'-bicarbazole (CCP), 1,3-bis(1,8-dimethyl-9H-carbazole-9-yl)benzene (mDCP), etc.
[0137] The hole transport region HTR may contain a compound of the hole transport region HTR as described in one or more embodiments in at least one of the hole injection layer HIL, hole transport layer HTL, emission auxiliary layer EAL, and electron blocking layer EBL.
[0138] The thickness of the hole transport region (HTR) can be from about 100 Å to about 10,000 Å, for example, from about 100 Å to about 5,000 Å. If the hole transport region (HTR) includes a hole injection layer (HIL) (e.g., when the hole transport region (HTR) includes a hole injection layer (HIL), the hole injection layer (HIL) can have a thickness of, for example, from about 30 Å to about 1,000 Å. If the hole transport region (HTR) includes a hole transport layer (HTL) (e.g., when the hole transport region (HTR) includes a hole transport layer (HTL), the hole transport layer (HTL) can have a thickness of from about 250 Å to about 1,000 Å. For example, if the hole transport region (HTR) includes an electron blocking layer (EBL) (e.g., when the hole transport region (HTR) includes an electron blocking layer (EBL), the electron blocking layer (EBL) can have a thickness of from about 10 Å to about 1,000 Å. If the thicknesses of the hole transport region HTR, hole injection layer HIL, hole transport layer HTL, and electron blocking layer EBL meet the above range (for example, when the thicknesses of the hole transport region HTR, hole injection layer HIL, hole transport layer HTL, and electron blocking layer EBL meet the above range), satisfactory or suitable hole transport properties can be achieved without a significant increase in driving voltage.
[0139] In addition to the materials described in one or more embodiments, the hole transport region (HTR) may further comprise a charge-generating material to increase or enhance conductivity (e.g., electrical conductivity). The charge-generating material may be uniformly (e.g., substantially uniformly) or non-uniformly dispersed in the hole transport region (HTR). The charge-generating material may be, for example, a p-dopant. A p-dopant may include at least one of halide metal compounds, quinone derivatives, metal oxides, and cyano-containing compounds, but embodiments of this disclosure are not limited thereto. For example, p-type dopants may include halometallic compounds (e.g., CuI and / or RbI), quinone derivatives (e.g., tetracyanoquinone dimethyl ether (TCNQ) and / or 2,3,5,6-tetrafluoro-7,7',8,8'-tetracyanoquinone dimethyl ether (F4-TCNQ)), metal oxides (e.g., tungsten oxide and / or molybdenum oxide), cyano-containing compounds (e.g., dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarboxynitrile (HAT-CN) and / or 4-[[2,3-bis[cyano-(4-cyano-2,3,5,6-tetrafluorophenyl)methylene]cyclopropyl]-cyanomethyl]-2,3,5,6-tetrafluorobenzyl nitrile (NDP9)), etc., but embodiments of this disclosure are not limited thereto.
[0140] As described in one or more embodiments, 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 an emission assist layer EAL and an electron blocking layer EBL. The emission assist layer EAL can compensate for the resonant distance and control the hole charge balance according to the wavelength of light emitted from the emission layer EML, and thus the luminous efficiency can be increased or enhanced. In one or more embodiments, the emission assist layer EAL can be used to prevent electrons from being injected into the hole transport region HTR (or reduce the extent or occurrence of electron injection into the hole transport region HTR). Materials that can be included in the hole transport region HTR may be included in the emission assist layer EAL. The electron blocking layer EBL can be a layer used to prevent electrons from being injected from the electron transport region ETR into the hole transport region HTR.
[0141] In a light-emitting element (ED) according to one or more embodiments, the emitter layer (EML) may contain a polycyclic compound according to one or more embodiments. The emitter layer (EML) may contain a polycyclic compound according to one or more embodiments as a dopant. The polycyclic compound according to one or more embodiments may be a dopant material in the emitter layer (EML). In this specification, the polycyclic compound according to one or more embodiments may be referred to as the first compound.
[0142] The polycyclic compound according to one or more embodiments may comprise a fused ring having at least nine rings as the core structure, the fused ring comprising four heteroatoms and two boron (B) atoms as cyclizing atoms. The polycyclic compound according to one or more embodiments may have a structure in which two fused rings each having five rings are connected by sharing a common ring, wherein each fused ring having five rings comprises two heteroatoms and one boron (B) atom as cyclizing atoms. For example, a first fused ring having five rings represented by formula a and a second fused ring having five rings represented by formula b1 may be connected by sharing ring c with each other. Therefore, the polycyclic compound according to one or more embodiments may have a core structure containing a fused ring with at least nine rings, wherein the first fused ring represented by formula a and the portion represented by formula b2 (which is the portion of the second fused ring represented by formula b1) are bonded.
[0143] Formula a
[0144] Formula b1
[0145] Formula b2
[0146] In formulas a, b1, and b2, rings a, b, c, d, and e can each be independently a substituted or unsubstituted aromatic hydrocarbon ring or a substituted or unsubstituted heterocycle. In one or more embodiments, each of rings a, b, c, d, and e can be attached to an adjacent group to form a ring. In formulas a, b1, and b2, if rings a, b, c, d, and e are each heterocycles (e.g., when each of rings a, b, c, d, and e is a heterocycle), then each of rings a, b, c, d, and e may not contain a boron atom as a cyclic atom. The polycyclic compound according to one or more embodiments can contain two boron atoms in its core structure, and thus its molecular planarity can be suitably or appropriately reduced. Therefore, in a light-emitting element (ED) containing a polycyclic compound according to one or more embodiments, concentration quenching that reduces luminous efficiency can be suppressed or reduced, and thus luminous efficiency and lifetime can be improved or increased.
[0147] In formulas a, b1, and b2, X1, X2, Z1, and Z2 can each independently be an oxygen (O) atom, a sulfur (S) atom, or a nitrogen (N) atom. If each of X1, X2, Z1, and Z2 is a nitrogen (N) atom (e.g., when each of X1, X2, Z1, and Z2 is a nitrogen (N) atom), then another substituent can be attached to the nitrogen atom. In one or more embodiments, in formulas a, b1, and b2, the further details described in Formula 1 herein can be similarly applied to rings a, b, c, d, and e.
[0148] In equation b2, This could be the part connected to ring c in equation a. For example, the two in equation b2. It can be bonded to two cyclic atoms, which are located consecutively between the atoms forming ring c.
[0149] The polycyclic compound according to one or more embodiments may contain a nitrogen atom as a cyclizing atom, which is substituted by at least one first substituent in a fused ring core structure having nine rings. At least two first daughter substituents may be attached to the first substituent. The first substituent and the first daughter substituent may each be a substituted or unsubstituted phenyl group. The polycyclic compound according to one or more embodiments may exhibit a molecular form in which the core structure is protected because the first substituent is attached to at least one nitrogen atom forming the core structure and at least two first daughter substituents are attached to the first substituent. In one or more embodiments, the p-orbitals of the boron (B) atom forming the fused ring core structure having nine rings may be well or suitably protected by the first substituent and the first daughter substituents, and thus the material stability may be increased or enhanced.
[0150] The light-emitting element (ED) according to one or more embodiments may comprise a polycyclic compound according to one or more embodiments. The polycyclic compound according to one or more embodiments may be represented by Formula 1.
[0151] Formula 1
[0152] In Formula 1, rings a, b, c, d, and e can each be independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heterocycle having 2 to 30 cyclic carbon atoms. If rings a, b, c, d, and e are each heterocycles (e.g., when rings a, b, c, d, and e are each heterocycles), boron atoms may not be included as cyclic atoms. For example, rings a, b, c, d, and e can each be a substituted or unsubstituted benzene ring (e.g., a substituted or unsubstituted phenyl group), but embodiments of this disclosure are not limited thereto. Rings a, b, c, d, and e, which are substituted or unsubstituted benzene rings, can each be attached to adjacent groups to form a ring.
[0153] In Equation 1, X1, X2, Z1, and Z2 can each independently be O, S, and NR, respectively. a or NR b In one or more embodiments, at least one of X1, X2, Z1, and Z2 can be NR. b Except for NR, X1, X2, Z1, and Z2. b The remaining ones can be O, S, or NR independently. a .
[0154] For example, X1, X2, and Z2 can each be independently O, S, NR. a or NR b At least one of X1, X2, and Z2 can be NR. b And X1, X2 or Z2 is not NR b The remainder can be O, S, or NR. a Z1 can be O, S, or NR. a However, the implementation of this disclosure is not limited to this.
[0155] In one or more implementations, R a It can be a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms. For example, R a It can be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted triphenyl group. If R a Substituted by different substituents (e.g., when R a When substituted by different substituents, then R a It can be substituted with deuterium atoms, alkyl groups, aryl groups, etc. In one or more embodiments, R a It can connect with adjacent groups to form a ring. For example, R a It can be bonded to any adjacent ring selected from ring a, ring b, ring c, ring d, and ring e to form a ring.
[0156] In one or more implementations, R b This can correspond to the first substituent as described in one or more embodiments. R b This can be represented by Equation 2. In Equation 2, It could refer to the location to be connected. It can be NR in X1, X2, Z1 and Z2 in Equation 1 b The part where nitrogen atoms are connected.
[0157] Formula 2
[0158] In Formula 2, R1 to R5 can each independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted amine group, a substituted or unsubstituted silyl 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 can be represented by Formula 3. In one or more embodiments, R1 to R5 can be bonded to adjacent groups to form a ring. For example, any one selected from R1 to R5 can be bonded to any adjacent one selected from ring a, ring b, ring c, ring d, and ring e to form a ring.
[0159] In one or more embodiments, at least two selected from R1 to R5 can be represented by Equation 3. For example, two or three selected from R1 to R5 can be represented by Equation 3. If two selected from R1 to R5 are represented by Equation 3 (e.g., when two selected from R1 to R5 are represented by Equation 3), then one selected from R1 and R5 and R3 can be represented by Equation 3, R1 and R4 can be represented by Equation 3, R1 and R5 can be represented by Equation 3, R2 and R5 can be represented by Equation 3, or R2 and R4 can be represented by Equation 3. If three of R1 to R5 are represented by Equation 3 (e.g., when three of R1 to R5 are represented by Equation 3), then R1, R3, and R5 can be represented by Equation 3, but embodiments of this disclosure are not limited thereto.
[0160] In one or more embodiments, the remaining members of R1 to R5 that are not represented by Formula 3 may each independently be 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. For example, the remaining members that are not represented by Formula 3 may each independently be a hydrogen atom, a deuterium atom, a cyano group, a substituted or unsubstituted propyl 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, the remaining members that are not represented by Formula 3 may each independently bond to adjacent groups to form a ring.
[0161] Formula 3
[0162] In Formula 3, Q1 to Q5 can each independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms. For example, Q1 to Q5 can each independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted tert-butyl group, or a substituted or unsubstituted phenyl group. In one or more embodiments, Q1 to Q5 can each independently bond to an adjacent group to form a ring. For example, any one selected from Q1 to Q5 can be bonded to any adjacent one selected from ring a, ring b, ring c, ring d, and ring e to form a ring.
[0163] In one or more embodiments, Q1 to Q5 can all be hydrogen atoms, but the embodiments of this disclosure are not limited thereto. In Equation 3, It could refer to the location to be connected.
[0164] In one or more embodiments, Equation 2 can be represented by Equation 2-1. As an example, Equation 2-1 is a structure in which Equation 3 is connected to R1 in Equation 2. Equation 2-1 can correspond to a structure in which Equation 3 is connected to R5 in Equation 2.
[0165] Equation 2-1
[0166] In Formula 2-1, one or two selected from R2', R3', R4', and R5' may be represented by Formula 3. For example, R3', R4', and R5' may be represented by Formula 3. In one or more embodiments, R3' and R5' may be represented by Formula 3. In Formula 2-1, the remaining R2', R3', R4', and R5' not represented by Formula 3 may each independently be 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.
[0167] In Formula 2-1, further details as described in one or more embodiments with reference to Formula 3 can be similarly applied to Q1 through Q5. For example, all of Q1 through Q5 can be hydrogen atoms, but embodiments of this disclosure are not limited thereto.
[0168] In a polycyclic compound according to one or more embodiments as represented by Formula 1, at least one selected from hydrogen atoms may be substituted with a deuterium atom. For example, in a polycyclic compound represented by Formula 1, in addition to the hydrogen atoms in rings a, b, c, d, e, X1, X2, Z1, and Z2, the hydrogen atom of each substituted substituent may be substituted with a deuterium atom.
[0169] In one or more embodiments, the polycyclic compound represented by Formula 1 can be represented by Formula 4. Further details as described with reference to Formula 1 in one or more embodiments can be similarly applied to X1, X2, Z1, and Z2 in Formula 4.
[0170] Formula 4
[0171] In equation 4, R6 to R 21 Each of these groups can independently be a hydrogen atom, a deuterium atom, a cyano group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 30 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, R6 to R 21 Each of these groups can independently be a hydrogen atom, a deuterium atom, a cyano group, a substituted or unsubstituted diphenylamine group, a substituted or unsubstituted propyl group, a substituted or unsubstituted tert-butyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted carbazole group, or a substituted or unsubstituted dibenzofuran group. In one or more embodiments, R6 to R 21 Each group can independently bond with adjacent groups to form a ring. For example, R6 can bond with the adjacent R group. a Or R bBonded to form a ring, and R 13 It can be with adjacent R a Or R b Bonding to form a ring.
[0172] In one or more embodiments, R6 to R6 are selected from Formula 4. 21 At least one of them can be represented by any one of the substituents selected from the substituent group 1. However, embodiments of the present disclosure are not limited thereto.
[0173] Substituted basis set 1
[0174] In one or more embodiments, the polycyclic compound represented by Formula 4 can be represented by any one of Formulas 5-1 to 5-3. Formulas 5-1 to 5-3 can correspond to the positions of X1, X2, and Z2 in the polycyclic compound represented by Formula 4, respectively. b And R b This can be represented by Formula 2. In one or more embodiments, in the polycyclic compound represented by Formula 1, Formulas 5-1 to 5-3 can respectively correspond to the positions of rings a, b, c, d, and e being substituted or unsubstituted benzene rings, and the corresponding parts of X1, X2, and Z2 are NR. b And R b The case represented by Equation 2.
[0175] Formula 5-1
[0176] Formula 5-2
[0177] Formula 5-3
[0178] In Equations 5-1 and 5-3, X 11 X 12 and Z 12 They can be O, S, and NR independently. a or NR b And Z 11 It can be O, S, or NR. a Further details as described in one or more embodiments of Reference Formula 1 can be similarly applied to R. a and R b .
[0179] For example, X in Equation 5-1 11 X12 and Z 11 They can be O, S, or NR independently. a In one or more implementation schemes, X 11 It can be NR b And X 12 and Z 11 They can be O, S, or NR independently. a In one or more implementation schemes, X 11 and X 12 Each can be an NR b And Z 11 It can be O, S, or NR. a If X 11 and X 12 Each is an NR b (For example, when X) 11 and X 12 Each is an NR b (when), then X 11 and X 12 They can be the same as or different from each other.
[0180] For example, X in Equation 5-2 11 Z 11 and Z 12 They can be O, S, or NR independently. a In one or more implementation schemes, Z 12 It can be NR b And X 11 and Z 11 They can be O, S, or NR independently. a In one or more implementation schemes, X 11 and Z 12 Each can be an NR b And Z 11 It can be O, S, or NR. a If X 11 and Z 12 Each is an NR b (For example, when X) 11 and Z 12 Each is an NR b (when), then X 11 and Z 12 They can be the same as or different from each other.
[0181] For example, X in Equation 5-3 12 Z 11 and Z 12 They can be O, S, or NR independently. a In one or more implementation schemes, Z12 It can be NR b And X 12 and Z 11 They can be O, S, or NR independently. a In one or more implementation schemes, X 12 and Z 12 Each can be an NR b And Z 11 It can be O, S, or NR. a If X 12 and Z 12 Each is an NR b (For example, when X) 12 and Z 12 Each is an NR b (when), then X 12 and Z 12 They can be the same as or different from each other.
[0182] In Equations 5-1 to 5-3, further details as described in one or more embodiments with reference to Equation 2 can be similarly applied to R1 to R5, and further details as described in one or more embodiments with reference to Equation 4 can be similarly applied to R6 to R7. 21 .
[0183] In one or more embodiments, the polycyclic compound represented by Formula 4 may be represented by any one selected from Formulas 6-1 to 6-6. Each of Formulas 6-1 to 6-6 may correspond to at least one corresponding position of X1, X2, and Z2 in the polycyclic compound represented by Formula 4 being NR. b And R b The case represented by Equation 2. In one or more embodiments, each of Equations 6-1 to 6-6 may correspond to a benzene ring in which the corresponding positions of ring a, ring b, ring c, ring d, and ring e are respectively substituted or unsubstituted, and at least one of X1, X2, or Z2 is NR. b And R b The case represented by Formula 2 in the polycyclic compound represented by Formula 1.
[0184] Formula 6-1
[0185] Formula 6-2
[0186] Formula 6-3
[0187] Formula 6-4
[0188] Formula 6-5
[0189] Formula 6-6
[0190] In equations 6-1 to 6-6, X 21 X 22 Z 21 and Z 22 They can be O, S, or NR independently. a Further details as described in one or more embodiments of Reference Formula 1 can be similarly applied to R. a .
[0191] In equations 6-1 to 6-6, selected from R a2 To R a5 At least one of them, selected from R b2 To R b5 At least one of them and selected from R c2 To R c5 At least one of them can be independently represented by Equation 3. For example, the ones selected from R in Equations 6-1, 6-4, 6-5 and 6-6 a2 To R a5 One or both of them can be represented by Equation 3. In one or more embodiments, the formulas selected from R in Equations 6-3, 6-5 and 6-6 are... c2 To R c5 One or both of them can be represented by Equation 3.
[0192] In Equations 6-1 to 6-6, R as described in one or more embodiments a2 To R a5 R b2 To R b5 and R c2 To R c5 The remainder not represented by Formula 3 may each 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 aryl group having 6 to 30 cyclic carbon atoms. For example, R as described in one or more embodiments a2 To R a5 R b2 To R b5 and R c2 To R c5 The remainder not represented by formula 3 can each independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted tert-butyl group, or a substituted or unsubstituted phenyl group.
[0193] In equations 6-1 to 6-6, Q 11 To Q 15 Q 21 To Q 25 and Q 31 To Q 35 Each of these can be an independent hydrogen atom, a deuterium atom, a substituted or unsubstituted tert-butyl group, or a substituted or unsubstituted phenyl group, but the embodiments disclosed herein are not limited thereto. Q 11 To Q 15 Q 21 To Q 25 and Q 31 To Q 35 Each can independently bond with adjacent groups to form a ring.
[0194] In Equations 6-1 to 6-6, further details as described in one or more embodiments with reference to Equation 4 can be similarly applied to R6 to R7. 21 .
[0195] In one or more embodiments, the polycyclic compound represented by Formula 1 may comprise a core of a fused ring having nine rings, wherein two fused rings having five rings each (each comprising two heteroatoms and one boron (B) atom as cyclizing atoms) are connected by sharing a common ring, and the core of the fused ring having nine rings contains at least one nitrogen atom, with a first substituent connected to said nitrogen atom. Therefore, the polycyclic compound according to one or more embodiments can contribute to achieving high luminous efficiency and long lifetime.
[0196] Polycyclic compounds according to one or more embodiments can exhibit high absorbance and narrow full width at half maximum (FWHM) characteristics by comprising a core of a fused ring having at least nine rings, and can provide both improved or enhanced luminescent efficiency and lifetime (e.g., simultaneously) because rapid reverse intersystem crossing (RISC) is feasible. In one or more embodiments, the polycyclic compound according to one or more embodiments can comprise at least one nitrogen atom through which a first substituent is connected to the core of the fused ring having nine rings, and at least two first daughter substituents can additionally bond to the first substituent, and thus the intermolecular interactions between the polycyclic compounds are reduced due to steric hindrance. Therefore, excellent or suitable material stability can be exhibited. For example, the polycyclic compound according to one or more embodiments can comprise at least one nitrogen atom through which a first substituent and first daughter substituents are connected, wherein the first substituent and first daughter substituents can protect the fused ring having nine rings, and thus increase the intermolecular distance. Therefore, Dexter energy transfer can be reduced. Therefore, the increase in triplet exciton concentration in polycyclic compounds can be suppressed or reduced, and thus the degradation in lifetime caused by the increase in triplet concentration can be suppressed or reduced. Therefore, if a polycyclic compound according to one or more embodiments is applied to an emitter layer EML (e.g., when a polycyclic compound according to one or more embodiments is applied to an emitter layer EML), not only can the luminous efficiency be increased or enhanced, but the lifetime of the device can also be improved or enhanced.
[0197] The polycyclic compound according to one or more embodiments may comprise a fused ring core having at least nine rings, and thus may exhibit high absorbance and narrow full width at half maximum (FWHM) characteristics, and the luminescent element (ED) may (e.g., simultaneously) have improved or enhanced effects on both luminous efficiency and lifetime, since fast reverse intersystem crossing (RISC) is feasible. In one or more embodiments, the polycyclic compound according to one or more embodiments may comprise at least one nitrogen atom, a first substituent attached to the nitrogen atom in the fused ring core having nine rings, and at least two first daughter substituents may additionally bond to the first substituent, and thus the intermolecular interactions between the polycyclic compounds are reduced due to steric hindrance. Therefore, excellent or suitable material stability may be exhibited. For example, the polycyclic compound according to one or more embodiments may comprise at least one nitrogen atom, with a first substituent and first daughter substituents attached to the nitrogen atom, the first substituent and first daughter substituents protecting the fused ring core having nine rings. Therefore, the intermolecular distance can be increased, and thus the Dexter energy transfer can be reduced. Therefore, the increase in the concentration of triplet excitons in polycyclic compounds can be suppressed or reduced, and thus the degradation in lifetime caused by the increase in the concentration of triplet excitons can be suppressed or reduced. Therefore, if a polycyclic compound according to one or more embodiments is applied to an emitting layer EML (e.g., when a polycyclic compound according to one or more embodiments is applied to an emitting layer EML), not only can the luminous efficiency be increased or enhanced, but the lifetime can also be improved or enhanced.
[0198] The polycyclic compound according to one or more embodiments may be represented by any of the compounds selected from Group 1. The light-emitting element ED according to one or more embodiments may contain at least one compound selected from Group 1. The light-emitting element ED according to one or more embodiments may contain at least one compound selected from Group 1 in the emitting layer EML.
[0199] Compound group 1
[0200] In a light-emitting element (ED) according to one or more embodiments, the emitting layer (EML) may be a delayed fluorescence emitting layer comprising a host and a dopant. For example, the emitting layer (EML) may emit thermally activated delayed fluorescence (TADF). A polycyclic compound according to one or more embodiments may be a delayed fluorescence dopant. For example, a polycyclic compound according to one or more embodiments may be a thermally activated delayed fluorescence dopant.
[0201] The emitting layer (EML) may contain a polycyclic compound as a dopant according to one or more embodiments. The polycyclic compound according to one or more embodiments may emit blue light. For example, the polycyclic compound according to one or more embodiments may be a luminescent material having a peak emission wavelength in the wavelength region of about 430 nm to about 490 nm. For example, the polycyclic compound according to one or more embodiments may be a luminescent material having a peak emission wavelength in the wavelength region of about 450 nm to about 470 nm.
[0202] In one or more embodiments, the emitter layer EML may comprise a polycyclic compound according to one or more embodiments and may further comprise at least one selected from the second to the fourth compound. In one or more embodiments, the emitter layer EML may comprise 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.
[0203] HT-1
[0204] In equation HT-1, A1 to A8 can each be N or CR independently. 51 For example, all A1 to A8 can be CR. 51 In one or more embodiments, any one of A1 to A8 can be N, and the remainder can be CR. 51 .
[0205] In formula HT-1, L1 can be a straight bond (e.g., a monocovalent bond), 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, L1 can be a straight bond (e.g., a monocovalent bond), a substituted or unsubstituted phenylene group, a substituted or unsubstituted divalent biphenyl group, a substituted or unsubstituted divalent carbazole group, etc., but the embodiments of this disclosure are not limited thereto.
[0206] In equation HT-1, Y a It can be a direct bond (e.g., a single covalent bond), CR 52 R53 or SiR 54 R 55 For example, it can refer to two benzene rings connected to the nitrogen atom in formula HT-1 via a direct bond (e.g., a single covalent bond). or connect. This refers to the position to be connected. In equation HT-1, if Y... a It is a direct bond (e.g., a single covalent bond) (e.g., when Y...) a When the bond is a direct bond (e.g., a monocovalent bond), the second compound represented by formula HT-1 may contain a carbazole moiety.
[0207] In formula HT-1, 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. For example, Ar1 can be a substituted or unsubstituted carbazole group, a substituted or unsubstituted dibenzofuran group, a substituted or unsubstituted dibenzothiophene group, a substituted or unsubstituted biphenyl group, etc., but the embodiments of this disclosure are not limited thereto.
[0208] In equation HT-1, R 51 To R 55 Each of the following can independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted thio group, a substituted or unsubstituted oxy group, a substituted or unsubstituted amine group, a substituted or unsubstituted boron group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 cyclic carbon atoms. In one or more embodiments, R 51 To R 55 Each of these groups can bond with an adjacent group to form a ring. For example, R 51 To R 55 Each can be either a hydrogen atom or a deuterium atom independently. R 51 To R 55 Each can be an unsubstituted methyl group or an unsubstituted phenyl group, which can be independent of each other.
[0209] In one or more embodiments, the second compound represented by formula HT-1 may be represented by any of the compounds selected from group 2. The emitter layer EML may contain at least one of the compounds selected from group 2 as the hole transport host material.
[0210] Compound group 2
[0211] In the compounds presented in Compound Group 2, "D" can refer to a deuterium atom, and "Ph" can refer to a substituted or unsubstituted phenyl group. For example, in the compounds presented in Compound Group 2, "Ph" can refer to an unsubstituted phenyl group.
[0212] In one or more embodiments, the emitter layer EML may contain a third compound represented by formula ET-1. For example, the third compound may be used as an electron transport host material for the emitter layer EML.
[0213] ET-1
[0214] In Equation ET-1, Z is selected. a To Z c At least one of them can be N, and the rest can be CR. 56 For example, selected from Z a To Z c Any one of them can be N, and the rest can each be CR independently. 56 In this case, the third compound represented by formula ET-1 may contain a pyridine moiety. In one or more embodiments, the compound is selected from Z... a To Z c Two of them can be N, and the remainder can be CR. 56 In this case, the third compound represented by formula ET-1 may contain a pyrimidine moiety. In one or more embodiments, Z a To Z c It can be entirely N. In this case, the third compound represented by formula ET-1 can contain a triazine moiety.
[0215] In equation ET-1, R 56 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 60 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 cyclic carbon atoms.
[0216] In Equation ET-1, e1 to e3 can each be an integer from 0 to 10 independently.
[0217] 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 each independently be a substituted or unsubstituted phenyl group or a substituted or unsubstituted carbazole group.
[0218] In formula ET-1, L2 to L4 can each be independently a straight bond (e.g., a monocovalent bond), 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. In one or more embodiments, if e1 to e3 is an integer of 2 or greater (e.g., when e1 to e3 is an integer 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.
[0219] In one or more embodiments, the third compound may be represented by any of the compounds selected from compound group 3. The light-emitting element ED of one or more embodiments may comprise any of the compounds selected from compound group 3.
[0220] Compound group 3
[0221] In the compounds presented in compound group 3, "D" can refer to a deuterium atom, and "Ph" can refer to an unsubstituted phenyl group.
[0222] The emitter layer EML can contain a second compound and a third compound, and the second and third compounds can form an excitocomplex. In the emitter layer EML, the excitocomplex can be formed or provided by a hole transport host and an electron transport host. In this case, the triplet energy level of the excitocomplex formed by the hole transport host and the electron transport host can correspond 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.
[0223] For example, the absolute value of the triplet level (T1) of the excimer complex formed by the hole transport host and the electron transport host can be from about 2.4 eV to about 3.0 eV. In one or more embodiments, the triplet level of the excimer complex can be smaller than the band gap value of each host material. The excimer complex can have a triplet level of about 3.0 eV or less, which is the band gap between the hole transport host and the electron transport host.
[0224] In one or more embodiments, the emitting layer EML may contain a fourth compound in addition to the first to third compounds described herein. The fourth compound may serve as a phosphorescent sensitizer for the emitting layer EML. Energy can be transferred from the fourth compound to the first compound, thereby emitting light.
[0225] For example, the emitting layer EML may include an organometallic complex comprising platinum (Pt) as a central metal atom and ligands attached to the central metal atom as a fourth compound. The emitting layer EML in one or more embodiments of the light-emitting element ED may include a compound represented by formula D-1 as the fourth compound: Formula D-1 .
[0226] In equation D-1, Q1 to Q4 can each be C or N independently.
[0227] In formula D-1, C1 to C4 can each be independently a substituted or unsubstituted hydrocarbon ring having 5 to 30 cyclic carbon atoms, or a substituted or unsubstituted heterocycle having 2 to 30 cyclic carbon atoms.
[0228] In equation D-1, L 11 To L 13 Each can be an independent direct bond (e.g., a single covalent bond). , , , The following are possible interpretations: 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," "This could refer to the part connected to C1 to C4."
[0229] In equation D-1, b11 to b13 can each be 0 or 1 independently. If b11 is 0 (for example, when b11 is 0), C1 and C2 can be unconnected to each other. If b12 is 0 (for example, when b11 is 0), C2 and C3 can be unconnected to each other. If b13 is 0 (for example, when b11 is 0), C3 and C4 can be unconnected to each other.
[0230] In equation D-1, R 61 To R 66 Each of the following can independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted thio group, a substituted or unsubstituted oxy group, a substituted or unsubstituted amine group, a substituted or unsubstituted boron group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 cyclic carbon atoms. In one or more embodiments, R 61 To R 66 Each of the groups can bond with an adjacent group to form a ring. R 61 To R 66 Each can be a substituted or unsubstituted methyl group or a substituted or unsubstituted tert-butyl group, which can be independent of each other.
[0231] In equation D-1, d1 to d4 can each be an integer from 0 to 4 independently. In equation D-1, if each of d1 to d4 is 0 (e.g., when each of d1 to d4 is 0), the fourth compound may not be affected by R. 61 To R 64 Each of d1 to d4 is replaced. Where each of d1 to d4 is 4 and R 61 To R 64 The case where each atom is hydrogen is essentially the same as the case where each of d1 to d4 is 0. If each of d1 to d4 is an integer of 2 or greater (e.g., when each of d1 to d4 is an integer of 2 or greater), R 61To R 64 Multiple elements can be identical, or selected from R. 61 To R 64 At least one of the multiple terms can be different from the others.
[0232] In formula D-1, C1 to C4 can each be an independently substituted or unsubstituted hydrocarbon ring, or a substituted or unsubstituted heterocycle represented by any one of formulas C-1 to C-4: .
[0233] In equations 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 group 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.
[0234] In one or more implementation schemes, in C-1 through C-4, " "This can correspond to the portion connected to Pt as the central metal atom, and" "This can correspond to the adjacent cyclic group (C1 to C4) or the linker (L)." 11 To L 13 (The part that is connected.)
[0235] An emitting layer EML of one or more embodiments may comprise a first compound, which is a fused polycyclic compound; and at least one selected from a second to a fourth compound. For example, the emitting layer EML may comprise a first compound, a second compound, and a third compound. In the emitting layer EML, the second and third compounds may form an excimer complex, and energy may be transferred from the excimer complex to the first compound, thereby emitting light.
[0236] In one or more embodiments, the emitter layer EML may comprise a first compound, a second compound, a third compound, and a fourth compound. In the emitter layer EML, the second and third compounds may form an exciton complex, and energy can be transferred from the exciton complex to the fourth and first compounds, thereby emitting light. In one or more embodiments, the fourth compound may be a sensitizer. The fourth compound included in the emitter layer EML of the light-emitting element ED in one or more embodiments can be used as a sensitizer to transfer energy from the host to the first compound, which is a light-emitting dopant. For example, the fourth compound, used as an auxiliary dopant, can accelerate the energy transfer to the first compound, which is a light-emitting dopant, thereby increasing the emission ratio of the first compound. Therefore, the emitter layer EML of one or more embodiments can improve or enhance luminous efficiency. In one or more embodiments, if the energy transfer to the first compound is increased or enhanced (e.g., when the energy transfer to the first compound is increased or enhanced), excitons formed in the emitter layer EML may not accumulate inside the emitter layer EML and can emit light rapidly, thus reducing device degradation. Therefore, the lifespan of the light-emitting element (ED) in one or more embodiments can be increased.
[0237] One or more embodiments of the light-emitting element (ED) may comprise all of the first, second, third, and fourth compounds, and the emission layer (EML) may comprise a combination of two host materials and two dopant materials. In one or more embodiments of the light-emitting element (ED), the emission layer (EML) may comprise, in parallel (e.g., simultaneously), the second and third compounds as two different hosts, the first compound emitting delayed fluorescence, and the fourth compound comprising an organometallic complex, thereby exhibiting excellent or suitable luminescent efficiency characteristics.
[0238] In one or more embodiments, the fourth compound represented by formula D-1 may be represented by at least one compound selected from group 4 of compounds. The emission layer EML may contain at least one compound selected from group 4 of compounds as a sensitizer material.
[0239] Compound group 4
[0240] In the compounds presented in compound group 4, "D" refers to the deuterium atom.
[0241] If the emitting layer EML in one or more embodiments of the light-emitting element ED contains all of the first compound, the second compound, and the third compound (e.g., when the emitting layer EML in one or more embodiments of the light-emitting element ED contains all of the first compound, the second compound, and the third compound), the content (e.g., amount) of the first compound may be from about 0.1 wt% to about 5 wt% relative to the total weight of the first compound, the second compound, and the third compound (e.g., based on 100 wt%). However, embodiments of this disclosure are not limited thereto. If the content (e.g., amount) of the first compound meets the proportions described in one or more embodiments (e.g., when the content (e.g., amount) of the first compound meets the proportions described in one or more embodiments), the energy transfer from the second and third compounds to the first compound may be increased or enhanced, and thus the luminous efficiency and device lifespan may be increased or enhanced.
[0242] The content (e.g., amount) of the second and third compounds in the emitter layer EML can be a margin excluding the weight of the first compound. For example, the content (e.g., amount) of the second and third compounds in the emitter layer EML can be from about 65 wt% to about 95 wt% relative to the total weight of the first, second, and third compounds (e.g., based on 100 wt%).
[0243] In the total weight of the second and third compounds (e.g., based on 100 wt%), the weight ratio of the second and third compounds can be from about 3:7 to about 7:3.
[0244] If the content (e.g., amount) of the second and third compounds meets the above-mentioned ratio (e.g., when the content (e.g., amount) of the second and third compounds meets the above-mentioned ratio), the charge balance characteristics in the emitter layer EML can be improved or enhanced, and therefore the luminous efficiency and device lifespan can be increased or enhanced. If the content (e.g., amount) of the second and third compounds deviates from the above-mentioned ratio range (e.g., when the content (e.g., amount) of the second and third compounds deviates from the above-mentioned ratio range), the charge balance in the emitter layer EML may be disrupted, and therefore the luminous efficiency will decrease and the device may be prone to degradation.
[0245] If the emitter layer EML contains a fourth compound (e.g., when the emitter layer EML contains a fourth compound), the content (e.g., amount) of the fourth compound in the emitter layer EML can be from about 10 wt% to about 30 wt% relative to the total weight of the first, second, third, and fourth compounds (e.g., based on 100 wt%). However, embodiments of this disclosure are not limited thereto. If the content (e.g., amount) of the fourth compound meets the aforementioned content (e.g., amount) (e.g., when the content (e.g., amount) of the fourth compound meets the aforementioned content (e.g., amount) range), the energy transfer from the host to the first compound, which is a light-emitting dopant, can be increased or enhanced, thereby improving or enhancing the light emission ratio, and thus improving or enhancing the luminous efficiency of the emitter layer EML. If the first, second, third, and fourth compounds contained in the emitter layer EML meet the aforementioned content (e.g., amount) ratio range (e.g., when the first, second, third, and fourth compounds contained in the emitter layer EML meet the aforementioned content (e.g., amount) ratio range), excellent or suitable luminous efficiency and long lifetime can be achieved.
[0246] An emitter layer (EML) can be provided on the hole transport region (HTR). The emitter layer EML can have a thickness of, for example, from about 100 Å to about 1,000 Å or from about 100 Å to about 300 Å. The emitter layer EML can have a monolayer structure formed or composed of a single material, a monolayer structure formed or composed of multiple different materials, or a multilayer structure having multiple layers formed or composed of multiple different materials.
[0247] In such Figures 5 to 9 In the light-emitting element (ED) illustrated according to one or more embodiments, the emitting layer (EML) may contain a polycyclic compound as a dopant according to one or more embodiments. In one or more embodiments, in such... Figures 5 to 9 In the light-emitting element ED according to one or more embodiments illustrated herein, the emitting layer EML may comprise a first compound being a polycyclic compound according to one or more embodiments, and may further comprise at least one selected from a second compound represented by formula 2 and a third compound represented by formula ET-1. In one or more embodiments, in such... Figures 5 to 9 In the light-emitting element ED illustrated according to one or more embodiments, the emitting layer EML may comprise a first compound, 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, a first compound represented by a polycyclic compound according to one or more embodiments.
[0248] In one or more embodiments of the light-emitting element (ED), the emitting layer (EML) may comprise anthracene derivatives, pyrene derivatives, fluoranthene derivatives, β-derived compounds, dihydrobenzanthene derivatives, and / or benzo[a]phenanthrene derivatives. For example, the emitting layer (EML) may comprise anthracene derivatives and / or pyrene derivatives.
[0249] In such Figures 5 to 9 In each of the one or more embodiments illustrated herein, the emitting layer EML may further comprise, in addition to the host and dopant as described in one or more embodiments, a host and dopant that are generally available or commonly used, such as a compound represented by Formula E-1. The compound represented by Formula E-1 can be used as a fluorescent host material.
[0250] E-1
[0251] In equation E-1, R 31 To R 40 Each group may independently be a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted silyl group, a substituted or unsubstituted thio group, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms, a substituted or unsubstituted 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 adjacent groups to form a ring. In one or more embodiments, R 31 To R 40 It can bond with adjacent groups to form saturated or unsaturated hydrocarbon rings, saturated heterocycles, or unsaturated heterocycles.
[0252] In E-1, c and d can each be an integer from 0 to 5 independently.
[0253] Formula E-1 can be represented by any one of compounds selected from E1 to E19: .
[0254] In one or more embodiments, the emitting layer EML may comprise 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 a fluorescent light-emitting element.
[0255] E-2a
[0256] In equation E-2a, a can be an integer from 0 to 10, and L a It can be a direct bond (e.g., a monocovalent bond), 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. In one or more embodiments, if a is an integer of 2 or greater (e.g., when a is an integer of 2 or greater), multiple L a Each can be an arylene group, either substituted or unsubstituted, having 6 to 30 cyclic carbon atoms, or a heteroarylene group, either substituted or unsubstituted, having 2 to 30 cyclic carbon atoms.
[0257] In one or more embodiments, in formula E-2a, A1 to A5 can each be N or CR independently. i R a To R i Each group can be independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted amine group, a substituted or unsubstituted thio group, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, or can be bonded to 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, S, etc. as cyclic atoms.
[0258] In one or more embodiments, in formula E-2a, two or three selected from A1 to A5 can be N, and the remainder can be CR. i .
[0259] E-2b
[0260] In formula E-2b, Cbz1 and Cbz2 can each be an unsubstituted carbazole group or a carbazole group substituted with an aryl group having 6 to 30 cyclic carbon atoms. bIt can be a direct bond (e.g., a monocovalent bond), 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. In one or more embodiments, b can be an integer from 0 to 10, and if b is an integer of 2 or greater (e.g., when b is an integer of 2 or greater), multiple L b Each can be an arylene group, either substituted or unsubstituted, having 6 to 30 cyclic carbon atoms, or a heteroarylene group, either substituted or unsubstituted, having 2 to 30 cyclic carbon atoms.
[0261] The compound represented by formula E-2a or E-2b may be represented by any of the compounds selected from group E-2. However, the compounds listed in group E-2 are examples, and the compounds represented by formula E-2a or E-2b are not limited to those listed in group E-2.
[0262] Compound group E-2
[0263] The emitter layer (EML) can contain compounds represented by the formula Ma. Compounds represented by the formula Ma can be used as phosphorescent dopant materials.
[0264] Formula Ma
[0265] In formula Ma, Y1 to Y4 and Z1 to Z4 can each be independently CR1 or N, and R1 to R4 can each be independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted amine group, a substituted or unsubstituted thio group, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, or can be bonded to adjacent groups to form a ring. In formula Ma, m can be 0 or 1, and n can be 2 or 3. In formula Ma, if m is 0 (e.g., when m is 0), n can be 3, or if m is 1 (e.g., when m is 1), n can be 2.
[0266] Compounds represented by the formula Ma can be used as phosphorescent dopants.
[0267] Compounds represented by formula Ma can be represented by any one of compounds selected from M-a1 to M-a25. However, compounds M-a1 to M-a25 are examples, and compounds represented by formula Ma are not limited to those represented by compounds M-a1 to M-a25.
[0268]
[0269] The emitter layer (EML) may contain a compound represented by any of the formulas Fa to Fc. Compounds represented by formulas Fa to Fc can be used as fluorescent dopant materials.
[0270] Formula Fa
[0271] 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 amine 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.
[0272] 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. This refers to the position to be connected.
[0273] Formula Fb
[0274] In equation Fb, R a and Rb Each of the Ar1 to Ar4 groups 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 can be bonded to adjacent groups to form a ring. Each of the Ar1 to Ar4 groups 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.
[0275] In formula Fb, U and V can each be independently a substituted or unsubstituted hydrocarbon ring having 5 to 30 cyclic carbon atoms, or a substituted or unsubstituted heterocycle having 2 to 30 cyclic carbon atoms. At least one selected from Ar1 to Ar4 can be a heteroaryl group containing O or S as a cyclic atom.
[0276] In formula Fb, the number of rings represented by U and V can each be 0 or 1 independently. For example, in formula Fb, if the number of U or V is 1 (e.g., when the number of U or V is 1), a ring can form a fused ring at the portion indicated by U or V, and if the number of U or V is 0 (e.g., when the number of U or V is 0), the ring indicated by U or V may not exist. For example, if the number of U is 0 and the number of V is 1 (e.g., when the number of U is 0 and the number of V is 1), or if the number of U is 1 and the number of V is 0 (e.g., when the number of U is 1 and the number of V is 0), the fused ring with a fluorene core in formula Fb can be a cyclic compound with 4 rings. In one or more embodiments, if the number of U and V is 0 (e.g., when the number of U and V is 0), the fused ring with a fluorene core in formula Fb can be a cyclic compound with 3 rings. In one or more embodiments, if the number of U and V is 1 each (e.g., when the number of U and V is 1 each), the fused ring with a fluorene core in formula Fb can be a cyclic compound with 5 rings.
[0277] Formula Fc
[0278] 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 R11 Each group may be independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted amine group, a substituted or unsubstituted boron group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thio group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 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.
[0279] In formula Fc, A1 and A2 can each independently bond with substituents of adjacent rings to form fused rings. For example, if A1 and A2 are each independently NR m (For example, when A1 and A2 are each independently NR) m In one or more embodiments, A1 can be bonded to R4 or R5 to form a ring.
[0280] In one or more embodiments, the emitter layer EML may further comprise a styrene derivative (e.g., 1,4-bis[2-(3-N-ethylcarbazolyl)vinyl]benzene (BCzVB), 4-(di-p-tolylamino)-4'-[(di-p-tolylamino)styrene]stilbene (DPAVB) and / or N-(4-((E)-2-(6-(((E)-4-(diphenylamino)styrene)naphth-2-yl)vinyl) )-N-phenylaniline (N-BDAVBi), 4,4'-bis[2-(4-(N,N-diphenylamino)phenyl)vinyl]biphenyl (DPAVBi), perylene and its derivatives (e.g., 2,5,8,11-tetra-tert-butylperylene (TBP)), pyrene and its derivatives (e.g., 1,1'-dipyrene, 1,4-dipyrenebenzene, 1,4-bis(N,N-diphenylamino)pyrene) are commonly used or frequently used dopant materials.
[0281] The emitter layer EML may further comprise commonly available or frequently used phosphorescent dopant materials. For example, metal complexes comprising 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, iridium(III) bis(4,6-difluorophenylpyridyl-N,C2')-pyridinecarboxylate (FIrpic), iridium(III) bis(2,4-difluorophenylpyridyl)tetra(1-pyrazolyl)borate (FIr6), and / or octaethylporphyrin platinum (PtOEP) can be used as phosphorescent dopant. However, embodiments of this disclosure are not limited thereto.
[0282] The emitter layer (EML) may contain quantum dot materials. The core of the quantum dots may be selected from group II-VI compounds, group I-II-VI compounds, group II-IV-VI compounds, group I-II-IV-VI compounds, group II-IV-V compounds, group III-VI compounds, group I-III-VI compounds, group III-V compounds, group III-II-V compounds, group IV-VI compounds, group IV elements, group IV compounds, or combinations thereof.
[0283] Group II-VI compounds may be selected from the group consisting of: binary compounds selected from CdSe, CdTe, CdS, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, MgSe, MgS, and mixtures thereof; and ternary compounds selected from CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnSeS, CdSeTe, CdS, CdTe, CdSe ... nS, CdZnSe, CdZnTe, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, MgZnSe, MgZnS and mixtures thereof; and quaternary compounds selected from HgZnTeS, CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe and mixtures thereof. In one or more embodiments, the group II-V compounds may further comprise group I metals and / or group IV elements. Group I-II-VI compounds may be selected from the group consisting of CuZnS, etc., and group II-IV-VI compounds may be selected from the group consisting of ZnSnS, etc. Group I-II-IV-VI compounds may be selected from quaternary compounds, which are selected from the group consisting of Cu2ZnSnS2, Cu2ZnSnS4, Cu2ZnSnSe4, Ag2ZnSnS2 and mixtures thereof.
[0284] III-VI compounds may include binary compounds (e.g., In2S3 and / or In2Se3), ternary compounds (e.g., InGaS3 and / or InGaSe3), or any combination thereof.
[0285] Group I-III-VI compounds may be selected from: ternary compounds, which are selected from the group consisting of AgInS, AgInS2, CuInS, CuInS2, AgGaS2, CuGaS2, CuGaO2, AgGaO2, AgAlO2 and mixtures thereof; or quaternary compounds, such as AgInGaS2 and / or CuInGaS2.
[0286] III-V group compounds may be selected from the group consisting of: binary compounds selected from GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, InSb and mixtures thereof; ternary compounds selected from GaNP, GaNAs, GaNSb, GaPAs, GaPSb, AlNP, AlNAs, AlNSb, AlPAs, AlPSb, InGaP, InAlP, InNP, InNAs, InNSb, InPAs, InPSb and mixtures thereof; and quaternary compounds selected from GaAlNP, GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNP, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs, InAlPSb and mixtures thereof. In one or more embodiments, the group III-V compound may further comprise a group II metal. For example, InZnP or similar materials may be selected as group III-II-V compounds.
[0287] Group IV-VI compounds may be selected from the group consisting of: binary compounds selected from SnS, SnSe, SnTe, PbS, PbSe, PbTe, and mixtures thereof; ternary compounds selected from SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, SnPbTe, and mixtures thereof; and quaternary compounds selected from SnPbSSe, SnPbSeTe, SnPbSTe, and mixtures thereof. Group IV elements may be selected from the group consisting of Si, Ge, and mixtures thereof. Group IV compounds may be binary compounds selected from the group consisting of SiC, SiGe, and mixtures thereof.
[0288] Each element contained in a multi-component compound (e.g., a binary, ternary, or quaternary compound) may exist in the particles with a homogeneous (e.g., substantially homogeneous) or non-homogeneous concentration distribution. For example, a formula refers to the type or kind of elements contained in the compound, and the ratio of elements in the compound can vary. For example, AgInGaS2 could refer to AgIn x Ga 1-x S2 (where x is a real number between 0 and 1).
[0289] In one or more embodiments, the quantum dot may have a single structure or a core-shell dual structure, wherein the concentration of each element contained in the quantum dot is uniform (e.g., substantially uniform). For example, the material contained in the core may be different from the material contained in the shell.
[0290] Examples of the shell for quantum dots may comprise metal oxides or non-metal oxides, semiconductor compounds, or combinations thereof. For example, metal oxides or non-metal oxides may include binary compounds (e.g., SiO2, Al2O3, TiO2, ZnO, MnO, Mn2O3, Mn3O4, CuO, FeO, Fe2O3, Fe3O4, CoO, Co3O4, or NiO) or ternary compounds (e.g., MgAl2O4, CoFe2O4, NiFe2O4, or CoMn2O4), but embodiments of this disclosure are not limited thereto.
[0291] In addition, examples of semiconductor compounds may include CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnSeS, ZnTeS, GaAs, GaP, GaSb, HgS, HgSe, HgTe, InAs, InP, InGaP, InSb, AlAs, AlP, AlSb, etc., but the embodiments of this disclosure are not limited thereto.
[0292] Each element contained in a multi-component compound (e.g., a binary or ternary compound) may exist in the particles in a homogeneous (e.g., substantially homogeneous) or non-homogeneous concentration distribution. For example, a formula refers to the type or kind of elements contained in a compound, and the ratio of elements in a compound can vary.
[0293] Quantum dots can have a full width at half maximum (FWHM) of an emission wavelength spectrum of about 45 nm or less, such as about 40 nm or less, or even about 30 nm or less, and within the aforementioned range, color purity or color reproducibility can be improved or enhanced. In one or more embodiments, light emitted through such quantum dots can be emitted in all directions, thereby (e.g., making) a wide viewing angle improved or enhanced.
[0294] In one or more embodiments, although the form of the quantum dots is not limited, as long as it is a form commonly used in the art, such as quantum dots in the form of spherical (e.g., substantially spherical), pyramidal (e.g., substantially pyramidal), multi-armed (e.g., substantially multi-armed), or cubic (e.g., substantially cubic) nanoparticles, nanotubes, nanowires, nanofibers, nanoplates, etc., can be utilized.
[0295] By adjusting the size of the quantum dots or the elemental ratios in the quantum dot compound, the band gap can be feasiblely controlled, and thus light within one or more suitable wavelength ranges can be obtained in the quantum dot emitting layer. Therefore, quantum dots as described in one or more embodiments (e.g., using quantum dots of different sizes and / or different elemental ratios in the quantum dot compound) can be utilized, and thus light-emitting elements emitting light of one or more suitable wavelengths can be realized. For example, the size of the quantum dots and / or the elemental ratios in the quantum dot compound can be selectively adjusted to emit red, green, and / or blue light. In one or more embodiments, the quantum dots can be configured or arranged to emit white light by combining one or more suitable colors of light.
[0296] In such Figures 5 to 9 In each of the light-emitting elements (EDs) of one or more embodiments illustrated herein, an electron transport region (ETR) may be 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 embodiments of this disclosure are not limited thereto.
[0297] The electron transport region (ETR) can have a single-layer structure formed or composed of a single material, a single-layer structure formed or composed of multiple different materials, or a multi-layer structure including multiple layers formed or composed of multiple different materials.
[0298] For example, the electron transport region (ETR) can have a monolayer structure of an electron injection layer (EIL) or an electron transport layer (ETL), and can have a monolayer structure formed or composed of an electron injection material and an electron transport material. In one or more embodiments, the electron transport region (ETR) can have a monolayer structure formed or composed of a variety of different materials, or can have a structure in which an electron transport layer (ETL) / electron injection layer (EIL), a hole blocking layer (HBL) / electron transport layer (ETL) / electron injection layer (EIL) are stacked sequentially from the emitter layer (EML), but embodiments of this disclosure are not limited thereto. The electron transport region (ETR) can have a thickness of, for example, from about 1,000 Å to about 1,500 Å.
[0299] The electron transport region (ETR) can be formed or provided using one or more suitable methods (e.g., vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) method, inkjet printing, laser printing and / or laser-induced thermal imaging (LITI) method).
[0300] The electron transport region (ETR) can contain compounds represented by formula ET-2: ET-2 .
[0301] In Equation ET-2, at least one of X1 to X3 can be N, and the remainder can be CR. a R a 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. Ar1 to Ar3 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.
[0302] In Formula ET-2, a to c can each be an integer from 0 to 10 independently. In Formula ET-2, L1 to L3 can each be a straight bond (e.g., a monovalent bond), 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. In one or more embodiments, if a to c are each an integer of 2 or greater (e.g., when a to c are each an integer of 2 or greater), L1 to L3 can each be an 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.
[0303] The electron transport region (ETR) may comprise anthracene-based compounds. However, embodiments of this disclosure are not limited thereto, and the ETR may comprise, for example, tris(8-hydroxyquinoline)aluminum (Alq3), 1,3,5-tris[(3-pyridyl)-benzene-3-yl]benzene, 2,4,6-tris(3'-(pyridin-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-yl)benzene (TPBi), 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), and 4,7-diphenyl-1,10-phenanthroline (Bphen). 3-(4-biphenyl)-4-phenyl-5-tert-butylphenyl-1,2,4-triazole (TAZ), 4-(naphth-1-yl)-3,5-diphenyl-4H-1,2,4-triazole (NTAZ), 2-(4-biphenyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (tBu-PBD), bis(2-methyl-8-quinoline-N1,O8)-(1,1'-biphenyl-4-oline)aluminum (BAlq), bis(benzoquinoline-10-oline)beryllium (Bebq2), 9,10-bis(naphth-2-yl)anthracene (ADN), 1,3-bis[3,5-bis(pyridin-3-yl)phenyl]benzene (BmPyPhB), or mixtures thereof.
[0304] The electron transport region (ETR) may contain at least one compound selected from compounds ET1 to ET36: .
[0305] In one or more embodiments, the electron transport region (ETR) may comprise a metal halide (e.g., LiF, NaCl, CsF, RbCl, RbI, CuI, and / or KI), a lanthanide (e.g., Yb), and / or a co-deposition material of a metal halide and a lanthanide. For example, the ETR may comprise KI:Yb, RbI:Yb, LiF:Yb, etc., as co-deposition materials. In one or more embodiments, the ETR may be formed or provided using metal oxides such as Li₂O and / or BaO, lithium 8-hydroxyquinoline (Liq), etc., but embodiments of this disclosure are not limited thereto. The ETR may also be formed or comprised of a mixture of an electron transport material and an insulating (e.g., electrically insulating) organometallic salt. The organometallic salt may be a material having a band gap of about 4 eV or greater than 4 eV. For example, the organometallic salt may include, for example, metal acetates, metal benzoates, metal acetoacetates, metal acetylacetonates, and / or metal stearates.
[0306] In addition to the materials described in one or more embodiments, the electron transport region (ETR) may further comprise at least one of 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), diphenyl(4-(triphenylsilyl)phenyl)phosphine oxide (TSPO1), and 4,7-diphenyl-1,10-phenanthroline (Bphen), but embodiments of this disclosure are not limited thereto.
[0307] The electron transport region (ETR) may contain a compound of the electron transport region (ETR) as described in one or more embodiments in at least one of the electron injection layer (EIL), the electron transport layer (ETL), and the hole blocking layer (HBL).
[0308] If the electron transport region (ETR) includes an electron transport layer (ETL) (e.g., when the ETR includes an ETL), the ETL can have a thickness of about 100 Å to about 1,000 Å, for example, about 150 Å to about 500 Å. If the thickness of the ETL meets the above range (e.g., when the ETL thickness meets the above range), satisfactory or suitable electron transport characteristics can be obtained without a significant increase in driving voltage. If the ETR includes an electron injection layer (EIL) (e.g., when the ETR includes an EIL), the EIL can have a thickness of about 1 Å to about 100 Å, for example, about 3 Å to about 90 Å. If the thickness of the EIL meets the above range (e.g., when the EIL thickness meets the above range), satisfactory or suitable electron injection characteristics can be obtained without a significant increase in driving voltage.
[0309] A second electrode EL2 may be 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 embodiments of this disclosure are not limited thereto. For example, if the first electrode EL1 is an anode (e.g., when the first electrode EL1 is an anode), the second electrode EL2 may be a cathode, and if the first electrode EL1 is a cathode (e.g., when the first electrode EL1 is a cathode), the second electrode EL2 may be an anode.
[0310] The second electrode EL2 can be a transmission electrode, a semi-transmissive reflective electrode, or a reflective electrode. If the second electrode EL2 is a transmission electrode (e.g., when the first electrode EL2 is a transmission electrode), the second electrode EL2 can be formed or composed of a transparent (e.g., substantially transparent) metal oxide, such as indium tin oxide (ITO), indium zinc oxide (IZO), or zinc oxide (e.g., ZnO). x , where 0 < x ≤ 2; for example, ZnO), indium tin zinc oxide (ITZO), etc.
[0311] If the second electrode EL2 is a semi-transparent reflective electrode or a reflective electrode (e.g., when the second electrode EL2 is a semi-transparent reflective electrode or a reflective electrode), the second electrode EL2 may comprise Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, Mo, Ti, Yb, W, or compounds or mixtures thereof (e.g., AgMg, AgYb, and / or MgYb); and / or LiF / Ca, or LiF / Al. In one or more embodiments, the second electrode EL2 may have a multilayer structure, said multilayer structure comprising a reflective or semi-transparent reflective film formed or composed of materials as described in one or more embodiments, and a transparent (e.g., substantially transparent) conductive (e.g., conductive) film formed or composed of ITO, IZO, ZnO, ITZO, etc. For example, the second electrode EL2 may comprise a metallic material as described in one or more embodiments, a combination of at least two metallic materials as described in one or more embodiments, an oxide of a metallic material as described in one or more embodiments, etc.
[0312] In one or more embodiments, the second electrode EL2 may be connected to an auxiliary electrode. If the second electrode EL2 is connected to the auxiliary electrode (e.g., when the second electrode EL2 is connected to the auxiliary electrode), the resistance (e.g., the resistance) of the second electrode EL2 may be reduced or decreased.
[0313] In one or more embodiments, a cover layer CPL may be further disposed or provided on the second electrode EL2 of the light-emitting element ED in one or more embodiments. The cover layer CPL may comprise multiple layers or a single layer.
[0314] In one or more embodiments, the capping layer CPL can be an organic layer or an inorganic layer. For example, if the capping layer CPL contains an inorganic material (e.g., when the capping layer CPL contains an inorganic material), the inorganic material may include an alkali metal compound (e.g., LiF), an alkaline earth metal compound (e.g., MgF2), silicon nitride oxide, or silicon oxynitride (e.g., SiO2). x N y Where 0 ≤ x ≤ 2 and 0 ≤ y ≤ 2; for example, SiON or Si2N2O), silicon nitrides (for example, SiN x Where 0 < x ≤ 2; for example, Si3N4), silicon oxide (for example, SiO2), where 0 < x ≤ 2. x , where 0 < x ≤ 2; for example, SiO2, etc.
[0315] For example, if the capping layer CPL contains an organic material (e.g., when the capping layer CPL contains 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), 4,4',4''-tris(carbazole-9-yl)triphenylamine (TCTA), etc., or epoxy-based resins, or acrylates (e.g., methacrylates). However, embodiments of this disclosure are not limited thereto, and the capping layer CPL may contain at least one selected from compounds P1 to P5: .
[0316] In one or more embodiments, the refractive index of the capping layer CPL may be about 1.6 or greater than 1.6. For example, the refractive index of the capping layer CPL may be about 1.6 or greater than 1.6 relative to light in the wavelength range of about 550 nm to about 660 nm.
[0317] Figures 10 to 13 Each of these is a cross-sectional view of a display device according to one or more embodiments of this disclosure. In the following, in reference to... Figures 10 to 13 When describing a display device of one or more embodiments in more detail, it is not necessary to repeat the descriptions already provided. Figures 1 to 9 The repetitive features described in the text are not the primary or main features that can be used to describe their differences.
[0318] refer to Figure 10According to one or more embodiments, the display device DD-a may include a display panel DP comprising a display device layer DP-ED, a light control layer CCL disposed on or provided on the display panel DP, and a color filter layer CFL. Figure 7 In one or more embodiments illustrated herein, the display panel DP may include a substrate layer BS, a circuit layer DP-CL on the substrate layer BS, and a display device layer DP-ED, wherein the display device layer DP-ED may include a light-emitting element ED.
[0319] A light-emitting element (ED) may include a first electrode EL1, a hole transport region HTR on the first electrode EL1, an emitter layer EML on the hole transport region HTR, an electron transport region ETR on the emitter layer EML, and a second electrode EL2 on the electron transport region ETR. In one or more embodiments, as described herein... Figures 5 to 9 The structure of the light-emitting element (ED) can be applied essentially equivalently to, for example... Figure 7 The structure of a light-emitting element (ED) is illustrated in the example. For example... Figure 10 The light-emitting element (ED) illustrated herein may comprise a polycyclic compound according to one or more embodiments. Therefore, the ED can exhibit high luminous efficiency and long lifespan characteristics.
[0320] refer to Figure 10 The emitting layer EML can be disposed or provided in the opening OH defined in the pixel-defining film PDL. For example, the emitting layer EML separated by the pixel-defining film PDL and provided corresponding to each emitting region PXA-R, PXA-G, and PXA-B can emit light in substantially the same wavelength range. In the display device DD-a of one or more embodiments, the emitting layer EML can emit blue light. In one or more embodiments, the emitting layer EML can be provided as a common layer in all emitting regions PXA-R, PXA-G, and PXA-B.
[0321] A light control layer (CCL) can be disposed on or provided on a display panel (DP). The CCL may include a light converter. The light converter can be a quantum dot, phosphor, etc. The light converter emits the provided light by converting its wavelength. For example, the CCL may be a layer containing quantum dots or a layer containing phosphors.
[0322] The optical control layer (CCL) may include multiple optical control components CCP1, CCP2, and CCP3. The optical control components CCP1, CCP2, and CCP3 may be spaced apart and / or separated from each other (e.g., separated or apart).
[0323] refer to Figure 10The partition pattern BMP may be provided between the light control components CCP1, CCP2 and CCP3 that are spaced apart and / or separated (e.g., separated or apart), but embodiments of this disclosure are not limited thereto. Figure 10 The example shows that the partition pattern BMP does not overlap with the light control components CCP1, CCP2 and CCP3, but at least a portion of the edges of the light control components CCP1, CCP2 and CCP3 may overlap with the partition pattern BMP.
[0324] The light control layer CCL may include: a first light control component CCP1 containing a first quantum dot QD1 that converts first color light provided by the light-emitting element ED into second color light, a second light control component CCP2 containing a second quantum dot QD2 that converts first color light into third color light, and a third light control component CCP3 that transmits first color light.
[0325] In one or more embodiments, a first light control component CCP1 can provide red light as a second color light, and a second light control component CCP2 can provide green light as a third color light. A third light control component CCP3 can provide blue light by transmitting blue light as a first color light provided by 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 principles as described herein can apply to quantum dots QD1 and QD2.
[0326] In one or more embodiments, the optical control layer CCL may further include a scatterer (e.g., a light scatterer) SP. The first optical control component CCP1 may include a first quantum dot QD1 and a scatterer SP, the second optical control component CCP2 may include a second quantum dot QD2 and a scatterer SP, and the third optical control component CCP3 may not contain any quantum dots but may include a scatterer SP.
[0327] The scatterer SP can be inorganic particles. For example, the scatterer SP can include at least one of TiO2, ZnO, Al2O3, SiO2, and hollow spherical silica. The scatterer SP can include any one selected from TiO2, ZnO, Al2O3, SiO2, and hollow spherical silica, or it can be a mixture of at least two materials selected from TiO2, ZnO, Al2O3, SiO2, and hollow spherical silica.
[0328] The first light control component CCP1, the second light control component CCP2, and the third light control component CCP3 may each comprise quantum dots QD1 and QD2 and a scatterer SP dispersed therein in matrix resins BR1, BR2, and BR3. In one or more embodiments, the first light control component CCP1 may comprise a first quantum dot QD1 and a scatterer SP dispersed in the first matrix resin BR1, the second light control component CCP2 may comprise a second quantum dot QD2 and a scatterer SP dispersed in the second matrix resin BR2, and the third light control component CCP3 may comprise a scatterer SP dispersed in the third matrix resin BR3.
[0329] The matrix resins BR1, BR2, and BR3 can be the medium in which quantum dots QD1 and QD2 and scatterers SP are dispersed, and can be formed or composed of one or more suitable resin compositions (which may generally be referred to as binders). For example, the matrix resins BR1, BR2, and BR3 can be acrylic-based resins, urethane-based resins, silicone-based resins, epoxy-based resins, etc. The matrix resins BR1, BR2, and BR3 can be transparent (e.g., substantially transparent) resins. In one or more embodiments, the first matrix resin BR1, the second matrix resin BR2, and the third matrix resin BR3 can be substantially the same as or different from each other.
[0330] The light control layer CCL may include a barrier layer BFL1. The barrier layer BFL1 can be used to prevent (or reduce the extent or occurrence of) moisture and / or oxygen (hereinafter referred to as "moisture / oxygen") penetration. The barrier layer BFL1 can block the light control components CCP1, CCP2, and CCP3 from exposure to moisture / oxygen (or reduce the extent or occurrence of exposure to moisture / oxygen). In one or more embodiments, the barrier layer BFL1 may cover the light control components CCP1, CCP2, and CCP3. In one or more embodiments, the barrier layer BFL2 may be provided between the light control components CCP1, CCP2, and CCP3 and the color filter layer CFL.
[0331] Barrier layers BFL1 and BFL2 may include at least one inorganic layer. For example, barrier layers BFL1 and BFL2 may contain inorganic materials. For instance, barrier layers BFL1 and BFL2 may contain silicon nitride, aluminum nitride, zirconium nitride, titanium nitride, hafnium nitride, tantalum nitride, silicon oxide, aluminum oxide, titanium oxide, tin oxide, cerium oxide, silicon nitride, metal thin films that ensure transmittance, etc. In one or more embodiments, barrier layers BFL1 and BFL2 may further include an organic film. Barrier layers BFL1 and BFL2 may be formed or composed of a single layer or multiple layers.
[0332] In one or more embodiments of the display device DD-a, the color filter layer CFL can be disposed on or provided on the light control layer CCL. For example, the color filter layer CFL can be directly disposed on or provided on the light control layer CCL. In this case, the blocking layer BFL2 may not be provided.
[0333] A color filter layer (CFL) may include filters CF1, CF2, and CF3. The CFL may include a first filter CF1 configured or arranged to transmit a second color of light, a second filter CF2 configured or arranged to transmit a third color of light, and a third filter CF3 configured or arranged to transmit 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 contain a polymeric photosensitive resin and / or pigments and / or dyes. The first filter CF1 may contain red pigments and / or dyes, the second filter CF2 may contain green pigments and / or dyes, and the third filter CF3 may contain blue pigments and / or dyes.
[0334] The embodiments disclosed herein are not limited thereto, and the third filter CF3 may not contain pigments and / or dyes. The third filter CF3 may contain a polymeric photosensitive resin and may not contain pigments and / or dyes. The third filter CF3 may be transparent (e.g., substantially transparent). The third filter CF3 may be formed or composed of a transparent (e.g., substantially transparent) photosensitive resin.
[0335] Furthermore, 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 but provided as a single filter.
[0336] In one or more embodiments, the color filter layer CFL may further include a light-shielding component. The light-shielding component may be a black matrix. The light-shielding component may comprise organic and / or inorganic light-shielding materials including black pigments and / or black dyes. The light-shielding component may prevent light leakage (or reduce the degree or occurrence of light leakage) and may separate the boundaries between adjacent filters CF1, CF2, and CF3.
[0337] The first to third filters CF1, CF2 and CF3 can be configured or provided to correspond to the red luminous area PXA-R, the green luminous area PXA-G and the blue luminous area PXA-B respectively.
[0338] The substrate BL can be disposed or provided on the color filter layer CFL. The substrate BL can be a component on a substrate surface in which the color filter layer CFL, light control layer CCL, etc., are disposed or provided. The substrate BL can be a glass substrate, a metal substrate, a plastic substrate, etc. However, embodiments of this disclosure are not limited thereto, and the substrate BL can be an inorganic layer, an organic layer, or an organic-inorganic composite layer. In one or more embodiments, the substrate BL may not be provided.
[0339] Figure 11 This is a cross-sectional view illustrating a portion of a display device according to one or more embodiments; in the display device DD-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. At least one of the plurality of light-emitting structures OL-B1, OL-B2, and OL-B3 may contain a polycyclic compound according to one or more embodiments. Therefore, the light-emitting element ED-BT can exhibit high luminous efficiency and long lifespan characteristics.
[0340] A light-emitting element (ED-BT) may include a first electrode EL1 and a second electrode EL2 opposite to each other (e.g., facing each other), and a plurality of light-emitting structures OL-B1, OL-B2, and OL-B3 sequentially stacked in the thickness direction between the first electrode EL1 and the second electrode EL2. Each of the light-emitting structures OL-B1, OL-B2, and OL-B3 may include an emissive layer EML. Figure 10 ), and hole transport region HTR and electron transport region ETR, with an emitter layer EML provided or positioned between the hole transport region HTR and the electron transport region ET. Figure 10 For example, the light-emitting element ED-BT included in one or more embodiments of the display device DD-TD can be a light-emitting element having a series structure and including multiple emitting layers.
[0341] In such Figure 11In one or more embodiments illustrated, all light beams emitted by the light-emitting structures OL-B1, OL-B2, and OL-B3 may be blue light. However, embodiments of this disclosure are not limited thereto, and the light beams emitted by the light-emitting structures OL-B1, OL-B2, and OL-B3 may have different wavelength ranges 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 beams with different wavelength ranges from each other may emit white light. Charge generation layers CGL1 and CGL2 may be disposed or provided between two of adjacent light-emitting structures OL-B1, OL-B2, and OL-B3, respectively. Charge generation layers CGL1 and CGL2 may comprise positive or positive-type (p-type or p-class) charge generation layers and / or negative or negative-type (n-type or n-class) charge generation layers.
[0342] refer to Figure 12 The display device DD-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. At least one of the light-emitting elements ED-1, ED-2, and ED-3 may contain a polycyclic compound according to one or more embodiments. Therefore, the light-emitting elements ED-1, ED-2, and ED-3 can exhibit high luminous efficiency and long lifespan characteristics.
[0343] and Figure 4 Compared to the display device DD of one or more embodiments illustrated in the example, such as Figure 12 One or more embodiments illustrated may differ in that: each of the first to third light-emitting elements ED-1, ED-2 and ED-3 includes 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 may emit light in substantially the same wavelength range.
[0344] 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. In one or more embodiments, the third light-emitting element ED-3 may include a first blue emitting layer EML-B1 and a second blue emitting layer EML-B2. An emission assist component OG may be disposed or provided 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.
[0345] The emission assist component OG may comprise a single layer or multiple layers. The emission assist component OG may include a charge generation layer. For example, the emission assist component OG may include an electron transport region, a charge generation layer, and a hole transport region stacked sequentially. The emission assist component OG may provide all the common layers of the first to third light-emitting elements ED-1, ED-2, and ED-3. However, embodiments of this disclosure are not limited thereto, and the emission assist component OG may be provided by patterning within an opening OH defined in a pixel-defining film PDL.
[0346] A first red emitter layer EML-R1, a first green emitter layer EML-G1, and a first blue emitter layer EML-B1 may be disposed or provided between the emission auxiliary component OG and the electron transport region ETR. A second red emitter layer EML-R2, a second green emitter layer EML-G2, and a second blue emitter layer EML-B2 may be disposed or provided between the hole transport region HTR and the emission auxiliary component OG.
[0347] For example, 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 assist component OG, the 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 assist component 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 assist component OG, a first blue emitting layer EML-B1, an electron transport region ETR, and a second electrode EL2, stacked sequentially.
[0348] In one or more embodiments, an optical auxiliary layer PL may be disposed or provided on the display device layer DP-ED. The optical auxiliary layer PL may include a polarizing layer. The optical auxiliary layer PL may be disposed or provided on the display panel DP and control the reflected light in the display panel DP due to external light. In one or more embodiments, an optical auxiliary layer PL may not be provided in the display device according to one or more embodiments.
[0349] Figure 13The display device DD-c is illustrated, comprising 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 opposite to each other (e.g., 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. At least one of the first to fourth light-emitting structures OL-B1, OL-B2, OL-B3, and OL-C1 may contain a polycyclic compound according to one or more embodiments. Therefore, the light-emitting element ED-CT can exhibit high luminous efficiency and long lifespan characteristics.
[0350] Charge generation layers CGL1, CGL2, and CGL3 may be disposed or provided between the first to fourth light-emitting structures OL-B1, OL-B2, OL-B3, and OL-C1. Of the four light-emitting structures, the first to third light-emitting structures OL-B1, OL-B2, and OL-B3 may emit blue light, and the fourth light-emitting structure OL-C1 may emit green light. However, embodiments of this disclosure are not limited thereto, and the first to fourth light-emitting structures OL-B1, OL-B2, OL-B3, and OL-C1 may emit light beams in different wavelength regions. The charge generation layers CGL1, CGL2, and CGL3 disposed or provided between adjacent light-emitting structures OL-B1, OL-B2, OL-B3, and OL-C1 may include p-type or p-class charge generation layers and / or n-type or n-class charge generation layers.
[0351] In one or more embodiments, the electronic device may include a display device and a control unit for controlling the display device, the display device including a display panel including a plurality of light-emitting elements. The electronic device according to one or more embodiments can be activated in response to an electrical signal. The electronic device may include the display device of one or more embodiments. For example, the electronic device may include not only large electronic devices (e.g., televisions, monitors, or billboards), but also small and medium-sized electronic devices (e.g., personal computers, laptops, personal digital terminals, vehicle display devices, game consoles, smartphones, tablets, smartwatches, or cameras). In one or more embodiments, these are presented by way of example only, and the display device according to one or more embodiments may be applied to another electronic device without departing from the spirit and scope of this disclosure.
[0352] Figure 14An example of a tablet terminal is shown as an electronic device (EA). A tablet terminal can be configured or arranged by placing electronic modules mounted on a motherboard, camera module, power module, etc., together with a display device (DM) in a bracket / housing (HAU), etc.
[0353] In one or more embodiments, an electronic device EA is illustrated, comprising a display device DD equipped with a flat (e.g., substantially flat) display surface; however, embodiments of this disclosure are not limited thereto. The electronic device EA may also include a curved or three-dimensional display surface. For example, a three-dimensional display surface may include multiple display areas indicating different orientations and may also include a curved display surface. The electronic device EA according to one or more embodiments of this disclosure may be a flexible electronic device. A flexible electronic device may be a foldable electronic device that can be folded.
[0354] like Figure 14 As illustrated, the display surface EA-IS may include an active area AA for displaying video and a border area NAA adjacent to the active area AA. The border area NAA may be an area in which video is not displayed. Figure 13 An icon image is shown as an example of a video. The active area AA can be referred to as the display area of the display device DM, and the border area BAA can be referred to as the non-display area of the display device DM.
[0355] like Figure 15 The electronic device EA-1 illustrated in the reference may include, as shown in the reference Figure 3 , Figure 4 , Figures 10 to 13 The display device of one or more embodiments described in more detail.
[0356] Figure 15 A portable terminal is illustrated as an example of an electronic device EA-1 according to one or more embodiments. Reference Figure 15 The electronic device EA-1 according to one or more embodiments may include multiple display surfaces. The electronic device EA-1 according to one or more embodiments may include display surfaces IS-M, IS-S1, IS-S2, IS-S3 and IS-S4, which have different main display orientations or primary display orientations from each other.
[0357] For example, in one or more embodiments, the electronic device EA-1 may be a three-dimensional display device including a top display surface IS-M and a plurality of side display surfaces IS-S1, IS-S2, IS-S3, and IS-S4. Each of the plurality of side display surfaces IS-S1, IS-S2, IS-S3, and IS-S4 may extend from one side of the top display surface IS-M. In one or more embodiments, the electronic device EA-1 may include a main display surface or primary display surface that primarily or mainly provides images in one direction, and a plurality of sub-display surfaces, each of which provides images in a direction different from the said one direction. Figure 14 In the electronic device EA illustrated according to one or more embodiments, the main display surface may be the top display surface IS-M, and the sub-display surfaces may be the side display surfaces IS-S1, IS-S2, IS-S3 and IS-S4.
[0358] Side display surfaces IS-S1, IS-S2, IS-S3, and IS-S4 may each have a display surface that is not parallel to the top display surface IS-M. In one or more embodiments, the multiple side display surfaces IS-S1, IS-S2, IS-S3, and IS-S4 may each be a display area that is curved and extends from one side of the top display surface IS-M, and for example, the multiple side display surfaces IS-S1, IS-S2, IS-S3, and IS-S4 may each be a curved display area.
[0359] like Figure 15 The electronic device EA illustrated in the example may include, according to, as referenced Figure 3 , Figure 4 , Figures 10 to 13 The display device of one or more embodiments described in more detail.
[0360] Figure 16 This is a view illustrating a vehicle AM, wherein a first display device to a fourth display device DD-1, DD-2, DD-3, and DD-4 are arranged or provided. At least one of the first to fourth display devices DD-1, DD-2, DD-3, and DD-4 may include, as shown in the reference... Figure 3 ,and Figure 4 as well as Figures 8 to 13 The display devices DD, DD-TD, DD-a, DD-b and DD-c described in more detail have essentially the same configuration or arrangement.
[0361] Figure 16The vehicle AM is illustrated, but this is merely an example, and the first to fourth display devices DD-1, DD-2, DD-3, and DD-4 can be arranged or provided in another mode of transport (e.g., bicycles, motorcycles, trains, ships, and airplanes). In one or more embodiments, at least one of the first to fourth display devices DD-1, DD-2, DD-3, and DD-4, selected from those comprising substantially the same configuration and arrangement as the display devices DD, DD-TD, DD-a, DD-b, and DD-c in one or more embodiments, can be used in personal computers, laptop computers, personal digital terminals, game consoles, portable electronic devices, televisions, monitors, billboards, etc. In one or more embodiments, these are provided merely as examples and can therefore be used in other electronic devices unless departing from the scope of this disclosure.
[0362] At least one of the first to fourth display devices DD-1, DD-2, DD-3, and DD-4 may include, as referenced Figures 5 to 9 The light-emitting element ED of one or more embodiments is described in more detail. At least one of the first to fourth display devices DD-1, DD-2, DD-3, and DD-4 may contain a polycyclic compound according to one or more embodiments. Therefore, the first to fourth display devices DD-1, DD-2, DD-3, and DD-4, each containing a polycyclic compound according to one or more embodiments, may have improved or enhanced display efficiency and display lifespan.
[0363] refer to Figure 16 The vehicle AM may include a steering wheel HA and a gear shifter GR to drive the vehicle AM. In one or more embodiments, the vehicle AM may include a windshield GL configured or provided opposite to the driver (e.g., facing the driver).
[0364] The first display device DD-1 may be located or provided in a first area overlapping with the steering wheel HA. For example, the first display device DD-1 may be a digital cluster component displaying first information about the vehicle AM. The first information may include a first scale indicating the vehicle AM's speed, a second scale indicating engine speed (e.g., revolutions per minute (RPM)), an image indicating fuel status, etc. The first and second scales may be displayed as digital images.
[0365] The second display device DD-2 may be positioned or provided in a second area opposite to (e.g., facing the driver's seat) and overlapping with the windshield GL. The driver's seat may be a seat in which the steering wheel HA is positioned or provided. For example, the second display device DD-2 may be a head-up display (HUD) displaying second information about the vehicle AM. The second display device DD-2 may optionally be optically transparent (e.g., substantially transparent). The second information may include a number indicating driving speed and may further include information such as the current time. In one or more embodiments, the second information of the second display device DD-2 may be projected onto the windshield GL to be displayed.
[0366] The third display device DD-3 may be located or provided in a third zone adjacent to the gear shift lever GR. For example, the third display device DD-3 may be located or provided between the driver's seat and the passenger seat, and may be a central information display (CID) for displaying third information in the vehicle's AM. The passenger seat may be a seat spaced apart from and / or separated from the driver's seat (e.g., partitioned or separated), with the gear shift lever GR located or provided therebetween. The third information may include information about traffic (e.g., navigation information), music or radio broadcasts or videos (or images), the temperature inside the vehicle's AM, etc.
[0367] The fourth display device DD-4 may be spaced apart from and / or separated from the steering wheel HA and gear shift GR (e.g., separated or separate), and may be disposed or provided in a fourth zone adjacent to the side of the vehicle AM. For example, the fourth display device DD-4 may be a digital side mirror displaying fourth information. The fourth display device DD-4 may display images of the exterior of the vehicle AM captured by a camera module CM disposed or provided outside the vehicle AM. The fourth information may include images of the exterior of the vehicle AM.
[0368] The first to fourth information as described in one or more embodiments may be examples, and the first to fourth display devices DD-1, DD-2, DD-3, and DD-4 may further display information about the interior and exterior of the vehicle AM. The first to fourth information may include different information. However, embodiments of this disclosure are not limited thereto, and a portion of the first to fourth information may include information that is substantially the same as each other.
[0369] In the following, with reference to embodiments and comparative examples, polycyclic compounds and light-emitting elements according to one or more embodiments of the present disclosure will be described in more detail. However, these embodiments are examples, and embodiments of the present disclosure are not limited thereto.
[0370] Example
[0371] 1. Synthesis of polycyclic compounds
[0372] The method for synthesizing polycyclic compounds according to one embodiment will be described in more detail by illustrating the synthetic methods of compounds B-17, C-18, C-26, H-1, and H-2. Furthermore, the methods for synthesizing polycyclic compounds described below are examples, and the methods for synthesizing compounds according to one or more embodiments of this disclosure are not limited to the embodiments described.
[0373] 1) Synthesis of intermediate a
[0374] Intermediate a can be synthesized, for example, by the method in reaction scheme A.
[0375] Reaction scheme A
[0376] Intermediate a-1 (300 mmol), intermediate a-2 (150 mmol), tBuONa (600 mmol), Pd(dba)2 (15 mmol), and [(tBu)3PH]BF4 (30 mmol) were placed in a three-necked flask, which was purged with argon (Ar), and then about 1000 mL of toluene was added. The resulting mixture was then stirred at about 60 °C for about 8 hours. Water was added to the reaction vessel, and the organic layer was extracted with toluene and then dried over magnesium sulfate to remove the solvent by evaporation. The obtained crude product was purified by silica gel column chromatography (using a mixed solvent of hexane / toluene) and recrystallization (using a mixed solvent of ethanol / toluene) to obtain about 131 mmol of white solid (about 87% yield). The purified product was identified by rapid atomic impact mass spectrometry (FAB-MS) with a molecular weight of 456 g / mol, thus confirming the yield of intermediate a-3.
[0377] Subsequently, intermediates a-3 (131 mmol), a-4 (1290 mmol), K₂CO₃ (645 mmol), and CuI (141 mmol) were placed in a three-necked flask, which was purged with argon, and the resulting mixture was stirred at approximately 210 °C for approximately 24 hours. Water was added to the reaction vessel, and the organic layer was extracted with toluene and then dried over magnesium sulfate to remove the solvent by evaporation. The obtained crude product was purified by silica gel column chromatography (using a mixed solvent of hexane / toluene) and recrystallization (using a mixed solvent of ethanol / toluene) to obtain approximately 112 mmol of white solid (approximately 85% yield). The purified product was identified by FAB-MS as having a molecular weight of 567 g / mol, thus confirming the yield of intermediate a-5.
[0378] Then, intermediates a-5 (112 mmol), a-2 (120 mmol), tBuONa (336 mmol), Pd(dba)2 (11 mmol), and [(tBu)3PH]BF4 (22 mmol) were placed in a three-necked flask, which was purged with argon. 1000 mL of toluene was added, and the mixture was stirred at 100 °C for about 2 hours. Water was added to the reaction vessel, and the organic layer was extracted with toluene and then dried over magnesium sulfate to remove the solvent by evaporation. The obtained crude product was purified by silica gel column chromatography (hexane / toluene mixed solvent) and recrystallization (ethanol / toluene mixed solvent) to obtain about 131 mmol of white solid (about 87% yield). The purified product was identified by FAB-MS as having a molecular weight of 731 g / mol, thus confirming the yield of intermediate a.
[0379] 2) Synthesis of intermediate b
[0380] Intermediate b can be synthesized, for example, by the method in reaction scheme B.
[0381] Reaction scheme B
[0382] Intermediate b-1 (300 mmol), intermediate b-2 (150 mmol), tBuONa (600 mmol), Pd(dba)2 (15 mmol), and [(tBu)3PH]BF4 (30 mmol) were placed in a three-necked flask, which was purged with argon. Approximately 1000 mL of toluene was then added, and the resulting mixture was stirred at approximately 70 °C for approximately 5 hours. Water was added to the reaction vessel, and the organic layer was extracted with toluene and dried over magnesium sulfate to remove the solvent by evaporation. The obtained crude product was purified by silica gel column chromatography (using a mixed solvent of hexane and toluene) and recrystallization (using a mixed solvent of ethanol and toluene) to obtain approximately 104 mmol of white solid (approximately 69% yield). The purified product was identified by FAB-MS as having a molecular weight of 532 g / mol, thus confirming the yield of intermediate b-3.
[0383] Then, intermediates b-3 (104 mmol), b-4 (1040 mmol), K₂CO₃ (520 mmol), and CuI (104 mmol) were placed in a three-necked flask, which was purged with argon, and the resulting mixture was stirred at approximately 210 °C for approximately 54 hours. Water was added to the reaction vessel, and the organic layer was extracted with toluene and then dried over magnesium sulfate to remove the solvent by evaporation. The obtained crude product was purified by silica gel column chromatography (using a mixed solvent of hexane and toluene) and recrystallization (using a mixed solvent of ethanol and toluene) to obtain approximately 98 mmol of white solid (approximately 94% yield). The purified product was identified by FAB-MS as having a molecular weight of 685 g / mol, thus confirming the yield of intermediate b-5.
[0384] Subsequently, intermediates b-5 (98 mmol), b-2 (104 mmol), tBuONa (300 mmol), Pd(dba)2 (10 mmol), and [(tBu)3PH]BF4 (20 mmol) were placed in a three-necked flask, which was purged with argon. Approximately 800 mL of toluene was then added, and the resulting mixture was stirred at approximately 100 °C for approximately 3 hours. Water was added to the reaction vessel, and the organic layer was extracted with toluene and then dried over magnesium sulfate to remove the solvent by evaporation. The obtained crude product was purified by silica gel column chromatography (using a mixed solvent of hexane and toluene) and recrystallization (using a mixed solvent of ethanol and toluene) to obtain approximately 90 mmol of white solid (approximately 92% yield). The purified product was identified by FAB-MS as having a molecular weight of 925 g / mol, thus confirming the yield of intermediate b.
[0385] 3) Synthesis of intermediate c
[0386] Intermediate c can be synthesized, for example, by the method in reaction scheme C.
[0387] Reaction scheme C
[0388] Intermediate c-1 (200 mmol), intermediate c-2 (220 mmol), and K₂CO₃ (600 mmol) were placed in a three-necked flask, which was purged with argon. Then, 200 mL of 1-methyl-2-pyrrolidone (NMP) was added, and the resulting mixture was stirred at approximately 150 °C for approximately 24 hours. Water was added to the reaction vessel, and the organic layer was extracted with toluene and then dried over magnesium sulfate to remove the solvent by evaporation. The obtained crude product was purified by silica gel column chromatography (using a mixed solvent of hexane and toluene) and recrystallization (using a mixed solvent of ethanol and toluene) to obtain approximately 154 mmol of white solid (approximately 77% yield). The purified product was identified by FAB-MS as having a molecular weight of 390 g / mol, thus confirming the yield of intermediate c.
[0389] 4) Synthesis of intermediate d
[0390] Intermediate d can be synthesized, for example, by the method in reaction scheme D.
[0391] Reaction scheme D
[0392] Intermediate d-1 (200 mmol), intermediate d-2 (440 mmol), and K₂CO₃ (600 mmol) were placed in a three-necked flask, which was purged with argon. 200 mL of NMP was then added, and the mixture was stirred at approximately 150 °C for approximately 32 hours. Water was added to the reaction vessel, and the organic layer was extracted with toluene and then dried over magnesium sulfate to remove the solvent by evaporation. The obtained crude product was purified by silica gel column chromatography (using a mixed solvent of hexane and toluene) and recrystallization (using a mixed solvent of ethanol and toluene) to obtain approximately 125 mmol of white solid (approximately 63% yield). The purified product was identified by FAB-MS as having a molecular weight of 540 g / mol, thus confirming the yield of intermediate d.
[0393] 5) Synthesis of compound B-17
[0394] Compound B-17 according to one embodiment can be synthesized by, for example, the method in reaction scheme 1.
[0395] Reaction Scheme 1
[0396] Intermediate a (131 mmol), intermediate c (1310 mmol), K₂CO₃ (655 mmol), and CuI (131 mmol) were placed in a three-necked flask, which was purged with argon, and the resulting mixture was stirred at approximately 200 °C for approximately 55 hours. Water was added to the reaction vessel, and the organic layer was extracted with toluene and then dried over magnesium sulfate to remove the solvent by evaporation. The obtained crude product was purified by silica gel column chromatography (using a mixed solvent of hexane and toluene) and recrystallization (using a mixed solvent of ethanol and toluene) to obtain approximately 116 mmol of white solid (approximately 89% yield). The purified product was identified by FAB-MS as having a molecular weight of 1055 g / mol, thus confirming the yield of intermediate B-17-1.
[0397] Subsequently, intermediates B-17-1 (116 mmol), B-17-2 (120 mmol), tBuONa (348 mmol), Pd(dba)2 (12 mmol), and [(tBu)3PH]BF4 (24 mmol) were placed in a three-necked flask, which was purged with argon. Then, 600 mL of toluene was added, and the resulting mixture was stirred at approximately 80 °C for approximately 8 hours. Water was added to the reaction vessel, and the organic layer was extracted with toluene and then dried over magnesium sulfate to remove the solvent by evaporation. The obtained crude product was purified by silica gel column chromatography (using a mixed solvent of hexane / toluene) and recrystallization (using a mixed solvent of ethanol / toluene) to obtain approximately 101 mmol of white solid (approximately 87% yield). The purified product was identified by FAB-MS as having a molecular weight of 1295 g / mol, thus confirming the yield of intermediate B-17-3.
[0398] Intermediate B-17-3 (101 mmol) was then placed in a three-necked flask, which was purged with argon. Intermediate B-17-3 was then dissolved by adding 50 mL of o-dichlorobenzene (ODCB), followed by the addition of boron triiodide (BI3) (404 mmol), and the resulting mixture was stirred at approximately 140 °C for approximately 3 hours. The reaction mixture was washed and dispersed with a large amount of acetonitrile, and the solid was then collected by filtration. The obtained crude product was purified by silica gel column chromatography (using a mixed solvent of hexane / toluene) and recrystallization (using a mixed solvent of ethanol / toluene) to obtain approximately 56 mmol of a yellow solid (approximately 55% yield). The purified product was identified by FAB-MS as having a molecular weight of 1311 g / mol, thus confirming the yield of intermediate B-17-4.
[0399] Subsequently, intermediate B-17-4 (56 mmol), carbazole (112 mmol), Pd(dba)2 (6 mmol), SPhos (12 mmol), and tBuONa (168 mmol) were placed in a three-necked flask, which was purged with argon. Then, 50 mL of toluene was added, and the resulting mixture was stirred at approximately 110 °C for approximately 8 hours. Water was added to the reaction vessel, and the organic layer was extracted with toluene and then dried over magnesium sulfate to remove the solvent by evaporation. The obtained crude product was purified by silica gel column chromatography (using a mixed solvent of hexane and toluene) and recrystallization (using a mixed solvent of ethanol and toluene) to obtain approximately 43 mmol of white solid (approximately 77% yield). The purified product was identified by FAB-MS as having a molecular weight of 1441 g / mol, thus confirming the acquisition of compound B-17.
[0400] 6) Synthesis of compound C-18
[0401] Compound C-18 according to one embodiment can be synthesized by, for example, the method in reaction scheme 2.
[0402] Reaction Scheme 2
[0403] Intermediate a (131 mmol), intermediate d (1310 mmol), K₂CO₃ (655 mmol), and CuI (131 mmol) were placed in a three-necked flask, which was purged with argon, and the resulting mixture was stirred at approximately 200 °C for approximately 25 hours. Water was added to the reaction vessel, and the organic layer was extracted with toluene and then dried over magnesium sulfate to remove the solvent by evaporation. The obtained crude product was purified by silica gel column chromatography (using a mixed solvent of hexane and toluene) and recrystallization (using a mixed solvent of ethanol and toluene) to obtain approximately 95 mmol of white solid (approximately 72% yield). The purified product was identified by FAB-MS as having a molecular weight of 1144 g / mol, thus confirming the yield of intermediate C-18-1.
[0404] Intermediate C-18-1 (95 mmol) was then placed in a three-necked flask, which was purged with argon. Intermediate C-18-1 was then dissolved by adding 30 mL of ODCB, followed by the addition of BI3 (380 mmol), and the resulting mixture was stirred at approximately 140 °C for approximately 1 hour. The reaction mixture was washed and dispersed with a large amount of acetonitrile, and the solid was then collected by filtration. The obtained crude product was purified by silica gel column chromatography (using a mixed solvent of hexane / toluene) and recrystallization (using a mixed solvent of ethanol / toluene) to obtain approximately 59 mmol of a yellow solid (approximately 62% yield). The purified product was identified by FAB-MS as having a molecular weight of 1159 g / mol, thus confirming the yield of intermediate C-18-2.
[0405] Subsequently, intermediates C-18-2 (59 mmol), C-18-3 (1310 mmol), K3PO4 (1310 mmol), and Pd(PPh3)4 (6 mmol) were placed in a three-necked flask, which was purged with argon. The resulting mixture was then dissolved in 400 mL toluene, 50 mL H2O, and 25 mL EtOH, and stirred at approximately 110 °C for about 2 hours. Water was added to the reaction vessel, and the organic layer was extracted with toluene and then dried over magnesium sulfate to remove the solvent by evaporation. The obtained crude product was purified by silica gel column chromatography (using a mixed solvent of hexane and toluene) and recrystallization (using a mixed solvent of ethanol and toluene) to give approximately 49 mmol of a yellow solid (approximately 83% yield). The purified product was identified by FAB-MS as having a molecular weight of 1201 g / mol, thus confirming the acquisition of compound C-18.
[0406] 7) Synthesis of compound C-26
[0407] Compound C-26 according to one embodiment can be synthesized by, for example, the method in reaction scheme 3.
[0408] Reaction scheme 3
[0409] Intermediate b (90 mmol), intermediate d (900 mmol), K₂CO₃ (450 mmol), and CuI (90 mmol) were placed in a three-necked flask, which was purged with argon, and the resulting mixture was stirred at approximately 200 °C for approximately 24 hours. Water was added to the reaction vessel, and the organic layer was extracted with toluene and then dried over magnesium sulfate to remove the solvent by evaporation. The obtained crude product was purified by silica gel column chromatography (using a mixed solvent of hexane and toluene) and recrystallization (using a mixed solvent of ethanol and toluene) to obtain approximately 75 mmol of white solid (approximately 83% yield). The purified product was identified by FAB-MS as having a molecular weight of 1338 g / mol, thus confirming the yield of intermediate C-26-1.
[0410] Intermediate C-26-1 was then placed in a three-necked flask, which was purged with argon. Intermediate C-26-1 was then dissolved by adding 30 mL of ODCB, followed by the addition of BI3 (380 mmol), and the resulting mixture was stirred at approximately 140 °C for approximately 2 hours. The reaction mixture was washed and dispersed with a large amount of acetonitrile, and the solid was then collected by filtration. The obtained crude product was purified by silica gel column chromatography (using a mixed solvent of hexane / toluene) and recrystallization (using a mixed solvent of ethanol / toluene) to obtain approximately 25 mmol of a yellow solid (approximately 33% yield). The purified product was identified by FAB-MS as having a molecular weight of 1353 g / mol, thus confirming the yield of intermediate C-26.
[0411] 8) Synthesis of compound H-1
[0412] Compound H-1 according to one embodiment can be synthesized by, for example, the method in reaction scheme 4.
[0413] Reaction scheme 4
[0414] Intermediate H-1-1 (300 mmol), intermediate h-1 (150 mmol), tBuONa (600 mmol), Pd(dba)2 (15 mmol), and (tBu)3PH]BF4 (30 mmol) were placed in a three-necked flask, which was purged with argon. 1000 mL of toluene was added, and the mixture was stirred at 60 °C for about 12 hours. Water was added to the reaction vessel, and the organic layer was extracted with toluene and then dried over magnesium sulfate to remove the solvent by evaporation. The obtained crude product was purified by silica gel column chromatography (hexane / toluene mixed solvent) and recrystallization (ethanol / toluene mixed solvent) to obtain about 120 mmol of white solid (about 40% yield). The purified product of the obtained white solid was identified by FAB-MS as having a molecular weight of 435 g / mol, thus confirming the yield of intermediate H-1-2.
[0415] Subsequently, intermediates H-1-2 (120 mmol), h-2 (1200 mmol), K₂CO₃ (1200 mmol), and CuI (120 mmol) were placed in a three-necked flask, which was purged with argon (Ar), and the mixture was stirred at approximately 210 °C for approximately 65 hours. Water was added to the reaction vessel, and the organic layer was extracted with toluene and then dried over magnesium sulfate to remove the solvent by evaporation. The obtained crude product was purified by silica gel column chromatography (using a mixed solvent of hexane / toluene) and recrystallization (using a mixed solvent of ethanol / toluene) to obtain approximately 105 mmol of white solid (approximately 88% yield). The purified product was identified by FAB-MS as having a molecular weight of 587 g / mol, thus confirming the yield of intermediate H-1-3.
[0416] Intermediate H-1-3 (105 mmol), intermediate h-1 (120 mmol), tBuONa (240 mmol), Pd(dba)2 (10 mmol), and [(tBu)3PH]BF4 (22 mmol) were placed in a three-necked flask, which was purged with argon (Ar), and 300 mL of toluene was added. The resulting mixture was then stirred at about 90 °C for about 6 hours. Water was added to the reaction vessel, and the organic layer was extracted with toluene and then dried over magnesium sulfate to remove the solvent by evaporation. The obtained crude product was purified by silica gel column chromatography (using a mixed solvent of hexane / toluene) and recrystallization (using a mixed solvent of ethanol / toluene) to obtain about 94 mmol of white solid (about 89% yield). The purified product of the obtained white solid was identified by FAB-MS as having a molecular weight of 751 g / mol, thus confirming the yield of intermediate H-1-4.
[0417] Subsequently, intermediates H-1-4 (94 mmol), H-3 (940 mmol), K₂CO₃ (940 mmol), and CuI (94 mmol) were placed in a three-necked flask, which was purged with argon (Ar), and the resulting mixture was stirred at approximately 210 °C for approximately 24 hours. Water was added to the reaction vessel, and the organic layer was extracted with toluene and then dried over magnesium sulfate to remove the solvent by evaporation. The obtained crude product was purified by silica gel column chromatography (using a mixed solvent of hexane / toluene) and recrystallization (using a mixed solvent of ethanol / toluene) to obtain approximately 74 mmol of a white solid (approximately 79% yield). The purified product of the obtained white solid was identified by FAB-MS as having a molecular weight of 985 g / mol, thus confirming the yield of intermediate H-1-5.
[0418] Intermediate H-1-5 (74 mmol), intermediate h-4 (222 mmol), K₂CO₃ (222 mmol), CuI (74 mmol), and dimethylformamide (DMF, 300 mL) were placed in a three-necked flask, which was purged with Ar, and the resulting mixture was stirred at approximately 160 °C for approximately 54 hours. Water was added to the reaction vessel, and the organic layer was extracted with toluene and then dried over magnesium sulfate to remove the solvent by evaporation. The obtained crude product was purified by silica gel column chromatography (using a mixed solvent of hexane / toluene) and recrystallization (using a mixed solvent of ethanol / toluene) to obtain approximately 54 mmol of white solid (approximately 73% yield). The purified product of the obtained white solid was identified by FAB-MS as having a molecular weight of 1164 g / mol, thus confirming the yield of intermediate H-1-6.
[0419] Intermediate H-1-6 (54 mmol) was placed in a three-necked flask, which was purged with argon (Ar). Intermediate H-1-6 was then dissolved by adding 50 mL of ODCB, followed by the addition of BI3 (216 mmol), and the resulting mixture was stirred at approximately 140 °C for approximately 3 hours. The reaction mixture was washed and dispersed with a large amount of acetonitrile, and the solid was then collected by filtration. The obtained crude product was purified by silica gel column chromatography (using a mixed solvent of hexane / toluene) and recrystallization (using a mixed solvent of ethanol / toluene) to obtain approximately 38 mmol of a yellow solid (approximately 70% yield). The purified product of the obtained yellow solid was identified by FAB-MS as having a molecular weight of 1179 g / mol, thus confirming the yield of intermediate H-1-7.
[0420] Intermediate H-1-7 (38 mmol), carbazole (57 mmol), Pd(dba)2 (6 mmol), SPhos (12 mmol), and tBuONa (168 mmol) were placed in a three-necked flask, which was purged with argon (Ar), and then 50 mL of toluene was added. The resulting mixture was then stirred at about 110 °C for about 8 hours. Water was added to the reaction vessel, and the organic layer was extracted with toluene and then dried over magnesium sulfate to remove the solvent by evaporation. The obtained crude product was purified by silica gel column chromatography (using a mixed solvent of hexane / toluene) and recrystallization (using a mixed solvent of ethanol / toluene) to obtain about 30 mmol of yellow solid (about 78% yield). The purified product of the obtained yellow solid was identified by FAB-MS as having a molecular weight of 1310 g / mol, and thus compound H-1 was confirmed.
[0421] 9) Synthesis of compound H-2
[0422] Compound H-2 according to one embodiment can be synthesized by, for example, the method in reaction scheme 5.
[0423] Reaction scheme 5
[0424] Intermediate H-2-1 (300 mmol), intermediate ha (150 mmol), tBuONa (600 mmol), Pd(dba)2 (15 mmol), and [(tBu)3PH]BF4 (30 mmol) were placed in a three-necked flask, which was purged with argon (Ar), and then 1000 mL of toluene was added. The resulting mixture was then stirred at about 60 °C for about 24 hours. Water was added to the reaction vessel, and the organic layer was extracted with toluene and then dried over magnesium sulfate to remove the solvent by evaporation. The obtained crude product was purified by silica gel column chromatography (hexane / toluene mixed solvent) and recrystallization (ethanol / toluene mixed solvent) to obtain about 160 mmol of white solid (about 53% yield). The purified product of the obtained white solid was identified by FAB-MS as having a molecular weight of 477 g / mol, and thus compound H-2-2 was confirmed.
[0425] Subsequently, intermediate H-2-2 (160 mmol), intermediate hb (1600 mmol), K2CO3 (1600 mmol), and CuI (160 mmol) were placed in a three-necked flask, which was purged with argon (Ar), and the resulting mixture was stirred at approximately 210 °C for approximately 24 hours. Water was added to the reaction vessel, and the organic layer was extracted with toluene and then dried over magnesium sulfate to remove the solvent by evaporation. The obtained crude product was purified by silica gel column chromatography (using a mixed solvent of hexane / toluene) and recrystallization (using a mixed solvent of ethanol / toluene) to obtain approximately 151 mmol of white solid (approximately 94% yield). The purified product of the obtained white solid was identified by FAB-MS as having a molecular weight of 553 g / mol, thus confirming the yield of intermediate H-2-3.
[0426] Intermediate H-2-3 (300 mmol), intermediate ha (200 mmol), tBuONa (300 mmol), Pd(dba)2 (10 mmol), and [(tBu)3PH]BF4 (22 mmol) were placed in a three-necked flask, which was purged with argon (Ar), and then 300 mL of toluene was added. The resulting mixture was then stirred at about 90 °C for about 9 hours. Water was added to the reaction vessel, and the organic layer was extracted with toluene and then dried over magnesium sulfate to remove the solvent by evaporation. The obtained crude product was purified by silica gel column chromatography (hexane / toluene mixed solvent) and recrystallization (ethanol / toluene mixed solvent) to obtain about 130 mmol of white solid (about 86% yield). The purified product of the obtained white solid was identified by FAB-MS as having a molecular weight of 717 g / mol, and thus compound H-2-4 was confirmed.
[0427] Subsequently, intermediate H-2-4 (130 mmol), intermediate hc (1300 mmol), K2CO3 (1300 mmol), and CuI (130 mmol) were placed in a three-necked flask, which was purged with argon (Ar), and the mixture was stirred at approximately 210 °C for approximately 30 hours. Water was added to the reaction vessel, and the organic layer was extracted with toluene and then dried over magnesium sulfate to remove the solvent by evaporation. The obtained crude product was purified by silica gel column chromatography (using a mixed solvent of hexane / toluene) and recrystallization (using a mixed solvent of ethanol / toluene) to obtain approximately 111 mmol of white solid (approximately 85% yield). The purified product of the obtained white solid was identified by FAB-MS as having a molecular weight of 1116 g / mol, thus confirming the acquisition of compound H-2-5.
[0428] Intermediate H-2-5 (111 mmol), intermediate hd (200 mmol), tBuONa (600 mmol), Pd(dba)2 (15 mmol), and [(tBu)3PH]BF4 (30 mmol) were placed in a three-necked flask, which was purged with argon (Ar), and then 200 mL of toluene was added. The resulting mixture was then stirred at about 90 °C for about 24 hours. Water was added to the reaction vessel, and the organic layer was extracted with toluene and then dried over magnesium sulfate to remove the solvent by evaporation. The obtained crude product was purified by silica gel column chromatography (hexane / toluene mixed solvent) and recrystallization (ethanol / toluene mixed solvent) to obtain about 105 mmol of white solid (about 95% yield). The purified product of the obtained white solid was identified by FAB-MS as having a molecular weight of 1281 g / mol, and thus compound H-2-6 was confirmed.
[0429] Intermediate H-2-6 (105 mmol) was placed in a three-necked flask, which was purged with argon (Ar). H-2-6 was then dissolved by adding 50 mL of ODCB, followed by the addition of BI3 (420 mmol), and the resulting mixture was stirred at approximately 140 °C for approximately 2 hours. The reaction mixture was washed and dispersed with a large amount of acetonitrile, and the solid was collected by filtration. The obtained crude product was purified by silica gel column chromatography (using a mixed solvent of hexane / toluene) and recrystallization (using a mixed solvent of ethanol / toluene) to obtain approximately 55 mmol of a yellow solid (approximately 52% yield). The purified product of the obtained yellow solid was identified by FAB-MS as having a molecular weight of 1296 g / mol, thus confirming the acquisition of compound H-2.
[0430] 2. Evaluation of the fluorescence and luminescence properties of the compound
[0431] The fluorescence and luminescence properties of the polycyclic compounds according to the examples and comparative examples were evaluated, and the results are listed in Table 1. To evaluate the luminescence properties, the fluorescence and luminescence spectra of a 20 wt% doped film generated by depositing PPF as a matrix onto quartz glass were measured using a JASCO V-670 spectrometer. The fluorescence quantum yield was measured using a JASCO ILF-835 integrating sphere system.
[0432] Compounds used to evaluate fluorescence properties
[0433] Example Compounds
[0434] Comparative compounds
[0435] Table 1
[0436] Referring to the results in Table 1, it is confirmed that compounds B-17, C-18, C-26, H-1, and H-2 of Examples are suitable as luminescent materials because each of them emits light in the wavelength region of about 450 nm to about 470 nm and their fluorescence quantum yield is measured to be about 80% or higher. Furthermore, it is confirmed that each comparative example compound emits light in the wavelength range of about 450 nm to about 470 nm and exhibits a fluorescence quantum yield at a level similar to that of the example compounds.
[0437] 3. Manufacturing and evaluation of light-emitting elements
[0438] The polycyclic compounds according to the examples and comparative examples were manufactured by the following methods. Compounds B-17, C-18, C-26, H-1, and H-2, which are polycyclic compounds according to one or more embodiments, were used as dopant materials for the emission layer to manufacture the light-emitting elements according to Examples 1 to 5. Comparative example compounds X-1 to X-3 were used as dopant materials for the emission layer to manufacture the light-emitting elements according to Comparative Examples 1 to 3.
[0439] (1) Manufacturing of light-emitting elements
[0440] A first electrode with a thickness of approximately 1500 Å was formed or composed of ITO, then cleaned with ultrapure water and subjected to UV ozone treatment for approximately 10 minutes. Subsequently, a hole injection layer with a thickness of approximately 100 Å was formed on the first electrode using dipyrazine-[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarboxynitrile (HAT-CN), and a hole transport layer with a thickness of approximately 400 Å was formed on the hole injection layer using α-NPD.
[0441] An electron blocking layer with a thickness of about 50 Å was formed on the hole transport layer using 3,3'-bis(9H-carbazole-9-yl)-1,1'-biphenyl (mCBP), and an emission layer was formed by mixing the compound of the examples or comparative examples with mCBP at a ratio of about 20:80. In this case, the emission layer was formed to a thickness of about 200 Å. An electron transport layer with a thickness of about 300 Å was formed on the emission layer using 2,2',2''-(1,3,5-phenyltriyl)-tris(1-phenyl-1-H-benzimidazole) (TPBi), and an electron injection layer with a thickness of about 5 Å was formed on the electron transport layer using Liq. Subsequently, a second electrode with a thickness of about 1000 Å was formed on the electron injection layer using aluminum (Al). Each layer was formed by deposition under a vacuum atmosphere.
[0442] This document discloses compounds for manufacturing light-emitting elements according to the examples and comparative examples. Each material is a commonly available material, and commercially available products are purified by sublimation and used in the manufacture of the elements.
[0443] The following compounds are used to manufacture light-emitting elements.
[0444] Common materials used in manufacturing light-emitting elements
[0445] (2) Evaluation of the characteristics of the light-emitting element
[0446] The characteristics of the light-emitting elements according to Examples 1 to 5 and Comparative Examples 1 to 3 were evaluated, and the results are listed in Table 2. For the evaluation of the light-emitting elements, voltage, current density, and maximum emission wavelength (λmax, nm) were measured using a source meter (Keithley Instrument, Inc., 2400 series) and a luminance meter PR650. Luminance and maximum external quantum efficiency (EQE) were measured using an external quantum efficiency measurement system C9920-12 manufactured by Hamamatsu Photonics KK. max , %). In Table 2, LT 50 Expressed as a relative value of the half-life of Comparative Example 1 relative to 100%.
[0447] Table 2
[0448] Referring to the results in Table 2, the light-emitting elements according to the embodiments exhibit similar emission wavelength characteristics to the light-emitting elements according to the comparative examples, which contain comparative example compounds, each having a core structure similar to that of the compound in the embodiments. Furthermore, it can be confirmed that, compared to the light-emitting elements according to the comparative examples, the light-emitting elements according to the embodiments using polycyclic compounds according to one or more embodiments as the light-emitting material have superior or suitable luminous efficiency, for example, significantly or substantially improved or enhanced characteristics in terms of element lifespan. For example, it can be seen that because the light-emitting elements according to the embodiments each contain a polycyclic compound according to one or more embodiments with improved or enhanced material stability in the emission layer, the polycyclic compound exhibits reduced degradation in the emission layer, and therefore the luminous efficiency of the emission layer and the lifespan characteristics of the element are improved or enhanced.
[0449] The results in Table 2 confirm that, because the first substituent is attached to at least one nitrogen atom of the core in the polycyclic compound according to one or more embodiments and at least two first substituents are additionally attached, the resonance stability is improved or enhanced, the molecular planarity is weakened, and the boron atom of the core is spatially protected. Therefore, it can be confirmed that if the polycyclic compound according to one or more embodiments is used as a luminescent material (e.g., when the polycyclic compound according to one or more embodiments is used as a luminescent material), it exhibits long service life characteristics.
[0450] In the compounds used in the light-emitting elements according to Examples 1 to 5, compared to the comparative example compounds, the first substituent of the phenyl group is connected to at least one nitrogen atom contained in the core, and two or three phenyl groups are additionally connected to the first substituent, thus increasing or enhancing the steric protection effect on the core. Therefore, the light-emitting elements according to Examples 1 to 5 each have increased or enhanced luminous efficiency and increased element stability.
[0451] Conversely, because only one unsubstituted phenyl group is connected to each of the nitrogen atoms in the nucleus of the comparative compound X-1 used in the light-emitting element according to Comparative Example 1, molecular distortion occurs due to steric hindrance, and thus the resonance stability of the nucleus deteriorates, and the lifespan of the element is shortened.
[0452] In the comparative example compound X-3 used in the light-emitting element according to Comparative Example 3, the overall planarity of the molecule is increased due to the introduction of three boron atoms into the nucleus, and therefore concentration quenching is more likely to occur. Therefore, compared to the light-emitting element according to the embodiments, the light-emitting element according to Comparative Example 3 exhibits slightly degraded luminous efficiency and lifespan characteristics.
[0453] In a light-emitting element according to one or more embodiments, the emitting layer may comprise a polycyclic compound according to one or more embodiments. The polycyclic compound according to one or more embodiments may comprise a fused ring having nine rings as the core structure, comprising four heteroatoms and two boron atoms as cyclic atoms, and the core of the fused ring with nine rings may comprise at least one nitrogen atom as a heteroatom linked to a first substituent and multiple first daughter substituents. Therefore, the polycyclic compound according to one or more embodiments may have a structure in which the fused ring core with nine rings is protected, and its molecular planarity is reduced. Therefore, in the polycyclic compound according to one or more embodiments, because the multi-resonance core region where the luminescence-related transition occurs is protected, intermolecular interactions that could cause side reactions other than luminescence can be suppressed or reduced, and thus the material stability can be increased or enhanced. Furthermore, light-emitting elements comprising a polycyclic compound according to one or more embodiments in the emitting layer can exhibit high luminous efficiency and long lifetime characteristics.
[0454] The light-emitting element according to one or more embodiments may contain polycyclic compounds according to one or more embodiments in the emitting layer, and thus may exhibit high luminous efficiency and long lifespan characteristics.
[0455] Polycyclic compounds according to one or more implementation schemes can help improve or enhance luminous efficiency and extend lifespan.
[0456] An electronic device according to one or more implementation schemes can exhibit excellent or adequate display quality.
[0457] In the foregoing, certain embodiments of this disclosure have been described and illustrated. However, it will be apparent to those skilled in the art that this disclosure is not limited to the described embodiments, and that suitable modifications and variations can be made without departing from the spirit and scope of this disclosure. Such modified or varied embodiments should not be understood independently of the technical concept and aspects of one or more embodiments of this disclosure, and the modified embodiments are within the scope of the appended claims and their equivalents.
Claims
1. Electronic devices, including: The display panel includes multiple light-emitting elements. At least one of the plurality of light-emitting elements includes a first electrode, a second electrode opposite to the first electrode, and an emitting layer provided between the first electrode and the second electrode and comprising a polycyclic compound represented by Formula 1: Formula 1 , In Equation 1, Rings a, b, c, d, and e are each independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heterocycle containing heteroatoms other than boron atoms as cyclic atoms and having 2 to 30 cyclic carbon atoms, or bonded to adjacent groups to form a ring. X1, X2, Z1, and Z2 are each independently O, S, and NR. a or NR b And at least one of X1, X2, Z1 and Z2 is NR. b , R a It is a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or bonded to an adjacent group to form a ring, and R b Equation 2 represents: Formula 2 , In Equation 2, R1 to R5 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted amine group, a substituted or unsubstituted silyl 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 are bonded to adjacent groups to form a ring, or are represented by Formula 3. This refers to the position to be connected, and At least two of the choices R1 to R5 are represented by Equation 3: Formula 3 , In Equation 3, Q1 to Q5 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, or bonded to an adjacent group to form a ring, and This refers to the position to be connected.
2. The electronic device as claimed in claim 1, comprising a display device, The display device includes the display panel. The display device further includes a first emitting region, a second emitting region, and a third emitting region, each of which is arranged to emit light in a different wavelength region and is distinguishable from one another on a plane. The first emitting region, the second emitting region, and the third emitting region are each of the regions arranged to emit light generated in each of the plurality of light-emitting elements.
3. The electronic device of claim 2, wherein each of the plurality of light-emitting elements includes a first light-emitting element arranged to correspond to the first emitting region, a second light-emitting element arranged to correspond to the second emitting region, and a third light-emitting element arranged to correspond to the third emitting region.
4. The electronic device of claim 2, wherein the display device comprises a plurality of display surfaces, each of the plurality of display surfaces having a different primary display orientation.
5. The electronic device as claimed in claim 1, comprising a plurality of independently controlled display devices. At least one of the plurality of display devices includes the display panel.
6. The electronic device of claim 1, further comprising at least one selected from a processor, a memory, and a power module.
7. The electronic device as claimed in claim 1, The electronic device is a television, monitor, billboard, personal computer, laptop computer, personal digital assistant, vehicle equipment, game console, smartphone, tablet computer, smartwatch, or camera.
8. Light-emitting elements, including: First electrode; The second electrode is opposite to the first electrode; as well as An emission layer is provided between the first electrode and the second electrode and comprises a first compound represented by Formula 1: Formula 1 , In Equation 1, Rings a, b, c, d, and e are each independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heterocycle containing heteroatoms other than boron atoms as cyclic atoms and having 2 to 30 cyclic carbon atoms, or bonded to adjacent groups to form a ring. X1, X2, Z1, and Z2 are each independently O, S, and NR. a or NR b And at least one of X1, X2, Z1 and Z2 is NR. b , R a It is a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or bonded to an adjacent group to form a ring, and R b Equation 2 represents: Formula 2 , In Equation 2, R1 to R5 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted amine group, a substituted or unsubstituted silyl 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 are bonded to adjacent groups to form a ring, or are represented by Formula 3. This refers to the position to be connected, and At least two of the choices R1 to R5 are represented by Equation 3: Formula 3 , In Equation 3, Q1 to Q5 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, or bonded to an adjacent group to form a ring, and This refers to the position to be connected.
9. The light-emitting element as claimed in claim 8, wherein formula 2 is represented by formula 2-1: Equation 2-1 , in, In Equation 2-1, The R2', R3', R4', and R5' are selected from one or two of them represented by Formula 3, and the remaining R2', R3', R4', and R5' that are not represented by Formula 3 are each 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. Q1 to Q5 are the same as those defined in Equation 3, and This refers to the position to be connected.
10. The light-emitting element as described in claim 8, At least one of X1, X2, and Z2 is NR. b ,as well as Z1, and X1, X2, and Z2 are not NR b The remainder are each independently O, S, or NR. a , R a and R b Same as defined in Equation 1.
11. The light-emitting element of claim 8, wherein the first compound represented by formula 1 is represented by formula 4: Formula 4 , in, In Equation 4, R6 to R 21 Each of the following is independently a hydrogen atom, a deuterium atom, a cyano group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 30 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 is bonded to an adjacent group to form a ring. X1, X2, Z1, and Z2 are the same as those defined in Equation 1.
12. The light-emitting element as described in claim 11, The first compound represented by Formula 4 is represented by any one of Formulas 5-1 to 5-3: Formula 5-1 , Formula 5-2 ,as well as Formula 5-3 , in, In equations 5-1 to 5-3, X 11 X 12 and Z 12 Each is independent of the other: O, S, NR. a or NR b , Z 11 Is it O, S, or NR? a , R a and R b Same as defined in Equation 1, R1 to R5 are the same as those defined in Equation 2, and R6 to R 21 Same as defined in Equation 4.
13. The light-emitting element of claim 11, wherein the first compound represented by formula 4 is represented by any one selected from formulas 6-1 to 6-6: Equation 6-1 , Formula 6-2 , Formula 6-3 , Formula 6-4 , Formula 6-5 ,as well as Formula 6-6 , in, In equations 6-1 to 6-6, X 21 X 22 Z 21 and Z 22 Each is independently O, S, or NR. a , Selected from R a2 To R a5 At least one of them, selected from R b2 To R b5 At least one of them and selected from R c2 To R c5 At least one of them is independently represented by Equation 3. R a2 To R a5 R b2 To R b5 and R c2 To R c5 The remainder not represented by Formula 3 are each 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. Q 11 To Q 15 Q 21 To Q 25 and Q 31 To Q 35 Each group is independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted tert-butyl group, or a substituted or unsubstituted phenyl group, or is bonded to an adjacent group to form a ring. R a Same as defined in Equation 1, and R6 to R 21 Same as defined in Equation 4.
14. The light-emitting element as claimed in claim 11, wherein R6 to R 21 Each of these groups is independently a hydrogen atom, a deuterium atom, a cyano group, a substituted or unsubstituted diphenylamine group, a substituted or unsubstituted propyl group, a substituted or unsubstituted tert-butyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted carbazole group, or a substituted or unsubstituted dibenzofuran group.
15. The light-emitting element of claim 8, wherein at least one of the hydrogen atoms selected from the first compound represented by Formula 1 is replaced by a deuterium atom.
16. The light-emitting element of claim 8, wherein the emitting layer emits blue light.
17. The light-emitting element of claim 8, wherein the emitting layer further comprises at least one selected from the following: 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 either N or CR. 51 , L1 is a linearly bonded, 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 It is a direct-connect key, 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 groups is independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted thio group, a substituted or unsubstituted oxy group, a substituted or unsubstituted amine group, a substituted or unsubstituted boron group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 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 is bonded to an adjacent group to form a ring: ET-1 , In Equation ET-1, Selected from Z a To Z c At least one of them is N, and the rest are CR. 56 , R 56 It is a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 cyclic carbon atoms. e1 to e3 are each an independent integer 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, and L2 to L4 are each independently a straight-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 through Q4 are each independently either C or N. C1 through C4 are each independently a substituted or unsubstituted hydrocarbon ring having 5 to 30 cyclic carbon atoms, or a substituted or unsubstituted heterocycle having 2 to 30 cyclic carbon atoms. L 11 To L 13 Each is an independent direct-connect key. , , , The following are considered 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. This refers to the position to be connected. b11 to b13 are each independently 0 or 1. R 61 To R 66 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 amine group, a substituted or unsubstituted boron group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 cyclic carbon atoms, or is bonded to an adjacent group to form a ring, and d1 to d4 are each an independent integer from 0 to 4.
18. Polycyclic compounds represented by Formula 1: Formula 1 In Equation 1, Rings a, b, c, d, and e are each independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heterocycle containing heteroatoms other than boron atoms as cyclic atoms and having 2 to 30 cyclic carbon atoms, or bonded to adjacent groups to form a ring. X1, X2, Z1, and Z2 are each independently O, S, and NR. a or NR b And at least one of X1, X2, Z1 and Z2 is NR. b , R a It is a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or bonded to an adjacent group to form a ring, and R b Equation 2 represents: Formula 2 , in, In Equation 2, R1 to R5 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted amine group, a substituted or unsubstituted silyl 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 are bonded to adjacent groups to form a ring, or are represented by Formula 3. This refers to the position to be connected, and At least two of the choices R1 to R5 are represented by Equation 3: Formula 3 , In Equation 3, Q1 to Q5 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, or bonded to an adjacent group to form a ring, and This refers to the position to be connected.
19. The polycyclic compound of claim 18, wherein formula 2 is represented by formula 2-1: Equation 2-1 , in, In Equation 2-1, The R2', R3', R4', and R5' are selected from one or two of them represented by Formula 3, and the remaining R2', R3', R4', and R5' that are not represented by Formula 3 are each 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. Q1 to Q5 are the same as those defined in Equation 3, and This refers to the position to be connected.
20. The polycyclic compound of claim 18, wherein formula 1 is represented by formula 4: Formula 4 , in, In Equation 4, R6 to R 21 Each of the following is independently a hydrogen atom, a deuterium atom, a cyano group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 30 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. X1, X2, Z1, and Z2 are the same as those defined in Equation 1.