Condensed polycyclic compound, light-emitting device, and display apparatus including light-emitting device
By using specific fused polycyclic compounds in the emission layer of an organic electroluminescent display device, the problem of insufficient emission efficiency and service life in the prior art is solved, and a more efficient and stable display effect is achieved.
Patent Information
- Application Number
- CN202411004534.1
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Priority Date
- 2023-07-28
- Filing Date
- 2024-07-25
- Publication Date
- 2025-02-14
AI Technical Summary
The emission efficiency and service life of existing organic electroluminescent display devices are insufficient, making it difficult to meet the demand for stable and efficient display.
The emission layer containing a specific fused polycyclic compound is used to improve the light efficiency and service life. The fused polycyclic compound is represented by Formula 1 and contains a variety of substituents and a ring-like structure for the emitting layer of a light emitting device.
The emission efficiency and service life of the light emitting device are improved, and a more stable image display effect is achieved.
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Figure CN119431413A_ABST
Abstract
Description
[0001] CROSS-REFERENCE TO RELATED APPLICATIONS
[0002] This application claims priority to and the benefit of Korean Patent Application No. 10-2023-0098786 filed in the Korean Intellectual Property Office on July 28, 2023, the entire contents of which are incorporated herein by reference. Technical Field
[0003] Embodiments of the present disclosure described herein relate to a light-emitting device, a fused polycyclic compound for the light-emitting device, and a display apparatus including the light-emitting device. Background Art
[0004] Recently, development of organic electroluminescent display devices as image display devices is being actively carried out. The organic electroluminescent display device is a display device including a self-luminous type or type light-emitting device in which holes and electrons injected from a first electrode and a second electrode (e.g., separately or individually) recombine in an emission layer so that the light-emitting material in the emission layer emits light to achieve display (e.g., of an image).
[0005] In the application of light emitting devices to display apparatuses, increases in emission efficiency and lifetime are required and / or desired, and thus development of materials for light emitting devices that stably achieve the requirements is continuously required and / or sought. Summary of the invention
[0006] Aspects according to one or more embodiments of the present disclosure are directed to a light emitting device having improved emission efficiency and lifetime, and a display apparatus including the light emitting device.
[0007] An aspect according to one or more embodiments of the present disclosure relates to a condensed polycyclic compound as a material for a light emitting device and improving light efficiency and lifetime.
[0008] Additional aspects will be set forth in part in the description which follows and, in part, will be obvious from the description, or may be learned by practice of the presented embodiments of the disclosure.
[0009] According to one or more embodiments, the light emitting device may include: a first electrode; a second electrode disposed on the first electrode; and an emission layer disposed between the first electrode and the second electrode and including a first compound represented by Formula 1.
[0010] Formula 1
[0011]
[0012] In formula 1, R1 To R 8 each independently may be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 ring-forming carbon atoms, and / or may combine (e.g., bond) with an adjacent group to form a ring, n1 to n4 may each independently be an integer of 0 to 5, R a1 To R a6 and R b1 To R b4 may each independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thiol group, a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 ring carbon atoms, and / or combine with an adjacent group to form a ring, m1 and m2 may each independently be an integer of 0 to 4, and R c1 and R c2 Each of them may independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thiol group, a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 ring-forming carbon atoms.
[0013] According to one or more embodiments, the emission layer may further include at least one selected from the second compound represented by Formula HT-1, the third compound represented by Formula ET-1, and the fourth compound represented by Formula D-1.
[0014] Formula HT-1
[0015]
[0016] In formula H-1, A 1 To A 8 Can be N or CR independently 51 , L 1is a direct bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms, Y a It is a direct key, CR 52 R 53 or SiR 54 R 55 ,Ar 1 may be a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, and R 51 and R 55 Each may independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted thiol 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 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 ring-forming carbon atoms, and / or combine with an adjacent group to form a ring.
[0017] Formula ET-1
[0018]
[0019] In formula ET-1, selected from X 1 To X 3 At least one of them is N, and the rest are CR 56 , R 56 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 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 ring carbon atoms, b1 to b3 may each independently be an integer of 0 to 10, Ar 2 To Ar 4 may 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 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, and L 2 To L 4 Each may independently be a direct bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms.
[0020] Formula D-1
[0021]
[0022] In formula D-1, Q 1 To Q 4 may be each independently C or N, C1 to C4 may each independently be a substituted or unsubstituted hydrocarbon ring having 5 to 30 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocycle having 2 to 30 ring carbon atoms, L 11 To L 13 Can be directly connected, *-O-*, *-S-*, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms, b11 to b13 may each independently be 0 or 1, R 61 To R 66 Each of d1 to d4 may be independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted thiol 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 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 ring carbon atoms, and d1 to d4 may be independently an integer of 0 to 4. In L 11 To L 13 In the figure, “-*” refers to the part connected to C1 to C4.
[0023] According to one or more embodiments, Formula 1 may be represented by Formula 1-A.
[0024] Formula 1-A
[0025]
[0026] In Formula 1-A, R 16 and R 17 may each independently be a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, R d1 To R d8each independently may be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted amine group, a substituted or unsubstituted thiol group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, and / or may combine with an adjacent group to form a ring, and n1 to n4, R a1 To R a6 , R b1 To R b4 、m1、m2、R c1 and R c2 and may be the same as defined in Formula 1, respectively, independently.
[0027] According to one or more embodiments, Formula 1-A can be represented by Formula 1-A1.
[0028] Formula 1-A1
[0029]
[0030] In Formula 1-A1, R d11 To R d18 each independently may be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted amine group, a substituted or unsubstituted thiol group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, and / or may combine with an adjacent group to form a ring, and n1 to n4, R a1 To R a6 , R b1 To R b4 、m1、m2、R c1 , R c2 , R d1 To R d8 and may be independently the same as defined in Formula 1-A.
[0031] According to one or more embodiments, in Formula 1, R 1 To R 8 Each may independently be a hydrogen atom, a deuterium atom, or be represented by one selected from R-1 to R-26.
[0032]
[0033] In R-5, R-9, R-13, and R-16 to R-26, D is a deuterium atom, and in R-1 to R-26, "-*" refers to a position to be linked.
[0034] According to one or more embodiments, in Formula 1, R 1 To R 8 Each may independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted tert-butyl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted carbazole group, a substituted or unsubstituted dibenzofuran group, or a substituted or unsubstituted benzothienylcarbazole group.
[0035] According to one or more embodiments, Formula 1 may be represented by one selected from Formula 1-B1 to Formula 1-B3.
[0036] Formula 1-B1
[0037]
[0038] Formula 1-B2
[0039]
[0040] Formula 1-B3
[0041]
[0042] In formula 1-B2, R b11 , R b12 , R b21 To R b23 , R b31 , R b32 and R b41 To R b43 may each independently be a hydrogen atom, a deuterium atom, a cyano group, a substituted or unsubstituted amine group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thiol group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, and / or combine with an adjacent group to form a ring. In Formula 1-B3, Q 11 and Q 12 Can be NR independently 21 , O or S, n5 and n6 may each independently be an integer from 0 to 7, and R 21 To R 23 may be independently a hydrogen atom, a deuterium atom, or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms. In Formula 1-B2 and Formula 1-B3, R a12 and R a15may each independently be a hydrogen atom, a deuterium atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, and in Formula 1-B1 to Formula 1-B3, R 1 To R 8 、n1、n3、R b1 , R b3 、m1、m2、R c1 and R c2 and may be the same as defined in Formula 1, respectively, independently.
[0043] According to one or more embodiments, in Formula 1, R c1 and R c2 They may each independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted methyl group, a substituted or unsubstituted tert-butyl group, or a substituted or unsubstituted phenyl group.
[0044] According to one or more embodiments, in Formula 1, R c1 and R c2 Each may independently be a hydrogen atom, a deuterium atom, or be represented by one selected from RC-1 to RC-4.
[0045]
[0046] In RC-1, D is a deuterium atom, and in RC-1 to RC-4, "-*" refers to the position to be attached.
[0047] According to one or more embodiments, the first compound may contain a deuterium atom, or a substituent containing a deuterium atom.
[0048] According to one or more than one embodiments, the fused polycyclic compound may be represented by Formula 1.
[0049] According to one or more embodiments, a display device may include: a base layer; a circuit layer disposed on the base layer; and a display device layer disposed on the circuit layer and including a light-emitting device, wherein the light-emitting device includes a first electrode, a second electrode disposed on the first electrode, and an emission layer, the emission layer being disposed between the first electrode and the second electrode and comprising a fused polycyclic compound represented by Formula 1.
[0050] According to one or more embodiments, the light-emitting device may include a first light-emitting device configured to emit red light, a second light-emitting device configured to emit green light, and a third light-emitting device configured to emit blue light, and the fused polycyclic compound may be contained in the third light-emitting device.
[0051] According to one or more embodiments, the light emitting device may be configured to emit blue light.
[0052] According to one or more embodiments, the display apparatus may further include a light management layer disposed on the display device layer and comprising quantum dots. BRIEF DESCRIPTION OF THE DRAWINGS
[0053] The accompanying drawings are included to provide a further understanding of the present disclosure and are incorporated in and constitute a part of this specification. The accompanying drawings illustrate embodiments of the present disclosure and together with the description serve to explain the principles of the present disclosure. In the drawings:
[0054] Figure 1 is a plan view showing a display device according to the embodiment;
[0055] Figure 2 is shown along Figure 1 A cross-sectional view of a portion taken along line II′;
[0056] Figure 3 is a cross-sectional view schematically showing a light emitting device of the embodiment;
[0057] Figure 4 is a cross-sectional view schematically showing a light emitting device of the embodiment;
[0058] Figure 5 is a cross-sectional view schematically showing a light emitting device of the embodiment;
[0059] Figure 6 is a cross-sectional view schematically showing a light emitting device of the embodiment;
[0060] Figure 7 is a cross-sectional view schematically showing a light emitting device of the embodiment;
[0061] Figure 8 is a cross-sectional view showing a display device according to the embodiment;
[0062] Fig. 9 is a cross-sectional view showing a display device according to the embodiment;
[0063] Fig.10 is a cross-sectional view showing a display device according to the embodiment;
[0064] Fig.11 is a cross-sectional view showing a display device according to the embodiment; and
[0065] Fig.12is a diagram showing the interior of a vehicle in which the display device of the embodiment is provided. DETAILED DESCRIPTION
[0066] Because the present disclosure can have different modified embodiments, specific embodiments are illustrated in the drawings and described in the detailed description of the present disclosure. However, this does not limit the present disclosure to specific embodiments, and it should be understood that the present disclosure covers all modifications, equivalents and substitutions within the concept and technical scope of the present disclosure.
[0067] In this specification, it should also be understood that when a component (or region, layer, part) is referred to as being "on", "connected to" or "coupled to" another component, it can be directly disposed on / directly connected to / directly coupled to a component, or a third component may also be present in between.
[0068] The same reference numerals refer to the same elements throughout the text, and their repeated descriptions may not be provided. In addition, in the accompanying drawings, the thickness, ratio and size of the components are exaggerated for clarity of illustration. The term "and / or" includes any combination and all combinations of one or more than one of the related components.
[0069] It should be understood that although terms such as "first" and "second" are used herein to describe one or more than one suitable element, these elements should not be limited by these terms. These terms are only used to distinguish one component from other components. For example, without departing from the scope of the appended claims, a first element referred to as a first element in an embodiment may be referred to as a second element in another embodiment. Terms in the singular may include plural forms unless otherwise indicated.
[0070] In addition, “lower”, “below”, “above”, “upper”, etc. are used to explain the relationship between elements illustrated in the drawings. These terms may be relative concepts and are described based on the directions shown in the drawings.
[0071] The meaning of “include” or “comprise” specifies properties, fixed values, processes, operations, elements, components or a combination thereof, but does not exclude other properties, fixed values, processes, operations, elements, components or a combination thereof.
[0072] Unless otherwise defined, all terms (including technical terms and scientific terms) used herein have the same meaning as commonly understood by those of ordinary skill in the art to which the present disclosure belongs. In some embodiments, terms (such as those defined in commonly used dictionaries) should be interpreted as having a meaning consistent with the meaning in the context of the relevant technology, and unless clearly defined herein, they should not be interpreted as overly ideal or overly formal meanings.
[0073] In the specification, term " replace or be unsubstituted " can refer to be selected from at least one substituent in the group including deuterium atom, halogen atom, cyano group, nitro group, amine group, silyl group, oxy group, sulfenyl group, sulfinyl group, sulfonyl group, carbonyl group, boron group, phosphine oxide group, phosphine sulfide group, alkyl group, alkenyl group, alkynyl group, hydrocarbon ring group, aryl group and heterocyclic group and replace, or unsubstituted.In some embodiments, each in previously described substituent can be replaced or be unsubstituted.For example, biphenyl group can be interpreted as aryl group or the phenyl group substituted by phenyl group.
[0074] In the specification, the phrase "bonded to an adjacent group to form a ring" may refer to a group bonded to an adjacent group to form a substituted or unsubstituted hydrocarbon ring, or a substituted or unsubstituted heterocycle. Hydrocarbon rings include aliphatic hydrocarbon rings and aromatic hydrocarbon rings. Heterocycles include aliphatic heterocycles and aromatic heterocycles. Hydrocarbon rings and heterocycles may be monocyclic or polycyclic. In some embodiments, the ring formed by bonding to each other may be connected to another ring to form a spiro structure.
[0075] In the specification, the term "adjacent group" may refer to a substituent that replaces an atom directly connected to the atom substituted by the corresponding substituent, another substituent that replaces the atom substituted by the corresponding substituent, or a substituent that is spatially located at the closest position to the corresponding substituent. For example, the two methyl groups in 1,2-dimethylbenzene may be interpreted as "adjacent groups" to each other, and the two ethyl groups in 1,1-diethylcyclopentane may be interpreted as "adjacent groups" to each other. In some embodiments, the two methyl groups in 4,5-dimethylphenanthrene may be interpreted as "adjacent groups" to each other.
[0076] In the specification, examples of the halogen atom may include a fluorine atom, a chlorine atom, a bromine atom or an iodine atom.
[0077] In the specification, the alkyl group may be straight chain or branched. The number of carbon atoms in the alkyl group is 1 to 60, 1 to 50, 1 to 30, 1 to 20, 1 to 10 or 1 to 6. Examples of the alkyl group may include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, a tert-butyl group, an isobutyl group, a 2-ethylbutyl group, a 3,3-dimethylbutyl group, an n-pentyl group, an isopentyl group, a neopentyl group, a tert-pentyl group, a 1-methylpentyl group, a 3-methylpentyl group, a 2-ethylpentyl group, a 4-methyl-2-pentyl group, an n-hexyl group, a 1-methylhexyl group, a 2-ethyl 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, An n-undecyl group, an n-dodecyl group, a 2-ethyldodecyl group, a 2-butyldodecyl group, a 2-hexyldodecyl group, a 2-octyldodecyl group, an n-tridecyl group, an n-tetradecyl group, an n-pentadecyl group, an n-hexadecyl group, a 2-ethylhexadecyl group, a 2-butylhexadecyl group, a 2-hexylhexadecyl group, a 2-octylhexadecyl group, an n-heptadecyl group, an n-octadecyl group, an n-nonadecyl group, an n-eicosyl group, a 2-ethyleicosyl group, a 2-butyleicosyl group, a 2-hexyleicosyl group, a 2-octyleicosyl group, an n-heneicosyl group, an n-docosyl group, an n-tricosyl group, an n-tetracosyl group, an n-pentacosyl group, an n-hexacosyl group, an n-heptacosyl group, an n-octacosyl group, an n-nonacosyl group, an n-triacontyl group, and the like, but the embodiments of the present disclosure are not limited thereto.
[0078] In the specification, the cycloalkyl group may refer to a cyclic alkyl group. The number of carbon atoms in the cycloalkyl group is 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 the present disclosure are not limited thereto.
[0079] In the specification, alkenyl group refers to a hydrocarbon group containing at least one carbon-carbon double bond in the middle or at the end of an alkyl group having 2 or more carbon atoms. The alkenyl group can be straight chain or branched. The number of carbon atoms in the alkenyl group is not particularly limited, but is 2 to 60, 2 to 30, 2 to 20 or 2 to 10. Examples of alkenyl groups include vinyl groups, 1-butenyl groups, 1-pentenyl groups, 1,3-butadienyl groups, styryl groups, styryl vinyl groups, etc., but the embodiments of the present disclosure are not limited thereto.
[0080] In the specification, alkynyl group refers to a hydrocarbon group containing at least one carbon-carbon triple bond in the middle or at the end of an alkyl group having 2 or more carbon atoms. Alkynyl group can be straight chain or branched. Although the number of carbon atoms is not particularly limited, it is 2 to 60, 2 to 30, 2 to 20 or 2 to 10. Specific examples of alkynyl group can include ethynyl group, propynyl group etc., but are not limited thereto.
[0081] In the specification, the hydrocarbon ring group refers to any functional group or substituent derived from an aliphatic hydrocarbon ring. The hydrocarbon ring group may be a saturated hydrocarbon ring group having 5 to 20 ring carbon atoms.
[0082] In the specification, an aryl group refers to any functional group or substituent derived from an aromatic hydrocarbon ring. The aryl group may be a monocyclic aryl group or a polycyclic aryl group. The number of ring carbon atoms in the aryl group may 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, anthracenyl groups, phenanthrenyl groups, biphenyl groups, terphenyl groups, quaterphenyl groups, pentaphenyl groups, hexaphenyl groups, triphenylenyl groups, pyrenyl groups, benzofluoranthenyl groups, However, the embodiments of the present disclosure are not limited thereto.
[0083] In the specification, the fluorenyl group may be substituted, and two substituents are combined with each other to form a spiro structure. Examples of substituted fluorenyl groups are as follows. However, the embodiments of the present disclosure are not limited thereto.
[0084]
[0085] The heterocyclic group herein refers to any functional group or substituent derived from a ring containing at least one of B, O, N, P, Si and Se as a heteroatom. The heterocyclic group includes an aliphatic heterocyclic group and an aromatic heterocyclic group. The aromatic heterocyclic group can be a heteroaryl group. The aliphatic heterocycle and the aromatic heterocycle can be monocyclic or polycyclic.
[0086] 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, such as 1, 2, 3, 4 or 5. When the heterocyclic group contains two or more heteroatoms, the two or more heteroatoms may be identical or different from each other. The heterocyclic group may be a monocyclic heterocyclic group or a polycyclic heterocyclic group, and includes a heteroaryl group. The number of ring carbon atoms in the heterocyclic group may be 2 to 60, 2 to 30, 2 to 20 or 2 to 10.
[0087] 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 ring carbon atoms in the aliphatic heterocyclic group may be 2 to 60, 2 to 30, 2 to 20 or 2 to 10. Examples of the aliphatic heterocyclic group may include an oxirane group, a thiirane group, a pyrrolidine group, a piperidine group, a tetrahydrofuran group, a tetrahydrothiophene group, a thihexane group, a tetrahydropyran group, a 1,4-dioxane group and the like, but embodiments of the present disclosure are not limited thereto.
[0088] In the specification, the heteroaryl group may contain at least one of B, O, N, P, Si, S and Se as a heteroatom. When the heteroaryl group contains two or more heteroatoms, 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 ring carbon atoms in the heteroaryl group may be 2 to 60, 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, thienothiophene group, benzofuran group, phenanthroline group, thiazole group, isoxazole group, oxazole group, oxadiazole group, thiadiazole group, phenothiazine group, dibenzosilole group, dibenzofuran group and the like, but the embodiments of the present disclosure are not limited thereto.
[0089] In the specification, the previous description of the aryl group may be applied to the arylene group, but the arylene group is a divalent group. The previous description of the heteroaryl group may be applied to the heteroarylene group, but the heteroarylene group is a divalent group.
[0090] In the specification, silyl groups 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 the present disclosure are not limited thereto.
[0091] In the specification, the number of carbon atoms in the carbonyl group is not particularly limited, but may be 1 to 40, 1 to 30, or 1 to 20. For example, the carbonyl group may have the following structure, but embodiments of the present disclosure are not limited thereto.
[0092]
[0093] In the specification, the carbon number of the sulfinyl group and the sulfonyl group is not particularly limited, but may be 1 to 30, 1 to 20, or 1 to 10. The sulfinyl group may include an alkylsulfinyl group and an arylsulfinyl group. The sulfonyl group may include an alkylsulfonyl group and an arylsulfonyl group.
[0094] In the specification, the sulfenyl group may include an alkylsulfenyl group and an arylsulfenyl group. The sulfenyl group may refer to a sulfur atom bonded to an alkyl group or an aryl group as previously defined. Examples of sulfenyl groups may include a methylsulfenyl group, an ethylsulfenyl group, a propylsulfenyl group, a pentylsulfenyl group, a hexylsulfenyl group, an octylsulfenyl group, a dodecylsulfenyl group, a cyclopentylsulfenyl group, a cyclohexylsulfenyl group, a phenylsulfenyl group, a naphthylsulfenyl group, but the embodiments of the present disclosure are not limited thereto.
[0095] In the specification, an oxy group may refer to an oxygen atom bonded to an alkyl group or an aryl group as previously defined. An oxy group may include an alkoxy group and an aryloxy group. An alkoxy group may be a straight chain, a branched chain or a cyclic chain. The number of carbon atoms in the alkoxy group is not particularly limited, but may be, for example, 1 to 20 or 1 to 10. Examples of oxy groups may include methoxy, ethoxy, n-propoxy, isopropoxy, butoxy, pentyloxy, hexyloxy, octyloxy, nonyloxy, decyloxy, benzyloxy, etc., but the embodiments of the present disclosure are not limited thereto.
[0096] Boron groups herein may refer to boron atoms bonded to alkyl groups or aryl groups as previously defined. Boron groups include alkyl boron groups and aryl boron groups. Examples of boron groups may include dimethyl boron groups, diphenyl boron groups, phenyl boron groups, etc., but embodiments of the present disclosure are not limited thereto.
[0097] In the 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 an alkylamine group and an arylamine group. Examples of the amine group can include a methylamine group, a dimethylamine group, a phenylamine group, a diphenylamine group, a naphthylamine group, a 9-methyl-anthrylamine group, etc., but the embodiments of the present disclosure are not limited thereto.
[0098] In the specification, the alkyl group in the alkylthio group, the alkylsulfonyloxy group, the alkylaryl group, the alkylamino group, the alkylboron group, the alkylsilyl group, and the alkylamine group is the same as the examples of the alkyl group described previously.
[0099] In the specification, the aryl group in the aryloxy group, arylthio group, arylsulfonyloxy group, arylamino group, arylboron group, arylsilyl group, arylamine group is the same as the examples of the aryl group described previously.
[0100] In the specification, a direct bond may refer to a single bond. In the specification, and "-*" can refer to the location to be linked.
[0101] Hereinafter, embodiments of the present disclosure will be described with reference to the accompanying drawings.
[0102] Figure 1 is a plan view illustrating an embodiment of a display device DD. Figure 2 is a cross-sectional view of a display device DD of the embodiment. Figure 2 is an example along Figure 1 A cross-sectional view of a portion taken along line II'.
[0103] The display device DD may include a display panel DP and an optical layer PP disposed on the display panel DP. The display panel DP includes light-emitting devices ED-1, ED-2, and ED-3. The display device DD may include a plurality of light-emitting devices ED-1, ED-2, and ED-3. The optical layer PP may be disposed on the display panel DP to control reflected light in the display panel DP due to external light. The optical layer PP may include, for example, a polarizing layer or a color filter layer. In some embodiments, unlike the configuration illustrated in the drawings, the optical layer PP may not be provided from the display device DD of the embodiment.
[0104] The base substrate BL may be disposed on the optical layer PP. The base substrate BL may be a member providing a base surface on which the optical layer PP is disposed. The base substrate BL may be a glass substrate, a metal substrate, a plastic substrate, etc. However, the embodiments of the present disclosure are not limited thereto, and the base substrate BL may be an inorganic layer, an organic layer, or an organic-inorganic composite material layer. In some embodiments, unlike the illustrated configuration, in the embodiments, the base substrate BL may not be provided.
[0105] The display device DD according to the embodiment may further include a filling layer. The filling layer may be disposed between the display device layer DP-ED and the base substrate BL. The filling layer may be an organic material layer. The filling layer may include at least one of an acrylic-based resin, a silicone-based resin, and an epoxy-based resin.
[0106] The display panel DP may include a base layer BS, a circuit layer DP-CL provided on the base layer BS, and a display device layer DP-ED. The display device layer DP-ED may include a pixel defining film PDL, light emitting devices ED-1, ED-2, and ED-3 disposed between portions of the pixel defining film PDL, and an encapsulation layer TFE disposed on the light emitting devices ED-1, ED-2, and ED-3.
[0107] The base layer BS may be a member that provides a base surface on which the display device layer DP-ED is disposed. The base layer BS may be a glass substrate, a metal substrate, a plastic substrate, etc. However, the embodiment is not limited thereto, and the base layer BS may be an inorganic layer, an organic layer, or an organic-inorganic composite material layer.
[0108] In the embodiment, the circuit layer DP-CL is disposed on the base layer 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 switch transistor and a driving transistor for driving the light-emitting devices ED-1, ED-2, and ED-3 of the display device layer DP-ED.
[0109] Each of the light emitting devices ED-1, ED-2, and ED-3 may have a configuration according to the following description. Figures 3 to 7 Each of the light-emitting devices ED-1, ED-2, and ED-3 may include a first electrode EL1, a hole transport region HTR, emission layers EML-R, EML-G, and EML-B, an electron transport region ETR, and a second electrode EL2.
[0110] Figure 2An embodiment is illustrated in which the emission layers EML-R, EML-G, and EML-B of the light-emitting devices ED-1, ED-2, and ED-3 are disposed in the opening OH defined in the pixel defining film PDL, and the hole transport region HTR, the electron transport region ETR, and the second electrode EL2 are provided as a common layer in the entire light-emitting devices ED-1, ED-2, and ED-3. However, the embodiments of the present disclosure are not limited thereto, and are different from Figure 2 In the configuration illustrated in the embodiment, the hole transport region HTR and the electron transport region ETR in the embodiment can be provided by patterning in the opening OH defined in the pixel definition film PDL. For example, the hole transport region HTR, the emission layers EML-R, EML-G and EML-B, and the electron transport region ETR of the light-emitting devices ED-1, ED-2 and ED-3 in the embodiment can be provided by patterning in an inkjet printing method.
[0111] The encapsulation layer TFE may cover the light emitting devices ED-1, ED-2 and ED-3. The encapsulation layer TFE may seal the display device layer DP-ED. The encapsulation layer TFE may be a thin film encapsulation layer. The encapsulation layer TFE may be formed by laminating one or more layers. The encapsulation layer TFE includes at least one insulating layer. The encapsulation layer TFE according to the embodiment may include at least one inorganic film (hereinafter, encapsulation inorganic film). The encapsulation layer TFE according to the embodiment may also include at least one organic film (hereinafter, encapsulation organic film) and at least one encapsulation inorganic film.
[0112] The encapsulated inorganic film protects the display device layer DP-ED from moisture / oxygen, and the encapsulated organic film protects the display device layer DP-ED from foreign substances such as dust particles. The encapsulated inorganic film may include silicon nitride, silicon oxynitride, silicon oxide, titanium oxide, aluminum oxide, etc., but the embodiments of the present disclosure are not particularly limited thereto. The encapsulated organic film may include an acrylic-based compound, an epoxy-based compound, etc. The encapsulated organic film may include a photopolymerizable organic material, but the embodiments of the present disclosure are not particularly limited thereto.
[0113] The encapsulation layer TFE may be disposed on the second electrode EL2 and may be disposed to fill the opening OH.
[0114] refer to Figure 1 and Figure 2 , the display device DD may include a non-light emitting area NPXA and light emitting areas PXA-R, PXA-G, and PXA-B. The light emitting areas PXA-R, PXA-G, and PXA-B may be areas in which light generated by the respective light emitting devices ED-1, ED-2, and ED-3 is emitted. The light emitting areas PXA-R, PXA-G, and PXA-B may be spaced apart from each other on a plane.
[0115] Each of the light-emitting areas PXA-R, PXA-G, and PXA-B may be an area separated by a pixel-defining film PDL. The non-light-emitting area NPXA may be an area between adjacent light-emitting areas PXA-R, PXA-G, and PXA-B, which corresponds to the pixel-defining film PDL. In some embodiments, in the specification, the light-emitting areas PXA-R, PXA-G, and PXA-B may correspond to pixels, respectively. The pixel-defining film PDL may separate the light-emitting devices ED-1, ED-2, and ED-3. The emission layers EML-R, EML-G, and EML-B of the light-emitting devices ED-1, ED-2, and ED-3 may be disposed in the opening OH defined in the pixel-defining film PDL and separated from each other.
[0116] The light emitting areas PXA-R, PXA-G, and PXA-B may be divided into a plurality of groups according to the colors of the lights generated by the light emitting devices ED-1, ED-2, and ED-3. Figure 1 and Figure 2 In the display device DD of the embodiment illustrated in the embodiment, three light-emitting areas PXA-R, PXA-G and PXA-B that emit red light, green light and blue light respectively are illustrated examples. For example, the display device DD of the embodiment may include a red light-emitting area PXA-R, a green light-emitting area PXA-G and a blue light-emitting area PXA-B that are separated from each other.
[0117] In the display device DD according to the embodiment, a plurality of light-emitting devices ED-1, ED-2, and ED-3 may be configured to emit light beams having different wavelengths from each other. For example, in the embodiment, the display device DD may include a first light-emitting device ED-1 configured to emit red light, a second light-emitting device ED-2 configured to emit green light, and a third light-emitting device ED-3 configured to emit 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 device ED-1, the second light-emitting device ED-2, and the third light-emitting device ED-3, respectively.
[0118] However, the embodiments of the present disclosure are not limited thereto, and the first to third light emitting devices ED-1, ED-2, and ED-3 may be configured to emit light beams in substantially the same wavelength range, or at least one light emitting device may be configured to emit a light beam in a wavelength range different from the others. For example, the first to third light emitting devices ED-1, ED-2, and ED-3 may all be configured to emit blue light.
[0119] The light emitting areas PXA-R, PXA-G, and PXA-B in the display device DD according to the embodiment may be arranged in a stripe form. Figure 1, a plurality of red light emitting areas PXA-R, a plurality of green light emitting areas PXA-G, and a plurality of blue light emitting areas PXA-B may each be arranged along the second direction axis DR2. In some embodiments, the red light emitting areas PXA-R, the green light emitting areas PXA-G, and the blue light emitting areas PXA-B may be alternately arranged in this order along the first direction axis DR1.
[0120] Figure 1 and Figure 2 It is illustrated that all the light-emitting regions PXA-R, PXA-G, and PXA-B have similar areas, but the embodiments of the present disclosure are not limited thereto. Therefore, the light-emitting regions PXA-R, PXA-G, and PXA-B may have different areas from each other according to the wavelength range of the emitted light. In this case, the areas of the light-emitting regions PXA-R, PXA-G, and PXA-B may refer to the areas when viewed on a plane defined by the first direction axis DR1 and the second direction axis DR2.
[0121] In some embodiments, the arrangement of the light-emitting areas PXA-R, PXA-G, and PXA-B is not limited to Figure 1 The configuration illustrated in FIG. 1 and the order in which the red light emitting area PXA-R, the green light emitting area PXA-G and the blue light emitting area PXA-B are arranged can be provided in one or more suitable combinations according to the characteristics of the display quality required in the display device DD. For example, the arrangement form of the light emitting areas PXA-R, PXA-G and PXA-B can be a wave-tile shape. Layout or diamond )Layout form.
[0122] In some embodiments, the areas of the light-emitting regions PXA-R, PXA-G, and PXA-B may be different from each other. For example, in an embodiment, the area of the green light-emitting region PXA-G may be smaller than the area of the blue light-emitting region PXA-B, but the embodiments of the present disclosure are not limited thereto.
[0123] In the following, Figures 3 to 7 2 is a cross-sectional view schematically showing a light emitting device ED according to the embodiment The light emitting device ED according to the embodiment 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.
[0124] When with Figure 3 When compared, Figure 4 1 shows a cross-sectional view of a light emitting device ED of an embodiment, 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 some embodiments, when Figure 3 When compared, Figure 5 A cross-sectional view of a light emitting device ED of the embodiment is shown, wherein the hole transport region HTR includes a hole injection layer HIL, a hole transport layer HTL and an electron blocking layer EBL, and the electron transport region ETR includes an electron injection layer EIL, an electron transport layer ETL and a hole blocking layer HBL. Figure 3 When compared, Figure 6 A cross-sectional view of a light emitting device ED of the embodiment is shown, 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 4 When compared, Figure 7 A cross-sectional view of a light emitting device ED according to the embodiment is shown, the light emitting device ED including a cover layer CPL disposed on the second electrode EL2.
[0125] The first electrode EL1 has conductivity (for example, is a conductor). The first electrode EL1 may be formed of a metal material, a metal alloy, or a conductive compound. The first electrode EL1 may be an anode or a cathode. However, the embodiments of the present disclosure are not limited thereto. In some 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 include 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, a compound selected from two or more of these, a mixture selected from two or more of these, and / or its oxide.
[0126] When the first electrode EL1 is a transmissive electrode, the first electrode EL1 may include a transparent metal oxide, such as indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), or indium tin zinc oxide (ITZO). When the first electrode EL1 is a semi-transmissive reflective electrode or a reflective electrode, the first electrode EL1 may include Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, Mo, Ti, W, a compound or a mixture thereof (e.g., a mixture of Ag and Mg); and / or LiF / Ca (a stacking structure of LiF and Ca), or LiF / Al (a stacking structure of LiF and Al). In some embodiments, the first electrode EL1 may have a multilayer structure including a reflective film or a semi-transmissive reflective film formed of the previously described materials, and a transparent conductive film formed 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 the present disclosure are not limited thereto. In some embodiments, the embodiments of the present disclosure are not limited thereto, and the first electrode EL1 may include the previously described metal material, a combination of at least two of the previously described metal materials, an oxide of the previously described metal material, etc. The thickness of the first electrode EL1 may be about 1000 Å. to about For example, the thickness of the first electrode EL1 may be about to about
[0127] A hole transport region HTR is provided on the first electrode EL1. The hole transport region HTR may include at least one of a hole injection layer HIL, a hole transport layer HTL, an emission auxiliary layer EAL, and an electron blocking layer EBL. The thickness of the hole transport region HTR may be, for example, about 100 Å. to about The emission assist layer EAL may be referred to as a buffer layer.
[0128] The hole transport region HTR may have a single-layer structure formed of a single material, a single-layer structure formed of a plurality of different materials, or a multi-layer structure including a plurality of layers formed of a plurality of different materials.
[0129] For example, the hole transport region HTR may have a single-layer structure of a hole injection layer HIL or a hole transport layer HTL, or may have a single-layer structure formed of a hole injection material and a hole transport material. In some embodiments, the hole transport region HTR may have a single-layer structure formed of a plurality of different materials, or a structure in which hole injection layer HIL / hole transport layer HTL, hole injection layer HIL / hole transport layer HTL / emission auxiliary layer EAL, hole injection layer HIL / emission auxiliary layer EAL, hole transport layer HTL / emission auxiliary layer EAL, or hole injection layer HIL / hole transport layer HTL / emission auxiliary layer EBL are stacked in sequence from the first electrode EL1, but the embodiments of the present disclosure are not limited thereto.
[0130] The hole transport region HTR may be formed using one or more suitable methods such as vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) method, inkjet printing, laser printing, and laser induced thermal imaging (LITI) method.
[0131] The hole transport region HTR may include a compound represented by Formula H-1:
[0132] Formula H-1
[0133]
[0134] In formula H-1, L 1 and L 2 Each of a and b may be independently a direct bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms. a and b may be independently an integer from 0 to 10. In some embodiments, when a or b is an integer of 2 or greater, multiple L 1 and L 2 Each may independently be a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms.
[0135] In formula H-1, Ar 1 and Ar 2 may be each independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms. 3 It may be a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms.
[0136] The compound represented by formula H-1 may be a monoamine compound. In some embodiments, the compound represented by formula H-1 may be a diamine compound, wherein the compound selected from Ar 1 To Ar 3 At least one of them contains an amine group as a substituent. In some embodiments, the compound represented by the above formula H-1 can be in Ar 1 and Ar 2 A carbazole-based compound including a substituted or unsubstituted carbazole group in at least one of Ar 1 and Ar 2 A fluorene-based compound including a substituted or unsubstituted fluorene group in at least one of the foregoing.
[0137] The compound represented by Formula H-1 may be represented by any one selected from the compounds in Compound Group H. However, the compounds listed in Compound Group H are examples, and the compound represented by Formula H-1 is not limited to those represented by Compound Group H:
[0138] Compound Group H
[0139]
[0140]
[0141] The hole transport region HTR may include a phthalocyanine compound, such as copper phthalocyanine; N 1 ,N 1 '-([1,1'-biphenyl]-4,4'-diyl)bis(N 1 -phenyl-N 4 ,N 4 -dimethylphenylbenzene-1,4-diamine) (DNTPD), 4,4',4"-[tri(3-methylphenyl)phenylamino]triphenylamine (m-MTDATA), 4,4',4"-tri(N,N-diphenylamino)triphenylamine (TDATA), 4,4',4"-tri[N-(2-naphthyl)-N-phenylamino]-triphenylamine (2-TNATA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / dodecylbenzenesulfonic acid ( The following are some of the raw materials: PANI / DBSA), polyaniline / camphorsulfonic acid (PANI / CSA), polyaniline / poly(4-styrenesulfonate) (PANI / PSS), N,N'-di(naphthalene-1-yl)-N,N'-diphenyl-benzidine (NPB), triphenylamine-containing polyetherketone (TPAPEK), 4-isopropyl-4'-methyldiphenyliodonium [tetrakis(pentafluorophenyl)borate], and dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile (HAT-CN).
[0142] The hole transport region HTR may include 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"-tri(N-carbazyl)triphenylamine (TCTA)), N,N'-di(naphthalene-1-yl)-N,N'-diphenyl-benzidine (NPB), 4,4'-cyclohexylenebis[N,N-bis(4-methylphenyl)aniline] (TAPC), 4,4'-bis[N,N'-(3-methylphenyl)amino]-3,3'-dimethylbiphenyl (HMTPD), 1,3-bis(carbazol-9-yl)benzene (mCP), and the like.
[0143] In some embodiments, the hole transport region HTR may include 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), or the like.
[0144] The hole transport region HTR may include the previously described compound of the hole transport region in at least one of the hole injection layer HIL, the hole transport layer HTL, the emission auxiliary layer EAL, and the electron blocking layer EBL.
[0145] The thickness of the hole transport region HTR may be about to about For example, about to about When the hole transport region HTR includes the hole injection layer HIL, the hole injection layer HIL may have, for example, about to about When the hole transport region HTR includes the hole transport layer HTL, the hole transport layer HTL may have a thickness of about to about For example, when the hole transport region HTR includes the electron blocking layer EBL, the electron blocking layer EBL may have a thickness of about to about When the thicknesses of the hole transport region HTR, the hole injection layer HIL, the hole transport layer HTL, and the electron blocking layer EBL satisfy the previously described ranges, satisfactory hole transport properties may be achieved without a significant increase in driving voltage.
[0146] In addition to the previously described materials, the hole transport region HTR may further include a charge generating material to increase conductivity. The charge generating material may be substantially uniformly or substantially non-uniformly dispersed in the hole transport region HTR. The charge generating material may be, for example, a p-dopant. The p-dopant may include at least one of a halogenated metal compound, a quinone derivative, a metal oxide, and a cyano group-containing compound, but the embodiments of the present disclosure are not limited thereto. For example, the p-dopant may include a metal halide (e.g., CuI or RbI), a quinone derivative (e.g., tetracyanoquinodimethane (TCNQ) or 2,3,5,6-tetrafluoro-7,7',8,8'-tetracyanoquinodimethane (F4-TCNQ)), a metal oxide (e.g., tungsten oxide or molybdenum oxide), a cyano group-containing compound (e.g., dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile (HAT-CN) or 4-[[2,3-bis[cyano-(4-cyano-2,3,5,6-tetrafluorophenyl)methylene]cyclopropylidene]-cyanomethyl]-2,3,5,6-tetrafluorobenzonitrile (NDP9)), etc., but the embodiments of the present disclosure are not limited thereto.
[0147] As previously described, 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 selected from an emission auxiliary layer EAL and an electron blocking layer EBL. The emission auxiliary layer EAL may compensate for the resonance distance according to the wavelength of the light emitted from the emission layer EML and control the hole charge balance to increase the luminous efficiency. In some embodiments, the emission auxiliary layer EAL may play a role in preventing or reducing electron injection into the hole transport region HTR. The material contained in the hole transport region HTR may be used as the material contained in the emission auxiliary layer EAL. The electron blocking layer EBL may be a layer that plays a role in preventing or reducing electron injection from the electron transport region ETR to the hole transport region HTR.
[0148] In the light-emitting device ED of the embodiment, the emission layer EML may include the first compound of the embodiment. In some embodiments, the emission layer EML according to the embodiment may further include at least one selected from the second compound to the fourth compound. The second compound may include a fused ring of three rings including nitrogen atoms as ring atoms. The third compound may include a hexagonal ring group including at least one nitrogen atom as a ring atom. The fourth compound may include an organic metal complex. The second compound to the fourth compound will be explained in more detail later.
[0149] In the description, the first compound may be referred to as a fused polycyclic compound of the embodiment. The fused polycyclic compound of the embodiment may include a fused ring of nine rings as a central structure, and the fused ring of the nine rings includes three nitrogen atoms and one boron atom as ring-forming atoms. Two nitrogen atoms and one boron atom in the ring-forming atoms are in a para-position relationship, and a fused ring of two rings may be formed in the fused ring of the nine rings. In the fused polycyclic compound of the embodiment, the fused ring of the nine rings may include an indole and carbazole moiety. The ortho-terphenyl may be directly bonded to two nitrogen atoms in the para position in the fused ring of the nine rings, respectively.
[0150] The light emitting device ED of the embodiment may include the condensed polycyclic compound of the embodiment. The condensed polycyclic compound of the embodiment may be represented by Formula 1.
[0151] Formula 1
[0152]
[0153] In formula 1, R 1 To R 8 Each of them may independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 ring carbon atoms, and / or combine with an adjacent group to form a ring. For example, R 1 To R 8 and R , R , R , R , R , R , R , R , R , R , R , R , R , R , R , R , R , R , R , R , R , R , R , R , R , R , R , R , R , R , R , R , R , R , R , R , R , R , R , R , R , R , R , R , R , R 1 To R 8 Each may independently be a hydrogen atom, a deuterium atom, or be represented by one selected from R-1 to R-26.
[0154]
[0155]
[0156] R-14 may represent an unsubstituted benzothiophene carbazole group. In R-5, R-9, R-13, and R-16 to R-26, D is a deuterium atom. In R-1 to R-26, "-*" refers to the position to be connected. For example, in Formula 1, R 6can be represented by R-6, and R 6 Can be done through R 6 Adjacent R 7 and R 6 The combination of the substituted ring groups forms a dibenzofuran group.
[0157] In Formula 1, n1 to n4 may each independently be an integer of 0 to 5. a1 To R a6 and R b1 To R b4 Each of R and R may independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thiol group, a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 ring carbon atoms, and / or combine with an adjacent group to form a ring. For example, R a3 and R b2 can be combined with each other to form a ring. n2 can be an integer of 2 or greater, and multiple R b2 They may be combined with each other to form a ring. However, this is an embodiment, and the embodiments of the present disclosure are not limited thereto.
[0158] When n1 is an integer of 2 or greater, multiple R b1 When n1 is 0, the fused polycyclic compound represented by Formula 1 may not be R b1 The case where n1 is 0 can be replaced with the case where n1 is 5 and five R b1 When n2 is an integer of 2 or greater, multiple R 2 When n2 is 0, the fused polycyclic compound represented by Formula 1 may not be R b2 The case where n2 is 0 can be replaced with the case where n2 is 5 and five R b2 The same is true for hydrogen atoms.
[0159] When n3 is an integer of 2 or greater, multiple R b3 When n3 is 0, the fused polycyclic compound represented by Formula 1 may not be R b3 The case where n3 is 0 can be replaced with the case where n3 is 5 and five R b3 When n4 is an integer of 2 or greater, multiple R b4When n4 is 0, the fused polycyclic compound represented by Formula 1 may not be R b4 The case where n4 is 0 can be replaced with the case where n4 is 5 and five R b4 The same is true for hydrogen atoms.
[0160] In Formula 1, m1 and m2 may each independently be an integer of 0 to 4. c1 and R c2 Each of them may independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thiol group, a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 ring-forming carbon atoms.
[0161] If m1 is an integer of 2 or greater, multiple R c1 When m1 is 0, the fused polycyclic compound represented by Formula 1 may not be R c1 The case where m1 is 0 can be replaced with the case where m1 is 4 and four R c1 The same is true for the case where m2 is an integer of 2 or greater than 2. c2 When m2 is 0, the fused polycyclic compound represented by Formula 1 may not be R c2 The case where m2 is 0 can be replaced with the case where m2 is 4 and four R c2 The same is true for hydrogen atoms.
[0162] For example, R c1 and R c2 and R and R are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted methyl group, a substituted or unsubstituted tert-butyl group, or a substituted or unsubstituted phenyl group. c1 and R c2 Each of them can be independently a hydrogen atom, a deuterium atom, or represented by one selected from RC-1 to RC-4. In RC-1, D is a deuterium atom. In RC-1 to RC-4, "-*" refers to the position to be connected.
[0163]
[0164] The fused polycyclic compound of the embodiment may contain a deuterium atom or a substituent containing a deuterium atom. In Formula 1, R 1 To R8 , R a1 To R a6 , R b1 To R b4 , R c1 and R c2 At least one of may be a deuterium atom or include a substituent containing a deuterium atom. For example, in Formula 1, R 1 To R 8 At least one of the groups may be a carbazole group substituted by a deuterium atom. a1 To R a6 , R c1 and R c2 At least one of may be a deuterium atom. However, this is an example, and embodiments of the present disclosure are not limited thereto.
[0165] In an embodiment, Formula 1 may be represented by Formula 1-A. Formula 1-A may represent Formula 1, wherein R 2 is a substituted or unsubstituted carbazole group, and R 1 , R 3 To R 5 and R 8 It's a hydrogen atom.
[0166] Formula 1-A
[0167]
[0168] In Formula 1-A, the same contents explained in Formula 1 can be applied to n1 to n4, R a1 To R a6 , R b1 To R b4 、m1、m2、R c1 and R c2 . R 16 and R 17 Each of them may independently be a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms. 16 and R 17 and R and R are each independently a hydrogen atom, a substituted or unsubstituted tert-butyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted carbazole group, a substituted or unsubstituted benzothienylcarbazole group, or a substituted or unsubstituted dibenzofuran group. 16 and R 17 Each may independently be a hydrogen atom or be represented by one selected from R-1 to R-26.
[0169] R d1 To R d8 Each of them may independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted amine group, a substituted or unsubstituted thiol group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, and / or combine with an adjacent group to form a ring. For example, R d1 To R d8 may each independently be a hydrogen atom, a deuterium atom, a cyano group, a substituted or unsubstituted diphenylamine group, a substituted or unsubstituted methyl group, a substituted or unsubstituted tert-butyl group, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted carbazole group, and / or combine with an adjacent group to form a ring. d1 To R d8 The bonded carbazole group may be represented by one selected from the previously described R-11 to R-26.
[0170] In an embodiment, Formula 1-A may be represented by Formula 1-A1. Formula 1-A1 may represent wherein R 16 is a hydrogen atom and R 17 is Formula 1-A which is a substituted or unsubstituted carbazole group.
[0171] Formula 1-A1
[0172]
[0173] In Formula 1-A1, the same contents explained in Formula 1-A can be applied to n1 to n4, R a1 To R a6 , R b1 To R b4 、m1、m2、R c1 , R c2 , and R d1 To R d8 . R d11 To R d18 Each of the above 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 thiol group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, and / or may be combined with an adjacent group to form a ring. For example, wherein R d11 To R d12 The carbazole group may be represented by one selected from R-11 to R-26 described previously.
[0174] In the embodiment, Formula 1 can be represented by one selected from Formula 1-B1 to Formula 1-B3. Formula 1-B1 represents wherein R a1 To R a6 and R b1 To R b4 Formula 1-B2 represents a hydrogen atom wherein R a1 , R a3 , R a4 and R a6 Formula 1-B3 represents a hydrogen atom wherein R a1 , R a3 , R a4 and R a6 is a hydrogen atom, multiple R b2 Combine with each other to form a ring, and multiple R b4 Combined with each other to form a ring of formula 1. b2 The groups may be adjacent to each other. b4 The groups may be adjacent to each other.
[0175] Formula 1-B1
[0176]
[0177] Formula 1-B2
[0178]
[0179] Formula 1-B3
[0180]
[0181] In Formula 1-B1 to Formula 1-B3, the same contents explained in Formula 1 can be applied to R 1 To R 8 、n1、n3、R b1 , R b3 、m1、m2、R c1 and R c2 .
[0182] In formula 1-B2, R b11 , R b12 , R b21 To R b23 , R b31 , R b32 , and R b41 To R b43Each of them may independently be a hydrogen atom, a deuterium atom, a cyano group, a substituted or unsubstituted amine group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thiol group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, and / or combine with an adjacent group to form a ring. For example, R b11 , R b12 , R b21 To R b23 , R b31 , R b32 , and R b41 To R b43 Each may independently be a hydrogen atom, a cyano group, or a substituted or unsubstituted phenyl group. However, this is an example, and the embodiments of the present disclosure are not limited thereto.
[0183] In formula 1-B3, Q 11 and Q 12 Can be NR independently 21 , O or S. When Q 11 YesNR 21 When Q 11 The three-ring fused ring may be a substituted or unsubstituted carbazole group. 11 When it is O, it contains Q 11 The fused ring of the three rings may be a substituted or unsubstituted dibenzofuran group. 11 When it is S, it includes Q 11 The three-ring fused ring may be a substituted or unsubstituted dibenzothiophene group. 12 YesNR 21 When Q 12 The three-ring fused ring may be a substituted or unsubstituted carbazole group. 12 When it is O, it contains Q 12 The fused ring of the three rings may be a substituted or unsubstituted dibenzofuran group. 12 When it is S, it includes Q 12 The fused ring of three rings may be a substituted or unsubstituted dibenzothiophene group.
[0184] In Formula 1-B3, n5 and n6 may each independently be an integer of 0 to 7. 21 To R 23 Each may independently be a hydrogen atom, a deuterium atom, or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms.
[0185] When n5 is an integer of 2 or greater, multiple R 22When n5 is 0, the fused polycyclic compound represented by Formula 1-B3 may not be R 22 The case where n5 is 0 can be replaced with the case where n5 is 7 and seven R 22 When n6 is an integer of 2 or greater, multiple R 23 When n6 is 0, the fused polycyclic compound represented by Formula 1-B3 may not be R 23 The case where n6 is 0 can be replaced with the case where n6 is 7 and seven R 23 The same is true for hydrogen atoms.
[0186] In Formula 1-B2 and Formula 1-B3, R a12 and R a15 R may be each independently a hydrogen atom, a deuterium atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms. a12 and R a15 Each may independently be a substituted or unsubstituted tert-butyl group or a substituted or unsubstituted phenyl group.
[0187] For example, Formula 1-B3 may be represented by one selected from Formula 1-B31 to Formula 1-B33. Formula 1-B31 to Formula 1-B33 may be a formula wherein Q 11 The three-ring fused ring and the ring containing Q 12 The bonding positions of the fused ring of the three rings are represented by Formula 1-B3.
[0188] Formula 1-B31
[0189]
[0190] Formula 1-B32
[0191]
[0192] Formula 1-B33
[0193]
[0194] In Formula 1-B31 to Formula 1-B33, the same contents explained in Formula 1-B3 can be applied to R 1 To R 8 、n1、n3、R b1 , R b3 、m1、m2、R c1 , R c2 , Q 11 , Q 12 、n5、n6、R22 and R 23 .
[0195] The condensed polycyclic compound of the embodiment may be represented by one of the compounds selected from the compound group 1. The light emitting device ED of the embodiment may include at least one of the compounds selected from the compound group 1. In the compound group 1, D is a deuterium atom.
[0196] Compound Group 1
[0197]
[0198]
[0199]
[0200]
[0201]
[0202]
[0203]
[0204]
[0205]
[0206]
[0207]
[0208]
[0209]
[0210]
[0211] The emission layer EML may include the fused polycyclic compound of the embodiment as a dopant. The fused polycyclic compound of the embodiment may be a thermally activated delayed fluorescence (TADF) material. The fused polycyclic compound of the embodiment may be a thermally activated delayed fluorescence material of a multi-resonance (MR) type or kind. The fused polycyclic compound of the embodiment may be configured to emit light by converting triplet excitons into singlet excitons through a reverse intersystem crossing (RISC) mechanism.
[0212] The fused polycyclic compound of the embodiment may include a nine-ring fused ring as a central structure, and the nine-ring fused ring includes three nitrogen atoms and one boron atom as ring atoms. The fused polycyclic compound of the embodiment may include a nine-ring fused ring represented by formula Z1 as a central structure. The nine-ring fused ring may have a fused structure of an indole and carbazole moiety and a five-ring fused ring represented by formula Z2.
[0213] Formula Z1
[0214]
[0215] Formula Z2
[0216]
[0217] In formula Z1, N a and N b is a nitrogen atom and is indicated together with letters (a, b) for ease of explanation. a and N b A nitrogen atom which is in a para-position relationship with the boron atom and may be a condensed ring of two rings constituting the condensed ring of nine rings. a and N b Each of the terphenyl groups may be independently combined with a substituted or unsubstituted o-terphenyl group. The o-terphenyl group may correspond to R a1 To R a6 The bound o-terphenyl group.
[0218] The five-ring fused ring represented by Formula Z2 can exhibit a variety of resonance properties. The fused polycyclic compound of the embodiment comprising a nine-ring fused ring (i.e., represented by Formula Z1) in which the indolocarbazole moiety is fused to the five-ring fused ring can have enhanced rigidity and multiple resonances to have a small ΔE ST , and may have an increased spin-orbit coupling (SOC) constant to have accelerated RISC. The fused polycyclic compound of the embodiment includes a fused indole and carbazole moiety and may have even more enhanced rigidity and multiple resonance. When the multiple resonance is enhanced, the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO) between atoms may increase, ΔE ST can be reduced, and RISC can be accelerated. ΔE STIt is the absolute value of the energy level difference between singlet state (S1) and triplet state (T1). In some embodiments, the fused polycyclic compound of the embodiment includes an ortho-terphenyl group that spatially protects the fused ring of nine rings, and can show excellent or suitable material stability. The ortho-terphenyl group corresponds to a bulky substituent and can protect the empty p orbital of the boron atom. The boron atom can be a ring-forming atom in the fused ring of nine rings. Therefore, the triangular bonding structure of the boron atom in the fused ring of nine rings can be effectively maintained.
[0219] The ortho-terphenyl group can be directly bonded to the nitrogen atom in the fused ring of nine rings to increase the intermolecular distance and prevent or reduce intermolecular interactions. Therefore, in the fused polycyclic compound of the embodiment, the Dexter energy transfer according to the intermolecular interaction can be suppressed or reduced. Dexter energy transfer is generated in triplet excitons, and when Dexter energy transfer is suppressed or reduced, the increase in the concentration of triplet excitons in the compound can be prevented or reduced. Because the triplet excitons with a high concentration are kept in an excited state for a long time, the decomposition of the compound can be caused, and the hot excitons can be generated by triplet triplet annihilation (TTA) to decay around (e.g., surround) the compound, thereby degrading the service life of the light-emitting device.
[0220] Intermolecular interactions include intermolecular aggregation, intermolecular quasi-molecular formation, intermolecular exciplexes, etc., and these lead to degradation of the emission efficiency and service life of the light-emitting device. When the intermolecular aggregation of the fused polycyclic compound of the embodiment is prevented or reduced, the purification of the compound during the synthesis of the fused polycyclic compound may be easy, and excellent or suitable stability may be shown relative to thermal decomposition in the sublimation purification step during the synthesis. In some embodiments, the fused polycyclic compound of the embodiment may be configured to emit light with high color purity.
[0221] The fused polycyclic compound of the embodiment comprises a fused ring of nine rings as a central structure, the fused ring of the nine rings comprises three nitrogen atoms and one boron atom as ring-forming atoms, and the ortho-terphenyl group can be combined with two nitrogen atoms in the central structure. Therefore, the fused polycyclic compound of the embodiment can show excellent or suitable material stability and accelerated RISC. The light-emitting device comprising the fused polycyclic compound of the embodiment can show low driving voltage, high emission efficiency and long service life characteristics.
[0222] The fused polycyclic compound of the embodiment can be configured to emit blue light and can have a light emission center wavelength in a wavelength region of about 430 nm to about 490 nm. The light emitting device ED including the fused polycyclic compound of the embodiment can be configured to emit light having a light emission center wavelength in a wavelength region of about 430 nm to about 490 nm. The light emitting device ED including the fused polycyclic compound of the embodiment can be configured to emit blue light. For example, the third light emitting device ED-3 ( Figure 2 ) may include a fused polycyclic compound of an embodiment.
[0223] In the embodiment, the emission layer EML may include the fused polycyclic compound of the embodiment, and may further include at least one selected from the second compound to the fourth compound. In the embodiment, the emission layer EML may include the second compound represented by formula HT-1. For example, the second compound may be used as a hole transport host material of the emission layer EML.
[0224] Formula HT-1
[0225]
[0226] In formula HT-1, A 1 To A 8 Can be N or CR independently 51 For example, all A 1 To A 8 Can be CR 51 In some embodiments, selected from A 1 To A 8 Any one of them can be N, and the rest can be CR 51 .
[0227] In formula HT-1, L 1 It may be a direct bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms. 1 It may be a direct bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted divalent biphenyl group, a substituted or unsubstituted divalent carbazole group, or the like, but embodiments of the present disclosure are not limited thereto.
[0228] In formula HT-1, Y a Can be direct key, CR 52 R 53 or SiR 54 R 55 For example, it may refer to two benzene rings connected to the nitrogen atom in formula HT-1 via a direct bond, In formula HT-1, when Y a When it is a direct bond, the second compound represented by Formula HT-1 may include a carbazole moiety.
[0229] In formula H-1, Ar 1 It may be a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms. 1 It may 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, or the like, but the embodiments of the present disclosure are not limited thereto.
[0230] In formula HT-1, R 51 To R 55 and R and R are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted thiol 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 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 ring carbon atoms. In some embodiments, R 51 To R 55 Each of R may be bonded to an adjacent group to form a ring. 51 To R 55 R may each independently be a hydrogen atom or a deuterium atom. 51 To R 55 Each may independently be an unsubstituted methyl group or an unsubstituted phenyl group.
[0231] In the embodiment, the second compound represented by Formula HT-1 may be represented by any one selected from the compounds represented by Compound Group 2. The emission layer EML may include at least one selected from the compounds represented by Compound Group 2 as a hole transport host material.
[0232] Compound Group 2
[0233]
[0234]
[0235]
[0236]
[0237] In the embodiment 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 embodiment compounds presented in compound group 2, "Ph" can refer to an unsubstituted phenyl group.
[0238] In the embodiment, the emission layer EML may include a third compound represented by Formula ET-1. For example, the third compound may be used as an electron transport host material for the emission layer EML.
[0239] Formula ET-1
[0240]
[0241] In formula ET-1, selected from X 1 To X 3 At least one of them is N, and the rest are CR 56 For example, select X 1 To X 3 Any one of them can be N, and the others can each independently be CR 56 In this case, the third compound represented by Formula ET-1 may include a pyridine moiety. In some embodiments, X 1 To X 3 Two of them can be N, and the rest can be CR 56 In this case, the third compound represented by Formula ET-1 may include a pyrimidine moiety. In some embodiments, X 1 To X 3 All may be N. In this case, the third compound represented by Formula ET-1 may include a triazine moiety.
[0242] In formula ET-1, R 56 It may be a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 ring carbon atoms.
[0243] In Formula ET-1, b1 to b3 may each independently be an integer of 0 to 10.
[0244] In formula ET-1, Ar 2 To Ar 4 Each of them may be independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms. 2To Ar 4 Each independently may be a substituted or unsubstituted phenyl group, or a substituted or unsubstituted carbazole group.
[0245] In formula ET-1, L 2 To L 4 and L may be independently a direct bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms. 2 To L 4 Each may independently be a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms.
[0246] In the embodiment, the third compound may be represented by any one of the compounds selected from the compound group 3. The light emitting device ED of the embodiment may include any one of the compounds selected from the compound group 3.
[0247] Compound Group 3
[0248]
[0249]
[0250]
[0251]
[0252]
[0253]
[0254]
[0255] In the embodiment compounds presented in Compound Group 3, "D" refers to a deuterium atom and "Ph" refers to an unsubstituted phenyl group.
[0256] The emission layer EML may include a second compound and a third compound, and the second compound and the third compound may form an exciplex. In the emission layer EML, an exciplex may be formed by a hole transport host material and an electron transport host material. In this case, the triplet energy level of the exciplex formed by the hole transport host material and the electron transport host material may correspond to the lowest unoccupied molecular orbital (LUMO) energy level of the electron transport host material and the highest occupied molecular orbital (HOMO) energy level of the hole transport host material.
[0257] For example, the absolute value of the triplet energy level (T1) of the exciplex formed by the hole transport host material and the electron transport host material can be about 2.4 eV to about 3.0 eV. In some embodiments, the triplet energy level of the exciplex can be a value less than the band gap of each host material. The exciplex can have a triplet energy level of about 3.0 eV or less than 3.0 eV, which is the band gap between the hole transport host material and the electron transport host material.
[0258] In an embodiment, the emission layer EML may include a fourth compound in addition to the first to third compounds as described previously. The fourth compound may be used as a phosphorescence sensitizer of the emission layer EML. Energy may be transferred from the fourth compound to the first compound, thereby emitting light.
[0259] For example, the emission layer EML may include an organic metal complex including platinum (Pt) as a central metal atom and a ligand connected to the central metal atom as the fourth compound. The emission layer EML in the light-emitting device ED of the embodiment may include a compound represented by Formula D-1 as the fourth compound:
[0260] Formula D-1
[0261]
[0262] In formula D-1, Q 1 To Q 4 can each independently be C or N.
[0263] In formula D-1, C1 to C4 may each independently be a substituted or unsubstituted hydrocarbon ring having 5 to 30 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocycle having 2 to 30 ring carbon atoms.
[0264] In formula D-1, L 11 To L 13 Can be directly connected, *-O-*, *-S-*, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms. 11 To L 13 In the figure, “-*” refers to the part connected to C1 to C4.
[0265] In formula D-1, b11 to b13 may each independently be 0 or 1. When b11 is 0, C1 and C2 may not be connected to each other. When b12 is 0, C2 and C3 may not be connected to each other. When b13 is 0, C3 and C4 may not be connected to each other.
[0266] In formula D-1, R 61 To R 66 and R and R are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted thiol 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 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 ring carbon atoms. In some embodiments, R 61 To R 66 Each of R may be bonded to an adjacent group to form a ring. 61 To R 66 Each may independently be a substituted or unsubstituted methyl group, or a substituted or unsubstituted tert-butyl group.
[0267] In Formula D-1, d1 to d4 may each independently be an integer of 0 to 4. In Formula D-1, when each of d1 to d4 is 0, the fourth compound may not be R 61 To R 64 Each of d1 to d4 is 4 and R 61 To R 64 The case where each of d1 to d4 is a hydrogen atom may be the same as the case where each of d1 to d4 is 0. When each of d1 to d4 is an integer of 2 or greater, a plurality of R 61 To R 64 They can be the same or selected from multiple R 61 To R 64 At least one of may be different from the others.
[0268] In Formula D-1, C1 to C4 may each independently be a substituted or unsubstituted hydrocarbon ring, or a substituted or unsubstituted heterocycle represented by any one selected from Formula C-1 to Formula C-4:
[0269]
[0270] In C-1 to C-4, P 1 Can be C-* or CR 74 , P 2 Can be N-* or NR81 , P 3 Can be N-* or NR 82 , and P 4 Can be C-* or CR 88 . R 71 To R 88 Each may independently be a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, and / or may be bonded to an adjacent group to form a ring.
[0271] In some embodiments, in C-1 to C-4, corresponds to a portion connected to Pt as a central metal atom, and “-*” corresponds to a portion connected to an adjacent cyclic group (C1 to C4) or a linker (L 11 To L 13 ) part.
[0272] The emission layer EML of the embodiment may include a first compound as a fused polycyclic compound, and at least one selected from the second compound to the fourth compound. For example, the emission layer EML may include a first compound, a second compound, and a third compound. In the emission layer EML, the second compound and the third compound may form an exciplex, and energy may be transferred from the exciplex to the first compound, thereby emitting light.
[0273] In some embodiments, the emission layer EML may include a first compound, a second compound, a third compound, and a fourth compound. In the emission layer EML, the second compound and the third compound may form an exciplex, and energy may be transferred from the exciplex to the fourth compound and the first compound, thereby emitting light. In the embodiment, the fourth compound may be a sensitizer. The fourth compound included in the emission layer EML in the light-emitting device ED of the embodiment may be used as a sensitizer to transfer energy from the host to the first compound as a light-emitting dopant. For example, the fourth compound acting as an auxiliary dopant accelerates the energy transfer to the first compound as a light-emitting dopant, thereby increasing the emission ratio of the first compound. Therefore, the emission layer EML of the embodiment can improve the luminous efficiency. In some embodiments, when the energy transfer to the first compound is increased, the excitons formed in the emission layer EML will not accumulate inside the emission layer EML and emit light quickly, and thus the degradation of the device can be reduced. Therefore, the service life of the light-emitting device ED of the embodiment can be increased.
[0274] The light-emitting device ED of the embodiment may include all of the first compound, the second compound, the third compound, and the fourth compound, and the emission layer EML may include a combination of two host materials and two dopant materials. In the light-emitting device ED of the embodiment, the emission layer EML may include in parallel (e.g., simultaneously) the second compound and the third compound as two different hosts, the first compound configured to emit delayed fluorescence, and the fourth compound including the organic metal complex, thereby exhibiting excellent or suitable luminous efficiency characteristics.
[0275] In an embodiment, the fourth compound represented by Formula D-1 may be represented by at least one selected from the compounds in Compound Group 4. The emission layer EML may include at least one selected from the compounds represented by Compound Group 4 as a sensitizer material.
[0276] Compound Group 4
[0277]
[0278]
[0279]
[0280] In the embodiment compounds presented in compound group 4, "D" refers to a deuterium atom.
[0281] When the emission layer EML in the light-emitting device ED of the embodiment includes all of the first compound, the second compound, and the third compound, the content (e.g., amount) of the first compound relative to the total weight of the first compound, the second compound, and the third compound may be about 0.1 wt% to about 5 wt%. However, the embodiments of the present disclosure are not limited thereto. When the content (e.g., amount) of the first compound satisfies the ratio described previously, the energy transfer from the second compound and the third compound to the first compound may be increased, and thus the luminous efficiency and the device service life may be increased.
[0282] The content of the second compound and the third compound in the emission layer EML may be the balance excluding the weight of the first compound. For example, the content of the second compound and the third compound in the emission layer EML may be about 65 wt % to about 95 wt % relative to the total weight of the first compound, the second compound and the third compound.
[0283] A weight ratio of the second compound to the third compound may be about 3:7 to about 7:3 in the total weight of the second compound and the third compound.
[0284] When the contents of the second compound and the third compound satisfy the ratio described previously, the charge balance characteristics in the emission layer EML are improved, and thus the luminous efficiency and the device lifespan can be increased. When the contents of the second compound and the third compound deviate from the ratio range described previously, the charge balance in the emission layer EML is destroyed, and thus the luminous efficiency may be reduced and the device may be easily degraded.
[0285] When the emission layer EML includes a fourth compound, the content (e.g., amount) of the fourth compound in the emission layer EML may be about 10 wt% to about 30 wt% relative to the total weight of the first compound, the second compound, the third compound, and the fourth compound. However, the embodiments of the present disclosure are not limited thereto. When the content (e.g., amount) of the fourth compound satisfies the previously described content (e.g., amount), the energy transfer from the host to the first compound as a light-emitting dopant can be increased, thereby improving the luminous efficiency, and thus improving the luminous efficiency of the emission layer EML. When the first compound, the second compound, the third compound, and the fourth compound contained in the emission layer EML meet the previously described content (e.g., amount) ratio range, excellent or suitable luminous efficiency and long service life can be achieved.
[0286] An emission layer EML is provided on the hole transport region HTR. The emission layer EML may have, for example, about to about or about to about The emission layer EML may have a single-layer structure formed of a single material, a single-layer structure formed of a plurality of different materials, or a multi-layer structure having a plurality of layers formed of a plurality of different materials.
[0287] The emission layer EML may further include a compound described in addition to the first to fourth compounds described previously. In the light emitting device ED of the embodiment, the emission layer EML may include an anthracene derivative, a pyrene derivative, a fluoranthene derivative, Derivatives, dihydrobenzanthracene derivatives or triphenylene derivatives. For example, the emission layer EML may include anthracene derivatives or pyrene derivatives.
[0288] exist Figures 3 to 7 In each light emitting device ED of the embodiment illustrated in the embodiment, the emission layer EML may further include a suitable host and dopant in addition to the previously described host and dopant, for example, the emission layer EML may include a compound represented by Formula E-1. The compound represented by Formula E-1 may be used as a fluorescent host material.
[0289] Formula E-1
[0290]
[0291] In formula E-1, R 31 To R 40 may each independently be a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted silyl group, a substituted or unsubstituted thiol group, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, and / or may be bonded to an adjacent group to form a ring. In some embodiments, R 31 To R 40 It may be bonded to an adjacent group to form a saturated hydrocarbon ring or an unsaturated hydrocarbon ring, a saturated heterocyclic ring, or an unsaturated heterocyclic ring. In Formula E-1, c and d may each independently be an integer of 0 to 5.
[0292] Formula E-1 can be represented by any one selected from Compound E1 to Compound E19:
[0293]
[0294]
[0295] In the embodiment, the emission layer EML may include a compound represented by Formula E-2a or Formula E-2b. The compound represented by Formula E-2a or Formula E-2b may be used as a phosphorescent host material.
[0296] Formula E-2a
[0297]
[0298] In Formula E-2a, a may be an integer from 0 to 10, and L a It may be a direct bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms. In some embodiments, when a is an integer of 2 or greater, multiple L a Each may independently be a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms.
[0299] In some embodiments, in Formula E-2a, A 1 To A 5 Can be N or CR independently i . R a To R iEach may independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted amine group, a substituted or unsubstituted thiol group, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, and / or may be bonded to an adjacent group to form a ring. a To R i It may be bonded to an adjacent group to form a hydrocarbon ring or a heterocyclic ring containing N, O, S, etc. as a ring-constituting atom.
[0300] In some embodiments, in Formula E-2a, selected from A 1 To A 5 Two or three of them can be N, and the rest can be CR i .
[0301] Formula E-2b
[0302]
[0303] In Formula E-2b, Cbz1 and Cbz2 may each independently be an unsubstituted carbazole group or a carbazole group substituted with an aryl group having 6 to 30 ring carbon atoms. b is a direct bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms. In some embodiments, b is an integer from 0 to 10, and when b is an integer of 2 or greater, multiple L b Each may independently be a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms.
[0304] The compound represented by formula E-2a or formula E-2b can be represented by any one of the compounds selected from compound group E-2. However, the compounds listed in compound group E-2 are examples, and the compounds represented by formula E-2a or formula E-2b are not limited to those represented in compound group E-2.
[0305] Compound Group E-2
[0306]
[0307]
[0308]
[0309] The emission layer EML may further include a general material available in the art as a host material. For example, the emission layer EML may include at least one of bis(4-(9H-carbazole-9-yl)phenyl)diphenylsilane (BCPDS), (4-(1-(4-(diphenylamino)phenyl)cyclohexyl)phenyl)diphenyl-phosphine oxide (POPCPA), bis[2-(diphenylphosphino)phenyl]ether oxide (DPEPO), 4,4'-bis(N-carbazolyl)-1,1'-biphenyl (CBP), 1,3-bis(carbazole-9-yl)benzene (mCP), 2,8-bis(diphenylphosphoryl)dibenzo[b,d]furan (PPF), 4,4',4"-tri(carbazole-9-yl)-triphenylamine (TCTA), and 1,3,5-tri(1-phenyl-1H-benzo[d]imidazol-2-yl)benzene (TPBi) as a host material. However, embodiments of the present disclosure are not limited thereto, and for example, tris(8-hydroxyquinolinolato)aluminum (Alq 3 ), 9,10-di(naphthalene-2-yl)anthracene (ADN), 2-tert-butyl-9,10-di(naphthalene-2-yl)anthracene (TBADN), distyryl arylide (DSA), 4,4'-bis(9-carbazolyl)-2,2'-dimethyl-biphenyl (CDBP), 2-methyl-9,10-bis(naphthalene-2-yl)anthracene (MADN), hexaphenylcyclotriphosphazene (CP1), 1,4-bis(triphenylsilyl)benzene (UGH2), hexaphenylcyclotrisiloxane (DPSiO 3 ), octaphenylcyclotetrasiloxane (DPSiO 4 ) etc. as the main material.
[0310] The emission layer EML may include a compound represented by Formula Ma. The compound represented by Formula Ma may be used as a phosphorescent dopant material.
[0311] Formula Ma
[0312]
[0313] In formula Ma, Y 1 To Y 4 and Z 1 To Z 4 Can be CR independently 1 or N, R 1 To R 4Each independently may be a hydrogen atom, a deuterium atom, a substituted or unsubstituted amine group, a substituted or unsubstituted sulfenyl group, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, and / or may be bonded to an adjacent group to form a ring. In formula Ma, m is 0 or 1, and n is 2 or 3. In formula Ma, when m is 0, n is 3, or when m is 1, n is 2.
[0314] The compound represented by the formula Ma may be used as a phosphorescent dopant.
[0315] The compound represented by formula Ma may be represented by any one selected from compound M-a1 to compound M-a25. However, compound M-a1 to compound M-a25 are examples, and the compound represented by formula Ma is not limited to those represented by compound M-a1 to compound M-a25.
[0316]
[0317]
[0318] The emission layer EML may include a compound represented by any one selected from Formula Fa to Formula Fc. The compound represented by Formula Fa to Formula Fc may be used as a fluorescent dopant material.
[0319] Formula
[0320]
[0321] In the formula Fa, R a To R j The two of them can be independently *-NAr 1 Ar 2 Replace. a To R j Unreacted*-NAr 1 Ar 2 The remainder of the substitutions may each independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms.
[0322] In *-NAr 1 Ar 2 in Ar1 and Ar 2 Each of them may be independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms. 1 and Ar 2 At least one of may be a heteroaryl group containing O or S as a ring-forming atom. "-*" refers to a position to be attached.
[0323] Formula Fb
[0324]
[0325] In formula Fb, R a and R b Each may independently be 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 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, and / or may be bonded to an adjacent group to form a ring. Ar 1 To Ar 4 Each may independently be a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms.
[0326] In formula Fb, U and V may each independently be a substituted or unsubstituted hydrocarbon ring having 5 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic ring having 2 to 30 ring carbon atoms. 1 To Ar 4 At least one of may be a heteroaryl group containing O or S as a ring-forming atom.
[0327] In formula Fb, the number of rings represented by U and V may be 0 or 1 independently of each other. For example, in formula Fb, it means that when the number of U or V is 1, one ring constitutes a fused ring at the portion indicated by U or V, and when the number of U or V is 0, there is no ring indicated by U or V. For example, when the number of U is 0 and the number of V is 1, or when the number of U is 1 and the number of V is 0, the fused ring with a fluorene core of formula Fb may be a cyclic compound with four rings. In some embodiments, when each number of U and V is 0, the fused ring with a fluorene core in formula Fb may be a cyclic compound with three rings. In some embodiments, when each number of U and V is 1, the fused ring with a fluorene core in formula Fb may be a cyclic compound with five rings.
[0328] Formula Fc
[0329]
[0330] In Formula Fc, A 1 and A 2 can be independently O, S, Se or NR m , and R m It may be a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms. 1 To R 11 Each may independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted amine group, a substituted or unsubstituted boryl group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thiol group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, or may be bonded to an adjacent group to form a ring.
[0331] In Formula Fc, A 1 and A 2 can each independently bond to the substituents of the adjacent rings to form a fused ring. 1 and A 2 Can be NR independently m When A 1 Can be bonded to R 4 or R 5 To form a ring. In some embodiments, A 2 Can be bonded to R 7 or R 8 to form a ring.
[0332] In an embodiment, the emission layer EML may further include styrene derivatives (e.g., 1,4-bis[2-(3-N-ethylcarbazolyl)vinyl]benzene (BCzVB), 4-(di-p-tolylamino)-4'-[(di-p-tolylamino)styrene]diphenylethylene (DPAVB) and N-(4-((E)-2-(6-((E)-4-(diphenylamino)styrene)naphthalene-2-yl)vinyl)phenyl)-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-dipyrenylbenzene, 1,4-bis(N,N-diphenylamino)pyrene), etc. as suitable dopant materials.
[0333] The emission layer EML may further include a suitable phosphorescent dopant material. For example, a metal complex including iridium (Ir), platinum (Pt), osmium (Os), gold (Au), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb) or thulium (Tm) may be used as a phosphorescent dopant. For example, bis(4,6-difluorophenylpyridinyl-N,C2')iridium (III) (FIrpic), bis(2,4-difluorophenylpyridinyl)-tetra(1-pyrazolyl)borate iridium (III) (FIr6) or octaethylporphyrin platinum (PtOEP) may be used as a phosphorescent dopant. However, the embodiments of the present disclosure are not limited thereto.
[0334] The emission layer EML may include a quantum dot material. The core of the quantum dot may be selected from II-VI group compounds, I-II-VI group compounds, II-IV-VI group compounds, I-II-IV-VI group compounds, II-IV-V group compounds, III-VI group compounds, I-III-VI group compounds, III-V group compounds, III-II-V group compounds, IV-VI group compounds, IV group elements, IV group compounds, and combinations thereof.
[0335] The II-VI compounds may be selected from the group consisting of binary compounds selected from the group consisting of CdSe, CdTe, CdS, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, MgSe, MgS and mixtures thereof; ternary compounds selected from the group consisting of CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZn S, CdZnSe, CdZnTe, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, MgZnSe, MgZnS and mixtures thereof; and a quaternary compound selected from the group consisting of HgZnTeS, CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe and mixtures thereof.
[0336] In some embodiments, the II-VI group compound may further include a group I metal and / or a group IV element. The I-II-VI group compound may be selected from CuSnS and CuZnS, and the II-IV-VI group compound may be ZnSnS, etc. The I-II-IV-VI group compound may be selected from a quaternary compound selected from a group including Cu 2 ZnSnS 2 , Cu 2 ZnSnS 4 , Cu 2 ZnSnSe 4 、Ag 2 ZnSnS 2 and mixtures thereof.
[0337] The II-IV-V group compound can be selected from a ternary compound selected from a group consisting of ZnSnP, ZnSnP 2 、ZnSnAs 2 、ZnGeP 2 、ZnGeAs 2 、CdSnP 2 、CdGeP 2 and mixtures thereof.
[0338] III-VI compounds can include binary compounds (e.g., GaS, Ga 2 S 3 ,GaSe,Ga 2 Se 3 , GaTe, InTe, InS, InSe, In 2 S 3andIn 2 Se 3 ), ternary compounds (such as InGaS 3 and InGaSe 3 ), or any optional combination thereof.
[0339] The I-III-VI group compound may be selected from: a ternary compound selected from AgInS, AgInS 2 、CuInS、CuInS 2 、AgGaS 2 、CuGaS 2 、CuGaO 2 、AgGaO 2 、AgAlO 2 and mixtures thereof; or quaternary compounds such as AgInGaS 2 and CuInGaS 2 .
[0340] The III-V compounds may be selected from the group comprising: binary compounds selected from the group comprising GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, InSb and mixtures thereof; ternary compounds selected from the group comprising GaNP, GaNAs, GaNSb, GaPAs, GaPSb, AlNP, AlNAs, AlNSb, AlPAs, AlPSb, InGaP, InAlP, InNP, InNAs, InNSb, InPAs, InPSb and mixtures thereof; and quaternary compounds selected from the group comprising GaAlNP, GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNP, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs, InAlPSb and mixtures thereof. In some embodiments, the III-V group compound may further comprise a Group II metal. For example, InZnP and the like may be selected from the III-II-V group compounds.
[0341] The IV-VI group compound may be selected from the group comprising: a binary compound selected from the group comprising SnS, SnSe, SnTe, PbS, PbSe, PbTe and mixtures thereof; a ternary compound selected from the group comprising SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, SnPbTe and mixtures thereof; and a quaternary compound selected from the group comprising SnPbSSe, SnPbSeTe, SnPbSTe and mixtures thereof. The IV group element may be selected from the group comprising Si, Ge and mixtures thereof. The IV group compound may be a binary compound selected from the group comprising SiC, SiGe and mixtures thereof.
[0342] Each element contained in a multinary compound (such as a binary compound, a ternary compound, and a quaternary compound) may be present in the particle in a substantially uniform concentration or in a substantially non-uniform concentration. For example, the chemical formula refers to the type (species) of the element contained in the compound, and the atomic ratio in the compound may be different. For example, AgInGaS 2 Can refer to AgIn x Ga 1-x S 2 (x is a real number between 0 and 1).
[0343] In some embodiments, the quantum dot may have a single structure in which the concentration of each element contained in the quantum dot is substantially uniform, or a core-shell dual structure. For example, the material contained in the core and the material contained in the shell may be different from each other.
[0344] The shell of the quantum dot can play the role of a protective layer for preventing or reducing the chemical denaturation of the core to maintain the semiconductor properties and / or a charging layer for imparting electrophoretic properties to the quantum dot. The shell can have a single layer or multiple layers. The interface between the core and the shell can have a concentration gradient, wherein the concentration of the element present in the shell decreases toward the center.
[0345] In some embodiments, the quantum dot may have a core-shell dual structure as previously described, comprising a core containing nanocrystals and a shell encapsulating the core. Examples of the shell of the quantum dot may include metal oxides or non-metal oxides, semiconductor compounds, and / or combinations thereof.
[0346] For example, metal oxides or non-metal oxides may include binary compounds (e.g., SiO 2 、Al 2 O 3 、TiO 2 、ZnO、MnO、Mn 2 O 3, Mn 3 O 4 , CuO, FeO, Fe 2 O 3 , Fe 3 O 4 , CoO, Co 3 O 4 and NiO) or ternary compounds (such as MgAl 2 O 4 、CoFe 2 O 4 、NiFe 2 O 4 and CoMn 2 O 4 ), but the embodiments of the present disclosure are not limited thereto.
[0347] In addition, the 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 the present disclosure are not limited thereto.
[0348] Each element contained in the multi-component compound (such as a binary compound and a ternary compound) may be present in the particle in a substantially uniform concentration or a substantially non-uniform concentration. For example, the chemical formula refers to the type (species) of the contained elements, and the atomic ratio in the compound may be different.
[0349] The quantum dots can have a full width at half maximum (FWHM) of an emission wavelength spectrum of about 45 nm or less, about 40 nm or less, or about 30 nm or less. Within this range, color purity or color reproducibility can be improved. In some embodiments, light emitted via quantum dots is emitted in all directions, and light viewing angle properties can be improved.
[0350] In some embodiments, the shape of the quantum dots can be a shape commonly used in the art, without specific limitation. In some embodiments, spherical, pyramidal, multi-armed or cubic nanoparticles, nanotubes, nanowires, nanofibers, nanoplates, etc. can be used.
[0351] By controlling the size of the quantum dots or by controlling the ratio of elements in the quantum dot compound, the band gap can be controlled or selected, and one or more suitable wavelength bands can be obtained from the quantum dot emission layer. Therefore, by utilizing quantum dots (utilizing quantum dots with different sizes or controlling the ratio of elements in the quantum dot compound differently), a light-emitting device that emits one or more suitable wavelengths of light can be realized. For example, the size of the quantum dots or the ratio of elements in the quantum dot compound can be controlled or selected to emit red light, green light, and / or blue light. In some embodiments, quantum dots can be provided to combine one or more suitable emission colors to emit white light.
[0352] exist Figures 3 to 7 In each light emitting device ED of the embodiment illustrated in , an electron transport region ETR is provided on the emission layer EML. The electron transport region ETR may include at least one of a hole blocking layer HBL, an electron transport layer ETL, and an electron injection layer EIL, but the embodiments of the present disclosure are not limited thereto.
[0353] The electron transport region ETR may have a single layer formed of a single material, a single layer formed of a plurality of different materials, or a multilayer structure including a plurality of layers formed of a plurality of different materials.
[0354] For example, the electron transport region ETR may have a single-layer structure of an electron injection layer EIL or an electron transport layer ETL, or may have a single-layer structure formed of an electron injection material and an electron transport material. In some embodiments, the electron transport region ETR may have a single-layer structure formed of a plurality of different materials, or may 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 sequentially stacked from the emission layer EML, but the embodiments of the present disclosure are not limited thereto. The electron transport region ETR may have, for example, about to about Thickness.
[0355] The electron transport region ETR may be formed using one or more suitable methods such as vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB), inkjet printing, laser printing, and / or laser induced thermal imaging (LITI).
[0356] The electron transport region ETR may include a compound represented by Formula ET-2:
[0357] Formula ET-2
[0358]
[0359] In formula ET-2, selected from X 1 To X3 At least one of them is N, and the rest are CR a . R a It may be a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms. 1 To Ar 3 Each may 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 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms.
[0360] In Formula ET-2, a to c may each independently be an integer from 0 to 10. In Formula ET-2, L 1 To L 3 Each of a to c may be independently a direct bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms. In some embodiments, when a to c may be independently an integer of 2 or greater, L 1 To L 3 Each may independently be a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms.
[0361] The electron transport region ETR may include an anthracene-based compound. However, the embodiments of the present disclosure are not limited thereto, and the electron transport region ETR may include, for example, tris(8-hydroxyquinolinato)aluminum (Alq 3), 1,3,5-tris[(3-pyridyl)-phenyl-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-benzo[d]imidazol-2-yl)benzene (TPBi), 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bp hen), 3-(4-biphenyl)-4-phenyl-5-tert-butylphenyl-1,2,4-triazole (TAZ), 4-(naphthalene-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-quinolinolato-N1,O8)-(1,1'-biphenyl-4-ato)aluminum (BAlq), bis(benzoquinolinolato-10-ato)beryllium (Bebq 2 ), 9,10-di(naphthalene-2-yl)anthracene (ADN), 1,3-bis[3,5-di(pyridin-3-yl)phenyl]benzene (BmPyPhB) or a mixture thereof.
[0362] The electron transport region ETR may include at least one selected from the group consisting of compounds ET1 to ET36:
[0363]
[0364]
[0365]
[0366] In some embodiments, the electron transport region ETR may include metal halides (e.g., LiF, NaCl, CsF, RbCl, RbI, CuI, and KI), lanthanide metals (e.g., Yb), and co-deposited materials of metal halides and lanthanide metals. For example, the electron transport region ETR may include KI:Yb, RbI:Yb, LiF:Yb, etc. as co-deposited materials. In some embodiments, the electron transport region ETR may use materials such as Li 2 The electron transport region ETR may be formed by a metal oxide of O or BaO or 8-hydroxy-quinoline lithium (Liq), etc., but the embodiments of the present disclosure are not limited thereto. The electron transport region ETR may also be formed by a mixture material of an electron transport material and an insulating organic metal salt. The organic metal salt may be a material having a band gap of about 4 eV or greater than 4 eV. For example, the organic metal salt may include, for example, a metal acetate, a metal benzoate, a metal acetoacetate, a metal acetylacetonate, or a metal stearate.
[0367] In addition to the materials described previously, the electron transport region ETR may further include at least one of 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), diphenyl(4-(triphenylsilyl)phenyl)phosphine oxide (TSPO1), and 4,7-diphenyl-1,10-phenanthroline (Bphen), but embodiments of the present disclosure are not limited thereto.
[0368] The electron transport region ETR may include the previously described compound of the electron transport region ETR in at least one of the electron injection layer EIL, the electron transport layer ETL, and the hole blocking layer HBL.
[0369] When the electron transport region ETR includes the electron transport layer ETL, the electron transport layer ETL may have a thickness of about to about For example, about to about When the thickness of the electron transport layer ETL satisfies the above range, satisfactory electron transport characteristics can be obtained without a significant increase in driving voltage. When the electron transport region ETR includes the electron injection layer EIL, the electron injection layer EIL may have a thickness of about to about For example, about to about When the thickness of the electron injection layer EIL satisfies the previously described range, satisfactory electron injection characteristics can be obtained without a significant increase in driving voltage.
[0370] The second electrode EL2 is provided on the electron transport region ETR. The second electrode EL2 may be a common electrode. The second electrode EL2 may be a cathode or an anode, but the embodiments of the present disclosure are not limited thereto. For example, when the first electrode EL1 is an anode, the second electrode EL2 may be a cathode, and when the first electrode EL1 is a cathode, the second electrode EL2 may be an anode.
[0371] The second electrode EL2 may be a transmissive electrode, a semi-transmissive reflective electrode or a reflective electrode. When the second electrode EL2 is a transmissive electrode, the second electrode EL2 may be formed of a transparent metal oxide (e.g., indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), indium tin zinc oxide (ITZO), etc.).
[0372] When the second electrode EL2 is a semi-transmissive reflective electrode or a reflective electrode, the second electrode EL2 may include Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, Mo, Ti, Yb, W, or a compound or mixture thereof (e.g., AgMg, AgYb, or MgYb); and / or LiF / Ca, or LiF / Al. In some embodiments, the second electrode EL2 may have a multilayer structure including a reflective film or a semi-transmissive reflective film formed of the previously described materials, and a transparent conductive film formed of ITO, IZO, ZnO, ITZO, etc. For example, the second electrode EL2 may include the previously described metal material, a combination of at least two of the previously described metal materials, an oxide of the previously described metal material, etc.
[0373] In some embodiments, the second electrode EL2 may be connected to the auxiliary electrode. When the second electrode EL2 is connected to the auxiliary electrode, the resistance of the second electrode EL2 may be reduced.
[0374] In some embodiments, a cover layer CPL may be further disposed on the second electrode EL2 of the light emitting device ED of the embodiments. The cover layer CPL may include a plurality of layers or a single layer.
[0375] In an embodiment, the capping layer CPL may be an organic layer or an inorganic layer. For example, when the capping layer CPL includes an inorganic material, the inorganic material may include an alkali metal compound (eg, LiF), an alkaline earth metal compound (eg, MgF 2 )、SiON、SiN x 、SiO y wait.
[0376] For example, when the capping layer CPL includes an organic material, the organic material may include α-NPD, NPB, TPD, m-MTDATA, Alq 3 , CuPc, N4,N4,N4',N4'-tetrakis(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, the embodiments of the present disclosure are not limited thereto, and the cover layer CPL may include at least one selected from Compound P1 to Compound P5:
[0377]
[0378] In some embodiments, the refractive index of the cover layer CPL may be about 1.6 or greater. For example, the refractive index of the cover layer CPL may be about 1.6 or greater with respect to light in a wavelength range of about 550 nm to about 660 nm.
[0379] Figures 8 to 11 is a cross-sectional view of a display device according to an embodiment. Figures 8 to 11 In explaining the display device according to the embodiment, the Figures 1 to 7 Those that overlap will be explained in , and the differences will be mainly explained.
[0380] refer to Figure 8 According to the embodiment, the display device DD-a may include a display panel DP including a display device layer DP-ED, a light control layer CCL disposed on the display panel DP, and a color filter layer CFL. Figure 8 In the embodiment shown in FIG. 4 , the display panel DP may include a base layer BS, a circuit layer DP-CL provided on the base layer BS, and a display device layer DP-ED, and the display device layer DP-ED may include a light emitting device ED.
[0381] The light emitting device ED may include a first electrode EL1, a hole transport region HTR disposed on the first electrode EL1, an emission layer EML disposed on the hole transport region HTR, an electron transport region ETR disposed on the emission layer EML, and a second electrode EL2 disposed on the electron transport region ETR. Figures 3 to 7 The same structure of the light emitting device can be applied to Figure 8 The structure of the light-emitting device ED is shown in FIG. Figure 8 The light emitting device ED shown in EMBODIMENTS includes the condensed polycyclic compound of the embodiment and can exhibit low driving voltage, high emission efficiency, and long lifetime characteristics.
[0382] refer to Figure 8 , the emission layer EML can be arranged in the opening OH defined in the pixel defining film PDL. For example, the emission layer EML separated by the pixel defining film PDL and provided corresponding to each light-emitting area PXA-R, PXA-G and PXA-B can be configured to emit light in substantially the same wavelength range. In the display device DD-a of the embodiment, the emission layer EML can be configured to emit blue light. In some embodiments, different from the illustrated configuration, in the embodiment, the emission layer EML can be provided as a common layer in all light-emitting areas PXA-R, PXA-G and PXA-B.
[0383] The light control layer CCL may be disposed on the display panel DP. The light control layer CCL may include a light converter. The light converter may be a quantum dot, a phosphor, etc. The light converter may be configured to emit the provided light by converting its wavelength. For example, the light control layer CCL may be a layer including quantum dots or a layer including phosphors.
[0384] The light-control layer CCL may include a plurality of light-control parts CCP1, CCP2, and CCP3. The light-control parts CCP1, CCP2, and CCP3 may be spaced apart from each other.
[0385] refer to Figure 8 , the separation pattern BMP may be disposed between the light control parts CCP1 , CCP2 , and CCP3 that are spaced apart from each other, but embodiments of the present disclosure are not limited thereto. Figure 8 It is illustrated that separation pattern BMP does not overlap light control parts CCP1 , CCP2 , and CCP3 , but at least a portion of edges of light control parts CCP1 , CCP2 , and CCP3 may overlap separation pattern BMP.
[0386] The light control layer CCL may include: a first light control component CCP1 containing first quantum dots QD1 that convert the first color light provided by the light emitting device ED into second color light, a second light control component CCP2 containing second quantum dots QD2 that convert the first color light into third color light, and a third light control component CCP3 that transmits the first color light.
[0387] In an embodiment, the first light control component CCP1 can provide red light as the second color light, and the second light control component CCP2 can provide green light as the third color light. The third light control component CCP3 can provide blue light by transmitting blue light as the first color light provided by the light emitting device ED. For example, the first quantum dot QD1 can be a red quantum dot, and the second quantum dot QD2 can be a green quantum dot. The same as previously described can be applied to the quantum dots QD1 and QD2.
[0388] In some embodiments, the light control layer CCL may further include a scatterer SP. The first light control component CCP1 may include a first quantum dot QD1 and a scatterer SP, the second light control component CCP2 may include a second quantum dot QD2 and a scatterer SP, and the third light control component CCP3 may not include (e.g., may exclude) any quantum dot but include a scatterer SP.
[0389] The scatterer SP may be inorganic particles. For example, the scatterer SP may include TiO 2 、ZnO、Al 2 O 3 、SiO 2 and hollow spherical silica. The scatterer SP may include a member selected from TiO 2 、ZnO、Al 2 O 3 、SiO 2 and hollow spherical silica, or may be selected from TiO 2 、ZnO、Al2 O 3 、SiO 2 and a mixture of at least two of the materials selected from hollow spherical silica.
[0390] The first light control component CCP1, the second light control component CCP2, and the third light control component CCP3 may each include matrix resins BR1, BR2, and BR3 in which quantum dots QD1 and QD2 and scatterers SP are dispersed. In an embodiment, the first light control component CCP1 may include first quantum dots QD1 and scatterers SP dispersed in a first matrix resin BR1, the second light control component CCP2 may include second quantum dots QD2 and scatterers SP dispersed in a second matrix resin BR2, and the third light control component CCP3 may include scatterers SP dispersed in a third matrix resin BR3.
[0391] The matrix resins BR1, BR2 and BR3 are media in which quantum dots QD1 and QD2 and scatterers SP are dispersed, and may be formed by one or more than one suitable resin composition (which may be generally referred to as an adhesive). For example, the matrix resins BR1, BR2 and BR3 may be acrylic-based resins, urethane-based resins, silicone-based resins, epoxy-based resins, etc. The matrix resins BR1, BR2 and BR3 may be transparent resins. In an embodiment, the first matrix resin BR1, the second matrix resin BR2 and the third matrix resin BR3 may be the same or different from each other.
[0392] The light control layer CCL may include a barrier layer BFL1. The barrier layer BFL1 may play a role in preventing or reducing the penetration of moisture and / or oxygen (hereinafter, referred to as "moisture / oxygen"). The barrier layer BFL1 may block or reduce the exposure of the light control components CCP1, CCP2, and CCP3 to moisture / oxygen. In some embodiments, the barrier layer BFL1 may cover the light control components CCP1, CCP2, and CCP3. In some embodiments, the barrier layer BFL2 may be provided between the light control components CCP1, CCP2, and CCP3 and the color filter layer CFL.
[0393] The barrier layers BFL1 and BFL2 may include at least one inorganic layer. For example, the barrier layers BFL1 and BFL2 may include an inorganic material. For example, the barrier layers BFL1 and BFL2 may include silicon nitride, aluminum nitride, zirconium nitride, titanium nitride, hafnium nitride, tantalum nitride, silicon oxide, aluminum oxide, titanium oxide, tin oxide, cerium oxide, silicon oxynitride, a metal film ensuring transmittance, etc. In some embodiments, the barrier layers BFL1 and BFL2 may further include an organic film. The barrier layers BFL1 and BFL2 may be formed by a single layer or a plurality of layers.
[0394] In the display device DD-a of the embodiment, the color filter layer CFL may be disposed on the light control layer CCL. For example, the color filter layer CFL may be directly disposed on the light control layer CCL. In this case, the blocking layer BFL2 may not be provided.
[0395] The color filter layer CFL may include color filters CF1, CF2, and CF3. The color filter layer CFL may include a first filter CF1 configured to transmit a second color light, a second filter CF2 configured to transmit a third color light, and a third filter CF3 configured to transmit the first color light. For example, the first filter CF1 may be a red filter, the second filter CF2 may be a green filter, and the third filter CF3 may be a blue filter. The filters CF1, CF2, and CF3 may each include a polymer photosensitive resin and a pigment or dye. The first filter CF1 may include a red pigment or dye, the second filter CF2 may include a green pigment or dye, and the third filter CF3 may include a blue pigment or dye.
[0396] In some embodiments, the embodiments of the present disclosure are not limited thereto, and the third filter CF3 may not include (e.g., may exclude) a pigment or dye. The third filter CF3 may include a polymer photosensitive resin and may not include (e.g., may exclude) a pigment or dye. The third filter CF3 may be transparent. The third filter CF3 may be formed of a transparent photosensitive resin.
[0397] Furthermore, in the embodiment, 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 separated but may be provided as one filter.
[0398] Although not illustrated, the color filter layer CFL may further include a light shielding member. The light shielding member may be a black matrix. The light shielding member may include an organic light shielding material or an inorganic light shielding material containing a black pigment or dye. The light shielding member may prevent or reduce light leakage and may separate the boundaries between adjacent filters CF1, CF2, and CF3. In addition, in the embodiment, the light shielding member may be formed by a blue filter.
[0399] The first to third filters CF1, CF2, and CF3 may be disposed to correspond to the red light emitting area PXA-R, the green light emitting area PXA-G, and the blue light emitting area PXA-B, respectively.
[0400] The base substrate BL may be disposed on the color filter layer CFL. The base substrate BL may be a member providing a base surface in which the color filter layer CFL, the light control layer CCL, etc. are disposed. The base substrate BL may be a glass substrate, a metal substrate, a plastic substrate, etc. However, the embodiments of the present disclosure are not limited thereto, and the base substrate BL may be an inorganic layer, an organic layer, or a composite material layer. In some embodiments, unlike the illustrated configuration, the base substrate BL may not be provided.
[0401] Fig. 9 is a cross-sectional view showing a portion of a display device according to an embodiment. In the display device DD-TD of the embodiment, the light-emitting device ED-BT may include a plurality of light-emitting structures OL-B1, OL-B2, and OL-B3. At least one selected from the plurality of light-emitting structures OL-B1, OL-B2, and OL-B3 may include the fused polycyclic compound of the embodiment. Therefore, the light-emitting device ED-BT may exhibit low driving voltage, high emission efficiency, and long service life characteristics.
[0402] The light emitting device ED-BT may include a first electrode EL1 and a second electrode EL2 facing each other, and a plurality of light emitting structures OL-B1, OL-B2, and OL-B3 sequentially stacked in a 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 emission layer EML ( Figure 8 ), and a hole transport region HTR and an electron transport region ETR ( Figure 8 ).
[0403] For example, the light emitting devices ED-BT included in the display devices DD-TD of the embodiments may be light emitting devices having a tandem structure and including a plurality of emission layers.
[0404] exist Fig. 9 In the embodiment illustrated in , all the light beams emitted from the light emitting structures OL-B1, OL-B2 and OL-B3, respectively, may be blue light. However, the embodiments of the present disclosure are not limited thereto, and the light beams emitted from the light emitting structures OL-B1, OL-B2 and OL-B3, respectively, may have wavelength ranges different from each other. For example, a light emitting device ED-BT including a plurality of light emitting structures OL-B1, OL-B2 and OL-B3 emitting light beams having wavelength ranges different from each other may be configured to emit white light (e.g., combined white light).
[0405] The charge generation layers CGL1 and CGL2 may be disposed between two of the adjacent light emitting structures OL-B1, OL-B2, and OL-B3, respectively. The charge generation layers CGL1 and CGL2 may include a p-type charge generation layer and / or an n-type charge generation layer.
[0406] refer to Fig.10 , the display device DD-b according to the embodiment may include light-emitting devices ED-1, ED-2 and ED-3 in which two emission layers are stacked. At least one selected from the light-emitting devices ED-1, ED-2 and ED-3 may contain the fused polycyclic compound of the embodiment. Therefore, at least one selected from the light-emitting devices ED-1, ED-2 and ED-3 may show low driving voltage, high emission efficiency and long service life characteristics.
[0407] and Figure 2 Compared with the display device DD of the embodiment illustrated in FIG. Fig.10 The embodiment illustrated in FIG. 1 is different in that each of the first to third light-emitting devices ED-1, ED-2, and ED-3 includes two emission layers stacked in the thickness direction. In each of the first to third light-emitting devices ED-1, ED-2, and ED-3, the two emission layers may be configured to emit light in substantially the same wavelength region.
[0408] The first light-emitting device ED-1 may include a first red emission layer EML-R1 and a second red emission layer EML-R2. The second light-emitting device ED-2 may include a first green emission layer EML-G1 and a second green emission layer EML-G2. In some embodiments, the third light-emitting device ED-3 may include a first blue emission layer EML-B1 and a second blue emission layer EML-B2. The emission auxiliary component OG may be disposed between the first red emission layer EML-R1 and the second red emission layer EML-R2, between the first green emission layer EML-G1 and the second green emission layer EML-G2, and between the first blue emission layer EML-B1 and the second blue emission layer EML-B2.
[0409] The emission auxiliary component OG may include a single layer or a multilayer. The emission auxiliary component OG may include a charge generation layer. More specifically, the emission auxiliary component OG may include an electron transport region, a charge generation layer, and a hole transport region stacked in sequence. The emission auxiliary component OG may be provided as a common layer in all of the first to third light-emitting devices ED-1, ED-2, and ED-3. However, the embodiments of the present disclosure are not limited thereto, and the emission auxiliary component OG may be provided by patterning in an opening OH defined in a pixel defining film PDL.
[0410] The first red emission layer EML-R1, the first green emission layer EML-G1 and the first blue emission layer EML-B1 may be disposed between the emission auxiliary component OG and the electron transport region ETR. The second red emission layer EML-R2, the second green emission layer EML-G2 and the second blue emission layer EML-B2 may be disposed between the hole transport region HTR and the emission auxiliary component OG.
[0411] For example, the first light-emitting device ED-1 may include a first electrode EL1, a hole transport region HTR, a second red emission layer EML-R2, an emission auxiliary component OG, a first red emission layer EML-R1, an electron transport region ETR, and a second electrode EL2 stacked in sequence. The second light-emitting device ED-2 may include a first electrode EL1, a hole transport region HTR, a second green emission layer EML-G2, an emission auxiliary component OG, a first green emission layer EML-G1, an electron transport region ETR, and a second electrode EL2 stacked in sequence. The third light-emitting device ED-3 may include a first electrode EL1, a hole transport region HTR, a second blue emission layer EML-B2, an emission auxiliary component OG, a first blue emission layer EML-B1, an electron transport region ETR, and a second electrode EL2 stacked in sequence.
[0412] In some embodiments, an optical auxiliary layer PL may be disposed 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 on the display panel DP and control reflected light due to external light in the display panel DP. Unlike the illustrated configuration, the optical auxiliary layer PL in the display device according to the embodiment may not be provided.
[0413] Different from Fig. 9 and Fig.10 , Fig.11 The display device DD-c is shown to include four light emitting structures OL-B1, OL-B2, OL-B3 and OL-C1. The light emitting device ED-CT may include a first electrode EL1 and a second electrode EL2 disposed opposite to each other, and first to fourth light emitting structures OL-B1, OL-B2, OL-B3 and OL-C1 stacked in sequence in the thickness direction between the first electrode EL1 and the second electrode EL2. At least one selected from the first to fourth light emitting structures OL-B1, OL-B2, OL-B3 and OL-C1 may include the fused polycyclic compound of the embodiment. Therefore, the light emitting device ED-CT may display low driving voltage, high emission efficiency and long service life characteristics.
[0414] The charge generation layers CGL1, CGL2, and CGL3 may be disposed between the first to fourth light emitting structures OL-B1, OL-B2, OL-B3, and OL-C1. Among the four light emitting structures, the first to third light emitting structures OL-B1, OL-B2, and OL-B3 may be configured to emit blue light, and the fourth light emitting structure OL-C1 may be configured to emit green light. However, the embodiments of the present disclosure are not limited thereto, and the first to fourth light emitting structures OL-B1, OL-B2, OL-B3, and OL-C1 may be configured to emit light beams in different wavelength regions.
[0415] The charge generation layers CGL1, CGL2, and CGL3 disposed between the adjacent light emitting structures OL-B1, OL-B2, OL-B3, and OL-C1 may include a p-type charge generation layer and / or an n-type charge generation layer.
[0416] In an embodiment, the electronic device may include a display device comprising a plurality of light emitting devices and a control unit for controlling the display device. The electronic device of the embodiment may be a device activated according to an electrical signal. The electronic device may include one or more than one display device of a suitable embodiment. For example, the electronic device may include not only large electronic devices such as televisions, monitors, or outdoor billboards, but may also include small electronic devices and medium-sized electronic devices such as personal computers, laptop computers, personal digital terminals, display devices for vehicles, game consoles, portable electronic devices, or cameras.
[0417] Fig.12 is a view illustrating a vehicle AM in which first to fourth display devices DD-1, DD-2, DD-3, and DD-4 are provided. At least one selected from the first to fourth display devices DD-1, DD-2, DD-3, and DD-4 may include the same Figure 1 and Figure 2 as well as Figures 8 to 11 The described display devices DD, DD-TD, DD-a, DD-b and DD-c have the same configuration.
[0418] Fig.12Vehicle AM is illustrated, but this is an example, and the first to fourth display devices DD-1, DD-2, DD-3, and DD-4 can be set in another vehicle such as a bicycle, a motorcycle, a train, a ship, and an airplane. In some embodiments, at least one of the first to fourth display devices DD-1, DD-2, DD-3, and DD-4 including the same configuration as the display devices DD, DD-TD, DD-a, DD-b, and DD-c of the embodiment can be used for a personal computer, a laptop computer, a personal digital terminal, a game console, a portable electronic device, a television, a monitor, an outdoor billboard, etc. In some embodiments, these are provided only as embodiments, and therefore can be used in other electronic devices, unless departing from the present disclosure.
[0419] At least one selected from the first to fourth display devices DD-1, DD-2, DD-3, and DD-4 may include a reference Figures 3 to 7 One of the light-emitting devices ED explained. At least one selected from the first to fourth display devices DD-1, DD-2, DD-3 and DD-4 may include the fused polycyclic compound of the embodiment. The first to fourth display devices DD-1, DD-2, DD-3 and DD-4 including the fused polycyclic compound of the embodiment may show improved display efficiency and display life.
[0420] refer to Fig.12 The vehicle AM may include a steering wheel HA and a gear member GR for driving the vehicle AM. In some embodiments, the vehicle AM may include a front window GL disposed to face the driver.
[0421] The first display device DD-1 may be disposed in a first area overlapping the steering wheel HA. For example, the first display device DD-1 may be a digital cluster device that displays first information of the vehicle AM. The first information may include a first scale indicating the vehicle travel speed AM, a second scale indicating the engine speed (i.e., revolutions per minute (RPM)), an image indicating the fuel status, etc. The first scale and the second scale may be indicated as digital images.
[0422] The second display device DD-2 can be arranged in a second zone facing the driver's seat and overlapping with the front window GL. The driver's seat can be a seat in which the steering wheel HA is arranged. For example, the second display device DD-2 can be a head-up display (HUD) that displays the second information of the vehicle AM. The second display device DD-2 can be optically transparent. The second information can include a number indicating the driving speed, and can further include information such as the current time. Different from the illustrated configuration, the second information of the second display device DD-2 can be projected onto the front window GL to be displayed.
[0423] The third display device DD-3 may be arranged in a third zone adjacent to the gear member GR. For example, the third display device DD-3 may be arranged between the driver's seat and the passenger seat and may be a central information display (CID) of the vehicle AM for displaying the third information. The passenger seat may be a seat spaced apart from the driver's seat, and the gear member GR is arranged between the passenger seat and the driver's seat. The third information may include information about traffic (e.g., navigation information), playing music or radio or video (or images), the temperature inside the vehicle AM, etc.
[0424] The fourth display device DD-4 may be spaced apart from the steering wheel HA and the shift member GR, and may be disposed 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 that displays the fourth information. The fourth display device DD-4 may display an image of the outside of the vehicle AM captured by a camera module CM disposed outside the vehicle AM.
[0425] The first to fourth information described previously 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, the embodiments of the present disclosure are not limited thereto, and a portion of the first to fourth information may include the same information as each other.
[0426] Hereinafter, the fused polycyclic compound according to the embodiment of the present disclosure and the light emitting device of the embodiment will be specifically explained with reference to the embodiment and the comparative embodiment. In some embodiments, the embodiment is an example intended to help understand the present disclosure, but the scope of the present disclosure is not limited thereto.
[0427] Example
[0428] 1. Synthesis of condensed polycyclic compounds according to the embodiment
[0429] The synthesis method of the compound according to the embodiment will be specifically explained by exemplifying the synthesis method of Compound 12, Compound 47, Compound 58, Compound 69, Compound 80, and Compound 110. In some embodiments, the synthesis method of the fused polycyclic compound explained below is an embodiment, and the synthesis method of the fused polycyclic compound according to the embodiment of the present disclosure is not limited to the embodiment described herein.
[0430] 1 Synthesis of fused polycyclic compound 12
[0431] The condensed polycyclic compound 12 according to the embodiment can be synthesized through the steps (eg, actions or tasks) of Reaction 1, for example.
[0432] Reaction 1
[0433]
[0434] Synthesis of intermediate 12-1
[0435] [1,1':3',1"-terphenyl]-2'-amine (2 equivalents), 1,3-dichloroindolo[3,2,1-jk]carbazole (1 equivalent), tris(dibenzylideneacetone)dipalladium(0) (0.05 equivalents), tri-tert-butylphosphine (0.1 equivalents) and sodium tert-butoxide (2 equivalents) were dissolved in o-xylene and stirred at about 140 degrees Celsius for about 10 hours. After cooling, the reaction product was washed three times with ethyl acetate and water (for example, diluted with ethyl acetate and then washed three times with water or washed three times with ethyl acetate and water), and layer separation was performed to obtain an organic layer. The organic layer thus obtained was washed with MgSO 4 Dried, and dried under reduced pressure. The crude product was purified by column chromatography using dichloromethane (MC) and n-hexane to obtain Intermediate 12-1 (yield: 75%).
[0436] Synthesis of intermediate 12-2
[0437] 1-Bromo-3-chlorobenzene (4 equivalents), intermediate 12-1 (1 equivalent), tris(dibenzylideneacetone)dipalladium(0) (0.1 equivalent), tri-tert-butylphosphine (0.2 equivalent) and sodium tert-butoxide (3 equivalents) were dissolved in o-xylene and stirred at about 160 degrees Celsius for about 36 hours. After cooling, the reaction product was washed three times with ethyl acetate and water, and layer separation was performed to obtain an organic layer. The organic layer thus obtained was treated with MgSO 4 Dried, and dried under reduced pressure. The crude product was purified by column chromatography using MC and n-hexane to obtain Intermediate 12-2 (yield: 83%).
[0438] Synthesis of intermediate 12-3
[0439] 9H-3,9'-bicarbazole-1,1',2,2',3',4,4',5,5',6,6',7,7',8,8'-d15 (2.1 equivalents), intermediate 12-2 (1 equivalent), tris(dibenzylideneacetone)dipalladium(0) (0.05 equivalents), tri-tert-butylphosphine (0.1 equivalents) and sodium tert-butoxide (3 equivalents) were dissolved in o-xylene and stirred at about 140 degrees Celsius for about 12 hours. After cooling, the reaction product was washed three times with ethyl acetate and water, and layer separation was performed to obtain an organic layer. The organic layer thus obtained was washed with MgSO 4Dried, and dried under reduced pressure. The crude product was purified by column chromatography using MC and n-hexane to obtain Intermediate 12-3 (yield: 80%).
[0440] Synthesis of compound 12
[0441] Intermediate 12-3 (1 equivalent) was dissolved in o-dichlorobenzene and cooled to 0 degrees Celsius, and BBr 3 (3 equivalents) was slowly injected therein. After completion of the dropwise addition, the temperature was raised to about 180 degrees Celsius, and stirring was performed for about 48 hours. After cooling the reaction product, triethylamine was slowly added dropwise to the flask containing the reaction product to complete the reaction, and ethanol was added to the reaction product to precipitate. The precipitate was filtered to obtain a crude product. The solid thus obtained was purified by column chromatography using MC and n-hexane to obtain compound 12 (yield: 6%).
[0442] 2 Synthesis of fused polycyclic compound 47
[0443] The condensed polycyclic compound 47 according to the embodiment can be synthesized through the step of Reaction 2, for example.
[0444] Reaction 2
[0445]
[0446] Synthesis of Intermediate 47-1
[0447] 5'-(tert-butyl)-[1,1':3',1"-terphenyl]-2'-amine (2 equivalents), 1,3-dichloroindolo[3,2,1-jk]carbazole (1 equivalent), tris(dibenzylideneacetone)dipalladium(0) (0.05 equivalents), tri-tert-butylphosphine (0.1 equivalents) and sodium tert-butoxide (2 equivalents) were dissolved in o-xylene and stirred at about 140 degrees Celsius for about 10 hours. After cooling, the reaction product was washed three times with ethyl acetate and water, and layer separation was performed to obtain an organic layer. The organic layer thus obtained was washed with MgSO 4 Dried, and dried under reduced pressure. The crude product was purified by column chromatography using MC and n-hexane to obtain Intermediate 47-1 (yield: 81%).
[0448] Synthesis of Intermediate 47-2
[0449] 1-Bromo-3-chlorobenzene (4 equivalents), Intermediate 47-1 (1 equivalent), tris(dibenzylideneacetone)dipalladium(0) (0.1 equivalent), tri-tert-butylphosphine (0.2 equivalent) and sodium tert-butoxide (3 equivalents) were dissolved in o-xylene and stirred at about 160 degrees Celsius for about 36 hours. After cooling, the reaction product was washed three times with ethyl acetate and water, and layer separation was performed to obtain an organic layer. The organic layer thus obtained was washed with MgSO 4 Dried, and dried under reduced pressure. The crude product was purified by column chromatography using MC and n-hexane to obtain Intermediate 47-2 (yield: 78%).
[0450] Synthesis of Intermediate 47-3
[0451] 3-(Phenyl-d5)-9H-carbazole-1,2,4,5,6,7,8-d7 (2 equivalents), intermediate 47-2 (1 equivalent), tris(dibenzylideneacetone)dipalladium(0) (0.05 equivalents), tri-tert-butylphosphine (0.1 equivalents) and sodium tert-butoxide (3 equivalents) were dissolved in o-xylene and stirred at about 140 degrees Celsius for about 12 hours. After cooling, the reaction product was washed three times with ethyl acetate and water, and layer separation was performed to obtain an organic layer. The organic layer thus obtained was treated with MgSO 4 Dried, and dried under reduced pressure. The crude product was purified by column chromatography using MC and n-hexane to obtain Intermediate 47-3 (yield: 78%).
[0452] Synthesis of compound 47
[0453] Intermediate 47-3 (1 equivalent) was dissolved in o-dichlorobenzene and cooled to 0 degrees Celsius, and under a nitrogen atmosphere, BBr 3 (3 equivalents) was slowly injected therein. After completion of the dropwise addition, the temperature was raised to about 180 degrees Celsius, and stirring was performed for about 48 hours. After cooling the reaction product, triethylamine was slowly added dropwise to the flask containing the reaction product to complete the reaction, and ethanol was added to the reaction product to precipitate. The precipitate was filtered to obtain a crude product. The solid thus obtained was purified by column chromatography using MC and n-hexane to obtain compound 47 (yield: 5%).
[0454] 3 Synthesis of fused polycyclic compound 58
[0455] The condensed polycyclic compound 58 according to the embodiment can be synthesized through the steps of Reaction 3, for example.
[0456] Reaction 3
[0457]
[0458] Synthesis of Intermediate 58-1
[0459] 5'-(tert-butyl)-[1,1':3',1"-terphenyl]-2'-amine (1 equivalent), 1,3-dichloroindolo[3,2,1-jk]carbazole (1 equivalent), tris(dibenzylideneacetone)dipalladium(0) (0.05 equivalent), 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (BINAP, 0.1 equivalent) and sodium tert-butoxide (2 equivalents) were dissolved in o-xylene and stirred at about 140 degrees Celsius for about 10 hours. After cooling, the reaction product was washed three times with ethyl acetate and water, and layer separation was performed to obtain an organic layer. The organic layer thus obtained was washed with MgSO 4 Dried, and dried under reduced pressure. The crude product was purified by column chromatography using MC and n-hexane to obtain Intermediate 58-1 (yield: 73%).
[0460] Synthesis of Intermediate 58-2
[0461] 1-Bromo-3-chlorobenzene (3 equivalents), Intermediate 58-1 (1 equivalent), tris(dibenzylideneacetone)dipalladium(0) (0.1 equivalent), tri-tert-butylphosphine (0.2 equivalent) and sodium tert-butoxide (3 equivalents) were dissolved in o-xylene and stirred at about 160 degrees Celsius for about 36 hours. After cooling, the reaction product was washed three times with ethyl acetate and water, and layer separation was performed to obtain an organic layer. The organic layer thus obtained was washed with MgSO 4 Dried, and dried under reduced pressure. The crude product was purified by column chromatography using MC and n-hexane to obtain Intermediate 58-2 (yield: 77%).
[0462] Synthesis of Intermediate 58-3
[0463] 5'-(tert-butyl)-[1,1':3',1"-terphenyl]-2'-amine (1 equivalent), intermediate 58-2 (1 equivalent), tris(dibenzylideneacetone)dipalladium(0) (0.05 equivalent), tri-tert-butylphosphine (0.1 equivalent) and sodium tert-butoxide (2 equivalents) were dissolved in o-xylene and stirred at about 140 degrees Celsius for about 10 hours. After cooling, the reaction product was washed three times with ethyl acetate and water, and layer separation was performed to obtain an organic layer. The organic layer thus obtained was washed with MgSO 4 Dried, and dried under reduced pressure. The crude product was purified by column chromatography using MC and n-hexane to obtain Intermediate 58-3 (yield: 84%).
[0464] Synthesis of Intermediate 58-4
[0465] 3,5-di-tert-butyl-4'-iodo-1,1'-biphenyl (4 equivalents), intermediate 58-3 (1 equivalent), tris(dibenzylideneacetone)dipalladium(0) (0.1 equivalent), tri-tert-butylphosphine (0.2 equivalent) and sodium tert-butoxide (3 equivalents) were dissolved in o-xylene and stirred at about 160 degrees Celsius for about 36 hours. After cooling, the reaction product was washed three times with ethyl acetate and water, and layer separation was performed to obtain an organic layer. The organic layer thus obtained was washed with MgSO 4 Dried, and dried under reduced pressure. The crude product was purified by column chromatography using MC and n-hexane to obtain Intermediate 58-4 (yield: 79%).
[0466] Synthesis of Intermediate 58-5
[0467] 3-phenyl-9H-carbazole-1,2,4,5,6,7,8-d7 (1 equivalent), intermediate 58-4 (1 equivalent), tris(dibenzylideneacetone)dipalladium(0) (0.05 equivalent), tri-tert-butylphosphine (0.1 equivalent) and sodium tert-butoxide (2 equivalents) were dissolved in o-xylene and stirred at about 140 degrees Celsius for about 10 hours. After cooling, the reaction product was washed three times with ethyl acetate and water, and layer separation was performed to obtain an organic layer. The organic layer thus obtained was treated with MgSO 4 Dried, and dried under reduced pressure. The crude product was purified by column chromatography using MC and n-hexane to obtain Intermediate 58-5 (yield: 83%).
[0468] Synthesis of compound 58
[0469] Intermediate 58-5 (1 equivalent) was dissolved in o-dichlorobenzene and cooled to 0 degrees Celsius, and under a nitrogen atmosphere, BBr 3 The mixture was stirred for about 48 hours. After the reaction product was cooled, triethylamine was slowly added dropwise to the flask containing the reaction product to complete the reaction, and ethanol was added to the reaction product to precipitate. The precipitate was filtered to obtain a crude product. The solid thus obtained was purified by column chromatography using MC and n-hexane to obtain compound 58 (yield: 5%).
[0470] 4 Synthesis of fused polycyclic compound 69
[0471] The condensed polycyclic compound 69 according to the embodiment can be synthesized through the steps of Reaction 4, for example.
[0472] Reaction 4
[0473]
[0474] Synthesis of Intermediate 69-1
[0475] 3-iodo-1,1'-biphenyl (4 equivalents), intermediate 58-3 (1 equivalent), tris(dibenzylideneacetone)dipalladium(0) (0.1 equivalent), tri-tert-butylphosphine (0.2 equivalent) and sodium tert-butoxide (3 equivalents) were dissolved in o-xylene and stirred at about 160 degrees Celsius for about 36 hours. After cooling, the reaction product was washed three times with ethyl acetate and water, and layer separation was performed to obtain an organic layer. The organic layer thus obtained was washed with MgSO 4 Dried, and dried under reduced pressure. The crude product was purified by column chromatography using MC and n-hexane to obtain Intermediate 69-1 (yield: 82%).
[0476] Synthesis of Intermediate 69-2
[0477] 2-(tert-butyl)-9H-carbazole-1,3,4,5,6,7,8-d7 (1 equivalent), intermediate 69-1 (1 equivalent), tris(dibenzylideneacetone)dipalladium(0) (0.05 equivalent), tri-tert-butylphosphine (0.1 equivalent) and sodium tert-butoxide (2 equivalents) were dissolved in o-xylene and stirred at about 140 degrees Celsius for about 10 hours. After cooling, the reaction product was washed three times with ethyl acetate and water, and layer separation was performed to obtain an organic layer. The organic layer thus obtained was washed with MgSO 4 Dried, and dried under reduced pressure. The crude product was purified by column chromatography using MC and n-hexane to obtain Intermediate 69-2 (yield: 81%).
[0478] Synthesis of compound 69
[0479] Intermediate 69-2 (1 equivalent) was dissolved in o-dichlorobenzene and cooled to 0 degrees Celsius, and under a nitrogen atmosphere, BBr 3 (3 equivalents) was slowly injected therein. After completion of the dropwise addition, the temperature was raised to about 180 degrees Celsius, and stirring was performed for about 48 hours. After cooling the reaction product, triethylamine was slowly added dropwise to the flask containing the reaction product to complete the reaction, and ethanol was added to the reaction product to precipitate. The precipitate was filtered to obtain a crude product. The solid thus obtained was purified by column chromatography using MC and n-hexane to obtain compound 69 (yield: 6%).
[0480] 5 Synthesis of fused polycyclic compound 80
[0481] The condensed polycyclic compound 80 according to the embodiment may be synthesized through the step of Reaction 5, for example.
[0482] Reaction 5
[0483]
[0484] Synthesis of Intermediate 80-1
[0485] 5-(tert-butyl)-3-(dibenzo[b,d]thiophen-3-yl)-[1,1'-biphenyl]-2-amine (2 equivalents), 1,3-dichloroindolo[3,2,1-jk]carbazole (1 equivalent), tris(dibenzylideneacetone)dipalladium(0) (0.05 equivalents), tri-tert-butylphosphine (0.1 equivalents) and sodium tert-butoxide (2 equivalents) were dissolved in o-xylene and stirred at about 140 degrees Celsius for about 10 hours. After cooling, the reaction product was washed three times with ethyl acetate and water, and layer separation was performed to obtain an organic layer. The organic layer thus obtained was washed with MgSO 4 Dried, and dried under reduced pressure. The crude product was purified by column chromatography using MC and n-hexane to obtain Intermediate 80-1 (yield: 73%).
[0486] Synthesis of Intermediate 80-2
[0487] 1-Bromo-3-chlorobenzene (4 equivalents), Intermediate 80-1 (1 equivalent), tris(dibenzylideneacetone)dipalladium(0) (0.1 equivalent), tri-tert-butylphosphine (0.2 equivalent) and sodium tert-butoxide (3 equivalents) were dissolved in o-xylene and stirred at about 160 degrees Celsius for about 36 hours. After cooling, the reaction product was washed three times with ethyl acetate and water, and the layers were separated to obtain an organic layer. The organic layer thus obtained was washed with MgSO 4 Dried, and dried under reduced pressure. The crude product was purified by column chromatography using MC and n-hexane to obtain Intermediate 80-2 (yield: 79%).
[0488] Synthesis of Intermediate 80-3
[0489] 9H-carbazole-3-carbonitrile (2.1 equivalents), intermediate 80-2 (1 equivalent), tris(dibenzylideneacetone)dipalladium(0) (0.05 equivalents), tri-tert-butylphosphine (0.1 equivalents) and sodium tert-butoxide (3 equivalents) were dissolved in o-xylene and stirred at about 140 degrees Celsius for about 12 hours. After cooling, the reaction product was washed three times with ethyl acetate and water, and the layers were separated to obtain an organic layer. The organic layer thus obtained was washed with MgSO 4 Dried, and dried under reduced pressure. The crude product was purified by column chromatography using MC and n-hexane to obtain Intermediate 80-3 (yield: 82%).
[0490] Synthesis of compound 80
[0491] Intermediate 80-3 (1 equivalent) was dissolved in o-dichlorobenzene and cooled to 0 degrees Celsius, and under a nitrogen atmosphere, BBr 3The mixture was stirred for about 48 hours. After the reaction product was cooled, triethylamine was slowly added dropwise to the flask containing the reaction product to complete the reaction, and ethanol was added to the reaction product to precipitate. The precipitate was filtered to obtain a crude product. The solid thus obtained was purified by column chromatography using MC and n-hexane to obtain compound 80 (yield: 4%).
[0492] 6 Synthesis of fused polycyclic compound 110
[0493] The condensed polycyclic compound 110 according to the embodiment may be synthesized through the step of Reaction 6, for example.
[0494] Reaction 6
[0495]
[0496] Synthesis of Intermediate 110-1
[0497] 5'-(tert-butyl)-[1,1':3',1":3",1''-quadrenyl]-2'-amine (2 equivalents), 5,11-di-tert-butyl-1,3-dichloroindolo[3,2,1-jk]carbazole (1 equivalent), tris(dibenzylideneacetone)dipalladium(0) (0.05 equivalents), tri-tert-butylphosphine (0.1 equivalents) and sodium tert-butoxide (2 equivalents) were dissolved in o-xylene and stirred at about 140 degrees Celsius for about 10 hours. After cooling, the reaction product was washed three times with ethyl acetate and water, and layer separation was performed to obtain an organic layer. The organic layer thus obtained was washed with MgSO 4 Dried, and dried under reduced pressure. The crude product was purified by column chromatography using MC and n-hexane to obtain Intermediate 110-1 (yield: 78%).
[0498] Synthesis of Intermediate 110-2
[0499] 1-Bromo-3-chlorobenzene (4 equivalents), Intermediate 110-1 (1 equivalent), tris(dibenzylideneacetone)dipalladium(0) (0.1 equivalent), tri-tert-butylphosphine (0.2 equivalent) and sodium tert-butoxide (3 equivalents) were dissolved in o-xylene and stirred at about 160 degrees Celsius for about 36 hours. After cooling, the reaction product was washed three times with ethyl acetate and water, and layer separation was performed to obtain an organic layer. The organic layer thus obtained was washed with MgSO 4 Dried, and dried under reduced pressure. The crude product was purified by column chromatography using MC and n-hexane to obtain Intermediate 110-2 (yield: 81%).
[0500] Synthesis of Intermediate 110-3
[0501] 3,6-di-tert-butyl-9H-carbazole (2.1 equivalents), intermediate 110-2 (1 equivalent), tris(dibenzylideneacetone)dipalladium(0) (0.05 equivalents), tri-tert-butylphosphine (0.1 equivalents) and sodium tert-butoxide (3 equivalents) were dissolved in o-xylene and stirred at about 140 degrees Celsius for about 12 hours. After cooling, the reaction product was washed three times with ethyl acetate and water, and layer separation was performed to obtain an organic layer. The organic layer thus obtained was washed with MgSO 4 Dried, and dried under reduced pressure. The crude product was purified by column chromatography using MC and n-hexane to obtain Intermediate 110-3 (yield: 84%).
[0502] Synthesis of compound 110
[0503] Intermediate 110-3 (1 equivalent) was dissolved in o-dichlorobenzene and cooled to 0 degrees Celsius, and BBr 3 (3 equivalents) was slowly injected therein. After completion of dropwise addition, the temperature was raised to about 180 degrees Celsius, and stirring was performed for about 48 hours. After cooling the reaction product, triethylamine was slowly added dropwise to the flask containing the reaction product to complete the reaction, and ethanol was added to the reaction product to precipitate. The precipitate was filtered to obtain a crude product. The solid thus obtained was purified by column chromatography using MC and n-hexane to obtain compound 110 (yield: 4%).
[0504] 2. Fabrication and evaluation of light-emitting devices
[0505] 1. Fabrication of Light Emitting Device
[0506] A light-emitting device of an embodiment comprising a fused polycyclic compound of the embodiment or a comparative compound in an emission layer is manufactured by the method. Example compound 12, example compound 47, example compound 58, example compound 69, example compound 80 and example compound 110, which are fused polycyclic compounds of the embodiment, are used as dopant materials for the emission layer to manufacture the light-emitting devices of Examples 1 to 12. Comparative compounds CX1 to CX4 are used as dopant materials for the emission layer to manufacture the light-emitting devices of Comparative Examples 1 to 4.
[0507] As the first electrode, a 15Ω / cm 2 A glass substrate (a product of Corning Co.) with an ITO electrode was cut into a size of 50 mm × 50 mm × 0.7 mm, washed with isopropyl alcohol and distilled water by ultrasonic waves for about 5 minutes each, and cleaned by irradiating ultraviolet rays for about 30 minutes and ozone. After that, the glass substrate was installed in a vacuum deposition device.
[0508] On the first electrode, NPD is deposited to form a A hole injection layer having a thickness of about 1000 mm was formed on the hole injection layer by depositing H-1-1. On the hole transport layer, a hole transport layer having a thickness of about 1000 nm is formed by depositing CzSi. The thickness of the emission auxiliary layer is .
[0509] On the emission-assisting layer, a host mixture of a first host (HT) and a second host (ET) in a weight ratio of about 5:5, a sensitizer, and a dopant in a weight ratio of about 85:14:1 are co-deposited to form a nanostructured carbon nanotube having a thickness of about 100 nm. As the dopant, the example compound or the comparative compound was used.
[0510] On the emission layer, TSPO1 is deposited to form a Then, on the hole blocking layer, a layer having a thickness of about On the electron transport layer, LiF is deposited to form an electron transport layer having a thickness of about An electron injection layer with a thickness of about 1000 mm was formed, and Al was deposited on the electron injection layer to form an electron injection layer with a thickness of about 1000 mm. A second electrode with a thickness of 100 Å to form a light emitting device.
[0511] Materials used to make light-emitting devices
[0512]
[0513] Example compounds
[0514]
[0515] Comparison of compounds
[0516]
[0517] 2 Evaluation of light-emitting devices
[0518] The light emitting devices of the comparative examples and the examples are evaluated and shown in Table 1. The light emitting devices of the comparative examples and the examples are measured using a Keithley MU236 and a luminance meter PR650 at about 10 mA / cm 2 The driving voltage, emission efficiency, maximum emission wavelength and service life at a current density of 100 ℃ and 100 ℃ were measured and are shown in Table 1. The service life (T95) was obtained by measuring the time taken for the initial luminance to decrease from 100% to 95% and calculating the relative life based on Comparative Example 1.
[0519] Table 1
[0520]
[0521]
[0522] With reference to Table 1, it can be found that the light-emitting devices of Examples 1 to 12 and Comparative Examples 1 to 4 emit blue light in a wavelength region of about 450 nm to about 470 nm. Compared with the light-emitting devices of Comparative Examples 1 to 4, it can be found that the light-emitting devices of Examples 1 to 12 have a reduced driving voltage, high emission efficiency and long service life. The light-emitting devices of Examples 1 to 12 include Compound 12, Compound 47, Compound 58, Compound 69, Compound 80 and Compound 110, and Compound 12, Compound 47, Compound 58, Compound 69, Compound 80 and Compound 110 are fused polycyclic compounds of the embodiment.
[0523] Compound 12, compound 47, compound 58, compound 69, compound 80 and compound 110 include a fused ring of nine rings as a central structure, wherein an indole and carbazole moiety is fused, and an ortho-terphenyl group is bonded to a fused ring of nine rings. Therefore, it can be found that the stability of the materials of compound 12, compound 47, compound 58, compound 69, compound 80 and compound 110 is improved, RISC is accelerated, and the emission efficiency and service life of the light-emitting device are improved. Therefore, the light-emitting device comprising the fused polycyclic compound of the embodiment can show low driving voltage, high emission efficiency and long service life characteristics.
[0524] The light-emitting device of Comparative Example 1 includes Comparative Compound CX1, and Comparative Compound CX1 includes a fused ring of five rings. Comparative Compound CX1 does not include a fused ring of nine rings in which an indole and carbazole moiety is fused and an ortho-terphenyl group, and is different from the fused polycyclic compound of the embodiment. Therefore, the light-emitting device of Comparative Example 1 including Comparative Compound CX1 shows a relatively high driving voltage, low emission efficiency, and short service life.
[0525] The light-emitting device of Comparative Example 2 includes Comparative Compound CX2. Comparative Compound CX2 includes a fused ring in which nine rings of an indole and carbazole part are fused, but the fusion position of the indole and carbazole part is different from the fusion position of the fused polycyclic compound of the embodiment. Therefore, the light-emitting device of Comparative Example 2 including Comparative Compound CX2 shows a relatively high driving voltage, low emission efficiency, and short service life.
[0526] The light-emitting device of Comparative Example 3 includes the comparative compound CX3. The comparative compound CX3 does not include a fused ring in which nine rings of the indole and carbazole moiety are fused, and is different from the fused polycyclic compound of the embodiment. Therefore, the light-emitting device of Comparative Example 3 including the comparative compound CX3 shows a relatively high driving voltage, low emission efficiency, and short service life.
[0527] The light-emitting device of Comparative Example 4 includes Comparative Compound CX4. Comparative Compound CX4 includes a fused ring in which nine rings of an indole and carbazole moiety are fused but does not include an ortho-terphenyl group, and is different from the fused polycyclic compound of the embodiment. Therefore, the light-emitting device of Comparative Example 4 including Comparative Compound CX4 shows a relatively high driving voltage, low emission efficiency, and short service life.
[0528] The light-emitting device of the embodiment may include an emission layer disposed between the first electrode and the second electrode. The emission layer may include a fused polycyclic compound of the embodiment. The fused polycyclic compound of the embodiment may include a fused ring of nine rings as a central structure, the fused ring of the nine rings including three nitrogen atoms and one boron atom as ring-forming atoms, and an ortho-terphenyl group may be bonded to two nitrogen atoms in the central structure. Therefore, in the fused polycyclic compound of the embodiment, Dexter energy transfer can be suppressed or reduced, excellent or suitable material stability can be displayed, and RISC can be accelerated. The light-emitting device including the fused polycyclic compound of the embodiment can display low driving voltage, high emission efficiency and long service life.
[0529] The light emitting device of the embodiment and the display apparatus including the same include the condensed polycyclic compound of the embodiment and can exhibit high efficiency and long lifespan characteristics.
[0530] The fused polycyclic compound of the embodiment may contribute to the improvement of emission efficiency and lifetime of a light emitting device.
[0531] In the present disclosure, singular expressions may include plural expressions unless the context clearly indicates otherwise. It should be further understood that the terms "comprise(s)", "include(s)" or "have / has" when used in the present disclosure indicate the presence of specified features, integers, steps, operations, elements and / or components, but do not exclude the presence or addition of one or more than one other features, integers, steps, operations, elements, components and / or groups thereof. The " / " used herein may be interpreted as "and" or "or" as appropriate.
[0532] Throughout the present disclosure, when it is mentioned that a component such as a layer, film, region, or plate is "placed" on another component, it should be understood that it can be directly on the other component, or another component can be interposed therebetween. In some embodiments, "directly on..." can mean that there are no additional layers, films, regions, plates, etc. between the layer, film, region, plate, etc. and other parts. For example, "directly on..." can mean that two layers or two components are disposed without using additional components, such as adhesive components, therebetween.
[0533] In the present disclosure, although the terms "first", "second", etc. may be used herein to describe one or more than one element, component, region and / or layer, these elements, components, regions and / or layers should not be limited by these terms. These terms are only used to distinguish one component from another component.
[0534] As used herein, the singular forms "a," "an," "one," and "the" are intended to include the plural forms as well, unless the context clearly indicates otherwise. In addition, the use of "may" when describing embodiments of the present disclosure means "one or more than one embodiment of the present disclosure."
[0535] In the present disclosure, when the particles (e.g., nanoparticles) are spherical, "size" means the particle diameter or the average particle diameter, and when the particles are non-spherical, "size" means the major axis length or the average major axis length. The diameter (or size) of the particles can be measured using a scanning electron microscope or a particle size analyzer. As a particle size analyzer, for example, HORIBA, LA-950 laser particle size analyzer can be used. When the size of the particles is measured using a particle size analyzer, the average particle diameter (or size) is referred to as D50. D50 refers to the average diameter (or size) of the particles whose cumulative volume corresponds to 50% by volume in a particle size distribution (e.g., cumulative distribution), and refers to the value of the particle size corresponding to 50% from the minimum particle when the total number of particles is 100% in a distribution curve accumulated in the order of the minimum particle size to the maximum particle size.
[0536] As used herein, the terms "substantially," "about," or similar terms are used as terms of approximation rather than as terms of degree, and are intended to account for the inherent deviations in measurements or calculations that one of ordinary skill in the art would recognize. "About," as used herein, includes the specified value and means within an acceptable range of deviations of the specified value as determined by one of ordinary skill in the art taking into account the relevant measurements and the errors associated with the measurement of the particular quantity (i.e., the limits of the measurement system). For example, "about" can mean within one or more than one standard deviation, or within ±30%, ±20%, ±10%, ±5% of the specified value.
[0537] In the present disclosure, "does not include a component or any 'component'", "excludes a 'component' or any 'component'", "does not contain a 'component'", etc. means that the 'component' is not added, selected or used as a component in the compound / composition, but due to other impurities and / or external factors in the composition, less than the appropriate amount of the 'component' may still be included.
[0538] Any numerical range listed herein is intended to include all sub-ranges of the same numerical precision within the listed range. For example, the range of "1.0 to 10.0" is intended to include all sub-ranges between the listed minimum value 1.0 and the listed maximum value 10.0 (and including the end value), that is, 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 value listed herein is intended to include all lower numerical limits included therein, and any minimum numerical value listed in this specification is intended to include all higher numerical limits included therein. Therefore, the applicant reserves the right to modify this specification (including claims) to clearly list any sub-ranges included in the range clearly listed herein.
[0539] As used herein, the term "and / or" includes any and all combinations of one or more than one of the associated listed items. Throughout the disclosure, the expressions "at least one of a, b, and c," "at least one of ac," "at least one of a to c," "at least one of a, b and / or c," "at least one of a to c," etc., mean only a, only b, only c, both a and b (e.g., simultaneously), both a and c (e.g., simultaneously), both b and c (e.g., simultaneously), all a, b, and c, or variations thereof.
[0540] In this specification, “including A or B”, “A and / or B”, etc. means A or B, or A and B.
[0541] Any suitable hardware, firmware (e.g., application specific integrated circuit), software, or a combination of software, firmware and hardware can be used to implement the light emitting device, display device, electronic device, electronic equipment or any other related device or component according to the embodiments of the present disclosure described herein. For example, the various components of the device can be formed on an integrated circuit (IC) chip or on a separate IC chip. In addition, the various components of the device can be implemented on a flexible printed circuit film, a tape carrier package (TCP), a printed circuit board (PCB), or formed on a substrate. In addition, the various components of the device can be a process or thread that runs on one or more processors in one or more computing devices, executes computer program instructions and interacts with other system components for performing various functions described herein. The computer program instructions are stored in a memory, which can be implemented in a computing device using a standard memory device (such as a random access memory (RAM) as an example). The computer program instructions can also be stored in other non-temporary computer-readable media, such as a CD-ROM, a flash drive, etc. as an example. Furthermore, those skilled in the art will recognize that the functionality of various computing devices may be combined or integrated into a single computing device, or the functionality of a particular computing device may be distributed across one or more other computing devices without departing from the scope of the embodiments of the present disclosure.
[0542] Although the embodiments of the present disclosure have been described, it should be understood that the present disclosure should not be limited to these embodiments, but one or more suitable changes and modifications may be made by one or more skilled in the art within the spirit and scope of the present disclosure.
Claims
1. A fused polycyclic compound represented by Formula 1: Formula 1 in, In formula 1, R1 to R8 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 ring-forming carbon atoms, and / or combine with an adjacent group to form a ring, n1 to n4 are each independently an integer from 0 to 5, R a1 To R a6 and R b1 To R b4 each independently represents a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thiol group, a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 ring-forming carbon atoms, and / or combines with an adjacent group to form a ring, m1 and m2 are each independently an integer from 0 to 4, and R c1 and R c2 Each is independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thiol group, a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 ring carbon atoms.
2. The fused polycyclic compound according to claim 1, wherein Formula 1 is represented by Formula 1-A: Formula 1-A in, In Formula 1-A, R 16 and R 17 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, R d1 To R d8 each independently represents a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted amine group, a substituted or unsubstituted thiol group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, and / or combines with an adjacent group to form a ring, and n1 to n4, R a1 To R a6 , R b1 To R b4 、m1、m2、R c1 and R c2 Same as defined in Formula 1.
3. The fused polycyclic compound as claimed in claim 2, wherein Formula 1-A is represented by Formula 1-A1: Formula 1-A1 in, In Formula 1-A1, R d11 To R d18 each independently represents a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted amine group, a substituted or unsubstituted thiol group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, and / or combines with an adjacent group to form a ring, and n1 to n4, R a1 To R a6 , R b1 To R b4 、m1、m2、R c1 , R c2 , and R d1 To R d8 The same as defined in Formula 1-A.
4. The fused polycyclic compound according to claim 1, wherein In Formula 1, R1 to R8 are each independently a hydrogen atom, a deuterium atom, or represented by one selected from R-1 to R-26: wherein, in R-5, R-9, R-13 and R-16 to R-26, D is a deuterium atom, In R-1 to R-26, "-*" refers to the position to be linked.
5. The fused polycyclic compound according to claim 1, wherein In Formula 1, R1 to R8 are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted tert-butyl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted carbazole group, a substituted or unsubstituted dibenzofuran group, or a substituted or unsubstituted benzothienylcarbazole group.
6. The fused polycyclic compound according to claim 1, wherein Formula 1 is represented by one selected from Formula 1-B1 to Formula 1-B3: Formula 1-B1 Formula 1-B2 Formula 1-B3 in, In formula 1-B2, R b11 , R b12 , R b21 To R b23 , R b31 , R b32 and R b41 To R b43 each independently represents a hydrogen atom, a deuterium atom, a cyano group, a substituted or unsubstituted amine group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thiol group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, and / or combines with an adjacent group to form a ring, Wherein, in Formula 1-B3, Q 11 and Q 12 Each is independently NR 21 , O or S, n5 and n6 are each independently an integer from 0 to 7, and R 21 To R 23 are each independently a hydrogen atom, a deuterium atom, or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, Wherein, in Formula 1-B2 and Formula 1-B3, R a12 and R a15 are each independently a hydrogen atom, a deuterium atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, and Among them, in Formula 1-B1 to Formula 1-B3, R1 to R8, n1, n3, R b1 , R b3 、m1、m2、R c1 and R c2 Same as defined in Formula 1.
7. The fused polycyclic compound according to claim 1, wherein In formula 1, R c1 and R c2 Each is independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted methyl group, a substituted or unsubstituted tert-butyl group, or a substituted or unsubstituted phenyl group.
8. The fused polycyclic compound according to claim 1, wherein In formula 1, R c1 and R c2 Each is independently a hydrogen atom, a deuterium atom, or represented by one selected from RC-1 to RC-4: Among them, in RC-1, D is a deuterium atom, In RC-1 to RC-4, "-*" indicates the location to be connected.
9. The fused polycyclic compound according to claim 1, wherein In Formula 1, R1 to R8, R a1 To R a6 , R b1 To R b4 , R c1 and R c2 At least one of the substituents contains a deuterium atom, or contains a deuterium atom.
10. The fused polycyclic compound according to claim 1, wherein Formula 1 is represented by one of the compounds selected from Compound Group 1: Compound Group 1 in, In compound group 1, D is a deuterium atom.
11. A light emitting device comprising: a first electrode; a second electrode on the first electrode; as well as an emission layer between the first electrode and the second electrode and comprising a first compound, The first compound is a fused polycyclic compound according to any one of claims 1 to 10.
12. The light-emitting device of claim 11, wherein the emission layer further comprises at least one selected from 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: Formula HT-1 in, In formula HT-1, A1 to A8 are each independently N or CR 51 , L1 is a direct bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms, Y a It is a direct key, CR 52 R 53 or SiR 54 R 55 , Ar1 is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, and R 51 To R 55 each independently represents a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted thiol 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 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 ring-forming carbon atoms, and / or combines with an adjacent group to form a ring, Formula ET-1 Among them, in formula ET-1, At least one selected from X1 to X3 is N, and the rest are CR 56 , R 56 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 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 ring carbon atoms, b1 to b3 are each independently an 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 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, and L2 to L4 are each independently a direct bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms, and Formula D-1 Wherein, in formula D-1, Q1 to Q4 are each independently C or N, C1 to C4 are each independently a substituted or unsubstituted hydrocarbon ring having 5 to 30 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocycle having 2 to 30 ring carbon atoms, L 11 To L 13 Each is independently a direct key, *-O-*, *—S—*, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms, in which L 11 To L 13 In the figure, "—*" refers to the part connected to C1 to C4. b11 to b13 are each independently 0 or 1, R 61 To R 66 each independently represents a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted thiol 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 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 ring carbon atoms, and d1 to d4 are each independently an integer of 0 to 4.
13. Display equipment, including: Base layer; a circuit layer on the substrate layer; as well as a display device layer on the circuit layer and including a light emitting device, The light emitting device comprises a first electrode, a second electrode on the first electrode, and an emission layer, wherein the emission layer is between the first electrode and the second electrode and comprises the fused polycyclic compound according to any one of claims 1 to 10.
14. The display device of claim 13, wherein the light emitting device comprises a first light emitting device configured to emit red light, a second light emitting device configured to emit green light, and a third light emitting device configured to emit blue light, and The fused polycyclic compound is contained in the third light emitting device.
15. The display apparatus of claim 13, further comprising a light control layer on the display device layer and comprising quantum dots.
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KR1020230098786A