Light-emitting element and amine compound for light-emitting element

Abstract

Disclosed are light-emitting elements and amine compounds for light-emitting elements. The light-emitting element includes: a first electrode; a second electrode; and at least one functional layer provided between the first electrode and the second electrode and including an amine compound represented by Formula 1. The light-emitting element can exhibit high emission efficiency and improved service life characteristics: Formula 1

Description

[0001] This application claims priority and benefit to Korean Patent Application No. 10-2021-0015237, filed on February 3, 2021, the entire contents of which are incorporated herein by reference. Technical Field

[0002] One or more aspects of embodiments of this disclosure relate to light-emitting elements and amine compounds therein, and for example to amine compounds for hole transport regions and light-emitting elements comprising the amine compound. Background Technology

[0003] Organic electroluminescent display devices (OLEDs) are being actively developed as image display devices. OLEDs are display devices that include so-called self-emissive elements, in which holes and electrons injected from a first electrode and a second electrode recombine in an emitting layer, and the luminescent material in the emitting layer emits light to achieve display.

[0004] In order to apply light-emitting elements to display devices, it is desirable to reduce the driving voltage, improve the emission efficiency and / or improve the lifespan, and it is desirable to develop materials for light-emitting elements that can stably achieve these requirements.

[0005] To achieve high-efficiency light-emitting devices, materials for hole transport regions are being developed to suppress exciton energy diffusion in the emitter layer. Summary of the Invention

[0006] One or more aspects of embodiments of this disclosure relate to a light-emitting element that exhibits excellent or suitable emission efficiency and long lifespan characteristics.

[0007] One or more aspects of embodiments of this disclosure relate to an amine compound as a material for a light-emitting element having the characteristics of high efficiency and long lifespan.

[0008] One or more embodiments of this disclosure provide an amine compound represented by Formula 1:

[0009] Formula 1

[0010]

[0011] In Formula 1, R1 can be adamantyl, cyclohexyl, or bicycloheptyl, and Ar1 and Ar2 can both be independently substituted or unsubstituted aryl groups having 6 to 30 cyclic carbon atoms. L can be a linearly bonded, substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, and FR can be represented by Formula 2:

[0012] Formula 2

[0013]

[0014] In Equation 2, X can be CR a R b , N, NR c , O or S, and R a To R c Each of the following can independently be a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, and optionally, can be incorporated into an adjacent group to form a ring. d and e can each independently be an integer from 0 to 4, and R d and R e Each of the following can be independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, and optionally, can be incorporated into an adjacent group to form a ring.

[0015] Equation 1 can be expressed by Equation 1-1 or Equation 1-2:

[0016] Formula 1-1

[0017]

[0018] Formula 1-2

[0019]

[0020] In Equations 1-1 and 1-2, R1, L, Ar1, and Ar2 can all be independently identical to those defined in Equation 1, and X, R d R e , d, and e can all be independently identical to those defined in Equation 2.

[0021] Equation 1-2 can be represented by Equation 1-2A.

[0022] Formula 1-2A

[0023]

[0024] In Equation 1-2A, R1, L, Ar1, and Ar2 can all be independently identical to those defined in Equation 1, and R a R d R e, d, and e can all be independently identical to those defined in Equation 2.

[0025] In Formula 1, Ar1 and Ar2 can be substituted or unsubstituted phenylene.

[0026] Equation 1 can be represented by Equation 1A:

[0027] Formula 1A

[0028]

[0029] In Equation 1A, R1, L, and FR can all be independently the same as those defined in Equation 1.

[0030] Equation 1A can be represented by Equation 1A-1:

[0031] Formula 1A-1

[0032]

[0033] In Equation 1A-1, R1, L, and FR can all be independently the same as those defined in Equation 1.

[0034] One or more embodiments of this disclosure provide a light-emitting element comprising: a first electrode; a second electrode disposed on the first electrode; and at least one functional layer disposed between the first electrode and the second electrode and comprising an amine compound according to the above embodiments.

[0035] The at least one functional layer may include an emitter layer, a hole transport region disposed between the first electrode and the emitter layer, and an electron transport region disposed between the emitter layer and the second electrode, wherein the hole transport region may include an amine compound.

[0036] The hole transport region may include a hole injection layer disposed on the first electrode and a hole transport layer disposed on the hole injection layer, and the hole transport layer may include an amine compound.

[0037] The at least one functional layer may include: an emitter layer; a first hole transport layer disposed between the first electrode and the emitter layer; a second hole transport layer disposed between the first hole transport layer and the emitter layer; and an electron transport region disposed between the emitter layer and the second electrode, wherein the first hole transport layer may include an amine compound.

[0038] The second hole transport layer may include an amine derivative compound represented by Formula 3:

[0039] Formula 3

[0040]

[0041] In Equation 3, L 11It can be a directly bonded, substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, and R 11 To R 14 Each of the groups may be independently substituted or unsubstituted alkyl groups having 1 to 10 carbon atoms, substituted or unsubstituted alkenyl groups having 2 to 10 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 cyclic carbon atoms, or substituted or unsubstituted heteroaryl groups having 2 to 30 cyclic carbon atoms, and optionally, may be incorporated into adjacent groups to form a ring.

[0042] Equation 3 can be expressed by Equation 3-1 or Equation 3-2:

[0043] Equation 3-1

[0044]

[0045] Equation 3-2

[0046]

[0047] In equations 3-1 and 3-2, L 11 and R 11 To R 14 They can all be independently identical to those defined in Equation 3. Attached Figure Description

[0048] The accompanying drawings are included to provide a further understanding of this disclosure, and are incorporated in and constitute a part of this specification. The drawings illustrate embodiments of the present disclosure and, together with the description, serve to explain the principles of the disclosure. In the drawings:

[0049] Figure 1 This is a plan view of a display device according to an embodiment;

[0050] Figure 2 This is a cross-sectional view of a display device according to an embodiment;

[0051] Figure 3 This is a schematic cross-sectional view of the light-emitting element according to an embodiment;

[0052] Figure 4 This is a schematic cross-sectional view of the light-emitting element according to an embodiment;

[0053] Figure 5 This is a schematic cross-sectional view of the light-emitting element according to an embodiment;

[0054] Figure 6 This is a schematic cross-sectional view of the light-emitting element according to an embodiment;

[0055] Figure 7 This is a schematic cross-sectional view of the light-emitting element according to an embodiment;

[0056] Figure 8 This is a cross-sectional view of a display device according to an embodiment; and

[0057] Figure 9 This is a cross-sectional view of a display device according to an embodiment. Detailed Implementation

[0058] The embodiments disclosed herein are compatible with various suitable modifications and alternatives, and selected embodiments are shown by way of example in the accompanying drawings and will be described in more detail herein. However, it should be understood that this disclosure is not intended to be limited to the specific forms disclosed, and all modifications, equivalents, and alternatives are included within the spirit and scope of this disclosure.

[0059] In describing the accompanying drawings, the same reference numerals are used for the same components, and their repeated descriptions may be omitted. In the drawings, for clarity, the dimensions of the structures may be shown at an enlarged scale. It will be understood that although the terms first, second, etc., may be used herein to describe various components, these components should not be limited by these terms. These terms are used only to distinguish one component from another. For example, without departing from the scope of this disclosure, a first component may optionally be named a second component, and similarly, a second component may optionally be named a first component. Unless the context clearly indicates otherwise, the singular forms such as “a,” “an,” and “the” are intended to include the plural forms as well.

[0060] It will also be understood that when the terms “comprising,” “including,” and / or “having,” etc., are used in this application, it indicates the presence of the stated feature, whole, step, operation, component, or part, but does not exclude the presence or addition of one or more other features, wholes, steps, operations, components, parts, or combinations thereof.

[0061] As used herein, the term “use” and its variations may be considered synonymous with the term “utilize” and its variations, respectively. As used herein, when expressions such as “at least one of…”, “one of…”, and “selected from…” follow a list of elements, they modify the entire list of elements, not individual elements within that list.

[0062] As used herein, the term “and / or” includes any and all combinations of one or more of the associated listed items. Furthermore, in describing embodiments of this disclosure, the use of “may” refers to “one or more embodiments of this disclosure”.

[0063] In this application, when a portion (component) such as a layer, film, region, or plate is referred to as being "on" or "above" another portion (component), the portion (component) may be "directly on" the other portion (component), or there may be an intermediate portion (component). When a portion (component) such as a layer, film, region, or plate is referred to as being "below" or "under" another portion (component), the portion (component) may be "directly below" the other portion (component), or there may be an intermediate portion (component). Conversely, when an element is referred to as being "directly on" or "directly below" another portion (component), there is no intermediate element. Furthermore, when a portion (component) is referred to as being positioned "on" another portion (component), the portion (component) may also be positioned on the upper portion (component) or the lower portion (component) (e.g., when viewed from different perspectives).

[0064] In this specification, the term "substituted or unsubstituted" means an unsubstituted state, or a state in which the substance is substituted by at least one substituent selected from the group consisting of deuterium, halogen, cyano, nitro, amino, silyl, oxy, thio, sulfinyl, sulfonyl, carbonyl, boron, phosphonium oxide, phosphonium sulfide, alkyl, alkenyl, alkynyl, alkoxy, cycloalkyl, aryl, and heterocyclic groups. In some embodiments, each of the example substituents may also be substituted or unsubstituted. For example, biphenyl can be interpreted as a so-called aryl or a phenyl group substituted with a phenyl group.

[0065] In this specification, the term "bonded to an adjacent group to form a ring" can refer to bonding to an adjacent group to form a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocycle. The term "hydrocarbon ring" includes aliphatic hydrocarbon rings and aromatic hydrocarbon rings. The term "heterocycle" includes aliphatic heterocycles and aromatic heterocycles. Hydrocarbon rings and heterocycles can each be independently monocyclic or polycyclic. In some embodiments, the ring formed by the bonded groups may also be attached to another ring to form a spirostructure.

[0066] In this specification, the term "adjacent group" can refer to a substituent on the same atom or point, a substituent directly connected to an atom or point on the base atom or point, or a substituent spatially positioned (e.g., within intramolecular bonding distance) with the corresponding substituent. For example, in 1,2-xylene, the two methyl groups can be interpreted as "adjacent groups," and in 1,1-diethylcyclopentane, the two ethyl groups can be interpreted as "adjacent groups." Furthermore, in 4,5-dimethylphenanthrene, the two methyl groups can be interpreted as "adjacent groups."

[0067] In this specification, examples of halogen atoms may include fluorine atoms, chlorine atoms, bromine atoms, or iodine atoms.

[0068] In this specification, alkyl groups can be straight-chain, branched, or cyclic. The number of carbon atoms in an alkyl group can be 1 to 50, 1 to 30, 1 to 20, 1 to 10, or 1 to 6. Examples of alkyl groups may include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, isobutyl, 2-ethylbutyl, 3,3-dimethylbutyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, cyclopentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 2-butylhexyl, cyclohexyl, 4-methylcyclohexyl, 4-tert-butylcyclohexyl, n-heptyl, 1-methylheptyl, 2,2-dimethylheptyl, 2-ethylheptyl, 2-butylheptyl, n-octyl, tert-octyl, 2-ethyloctyl, 2-butyloctyl, 2-hexyloctyl, 3,7-dimethyloctyl, cyclooctyl, n-nonyl, n-decyl, adamantyl, 2-ethyldecyl, 2-butyl 2-Hexyldecyl, 2-Hexyldecyl, 2-Octyldecyl, undecyl, dodecyl, 2-Ethyldodecyl, 2-Butyldodecyl, 2-Hexyldodecyl, 2-Octyldodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, 2-Ethylhexadecyl, 2-Butylhexadecyl, 2-Hexylhexadecyl, 2-Octylhexadecyl, heptadecanyl, octadecyl, nonadecanyl, eicosyl, 2-Ethyleicosyl, 2-Butyleicosyl, 2-Hexyleicosyl, 2-Octyleicosyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecanyl, octadecyl, nonadecanyl, and / or triadecyl, etc.

[0069] In this specification, the term "hydrocycloyl group" refers to an optional functional group or substituent derived from an aliphatic or aromatic hydrocarbon ring. The hydrocycloyl group can be a saturated hydrocycloyl group having 5 to 20 cyclic carbon atoms.

[0070] In this specification, the term "aryl" refers to any functional group or substituent derived from an aromatic hydrocarbon ring. An aryl group can be monocyclic or polycyclic. The number of carbon atoms in the cyclic aryl group can be 6 to 30, 6 to 20, or 6 to 15. Examples of aryl groups may include, but are not limited to, phenyl, naphthyl, fluorenyl, anthraceneyl, phenanthryl, biphenyl, triphenyl, tetraphenyl, pentaphenyl, hexaphenyl, benzo[9,10]phenanthryl, pyrene, benzofluoranthracene, and / or Base, etc.

[0071] In some embodiments, the fluorene group may be substituted (e.g., at the 9H position), and the two substituents may bond together to form a spirostructure. Examples of fluorene group substitution are given below. However, embodiments of this disclosure are not limited thereto:

[0072]

[0073] In this specification, the term "heterocyclic group" refers to any functional group or substituent derived from a ring comprising at least one heteroatom, including boron (B), oxygen (O), nitrogen (N), phosphorus (P), silicon (Si), and sulfur (S). The term "heterocyclic group" includes aliphatic heterocyclic groups and aromatic heterocyclic groups. Aromatic heterocyclic groups may be heteroaryl groups. Aliphatic and aromatic heterocycles may be monocyclic or polycyclic.

[0074] In this specification, a heterocyclic group may include at least one of B, O, N, P, Si, and S as a heteroatom. When a heterocyclic group includes two or more heteroatoms, the two or more heteroatoms may be the same as or different from each other. The heterocyclic group may be a monocyclic or polycyclic heterocyclic group, and has the concept of including a heteroaryl group. The number of cyclic carbon atoms in the heterocyclic group may be 2 to 30, 2 to 20, or 2 to 10.

[0075] In this specification, the aliphatic heterocyclic group may include at least one of B, O, N, P, Si, and S as a heteroatom. The number of cyclic carbon atoms in the aliphatic heterocyclic group may be 2 to 30, 2 to 20, or 2 to 10. Examples of aliphatic heterocyclic groups may include, but are not limited to, ethylene oxide, cyclothioethane, pyrrolidinyl, piperidinyl, tetrahydrofuranyl, tetrahydrothiophenyl, thiocyclopentyl, tetrahydropyranyl, and / or 1,4-dioxane, etc.

[0076] In this specification, a heteroaryl group may include at least one of B, O, N, P, Si, and S as a heteroatom. When a heteroaryl group includes two or more heteroatoms, the two or more heteroatoms may be the same as or different from each other. The heteroaryl group may be a monocyclic heteroaryl group or a polycyclic heteroaryl group. The number of cyclic carbon atoms in the heteroaryl group may be 2 to 30, 2 to 20, or 2 to 10. Examples of heteroaryl groups may include, but are not limited to, thienyl, furanyl, pyrrolyl, imidazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridineyl, pyridazinyl, quinolinyl, quinazolinyl, quinoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, N-arylcarbazolyl, N-heteroarylcarbazolyl, N-alkylcarbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothiaphenyl, dibenzothiaphenyl, thiaphenothiaphenyl, benzofuranyl, phenanthrololinyl, thiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, thiadiazolyl, phenthiazolyl, dibenzothiazolyl, and / or dibenzofuranyl.

[0077] In this specification, except that arylene is a divalent group, the same description of aryl groups as stated above can be applied to arylene. Except that heteroarylene is a divalent group, the same description of heteroarylene can be applied to heteroarylene.

[0078] In this specification, the term "silyl" includes alkylsilyl and arylsilyl. Examples of silyl may include, but are not limited to, trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, and / or phenylsilyl.

[0079] In this specification, the number of carbon atoms in an amino group can be from 1 to 30, but is not particularly limited thereto. Amino groups can include alkylamino, aromatic amino, or heteroaromatic amino groups. Examples of amino groups include, but are not limited to, methylamino, dimethylamino, phenylamino, diphenylamino, naphthylamino, and / or 9-methyl-anthraylamino.

[0080] In this specification, the number of carbon atoms in the carbonyl group is not particularly limited, and can be from 1 to 40, 1 to 30, or 1 to 20. For example, the carbonyl group can have the following structure, but the embodiments of this disclosure are not limited thereto.

[0081]

[0082] In this specification, the number of carbon atoms in a sulfinyl group or sulfonyl group can be from 1 to 30, but is not particularly limited thereto. The term "sulfinyl" can include alkylsulfinyl and arylsulfinyl. The term "sulfonyl" can include alkylsulfonyl and arylsulfonyl.

[0083] In this specification, the term "thio group" may include alkylthio or arylthio. The term "thio group" may refer to a group in which a sulfur atom is bonded to an alkyl or aryl group as defined above. Examples of thio groups may include, but are not limited to, methylthio, ethylthio, propanethio, pentanethio, hexanethio, octylthio, dodecylthio, cyclopentanethio, cyclohexanethio, phenylthio, and naphthio.

[0084] In this specification, the term "oxygen group" can refer to a group in which an oxygen atom is bonded to an alkyl or aryl group as defined above. Oxide groups can include alkoxy and aryloxy groups. Alkoxy groups can include straight-chain, branched, or cyclic groups. The number of carbon atoms in an alkoxy group can be, for example, 1 to 20 or 1 to 10, but is not particularly limited. Examples of oxygen groups may include, but are not limited to, methoxy, ethoxy, n-propoxy, isopropoxy, butoxy, pentoxy, hexoxy, octoxy, nonoxy, decoxy, and / or benzyloxy.

[0085] In this specification, the term "boron-based" may refer to a group in which a boron atom is bonded to an alkyl or aryl group as defined above. The term "boron-based" includes alkylboron-based and arylboron-based groups. Examples of boron-based groups may include, but are not limited to, diphenylboron-based and / or phenylboron-based groups.

[0086] In this specification, the term "alkenyl" can be straight-chain or branched. There is no particular limitation on the number of carbon atoms, which can be 2 to 30, 2 to 20, or 2 to 10. Examples of alkenyl groups include, but are not limited to, vinyl, 1-butenyl, 1-pentenyl, 1,3-butadienyl, styryl, and / or styrylvinyl.

[0087] In this specification, the number of carbon atoms in an amino group can be from 1 to 30, but is not particularly limited thereto. The term "amino group" can include alkylamino and aromatic amino groups. Examples of amino groups may include, but are not limited to, methylamino, dimethylamino, aniline, diphenylamino, naphthylamino, and / or 9-methyl-anthraylamino.

[0088] In this specification, the alkyl group in alkylthio, alkylsulfonyl, alkylaryl, alkylamino, alkylboryl, alkylsilyl and / or alkylamine can be the same as the examples of alkyl groups described above.

[0089] In this specification, the aryl groups in aryloxy, arylthio, arylsulfonyl, arylamino, arylboryl, arylsilyl, and arylamine are substantially the same as the examples of aryl groups described above.

[0090] In this specification, the term "direct-connect key" may refer to a single key.

[0091] In some embodiments, as described in this specification and This refers to the position to be connected.

[0092] In the following text, embodiments of the present disclosure will be explained with reference to the accompanying drawings.

[0093] Figure 1 This is a plan view showing an embodiment of the display device DD. Figure 2 This is a cross-sectional view of the display device DD according to an embodiment. Figure 2 It shows along Figure 1 A sectional view of a portion cut off by line I-I' in the diagram.

[0094] The display device DD may include a display panel DP and an optical layer PP disposed on the display panel DP on a third directional axis DR3. The display panel DP includes light-emitting elements ED-1, ED-2, and ED-3. The display device DD may include multiple light-emitting elements ED-1, ED-2, and ED-3. The optical layer PP may be disposed on the display panel DP and control the light reflected from external light on the display panel DP. The optical layer PP may include, for example, a polarizing layer or a color filter layer. In some embodiments, the optical layer PP may not be disposed in the display device DD according to the embodiment.

[0095] The substrate BL can be disposed on the optical layer PP. The substrate BL can be a component providing a substrate surface on which the optical layer PP is disposed. The substrate BL can be a glass substrate, a metal substrate, and / or a plastic substrate, etc. However, embodiments of this disclosure are not limited thereto, and the substrate BL can be an inorganic layer, an organic layer, or a composite material layer. In some embodiments, the substrate BL may not be disposed.

[0096] The display device DD according to an embodiment may further include a filler layer. The filler layer may be disposed between the display element layer DP-ED and the substrate BL. The filler layer may be an organic material layer. The filler layer may include at least one selected from acrylic resin, silicone resin, and epoxy resin.

[0097] The display panel DP may include a substrate layer BS, a circuit layer DP-CL disposed on the substrate layer BS, and a display element layer DP-ED. The display element layer DP-ED may include a pixel defining film PDL, light-emitting elements ED-1, ED-2, and ED-3 disposed between the pixel defining films PDL, and an encapsulation layer TFE disposed on the light-emitting elements ED-1, ED-2, and ED-3.

[0098] The substrate layer BS can be a component that provides a substrate surface on which the display element layer DP-ED is disposed. The substrate layer BS can be a glass substrate, a metal substrate, and / or a plastic substrate, etc. However, the embodiments of this disclosure are not limited thereto, and the substrate layer BS can be an inorganic layer, an organic layer, or a composite material layer.

[0099] In this embodiment, the circuit layer DP-CL is disposed on the substrate layer BS, and the circuit layer DP-CL may include multiple transistors. Each transistor may include a control electrode, an input electrode, and an output electrode. For example, the circuit layer DP-CL may include a switching transistor and a driving transistor for driving the light-emitting elements ED-1, ED-2, and ED-3 of the display element layer DP-ED.

[0100] Each of the light-emitting elements ED-1, ED-2, and ED-3 may have the characteristics described later. Figure 3 to Figure 7The structure of the light-emitting element ED in the embodiments. Each of the light-emitting elements ED-1, ED-2 and ED-3 may include a first electrode EL1, a hole transport region HTR, an emitter layer EML-R, EML-G and EML-B, an electron transport region ETR and a second electrode EL2.

[0101] exist Figure 2 In this embodiment, the emitting layers EML-R, EML-G, and EML-B of light-emitting elements ED-1, ED-2, and ED-3 are disposed in openings OH defined in a pixel-defining film PDL, and the hole transport region HTR, electron transport region ETR, and second electrode EL2 can be disposed as a common layer in all of the light-emitting elements ED-1, ED-2, and ED-3. However, embodiments of this disclosure are not limited thereto. In some embodiments, the hole transport region HTR and the electron transport region ETR can be patterned and disposed (e.g., only) in openings OH defined in the pixel-defining film PDL. For example, in an embodiment, the hole transport region HTR, emitting layers EML-R, EML-G, and EML-B, and the electron transport region ETR of light-emitting elements ED-1, ED-2, and ED-3 can be patterned and disposed by inkjet printing.

[0102] The encapsulation layer TFE can cover the light-emitting elements ED-1, ED-2, and ED-3. The encapsulation layer TFE can seal the display element layer DP-ED. The encapsulation layer TFE can be a thin-film encapsulation layer. The encapsulation layer TFE can be a single layer or multiple stacked layers. The encapsulation layer TFE includes at least one insulating layer. According to embodiments, the encapsulation layer TFE can include at least one inorganic film (hereinafter, encapsulating inorganic film). In some embodiments, the encapsulation layer TFE according to embodiments can include at least one organic film (hereinafter, encapsulating organic film) and at least one encapsulating inorganic film.

[0103] An inorganic encapsulation film protects the display element layer (DP-ED) from moisture / oxygen, while an organic encapsulation film protects the DP-ED from foreign matter (such as dust particles). The inorganic encapsulation film may include silicon nitride, silicon oxynitride, silicon oxide, titanium dioxide, and / or aluminum oxide, but embodiments of this disclosure are not particularly limited thereto. The organic encapsulation film may include acrylic compounds and / or epoxy compounds, etc. The organic encapsulation film may include photopolymerizable organic materials, but embodiments of this disclosure are not particularly limited thereto.

[0104] The encapsulation layer TFE can be placed on the second electrode EL2, and can be placed at the same time as filling the opening OH.

[0105] Reference Figure 1 and Figure 2The 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 correspond to areas therein that emit light generated from light-emitting elements ED-1, ED-2, and ED-3, respectively. The light-emitting areas PXA-R, PXA-G, and PXA-B may be separated from each other in a plane (e.g., in a plan view).

[0106] The light-emitting regions PXA-R, PXA-G, and PXA-B can be separated by a pixel defining film PDL. The non-light-emitting region NPXA can be a region disposed between adjacent light-emitting regions PXA-R, PXA-G, and PXA-B and corresponding to the pixel defining film PDL. In this specification, the light-emitting regions PXA-R, PXA-G, and PXA-B can each correspond to a pixel. The pixel defining film PDL can separate the light-emitting elements ED-1, ED-2, and ED-3. The emitting layers EML-R, EML-G, and EML-B of the light-emitting elements ED-1, ED-2, and ED-3 can be disposed and separated within openings OH defined in the pixel defining film PDL.

[0107] The luminescent regions PXA-R, PXA-G, and PXA-B can be classified into multiple groups based on the color of the light emitted from luminescent elements ED-1, ED-2, and ED-3. Figure 1 and Figure 2 In the display device DD according to the embodiment shown, three light-emitting regions PXA-R, PXA-G, and PXA-B can emit red light, green light, and blue light respectively, and are illustrated by way of example. For example, the display device DD according to the embodiment may include red light-emitting regions PXA-R, green light-emitting regions PXA-G, and blue light-emitting regions PXA-B that are distinct from each other.

[0108] In the display device DD according to an embodiment, a plurality of light-emitting elements ED-1, ED-2, and ED-3 can emit light with different wavelength ranges. For example, in an embodiment, the display device DD may include a first light-emitting element ED-1 that emits red light, a second light-emitting element ED-2 that emits green light, and a third light-emitting element ED-3 that emits blue light. For example, the red emitting region PXA-R, the green emitting region PXA-G, and the blue emitting region PXA-B of the display device DD may correspond to the first light-emitting element ED-1, the second light-emitting element ED-2, and the third light-emitting element ED-3, respectively.

[0109] However, the embodiments disclosed herein are not limited thereto, and the first to third light-emitting elements ED-1, ED-2, and ED-3 may emit light in substantially the same wavelength range, or at least one of the first to third light-emitting elements ED-1, ED-2, and ED-3 may emit light in different wavelength ranges. For example, all of the first to third light-emitting elements ED-1, ED-2, and ED-3 may emit blue light.

[0110] According to an embodiment, the light-emitting regions PXA-R, PXA-G, and PXA-B in the display device DD can be arranged in a stripe pattern. (Refer to...) Figure 1 Multiple red emitting regions PXA-R can be arranged relative to each other along the second direction axis DR2, multiple green emitting regions PXA-G can be arranged relative to each other along the second direction axis DR2, and multiple blue emitting regions PXA-B can be arranged relative to each other along the second direction axis DR2. In some embodiments, the red emitting regions PXA-R, green emitting regions PXA-G, and blue emitting regions PXA-B can be arranged alternately relative to each other along the first direction axis DR1.

[0111] Figure 1 and Figure 2 The illustration shows that all emitting regions PXA-R, PXA-G, and PXA-B have similar areas, but embodiments of this disclosure are not limited thereto. The areas (e.g., planar areas) of the emitting regions PXA-R, PXA-G, and PXA-B can differ from each other depending on the wavelength range of the emitted light. In some embodiments, the areas of the emitting regions PXA-R, PXA-G, and PXA-B can be represented as the areas observed on a plane defined by a first directional axis DR1 and a second directional axis DR2 (e.g., in a plan view).

[0112] The arrangement of the luminescent regions PXA-R, PXA-G, and PXA-B is not limited to... Figure 1 The configuration shown, and in some embodiments, allows the red emitting regions PXA-R, green emitting regions PXA-G, and blue emitting regions PXA-B to be arranged in one or more suitable combinations or patterns according to the display quality characteristics required by the display device DD. For example, the emitting regions PXA-R, PXA-G, and PXA-B can be arranged in... Structure or rhomboid structure arrangement.

[0113] 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 this disclosure are not limited thereto.

[0114] In the following text, Figure 3 to Figure 7This is a schematic cross-sectional view of a light-emitting element according to an embodiment. The light-emitting element ED according to an embodiment may include a first electrode EL1, a second electrode EL2 facing the first electrode EL1, and at least one functional layer disposed between the first electrode EL1 and the second electrode EL2. The at least one functional layer may include a hole transport region HTR, an emitter layer EML, and an electron transport region ETR sequentially stacked. For example, the light-emitting element ED according to an embodiment may include a first electrode EL1, a hole transport region HTR, an emitter layer EML, an electron transport region ETR, and a second electrode EL2 sequentially stacked.

[0115] and Figure 3 compared to, Figure 4 A cross-sectional view of a light-emitting element (ED) according to an embodiment is shown, wherein the hole transport region (HTR) includes a hole injection layer (HIL) and a hole transport layer (HTL), and the electron transport region (ETR) includes an electron injection layer (EIL) and an electron transport layer (ETL). Figure 3 compared to, Figure 5 A cross-sectional view of a light-emitting element (ED) according to an 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 4 compared to, Figure 6 A cross-sectional view of a light-emitting element ED according to an embodiment is shown, wherein a capping layer CPL is disposed on (e.g., externally) the second electrode EL2. With Figure 4 compared to, Figure 7 A cross-sectional view of a light-emitting element ED according to an embodiment is shown, wherein the hole transport region HTR includes a plurality of hole transport layers HTL1 and HTL2.

[0116] According to embodiments, the light-emitting element (ED) may include an amine compound (described later) in at least one functional layer (such as a hole transport region (HTR), an emitter layer (EML), and / or an electron transport region (ETR).

[0117] In the light-emitting element ED according to the embodiments, the first electrode EL1 is conductive. The first electrode EL1 may be formed of a metallic material, a metal alloy, and / or a conductive compound. The first electrode EL1 may be an anode or a cathode. However, the embodiments of this 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 transmissive-reflective electrode, or a reflective electrode. 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), and / or indium tin zinc oxide (ITZO), etc.). When the first electrode EL1 is a transmissive or reflective electrode, the first electrode EL1 may comprise silver (Ag), magnesium (Mg), copper (Cu), aluminum (Al), platinum (Pt), palladium (Pd), gold (Au), nickel (Ni), neodymium (Nd), iridium (Ir), chromium (Cr), lithium (Li), calcium (Ca), LiF, molybdenum (Mo), titanium (Ti), tungsten (W), or compounds or mixtures thereof (e.g., a mixture of Ag and Mg), or materials having a multilayer structure such as LiF / Ca or LiF / Al. In some embodiments, the first electrode EL1 may have a multilayer structure, which includes a reflective or transmissive film formed from the above-described materials and a transparent conductive film formed from indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), and / or indium tin zinc oxide (ITZO). For example, the first electrode EL1 may have a three-layer structure of ITO / Ag / ITO, but the embodiments of this disclosure are not limited thereto. In some embodiments, the first electrode EL1 may comprise the aforementioned metallic material, a combination of two or more metallic materials selected from the aforementioned metallic materials, or one or more oxides of the aforementioned metallic material. The thickness of the first electrode EL1 may be approximately to approximately For example, the thickness of the first electrode EL1 can be approximately to approximately

[0118] A hole transport region (HTR) is disposed on the first electrode EL1. The HTR may include at least one of a hole injection layer (HIL), a hole transport layer (HTL), a buffer layer or a light-emitting auxiliary layer, and an electron blocking layer (EBL). The thickness of the HTR may be, for example, approximately... to approximately

[0119] Hole transport region (HTR) can have a single layer formed of a single material, a single layer structure formed of multiple different materials, or a multilayer structure with multiple layers formed of multiple different materials.

[0120] For example, the hole transport region HTR can have a single-layer structure of a hole injection layer HIL or a hole transport layer HTL, or it can have a single-layer structure formed of a hole injection material and a hole transport material. Furthermore, the hole transport region HTR can have a single-layer structure formed of multiple different materials, or a structure in which hole injection layer HIL / hole transport layer HTL, hole injection layer HIL / hole transport layer HTL / buffer layer, hole injection layer HIL / buffer layer, hole transport layer HTL / buffer layer, or hole injection layer HIL / hole transport layer HTL / electron blocking layer EBL are stacked sequentially from the first electrode EL1. However, the embodiments of this disclosure are not limited thereto.

[0121] In some embodiments, the hole transport region (HTR) may have a stacked structure of multiple hole transport layers. For example, the hole transport region (HTR) may have a structure of hole injection layer HIL / first hole transport layer HTL1 / second hole transport layer HTL2. However, the embodiments of this disclosure are not limited thereto.

[0122] Hole transport regions (HTRs) can be formed using one or more suitable methods, such as vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) method, inkjet printing, laser printing and / or laser-induced thermal imaging (LITI).

[0123] In the light-emitting element ED according to the embodiment, the hole transport region HTR may include an amine compound represented by Formula 1. In the light-emitting element ED according to the embodiment, the hole transport layer HTL may include an amine compound represented by Formula 1, and for example, in the light-emitting element ED according to the embodiment, the first hole transport layer HTL1 may include an amine compound represented by Formula 1:

[0124] Formula 1

[0125]

[0126] In Formula 1, R1 can be adamantyl, cyclohexyl, or bicycloheptyl, and FR can be represented by Formula 2:

[0127] Formula 2

[0128]

[0129] For example, the amine compound according to the embodiments may include: (e.g.,) a first substituent of bicyclohepyl; a second substituent selected from adamantyl, cyclohexyl, and bicyclohepyl; and a third substituent selected from fluorenyl and dibenzoheptocyclic groups, each substituent being bonded to an N atom (e.g., the central N atom). For example, the bicyclohepyl used as a substituent in the amine compound according to the embodiments may be an unsubstituted bicyclo[2,2,1]heptyl (e.g., norbornyl). For example, in the amine compound according to the embodiments, R1 may be an unsubstituted adamantyl, an unsubstituted cyclohexyl, or an unsubstituted bicyclo[2,2,1]heptyl.

[0130] In some embodiments, such as those represented by Formula 2A or Formula 2B, the FR represented by Formula 2 may be bonded to the L or N atom of the amine compound of Formula 1 via position X or via any of the cyclic carbon atoms of the benzene ring (e.g., when L is a direct bond). In Formulas 2A and 2B, This refers to the position to be connected.

[0131]

[0132] In Formula 1, Ar1 and Ar2 can each be independently substituted or unsubstituted aryl groups having 6 to 30 cyclic carbon atoms. For example, Ar1 and Ar2 can each be independently substituted or unsubstituted phenylene. For example, in the embodiments, Ar1 and Ar2 can both be unsubstituted phenylene.

[0133] In Formula 1, L can be a direct bond, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms. When L is a direct bond, the nitrogen atom (N) of the amine in Formula 1 and FR can be directly bonded to each other via a single bond. In some embodiments, L can be a substituted or unsubstituted phenylene group.

[0134] In Equation 2, X can be CR a R b , N, NR c O or S. For example, FR represented by Formula 2 can be a substituted or unsubstituted fluorene derivative, a substituted or unsubstituted carbazole derivative, a substituted or unsubstituted dibenzofuran derivative, or a substituted or unsubstituted dibenzothiophene derivative.

[0135] In Equation 2, R a To R cEach of the following can be independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, and optionally, can be incorporated into an adjacent group to form a ring.

[0136] In Equation 2, d and e can both be independent integers from 0 to 4. In some embodiments, in Equation 2, R d and R e Each of the following can be independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, and optionally, can be incorporated into an adjacent group to form a ring.

[0137] In Equation 2, when d is 0, R d Unsubstituted in Equation 2 (e.g., Equation 2 does not include any R) d (substituents), and when e is 0, R e Unsubstituted in Equation 2 (e.g., Equation 2 does not include any R) e Substituents). For example, when both d and e in Formula 2 (e.g., simultaneously) are 0, the benzene ring in Formula 2 may be unsubstituted. When d in Formula 2 is an integer of 2 or greater, multiple R... d They can all be the same, or multiple Rs. d At least one of them can be different from the others. In some embodiments, when e is an integer of 2 or greater, multiple R e They can be the same, or multiple Rs. e At least one of them can be different from the others.

[0138] In some embodiments, when X in equation 2 is determined by CR a R b When representing, R a and R b Each of these can be independently a straight-chain alkyl, cycloalkyl, and / or aryl group, etc. In some embodiments, R a and R b They can combine to form a ring. R a and R b They can be combined into a fluorene ring, and the FR represented by Equation 2 can have a screw structure.

[0139] In some embodiments, when FR is a function of X, where X is CR a R b When Equation 2 is expressed, R aOr R b It can be directly combined with L or R. a Or R b It can bind directly to the nitrogen atom (N) of the amine (e.g., when L is a direct bond).

[0140] In the embodiments, the amine compound represented by Formula 1 may be represented by Formula 1-1 or Formula 1-2. In Formula 1-1 and Formula 1-2, R1, L, Ar1, and Ar2 may all be independently the same as those described for Formula 1, and X, R d R e , d, and e can all be independently identical to those described for Equation 2:

[0141] Equation 1-1

[0142]

[0143] Formula 1-2

[0144]

[0145] In some embodiments, the amine compounds represented by formulas 1-2 can be represented by formula 1-2A. In formula 1-2A, R1, L, Ar1, and Ar2 can all be independently the same as those described for formula 1, and R a R d R e , d, and e can all be independently identical to those described for Equation 2:

[0146] Formula 1-2A

[0147]

[0148] In some embodiments, the amine compound represented by Formula 1 may be represented by Formula 1A. For example, in the amine compound represented by Formula 1 according to the embodiments, both Ar1 and Ar2 may be unsubstituted phenylene oxides (e.g., Ar1 and Ar2 may be unsubstituted phenylene oxides simultaneously):

[0149] Formula 1A

[0150]

[0151] In some embodiments, the amine compound represented by Formula 1A may be represented by Formula 1A-1. For example, in the amine compound represented by Formula 1 according to the embodiments, the bicyclic heptyl (e.g., bicyclic [2,2,1]heptyl) and the substituent represented by R1 may be attached to the nitrogen atom (N) at the para position of the amine via a phenylene linker, respectively. However, the embodiments of this disclosure are not limited thereto.

[0152] Formula 1A-1

[0153]

[0154] In some embodiments, in Formula 1A and Formula 1A-1, R1, L, and FR can all be independently the same as those described for Formula 1.

[0155] The amine compound represented by Formula 1 according to the embodiments can be represented by any of the compounds in Group 1 of compounds. The hole transport region HTR of the light-emitting element ED according to the embodiments can include at least one of the amine compounds disclosed in Group 1 of compounds.

[0156] Compound group 1

[0157]

[0158]

[0159]

[0160]

[0161] The amine compound represented by Formula 1 according to the embodiments has a substituent structure that must include a bicyclic heptyl group and also must include one of bicyclic heptyl, cyclohexyl, and adamantyl, and therefore can have high glass transition temperature characteristics. This high glass transition temperature characteristic can result in excellent or suitable heat resistance and / or durability. In some embodiments, the substituent structure of the presented amine compound can facilitate low deposition temperatures in the deposition process to form a film, and thus can increase the productivity of the process used to form the film.

[0162] When the amine compound according to the embodiments is used in the hole transport region, the external quantum efficiency of the device can be increased by changing the light extraction mode and / or refractive index change between the first and second electrodes. Therefore, using the amine compound according to the embodiments in the hole transport region can increase the emission efficiency of the light-emitting element and improve its lifetime. In some embodiments, the lifetime and / or emission efficiency of the light-emitting element according to the embodiments can be improved by including the amine compound according to the embodiments, which has excellent or suitable heat resistance and / or durability, as a material for the light-emitting element.

[0163] In some embodiments, when the light-emitting element ED according to the embodiment includes a plurality of hole transport layers HTL1 and HTL2, the first hole transport layer HTL1 adjacent to the first electrode EL1 may include an amine compound represented by Formula 1 as described in the embodiment. In some embodiments, the second hole transport layer HTL2 disposed on the first hole transport layer HTL1 and adjacent to the emitter layer EML may include an amine derivative compound represented by Formula 3.

[0164] Formula 3

[0165]

[0166] In Equation 3, L 11 It can be a directly bonded, substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms. In some embodiments, in Formula 3, R 11 To R 14 Each of the groups may be independently substituted or unsubstituted alkyl groups having 1 to 10 carbon atoms, substituted or unsubstituted alkenyl groups having 2 to 10 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 cyclic carbon atoms, or substituted or unsubstituted heteroaryl groups having 2 to 30 cyclic carbon atoms, and optionally, may be incorporated into adjacent groups to form a ring.

[0167] For example, L 11 It can be a direct linker or a substituted or unsubstituted phenylene oxide. In some embodiments, R 11 It can be a substituted or unsubstituted phenyl group. However, the embodiments disclosed herein are not limited thereto.

[0168] In the amine derivatives represented by formula 3, R 12 It can be aryl or heteroaryl. For example, R 12 It can be a substituted or unsubstituted phenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted dibenzofuranyl, or a substituted or unsubstituted dibenzothiopheneyl.

[0169] The amine derivative represented by Formula 3 can also be represented by Formula 3-1 or Formula 3-2. In Formula 3-1 and Formula 3-2, L 11 and R 11 To R 14 Each can be independently identical to that described for Equation 3:

[0170] Equation 3-1

[0171]

[0172] Equation 3-2

[0173]

[0174] The light-emitting element ED according to the embodiment may include the amine compound according to the embodiment in the first hole transport layer HTL1, and include an amine derivative represented by Formula 3-1 or an amine derivative represented by Formula 3-2 in the second hole transport layer HTL2.

[0175] The amine derivative represented by Formula 3-1 can be represented by any of the compounds represented in compound group 2-1. For example, the second hole transport layer HTL2 can include any of the compounds represented in compound group 2-1:

[0176] Compound group 2-1

[0177]

[0178] The amine derivative compound represented by Formula 3-2 can be represented by any of the compounds represented in compound group 2-2. For example, the second hole transport layer HTL2 can include any of the compounds represented in compound group 2-2:

[0179] Compound group 2-2

[0180]

[0181] In some embodiments, the light-emitting element ED according to the embodiments may also include materials for the hole transport region (described later) in the hole transport region HTR, in addition to the amine compound and the amine derivative compound represented by Formula 3 according to the embodiments.

[0182] The hole transport region (HTR) can include a compound represented by formula H-1:

[0183] Formula H-1

[0184]

[0185] In formula H-1, L1 and L2 can each be independently a straight-linked, substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms. a and b can each be independently an integer from 0 to 10. In some embodiments, when a or b is an integer of 2 or greater, the plurality of L1 and L2 can each be independently a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms.

[0186] In formula H-1, Ar1 and Ar2 can each be independently a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms. In some embodiments, in formula H-1, Ar3 can be a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms.

[0187] The compound represented by formula H-1 can be a monoamine compound. In some embodiments, the compound represented by formula H-1 can be a diamine compound in which at least one of Ar1 to Ar3 includes an amino group as a substituent. In some embodiments, the compound represented by formula H-1 can be a carbazole compound in which at least one of Ar1 and Ar2 includes a substituted or unsubstituted carbazole group, or a fluorene compound in which at least one of Ar1 and Ar2 includes a substituted or unsubstituted fluorene group.

[0188] The compound represented by formula H-1 can be represented by any of the compounds in group H. However, the compounds listed in group H are illustrative, and the compound represented by formula H-1 is not limited to those represented in group H.

[0189] Compound group H

[0190]

[0191] Hole transport region (HTR) may include phthalocyanine compounds (such as copper phthalocyanine), N 1 N 1 '-([1,1'-biphenyl]-4,4'-diyl)bis(N 1 -Phenyl-N 4 N 4 1,4-Di-di-m-tolylphenyl-1,4-diamine (DNTPD), 4,4',4”-[tris(3-methylphenyl)phenylamino]triphenylamine (m-MTDATA), 4,4',4”-tris(N,N-diphenylamino)triphenylamine (TDATA), 4,4',4”-tris[N-(2-naphthyl)-N-phenylamino]triphenylamine (2-TNATA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / dodecylbenzenesulfonic acid (PA) NI / DBSA), polyaniline / camphor sulfonic acid (PANI / CSA), polyaniline / poly(4-styrene sulfonate) (PANI / PSS), N,N'-di(naphthyl-1-yl)-N,N'-diphenyl-benzidine (NPD), triphenylamine-containing polyether ketone (TPAPEK), 4-isopropyl-4'-methyldiphenyliodonium [tetra(pentafluorophenyl)borate] and / or dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexaonitrile (HAT-CN), etc.

[0192] Hole transport regions (HTRs) may include carbazole derivatives (such as N-phenylcarbazole and / or polyvinylcarbazole), fluorene derivatives, N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (TPD), triphenylamine derivatives (such as 4,4',4"-tris(N-carbazolyl)triphenylamine (TCTA)), N,N'-bis(naphthyl-l-yl)-N,N'-diphenyl-benzidine (NPB), 4,4'-cyclohexylene-bis[N,N-bis(4-methylphenyl)aniline] (TAPC), 4,4'-bis[N,N'-(3-tolyl)amino]-3,3'-dimethylbiphenyl (HMTPD) and / or 1,3-bis(N-carbazolyl)benzene (mCP), etc.

[0193] 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'-biscarbazole (CCP), 1,3-bis(N-carbazolyl)benzene (mCP) and / or 1,3-bis(1,8-dimethyl-9H-carbazol-9-yl)benzene (mDCP), etc.

[0194] The hole transport region HTR may include the aforementioned compound in at least one of the hole injection layer HIL, the hole transport layer HTL, and the electron blocking layer EBL.

[0195] The thickness of the hole transport region (HTR) can be approximately to approximately For example, about to approximately When the hole transport region (HTR) includes a hole injection layer (HIL), the thickness of the hole injection layer (HIL) can be, for example, approximately to approximately When the hole transport region (HTR) includes the hole transport layer (HTL), the thickness of the hole transport layer (HTL) can be approximately to approximately For example, when the hole transport region HTR includes an electron blocking layer EBL, the thickness of the electron blocking layer EBL can be approximately to approximately When the thicknesses of the hole transport region (HTR), hole injection layer (HIL), hole transport layer (HTL), and electron blocking layer (EBL) meet the above-mentioned ranges, satisfactory hole transport properties can be obtained without significantly increasing the driving voltage.

[0196] In addition to the materials described above, the hole transport region (HTR) may also include a charge-generating material to improve conductivity. The charge-generating material may be substantially uniformly or non-uniformly dispersed in the hole transport region (HTR). The charge-generating material may be, for example, a p-doped agent. The p-doped agent may include at least one selected from metal halide compounds, quinone derivatives, metal oxides, and cyano-containing compounds, but embodiments of this disclosure are not limited thereto. For example, p-dopers may include metal halide compounds (such as CuI and / or RbI), quinone derivatives (such as tetracyanoquinone dimethyl ether (TCNQ) and / or 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinone dimethyl ether (F4-TCNQ)), metal oxides (such as tungsten oxide and / or molybdenum oxide), cyano-containing compounds (such as dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexanitrile (HAT-CN) and / or 4-[[2,3-bis[cyano-(4-cyano-2,3,5,6-tetrafluorophenyl)methylene]cyclopropylidene]-cyanomethyl]-2,3,5,6-tetrafluorobenzonitrile (NDP9)), but the embodiments of this disclosure are not limited thereto.

[0197] As described above, in addition to the hole injection layer (HIL) and the hole transport layer (HTL), the hole transport region (HTR) may also include at least one of a buffer layer and an electron blocking layer (EBL). The buffer layer can compensate for the optical resonant distance based on the wavelength of light emitted from the emitter layer (EML), thereby increasing the luminous efficiency of the device. Materials that can be included in the hole transport region (HTR) can be used as materials included in the buffer layer. The electron blocking layer (EBL) is a layer that prevents or reduces the injection of electrons from the electron transport region (ETR) into the hole transport region (HTR).

[0198] The emitter layer EML is disposed on the hole transmission region HTR. The emitter layer EML can have, for example, approximately to approximately or about to approximately The thickness of the emitter layer (EML) is as follows. The EML can be a single layer formed of a single material, a single layer formed of multiple different materials, or a multilayer structure with multiple layers formed of multiple different materials.

[0199] In a light-emitting element (ED), the emitting layer (EML) may include anthracene derivatives, pyrene derivatives, fluoranthene derivatives, etc. Derivatives, dihydrobenzanthracene derivatives, and / or benzo[9,10]phenanthrene derivatives. For example, the emission layer EML may include anthracene derivatives and / or pyrene derivatives.

[0200] exist Figure 3 to Figure 7In the light-emitting element ED shown according to the embodiment, the emitting layer EML may include a host and a dopant, and the emitting layer EML may include a compound represented by Formula E-1. The compound represented by Formula E-1 can be used as a fluorescent host material.

[0201] E-1

[0202]

[0203] In equation E-1, R 31 To R 40 Each of these groups may independently be a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted silyl group, a substituted or unsubstituted thio group, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, and optionally, may be incorporated into an adjacent group to form a ring. In some embodiments, R 31 To R 40 It can optionally be incorporated into adjacent groups to form a saturated hydrocarbon ring, an unsaturated hydrocarbon ring, a saturated heterocycle, or an unsaturated heterocycle.

[0204] In E-1, "c" and "d" can both be independent integers from 0 to 5.

[0205] The compound represented by formula E-1 can be represented by any one of compounds E1 to E19.

[0206]

[0207]

[0208] In an embodiment, the emitting layer EML may include a compound represented by formula E-2a or E-2b. The compound represented by formula E-2a or E-2b can be used as a phosphorescent host material.

[0209] E-2a

[0210]

[0211] In formula E-2a, a can be an integer from 0 to 10, and La can each be independently a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms. In some embodiments, when a is an integer of 2 or greater, the plurality of La can each be independently a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms.

[0212] In some embodiments, in formula E-2a, A1 to A5 can each be independently N or CR. i R a To R i Each group may independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted amino group, a substituted or unsubstituted thio group, a substituted or unsubstituted oxygen group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, and optionally, may be incorporated into an adjacent group to form a ring. In some embodiments, R a To R i It can optionally be incorporated into adjacent groups to form a hydrocarbon ring or a heterocycle including N, O and / or S as cyclic atoms.

[0213] In some embodiments, in formula E-2a, two or three selected from A1 to A5 may be N, and the remaining part may be CR. i .

[0214] E-2b

[0215]

[0216] In formula E-2b, Cbz1 and Cbz2 can both be independently unsubstituted carbazole groups or carbazole groups substituted with aryl groups having 6 to 30 cyclic carbon atoms. b It can be a directly bonded, substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms. When "b" is an integer from 0 to 10 and b is an integer of 2 or greater, multiple L... b They can all be independently substituted or unsubstituted aryl groups having 6 to 30 cyclic carbon atoms, or substituted or unsubstituted heteroaryl groups having 2 to 30 cyclic carbon atoms.

[0217] The compound represented by formula E-2a or E-2b can be represented by any of the compounds in group E-2. However, the compounds listed in group E-2 are illustrative, and the compound represented by formula E-2a or E-2b is not limited to the compounds represented in group E-2.

[0218] Compound group E-2

[0219]

[0220]

[0221] The emitter layer EML may also include any suitable material in the art as the host material. For example, the emitter layer EML may include at least one selected from bis[2-(diphenylphosphino)phenyl]ether oxide (DPEPO), 4,4'-bis(N-carbazolyl)-1,1'-biphenyl (CBP), 1,3-bis(carbazol-9-yl)benzene (mCP), 2,8-bis(diphenylphospho)dibenzo[b,d]furan (PPF), 4,4',4”-tris(carbazol-9-yl)triphenylamine (TCTA), and 1,3,5-tris(1-phenyl-1H-benzo[d]imidazol-2-yl)benzene (TPBi) as the host material. However, the embodiments of this disclosure are not limited thereto; for example, tris(8- Hydroxyquinoline aluminum (Alq3), 9,10-bis(naphthyl-2-yl)anthracene (ADN), 2-tert-butyl-9,10-bis(naphthyl-2-yl)anthracene (TBADN), stilbeneyl aryl compounds (DSA), 4,4'-bis(9-carbazolyl)-2,2'-dimethyl-biphenyl (CDBP), 2-methyl-9,10-bis(naphthyl-2-yl)anthracene (MADN), hexaphenylcyclotriphosphazene (CP1), 1,4-bis(triphenylsilyl)benzene (UGH2), hexaphenylcyclotrisiloxane (DPSiO3) and / or octaphenylcyclotetrasiloxane (DPSiO4) can be used as host materials.

[0222] The emitter layer (EML) may include compounds represented by the formula Ma or Mb. Compounds represented by the formula Ma or Mb can be used as phosphorescent dopant materials.

[0223] Formula Ma

[0224]

[0225] In formula Ma, Y1 to Y4 and Z1 to Z4 can each be independently CR1 or N, and R1 to R4 can each be independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted amino group, a substituted or unsubstituted thio group, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, and optionally, they can be incorporated into adjacent groups to form a ring. In formula Ma, "m" can be 0 or 1, and "n" can be 2 or 3. In formula Ma, when "m" is 0, "n" can be 3, and when "m" is 1, "n" can be 2.

[0226] Compounds represented by the formula Ma can be used as phosphorescent dopants.

[0227] Compounds represented by formula Ma can be represented by any one of compounds selected from M-a1 to M-a25. However, compounds M-a1 to M-a25 are illustrative, and compounds represented by formula Ma are not limited to those represented by compounds M-a1 to M-a25.

[0228]

[0229]

[0230]

[0231] Compounds M-a1 and M-a2 can be used as red dopant materials, and compounds M-a3 to M-a7 can be used as green dopant materials.

[0232] Formula Mb

[0233]

[0234] In formula Mb, Q1 to Q4 can each be independently C or N, and C1 to C4 can each be independently a substituted or unsubstituted hydrocarbon ring having 5 to 30 cyclic carbon atoms or a substituted or unsubstituted heterocycle having 2 to 30 cyclic carbon atoms. L 21 To L 24 Each can be a direct-connect key independently.

[0235]

[0236] The substituted or unsubstituted divalent alkyl group having 1 to 20 carbon atoms, the substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or the substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, wherein e1 to e4 can each be independently 0 or 1. R 31 To R 39 Each of the following groups may be independently a hydrogen atom, a deuterium atom, a cyano group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, and optionally, may be incorporated into an adjacent group to form a ring, and d1 to d4 may each be independently an integer from 0 to 4.

[0237] Compounds represented by the formula Mb can be used as blue or green phosphorescent dopants.

[0238] The compound represented by formula Mb can be represented by any of the following compounds. However, the compounds are illustrative, and the compound represented by formula Mb is not limited to the compounds shown below:

[0239]

[0240] In the above compounds, R, R 38 and R 39 Each of these can be independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms.

[0241] The emitter layer (EML) may include compounds represented by any one of the formulas Fa to Fc. Compounds represented by formulas Fa to Fc can be used as fluorescent dopant materials.

[0242] Formula Fa

[0243]

[0244] In formula Fa, the formula is selected from R. a To R j Both of them can independently replace the one mentioned. R a To R j The un-included The remaining substituted portion can be independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms. In this context, Ar1 and Ar2 can each be independently a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms. For example, at least one of Ar1 and Ar2 can be a heteroaryl group including O or S as a cyclic atom.

[0245] Formula Fb

[0246]

[0247] In equation Fb, R a and R bEach of the Ar1 to Ar4 groups can be independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, and optionally, can be bonded to an adjacent group to form a ring. Each of the Ar1 to Ar4 groups can be independently a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms.

[0248] In formula Fb, U and V can both be independently substituted or unsubstituted hydrocarbon rings having 5 to 30 cyclic carbon atoms or substituted or unsubstituted heterocycles having 2 to 30 cyclic carbon atoms.

[0249] In formula Fb, the number of rings represented by U and V can both be independently 0 or 1. For example, in formula Fb, when the number of U or V is 1, a condensed ring is formed at the portion indicated by U or V, and when the number of U or V is 0, the ring indicated by U or V does not exist. 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 condensed ring of the fluorene nucleus having formula Fb can be a tetracyclic compound. When the number of both U and V (e.g., simultaneously) is 0, the condensed ring of the fluorene nucleus having formula Fb can be a tricyclic compound. Furthermore, when the number of both U and V (e.g., simultaneously) is 1, the condensed ring of the fluorene nucleus having formula Fb can be a pentacyclic compound.

[0250] Formula Fc

[0251]

[0252] In equation Fc, A1 and A2 can both be independently O, S, Se, or NR. m And R m It can be a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms. R1 to R 11 Each group may independently be a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted amino group, a substituted or unsubstituted boron group, a substituted or unsubstituted oxygen group, a substituted or unsubstituted thio group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms, and optionally, may be incorporated into an adjacent group to form a ring.

[0253] In formula Fc, A1 and A2 can each independently bind to substituents in adjacent rings to form condensed rings. For example, when A1 and A2 are both independently NR... m In this case, A1 can be bonded to R4 or R5 to form a ring. In some embodiments, A2 can be bonded to R7 or R8 to form a ring.

[0254] In embodiments, the emitter layer EML may include styrene derivatives (e.g., 1,4-bis[2-(3-N-ethylcarbazolyl)vinyl]benzene (BCzVB), 4-(di-p-tolylamino)-4'-[(di-p-tolylamino)styrene]benzene (DPAVB), N-(4-((E)-2-(6-(((E)-4-(diphenylamino)styrene)naphth-2-yl)vinyl)phenyl)-N-phenyl) Aniline (N-BDAVBi)), 4,4'-bis[2-(4-(N,N-diphenylamino)phenyl)vinyl]biphenyl (DPAVBi), perylene and / or its derivatives (e.g., 2,5,8,11-tetra-tert-butylperylene (TBP)) and / or pyrene and / or its derivatives (e.g., 1,1'-dipyrene, 1,4-dipyrenebenzene, 1,4-bis(N,N-diphenylamino)pyrene) are used as suitable dopant materials.

[0255] The emitter layer (EML) can include any suitable phosphorescent dopant material. For example, metal complexes including iridium (Ir), platinum (Pt), osmium (Os), gold (Au), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), or thulium (Tm) can be used as phosphorescent dopant. For example, bis(4,6-difluorophenylpyridine-N,C2'-pyridinecarboxylic acid)iridium(III) (FIrpic), bis(2,4-difluorophenylpyridine)tetra(1-pyrazolyl)boronic acidiridium(III) (Fir6), and / or octaethylporphyrin platinum (PtOEP) can be used as phosphorescent dopant. However, the embodiments of this disclosure are not limited thereto.

[0256] The emitter layer (EML) may include quantum dot materials. The core of the quantum dots may be selected from group II-VI compounds, group III-VI compounds, group I-III-VI compounds, group III-V compounds, group III-II-V compounds, group IV-VI compounds, group IV elements, group IV compounds, and combinations thereof.

[0257] Group 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, CdZnS, CdZnSe The group consisting of CdZnTe, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, MgZnSe, MgZnS and mixtures thereof; and quaternary compounds selected from the group consisting of HgZnTeS, CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe, HgZnSTe and mixtures thereof.

[0258] III-VI compounds may include binary compounds (such as In2S3 and / or In2Se3), ternary compounds (such as InGaS3 and InGaSe3), or any combination thereof.

[0259] Group I-III-VI compounds may be selected from: ternary compounds selected from the group consisting of AgInS, AgInS2, CuInS, CuInS2, AgGaS2, CuGaS2, CuGaO2, AgGaO2, AgAlO2 and mixtures thereof; and quaternary compounds (such as AgInGaS2 and / or CuInGaS2).

[0260] Group III-V compounds may be selected from the group consisting of: binary compounds selected from the group consisting of GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, InSb and mixtures thereof; ternary compounds selected from the group consisting of GaNP, GaNAs, GaNSb, GaPAs, GaPSb, AlNP, AlNAs, AlNSb, AlPAs, AlPSb, InGaP, InAlP, InNP, InNAs, InNSb, InPAs, InPSb and mixtures thereof; and quaternary compounds selected from the group consisting of GaAlNP, GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNP, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs, InAlPSb and mixtures thereof. In some embodiments, Group III-V compounds may also include Group II metals. For example, InZnP and other compounds can be selected as III-II-V group compounds.

[0261] Group IV-VI compounds may be selected from the group consisting of: binary compounds selected from the group consisting of SnS, SnSe, SnTe, PbS, PbSe, PbTe and mixtures thereof; ternary compounds selected from the group consisting of SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, SnPbTe and mixtures thereof; and quaternary compounds selected from the group consisting of SnPbSSe, SnPbSeTe, SnPbSTe and mixtures thereof. Group IV elements may be selected from the group consisting of Si, Ge and mixtures thereof. Group IV compounds may be binary compounds selected from the group consisting of SiC, SiGe and mixtures thereof.

[0262] In this context, binary, ternary, and / or quaternary compounds may exist in the particles at substantially uniform concentrations (e.g., distributions), or they may exist in the same particles at varying or partially different concentration distributions. In some embodiments, the quantum dots may have a core-shell structure in which one quantum dot surrounds another quantum dot. The core-shell structure may have (e.g., may form) a concentration gradient, for example, in which the concentration of an element or compound present in the shell gradually decreases toward the core.

[0263] In some examples, quantum dots can have a core-shell structure comprising a core containing the aforementioned nanocrystals and a shell surrounding (e.g., around) the core. The shell of the quantum dot can serve as a protective layer to maintain semiconductor properties by preventing or reducing chemical denaturation of the core, and / or as a charged layer to impart electrophoretic properties to the quantum dot. The shell can be a single layer or can have multiple layers. Examples of materials in the shell of a quantum dot can include metal or non-metal oxides, semiconductor compounds, or combinations thereof.

[0264] For example, metal or non-metal oxides may be shown as binary compounds (such as SiO2, Al2O3, TiO2, ZnO, MnO, Mn2O3, Mn3O4, CuO, FeO, Fe2O3, Fe3O4, CoO, Co3O4 and / or NiO) or ternary compounds (such as MgAl2O4, CoFe2O4, NiFe2O4 and / or CoMn2O4), but the embodiments of this disclosure are not limited thereto.

[0265] In some embodiments, the semiconductor compound may be CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnSeS, ZnTeS, GaAs, GaP, GaSb, HgS, HgSe, HgTe, InAs, InP, InGaP, InSb, AlAs, AlP and / or AlSb, etc., but the embodiments of this disclosure are not limited thereto.

[0266] Quantum dots can have a full width at half maximum (FWHM) of an emission wavelength spectrum of about 45 nm or less (e.g., about 40 nm or less or about 30 nm or less), and color purity and / or color gamut can be improved within this range. Because light emitted through quantum dots is emitted in all directions, a wide viewing angle can be improved.

[0267] In some embodiments, the quantum dots have any suitable shape in the art, and for example, spherical nanoparticles, pyramidal nanoparticles, multi-armed nanoparticles or cubic nanoparticles, nanotubes, nanowires, nanofibers and / or plate-like nanoparticles may be used.

[0268] Quantum dots can control the color of emitted light based on particle size; therefore, quantum dots can have one or more suitable emission colors (such as blue, red, and / or green).

[0269] exist Figure 3 to Figure 7 In the light-emitting element ED shown according to an embodiment, the electron transport region ETR is disposed on the emitter layer EML. The electron transport region ETR may include at least one of the hole blocking layer HBL, the electron transport layer ETL, and the electron injection layer EIL, but the embodiments of this disclosure are not limited thereto.

[0270] The electron transport region (ETR) can have a single-layer structure formed of a single material, a single-layer structure formed of multiple different materials, or a multi-layer structure with multiple layers formed of multiple different materials.

[0271] For example, the electron transport region (ETR) can have a single-layer structure of an electron injection layer (EIL) or an electron transport layer (ETL), and can also have a single-layer structure formed of an electron injection material and an electron transport material. Furthermore, the ETR can have a single-layer structure formed of multiple different materials, or a structure in which an electron transport layer (ETL) / electron injection layer (EIL) or a hole blocking layer (HBL) / electron transport layer (ETL) / electron injection layer (EIL) are sequentially stacked from the emitter layer (EML), but the embodiments of this disclosure are not limited thereto. The thickness of the ETR can be, for example, approximately... to approximately

[0272] Electron transport regions (ETRs) can be formed using one or more suitable methods, such as vacuum deposition, spin coating, casting, Langmuir-Blodget (LB) method, inkjet printing, laser printing and / or laser-induced thermal imaging (LITI).

[0273] The electron transport region (ETR) can include compounds represented by formula ET-1.

[0274] ET-1

[0275]

[0276] In Equation ET-1, at least one selected from X1 to X3 is N, and the remainder is CR. a R a It can be a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms. Ar1 to Ar3 can each independently be a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms.

[0277] In Formula ET-1, a to c can each be an independent integer from 0 to 10. In Formula ET-1, L1 to L3 can each be an independent, directly bonded, substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms. In some embodiments, when a to c are integers of 2 or greater, L1 to L3 can each be an independent, substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 cyclic carbon atoms.

[0278] The electron transport region (ETR) may include anthracene compounds. However, embodiments of this disclosure are not limited thereto, and the ETR may include, for example, tris(8-hydroxyquinoline)aluminum (Alq3), 1,3,5-tris[(3-pyridyl)-benzene-3-yl]benzene, 2,4,6-tris(3'-(pyridin-3-yl)biphenyl-3-yl)-1,3,5-triazine, 2-(4-(N-phenylbenzimidazol-1-yl)phenyl)-9,10-dinaphthylanthracene, 1,3,5-tris(1-phenyl-1H-benzimidazol-2-yl)benzene (TPBi), 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), 3-(4 4-(naphthyl-1-yl)-4-phenyl-5-tert-butylphenyl-1,2,4-triazole (TAZ), 4-(naphthyl-1-yl)-3,5-diphenyl-4H-1,2,4-triazole (NTAZ), 2-(4-biphenyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (tBu-PBD), bis(2-methyl-8-hydroxyquinoline-N1,O8)-(1,1'-biphenyl-4-hydroxy)aluminum (BAlq), bis(benzoquinoline-10-hydroxy)beryllium (Bebq2), 9,10-bis(naphthyl-2-yl)anthracene (ADN), 1,3-bis[3,5-bis(pyridin-3-yl)phenyl]benzene (BmPyPhB), or mixtures thereof.

[0279] In some embodiments, the electron transport region (ETR) may also include metal halides (such as LiF, NaCl, CsF, RbCl, RbI, CuI, and / or KI), lanthanides (such as Yb), and co-deposited materials of the aforementioned metal halides and lanthanides. For example, the ETR may include KI:Yb and / or RbI:Yb as co-deposited materials. In some embodiments, the ETR may include metal oxides (such as Li₂O, BaO, and / or Liq (8-hydroxy-quinoline lithium)), but the embodiments of this disclosure are not limited thereto. The ETR may also be formed from a mixture of an electron transport material and an insulating organometallic salt. The organometallic salt may be a material having a band gap of about 4 eV or greater. For example, the organometallic salt may include, for example, metal acetates, metal benzoates, metal acetoacetates, metal acetylacetonates, and / or metal stearates.

[0280] In addition to the materials described above, the electron transport region (ETR) may also include at least one of 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP) and 4,7-diphenyl-1,10-phenanthroline (Bphen), but the embodiments disclosed herein are not limited thereto.

[0281] The electron transport region (ETR) may include the aforementioned 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).

[0282] When the electron transport region (ETR) includes the electron transport layer (ETL), the thickness of the ETL can be approximately... to approximately For example, about to approximately When the thickness of the electron transport layer (ETL) meets the above-mentioned range, satisfactory electron transport properties can be achieved without significantly increasing the driving voltage. When the electron transport region (ETR) includes the electron injection layer (EIL), the thickness of the electron injection layer (EIL) can be approximately... to approximately For example, about to approximately When the thickness of the electron injection layer (EIL) meets the above range, satisfactory electron injection properties can be achieved without significantly increasing the driving voltage.

[0283] The second electrode EL2 is disposed on the electron transport region ETR. The second electrode EL2 can be a common electrode. The second electrode EL2 can be a cathode or an anode, but the embodiments of this disclosure are not limited thereto. For example, when the first electrode EL1 is an anode, the second electrode EL2 can be a cathode, and when the first electrode EL1 is a cathode, the second electrode EL2 can be an anode.

[0284] The second electrode EL2 can be a transmission electrode, a transmission-reflection electrode, or a reflection electrode. When the second electrode EL2 is a transmission electrode, it can include a transparent metal oxide (such as indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), and / or indium tin zinc oxide (ITZO), etc.).

[0285] When the second electrode EL2 is a transmissive or reflective electrode, it may comprise Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF, Mo, Ti, Yb, W, or compounds or mixtures thereof (e.g., AgMg, AgYb, or MgYb), or a material having a multilayer structure such as LiF / Ca or LiF / Al. In some embodiments, the second electrode EL2 may have a multilayer structure comprising a reflective or transmissive film formed from the aforementioned materials and a transparent conductive film formed from indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), and / or indium tin zinc oxide (ITZO). For example, the second electrode EL2 may comprise the aforementioned metallic materials, a combination of two or more metallic materials selected from the aforementioned metallic materials, or oxides of the aforementioned metallic materials.

[0286] In some embodiments, the second electrode EL2 can be connected to an auxiliary electrode. When the second electrode EL2 is connected to the auxiliary electrode, the resistance of the second electrode EL2 can be reduced.

[0287] In some embodiments, the capping layer CPL may also be disposed on the second electrode EL2 of the light-emitting element ED according to the embodiment (e.g., externally). The capping layer CPL may comprise multiple layers or a single layer. In embodiments, the capping layer CPL may comprise an amine compound according to the above embodiments.

[0288] In embodiments, the capping layer CPL can be an organic layer or an inorganic layer. For example, when the capping layer CPL comprises an inorganic material, the inorganic material may include alkali metal compounds (such as LiF) and / or alkaline earth metal compounds (such as MgF2, SiON, SiN). x and / or SiO y wait).

[0289] For example, when the capping CPL comprises an organic material, the organic material may include α-NPD, NPB, TPD, m-MTDATA, Alq3, CuPc, N4,N4,N4',N4'-tetra(biphenyl-4-yl)biphenyl-4,4'-diamine (TPD15), 4,4',4"-tris(carbazole-9-yl)triphenylamine (TCTA), epoxy resin, or acrylate (such as methacrylate). However, embodiments of this disclosure are not limited thereto, and the capping CPL may include at least one selected from compounds P1 to P5:

[0290]

[0291] In some embodiments, the refractive index of the capping layer CPL may be about 1.6 or greater. For example, for light in the wavelength range of about 550 nm to about 660 nm, the refractive index of the capping layer CPL may be about 1.6 or greater.

[0292] Figure 8 and Figure 9 All are cross-sectional views of the display device according to the embodiments. (Referring to...) Figure 8 and Figure 9 In the description of the display device according to the embodiments, the following will not be described again: Figure 1 to Figure 7 The content described in the document overlaps with the content described elsewhere, and the main focus will be on the differences.

[0293] Reference Figure 8 According to an embodiment, the display device DD may include a display panel DP containing a display element layer DP-ED, a light control layer CCL and a color filter layer CFL disposed on the display panel DP.

[0294] exist Figure 8 In the embodiment shown, the display panel DP may include a substrate layer BS, a circuit layer DP-CL disposed on the substrate layer BS, and a display element layer DP-ED, and the display element layer DP-ED may include a light-emitting element ED.

[0295] The light-emitting element (ED) may include a first electrode EL1, a hole transport region HTR disposed on the first electrode EL1, an emitter layer EML disposed on the hole transport region HTR, an electron transport region ETR disposed on the emitter layer EML, and a second electrode EL2 disposed on the electron transport region ETR. In some embodiments, the above... Figure 3 to Figure 7 The same structure as any light-emitting element can be applied to Figure 8 The light-emitting element ED is shown in the figure.

[0296] Reference Figure 8The emitting layer EML can be disposed in the opening OH defined in the pixel defining film PDL. For example, the emitting layer EML separated by the pixel defining film PDL and configured to emit light in the same wavelength range as each of the light-emitting regions PXA-R, PXA-G, and PXA-B. In the display device DD according to an embodiment, the emitting layer EML can emit blue light. In some embodiments, the emitting layer EML can be configured as a common layer covering all of the light-emitting regions PXA-R, PXA-G, and PXA-B.

[0297] A light control layer (CCL) can be disposed on a display panel (DP). The CCL may include a light conversion element. The light conversion element may be a quantum dot or a phosphor. The light conversion element can convert the wavelength of received light and emit the converted light. For example, the CCL may be a layer comprising quantum dots or a layer comprising phosphors.

[0298] The optical control layer (CCL) may include multiple optical control units CCP1, CCP2, and CCP3. The optical control units CCP1, CCP2, and CCP3 may be separated from each other.

[0299] Reference Figure 8 The segmented pattern BMP can be disposed between the mutually separated light control units CCP1, CCP2, and CCP3, but the embodiment is not limited to this. Figure 8 In the diagram, the segmentation pattern BMP is shown as not overlapping with the light control units CCP1, CCP2 and CCP3, but the edges of the light control units CCP1, CCP2 and CCP3 may overlap with the segmentation pattern BMP at least partially.

[0300] The light control layer CCL may include a first light control unit CCP1, a second light control unit CCP2, and a third light control unit CCP3. The first light control unit CCP1 includes a first quantum dot QD1 configured to convert the first color light provided in the light-emitting element ED into a second color light. The second light control unit CCP2 includes a second quantum dot QD2 configured to convert the first color light into a third color light. The third light control unit CCP3 is configured to transmit the first color light.

[0301] In this embodiment, the first light control unit CCP1 can provide red light as the second color light, and the second light control unit CCP2 can provide green light as the third color light. The third light control unit CCP3 can transmit and provide blue light as the first color light provided by the light-emitting element 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 description as described above can be applied to quantum dots QD1 and QD2.

[0302] In some embodiments, the light control layer CCL may further include a scatterer SP. The first light control unit CCP1 may include a first quantum dot QD1 and a scatterer SP, the second light control unit CCP2 may include a second quantum dot QD2 and a scatterer SP, and the third light control unit CCP3 may not include a quantum dot but may include a scatterer SP.

[0303] The scatterer SP can be inorganic particles. For example, the scatterer SP can include at least one of TiO2, ZnO, Al2O3, SiO2 and hollow silica, or it can be a mixture of two or more scatterer materials, all of which include at least one selected from TiO2, ZnO, Al2O3, SiO2 and hollow silica.

[0304] The first light control unit CCP1, the second light control unit CCP2, and the third light control unit CCP3 may each comprise a matrix resin BR1, BR2, and BR3, and these matrix resins BR1, BR2, and BR3 may disperse quantum dots QD1 and QD2 and a scatterer SP. In an embodiment, the first light control unit CCP1 may include the first quantum dot QD1 and the scatterer SP dispersed in the first matrix resin BR1, the second light control unit CCP2 may include the second quantum dot QD2 and the scatterer SP dispersed in the second matrix resin BR2, and the third light control unit CCP3 may include the scatterer SP dispersed in the third matrix resin BR3. The matrix resins BR1, BR2, and BR3 are media in which quantum dots QD1 and QD2 and the scatterer SP are dispersed, and may be formed into a suitable resin composition comprising one or more commonly referred to as binders. For example, the matrix resins BR1, BR2, and BR3 may be acrylic resins, urethane resins, acrylic resins, and / or epoxy resins, etc. The matrix resins BR1, BR2, and BR3 may be transparent resins. In the embodiments, the first matrix resin BR1, the second matrix resin BR2, and the third matrix resin BR3 may be the same as or different from each other.

[0305] The light control layer CCL may include a barrier layer BFL1. The barrier layer BFL1 can be used to prevent or reduce the penetration of moisture and / or oxygen (hereinafter referred to as "moisture / oxygen"). The barrier layer BFL1 may be disposed on the light control units CCP1, CCP2, and CCP3 to prevent or reduce the exposure of the light control units CCP1, CCP2, and CCP3 to moisture / oxygen. In some embodiments, the barrier layer BFL1 may cover the light control units CCP1, CCP2, and CCP3. In some embodiments, the barrier layer BFL2 may also be disposed between the light control units CCP1, CCP2, and CCP3 and the color filter layer CFL.

[0306] Barrier layers BFL1 and BFL2 may include at least one inorganic layer. For example, barrier layers BFL1 and BFL2 can be formed by including inorganic materials. For example, barrier layers BFL1 and BFL2 can be formed as thin films comprising silicon nitride, aluminum nitride, zirconium nitride, titanium nitride, hafnium nitride, tantalum nitride, silicon oxide, aluminum oxide, titanium oxide, tin oxide, cerium oxide, silicon oxynitride, and / or metal films that ensure light transmittance. In some embodiments, barrier layers BFL1 and BFL2 may also each independently include an organic film. Barrier layers BFL1 and BFL2 may consist of a single layer or multiple layers.

[0307] In the display device DD according to the embodiment, the color filter layer CFL can be disposed on the light control layer CCL. For example, the color filter layer CFL can be directly disposed on the light control layer CCL. In this case, the blocking layer BFL2 may not be disposed.

[0308] A color filter layer CFL may include a light-shielding portion BM and filters CF1, CF2, and CF3. The color filter layer CFL may include a first filter CF1 configured to transmit a second color of light, a second filter CF2 configured to transmit a third color of light, and a third filter CF3 configured to transmit a first color of light. For example, the first filter CF1 may be a red filter, the second filter CF2 may be a green filter, and the third filter CF3 may be a blue filter. Each of filters CF1, CF2, and CF3 may include a polymeric photosensitive resin and / or pigments and / or dyes. The first filter CF1 may include red pigments and / or dyes, the second filter CF2 may include green pigments and / or dyes, and the third filter CF3 may include blue pigments and / or dyes. In some embodiments, the third filter CF3 may not include pigments or dyes. For example, the third filter CF3 may include a polymeric photosensitive resin and may not include pigments or dyes. The third filter CF3 may be transparent. The third filter CF3 may be formed of a transparent photosensitive resin.

[0309] In some embodiments, the first filter CF1 and the second filter CF2 may both be yellow filters. The first filter CF1 and the second filter CF2 may not be separate from each other and may be integrally arranged.

[0310] The light-shielding portion BM can be a black matrix. The light-shielding portion BM can be formed using organic or inorganic light-shielding materials comprising black pigments or dyes. The light-shielding portion BM can prevent or reduce light leakage and can separate the boundaries between adjacent filters CF1, CF2, and CF3. In some embodiments, the light-shielding portion BM can be formed from a blue filter.

[0311] The first to third filters CF1, CF2 and CF3 can be set to correspond to the red emitting area PXA-R, the green emitting area PXA-G and the blue emitting area PXA-B, respectively.

[0312] The substrate BL can be disposed on the color filter layer CFL. The substrate BL can be a component configured to provide a substrate surface on which the color filter layer CFL and the light control layer CCL are disposed. The substrate BL can be a glass substrate, a metal substrate, and / or a plastic substrate, etc. However, embodiments of this disclosure are not limited thereto, and the substrate BL can be an inorganic layer, an organic layer, or a composite material layer. In some embodiments, unlike the configuration shown, the substrate BL may not be disposed in the embodiment.

[0313] Figure 9 This is a cross-sectional view showing a portion of a display device according to an embodiment. Figure 9 It shows the relationship with Figure 8 A cross-sectional view of the portion corresponding to the display panel DP. In the display device DD-TD according to an embodiment, the light-emitting element ED-BT may include a plurality of light-emitting structures OL-B1, OL-B2, and OL-B3. The light-emitting element ED-BT may include a 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 disposed between the first electrode EL1 and the second electrode EL2 by sequentially stacking them in the thickness direction. Each of the light-emitting structures OL-B1, OL-B2, and OL-B3 may include an emissive layer EML (Emitting Layer, Emulsion ... Figure 7 ) and respectively set in the emission layer EML ( Figure 7 Hole transport region (HTR) and electron transport region (ETR) above and below.

[0314] For example, the light-emitting element ED-BT included in the display device DD-TD according to the embodiment may be a light-emitting element having a series structure including multiple emission layers.

[0315] exist Figure 9 In the illustrated embodiment, all light emitted from each of the light-emitting structures OL-B1, OL-B2, and OL-B3 can be blue light. However, the embodiments of this disclosure are not limited thereto, and the wavelength ranges of light emitted from each of the light-emitting structures OL-B1, OL-B2, and OL-B3 can be different from each other. For example, a light-emitting element ED-BT comprising multiple light-emitting structures OL-B1, OL-B2, and OL-B3 emitting light in different wavelength ranges can emit white light.

[0316] The charge generation layers CGL1 and CGL2 can be disposed between adjacent light-emitting structures OL-B1, OL-B2, and OL-B3. The charge generation layers CGL1 and CGL2 may include p-type charge generation layers and / or n-type charge generation layers.

[0317] At least one of the light-emitting structures OL-B1, OL-B2, and OL-B3 included in the display device DD-TD may include an amine compound according to the embodiments as described above.

[0318] The light-emitting element (ED) may include an amine compound according to embodiments in at least one functional layer disposed between the first electrode EL1 and the second electrode EL2, thereby achieving improved emission efficiency and / or improved lifetime characteristics. The ED may include an amine compound according to embodiments in at least one of the hole transport region HTR, the emitter layer EML, and the electron transport region ETR disposed between the first electrode EL1 and the second electrode EL2, or in the capping layer CPL.

[0319] For example, the amine compound according to the embodiments may be included in the hole transport region (HTR) of the light-emitting element ED, and the light-emitting element according to the embodiments may exhibit excellent or suitable emission efficiency and / or long lifespan characteristics.

[0320] The amine compounds according to the above embodiments have a molecular structure that necessarily includes a bicycloheptanyl group and an additional one of adamantyl, cyclohexyl, and bicycloheptanyl, thereby exhibiting excellent or suitable durability and / or heat resistance, and thus enabling improved lifespan characteristics. In some embodiments, the improved material stability and hole transport capability of the amine compounds according to the embodiments can contribute to long lifespan and / or high efficiency characteristics of the light-emitting element.

[0321] In the following, the amine compounds according to the embodiments and the light-emitting elements according to the embodiments of the present disclosure will be described in more detail with reference to examples and comparative examples. The following examples are provided to aid in understanding the present disclosure, and the scope of the present disclosure is not limited thereto.

[0322] Example

[0323] 1. Synthesis of amine compounds

[0324] First, the synthesis methods of amine compounds according to embodiments of the present disclosure will be described in more detail with reference to the synthesis methods of compounds 1, 2, 30, 41, 50 and 65 in compound group 1. In some embodiments, the synthesis methods of amine compounds explained are merely examples, and the synthesis methods of amine compounds according to embodiments of the present disclosure are not limited thereto.

[0325] (1) Synthesis of Compound 1

[0326] According to the example, amine compound 1 can be synthesized by the following reaction steps.

[0327] Synthesis of intermediate A

[0328]

[0329] 12.9 g (100 mmol) of 1-bromo-4-iodobenzene, 23.3 g of bicyclo[2,2,1]hept-2-ene, 19.5 g (100 mmol) of CuI, and 25.8 g (200 mmol) of K₂CO₃ were added to 200 mL of DMF solution, and the mixture was stirred at approximately 150 °C for approximately 96 hours. After the reaction was complete, the mixture was cooled to room temperature and extracted three times with ethyl acetate / H₂O. The resulting mixture was then dried over anhydrous magnesium sulfate and purified by column chromatography using a mixed solvent (MC:HEX = 1:10) to give intermediate A (18.8 g, 80% yield).

[0330] Synthesis of intermediate B

[0331]

[0332] Synthesis of intermediate B-1

[0333] 21.4 g (100 mmol) of 1-bromoadamantane was added to 100 mL of phenol, and the mixture was stirred at approximately 110 °C for about 24 hours. After the reaction was complete, the resulting solid was washed three times with H₂O at 60 °C. After dissolving the solid in MC, the resulting solution was dried over anhydrous magnesium sulfate to give intermediate B-1 (22 g, 100% yield).

[0334] Synthesis of intermediate B

[0335] 22 g of intermediate B-1 and 10 g of Et3N were dissolved in MC, and the solution was then cooled to approximately 0 °C. 50 g of trifluoromethanesulfonic anhydride was added for 1 hour. The mixture was then heated to room temperature and stirred for 4 hours. After the reaction was complete, the resulting solid was extracted three times with Et2O / H2O at 60 °C. The resulting mixture was dried over anhydrous magnesium sulfate and then separated and purified by column chromatography to obtain intermediate B (33 g, 90% yield).

[0336] Synthesis of Compound 1

[0337]

[0338] Synthesis of intermediate 1-1

[0339] 4.2 g (20 mmol) of 9,9-dimethyl-9H-fluorene-2-amine, 5 g (20 mmol) of intermediate A, 0.915 g (1 mol) of Pd2(dba)3, 0.410 g (1 mL) of Sphos and 3.6 g (40 mmol) of NaO were added. t Bu was dissolved in toluene (200 mL), stirred at about 90 °C for about 2 hours, and then extracted three times with Et2O / H2O. The resulting product was dried over anhydrous magnesium sulfate and then separated and purified by column chromatography to obtain intermediate 1-1 (6.8 g (18 mmol), yield 90%).

[0340] Synthesis of Compound 1

[0341] Compound 1 (5.3 g (9 mmol), 90% yield) was obtained by means substantially the same method as the synthesis of intermediate 1-1, except that intermediate 1-1 was used instead of 9,9-dimethyl-9H-fluorene-2-amine and intermediate B was used instead of intermediate A.

[0342] Compound 1 was identified by confirming its molecular weight and NMR results as follows. [C] 44 H 47 N M+1:590.45, 1 H NMR (500MHz, CDCl3) δ = 7.80 (m, 2H), 7.60 (d, 1H), 7.55-7.10 (m, 12H), 2.5-0.9 (m, 32H)].

[0343] (2) Synthesis of compound 2

[0344] According to the embodiments, amine compound 2 can be synthesized by the following reaction steps or tasks.

[0345]

[0346] Synthesis of intermediate 2-1

[0347] Except for using 9,9-diphenyl-9H-fluorene-2-amine instead of 9,9-dimethyl-9H-fluorene-2-amine, intermediate 2-1 was obtained by essentially the same method as that used for intermediate 1-1 (9 g (18 mmol), 90% yield).

[0348] Synthesis of Compound 2

[0349] Compound 2 (6.4 g (9 mmol), 90% yield) was obtained by essentially the same method as that used to synthesize compound 1, except that intermediate 2-1 was used instead of intermediate 1-1.

[0350] Compound 2 was identified by confirming its molecular weight and NMR results as follows. [C]54 H 51 N M+1:714.55, 1 H NMR (500MHz, CDCl3) δ = 7.80 (m, 2H), 7.60 (d, 1H), 7.55-7.10 (m, 22H), 2.5-1.5 (m, 26H)].

[0351] (3) Synthesis of compound 30

[0352] According to the embodiments, amine compound 30 can be synthesized by the following reaction steps or tasks.

[0353]

[0354] Synthesis of intermediate 30-1

[0355] Except for the use of 9-phenyl-9H-carbazole-3-amine instead of 9,9-dimethyl-9H-fluorene-2-amine, intermediate 30-1 was obtained by essentially the same method as that used for intermediate 1-1 (7.7 g (18 mmol), 90% yield).

[0356] Synthesis of Compound 30

[0357] Compound 30 (5.2 g (9 mmol), 90% yield) was obtained by essentially the same method as that used to synthesize compound 1, except that intermediate 30-1 was used instead of intermediate 1-1 and 1-bromo-4-cyclohexylbenzene was used instead of intermediate A.

[0358] Compound 30 was identified by confirming its molecular weight and NMR results as follows. [C] 43 H 42 N2 M+1:587.33, 1 H NMR (500MHz, CDCl3) δ = 7.80 (m, 2H), 7.60 (d, 1H), 7.55-7.10 (m, 17H), 2.5-1.5 (m, 22H)].

[0359] (4) Synthesis of compound 41

[0360] According to the embodiments, amine compound 41 can be synthesized by the following reaction steps or tasks.

[0361]

[0362] Except that 2.1 g (10 mmol) of 9,9-dimethyl-9H-fluorene-2-amine was used to replace intermediate 1-1, compound 41 (5.2 g (9 mmol), 90% yield) was obtained by essentially the same method as that used to synthesize compound 1.

[0363] Compound 41 was identified by confirming its molecular weight and NMR results as follows. [C] 41 H 43 N M+1:550.52, 1 H NMR (500MHz, CDCl3) δ = 7.80 (m, 2H), 7.60 (d, 1H), 7.55-7.10 (m, 12H), 2.5-1.5 (m, 22H), 1.3 (d, 6H)].

[0364] (5) Synthesis of compound 50

[0365] According to the embodiments, amine compound 50 can be synthesized by the following reaction steps or tasks.

[0366]

[0367] Except that 2,6-(10 mmol) 9-phenyl-9H-carbazole-2-amine was used instead of 9,9-dimethyl-9H-fluorene-2-amine, compound 50 was obtained by essentially the same method as that used to synthesize compound 41 (5.38 g (9 mmol), 90% yield).

[0368] Compound 50 was identified by confirming its molecular weight and NMR results as follows. [C] 44 H 42 N2 M+1:599.22, 1 H NMR (500MHz, CDCl3) δ = 7.80 (m, 2H), 7.60 (d, 1H), 7.55-7.10 (m, 17H), 2.5-1.5 (m, 22H)].

[0369] (6) Synthesis of compound 65

[0370] According to the embodiments, amine compound 65 can be synthesized by the following reaction steps or tasks.

[0371]

[0372] Synthesis of intermediate 65-1

[0373] Except for the use of 4-(9,9-dimethyl-9H-fluoren-2-yl)aniline instead of 9,9-dimethyl-9H-fluoren-2-amine, intermediate 65-1 was obtained by essentially the same method as that used for intermediate 1-1 (8.19 g (18 mmol), 90% yield).

[0374] Synthesis of Compound 65

[0375] Compound 65 was obtained by essentially the same method as that used to synthesize compound 1, except that intermediate 65-1 was used instead of intermediate 1-1 and 1-bromo-4-cyclohexylbenzene was used instead of intermediate A.

[0376] Compound 65 was identified by confirming its molecular weight and NMR results as follows. [C] 46 H 47 N M+1:614.44, 1 H NMR (500MHz, CDCl3) δ = 7.80 (m, 2H), 7.60 (d, 1H), 7.55-7.10 (m, 16H), 2.5-1.5 (m, 22H), 1.3 (d, 6H)].

[0377] 2. Manufacturing and evaluation of light-emitting elements

[0378] (Manufacturing of light-emitting elements)

[0379] The following methods are used to manufacture light-emitting elements comprising an amine compound according to embodiments in a hole transport layer. Examples 1 to 6, as well as Comparative Examples 1 and 2, are light-emitting elements manufactured to include one hole transport layer, and Examples 7 and 8 are light-emitting elements manufactured to include two hole transport layers.

[0380] Compounds 1, 2, 30, 41, 50, and 65 were all used as hole transport materials to manufacture the light-emitting elements of Examples 1 to 6, respectively. Light-emitting elements of Examples 7 and 8 were manufactured using compound 1 as the first hole transport layer material and the corresponding amine derivatives of compounds 85 and 97 as the second hole transport layer materials, respectively.

[0381] In Comparative Example 1, the comparative compound NPB(C1) was used as the hole transport layer material to fabricate the light-emitting element. In Comparative Example 2, the comparative compound C2 was used as the hole transport layer material to fabricate the light-emitting element.

[0382] Example compounds and comparative compounds used in component manufacturing are shown.

[0383] Example compounds

[0384]

[0385] Comparative compounds

[0386]

[0387] Other compounds used in component manufacturing

[0388]

[0389] Patterns were created on a glass substrate using isopropyl alcohol and pure water via ultrasonic cleaning. Thick ITO layer for 5 minutes. After ultrasonic cleaning, the substrate is irradiated with UV rays for approximately 30 minutes and then treated with ozone. Then, 2-TNATA is deposited to approximately [amount missing]. The thickness is adjusted to form a hole injection layer. Subsequently, in Examples 1 to 6 and Comparative Examples 1 to 2, the corresponding example or comparative compound is deposited to approximately [amount missing]. The thickness is adjusted to form a hole transport layer. In some embodiments, in Examples 7 and 8, compound 1 is deposited to form a first hole transport layer, and then compounds 85 and 97 are deposited, respectively, to form a second hole transport layer. In Examples 7 and 8, each of the first and second hole transport layers is deposited to approximately [thickness missing]. The thickness.

[0390] Then, ADN and DPAVBi (blue fluorescent dopant) were co-deposited at a weight ratio of approximately 98:2 to form A thick emission layer. Then, Alq3 is deposited to... To form an electron transport layer, and to deposit LiF to To form an electron injection layer.

[0391] Then, set Al to approximately The thickness is used to form the second electrode.

[0392] In each of the example and comparative examples, a hole injection layer, a hole transport layer, an emission layer, an electron transport layer, an electron injection layer, and a second electrode are formed using a vacuum deposition apparatus.

[0393] Evaluation of the characteristics of light-emitting elements

[0394] The evaluation results of the light-emitting elements according to Examples 1 to 8 and Comparative Examples 1 to 2 are shown in Table 1. The driving voltage, brightness, emission efficiency, and half-life of each light-emitting element thus manufactured are compared and shown in Table 1. In the evaluation results of the characteristics of the examples and comparative examples shown in Table 1, the emission efficiency is expressed in approximately 50 mA / cm². 2 The efficiency value at the current density, with the half-life expressed at approximately 100 mA / cm². 2 The brightness reduction time is measured. In some embodiments, it is confirmed that all manufactured elements exhibit a blue emission color.

[0395] The half-life, driving voltage, and emission efficiency of the light-emitting elements of the example and comparative examples were determined in a dark room using a 2400 series SourceMeter from Keithley Instrument Co., a CS-200 luminance meter from Konica Minolta, Inc., and LabVIEW 2.0, a PC program for measurement from National Instrument Co.

[0396] [Table 1]

[0397]

[0398]

[0399] Referring to the results in Table 1, it can be seen that the light-emitting elements using the amine compounds according to the embodiments as hole transport layer materials exhibit low driving voltage, high brightness characteristics, excellent or suitable device efficiency, and improved device lifespan characteristics.

[0400] For example, referring to Table 1, it can be seen that, compared with Comparative Example 1 and Comparative Example 2, Examples 1 to 8 exhibit low voltage, high brightness, long lifespan, and high efficiency characteristics.

[0401] Therefore, the results show that, compared with Comparative Examples 1 and 2, Examples 1 to 8 exhibit improvements in both emission efficiency and emission lifetime (e.g., simultaneously). For example, by utilizing the amine compound according to the embodiments having a compound structure including at least one bicyclic heptyl group, both the element efficiency and element lifetime of the light-emitting element according to the embodiments can be improved (e.g., simultaneously).

[0402] Because of their compound structure comprising a bicycloheptanyl group and also comprising at least one of adamantyl, cyclohexyl, and bicycloheptanyl, the amine compounds according to the embodiments can contribute to the low voltage, long lifespan, and high efficiency characteristics of light-emitting devices. The light-emitting elements have the amine compounds according to the embodiments and can therefore exhibit both long lifespan and / or high efficiency characteristics (e.g., simultaneously).

[0403] The light-emitting element according to the embodiment may include an amine compound according to the embodiment in the hole transport region, thereby exhibiting high efficiency and / or long service life characteristics.

[0404] The amine compounds according to the embodiments can improve the emission efficiency and / or lifespan of light-emitting elements.

[0405] While exemplary embodiments of this disclosure have been described herein, it is understood that one or more suitable changes and modifications may be made by those skilled in the art within the spirit and scope of this disclosure as defined by the claims and their equivalents.

[0406] As used herein, the terms “substantially,” “approximately,” and similar terms are used as approximations rather than terms of degree and are intended to take into account the inherent biases in measured or calculated values ​​that would be recognized by one of ordinary skill in the art. As used herein, “approximately” or “approximately” includes the stated value and indicates an acceptable range of deviation from the specific value as determined by one of ordinary skill in the art, taking into account the measurement in question and the errors associated with the measurement of the particular quantity (i.e., the limitations of the measurement system). For example, “approximately” may mean within one or more standard deviations, or within ±30%, ±20%, ±10%, ±5% of the stated value.

[0407] Any numerical range described herein is intended to include all subranges with the same numerical precision contained within the described range. For example, the range “1.0 to 10.0” is intended to include all subranges between the described minimum value 1.0 and the described maximum value 10.0 (and including both the described minimum value 1.0 and the described maximum value 10.0), i.e., having a minimum value equal to or greater than 1.0 and a maximum value equal to or less than 10.0, such as 2.4 to 7.6. Any maximum numerical limit described herein is intended to include all lower numerical limits contained therein, and any minimum numerical limit described in this specification is intended to include all higher numerical limits contained therein. Therefore, the applicant reserves the right to amend this specification (including the claims) to expressly describe any subranges contained within the scope expressly described herein.

[0408] Therefore, the technical scope of this disclosure is not limited to the specific embodiments described in the specification, and various changes in form and detail may be made without departing from the spirit and scope of this disclosure as set forth in the claims and their equivalents.

Claims

1. An amine compound, said amine compound being represented by Formula 1: Formula 1 ， in, In Equation 1, R1 is adamantyl, cyclohexyl, or bicycloheptyl. Ar1 and Ar2 are both independently substituted alkyl groups having one to six carbon atoms or unsubstituted aryl groups having six to fifteen cyclic carbon atoms. L is a straight-linked bond or a substituted alkyl group having 1 to 6 carbon atoms or an unsubstituted aryl group having 6 to 15 cyclic carbon atoms, and FR is represented by Equation 2: Formula 2 ,and In Equation 2, X is CR a R b , R a and R b Each of the following groups is independently a hydrogen atom, a deuterium atom, a halogen atom, an alkyl group substituted with a deuterium atom, a halogen atom, or an alkyl group having 1 to 6 carbon atoms, or an unsubstituted alkyl group having 1 to 10 carbon atoms, or an alkyl group substituted with a deuterium atom, a halogen atom, or an alkyl group having 1 to 6 carbon atoms, or an unsubstituted aryl group having 6 to 15 cyclic carbon atoms, and optionally, is incorporated into an adjacent group to form a ring. d and e are both independent integers from 0 to 4, and R d and R e Each is independently a hydrogen atom, a deuterium atom, a halogen atom, or an alkyl group substituted with a deuterium atom, a halogen atom, or having 1 to 6 carbon atoms, or an unsubstituted alkyl group having 1 to 10 carbon atoms.

2. The amine compound according to claim 1, wherein, The amine compound represented by Formula 1 is represented by Formula 1-1 or Formula 1-2: Formula 1-1 ， Formula 1-2 ,and In Equations 1-1 and 1-2, R1, L, Ar1, and Ar2 are all independently identical to those defined in Equation 1, and X, R d R e , d, and e are all independently identical to those defined in Equation 2.

3. The amine compound according to claim 2, wherein, The amine compound represented by formula 1-2 is represented by formula 1-2A: Formula 1-2A ,and In Equation 1-2A, R1, L, Ar1, and Ar2 are all independently identical to those defined in Equation 1, and R a R d R e , d, and e are all independently identical to those defined in Equation 2.

4. The amine compound according to claim 1, wherein, In Formula 1, Ar1 and Ar2 are alkyl or unsubstituted phenylene atoms with deuterium atoms, halogen atoms, or having one to six carbon atoms.

5. The amine compound according to claim 1, wherein, The amine compound represented by Formula 1 is represented by Formula 1A: Formula 1A ,and In Equation 1A, R1, L, and FR are all independently the same as those defined in Equation 1.

6. The amine compound according to claim 5, wherein, The amine compound represented by formula 1A is represented by formula 1A-1: Formula 1A-1 ,and In Equation 1A-1, R1, L, and FR are all independently the same as those defined in Equation 1.

7. The amine compound according to claim 1, wherein, The amine compound represented by Formula 1 is represented by any one of the compounds in Group 1: Compound group 1 。 8. A light-emitting element, the light-emitting element comprising: First electrode; The second electrode is located on the first electrode; as well as At least one functional layer is located between the first electrode and the second electrode, and includes an amine compound according to any one of claims 1 to 7.

9. The light-emitting element according to claim 8, wherein: The at least one functional layer includes an emitter layer, a hole transport region between the first electrode and the emitter layer, and an electron transport region between the emitter layer and the second electrode. The hole transport region includes the amine compound.

10. The light-emitting element according to claim 8, wherein: The at least one functional layer includes: an emitter layer; a first hole transport layer between the first electrode and the emitter layer; a second hole transport layer between the first hole transport layer and the emitter layer; and an electron transport region between the emitter layer and the second electrode. The first hole transport layer includes the amine compound, and The second hole transport layer comprises an amine derivative compound represented by Formula 3: Formula 3 ,and In Equation 3, L 11 It is a straight-linked, substituted alkyl group with deuterium atom, halogen atom, or having 1 to 6 carbon atoms, or an unsubstituted aryl group with 6 to 30 cyclic carbon atoms, or a substituted alkyl group with deuterium atom, halogen atom, or having 1 to 6 carbon atoms, or an unsubstituted heteroaryl group with 2 to 30 cyclic carbon atoms. R 11 To R 14 Each of the following is independently a substituted alkyl group having one to six carbon atoms or an unsubstituted alkyl group having one to ten carbon atoms, a substituted alkyl group having one to six carbon atoms or an unsubstituted alkenyl group having two to ten carbon atoms, a substituted alkyl group having one to six carbon atoms or an unsubstituted aryl group having six to thirty cyclic carbon atoms, or a substituted alkyl group having one to six carbon atoms or an unsubstituted heteroaryl group having two to thirty cyclic carbon atoms, and optionally, is incorporated into an adjacent group to form a ring.

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