Light-emitting element, amine compound used in same, and electronic device

Abstract

Provided are a light-emitting element, an electronic device, and an amine compound represented by Formula 1 for the same. The light emitting element includes: a first electrode; a second electrode on the first electrode; and at least one functional layer between the first electrode and the second electrode and including the amine compound represented by Formula 1. Formula 1 # imgabs0 #

Description

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS

[0002] This application claims priority to and the benefit of Korean Patent Application No. 10-2023-0090609 filed in the Korean Intellectual Property Office on July 12, 2023, the entire contents of which are incorporated herein by reference. Technical Field

[0003] One or more embodiments of the present disclosure relate to a light-emitting element, an amine compound for the light-emitting element, and an electronic device including the light-emitting element. Background Art

[0004] Recently, organic electroluminescent display devices and the like have been actively developed as image display devices. The organic electroluminescent display device and the like are display devices including a self-luminous type or kind of light-emitting element in which holes and electrons injected from a first electrode and a second electrode, respectively (e.g., separately), recombine in a light-emitting layer, thereby causing the light-emitting material of the light-emitting layer to emit light to realize display of an image.

[0005] When a light-emitting element is applied to a display device, improvements in luminous efficiency and lifetime are required and / or desired, and thus material development for a light-emitting element capable of stably achieving such improvements is continuously required and / or sought.

[0006] For example, in order to realize a light-emitting element having relatively high efficiency and relatively long lifetime, materials having excellent or suitable hole transporting ability and stability of a hole transporting zone for a light-emitting element are particularly under development and research. Summary of the invention

[0007] One or more aspects of embodiments of the present disclosure relate to a light emitting element having improved luminous efficiency and element lifespan.

[0008] One or more aspects of an embodiment of the present disclosure relate to an amine compound capable of improving the luminous efficiency and service life of a light-emitting element.

[0009] One or more aspects of an embodiment of the present disclosure are directed to an electronic device having excellent or suitable display quality by including a light emitting element having improved light emitting efficiency and lifetime.

[0010] Additional aspects will be set forth in part in the description which follows and, in part, will be obvious from the description, or may be learned by practice of the presented embodiments.

[0011] According to one or more embodiments of the present disclosure, a light emitting element includes a first electrode, a second electrode on the first electrode, and at least one functional layer between the first electrode and the second electrode and including an amine compound represented by Formula 1.

[0012] Formula 1

[0013]

[0014] In formula 1, Ar 1 To Ar 3 may each independently be a substituted or unsubstituted oxy group, a substituted or unsubstituted silyl 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 alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, excluding Ar 1 In embodiments or instances comprising a fluorene group, a dibenzofuran group, or a dibenzothiophene group, L 1 It may be a substituted or unsubstituted phenylene group, R a It may be a substituted or unsubstituted oxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, R 1 It may be hydrogen, tritium, halogen, substituted or unsubstituted oxy group, substituted or unsubstituted silyl group, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, n1 may be an integer from 0 to 6, m1 may be an integer from 1 to 4, and when m1 is 2, L is excluded 1 An embodiment represented by formula A-1.

[0015] Formula A-1

[0016]

[0017] In formula A-1, -* is the same as Ar in formula 1 1 The position of the attached nitrogen atom, and is the same as Ar in formula 1 2 and Ar 3 The position of the attached nitrogen atom.

[0018] In one or more embodiments, the at least one functional layer may include a light-emitting layer, a hole transport region between the first electrode and the light-emitting layer, and an electron transport region between the light-emitting layer and the second electrode, and the hole transport region may contain the amine compound represented by Formula 1.

[0019] In one or more embodiments, the hole transport region may include a hole injection layer on the first electrode and a hole transport layer on the hole injection layer, wherein the hole transport layer may include the amine compound represented by Formula 1.

[0020] In one or more than one embodiments, a layer adjacent to the light-emitting layer among the plurality of layers included in the hole transporting zone may include the amine compound represented by Formula 1.

[0021] In one or more than one embodiments, the amine compound represented by Formula 1 may be a diamine compound.

[0022] In one or more than one embodiments, the amine compound represented by Formula 1 may be represented by Formula 2.

[0023] Formula 2

[0024]

[0025] In formula 2, R 2 It can be hydrogen, deuterium, halogen, substituted or unsubstituted oxy group, substituted or unsubstituted silyl group, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, and n2 can be an integer from 0 to 4.

[0026] In Formula 2, the same description as defined in Formula 1 can be applied to Ar 1 To Ar 3 , R a , R 1 , n1 and m1.

[0027] In one or more than one embodiments, the amine compound represented by Formula 1 may be represented by Formula 3.

[0028] Formula 3

[0029]

[0030] In formula 3, R 3It can be hydrogen, deuterium, halogen, substituted or unsubstituted oxy group, substituted or unsubstituted silyl group, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, and n3 can be an integer from 0 to 5.

[0031] In Formula 3, the same description as defined in Formula 1 can be applied to Ar 1 To Ar 3 , L 1 , R 1 , n1 and m1.

[0032] In one or more than one embodiments, the amine compound represented by Formula 3 may be represented by Formula 4-1 or Formula 4-2.

[0033] Formula 4-1

[0034]

[0035] Formula 4-2

[0036]

[0037] In Formula 4-1 and Formula 4-2, the same description as defined in Formula 1 and Formula 3 can be applied to Ar 1 To Ar 3 , L 1 , R 1 , R 3 , n1, n3 and m1.

[0038] In one or more than one embodiments, the amine compound represented by Formula 1 may be represented by any one selected from Formula 5-1 to Formula 5-5.

[0039] Formula 5-1

[0040]

[0041] Formula 5-2

[0042]

[0043] Formula 5-3

[0044]

[0045] Formula 5-4

[0046]

[0047] Formula 5-5

[0048]

[0049] In formulas 5-1 to 5-5, R 11 To R 20 Each of n11 to n20 may independently be hydrogen, deuterium, halogen, a substituted or unsubstituted oxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, and n11 to n20 may independently be an integer from 0 to 4.

[0050] In Formula 5-1 to Formula 5-5, the same description as defined in Formula 1 can be applied to Ar 1 To Ar 3 , R a , R 1 and n1.

[0051] In one or more than one embodiment, L 1 It may be represented by any one selected from Formula L-1 to Formula L-22.

[0052] Formula L-1

[0053]

[0054] Formula L-2

[0055]

[0056] Formula L-3

[0057]

[0058] Formula L-4

[0059]

[0060] Formula L-5

[0061]

[0062] Formula L-6

[0063]

[0064] Formula L-7

[0065]

[0066] Formula L-8

[0067]

[0068] Formula L-9

[0069]

[0070] Formula L-10

[0071]

[0072] Formula L-11

[0073]

[0074] Formula L-12

[0075]

[0076] Formula L-13

[0077]

[0078] Formula L-14

[0079]

[0080] Formula L-15

[0081]

[0082] Type L-16

[0083]

[0084] Formula L-17

[0085]

[0086] Formula L-18

[0087]

[0088] Type L-19

[0089]

[0090] Formula L-20

[0091]

[0092] Formula L-21

[0093]

[0094] Formula L-22

[0095]

[0096] In Formula L-1 to Formula L-22, R b1To R b65 may be each independently hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, m1 to m65 may each independently be an integer from 0 to 4, -* is the same as Ar in Formula 1 1 the position of the attached nitrogen atom, and is the same as Ar in formula 1 2 and Ar 3 The position of the attached nitrogen atom.

[0097] In one or more than one embodiment, Ar 1 may be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted naphthyl group, and Ar 2 and Ar 3 Each may independently be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted fluorenyl group.

[0098] In one or more than one embodiment, Ar 1 can be represented by any one selected from Formula B-1 to Formula B-4, and Ar 2 and Ar 3 Each may be independently represented by any one selected from Formula B-1 to Formula B-7.

[0099] Formula B-1

[0100]

[0101] Formula B-2

[0102]

[0103] Formula B-3

[0104]

[0105] Formula B-4

[0106]

[0107] Formula B-5

[0108]

[0109] Formula B-6

[0110]

[0111] Formula B-7

[0112]

[0113] In Formula B-1 to Formula B-7, R d1 To R d18 may each independently be hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, p1, p3, p11 and p12 may each independently be an integer from 0 to 5, p2, p4, p10, p14, p15, p16 and p18 may each independently be an integer from 0 to 4, p5 is an integer from 0 to 11, p6 is an integer from 0 to 7, and p9, p13 and p17 may each independently be an integer from 0 to 3, and -* is a position connected to the corresponding nitrogen atom in Formula 1.

[0114] In one or more than one embodiments, the amine compound represented by Formula 1 may be represented by Formula 6-1 or Formula 6-2.

[0115] Formula 6-1

[0116]

[0117] Formula 6-2

[0118]

[0119] In equations 6-1 and 6-2, R 3 may be hydrogen, deuterium, halogen, substituted or unsubstituted oxy group, substituted or unsubstituted silyl group, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, n3 may be an integer from 0 to 5, and Ar 1 'To Ar 3 ' may be independently selected from substituent group A, provided that Ar 1 ' may not be selected from any one of a36 to a47.

[0120] Substituent Group A

[0121]

[0122]

[0123]

[0124] In the substituent group A, -* is a position to which the corresponding nitrogen atom in Formula 1 is bonded. In Formula 6-1 and Formula 6-2, the same description as defined in Formula 1 may apply to L 1 , R 1 , n1 and m1.

[0125] In one or more embodiments of the present disclosure, for an electronic device selected from large electronic devices such as televisions, monitors, and external advertising boards, and small electronic devices and medium-sized electronic devices such as personal computers, laptop computers, personal digital terminals, display devices for vehicles, game consoles, portable electronic devices, and cameras, the electronic device may include at least one of the light-emitting elements, and the light-emitting element contains the amine compound represented by Formula 1.

[0126] Formula 1

[0127]

[0128] In formula 1, Ar 1 To Ar 3 may each independently be a substituted or unsubstituted oxy group, a substituted or unsubstituted silyl 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 alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, excluding Ar 1 In the embodiment comprising a fluorene group, a dibenzofuran group, or a dibenzothiophene group, L 1 It may be a substituted or unsubstituted phenylene group, R a It may be a substituted or unsubstituted oxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, R 1 It may be hydrogen, tritium, halogen, substituted or unsubstituted oxy group, substituted or unsubstituted silyl group, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, n1 may be an integer from 0 to 6, m1 may be an integer from 1 to 4, and when m1 is 2, L is excluded 1 An embodiment represented by formula A-1.

[0129] Formula A-1

[0130]

[0131] In formula A-1, —* is the same as Ar in formula 1 1 The position of the attached nitrogen atom, and is the same as Ar in formula 1 2 and Ar 3 The position of the attached nitrogen atom.

[0132] In one or more embodiments, the electronic device may include a substrate layer, a circuit layer on the substrate layer, a display element layer on the circuit layer and including the light-emitting element, and an encapsulation layer arranged on the display element layer, wherein the light-emitting element may include a first electrode, a second electrode on the first electrode, and at least one functional layer between the first electrode and the second electrode and including the amine compound represented by Formula 1.

[0133] In one or more embodiments, the light emitting element may further include a capping layer on the second electrode, and the capping layer may have a refractive index of at least about 1.6 for light in a wavelength range of about 550 nm to about 660 nm.

[0134] In one or more embodiments, a light control layer may be further included on the encapsulation layer and comprising quantum dots, and the light-emitting element is intended to emit a first color light, wherein the light control layer may include a first light control component comprising first quantum dots that convert the first color light into a second color light having a wavelength longer than the first color light, a second light control component comprising second quantum dots that convert the first color light into a third color light having a wavelength longer than the first color light and the second color light, and a third light control component that transmits the first color light.

[0135] In one or more embodiments, a color filter layer may be further included on the light control layer, and the color filter layer may include a first filter that transmits the second color light, a second filter that transmits the third color light, and a third filter that transmits the first color light.

[0136] In one or more than one embodiments of the present disclosure, an amine compound represented by Formula 1 is provided. BRIEF DESCRIPTION OF THE DRAWINGS

[0137] The accompanying drawings are included to provide a further understanding of the present disclosure, and are incorporated into and constitute a part of the present disclosure. The accompanying drawings illustrate exemplary embodiments of the present disclosure and, together with the description, serve to explain the principles of the present disclosure. The above and / or other aspects of the present disclosure should become apparent and understood from the following description of the embodiments in conjunction with the accompanying drawings. In the drawings:

[0138] Figure 1 is a plan view illustrating a display device according to one or more embodiments of the present disclosure;

[0139] Figure 2 is a cross-sectional view of a display device according to one or more embodiments of the present disclosure;

[0140] Figure 3 is a cross-sectional view schematically illustrating a light emitting element according to one or more embodiments of the present disclosure;

[0141] Figure 4 is a cross-sectional view schematically illustrating a light emitting element according to one or more embodiments of the present disclosure;

[0142] Figure 5 is a cross-sectional view schematically illustrating a light emitting element according to one or more embodiments of the present disclosure;

[0143] Figure 6 is a cross-sectional view schematically illustrating a light emitting element according to one or more embodiments of the present disclosure;

[0144] Figure 7 is a cross-sectional view of a display device according to one or more embodiments of the present disclosure;

[0145] Figure 8 is a cross-sectional view of a display device according to one or more embodiments of the present disclosure;

[0146] Fig. 9 is a cross-sectional view illustrating a display device according to one or more embodiments of the present disclosure;

[0147] Fig.10 is a cross-sectional view illustrating a display device according to one or more embodiments of the present disclosure; and

[0148] Fig.11 is a view illustrating a vehicle in which a display device according to one or more embodiments is provided. DETAILED DESCRIPTION

[0149] The present disclosure may be modified in one or more than one suitable manner and have a variety of forms, and therefore specific embodiments will be illustrated in the accompanying drawings and described in more detail in the detailed description of the present disclosure. However, it should be understood that it is not intended to limit the present disclosure to the specific form disclosed, but is intended to cover all modifications, equivalents and substitutions that fall within the spirit and scope of the present disclosure.

[0150] When explaining each accompanying drawing, the same reference numerals are used to refer to the same elements. In the accompanying drawings, for the clarity of the present disclosure, the size of each structure can be illustrated in an amplified manner. It should be understood that although the terms "first", "second", etc. can be used to describe one or more than one suitable components in this article, these components should not be limited by these terms. These terms are only used to distinguish one component from another component. For example, without departing from the scope of the exemplary embodiments of the present disclosure, the first component can be referred to as the second component, and similarly, the second component can be referred to as the first component. As used herein, the singular forms "a", "an", "one", and "the" are intended to also include plural forms, unless the context clearly indicates otherwise. In addition, the use of "can" refers to "one or more than one embodiment of the present disclosure" when describing the embodiment of the present disclosure.

[0151] In the present disclosure, it should be understood that the terms "comprising", "including", "having", etc. indicate the presence of features, numbers, steps, operations, components, parts or combinations thereof disclosed in the present disclosure, but do not exclude the possibility of the presence or addition of one or more other features, numbers, steps, operations, components, parts or combinations thereof. As used herein, the terms "and", "or" and "and / or" may include any combination and all combinations of one or more of the related listed items. Expressions such as "at least one (kind) of ......", "one (kind) of ......" and "selected from" when preceding a list of elements modify the elements of the entire list and do not modify the individual elements of the list. For example, "at least one (kind) of a, b and c", "selected from at least one (kind) of a, b and c" and "selected from at least one (kind) of a to c" may represent only a, only b, only c, both a and b (e.g., simultaneously), both a and c (e.g., simultaneously), both b and c (e.g., simultaneously), all a, b and c, or variations thereof. As used herein, “ / ” may be interpreted as “and” or “or” depending on the circumstances.

[0152] In the present disclosure, when a layer, film, region, or plate is referred to as being "on" or "in the upper portion of" another layer, film, region, or plate, it may not only be "directly on" the layer, film, region, or plate, but there may also be one or more intervening layers, films, regions, or plates. In contrast, when a layer, film, region, or plate is referred to as being "below" or "in the lower portion of" another layer, film, region, or plate, it may not only be directly below the layer, film, region, or plate, but there may also be one or more intervening layers, films, regions, or plates. In some embodiments, it should be understood that when a component is referred to as being "on" another component, it may be disposed above the other component, or it may also be disposed under the other component. In one or more than one embodiments, "directly on..." may mean that there are no additional layers, films, regions, plates, etc. between the layer, film, region, plate, etc. and other parts. For example, "directly on..." may mean that two layers or two components are disposed without using additional components, such as bonding components, therebetween.

[0153] In the present disclosure, the term "substituted or unsubstituted" may refer to being selected from at least one substituent in the group consisting of deuterium, halogen, cyano group, nitro group, amino group, silyl group, oxy group, sulfenyl group, sulfinyl group, sulfonyl group, carbonyl group, boron group, phosphine oxide group, phosphine sulfide group, alkyl group, alkenyl group, alkynyl group, hydrocarbon ring group, aryl group and heterocyclic group or unsubstituted. In some embodiments, each of the substituents exemplified above may be substituted or unsubstituted. For example, a biphenyl group may be interpreted as an aryl group or a phenyl group substituted by a phenyl group.

[0154] In the present disclosure, the phrase "bonded to an adjacent group to form a ring" may refer to a group bonded to an adjacent group to form a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocycle. The hydrocarbon ring may include an aliphatic hydrocarbon ring and / or an aromatic hydrocarbon ring. The heterocycle includes an aliphatic heterocycle and an aromatic heterocycle. The hydrocarbon ring and the heterocycle may each be monocyclic or polycyclic. In some embodiments, the ring formed by the adjacent groups bonding to each other may be connected to another ring to form a spiro structure.

[0155] In the present disclosure, the term "adjacent group" may refer to a substituent that replaces an atom directly connected to the atom substituted by the corresponding substituent, another substituent that replaces the atom substituted by the corresponding substituent, or a substituent that is spatially positioned at the closest position to the corresponding substituent. For example, the two methyl groups in 1,2-dimethylbenzene may be interpreted as "adjacent groups" to each other, and the two ethyl groups in 1,1-diethylcyclopentane may be interpreted as "adjacent groups" to each other. In one or more than one embodiment, the two methyl groups in 4,5-dimethylphenanthrene may be interpreted as "adjacent groups" to each other.

[0156] In the present disclosure, examples of halogen may include fluorine, chlorine, bromine or iodine.

[0157] In the present disclosure, the alkyl group may be straight chain or branched. The number of carbons in the alkyl group may be 1 to 50, 1 to 30, 1 to 20, 1 to 10 or 1 to 6. Examples of the alkyl group may include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, a tert-butyl group, an isobutyl group, a 2-ethylbutyl group, a 3,3-dimethylbutyl group, an n-pentyl group, an isopentyl group, a neopentyl group, a tert-pentyl group, a 1-methylpentyl group, a 3-methylpentyl group, a 2-ethylpentyl group, a 4-methyl-2-pentyl group, an n-hexyl group, a 1-methylhexyl group, a 2-ethyl tert-octyl group, 2-ethyloctyl group, 2-butyloctyl group, 2-hexyloctyl group, 3,7-dimethyloctyl group, n-nonyl group, n-decyl group, 2-ethyldecyl group, 2-butyldecyl group, 2-hexyldecyl group, 2-octyldecyl group, An n-undecyl group, an n-dodecyl group, a 2-ethyldodecyl group, a 2-butyldodecyl group, a 2-hexyldodecyl group, a 2-octyldodecyl group, an n-tridecyl group, an n-tetradecyl group, an n-pentadecyl group, an n-hexadecyl group, a 2-ethylhexadecyl group, a 2-butylhexadecyl group, a 2-hexylhexadecyl group, a 2-octylhexadecyl group, an n-heptadecyl group, an n-octadecyl group, an n-nonadecyl group, an n-eicosyl group, a 2-ethyleicosyl group, a 2-butyleicosyl group, a 2-hexyleicosyl group, a 2-octyleicosyl group, an n-heneicosyl group, an n-docosyl group, an n-tricosyl group, an n-tetracosyl group, an n-pentacosyl group, an n-hexacosyl group, an n-heptacosyl group, an n-octacosyl group, an n-nonacosyl group, an n-triacontyl group, and the like, but the embodiments of the present disclosure are not limited thereto.

[0158] In the present disclosure, a cycloalkyl group may refer to a cyclic alkyl group. The carbon number in the cycloalkyl group may be 3 to 50, 3 to 30, 3 to 20, or 3 to 10. Examples of cycloalkyl groups may include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a 4-methylcyclohexyl group, a 4-tert-butylcyclohexyl group, a cycloheptyl group, a cyclooctyl group, a cyclononyl group, a cyclodecyl group, a norbornyl group, a 1-adamantyl group, a 2-adamantyl group, an isobornyl group, a bicycloheptyl group, etc., but the embodiments of the present disclosure are not limited thereto.

[0159] In the present disclosure, an alkenyl group refers to a hydrocarbon group containing at least one carbon-carbon double bond in the middle or at the end of an alkyl group having 2 or more carbon atoms. An alkenyl group may be straight or branched. The number of carbon atoms in the alkenyl group is not particularly limited, and may be, for example, 2 to 30, 2 to 20, or 2 to 10. Examples of alkenyl groups may include vinyl groups, 1-butenyl groups, 1-pentenyl groups, 1,3-butadienyl groups, styryl groups, styryl vinyl groups, etc., but embodiments of the present disclosure are not limited thereto.

[0160] In the present disclosure, an alkynyl group refers to a hydrocarbon group containing at least one carbon-carbon triple bond in the middle or at the end of an alkyl group having 2 or more carbon atoms. An alkynyl group can be straight or branched. Although the number of carbon atoms is not specifically limited, it can be 2 to 30, 2 to 20, or 2 to 10. Examples of alkynyl groups can include ethynyl groups, propynyl groups, etc., but embodiments of the present disclosure are not limited thereto.

[0161] In the present disclosure, a hydrocarbon ring refers to any functional group or substituent derived from an aliphatic hydrocarbon ring. The hydrocarbon ring group may be a saturated hydrocarbon ring group having 5 to 20 ring-forming carbon atoms.

[0162] In the present disclosure, an aryl group refers to any functional group or substituent derived from an aromatic hydrocarbon ring. The aryl group may be a monocyclic aryl group or a polycyclic aryl group. The number of ring carbon atoms in the aryl group may be 6 to 60, 6 to 50, 6 to 40, 6 to 30, 6 to 20, or 6 to 15. Examples of aryl groups may include phenyl groups, naphthyl groups, fluorenyl groups, anthracenyl groups, phenanthrenyl groups, biphenyl groups, terphenyl groups, quaterphenyl groups, pentaphenyl groups, hexaphenyl groups, triphenylenyl groups, pyrenyl groups, benzofluoranthenyl groups, However, the embodiments of the present disclosure are not limited thereto.

[0163] In the present disclosure, the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure. Examples of substituted fluorenyl groups are as follows. However, embodiments of the present disclosure are not limited thereto.

[0164]

[0165] As used herein, a heterocyclic group may refer to any functional group or substituent derived from a ring containing at least one of B, O, N, P, Si and S as a heteroatom (e.g., 1 to 15, 1 to 10, 1 to 5 or 1 to 3 heteroatoms). A heterocyclic group may include an aliphatic heterocyclic group and / or an aromatic heterocyclic group. An aromatic heterocyclic group may be a heteroaryl group. Aliphatic heterocycles and aromatic heterocycles may each be monocyclic or polycyclic.

[0166] In the present disclosure, the heterocyclic group may contain at least one of B, O, N, P, Si and S as a heteroatom. When the heterocyclic group contains two or more heteroatoms, the two or more heteroatoms may be the same or different from each other. The heterocyclic group may be a monocyclic heterocyclic group or a polycyclic heterocyclic group, and may include a heteroaryl group. The number of ring carbon atoms in the heterocyclic group may be 2 to 60, 2 to 50, 2 to 40, 2 to 30, 2 to 20 or 2 to 10.

[0167] In the present disclosure, the aliphatic heterocyclic group may contain at least one of B, O, N, P, Si and S as a heteroatom. The number of ring carbon atoms in the aliphatic heterocyclic group may be 2 to 30, 2 to 20, or 2 to 10. Examples of the aliphatic heterocyclic group may include an oxirane group, a thiirane group, a pyrrolidine group, a piperidine group, a tetrahydrofuran group, a tetrahydrothiophene group, a thihexane group, a tetrahydropyran group, a 1,4-dioxane group, and the like, but embodiments of the present disclosure are not limited thereto.

[0168] In the present disclosure, the heteroaryl group may include at least one of B, O, N, P, Si and S as a heteroatom (e.g., 1 to 15, 1 to 10, 1 to 5 or 1 to 3 heteroatoms). When the heteroaryl group includes two or more heteroatoms, the two or more heteroatoms may be the same or different from each other. The heteroaryl group may be a monocyclic heterocyclic group or a polycyclic heterocyclic group. The number of ring carbon atoms in the heteroaryl group may be 2 to 60, 2 to 50, 2 to 40, 2 to 30, 2 to 20 or 2 to 10. Examples of the heteroaryl group may include a thiophene group, a furan group, a pyrrole group, an imidazole group, a pyridine group, a bipyridine group, a pyrimidine group, a triazine group, a triazole group, an acridine group, a pyridazine group, a pyrazine group, a quinoline group, a quinazoline group, a quinoxaline group, a phenoxazine group, a phthalazine group, a pyridopyrimidine group, a pyridopyrazine group, a pyrazinopyrazine group, an isoquinoline group, an indole group, a carbazole group, an N-arylcarbazole group, N-heteroarylcarbazole group, N-alkylcarbazole group, benzoxazole group, benzimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, thienothiophene group, benzofuran group, phenanthroline group, thiazole group, isoxazole group, oxazole group, oxadiazole group, thiadiazole group, phenothiazine group, dibenzosilole group, dibenzofuran group and the like, but the embodiments of the present disclosure are not limited thereto.

[0169] In the present disclosure, the above description of the aryl group may be applied to the arylene group, but the arylene group is a divalent group. The above description of the heteroaryl group may be applied to the heteroarylene group, but the heteroarylene group is a divalent group.

[0170] In the present disclosure, the silyl group may include an alkylsilyl group and / or an arylsilyl group. Examples of the silyl group may include a trimethylsilyl group, a triethylsilyl group, a tert-butyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, a phenylsilyl group, etc., but the embodiments of the present disclosure are not limited thereto.

[0171] In the present disclosure, the number of carbon atoms and / or the number of ring carbon atoms in the carbonyl group is not particularly limited, and may be, for example, 1 to 40, 1 to 30, or 1 to 20. For example, the carbonyl group may have the following structure, but embodiments of the present disclosure are not limited thereto.

[0172]

[0173] In the present disclosure, the number of carbon atoms in the sulfinyl group or the sulfonyl group is not particularly limited, and for example, may be 1 to 30, 1 to 20, 1 to 10, or 1 to 6. The sulfinyl group may include an alkylsulfinyl group and / or an arylsulfinyl group. The sulfonyl group may include an alkylsulfonyl group and / or an arylsulfonyl group.

[0174] In the present disclosure, the sulfenyl group may include an alkylsulfenyl group and / or an arylsulfenyl group. The sulfenyl group may refer to a sulfur atom bonded to an alkyl group or an aryl group defined above. Examples of sulfenyl groups may include a methylsulfenyl group, an ethylsulfenyl group, a propylsulfenyl group, a pentylsulfenyl group, a hexylsulfenyl group, an octylsulfenyl group, a dodecylsulfenyl group, a cyclopentylsulfenyl group, a cyclohexylsulfenyl group, a phenylsulfenyl group, a naphthylsulfenyl group, but the embodiments of the present disclosure are not limited thereto.

[0175] In the present disclosure, an oxy group may refer to an oxygen atom bonded to an alkyl group or an aryl group defined above. An oxy group may include an alkoxy group and / or an aryloxy group. An alkoxy group may be a straight chain, a branched chain or a ring. The number of carbon atoms in the alkoxy group is not particularly limited, but may be, for example, 1 to 20 or 1 to 10. Examples of oxy groups may include methoxy, ethoxy, n-propoxy, isopropoxy, butoxy, pentyloxy, hexyloxy, octyloxy, nonyloxy, decyloxy, benzyloxy, etc., but the embodiments of the present disclosure are not limited thereto.

[0176] Boron groups herein may refer to boron atoms bonded to an alkyl group or an aryl group defined above. Boron groups may include alkyl boron groups and / or aryl boron groups. Examples of boron groups may include dimethyl boron groups, tert-butyl methyl boron groups, diphenyl boron groups, phenyl boron groups, etc., but embodiments of the present disclosure are not limited thereto.

[0177] In the present disclosure, the number of carbon atoms in the amine group is not particularly limited, and for example, may be 1 to 30, 1 to 20, 1 to 10, or 1 to 6. The amine group may include an alkylamine group and / or an arylamine group. Examples of the amine group may include a methylamine group, a dimethylamine group, a phenylamine group, a diphenylamine group, a naphthylamine group, a 9-methyl-anthrylamine group, etc., but the embodiments of the present disclosure are not limited thereto.

[0178] In the present disclosure, the alkyl group in the alkylthio group, the alkylsulfonyloxy group, the alkylaryl group, the alkylamino group, the alkylboron group, the alkylsilyl group, and the alkylamine group may be the same as the examples of the alkyl group described above.

[0179] In the present disclosure, the aryl group in the aryloxy group, arylthio group, arylsulfonyloxy group, arylamino group, arylboron group, arylsilyl group, arylamine group may be the same as the examples of the aryl group described above.

[0180] In the present disclosure, a direct bond may refer to a single bond.

[0181] In this disclosure, and “—*” refer to the location to be connected.

[0182] Hereinafter, embodiments of the present disclosure will be described in more detail with reference to the accompanying drawings.

[0183] Figure 1 is a plan view illustrating a display device DD according to one or more embodiments of the present disclosure. Figure 2 is a cross-sectional view of a display device DD according to one or more embodiments. Figure 2 is an example along Figure 1 A cross-sectional view of a portion taken along line II'.

[0184] The display device DD may include a display panel DP and an optical layer PP disposed on the display panel DP. The display panel DP may include light-emitting elements ED-1, ED-2, and ED-3. The display device DD may include a plurality of light-emitting elements ED-1, ED-2, and ED-3. The optical layer PP may be disposed on the display panel DP to control reflected light in the display panel DP due to external light. The optical layer PP may include, for example, a polarizing layer and / or a color filter layer. In some embodiments, the optical layer PP may not be provided in the display device DD.

[0185] The base substrate BL may be disposed or provided on the optical layer PP. The base substrate BL may be a member providing a base surface on which the optical layer PP is disposed. The base substrate BL may be a glass substrate, a metal substrate, a plastic substrate, etc. However, the embodiments of the present disclosure are not limited thereto, and the base substrate BL may be an inorganic layer, an organic layer, or an organic-inorganic composite material layer. In some embodiments, the base substrate BL may not be provided.

[0186] The display device DD according to one or more embodiments may further include a filling layer. The filling layer may be disposed between the display device layer DP-ED and the base substrate BL. The filling layer may be an organic material layer. The filling layer may include at least one of an acrylic-based resin, a silicone-based resin, and an epoxy-based resin.

[0187] The display panel DP may include a base layer BS, a circuit layer DP-CL provided on the base layer BS, and a display device layer DP-ED. The display device layer DP-ED may include a pixel defining layer PDL, light emitting elements ED-1, ED-2, and ED-3 disposed between corresponding portions of the pixel defining layer PDL, and an encapsulation layer TFE disposed on the light emitting elements ED-1, ED-2, and ED-3.

[0188] The base layer BS may be a member that provides a base surface on which the display device layer DP-ED is disposed. The base layer BS may be a glass substrate, a metal substrate, a plastic substrate, etc. However, the embodiments of the present disclosure are not limited thereto, and the base layer BS may be an inorganic layer, an organic layer, or an organic-inorganic composite material layer.

[0189] In one or more embodiments, the circuit layer DP-CL may be disposed on the base layer BS, and the circuit layer DP-CL may include a plurality of transistors. Each of the transistors may include a control electrode, an input electrode, and an output electrode. For example, in some embodiments, the circuit layer DP-CL may include a switch transistor and a driving transistor for driving the light emitting elements ED-1, ED-2, and ED-3 of the display device layer DP-ED.

[0190] Each of the light emitting elements ED-1, ED-2, and ED-3 may have a light emitting element having a light emitting characteristic as will be described later. Figures 3 to 6 The structure of one of the light-emitting elements ED of the embodiment. Each of the light-emitting elements ED-1, ED-2 and ED-3 may include a first electrode EL1, a hole transport region HTR, respective light-emitting layers EML-R, EML-G and EML-B, an electron transport region ETR and a second electrode EL2.

[0191] Figure 2 An embodiment is illustrated in which the respective light-emitting layers EML-R, EML-G, and EML-B of the light-emitting elements ED-1, ED-2, and ED-3 are disposed in an opening OH defined in the pixel defining layer PDL, and the hole transport region HTR, the electron transport region ETR, and the second electrode EL2 are provided as a common layer in the entire light-emitting elements ED-1, ED-2, and ED-3. However, the embodiments of the present disclosure are not limited thereto, for example, in one or more than one embodiments, the hole transport region HTR and the electron transport region ETR may be provided by patterning in the opening OH defined in the pixel defining layer PDL. For example, in some embodiments, the hole transport region HTR, the respective light-emitting layers EML-R, EML-G, and EML-B, and the electron transport region ETR of the light-emitting elements ED-1, ED-2, and ED-3 may be provided by patterning in an inkjet printing method.

[0192] The encapsulation layer TFE may cover the light emitting elements ED-1, ED-2 and ED-3. The encapsulation layer TFE may seal the display device layer DP-ED. The encapsulation layer TFE may be a thin film encapsulation layer. The encapsulation layer TFE may be formed by laminating one or more layers. The encapsulation layer TFE may include at least one insulating layer. In some embodiments, the encapsulation layer TFE may include at least one inorganic film (hereinafter, encapsulation inorganic film). In some embodiments, the encapsulation layer TFE may include at least one organic film (hereinafter, encapsulation organic film) and at least one encapsulation inorganic film.

[0193] The encapsulated inorganic film protects the display device layer DP-ED from moisture / oxygen, and the encapsulated organic film protects the display device layer DP-ED from foreign substances such as dust particles. The encapsulated inorganic film may include silicon nitride, silicon oxynitride, silicon oxide, titanium oxide, aluminum oxide, etc., but the embodiments of the present disclosure are not particularly limited thereto. In some embodiments, the encapsulated organic film may include an acrylic-based compound, an epoxy-based compound, etc. In some embodiments, the encapsulated organic film may include a photopolymerizable organic material, but the embodiments of the present disclosure are not particularly limited thereto.

[0194] The encapsulation layer TFE may be disposed on the second electrode EL2 and may be disposed to fill the opening OH.

[0195] refer to Figure 1 and Figure 2 , the display device DD may include a non-light emitting area NPXA and light emitting areas PXA-R, PXA-G, and PXA-B. The light emitting areas PXA-R, PXA-G, and PXA-B may be areas in which light generated by the respective light emitting elements ED-1, ED-2, and ED-3 is emitted. The light emitting areas PXA-R, PXA-G, and PXA-B may be spaced and / or separated (e.g., spaced apart) from each other on a plane.

[0196] Each of the light-emitting regions PXA-R, PXA-G, and PXA-B may be a region separated by a pixel defining layer PDL. The non-light-emitting region NPXA may be a region between adjacent light-emitting regions PXA-R, PXA-G, and PXA-B, which corresponds to the pixel defining layer PDL. In one or more embodiments, the light-emitting regions PXA-R, PXA-G, and PXA-B may correspond to pixels, respectively. The pixel defining layer PDL may separate the light-emitting elements ED-1, ED-2, and ED-3. The respective light-emitting layers EML-R, EML-G, and EML-B of the light-emitting elements ED-1, ED-2, and ED-3 may be disposed in an opening OH defined in the pixel defining layer PDL and separated from each other.

[0197] The light emitting areas PXA-R, PXA-G, and PXA-B may be divided into a plurality of groups according to the colors of the lights generated by the light emitting elements ED-1, ED-2, and ED-3. Figure 1 and Figure 2 In the display device DD of one or more embodiments illustrated in the embodiment, three light-emitting areas PXA-R, PXA-G and PXA-B that emit red light, green light and blue light, respectively, are exemplarily illustrated. For example, in one or more embodiments, the display device DD may include a red light-emitting area PXA-R, a green light-emitting area PXA-G and a blue light-emitting area PXA-B that are separated from each other.

[0198] In a display device DD according to one or more embodiments, a plurality of light-emitting elements ED-1, ED-2, and ED-3 may be intended to emit light beams having wavelengths different from each other. For example, in some embodiments, 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, in some embodiments, a red light-emitting region PXA-R, a green light-emitting region PXA-G, and a blue light-emitting region PXA-B of the display device DD may correspond to the first light-emitting element ED-1, the second light-emitting element ED-2, and the third light-emitting element ED-3, respectively.

[0199] However, the embodiments of the present disclosure are not limited thereto, and the first to third light-emitting elements ED-1, ED-2, and ED-3 may be intended to emit light beams in substantially the same wavelength range, or at least one light-emitting element may be intended to emit a light beam in a wavelength range different from the others. For example, in some embodiments, the first to third light-emitting elements ED-1, ED-2, and ED-3 may all emit blue light.

[0200] The light emitting areas PXA-R, PXA-G, and PXA-B in the display device DD according to one or more embodiments may be arranged in a stripe form. Figure 1 , a plurality of red light emitting areas PXA-R may be arranged along the second direction axis DR2, a plurality of green light emitting areas PXA-G may be arranged along the second direction axis DR2, and a plurality of blue light emitting areas PXA-B may each be arranged along the second direction axis DR2. In some embodiments, the red light emitting areas PXA-R, the green light emitting areas PXA-G, and the blue light emitting areas PXA-B may be alternately arranged in a prescribed order along the first direction axis DR1.

[0201] Figure 1 and Figure 2It is illustrated that all the light-emitting regions PXA-R, PXA-G, and PXA-B have similar areas, but the embodiments of the present disclosure are not limited thereto. Therefore, the light-emitting regions PXA-R, PXA-G, and PXA-B may have different areas from each other according to the wavelength range of the emitted light. The area of ​​the light-emitting regions PXA-R, PXA-G, and PXA-B may refer to an area when viewed on a plane defined by the first direction axis DR1 and the second direction axis DR2 (e.g., an area in a plan view).

[0202] In some embodiments, the arrangement of the light-emitting areas PXA-R, PXA-G, and PXA-B is not limited to Figure 1 The configuration illustrated in FIG. 1 and the order in which the red light emitting area PXA-R, the green light emitting area PXA-G and the blue light emitting area PXA-B are arranged can be provided in one or more suitable combinations according to the characteristics of the display quality required in the display device DD. For example, in one or more embodiments, the arrangement form of the light emitting areas PXA-R, PXA-G and PXA-B can be a corrugated tile. Arrangement (e.g., RGBG matrix, RGBG structure, or RGBG matrix structure) or diamond (DiamondPixel TM ) arrangement form (for example, a display (for example, an OLED display) includes red, blue and green (RGB) light-emitting areas arranged in a diamond shape). is an officially registered trademark of Samsung Display Co., Ltd. Diamond Pixel TM is a trademark of Samsung Display Co., Ltd.

[0203] In some embodiments, the areas of the light-emitting regions PXA-R, PXA-G, and PXA-B may be different from each other. For example, in an embodiment, the area of ​​the green light-emitting region PXA-G may be smaller than the area of ​​the blue light-emitting region PXA-B, but the embodiments of the present disclosure are not limited thereto.

[0204] In the following, Figures 3 to 6 Each is a cross-sectional view schematically showing a light emitting element ED according to one or more embodiments. The light emitting element ED according to one or more embodiments may include a first electrode EL1, a second electrode EL2 facing the first electrode EL1, and at least one functional layer between the first electrode EL1 and the second electrode EL2. The light emitting element ED of one or more embodiments may include an amine compound of one or more embodiments to be explained later in at least one functional layer.

[0205] The light emitting element ED may include a hole transport region HTR, a light emitting layer EML, an electron transport region ETR, etc. stacked in sequence (eg, in a prescribed order) as at least one functional layer. Figure 3 In one or more embodiments, the light emitting element ED may include a first electrode EL1, a hole transport region HTR, a light emitting layer EML, an electron transport region ETR, and a second electrode EL2 stacked in sequence (eg, in a prescribed order).

[0206] The light-emitting element ED according to one or more embodiments may include an amine compound of one or more embodiments to be explained later in the hole transport region HTR between the first electrode EL1 and the second electrode EL2. However, the embodiments of the present disclosure are not limited thereto. In addition to the hole transport region HTR, the light-emitting element ED according to one or more embodiments may include an amine compound of one or more embodiments to be explained later in the light-emitting layer EML or the electron transport region ETR as a plurality of functional layers between the first electrode EL1 and the second electrode EL2, or may include an amine compound of one or more embodiments to be explained later in the cover layer CPL on the second electrode EL2.

[0207] and Figure 3 compared to, Figure 4 A cross-sectional view of a light emitting element ED according to one or more embodiments is illustrated, 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 one or more embodiments is illustrated, 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 illustrating one or more embodiments including a cover layer CPL on the second electrode EL2.

[0208] The light-emitting element ED according to one or more embodiments may include an amine compound of an embodiment to be explained later in the hole transport region HTR. In the light-emitting element ED according to one or more embodiments, at least one selected from the hole injection layer HIL, the hole transport layer HTL, and the electron blocking layer EBL may include an amine compound of one or more embodiments. In one or more embodiments, a layer adjacent to the light-emitting layer in the plurality of layers included in the hole transport region HTR may include an amine compound represented by Formula 1 of one or more embodiments. For example, in the light-emitting element ED according to one or more embodiments, the hole transport layer HTL may include an amine compound of one or more embodiments.

[0209] The first electrode EL1 has conductivity (for example, it is a conductor). The first electrode EL1 may be formed of a metal material, a metal alloy and / or a conductive compound. The first electrode EL1 may be an anode or a cathode. However, the embodiments of the present disclosure are not limited thereto. In one or more than one embodiments, the first electrode EL1 may be a pixel electrode. The first electrode EL1 may be a transmissive electrode, a semi-transmissive reflective electrode or a reflective electrode. The first electrode EL1 may include at least one selected from 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), lithium fluoride (LiF), molybdenum (Mo), titanium (Ti), tungsten (W), indium (In), tin (Sn) and zinc (Zn), selected from any compound of two or more than two thereof, selected from any mixture of two or more than two of these, and / or any oxide thereof.

[0210] 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). When the first electrode EL1 is a semi-transmissive reflective electrode or a reflective electrode, the first electrode EL1 may include Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, Mo, Ti, W, any compound thereof, or any mixture thereof (e.g., a mixture of Ag and Mg); or LiF / Ca (a stacked structure of LiF and Ca) or LiF / Al (a stacked structure of LiF and Al). In some embodiments, the first electrode EL1 may have a multilayer structure including a reflective film or a semi-transmissive reflective film formed of one or more of the materials described above, and a transparent conductive film formed of ITO, IZO, ZnO, ITZO, etc. For example, in some embodiments, the first electrode EL1 may have a three-layer structure of ITO / Ag / ITO, but the embodiments of the present disclosure are not limited thereto. The first electrode EL1 may include one of the metal materials described above, any combination of at least two of the metal materials described above, any oxide of the metal materials described above, etc. The thickness of the first electrode EL1 may be about to about For example, in one or more embodiments, the thickness of the first electrode EL1 may be about to about

[0211] A hole transport region HTR may be provided on the first electrode EL1. The hole transport region HTR may include at least one of a hole injection layer HIL, a hole transport layer HTL, a buffer layer, an emission auxiliary layer, and an electron blocking layer EBL. The thickness of the hole transport region HTR may be, for example, about 100 Å. to about

[0212] The hole transport region HTR may have a single layer formed of a single material, a single layer formed of a plurality of different materials, or a multi-layer structure including a plurality of layers formed of a plurality of different materials.

[0213] For example, in one or more embodiments, the hole transport region HTR may have a single-layer structure of a hole injection layer HIL or a hole transport layer HTL, or may have a single-layer structure formed of a hole injection material and a hole transport material. In some embodiments, the hole transport region HTR may have a single-layer structure formed of a plurality of different materials, or a structure in which a hole injection layer HIL / hole transport layer HTL, a hole injection layer HIL / hole transport layer HTL / buffer layer, a hole injection layer HIL / buffer layer, a hole transport layer HTL / buffer layer, or a hole injection layer HIL / hole transport layer HTL / electron blocking layer EBL are stacked in sequence (e.g., in a prescribed order) from the first electrode EL1, but the embodiments of the present disclosure are not limited thereto.

[0214] The hole transport region HTR may be formed using one or more suitable methods such as vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) method, inkjet printing, laser printing and / or laser induced thermal imaging (LITI) method.

[0215] In one or more embodiments, the light emitting element ED may include an amine compound according to one or more embodiments in the hole transport region HTR. In the light emitting element ED according to one or more embodiments, the hole transport region HTR may include a hole injection layer HIL and a hole transport layer HTL, and the hole transport layer HTL may include an amine compound according to one or more embodiments. The amine compound according to one or more embodiments may be included in a layer adjacent to the light emitting layer EML in the layer included in the hole transport region HTR.

[0216] The amine compound according to one or more embodiments comprises a structure in which two amine groups are connected via a linker. The amine compound according to one or more embodiments comprises a first amine group, a second amine group, and a first linker connecting the first amine group and the second amine group. In one or more embodiments, the first linker can be a substituted or unsubstituted arylene group with 6 to 30 ring-forming carbon atoms.

[0217] According to the amine compound of one or more than one embodiment, the first substituent group connected to the first amine group may be included. The first substituent group may include a naphthyl moiety and a first substituent group connected to the naphthyl moiety. The naphthyl moiety included in the first substituent group may be connected to the first amine group. One of the carbon atoms forming the naphthyl moiety may be connected to the nitrogen atom of the first amine group, and one of the remaining carbon atoms may be connected to the first substituent group. The first substituent group is directly connected to the naphthyl moiety. In one or more than one embodiment, the first substituent group may be a substituted or unsubstituted oxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted aryl group with 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group with 2 to 30 ring carbon atoms. For example, in some embodiments, the first substituent group may be a substituted or unsubstituted phenyl group.

[0218] As used herein, the first substituent may be represented by Formula S1.

[0219] Formula S1

[0220]

[0221] In formula S1, R a may correspond to the first substituent described above. a It may be a substituted or unsubstituted oxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms. In one or more than one embodiment, R a It may be a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms.

[0222] In formula S1, R 1 It may be hydrogen, deuterium, halogen, substituted or unsubstituted oxy group, substituted or unsubstituted silyl group, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms. For example, in some embodiments, R 1 It may be hydrogen.

[0223] In Formula S1, n1 is an integer from 0 to 6. In Formula 1, when n1 is 0, the amine compound according to one or more embodiments may not be R 1 In Formula 1, where n1 is 6 and R 1The embodiment in which all are hydrogen can be the same as the embodiment in which n1 is 0. When n1 is an integer of 2 or greater, the plurality of R provided 1 Can be all the same or selected from multiple R 1 At least one of may be different.

[0224] In Formula S1, —* may be the position to which the above-described nitrogen atom of the first amine group is attached.

[0225] The amine compound according to one or more embodiments has a structure in which the first amine group and the second amine group are connected via a first linker as a basic structure, and the first linker can be a substituted or unsubstituted phenylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted terphenylene, or a substituted or unsubstituted quaterphenylene. However, due to spatial reasons, embodiments in which the first linker is a substituted or unsubstituted p,p-biphenylene can be excluded. For example, when the first linker is a substituted or unsubstituted biphenylene, the first linker can be, for example, a substituted or unsubstituted m,p-biphenylene, a substituted or unsubstituted m,m-biphenylene, a substituted or unsubstituted o,p-biphenylene, a substituted or unsubstituted o,o-biphenylene, or a substituted or unsubstituted o,m-biphenylene.

[0226] As used herein, the m,p-biphenylene group may be represented by Formula B1-a.

[0227] Formula B1-a

[0228]

[0229] As used herein, the m,m-biphenylene group may be represented by Formula B1-b.

[0230] Formula B1-b

[0231]

[0232] As used herein, the o,p-biphenylene group may be represented by Formula B1-c.

[0233] Formula B1-c

[0234]

[0235] As used herein, the o,o-biphenylene group may be represented by Formula B1-d.

[0236] Formula B1-d

[0237]

[0238] As used herein, the o,m-biphenylene group may be represented by Formula B1-e.

[0239] Formula B1-e

[0240]

[0241] As used herein, the p,p-biphenylene group may be represented by Formula B1-f.

[0242] Formula B1-f

[0243]

[0244] In one or more than one embodiment, the nitrogen atom of the first amine group of the naphthyl part of each substituent and the first substituent can be connected to the naphthyl part, so as to be in an ortho relationship. For example, in some embodiments, the first substituent can be connected to the first carbon position of the naphthyl part, and the nitrogen atom of the first amine group can be connected to the second carbon position of the naphthyl part. In some embodiments, the nitrogen atom of the first amine group can be connected to the second carbon position or the third carbon position of the naphthyl part, and the first substituent can be connected to the remaining carbon atoms selected from the second carbon and the third carbon of the naphthyl part. However, the embodiments of the present disclosure are not limited thereto. As used herein, the carbon of the naphthyl part is numbered as represented in formula N1. Meanwhile, for ease of explanation, the carbon number at the position where two benzene rings are fused in formula N1 is omitted is shown.

[0245] Formula N1

[0246]

[0247] In one or more than one embodiment, the naphthyl moiety represented by formula S1 can be represented by formula S1-a or formula S1-b.

[0248] Formula S1-a

[0249]

[0250] Formula S1-b

[0251]

[0252] In Formula S1-a and Formula S1-b, the same description as in Formula S1 can be applied to R a , R 1 and n1.

[0253] In Formula S1-a and Formula S1-b, —* may be the position to which the nitrogen atom of the first amine group is attached.

[0254] The amine compound according to one or more embodiments may be a diamine compound including two amine groups.The amine compound according to one or more embodiments may be a diamine compound in which only two (precisely two) amine groups exist without forming a ring in the molecular structure.

[0255] In one or more than one embodiments, the amine compound can be represented by Formula 1.

[0256] Formula 1

[0257]

[0258] In formula 1, Ar 1 The attached amine group may correspond to the first amine group described above, and Ar 2 and Ar 3 The attached amine group may correspond to the second amine group described above. 1 It may correspond to the first linker described above. 1 The naphthyl group substituted with a substituent represented by may correspond to the naphthyl moiety described above and is represented by R a The substituent represented may correspond to the first substituent described above.

[0259] In formula 1, Ar 1 To Ar 3 Each may independently be a substituted or unsubstituted oxy group, a substituted or unsubstituted silyl 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 alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms.

[0260] In one or more than one embodiment, Ar 1 Ar may be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted cyclohexylphenyl group, or a substituted or unsubstituted naphthyl group. 2 and Ar 3 Each may independently be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted cyclohexylphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted fluorene group, or a substituted or unsubstituted dibenzofuran group.

[0261] In one or more than one embodiment, Ar 1 To Ar 3Each may be independently selected from Substituent Group A which will be described later.

[0262] In the amine compound represented by Formula 1, according to some embodiments, excluding Ar 1 In some embodiments, the embodiments wherein Ar 1 is an embodiment of a fluorene group or a heteroaryl group having 2 to 30 ring-forming carbon atoms such as a dibenzofuran group or a dibenzothiophene group. For example, in the amine compound represented by Formula 1, according to some embodiments, in addition to the first substituent, the substituent connected to the first amine group may not include a fluorene group, a dibenzofuran group, or a dibenzothiophene group (for example, a fluorene group, a dibenzofuran group, or a dibenzothiophene group may be excluded). When Ar in Formula 1 1 When a fluorene group, a dibenzofuran group, or a dibenzothiophene group is included, the distance between molecules increases, and thus π-π stacking decreases. Therefore, the hole transport capability may decrease, and the hole mobility may decrease. According to the present disclosure, since the Ar included in the amine compound is excluded, 1 The embodiment including the fluorene group, the dibenzofuran group, or the dibenzothiophene group can improve the hole transport characteristics. Therefore, it can show improved luminous efficiency and device life characteristics. In Formula 1, L 1 The phenylene group may be substituted or unsubstituted.

[0263] In formula 1, R a It may be a substituted or unsubstituted oxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms. For example, in some embodiments, R a The phenyl group may be substituted or unsubstituted.

[0264] In formula 1, R 1 It may be hydrogen, deuterium, halogen, substituted or unsubstituted oxy group, substituted or unsubstituted silyl group, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms. For example, in some embodiments, R 1 It may be hydrogen.

[0265] In Formula 1, n1 is an integer of 0 to 6. In Formula 1, when n1 is 0, the amine compound according to one or more embodiments may not be R 1Wherein n1 in Formula 1 is 6 and all R 1 The embodiment in which n1 is hydrogen may be the same as the embodiment in which n1 is 0 in Formula 1. When n1 is an integer of 2 or greater, the plurality of R 1 Can be all the same, or selected from multiple R 1 At least one of may be different.

[0266] In Formula 1, m1 is an integer from 1 to 4. For example, m1 may be 1, 3, or 4.

[0267] In the amine compound represented by Formula 1, according to one or more embodiments, when m1 is 2, excluding L 1 Embodiment represented by formula A-1. In the amine compound represented by formula 1, according to one or more embodiments, the embodiment in which the first linker connecting the first amine group and the second amine group is represented by formula A-1 can be excluded, and the p,p-biphenylene embodiment. The linker represented by formula A-1 has a structure in which two benzene rings are connected to the first amine group and the second amine group so as to be in a para-position relationship, so the planarity within the molecule may increase, and may cause the charge mobility to decrease. According to the present disclosure, in the amine compound represented by formula 1, according to one or more embodiments, because the embodiment in which the first linker connecting the first amine group and the second amine group is represented by formula A-1 is excluded, the charge mobility can be improved. Therefore, the luminous efficiency and the element service life characteristics can be improved.

[0268] Formula A-1

[0269]

[0270] In formula A-1, —* is the same as Ar in formula 1 1 The position of the attached nitrogen atom, and is the same as Ar in formula 1 2 and Ar 3 The position of the attached nitrogen atom.

[0271] In one or more than one embodiments, the amine compound represented by Formula 1 may be represented by Formula 2.

[0272] Formula 2

[0273]

[0274] In formula 2, R 2It may be hydrogen, deuterium, halogen, substituted or unsubstituted oxy group, substituted or unsubstituted silyl group, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms. For example, in some embodiments, R 2 It may be hydrogen.

[0275] In Formula 2, n2 may be an integer from 0 to 4. In Formula 2, when n2 is 0, the amine compound according to one or more embodiments may be 2 substituted. Wherein n2 in Formula 2 is 4 and all R 2 The embodiment in which n2 is hydrogen may be the same as the embodiment in which n2 in Formula 2 is 0. When n2 is an integer of 2 or greater, the plurality of R provided 2 Can be all the same, or selected from multiple R 2 At least one of may be different.

[0276] In Formula 2, the same description as in Formula 1 can be applied to Ar 1 To Ar 3 , R a , R 1 , n1 and m1.

[0277] In one or more than one embodiments, the amine compound represented by Formula 1 may be represented by Formula 3.

[0278] Formula 3

[0279]

[0280] Formula 3 represents the formula in which R is indicated in Formula 1 a Formula 3 may correspond to the embodiment in which R a is an embodiment of a substituted or unsubstituted phenyl group.

[0281] In formula 3, R 3 It may be hydrogen, deuterium, halogen, substituted or unsubstituted oxy group, substituted or unsubstituted silyl group, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms. For example, in some embodiments, R 3 It may be hydrogen.

[0282] In Formula 3, n3 may be an integer from 0 to 5. In Formula 3, when n3 is 0, the amine compound according to one or more embodiments may be 3substituted. Wherein n3 in Formula 3 is 5 and all R 3 The embodiment in which n3 is hydrogen may be the same as the embodiment in which n3 in Formula 3 is 0. When n3 is an integer of 2 or greater, the plurality of R 3 Can be all the same, or selected from multiple R 3 At least one of may be different.

[0283] In Formula 3, the same description as in Formula 1 can be applied to Ar 1 To Ar 3 , L 1 , R 1 , n1 and m1.

[0284] In one or more than one embodiments, the amine compound represented by Formula 3 may be represented by Formula 4-1 or Formula 4-2.

[0285] Formula 4-1

[0286]

[0287] Formula 4-2

[0288]

[0289] Formula 4-1 and Formula 4-2 represent the first amine group and R each connected to a naphthyl moiety. a In addition, Formula 4-1 and Formula 4-2 represent that R a is an embodiment of a substituted or unsubstituted phenyl group.

[0290] In Formula 4-1 and Formula 4-2, the same description as in Formula 1 and Formula 3 can be applied to Ar 1 To Ar 3 , L 1 , R 1 , R 3 , n1, n3 and m1.

[0291] In one or more than one embodiments, the amine compound represented by Formula 1 may be represented by any one selected from Formula 5-1 to Formula 5-5.

[0292] Formula 5-1

[0293]

[0294] Formula 5-2

[0295]

[0296] Formula 5-3

[0297]

[0298] Formula 5-4

[0299]

[0300] Formula 5-5

[0301]

[0302] Formula 5-1 to Formula 5-5 represent that L is indicated in Formula 1 1 The type (kind) and number of m1 implementation schemes.

[0303] In Formula 5-1 to Formula 5-5, R 11 To R 20 and R and R are each independently hydrogen, deuterium, halogen, substituted or unsubstituted oxy group, substituted or unsubstituted silyl group, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms. For example, in some embodiments, R 11 To R 20 may each independently be hydrogen.

[0304] In Formula 5-1 to Formula 5-5, n11 to n20 may each independently be an integer of 0 to 4. In Formula 5-1 to Formula 5-5, when n11 to n20 are each 0, the amine compound according to one or more embodiments may be respectively not R 11 To R 20 Wherein in Formula 5-1 to Formula 5-5, n11 to n20 are each 4 and all R 11 To R 20 The embodiments in which n11 to n20 are each hydrogen may be the same as the embodiments in which n11 to n20 are each 0 in Formula 5-1 to Formula 5-5. When n11 to n20 are each an integer of 2 or greater, the plurality of R 11 To multiple R 20 Each may be all the same or selected from a plurality of R 11 To multiple R 20 At least one of the respective ones may be different.

[0305] In Formula 5-1 to Formula 5-5, the same description as in Formula 1 can be applied to Ar 1 To Ar 3 , R a , R 1 and n1.

[0306] In one or more than one embodiment, L 1It may be represented by any one selected from Formula L-1 to Formula L-22.

[0307] Formula L-1

[0308]

[0309] Formula L-2

[0310]

[0311] Formula L-3

[0312]

[0313] Formula L-4

[0314]

[0315] Formula L-5

[0316]

[0317] Formula L-6

[0318]

[0319] Formula L-7

[0320]

[0321] Formula L-8

[0322]

[0323] Formula L-9

[0324]

[0325] Formula L-10

[0326]

[0327] Formula L-11

[0328]

[0329] Formula L-12

[0330]

[0331] Formula L-13

[0332]

[0333] Formula L-14

[0334]

[0335] Formula L-15

[0336]

[0337] Type L-16

[0338]

[0339] Formula L-17

[0340]

[0341] Formula L-18

[0342]

[0343] Type L-19

[0344]

[0345] Formula L-20

[0346]

[0347] Formula L-21

[0348]

[0349] Formula L-22

[0350]

[0351] In Formula L-1 to Formula L-22, R b1 To R b65 and R and R are each independently hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms. b1 To R b65 can be independently hydrogen. —* is the same as Ar in formula 1 1 the position of the attached nitrogen atom, and is the same as Ar in formula 1 2 and Ar 3 The position of the attached nitrogen atom.

[0352] In Formula L-1 to Formula L-22, m1 to m65 may each independently be an integer of 0 to 4. In Formula L-1 to Formula L-22, when m1 to m65 are each 0, the amine compound according to one or more embodiments may be unreacted by R b1 To Rb65 wherein in formula L-1 to formula L-22, m1 to m65 are each 4 and all R b1 To R b65 The embodiment in which each is hydrogen may be the same as the embodiment in which m1 to m65 in L-1 to formula L-22 are each 0. When m1 to m65 are each an integer of 2 or greater, the plurality of R provided b1 To multiple R b65 Each may be the same, or selected from a plurality of R b1 To multiple R b65 At least one of the respective ones may be different.

[0353] In one or more than one embodiment, Ar 1 may be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted naphthyl group, and Ar 2 and Ar 3 Each may independently be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted fluorenyl group.

[0354] In one or more than one embodiment, Ar 1 can be represented by any one selected from Formula B-1 to Formula B-4, and Ar 2 and Ar 3 Each may be independently represented by any one selected from Formula B-1 to Formula B-7.

[0355] Formula B-1

[0356]

[0357] Formula B-2

[0358]

[0359] Formula B-3

[0360]

[0361] Formula B-4

[0362]

[0363] Formula B-5

[0364]

[0365] Formula B-6

[0366]

[0367] Formula B-7

[0368]

[0369] In Formula B-1 to Formula B-7, R d1 To R d18 and R and R are each independently hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms. d1 To R d18 and * are each independently hydrogen. —* is the position of connection to the corresponding nitrogen atom in Formula 1.

[0370] In Formula B-1 to Formula B-7, p1, p3, p11 and p12 can each independently be an integer from 0 to 5, p2, p4, p10, p14, p15, p16 and p18 can each independently be an integer from 0 to 4, p5 is an integer from 0 to 11, p6 is an integer from 0 to 7, and p9, p13 and p17 can each independently be an integer from 0 to 3.

[0371] When p1, p3, p11 and p12 are each 0, the amine compound according to one or more embodiments may be respectively not R d1 , R d3 , R d11 and R d12 Wherein p1, p3, p11 and p12 are each 5 and R d1 , R d3 , R d11 and R d12 The embodiment in which each is hydrogen may be the same as the embodiment in which each of p1, p3, p11 and p12 is 0.

[0372] When p2, p4, p10, p14, p15, p16, and p18 are each 0, the amine compound according to one or more embodiments may be respectively not R d2 , R d4 , R d10 , R d14 , R d15 , R d16 and R d18 wherein p2, p4, p10, p14, p15, p16 and p18 are each 4 and R d2 , R d4 , R d10 , R d14 , R d15 , R d16 and R d18The embodiment where each is hydrogen can be the same as the embodiment where each of p2, p4, p10, p14, p15, p16 and p18 is 0.

[0373] When p5 is 0, the amine compound according to one or more embodiments may not be R d5 Where p5 is 11 and all R d5 The embodiment in which each is hydrogen may be the same as the embodiment in which p5 is 0. When p6 is 0, the amine compound according to one or more embodiments may not be R d6 Where p6 is 7 and R d6 The embodiment where each is hydrogen may be the same as the embodiment where p6 is 0.

[0374] When p9, p13, and p17 are each 0, the amine compound according to one or more embodiments may be respectively unreacted by R d9 , R d13 and R d17 Wherein p9, p13 and p17 are each 3 and R d9 , R d13 and R d17 The embodiment in which each is hydrogen can be the same as the embodiment in which p9, p13 and p17 are each 0.

[0375] When p1 to p6 and p9 to p18 are each an integer of 2 or greater, a plurality of R d1 To multiple R d6 and multiple R d9 To multiple R d18 Each can be the same, or multiple R d1 To multiple R d6 and multiple R d9 To multiple R d18 At least one of the respective ones may be different.

[0376] In one or more than one embodiments, the amine compound represented by Formula 1 may be represented by Formula 6-1 or Formula 6-2.

[0377] Formula 6-1

[0378]

[0379] Formula 6-2

[0380]

[0381] In equations 6-1 and 6-2, R 3It may be hydrogen, deuterium, halogen, substituted or unsubstituted oxy group, substituted or unsubstituted silyl group, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms. For example, in some embodiments, R 3 It may be hydrogen.

[0382] In Formula 6-1 and Formula 6-2, n3 is an integer from 0 to 5. In Formula 6-1 and Formula 6-2, when n3 is 0, the amine compound according to one or more embodiments may not be R 3 Wherein in Formula 6-1 and Formula 6-2, n3 is 5 and all R 3 The embodiment in which each is hydrogen may be the same as the embodiment in which n3 is 0 in Formula 6-1 and Formula 6-2. When n3 is an integer of 2 or greater, the plurality of R 3 Can be all the same or selected from multiple R 3 At least one of may be different.

[0383] In Formula 6-1 and Formula 6-2, the same description as in Formula 1 can be applied to L 1 , R 1 , n1 and m1.

[0384] In Formula 6-1 and Formula 6-2, Ar 1 'To Ar 3 ' may be independently selected from substituent group A, provided that Ar 1 ' may not be selected from any one of a36 to a47.

[0385] Substituent Group A

[0386]

[0387]

[0388]

[0389] In the substituent group A, —* is a position to which the corresponding nitrogen atom in Formula 1 is bonded. In one or more than one embodiments, the amine compound represented by Formula 1 may be represented by Formula 7.

[0390] Formula 7

[0391]

[0392] In formula 7, R 4It may be hydrogen, deuterium, halogen, substituted or unsubstituted oxy group, substituted or unsubstituted silyl group, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms. For example, in some embodiments, R 4 It may be hydrogen.

[0393] In Formula 7, n4 is an integer of 0 to 6. In Formula 7, when n4 is 0, the amine compound according to one or more embodiments may not be R 4 Wherein n4 in Formula 7 is 6 and all R 4 The embodiment in which n4 is hydrogen may be the same as the embodiment in which n4 in Formula 7 is 0. When n4 is an integer of 2 or greater, the plurality of R 4 Can be all the same, or selected from multiple R 4 At least one of may be different.

[0394] In formula 7, R b It may be a substituted or unsubstituted oxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms. For example, in some embodiments, R b The phenyl group may be substituted or unsubstituted.

[0395] In Formula 7, the same description as in Formula 1 can be applied to Ar 1 ,Ar 2 , R a , R 1 , n1, L1 and m1.

[0396] In one or more than one embodiments, the amine compound represented by Formula 1 may be represented by Formula 8-1 or Formula 8-2.

[0397] Formula 8-1

[0398]

[0399] Formula 8-2

[0400]

[0401] In formula 8-2, R 5It may be hydrogen, deuterium, halogen, substituted or unsubstituted oxy group, substituted or unsubstituted silyl group, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms. For example, in some embodiments, R 5 It may be hydrogen.

[0402] In Formula 8-2, n5 is an integer from 0 to 5. In Formula 8-2, when n5 is 0, the amine compound according to one or more embodiments may not be R 5 In formula 8-2, n5 is 5 and all R 5 The embodiment in which n5 is hydrogen may be the same as the embodiment in which n5 in Formula 8-2 is 0. When n5 is an integer of 2 or greater, the plurality of R 5 Can be all the same, or selected from multiple R 5 At least one of may be different.

[0403] In formula 8-1 and formula 8-2, Ar 1 " may be a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms.

[0404] In formula 8-1 and formula 8-2, Ar 2 " and Ar 3 " may each independently be a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms.

[0405] In one or more than one embodiment, Ar 1 " may be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted cyclohexylphenyl group, or a substituted or unsubstituted naphthyl group.

[0406] In one or more than one embodiment, Ar 2 " and Ar 3 " may each independently be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted cyclohexylphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted fluorene group, or a substituted or unsubstituted dibenzofuran group.

[0407] In one or more than one embodiment, Ar 1 "、Ar 2 " and Ar 3 " can be each independently represented by any one selected from Formula B-1 to Formula B-7, provided that Ar 1 " may not be represented by any one selected from Formula B-5 to Formula B-7 .

[0408] In one or more than one embodiment, Ar 1 "、Ar 2 " and Ar 3 " may be independently selected from substituent group A, provided that Ar 1 " may not be selected from any one of a36 to a47.

[0409] In one or more than one embodiment, selected from Ar 1 "、Ar 2 " and Ar 3 " may be a substituted or unsubstituted aryl group having 6 to 15 carbon atoms. In some embodiments, the group selected from Ar 1 "、Ar 2 " and Ar 3 At least one of " may be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted fluorene group. However, embodiments of the present disclosure are not limited thereto.

[0410] In Formula 8-1 and Formula 8-2, the same description as in Formula 1 can be applied to R 1 、n1、L 1 and m1.

[0411] In Equation 8-1 and Equation 8-2, the same description as in Equation 3 can be applied to R 3 and n3.

[0412] In Equation 8-1 and Equation 8-2, the same description as in Equation 7 can be applied to R 4 and n4.

[0413] The amine compound according to one or more embodiments may be represented by one of the compounds selected from compound group 1. The hole transport region HTR of the light-emitting element ED according to one or more embodiments may include at least one selected from the amine compounds disclosed in compound group 1. For example, in one or more embodiments, the hole transport layer HTL of the light-emitting element ED may include at least one selected from the amine compounds disclosed in compound group 1.

[0414] Compound Group 1

[0415]

[0416]

[0417]

[0418]

[0419]

[0420]

[0421]

[0422]

[0423]

[0424] The amine compound according to one or more embodiments includes a structure in which two amine groups are connected via a connector. The amine compound according to one or more embodiments includes a first amine group, a second amine group, and a first connector connecting the first amine group and the second amine group. The amine compound according to one or more embodiments may include a first substituent connected to the first amine group. The first substituent may include a naphthyl moiety and a first substituent connected to the naphthyl moiety. The naphthyl moiety included in the first substituent may be connected to the first amine group. One of the carbon atoms forming the naphthyl moiety may be connected to the nitrogen atom of the first amine group, and one of the remaining carbon atoms may be connected to the first substituent. The first substituent may be directly connected to the naphthyl moiety. According to one or more embodiments, the amine compound with such a structure may exhibit excellent or suitable electrical stability and high charge transport capability, and therefore, when the amine compound according to one or more embodiments is applied to a light-emitting element, luminous efficiency and element service life may be improved. Therefore, when the amine compound according to one or more embodiments of the present disclosure is applied to the hole transport region HTR of the light emitting element ED, a light emitting element having high efficiency, low driving voltage, and long lifetime may be realized.

[0425] Reference again Figures 3 to 6 , and then the light-emitting element according to one or more than one embodiments of the present disclosure will be further described.

[0426] As described above, the hole transport region HTR may include the amine compound according to one or more embodiments of the present disclosure described above. For example, the hole transport region HTR may include the amine compound represented by Formula 1.

[0427] When the hole transport region HTR has a multilayer structure including a plurality of layers, then any one of the plurality of layers may include an amine compound represented by Formula 1. For example, in one or more embodiments, the hole transport region HTR may include a hole injection layer HIL on the first electrode EL1 and a hole transport layer HTL on the hole injection layer HIL, wherein the hole transport layer HTL may include an amine compound represented by Formula 1. However, embodiments of the present disclosure are not limited thereto, and for example, in some embodiments, the hole injection layer HIL may include an amine compound represented by Formula 1.

[0428] The hole transport region HTR may include one or two or more types (kinds) of the amine compound represented by Formula 1. For example, in one or more embodiments, the hole transport region HTR may include at least one selected from the compounds presented in Compound Group 1 described above.

[0429] In one or more than one embodiment, the hole transport region HTR may further comprise a compound represented by Formula H-1:

[0430] Formula H-1

[0431]

[0432] In formula H-1, L 1 and L 2 Each of a and b may be independently a direct bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms. a and b may be independently an integer from 0 to 10. In some embodiments, when a or b is an integer of 2 or greater, multiple L 1 and multiple L 2 Each may independently be a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms.

[0433] In formula H-1, Ar a and Ar b may be each independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms. In one or more than one embodiment, in formula H-1, Ar c It may be a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms.

[0434] The compound represented by formula H-1 may be a monoamine compound. In some embodiments, the compound represented by formula H-1 may be a diamine compound, wherein the compound selected from Ar a To Ar c At least one of them contains an amine group as a substituent. In some embodiments, the compound represented by formula H-1 can be a and Ar b A carbazole-based compound including a substituted or unsubstituted carbazole group in at least one of Ar a and Ar b A fluorene-based compound including a substituted or unsubstituted fluorene group in at least one of the foregoing.

[0435] The compound represented by Formula H-1 may be any one selected from the compounds in Compound Group H. However, the compounds listed in Compound Group H are only examples, and the compound represented by Formula H-1 is not limited to those represented in Compound Group H:

[0436] Compound Group H

[0437]

[0438]

[0439] In some embodiments, the hole transport region HTR may further include any suitable material generally available in the art.

[0440] For example, in some embodiments, the hole transport region HTR may include a phthalocyanine compound (eg, copper phthalocyanine), N 1 ,N 1 '-([1,1'-biphenyl]-4,4'-diyl)bis(N 1 -(phenyl-N 4 ,N 4-dimethylphenylbenzene-1,4-diamine) (DNTPD), 4,4',4"-[tri(3-methylphenyl)phenylamino]triphenylamine (m-MTDATA), 4,4',4"-tri(N,N-diphenylamino)triphenylamine (TDATA), 4,4',4"-tri[N-(2-naphthyl)-N-phenylamino]-triphenylamine (2-TNATA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / dodecylbenzenesulfonic acid (PANI / DBSA), polyaniline / camphorsulfonic acid (PANI / CSA), polyaniline / poly(4-styrenesulfonate) (PANI / PSS), N,N'-di(naphthalene-l-yl)-N,N'-diphenyl-benzidine (NPB), triphenylamine-containing polyether ketone (TPAPEK), 4-isopropyl-4'-methyldiphenyliodonium [tetrakis(pentafluorophenyl)borate], dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile (HAT-CN), etc.

[0441] In one or more than one embodiments, the hole transport region HTR may include at least one selected from carbazole-based derivatives (e.g., N-phenylcarbazole or polyvinylcarbazole), fluorene-based derivatives, triphenylamine-based derivatives (e.g., N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1-biphenyl]-4,4'-diamine (TPD) or 4,4',4"-tri(N-carbazolyl)triphenylamine (TCTA)), N,N'-di(naphthalene-l-yl)-N,N'-diphenyl-benzidine (NPB), 4,4'-cyclohexylenebis[N,N-bis(4-methylphenyl)aniline] (TAPC), 4,4'-bis[N,N'-(3-tolyl)amino]-3,3'-dimethylbiphenyl (HMTPD), 1,3-bis(N-carbazolyl)benzene (mCP), and the like.

[0442] In some embodiments, the hole transport region HTR may include at least one selected from 9-(4-tert-butylphenyl)-3,6-bis(triphenylsilyl)-9H-carbazole (CzSi), 9-phenyl-9H-3,9'-bicarbazole (CCP), 1,3-bis(1,8-dimethyl-9H-carbazole-9-yl)benzene (mDCP), and the like.

[0443] The hole transport region HTR may include one or more than one of the above-described compounds of the hole transport region in at least one of the hole injection layer HIL, the hole transport layer HTL, and the electron blocking layer EBL.

[0444] The thickness of the hole transport region HTR may be about to about For example, about to about When the hole transport region HTR includes the hole injection layer HIL, the hole injection layer HIL may have, for example, about to about When the hole transport region HTR includes the hole transport layer HTL, the hole transport layer HTL may have a thickness of about to about For example, when the hole transport region HTR includes the electron blocking layer EBL, the electron blocking layer EBL may have a thickness of about to about When the thicknesses of the hole transport region HTR, the hole injection layer HIL, the hole transport layer HTL, and the electron blocking layer EBL satisfy the above-described ranges, satisfactory hole transport properties may be achieved without a significant increase in driving voltage.

[0445] In one or more embodiments, in addition to the materials described above, the hole transport region HTR may further include a charge generating material to increase conductivity. The charge generating material may be substantially uniformly or non-uniformly dispersed in the hole transport region HTR. The charge generating material may be, for example, a p-dopant. The p-dopant may include at least one of a halogenated metal compound, a quinone derivative, a metal oxide, or a compound containing a cyano group, but the embodiments of the present disclosure are not limited thereto. For example, in some embodiments, the p-dopant may include a metal halide compound (e.g., CuI and / or RbI), a quinone derivative (e.g., tetracyanoquinodimethane (TCNQ) and / or 2,3,5,6-tetrafluoro-7,7',8,8'-tetracyanoquinodimethane (F4-TCNQ)), a metal oxide (e.g., tungsten oxide and / or molybdenum oxide), a cyano group-containing compound (e.g., dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile (HAT-CN) and / or 4-[[2,3-bis[cyano-(4-cyano-2,3,5,6-tetrafluorophenyl)methylene]cyclopropylidene]-cyanomethyl]-2,3,5,6-tetrafluorobenzonitrile (NDP9)), etc., but the embodiments of the present disclosure are not limited thereto.

[0446] As described above, in addition to the hole injection layer HIL and the hole transport layer HTL, the hole transport region HTR may further include at least one of a buffer layer and an electron blocking layer EBL. The buffer layer may compensate for the resonance distance according to the wavelength of light emitted from the light emitting layer EML and may thus increase the light emission efficiency. The material that may be included in the hole transport region HTR may be used as the material included in the buffer layer. The electron blocking layer EBL is a layer for preventing or reducing electron injection from the electron transport region ETR to the hole transport region HTR.

[0447] The light emitting layer EML may be provided on the hole transport region HTR. The light emitting layer EML may have, for example, about to about or about to about The light emitting layer EML may have a single layer formed of a single material, a single layer formed of a plurality of different materials, or a multilayer structure having a plurality of layers formed of a plurality of different materials.

[0448] In the light-emitting element ED according to one or more embodiments, the light-emitting layer EML may be intended to emit blue light. The light-emitting element ED according to one or more embodiments may include the amine compound according to one or more embodiments described above in the hole transport region HTR to exhibit high luminous efficiency and long life characteristics in the blue light-emitting region. However, the embodiments of the present disclosure are not limited thereto.

[0449] In the light-emitting element ED of one or more embodiments, the light-emitting layer EML may include an anthracene derivative, a pyrene derivative, a fluoranthene derivative, At least one of anthracene derivatives, dihydrobenzanthracene derivatives, and triphenylene derivatives. For example, in some embodiments, the light emitting layer EML may include one or more than one anthracene derivative and / or one or more than one pyrene derivative.

[0450] exist Figures 3 to 6 In the light-emitting element ED of one or more embodiments shown in the figure, the light-emitting layer EML may include a host and a dopant. For example, in some embodiments, the light-emitting layer EML may include a compound represented by formula E-1. The compound represented by formula E-1 may be used as a fluorescent host material.

[0451] Formula E-1

[0452]

[0453] In formula E-1, R 31 To R 40 Each of R and R may be independently hydrogen, deuterium, halogen, substituted or unsubstituted silyl group, substituted or unsubstituted thiol group, substituted or unsubstituted oxy group, substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, and / or may be combined with an adjacent group (e.g., bonded) to form a ring. In some embodiments, R 31 To R 40One or more than one of the may combine with an adjacent group to form a saturated hydrocarbon ring, an unsaturated hydrocarbon ring, a saturated heterocyclic ring or an unsaturated heterocyclic ring.

[0454] In Formula E-1, "c" and "d" may each independently be an integer of 0 to 5.

[0455] The compound represented by Formula E-1 may be any one selected from Compound E1 to Compound E19.

[0456]

[0457]

[0458] In one or more than one embodiments, the light emitting layer EML may include a compound represented by Formula E-2a or Formula E-2b. The compound represented by Formula E-2a or Formula E-2b may be used as a phosphorescent host material.

[0459] Formula E-2a

[0460]

[0461] In formula E-2a, "a" may be an integer from 0 to 10, and La may be a direct bond, a substituted or unsubstituted arylene group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring-forming carbon atoms. In some embodiments, when "a" is an integer of 2 or greater, multiple La may each independently be a substituted or unsubstituted arylene group having 6 to 30 ring-forming carbon atoms or a substituted or unsubstituted heteroarylene group having 2 to 30 ring-forming carbon atoms.

[0462] In some embodiments, in Formula E-2a, A 1 To A 5 Can be N or CR independently i . R a To R i may each independently be hydrogen, deuterium, a substituted or unsubstituted amine group, a substituted or unsubstituted thiol group, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, and / or may be combined with an adjacent group to form a ring. In some embodiments, the group selected from R a To R i One or more than one of them may combine with an adjacent group to form a hydrocarbon ring or a heterocyclic ring containing N, O, S, etc. as a ring atom.

[0463] In some embodiments, in Formula E-2a, selected from A 1 To A 5 Two or three of them can be N, and the rest can be CR i .

[0464] Formula E-2b

[0465]

[0466] In Formula E-2b, Cbz1 and Cbz2 may each independently be an unsubstituted carbazole group or a carbazole group substituted with an aryl group having 6 to 30 ring carbon atoms. b It may be a direct bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms. "b" is an integer from 0 to 10, and when "b" is an integer of 2 or more, multiple L b Each may independently be a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms.

[0467] The compound represented by Formula E-2a or Formula E-2b may be any one selected from the compounds in Compound Group E-2. However, the compounds shown in Compound Group E-2 are only examples, and the compounds represented by Formula E-2a or Formula E-2b are not limited to the compounds represented in Compound Group E-2.

[0468] Compound Group E-2

[0469]

[0470]

[0471] In one or more than one embodiments, the light emitting layer EML may further include a material very suitable in the art as a host material. For example, the light emitting layer EML may include at least one of bis(4-(9H-carbazol-9-yl)phenyl)diphenylsilane (BCPDS), (4-(1-(4-(diphenylamino)phenyl)cyclohexyl)phenyl)diphenyl-phosphine oxide (POPCPA), bis[2-(diphenylphosphino)phenyl]ether oxide (DPEPO), 4,4′-bis(N-carbazyl)-1,1′-biphenyl (CBP), 1,3-bis(N-carbazyl)benzene (mCP), 2,8-bis(diphenylphosphino)dibenzo[b,d]furan (PPF), 4,4′,4″-tri(carbazol-9-yl)-triphenylamine (TCTA), and 1,3,5-tri(1-phenyl-1H-benzo[d]imidazol-2-yl)benzene (TPBi) as a host material. However, embodiments of the present disclosure are not limited thereto. For example, tris(8-hydroxyquinolinolato)aluminum (Alq 3 ), 9,10-di(naphthalene-2-yl)anthracene (ADN), 2-tert-butyl-9,10-di(naphthalene-2-yl)anthracene (TBADN), distyryl arylide (DSA), 4,4′-bis(9-carbazolyl)-2,2′-dimethyl-biphenyl (CDBP), 2-methyl-9,10-bis(naphthalene-2-yl)anthracene (MADN), hexaphenylcyclotriphosphazene (CP1), 1,4-bis(triphenylsilyl)benzene (UGH2), hexaphenylcyclotrisiloxane (DPSiO 3 ), octaphenylcyclotetrasiloxane (DPSiO 4 ) etc. can be used as the main material.

[0472] In one or more than one embodiments, the light emitting layer EML may include a compound represented by formula Ma or formula Mb. The compound represented by formula Ma or formula Mb may be used as a phosphorescent dopant material. In some embodiments, the compound represented by formula Ma or formula Mb may be used as an auxiliary dopant material.

[0473] Formula Ma

[0474]

[0475] In formula Ma, Y 1 To Y 4 and Z 1 To Z 4 Can be CR independently 1 or N, and R 1 To R 4Each independently may be hydrogen, deuterium, a substituted or unsubstituted amine group, a substituted or unsubstituted thiol group, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, and / or may be combined with an adjacent group to form a ring. In formula Ma, "m" is 0 or 1, and "n" is 2 or 3. In formula Ma, when "m" is 0, "n" is 3, or when "m" is 1, "n" is 2.

[0476] The compound represented by the formula Ma may be used as a phosphorescent dopant.

[0477] The compound represented by formula Ma may be any one selected from compound M-a1 to compound M-a25. However, compound M-a1 to compound M-a25 are only examples, and the compound represented by formula Ma is not limited to the compounds represented by compound M-a1 to compound M-a25.

[0478]

[0479]

[0480] Formula Mb

[0481]

[0482] In formula Mb, Q 1 To Q 4 may be each independently C or N, and C1 to C4 may each independently be a substituted or unsubstituted hydrocarbon ring having 5 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic ring having 2 to 30 ring carbon atoms. 21 To L 24 Can be directly connected, *—O—*, *—S—*, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms, and e1 to e4 may each independently be 0 or 1. 21 To L 24 In the formula, "—*" is the site of connection with C1 to C4. 31 To R 39Each of d1 to d4 may independently be hydrogen, deuterium, a halogen, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, and / or combine with an adjacent group to form a ring, and d1 to d4 may independently be an integer of 0 to 4.

[0483] The compound represented by Formula Mb may be used as a blue phosphorescent dopant or a green phosphorescent dopant. In some embodiments, the compound represented by Formula Mb may be an auxiliary dopant and may be further included in the emission layer EML.

[0484] The compound represented by Formula Mb may be any one selected from Compound Mb-1 to Compound Mb-11. However, the compound is only an example, and the compound represented by Formula Mb is not limited to Compound Mb-1 to Compound Mb-11.

[0485]

[0486] In the above compounds, R, R 38 and R 39 Each may independently be hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms.

[0487] In one or more embodiments, the light-emitting layer EML may include a first compound represented by any one selected from Formula Fa to Formula Fc, a second compound represented by Formula HT-1, a third compound represented by Formula ET-1, and / or a fourth compound represented by Formula D-1.

[0488] Formula

[0489]

[0490] In the formula Fa, R a To R j The two of them can be independently *—NAr 1 Ar 2 Replace. a To R j The unrecognized in the 1 Ar 2The remainder of the substitution may be independently hydrogen, deuterium, halogen, cyano group, substituted or unsubstituted amine group, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms. 1 Ar 2 in Ar 1 and Ar 2 Each of them may be independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms. For example, in some embodiments, the group selected from Ar 1 and Ar 2 At least one of may be a heteroaryl group containing O or S as a ring-forming atom. —* indicates a position to be attached.

[0491] Formula Fb

[0492]

[0493] In formula Fb, R a and R b Each may independently be hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, and / or may combine with an adjacent group to form a ring. Ar 1 To Ar 4 Each may independently be a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms.

[0494] In Formula Fb, U and V may each independently be a substituted or unsubstituted hydrocarbon ring having 5 to 30 ring carbon atoms or a substituted or unsubstituted heterocyclic ring having 2 to 30 ring carbon atoms. 1 To Ar 4 At least one of may be a heteroaryl group containing O or S as a ring-forming atom.

[0495] In formula Fb, the number of rings represented by U and V can be 0 or 1 independently of each other. For example, in formula Fb, when the number of U or V is 1, a ring forms a fused ring at a specified portion of U or V, and when the number of U or V is 0, there is no ring at a specified portion of U or V. For example, when the number of U is 0 and the number of V is 1, or when the number of U is 1 and the number of V is 0, the fused ring with fluorene core of formula Fb can be a ring compound with four rings. In some embodiments, when the number of U and V is 0 (for example, simultaneously), the fused ring with fluorene core of formula Fb can be a ring compound with three rings. In some embodiments, when the number of U and V is 1 (for example, simultaneously), the fused ring with fluorene core of formula Fb can be a ring compound with five rings.

[0496] Formula Fc

[0497]

[0498] In Formula Fc, A 1 and A 2 can be independently O, S, Se or NR m , and R m It may be hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms. 1 To R 11 Each may independently be hydrogen, deuterium, halogen, a cyano group, a substituted or unsubstituted amine group, a substituted or unsubstituted boryl group, a substituted or unsubstituted oxy group, a substituted or unsubstituted thiol group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, and / or combine with an adjacent group to form a ring.

[0499] In Formula Fc, A 1 and A 2 Each of the substituents may independently combine with the substituents of the adjacent ring to form a fused ring. 1 and A 2 Can be NR independently m When A 1 Can be used with R 4 or R 5 In some embodiments, A 2 Can be used with R 7 or R 8 Combine to form a ring.

[0500] In one or more than one embodiments, the second compound can be used as a hole transport host material of the light emitting layer EML.

[0501] Formula HT-1

[0502]

[0503] In formula HT-1, A 1 To A 8 Can be N or CR independently 51 For example, in some embodiments, all A 1 To A 8 Can be CR 51 In some embodiments, selected from A 1 To A 8 Any one of them can be N, and the rest can be CR 51 .

[0504] In formula HT-1, L 1 It may be a direct bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms. For example, in some embodiments, L 1 It may be a direct bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted divalent biphenyl group, a substituted or unsubstituted divalent carbazole group, or the like, but embodiments of the present disclosure are not limited thereto.

[0505] In formula HT-1, Y a Can be direct key, CR 52 R 53 or SiR 54 R 55 For example, it may mean that the two benzene rings connected to the nitrogen atom of formula HT-1 may be connected via a direct bond, or connection. —* indicates the position to be connected. In formula HT-1, when Y a When it is a direct bond, the substituent represented by formula HT-1 may include a carbazole moiety.

[0506] In formula HT-1, Ar 1 It may be a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms. For example, in some embodiments, Ar 1 It may be a substituted or unsubstituted carbazole group, a substituted or unsubstituted dibenzofuran group, a substituted or unsubstituted dibenzothiophene group, a substituted or unsubstituted biphenyl group, or the like, but the embodiments of the present disclosure are not limited thereto.

[0507] In formula HT-1, R 51 To R 55 and R and R are each independently hydrogen, deuterium, halogen, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted thiol group, a substituted or unsubstituted oxy group, a substituted or unsubstituted amine group, a substituted or unsubstituted boron group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 ring-forming carbon atoms. In some embodiments, R 51 To R 55 One or more than one of can combine with adjacent groups to form a ring. For example, in some embodiments, R 51 To R 55 can each independently be hydrogen or deuterium. In some embodiments, R 51 To R 55 Each may independently be an unsubstituted methyl group or an unsubstituted phenyl group.

[0508] In one or more embodiments, the second compound represented by Formula HT-1 may be any one selected from the compounds represented in Compound Group 2. The light emitting layer EML may include at least one selected from the compounds represented in Compound Group 2 as a hole transport host material.

[0509] Compound Group 2

[0510]

[0511]

[0512]

[0513] In the exemplary compounds suggested in compound group 2, "D" refers to deuterium, and "Ph" can refer to a substituted or unsubstituted phenyl group. For example, in some embodiments, in the exemplary compounds suggested in compound group 2, "Ph" can be an unsubstituted phenyl group.

[0514] In one or more than one embodiments, the light emitting layer EML may include a third compound represented by Formula ET-1. For example, the third compound may be used as an electron transport host material of the light emitting layer EML.

[0515] Formula ET-1

[0516]

[0517] In formula ET-1, selected from X 1 To X 3 At least one of them may be N, and the rest may be CR 56 For example, in some embodiments, selected from X 1 To X 3 Only one of them can be N, and the remaining two can each independently be CR 56 In these embodiments, the third compound represented by Formula ET-1 may include a pyridine moiety. In some embodiments, the compound selected from X 1 To X 3 Two of them can be N, and the rest can be CR 56 In these embodiments, the third compound represented by Formula ET-1 may include a pyrimidine moiety. In some embodiments, X 1 To X 3 and may each be N. In these embodiments, the third compound represented by Formula ET-1 may include a triazine moiety.

[0518] In formula ET-1, R 56 It may be hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 ring carbon atoms.

[0519] In Formula ET-1, b1 to b3 may each independently be an integer of 0 to 10.

[0520] In formula ET-1, Ar 2 To Ar 4 and Ar may each independently be hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms. For example, in some embodiments, Ar 2 To Ar 4 It may be a substituted or unsubstituted phenyl group or a substituted or unsubstituted carbazole group.

[0521] In formula ET-1, L 2 To L 4 and L may be each independently a direct bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms. In some embodiments, when each of b1 to b3 is an integer of 2 or greater, L 2 To L 4Each may independently be a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms.

[0522] In one or more embodiments, the third compound may be any one of the compounds selected from compound group 3. The light-emitting element ED of one or more embodiments may include any one of the compounds selected from compound group 3.

[0523] Compound Group 3

[0524]

[0525]

[0526]

[0527]

[0528]

[0529]

[0530]

[0531] In the exemplary compounds suggested in Compound Group 3, "D" refers to deuterium, and "Ph" refers to an unsubstituted phenyl group.

[0532] In one or more embodiments, the light-emitting layer EML may include a second compound and a third compound, and the second compound and the third compound may form an exciplex. In the light-emitting layer EML, an exciplex may be formed by a hole transport host and an electron transport host. The triplet energy level of the exciplex formed by the hole transport host and the electron transport host may correspond to the difference between the lowest unoccupied molecular orbital (LUMO) energy level of the electron transport host and the highest occupied molecular orbital (HOMO) energy level of the hole transport host.

[0533] For example, the absolute value of the triplet energy level (T1) of the exciplex formed by the hole transport host and the electron transport host can be about 2.4 eV to about 3.0 eV. In some embodiments, the triplet energy level of the exciplex can be a value smaller than the energy gap of each host material. The exciplex can have a triplet energy level of about 3.0 eV or less, which is the energy gap between the hole transport host and the electron transport host.

[0534] In one or more embodiments, the light emitting layer EML may include a fourth compound in addition to the first to third compounds. The fourth compound may be used as a phosphorescence sensitizer of the light emitting layer EML. Because energy may be transferred from the fourth compound to the first compound, light emission may occur.

[0535] For example, in one or more embodiments, the light-emitting layer EML may include an organic metal complex including platinum (Pt) as a central metal atom and including a ligand bonded to the central metal atom as a fourth compound. In the light-emitting element ED according to one or more embodiments, the light-emitting layer EML may include a compound represented by formula D-1 as a fourth compound.

[0536] Formula D-1

[0537]

[0538] In formula D-1, Q 1 To Q 4 can each independently be C or N.

[0539] In Formula D-1, C1 to C4 may each independently be a substituted or unsubstituted hydrocarbon ring having 5 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic ring having 2 to 30 ring carbon atoms.

[0540] In formula D-1, L 11 To L 13 Can be directly connected, *—O—*, *—S—*, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms. 11 To L 13 In the above, “—*” refers to the part connecting to C1 to C4.

[0541] In formula D-1, b1 to b3 may each independently be 0 or 1. When b1 is 0, C1 and C2 may not be connected. When b2 is 0, C2 and C3 may not be connected. When b3 is 0, C3 and C4 may not be connected.

[0542] In formula D-1, R 61 To R 66and R and R are each independently hydrogen, deuterium, halogen, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted thiol group, a substituted or unsubstituted oxy group, a substituted or unsubstituted amine group, a substituted or unsubstituted boron group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 ring-forming carbon atoms. In some embodiments, R 61 To R 66 One or more than one of may combine with an adjacent group to form a ring. 61 To R 66 Each may independently be a substituted or unsubstituted methyl group or a substituted or unsubstituted tert-butyl group.

[0543] In Formula D-1, d1 to d4 may each independently be an integer of 0 to 4. In Formula D-1, when d1 to d4 are each 0, the fourth compound may be unreacted by R 61 To R 64 wherein d1 to d4 are each 4, and R 61 To R 64 The embodiment in which d1 to d4 are each hydrogen may be the same as the embodiment in which d1 to d4 are each 0. When d1 to d4 are integers of 2 or greater, the plurality of R 61 To multiple R 64 Each may be the same, or selected from a plurality of R 61 To multiple R 64 At least one of the respective ones may be different.

[0544] In Formula D-1, C1 to C4 may each independently be a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocyclic ring represented by any one selected from Formula C-1 to Formula C-4.

[0545]

[0546] In C-1 to C-4, P 1 Can be C—* or CR 74 , P 2 Can be N—* or NR 81 , P 3 Can be N—* or NR 82 , and P 4 Can be C—* or CR 88 . R 71 To R 88Each may independently be a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, and / or combine with adjacent atoms to form a ring.

[0547] Furthermore, in C-1 to C-4, is the part connected to the central metal atom of Pt, and “—*” corresponds to the part connected to the adjacent ring group (C1 to C4) or the linker (L 11 To L 13 ) connected part.

[0548] The light-emitting layer EML of one or more embodiments may include a first compound as a fused polycyclic compound, and at least one selected from the second compound to the fourth compound. For example, in some embodiments, the light-emitting layer EML may include a first compound, a second compound, and a third compound. In the light-emitting layer EML, the second compound and the third compound may form an exciplex, and energy transfer to the first compound may occur via the exciplex, and light emission may occur.

[0549] In some embodiments, the light-emitting layer EML may include a first compound, a second compound, a third compound, and a fourth compound. In the light-emitting layer EML, the second compound and the third compound may form an exciplex, and via the exciplex, energy transfer to the fourth compound and to the first compound may occur, and light emission may occur. In some embodiments, the fourth compound may be a sensitizer. In the light-emitting element ED of one or more embodiments, the fourth compound contained in the light-emitting layer EML may be used as a sensitizer, and may play a role in transferring energy from the host to the first compound as a light-emitting dopant. For example, the fourth compound acting as an auxiliary dopant may accelerate the energy transfer to the first compound as a light-emitting dopant, and increase the luminescence ratio of the first compound. Therefore, the emission efficiency of the light-emitting layer EML of one or more embodiments may be improved. In some embodiments, when the energy transfer to the first compound is increased, the excitons formed in the light-emitting layer EML may not accumulate but emit light quickly, and thus the degradation of the light-emitting element may be reduced. Therefore, the life of the light-emitting element ED of one or more embodiments may be increased.

[0550] The light-emitting element ED of one or more embodiments includes all of the first compound, the second compound, the third compound, and the fourth compound, and the light-emitting layer EML may include a combination of two host materials and two dopant materials. In the light-emitting element ED of one or more embodiments, the light-emitting layer EML may include the second compound and the third compound as two different hosts, the first compound emitting delayed fluorescence, and the fourth compound including the organic metal complex in parallel (e.g., simultaneously), and may exhibit excellent or suitable emission efficiency properties.

[0551] In one or more embodiments, the fourth compound represented by Formula D-1 may be at least one selected from the compounds represented in Compound Group 4. The light emitting layer EML may include at least one selected from the compounds represented in Compound Group 4 as a sensitizer material.

[0552] Compound Group 4

[0553]

[0554]

[0555] In the exemplary compounds suggested in Compound Group 4, "D" refers to deuterium.

[0556] In the light-emitting element ED of one or more embodiments, when the light-emitting layer EML includes all of the first compound, the second compound, the third compound, and the fourth compound, the amount of the first compound can be about 0.1 wt% to about 5 wt% based on the total weight of the first compound, the second compound, the third compound, and the fourth compound. However, the embodiments of the present disclosure are not limited thereto. When the amount of the first compound satisfies the ratio described above, the energy transfer from the second compound and the third compound to the first compound can be increased, and therefore, the emission efficiency and the device life can be increased.

[0557] In the light emitting layer EML, the total amount of the second compound and the third compound may be a residual amount excluding the amount of the first compound and the fourth compound. For example, the total amount of the second compound and the third compound may be about 65 wt % to about 95 wt % based on the total weight of the first compound, the second compound, the third compound, and the fourth compound.

[0558] In the total amount of the second compound and the third compound, a weight ratio of the second compound to the third compound may be about 3:7 to about 7:3.

[0559] When the total amount of the second compound and the third compound satisfies the ratio described above, the charge balance property in the light-emitting layer EML can be improved, and the emission efficiency and device life can be improved and / or increased. When the total amount of the second compound and the third compound deviates from the ratio range described above, the charge balance in the light-emitting layer EML may be destroyed, the emission efficiency may deteriorate and / or decrease, and the device may be easily degraded.

[0560] When the light-emitting layer EML includes a fourth compound, the amount of the fourth compound may be about 4 wt % to about 30 wt % based on the total weight of the first compound, the second compound, the third compound, and the fourth compound in the light-emitting layer EML. However, the embodiments of the present disclosure are not limited thereto. When the amount of the fourth compound satisfies the amount described above, the energy transfer from the host to the first compound as a light-emitting dopant can be increased, and the emissivity can be improved. Therefore, the emission efficiency of the light-emitting layer EML can be improved. When the amount ratio of the first compound, the second compound, the third compound, and the fourth compound contained in the light-emitting layer EML satisfies the amount ratio described above, the excellent or suitable emission efficiency and long life of the light-emitting element can be achieved.

[0561] In one or more embodiments, the light-emitting layer EML may include a styryl derivative (e.g., 1,4-bis[2-(3-N-ethylcarbazolyl)vinyl]benzene (BCzVB), 4-(di-p-tolylamino)-4'-[(di-p-tolylamino)styryl]phenylene (DPAVB), N-(4-((E)-2-(6-((E)-4-(diphenylamino)styryl)naphthalene-2-yl)vinyl)benzene One or more of the following can be used as suitable dopant materials: 4-(N,N-diphenylamino)-N-phenylaniline (N-BDAVBi) and 4,4'-bis[2-(4-(N,N-diphenylamino)phenyl)vinyl]biphenyl (DPAVBi)), perylene and its derivatives (e.g., 2,5,8,11-tetra-tert-butylperylene (TBP)), pyrene and its derivatives (e.g., 1,1'-dipyrene, 1,4-dipyrenylbenzene and 1,4-bis(N,N-diphenylamino)pyrene), etc.

[0562] In one or more than one embodiments, the light-emitting layer EML may include a suitable phosphorescent dopant material. For example, the phosphorescent dopant may utilize a metal complex comprising iridium (Ir), platinum (Pt), osmium (Os), gold (Au), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb) or thulium (Tm). For example, in some embodiments, bis (4,6-difluorophenylpyridinyl-N, C2') iridium (III) picolinate (FIrpic), bis (2,4-difluorophenylpyridinyl)-tetrakis (1-pyrazolyl) borate iridium (III) (FIr6) or octaethylporphyrin platinum (PtOEP) may be used as a phosphorescent dopant. However, the embodiments of the present disclosure are not limited thereto.

[0563] In some embodiments, the light-emitting layer EML may include a hole transport host and an electron transport host. In some embodiments, the light-emitting layer EML may include an auxiliary dopant and a light-emitting dopant. In some embodiments, the auxiliary dopant may include a phosphorescent dopant material and / or a thermally activated delayed fluorescent dopant. For example, in some embodiments, the light-emitting layer EML may include a hole transport host, an electron transport host, an auxiliary dopant, and a light-emitting dopant.

[0564] In one or more than one embodiments, the light emitting layer may comprise quantum dots.

[0565] In the present disclosure, quantum dots refer to crystals of semiconductor compounds. Quantum dots can emit light in one or more suitable emission wavelengths depending on the size of the crystal. Quantum dots can emit light in one or more suitable emission wavelengths by controlling the element ratio in the quantum dot compound.

[0566] The diameter of a quantum dot can be, for example, about 1 nm to about 10 nm.

[0567] Quantum dots can be synthesized by chemical bath deposition, metal organic chemical vapor deposition process, molecular beam epitaxy or a process similar thereto.

[0568] Chemical bath deposition is a method of mixing an organic solvent with a precursor material of a quantum dot and then growing a quantum dot particle crystal. During the crystal growth process, the organic solvent can naturally act as a dispersant coordinated to the surface of the quantum dot crystal and can control the growth of the crystal. Therefore, when compared with vapor deposition methods including metal organic chemical vapor deposition (MOCVD) and / or molecular beam epitaxy (MBE), chemical bath deposition is more advantageous, and the growth of quantum dot particles can be controlled or selected by a low-cost process.

[0569] In one or more embodiments, the light emitting layer EML may include a quantum dot material. In one or more embodiments, the quantum dot material may have a core / shell structure. The core of the quantum dot may be selected from II-VI compounds, III-VI compounds, I-III-VI compounds, III-V compounds, III-II-V compounds, IV-VI compounds, IV elements, IV compounds, and combinations thereof.

[0570] The II-VI compound may be selected from the group consisting of a binary compound selected from the group consisting of CdSe, CdTe, CdS, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, MgSe, MgS, and mixtures thereof; a ternary compound selected from the group consisting of CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS , CdZnSe, 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 and mixtures thereof. In some embodiments, the II-VI group compound may further comprise a Group I metal and / or a Group IV element. The I-II-VI group compound may be selected from CuSnS and / or CuZnS, and the II-IV-VI group compound may be selected from ZnSnS and the like. The I-II-IV-VI group compound may be selected from the group consisting of Cu 2 ZnSnS 2 , Cu 2 ZnSnS 4 , Cu 2 ZnSnSe 4 、Ag 2 ZnSnS 2 and any mixture thereof.

[0571] III-VI compounds may include: binary compounds, such as In 2 S 3 and / or In 2 Se 3 ; Ternary compounds, such as InGaS 3 and / or InGaSe 3 ; or any combination thereof.

[0572] The I-III-VI group compound may be selected from: a ternary compound selected from AgInS, AgInS 2 、CuInS、CuInS 2 、AgGaS 2 、CuGaS 2 、CuGaO 2 、AgGaO 2 、AgAlO 2 and mixtures thereof; and / or quaternary compounds such as AgInGaS 2 and / or CuInGaS 2 .

[0573] The III-V compound may be selected from the group consisting of: a binary compound selected from the group consisting of GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, InSb and a mixture thereof; a ternary compound selected from the group consisting of GaNP, GaNAs, GaNSb, GaPAs, GaPSb, AlNP, AlNAs, AlNSb, AlPAs, AlPSb, InGaP, InAlP, InNP, InNAs, InNSb, InPAs, InPSb and a mixture thereof; and a quaternary compound selected from the group consisting of GaAlNP, GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNP, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs, InAlPSb and a mixture thereof. In some embodiments, the III-V group compound may further include a II group metal. For example, InZnP or the like may be selected as the III-II-V group compound.

[0574] The IV-VI Group compound can be selected from the following groups: binary compounds, the binary compounds are selected from the group consisting of SnS, SnSe, SnTe, PbS, PbSe, PbTe and any mixture thereof; ternary compounds, the ternary compounds are selected from the group consisting of SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, SnPbTe and any mixture thereof; and quaternary compounds, the quaternary compounds are selected from the group consisting of SnPbSSe, SnPbSeTe, SnPbSTe and any mixture thereof.

[0575] The II-IV-V group compound can be selected from the group consisting of ZnSnP, ZnSnP2 、ZnSnAs 2 、ZnGeP 2 、ZnGeAs 2 、CdSnP 2 、CdGeP 2 and any mixture thereof.

[0576] The Group IV element may be selected from the group consisting of Si, Ge, and mixtures thereof. The Group IV compound may be a binary compound selected from the group consisting of SiC, SiGe, and any mixtures thereof.

[0577] Each element contained in the multi-element compound (such as a binary compound, a ternary compound, and a quaternary compound) may be present in the particle in a substantially uniform concentration or a substantially non-uniform concentration. For example, the above formula represents the type (species) of the element contained in the compound, and the ratio of the elements in the compound may be different. For example, AgInGaS 2 Can represent AgIn x Ga 1-x S 2 (x is a real number between 0 and 1).

[0578] In one or more than one embodiments, the constituent elements of the binary compound, ternary compound, or quaternary compound may be present in the particle at a substantially uniform concentration, or may be present in substantially the same particle at a partially different concentration distribution. In some embodiments, a core / shell structure in which one quantum dot surrounds another quantum dot may be ideal. The interface of the core and the shell may have a concentration gradient in which the concentration of the element present in the shell decreases toward the center.

[0579] In some embodiments, the quantum dot may have a core / shell structure as described above, comprising a core comprising a nanocrystal and a shell encapsulating the core. The shell of the quantum dot may act as a protective layer for preventing or reducing the chemical denaturation of the core to maintain semiconductor properties and / or as a charging layer for imparting electrophoretic properties to the quantum dot. The shell may have a single layer or multiple layers. Examples of the shell of the quantum dot may include metal or non-metal oxides, semiconductor compounds, or combinations thereof.

[0580] For example, the metal or nonmetal oxide used for the shell may include a binary compound (e.g. SiO 2 、Al 2 O 3 、TiO 2 、ZnO、MnO、Mn 2 O 3 , Mn 3 O 4 , CuO, FeO, Fe 2O 3 , Fe 3 O 4 , CoO, Co 3 O 4 and / or NiO), and / or ternary compounds (such as MgAl 2 O 4 、CoFe 2 O 4 、NiFe 2 O 4 and / or CoMn 2 O 4 ), but the embodiments of the present disclosure are not limited thereto.

[0581] In addition, semiconductor compounds suitable as shells may include CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnSeS, ZnTeS, GaAs, GaP, GaSb, HgS, HgSe, HgTe, InAs, InP, InGaP, InSb, AlAs, AlP, AlSb, etc., but the embodiments of the present disclosure are not limited thereto.

[0582] The quantum dots can have a full width at half maximum (FWHM) of an emission spectrum of about 45 nm or less, about 40 nm or less, or about 30 nm or less. Within this range, color purity or color reproducibility can be improved. In some embodiments, light emitted via such quantum dots is emitted in all directions, and light viewing angle properties can be improved.

[0583] In addition, the shape of the quantum dots can be any shape commonly used in the art without specific limitation. For example, spherical nanoparticles, pyramidal nanoparticles, multi-arm nanoparticles, or cubic nanoparticles, nanotubes, nanowires, nanofibers or nanoplates can be used.

[0584] As the size of the quantum dots or the ratio of elements in the quantum dot compound is adjusted, the band gap of the quantum dots can be controlled or selected accordingly to obtain one or more suitable wavelengths of light from the quantum dot emission layer. Therefore, by using quantum dots as described above (e.g., using quantum dots of different sizes and / or having different element ratios in the quantum dot compound), a light-emitting element that emits one or more suitable wavelengths of light can be obtained. For example, the size of the quantum dots and / or the ratio of elements in the quantum dot compound can be adjusted to emit red light, green light, and / or blue light. In some embodiments, the quantum dots can be configured to emit white light by combining one or more suitable colors of light.

[0585] In such Figures 3 to 6In the light-emitting element ED of one or more embodiments shown in the figure, an electron transport region ETR may be provided on the light-emitting layer EML. The electron transport region ETR may include at least one of an electron blocking layer EBL, an electron transport layer ETL, and an electron injection layer EIL. However, the embodiments of the present disclosure are not limited thereto.

[0586] The electron transport region ETR may have a single layer formed using a single material, a single layer formed using a plurality of different materials, or a multi-layered structure having a plurality of layers formed using a plurality of different materials.

[0587] For example, in one or more embodiments, the electron transport region ETR may have a single layer structure of an electron injection layer EIL or an electron transport layer ETL, or a single layer structure formed using an electron injection material and an electron transport material. In addition, in some embodiments, the electron transport region ETR may have a single layer structure formed using a plurality of different materials, or a structure of an electron transport layer ETL / electron injection layer EIL, or a hole blocking layer HBL / electron transport layer ETL / electron injection layer EIL stacked from the light emitting layer EML, without limitation. The thickness of the electron transport region ETR may be, for example, about 100 Å. to about

[0588] The electron transport region ETR may be formed using one or more suitable methods such as vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) method, inkjet printing, laser printing and / or laser induced thermal imaging (LITI) method.

[0589] In one or more than one embodiments, the electron transport region ETR may include a compound represented by Formula ET-2.

[0590] Formula ET-2

[0591]

[0592] In formula ET-2, selected from X 1 To X 3 At least one of them can be N, and the rest are CR a . R a It may be hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms. 1 To Ar 3Each may independently be hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms.

[0593] In Formula ET-2, "a" to "c" may each independently be an integer of 0 to 10. In Formula ET-2, L 1 To L 3 "a" to "c" may each independently be a direct bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms. In some embodiments, when "a" to "c" are each independently an integer of 2 or greater, L 1 To L 3 Each may independently be a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms.

[0594] In one or more than one embodiment, the electron transport region ETR may include an anthracene-based compound. However, the embodiments of the present disclosure are not limited thereto. For example, in some embodiments, the electron transport region ETR may include, for example, a compound selected from tris(8-hydroxyquinolinato)aluminum (Alq 3 ), 1,3,5-tris[(3-pyridyl)-phenyl-3-yl]benzene, 2,4,6-tris(3'-(pyridin-3-yl)biphenyl-3-yl)-1,3,5-triazine, 2-(4-(N-phenylbenzimidazol-1-yl)phenyl)-9,10-dinaphthylanthracene, 1,3,5-tris(1-phenyl-1H-benzo[d]imidazol-2-yl)benzene (TPBi), 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphe n), 3-(biphenyl-4-yl)-4-phenyl-5-tert-butylphenyl-1,2,4-triazole (TAZ), 4-(naphthalene-1-yl)-3,5-diphenyl-4H-1,2,4-triazole (NTAZ), 2-(biphenyl-4-yl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (tBu-PBD), bis(2-methyl-8-quinolinolato-N1,O8)-(1,1'-biphenyl-4-ato)aluminum (BAlq), bis(benzoquinolinolato-10-atoberyllium) (Bebq 2), 9,10-di(naphthalene-2-yl)anthracene (ADN), 1,3-bis[3,5-di(pyridin-3-yl)phenyl]benzene (BmPyPhB), CNNPTRZ (4'-(4-(4-(4,6-diphenyl-1,3,5-triazine-2-yl)phenyl)naphthalene-1-yl)-[1,1'-biphenyl]-4-carbonitrile) and mixtures thereof, without limitation.

[0595] In one or more than one embodiments, the electron transport region ETR may include at least one selected from compounds ET1 to ET36.

[0596]

[0597]

[0598]

[0599]

[0600] In some embodiments, the electron transport region ETR may include a metal halide (e.g., LiF, NaCl, CsF, RbCl, RbI, CuI, and / or KI), a lanthanide metal (e.g., Yb), or a co-deposited material of a metal halide and a lanthanide metal. For example, in some embodiments, the electron transport region ETR may include KI:Yb, RbI:Yb, LiF:Yb, etc. as a co-deposited material. In some embodiments, the electron transport region ETR may use a metal oxide (e.g., Li 2 O and / or BaO) or 8-hydroxy-quinoline lithium (Liq). However, the embodiments of the present disclosure are not limited thereto. In some embodiments, a mixture material of an electron transport material and an insulating organic metal salt can also be used to form an electron transport region ETR. The organic metal salt can be a material having an energy band gap of about 4 eV or greater than 4 eV. For example, the organic metal salt can include, for example, metal acetates, metal benzoates, metal acetoacetates, metal acetylacetonates and / or metal stearates.

[0601] In one or more than one embodiment, in addition to the above materials, the electron transport region ETR may include at least one of 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), diphenyl (4- (triphenylsilyl) phenyl) phosphine oxide (TSPO1) and 4,7-diphenyl-1,10-phenanthroline (Bphen). However, the embodiments of the present disclosure are not limited thereto.

[0602] The electron transport region ETR may include a compound of the electron transport region in at least one selected from the electron injection layer EIL, the electron transport layer ETL, and the hole blocking layer HBL.

[0603] When the electron transport region ETR includes the electron transport layer ETL, the thickness of the electron transport layer ETL may be about 100 Å. to about For example, about to about When the thickness of the electron transport layer ETL satisfies the above-described range, satisfactory electron transport properties can be obtained without a significant increase in driving voltage. When the electron transport region ETR includes the electron injection layer EIL, the thickness of the electron injection layer EIL can be about 1000 Å. to about or about to about When the thickness of the electron injection layer EIL satisfies the above range, satisfactory electron injection properties can be obtained without causing a significant increase in driving voltage.

[0604] A second electrode EL2 may be provided on the electron transport region ETR. The second electrode EL2 may be a common electrode. The second electrode EL2 may be a cathode or an anode, but the embodiments of the present disclosure are not limited thereto. For example, when the first electrode EL1 is an anode, the second cathode EL2 may be a cathode, and when the first electrode EL1 is a cathode, the second electrode EL2 may be an anode.

[0605] The second electrode EL2 may be a transmissive electrode, a semi-transmissive reflective electrode or a reflective electrode. When the second electrode EL2 is a transmissive electrode, the second electrode EL2 may include a transparent metal oxide, such as ITO, IZO, ZnO, ITZO, or the like.

[0606] When the second electrode EL2 is a semi-transmissive reflective electrode or a reflective electrode, the second electrode EL2 may include Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, Mo, Ti, Yb, W, one or more compounds thereof, or one or more mixtures thereof (e.g., AgMg, AgYb, or MgYb); or LiF / Ca or LiF / Al. In some embodiments, the second electrode EL2 may have a multilayer structure including a reflective layer or a semi-transmissive reflective layer formed using one or more materials selected from the materials described above, and a transparent conductive layer formed using ITO, IZO, ZnO, ITZO, etc. For example, the second electrode EL2 may include one or more selected from the aforementioned metal materials, any combination of two or more selected from the aforementioned metal materials, or any oxide of the aforementioned metal materials.

[0607] In some embodiments, the second electrode EL2 may be connected to an auxiliary electrode. When the second electrode EL2 is connected to the auxiliary electrode, the resistance of the second electrode EL2 may be reduced.

[0608] In some embodiments, a cover layer CPL may be further disposed on the second electrode EL2 in the light emitting element ED. The cover layer CPL may include a plurality of layers or a single layer.

[0609] In one or more embodiments, the capping layer CPL may be an organic layer or an inorganic layer. For example, in some embodiments, when the capping layer CPL comprises an inorganic material, the inorganic material may include an alkali metal compound (e.g., LiF), an alkaline earth metal compound (e.g., MgF 2 、SiON、SiN x 、SiO y )wait.

[0610] For example, in some embodiments, when the cover layer CPL includes an organic material, the organic material may include 2,2'-dimethyl-N,N'-di-[(1-naphthyl)-N,N'-diphenyl]-1,1'-biphenyl-4,4'-diamine (α-NPD), NPB, TPD, m-MTDATA, Alq 3 , CuPc, N4,N4,N4',N4'-tetrakis(biphenyl-4-yl)biphenyl-4,4'-diamine (TPD15), 4,4',4"-tris(carbazole-9-yl)triphenylamine (TCTA), etc., or may contain epoxy resin, and / or acrylate (e.g., methacrylate). In some embodiments, the cover layer CPL may contain at least one selected from compounds P1 to P5, but the embodiments of the present disclosure are not limited thereto.

[0611]

[0612]

[0613]

[0614] In some embodiments, the refractive index of the cover layer CPL can be about 1.6 or greater. For example, in one or more embodiments, the refractive index of the cover layer CPL can be about 1.6 or greater with respect to light in the wavelength range of about 550nm to about 660nm.

[0615] Figures 7 to 10 Each is a cross-sectional view of a display device according to one or more embodiments of the present disclosure. Figures 7 to 10In the explanation of the display device of the embodiment of the present invention, for the sake of simplicity, the explanation / description of the embodiment of the present invention will not be repeated. Figures 1 to 6 The explanations of the embodiments overlap, and only the different features will be explained first and primarily.

[0616] refer to Figure 7 , a display device DD-a according to one or more embodiments may include a display panel DP including a display device layer DP-ED, a light control layer CCL on the display panel DP, and a color filter layer CFL.

[0617] exist Figure 7 In one or more embodiments shown in the drawings, the display panel DP may include a base layer BS, a circuit layer DP-CL provided on the base layer BS, and a display device layer DP-ED, and the display device layer DP-ED may include a light emitting element ED.

[0618] The light emitting element ED may include a first electrode EL1, a hole transport region HTR on the first electrode EL1, an emission layer EML on the hole transport region HTR, an electron transport region ETR on the emission layer EML, and a second electrode EL2 on the electron transport region ETR. In one or more embodiments, as Figures 3 to 6 The same structure of any one of the light emitting elements can be applied to Figure 7 The structure of the light-emitting element ED is shown in FIG.

[0619] The hole transport region HTR of the light emitting element ED included in the display device DD-a according to one or more embodiments may include the amine compound of one or more embodiments described above.

[0620] refer to Figure 7 , the light-emitting layer EML may be disposed in the opening part OH defined in the pixel defining layer PDL. For example, the light-emitting layer EML divided by the pixel defining layer PDL and provided corresponding to each of the light-emitting regions PXA-R, PXA-G, and PXA-B may be intended to emit light in substantially the same wavelength region. In the display device DD-a of one or more embodiments, the light-emitting layer EML may be intended to emit blue light. In some embodiments, the light-emitting layer EML may be provided as a common layer for all light-emitting regions PXA-R, PXA-G, and PXA-B.

[0621] The light control layer CCL may be disposed on the display panel DP. The light control layer CCL may include a light converter. The light converter may be a quantum dot and / or a phosphor. The light converter may convert the wavelength of the provided light and then emit it. For example, the light control layer CCL may be a layer including quantum dots or a layer including phosphors.

[0622] The light-control layer CCL may include a plurality of light-control parts CCP1, CCP2, and CCP3. The light-control parts CCP1, CCP2, and CCP3 may be spaced apart and separated from each other.

[0623] refer to Figure 7 , the partition pattern BMP may be disposed between the separated light control parts CCP1, CCP2, and CCP3, but the embodiments of the present disclosure are not limited thereto. Figure 7 , the partitioning pattern BMP is shown not to overlap with the light control parts CCP1, CCP2, and CCP3, however, in some embodiments, at least a portion of the edges of the light control parts CCP1, CCP2, and CCP3 may overlap with the partitioning pattern BMP.

[0624] The light control layer CCL may include a first light control component CCP1 including first quantum dots QD1 that convert the first color light provided by the light emitting element ED into second color light, a second light control component CCP2 including second quantum dots QD2 that convert the first color light into third color light, and a third light control component CCP3 that transmits the first color light.

[0625] In one or more embodiments, the first light control component CCP1 can provide red light as the second color light, and the second light control component CCP2 can provide green light as the third color light. The third color control component CCP3 can be intended to transmit and provide blue light as the first color light provided by the light emitting element ED. For example, in some embodiments, the first quantum dot QD1 can be a red quantum dot to emit red light, and the second quantum dot QD2 can be a green quantum dot to emit green light. With respect to quantum dots QD1 and quantum dots QD2, the same contents as those described above can apply.

[0626] In some embodiments, the light control layer CCL may further include a scatterer SP. The first light control component CCP1 may include a first quantum dot QD1 and a scatterer SP, the second light control component CCP2 may include a second quantum dot QD2 and a scatterer SP, and the third light control component CCP3 may not include (e.g., may exclude) any quantum dot but may include a scatterer SP.

[0627] The scatterer SP may be an inorganic particle. For example, the scatterer SP may include a particle selected from TiO 2 、ZnO、Al 2 O 3 、SiO 2 In one or more embodiments, the scatterer SP may include at least one selected from TiO 2 、ZnO、Al 2 O3 、SiO 2 and hollow silica, or may be selected from TiO 2 、ZnO、Al 2 O 3 、SiO 2 and a mixture of two or more materials in hollow silica.

[0628] The first light control component CCP1, the second light control component CCP2 and the third light control component CCP3 may respectively include matrix resins BR1, BR2 and BR3 of dispersed quantum dots QD1 and QD2 and scatterers SP. In one or more embodiments, the first light control component CCP1 may include first quantum dots QD1 and scatterers SP dispersed in the first matrix resin BR1, the second light control component CCP2 may include second quantum dots QD2 and scatterers SP dispersed in the second matrix resin BR2, and the third light control component CCP3 may include scatterer particles SP dispersed in the third matrix resin BR3.

[0629] The matrix resins BR1, BR2 and BR3 are media in which quantum dots QD1 and QD2 and scatterers SP are dispersed, and may be composed of one or more suitable resin compositions (which may be generally referred to as adhesives). For example, the matrix resins BR1, BR2 and BR3 may each independently be an acrylic-based resin, a urethane-based resin, a silicone-based resin, an epoxy-based resin, etc. The matrix resins BR1, BR2 and BR3 may be transparent resins. In one or more than one embodiments, the first matrix resin BR1, the second matrix resin BR2 and the third matrix resin BR3 may be the same or different from each other.

[0630] In one or more than one embodiments, the light control layer CCL may include a barrier layer BFL1. The barrier layer BFL1 may play a role in blocking the penetration of moisture and / or oxygen (hereinafter, referred to as "moisture / oxygen"). The barrier layer BFL1 may block or reduce the exposure of the light control components CCP1, CCP2, and CCP3 to moisture / oxygen. In some embodiments, the barrier layer BFL1 may cover the light control components CCP1, CCP2, and CCP3. In some embodiments, the color filter layer CFL, which will be explained later, may include a barrier layer BFL2 disposed on the light control components CCP1, CCP2, and CCP3.

[0631] The barrier layers BFL1 and BFL2 may include at least one inorganic layer. For example, in some embodiments, the barrier layers BFL1 and BFL2 may be formed by including an inorganic material. For example, the barrier layers BFL1 and BFL2 may be formed by including one or more than one selected from 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 a metal film that ensures light transmittance. In some embodiments, the barrier layers BFL1 and BFL2 may further include an organic layer. The barrier layers BFL1 and BFL2 may be composed of a single layer or multiple layers.

[0632] In the display device DD-a of one or more embodiments, the color filter layer CFL may be disposed on the light control layer CCL. For example, the color filter layer CFL may be disposed directly on the light control layer CCL. In these embodiments, the blocking layer BFL2 may not be provided.

[0633] The color filter layer CFL may include filters CF1, CF2, and CF3. Each of the first to third filters CF1, CF2, and CF3 may be disposed corresponding to the red light emitting area PXA-R, the green light emitting area PXA-G, and the blue light emitting area PXA-B, respectively.

[0634] The color filter layer CFL may include a first filter CF1 that transmits a second color light, a second filter CF2 that transmits a third color light, and a third filter CF3 that transmits the first color light. For example, in some embodiments, 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 the filters CF1, CF2, and CF3 may include a polymer photosensitive resin and a pigment and / or dye. The first filter CF1 may include a red pigment and / or dye, the second filter CF2 may include a green pigment and / or dye, and the third filter CF3 may include a blue pigment and / or dye.

[0635] In some embodiments, the third filter CF3 may not include (e.g., may exclude) any pigment and / or dye. The third filter CF3 may include a polymer photosensitive resin and may not include any pigment and / or dye. The third filter CF3 may be transparent. The third filter CF3 may be formed using a transparent photosensitive resin.

[0636] In some embodiments, the first filter CF1 and the second filter CF2 may each be a yellow filter. The first filter CF1 and the second filter CF2 may be provided integrally without distinction.

[0637] In one or more embodiments, the color filter layer CFL may further include a light blocking member. The color filter layer CFL may include a light blocking member arranged to overlap the boundaries of adjacent filters CF1, CF2, and CF3. The light blocking member may be a black matrix. The light blocking member may be formed by including an organic light blocking material and / or an inorganic light blocking material (including a black pigment and / or a black dye). The light blocking member may prevent or reduce light leakage and divide the boundaries between adjacent filters CF1, CF2, and CF3.

[0638] On the color filter layer CFL, a base substrate BL may be disposed / provided. The base substrate BL may be a member that provides a base surface on which the color filter layer CFL, the light control layer CCL, etc. are disposed. The base substrate BL may be a glass substrate, a metal substrate, a plastic substrate, etc. However, the embodiments of the present disclosure are not limited thereto, and the base substrate BL may be an inorganic layer, an organic layer, or an organic-inorganic composite material layer. In some embodiments, the base substrate BL may not be provided.

[0639] Figure 8 is a cross-sectional view showing a portion of a display device according to one or more embodiments. In the display device DD-TD of one or more embodiments, the light emitting element ED-BT may include a plurality of light emitting structures OL-B1, OL-B2, and OL-B3. The light emitting element ED-BT may include a first electrode EL1 and a second electrode EL2 disposed opposite to each other, and a plurality of light emitting structures OL-B1, OL-B2, and OL-B3 stacked in sequence in the thickness direction and provided between the first electrode EL1 and the second electrode EL2. Each of the light emitting structures OL-B1, OL-B2, and OL-B3 may include a light emitting layer EML ( Figure 7 ), and the hole transport region HTR and the electron transport region ETR ( Figure 7 ).

[0640] For example, in some embodiments, the light emitting elements ED-BT included in the display devices DD-TD may be light emitting elements of a series structure including a plurality of light emitting layers.

[0641] exist Figure 8In one or more embodiments shown in the figure, the light emitted by the light emitting structures OL-B1, OL-B2 and OL-B3 may all be blue light. However, the embodiments of the present disclosure are not limited thereto, and the wavelength regions of the light emitted from the light emitting structures OL-B1, OL-B2 and OL-B3 may be different from each other. For example, in one or more embodiments, the light emitting element ED-BT including a plurality of light emitting structures OL-B1, OL-B2 and OL-B3, each emitting light in a different wavelength region, may be intended to emit white light (e.g., combined white light).

[0642] Charge generation layers CGL1 and CGL2 may 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 or species charge (e.g., P-charge) generation layers and / or n-type or species charge (e.g., N-charge) generation layers.

[0643] The above-described amine compound according to one or more embodiments may be included in at least one selected from the light emitting structures OL-B1, OL-B2, and OL-B3 included in the display devices DD-TD according to one or more embodiments.

[0644] Fig. 9 is a cross-sectional view showing a display device according to one or more embodiments of the present disclosure. Fig.10 is a cross-sectional view showing a display device according to one or more embodiments of the present disclosure.

[0645] refer to Fig. 9 , the display device DD-b according to one or more embodiments may include light emitting elements ED-1, ED-2, and ED-3, each formed by stacking two light emitting layers. Figure 2 Compared with the display device DD shown in Fig. 9 The display device DD-b shown in FIG. 1 is different in that the first to third light-emitting elements ED-1, ED-2, and ED-3 each include two light-emitting layers stacked in the thickness direction. In the first to third light-emitting elements ED-1, ED-2, and ED-3, the two light-emitting layers may be intended to emit light in substantially the same wavelength region.

[0646] In one or more embodiments, the first light-emitting element ED-1 may include a first red light-emitting layer EML-R1 and a second red light-emitting layer EML-R2. The second light-emitting element ED-2 may include a first green light-emitting layer EML-G1 and a second green light-emitting layer EML-G2. In addition, the third light-emitting element ED-3 may include a first blue light-emitting layer EML-B1 and a second blue light-emitting layer EML-B2. An emission auxiliary component OG may be provided between the first red light-emitting layer EML-R1 and the second red light-emitting layer EML-R2, between the first green light-emitting layer EML-G1 and the second green light-emitting layer EML-G2, and between the first blue light-emitting layer EML-B1 and the second blue light-emitting layer EML-B2.

[0647] The emission auxiliary component OG may include a single layer or a multilayer. The emission auxiliary component OG may include a charge generation layer. For example, the emission auxiliary component OG may include an electron transport region, a charge generation layer, and a hole transport region stacked in sequence (e.g., a prescribed order). The emission auxiliary component OG may be provided as a common layer in all the first to third light-emitting elements ED-1, ED-2, and ED-3. However, the embodiments of the present disclosure are not limited thereto, and the emission auxiliary component OG may be patterned and provided in an opening component OH defined in the pixel defining layer PDL.

[0648] The first red light emitting layer EML-R1, the first green light emitting layer EML-G1, and the first blue light emitting layer EML-B1 may be disposed between the electron transport region ETR and the emission auxiliary component OG. The second red light emitting layer EML-R2, the second green light emitting layer EML-G2, and the second blue light emitting layer EML-B2 may be disposed between the emission auxiliary component OG and the hole transport region HTR.

[0649] For example, in one or more embodiments, the first light-emitting element ED-1 may include a first electrode EL1, a hole transport region HTR, a second red light-emitting layer EML-R2, an emission auxiliary component OG, a first red light-emitting layer EML-R1, an electron transport region ETR, and a second electrode EL2 stacked in sequence (e.g., in a prescribed order). The second light-emitting element ED-2 may include a first electrode EL1, a hole transport region HTR, a second green light-emitting layer EML-G2, an emission auxiliary component OG, a first green light-emitting layer EML-G1, an electron transport region ETR, and a second electrode EL2 stacked in sequence (e.g., in a prescribed order). The third light-emitting element ED-3 may include a first electrode EL1, a hole transport region HTR, a second blue light-emitting layer EML-B2, an emission auxiliary component OG, a first blue light-emitting layer EML-B1, an electron transport region ETR, and a second electrode EL2 stacked in sequence (e.g., in a prescribed order).

[0650] In one or more embodiments, an optical auxiliary layer PL may be disposed on the display device layer DP-ED. The optical auxiliary layer PL may include a polarizing layer. The optical auxiliary layer PL may be disposed on the display panel DP and may control light reflected by external light at the display panel DP. In some embodiments, the display device may not provide an optical auxiliary layer PL.

[0651] Different from Figure 8 and Fig. 9 , Fig.10 The display device DD-c in FIG. 1 is shown to include four light emitting structures OL-B1, OL-B2, OL-B3, and OL-C1. The light emitting element ED-CT may include a first electrode EL1 and a second electrode EL2 disposed opposite to each other, and first to fourth light emitting structures OL-B1, OL-B2, OL-B3, and OL-C1 stacked in the thickness direction between the first electrode EL1 and the second electrode EL2. For example, the third light emitting structure OL-B3, the second light emitting structure OL-B2, the first light emitting structure OL-B1, and the fourth light emitting structure OL-C1 are stacked in sequence (e.g., in a prescribed order) in the thickness direction. Between the first to fourth light emitting structures OL-B1, OL-B2, OL-B3, and OL-C1, charge generation layers CGL1, CGL2, and CGL3 may be disposed. For example, the first charge generation layer CGL1 is disposed between the first light emitting structure OL-B1 and the fourth light emitting structure OL-C1. The second charge generation layer CGL2 is disposed between the first light emitting structure OL-B1 and the second light emitting structure OL-B2. The third charge generation layer CGL3 is disposed between the second light emitting structure OL-B2 and the third light emitting structure OL-B3.

[0652] Among the four light emitting structures, the first to third light emitting structures OL-B1, OL-B2, and OL-B3 may be intended to emit blue light, and the fourth light emitting structure OL-C1 may be intended to emit green light. However, the embodiments of the present disclosure are not limited thereto, and the first to fourth light emitting structures OL-B1, OL-B2, OL-B3, and OL-C1 may be intended to emit light of different wavelengths.

[0653] The above-described amine compound according to one or more embodiments may be included in at least one selected from the light emitting structures OL-B1, OL-B2, OL-B3, and OL-C1 included in the display device DD-c according to one or more embodiments.

[0654] The light-emitting element ED according to one or more embodiments of the present disclosure may include the amine compound described above according to one or more embodiments in at least one functional layer disposed between the first electrode EL1 and the second electrode EL2, and thus may exhibit improved luminous efficiency and improved service life characteristics. The light-emitting element ED according to one or more embodiments may include the amine compound described above according to one or more embodiments in at least one of the hole transport region HTR, the light-emitting layer EML, and the electron transport region ETR, each disposed between the first electrode EL1 and the second electrode EL2, or also in the cover layer CPL. For example, the amine compound according to one or more embodiments may be included in the hole transport region HTR of the light-emitting element ED according to one or more embodiments, and the light-emitting element ED according to one or more embodiments may exhibit high efficiency and long service life characteristics.

[0655] The amine compound described above according to one or more embodiments includes a first amine group, a second amine group, a first connector connecting the first amine group and the second amine group, and a first substituent connected to the first amine group, the first substituent includes a naphthyl moiety and a first substituent, and thus the stability of the material can be increased and the hole transport capability can be improved. Therefore, the light-emitting element comprising the amine compound according to one or more embodiments can have improved service life and efficiency. In some embodiments, the light-emitting element according to one or more embodiments can include the amine compound according to one or more embodiments in the hole transport layer, thereby showing improved efficiency and service life characteristics.

[0656] Fig.11 is a diagram showing an automobile AM ​​in which first to fourth display devices DD-1, DD-2, DD-3, and DD-4 are arranged. At least one selected from the first to fourth display devices DD-1, DD-2, DD-3, and DD-4 may include reference Figure 1 , Figure 2 and Figures 7 to 10 The explained display devices DD, DD-TD, DD-a, DD-b and / or DD-c have substantially the same configuration.

[0657] exist Fig.11In, the vehicle is shown as a car AM, but this is only an example. The first display device to the fourth display device DD-1, DD-2, DD-3 and DD-4 can be arranged on other transportation equipment such as bicycles, motorcycles, trains, ships and / or airplanes. In some embodiments, at least one of the first display device to the fourth display device DD-1, DD-2, DD-3 and DD-4 of the substantially identical configuration including display device DD, DD-TD, DD-a, DD-b and / or DD-c can be introduced into a personal computer, a laptop computer, a personal digital terminal, a game console, a portable electronic device, a television, a monitor, an external billboard, etc. These are only shown as examples, and the display device can be introduced into other electronic devices, as long as it does not deviate from the present disclosure.

[0658] In one or more embodiments, at least one selected from the first to fourth display devices DD-1, DD-2, DD-3, and DD-4 may include a reference Figures 3 to 6 The light-emitting element ED of one or more embodiments described. The light-emitting element ED according to one or more embodiments may include the amine compound of one or more embodiments. In one or more embodiments, at least one selected from the first to fourth display devices DD-1, DD-2, DD-3 and DD-4 may include a light-emitting element ED including the amine compound of one or more embodiments, thereby increasing the service life.

[0659] refer to Fig.11 The automobile AM ​​may include a steering wheel HA and a shift member GR for operating the automobile AM. In addition, the automobile AM ​​may include a front window GL disposed toward the driver.

[0660] The first display device DD-1 may be arranged in a first area overlapping with the steering wheel HA. For example, the first display device DD-1 may be a digital cluster device displaying first information of the automobile AM. The first information may include a first scale showing the driving speed of the automobile AM, a second scale showing the engine revolutions (i.e., revolutions per minute (RPM)), and an image showing the fuel status. The first scale and the second scale may be represented by digital images.

[0661] The second display device DD-2 can be arranged in a second zone facing the driver's seat and overlapping with the front window GL. The driver's seat can be the seat to which the steering wheel HA faces. For example, the second display device DD-2 can be a head-up display (HUD) showing the second information of the automobile AM. The second display device DD-2 can be optically transparent. The second information can include a digital number showing the driving speed of the automobile AM, and can further include information including the current time. In some embodiments, the second information of the second display device DD-2 can be projected and displayed on the front window GL.

[0662] The third display device DD-3 may be disposed in a third zone adjacent to the shift member GR. For example, the third display device DD-3 may be a central information display (CID) for a car disposed between a driver's seat and a passenger seat and displaying the third information. The passenger seat may be a seat separated from the driver's seat, with the shift member GR therebetween. The third information may include information about road conditions (e.g., navigation information), information about playing music or broadcasting, information about playing dynamic images (or images), information about the temperature inside the car AM, and the like.

[0663] The fourth display device DD-4 may be disposed in a fourth area separated from the steering wheel HA and the shift member GR and adjacent to one side of the automobile AM. For example, the fourth display device DD-4 may be a digital side mirror that displays the fourth information. The fourth display device DD-4 may display an external image of the automobile AM ​​captured by a camera module CM disposed outside the automobile AM. The fourth information may include an external image of the automobile AM.

[0664] The first to fourth information described above are only examples, and the first to fourth display devices DD-1, DD-2, DD-3, and DD-4 can further display information about the interior and exterior of the car. The first to fourth information may include information that is different from each other. However, the embodiments of the present disclosure are not limited thereto, for example, in some embodiments, a portion of the first to fourth information may include the same information.

[0665] Hereinafter, the amine compound according to one or more embodiments of the present disclosure and the light-emitting element according to one or more embodiments will be described in more detail with reference to Examples and Comparative Examples. In addition, the described examples are only for understanding the present disclosure, but the scope of the present disclosure is not limited thereto.

[0666] Example

[0667] 1. Synthesis of amine compounds

[0668] First, the synthesis method of the amine compound according to one or more embodiments will be described in more detail by the exemplary synthesis method of compound 64, compound 67, compound 73, compound 76, compound 81, compound 84, compound 88, compound 91, compound 92, compound 94, compound 96, compound 100, compound 121, compound 122, compound 127, compound 128, compound 130, compound 135, compound 140, compound 145, compound 147, compound 153, compound 155, compound 157 and compound 181. In some embodiments, the synthesis method of the described amine compound is provided as an example, but the synthesis method of the compound according to the embodiment according to the present disclosure is not limited to the example.

[0669] (1) Synthesis of Compound 64

[0670] Synthesis of Intermediate 64-1

[0671]

[0672] 1,4-Dibromobenzene (26 mmol, 1.3 equivalents), N-phenyl-[1,1'-biphenyl]-4-amine (20 mmol, 1 equivalent), tris(dibenzylideneacetone)dipalladium(0) (Pd 2 (dba) 3 ) (1 mmol, 0.05 equivalent), sodium tert-butoxide (t-BuONa) (40 mmol, 2 equivalents), 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (BINAP, 2 mmol, 0.1 equivalents) and 300 mL of toluene were put into a single-necked round-bottom flask, and the mixture was stirred at about 110° C. for about 1 hour. After the reaction was completed, the resultant was washed with ether / H 2 O, and then purified by column chromatography using dichloromethane / hexane = 1 / 5 (v / v) as the eluent to obtain about 12 mmol of Intermediate 64-1 (yield = 60%).

[0673] Synthesis of compound 64

[0674]

[0675] Intermediate 64-1 (12 mmol, 1.2 equivalents), N-(4-cyclohexylphenyl)-1-phenylnaphthalen-2-amine (10 mmol, 1 equivalent), Pd 2 (dba) 3 (0.5 mol, 0.05 equivalent), t-BuONa (20 mmol, 2 equivalents), t-Bu 3P (0.1 mmol, 0.1 equivalent) and 150 mL of toluene were placed in a single-necked round-bottom flask, and the mixture was stirred at about 110° C. for about 1 hour. After the reaction was completed, the resultant was washed with ether / H 2 O, and then purified by column chromatography using dichloromethane / hexane = 1 / 8 (v / v) as an eluent to obtain about 6.3 mmol of Compound 64 (yield = 63%).

[0676] (2) Synthesis of Compound 67

[0677] Synthesis of Intermediate 67-1

[0678]

[0679] 1,4-dibromobenzene (26 mmol, 1.3 equivalents), N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-9H-fluoren-2-amine (20 mmol, 1 equivalent), Pd 2 (dba) 3 (1 mmol, 0.05 equivalent), t-BuONa (40 mmol, 2 equivalents), BINAP (2 mmol, 0.1 equivalents) and 300 mL of toluene were placed in a single-necked round-bottom flask, and the mixture was stirred at about 110° C. for about 1 hour. After the reaction was completed, the resultant was washed with ether / H 2 O, and then purified by column chromatography using dichloromethane / hexane=1 / 5 (v / v) as the eluent to obtain about 13 mmol of Intermediate 67-1 (yield=65%).

[0680] Synthesis of compound 67

[0681]

[0682] Intermediate 67-1 (12 mmol, 1.2 equivalents), N,1-diphenylnaphthalene-2-amine (10 mmol, 1 equivalent), Pd 2 (dba) 3 (0.5 mol, 0.05 equivalent), t-BuONa (20 mmol, 2 equivalents), t-Bu 3 P (0.1 mmol, 0.1 equivalent) and 150 mL of toluene were placed in a single-necked round-bottom flask, and the mixture was stirred at about 110° C. for about 1 hour. After the reaction was completed, the resultant was washed with ether / H 2 O, and then purified by column chromatography using dichloromethane / hexane = 1 / 8 (v / v) as an eluent to obtain about 5.9 mmol of Compound 67 (yield = 59%).

[0683] (3) Synthesis of Compound 73

[0684] Synthesis of Intermediate 73-1

[0685]

[0686] 1,3-Dibromobenzene (26 mmol, 1.3 equivalents), 9,9-dimethyl-N-phenyl-9H-fluoren-2-amine (20 mmol, 1 equivalent), Pd 2 (dba) 3 (1 mmol, 0.05 equivalent), t-BuONa (40 mmol, 2 equivalents), BINAP (2 mmol, 0.1 equivalents) and 300 mL of toluene were placed in a single-necked round-bottom flask, and the mixture was stirred at about 110° C. for about 1 hour. After the reaction was completed, the resultant was washed with ether / H 2 O, and then purified by column chromatography using dichloromethane / hexane = 1 / 5 (v / v) as an eluent to obtain about 13 mmol of Intermediate 73-1 (yield = 65%).

[0687] Synthesis of compound 73

[0688]

[0689] Intermediate 73-1 (12 mmol, 1.2 equivalents), N-(naphthalen-2-yl)-1-phenylnaphthalen-2-amine (10 mmol, 1 equivalent), Pd 2 (dba) 3 (0.5 mol, 0.05 equivalent), t-BuONa (20 mmol, 2 equivalents), t-Bu 3 P (0.1 mmol, 0.1 equivalent) and 150 mL of toluene were placed in a single-necked round-bottom flask, and the mixture was stirred at about 110° C. for about 1 hour. After the reaction was completed, the resultant was washed with ether / H 2 O, and then purified by column chromatography using dichloromethane / hexane = 1 / 8 (v / v) as an eluent to obtain about 6.0 mmol of Compound 73 (yield = 60%).

[0690] (4) Synthesis of Compound 76

[0691] Synthesis of Intermediate 76-1

[0692]

[0693] 1,3-Dibromobenzene (26 mmol, 1.3 equivalents), N-(4-cyclohexylphenyl)-9,9-dimethyl-9H-fluoren-2-amine (20 mmol, 1 equivalent), Pd 2 (dba) 3(1 mmol, 0.05 equivalent), t-BuONa (40 mmol, 2 equivalents), BINAP (2 mmol, 0.1 equivalents) and 300 mL of toluene were placed in a single-necked round-bottom flask, and the mixture was stirred at about 110° C. for about 1 hour. After the reaction was completed, the resultant was washed with ether / H 2 O, and then purified by column chromatography using dichloromethane / hexane = 1 / 5 (v / v) as the eluent to obtain about 12 mmol of Intermediate 76-1 (yield = 60%).

[0694] Synthesis of compound 76

[0695]

[0696] Intermediate 76-1 (12 mmol, 1.2 equivalents), N-(naphthalen-2-yl)-1-phenylnaphthalen-2-amine (10 mmol, 1 equivalent), Pd 2 (dba) 3 (0.5 mol, 0.05 equivalent), t-BuONa (20 mmol, 2 equivalents), t-Bu 3 P (0.1 mmol, 0.1 equivalent) and 150 mL of toluene were placed in a single-necked round-bottom flask, and the mixture was stirred at about 110° C. for about 1 hour. After the reaction was completed, the resultant was washed with ether / H 2 O, and then purified by column chromatography using dichloromethane / hexane = 1 / 8 (v / v) as an eluent to obtain about 5.0 mmol of Compound 76 (yield = 50%).

[0697] (5) Synthesis of Compound 81

[0698] Synthesis of Intermediate 81-1

[0699]

[0700] 1,4-dibromobenzene (26 mmol, 1.3 equivalents), N-([1,1'-biphenyl]-4-yl)-9,9-diphenyl-9H-fluoren-2-amine (20 mmol, 1 equivalent), Pd 2 (dba) 3 (1 mmol, 0.05 equivalent), t-BuONa (40 mmol, 2 equivalents), BINAP (2 mmol, 0.1 equivalents) and 300 mL of toluene were placed in a single-necked round-bottom flask, and the mixture was stirred at about 110° C. for about 1 hour. After the reaction was completed, the resultant was washed with ether / H 2O, and then purified by column chromatography using dichloromethane / hexane=1 / 5 (v / v) as an eluent to obtain about 15 mmol of Intermediate 81-1 (yield=75%).

[0701] Synthesis of compound 81

[0702]

[0703] Intermediate 81-1 (12 mmol, 1.2 equivalents), N,1-diphenylnaphthalene-2-amine (10 mmol, 1 equivalent), Pd 2 (dba) 3 (0.5 mol, 0.05 equivalent), t-BuONa (20 mmol, 2 equivalents), t-Bu 3 P (0.1 mmol, 0.1 equivalent) and 150 mL of toluene were placed in a single-necked round-bottom flask, and the mixture was stirred at about 110° C. for about 1 hour. After the reaction was completed, the resultant was washed with ether / H 2 O, and then purified by column chromatography using dichloromethane / hexane = 1 / 8 (v / v) as an eluent to obtain about 7.0 mmol of Compound 81 (yield = 70%).

[0704] (6) Synthesis of Compound 84

[0705] Synthesis of Intermediate 84-1

[0706]

[0707] 1,4-dibromobenzene (26 mmol, 1.3 equivalents), N-(4-cyclohexylphenyl)-9,9'-spirobis[fluorene]-2-amine (20 mmol, 1 equivalent), Pd 2 (dba) 3 (1 mmol, 0.05 equivalent), t-BuONa (40 mmol, 2 equivalents), BINAP (2 mmol, 0.1 equivalents) and 300 mL of toluene were placed in a single-necked round-bottom flask, and the mixture was stirred at about 110° C. for about 1 hour. After the reaction was completed, the resultant was washed with ether / H 2 O, and then purified by column chromatography using dichloromethane / hexane = 1 / 5 (v / v) as the eluent to obtain about 14 mmol of Intermediate 84-1 (yield = 70%).

[0708] Synthesis of compound 84

[0709]

[0710] Intermediate 84-1 (12 mmol, 1.2 equivalents), N-([1,1'-biphenyl]-4-yl)-1-phenylnaphthalen-2-amine (10 mmol, 1 equivalent), Pd 2 (dba) 3 (0.5 mol, 0.05 equivalent), t-BuONa (20 mmol, 2 equivalents), t-Bu 3 P (0.1 mmol, 0.1 equivalent) and 150 mL of toluene were placed in a single-necked round-bottom flask, and the mixture was stirred at about 110° C. for about 1 hour. After the reaction was completed, the resultant was washed with ether / H 2 O, and then purified by column chromatography using dichloromethane / hexane = 1 / 8 (v / v) as an eluent to obtain about 7.0 mmol of Compound 84 (yield = 70%).

[0711] (7) Synthesis of Compound 88

[0712] Synthesis of Intermediate 88-1

[0713]

[0714] 1,4-dibromobenzene (26 mmol, 1.3 equivalents), N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-9H-fluoren-4-amine (20 mmol, 1 equivalent), Pd 2 (dba) 3 (1 mmol, 0.05 equivalent), t-BuONa (40 mmol, 2 equivalents), BINAP (2 mmol, 0.1 equivalents) and 300 mL of toluene were placed in a single-necked round-bottom flask, and the mixture was stirred at about 110° C. for about 1 hour. After the reaction was completed, the resultant was washed with ether / H 2 O, and then purified by column chromatography using dichloromethane / hexane=1 / 5 (v / v) as the eluent to obtain about 13 mmol of Intermediate 88-1 (yield=65%).

[0715] Synthesis of compound 88

[0716]

[0717] Intermediate 88-1 (12 mmol, 1.2 equivalents), N,1-diphenylnaphthalene-2-amine (10 mmol, 1 equivalent), Pd 2 (dba) 3 (0.5 mol, 0.05 equivalent), t-BuONa (20 mmol, 2 equivalents), t-Bu 3P (0.1 mmol, 0.1 equivalent) and 150 mL of toluene were placed in a single-necked round-bottom flask, and the mixture was stirred at about 110° C. for about 1 hour. After the reaction was completed, the resultant was washed with ether / H 2 O, and then purified by column chromatography using dichloromethane / hexane=1 / 8 (v / v) as an eluent to obtain about 5.9 mmol of Compound 88 (yield=59%).

[0718] (8) Synthesis of Compound 91

[0719] Synthesis of Intermediate 91-1

[0720]

[0721] 1,4-dibromobenzene (26 mmol, 1.3 equivalents), N-(4-cyclohexylphenyl)-9,9-dimethyl-9H-fluoren-2-amine (20 mmol, 1 equivalent), Pd 2 (dba) 3 (1 mmol, 0.05 equivalent), t-BuONa (40 mmol, 2 equivalents), BINAP (2 mmol, 0.1 equivalents) and 300 mL of toluene were placed in a single-necked round-bottom flask, and the mixture was stirred at about 110° C. for about 1 hour. After the reaction was completed, the resultant was washed with ether / H 2 O, and then purified by column chromatography using dichloromethane / hexane=1 / 5 (v / v) as an eluent to obtain about 12 mmol of Intermediate 91-1 (yield=60%).

[0722] Synthesis of compound 91

[0723]

[0724] Intermediate 91-1 (12 mmol, 1.2 equivalents), N-(naphthalen-2-yl)-1-phenylnaphthalen-2-amine (10 mmol, 1 equivalent), Pd 2 (dba) 3 (0.5 mol, 0.05 equivalent), t-BuONa (20 mmol, 2 equivalents), t-Bu 3 P (0.1 mmol, 0.1 equivalent) and 150 mL of toluene were placed in a single-necked round-bottom flask, and the mixture was stirred at about 110° C. for about 1 hour. After the reaction was completed, the resultant was washed with ether / H 2 O, and then purified by column chromatography using dichloromethane / hexane = 1 / 8 (v / v) as an eluent to obtain about 5.0 mmol of Compound 91 (yield = 50%).

[0725] (9) Synthesis of Compound 92

[0726] Synthesis of Intermediate 92-1

[0727]

[0728] 1,4-dibromobenzene (26 mmol, 1.3 equivalents), N-(4-cyclohexylphenyl)-9,9-dimethyl-9H-fluoren-4-amine (20 mmol, 1 equivalent), Pd 2 (dba) 3 (1 mmol, 0.05 equivalent), t-BuONa (40 mmol, 2 equivalents), BINAP (2 mmol, 0.1 equivalents) and 300 mL of toluene were placed in a single-necked round-bottom flask, and the mixture was stirred at about 110° C. for about 1 hour. After the reaction was completed, the resultant was washed with ether / H 2 O, and then purified by column chromatography using dichloromethane / hexane=1 / 5 (v / v) as an eluent to obtain about 13 mmol of Intermediate 92-1 (yield=65%).

[0729] Synthesis of compound 92

[0730]

[0731] Intermediate 92-1 (12 mmol, 1.2 eq), N-(naphthalen-1-yl)-1-phenylnaphthalen-2-amine (10 mmol, 1 eq), Pd 2 (dba) 3 (0.5 mol, 0.05 equivalent), t-BuONa (20 mmol, 2 equivalents), t-Bu 3 P (0.1 mmol, 0.1 equivalent) and 150 mL of toluene were placed in a single-necked round-bottom flask, and the mixture was stirred at about 110° C. for about 1 hour. After the reaction was completed, the resultant was washed with ether / H 2 O, and then purified by column chromatography using dichloromethane / hexane = 1 / 8 (v / v) as an eluent to obtain about 4.0 mmol of Compound 92 (yield = 40%).

[0732] (10) Synthesis of Compound 94

[0733] Synthesis of Intermediate 94-1

[0734]

[0735] 1,3-Dibromobenzene (26 mmol, 1.3 equivalents), N-([1,1'-biphenyl]-4-yl)-9,9'-spirobi[fluorene]-4-amine (20 mmol, 1 equivalent), Pd 2 (dba)3 (1 mmol, 0.05 equivalent), t-BuONa (40 mmol, 2 equivalents), BINAP (2 mmol, 0.1 equivalents) and 300 mL of toluene were placed in a single-necked round-bottom flask, and the mixture was stirred at about 110° C. for about 1 hour. After the reaction was completed, the resultant was washed with ether / H 2 O, and then purified by column chromatography using dichloromethane / hexane=1 / 5 (v / v) as the eluent to obtain about 15 mmol of Intermediate 94-1 (yield=75%).

[0736] Synthesis of compound 94

[0737]

[0738] Intermediate 94-1 (12 mmol, 1.2 equivalents), N,1-diphenylnaphthalene-2-amine (10 mmol, 1 equivalent), Pd 2 (dba) 3 (0.5 mol, 0.05 equivalent), t-BuONa (20 mmol, 2 equivalents), t-Bu 3 P (0.1 mmol, 0.1 equivalent) and 150 mL of toluene were placed in a single-necked round-bottom flask, and the mixture was stirred at about 110° C. for about 1 hour. After the reaction was completed, the resultant was washed with ether / H 2 O, and then purified by column chromatography using dichloromethane / hexane = 1 / 8 (v / v) as an eluent to obtain about 6.8 mmol of Compound 94 (yield = 68%).

[0739] (11) Synthesis of Compound 96

[0740] Synthesis of Intermediate 96-1

[0741]

[0742] 1,3-Dibromobenzene (26 mmol, 1.3 equivalents), N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-9H-fluoren-4-amine (20 mmol, 1 equivalent), Pd 2 (dba) 3 (1 mmol, 0.05 equivalent), t-BuONa (40 mmol, 2 equivalents), BINAP (2 mmol, 0.1 equivalents) and 300 mL of toluene were placed in a single-necked round-bottom flask, and the mixture was stirred at about 110° C. for about 1 hour. After the reaction was completed, the resultant was washed with ether / H 2O, and then purified by column chromatography using dichloromethane / hexane=1 / 5 (v / v) as an eluent to obtain about 16 mmol of Intermediate 96-1 (yield=80%).

[0743] Synthesis of compound 96

[0744]

[0745] Intermediate 96-1 (12 mmol, 1.2 equivalents), N,1-diphenylnaphthalene-2-amine (10 mmol, 1 equivalent), Pd 2 (dba) 3 (0.5 mol, 0.05 equivalent), t-BuONa (20 mmol, 2 equivalents), t-Bu 3 P (0.1 mmol, 0.1 equivalent) and 150 mL of toluene were placed in a single-necked round-bottom flask, and the mixture was stirred at about 110° C. for about 1 hour. After the reaction was completed, the resultant was washed with ether / H 2 O, and then purified by column chromatography using dichloromethane / hexane = 1 / 8 (v / v) as an eluent to obtain about 6.4 mmol of Compound 96 (yield = 64%).

[0746] (12) Synthesis of Compound 100

[0747] Synthesis of Intermediate 100-1

[0748]

[0749] 1,3-Dibromobenzene (26 mmol, 1.3 equivalents), N-(4-cyclohexylphenyl)-9,9-dimethyl-9H-fluoren-4-amine (20 mmol, 1 equivalent), Pd 2 (dba) 3 (1 mmol, 0.05 equivalent), t-BuONa (40 mmol, 2 equivalents), BINAP (2 mmol, 0.1 equivalents) and 300 mL of toluene were placed in a single-necked round-bottom flask, and the mixture was stirred at about 110° C. for about 1 hour. After the reaction was completed, the resultant was washed with ether / H 2 O, and then purified by column chromatography using dichloromethane / hexane=1 / 5 (v / v) as an eluent to obtain about 13 mmol of Intermediate 100-1 (yield=65%).

[0750] Synthesis of compound 100

[0751]

[0752] Intermediate 100-1 (12 mmol, 1.2 equivalents), N-(naphthalen-1-yl)-1-phenylnaphthalen-2-amine (10 mmol, 1 equivalent), Pd 2 (dba) 3 (0.5 mol, 0.05 equivalent), t-BuONa (20 mmol, 2 equivalents), t-Bu 3 P (0.1 mmol, 0.1 equivalent) and 150 mL of toluene were placed in a single-necked round-bottom flask, and the mixture was stirred at about 110° C. for about 1 hour. After the reaction was completed, the resultant was washed with ether / H 2 O, and then purified by column chromatography using dichloromethane / hexane=1 / 8 (v / v) as an eluent to obtain about 4.2 mmol of Compound 100 (yield=42%).

[0753] (13) Synthesis of Compound 121

[0754] Synthesis of Intermediate 121-1

[0755]

[0756] 3,4'-dibromo-1,1'-biphenyl (26 mmol, 1.3 equivalents), diphenylamine (20 mmol, 1 equivalent), Pd 2 (dba) 3 (1 mmol, 0.05 equivalent), t-BuONa (40 mmol, 2 equivalents), BINAP (2 mmol, 0.1 equivalents) and 300 mL of toluene were placed in a single-necked round-bottom flask, and the mixture was stirred at about 110° C. for about 1 hour. After the reaction was completed, the resultant was washed with ether / H 2 O, and then purified by column chromatography using dichloromethane / hexane = 1 / 5 (v / v) as the eluent to obtain about 15 mmol of Intermediate 121-1 (yield = 75%).

[0757] Synthesis of compound 121

[0758]

[0759] Intermediate 121-1 (12 mmol, 1.2 eq), N-(naphthalen-2-yl)-1-phenylnaphthalen-2-amine (10 mmol, 1 eq), Pd 2 (dba) 3 (0.5 mol, 0.05 equivalent), t-BuONa (20 mmol, 2 equivalents), t-Bu 3P (0.1 mmol, 0.1 equivalent) and 150 mL of toluene were placed in a single-necked round-bottom flask, and the mixture was stirred at about 110° C. for about 1 hour. After the reaction was completed, the resultant was washed with ether / H 2 O, and then purified by column chromatography using dichloromethane / hexane = 1 / 8 (v / v) as an eluent to obtain about 5.0 mmol of Compound 121 (yield = 50%).

[0760] (14) Synthesis of Compound 122

[0761] Synthesis of Intermediate 122-1

[0762]

[0763] 3,4'-dibromo-1,1'-biphenyl (26 mmol, 1.3 equivalents), N-(4-cyclohexylphenyl)-[1,1'-biphenyl]-4-amine (20 mmol, 1 equivalent), Pd 2 (dba) 3 (1 mmol, 0.05 equivalent), t-BuONa (40 mmol, 2 equivalents), BINAP (2 mmol, 0.1 equivalents) and 300 mL of toluene were placed in a single-necked round-bottom flask, and the mixture was stirred at about 110° C. for about 1 hour. After the reaction was completed, the resultant was washed with ether / H 2 O, and then purified by column chromatography using dichloromethane / hexane=1 / 5 (v / v) as the eluent to obtain about 12 mmol of intermediate 122-1 (yield=60%).

[0764] Synthesis of compound 122

[0765]

[0766] Intermediate 122-1 (12 mmol, 1.2 eq), N-(naphthalen-2-yl)-1-phenylnaphthalen-2-amine (10 mmol, 1 eq), Pd 2 (dba) 3 (0.5 mol, 0.05 equivalent), t-BuONa (20 mmol, 2 equivalents), t-Bu 3 P (0.1 mmol, 0.1 equivalent) and 150 mL of toluene were placed in a single-necked round-bottom flask, and the mixture was stirred at about 110° C. for about 1 hour. After the reaction was completed, the resultant was washed with ether / H 2 O, and then purified by column chromatography using dichloromethane / hexane = 1 / 8 (v / v) as an eluent to obtain about 4.8 mmol of Compound 122 (yield = 48%).

[0767] (15) Synthesis of Compound 127

[0768] Synthesis of Intermediate 127-1

[0769]

[0770] 3,4'-dibromo-1,1'-biphenyl (26 mmol, 1.3 equivalents), N-(4-cyclohexylphenyl)-9,9'-spirobi[fluorene]-4-amine (20 mmol, 1 equivalent), Pd 2 (dba) 3 (1 mmol, 0.05 equivalent), t-BuONa (40 mmol, 2 equivalents), BINAP (2 mmol, 0.1 equivalents) and 300 mL of toluene were placed in a single-necked round-bottom flask, and the mixture was stirred at about 110° C. for about 1 hour. After the reaction was completed, the resultant was washed with ether / H 2 O, and then purified by column chromatography using dichloromethane / hexane=1 / 5 (v / v) as the eluent to obtain about 12 mmol of Intermediate 127-1 (yield=60%).

[0771] Synthesis of compound 127

[0772]

[0773] Intermediate 127-1 (12 mmol, 1.2 equivalents), N,1-diphenylnaphthalene-2-amine (10 mmol, 1 equivalent), Pd 2 (dba) 3 (0.5 mol, 0.05 equivalent), t-BuONa (20 mmol, 2 equivalents), t-Bu 3 P (0.1 mmol, 0.1 equivalent) and 150 mL of toluene were placed in a single-necked round-bottom flask, and the mixture was stirred at about 110° C. for about 1 hour. After the reaction was completed, the resultant was washed with ether / H 2 O, and then purified by column chromatography using dichloromethane / hexane = 1 / 8 (v / v) as an eluent to obtain about 5.8 mmol of Compound 127 (yield = 58%).

[0774] (16) Synthesis of Compound 128

[0775] Synthesis of Intermediate 128-1

[0776]

[0777] 3,4'-dibromo-1,1'-biphenyl (26 mmol, 1.3 equivalents), N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-9H-fluoren-4-amine (20 mmol, 1 equivalent), Pd 2 (dba) 3 (1 mmol, 0.05 equivalent), t-BuONa (40 mmol, 2 equivalents), BINAP (2 mmol, 0.1 equivalents) and 300 mL of toluene were placed in a single-necked round-bottom flask, and the mixture was stirred at about 110° C. for about 1 hour. After the reaction was completed, the resultant was washed with ether / H 2 O, and then purified by column chromatography using dichloromethane / hexane = 1 / 5 (v / v) as the eluent to obtain about 13 mmol of Intermediate 128-1 (yield = 65%).

[0778] Synthesis of compound 128

[0779]

[0780] Intermediate 128-1 (12 mmol, 1.2 equivalents), N,1-diphenylnaphthalene-2-amine (10 mmol, 1 equivalent), Pd 2 (dba) 3 (0.5 mol, 0.05 equivalent), t-BuONa (20 mmol, 2 equivalents), t-Bu 3 P (0.1 mmol, 0.1 equivalent) and 150 mL of toluene were placed in a single-necked round-bottom flask, and the mixture was stirred at about 110° C. for about 1 hour. After the reaction was completed, the resultant was washed with ether / H 2 O, and then purified by column chromatography using dichloromethane / hexane = 1 / 8 (v / v) as an eluent to obtain about 6.2 mmol of Compound 128 (yield = 62%).

[0781] (17) Synthesis of Compound 130

[0782] Synthesis of Intermediate 130-1

[0783]

[0784] 3,4'-dibromo-1,1'-biphenyl (26 mmol, 1.3 equivalents), N-(4-cyclohexylphenyl)-[1,1'-biphenyl]-4-amine (20 mmol, 1 equivalent), Pd 2 (dba) 3(1 mmol, 0.05 equivalent), t-BuONa (40 mmol, 2 equivalents), BINAP (2 mmol, 0.1 equivalents) and 300 mL of toluene were placed in a single-necked round-bottom flask, and the mixture was stirred at about 110° C. for about 1 hour. After the reaction was completed, the resultant was washed with ether / H 2 O, and then purified by column chromatography using dichloromethane / hexane = 1 / 5 (v / v) as the eluent to obtain about 15 mmol of intermediate 130-1 (yield = 65%).

[0785] Synthesis of compound 130

[0786]

[0787] Intermediate 130-1 (12 mmol, 1.2 eq), N-(naphthalen-2-yl)-1-phenylnaphthalen-2-amine (10 mmol, 1 eq), Pd 2 (dba) 3 (0.5 mol, 0.05 equivalent), t-BuONa (20 mmol, 2 equivalents), t-Bu 3 P (0.1 mmol, 0.1 equivalent) and 150 mL of toluene were placed in a single-necked round-bottom flask, and the mixture was stirred at about 110° C. for about 1 hour. After the reaction was completed, the resultant was washed with ether / H 2 O, and then purified by column chromatography using dichloromethane / hexane = 1 / 8 (v / v) as an eluent to obtain about 6.1 mmol of Compound 130 (yield = 61%).

[0788] (18) Synthesis of Compound 135

[0789] Synthesis of Intermediate 135-1

[0790]

[0791] 4,4"-dibromo-1,1':4',1"-terphenyl (26 mmol, 1.3 equivalents), diphenylamine (20 mmol, 1 equivalent), Pd 2 (dba) 3 (1 mmol, 0.05 equivalent), t-BuONa (40 mmol, 2 equivalents), BINAP (2 mmol, 0.1 equivalents) and 300 mL of toluene were placed in a single-necked round-bottom flask, and the mixture was stirred at about 110° C. for about 1 hour. After the reaction was completed, the resultant was washed with ether / H 2 O, and then purified by column chromatography using dichloromethane / hexane = 1 / 5 (v / v) as the eluent to obtain about 12 mmol of intermediate 135-1 (yield = 60%).

[0792] Synthesis of compound 135

[0793]

[0794] Intermediate 135-1 (12 mmol, 1.2 equivalents), N-(4-cyclohexylphenyl)-1-phenylnaphthalen-2-amine (10 mmol, 1 equivalent), Pd 2 (dba) 3 (0.5 mol, 0.05 equivalent), t-BuONa (20 mmol, 2 equivalents), t-Bu 3 P (0.1 mmol, 0.1 equivalent) and 150 mL of toluene were placed in a single-necked round-bottom flask, and the mixture was stirred at about 110° C. for about 1 hour. After the reaction was completed, the resultant was washed with ether / H 2 O, and then purified by column chromatography using dichloromethane / hexane=1 / 8 (v / v) as an eluent to obtain about 6.9 mmol of Compound 135 (yield=69%).

[0795] (19) Synthesis of Compound 140

[0796] Synthesis of Intermediate 140-1

[0797]

[0798] 4,4"-dibromo-1,1':4',1"-terphenyl (26 mmol, 1.3 equivalents), N-phenyldibenzo[b,d]furan-1-amine (20 mmol, 1 equivalent), Pd 2 (dba) 3 (1 mmol, 0.05 equivalent), t-BuONa (40 mmol, 2 equivalents), BINAP (2 mmol, 0.1 equivalents) and 300 mL of toluene were placed in a single-necked round-bottom flask, and the mixture was stirred at about 110° C. for about 1 hour. After the reaction was completed, the resultant was washed with ether / H 2 O, and then purified by column chromatography using dichloromethane / hexane = 1 / 5 (v / v) as the eluent to obtain about 14 mmol of intermediate 140-1 (yield = 70%).

[0799] Synthesis of compound 140

[0800]

[0801] Intermediate 140-1 (12 mmol, 1.2 equivalents), N,1-diphenylnaphthalene-2-amine (10 mmol, 1 equivalent), Pd 2 (dba)3 (0.5 mol, 0.05 equivalent), t-BuONa (20 mmol, 2 equivalents), t-Bu 3 P (0.1 mmol, 0.1 equivalent) and 150 mL of toluene were placed in a single-necked round-bottom flask, and the mixture was stirred at about 110° C. for about 1 hour. After the reaction was completed, the resultant was washed with ether / H 2 O, and then purified by column chromatography using dichloromethane / hexane = 1 / 8 (v / v) as an eluent to obtain about 6.0 mmol of Compound 140 (yield = 60%).

[0802] (20) Synthesis of Compound 145

[0803] Synthesis of Intermediate 145-1

[0804]

[0805] 3,4"-dibromo-1,1':4',1"-terphenyl (26 mmol, 1.3 equivalents), diphenylamine (20 mmol, 1 equivalent), Pd 2 (dba) 3 (1 mmol, 0.05 equivalent), t-BuONa (40 mmol, 2 equivalents), BINAP (2 mmol, 0.1 equivalents) and 300 mL of toluene were placed in a single-necked round-bottom flask, and the mixture was stirred at about 110° C. for about 1 hour. After the reaction was completed, the resultant was washed with ether / H 2 O, and then purified by column chromatography using dichloromethane / hexane=1 / 5 (v / v) as the eluent to obtain about 12 mmol of Intermediate 145-1 (yield=60%).

[0806] Synthesis of compound 145

[0807]

[0808] Intermediate 145-1 (12 mmol, 1.2 equivalents), N,1-diphenylnaphthalene-2-amine (10 mmol, 1 equivalent), Pd 2 (dba) 3 (0.5 mol, 0.05 equivalent), t-BuONa (20 mmol, 2 equivalents), t-Bu 3 P (0.1 mmol, 0.1 equivalent) and 150 mL of toluene were placed in a single-necked round-bottom flask, and the mixture was stirred at about 110° C. for about 1 hour. After the reaction was completed, the resultant was washed with ether / H 2O, and then purified by column chromatography using dichloromethane / hexane = 1 / 8 (v / v) as an eluent to obtain about 5.9 mmol of Compound 145 (yield = 59%).

[0809] (21) Synthesis of Compound 147

[0810] Synthesis of Intermediate 147-1

[0811]

[0812] 3,4"-dibromo-1,1':4',1"-terphenyl (26 mmol, 1.3 equivalents), diphenylamine (20 mmol, 1 equivalent), Pd 2 (dba) 3 (1 mmol, 0.05 equivalent), t-BuONa (40 mmol, 2 equivalents), BINAP (2 mmol, 0.1 equivalents) and 300 mL of toluene were placed in a single-necked round-bottom flask, and the mixture was stirred at about 110° C. for about 1 hour. After the reaction was completed, the resultant was washed with ether / H 2 O, and then purified by column chromatography using dichloromethane / hexane = 1 / 5 (v / v) as the eluent to obtain about 14 mmol of Intermediate 147-1 (yield = 70%).

[0813] Synthesis of compound 147

[0814]

[0815] Intermediate 147-1 (12 mmol, 1.2 equivalents), N-(4-cyclohexylphenyl)-1-phenylnaphthalen-2-amine (10 mmol, 1 equivalent), Pd 2 (dba) 3 (0.5 mol, 0.05 equivalent), t-BuONa (20 mmol, 2 equivalents), t-Bu 3 P (0.1 mmol, 0.1 equivalent) and 150 mL of toluene were placed in a single-necked round-bottom flask, and the mixture was stirred at about 110° C. for about 1 hour. After the reaction was completed, the resultant was washed with ether / H 2 O, and then purified by column chromatography using dichloromethane / hexane = 1 / 8 (v / v) as an eluent to obtain about 6.0 mmol of Compound 147 (yield = 60%).

[0816] (22) Synthesis of Compound 153

[0817] Synthesis of Intermediate 153-1

[0818]

[0819] 2,4"-dibromo-1,1':4',1"-terphenyl (26 mmol, 1.3 equivalents), diphenylamine (20 mmol, 1 equivalent), Pd 2 (dba) 3 (1 mmol, 0.05 equivalent), t-BuONa (40 mmol, 2 equivalents), BINAP (2 mmol, 0.1 equivalents) and 300 mL of toluene were placed in a single-necked round-bottom flask, and the mixture was stirred at about 110° C. for about 1 hour. After the reaction was completed, the resultant was washed with ether / H 2 O, and then purified by column chromatography using dichloromethane / hexane = 1 / 5 (v / v) as the eluent to obtain about 12 mmol of Intermediate 153-1 (yield = 60%).

[0820] Synthesis of compound 153

[0821]

[0822] Intermediate 153-1 (12 mmol, 1.2 equivalents), N,1-diphenylnaphthalene-2-amine (10 mmol, 1 equivalent), Pd 2 (dba) 3 (0.5 mol, 0.05 equivalent), t-BuONa (20 mmol, 2 equivalents), t-Bu 3 P (0.1 mmol, 0.1 equivalent) and 150 mL of toluene were placed in a single-necked round-bottom flask, and the mixture was stirred at about 110° C. for about 1 hour. After the reaction was completed, the resultant was washed with ether / H 2 O, and then purified by column chromatography using dichloromethane / hexane=1 / 8 (v / v) as an eluent to obtain about 4.9 mmol of Compound 153 (yield=49%).

[0823] (23) Synthesis of Compound 155

[0824] Synthesis of Intermediate 155-1

[0825]

[0826] 2,4"-dibromo-1,1':4',1"-terphenyl (26 mmol, 1.3 equivalents), diphenylamine (20 mmol, 1 equivalent), Pd 2 (dba) 3(1 mmol, 0.05 equivalent), t-BuONa (40 mmol, 2 equivalents), BINAP (2 mmol, 0.1 equivalents) and 300 mL of toluene were placed in a single-necked round-bottom flask, and the mixture was stirred at about 110° C. for about 1 hour. After the reaction was completed, the resultant was washed with ether / H 2 O, and then purified by column chromatography using dichloromethane / hexane=1 / 5 (v / v) as the eluent to obtain about 12 mmol of intermediate 155-1 (yield=60%).

[0827] Synthesis of compound 155

[0828]

[0829] Intermediate 155-1 (12 mmol, 1.2 equivalents), N-(4-cyclohexylphenyl)-1-phenylnaphthalen-2-amine (10 mmol, 1 equivalent), Pd 2 (dba) 3 (0.5 mol, 0.05 equivalent), t-BuONa (20 mmol, 2 equivalents), t-Bu 3 P (0.1 mmol, 0.1 equivalent) and 150 mL of toluene were placed in a single-necked round-bottom flask, and the mixture was stirred at about 110° C. for about 1 hour. After the reaction was completed, the resultant was washed with ether / H 2 O, and then purified by column chromatography using dichloromethane / hexane = 1 / 8 (v / v) as an eluent to obtain about 4.3 mmol of Compound 155 (yield = 43%).

[0830] (24) Synthesis of Compound 157

[0831] Synthesis of Intermediate 157-1

[0832]

[0833] 2,4"-dibromo-1,1':4',1"-terphenyl (26 mmol, 1.3 equivalents), N-phenyl-9,9-dimethyl-9H-fluoren-4-amine (20 mmol, 1 equivalent), Pd 2 (dba) 3 (1 mmol, 0.05 equivalent), t-BuONa (40 mmol, 2 equivalents), BINAP (2 mmol, 0.1 equivalents) and 300 mL of toluene were placed in a single-necked round-bottom flask, and the mixture was stirred at about 110° C. for about 1 hour. After the reaction was completed, the resultant was washed with ether / H 2O, and then purified by column chromatography using dichloromethane / hexane=1 / 5 (v / v) as the eluent to obtain about 12 mmol of Intermediate 157-1 (yield=60%).

[0834] Synthesis of compound 157

[0835]

[0836] Intermediate 157-1 (12 mmol, 1.2 equivalents), N,1-diphenylnaphthalene-2-amine (10 mmol, 1 equivalent), Pd 2 (dba) 3 (0.5 mol, 0.05 equivalent), t-BuONa (20 mmol, 2 equivalents), t-Bu 3 P (0.1 mmol, 0.1 equivalent) and 150 mL of toluene were placed in a single-necked round-bottom flask, and the mixture was stirred at about 110° C. for about 1 hour. After the reaction was completed, the resultant was washed with ether / H 2 O, and then purified by column chromatography using dichloromethane / hexane = 1 / 8 (v / v) as an eluent to obtain about 4.5 mmol of Compound 157 (yield = 45%).

[0837] (25) Synthesis of Compound 181

[0838] Synthesis of Intermediate 181-1

[0839]

[0840] 2,4"-dibromo-1,1':4',1"-terphenyl (26 mmol, 1.3 equivalents), N-(4-cyclohexylphenyl)aniline (20 mmol, 1 equivalent), Pd 2 (dba) 3 (1 mmol, 0.05 equivalent), t-BuONa (40 mmol, 2 equivalents), BINAP (2 mmol, 0.1 equivalents) and 300 mL of toluene were placed in a single-necked round-bottom flask, and the mixture was stirred at about 110° C. for about 1 hour. After the reaction was completed, the resultant was washed with ether / H 2 O, and then purified by column chromatography using dichloromethane / hexane=1 / 5 (v / v) as the eluent to obtain about 13 mmol of Intermediate 181-1 (yield=65%).

[0841] Synthesis of compound 181

[0842]

[0843] Intermediate 181-1 (12 mmol, 1.2 equivalents), N,1-diphenylnaphthalene-2-amine (10 mmol, 1 equivalent), Pd 2 (dba) 3 (0.5 mol, 0.05 equivalent), t-BuONa (20 mmol, 2 equivalents), t-Bu 3 P (0.1 mmol, 0.1 equivalent) and 150 mL of toluene were placed in a single-necked round-bottom flask, and the mixture was stirred at about 110° C. for about 1 hour. After the reaction was completed, the resultant was washed with ether / H 2 O, and then purified by column chromatography using dichloromethane / hexane = 1 / 8 (v / v) as an eluent to obtain about 4.0 mmol of Compound 181 (yield = 40%).

[0844] The compounds synthesized in Examples 1 to 25 1 H NMR and MS / FAB are shown in the following Table 1. With reference to the previously mentioned synthetic procedures and starting materials, one skilled in the art can readily recognize the synthetic methods of other compounds.

[0845] Table 1

[0846]

[0847]

[0848]

[0849] 2. Fabrication and evaluation of light-emitting elements

[0850] The light-emitting elements including the amine compounds according to the examples were each manufactured as follows. Amine compound 64, amine compound 67, amine compound 73, amine compound 76, amine compound 81, amine compound 84, amine compound 88, amine compound 91, amine compound 92, amine compound 94, amine compound 96, amine compound 100, amine compound 121, amine compound 122, amine compound 127, amine compound 128, amine compound 130, amine compound 135, amine compound 140, amine compound 145, amine compound 147, amine compound 153, amine compound 155, amine compound 157, and amine compound 181, which are the example compounds described above, were each used as a hole transport layer material to manufacture the light-emitting elements according to Examples 1 to 25, respectively. The light-emitting elements according to Comparative Examples 1 to 5 correspond to the light-emitting elements each manufactured using Comparative Example Compounds C1 to C5, respectively, as hole transport layer materials.

[0851] Example compounds

[0852]

[0853]

[0854]

[0855] Comparative Example Compounds

[0856]

[0857] Manufacturing of light-emitting components

[0858] The 15Ω / cm manufactured by Corning Co. Ltd. 2 The ITO glass substrate was cut into a size of about 50 mm × 50 mm × 0.7 mm, washed with isopropyl alcohol and pure water, each cleaned by ultrasonic wave for about five minutes, and then irradiated with UV rays for about 30 minutes. Thereafter, ozone treatment was performed. Thereafter, NPD was vacuum deposited to form a substrate having a size of about Then, the Example compound or the Comparative Example compound was vacuum deposited to form a hole injection layer having a thickness of about CzSi was vacuum deposited on the hole transport layer to form a hole transport layer having a thickness of about A light-emitting auxiliary layer of thickness.

[0859] HT3, EHT66, AD-38 and D1 were co-deposited on the light-emitting auxiliary layer in a weight ratio of about 42:42:15:1 to form a light-emitting auxiliary layer having a thickness of about 100 nm. TSPO1 is deposited on the light-emitting layer to form a light-emitting layer having a thickness of about A hole blocking layer with a thickness of about 1000 nm was formed, and TPBi was then deposited on the hole blocking layer to form a layer having a thickness of about 1000 nm. Then, LiF is deposited on the electron transport layer to form a layer having a thickness of about Al is deposited on the electron injection layer to form an electron injection layer having a thickness of about The thickness of the cathode.

[0860] Furthermore, the compound used for manufacturing each functional layer of the light-emitting element is as follows.

[0861]

[0862] Manufacturing of light-emitting components

[0863] The light emitting elements according to Examples 1 to 25 and Comparative Examples 1 to 5 were each evaluated, and the results are listed in Table 2. Table 2 lists the driving voltage, luminous efficiency, emission wavelength, and lifetime of each manufactured light emitting element.

[0864] In the characteristic evaluation results of the examples and comparative examples in Table 2, the values ​​of the driving voltage (V) and the current density were measured by using a V7000OLED IVL test system (Polaronix). For the evaluation of the characteristics of each of the light-emitting elements manufactured according to Examples 1 to 25 and Comparative Examples 1 to 5, the driving voltage (V) and the current density were measured at about 50 mA / cm 2 The driving voltage and luminous efficiency were measured at a current density of about 100 mA / cm 2 The time taken for the brightness to decrease to 95% of the initial brightness during substantially continuous driving at a current density of 1.547 W was measured as the service life.

[0865] Table 2

[0866]

[0867]

[0868] With reference to Table 2, it can be seen that, compared with the light-emitting element according to the comparative example, the light-emitting element according to the embodiment using the amine compound according to one or more embodiments of the present disclosure as the hole transport layer material each exhibits a relatively low driving voltage, a relatively high luminous efficiency and a relatively long service life. In the embodiment of the comparative example compound, compared with the example compound, it can be confirmed that when the comparative example compound is each applied to the light-emitting element, the driving voltage is high, the luminous efficiency is reduced, and the service life is reduced. For example, with reference to Table 2, it can be confirmed that the light-emitting element using the amine compound according to one or more embodiments of the present disclosure each exhibits improved element characteristics in terms of luminous efficiency or element service life than the light-emitting element according to the comparative example.

[0869] The amine compound according to the embodiment may have a structure in which two amine groups are connected via a first connector, and a first substituent is connected to at least one of the two amine groups. The first substituent may include a naphthyl moiety and a first substituent connected to the naphthyl moiety. Because each of the amine compounds according to the embodiment includes a structure in which the first substituent is connected to at least one of the two amine groups, the hole transport capability and the stability of the radical cation state can be improved. Therefore, the light-emitting element according to the embodiment comprising such an amine compound according to the embodiment as a hole transport layer material can be expected to exhibit high luminous efficiency and long element service life.

[0870] Comparative Example Compounds C1 to C3 used in Comparative Examples 1 to 3, respectively, are each a diamine compound including two amine groups but not including the first substituent suggested in the present disclosure. Therefore, compared with the hole transport characteristics of the light-emitting element according to the embodiment, the hole transport characteristics of the light-emitting element according to the comparative example may be deteriorated. Due to such results, it is believed that the light-emitting elements according to Comparative Examples 1-3 may have lower luminous efficiency and service life than the light-emitting element according to the embodiment.

[0871] When Comparative Examples 4 and 5 are compared with Examples 13 to 17, Comparative Example Compounds C4 and C5 used in Comparative Examples 4 and 5 correspond to embodiments in which the linker connecting two amine groups is p, p-biphenylene. For example, Comparative Example Compounds C4 and C5 are each a compound having a structure in which two amine groups are connected via p, p-biphenylene corresponding to Formula A-1, and therefore can have increased planarity compared to Example Compounds 121, 122, 127, 128, and 130, each having m, p-biphenylene. Therefore, charge mobility can be reduced.

[0872] In addition, it can be confirmed that when Comparative Examples 4 and 5 are compared with Examples 18 and 19, the light-emitting elements according to Examples 18 and 19 each have a lower driving voltage and a longer element life, and a higher efficiency than the light-emitting elements according to Comparative Examples 4 and 5. Compounds 135 and 140 used in Examples 18 and 19, respectively, are compounds each containing a terphenylene as a linker connecting two amine groups. It can be seen that, compared with Comparative Example Compounds C4 and C5, even if all three benzene structures contained in the linkers of Compounds 135 and 140 are connected in a para-position relationship, the distance that the charge can move is ensured by increasing the number of phenyl groups in the linker, and thus the charge mobility is restored again, resulting in an improvement in the service life and efficiency of the light-emitting element. For example, in the amine compound according to one or more embodiments, when the phenyl structure included in the linker contains three or more benzene structures, the movement distance of the charge in the molecule can be fully ensured, and thus even if all three or more benzene structures are connected in a para relationship, the charge mobility can be improved compared to the amine compound having p,p-biphenyl as a linker in which two benzene structures are connected in a para relationship.

[0873] By including the amine compound according to one or more embodiments, the light emitting element according to one or more embodiments may exhibit characteristics of high efficiency and long lifetime.

[0874] When the amine compound according to one or more embodiments is applied to a light emitting element, characteristics of high efficiency and long lifespan may be exhibited.

[0875] An electronic device according to one or more embodiments may exhibit excellent or suitable display quality.

[0876] As used herein, the terms "substantially," "about," or similar terms are used as terms of approximation rather than as terms of degree, and are intended to account for the inherent deviations in measurements or calculations that one of ordinary skill in the art would recognize. "About," as used herein, includes the specified value and means within an acceptable range of deviations of the specified value as determined by one of ordinary skill in the art taking into account the relevant measurements and the errors associated with the measurement of the particular quantity (i.e., the limits of the measurement system). For example, "about" can mean within one or more than one standard deviation, or within ±30%, ±20%, ±10%, ±5% of the specified value.

[0877] In the present disclosure, "does not include 'component' or does not include any 'component'", "excludes 'component' or excludes any 'component'", "does not contain 'component'", etc. means that the 'component' is not added, selected or used as a component in the compound / composition, but due to other impurities and / or external factors in the composition, less than the appropriate amount of the 'component' may still be included.

[0878] Any numerical range listed herein is intended to include all sub-ranges of the same numerical precision within the listed range. For example, the range of "1.0 to 10.0" is intended to include all sub-ranges between the listed minimum value 1.0 and the listed maximum value 10.0 (and including the end value), that is, having a minimum value equal to or greater than 1.0 and a maximum value equal to or less than 10.0, such as 2.4 to 7.6. Any maximum numerical value listed herein is intended to include all lower numerical limits included therein, and any minimum numerical value listed in this specification is intended to include all higher numerical limits included therein. Therefore, the applicant reserves the right to modify this specification (including claims) to clearly list any sub-ranges included in the range clearly listed herein.

[0879] In the present disclosure, when the particles are spherical, "size / size" means the particle diameter or the average particle diameter, and when the particles are non-spherical, "size / size" means the major axis length or the average major axis length. The diameter (or size) of the particles can be measured using a scanning electron microscope or a particle size analyzer. As a particle size analyzer, for example, HORIBA, LA-950 laser particle size analyzer can be used. When the size of the particles is measured using a particle size analyzer, the average particle diameter (or size) is referred to as D50. D50 refers to the average diameter (or size) of the particles whose cumulative volume corresponds to 50% by volume in a particle size distribution (e.g., cumulative distribution), and refers to the value of the particle size corresponding to 50% from the smallest particle when the total number of particles is 100% in a distribution curve accumulated in the order of the smallest particle size to the largest particle size.

[0880] Any suitable hardware, firmware (e.g., application specific integrated circuit), software, or a combination of software, firmware and hardware can be used to implement the light-emitting element, display device, electronic device, or any other related device / device or component according to the embodiments of the present disclosure described herein. For example, the various components of the device can be formed on an integrated circuit (IC) chip or on a separate IC chip. In addition, the various components of the device can be implemented on a flexible printed circuit film, a tape carrier package (TCP), a printed circuit board (PCB), or formed on a substrate. In addition, the various components of the device can be a process or thread that runs on one or more processors in one or more computing devices, executes computer program instructions and interacts with other system components for performing various functions described herein. The computer program instructions are stored in a memory, which can be implemented in a computing device using a standard memory device (such as a random access memory (RAM) as an example). The computer program instructions can also be stored in other non-temporary computer-readable media, such as a CD-ROM, a flash drive, etc. as an example. Furthermore, those skilled in the art will recognize that the functionality of various computing devices may be combined or integrated into a single computing device, or that the functionality of a particular computing device may be distributed across one or more other computing devices without departing from the scope of the embodiments of the present disclosure.

[0881] So far, although the embodiments of the present disclosure have been described, it should be understood that the present disclosure should not be limited to these embodiments, but within the spirit and scope of the claimed disclosure, one or more than one suitable changes and modifications may be made by a person of ordinary skill in the art. Therefore, the technical scope of the present disclosure is not intended to be limited to the contents set forth in the detailed description of the present disclosure, but is intended to be defined by the appended claims and their equivalents.

Claims

1. An amine compound represented by Formula 1: Formula 1 in, In formula 1, Ar1 to Ar3 are each independently a substituted or unsubstituted oxy group, a substituted or unsubstituted silyl 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 alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, Excluding the case where Ar1 contains a fluorene group, a dibenzofuran group or a dibenzothiophene group, L1 is a substituted or unsubstituted phenylene group, R a is a substituted or unsubstituted oxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, R1 is hydrogen, deuterium, halogen, a substituted or unsubstituted oxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, n1 is an integer from 0 to 6, m1 is an integer from 1 to 4, and When m1 is 2, the case where L1 is represented by formula A-1 is excluded: Formula A-1 Wherein, in formula A-1, is the position of connection to the nitrogen atom to which Ar1 in Formula 1 is connected, and It is the position of connection to the nitrogen atom to which Ar2 and Ar3 in Formula 1 are connected. 2 . The amine compound according to claim 1 , wherein the amine compound represented by Formula 1 is a diamine compound.

3. The amine compound according to claim 1, The amine compound represented by Formula 1 is represented by Formula 2: Formula 2 in, In formula 2, R2 is hydrogen, deuterium, halogen, a substituted or unsubstituted oxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, n2 is an integer from 0 to 4, and Ar1 to Ar3, R a , R1, n1 and m1 are each the same as defined in Formula 1.

4. The amine compound according to claim 1, The amine compound represented by Formula 1 is represented by Formula 3: Formula 3 in, In formula 3, R3 is hydrogen, deuterium, halogen, a substituted or unsubstituted oxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, n3 is an integer from 0 to 5, and Ar1 to Ar3, L1, R1, n1 and m1 are the same as defined in Formula 1.

5. The amine compound according to claim 4, The amine compound represented by Formula 3 is represented by Formula 4-1 or Formula 4-2: Formula 4-1 Formula 4-2 in, In formula 4-1 and formula 4-2, Ar1 to Ar3, L1, R1, R3, n1, n3 and m1 are each the same as defined in Formula 1 and Formula 3.

6. The amine compound according to claim 1, The amine compound represented by Formula 1 is represented by any one selected from Formula 5-1 to Formula 5-5: Formula 5-1 Formula 5-2 Formula 5-3 Formula 5-4 Formula 5-5 in, In Formula 5-1 to Formula 5-5, R 11 To R 20 are each independently hydrogen, deuterium, halogen, substituted or unsubstituted oxy group, substituted or unsubstituted silyl group, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, n11 to n20 are each independently an integer from 0 to 4, and Ar1 to Ar3, R a , R1 and n1 are each the same as defined in Formula 1.

7. The amine compound according to claim 1, Wherein L1 is represented by any one selected from Formula L-1 to Formula L-22: Formula L-1 Formula L-2 Formula L-3 Formula L-4 Formula L-5 Formula L-6 Formula L-7 Formula L-8 Formula L-9 Formula L-10 Formula L-11 Formula L-12 Formula L-13 Formula L-14 Formula L-15 Type L-16 Formula L-17 Formula L-18 Type L-19 Formula L-20 Formula L-21 Formula L-22 in, In Formula L-1 to Formula L-22, R b1 To R b65 are each independently hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, m1 to m65 are each independently an integer from 0 to 4, is the position of connection to the nitrogen atom to which Ar1 in Formula 1 is connected, and It is the position of connection to the nitrogen atom to which Ar2 and Ar3 in Formula 1 are connected.

8. The amine compound of claim 1, wherein Ar1 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted naphthyl group, and Ar2 and Ar3 are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted fluorenyl group.

9. The amine compound according to claim 1, wherein Ar1 is represented by any one selected from Formula B-1 to Formula B-4, and Ar2 and Ar3 are each independently represented by any one selected from Formula B-1 to Formula B-7: Formula B-1 Formula B-2 Formula B-3 Formula B-4 Formula B-5 Formula B-6 Formula B-7 in, In Formula B-1 to Formula B-7, R d1 To R d18 are each independently hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, p1, p3, p11 and p12 are each independently an integer from 0 to 5, p2, p4, p10, p14, p15, p16 and p18 are each independently an integer from 0 to 4, p5 is an integer from 0 to 11, p6 is an integer from 0 to 7, p9, p13 and p17 are each independently an integer from 0 to 3, and is the position of connection to the corresponding nitrogen atom in Formula 1.

10. The amine compound according to claim 1, The amine compound represented by Formula 1 is represented by Formula 6-1 or Formula 6-2: Formula 6-1 Formula 6-2 in, In equation 6-1 and equation 6-2, R3 is hydrogen, deuterium, halogen, a substituted or unsubstituted oxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, n3 is an integer from 0 to 5, and Ar1' to Ar3' are each independently selected from Substituent Group A, provided that Ar1' is not selected from any one of a36 to a47: Substituent Group A In substituent group A, is the position of connection to the corresponding nitrogen atom in Formula 1, Among them, in formula 6-1 and formula 6-2, L1, R1, n1 and m1 are each the same as defined in Formula 1.

11. The amine compound according to claim 1, The amine compound represented by Formula 1 is any one of the compounds selected from Compound Group 1: Compound Group 1 12. Light-emitting element, comprising: a first electrode; a second electrode on the first electrode; as well as At least one functional layer between the first electrode and the second electrode and containing the amine compound according to any one of claims 1 to 11.

13. The light-emitting element according to claim 12, wherein the at least one functional layer comprises: Luminescent layer; a hole transport region between the first electrode and the light emitting layer; as well as an electron transport region between the light emitting layer and the second electrode, and The hole transporting region includes the amine compound.

14. The light-emitting element according to claim 13, wherein the hole transport region comprises: a hole injection layer on the first electrode; as well as a hole transport layer on the hole injection layer, and The hole transport layer includes the amine compound. 15 . The light-emitting element according to claim 13 , wherein a layer adjacent to the light-emitting layer selected from a plurality of layers included in the hole transporting region contains the amine compound.

16. An electronic device selected from the group consisting of a television, a monitor, an outdoor advertising board, a personal computer, a laptop computer, a personal digital assistant, a display device for a vehicle, a game console, a portable electronic device, and a camera, and comprising at least one light emitting element, wherein the at least one light-emitting element comprises the amine compound according to any one of claims 1 to 11.

17. The electronic device of claim 16, wherein the electronic device comprises: Base layer; a circuit layer on the substrate layer; A display element layer on the circuit layer and including the light-emitting element; as well as an encapsulation layer on the display element layer, and The light emitting element comprises: a first electrode; a second electrode on the first electrode; and At least one functional layer is between the first electrode and the second electrode and includes the amine compound.

18. The electronic device of claim 17, wherein: The light emitting element further includes a capping layer on the second electrode, the capping layer having a refractive index of at least 1.6 with respect to light in a wavelength range of 550 nm to 660 nm.

19. The electronic device of claim 17, further comprising a light control layer on the encapsulation layer, wherein the light emitting element is intended to emit light of a first color, and The light control layer comprises: a first light control component including first quantum dots that convert the first color light into a second color light having a longer wavelength than the first color light; a second light control component including second quantum dots that convert the first color light into a third color light having a longer wavelength than the first color light and the second color light; as well as A third light control component transmits the first color light.

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