CN116903565A

CN116903565A - Light-emitting element and amine compound for light-emitting element

Info

Publication number: CN116903565A
Application number: CN202310395188.3A
Authority: CN
Inventors: 山谷昭德
Original assignee: Samsung Display Co Ltd
Current assignee: Samsung Display Co Ltd
Priority date: 2022-04-15
Filing date: 2023-04-13
Publication date: 2023-10-20

Abstract

The present invention relates to a light-emitting element and an amine compound for a light-emitting element, and a light-emitting element according to an embodiment includes: a first electrode; a second electrode disposed on the first electrode; and at least one functional layer disposed between the first electrode and the second electrode, wherein an amine compound represented by a specific chemical formula structure is included in the functional layer, thereby enabling improvement of light emitting efficiency and element lifetime of the light emitting element.

Description

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

Technical Field

The present invention relates to a light-emitting element and an amine compound for a light-emitting element, and more particularly, to a light-emitting element in which a functional layer includes a novel amine compound.

Background

Recently, organic electroluminescent display devices (Organic Electroluminescence Display Device) and the like have been actively developed as image display devices. An organic electroluminescent display device or the like is a display device including a so-called self-emission type light emitting element in which holes and electrons injected from a first electrode and a second electrode are recombined in a light emitting layer to emit light from a light emitting material of the light emitting layer to realize display.

As light emitting elements are applied to display devices, there is a need for a low driving voltage, high light emitting efficiency, and long life, and there is a continuing need for development of materials for light emitting elements that can stably meet the above-mentioned needs.

In order to realize a long-life light-emitting element, development of a material for a hole transport region excellent in hole transport property and stability is underway.

Disclosure of Invention

The present invention provides a light-emitting element which has long-life characteristics.

Another object of the present invention is to provide an amine compound as a material for a light-emitting element for improving the lifetime of the element.

The light emitting element of one embodiment includes: a first electrode; a second electrode disposed on the first electrode; and at least one functional layer disposed between the first electrode and the second electrode and including an amine compound represented by the following chemical formula 1.

[ chemical formula 1]

In the chemical formula 1, Q ¹ Is O or S, ar ¹ R is a substituted or unsubstituted phenyl group ¹ And R is ² Are each independently a hydrogen atom, a heavy hydrogen atom,A halogen atom, a substituted or unsubstituted silyl group, a substituted or unsubstituted aryl group having 6 or more and 30 or less of a ring-forming carbon atom, or a substituted or unsubstituted heteroaryl group having 2 or more and 30 or less of a ring-forming carbon atom, X ¹ In order to obtain a substituted or unsubstituted naphthyl group or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, n1 is an integer of 1 to 3, k1 is an integer of 0 to 6, k2 is an integer of 0 to 4, and FG is represented by the following chemical formula 2-1 or 2-2.

[ chemical formula 2-1]

[ chemical formula 2-2]

In the chemical formula 2-1 and the chemical formula 2-2, X ² Is a substituted or unsubstituted naphthyl group or a substituted or unsubstituted heteroaryl group having 2 or more and 30 or less ring-forming carbon atoms, R ³ And R is ⁴ Each independently is a hydrogen atom, a heavy hydrogen atom, a halogen atom, a substituted or unsubstituted silyl group, a substituted or unsubstituted aryl group having 6 or more and 30 or less of a ring-forming carbon atom, or a substituted or unsubstituted heteroaryl group having 2 or more and 30 or less of a ring-forming carbon atom, Q ² O, S, NR of a shape of O, S, NR ⁵ Or CR ⁶ R ⁷ ，R ⁵ To R ⁷ Each independently is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 50 ring-forming carbon atoms, Z is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 carbon atoms, or a substituted or unsubstituted aromatic heterocyclic ring having 2 to 30 ring-forming carbon atoms, and k3 is 0 or more An integer of up to 4, k4 is an integer of 0 to 7, n2 is an integer of 1 to 3, wherein X ¹ And X ² Is thatExcept for the case of (2).

In an embodiment, the at least one functional layer may include: a light emitting layer; a hole transport region disposed between the first electrode and the light emitting layer; and an electron transport region disposed between the light emitting layer and the second electrode, wherein the hole transport region may include an amine compound represented by the chemical formula 1.

In an embodiment, the hole transport region may include: a hole injection layer disposed on the first electrode; and an electron blocking layer disposed on the hole injection layer, wherein the electron blocking layer may include an amine compound represented by the chemical formula 1.

In one embodiment, the chemical formula 2-1 may be represented by the following chemical formula 2-1a or the following chemical formula 2-1 b.

[ chemical formula 2-1a ]

[ chemical formula 2-1b ]

In the chemical formula 2-1a and the chemical formula 2-1b, R ^3-1 To R ^3-3 Each independently is a hydrogen atom, a heavy hydrogen atom, a halogen atom, a substituted or unsubstituted aryl group having 6 or more and 15 or a substituted or unsubstituted heteroaryl group having 2 or more and 15 or less, k3-1 to k3-3 are each independently an integer of 0 or more and 4 or less, n2-1 is an integer of 0 or more and 2 or less, X ² And n2 is the same as that defined in the chemical formula 2-1。

In one embodiment, the chemical formula 2-2 may be represented by any one of the following chemical formulas 2-2a to 2-2 c.

[ chemical formula 2-2a ]

[ chemical formula 2-2b ]

[ chemical formula 2-2c ]

In the chemical formulas 2-2a to 2-2c, Z _a Is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 10 carbon atoms in the ring, R ^4-1 Is a hydrogen atom, a heavy hydrogen atom, a halogen atom or a substituted or unsubstituted aryl group having 6 to 15 ring-forming carbon atoms, k4-1 is an integer of 0 to 7 inclusive, Q ² The same as defined in the chemical formula 2-2.

In an embodiment, the FG may be represented by any of the following formulas FG-1 to FG-6.

[ chemical formula FG-1]

[ chemical formula FG-2]

[ chemical formula FG-3]

[ chemical formula FG-4]

[ chemical formula FG-5]

[ chemical formula FG-6]

In the formulae FG-1 to FG-6, R ³ⁱ 、R ³ⁱⁱ And R is ⁴ⁱ To R ⁴ⁱⁱⁱ Each independently is a hydrogen atom, a heavy hydrogen atom, a halogen atom, or a substituted or unsubstituted phenyl group, k3i, k3ii, and k4ii are each independently an integer of 0 to 4, k4i is an integer of 0 to 3, k4iii is an integer of 0 to 2, X ² And Q ² The same as defined in the chemical formula 2-1 and the chemical formula 2-2.

In one embodiment, the chemical formula 1 may be represented by the following chemical formula 3-1 or the following chemical formula 3-2.

[ chemical formula 3-1]

[ chemical formula 3-2]

In the chemical formula 3-1 and the chemical formula 3-2, Y is O or NR ¹¹ ，R ⁸ To R ¹¹ Each independently is a hydrogen atom, a heavy hydrogen atom, a halogen atom, or a substituted or unsubstituted aryl group having 6 to 20 ring-forming carbon atoms, m1 is an integer of 0 to 5, m2 and m3 are each independently an integer of 0 to 7, Q ¹ 、R ¹ 、R ² N1, k2 and FG are the same as defined in the chemical formula 1.

In one embodiment, the chemical formula 1 may be represented by the following chemical formula 4-1 or the following chemical formula 4-2.

[ chemical formula 4-1]

[ chemical formula 4-2]

In the chemical formula 4-1 and the chemical formula 4-2, R ^2a To R ^4a Each independently is a hydrogen atom, a heavy hydrogen atom, a halogen atom, or a substituted or unsubstituted phenyl group, k2a and k3a are each independently an integer of 0 to 4, k4a is an integer of 0 to 7, l1 is 1 or 2, ar ¹ 、R ¹ 、X ¹ 、X ² 、Q ¹ 、Q ² Z and k1 are the same as those defined in the chemical formula 1, the chemical formula 2-1 and the chemical formula 2-2.

In an embodiment, X in the case where the FG is represented by the chemical formula 2-1 ¹ And X ² At least one of which may be a substituted or unsubstituted naphthyl group, X in the case where the FG is represented by the chemical formula 2-2 ¹ May be substituted or unsubstituted naphthyl.

In one embodiment, X ¹ And X ² May be represented by any one of XS-1 to XS-6 described below, respectively and independently.

In said XS-1 to said XS-6, R ^s1 To R ^s6 Each independently is a hydrogen atom, a heavy hydrogen atom, a halogen atom, or a substituted or unsubstituted aryl group having 6 to 20 ring-forming carbon atoms, s1 to s3 and s5 are each independently an integer of 0 to 7, and s4 is an integer of 0 to 8.

In one embodiment, the light emitting layer may include a compound represented by the following chemical formula E-1.

[ chemical formula E-1]

In said formula E-1, R ₃₁ To R ₄₀ Each independently is a hydrogen atom, a heavy hydrogen atom, a halogen atom, a substituted or unsubstituted silyl group, a substituted or unsubstituted thio group, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group having 1 or more and 10 or less carbon atoms, a substituted or unsubstituted alkenyl group having 2 or more and 10 or less carbon atoms, a substituted or unsubstituted aryl group having 6 or more and 30 or less ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 or more and 30 or less ring-forming carbon atoms, and is optionally combined with an adjacent group to form a ring, and c and d are each independently an integer of 0 or more and 5 or less.

In one embodiment, the amine compound may be represented by any one of the compounds of the compound group 1 described later.

The light-emitting element of an embodiment may include the amine compound of an embodiment, and thus may exhibit long-life characteristics.

The amine compound of one embodiment can be used as a material for achieving the characteristics of the light-emitting element with improved long life.

Drawings

Fig. 1 is a plan view illustrating a display device according to an embodiment.

Fig. 2 is a cross-sectional view of a display device according to an embodiment.

Fig. 3 is a sectional view schematically showing a light emitting element according to an embodiment.

Fig. 4 is a sectional view schematically showing a light emitting element according to an embodiment.

Fig. 5 is a sectional view schematically showing a light emitting element according to an embodiment.

Fig. 6 is a sectional view schematically showing a light emitting element according to an embodiment.

Fig. 7 is a cross-sectional view of a display device according to an embodiment.

Fig. 8 is a cross-sectional view of a display device according to an embodiment.

Fig. 9 is a cross-sectional view illustrating a display device according to an embodiment.

Fig. 10 is a cross-sectional view illustrating a display device according to an embodiment.

Description of the reference numerals

DD. DD-TD, DD-a, DD-b and DD-c: display device

ED: light emitting element EL1: first electrode

EL2: second electrode HTR: hole transport region

EML: light emitting layer ETR: electron transport region

HTL: hole transport layer CPL: cover layer

Detailed Description

While the invention is susceptible to various modifications and alternative forms, specific embodiments have been shown by way of example in the drawings and will be described in detail herein. However, it is not intended to limit the invention to the particular form disclosed, but it is to be understood that the invention is to include all modifications, equivalents, and alternatives falling within the spirit and scope of the invention.

Like reference numerals are used for like components while describing the respective drawings. In the drawings, the size of the structures is shown exaggerated compared to actual for the clarity of the invention. The terms "first," "second," and the like may be used to describe various elements, but the elements should not be limited by the terms. The term is used only for the purpose of distinguishing one component from other components. For example, a first component may be termed a second component, and, similarly, a second component may be termed a first component, without departing from the scope of the present disclosure. The expression "singular" includes the expression "plural" if the context does not explicitly indicate a different meaning.

In this specification, the terms "comprises" and "comprising" and the like are to be understood to mean that the features, numbers, steps, operations, components, parts, or combinations thereof described in the specification are present, but that the presence or additional possibility of one or more other features, numbers, steps, operations, components, parts, or combinations thereof is not pre-excluded.

In this specification, when a portion of a layer, a film, a region, a plate, or the like is referred to as being "on" or "upper" other portion, this includes not only the case of being "immediately above" other portion but also the case of having another portion in the middle thereof. Conversely, when a portion of a layer, film, region, plate, or the like is referred to as being "under" or "lower" other portion, this includes not only the case of being "immediately under" the other portion but also the case of having another portion in the middle thereof. Also, in the present application, the expression "disposed on" is not only disposed on the upper portion but also includes the case of being disposed on the lower portion.

In the present specification, "substituted or unsubstituted" may mean substituted or unsubstituted with one or more substituents selected from the group consisting of: heavy hydrogen atom, halogen atom, cyano group, nitro group, amino group, silyl group, oxy group, thio group, sulfinyl group, sulfonyl group, carbonyl group, boron group, phosphine oxide group, phosphine sulfide group, alkyl group, alkenyl group, alkynyl group, hydrocarbon ring group, aryl group, and heterocyclic group. And, each of the substituents shown may be a substituted or unsubstituted substituent. For example, biphenyl may also be interpreted as aryl, and may be interpreted as phenyl substituted with phenyl.

In this specification, "combine with adjacent groups to form a ring" may mean combine with adjacent groups to form a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocyclic ring. The hydrocarbon ring includes aliphatic hydrocarbon rings and aromatic hydrocarbon rings. The heterocyclic ring includes aliphatic heterocyclic ring and aromatic heterocyclic ring. The hydrocarbon ring and the heterocyclic ring may be monocyclic or polycyclic. And, the rings formed by being combined with each other may be connected with another ring to form a screw structure.

In this specification, "an adjacent group" may mean a substituent substituted at an atom directly connected to an atom substituted with a corresponding substituent, another substituent substituted at an atom substituted with a corresponding substituent, or a substituent most adjacent to a corresponding substituent in a steric structure. For example, in 1, 2-xylene (1, 2-dimethyllbenzene), two methyl groups may be interpreted as "adjacent groups" to each other, and in 1,1-diethylcyclopentane (1, 1-diethylcyclopen), two ethyl groups may be interpreted as "adjacent groups" to each other. Also, in 4,5-dimethylphenanthrene (4, 5-dimethylphenanthrene), two methyl groups may be interpreted as "adjacent groups" to each other.

In this specification, examples of the halogen atom are a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom.

In the present specification, the alkyl group may be straight chain, branched chain or cyclic. The carbon number of the alkyl group is 1 to 50, 1 to 30, 1 to 20, 1 to 10, or 1 to 6. Examples of alkyl groups include: methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, isobutyl, 2-ethylbutyl, 3-dimethylbutyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, cyclopentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 2-butylhexyl, cyclohexyl, 4-methylcyclohexyl, 4-tert-butylcyclohexyl, n-heptyl, 1-methylheptyl, 2-dimethylheptyl, 2-ethylheptyl, 2-butylheptyl, n-octyl, tert-octyl, 2-ethyloctyl, 2-butyloctyl, 2-hexyloctyl, 3, 7-dimethyloctyl, cyclooctyl, n-nonyl n-decyl, adamantyl, 2-ethyldecyl, 2-butyldecyl, 2-hexyldecyl, 2-octyldecyl, n-undecyl, n-dodecyl, 2-ethyldodecyl, 2-butyldodecyl, 2-hexyldodecyl, 2-octyldodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, 2-ethylhexadecyl, 2-butylhexadecyl, 2-hexylhexadecyl, 2-octylhexadecyl, n-heptadecyl, n-octadecyl, n-nonadecyl, n-eicosyl, 2-ethyleicosyl, 2-butyleicosyl, 2-hexyleicosyl, 2-octyleicosyl, n-eicosyl, n-docosyl, n-eicosyl, N-tricosyl, n-tetracosyl, n-pentacosyl, n-hexacosyl, n-heptacosyl, n-octacosyl, n-nonacosyl, n-triacontyl, etc., but are not limited thereto.

In the present specification, an alkenyl group means a hydrocarbon group including one or more carbon double bonds in the middle or at the end of an alkyl group having two or more carbon atoms. Alkenyl groups may be straight or branched. The number of carbon atoms is not particularly limited, but is 2 to 30, 2 to 20, or 2 to 10. Examples of alkenyl groups include, but are not limited to, vinyl, 1-butenyl, 1-pentenyl, 1, 3-butadienyl, styryl and the like.

In the present specification, alkynyl means a hydrocarbon group including a carbon triple bond in the middle or at the end of an alkyl group having two or more carbon atoms. Alkynyl groups may be straight or branched. The number of carbon atoms is not particularly limited, but is 2 to 30, 2 to 20, or 2 to 10. Specific examples of the alkynyl group may include an ethynyl group, a propynyl group, and the like, but are not limited thereto.

In the present specification, a hydrocarbon ring group means any functional group or substituent derived from an aliphatic hydrocarbon ring. The hydrocarbon ring group may be a saturated hydrocarbon ring group having 5 or more and 20 or less ring-forming carbon atoms.

In the present specification, aryl means any functional group or substituent derived from an aromatic hydrocarbon ring. Aromatic hydrocarbon The radicals may be monocyclic aryl or polycyclic aryl. The number of ring-forming carbon atoms of the aryl group may be 6 to 50, 6 to 30, 6 to 20, or 6 to 15. Examples of aryl groups include phenyl, naphthyl, fluorenyl, anthryl, phenanthryl, biphenyl, terphenyl, tetrabiphenyl, pentabiphenyl (quinquephenyl), p-hexabiphenyl, and benzo [9,10 ]]Phenanthryl, pyrenyl, benzofluoranthenyl,A base, etc., but is not limited thereto.

In the present specification, the fluorenyl group may be substituted, or two substituents may be bonded to each other to form a spiro structure. Examples of the case where the fluorenyl group is substituted are as follows. However, it is not limited thereto.

In this specification, a heterocyclic group means any functional group or substituent derived from a ring including one or more of B, O, N, P, si and S as a hetero atom. Heterocyclic groups include aliphatic heterocyclic groups and aromatic heterocyclic groups. The aromatic heterocyclic group may be a heteroaryl group. The aliphatic and aromatic heterocycles may be monocyclic or polycyclic.

In the present specification, the heterocyclic group may include one or more of B, O, N, P, si and S as a hetero atom. When the heterocyclic group includes two or more hetero atoms, the two or more hetero atoms may be the same as or different from each other. In the present specification, a heterocyclic group may be a monocyclic heterocyclic group or a polycyclic heterocyclic group, and is a concept including heteroaryl groups. The number of ring-forming carbon atoms of the heterocyclic group may be 2 or more and 50 or less, 2 or more and 30 or less, 2 or more and 20 or less, or 2 or more and 10 or less.

In the present specification, the aliphatic heterocyclic group may include one or more of B, O, N, P, si and S as a hetero atom. The number of ring-forming carbon atoms of the aliphatic heterocyclic group may be 2 or more and 30 or less, 2 or more and 20 or less, or 2 or more and 10 or less. Examples of the aliphatic heterocyclic group include, but are not limited to, ethylene oxide group, pyrrolidinyl group, piperidinyl group, tetrahydrofuranyl group, tetrahydrothienyl group, thiocyclopentanyl group, tetrahydropyranyl group, 1, 4-dioxanyl group, and the like.

In this specification, heteroaryl groups may include B, O, N, P, si and one or more of S species as heteroatoms. When the heteroaryl group includes two or more heteroatoms, the two or more heteroatoms may be the same as each other or different from each other. Heteroaryl groups may be monocyclic or polycyclic. The number of ring-forming carbon atoms of the heteroaryl group may be 2 or more and 50 or less, 2 or more and 30 or less, 2 or more and 20 or less, or 2 or more and 10 or less. Examples of heteroaryl groups include thienyl, furyl, pyrrolyl, imidazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, isoquinolinyl, indolyl, carbazolyl, N-arylcarbazolyl, N-heteroarylcarbazolyl, N-alkylcarbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, thiophenyl, benzofuranyl, phenanthroline, thiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, thiadiazolyl, phenothiazinyl, dibenzosilol, dibenzofuranyl, and the like, but are not limited thereto.

In this specification, for arylene groups, the description above regarding aryl groups may be applied in addition to being divalent. For heteroarylene groups, the description above regarding heteroaryl groups may be applied in addition to being divalent.

In the present specification, boron group may mean that a boron atom is bonded to an alkyl group or an aryl group as defined above. Boron groups include alkyl boron groups and aryl boron groups. Examples of the boron group include, but are not limited to, dimethylboronyl, diethylboronyl, t-butylmethylboronyl, diphenylboronyl, phenylboronyl, and the like.

In the present specification, silyl groups include alkylsilyl groups and arylsilyl groups. Examples of the silyl group include, but are not limited to, trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, and the like.

In the present specification, the number of carbon atoms of the carbonyl group is not particularly limited, and the number of carbon atoms may be 1 to 40 or less, 1 to 30 or less, or 1 to 20 or less. For example, the following structure may be available, but is not limited thereto.

In the present specification, the number of carbon atoms of the sulfinyl group and the sulfonyl group is not particularly limited, but may be 1 or more and 30 or less. Sulfinyl groups may include alkylsulfinyl and arylsulfinyl groups. The sulfonyl group may include alkylsulfonyl and arylsulfonyl.

In the present specification, a thio group may include an alkylthio group and an arylthio group. Thio may mean that the sulfur atom is bound to an alkyl or aryl group as defined above. Examples of the thio group include, but are not limited to, a methylthio group, an ethylthio group, a propylthio group, a pentylthio group, a hexylthio group, an octylthio group, a dodecylthio group, a cyclopentylthio group, a cyclohexylthio group, a phenylthio group, a naphthylthio group, and the like.

In the present specification, an oxygen group may mean that an oxygen atom is bonded to an alkyl group or an aryl group as defined above. The oxy group may include an alkoxy group and an aryloxy group. Alkoxy groups may be straight, branched or cyclic. The number of carbon atoms of the alkoxy group is not particularly limited, but may be, for example, 1 to 20 or less, or 1 to 10 or more. Examples of the oxygen group include, but are not limited to, methoxy, ethoxy, n-propoxy, isopropoxy, butoxy, pentyloxy, hexyloxy, octyloxy, nonyloxy, decyloxy, benzyloxy, and the like.

In the present specification, the number of carbon atoms of the amine group is not particularly limited, but may be 1 or more and 30 or less. Amine groups may include alkyl amine groups and aryl amine groups. Examples of the amine group include, but are not limited to, methylamino group, dimethylamino group, phenylamino group, diphenylamino group, naphthylamino group, 9-methyl-anthracenylamino group, and the like.

In the present specification, the alkyl group in the alkylthio group, the alkylsulfinyl group, the alkylsulfonyl group, the alkoxy group, the alkylboron group, the alkylsilyl group, and the alkylamino group is the same as the examples of the alkyl group described above.

In this specification, the aryl groups in the aryloxy group, the arylthio group, the arylsulfinyl group, the arylsulfonyl group, the arylboron group, the arylsilyl group, and the arylamine group are the same as those exemplified above.

In the present specification, direct bonding (direct linkage) may mean a single bond.

In addition, the method comprises the following steps. In the present description of the invention,or "-" refers to the location of the connection.

An embodiment of the present invention will be described below with reference to the drawings.

Fig. 1 is a plan view showing an embodiment of the display device DD. Fig. 2 is a cross-sectional view of a display device DD according to an embodiment. Fig. 2 is a sectional view showing a portion corresponding to the line I-I' of fig. 1.

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 comprises light emitting elements ED-1, ED-2, ED-3. The display device DD may comprise a plurality of light emitting elements ED-1, ED-2, ED-3. The optical layer PP may be disposed on the display panel DP to control reflected light from the display panel DP caused by external light. For example, the optical layer PP may include a polarizing layer or a color filter layer. In addition, the optical layer PP may be omitted in the display device DD of an embodiment, unlike that shown in the drawings.

The base substrate BL may be disposed on the optical layer PP. The base substrate BL may be a member providing a base surface on which the optical layer PP is disposed. The base substrate BL may be a glass substrate, a metal substrate, a plastic substrate, or the like. However, the embodiment is not limited thereto, and the base substrate BL may be an inorganic layer, an organic layer, or a composite material layer. Further, unlike what is shown, in an embodiment, the base substrate BL may be omitted.

The display device DD according to an embodiment may further comprise a filler layer (not shown). A filling layer (not shown) may be disposed between the display element layer DP-ED and the base substrate BL. The filling layer (not shown) may be an organic layer. The filling layer (not shown) may include at least one of an acrylic resin, a silicone resin, and an epoxy resin.

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

The base layer BS may be a member providing a base surface on which the display element layers DP-ED are arranged. The base layer BS may be a glass substrate, a metal substrate, a plastic substrate, or the like. However, the embodiment is not limited thereto, and the base layer BS may be an inorganic layer, an organic layer, or a composite material layer.

In an embodiment, 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 (not shown). The transistors (not shown) may include a control electrode, an input electrode, and an output electrode, respectively. For example, the circuit layer DP-CL may include switching transistors and driving transistors for driving the light emitting elements ED-1, ED-2, ED-3 of the display element layer DP-ED.

Each of the light emitting elements ED-1, ED-2, ED-3 may have a structure of the light emitting element ED according to an embodiment of fig. 3 to 6 described later. Each of the light emitting elements ED-1, ED-2, ED-3 may include a first electrode EL1, a hole transporting region HTR, a light emitting layer EML-R, EML-G, EML-B, an electron transporting region ETR, and a second electrode EL2.

Fig. 2 shows an embodiment in which the light emitting layers EML-R, EML-G, EML-B of the light emitting elements ED-1, ED-2, ED-3 are arranged within the opening OH defined by the pixel defining film PDL and the hole transporting region HTR, the electron transporting region ETR, and the second electrode EL2 are provided as a common layer in the entire light emitting elements ED-1, ED-2, ED-3. However, the embodiment is not limited thereto, and in an embodiment, the hole transport region HTR and the electron transport region ETR may be provided by patterning inside the opening OH defined by the pixel definition film PDL, unlike the case shown in fig. 2. For example, in one embodiment, the hole transport regions HTR, the light emitting layers EML-R, EML-G, EML-B, and the electron transport regions ETR, etc. of the light emitting elements ED-1, ED-2, ED-3 may be provided by patterning by ink jet printing.

The encapsulation layer TFE may cover the light emitting elements ED-1, ED-2, ED-3. The encapsulation layer TFE may encapsulate the display element layer DP-ED. The encapsulation layer TFE may be a thin film encapsulation layer. The encapsulation layer TFE may be a layer or a stack of layers. The encapsulation layer TFE includes at least one insulating layer. The encapsulation layer TFE according to an embodiment may include at least one inorganic film (hereinafter, referred to as an encapsulation inorganic film). Also, the encapsulation layer TFE according to an embodiment may include at least one organic film (hereinafter, referred to as an encapsulation organic film) and at least one encapsulation inorganic film.

The encapsulation inorganic film protects the display element layer DP-ED from moisture/oxygen, and the encapsulation organic film protects the display element layer DP-ED from foreign substances such as dust particles. The encapsulating inorganic film may include silicon nitride, silicon oxynitride, silicon oxide, titanium oxide, aluminum oxide, or the like, but is not particularly limited. The encapsulating organic film may include an acrylic compound, an epoxy compound, and the like. The encapsulating organic film may include an organic substance capable of photopolymerization, and is not particularly limited.

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

Referring to fig. 1 and 2, the display device DD may include a non-light emitting area NPXA and a light emitting area PXA-R, PXA-G, PXA-B. Each of the light emitting regions PXA-R, PXA-G, PXA-B may be a region that emits light generated from each of the light emitting elements ED-1, ED-2, ED-3. The light emitting areas PXA-R, PXA-G, PXA-B may be spaced apart from each other in a plane.

Each of the light emitting areas PXA-R, PXA-G, PXA-B may be an area divided by the pixel defining film PDL. The non-light emitting region NPXA may be a region between adjacent light emitting regions PXA-R, PXA-G, PXA-B, and may be a region corresponding to the pixel definition film PDL. In addition, in the present specification, each of the light emitting areas PXA-R, PXA-G, PXA-B may correspond to a Pixel (Pixel). The pixel definition film PDL may divide the light emitting elements ED-1, ED-2, ED-3. The light emitting layers EML-R, EML-G, EML-B of the light emitting elements ED-1, ED-2, ED-3 may be arranged in the opening portion OH defined by the pixel defining film PDL to be divided.

The light emitting areas PXA-R, PXA-G, PXA-B may be divided into a plurality of groups according to the color of light generated from the light emitting elements ED-1, ED-2, ED-3. In the display device DD of an embodiment shown in fig. 1 and 2, three light emitting areas PXA-R, PXA-G, PXA-B emitting red, green and blue light are exemplarily shown. For example, the display device DD of an embodiment may include red, green, and blue light-emitting regions PXA-R, PXA-G, and PXA-B that are divided from one another.

In the display device DD according to an embodiment, the plurality of light emitting elements ED-1, ED-2, ED-3 may emit light in wavelength regions different from each other. For example, in one embodiment, the display device DD may include a first light emitting element ED-1 emitting red light, a second light emitting element ED-2 emitting green light, and a third light emitting element ED-3 emitting blue light. That is, the red, green, and blue light emitting regions PXA-R, PXA-G, and PXA-B of the display device DD may correspond to the first, second, and third light emitting elements ED-1, ED-2, and ED-3, respectively.

However, the embodiment is not limited thereto, and the first, second, and third light emitting elements ED-1, ED-2, and ED-3 may emit light of the same wavelength region, or at least one may emit light of different wavelength regions. For example, the first light-emitting element ED-1, the second light-emitting element ED-2, and the third light-emitting element ED-3 may each emit blue light.

The light emitting areas PXA-R, PXA-G, PXA-B in the display device DD according to an embodiment may be arranged in a stripe pattern. Referring to fig. 1, the plurality of red light emitting areas PXA-R, the plurality of green light emitting areas PXA-G, and the plurality of blue light emitting areas PXA-B may be aligned along the second direction axis DR2, respectively. Also, the red light emitting regions PXA-R, the green light emitting regions PXA-G, and the blue light emitting regions PXA-B may be alternately arranged in this order along the first direction axis DR 1.

In fig. 1 and 2, the areas of the light emitting areas PXA-R, PXA-G, PXA-B are shown to be all similar, but the embodiment is not limited thereto, and the areas of the light emitting areas PXA-R, PXA-G, PXA-B may be different from each other according to the wavelength region of the emitted light. In addition, the area of the light emitting region PXA-R, PXA-G, PXA-B may refer to an area as viewed on a plane defined by the first direction axis DR1 and the second direction axis DR 2.

The arrangement of the light emitting regions PXA-R, PXA-G, PXA-B is not limited to that shown in fig. 1, and the arrangement order of the red light emitting regions PXA-R, the green light emitting regions PXA-G, and the blue light emitting regions PXA-B may be variously combined and provided according to the characteristics of the display quality required for the display device DD. For example, the arrangement of the light emitting areas PXA-R, PXA-G, PXA-B may be five tiles Arrangement form or Diamond (Diamond pixels) ^TM ) The arrangement form.

Also, the areas of the light emitting areas PXA-R, PXA-G, PXA-B may be different from each other. For example, in an embodiment, the area of the green light emitting areas PXA-G may be smaller than that of the blue light emitting areas PXA-B, but the embodiment is not limited thereto.

Hereinafter, fig. 3 to 6 are sectional views schematically showing a light emitting element according to an embodiment. The light emitting element ED according to an embodiment may include a first electrode EL1, a second electrode EL2 facing the first electrode EL1, and at least one functional layer disposed between the first electrode EL1 and the second electrode EL2. The light-emitting element ED of one embodiment may include an amine compound of one embodiment described later in at least one functional layer.

The light emitting element ED may include a hole transport region HTR, a light emitting layer EML, an electron transport region ETR, and the like, which are stacked in order, as at least one functional layer. Referring to fig. 3, the light emitting element ED of an embodiment may include a first electrode EL1, a hole transporting region HTR, a light emitting layer EML, an electron transporting region ETR, and a second electrode EL2, which are sequentially stacked.

In comparison with fig. 3, fig. 4 shows a cross-sectional view of a light emitting element ED of an embodiment in which the hole transport region HTR includes the hole injection layer HIL and the electron blocking layer EBL and the electron transport region ETR includes the electron injection layer EIL and the electron transport layer ETL. In addition, fig. 5 is a cross-sectional view of a light-emitting element ED according to an embodiment in which the hole transport region HTR includes the hole injection layer HIL, the hole transport layer HTL, and the electron blocking layer EBL, and the electron transport region ETR includes the electron injection layer EIL, the electron transport layer ETL, and the hole blocking layer HBL, as compared with fig. 3. Fig. 6 is a sectional view showing a light-emitting element ED of an embodiment including the cover layer CPL disposed on the second electrode EL2, as compared with fig. 4.

The light emitting element ED of an embodiment may include an amine compound of an embodiment described later in the hole transport region HTR. In the light emitting element ED of an embodiment, at least one of the hole injection layer HIL, the hole transport layer HTL, and the electron blocking layer EBL in the hole transport region HTR may include the amine compound of an embodiment. For example, in the light emitting element ED of an embodiment, the electron blocking layer EBL may include the amine compound of an embodiment. The electron blocking layer EBL is a layer for preventing electrons from being injected from the electron transport region ETR to the hole transport region HTR.

In the light emitting element ED according to an embodiment, the first electrode EL1 has conductivity. The first electrode EL1 may be formed using a metal material, a metal alloy, or a conductive compound. The first electrode EL1 may be an anode (anode) or a cathode (cathode). However, the embodiment is not limited thereto. Also, the first electrode EL1 may be a pixel electrode. The first electrode EL1 may be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode. The first electrode EL1 may include at least one selected from Ag, mg, cu, al, pt, pd, au, ni, nd, ir, cr, li, ca, liF, mo, ti, W, in, sn and Zn, two or more compounds selected from them, a mixture of two or more compounds selected from them, or an oxide thereof.

In the first placeIn the case where one electrode EL1 is a transmissive electrode, the first electrode EL1 may include a transparent metal oxide (for example, indium Tin Oxide (ITO), indium zinc oxide (IZO: indium zinc oxide), zinc oxide (ZnO: zinc oxide), indium tin zinc oxide (ITZO: indium tin zinc oxide)). In the case where the first electrode EL1 is a semi-transmissive electrode or a reflective electrode, the first electrode EL1 may include Ag, mg, cu, al, pt, pd, au, ni, nd, ir, cr, li, ca, liF, mo, ti, W or a compound or mixture thereof (e.g., a mixture of Ag and Mg) or a material having a multilayer structure including two or more selected from them (e.g., liF/Ca (a stacked structure of LiF and Ca) or LiF/Al (a stacked structure of LiF and Al)). Alternatively, the first electrode EL1 may be a multilayer structure including a reflective film or a semi-transmissive film formed using the above-described substance, a transparent conductive film formed using Indium Tin Oxide (ITO), indium zinc oxide (IZO: indium zinc oxide), zinc oxide (ZnO: zinc oxide), indium tin zinc oxide (ITZO: indium tin zinc oxide), or the like. For example, the first electrode EL1 may have a three-layer structure of ITO/Ag/ITO, but is not limited thereto. Alternatively, the embodiment is not limited thereto, and the first electrode EL1 may include the above-described metal material, a combination of two or more metal materials selected from the above-described metal materials, an oxide of the above-described metal material, or the like. The thickness of the first electrode EL1 may be about To about->For example, the thickness of the first electrode EL1 may be aboutTo about->

The hole transport region HTR is provided on the first electrode EL 1. The hole transport region HTR may have: a single layer structure formed by a single substance; a single-layer structure configured by a plurality of substances different from each other; or a multi-layer structure having a plurality of layers made of a plurality of substances different from each other.

The hole transport region HTR may include at least one of a hole injection layer HIL, a hole transport layer HTL, and an electron blocking layer EBL. Also, although not shown, the hole transport region HTR may further include a plurality of stacked hole transport layers.

In contrast, the hole transport region HTR may have a single-layer structure of the hole injection layer HIL or the hole transport layer HTL, or may have a single-layer structure formed using, for example, a hole injection material and a hole transport material. In an embodiment, the hole transport region HTR may have a single layer structure composed of a plurality of substances different from each other, or a structure having a hole injection layer HIL/hole transport layer HTL, a hole injection layer HIL/hole transport layer HTL/buffer layer (not shown), a hole injection layer HIL/buffer layer (not shown), or a hole transport layer HTL/buffer layer (not shown) stacked in order from the first electrode EL1, but the embodiment is not limited thereto.

The hole transport region HTR may have a thickness of, for example, aboutTo about->The hole transport region HTR may be formed using various methods such as a vacuum deposition method, a spin coating method, a casting method, langmuir-Blodgett (LB), an inkjet printing method, a laser thermal transfer method (LITI: laser Induced Thermal Imaging), and the like.

The light emitting element ED of an embodiment may include the amine compound of an embodiment in the hole transport region HTR. In the light emitting element ED of an embodiment, the hole transport region HTR may include an electron injection layer EIL, a hole transport layer HTL, and an electron blocking layer EBL. For example, the electron blocking layer EBL may include an amine compound of an embodiment. In one embodiment, the amine compound may be represented by the following chemical formula 1.

[ chemical formula 1]

In the chemical formula 1, Q ¹ May be O or S, ar ¹ May be a substituted or unsubstituted phenyl group. For example, at Q ¹ In the case of O, a substituted or unsubstituted phenyl group may be bonded to the 6-position of the dibenzofuranyl group, and the nitrogen atom (N) of the amine compound may be bonded to the 3-position of the dibenzofuranyl group. And at Q ¹ In the case of S, a substituted or unsubstituted phenyl group may be bonded to the 6-position of dibenzothienyl, and the nitrogen atom (N) of the amine compound may be bonded to the 3-position of dibenzothienyl.

That is, the amine compound of an embodiment represented by chemical formula 1 may include a substituent of a dibenzoheteroskeleton to which a substituted or unsubstituted phenyl group is bonded at the 6-position and a nitrogen atom (N) of the amine compound is bonded at the 3-position. Thus, the amine compound of one embodiment has high stability, contributes to improvement of the lifetime of a light-emitting element when used as a hole transport material of the light-emitting element, and can be suitably applied to an electron blocking layer of the light-emitting element by appropriately adjusting the LUMO level.

In chemical formula 1, R ¹ And R is ² Each independently represents a hydrogen atom, a heavy hydrogen atom, a halogen atom, a substituted or unsubstituted silyl group, a substituted or unsubstituted aryl group having 6 or more and 30 or less ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 or more and 30 or less ring-forming carbon atoms. For example, R ¹ And R is ² May each be independently a hydrogen atom, a heavy hydrogen atom or a halogen atom. At R ¹ And R is ² In the case where each of these is a halogen atom, the amine compound of an embodiment may include a fluorine atom (F) as a halogen atom.

In chemical formula 1, n1 may be an integer of 1 to 3. For example, n1 may be 1 or 2. k1 may be an integer of 0 to 6 inclusive K2 may be an integer of 0 to 4. The case where k1 is 0 may be as same as where k1 is 6 and R ¹ The same applies to the case of a hydrogen atom. The case where k2 is 0 may be 4 with k2 and R ² The same applies to the case of a hydrogen atom.

In one embodiment, where k1 is an integer greater than 2, a plurality of R ¹ Can be the same or at least one can be the same as the rest of R ¹ Different. In addition, in the case where k1 is 0, the substituent of the dibenzoheteroskeleton in chemical formula 1 may not be R ¹ And (3) substitution. When k2 is an integer of 2 or more, a plurality of R ² Can be the same or at least one can be the same as the rest of R ² Different. In addition, in the case where k2 is 0, the phenylene group in chemical formula 1 may not be R ² And (3) substitution.

In chemical formula 1, X ¹ May be a substituted or unsubstituted naphthyl group or a substituted or unsubstituted heteroaryl group having 2 or more and 30 or less ring-forming carbon atoms. For example, X ¹ The substituted or unsubstituted naphthyl group may be a naphthyl group substituted with a heavy hydrogen atom, a halogen atom, or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms in a ring, or may be a heteroaryl group having 2 to 20 carbon atoms in a ring, which contains an oxygen atom (O) or a nitrogen atom (N). However, due to The stability to holes and electrons is low, and thus X can be excluded from the amine compound of one embodiment ¹ Is->Is the case in (a).

In one embodiment, X ¹ May be represented by any one of XS-1 to XS-6 described below.

In the XS-1 to XS-6, s1 to s3 and s5 may be respectivelyIndependently, s4 is an integer of 0 to 7, and s4 is an integer of 0 to 8. R is R ^s1 To R ^s6 Each independently represents a hydrogen atom, a heavy hydrogen atom, a halogen atom, or a substituted or unsubstituted aryl group having 6 to 20 ring-forming carbon atoms. For example, R ^s1 To R ^s6 May be a hydrogen atom, a heavy hydrogen atom, a halogen atom, or a substituted or unsubstituted phenyl group. At R ^s1 To R ^s6 In the case where each of these is a halogen atom, the amine compound of an embodiment may include a fluorine atom (F) as a halogen atom.

In one embodiment, s1 is 0 may be equal to s1 is 7 and R ^s1 The same applies to the case of a hydrogen atom. The case where s2 is 0 may be equal to s2 being 7 and R ^s2 In the same manner as in the case of hydrogen, s3 is 0 and s3 is 7 and R ^s3 The same applies to the case of a hydrogen atom. And, the case where s4 is 0 may be equal to s4 is 8 and R ^s4 The same as in the case of hydrogen, s5 is 0 and s5 is 7 and R ^s5 The same applies to the case of a hydrogen atom.

In one embodiment, where s1 is an integer of 2 or more, a plurality of R ^s1 Can be the same as or at least one of the same as the remainder of R ^s1 Different. In addition, XS-1 may not be R in the case where s1 is 0 ^s1 And (3) substitution. When s2 is an integer of 2 or more, a plurality of R ^s2 Can be the same as or at least one of the same as the remainder of R ^s2 Different. In addition, XS-2 may not be R in the case where s2 is 0 ^s2 And (3) substitution. When s3 is an integer of 2 or more, a plurality of R ^s3 Can be the same as or at least one of the same as the remainder of R ^s3 Different. In addition, in the case where s3 is 0, XS-3 may not be R ^s3 And (3) substitution. When s4 is an integer of 2 or more, a plurality of R ^s4 Can be the same as or at least one of the same as the remainder of R ^s4 Different. In addition, in the case where s4 is 0, XS-4 may not be R ^s4 And (3) substitution.

In chemical formula 1, FG may be represented by chemical formula 2-1 or chemical formula 2-2 below.

[ chemical formula 2-1]

[ chemical formula 2-2]

In chemical formula 2-1, n2 may be an integer of 1 to 3. For example, n2 may be 1 or 2.X is X ² May be a substituted or unsubstituted naphthyl group or a substituted or unsubstituted heteroaryl group having 2 or more and 30 or less ring-forming carbon atoms. For example, X ² The substituted or unsubstituted naphthyl group may be a naphthyl group or an unsubstituted naphthyl group substituted with a heavy hydrogen atom, a halogen atom, or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms in a ring, or may be a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms in a ring, which contains an oxygen atom (O) or a nitrogen atom (N) as a ring-forming atom. However, due toThe stability to holes and electrons is low, and thus X can be excluded from the amine compound of one embodiment ² Is thatIs the case in (a).

In one embodiment, X ² May be represented by any one of XS-1 to XS-6. At X ² Where represented by any one of the XS-1 to XS-6, the same contents as those described in the XS-1 to XS-6 may be applied to X ² 。

In chemical formulas 2-1 and 2-2, R ³ And R is ⁴ Each independently represents a hydrogen atom, a heavy hydrogen atom, a halogen atom, a substituted or unsubstituted silyl group, a substituted or unsubstituted aryl group having 6 or more and 30 or less ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 or more and 30 or less ring-forming carbon atoms. At the position ofIn one embodiment, R ³ And R is ⁴ Each independently represents a hydrogen atom, a heavy hydrogen atom, a halogen atom, a substituted or unsubstituted aryl group having 6 or more and 15 or less ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 or more and 15 or less ring-forming carbon atoms. For example, R ³ And R is ⁴ May each be independently a hydrogen atom, a heavy hydrogen atom, a halogen atom, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted dibenzofuranyl group. In addition, at R ³ And R is ⁴ In the case where each of these is a halogen atom, the amine compound of an embodiment may include a fluorine atom (F) as a halogen atom.

In chemical formulas 2-1 and 2-2, k3 may be an integer of 0 to 4, and k4 may be an integer of 0 to 7. The case where k3 is 0 may be equal to k3 being 4 and R ³ The same applies to the case of a hydrogen atom. The case where k4 is 0 may be as described for k4 being 7 and R ⁴ The same applies to the case of a hydrogen atom.

In one embodiment, where k3 is an integer greater than 2, a plurality of R ³ Can be the same or at least one can be the same as the rest of R ³ Different. In addition, in the case where k3 is 0, the phenylene group in the chemical formula 2-1 may not be R ³ And (3) substitution. When k4 is an integer of 2 or more, a plurality of R ⁴ Can be the same or at least one can be the same as the rest of R ⁴ Different. In addition, in the case where k4 is 0, the substituent condensed in the chemical formula 2-2 may not be R ⁴ And (3) substitution.

In chemical formula 2-2, Q ² Can be O, S, NR ⁵ Or CR ⁶ R ⁷ 。R ⁵ To R ⁷ Each independently represents a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 50 ring-forming carbon atoms. For example, R ⁵ To R ⁷ May be a substituted or unsubstituted phenyl group.

In chemical formula 2-2, Z may be a substituted or unsubstituted aromatic hydrocarbon ring having 6 or more and 30 or less ring-forming carbon atoms or a substituted or unsubstituted aromatic heterocyclic ring having 2 or more and 30 or less ring-forming carbon atoms. In one embodiment, Z may be a substituted or unsubstituted aromatic hydrocarbon ring having 6 or more and 10 or less ring-forming carbon atoms.

In chemical formula 2-2, the number of rings represented by Z may be one or two. For example, in chemical formula 2-2, in the case where the number of rings represented by Z is one, one ring in the portion represented by Z constitutes a condensed ring, and in the case where the number of rings represented by Z is two, two rings in the portion represented by Z constitute a condensed ring. Specifically, in the case where the number of rings represented by Z is one, the condensed ring represented by chemical formula 2-2 may be a substituent of a ring having a tricyclic ring. Also, in the case where the number of rings represented by Z is two, the condensed ring represented by chemical formula 2-2 may be a substituent having four rings.

The amine compound of an embodiment may include at least one substituted or unsubstituted naphthyl group as a substituent. For example, in chemical formula 1, in the case where FG is represented by chemical formula 2-1, X ¹ And X ² May be a substituted or unsubstituted naphthyl group. And, in the case where FG is represented by chemical formula 2-2, X ¹ May be substituted or unsubstituted naphthyl.

In addition, ar of chemical formula 1 ¹ 、R ¹ 、R ² 、X ¹ And FG may include a heavy hydrogen atom or a substituent containing a heavy hydrogen atom. That is, the amine compound of an embodiment may include at least one heavy hydrogen atom as a substituent.

In one embodiment, chemical formula 2-1 may be represented by chemical formula 2-1a or chemical formula 2-1b below. That is, in the amine compound of an embodiment, FG of chemical formula 1 may be represented by chemical formula 2-1a or chemical formula 2-1 b. In chemical formula 2-1a, n2 may be the same as that described in chemical formula 2-1. In chemical formulas 2-1a and 2-1b, X ² The same inner points as those described in chemical formulas 2-1 and 2-2 can be appliedAnd (3) capacity.

[ chemical formula 2-1a ]

[ chemical formula 2-1b ]

In chemical formulas 2-1a and 2-1b, R ^3-1 To R ^3-3 Each independently represents a hydrogen atom, a heavy hydrogen atom, a halogen atom, a substituted or unsubstituted aryl group having 6 or more and 15 or less ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 or more and 15 or less ring-forming carbon atoms. For example, R ^3-1 To R ^3-3 May be a hydrogen atom, a heavy hydrogen atom, a halogen atom, or a substituted or unsubstituted phenyl group. In addition, at R ^3-1 To R ^3-3 In the case where each of these is a halogen atom, the amine compound of an embodiment may include a fluorine atom (F) as a halogen atom.

In the chemical formula 2-1b, n2-1 may be an integer of 0 to 2. For example, n2-1 may be 0 or 1. In the case where n2-1 is 0, X is bonded in the chemical formula 2-1b ₂ And is R ^3-3 The substituted or unsubstituted phenyl group may be directly bonded to the nitrogen atom of chemical formula 1.

In chemical formulas 2-1a and 2-1b, k3-1 to k3-3 may each independently be an integer of 0 or more and 4 or less. The case where k3-1 is 0 may be identical to the case where k3-1 is 4 and R ^3-1 The same applies to the case of a hydrogen atom. The case where k3-2 is 0 may be identical to the case where k3-2 is 4 and R ^3-2 The same applies to the case of a hydrogen atom. The case where k3-3 is 0 may be equal to k3-3 being 4 and R ^3-3 The same applies to the case of a hydrogen atom.

In one embodiment, where k3-1 is an integer greater than 2, a plurality of R ^3-1 Can be the same or at least one can be the same as the rest of R ^3-1 Different. In addition, when k3-1 is 0, thenThe phenylene group in the chemical formula 2-1a may not be R ^3-1 And (3) substitution. When k3-2 is an integer of 2 or more, a plurality of R ^3-2 Can be the same or at least one can be the same as the rest of R ^3-2 Different. In addition, in the case where k3-2 is 0, the phenylene group in the chemical formula 2-1b may not be R ^3-2 And (3) substitution. When k3-3 is an integer of 2 or more, a plurality of R ^3-3 Can be the same or at least one can be the same as the rest of R ^3-3 Different. In addition, in the case where k3-3 is 0, the phenylene group in the chemical formula 2-1b may not be R ^3-3 And (3) substitution.

In one embodiment, chemical formula 2-2 may be represented by chemical formulas 2-2a to 2-2c below. That is, in the amine compound of an embodiment, FG of chemical formula 1 may be represented by any one of chemical formulas 2-2a to 2-2 c. In chemical formulas 2-2a to 2-2c, Q ² The same contents as those described in chemical formula 2-2 can be applied.

[ chemical formula 2-2a ]

[ chemical formula 2-2b ]

[ chemical formula 2-2c ]

In chemical formulas 2-2a to 2-2c, Z _a The aromatic hydrocarbon ring may be a substituted or unsubstituted aromatic hydrocarbon ring having 6 or more and 10 or less ring-forming carbon atoms. In one embodiment, the method comprises Z _a The number of rings represented may be one or two. For example, in the case of Z _a In the case where the number of rings represented is one, the number represented by Z _a In the moiety indicated, one ring may constitute a condensed ring, in the sense of Z _a In the case where the number of rings represented is two, in the case of a ring represented by Z _a In the indicated section, two rings may constitute a condensed ring. Specifically, in the Z _a In the case where the number of the represented rings is one, the condensed ring represented by chemical formulas 2-2a to 2-2c may be a substituent of a ring having a tricyclic ring. And, at Z _a In the case where the number of the represented rings is two, the condensed rings represented by chemical formulas 2-2a to 2-2c may be substituents of the ring having four rings.

In chemical formulas 2-2a to 2-2c, R ^4-1 Each independently represents a hydrogen atom, a heavy hydrogen atom, a halogen atom, or a substituted or unsubstituted aryl group having 6 or more and 15 or less ring-forming carbon atoms. For example, R ^4-1 May be a hydrogen atom, a heavy hydrogen atom, a halogen atom, or a substituted or unsubstituted phenyl group. In addition, at R ^4-1 In the case of a halogen atom, the amine compound of an embodiment may include a fluorine atom (F) as the halogen atom.

In chemical formulas 2-2a to 2-2c, k4-1 may be an integer of 0 or more and 7 or less. The case where k4-1 is 0 may be the same as the case where k4-1 is 7 and R ^4-1 The same applies to the case of a hydrogen atom. In one embodiment, where k4-1 is an integer greater than 2, a plurality of R ^4-1 Can be the same or at least one can be the same as the rest of R ^4-1 Different. In addition, in the case where k4-1 is 0, the substituents condensed in chemical formulas 2-2a to 2-2c may not be R ^4-1 And (3) substitution.

In one embodiment, in the amine compound represented by chemical formula 1, FG may be represented by any one of the following chemical formulas FG-1 to FG-6. In formulas FG-1 to FG-6, X ² And Q ² The same contents as those described in chemical formula 2-1 and chemical formula 2-2 can be applied. Specifically, in the formulas FG-1 to FG-4, X ² The same applies to the contents described in chemical formula 2-1, in chemical formulas FG-5 and FG-6, Q ² The same contents as those described in chemical formula 2-2 can be applied.

[ chemical formula FG-1]

[ chemical formula FG-2]

[ chemical formula FG-3]

[ chemical formula FG-4]

[ chemical formula FG-5]

[ chemical formula FG-6]

In the formulae FG-1 to FG-6, R ³ⁱ 、R ³ⁱⁱ R is as follows ⁴ⁱ To R ⁴ⁱⁱⁱ May each be independently a hydrogen atom, a heavy hydrogen atom, a halogen atom, or a substituted or unsubstituted phenyl group. For example, R ³ⁱ And R is ³ⁱⁱ Can be independently a hydrogen atom, a heavy hydrogen atom or a halogen atom, R ⁴ⁱ To R ⁴ⁱⁱⁱ May each be independently a hydrogen atom, a heavy hydrogen atom, a halogen atom, or a substituted or unsubstituted phenyl group. In addition, at R ³ⁱ 、R ³ⁱⁱ R is as follows ⁴ⁱ To R ⁴ⁱⁱⁱ In the case where each of them is a halogen atom, the amine compound of one embodiment may include fluorineThe atom (F) serves as a halogen atom.

In the chemical formulas FG-1 to FG-6, k3i, k3ii, and k4ii may each independently be an integer of 0 or more and 4 or less, k4i may be an integer of 0 or more and 3 or less, and k4iii may be an integer of 0 or more and 2 or less. The case where k3i is 0 may be equal to k3i being 4 and R ³ⁱ The same applies to the case of a hydrogen atom. The same applies to the case where each of k3ii and k4i to k4iii is 0.

In an embodiment, where each of k3i, k3ii, and k4i through k4iii is an integer of 2 or more, R is provided as a plurality ³ⁱ 、R ³ⁱⁱ R is as follows ⁴ⁱ To R ⁴ⁱⁱⁱ Each of which is the same or at least one of which is different from the remainder. In addition, in the case where each of k3i, k3ii, and k4i to k4iii is 0, the amine compound of one embodiment may not include R ³ⁱ 、R ³ⁱⁱ 、R ⁴ⁱ 、R ⁴ⁱⁱ And/or R ⁴ⁱⁱⁱ Is a substituent of (a).

In an embodiment, the amine compound of an embodiment represented by the chemical formula 1 may be represented by the following chemical formula 3-1 or chemical formula 3-2. Ar of chemical formula 1 is represented by chemical formula 3-1 and chemical formula 3-2 ¹ And X ¹ Materialized case. In chemical formulas 3-1 and 3-2, Q ¹ 、R ¹ 、R ² The same contents as those described in the chemical formula 1 can be applied to n1, k2, and FG.

[ chemical formula 3-1]

[ chemical formula 3-2]

In chemical formula 3-2, Y may be O or NR ¹¹ . For example, where Y is O, the amine compound of an embodiment may include a substituted or unsubstituted dibenzoFuryl as a substituent. And, at Y, NR ¹¹ In the case of (a), the amine compound of an embodiment may include a compound represented by R ¹¹ A substituted carbazolyl group or an unsubstituted carbazolyl group as a substituent.

In chemical formulas 3-1 and 3-2, R ⁸ To R ¹¹ Each independently represents a hydrogen atom, a heavy hydrogen atom, a halogen atom, or a substituted or unsubstituted aryl group having 6 to 20 ring-forming carbon atoms. For example, R ⁸ To R ¹¹ May be a hydrogen atom, a heavy hydrogen atom, a halogen atom, or a substituted or unsubstituted phenyl group. In addition, at R ⁸ To R ¹¹ In the case where each of them is a halogen atom, the amine compound of one embodiment represented by chemical formula 3-1 and chemical formula 3-2 may include a fluorine atom (F) as a halogen atom.

In chemical formulas 3-1 and 3-2, m1 may be an integer of 0 to 5, and m2 and m3 may each independently be an integer of 0 to 7. The case where m1 is 0 may be the same as that where m1 is 5 and R ⁸ The same applies to the case of a hydrogen atom. The case where m2 is 0 may be as described in the case where m2 is 7 and R ⁹ The same applies to the case of a hydrogen atom. The case where m3 is 0 may be as described in the case where m3 is 7 and R ¹⁰ The same applies to the case of a hydrogen atom.

In one embodiment, where m1 is an integer greater than 2, a plurality of R ⁸ Can be the same or at least one can be the same as the rest of R ⁸ Different. In addition, in the case where m1 is 0, the amine compound of one embodiment represented by chemical formula 3-1 and chemical formula 3-2 may not be R ⁸ And (3) substitution. When m2 is an integer of 2 or more, a plurality of R ⁹ Can be the same or at least one can be the same as the rest of R ⁹ Different. In addition, in the case where m2 is 0, the amine compound of one embodiment represented by chemical formula 3-1 may not be R ⁹ And (3) substitution. When m3 is an integer of 2 or more, a plurality of R ¹⁰ Can be the same or at least one can be the same as the rest of R ¹⁰ Different. In addition, in the case where m3 is 0, the amine compound of one embodiment represented by chemical formula 3-2 may not be R ¹⁰ And (3) substitution.

In one placeIn an embodiment, the amine compound of an embodiment represented by the chemical formula 1 may be represented by the following chemical formula 4-1 or chemical formula 4-2. Chemical formula 4-1 and chemical formula 4-2 are represented by formula 1 n1, R ² And FG materialization. Ar in chemical formulas 4-1 and 4-2 ¹ 、R ¹ 、X ¹ 、X ² 、Q ¹ 、Q ² Z and k1 may be the same as those described in the chemical formula 1, chemical formula 2-1 and chemical formula 2-2.

[ chemical formula 4-1]

[ chemical formula 4-2]

In chemical formulas 4-1 and 4-2, l1 may be 1 or 2.R is R ^2a To R ^4a May each be independently a hydrogen atom, a heavy hydrogen atom, a halogen atom, or a substituted or unsubstituted phenyl group. For example, R ^2a And R is ^3a Can be independently a hydrogen atom, a heavy hydrogen atom or a halogen atom, R ^4a May be a hydrogen atom, a heavy hydrogen atom, a halogen atom, or a substituted or unsubstituted phenyl group.

In chemical formulas 4-1 and 4-2, k2a and k3a may each independently be an integer of 0 to 4, and k4a may be an integer of 0 to 7. The case where k2a is 0 may be equal to k2a being 4 and R ^2a The same applies to the case of a hydrogen atom. The same applies to the case where each of k3a and k4a is 0.

In an embodiment, where each of k2a to k4a is an integer of 2 or more, R is provided as a plurality ^2a 、R ^3a And R is ^4a Each of which is the same or at least one of which may be different from the remainder. In addition, in the case where each of k2a to k4a is 0, the amine compound of one embodiment may not include R ^2a 、R ^3a And R is ^4a Is a substituent of (a).

The amine compound of one embodiment represented by chemical formula 1 may be represented by any one of the compounds of the following compound group 1. The hole transport region HTR of the light emitting element ED of an embodiment may include at least one of amine compounds disclosed in the following compound group 1. For example, at least one of the amine compounds disclosed in the following compound group 1 may be included in the electron blocking layer EBL of the light emitting element ED. In the following group 1 of compounds, "D" is a heavy hydrogen atom.

[ Compound group 1]

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The amine compound of an embodiment may be a tertiary amine compound. For example, an amine compound of an embodiment may include a first substituent, a second substituent, and a third substituent.

The first substituent may be a substituent having a dibenzoheteroskeleton. For example, the first substituent may include a dibenzofuranyl group or a dibenzothienyl group to which a substituted or unsubstituted phenyl group is bonded at the 6-position, and in particular, may have a feature of directly bonding the nitrogen atom of an amine in the 3-position of the dibenzofuranyl group and the dibenzothienyl group. The amine compound of an embodiment includes a first substituent so as not to cause instability due to steric twisting around the amine, can have high stability, and can appropriately adjust LUMO energy level so as to be suitably used as a material of the electron blocking layer EBL.

The second substituent and the third substituent may each independently be a substituted or unsubstituted naphthyl group or a substituted or unsubstituted heteroaryl group bonded to or directly bonded to the nitrogen atom of the amine through a linking group. In an embodiment of the amine compound, at least one of the second substituent and the third substituent may be a substituted or unsubstituted naphthyl group or a substituted or unsubstituted heteroaryl group bonded in para (para) relationship to the nitrogen atom of the amine through a linker. Accordingly, the amine compound of an embodiment may have improved hole transport properties and stability.

The amine compound of an embodiment includes a first substituent, a second substituent, and a third substituent having high electron resistance, and thus may have high electron resistance. Also, since the first substituent, the second substituent, and the third substituent are substituents which are difficult to thermally decompose, the amine compound of one embodiment can suppress an excessive increase in deposition temperature, and can suppress material deterioration caused by the deposition process. Accordingly, the lifetime of the light-emitting element of one embodiment including the amine compound of one embodiment can be improved.

In the light emitting element ED of an embodiment, the hole transport region HTR may further include a compound represented by the following chemical formula H-1.

[ chemical formula H-1]

In the formula H-1, L ₁ And L ₂ Can be respectively and independently direct binding (direct linking), quiltA 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. a and b may be each independently an integer of 0 to 10. In addition, when a or b is an integer of 2 or more, a plurality of L ₁ And a plurality of L ₂ Each independently represents a substituted or unsubstituted arylene group having 6 or more and 30 or less ring-forming carbon atoms or a substituted or unsubstituted heteroarylene group having 2 or more and 30 or less ring-forming carbon atoms.

In the formula H-1, ar _a And Ar is a group _b Each independently represents a substituted or unsubstituted aryl group having 6 or more and 30 or less ring-forming carbon atoms or a substituted or unsubstituted heteroaryl group having 2 or more and 30 or less ring-forming carbon atoms. And in the chemical formula H-1, ar _c May be a substituted or unsubstituted aryl group having 6 or more and 30 or less ring-forming carbon atoms.

The compound represented by the chemical formula H-1 may be a monoamine compound. Alternatively, the compound represented by the formula H-1 may be Ar _a To Ar _c A diamine compound containing an amine group as a substituent. And, the compound represented by the formula H-1 may be represented by Ar _a And Ar is a group _b Carbazole compound including substituted or unsubstituted carbazolyl group in at least one of them, or in Ar _a And Ar is a group _b A fluorene compound containing a substituted or unsubstituted fluorenyl group in at least one of them.

The compound represented by the formula H-1 may be represented by any one of the compounds of the following compound group H. However, the compounds listed in the following compound group H are exemplary, and the compound represented by the chemical formula H-1 is not limited to the compounds represented in the following compound group H.

[ Compound group H ]

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In addition, the hole transport region HTR may further include a well-known hole transport material.

For example, the hole transport region HTR may include a phthalocyanine (phtalocyanine) compound, N, etc., of copper phthalocyanine (copper phthalocyanine) ¹ ,N ^1' - ([ 1,1' -biphenyl)]-4,4' -diyl) bis (N ¹ -phenyl-N ⁴ ,N ⁴ -di-m-tolylbenzene-1, 4-diamine) (DNTPD: n (N) ¹ ,N ^1' -([1,1'-biphenyl]-4,4'-diyl)bis(N ¹ -phenyl-N ⁴ ,N ⁴ -di-m-tolyllbenzene-1, 4-diamine)), 4',4"- [ tris (3-methylphenyl) phenylamino group]Triphenylamine (m-MTDATA: 4,4',4"- [ tris (3-methylphenyl) phenyl ] amino ]]triphenylamine), 4',4"-tris (N, N-diphenylamino) triphenylamine (TDATA: 4,4',4"-Tris (N, N-diphenylamino) triphenylamine), 4',4" -Tris [ N- (1-naphthyl) -N-phenylamino ]Triphenylamine (1-TNATA: 4,4' -tris [ N- (1-workbench) -N-phenylamino)]-triphenylamine), 4' -tris [ N- (2-naphthyl) -N-phenylamino]Triphenylamine (2-TNATA: 4,4' -tris [ N- (2-workbench) -N-phenylamino)]Triphenylamine), poly (3, 4-ethylenedioxythiophene)/poly (4-styrenesulfonate) (PEDOT/PSS: poly (3, 4-ethylidenoxythiophene)/Poly (4-styrenesulfonate)), polyaniline/dodecylbenzenesulfonic acid (PANI/DBSA: polyaniline/Dodecylbenzenesulfonic acid), polyaniline/camphorsulfonic acid (PANI/CSA: polyaniline/Camphor sulfonicacid), polyaniline/poly (4-styrene sulfonate) (PANI/PSS: polyaniline/Poly (4-styrenesulfonate)), N '-di (naphthalen-1-yl) -N, N' -diphenyl-benzidine (NPB (or NPD): n, N ' -di (naphthalenyl-1-yl) -N, N ' -diphenyl-benzodine, polyetherketone containing Triphenylamine (TPAPEK), 4-isopropyl-4 ' -methyldiphenyliodonium [ tetra (pentafluorophenyl) borate](4-Isopropyl-4'-methyldiphenyliodonium[Tetrakis(pentafluorophenyl)borate]) Bipyrazino [2,3-f:2',3' -h]Quinoxaline-2,3,6,7,10, 11-hexanitrile (HATCN: dipyrazino [2,3-f:2',3' -h)]quinoxaline-2,3,6,7,10, 11-hexacarbonifile), and the like.

The hole transport region HTR may further include carbazole-based derivatives such as N-phenylcarbazole, polyvinylcarbazole, etc., fluorene (fluorene) based derivatives, and a method of forming a hole transport region HTR such as 4,4',4″ -tris (N-carbazolyl) triphenylamine (TCTA: triphenylamine derivatives such as 4,4',4"-tris (N-carbazolyl) triphenylamine or N, N '-Bis (3-methylphenyl) -N, N' -diphenyl- [1,1'-biphenyl ] -4,4' -diamine (TPD: N, N '-Bis (3-methylphenyl) -N, N' -biphen yl- [1,1'-biphen yl ] -4,4' -diamine), N '-di (naphthalen-1-yl) -N, N' -diphenyl-benzidine (NPB: N, N '-di (naphthalen-1-yl) -N, N' -diphenyl-benzodine), 4 '-cyclohexylidenebis [ N, N-Bis (4-methylphenyl) aniline ] (TAPC: 4,4' -Cyclohexylidene Bis [ N, N-Bis (4-methylphen zenimine ]), 4'-Bis [ N, N' - (3-tolyl) amino ] -3,3'-dimethylbiphenyl (HMTPD: 4,4' -Bis [ N, N '- (3-tolyl) amino ] -3,3' -dimethylbiphenyl) phenyl ], 1,3-Bis (N-carbazolyl) benzene (mCP: 1,3-Bis (N-carbazolyl) benzone) and the like

And, the hole transport region HTR may further include 9- (4-tert-Butylphenyl) -3,6-bis (triphenylsilyl) -9H-carbazole (CzSi: 9- (4-tert-Butylphenyl) -3,6-bis (triphenylsilyl) -9H-carbazole), 9-phenyl-9H-3,9 '-dicarbazole (CCP: 9-phenyl-9H-3,9' -dicarbazole), or 1,3-bis (1, 8-dimethyl-9H-carbazol-9-yl) benzene (mDCP: 1,3-bis (1, 8-dimethyl-9H-carbazol-9-yl) benzene), and the like.

The hole transport region HTR may contain a compound of the hole transport region HTR described above in at least one of the hole injection layer HIL, the hole transport layer HTL, and the electron blocking layer EBL.

The hole transport region HTR may have a thickness of aboutTo about->For example, about->To aboutIn the case where the hole transport region HTR includes the hole injection layer HIL, the hole injection layer HILThe thickness may be, for example, about +.>To about->In the case where the hole transport region HTR includes a hole transport layer HTL, the thickness of the hole transport layer HTL may be about +.>To about->For example, in the case where the hole transport region HTR includes an electron blocking layer EBL, the thickness of the electron blocking layer EBL may be about +.>To about->In the case where 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 ranges described above, a satisfactory degree of hole transport characteristics can be obtained without substantially increasing the driving voltage.

The hole transport region HTR may include a charge generating substance in addition to the aforementioned substances to improve conductivity. The charge generating substance may be uniformly or non-uniformly dispersed in the hole transport region HTR. The charge generating substance may be, for example, a p-dopant (dopant). The p-dopant may include at least one of a halogenated metal compound, a quinone (quinone) derivative, a metal oxide, and a cyano (cyano) containing compound, but is not limited thereto. For example, the p-dopant may include halogenated metal compounds such as CuI and RbI, tetracyanoquinodimethane (TCNQ: tetracyanoquinodimethane) and 2,3,5,6-tetrafluoro-7, 8-Tetracyanoquinodimethane (F4-TCNQ: 2,3,5,6-tetrafluoro-7, 8-Tetracyanoquinodimethane), and the like, metal oxides such as tungsten oxide and molybdenum oxide, and bipyrazino [2,3-F: cyano-containing compounds such as 2',3' -h ] quinoxaline-2,3,6,7,10, 11-hexanitrile (HATCN: dipyrazino [2,3-F:2',3' -h ] quinoxaline-2,3,6,7,10, 11-hexacarbonifole) and 4- [ [2,3-bis [ cyano- (4-cyano-2, 3,5, 6-tetrafluorophenyl) methylene ] cyclopropyl ] -cyanomethyl ] -2,3,5,6-tetrafluorobenzonitrile (NDP 9:4- [ [2,3-bis [ cyano- (4-cyano-2, 3,5, 6-tetrafluorophenyl) methyl ] cyclopropylide ne ] -cyanaminomethyl ] -2,3,5,6-tetrafluorobenzonitrile, and the like, but the embodiment is not limited thereto.

As described above, the hole transport region HTR may include a buffer layer (not shown) in addition to the hole injection layer HIL, the hole transport layer HTL, and the electron blocking layer EBL. The buffer layer (not shown) may improve light emission efficiency by compensating for a resonance distance according to a wavelength of light emitted from the light emitting layer EML. As a material contained in the buffer layer (not shown), a substance that can be contained in the hole transport region HTR can be used.

The emission layer EML is disposed on the hole transport region HTR. The light emitting layer EML may have, for example, aboutTo aboutOr about->To about->Is a thickness of (c). The light emitting layer EML may have: a single layer structure formed by a single substance; a single-layer structure configured by a plurality of substances different from each other; or a multi-layer structure having a plurality of layers made of a plurality of substances different from each other.

In the light emitting device ED of an embodiment, the light emitting layer EML may emit blue light. The light emitting element ED of an embodiment includes the amine compound of an embodiment described above in the hole transport region HTR, and thus can exhibit characteristics of high light emitting efficiency and long lifetime in the blue light emitting region. However, the embodiment is not limited thereto.

In the light emitting element ED of an embodiment, the light emitting layer EML may include anthracene derivatives, pyrene derivatives, fluoranthene derivatives, Derivatives, dihydrobenzanthracene derivatives, benzo [9,10]Phenanthrene derivatives, and the like. Specifically, the light emitting layer EML may include an anthracene derivative, a pyrene derivative, or the like.

In the light emitting element ED of an embodiment shown in fig. 3 to 6, the light emitting layer EML may include a host and a dopant, and the light emitting layer EML may include a compound represented by the following chemical formula E-1. The compound represented by the following chemical formula E-1 can be used as a fluorescent host material.

[ chemical formula E-1]

In formula E-1, R ₃₁ To R ₄₀ Each may be independently a hydrogen atom, a heavy hydrogen atom, a halogen atom, a substituted or unsubstituted silyl group, a substituted or unsubstituted thio group, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group having 1 or more and 10 or less carbon atoms, a substituted or unsubstituted alkenyl group having 2 or more and 10 or less carbon atoms, a substituted or unsubstituted aryl group having 6 or more and 30 or less ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 or more and 30 or less ring-forming carbon atoms, and may be optionally bonded to an adjacent group to form a ring. In addition, R ₃₁ To R ₄₀ Can combine with adjacent groups to form a saturated hydrocarbon ring, an unsaturated hydrocarbon ring, a saturated heterocyclic ring or an unsaturated heterocyclic ring.

In the chemical formula E-1, c and d may each independently be an integer of 0 or more and 5 or less.

The chemical formula E-1 may be represented by any one of the following compounds E1 to E19.

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In one embodiment, the light emitting layer EML may include a compound represented by the following chemical formula E-2a or chemical formula E-2 b. A compound represented by the following chemical formula E-2a or chemical formula E-2b may be used as the phosphorescent host material.

[ formula E-2a ]

In the chemical formula E-2a, a may be an integer of 0 to 10 inclusive, L _a The aryl group may be a directly bonded, substituted or unsubstituted arylene group having 6 or more and 30 or less ring-forming carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 or more and 30 or less ring-forming carbon atoms. In addition, when a is an integer of 2 or more, a plurality of L _a Each independently represents a substituted or unsubstituted arylene group having 6 or more and 30 or less ring-forming carbon atoms or a substituted or unsubstituted heteroarylene group having 2 or more and 30 or less ring-forming carbon atoms.

And, in the chemical formula E-2a, A ₁ To A ₅ Can be N or CR respectively and independently _i 。R _a To R _i Can be independently a hydrogen atom, a heavy hydrogen atom, a substituted or unsubstituted amine group, a substituted or unsubstituted sulfide 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 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, And optionally with adjacent groups to form a ring. R is R _a To R _i Can combine with adjacent groups to form a hydrocarbon ring or a heterocyclic ring including N, O, S or the like as a ring-forming atom.

In addition, in the chemical formula E-2a, selected from A ₁ To A ₅ Two or three of them may be N, and the remainder may be CR _i 。

[ formula E-2b ]

In the chemical formula E-2b, cbz1 and Cbz2 may each independently be an unsubstituted carbazolyl group or a carbazolyl group substituted with an aryl group having 6 or more and 30 or less ring carbon atoms. L (L) _b The aryl group may be a directly bonded, substituted or unsubstituted arylene group having 6 or more and 30 or less ring-forming carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 or more and 30 or less ring-forming carbon atoms. b may be an integer of 0 to 10, and when b is an integer of 2 or more, a plurality of L' s _b Each independently represents a substituted or unsubstituted arylene group having 6 or more and 30 or less ring-forming carbon atoms or a substituted or unsubstituted heteroarylene group having 2 or more and 30 or less ring-forming carbon atoms.

The compound represented by the formula E-2a or the formula E-2b may be represented by any one of the compounds of the following group of compounds E-2. However, the compounds listed in the following compound group E-2 are exemplary, and the compounds represented by the chemical formula E-2a or the chemical formula E-2b are not limited to the compounds shown in the following compound group E-2.

[ Compound group E-2]

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The light emitting layer EML may further include a general material known in the art as a host substance. For example, the light emitting layer EML may include bis [4- (9H-carbazol-9-yl) phenyl ]]Diphenylsilane (BCPDS: bis (4- (9H-carbazol-9-yl) phenyl) diphenylsilane), (4- (1- (4- (diphenylamino) phenyl) cyclohexyl) phenyl) diphenyl-Phosphine Oxide (POPCPA) (4- (1- (4- (diphenylamino) phenyl) cyclohexyl) phenyl) dipheny-phosphine oxide), bis [2- (diphenylphosphino) phenyl]Ether oxide (DPEPO: bis [2- (dipheny phosphino) phenyl)]ether oxide), 4'-bis (N-carbazolyl) -1,1' -biphenyl (CBP: 4,4'-bis (N-carbazolyl) -1,1' -biphenyl), 1,3-bis (carbazol-9-yl) benzene (mCP: 1,3-Bis (carbazol-9-yl) benzone), 2,8-Bis (diphenylphosphoryl) dibenzo [ b, d]Furan (PPF: 2,8-Bis (diphenylphosphoryl) dibenzo [ b, d ]]furan), 4',4″ -tris (carbazol-9-yl) -triphenylamine (TCTA: 4,4' -Tris (carbazol-9-yl) -triphenylamine) and 1,3,5-Tris (1-phenyl-1H-benzo [ d ]]Imidazol-2-yl) benzene (TPBi: 1,3,5-tris (1-phenyl-1H-benzol [ d ]]imidozole-2-yl) benzene) as a host substance. However, not limited thereto, for example, tris (8-hydroxyquinoline) aluminum (Alq ₃ : tris (8-hydroxyquinone) aluminum), 9,10-di (naphthalen-2-yl) anthracene (ADN: 9,10-di (naphthalen-2-yl) anthracenes), 2-tert-butyl-9,10-di (naphthalen-2-yl) anthracene (TBADN: 2-tert-butyl-9,10-di (naphthalth-2-yl) anthracene), distyrylarylide (DSA: distyrylacrylene), 4'-bis (9-carbazolyl) -2,2' -dimethyl-biphenyl (CDBP: 4,4'-bis (9-carbazolyl) -2,2' -dimethyl-biphenyl), 2-methyl-9,10-bis (naphthalen-2-yl) anthracene (MADN: 2-Methyl-9,10-bis (naphthalen-2-yl) anthracenene), hexaphenyl cyclotriphosphazene (CP 1: hexaphenyl cyclotriphosphazene), 1,4-bis (triphenylsilyl) benzene (UGH 2:1,4-Bis (triphenylsilyl) Benzene), hexaphenylcyclotrisiloxane (DPSiO) ₃ : hexaphenyl cyclotriosiloxane), octylphenyl cyclotetrasiloxane (DPSiO) ₄ : octaphenylcyclotetra siloxane) or the like can be used as a host material.

The light emitting layer EML may include a compound represented by the following chemical formula M-a or chemical formula M-b. A compound represented by the following chemical formula M-a or chemical formula M-b may be used as the phosphorescent dopant material. Also, in an embodiment, a compound represented by the following chemical formula M-a or chemical formula M-b may be used as the auxiliary dopant material.

[ chemical formula M-a ]

In the formula M-a, Y ₁ To Y ₄ And Z ₁ To Z ₄ Can be CR independently ₁ Or N, R ₁ To R ₄ Each independently may be a hydrogen atom, a heavy hydrogen atom, a substituted or unsubstituted amine group, a substituted or unsubstituted sulfide group, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group having 1 or more and 20 or less carbon atoms, a substituted or unsubstituted alkenyl group having 2 or more and 20 or less carbon atoms, a substituted or unsubstituted aryl group having 6 or more and 30 or less ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 or more and 30 or less ring-forming carbon atoms, and may be optionally bonded to each other with an adjacent group to form a ring. In the formula M-a, M is 0 or 1, and n is 2 or 3. In the chemical formula M-a, n is 3 when M is 0, and n is 2 when M is 1.

The compound represented by the formula M-a may be used as a phosphorescent dopant.

The compound represented by the chemical formula M-a may be represented by any one of the following compounds M-a1 to M-a 25. However, the following compounds M-a1 to M-a25 are exemplary, and the compounds represented by the chemical formula M-a are not limited to the compounds represented by the following compounds M-a1 to M-a 25.

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The compounds M-a1 and M-a2 may be used as red dopant materials, and the compounds M-a3 to M-a7 may be used as green dopant materials.

[ chemical formula M-b ]

In the formula M-b, Q ₁ To Q ₄ Each independently is C or N, and C1 to C4 are each independently a substituted or unsubstituted hydrocarbon ring having 5 or more and 30 or less ring-forming carbon atoms or a substituted or unsubstituted heterocyclic ring having 2 or more and 30 or less ring-forming carbon atoms. L (L) ₂₁ To L ₂₄ Are respectively and independently direct combined, A substituted or unsubstituted divalent alkyl group having 1 to 20 carbon atoms, 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, and e1 to e4 are each independently 0 or 1.R is R ₃₁ To R ₃₉ Each independently is a hydrogen atom, a heavy hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, and optionally is bonded to each other with an adjacent group to form a ring, and d1 to d4 are each independently an integer of 0 to 4.

The compound represented by the formula M-b may be used as a blue phosphorescent dopant or a green phosphorescent dopant. Also, in an embodiment, the compound represented by the chemical formula M-b may be further included in the emission layer EML as an auxiliary dopant.

The compound represented by the chemical formula M-b may be represented by any one of the following compounds. However, the following compounds are exemplary, and the compounds represented by the chemical formula M-b are not limited to the compounds represented by the following compounds.

R, R among the compounds ₃₈ R is as follows ₃₉ Each independently represents a hydrogen atom, a heavy hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms.

The light emitting layer EML may further include a compound represented by any one of the following chemical formulas F-a to F-c. Compounds represented by the following chemical formulas F-a to F-c may be used as the fluorescent dopant material.

[ chemical formula F-a ]

In the formula F-a, R is selected from _a To R _j Can be independently of each other-NAr ₁ Ar ₂ And (3) substitution. R is R _a To R _j Is not shown by NAr ₁ Ar ₂ The remainder of the substitution may be each independently a hydrogen atom, a heavy hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms. at-NAr ₁ Ar ₂ Ar in (1) ₁ And Ar is a group ₂ Can be independently substituted or unsubstituted, and has 6 to 30 carbon atoms in the ringAryl or substituted or unsubstituted heteroaryl having 2 or more and 30 or less ring-forming carbon atoms. For example, ar ₁ And Ar is a group ₂ At least one of which may be a heteroaryl group containing O or S as a ring-forming atom.

[ chemical formula F-b ]

In the formula F-b, R _a And R is _b Each independently may be a hydrogen atom, a heavy hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, and may be optionally bonded to each other with adjacent groups to form a ring. Ar (Ar) ₁ To Ar ₄ Each independently represents a substituted or unsubstituted aryl group having 6 or more and 30 or less ring-forming carbon atoms or a substituted or unsubstituted heteroaryl group having 2 or more and 30 or less ring-forming carbon atoms.

In the chemical formula F-b, U and V may each independently be a substituted or unsubstituted cyclic hydrocarbon having 5 or more and 30 or less ring-forming carbon atoms or a substituted or unsubstituted heterocyclic ring having 2 or more and 30 or less ring-forming carbon atoms.

In the chemical formula F-b, the number of rings represented by U and V may be 0 or 1, respectively, independently. For example, when the number of U or V in the chemical formula F-b is 1, the condensed ring is constituted by one ring in the portion described as U or V, and when the number of U or V is 0, it means that the ring described as U or V does not exist. Specifically, in the case where the number of U is 0 and the number of V is 1, or in the case where the number of U is 1 and the number of V is 0, the condensed ring having a fluorene core of the chemical formula F-b may be a four-membered ring compound. And, in the case where the number of both U and V is 0, the condensed ring having a fluorene core of the chemical formula F-b may be a tricyclic compound. Also, in the case where the number of both U and V is 1, the condensed ring having a fluorene core of the chemical formula F-b may be a five-membered ring compound.

[ chemical formula F-c ]

In the formula F-c, A ₁ And A ₂ O, S, se or NR respectively and independently _m And R is _m The aromatic hydrocarbon may be a hydrogen atom, a heavy hydrogen atom, 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. R is R ₁ To R ₁₁ Each independently is a hydrogen atom, a heavy hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted amine group, a substituted or unsubstituted boron group, a substituted or unsubstituted oxygen group, a substituted or unsubstituted sulfur 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 optionally, is bonded to each other with an adjacent group to form a ring.

In the formula F-c, A ₁ And A ₂ Can each independently combine with substituents of adjacent rings to form condensed rings. For example, when A ₁ And A ₂ Are each independently NR _m When A is ₁ Can be combined with R ₄ Or R is ₅ And combine to form a ring. And A is ₂ Can be combined with R ₇ Or R is ₈ And combine to form a ring.

In an embodiment, the light emitting layer EML may include a styryl derivative (e.g., 1,4-bis [2- (3-N-ethylcarbazolyl) vinyl ] benzene (BCzVB: 1,4-bis [2- (3-N-ethylcarbazolyl) vinyl ] benzene), 4- (di-p-tolylamino) -4'- [ (di-p-tolylamino) styryl ] stilbene (DPAVB: 4- (di-p-tolylamino) -4' - [ (di-p-tolylamino) styryl ] stilbene), N- (4- ((E) -2- (6- ((E) -4- (diphenylamino) styryl) naphthalen-2-yl) vinyl) phenyl) -N-phenylaniline (N-BDAVBi: N- (4- ((E) -2- (6- ((E) -4- (diphenylamino) styryl) nanophenyl-2-yl) phenyl) -N-phe nylbenzenamine), 4'-bis [2- (4- (N, N-diphenylamino) phenyl) vinyl ] biphenyl (DPAVBi: 4,4' -bis [2- (4- (N, N-diphenylamino) phenyl) vinyl ] biphenyl)), perylene and derivatives thereof (e.g., 2,5,8, 11-Tetra-tert-butylperylene (TBP: 2,5,8, 11-Tetra-butyl) phenyl)) Pyrene and derivatives thereof (e.g., 1' -dipyrene, 1, 4-dipyrene benzene (1, 4-dipyrene lbenzenene), 1,4-Bis (N, N-Diphenylamino) pyrene), and the like are known as dopant materials.

In an embodiment, where multiple light emitting layers EML are included, at least one of the light emitting layers EML may include a known phosphorescent dopant species. For example, a metal complex including iridium (Ir), platinum (Pt), osmium (Os), gold (Au), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), or thulium (Tm) may be used as the phosphorescent dopant. Specifically, bis (4, 6-difluorophenylpyridine-N, C2 ') picolinated iridium (III) (FIrpic: iridium (III) bis (4, 6-difluorophenylpyristo-N, C2') picolinate), bis (2, 4-difluorophenylpyridine) -tetrakis (1-pyrazolyl) iridium (III) (Fir) ₆ : bis (2, 4-difluorophenyl writer) -tetrakis (1-pyrazolyl) boron (iii)) or octaethylporphin platinum (PtOEP: platinum octaethyl porphyrin) can be used as phosphorescent dopants. However, the embodiment is not limited thereto.

In addition, in an embodiment, the light emitting layer EML may include a hole transporting host and an electron transporting host. In addition, the emission layer EML may include an auxiliary dopant and an emission dopant. In addition, as the auxiliary dopant, a phosphorescent dopant material or a thermally active delayed fluorescence dopant material may be included. That is, in an embodiment, the emission layer EML may include a hole transporting body, an electron transporting body, an auxiliary dopant, and an emission dopant.

The light-emitting layer EML may be formed of an exciplex by a hole-transporting host and an electron-transporting host. In this case, the triplet energy of the exciplex formed by the hole-transporting host and the electron-transporting host may be T1, which is the interval between the LUMO level of the electron-transporting host and the HOMO level of the hole-transporting host.

In one embodiment, the triplet energy (T1) of the exciplex formed by the hole transporting host and the electron transporting host may be 2.4eV or more and 3.0eV or less. And, the triplet energy of the exciplex may be a value smaller than the band gap of each host material. Therefore, the exciplex may have triplet energy of 3.0eV or less as the energy band gap of the hole-transporting host and the electron-transporting host.

In addition, the at least one light emitting layer EML may include a Quantum dot (Quantum dot) substance. The core of the quantum dot may be selected from group II-VI compounds, group III-VI compounds, group I-III-VI compounds, group III-V compounds, group III-II-V compounds, group IV-VI compounds, group IV elements, group IV compounds, and combinations thereof.

The group II-VI compound may be selected from the group consisting of binary compounds selected from the group consisting of CdSe, cdTe, cdS, znS, znSe, znTe, znO, hgS, hgSe, hgTe, mgSe, mgS and mixtures thereof, ternary compounds selected from the group consisting of CdSeS, cdSeTe, cdSTe, znSeS, znSeTe, znSTe, hgSeS, hgSeTe, hgSTe, cdZnS, cdZnSe, cdZnTe, cdHgS, cdHgSe, cdHgTe, hgZnS, hgZnSe, hgZnTe, mgZnSe, mgZnS and mixtures thereof, and quaternary compounds selected from the group consisting of CdZnSeS, cdZnSeTe, cdZnSTe, cdHgSeS, cdHgSeTe, cdHgSTe, hgZnSeS, hgZnSeTe, hgZnSTe and mixtures thereof.

The III-VI compound may include, for example, in ₂ S ₃ 、In ₂ Se ₃ Binary compounds such as InGaS ₃ 、InGaSe ₃ Or a combination thereof.

The group I-III-VI compound may be selected from AgInS, agInS ₂ 、CuInS、CuInS ₂ 、AgGaS ₂ 、CuGaS ₂ 、CuGaO ₂ 、AgGaO ₂ 、AgAlO ₂ Ternary compounds or compounds derived from AgInGaS, and mixtures thereof ₂ 、CuInGaS ₂ And the like.

The group II-V compound may be selected from the group consisting of binary compounds selected from the group consisting of GaN, gaP, gaAs, gaSb, alN, alP, alAs, alSb, inN, inP, inAs, inSb and mixtures thereof, ternary compounds selected from the group consisting of GaNP, gaNAs, gaNSb, gaPAs, gaPSb, alNP, alNAs, alNSb, alPAs, alPSb, inGaP, inAlP, inNP, inNAs, inNSb, inPAs, inPSb and mixtures thereof, and quaternary compounds selected from the group consisting of GaAlNP, gaAlNAs, gaAlNSb, gaAlPAs, gaAlPSb, gaInNP, gaInNAs, gaInNSb, gaInPAs, gaInPSb, inAlNP, inAlNAs, inAlNSb, inAlPAs, inAlPSb and mixtures thereof. In addition, the III-V compounds may also include group II metals. For example, the III-II-V compound may be selected from InZnP and the like.

The group IV-VI compounds may be selected from the group consisting of binary compounds selected from the group consisting of SnS, snSe, snTe, pbS, pbSe, pbTe and mixtures thereof, ternary compounds selected from the group consisting of SnSeS, snSeTe, snSTe, pbSeS, pbSeTe, pbSTe, snPbS, snPbSe, snPbTe and mixtures thereof, and quaternary compounds selected from the group consisting of SnPbSSe, snPbSeTe, snPbSTe and mixtures thereof. 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 mixtures thereof.

In this case, the binary compound, the ternary compound, or the quaternary compound may exist in the particle at a uniform concentration, or may exist in the same particle in a state in which the concentration distribution is locally different. And, it is also possible to have a core/shell structure in which one quantum dot surrounds another quantum dot. In the core/shell structure, there may be a concentration gradient (gradient) in which the concentration of the element present in the shell decreases toward the core.

In several embodiments, the quantum dot may have a core comprising nanocrystals described above and a core-shell structure comprising a shell surrounding the core. The shell of the quantum dot may function as a protective layer for maintaining semiconductor characteristics by preventing chemical modification of the core and/or a charge layer (charging layer) for imparting electrophoretic characteristics to the quantum dot. The shell may be a single layer or multiple layers. Examples of the shell of the quantum dot may be exemplified by metal or nonmetal oxides, semiconductor compounds, combinations thereof, or the like.

For example, the metal or nonmetal compound may be exemplified by SiO ₂ 、Al ₂ O ₃ 、TiO ₂ 、ZnO、MnO、Mn ₂ O ₃ 、Mn ₃ O ₄ 、CuO、FeO、Fe ₂ O ₃ 、Fe ₃ O ₄ 、CoO、Co ₃ O ₄ Binary compounds of NiO or the like or MgAl ₂ O ₄ 、CoFe ₂ O ₄ 、NiFe ₂ O ₄ 、CoMn ₂ O ₄ And the like, but the present invention is not limited thereto.

Also, the semiconductor compound may show CdS, cdSe, cdTe, znS, znSe, znTe, znSeS, znTeS, gaAs, gaP, gaSb, hgS, hgSe, hgTe, inAs, inP, inGaP, inSb, alAs, alP, alSb and the like, but the present invention is not limited thereto.

The quantum dot may have a full width at half maximum (FWHM: full width of half maximum) of an emission wavelength spectrum of about 45nm or less, preferably about 40nm or less, more preferably about 30nm or less, in which the color purity or color reproducibility may be improved. Also, since light emitted through the quantum dots can be emitted in all directions, a wide viewing angle can be improved.

The form of the quantum dot is a form commonly used in the art, and more specifically, a form of a nanoparticle, a nanotube, a nanowire, a nanofiber, a nano-plate, or the like of a sphere, a pyramid, a multi-arm (cube), or a cube (cubic) may be used, although not particularly limited.

The quantum dots can adjust the color of emitted light according to the size of the particles, and accordingly, the quantum dots can have various light emission colors such as blue, red, green, and the like.

In the light emitting element ED of the embodiment shown in fig. 3 to 6, the electron transport region ETR is provided on the light emitting layer EML. The electron transport region ETR may include at least one of a hole blocking layer HBL, an electron transport layer ETL, and an electron injection layer EIL, but the embodiment is not limited thereto.

The electron transport region ETR may have: a single layer structure formed by a single substance; a single-layer structure configured by a plurality of substances different from each other; or a multi-layer structure having a plurality of layers made of a plurality of substances different from each other.

For example, the electron transport region ETR may have a single layer structure of the electron injection layer EIL or the electron transport layer ETL, or may have a single layer structure of an electron injection material and an electron transport material. Further, the electron transport region ETR may have a structure of a single layer composed of a plurality of substances different from each other, or a structure of an electron transport layer ETL/electron injection layer EIL, a hole blocking layer HBL/electron transport layer ETL/electron injection layer EIL, an electron transport layer ETL/buffer layer (not shown)/electron injection layer EIL, or the like stacked in order from the light emitting layer EML, but is not limited thereto. The electron transport region ETR may have a thickness of, for example, about To about->

The electron transport region ETR may be formed using various methods such as a vacuum deposition method, a spin coating method, a casting method, langmuir-Blodgett (LB: langmuir-Blodgett), an inkjet printing method, a laser thermal transfer method (LITI: laser Induced Thermal Imaging), and the like.

The electron transport region ETR may include a compound represented by the following chemical formula ET-1.

[ chemical formula ET-1]

In formula ET-1, X ₁ To X ₃ At least one of which is N, the rest is CR _a 。R _a The aromatic hydrocarbon may be a hydrogen atom, a heavy hydrogen atom, 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. Ar (Ar) ₁ To Ar ₃ Each independently represents a hydrogen atom, a heavy hydrogen atom, 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.

In the chemical formula ET-1, a to c may each independently be an integer of 0 to 10 or less. In formula ET-1, L ₁ To L ₃ Each independently may be a direct bond (direct link), a substituted or unsubstituted arylene group having 6 or more and 30 or less ring-forming carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 or more and 30 or less ring-forming carbon atoms. In addition, when a to c are integers of 2 or more, L ₁ To L ₃ Each independently represents a substituted or unsubstituted arylene group having 6 or more and 30 or less ring-forming carbon atoms or a substituted or unsubstituted heteroarylene group having 2 or more and 30 or less ring-forming carbon atoms.

The electron transport region ETR may include an anthracene compound. However, not limited thereto, the electron transport region ETR may include tris (8-hydroxyquinoline) aluminum (Alq), for example ₃ : tris (8-hydroxyquinoline) aluminum), 1,3, 5-Tris [ (3-pyridyl) -benzene-3-yl]Benzene (1, 3,5-tri [ (3-pyridil) -phen-3-yl)]Benzene), 2,4,6-tris (3 '- (pyridin-3-yl) biphenyl-3-yl) -1,3,5-triazine (2, 4,6-tris (3' - (pyridin-3-yl) biphen yl-3-yl) -1,3, 5-triazine), 2- (4- (N-phenylbenzimidazol-1-yl) phenyl) -9, 10-dinaphthyl anthracene (2- (4- (N-phenylbenzoimidazole-1-yl) phenyl) -9, 10-dinaphthhylanthracene), 1,3, 5-tris (1-phenyl-1H-benzo [ d ]]Imidazol-2-yl) benzene (TPBi: 1,3,5-Tri (1-phenyl-1H-benzol [ d ] ]imidazol-2-yl) benzene), 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP: 2,9-Dimethyl-4,7-diphenyl-1, 10-phenanthrine), 4,7-diphenyl-1,10-phenanthroline (Bphen: 4,7-Diphenyl-1, 10-phenanthrine), 3- (4-biphenyl) -4-phenyl-5-tert-butylphenyl-1,2,4-triazole (TAZ: 3- (4-biphenyl) -4-phenyl-5-tert-butyl-phenyl-1, 2, 4-triazole), 4- (naphthalen-1-yl) -3,5-diphenyl-4H-1,2,4-triazole (NTAZ: 4- (napthalen-1-yl) -3,5-diphenyl-4H-1,2, 4-triazole), 2- (4-biphenyl) -5- (4-tert-butylphenyl) -1,3,4-oxadiazole (tBu-PBD: 2- (4-biphenyl) -5- (4-tert-butyl-phenyl) -1,3, 4-oxadiazole), bis (2-methyl-8-hydroxyquinoline-N1, O8) - (1, 1' -biphenyl-4-hydroxy) aluminum (BAlq: bis (2-methyl-8-quinolato-N1, O8) - (1, 1' -biphen-4-olato) aluminum), bis (benzoquinolin-10-hydroxy) beryllium (Bebq) ₂ : berylinmbis (benzoquinone-10-olate)), 9, 10-bis (naphthalen-2-yl) anthracene (ADN: 9,10-di (naphthalen-2-yl) anthraquinone), 1,3-bis [3,5-di (pyridin-3-yl) phenyl]Benzene (BmPyPhB: 1,3-Bis [3,5-di (pyridin-3-yl) phenyl)]benzene), diphenyl (4- (triphenylsilyl) phenyl) phosphine oxide (TSPO 1: diphenyl (4- (triphenylsilyl) phenyl) phosphine oxide and their mixture.

The electron transport region ETR may include at least one of the following compounds ET1 to ET 36.

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And the electron transport region ETR may include a halogenated metal such as LiF, naCl, csF, rbCl, rbI, cuI, KI, a lanthanide such as YbMetal and/or co-deposited materials of the above-mentioned halogenated metals and lanthanide metals. For example, the electron transport region ETR may include KI: yb, rbI: yb, liF: yb, or the like as the co-deposited material. In addition, li can be used for the electron transport region ETR ₂ O, baO, or lithium 8-hydroxy-quinoline (Liq: 8-hydroxy-Lithium quinolate), but the embodiment is not limited thereto. The electron transport region ETR may also be formed using a substance in which an electron transport substance and an insulating organic metal salt (organo metal salt) are mixed. The organometallic salt may have an energy band gap (band gap) of approximately 4eV or more. Specifically, for example, the organic metal salt may include a metal acetate (metal acetate), a metal benzoate (metal benzoate), a metal acetoacetate (metal acetoacetate), a metal acetylacetonate (metal acetylacetonate), or a metal stearate (stearate).

The electron transport region ETR may include at least one of 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP: 2,9-dimethyl-4,7-diphenyl-1, 10-phenanthroline), diphenyl (4- (triphenylsilyl) phenyl) phosphine oxide (TSPO 1: diphenyl (4- (triphenylsilyl) phenyl) phosphine oxide), and 4,7-diphenyl-1,10-phenanthroline (Bphen: 4,7-diphenyl-1, 10-phenanthroline), in addition to the above-described materials, but the embodiment is not limited thereto.

As for the electron transport region ETR, the above-described compound of the electron transport region may be included in at least one of the electron injection layer EIL, the electron transport layer ETL, and the hole blocking layer HBL.

In the case where the electron transport region ETR includes the electron transport layer ETL, the thickness of the electron transport layer ETL may be aboutTo about->(e.g., about->To about->). In the case where the thickness of the electron transport layer ETL satisfies the range as described above, a satisfactory degree of electron transport characteristics can be obtained without substantially increasing the driving voltage. In the case where the electron transport region ETR includes the electron injection layer EIL, the thickness of the electron injection layer EIL may be aboutTo about->About->To about->In the case where the thickness of the electron injection layer EIL satisfies the range as described above, a satisfactory degree of electron injection characteristics can be obtained without substantially increasing the driving voltage.

The second electrode EL2 is provided on the electron transport region ETR. The second electrode EL2 may be a common electrode. The second electrode EL2 may be a cathode (cathode) or an anode (anode), but the embodiment is not limited thereto. For example, in the case where the first electrode EL1 is an anode, the second electrode EL2 may be a cathode, and in the case where the first electrode EL1 is a cathode, the second electrode EL2 may be an anode. The second electrode may include at least one selected from Ag, mg, cu, al, pt, pd, au, ni, nd, ir, cr, li, ca, liF, mo, ti, W, in, sn and Zn, two or more compounds selected from them, a mixture of two or more selected from them, or oxides thereof.

The second electrode EL2 may be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode. In the case where the second electrode EL2 is a transmissive electrode, the second electrode EL2 may be formed using a transparent metal oxide (for example, indium Tin Oxide (ITO), indium zinc oxide (IZO: indium zinc oxide), zinc oxide (ZnO: zinc oxide), indium tin zinc oxide (ITZO: indium tin zinc oxide)), or the like.

In the case where the second electrode EL2 is a semi-transmissive electrode or a reflective electrode, the second electrode EL2 may include Ag, mg, cu, al, pt, pd, au, ni, nd, ir, cr, li, ca, liF, mo, ti, W or a compound or mixture thereof (for example, agMg, agYb, or MgYb) or a material having a multilayer structure including two or more kinds selected from them (for example, liF/Ca (a stacked structure of LiF and Ca) or LiF/Al (a stacked structure of LiF and Al)). Alternatively, the second electrode EL2 may have a multi-layer structure including a reflective film or a semi-transmissive film formed using the above materials, and a transparent conductive film formed using Indium Tin Oxide (ITO), indium zinc oxide (IZO: indium zinc oxide), zinc oxide (ZnO: zinc oxide), indium tin zinc oxide (ITZO: indium tin zinc oxide), or the like. For example, the second electrode EL2 may include the above-described metal material, a combination of two or more metal materials selected from the above-described metal materials, an oxide of the above-described metal material, or the like.

Although not shown, the second electrode EL2 may be connected to an auxiliary electrode. If the second electrode EL2 is connected to the auxiliary electrode, the resistance of the second electrode EL2 can be reduced.

In addition, a cover layer CPL may also be disposed on the second electrode EL2 of the light-emitting element ED of an embodiment. The cover layer CPL may comprise multiple layers or a single layer.

In one embodiment, the capping layer CPL may be an organic layer or an inorganic layer. For example, in the case where the capping layer CPL includes an inorganic substance, the inorganic substance may include an alkali metal compound such as LiF, mgF, or the like ₂ Alkaline earth metal compound such as SiON, siN _X 、SiO _y Etc.

For example, in the case where the capping layer CPL includes an organic matter, the organic matter may include α -NPD, NPB, TPD, m-MTDATA, alq ₃ CuPc, N4, N4, N4', N4' -tetra (biphenyl-4-yl) biphenyl-4,4'-diamine (TPD 15: N4, N4, N4', N4'-tetra (biphen-4-yl) biphen-4, 4' -diamine), 4 '-Tris (carbazol-9-yl) triphenylamine (TCTA: 4,4' -Tris (carbazol-9-yl) triphenyl amine), or the like, or may include an epoxy resin or an acrylate such as a methacrylate. However, the embodiment is not limited thereto, and the capping layer CPL may include at least one of the compounds P1 to P5 described below.

The refractive index of the cover layer CPL may be 1.6 or more. Specifically, the refractive index of the cover layer CPL may be 1.6 or more for light in the wavelength range of 550nm to 660 nm.

Fig. 7 to 10 are sectional views of a display device according to an embodiment, respectively. In the following, in the description of the display device according to the embodiment described with reference to fig. 7 to 10, description will be given mainly on the point of distinction without repeating the description of the contents described in fig. 1 to 6.

Referring to fig. 7, a display device DD-a according to an embodiment may include a display panel DP including a display element layer DP-ED, a light control layer CCL disposed on the display panel DP, and a color filter layer CFL.

In one embodiment as shown in fig. 7, the display panel DP may include a base layer BS, a circuit layer DP-CL provided on the base layer BS, and a display element layer DP-ED, which may include light emitting elements ED.

The light emitting element ED may include a first electrode EL1, a hole transporting region HTR disposed on the first electrode EL1, a light emitting layer EML disposed on the hole transporting region HTR, an electron transporting region ETR disposed on the light emitting layer EML, and a second electrode EL2 disposed on the electron transporting region ETR. The structure of the light-emitting element shown in fig. 3 to 6 described above can be similarly applied to the structure of the light-emitting element ED shown in fig. 7.

The hole transport region HTR of the light emitting element ED included in the display device DD-a according to an embodiment may include the amine compound of the above-described one embodiment.

Referring to fig. 7, the light emitting layer EML may be disposed within the opening OH defined in the pixel defining film PDL. For example, the light emitting layers EML provided in a corresponding manner to the respective light emitting areas PXA-R, PXA-G, PXA-B by the pixel defining film PDL division can emit light of the same wavelength band. In the display device DD-a of an embodiment, the light emitting layer EML may emit blue light. In addition, unlike the illustration, in an embodiment, the light emitting layer EML may be provided as a common layer throughout the light emitting region PXA-R, PXA-G, PXA-B.

The light control layer CCL may be disposed on the display panel DP. The light control layer CCL may comprise a light converting body. The light converter may be a quantum dot, a phosphor, or the like. The light conversion body may wavelength-convert the received light to emit the light. That is, the light control layer CCL may be a layer containing quantum dots or a layer containing a phosphor.

The light control layer CCL may include a plurality of light control parts CCP1, CCP2, CCP3. The light control parts CCP1, CCP2, CCP3 may be spaced apart from each other.

Referring to fig. 7, a division pattern BMP may be arranged between the light control parts CCP1, CCP2, CCP3 spaced apart from each other, but the embodiment is not limited thereto. Although fig. 8 shows a case where the division pattern BMP does not overlap with the light control parts CCP1, CCP2, CCP3, at least a portion of the edges of the light control parts CCP1, CCP2, CCP3 may overlap with the division pattern BMP.

The light control layer CCL may include: the first light control part CCP1 includes first quantum dots QD1 converting first color light supplied from the light emitting element ED into second color light; a second light control part CCP2 including second quantum dots QD2 converting the first color light into a third color light; and a third light control section CCP3 transmitting the first color light.

In an embodiment, the first light control part CCP1 may provide red light as the second color light, and the second light control part CCP2 may provide green light as the third color light. The third light control section CCP3 may transmit blue light as the first color light supplied from the light emitting element ED. For example, the first quantum dot QD1 may be a red quantum dot and the second quantum dot QD2 may be a green quantum dot. The same applies to the quantum dots QD1 and QD2 as described above.

And the light control layer CCL may further comprise a diffuser SP. The first light control part CCP1 may include first quantum dots QD1 and a diffuser SP, the second light control part CCP2 may include second quantum dots QD2 and a diffuser SP, and the third light control part CCP3 may include no quantum dots but a diffuser SP.

The scatterers SP may be inorganic particles. For example, the diffuser SP may include TiO ₂ 、ZnO、Al ₂ O ₃ 、SiO ₂ And at least one of hollow silica. The diffuser SP may comprise TiO ₂ 、ZnO、Al ₂ O ₃ 、SiO ₂ And hollow silica, or may be mixed with a material selected from TiO ₂ 、ZnO、Al ₂ O ₃ 、SiO ₂ And two or more kinds of hollow silica.

Each of the first, second, and third light control parts CCP1, CCP2, and CCP3 may include base resins BR1, BR2, BR3 dispersing quantum dots QD1, QD2, and a diffuser SP. In an embodiment, the first light control part CCP1 may include first quantum dots QD1 and a diffuser SP dispersed in the first base resin BR1, the second light control part CCP2 may include second quantum dots QD2 and a diffuser SP dispersed in the second base resin BR2, and the third light control part CCP3 may include a diffuser SP dispersed in the third base resin BR3. The base resins BR1, BR2, BR3 are generally used as a medium for dispersing the quantum dots QD1, QD2 and the scatterer SP, and may be composed of various resin compositions which may be called binders. For example, the base resins BR1, BR2, BR3 may be acrylic resins, urethane resins, silicone resins, epoxy resins, or the like. The base resins BR1, BR2, BR3 may be transparent resins. In an embodiment, each of the first base resin BR1, the second base resin BR2, and the third base resin BR3 may be the same or different from each other.

The light control layer CCL may include a first barrier layer BFL1. The first barrier layer BFL1 may prevent permeation of moisture and/or oxygen (hereinafter, referred to as "moisture/oxygen"). The first barrier layer BFL1 may be disposed under the light control parts CCP1, CCP2, CCP3 to block the light control parts CCP1, CCP2, CCP3 from being exposed to moisture/oxygen. The first barrier layer BFL1 may cover the light control parts CCP1, CCP2, and CCP3. The second barrier layer BFL2 may be provided between the light control units CCP1, CCP2, CCP3 and the color filters CF1, CF2, CF 3.

The barrier layers BFL1, BFL2 may comprise at least one inorganic layer. That is, the barrier layers BFL1, BFL2 may be configured to include an inorganic substance. For example, the barrier layers BFL1, BFL2 may be composed of silicon nitride, aluminum nitride, zirconium nitride, titanium nitride, hafnium nitride, tantalum nitride, silicon oxide, aluminum oxide, titanium oxide, tin oxide, cerium oxide, silicon oxynitride, a metal film ensuring transmittance, or the like. In addition, the barrier layers BFL1, BFL2 may further comprise an organic film. The barrier layers BFL1, BFL2 may be constructed as a single layer or as multiple layers.

In one embodiment of the display device DD, a color filter layer CFL may be disposed on the light control layer CCL. For example, the color filter layer CFL may be disposed directly on the light control layer CCL. In this case, the second barrier layer BFL2 may be omitted.

The color filter layer CFL may include color filters CF1, CF2, CF3. The color filter layer CFL may include a first color filter CF1 transmitting light of the second color, a second color filter CF2 transmitting light of the third color, and a third color filter CF3 transmitting light of the first color. For example, the first color filter CF1 may be a red color filter, the second color filter CF2 may be a green color filter, and the third color filter CF3 may be a blue color filter. Each of the color filters CF1, CF2, CF3 may include a high molecular photosensitive resin and a pigment or dye. The first color filter CF1 may include a red pigment or dye, the second color filter CF2 may include a green pigment or dye, and the third color filter CF3 may include a blue pigment or dye. In addition, the embodiment is not limited thereto, and the third color filter CF3 may not include pigment or dye. The third color filter CF3 may include a high molecular photosensitive resin without including a pigment or dye. The third color filter CF3 may be transparent. The third color filter CF3 may be formed using a transparent photosensitive resin.

Also, in an embodiment, the first and second color filters CF1 and CF2 may be yellow (yellow) color filters. The first and second color filters CF1 and CF2 may also be integrally provided without distinguishing from each other. Each of the first, second, and third color filters CF1, CF2, and CF3 may correspond to a red light emitting region PXA-R, a green light emitting region PXA-G, and a blue light emitting region PXA-B, respectively.

In addition, although not shown, the color filter layer CFL may include a light shielding portion (not shown). The color filter layer CFL may include a light shielding portion (not shown) arranged to overlap with the boundary line of the adjacent color filters CF1, CF2, CF 3. The light shielding portion (not shown) may be a black matrix. The light shielding portion (not shown) may be formed of an organic light shielding material or an inorganic light shielding material including a black pigment or a black dye. The light shielding portion (not shown) can distinguish the boundary between the adjacent color filters CF1, CF2, CF 3. Also, in an embodiment, the light shielding portion (not shown) may be formed of a blue color filter.

The color filter layer CFL may have a base substrate BL disposed thereon. The base substrate BL may be a member providing a base surface on which the color filter layer CFL, the light control layer CCL, and the like are arranged. The base substrate BL may be a glass substrate, a metal substrate, a plastic substrate, or the like. However, the embodiment is not limited thereto, and the base substrate BL may be an inorganic layer, an organic layer, or a composite material layer. Further, unlike the illustration, in an embodiment, the base substrate BL may be omitted.

Fig. 8 is a cross-sectional view showing a part of a display device according to an embodiment. Fig. 8 is a cross-sectional view of a portion corresponding to the display panel DP of fig. 7. In the display device DD-TD of an embodiment, the light emitting element ED-BT may include a plurality of light emitting structures OL-B1, OL-B2, OL-B3. The light emitting element ED-BT may include a first electrode EL1 and a second electrode EL2 facing each other and a plurality of light emitting structures OL-B1, OL-B2, OL-B3 provided between the first electrode EL1 and the second electrode EL2 sequentially stacked in the thickness direction. Each of the light emitting structures OL-B1, OL-B2, OL-B3 may include a light emitting layer EML (fig. 7), a hole transporting region HTR (fig. 7) and an electron transporting region ETR (fig. 7) disposed with the light emitting layer EML interposed therebetween.

That is, the light emitting elements ED to BT included in the display device DD to TD of an embodiment may be light emitting elements of a Tandem (Tandem) structure including a plurality of light emitting layers.

In one embodiment shown in fig. 8, the light emitted from each of the light emitting structures OL-B1, OL-B2, OL-B3 may be all blue light. However, the embodiment is not limited thereto, and the wavelength bands of light emitted from each of the light emitting structures OL-B1, OL-B2, OL-B3 may be different from each other. For example, the light emitting element ED-BT including the plurality of light emitting structures OL-B1, OL-B2, OL-B3 emitting light of different wavelength bands from each other may emit white light.

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

At least one of the light emitting structures OL-B1, OL-B2, OL-B3 included in the display device DD-TD of an embodiment may include the amine compound of the above-described one embodiment.

Referring to fig. 9, a display device DD-b according to an embodiment may include light emitting elements ED-1, ED-2, ED-3 stacked with two light emitting layers. In comparison with the display device DD of the embodiment shown in fig. 2, the embodiment shown in fig. 9 is different in that each of the first light emitting element ED-1, the second light emitting element ED-2, and the third light emitting element ED-3 includes two light emitting layers stacked in the thickness direction. In each of the first light emitting element ED-1, the second light emitting element ED-2, and the third light emitting element ED-3, the two light emitting layers may emit light of the same wavelength region.

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. Also, 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. The light emission auxiliary portion OG may be disposed between the first and second red light emitting layers EML-R1 and EML-R2, between the first and second green light emitting layers EML-G1 and EML-G2, and between the first and second blue light emitting layers EML-B1 and EML-B2.

The light emitting auxiliary portion OG may include a single layer or multiple layers. The light emission auxiliary portion OG may include a charge generation layer. More specifically, the light emission auxiliary portion OG may include an electron transport region, a charge generation layer, and a hole transport region stacked in this order. The light emission auxiliary portion OG may be provided as a common layer among the entire first, second, and third light emitting elements ED-1, ED-2, and ED-3. However, the embodiment is not limited thereto, and the light emission assisting portion OG may be provided by patterning in the opening portion OH defined by the pixel definition film PDL.

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 light emission auxiliary OG and the electron transport region ETR. 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 hole transporting region HTR and the light emitting auxiliary portion OG.

That is, 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, a light emitting auxiliary portion OG, a first red light emitting layer EML-R1, an electron transport region ETR, and a second electrode EL2, which are sequentially stacked. The second light emitting element ED-2 may include a first electrode EL1, a hole transporting region HTR, a second green light emitting layer EML-G2, a light emitting auxiliary portion OG, a first green light emitting layer EML-G1, an electron transporting region ETR, and a second electrode EL2, which are sequentially stacked. The third light emitting element ED-3 may include a first electrode EL1, a hole transporting region HTR, a second blue light emitting layer EML-B2, a light emitting auxiliary portion OG, a first blue light emitting layer EML-B1, an electron transporting region ETR, and a second electrode EL2, which are sequentially stacked.

In addition, the optical auxiliary layer PL may be disposed on the display element layer DP-ED. The optical auxiliary layer PL may include a polarizing layer. The optical auxiliary layer PL may be disposed on the display panel DP to control reflected light from the display panel DP due to external light. Unlike what is shown, in the display device according to an embodiment, the optical auxiliary layer PL may be omitted.

Unlike fig. 8 and 9, the display device DD-C of fig. 10 is shown to include four light emitting structures OL-B1, OL-B2, OL-B3, OL-C1. The light emitting element ED-CT may include a first electrode EL1 and a second electrode EL2 facing each other, and a fourth light emitting structure OL-C1, a first light emitting structure OL-B1, a second light emitting structure OL-B2, and a third light emitting structure OL-B3 stacked in order in a thickness direction between the first electrode EL1 and the second electrode EL2. The charge generation layers CGL1, CGL2, CGL3 may be arranged between the first light emitting structure OL-B1, the second light emitting structure OL-B2, the third light emitting structure OL-B3, and the fourth light emitting structure OL-C1. Of the four light emitting structures, the first, second and third light emitting structures OL-B1, OL-B2 and OL-B3 may emit blue light, and the fourth light emitting structure OL-C1 may emit green light. However, the embodiment is not limited thereto, and the first, second, third, and fourth light emitting structures OL-B1, OL-B2, OL-B3, and OL-C1 may emit light of different wavelength regions from each other.

The charge generation layers CGL1, CGL2, CGL3 arranged between adjacent light emitting structures OL-B1, OL-B2, OL-B3, OL-C1 may comprise a p-type charge generation layer and/or an n-type charge generation layer.

The display device DD-C of an embodiment may include at least one of the light emitting structures OL-B1, OL-B2, OL-B3, OL-C1 including the amine compound of an embodiment described above.

The light emitting element ED according to an embodiment of the present invention may include the amine compound of the above-described embodiment in at least one functional layer disposed between the first electrode EL1 and the second electrode EL2, thereby exhibiting improved light emitting efficiency and improved lifetime characteristics. The light-emitting element ED according to an embodiment may contain the amine compound of the above-described one embodiment in at least one of the hole transport region HTR, the light-emitting layer EML, and the electron transport region ETR disposed between the first electrode EL1 and the second electrode EL2, or the amine compound of the above-described one embodiment in the capping layer CPL. For example, an amine compound according to an embodiment may be contained in the hole transport region HTR of the light emitting element ED of an embodiment, and the light emitting element ED of an embodiment may exhibit long-life characteristics.

The amine compound of the above-described embodiment may include a first substituent, a second substituent, and a third substituent, so that stability of a material may be improved and hole transport property may be improved. Accordingly, the lifetime of the light-emitting element including the amine compound of one embodiment can be improved. Also, the light emitting element of an embodiment may exhibit an increased lifetime characteristic by including the amine compound according to an embodiment in the electron blocking layer.

Hereinafter, the amine compound according to one embodiment of the present invention and the light-emitting element according to one embodiment will be described in detail with reference to examples and comparative examples. Also, the embodiment shown below is one example for aiding in understanding the present invention, and the scope of the present invention is not limited thereto.

Examples (example)

1. Synthesis of amine Compounds

First, the synthetic method of the amine compound of this example will be specifically described by illustrating the synthetic methods of the compound 1, the compound 3, the compound 4, the compound 5, the compound 6, the compound 7, the compound 8, the compound 9, the compound 10, the compound 11, the compound 12, the compound 13, the compound 14, the compound 18, the compound 28, the compound 61, and the compound 70 disclosed in table 1 below. Also, the method of synthesizing an amine compound described below is an example, and the method of synthesizing an amine compound according to the embodiment of the present invention is not limited to the following embodiment.

< method for synthesizing Compound >

10.0mmol of intermediate compound P, 11.0mmol of intermediate compound Q, 0.29g (0.50 mmol) of Pd (dba) were reacted under an atmosphere of argon (Ar) ₂ 、0.59g(2.0mmol)P(tBu) ₃ ·HBF ₄ And 1.45g (15.0 mmol) of NaOtBu was added to a 200mL three-necked flask and stirred in 50mL of toluene solvent at 130℃for 8 hours. The stirred mixture was cooled and then washed with water to separate an organic layer. The separated organic layer was purified by column chromatography (Silica gel) to obtain the objective compound. For the identification of compounds, FAB-MS and ¹ H-NMR(CDCl ₃ ) Measurements were made.

Structure and added weight of intermediate compound P, structure and added weight of intermediate compound Q, and resultant target compoundThe yields and FAB-MS are shown in Table 1 below. Of a compound of interest ¹ H-NMR is shown in Table 2 below. In addition, FAB-MS was measured for the molecular weight of the example compound using JMS-700V from JEOL corporation. In addition, the compounds of the examples were measured using AVAVCE300M manufactured by Bruker Biospin K.K ¹ H-NMR。

TABLE 1

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TABLE 2

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2. Manufacturing and evaluation of light emitting element

(1) Manufacturing of light emitting element

An embodiment light-emitting element including the amine compound of one embodiment in the electron blocking layer was manufactured by the following method.

On a glass substrateAfter patterning the ITO with the thickness of (a), washing with ultrapure water and UV ozone treatment was performed for 10 minutes, thereby forming a first electrode. Thereafter, by +.>2-TNATA is deposited to form a hole injection layer. Thereafter, by +.>The example compound or the comparative example compound is deposited to form an electron blocking layer.

Then, by doping TBP 3% in ADN, a thickness ofIs provided. Next, use +.>Thickness deposition Alq of (2) ₃ Thereby forming an electron transport layer, and then +.>LiF is deposited to form an electron injection layer.

Then, byAluminum (Al) is provided to form the second electrode. In an embodiment, the hole injection layer, the electron blocking layer, the light emitting layer, the electron transport layer, the electron injection layer, and the second electrode are formed using a vacuum deposition apparatus.

< comparative example Compound >

In addition, the compounds of the respective functional layers used in manufacturing the light-emitting element are as follows.

(2) Evaluation of light-emitting element

Table 3 shows the results for examples 1 to 14And the evaluation results of the light emitting elements of comparative examples 1 to 14. In the results of characteristic evaluation for examples and comparative examples shown in Table 3, the luminous efficiency was shown to be 10mA/cm ² The half-life represents an efficiency value at a current density of from 1000cd/m ² Is a luminance half-decay time of (c). The purity of the film represents a value obtained by measuring the purity of the electron blocking layer material deposited on the substrate after depositing the respective electron blocking layer materials at 0.2nm/s by HPLC. All electron blocking layer materials had a purity of 99.9% prior to deposition. The absorption end wavelength represents a wavelength at a start position on a long wavelength side of an absorption spectrum of a deposition film on which each electron blocking layer material is deposited.

TABLE 3

/>

Referring to the results of table 3, it can be seen that the embodiment of the light emitting element using the amine compound according to an embodiment of the present invention as an electron blocking layer material exhibited long life characteristics.

The amine compound of the embodiment including the first substituent, the second substituent, and the third substituent having high electron resistance has high electron resistance. Also, the amine compound of the embodiment can suppress an excessive increase in deposition temperature, and can suppress material degradation caused by the deposition process. Therefore, it can be seen that the light emitting element of the embodiment using the amine compound of the embodiment as an electron blocking layer material has excellent lifetime.

Specifically, the first substituent includes a dibenzofuranyl group or a dibenzothienyl group to which an aryl group is bonded in the 6-position, and a nitrogen atom of an amine is directly bonded in the 3-position of the dibenzofuranyl group and the dibenzothienyl group. The amine compound of the embodiment contains the first substituent so as not to cause instability due to steric twisting around the amine, and thus can have high stability.

In the amine compound of an embodiment, at least one of the second substituent and the third substituent is a substituted or unsubstituted naphthyl group or a substituted or unsubstituted heteroaryl group bonded in para (para) relationship to the nitrogen atom of the amine through a linking group. The amine compound of the embodiment includes the second substituent and the third substituent, and thus may have further improved hole transport property and stability.

The compound of comparative example used in comparative example 1 was substituted with naphthalene (naphthalene) group at the 6-position of dibenzofuran (dibenzofuran) compared with the compound used in example 1, and thus the light-emitting element of comparative example 1 exhibited low light-emitting efficiency/short lifetime. This is considered to be because the absorption wavelength of the molecules is too long to be long, and a part of the light emitted from the light-emitting layer is absorbed, so that the transport layer itself is excited.

In the comparative example compounds used in comparative example 2, two groups among the groups bound to amine (amine) included a benzene (phenyl) group having a substituent at meta (meta) compared with the example compounds used in examples 1 to 4, 11 and 12. Accordingly, the light-emitting element of comparative example 2 exhibited low light-emitting efficiency and short lifetime. This is considered to be because of the substituents bonded to the amine (amine), both substituents other than the 3-dibenzofuran (3-dibenzofuran) group have no substituent at the para position (para), thereby reducing hole stability.

In the comparative example compound used in comparative example 3, one of the groups bonded to the amine (amine) is composed of a benzene (phenyl) group substituted with a dibenzosiloxane (phenyloxacillin) group at the para-position (para) compared with the example compound used in example 1, and thus the light-emitting element of comparative example 3 exhibits low light-emitting efficiency and short lifetime. This is believed to be due to the low stability of the dibenzosiloxane (phenoxilin) group to holes/electrons.

In the comparative example compounds used in comparative examples 4 and 5, one group among the groups bonded to amine (amine) was constituted of biphenyl (biphenyl) groups, so that the lifetime of the fabricated element was slightly shortened, as compared with the compounds used in examples 1 to 6, example 9 and example 10. This is considered to be because the compound is composed of biphenyl groups, as compared with the example compound in which three groups bonded to amine (amine) include naphthalene (naphthalene) group or heteroaryl (heteroaryl) group each having high electron resistance, thereby correspondingly decreasing electron resistance.

In the compounds used in comparative examples 6 and 7, the position No. 6 of dibenzofuran/dibenzothiophene was not substituted, as compared with the compounds used in examples 1 and 13, so that the light-emitting elements of comparative examples 6 and 7 exhibited short lives. This is considered to be because the O, S atom periphery of the 3-dibenzofuran (3-dibenzothiophene) group/3-dibenzothiophene (3-dibenzothiophene) group directly bonded to the amine is not sterically protected, and thus the stability is lowered.

In the comparative example compound used in comparative example 8, one group among the groups bonded to amine (amine) was directly bonded to an α -naphthalene (α -naphthalene) group, as compared with the example compounds used in examples 1 to 5, example 7 and example 8, and thus, the result of reduced lifetime of the light emitting element of comparative example 8 was exhibited. This is thought to be because the stability of the α -naphthalene (α -naphthalenyl) group directly bonded to the amine (amine) is low.

In the comparative example compound used in comparative example 9, one of the groups bonded to amine (amine) was directly bonded to β -naphthalene (β -naphthalene) group, compared with the example compounds used in examples 1 to 6, example 9 and example 10, and thus the light-emitting element of comparative example 9 exhibited low light-emitting efficiency and short lifetime. This is considered to be because the absorption wavelength of the molecule is too long to be a long wavelength, and a part of the light emitted from the light-emitting layer is absorbed, so that the transport layer itself is excited.

In the comparative example compound used in comparative example 10, one of the groups bound to amine (amine) is composed of a 4-dibenzofuran (4-dibenzofuran) group and the other group is composed of a benzene (phenyl) group having a substituent at the meta position, compared with the example compounds used in examples 7 and 10, and thus the light-emitting element of comparative example 10 exhibits low light-emitting efficiency and short lifetime. This is thought to be because of the fact that two groups other than the 3-dibenzofuran (3-dibenzofuran) group among the groups bound to the amine have no substituent at the para position (para), thereby reducing the stability against holes.

The compound of comparative example used in comparative example 11 was substituted with a benzene (phenyl) group at the 7-position of dibenzofuran (dibenzofuran) instead of the 6-position, as compared with the compound of example used in example 1, so that the light-emitting element of comparative example 11 exhibited low light-emitting efficiency and short lifetime. This is considered to be because the absorption wavelength of the molecule is excessively long to become a long wavelength, a part of light emitted from the light emitting layer is absorbed, and thus the transport layer itself is excited, and the O atom of the 3-dibenzofuran group directly bonded to the amine is not stereoscopically protected around the O atom, resulting in a decrease in stability.

Compared with the example compound used in example 13, the comparative example compound used in comparative example 12 was substituted with a benzene (phenyl) group at the 2-position of dibenzothiophene (dibenzothiophene) instead of the 6-position, so that the light-emitting element of comparative example 12 exhibited low light-emitting efficiency and short lifetime. In this case, the S atom around the 3-dibenzothiophene (3-dibenzothiophene) group which is considered to be directly bonded to the amine (amine) is not stereoscopically protected, thus resulting in a decrease in stability, and the bond between the dibenzothiophene (dibenzothiophene) and nitrogen is distorted to become unstable, thus exhibiting a short lifetime.

The comparative example compounds used in comparative examples 13 and 14 were combined with nitrogen at the No. 4 position of dibenzofuran/dibenzothiophene compared with the example compounds used in examples 1 and 13, so that the light-emitting elements of comparative examples 13 and 14 exhibited slightly reduced lifetime compared with the light-emitting elements of examples. This is considered to be because it is difficult for a unit (unit) of dibenzofuran/dibenzothiophene to transport holes by using a substitution pattern having no substituent at the para position (para) of amine (amine).

Although the present invention has been described with reference to the preferred embodiments, it will be understood by those skilled in the art or those having ordinary skill in the art that various modifications and changes may be made to the present invention without departing from the spirit and scope of the invention as set forth in the appended claims. Therefore, the technical scope of the present invention should not be limited to what is described in the detailed description of the specification, but should be determined by the claims.

Claims

1. An amine compound represented by the following chemical formula 1:

[ chemical formula 1]

In the chemical formula 1 described above, a compound having the formula,

Q ¹ is either O or S, and is preferably selected from the group consisting of,

Ar ¹ in the case of a substituted or unsubstituted phenyl group,

R ¹ and R is ² Each independently represents a hydrogen atom, a heavy hydrogen atom, a halogen atom, a substituted or unsubstituted silyl group, a substituted or unsubstituted aryl group having 6 or more and 30 or less ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 or more and 30 or less ring-forming carbon atoms,

X ¹ is a substituted or unsubstituted naphthyl group or a substituted or unsubstituted heteroaryl group having 2 or more and 30 or less ring-forming carbon atoms,

n1 is an integer of 1 to 3, k1 is an integer of 0 to 6, k2 is an integer of 0 to 4,

FG is represented by the following chemical formula 2-1 or the following chemical formula 2-2:

[ chemical formula 2-1]

[ chemical formula 2-2]

In the chemical formula 2-1 and the chemical formula 2-2,

X ² is a substituted or unsubstituted naphthyl group or a substituted or unsubstituted heteroaryl group having 2 or more and 30 or less ring-forming carbon atoms,

R ³ and R is ⁴ Each independently represents a hydrogen atom, a heavy hydrogen atom, a halogen atom, a substituted or unsubstituted silyl group, a substituted or unsubstituted aryl group having 6 or more and 30 or less ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 or more and 30 or less ring-forming carbon atoms,

Q ² O, S, NR of a shape of O, S, NR ⁵ Or CR ⁶ R ⁷ ，

R ⁵ To R ⁷ Each independently represents a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 50 ring-forming carbon atoms,

z is a substituted or unsubstituted aromatic hydrocarbon ring having 6 or more and 30 or less ring-forming carbon atoms or a substituted or unsubstituted aromatic heterocyclic ring having 2 or more and 30 or less ring-forming carbon atoms,

k3 is an integer of 0 to 4, k4 is an integer of 0 to 7, n2 is an integer of 1 to 3,

wherein X is ₁ And X ₂ Is thatExcept for the case of (2).

2. The amine compound according to claim 1, wherein,

the chemical formula 2-1 is represented by the following chemical formula 2-1a or the following chemical formula 2-1 b:

[ chemical formula 2-1a ]

[ chemical formula 2-1b ]

In the chemical formula 2-1a and the chemical formula 2-1b,

R ^3-1 to R ^3-3 Each independently represents a hydrogen atom, a heavy hydrogen atom, a halogen atom, a substituted or unsubstituted aryl group having 6 to 15 ring-forming carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 15 ring-forming carbon atoms,

k3-1 to k3-3 are each independently an integer of 0 to 4,

n2-1 is an integer of 0 to 2,

X ² and n2 is the same as that defined in the chemical formula 2-1.

3. The amine compound according to claim 1, wherein,

the chemical formula 2-2 is represented by any one of the following chemical formulas 2-2a to 2-2 c:

[ chemical formula 2-2a ]

[ chemical formula 2-2b ]

[ chemical formula 2-2c ]

In the chemical formulas 2-2a to 2-2c,

Z _a is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 10 carbon atoms in the ring, R ^4-1 Is a hydrogen atom, a heavy hydrogen atom, a halogen atom or a substituted or unsubstituted aryl group having 6 to 15 ring-forming carbon atoms,

k4-1 is an integer of 0 to 7,

Q ² the same as defined in the chemical formula 2-2.

4. The amine compound according to claim 1, wherein,

the FG is represented by any one of the following chemical formulas FG-1 to FG-6:

[ chemical formula FG-1]

[ chemical formula FG-2]

[ chemical formula FG-3]

[ chemical formula FG-4]

[ chemical formula FG-5]

[ chemical formula FG-6]

In the formulas FG-1 to FG-6,

R ³ⁱ 、R ³ⁱⁱ r is R ⁴ⁱ To R ⁴ⁱⁱⁱ Each independently is a hydrogen atom, a heavy hydrogen atom, a halogen atom, or a substituted or unsubstituted phenyl group,

k3i, k3ii and k4ii are each independently integers of 0 to 4,

k4i is an integer of 0 to 3,

k4iii is an integer of 0 to 2,

X ² and Q ² The same as defined in the chemical formula 2-1 and the chemical formula 2-2.

5. The amine compound according to claim 1, wherein,

the chemical formula 1 is represented by the following chemical formula 3-1 or the following chemical formula 3-2:

[ chemical formula 3-1]

[ chemical formula 3-2]

In the chemical formula 3-1 and the chemical formula 3-2,

y is O or NR ¹¹ ，

R ⁸ To R ¹¹ Each independently represents a hydrogen atom, a heavy hydrogen atom, a halogen atom, or a substituted or unsubstituted aryl group having 6 to 20 ring-forming carbon atoms,

m1 is an integer of 0 to 5, m2 and m3 are each independently an integer of 0 to 7,

Q ¹ 、R ¹ 、R ² n1, k2 and FG are the same as defined in the chemical formula 1.

6. The amine compound according to claim 1, wherein,

the chemical formula 1 is represented by the following chemical formula 4-1 or the following chemical formula 4-2:

[ chemical formula 4-1]

[ chemical formula 4-2]

In the chemical formula 4-1 and the chemical formula 4-2,

R ^2a to R ^4a Each independently is a hydrogen atom, a heavy hydrogen atom, a halogen atom, or a substituted or unsubstituted phenyl group,

k2a and k3a are each independently an integer of 0 to 4 inclusive, k4a is an integer of 0 to 7 inclusive,

l1 is 1 or 2, and the number of the components is 1,

Ar ¹ 、R ¹ 、X ¹ 、X ² 、Q ¹ 、Q ² z and k1 are the same as those defined in the chemical formula 1, the chemical formula 2-1 and the chemical formula 2-2.

7. The amine compound according to claim 1, wherein,

represented by the chemical formula 2-1 at the FGIn the case of (1), X ¹ And X ² At least one of which is a substituted or unsubstituted naphthyl group,

in the case where the FG is represented by the chemical formula 2-2, X ¹ Is a substituted or unsubstituted naphthyl group.

8. The amine compound according to claim 1, wherein,

the amine compound represented by the chemical formula 1 is represented by any one of the following compounds of the compound group 1:

[ Compound group 1]

9. A light emitting element comprising:

a first electrode;

a second electrode disposed on the first electrode; and

at least one functional layer arranged between the first electrode and the second electrode and comprising the amine compound according to any one of claims 1 to 8.

10. The light-emitting element according to claim 9, wherein,

the at least one functional layer comprises: a light emitting layer; a hole transport region disposed between the first electrode and the light emitting layer; and an electron transport region disposed between the light emitting layer and the second electrode,

Wherein the hole transport region comprises the amine compound according to any one of claims 1 to 8.