KR20230159799A - Light emitting element and amine compound for the same - Google Patents

Abstract

The present invention relates to a light-emitting device and an amine compound for a light-emitting device. The light-emitting device in one embodiment includes a first electrode, a second electrode disposed on the first electrode, and a second electrode disposed between the first electrode and the second electrode. By including at least one functional layer and including an amine compound represented by the following formula (1) in the at least one functional layer, the luminous efficiency and device life of the light emitting device can be improved.
[Formula 1]

Description

Light emitting element and amine compound for light emitting element {LIGHT EMITTING ELEMENT AND AMINE COMPOUND FOR THE SAME}

The present invention relates to light-emitting devices and amine compounds for light-emitting devices, and more specifically, to light-emitting devices containing a novel amine compound in a functional layer.

Recently, as an image display device, there has been active development of organic electroluminescence display devices and the like. An organic electroluminescent display device or the like is a display device including a so-called self-luminous light-emitting element that realizes display by causing the light-emitting material of the light-emitting layer to emit light by recombining holes and electrons injected from the first electrode and the second electrode in the light-emitting layer.

When applying light-emitting devices to display devices, high luminous efficiency and long lifespan are required, and the development of materials for light-emitting devices that can stably implement these is continuously required.

In particular, in order to realize light emitting devices with high efficiency and long lifespan, the development of materials in the hole transport region with excellent hole transport properties and stability is in progress.

The purpose of the present invention is to provide a light emitting device that exhibits high efficiency and long lifespan characteristics.

Another object of the present invention is to provide an amine compound as a material for light emitting devices to increase efficiency and improve device lifespan.

The light emitting device of the present invention 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 formula (1); Includes:

[Formula 1]

In Formula 1, L ₁ and L ₂ are each independently a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms, x is 1 or 2, Ar is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, and R ₁ and R ₂ are each independent hydrogen atom, deuterium atom, halogen atom, substituted or unsubstituted silyl group, substituted or unsubstituted aryl group with 6 to 30 ring carbon atoms, or substituted or unsubstituted heteroaryl with 2 to 30 ring carbon atoms. It forms a ring by grouping or bonding with adjacent groups, and R ₃ is a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, or a substituted or an unsubstituted aryl group with 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group with 2 to 30 ring carbon atoms, or a ring is formed by combining with adjacent groups, provided that R ₃ Except in the case where the amine group is a substituted aryl group, R ₄ and R ₅ each independently represent a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted silyl group, or a substituted or unsubstituted ring-forming group with 6 to 30 carbon atoms. Aryl group, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, a and b are each independently an integer of 0 to 4, c is an integer of 0 to 5, and d is 0 or more. It is an integer of 3 or less, e is an integer of 0 to 3, at least one R ₄ is a hydrogen atom, and includes a structure in which any hydrogen in the molecule is replaced with deuterium.

In one embodiment, the at least one functional layer includes 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, The transport region may include an amine compound represented by Formula 1 above.

In one embodiment, the hole transport region includes a hole injection layer disposed on the first electrode, and a hole transport layer disposed on the hole injection layer, and the hole transport layer includes an amine compound represented by Formula 1. It can be included.

In one embodiment, the amine compound represented by Formula 1 may be a monoamine compound.

In one embodiment, R ₁ and R ₂ are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted methyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted dibenzofuran group, or a substituted or unsubstituted group. It may be a dibenzoheterol group, or it may be combined with adjacent groups to form a ring.

In one embodiment, R ₃ is a hydrogen atom, a deuterium atom, a substituted or unsubstituted allyl group, a substituted or unsubstituted pyridine group, a substituted or unsubstituted tetrazole group, a substituted or unsubstituted dibenzofuran group, or a substituted Alternatively, it may be an unsubstituted triazine group, or it may form a ring by combining with adjacent groups.

In one embodiment, R ₄ and R ₅ may each independently be a hydrogen atom or a deuterium atom.

In one embodiment, Ar is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted quaterphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted group, and It may be a phenanthryl group, a substituted or unsubstituted fluorene group, a substituted or unsubstituted dibenzofuran group, or a substituted or unsubstituted dibenzoheterol group.

In one embodiment, L ₁ is a substituted or unsubstituted phenylene group, a substituted or unsubstituted divalent biphenyl group, a substituted or unsubstituted divalent terphenyl group, a substituted or unsubstituted divalent quaterphenyl group, or a substituted or unsubstituted group. A divalent fluorene group, a substituted or unsubstituted divalent dibenzofuran group, a substituted or unsubstituted divalent dibenzoheterol group, a substituted or unsubstituted dibenzosilol group, or a substituted or unsubstituted divalent dibenzosilol group. It may be a divalent naphthyl group.

In one embodiment, L ₂ is a substituted or unsubstituted phenylene group, a substituted or unsubstituted divalent biphenyl group, a substituted or unsubstituted divalent naphthyl group, a substituted or unsubstituted divalent phenanthryl group, or a substituted or It may be an unsubstituted divalent triphenylenyl group.

In one embodiment, the amine compound represented by Formula 1 may be represented by any of the following Formulas 1-1 to 1-3:

[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

In Formulas 1-1 to 1-3, R ₃₁ , R ₃₂ , and R ₃₃ are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted silyl group, or a substituted or unsubstituted carbon number of 2 or more. An alkenyl group of 30 or less, a substituted or unsubstituted aryl group of 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring carbon atoms, c1 is an integer of 0 to 5, c2 and c3 are each integers from 0 to 7, except that each of R ₃₁ , R ₃₂ , and R ₃₃ is an aryl group substituted with an amine group, and Ar, R ₁ , R ₂ , R ₄ , R ₅ , L ₁ , L ₂ , a, b, d, e, and x are the same as defined in Formula 1.

The amine compound of the present invention is represented by the following formula (1):

[Formula 1]

In Formula 1, L ₁ and L ₂ are each independently a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms, x is 1 or 2, Ar is a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, and R ₁ and R ₂ are each independently a hydrogen atom, a deuterium atom, a halogen atom, or a substituted or unsubstituted silyl group. group, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, or forming a ring by combining with adjacent groups, R ₃ is a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkenyl group with 2 to 30 carbon atoms, a substituted or unsubstituted aryl group with 6 to 30 ring carbon atoms, or A substituted or unsubstituted ring-forming heteroaryl group having 2 to 30 carbon atoms, or a ring formed by combining with an adjacent group, except in the case where R ₃ is an aryl group substituted with an amine group, R ₄ and R ₅ are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted silyl group, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted ring forming carbon number of 2 to 30 is a heteroaryl group, a and b are each independently an integer of 0 to 4, c is an integer of 0 to 5, d is an integer of 0 to 3, and e is an integer of 0 to 3, At least one R ₄ is a hydrogen atom, and includes structures in which any hydrogen in the molecule is replaced with deuterium.

In one embodiment, L ₁ may be represented by at least one of the substituents of the following substituent group S:

[Substituent group S]

In the substituent group S, R _S1 to R _S49 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted silyl group, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or an unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, y1 to y4, and y6 to y42 are each independently an integer of 0 to 4, and y5 and y43 to y49 are each independently an integer of 0 to 6. is an integer, and in the substituent group S, " " means the position connected to the nitrogen atom in Formula 1, " " means the position connected to the nitrogen atom of carbazole in Formula 1 above.

In one embodiment, the amine compound represented by Formula 1 may be represented by any one of the following Formulas 2-1 to 2-6:

[Formula 2-1]

[Formula 2-2]

[Formula 2-3]

[Formula 2-4]

[Formula 2-5]

[Formula 2-6]

In Formulas 2-1 to 2-6, R ₆ to R ₁₈ are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted silyl group, or a substituted or unsubstituted ring-forming carbon number of 6 to 30. an aryl group, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, f, g, h, j, and q are each independently integers from 0 to 4, and i and n are each independently are independently integers from 0 to 2, and k, l, m, o, p, and r are each independently integers from 0 to 3, Ar, R ₁ to R ₅ , L ₁ , a to e, and x is the same as defined in Formula 1.

The light emitting device of one embodiment may exhibit high efficiency and long lifespan characteristics by including the amine compound of one embodiment.

The amine compound of one embodiment may exhibit high efficiency and long lifespan characteristics when applied to a light emitting device.

1 is a plan view showing a display device according to an embodiment.
Figure 2 is a cross-sectional view of a display device according to an embodiment.
Figure 3 is a cross-sectional view schematically showing a light-emitting device according to an embodiment.
Figure 4 is a cross-sectional view schematically showing a light-emitting device according to an embodiment.
Figure 5 is a cross-sectional view schematically showing a light-emitting device according to an embodiment.
Figure 6 is a cross-sectional view schematically showing a light-emitting device according to an embodiment.
Figure 7 is a cross-sectional view of a display device according to an embodiment.
8 is a cross-sectional view of a display device according to an embodiment.
Figure 9 is a cross-sectional view showing a display device according to an embodiment.
Figure 10 is a cross-sectional view showing a display device according to an embodiment.

Since the present invention can be subject to various changes and have various forms, specific embodiments will be illustrated in the drawings and described in detail in the text. However, this is not intended to limit the present invention to a specific disclosed form, and should be understood to include all changes, equivalents, and substitutes included in the spirit and technical scope of the present invention.

While describing each drawing, similar reference numerals are used for similar components. In the attached drawings, the dimensions of the structures are enlarged from the actual size for clarity of the present invention. Terms such as first, second, etc. may be used to describe various components, but the components should not be limited by the terms. The above terms are used only for the purpose of distinguishing one component from another. For example, a first component may be named a second component, and similarly, the second component may also be named a first component without departing from the scope of the present invention. Singular expressions include plural expressions unless the context clearly dictates otherwise.

In this specification, terms such as “comprise” or “have” are intended to designate the presence of features, numbers, steps, operations, components, parts, or combinations thereof described in the specification, but are not intended to indicate the presence of one or more other features. It should be understood that this does not exclude in advance the possibility of the existence or addition of elements, numbers, steps, operations, components, parts, or combinations thereof.

In this specification, when a part of a layer, membrane, region, plate, etc. is said to be “on” or “on” another part, it means not only “directly above” the other part, but also when there is another part in between. Also includes. Conversely, when a part of a layer, membrane, region, plate, etc. is said to be "under" or "underneath" another part, this includes not only being "immediately below" the other part, but also cases where there is another part in between. . Additionally, in this application, being placed “on” may include being placed not only at the top but also at the bottom.

In this specification, “substituted or unsubstituted” refers to a deuterium 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. It may mean substituted or unsubstituted with one or more substituents selected from the group consisting of a phosphine sulfide group, an alkyl group, an alkenyl group, an alkynyl group, a hydrocarbon ring group, an aryl group, and a heterocyclic group. Additionally, each of the above-exemplified substituents may be substituted or unsubstituted. For example, a biphenyl group may be interpreted as an aryl group, or as a phenyl group substituted with a phenyl group.

In the present specification, "forming a ring by combining with adjacent groups" may mean combining with adjacent groups to form a substituted or unsubstituted hydrocarbon ring, or a substituted or unsubstituted hetero ring. Hydrocarbon rings include aliphatic hydrocarbon rings and aromatic hydrocarbon rings. Heterocycles include aliphatic heterocycles and aromatic heterocycles. Hydrocarbon rings and heterocycles may be monocyclic or polycyclic. Additionally, rings formed by combining with each other may be connected to other rings to form a spiro structure.

As used herein, “adjacent group” may mean a substituent substituted on an atom directly connected to the atom on which the substituent is substituted, another substituent substituted on the atom on which the substituent is substituted, or a substituent that is sterically closest to the substituent. You can. For example, in 1,2-dimethylbenzene, the two methyl groups can be interpreted as “adjacent groups,” and in 1,1-diethylcyclopentane, the two methyl groups can be interpreted as “adjacent groups.” Two ethyl groups can be interpreted as “adjacent groups” to each other. Additionally, the two methyl groups in 4,5-dimethylphenanthrene can be interpreted as “adjacent groups”.

In this specification, examples of halogen atoms include fluorine atom, chlorine atom, bromine atom, or iodine atom.

As used herein, alkyl groups 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 group, ethyl group, n-propyl group, isopropyl group, n-butyl group, s-butyl group, t-butyl group, i-butyl group, 2-ethylbutyl group, and 3, 3-dimethylbutyl group. , n-pentyl group, i-pentyl group, neopentyl group, t-pentyl group, cyclopentyl group, 1-methylpentyl group, 3-methylpentyl group, 2-ethylpentyl group, 4-methyl-2-pentyl group. , n-hexyl group, 1-methylhexyl group, 2-ethylhexyl group, 2-butylhexyl group, cyclohexyl group, 4-methylcyclohexyl group, 4-t-butylcyclohexyl group, n-heptyl group, 1 -Methylheptyl group, 2,2-dimethylheptyl group, 2-ethylheptyl group, 2-butylheptyl group, n-octyl group, t-octyl group, 2-ethyloctyl group, 2-butyloctyl group, 2-hexyl group Siloctyl group, 3,7-dimethyloctyl group, cyclooctyl group, n-nonyl group, n-decyl group, adamantyl group, 2-ethyldecyl group, 2-butyldecyl group, 2-hexyldecyl group, 2-octyl group Tyldecyl group, n-undecyl group, n-dodecyl group, 2-ethyldodecyl group, 2-butyldodecyl group, 2-hexyldodecyl group, 2-octyldodecyl group, n-tridecyl group, n-tetradecyl group, n -Pentadecyl group, n-hexadecyl group, 2-ethylhexadecyl group, 2-butylhexadecyl group, 2-hexylhexadecyl group, 2-octylhexadecyl group, n-heptadecyl group, n-octadecyl group , n-nonadecyl group, n-icosyl group, 2-ethyl icosyl group, 2-butyl icosyl group, 2-hexyl icosyl group, 2-octyl icosyl group, n-henicosyl group, n-docosyl group, n-tricosyl group Examples include syl group, n-tetracosyl group, n-pentacosyl group, n-hexacosyl group, n-heptacosyl group, n-octacosyl group, n-nonacosyl group, and n-triacontyl group, It is not limited to these.

As used herein, an alkenyl group refers to a hydrocarbon group containing at least one carbon double bond at the middle or end of an alkyl group having 2 or more carbon atoms. Alkenyl groups can 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, allyl, 1-butenyl, 1-pentenyl, 1,3-butadienyl aryl, styrenyl, and styrylvinyl groups.

As used herein, an alkynyl group refers to a hydrocarbon group containing at least one carbon triple bond at the middle or end of an alkyl group having 2 or more carbon atoms. Alkynyl groups can be straight chain 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 alkynyl groups may include, but are not limited to, ethynyl groups, propynyl groups, etc.

As used herein, hydrocarbon ring group refers to any functional group or substituent derived from an aliphatic hydrocarbon ring. The hydrocarbon ring group may be a saturated hydrocarbon ring group having 5 to 20 ring carbon atoms.

As used herein, an aryl group refers to any functional group or substituent derived from an aromatic hydrocarbon ring. The aryl group may be a monocyclic aryl group or a polycyclic aryl group. The ring-forming carbon number 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 group, naphthyl group, fluorenyl group, anthracenyl group, phenanthryl group, biphenyl group, terphenyl group, quarterphenyl group, quinquephenyl group, sexiphenyl group, triphenylenyl group, pyrenyl group, and benzofluoro. Examples include lanthenyl group and chrysenyl group, but it is not limited to these.

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

As used herein, a heterocyclic group refers to any functional group or substituent derived from a ring containing one or more of B, O, N, P, Si, and S as heteroatoms. Heterocyclic groups include aliphatic heterocyclic groups and aromatic heterocyclic groups. The aromatic heterocyclic group may be a heteroaryl group. Aliphatic heterocycles 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 hetero atoms. When the heterocyclic group contains two or more heteroatoms, the two or more heteroatoms may be the same or different from each other. In the present specification, the heterocyclic group may be a monocyclic heterocyclic group or a polycyclic heterocyclic group, and is a concept including a heteroaryl group. The number of ring carbon atoms of the heterocyclic group may be 2 to 50, 2 to 30, 2 to 20, or 2 to 10.

In the present specification, the aliphatic heterocyclic group may include one or more of B, O, N, P, Si, and S as hetero atoms. The aliphatic heterocyclic group may have 2 to 30 ring carbon atoms, 2 to 20 carbon atoms, or 2 to 10 ring carbon atoms. Examples of aliphatic heterocyclic groups include oxirane group, thiirane group, pyrrolidine group, piperidine group, tetrahydrofuran group, tetrahydrothiophene group, thiane group, tetrahydropyran group, 1,4-dioxane group, etc., but is not limited to these.

In the present specification, the heteroaryl group may include one or more of B, O, N, P, Si, and S as hetero atoms. When the heteroaryl group contains two or more heteroatoms, the two or more heteroatoms may be the same or different from each other. The heteroaryl group may be a monocyclic heterocyclic group or a polycyclic heterocyclic group. The number of ring carbon atoms of the heteroaryl group may be 2 to 50, 2 to 30, 2 to 20, or 2 to 10. Examples of heteroaryl groups include thiophene group, furan group, pyrrole group, imidazole group, triazole group, tetrazole group, pyridine group, bipyridine group, pyrimidine group, triazine group, acridyl group, pyridazine group, and pyrazinyl group. group, quinoline group, quinazoline group, quinoxaline group, phenoxazine group, phthalazine group, pyrido pyrimidine group, pyrido pyrazine group, pyrazino pyrazine group, isoquinoline group, indole group, carbazole group, N-arylcarba Sol group, N-heteroarylcarbazole group, N-alkylcarbazole group, benzoxazole group, benzoimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, thienothiophene group, benzofuran group, phenanthroline group, thiazole group, isoxazole group, oxazole group, oxadiazole group, thiadiazole group, phenothiazine group, dibenzosilol group, and dibenzofuran group, etc., but is not limited to these.

In this specification, the description regarding the aryl group described above can be applied, except that the arylene group is a divalent group. The description of the heteroaryl group described above can be applied, except that the heteroarylene group is a divalent group.

In the present specification, a boron group may mean a boron atom bonded to an alkyl group or an aryl group as defined above. Boron groups include alkyl boron groups and aryl boron groups. Examples of boron groups include, but are not limited to, dimethyl boron group, diethyl boron group, t-butylmethyl boron group, diphenyl boron group, and phenyl boron group.

In this specification, silyl groups include alkyl silyl groups and aryl silyl groups. Examples of silyl groups include trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, and phenylsilyl group. It is not limited.

In this specification, the carbon number of the carbonyl group is not particularly limited, but may be 1 to 40 carbon atoms, 1 to 30 carbon atoms, or 1 to 20 carbon atoms. For example, it may have the following structure, but is not limited to this.

In this specification, the number of carbon atoms of the sulfinyl group and sulfonyl group is not particularly limited, but may be 1 to 30. Sulfinyl groups may include alkyl sulfinyl groups and aryl sulfinyl groups. Sulfonyl groups may include alkyl sulfonyl groups and aryl sulfonyl groups.

In this specification, the thio group may include an alkyl thio group and an aryl thio group. Thio group may mean a sulfur atom bonded to an alkyl group or an aryl group as defined above. Examples of thio groups include methylthio group, ethylthio group, propylthio group, pentylthio group, hexylthio group, octylthio group, dodecylthio group, cyclopentylthio group, cyclohexylthio group, phenylthio group, and naphthylthio group. etc., but is not limited to these.

In the present specification, an oxy group may mean an oxygen atom bonded to an alkyl group or an aryl group as defined above. Oxy groups may include alkoxy groups and aryloxy groups. The alkoxy group may be straight chain, 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 1 to 10. Examples of oxy groups include methoxy, ethoxy, n-propoxy, isopropoxy, butoxy, pentyloxy, hexyloxy, octyloxy, nonyloxy, decyloxy, and benzyloxy, but are limited to these. That is not the case.

In this specification, the number of carbon atoms of the amine group is not particularly limited, but may be 1 to 30. Amine groups may include alkyl amine groups and aryl amine groups. Examples of amine groups include, but are not limited to, methylamine group, dimethylamine group, phenylamine group, diphenylamine group, naphthylamine group, and 9-methyl-anthracenylamine group.

In this specification, the alkyl group among the alkylthio group, alkylsulfoxy group, alkylaryl group, alkylamino group, alkyl boron group, alkyl silyl group, and alkyl amine group is the same as the example of the alkyl group described above.

In this specification, the aryl groups among the aryloxy group, arylthio group, arylsulfoxy group, arylamino group, aryl boron group, aryl silyl group, and aryl amine group are the same as examples of the aryl groups described above.

In this specification, direct linkage may mean a single bond.

Meanwhile, in this specification " " or " " means the location where it is connected.

Hereinafter, embodiments of the present invention will be described with reference to the drawings.

1 is a plan view showing an embodiment of the display device DD. Figure 2 is a cross-sectional view of the display device DD according to one embodiment. Figure 2 is a cross-sectional view showing a portion corresponding to line II' of Figure 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 includes light emitting elements ED-1, ED-2, and ED-3. The display device DD may include a plurality of light emitting elements ED-1, ED-2, and ED-3. The optical layer PP is disposed on the display panel DP to control reflected light from the display panel DP due to external light. The optical layer PP may include, for example, a polarizing layer or a color filter layer. Meanwhile, unlike shown in the drawing, the optical layer PP may be omitted in the display device DD of one embodiment.

A base substrate BL may be disposed on the optical layer PP. The base substrate BL may be a member that provides a base surface on which the optical layer PP is disposed. The base substrate (BL) may be a glass substrate, a metal substrate, or a plastic substrate. However, the embodiment is not limited to this, and the base substrate BL may be an inorganic layer, an organic layer, or a composite material layer. Additionally, unlike what is shown, in one embodiment, the base substrate BL may be omitted.

The display device DD according to an embodiment may further include a charging layer (not shown). The charging layer (not shown) may be disposed between the display element layer (DP-ED) and the base substrate (BL). The filled layer (not shown) may be an organic material layer. The filling layer (not shown) may include at least one of acrylic resin, silicone resin, and 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) includes a pixel defining layer (PDL), light emitting elements (ED-1, ED-2, ED-3) disposed between the pixel defining layers (PDL), and light emitting elements (ED- 1, ED-2, ED-3) and may include an encapsulation layer (TFE) disposed on the layer.

The base layer BS may be a member that provides a base surface on which the display element layer DP-ED is disposed. The base layer (BS) may be a glass substrate, a metal substrate, or a plastic substrate. However, the embodiment is not limited to this, and the base layer BS may be an inorganic layer, an organic layer, or a composite material layer.

In one embodiment, the circuit layer DP-CL is disposed on the base layer BS, and the circuit layer DP-CL may include a plurality of transistors (not shown). Transistors (not shown) may each include a control electrode, an input electrode, and an output electrode. For example, the circuit layer (DP-CL) may include a switching transistor and a driving transistor for driving the light emitting elements (ED-1, ED-2, and ED-3) of the display element layer (DP-ED). You can.

Each of the light emitting devices ED-1, ED-2, and ED-3 may have the structure of the light emitting device ED of an embodiment according to FIGS. 3 to 6, which will be described later. Each of the light emitting elements (ED-1, ED-2, and ED-3) includes a first electrode (EL1), a hole transport region (HTR), an emission layer (EML-R, EML-G, EML-B), and an electron transport region. (ETR), and a second electrode (EL2).

In Figure 2, the light emitting layers (EML-R, EML-G, EML-B) of the light emitting elements (ED-1, ED-2, and ED-3) are arranged within the opening (OH) defined in the pixel defining layer (PDL). In this example, the hole transport region (HTR), the electron transport region (ETR), and the second electrode EL2 are provided as common layers throughout the light emitting elements ED-1, ED-2, and ED-3. did. However, the embodiment is not limited to this, and unlike what is shown in FIG. 2, in one embodiment, the hole transport region (HTR) and the electron transport region (ETR) are located inside the opening (OH) defined in the pixel defining layer (PDL). It may be patterned and provided. For example, in one embodiment, the hole transport region (HTR), the emission layer (EML-R, EML-G, EML-B), and the electron transport region of the light emitting devices (ED-1, ED-2, and ED-3) (ETR), etc. may be provided by being patterned using an inkjet printing method.

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

The inorganic encapsulation film protects the display device layer (DP-ED) from moisture/oxygen, and the organic encapsulation film protects the display device layer (DP-ED) from foreign substances such as dust particles. The encapsulating inorganic film may include silicon nitride, silicon oxy nitride, silicon oxide, titanium oxide, or aluminum oxide, but is not particularly limited thereto. The encapsulation organic film may contain an acrylic compound, an epoxy compound, or the like. The encapsulating organic film may contain a photopolymerizable organic material 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 FIGS. 1 and 2 , the display device DD may include a non-emission area NPXA and emission areas PXA-R, PXA-G, and PXA-B. Each of the light emitting areas (PXA-R, PXA-G, and PXA-B) may be an area where light generated by each of the light emitting elements (ED-1, ED-2, and ED-3) is emitted. The light emitting areas (PXA-R, PXA-G, and PXA-B) may be spaced apart from each other on a plane.

Each of the light emitting areas (PXA-R, PXA-G, and PXA-B) may be an area divided by a pixel defining layer (PDL). The non-emission areas NPXA are areas between neighboring light emitting areas PXA-R, PXA-G, and PXA-B and may correspond to the pixel defining layer PDL. Meanwhile, in this specification, each of the light emitting areas (PXA-R, PXA-G, and PXA-B) may correspond to a pixel (Pixel). The pixel defining layer (PDL) may distinguish the light emitting elements (ED-1, ED-2, and ED-3). The light emitting layers (EML-R, EML-G, EML-B) of the light emitting elements (ED-1, ED-2, ED-3) are placed in the opening (OH) defined in the pixel defining layer (PDL) to be distinguished. You can.

The light emitting areas (PXA-R, PXA-G, and 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, and ED-3). The display device DD of one embodiment shown in FIGS. 1 and 2 includes three light-emitting areas (PXA-R, PXA-G, and PXA-B) that emit red light, green light, and blue light. . For example, the display device DD of one embodiment may include a red light-emitting area (PXA-R), a green light-emitting area (PXA-G), and a blue light-emitting area (PXA-B) that are distinct from each other.

In the display device DD according to an embodiment, the plurality of light emitting elements ED-1, ED-2, and ED-3 may emit light in different wavelength ranges. For example, in one embodiment, the display device DD includes a first light emitting device ED-1 that emits red light, a second light emitting device ED-2 that emits green light, and a third light emitting device that emits blue light. It may include an element (ED-3). That is, the red light-emitting area (PXA-R), green light-emitting area (PXA-G), and blue light-emitting area (PXA-B) of the display device (DD) are the first light-emitting element (ED-1) and the second light-emitting element (ED-1), respectively. It can correspond to the element ED-2 and the third light emitting element ED-3.

However, the embodiment is not limited to this, and the first to third light emitting elements ED-1, ED-2, and ED-3 emit light in the same wavelength range, or at least one emits light in a different wavelength range. It may be emitting light. For example, the first to third light emitting elements ED-1, ED-2, and ED-3 may all emit blue light.

The light emitting areas (PXA-R, PXA-G, and PXA-B) in the display device (DD) according to one embodiment may be arranged in a stripe shape. Referring to FIG. 1, a plurality of red light-emitting areas (PXA-R), a plurality of green light-emitting areas (PXA-G), and a plurality of blue light-emitting areas (PXA-B) each extend along the second direction DR2. ) may be aligned. Additionally, the red light emitting area (PXA-R), the green light emitting area (PXA-G), and the blue light emitting area (PXA-B) may be alternately arranged along the first direction axis DR1.

1 and 2 show that the areas of the light emitting areas (PXA-R, PXA-G, and PXA-B) are all similar, but the embodiment is not limited thereto and the areas of the light emitting areas (PXA-R, PXA-G, and PXA) are similar. The area of -B) may be different depending on the wavelength range of the emitted light. Meanwhile, the area of the light emitting areas (PXA-R, PXA-G, and PXA-B) may refer to the area when viewed on the plane defined by the first direction axis (DR1) and the second direction axis (DR2). .

Meanwhile, the arrangement form of the light-emitting areas (PXA-R, PXA-G, and PXA-B) is not limited to that shown in Figure 1, and includes a red light-emitting area (PXA-R), a green light-emitting area (PXA-G), and the order in which the blue light emitting area (PXA-B) is arranged may be provided in various combinations depending on the display quality characteristics required for the display device (DD). For example, the arrangement of the light emitting areas (PXA-R, PXA-G, and PXA-B) may be a PENTILE ^™ arrangement or a Diamond Pixel™ arrangement.

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

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

The light emitting device (ED) may include a hole transport region (HTR), an emission layer (EML), an electron transport region (ETR), etc., sequentially stacked as at least one functional layer. Referring to FIG. 3, the light emitting device (ED) of one embodiment includes a first electrode (EL1), a hole transport region (HTR), an emission layer (EML), an electron transport region (ETR), and a second electrode ( EL2) may be included.

4 shows that, compared to FIG. 3, the hole transport region (HTR) includes a hole injection layer (HIL) and a hole transport layer (HTL), and the electron transport region (ETR) includes an electron injection layer (EIL) and an electron transport layer (ETL). ) shows a cross-sectional view of the light emitting device (ED) of an embodiment including. In addition, compared to FIG. 3, FIG. 5 shows that the hole transport region (HTR) includes a hole injection layer (HIL), a hole transport layer (HTL), and an electron blocking layer (EBL), and the electron transport region (ETR) includes an electron injection layer (EBL). It shows a cross-sectional view of a light emitting device (ED) of one embodiment including a layer (EIL), an electron transport layer (ETL), and a hole blocking layer (HBL). FIG. 6 shows a cross-sectional view of the light emitting device ED of one embodiment including the capping layer CPL disposed on the second electrode EL2 compared to FIG. 4 .

The light emitting device (ED) of one embodiment may include the amine compound of one embodiment described later in the hole transport region (HTR). In the light emitting device (ED) of one embodiment, the amine compound of one embodiment may be included in at least one of the hole injection layer (HIL), the hole transport layer (HTL), and the electron blocking layer (EBL) of the hole transport region (HTR). . For example, in the light emitting device ED of one embodiment, the hole transport layer (HTL) may include an amine compound of one embodiment.

In the light emitting device ED according to one embodiment, the first electrode EL1 has conductivity. The first electrode EL1 may be formed of a metal material, metal alloy, or conductive compound. The first electrode EL1 may be an anode or a cathode. However, the embodiment is not limited to this. Additionally, 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 is selected from Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF, Mo, Ti, W, In, Sn, and Zn. It may contain at least one, two or more compounds selected from these, a mixture of two or more types selected from these, or oxides thereof.

When the first electrode EL1 is a transparent electrode, the first electrode EL1 is made of a transparent metal oxide, for example, indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), or indium ITZO. tin zinc oxide), etc. When the first electrode EL1 is a transflective electrode or a reflective electrode, the first electrode EL1 is made of Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, It may include LiF/Ca (stacked structure of LiF and Ca), LiF/Al (stacked structure of LiF and Al), Mo, Ti, W, or a compound or mixture thereof (e.g., a mixture of Ag and Mg). there is. Alternatively, the first electrode EL1 may be a transparent film formed of a reflective film or semi-transmissive film made of the above materials and a transparent film made of ITO (indium tin oxide), IZO (indium zinc oxide), ZnO (zinc oxide), ITZO (indium tin zinc oxide), etc. It may have a multiple layer structure including a conductive film. For example, the first electrode EL1 may have a three-layer structure of ITO/Ag/ITO, but is not limited thereto. In addition, the embodiment is not limited to this, 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, or oxides of the above-described metal materials. there is. The thickness of the first electrode EL1 may be about 700Å to about 10000Å. For example, the thickness of the first electrode EL1 may be about 1000Å to about 3000Å.

The hole transport region (HTR) is provided on the first electrode (EL1). The hole transport region (HTR) may have a single layer made of a single material, a single layer made of a plurality of different materials, or a multilayer structure having a plurality of layers made of a plurality of different materials.

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). Additionally, although not shown, the hole transport region (HTR) may include a plurality of stacked hole transport layers.

Additionally, differently from this, the hole transport region (HTR) may have a single-layer structure of a hole injection layer (HIL) or a hole transport layer (HTL), or may have a single-layer structure composed of a hole injection material and a hole transport material. In one embodiment, the hole transport region (HTR) has a single-layer structure made of a plurality of different materials, or a hole injection layer (HIL)/hole transport layer (HTL) sequentially stacked from the first electrode (EL1), It may have 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). , the examples are not limited thereto.

The thickness of the hole transport region (HTR) may be, for example, about 50 Å to about 15,000 Å. The hole transport region (HTR) is created using various methods such as vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB), inkjet printing, laser printing, and laser induced thermal imaging (LITI). It can be formed using

The light emitting device (ED) of one embodiment may include the amine compound of one embodiment in the hole transport region (HTR). In the light emitting device ED of one 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 hole transport layer (HTL) may include an amine compound of one embodiment.

In one embodiment, the amine compound may be represented by Formula 1 below.

[Formula 1]

In Formula 1, L ₁ and L ₂ may each independently be a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group. For example, L ₁ is a substituted or unsubstituted phenylene group, a substituted or unsubstituted divalent biphenyl group, a substituted or unsubstituted divalent terphenyl group, a substituted or unsubstituted divalent quarterphenyl group, or a substituted or unsubstituted divalent quarterphenyl group. A divalent fluorene group, a substituted or unsubstituted dibenzofuran group, a substituted or unsubstituted dibenzothiophene group, a substituted or unsubstituted dibenzosilol group, or a substituted or unsubstituted dibenzothiophene group. It may be a naphthyl group.

In one embodiment, L ₁ may be represented by at least one of the substituents of the substituent group S below.

[Substituent group S]

In the substituent group S, " " means the position connected to the nitrogen atom in Formula 1, " " means the position connected to the nitrogen atom of carbazole in Formula 1 above.

In the substituent group S, R _S1 to R _S49 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted silyl group, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted Alternatively, it may be an unsubstituted heteroaryl group having 2 to 30 ring carbon atoms. For example, R _S1 to R _S49 may each independently be a hydrogen atom or a deuterium atom. However, each embodiment of R _S1 to R _S49 is not limited thereto.

y1 to y4, and y6 to y42 may each independently be an integer of 0 to 4, and y5 and y43 to y49 may each independently be an integer of 0 to 6. For example, y1 to y49 may each be 0. However, each example y1 to y49 is not limited thereto.

Meanwhile, the case where y1 is 0 may be the same as the case where y1 is 4 and R _S1 is a hydrogen atom. This can be equally applied when each of y2 to y4 and y6 to y42 is 0.

Meanwhile, the case where y5 is 0 may be the same as the case where y5 is 6 and R _S5 is a hydrogen atom. This can be equally applied when each of y43 to y49 is 0.

However, L ₁ is not limited to the substituent group S above.

For example, L ₂ is a substituted or unsubstituted phenylene group, a substituted or unsubstituted divalent biphenyl group, a substituted or unsubstituted divalent naphthyl group, a substituted or unsubstituted divalent phenanthryl group, or a substituted or unsubstituted divalent phenanthryl group. It may be a ringed divalent triphenylenyl group.

Specifically, L ₂ may be an unsubstituted phenyl group, unsubstituted biphenyl group, unsubstituted naphthyl group, unsubstituted phenanthryl group, or unsubstituted triphenylenyl group. However, the examples are not limited thereto.

x is 1 or 2. When x is 1, the carbazole group in Formula 1 may be connected to the nitrogen atom of the amine through one L ₁ linker. When x is 2, the carbazole group in Formula 1 may be connected to the nitrogen atom of the amine through two L ₁ linkers directly connected to each other.

Ar may be a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. For example, Ar is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted quaterphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted It may be a phenanthryl group, a substituted or unsubstituted fluorene group, a substituted or unsubstituted dibenzofuran group, or a substituted or unsubstituted dibenzothiophene group. However, the embodiment of Ar is not limited to this.

R ₁ and R ₂ are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted silyl group, a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming group. It may be a heteroaryl group having 2 to 30 carbon atoms, or a ring may be formed by combining with adjacent groups. For example, R ₁ and R ₂ are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted methyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted dibenzofuran group, or a substituted or unsubstituted dibenzofuran group. It may be a benzothiophene group, or it may form a ring by combining with adjacent groups.

R ₃ is a hydrogen atom, a heavy hydrogen atom, a halogen atom, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkenyl group with 2 to 30 carbon atoms, a substituted or unsubstituted aryl group with 6 to 30 carbon atoms to form a ring, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, or a ring can be formed by combining with adjacent groups, except for cases where R ₃ is an aryl group substituted with an amine group. For example, R ₃ is a hydrogen atom, a deuterium atom, a substituted or unsubstituted pyridine group, a substituted or unsubstituted allyl group, a substituted or unsubstituted tetrazole group, a substituted or unsubstituted dibenzofuran group, or a substituted or It is an unsubstituted triazine group or can form a ring by combining with adjacent groups, excluding cases where an amine group is substituted.

R ₄ and R ₅ each independently represent a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted silyl group, a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming group. It is a heteroaryl group having 2 to 30 carbon atoms. That is, R ₄ and R ₅ may not form a ring by combining with adjacent groups. For example, R ₄ and R ₅ may each independently be a hydrogen atom or a deuterium atom. Meanwhile, in the present invention, at least one R ₄ is a hydrogen atom.

a and b are each independently integers from 0 to 4. For example, a and b may each independently be 0 or 1. The case where a is 0 may be the same as the case where a is 4 and R ₁ is a hydrogen atom. The case where b is 0 may be the same as the case where b is 4 and R ₂ is a hydrogen atom.

c is an integer between 0 and 5. For example, c can be 0 to 2. The case where c is 0 may be the same as the case where c is 5 and R ₃ is a hydrogen atom. When c is 2, two R ₃ can be combined with each other to form a ring.

d is an integer between 0 and 3. For example, d may be 0. The case where d is 0 may be the same as the case where d is 3 and R ₄ is a hydrogen atom.

e is an integer between 0 and 3. For example, e may be 0. The case where e is 0 may be the same as the case where e is 3 and R ₅ is a hydrogen atom.

Meanwhile, when a is an integer of 2 or more, a plurality of R ₁ may be identical to each other, or at least one R ₁ may be different from the remaining R ₁ . The same explanation can be applied even when b to e are each an integer of 2 or more.

The amine compound of the present invention may include a substituent of a carbazole skeleton bonded to the nitrogen atom of the amine, a substituent of a naphthalene skeleton substituted with a phenyl group, and a substituent of an aryl group or heteroaryl group. As a result, the amine compound of one embodiment exhibits high molecular stability and excellent hole transport properties, and can contribute to improving the lifespan of a light emitting device when used as a hole transport material for a light emitting device.

In one embodiment, the amine compound may be a mono amine compound.

In one embodiment, the amine compound represented by Formula 1 may be represented by any one of the following Formulas 1-1 to 1-3.

[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

Formulas 1-1 to 1-3 specify R ₃ in Formula 1.

In Formulas 1-1 to 1-3, R ₃₁ , R ₃₂ , and R ₃₃ are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted silyl group, or a substituted or unsubstituted carbon number of 2 or more. It may be an alkenyl group of 30 or less, a substituted or unsubstituted aryl group of 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring carbon atoms. However, cases where R ₃₁ , R ₃₂ , and R ₃₃ are each an aryl group substituted with an amine group are excluded. For example, R ₃₁ is a hydrogen atom, a deuterium atom, a substituted or unsubstituted allyl group, a substituted or unsubstituted pyridine group, a substituted or unsubstituted dibenzofuran group, a substituted or unsubstituted tetrazole group, or a substituted or It may be an unsubstituted triazine group.

For example, R ₃₂ and R ₃₃ may each independently be a hydrogen atom, a deuterium atom, or a substituted or unsubstituted allyl group.

c1 is an integer between 0 and 5. For example, c1 can be 0 or 1. The case where c1 is 0 may be the same as the case where c1 is 5 and R ₃₁ is a hydrogen atom.

c2 and c3 are each integers from 0 to 7. For example, c2 and c3 may each be 0. The case where c2 is 0 may be the same as the case where c2 is 7 and R ₃₂ is a hydrogen atom. The case where c3 is 0 may be the same as the case where c3 is 7 and R ₃₃ is a hydrogen atom.

In Formulas 1-1 to 1-3, Ar, R ₁ , R ₂ , R ₄ , R ₅ , L ₁ , L ₂ , a, b, d, e, and x are the same as defined in Formula 1.

Referring to Chemical Formulas 1-1 to 1-3, the amine compound of one embodiment may have a feature in which a naphthyl group substituted with a phenyl group or a naphthyl group substituted with a naphthyl group is connected to the nitrogen atom of the amine through a linker. Accordingly, the area around the nitrogen atom of the amine compound is sterically protected, and molecular stability during charge transport can be improved. In addition, the naphthyl group substituted with the phenyl group or the naphthyl group substituted with the naphthyl group interacts with the linker to further improve the charge transport ability of the amine compound, and the hole transport layer containing the amine compound of the present invention provides holes in the light emitting layer. Can be transported efficiently.

In one embodiment, the amine compound represented by Formula 1 may be represented by any one of the following Formulas 2-1 to 2-6.

[Formula 2-1]

[Formula 2-2]

[Formula 2-3]

[Formula 2-4]

[Formula 2-5]

[Formula 2-6]

Formulas 2-1 to 2-6 are specific embodiments of L ₂ in Formula 1.

In Formulas 2-1 to 2-6, R ₆ to R ₁₈ are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted silyl group, or a substituted or unsubstituted ring-forming carbon number of 6 to 30. It may be an aryl group, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms. For example, R ₆ to R ₁₈ may each independently be a hydrogen atom or a deuterium atom.

f, g, h, j, and q are each independently integers from 0 to 4. For example, f, g, h, j, and q may each be 0. The case where f is 0 may be the same as the case where f is 4 and R ₆ is a hydrogen atom. The same explanation can be applied even when g, h, j, and q are each 0.

i, and n are each independently integers from 0 to 2. For example, i, and n can each be 0. The case where i is 0 may be the same as the case where i is 2 and R ₉ is a hydrogen atom. The same explanation can be applied even when n is 0.

k, l, m, o, p, and r are each independently integers from 0 to 3. For example, k, l, m, o, p, and r can each be 0. The case where k is 0 may be the same as the case where k is 3 and R ₁₁ is a hydrogen atom. The same explanation can be applied even when l, m, o, p, and r are 0.

In Formulas 2-1 to 2-6, Ar, R ₁ to R ₅ , L ₁ , a to e, and x are the same as defined in Formula 1.

In one embodiment, the amine compound represented by Formula 1 may be represented by Formula 3-1 or Formula 3-2 below.

[Formula 3-1]

[Formula 3-2]

Formula 3-1 and Formula 3-2 _specify (L ₁ ) Chemical Formula 3-1 illustrates the case where x is 1 and L ₁ is L ₁₁ in Chemical Formula 1. Formula 3-2 shows the case where x is 2 and two L ₁ are L ₁₂ and L ₁₃ .

In Formula 3-1 and Formula 3-2, L ₁₁ to L ₁₃ are each independently a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted arylene group having 2 to 30 ring carbon atoms. It may be a heteroarylene group. For example, L ₁₁ is a substituted or unsubstituted phenylene group, a substituted or unsubstituted divalent biphenyl group, a substituted or unsubstituted divalent terphenyl group, a substituted or unsubstituted divalent quarterphenyl group, or a substituted or unsubstituted divalent quarterphenyl group. A divalent fluorene group, a substituted or unsubstituted dibenzofuran group, a substituted or unsubstituted dibenzothiophene group, a substituted or unsubstituted dibenzosilol group, or a substituted or unsubstituted dibenzothiophene group. It may be a naphthyl group. For example, L ₁₂ may be a substituted or unsubstituted phenylene group and L ₁₃ may be a substituted or unsubstituted divalent naphthyl group. However, examples L ₁₁ to L ₁₃ are not limited thereto.

The amine compound of an example represented by Formula 1 may be represented by one of the compounds of compound group 1 below. The hole transport region (HTR) of the light emitting device (ED) of one embodiment may include at least one of the amine compounds disclosed in compound group 1 below. For example, the hole transport layer (HTL) of the light emitting device (ED) may include at least one of the amine compounds disclosed in compound group 1 below. In compound group 1 below, D is a deuterium atom.

[Compound Group 1]

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

The first substituent may be a substituent having a carbazole skeleton. For example, the first substituent may be one in which the nitrogen atom at position 9 of carbazole is bonded to the nitrogen atom of amine through a linker. The amine compound of one embodiment may exhibit high hole transport properties by including a first substituent.

The second substituent may be a substituent having a naphthalene skeleton in which a substituted or unsubstituted phenyl group is substituted. For example, the second substituent may be one in which the naphthalene skeleton is bonded to the nitrogen atom of the amine through a linker.

The third substituent may be an aryl group or a heteroaryl group. For example, the third substituent may be an aryl group or hetero aryl group directly bonded to the nitrogen atom of the amine.

The amine compound of one embodiment may have improved electron resistance, excellent hole transport properties, and high stability by including the first to third substituents. In addition, the first to third substituents have excellent thermal stability and can suppress material deterioration that occurs during the process of depositing the amine compound of one embodiment. Accordingly, the lifespan of the light emitting device of one embodiment including the amine compound may be improved.

In the light emitting device (ED) of one embodiment, the hole transport region (HTR) may further include a compound represented by the following formula H-1.

[Formula H-1]

In the above formula H-1, L ₁ and L ₂ are each independently a direct linkage, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted arylene group having 2 or more ring carbon atoms. It may be a heteroarylene group of 30 or less. a and b may each independently be an integer between 0 and 10. Meanwhile, when a or b is an integer of 2 or more, a plurality of L ₁ and L ₂ are each independently a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted arylene group having 2 to 30 ring carbon atoms. It may be a heteroarylene group.

In Formula H-1, Ar _a and Ar _b may each independently be a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms. . Additionally, in Formula H-1, Ar _c may be a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms.

The compound represented by Formula H-1 may be a monoamine compound. Alternatively, the compound represented by the formula H-1 may be a diamine compound in which at least one of Ar _a to Ar _c contains an amine group as a substituent. In addition, the compound represented by the formula H-1 is a carbazole-based compound containing a carbazole group substituted or unsubstituted in at least one of Ar _a and Ar _b , or a carbazole-based compound containing a substituted or unsubstituted carbazole group in at least one of Ar _a and Ar _b . It may be a fluorene-based compound containing a fluorene group.

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

[Compound group H]

In addition, the hole transport region (HTR) may further include a known hole transport material.

For example, the hole transport region (HTR) is a phthalocyanine compound such as copper phthalocyanine, DNTPD(N ¹ ,N ^1' -([1,1'-biphenyl]-4,4'-diyl )bis(N ¹ -phenyl-N ⁴ ,N ⁴ -di-m-tolylbenzene-1,4-diamine)), m-MTDATA(4,4',4"-[tris(3-methylphenyl)phenylamino] triphenylamine ), TDATA(4,4'4"-Tris(N,N-diphenylamino)triphenylamine), 1-TNATA(4,4',4"-tris[N-(1-naphthyl)-N-phenylamino]-triphenylamine) ), 2-TNATA(4,4',4"-tris[N(2-naphthyl)-N-phenylamino]-triphenylamine), PEDOT/PSS(Poly(3,4-ethylenedioxythiophene)/Poly(4-styrenesulfonate) ), PANI/DBSA (Polyaniline/Dodecylbenzenesulfonic acid), PANI/CSA (Polyaniline/Camphor sulfonicacid), PANI/PSS (Polyaniline/Poly(4-styrenesulfonate)), NPB (or NPD) (N,N'-di(naphthalene) -l-yl)-N,N'-diphenyl-benzidine), polyether ketone containing triphenylamine (TPAPEK), 4-Isopropyl-4'-methyldiphenyliodonium [Tetrakis(pentafluorophenyl)borate], HATCN (dipyrazino[2 ,3-f: 2',3'-h] quinoxaline-2,3,6,7,10,11-hexacarbonitrile), etc.

The hole transport region (HTR) is composed of carbazole-based derivatives such as N-phenylcarbazole and polyvinylcarbazole, fluorene-based derivatives, TCTA (4,4',4"-tris(N-carbazolyl)triphenylamine), etc. Same triphenylamine derivatives, or TPD (N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine), NPB(N, N'-di(naphthalene-l-yl)-N,N'-diphenyl-benzidine), TAPC(4,4′-Cyclohexylidene bis[N,N-bis(4-methylphenyl)benzenamine]), HMTPD(4, It may include 4'-Bis[N,N'-(3-tolyl)amino]-3,3'-dimethylbiphenyl), mCP(1,3-Bis(N-carbazolyl)benzene), etc.

In addition, the hole transport region (HTR) is CzSi (9-(4-tert-Butylphenyl)-3,6-bis(triphenylsilyl)-9H-carbazole), CCP (9-phenyl-9H-3,9'-bicarbazole) , or mDCP (1,3-bis(1,8-dimethyl-9H-carbazol-9-yl)benzene).

The hole transport region (HTR) may include the compounds of the hole transport region described above in at least one of the hole injection layer (HIL), the hole transport layer (HTL), and the electron blocking layer (EBL).

The thickness of the hole transport region (HTR) may be about 100 Å to about 10000 Å, for example, about 100 Å to about 5000 Å. When the hole transport region (HTR) includes a hole injection layer (HIL), the thickness of the hole injection layer (HIL) may be, for example, about 30 Å to about 1000 Å.

When the hole transport region (HTR) includes a hole transport layer (HTL), the thickness of the hole transport layer (HTL) may be about 30 Å to about 1000 Å. For example, when the hole transport region (HTR) includes an electron blocking layer (EBL), the thickness of the electron blocking layer (EBL) may be about 10 Å to about 1000 Å. When the thickness of the hole transport region (HTR), hole injection layer (HIL), hole transport layer (HTL), and electron blocking layer (EBL) satisfies the above-mentioned range, the hole transport characteristics are satisfactory without a substantial increase in driving voltage. can be obtained.

In addition to the previously mentioned materials, the hole transport region (HTR) may further include a charge generating material to improve conductivity. The charge generating material may be uniformly or non-uniformly dispersed within the hole transport region (HTR). The charge generating material may be, for example, a p-dopant. The p-dopant may include at least one of a halogenated metal compound, a quinone derivative, a metal oxide, and a cyano group-containing compound, but is not limited thereto. For example, p-dopants include halogenated metal compounds such as CuI and RbI, quinone derivatives such as TCNQ (Tetracyanoquinodimethane) and F4-TCNQ (2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane). , metal oxides such as tungsten oxide and molybdenum oxide, HATCN (dipyrazino[2,3-f: 2',3'-h] quinoxaline-2,3,6,7,10,11-hexacarbonitrile) and NDP9(4- Cyano group-containing compounds such as [[2,3-bis[cyano-(4-cyano-2,3,5,6-tetrafluorophenyl)methylidene]cyclopropylidene]-cyanomethyl]-2,3,5,6-tetrafluorobenzonitrile), etc. However, the examples are not limited thereto.

As described above, the hole transport region (HTR) may further 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). A buffer layer (not shown) may increase light emission efficiency by compensating for a resonance distance depending on the wavelength of light emitted from the light emitting layer (EML). The material included in the buffer layer (not shown) may be a material that can be included in the hole transport region (HTR).

The light emitting layer (EML) is provided on the hole transport region (HTR). For example, the light emitting layer (EML) may have a thickness of about 100 Å to about 1000 Å or about 100 Å to about 300 Å. The light emitting layer (EML) may have a single layer made of a single material, a single layer made of a plurality of different materials, or a multi-layer structure having a plurality of layers made of a plurality of different materials.

In the light emitting device ED of one embodiment, the light emitting layer EML may emit blue light. The light emitting device (ED) of one embodiment includes the amine compound of the above-described embodiment in the hole transport region (HTR) and may exhibit high efficiency and long lifespan characteristics in the blue light emitting region. However, the embodiment is not limited to this.

In the light emitting device (ED) of one embodiment, the light emitting layer (EML) may include an anthracene derivative, a pyrene derivative, a fluoranthene derivative, a chrysene derivative, a dihydrobenzanthracene derivative, or a triphenylene derivative. Specifically, the light emitting layer (EML) may include an anthracene derivative or a pyrene derivative.

In the light emitting device (ED) of an embodiment shown in FIGS. 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 formula E-1. . A compound represented by the following formula E-1 can be used as a fluorescent host material.

[Formula E-1]

In Formula E-1, R ₃₁ to R ₄₀ are each independently hydrogen atom, deuterium atom, halogen atom, substituted or unsubstituted silyl group, substituted or unsubstituted thio group, substituted or unsubstituted oxy group, substituted or an unsubstituted alkyl group with 1 to 10 carbon atoms, a substituted or unsubstituted alkenyl group with 2 to 10 carbon atoms, a substituted or unsubstituted ring-forming aryl group with 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming group. It may be a heteroaryl group having from 2 to 30 carbon atoms, or it may form a ring by combining with an adjacent group. Meanwhile, R ₃₁ to R ₄₀ may be combined with adjacent groups to form a saturated hydrocarbon ring, an unsaturated hydrocarbon ring, a saturated hetero ring, or an unsaturated hetero ring.

In Formula E-1, c and d may each independently be an integer between 0 and 5.

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

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

[Formula E-2a]

In Formula E-2a, a is an integer from 0 to 10, and L _a is a direct bond, a substituted or unsubstituted arylene group with 6 to 30 carbon atoms to form a ring, or a substituted or unsubstituted arylene group with 2 to 30 carbon atoms to form a ring. It may be a heteroarylene group. Meanwhile, when a is an integer of 2 or more, the plurality of L _a are each independently a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms. You can.

Additionally, in Formula E-2a, A ₁ to A ₅ may each independently be N or CR _i . R _a to R _i are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted amine group, a substituted or unsubstituted thio group, a substituted or unsubstituted oxy group, and a substituted or unsubstituted carbon number of 1 to 20. an alkyl group, a substituted or unsubstituted alkenyl group with 2 to 20 carbon atoms, a substituted or unsubstituted aryl group with 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group with 2 to 30 ring carbon atoms. Alternatively, it may form a ring by combining with adjacent groups. R _a to R _i may combine with adjacent groups to form a hydrocarbon ring or a hetero ring containing N, O, S, etc. as ring forming atoms.

Meanwhile, in Formula E-2a, two or three of A ₁ to A ₅ may be N and the remainder may be CR _i .

[Formula E-2b]

In Formula E-2b, Cbz1 and Cbz2 may each independently be an unsubstituted carbazole group or a carbazole group substituted with an aryl group having 6 to 30 ring carbon atoms. L _b may be a direct bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms. b is an integer of 0 to 10, and when b is an integer of 2 or more, the plurality of L _b are each independently a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted ring carbon number of 2 It may be a heteroarylene group of more than 30 or less.

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

[Compound group E-2]

The light emitting layer (EML) may further include a general material known in the art as a host material. For example, the emitting layer (EML) uses BCPDS (bis (4-(9H-carbazol-9-yl) phenyl) diphenylsilane), POPCPA ((4-(1-(4-(diphenylamino) phenyl) cyclohexyl) as host materials. phenyl) diphenyl-phosphine oxide), DPEPO (Bis[2-(diphenylphosphino)phenyl] ether oxide), CBP(4,4'-bis(N-carbazolyl)-1,1'-biphenyl), mCP(1,3 -Bis(carbazol-9-yl)benzene), PPF (2,8-Bis(diphenylphosphoryl)dibenzo[b,d]furan), TCTA(4,4',4''-Tris(carbazol-9-yl) -triphenylamine) and TPBi (1,3,5-tris(1-phenyl-1H-benzo[d]imidazole-2-yl)benzene). However, it is not limited thereto, and for example, Alq ₃ (tris(8-hydroxyquinolino)aluminum), ADN(9,10-di(naphthalene-2-yl)anthracene), TBADN(2-tert-butyl- 9,10-di(naphth-2-yl)anthracene), DSA(distyrylarylene), CDBP(4,4′-bis(9-carbazolyl)-2,2′-dimethyl-biphenyl), MADN(2-Methyl- Host 9,10-bis(naphthalen-2-yl)anthracene), CP1(Hexaphenyl cyclotriphosphazene), UGH2 (1,4-Bis(triphenylsilyl)benzene), DPSiO ₃ (Hexaphenylcyclotrisiloxane), DPSiO ₄ (Octaphenylcyclotetra siloxane), etc. It can be used as a material.

The light emitting layer (EML) may include a compound represented by the following formula M-a or formula M-b. A compound represented by the following formula M-a or formula M-b can be used as a phosphorescent dopant material. Additionally, in one embodiment, a compound represented by Formula M-a or Formula M-b may be used as an auxiliary dopant material.

[Formula M-a]

In the formula Ma, Y ₁ to Y ₄ and Z ₁ to Z ₄ are each independently CR ₁ or N, and R ₁ to R ₄ are each independently a hydrogen atom, a deuterium atom, or a substituted or unsubstituted amine group. , a substituted or unsubstituted thio group, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group with 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group with 2 to 20 carbon atoms, a substituted or unsubstituted ring It may be an aryl group with 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group with 2 to 30 carbon atoms, or a ring formed by combining with adjacent groups. In the formula Ma, m is 0 or 1 and n is 2 or 3. In the chemical formula Ma, when m is 0, n is 3, and when m is 1, n is 2.

A compound represented by formula M-a can be used as a phosphorescent dopant.

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

Compound M-a1 and Compound M-a2 can be used as red dopant materials, and Compounds M-a3 to Compound M-a7 can be used as green dopant materials.

[Formula M-b]

In the formula Mb, Q ₁ to Q ₄ are each independently C or N, and C 1 to C 4 are each independently a substituted or unsubstituted hydrocarbon ring having 5 to 30 carbon atoms, or a substituted or unsubstituted hydrocarbon ring having 5 to 30 ring carbon atoms. It is a heterocycle of 2 or more and 30 or less. L ₂₁ to L ₂₄ are each independently directly bonded, , , , , , , a substituted or unsubstituted divalent alkyl group with 1 to 20 carbon atoms, a substituted or unsubstituted arylene group with 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group with 2 to 30 ring carbon atoms. , e1 to e4 are each independently 0 or 1. R ₃₁ to R ₃₉ each independently represent a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted ring-forming carbon number. It is an aryl group with 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group with 2 to 30 carbon atoms, or a ring is formed by combining with adjacent groups, and d1 to d4 are each independently 0 to 4. is the integer of

The compound represented by formula M-b can be used as a blue phosphorescent dopant or a green phosphorescent dopant. Additionally, in one embodiment, the compound represented by the formula M-b may be further included in the light emitting layer (EML) as an auxiliary dopant.

The compound represented by the formula M-b may be represented by any one of the following compounds M-b-1 to compounds M-b-11. However, the following compounds are illustrative, and the compound represented by the formula M-b is not limited to the following compounds M-b-1 to M-b-11.

In the above compounds, R, R ₃₈ , and R ₃₉ are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, It may be a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms.

The light emitting layer (EML) may further include a compound represented by any of the following formulas F-a to formula F-c. Compounds represented by the following formulas F-a to F-c can be used as fluorescent dopant materials.

[Formula F-a]

In the formula Fa, two selected from R _a to R _j are each independently It may be replaced with . Between R _a and R _j The remainders that are not substituted are each independently hydrogen atom, deuterium atom, halogen atom, cyano group, substituted or unsubstituted amine group, substituted or unsubstituted alkyl group with 1 to 20 carbon atoms, and substituted or unsubstituted ring-forming carbon number. It may be an aryl group with 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group with 2 to 30 ring carbon atoms. Ar ₁ and Ar ₂ may each independently be a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms. For example, at least one of Ar ₁ and Ar ₂ may be a heteroaryl group containing O or S as a ring-forming atom.

[Formula F-b]

In the above formula Fb, R _a and R _b are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or It may be an unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, or a ring formed by combining with adjacent groups.

In the formula Fb, Ar ₁ to Ar ₄ may each independently be a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms. .

In the formula F-b, U and V may each independently be a substituted or unsubstituted hydrocarbon ring having 5 to 30 ring carbon atoms, or a substituted or unsubstituted heterocycle having 2 to 30 ring carbon atoms.

In Formula F-b, the number of rings represented by U and V may each independently be 0 or 1. For example, in the formula F-b, if the number of U or V is 1, one ring forms a condensed ring at the part indicated by U or V, and if the number of U or V is 0, then U or V is indicated. A ring means non-existence. Specifically, when the number of U is 0 and the number of V is 1, or when the number of U is 1 and the number of V is 0, the condensed ring having a fluorene core of the formula F-b may be a four-ring ring compound. Additionally, when the numbers of U and V are both 0, the condensed ring of formula F-b may be a tricyclic ring compound. Additionally, when the numbers of U and V are both 1, the condensed ring having a fluorene core of formula F-b may be a 5-ring ring compound.

[Formula F-c]

In the formula Fc, A ₁ and A ₂ are each independently O, S, Se, or NR _m , and R _m is a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted. It may be a ring-forming aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms. R ₁ to R ₁₁ are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted amine group, a substituted or unsubstituted boryl group, a substituted or unsubstituted oxy group, or a substituted or unsubstituted group. a thio group, a substituted or unsubstituted alkyl group with 1 to 20 carbon atoms, a substituted or unsubstituted aryl group with 6 to 30 carbon atoms to form a ring, or a substituted or unsubstituted heteroaryl group with 2 to 30 carbon atoms to form a ring. Or, it forms a ring by combining with adjacent groups.

In the formula Fc, A ₁ and A ₂ can each independently combine with substituents of neighboring rings to form a condensed ring. For example, when A ₁ and A ₂ are each independently NR _m , A ₁ may be combined with R ₄ or R ₅ to form a ring. Additionally, A ₂ may be combined with R ₇ or R ₈ to form a ring.

In one embodiment, the emitting layer (EML) is a known dopant material, such as a styryl derivative (e.g., 1, 4-bis[2-(3-N-ethylcarbazoryl)vinyl]benzene (BCzVB), 4-(di- p-tolylamino)-4'-[(di-p-tolylamino)styryl]stilbene(DPAVB), N-(4-((E)-2-(6-((E)-4-(diphenylamino)styryl) naphthalen-2-yl)vinyl)phenyl)-N-phenylbenzenamine(N-BDAVBi)), 4,4'-bis[2-(4-(N,N-diphenylamino)phenyl)vinyl]biphenyl(DPAVBi), Rylene and its derivatives (e.g., 2, 5, 8, 11-Tetra-t-butylperylene (TBP)), pyrene and its derivatives (e.g., 1, 1-dipyrene, 1, 4-dipyrenylbenzene, 1, It may include 4-Bis(N, N-Diphenylamino)pyrene), etc.

In one embodiment, when a plurality of emitting layers (EML) is included, at least one emitting layer (EML) may include a known phosphorescent dopant material. For example, phosphorescent dopants include iridium (Ir), platinum (Pt), osmium (Os), gold (Au), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), and terbium (Tb). ) or a metal complex containing thulium (Tm) may be used. Specifically, FIrpic(iridium(III) bis(4,6-difluorophenylpyridinato-N,C2'), Fir6(Bis(2,4-difluorophenylpyridinato)-tetrakis(1-pyrazolyl)borate iridium(III)), or PtOEP( platinum octaethyl porphyrin) may be used as a phosphorescent dopant, but the embodiment is not limited thereto.

Meanwhile, in one embodiment, the light-emitting layer (EML) may include a hole-transporting host and an electron-transporting host. Additionally, the emitting layer (EML) may include an auxiliary dopant and an emitting dopant. Meanwhile, the auxiliary dopant may include a phosphorescent dopant material or a thermally activated delayed fluorescence dopant material. That is, in one embodiment, the light-emitting layer (EML) may include a hole-transporting host, an electron-transporting host, an auxiliary dopant, and a light-emitting dopant.

Additionally, an exciplex may be formed in the emitting layer (EML) by a hole-transporting host and an electron-transporting host. At this time, the triplet energy of the exciplex formed by the hole-transporting host and the electron-transporting host may correspond to T1, which is the interval between the LUMO energy level of the electron-transporting host and the HOMO energy 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 2.4 eV or more and 3.0 eV or less. Additionally, the triplet energy of the exciplex may be smaller than the energy gap of each host material. Therefore, the exciplex may have a triplet energy of 3.0 eV or less, which is the energy gap between the hole-transporting host and the electron-transporting host.

Meanwhile, at least one light emitting layer (EML) may include a quantum dot material. The core of the quantum dot is a group II-VI compound, a group III-VI compound, a group I-III-VI compound, a group III-V compound, a group III-II-V compound, a group IV-VI compound, a group IV element, and a group IV It may be selected from compounds and combinations thereof.

Group II-VI compounds include binary compounds selected from the group consisting of CdSe, CdTe, CdS, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, MgSe, MgS and mixtures thereof; CDSES, CDSETE, CDSTE, ZNSES, ZNSETE, ZNSTE, HGSES, HGSETE, HGSES, CDZNS, CDZNSE, CDZNTE, CDHGS, CDHGSE, CDHGTE, HGZNS Samwon selected from the group consisting of, mgzns and mixtures thereof small compounds; and a tetraelement compound selected from the group consisting of HgZnTeS, CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe, HgZnSTe, and mixtures thereof.

Group III-VI compounds may include binary compounds such as In ₂ S ₃ , In ₂ Se ₃ , ternary compounds such as InGaS ₃ , InGaSe ₃ , or any combination thereof.

Group I-III-VI compounds are three element compounds selected from the group consisting of AgInS, AgInS ₂ , CuInS, CuInS ₂ , AgGaS ₂ , CuGaS ₂ CuGaO ₂ , AgGaO ₂ , AgAlO ₂ and mixtures thereof, or AgInGaS ₂ , It may be selected from quaternary element compounds such as CuInGaS ₂ .

Group III-V compounds are binary compounds selected from the group consisting of GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, InSb and mixtures thereof, GaNP, GaNAs, GaNSb, GaPAs , a ternary compound selected from the group consisting of GaPSb, AlNP, AlNAs, AlNSb, AlPAs, AlPSb, InGaP, InAlP, InNP, InNAs, InNSb, InPAs, InPSb and mixtures thereof, and GaAlNP, GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb , GaInNP, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs, InAlPSb, and mixtures thereof. Meanwhile, the group III-V compound may further include a group II metal. For example, InZnP, etc. may be selected as the group III-II-V compound.

Group IV-VI compounds are binary compounds selected from the group consisting of SnS, SnSe, SnTe, PbS, PbSe, PbTe and mixtures thereof, SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, SnPbTe and these It may be selected from the group consisting of a tri-element compound selected from the group consisting of mixtures of, and a quaternary element compound selected from the group consisting of SnPbSSe, SnPbSeTe, SnPbSTe, and mixtures thereof. Group IV elements may be selected from the group consisting of Si, Ge, and mixtures thereof. The group IV compound may be a binary compound selected from the group consisting of SiC, SiGe, and mixtures thereof.

At this time, the di-element compound, tri-element compound, or quaternary compound may exist in the particle at a uniform concentration, or may exist in the same particle with a partially different concentration distribution. Additionally, one quantum dot may have a core/shell structure surrounding other quantum dots. In a core/shell structure, there may be a concentration gradient in which the concentration of elements present in the shell decreases toward the core.

In some embodiments, quantum dots may have a core-shell structure including a core including the above-described nanocrystals and a shell surrounding the core. The shell of the quantum dot may serve as a protective layer to maintain semiconductor properties by preventing chemical denaturation of the core and/or as a charging layer to impart electrophoretic properties to the quantum dot. The shell may be single or multi-layered. Examples of the shell of the quantum dot include metal or non-metal oxides, semiconductor compounds, or combinations thereof.

For example, the oxides of the metal or non-metal include 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 , Examples may include binary compounds such as CoO, Co ₃ O ₄ , NiO, or ternary compounds such as MgAl ₂ O ₄ , CoFe ₂ O ₄ , NiFe ₂ O ₄ , and CoMn ₂ O ₄ , but the present invention is limited thereto. That is not the case.

In addition, the semiconductor compounds include CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnSeS, ZnTeS, GaAs, GaP, GaSb, HgS, HgSe, HgTe, InAs, InP, InGaP, InSb, AlAs, AlP, AlSb, etc. However, the present invention is not limited thereto.

Quantum dots may have a full width of half maximum (FWHM) of the emission wavelength spectrum of about 45 nm or less, preferably about 40 nm or less, more preferably about 30 nm or less, and can improve color purity or color reproducibility in this range. You can. Additionally, since the light emitted through these quantum dots is emitted in all directions, the optical viewing angle can be improved.

In addition, the shape of the quantum dots is not particularly limited to those commonly used in the art, but more specifically, spherical, pyramidal, multi-arm, or cubic nanoparticles, nanotubes, Things in the form of nanowires, nanofibers, nanoplate particles, etc. can be used.

Quantum dots can control the color of light they emit depending on the particle size, and accordingly, quantum dots can have various emission colors such as blue, red, and green.

In the light emitting device ED of one embodiment shown in FIGS. 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 made of a single material, a single layer made of a plurality of different materials, or a multilayer structure having a plurality of layers made of a plurality of different materials.

For example, the electron transport region (ETR) may have a single-layer structure of an electron injection layer (EIL) or an electron transport layer (ETL), or may have a single-layer structure composed of an electron injection material and an electron transport material. In addition, the electron transport region (ETR) has a single-layer structure made of a plurality of different materials, or an electron transport layer (ETL)/electron injection layer (EIL), a hole blocking layer ( It may have a structure such as HBL)/electron transport layer (ETL)/electron injection layer (EIL), electron transport layer (ETL)/buffer layer (not shown)/electron injection layer (EIL), but is not limited thereto. The thickness of the electron transport region (ETR) may be, for example, about 1000Å to about 1500Å.

The electron transport region (ETR) is created using various methods such as vacuum deposition, spin coating, cast, LB (Langmuir-Blodgett), inkjet printing, laser printing, and laser induced thermal imaging (LITI). It can be formed using

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

[Formula ET-1]

In the formula ET-1, at least one of X ₁ to X ₃ is N and the others are CR _a . R _a is a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group with 1 to 20 carbon atoms, a substituted or unsubstituted aryl group with 6 to 30 carbon atoms to form a ring, or a substituted or unsubstituted aryl group with 2 to 30 carbon atoms to form a ring. It may be the following heteroaryl group. Ar ₁ to Ar ₃ are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms. It may be a heteroaryl group having 2 to 30 ring carbon atoms.

In Formula ET-1, a to c may each independently be an integer from 0 to 10 or less. In the formula ET-1, L ₁ to L ₃ are each independently a direct linkage, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted arylene group having 2 to 30 ring carbon atoms. It may be a heteroarylene group. Meanwhile, when a to c are integers of 2 or more, L ₁ to L ₃ are each independently a substituted or unsubstituted arylene group with 6 to 30 ring carbon atoms, or a substituted or unsubstituted hetero group with 2 to 30 ring carbon atoms. It may be an arylene group.

The electron transport region (ETR) may include an anthracene-based compound. However, it is not limited to this, and the electron transport region (ETR) is, for example, Alq ₃ (Tris(8-hydroxyquinolinato)aluminum), 1,3,5-tri[(3-pyridyl)-phen-3-yl ]benzene, 2,4,6-tris(3'-(pyridin-3-yl)biphenyl-3-yl)-1,3,5-triazine, 2-(4-(N-phenylbenzoimidazol-1-yl) phenyl)-9,10-dinaphthylanthracene, TPBi(1,3,5-Tri(1-phenyl-1H-benzo[d]imidazol-2-yl)benzene), BCP(2,9-Dimethyl-4,7- diphenyl-1,10-phenanthroline), Bphen(4,7-Diphenyl-1,10-phenanthroline), TAZ(3-(4-Biphenylyl)-4-phenyl-5-tert-butylphenyl-1,2,4- triazole), NTAZ(4-(Naphthalen-1-yl)-3,5-diphenyl-4H-1,2,4-triazole), tBu-PBD(2-(4-Biphenylyl)-5-(4-tert -butylphenyl)-1,3,4-oxadiazole), BAlq(Bis(2-methyl-8-quinolinolato-N1,O8)-(1,1'-Biphenyl-4-olato)aluminum), Bebq ₂ (berylliumbis( benzoquinolin-10-olate)), ADN(9,10-di(naphthalene-2-yl)anthracene), BmPyPhB(1,3-Bis[3,5-di(pyridin-3-yl)phenyl]benzene), It may include TSPO1 (diphenyl(4-(triphenylsilyl)phenyl)phosphine oxide) and mixtures thereof.

The electron transport region (ETR) may include at least one of the following compounds ET1 to ET36.

In addition, the electron transport region (ETR) may include a halide metal such as LiF, NaCl, CsF, RbCl, RbI, CuI, KI, a lanthanide metal such as Yb, and a co-deposition material of the above halide metal and lanthanide metal. You can. For example, the electron transport region (ETR) may include KI:Yb, RbI:Yb, LiF:Yb, etc. as co-deposited materials. Meanwhile, the electron transport region (ETR) may be made of a metal oxide such as Li ₂ O, BaO, or Liq (8-hydroxyl-Lithium quinolate), but the embodiment is not limited thereto. The electron transport region (ETR) may also be made of a mixture of an electron transport material and an insulating organo metal salt. Organic metal salts can be materials with an energy band gap of approximately 4 eV or more. Specifically, for example, the organometallic salt may include metal acetate, metal benzoate, metal acetoacetate, metal acetylacetonate, or metal stearate. You can.

In addition to the previously mentioned materials, the electron transport region (ETR) is composed of 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), diphenyl(4-(triphenylsilyl)phenyl)phosphine oxide (TSPO1), and Bphen( It may further include at least one of 4,7-diphenyl-1,10-phenanthroline), but the example is not limited thereto.

The electron transport region (ETR) may include the compounds of the electron transport region described above in at least one of the electron injection layer (EIL), the electron transport layer (ETL), and the hole blocking layer (HBL).

When the electron transport region (ETR) includes an electron transport layer (ETL), the thickness of the electron transport layer (ETL) may be about 100 Å to about 1000 Å, for example, about 150 Å to about 500 Å. When the thickness of the electron transport layer (ETL) satisfies the range described above, satisfactory electron transport characteristics can be obtained without a substantial increase in driving voltage. When the electron transport region (ETR) includes an electron injection layer (EIL), the thickness of the electron injection layer (EIL) may be about 1 Å to about 100 Å, or about 3 Å to about 90 Å. When the thickness of the electron injection layer (EIL) satisfies the range described above, satisfactory electron injection characteristics can be obtained without a substantial increase in 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 or an anode, but the embodiment is not limited thereto. For example, if the first electrode EL1 is an anode, the second electrode EL2 may be a cathode, and if the first electrode EL1 is a cathode, the second electrode EL2 may be an anode. The second electrode is 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, It may contain two or more compounds selected from these, a mixture of two or more types selected from these, or oxides thereof.

The second electrode EL2 may be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode. When the second electrode EL2 is a transparent electrode, the second electrode EL2 is made of a transparent metal oxide, for example, indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), or indium ITZO. It may be made of tin zinc oxide, etc.

When the second electrode EL2 is a transflective electrode or a reflective electrode, the second electrode EL2 is made of Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF/Ca (stacked structure of LiF and Ca), LiF/Al (laminated structure of LiF and Al), Mo, Ti, Yb, W, or compounds or mixtures containing them (e.g., AgMg, AgYb, or MgYb) may include. Alternatively, the second electrode EL2 may be a reflective film or semi-transmissive film formed of the above materials and a transparent conductive film formed of ITO (indium tin oxide), IZO (indium zinc oxide), ZnO (zinc oxide), ITZO (indium tin zinc oxide), etc. It may be a multiple layer structure including a membrane. 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, or oxides of the above-mentioned metal materials.

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

Meanwhile, a capping layer (CPL) may be further disposed on the second electrode (EL2) of the light emitting device (ED) in one embodiment. The capping layer (CPL) may include multiple layers or a single layer.

In one embodiment, the capping layer (CPL) may be an organic layer or an inorganic layer. For example, when the capping layer (CPL) includes an inorganic material, the inorganic material may include an alkali metal compound such as LiF, an alkaline earth metal compound such as MgF ₂ , _SiON , SiN

For example, if the capping layer (CPL) contains an organic material, the organic material may be α-NPD, NPB, TPD, m-MTDATA, Alq ₃ , CuPc, TPD15(N4,N4,N4',N4'-tetra (biphenyl -4-yl) biphenyl-4,4'-diamine), TCTA (4,4',4"- Tris (carbazol sol-9-yl) triphenylamine), etc., epoxy resin, or methacrylate. It may include acrylate. However, the example is not limited thereto, and the capping layer (CPL) may include at least one of the following compounds P1 to P5.

Meanwhile, the refractive index of the capping layer (CPL) may be 1.6 or more. Specifically, the refractive index of the capping layer (CPL) may be 1.6 or more for light in a wavelength range of 550 nm to 660 nm.

7 to 10 are cross-sectional views of a display device according to an exemplary embodiment, respectively. Hereinafter, in the description of the display device of an embodiment described with reference to FIGS. 7 to 10, content that overlaps with the content described in FIGS. 1 to 6 will not be described again, and the differences will be mainly explained.

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

In one embodiment shown in FIG. 7, the display panel DP includes a base layer (BS), a circuit layer (DP-CL) provided on the base layer (BS), and a display element layer (DP-ED), and displays The device layer (DP-ED) may include a light emitting device (ED).

The light emitting device (ED) includes a first electrode (EL1), a hole transport region (HTR) disposed on the first electrode (EL1), an emitting layer (EML) disposed on the hole transport region (HTR), and an emitting layer (EML) disposed on the first electrode (EL1). It may include an electron transport region (ETR) disposed in and a second electrode (EL2) disposed on the electron transport region (ETR). Meanwhile, the structure of the light emitting device ED shown in FIG. 7 may be identical to the structure of the light emitting device shown in FIGS. 3 to 6 described above.

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

Referring to FIG. 7 , the light emitting layer (EML) may be disposed within the opening (OH) defined in the pixel defining layer (PDL). For example, the emitting layer (EML) divided by a pixel defining layer (PDL) and provided corresponding to each emitting region (PXA-R, PXA-G, PXA-B) may emit light in the same wavelength region. . In the display device DD-a of one embodiment, the emission layer EML may emit blue light. Meanwhile, unlike what is shown, in one embodiment, the light emitting layer (EML) may be provided as a common layer throughout the light emitting areas (PXA-R, PXA-G, and PXA-B).

The light control layer (CCL) may be disposed on the display panel (DP). The light control layer (CCL) may include a light converter. The photoconverter may be a quantum dot or a phosphor. The photoconverter may convert the received light into wavelengths and emit it. That is, the light control layer (CCL) may be a layer containing quantum dots or a layer containing phosphors.

The light control layer (CCL) may include a plurality of light control units (CCP1, CCP2, and CCP3). The optical control units (CCP1, CCP2, and CCP3) may be spaced apart from each other.

Referring to FIG. 7 , a split pattern (BMP) may be disposed between the light control units CCP1, CCP2, and CCP3 that are spaced apart from each other, but the embodiment is not limited thereto. In FIG. 8, the split pattern BMP is shown as non-overlapping with the optical control units CCP1, CCP2, and CCP3, but the edges of the optical control units CCP1, CCP2, and CCP3 overlap at least part of the split pattern BMP. can do.

The light control layer (CCL) includes a first light control unit (CCP1) including a first quantum dot (QD1) that converts the first color light provided from the light emitting device (ED) into second color light, and converts the first color light into third color light. It may include a second light control unit (CCP2) including a second quantum dot (QD2) for conversion, and a third light control unit (CCP3) for transmitting the first color light.

In one embodiment, the first light control unit CCP1 may provide red light, which is a second color light, and the second light control unit CCP2 may provide green light, a third color light. The third light control unit CCP3 may transmit and provide blue light, which is the first color light provided from the light emitting device 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 contents as described above may be applied to quantum dots (QD1, QD2).

Additionally, the light control layer (CCL) may further include a scatterer (SP). The first light control unit (CCP1) includes a first quantum dot (QD1) and a scatterer (SP), the second light control unit (CCP2) includes a second quantum dot (QD2) and a scatterer (SP), and the third light control unit (CCP1) includes a first quantum dot (QD1) and a scatterer (SP). The light control unit (CCP3) may not include quantum dots but may include a scatterer (SP).

Scatterers (SP) may be inorganic particles. For example, the scatterer (SP) may include at least one of TiO ₂ , ZnO, Al ₂ O ₃ , SiO ₂ , and hollow silica. The scatterer (SP) includes any one of TiO ₂ , ZnO, Al ₂ O ₃ , SiO ₂ , and hollow silica, or is selected from TiO ₂ , ZnO, Al ₂ O ₃ , SiO ₂ , and hollow silica. It may be a mixture of two or more substances.

The first light control unit (CCP1), the second light control unit (CCP2), and the third light control unit (CCP3) each use a base resin (BR1, BR2, BR3) for dispersing quantum dots (QD1, QD2) and scatterers (SP). may include. In one embodiment, the first light control unit (CCP1) includes a first quantum dot (QD1) and a scatterer (SP) dispersed in the first base resin (BR1), and the second light control unit (CCP2) includes the second base resin (BR1). It includes a second quantum dot (QD2) and a scatterer (SP) dispersed in the resin (BR2), and the third light control unit (CCP3) includes a scatterer (SP) dispersed in the third base resin (BR3). You can. The base resin (BR1, BR2, BR3) is a medium in which quantum dots (QD1, QD2) and scatterers (SP) are dispersed, and may be made of various resin compositions that can generally be referred to as binders. For example, the base resins (BR1, BR2, BR3) may be acrylic resin, urethane resin, silicone resin, epoxy resin, etc. The base resin (BR1, BR2, BR3) may be a transparent resin. In one 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 barrier layer (BFL1). The barrier layer (BFL1) may serve to prevent penetration of moisture and/or oxygen (hereinafter referred to as 'moisture/oxygen'). The barrier layer BFL1 is disposed on the light control units CCP1, CCP2, and CCP3 to block the light control units CCP1, CCP2, and CCP3 from being exposed to moisture/oxygen. Meanwhile, the barrier layer BFL1 may cover the light control units CCP1, CCP2, and CCP3. Additionally, a barrier layer (BFL2) may be provided between the light control units (CCP1, CCP2, and CCP3) and the filters (CF1, CF2, and CF3).

The barrier layers BFL1 and BFL2 may include at least one inorganic layer. That is, the barrier layers BFL1 and BFL2 may include an inorganic material. For example, the barrier layers (BFL1, BFL2) are silicon nitride, aluminum nitride, zirconium nitride, titanium nitride, hafnium nitride, tantalum nitride, silicon oxide, aluminum oxide, titanium oxide, tin oxide, cerium oxide, and silicon oxynitride or optical nitride. It may include a metal thin film with guaranteed transmittance. Meanwhile, the barrier layers BFL1 and BFL2 may further include an organic layer. The barrier layers BFL1 and BFL2 may be composed of a single layer or multiple layers.

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

The color filter layer (CFL) may include filters CF1, CF2, and CF3. The color filter layer (CFL) may include a first filter (CF1) that transmits the second color light, a second filter (CF2) that transmits the third color light, and a third filter (CF3) that transmits the first color light. . For example, the first filter (CF1) may be a red filter, the second filter (CF2) may be a green filter, and the third filter (CF3) may be a blue filter. Each of the filters CF1, CF2, and CF3 may contain a polymer photosensitive resin and a pigment or dye. The first filter (CF1) may contain a red pigment or dye, the second filter (CF2) may contain a green pigment or dye, and the third filter (CF3) may contain a blue pigment or dye. Meanwhile, the embodiment is not limited to this, and the third filter CF3 may not contain pigment or dye. The third filter (CF3) may contain a polymer photosensitive resin and may not contain pigment or dye. The third filter CF3 may be transparent. The third filter CF3 may be made of transparent photoresist.

Additionally, in one embodiment, the first filter (CF1) and the second filter (CF2) may be yellow filters. The first filter (CF1) and the second filter (CF2) may not be separated from each other and may be provided as one unit. Each of the first to third filters CF1, CF2, and CF3 may be arranged to correspond to the red light-emitting area (PXA-R), the green light-emitting area (PXA-G), and the blue light-emitting area (PXA-B), respectively. .

Meanwhile, although not shown, the color filter layer (CFL) may include a light blocking portion (not shown). The color filter layer CFL may include a light blocking portion (not shown) arranged to overlap the boundaries of neighboring filters CF1, CF2, and CF3. The light blocking portion (not shown) may be a black matrix. The light blocking portion (not shown) may be formed of an organic light blocking material or an inorganic light blocking material containing black pigment or black dye. The light blocking portion (not shown) may separate the boundary between adjacent filters CF1, CF2, and CF3. Additionally, in one embodiment, the light blocking portion (not shown) may be formed of a blue filter.

A base substrate BL may be disposed on the color filter layer CFL. The base substrate BL may be a member that provides a base surface on which a color filter layer (CFL) and a light control layer (CCL) are disposed. The base substrate (BL) may be a glass substrate, a metal substrate, or a plastic substrate. However, the embodiment is not limited to this, and the base substrate BL may be an inorganic layer, an organic layer, or a composite material layer. Additionally, unlike what is shown, in one embodiment, the base substrate BL may be omitted.

Figure 8 is a cross-sectional view showing a portion of a display device according to an embodiment. FIG. 8 shows a cross-sectional view of a portion corresponding to the display panel DP of FIG. 7 . In the display device DD-TD of one embodiment, the light emitting element ED-BT may include a plurality of light emitting structures OL-B1, OL-B2, and OL-B3. The light emitting device (ED-BT) includes a plurality of first electrodes (EL1) and second electrodes (EL2) facing each other, sequentially stacked in the thickness direction between the first electrodes (EL1) and the second electrodes (EL2). It may include two light-emitting structures (OL-B1, OL-B2, OL-B3). Each of the light-emitting structures (OL-B1, OL-B2, OL-B3) has a light-emitting layer (EML, Figure 7), a hole transport region (HTR) and an electron transport region (EML, Figure 7) disposed between them. It may include ETR).

That is, the light-emitting device (ED-BT) included in the display device (DD-TD) of one embodiment may be a light-emitting device of a tandem structure including a plurality of light-emitting layers.

In one embodiment shown in FIG. 8, all light emitted from each of the light emitting structures OL-B1, OL-B2, and OL-B3 may be blue light. However, the embodiment is not limited to this, and the wavelength range of light emitted from each of the light emitting structures OL-B1, OL-B2, and OL-B3 may be different. For example, a light-emitting device (ED-BT) including a plurality of light-emitting structures (OL-B1, OL-B2, OL-B3) that emit light in different wavelength ranges may emit white light.

Charge generation layers (CGL1 and CGL2) may be disposed between neighboring light emitting structures (OL-B1, OL-B2, and 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, and OL-B3) included in the display device (DD-TD) of one embodiment may include the amine compound of one embodiment described above.

Referring to FIG. 9 , the display device DD-b according to one embodiment may include light emitting elements ED-1, ED-2, and ED-3 in which two light emitting layers are stacked. Compared to the display device DD of the embodiment shown in FIG. 2, in the embodiment shown in FIG. 9, the first to third light emitting elements ED-1, ED-2, and ED-3 are each disposed in the thickness direction. The difference is that it includes two stacked light emitting layers. The two light emitting layers in each of the first to third light emitting devices (ED-1, ED-2, and ED-3) may emit light in the same wavelength range.

The first light emitting device (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 device (ED-2) may include a first green light emitting layer (EML-G1) and a second green light emitting layer (EML-G2). Additionally, the third light emitting device (ED-3) may include a first blue light emitting layer (EML-B1) and a second blue light emitting layer (EML-B2). Between the first red light emitting layer (EML-R1) and the second red light emitting layer (EML-R2), between the first green light emitting layer (EML-G1) and the second green light emitting layer (EML-G2), and the first blue light emitting layer (EML- A light emitting auxiliary part (OG) may be disposed between B1) and the second blue light emitting layer (EML-B2).

The light emitting auxiliary part (OG) may include a single layer or multiple layers. The light emitting auxiliary part (OG) may include a charge generation layer. More specifically, the light emitting auxiliary part (OG) may include an electron transport region, a charge generation layer, and a hole transport region stacked sequentially. The light emitting auxiliary part (OG) may be provided as a common layer throughout the first to third light emitting devices (ED-1, ED-2, and ED-3). However, the embodiment is not limited to this, and the light emitting auxiliary portion (OG) may be provided by being patterned within the opening (OH) defined in the pixel defining layer (PDL).

The first red emission layer (EML-R1), the first green emission layer (EML-G1), and the first blue emission layer (EML-B1) may be disposed between the emission auxiliary part (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 transport region (HTR) and the light emitting auxiliary portion (OG).

That is, the first light-emitting device (ED-1) consists of a sequentially stacked first electrode (EL1), a hole transport region (HTR), a second red light-emitting layer (EML-R2), a light-emitting auxiliary part (OG), and a first red light-emitting layer. (EML-R1), an electron transport region (ETR), and a second electrode (EL2). The second light emitting device (ED-2) consists of a sequentially stacked first electrode (EL1), a hole transport region (HTR), a second green light emitting layer (EML-G2), a light emitting auxiliary part (OG), and a first green light emitting layer (EML). -G1), an electron transport region (ETR), and a second electrode (EL2). The third light-emitting device (ED-3) consists of a sequentially stacked first electrode (EL1), a hole transport region (HTR), a second blue light-emitting layer (EML-B2), a light-emitting auxiliary part (OG), and a first blue light-emitting layer (EML-B2). -B1), an electron transport region (ETR), and a second electrode (EL2).

Meanwhile, an 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 is disposed on the display panel DP to control light reflected from the display panel DP by external light. Unlike what is shown, the optical auxiliary layer PL may be omitted in the display device according to one embodiment.

Unlike FIGS. 8 and 9, the display device DD-c in FIG. 10 is shown as including four light emitting structures (OL-B1, OL-B2, OL-B3, and OL-C1). The light emitting device (ED-CT) includes a first electrode (EL1) and a second electrode (EL2) facing each other, and first to second electrodes sequentially stacked in the thickness direction between the first electrode (EL1) and the second electrode (EL2). It may include fourth light emitting structures (OL-B1, OL-B2, OL-B3, and OL-C1). Charge generation layers (CGL1, CGL2, CGL3) may be disposed between the first to fourth light emitting structures (OL-B1, OL-B2, OL-B3, and OL-C1). Among the four light-emitting structures, the first to third light-emitting structures (OL-B1, OL-B2, and OL-B3) may emit blue light, and the fourth light-emitting structure (OL-C1) may emit green light. However, the embodiment is not limited to this, and the first to fourth light emitting structures OL-B1, OL-B2, OL-B3, and OL-C1 may emit light in different wavelength ranges.

The charge generation layer (CGL1, CGL2, CGL3) disposed between neighboring light emitting structures (OL-B1, OL-B2, OL-B3, OL-C1) is a p-type charge generation layer and/or an n-type charge generation layer. It may include.

At least one of the light emitting structures (OL-B1, OL-B2, OL-B3, and OL-C1) included in the display device (DD-c) of one embodiment may include the amine compound of one embodiment described above.

The light emitting device (ED) according to an embodiment of the present invention has improved light emission by including 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). It can exhibit efficiency and improved lifespan characteristics. The light emitting device (ED) according to one embodiment includes the amine compound of the above-described embodiment in a hole transport region (HTR) disposed between the first electrode (EL1) and the second electrode (EL2), an emission layer (EML), and an electron It may be included in at least one of the transport regions (ETR) or in the capping layer (CPL). For example, the amine compound according to one embodiment may be included in the hole transport region (HTR) of the light emitting device (ED) of one embodiment, and the light emitting device of one embodiment may exhibit high efficiency and long lifespan characteristics.

The amine compound of the above-described embodiment includes first to third substituents, which can increase the stability of the material and improve hole transport properties. Accordingly, the lifespan and efficiency of the light emitting device including the amine compound of one embodiment may be increased. Additionally, the light emitting device of one embodiment may exhibit increased efficiency and lifespan characteristics by including the amine compound according to one embodiment in the hole transport layer.

Hereinafter, the amine compound according to one embodiment of the present invention and the light emitting device of one example will be described in detail, referring to Examples and Comparative Examples. In addition, the Example shown below is an example to aid understanding of the present invention, and the scope of the present invention is not limited thereto.

[Example]

1. Synthesis of amine compounds

First, regarding the method of synthesizing the amine compound according to the present embodiment, Compound 3, Compound 57, Compound 115, Compound 131, Compound 169, Compound 173, Compound 241, Compound 246, Compound 266, Compound 274, Methods for synthesizing Compound 275 and Compound 317 will be described in detail by way of example. In addition, the method for synthesizing an amine compound described below is an example, and the method for synthesizing an amine compound according to an embodiment of the present invention is not limited to the example below.

<Methods for synthesizing compounds>

1) Synthesis of Compound 3

[Scheme 1]

Under Ar atmosphere, 9-(4-Bromophenyl)carbazole (20.0 g), (4-Chlorophenyl)boronic acid (9.70 g), Tetrakis(triphenylphosphine)palladium(0) (Pd(PPh ₃ )) in a 1L three-necked flask. ₄ , 3.5 g), potassium carbonate (K ₂ CO ₃ , 17.2 g), dissolved in a mixed solvent of toluene, water, and ethanol (10:2:1, 300 mL), and heated at 80°C for 5 hours. Stirred. After cooling, the resulting precipitate was recovered and washed with toluene and ethanol to obtain 18.9 g of intermediate A (yield 86%). The molecular weight of intermediate A measured by FAB-MS measurement was 353.

[Scheme 2]

Under Ar atmosphere, 9-(3-Bromophenyl)carbazole (20.0 g), (4-Chlorophenyl)boronic acid (9.70 g), Pd(PPh ₃ ) ₄ (3.5 g), K ₂ CO in a 1L three-necked flask. ₃ (17.3 g) was added, dissolved in a mixed solvent of toluene, water, and ethanol (10:2:1, 300 mL), and heated and stirred at 80°C for 6 hours. Water was added and extracted with CH ₂ Cl ₂ , the organic layers were collected and dried over MgSO ₄ , and the solvent was removed under reduced pressure. The obtained composition was purified by silica gel column chromatography to obtain 17.3 g of intermediate B (yield 79%). The molecular weight of intermediate B measured by FAB-MS measurement was 353.

[Scheme 3]

Under Ar atmosphere, in a 1L three-necked flask, Carbazole (10.0 g), 2-Bromo-6-iodonaphthalene (30.0 g), Copper(I) iodide (CuI, 1.2 g), 1,10-Phenanthroline (1,10) -Phen, 2.2 g) and Cesium carbonate (Cs ₂ CO ₃ , 58 g) were added, dissolved in 1,2-Dichlorobenzene (300 mL), and heated and stirred at 150°C for 12 hours. Water was added and extracted with CH ₂ Cl ₂ , the organic layers were collected and dried over MgSO ₄ , and the solvent was removed under reduced pressure. The obtained composition was purified by silica gel column chromatography to obtain 12.9 g of intermediate C (yield 58%). The molecular weight of intermediate C measured by FAB-MS measurement was 372.

[Scheme 4]

Under Ar atmosphere, add 3,6-Diphenylcarbazole (10.0 g), 1-Bromo-3-fluorobenzene (8.2 g), Cs ₂ CO ₃ (20 g) to a 500 mL three-neck flask, and add DMSO (150 mL). was dissolved in and heated and stirred at 150°C for 20 hours. After cooling, the reaction solvent was poured into water, and the resulting precipitate was recovered and washed with toluene and ethanol to obtain 9.65 g of intermediate D (yield 65%). The molecular weight of intermediate D measured by FAB-MS measurement was 474.

[Scheme 5]

In the same manner as the synthesis of Intermediate B, 10.8 g (80% yield) of Intermediate E was obtained from 3-Bromocarbazole (10.0 g) and Dibenzofuran-4-ylboronic acid (8.6 g). The molecular weight of intermediate E measured by FAB-MS measurement was 333.

In the same manner as the synthesis of intermediate D, 8.2 g (56% yield) of intermediate F was obtained from E (10.0 g) and 1-Bromo-3-fluorobenzene (7.9 g). The molecular weight of intermediate F measured by FAB-MS measurement was 488.

[Scheme 6]

Under Ar atmosphere, 1,8-Dibromonaphthalene (20.0 g), Phenylboronic acid (8.52 g), Pd(PPh ₃ ) ₄ (4.0 g), Sodium carbonate (Na ₂ CO ₃ , 15 g) in a 1L three-necked flask. was added, dissolved in a mixed solvent of THF and water (8:2, 350 mL), and heated and stirred at 70°C for 10 hours. Water was added and extracted with CH ₂ Cl ₂ , the organic layers were collected and dried over MgSO ₄ , and the solvent was removed under reduced pressure. The obtained composition was purified by silica gel column chromatography to obtain 14.8 g of intermediate G (yield 75%). The molecular weight of intermediate G measured by FAB-MS measurement was 283.

In an Ar atmosphere, place intermediate G (20.0 g), 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (15.5 g), and Pd in a 1L three-necked flask. Add (PPh ₃ ) ₄ (4.0 g) and K ₂ CO ₃ (20 g), dissolve in a mixed solvent of toluene, water, and ethanol (10:2:1, 350 mL), and stir at 80°C for 10 hours. Heated and stirred. Water was added and extracted with CH ₂ Cl ₂ , the organic layers were collected and dried over MgSO ₄ , and the solvent was removed under reduced pressure. The obtained composition was purified by silica gel column chromatography to obtain 15.8 g of intermediate H (yield 76%). The molecular weight of intermediate H measured by FAB-MS measurement was 295.

[Scheme 7]

In the same manner as the synthesis of Intermediate H, 7.45 g (67% yield) of Intermediate I was obtained from Intermediate G (10.0 g) and (3-Chlorophenyl)boronic acid (5.52 g). The molecular weight of intermediate I measured by FAB-MS measurement was 314.

[Scheme 8]

Under Ar atmosphere, in a 500 mL three-neck flask, intermediate H (10.0 g), 3-Bromobiphenyl (7.89 g), Bis(dibenzylideneacetone)palladium(0) (Pd(dba) ₂ , 0.97 g), Sodium tert-butoxide (NaO t Bu, 3.26 g) was added and dissolved in toluene (170 mL), Tri- tert -butylphosphine (P( t Bu) ₃ , 2.0 M in toluene, 1.5 mL) was added, and stirred at room temperature for 6 hours. did. Water was added and extracted with CH ₂ Cl ₂ , the organic layers were collected and dried over MgSO ₄ , and the solvent was removed under reduced pressure. The obtained composition was purified by silica gel column chromatography to obtain 12.8 g of intermediate J (yield 85%). The molecular weight of intermediate J measured by FAB-MS measurement was 447.

In an Ar atmosphere, add intermediate J (3.0 g), 9-(4-Bromophenyl)carbazole (2.16 g), Pd(dba) ₂ (0.2 g), and NaO t Bu (1.0 g) to a 200 mL three-necked flask. It was dissolved in toluene (50 mL), P( tBu ) ₃ (2.0 M in toluene, 0.3 mL) was added, and heated and stirred at 100°C for 6 hours. Water was added and extracted with CH ₂ Cl ₂ , the organic layers were collected and dried over MgSO ₄ , and the solvent was removed under reduced pressure. The obtained composition was purified by silica gel column chromatography, and 3.51 g of Compound 3 (yield 76%) was obtained. The molecular weight of compound 3 measured by FAB-MS measurement was 688.

2) Synthesis of compound 57

[Scheme 9]

In the same manner as the synthesis of Intermediate J, 21.9 g of Intermediate K (yield 87%) was obtained using Intermediate H (20.0 g) instead of Intermediate H (10.0 g) and 4-Bromobenzene (10.6 g) instead of 3-Bromobiphenyl. ) got it. The molecular weight of intermediate K measured by FAB-MS measurement was 371.

In the same manner as the synthesis of compound 3, using intermediate K (3.0 g) instead of intermediate J and intermediate A (2.85 g) instead of 9-(4-Bromophenyl)carbazole, 4.67 g of compound 57 (yield 84%) ) got it. The molecular weight of compound 57 measured by FAB-MS measurement was 688.

3) Synthesis of compound 115

[Scheme 10]

In the same manner as the synthesis of Compound 3, 3.65 g of Compound 115 (yield 79%) was obtained using 9-(3-Bromophenyl)carbazole (2.16 g) instead of 9-(4-Bromophenyl)carbazole. The molecular weight of compound 115 measured by FAB-MS measurement was 688.

4) Synthesis of compound 131

[Scheme 11]

In the same manner as the synthesis of Compound 3, using Intermediate H (5.0 g) instead of Intermediate J and Intermediate I (5.32 g) instead of 9-(4-Bromophenyl)carbazole, 5.63 g of Intermediate L (yield 58%) got it The molecular weight of intermediate L measured by FAB-MS measurement was 573.

Compound 131 was prepared in the same manner as the synthesis of Compound 3, using Intermediate L (3.0 g) instead of Intermediate J, and 9-(3-Bromophenyl)carbazole (1.68 g) instead of 9-(4-Bromophenyl)carbazole. 3.32 g (78% yield) was obtained. The molecular weight of compound 131 measured by FAB-MS measurement was 815.

5) Synthesis of compound 169

[Scheme 12]

In the same manner as the synthesis of Compound 3, using Intermediate K (3.0 g) instead of Intermediate J and Intermediate B (2.86 g) instead of 9-(4-Bromophenyl)carbazole, 4.73 g of Compound 169 (yield 85%) ) got it. The molecular weight of compound 169 measured by FAB-MS measurement was 688.

6) Synthesis of compound 173

[Scheme 13]

In the same manner as the synthesis of J above, 4.42 g of intermediate M (yield 62%) was obtained using intermediate H (5.0 g) and 1-Iodonaphthalene (4.30 g) instead of 3-Bromobiphenyl. The molecular weight of intermediate M measured by FAB-MS measurement was 421.

In the same manner as the synthesis of Compound 3, using Intermediate M (3.0 g) instead of Intermediate J and Intermediate B (2.52 g) instead of 9-(4-Bromophenyl)carbazole, 4.42 g of Compound 173 (yield 84%) ) got it. The molecular weight of compound 173 measured by FAB-MS measurement was 738.

7) Synthesis of compound 241

[Scheme 14]

In the same manner as the synthesis of Compound 3, using Intermediate K (3.0 g) instead of Intermediate J and Intermediate C (3.00 g) instead of 9-(4-Bromophenyl)carbazole, 4.55 g of Compound 241 (yield 85%) ) got it. The molecular weight of compound 241 measured by FAB-MS measurement was 662.

8) Synthesis of compound 246

[Scheme 15]

In the same manner as the synthesis of compound K, 10.7 g (71% yield) of compound P was obtained by using intermediate N (10.0 g) instead of intermediate H and 4-Bromobiphenyl (7.9 g) instead of 4-Bromobenzene. The molecular weight of compound P measured by FAB-MS measurement was 447.

In the same manner as the synthesis of Compound 3, 3.79 g (82% yield) of Compound 246 was obtained using Intermediate P (3.0 g) instead of Intermediate J and 9-(4-Bromophenyl)carbazole (2.16 g). The molecular weight of compound 246 measured by FAB-MS measurement was 688.

9) Synthesis of Compound 266

[Scheme 16]

Compound 266 was prepared in the same manner as the synthesis of Compound 3, using Intermediate P (3.0 g) instead of Intermediate J and 9-(3-Bromophenyl)carbazole (2.16 g) instead of 9-(4-Bromophenyl)carbazole. 3.51 g (yield 76%) was obtained. The molecular weight of compound 266 measured by FAB-MS measurement was 688.

10) Synthesis of compound 274

[Scheme 17]

In the same manner as the synthesis of Compound 3, using Intermediate K (3.0 g) instead of Intermediate J and Intermediate D (3.83 g) instead of 9-(4-Bromophenyl)carbazole, 4.57 g of Compound 274 (yield 74%) ) got it. The molecular weight of compound 274 measured by FAB-MS measurement was 764.

11) Synthesis of compound 275

[Scheme 18]

In the same manner as the synthesis of Compound 3, using Intermediate K (3.0 g) instead of Intermediate J and Intermediate F (3.94 g) instead of 9-(4-Bromophenyl)carbazole, 4.59 g of Compound 275 (yield 73%) ) got it. The molecular weight of compound 275 measured by FAB-MS measurement was 778.

12) Synthesis of compound 317

[Scheme 19]

In the same manner as the synthesis of compound H, intermediate G (3.0 g), 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)aniline was replaced with 3-(4,4 , 13.8 g of compound N (yield 66%) was obtained using 5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (15.5 g). The molecular weight of compound N measured by FAB-MS measurement was 295.

In the same manner as the synthesis of Compound K, 12.9 g (79% yield) of Compound O was obtained using Intermediate N (13.0 g) instead of Intermediate H and 4-Bromobenzene (6.91 g). The molecular weight of compound O measured by FAB-MS measurement was 371.

In the same manner as the synthesis of Compound 3, using Intermediate O (3.0 g) instead of Intermediate J and Intermediate B (2.86 g) instead of 9-(4-Bromophenyl)carbazole, 4.45 g of Compound 317 (yield 80%) ) got it. The molecular weight of compound 317 measured by FAB-MS measurement was 688.

2. Fabrication and evaluation of light emitting devices

(1) Production of light-emitting devices

A light emitting device including an amine compound of an example in a hole transport layer was manufactured by the method below.

After patterning ITO with a thickness of 1500Å on a glass substrate, it was washed with ultrapure water and treated with UV ozone for 10 minutes to form a first electrode. Afterwards, 2-TNATA was deposited to a thickness of 600Å to form a hole injection layer. Next, the example compound or comparative example compound was deposited to a thickness of 300 Å to form a hole transport layer.

Afterwards, a 250 Å thick light emitting layer was formed by doping ADN with 3% TBP. Next, Alq ₃ was deposited to a thickness of 250 Å to form an electron transport layer, and LiF was deposited to a thickness of 10 Å to form an electron injection layer.

Next, aluminum (Al) was provided with a thickness of 1000 Å to form a second electrode. In the example, the hole injection layer, the hole transport layer, the light emitting layer, the electron transport layer, the electron injection layer, and the second electrode were formed using a vacuum deposition apparatus.

<Example compounds>

<Comparative Example Compound>

In addition, the compounds of each functional layer used in the production of the light emitting device are as follows.

(2) Evaluation of light emitting devices

Table 1 shows the evaluation results of the light emitting devices of Examples 1 to 12 and Comparative Examples 1 to 5. In the characteristic evaluation results for the Examples and Comparative Examples shown in Table 1, the luminous efficiency represents the efficiency value at a current density of 10 mA/cm ² , and the half life represents the luminance half-decay time from 1000 cd/m ² . To evaluate the luminescence characteristics of the device, a C9920-11 luminance orientation characteristic measurement device manufactured by Hamamatsu Photonics KK was used.

Table 1 shows the relative values of the luminous efficiency and lifespan of Comparative Example 1 based on 100.

division Hole transport layer (HTL) material luminous efficiency
(cd/A) life span
LT50(h) Example 1 Example Compound 3 108% 120% Example 2 Example Compound 57 107% 160% Example 3 Example Compound 115 108% 150% Example 4 Example Compound 131 110% 150% Example 5 Example Compound 169 107% 155% Example 6 Example Compound 173 108% 160% Example 7 Example Compound 241 107% 130% Example 8 Example Compound 246 110% 110% Example 9 Example Compound 266 110% 120% Example 10 Example Compound 274 110% 130% Example 11 Example Compound 275 110% 110% Example 12 Example Compound 317 109% 160% Comparative Example 1 Comparative Example Compound X-1 100% 100% Comparative Example 2 Comparative Example Compound X-2 98% 50% Comparative Example 3 Comparative Example Compound X-3 100% 90% Comparative Example 4 Comparative Example Compound X-4 97% 60% Comparative Example 5 Comparative Example Compound X-5 95% 40%

Referring to the results in Table 1, the light emitting devices of Examples 1 to 12 using the amine compound of an example according to the present invention as the hole transport layer material are the light emitting devices of Comparative Examples 1 to 12 using the amine compound of the comparative example as the hole transport layer material. It can be seen that it exhibits excellent luminous efficiency and long life characteristics compared to the light emitting devices of 5.

Comparative Example Compound

Comparative Example Compound

Comparative Example Compound

Comparative Example Compound It is believed that the efficiency and lifespan characteristics are lowered compared to the example due to the phenyl group being connected.

Comparative Example Compound It is thought that the efficiency and lifespan characteristics are lowered compared to the examples due to condensation including this condensed structure.

The amine compound of the present invention has a first substituent having a carbazole skeleton connected through a linker, a second substituent that is a naphthyl group substituted with a substituted or unsubstituted phenyl group connected through a linker, and an aryl group or hetero It may have high stability and high hole transport ability by including a third substituent having an aryl group skeleton.

The light emitting device of the present invention includes the amine compound of one embodiment in the hole transport layer, so that hole transport ability is improved and material deterioration is suppressed, thereby improving efficiency and lifespan characteristics.

Although the present invention has been described above with reference to preferred embodiments, those skilled in the art or have ordinary knowledge in the relevant technical field will understand that it does not deviate from the spirit and technical scope of the present invention as set forth in the claims to be described later. It will be understood that various modifications and changes can be made to the present invention within the scope. Accordingly, 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 defined by the claims.

DD, DD-TD, DD-a, DD-b and DD-c: display devices
ED: light emitting element EL1: first electrode
EL2: Second electrode HTR: Hole transport region
EML: Emissive layer ETR: Electron transport region
HTL: hole transport layer CPL: capping layer

Claims (22)

first electrode;
a second electrode disposed on the first electrode; and
A light emitting device comprising: at least one functional layer disposed between the first electrode and the second electrode and containing an amine compound represented by the following formula (1):
[Formula 1]

In Formula 1,
L ₁ and L ₂ are each independently a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms,
x is 1 or 2,
Ar is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms,
R ₁ and R ₂ are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted silyl group, a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming group. It is a heteroaryl group having 2 to 30 carbon atoms, or a ring is formed by combining with an adjacent group,
R ₃ is a hydrogen atom, a heavy hydrogen atom, a halogen atom, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkenyl group with 2 to 30 carbon atoms, a substituted or unsubstituted aryl group with 6 to 30 carbon atoms to form a ring, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, or a ring formed by combining with adjacent groups, except in the case where R ₃ is an aryl group substituted with an amine group,
R ₄ and R ₅ each independently represent a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted silyl group, a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming group. heteroaryl group having 2 to 30 carbon atoms,
a and b are each independently integers from 0 to 4,
c is an integer between 0 and 5,
d is an integer between 0 and 3,
e is an integer between 0 and 3,
at least one R ₄ is a hydrogen atom,
It includes a structure in which any hydrogen in the molecule is replaced with deuterium. According to claim 1,
The at least one functional layer includes 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,
The hole transport region is a light emitting device comprising an amine compound represented by Formula 1. According to clause 2,
The hole transport region includes a hole injection layer disposed on the first electrode, and a hole transport layer disposed on the hole injection layer,
The hole transport layer is a light emitting device comprising an amine compound represented by Formula 1. According to claim 1,
A light emitting device wherein the amine compound represented by Formula 1 is a monoamine compound. According to claim 1,
R ₁ and R ₂ are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted methyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted dibenzofuran group, or a substituted or unsubstituted dibenzoheterol group. or a light-emitting device that forms a ring by combining with adjacent groups. According to claim 1,
R ₃ is a hydrogen atom, a deuterium atom, a substituted or unsubstituted allyl group, a substituted or unsubstituted pyridine group, a substituted or unsubstituted tetrazole group, a substituted or unsubstituted dibenzofuran group, or a substituted or unsubstituted tria group. A light emitting element that is a rare element or combines with adjacent groups to form a ring. According to claim 1,
A light emitting device where R ₄ and R ₅ are each independently a hydrogen atom or a deuterium atom. According to claim 1,
Ar is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted quaterphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, A light emitting device comprising a substituted or unsubstituted fluorene group, a substituted or unsubstituted dibenzofuran group, or a substituted or unsubstituted dibenzoheterol group. According to claim 1,
L ₁ is a substituted or unsubstituted phenylene group, a substituted or unsubstituted divalent biphenyl group, a substituted or unsubstituted divalent terphenyl group, a substituted or unsubstituted divalent quaterphenyl group, or a substituted or unsubstituted divalent fluorene. group, a substituted or unsubstituted dibenzofuran group, a substituted or unsubstituted divalent dibenzoheterol group, a substituted or unsubstituted dibenzosilol group, or a substituted or unsubstituted divalent naphthyl group. Light-emitting device. According to claim 1,
L ₂ is a substituted or unsubstituted phenylene group, a substituted or unsubstituted divalent biphenyl group, a substituted or unsubstituted divalent naphthyl group, a substituted or unsubstituted divalent phenanthryl group, or a substituted or unsubstituted divalent A light-emitting device containing a triphenylenyl group. According to claim 1,
The amine compound represented by Formula 1 is a light emitting device represented by any one of the following Formulas 1-1 to 1-3:
[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

In Formulas 1-1 to 1-3,
R ₃₁ , R ₃₂ , and R ₃₃ are each independently a hydrogen atom, a heavy hydrogen atom, a halogen atom, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, or a substituted or unsubstituted ring. An aryl group with 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group with 2 to 30 ring carbon atoms,
c1 is an integer between 0 and 5,
c2 and c3 are each integers from 0 to 7,
However, except for the case where R ₃₁ , R ₃₂ , and R ₃₃ are each an aryl group substituted with an amine group,
Ar, R ₁ , R ₂ , R ₄ , R ₅ , L ₁ , L ₂ , a, b, d, e, and x are the same as defined in Formula 1. According to claim 1,
The amine compound represented by Formula 1 is a light emitting device represented by any one of the compounds of the following compound group 1:
[Compound Group 1]

In compound group 1, D is a deuterium atom. Amine compound represented by the following formula (1):
[Formula 1]

In Formula 1,
L ₁ and L ₂ are each independently a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms,
x is 1 or 2,
Ar is a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,
R ₁ and R ₂ are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted silyl group, a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming group. It is a heteroaryl group having 2 to 30 carbon atoms, or a ring is formed by combining with an adjacent group,
R ₃ is a hydrogen atom, a heavy hydrogen atom, a halogen atom, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkenyl group with 2 to 30 carbon atoms, a substituted or unsubstituted aryl group with 6 to 30 carbon atoms to form a ring, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, or a ring formed by combining with adjacent groups, except in the case where R ₃ is an aryl group substituted with an amine group,
R ₄ and R ₅ each independently represent a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted silyl group, a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming group. heteroaryl group having 2 to 30 carbon atoms,
a and b are each independently integers from 0 to 4,
c is an integer between 0 and 5,
d is an integer between 0 and 3,
e is an integer between 0 and 3,
at least one R ₄ is a hydrogen atom,
It includes a structure in which any hydrogen in the molecule is replaced with deuterium. According to claim 13,
The amine compound represented by Formula 1 is a mono amine compound. According to claim 13,
Ar is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted quaterphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, An amine compound that is a substituted or unsubstituted fluorene group, a substituted or unsubstituted dibenzofuran group, or a substituted or unsubstituted dibenzoheterol group. According to claim 13,
The amine compound represented by Formula 1 is an amine compound represented by any one of the following Formulas 1-1 to 1-3:
[Formula 1-1]

[Formula 1-2]

[Formula 1-3]


In Formulas 1-1 to 1-3,
R ₃₁ , R ₃₂ , and R ₃₃ are each independently a hydrogen atom, a heavy hydrogen atom, a halogen atom, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, or a substituted or unsubstituted ring. An aryl group with 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group with 2 to 30 ring carbon atoms,
c1 is an integer between 0 and 5,
c2 and c3 are each integers from 0 to 7,
However, except for the case where R ₃₁ , R ₃₂ , and R ₃₃ are each an aryl group substituted with an amine group,
Ar, R ₁ , R ₂ , R ₄ , R ₅ , L ₁ , L ₂ , a, b, d, e, and x are the same as defined in Formula 1. According to claim 13,
L ₁ is an amine compound represented by at least one of the substituents of the following substituent group S:
[Substituent group S]

In the substituent group S,
R _S1 to R _S49 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted silyl group, a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming group. heteroaryl group having 2 to 30 carbon atoms,
y1 to y4 and y6 to y42 are each independently integers from 0 to 4,
y5 and y43 to y49 are each independently integers from 0 to 6,
In the substituent group S, " " means the position connected to the nitrogen atom in Formula 1, " " means the position connected to the nitrogen atom of carbazole in Formula 1 above. According to claim 13,
The amine compound represented by Formula 1 is an amine compound represented by any one of the following Formulas 2-1 to 2-6:
[Formula 2-1]

[Formula 2-2]

[Formula 2-3]

[Formula 2-4]

[Formula 2-5]

[Formula 2-6]

In Formulas 2-1 to 2-6,
R ₆ to R ₁₈ each independently represent a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted silyl group, a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming group. heteroaryl group having 2 to 30 carbon atoms,
f, g, h, j, and q are each independently integers from 0 to 4,
i, and n are each independently integers from 0 to 2,
k, l, m, o, p, and r are each independently integers from 0 to 3,
Ar, R ₁ to R ₅ , L ₁ , a to e, and x are the same as defined in Formula 1. According to claim 13,
R ₁ and R ₂ are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted methyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted dibenzofuran group, or a substituted or unsubstituted dibenzoheterol group. or an amine compound that forms a ring by combining with adjacent groups. According to claim 13,
R ₃ is a hydrogen atom, a deuterium atom, a substituted or unsubstituted allyl group, a substituted or unsubstituted pyridine group, a substituted or unsubstituted tetrazole group, a substituted or unsubstituted dibenzofuran group, or a substituted or unsubstituted tria group. An amine compound that is a rare group or combines with an adjacent group to form a ring. According to claim 13,
An amine compound in which R ₄ and R ₅ are each independently a hydrogen atom or a deuterium atom. According to claim 13,
The amine compound represented by Formula 1 is an amine compound represented by any one of the compounds of the following compound group 1:
[Compound Group 1]

In compound group 1, D is a deuterium atom.

Images